DYES CLASSIFIEI BY INTERMEDIATE! data for both...
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D Y E S C L A S S I F I E I
B Y I N T E R M E D I A T E !
D y e s t abu l a r ly a r r a n g e d u n d e r e a c h
in te rmedia te , w i t h s ta t i s t ica l a n d o t h e r
d a t a for b o t h dyes a n d i n t e r m e d i a t e s .
Glossary of D y e a n d I n t e r m e d i a t e
n a m e s a l p h a b e t i c a l l y a r r a n g e d .
BY
R. X O R R I S S H R E V EConsulting Chemist
EN" COLLABORATION WITH
WARREN N. WATSON
AND
A. R. WILLISChemists, U. S. Tariff Commission
BOOK DEPARTMENT
The CHEMICAL CATALOG CCttBPANY, Inc.ONE MADISON AVKNUJS, NEW YORK, TJ. 8. A.
COPYRIGHT, 1922, BY
The CHEMICAL CATALOG COMPANY, Inc.All Rights Reserved
Press ofJ. J. Little & Ives Company
New York, U. S. A.
T A B L E OF C O N T E X T SPAGE
PREFACE 3
ABBREVIATION'S 5
INTRODUCTION 7
PART I. INTERMEDIATES AND DYE TABLES . . . 17
KEY TO PART I 18
INTERMEDIATES WITH DYE TABLES. THE ARRANGEMENT OF INTER-MEDL^TE NAMES 15 ALPHABETICAL AND INCLUDES CHEMICAL ANDCOMMON OR TRIVIAL- NAMES 19
FORMULA INDEX OF INTERMEDIATES 581
PAET II. DYE NAMES 587
GLOSSARY OF DYE NAMES 589
PAGE INDEX OF SCHULTZ NUMBERS FOR DYES 625
P R E F A C E
Experience in the manufacture of dyes indicates that the properviewpoint for a correct technical program is from the intermediate side.This is a direct corollary of the fact that the intermediates are thematerials out of which dyes are fabricated. Furthermore, the tremen-dous complexity of the dye industry, the interrelationship of one dye toanother or of one intermediate to another, as well as the relationship ofdyes and intermediates to the whole organic chemical industry, allrequire that there be available tables showing the commercial dyesderived from each important intermediate. To give this is the primeobject of this work.
I t is believed that this book will be of service not only to manufac-turers in looking for uses of any intermediate, but to research chemistsand to students. Since the tables give the various outlets and thepoundage imported and manufactured, the book will aid the merchantin the buying or selling of dyes and intermediates. The very com-plete glossary of names, both of dyes and intermediates, will help inmany directions, especially as the intermediate part includes theso-called common or trivial names. This feature will be of greatservice in reading the older literature and patents.
The intermediate names are alphabetically arranged. Under eachprincipal name is given the synonyms, which are also cross-indexed intheir alphabetical order. A special feature is the giving of the nameused by Chemical Abstracts; this, together with the listing of the prin-cipal formulas, will aid in the use of the Chemical Abstracts by the DyeChemist.
A Formula Index to the names of the intermediates and to the pagesis given following the main part of this book containing the alphabeticaltreatment of the intermediates. Here the formulas of the intermediatesare listed in an alphabetical order as in a dictionary, except that CHcomes first; and in this way a 5-atom formula may precede a 3-atomone. This is similar to the excellent formula index of the 1920 ChemicalAbstracts.
After the writer had been engaged for some time in the preparationof this book, he was informed of a somewhat similar classificationundertaken by Messrs. Warren N. Watson and A. R. Willis of theTariff Commission, Washington, D.C. It was deemed fair to cooper-
Z
4 PREFACE
ate and to associate the two works by the mutual use of the other namesas " collaborators/7 Messrs. Watson and Willis have published a partof their work, comprising about a third of the Schultz dyes, in theColor Trade Journal serially from May to September during 1921.This serial publication by Messrs. Watson and Willis and this book bythe writer are separate and independent productions. The writer,however, takes this occasion to express his appreciation for advice andhelp to Messrs. Watson and Willis.
I t is a pleasure to acknowledge help from Dr. Austin M. Pattersonon the Chemical Abstracts nomenclature. Aid has also been renderedby J. R. Minevitch, M. N. Conklin and Oscar Newman. The statisticaldata are taken from the yearly Census of Dyes and Coal Tar Chemicalscompiled by the U. S. Tariff Commission, and from Artificial DyestuffsUsed in the United States by Thomas H. Norton.
R. NORKIS SHREVE.NEW YORK CITY
December, 1921.
A B B R E V I A T I O N S
Dye Application ColumnA Acid dyeACr Acid chrome dyeB Basic dyeCL Color lakeD Direct dyeMF Color made on fiberM Mordant dyeS Sulfur dyess Spirit soluble dyeV Vat dye
Statistics ColumnI '14 Imports, Fiscal Year 1914 (year ending
June 30, 1914)I '20 Imports, Calendar Year 1920M717M'18M'19
Manufactured in Calendar Year1917, 1918, 1919, or 1920
M'20
Literature ReferencesBARNETT, ANTHRACENE AND ANTURAQUINONE
E. de Barry Barnct t , Anthracene and Anthraquinone, 1921.
D . Van Nostrand & Co.
B E I L .
Beilstcin, Handbuch clcr organischen Chemie (3rd Ed . ) .
B E R .
Berichte dcr Deutschen Chcmischen Gesellschaft.
C A I N , INTERMEDIATE PRODUCTS
J. C. Cain, The Manufacture of In te rmedia te Products for Dyes,
Second Edition 1919, Macmillan & Co.
F R D L .
P . Friedlacnder, Fortschrit te dcr Teerfarbcnfabrikation, 1877-1916,12 vols., Julius Springer.
5
6 ABBREVIATIONS
GREEN, ORGANIC COLORING MATTERS
A. G. Green, A Systematic Survey of the Organic Colouring Matters,1908 Edition, Macmillan & Co.
GEORGIEVICS AND GRANDMOUGIN, DYE CHEMISTRY
G. von Georgievics and E. Grandmougin, translated by F. A.Mason. A Textbook of Dye Chemistry, 1920. Scott Green-wood & Son.
HEUMANN, ANILINFARBEN
K. Heumann (Fourth part edited by G. Schultz), Die Anilinfarbenund ihre Fabrikation, Four Parts, 1888-1906, Friedrich Viewig.
LANGE, SCHWEPELFARBSTOFFE
Otto Lange, Die Schwefelfarbstoffe, ihre Herstellung und Verwen-dung, 1912, Otto Spamer.
LANGE, ZWISCHENPRODTJKTE
Otto Lange, Die Zwischenprodukte der Teerfarbenfabrikation,1920, Otto Spamer.
THORPE, Die. CHEMISTRY
Edw. Thorpe, A Dictionary of Applied Chemistry, First Edition,Longmans Green & Co.
ULLMANN, ENZY. TECH. CHEMIE
Enzyklopaedie der technischen Chemie, Edited by Dr. Fritz Ull-rnann, 1914. Urban & Schwarzenberg.
Miscellaneouso orthom metap paraa alpha/3 betaN Nitrogen (signifies nitrogen attachment
of radical)C. A. nomen. . . Chemical Abstracts nomenclature(mols) MoleculesSchultz Number . Number for dye as given in Schultz,
Farbstofftabellen, 1914 Edition.
I N T R O D U C T I O N
The contents of this book fall into two parts: first, an alphabeticallist of intermediates with their data and dye tables, and second, anaphabetical list of dye names referring to their Schultz numbers whenknown, by which any dye here classified can be found in the tables bylooking in the "Page Index of Schultz Numbers" at the end of the bookfor the appropriate pages.
Often an intermediate is known by as many as half a dozen names,and each one is listed in its alphabetical order, but the synonyms allrefer to one name under which are arranged the tables and other da ta .Thus the book is a glossary of intermediate names. In selecting thename given at the head of the data for a certain intermediate, thewriter was influenced first by considerations of clearness and thenof custom and usage. For a full discussion of this important nomen-clature question, reference is made to the nomenclature section of thisintroduction.
Following the synonyms, is given the structural formula, the empiricalformula, and the molecular weight. It is the emphatic opinion of thewriter that the indexing of organic compounds by their formulas is thesimplest, the most universal, and the clearest. Chemical Abstracts,starting with 1920, has inserted a formula index, and it is believed t h a tchemists can find a given intermediate quicker and more surely inChemical Abstracts by the use of this formula index than by the ordinarysubject index. The formulas given here will be an aid in this direction.Furthermore a formula index is included in this book.
Under each intermediate there is listed a short description of methodsof Formation followed by Literature References. These are not exhaustivein any sense, but the aim has been to give the usual commercial prepa-ration together with several references to the literature for any one whodesires more details. The references to Lange, Zwischcnproduklo,cover the German patents.
In order to give some basis for judging the extent to which a dye oran intermediate is used, the statistical data for importation and manu-facture in the United States is given under Statistics, These data aretaken from the following government reports: Census of Dyes and Coal-Tar Chemicals, by U. S. Tariff Commission; Artificial Dyestujfs Used inthe U. S.9 by Thomas H. Norton, and Chemicals and Allied Products
7
8 INTRODUCTION
Used in the U. S. by E. R. Pickrell. The Imports 1914 both under inter-mediates and under dyes refer to the imports for the fiscal year endingJune 30, 1914. Otherwise the imports, and always the amounts manu-factured, refer to the calendar year marked. It is believed that theaddition of these statistical data to the tables will be of much service inpointing out forcibly the relative commercial importance of the dyesand intermediates, and will help to complete development of the dyeindustry in America. In considering these statistics, it must be bornein mind that since 1914 the United States has been endeavoring tofully supply her own needs, and proceeded naturally along the lines ofleast resistance, so that often a dye was manufactured because of itscomparative simplicity, to be later superseded by a more suitable dyeof more complexity. The Imports for 1914 (fiscal year ending June30, 1914) are "normal" except that Vat Dyes were not imported asheavily that year as had been the usual case.
The statistics of import of a dye, especially for the fiscal year endingJune 30, 1914, often include a number of very similar though notidentical dyes. These statistics were obtained by adding together theindividual dye weights as listed by Norton under a given Schultznumber.
Where Tlh M'19, Manufactured 1919, etc., are given followed by aquestion mark, it indicates that the dye or intermediate was importedor manufactured for the year marked but in amounts that have notbeen disclosed by the U. S. Government.
When a figure is given for imports or manufactures of dyes or inter-mediates, this figure always refers to pounds.
The tables proper give for any intermediate all the dyes listed inSchultz, Farbstofftabellen, 1914 Edition, that are derived from thisintermediate. This includes practically all of the important dyesexcept a few of the newer ones of undisclosed constitution. Thus agiven dye is separately arranged under each of its intermediates. Asthere is named in a special column the Other Intermediates constitutinga dye besides the one at the head of each table, the intermediate rela-tionship is clearly stated.
The following dyes listed in Schultz, Farbstofftabellen (1914), arenot classified, on account of lack of information as to their composition-
30 Radial Yellow G 706 Cachou de Laval87 Peri Wool Blue 707 Sulfine Brown
608 Euchrysine 708 Sulfaniline Brown609 Homophosphine G 744 Sulfo Black B, 2B
INTRODUCTION 0
751 Krygene Brown RB 756 Kryogene Black TGO752 Kryogene Direct Blue GO 757 Sulfogcnc Brown G, D753 Kryogene Direct Blue B 863 Anthraquinone Blue Green B XO754 Kryogene Direct Blue 3B 871 Indanthrcne Violet RN Extra755 Kryogene Black BNX
In very many cases, the writer has supplemented the informationin Schultz, Farbstofflabellen, as to composition of dyes, and hence hasbeen able to classify many dyes whose composition is indefinite in thisbook. In a number of instances when Schultz refers the dyes to com-plex intermediates, these have been split into simpler components, andthe components as well as the complex parent compound have all beenindexed. Also certain obvious errors in Schultz, Farbstofftabcllen, havebeen corrected, as for example, where in //182, reference is made toL-amino-4-naphthol-sulfonic acids which the patent refers to ar.a-rsulfonic acids (l-amino-8-naphthol-sulfonic acids) and specifically namesH acid in the example given.
When the patents describing a dye list a number of intermediates,then those listed under Example I of the patent are chosen for classifica-tion unless, of course, Schultz, Farbstofftabdlen, gives definite composi-tion to the dye. Quite often intermediates arc indexed even thoughnot a component part of the final dye, provided they were necessaryto its manufacture, e.g. benzoic acid in the manufacture of certain ofthe Triphenyl-methane Dyes as Diphenylamine Blue and Aniline Blue.
All possible intermediates for any given dye are not indexed, but itis hoped to extend the present classification at a later date. Previoustables resembling those given here, but along much less extensive lines,are to be found in Heumann, Die Anilinfarben und ihre FabricationIV, II , 2, pages 1943-2013, and Lefevre, Traite des Matures Coloranlca(1896), pages 140-407.
In the column in the tables headed Other Intermediates Used andNotes, there is given first the intermediates other than the one at thehead of the table, which compose the dye in question. Unless other-wise marked, it is to be understood that one molecule of an intermediateis used. When more than one molecule is employed, of the intermediateheading the table, then the name of this intermediate is also given inthe Other Intermediates column followed by the number of molecules(mols) that are used in the dye.
The notes are in brackets, and are mostly self-explanatory, and referchiefly to constituents, such as sulfur (S), sodium sulfide (Na2S), andthe like, which enter into the formation of the dye. Such steps op
10 INTRODUCTION
Sulfonation, Bromination, and Chlorination are given, but Couplingby Diazotization and Condensation are to be understood.
Under notes is generally listed the name of a given dye if it is a stepin the preparation of the dye classified in the table, but this componentdye is not used as the index or heading for any of the dye classificationtables, and this fact is indicated by placing the name of the componentdye in a bracket.
Indigo is an exception, and the dyes based on it are tabulated there-under as well as under the various component intermediates.
The last column in the tables classifies the dyes by their usual methodof application as indicated by the following abbreviations.
A Acid dyeACr Acid chrome dyeB Basic dyeCL Color lakeD Direct dyeM F Color made on fiberM Mordant dyeS Sulfur dyess Spirit soluble dyeV Vat dye
A classification of this kind is not very exact in certain cases wherea dye is susceptible of several different methods of application. Theaim has been to give the mode of application most generally employed.
Regarding the naming of the dyes, there is used in the tables thatname first given in Schultz, Farbstojftabellen (1914), followed by asecond name in those cases where the second name is more generallyused in the United States than the first Schultz name.
A glossary of the ordinary German and Swiss names, together withmany of the American and English names, is given in the back of thebook. I t would have been very helpful to have added to this list allthe current American and English marks, but in the present develop-ment stage of the American dye industry, this turned out to be im-practical. The list as given includes those listed and classified byNorton in Artificial Dyestuffs Used in U. £., with various correctionsand a considerable number of additions. These names refer to "Schultz"numbers where known, and as the last few pages of the book give a listof the pages on which occur references to any "Schultz" number, theplace of any dye of known constitution can be readily found, togetherwith the data regarding that dye.
INTRODUCTION 11
In the tables, the dyes are classified under the usual constitutionalheadings, which are here grouped in the following list:
Nitroso DyesNitro DyesStilbcne DyesPyrazolone DyesMonoazo DyesDisazo DyesTrisazo DyesTetrakisazo DyesAuramincsTriphenyl-methane DyesDiphenyl-naphihyl-mcthane DyesXanthone DyesAcridine DyesQuinoline DyesThiobcnzcnyl DyesIndophcnolOxazinc DyesThiazinc DyesAzinc DyesSulfur DyesAnthraquinone and Allied DyesIndigo Group DyesAniline Black Group
NOMENCLATURE
The scientific naming of intermediates has indeed been confused,and in many instances a number of names have been used for the samecompound, or the same name for several different compounds. I t hasbeen the aim of this book to give the various names met with in theliterature for the intermediates, and to cross-index these names in thealphabetical arrangement,—thus giving a glossary of intermediatenames for all those common intermediates here considered. Further-more the common or trivial names are listed in a very complete mannerand include the trivial names for many intermediates not speciallyconsidered here. As mentioned before, there has been chosen for theprincipal name from among the various synonyms that name which isclear and which is sanctioned by custom. In so choosing, the tendencyhas been to adopt a few of the well-known trivial or common names,
12 INTRODUCTION
such as H Acid and Nevile-Winther's Acid, in place of the strictlychemical names; for the writer's experience is that dye men, whetherin the research laboratory, the factory, or the office, speak of H Acid forexample, and not l~amino-8-naphthol-3: 6-disulfonic acid.
The most scientific nomenclature is that used by Chemical Abstractsof the American Chemical Society. This is fully explained in theIntroduction to Decennial Index of Chemical Abstracts, as well as inthe Journal of the American Chemical Society.1
It, however, offers the disadvantage of requiring considerable studyto master its principles, which often vary from the practice of the dyeindustry, and furthermore there is comparatively little literature per-taining to dyes and intermediates in the years covered by ChemicalAbstracts.
On the other hand, organic chemistry is now so complex that moreattention must be paid to scientific naming of organic compounds,and also the amount of dye literature contained in Chemical Abstractsis increasing yearly, so that it is to the advantage of the dye chemistto familiarize himself with the procedure of Chemical Abstracts, and itcannot be too strongly recommended that every one make a studyof the principles of Chemical Abstracts nomenclature as disclosed inthe references given above.
This book aims to give the Chemical Abstracts name for each inter-mediate; and in the many cases where this name differs from the onein common use, this Chemical Abstracts name is so designated bybeing marked C. A. nomen., as an abbreviation for Chemical AbstractsNomenclature. If only one name is listed, it is to be understood thatthis is the one sanctioned by Chemical Abstracts.
Beginning with the 1920 volumes of Chemical Abstracts, a FormulaIndex is included, which offers the easiest way to find reference to achemical compound or its nomenclature.
In case of many benzene derivatives, the writer has adopted theChemical Abstracts nomenclature, as there is considerable confusionin the literature regarding these names, and as the Chemical Abstractsprocedure does not vary greatly as a rule from well-recognized practice.However, in case of many of the naphthalene derivatives the ChemicalAbstracts practice is so far from what is commonly used that the Chem-ical Abstracts names are only given as synonyms. The men responsiblefor Chemical Abstracts are showing a great willingness to bring their
1 Patterson and Curran, J. Amer. Chem. Soc. 39, 1623-38 (1917).
INTRODUCTION 13
system as near to that used in practice as possible, and in all probabilitythe near future will show closer accord.
The very common use of more than one of the terms ortho, mela, andpara, to indicate position of substitucnts, is very confusing and shouldbe dropped in preference either to the procedure of Chemical Abstractswhere one such term is used in connection with numbers, or to theuse of numbers alone. For example, m-nilro-p-toluidine (CH3=1) ando-amino-phenol-p-sulfonic acid should be replaced by 2-nitro-p-toluidine(NH2=1) and 2-amino-l-phenol-4-sulfonic add, the present ChemicalAbstracts usage. In the former case the writer much prefers the namel-amino-2-nitron-toluene.
Chemical Abstracts uses p-tolwidine (NH2=1) and p-phenylene-dia-mine and the like as "index compounds" with the various substituentsas modifiers, arranged in an inverted order in their indices. In thisbook the practice of Chemical Abstracts in this regard is followed,except for the inversion for the principal name of the intermediate.The other names arc given as synonyms and cross-indexed. However,in the body of the tables, such terms as o-amino-phenol-p-sulfonic acidarc used in a few cases because of their very common usage, and conse-quent quick recognition.
Treating the matter broadly, the gist of the Chemical Abstractsnomenclature practice is that the "chief function" of a compound isexpressed in the main part of the name, which with "its functionalending, if any, is placed first in the index, the names of the substituentsfollowing." The numbering starts from the "chief function" and isnot varied by the addition of substituents, for instance,—2: 7-naphtha-lene-sulfonic acid is an "index compound," as is likewise 1 naphthalene-sulfonic acid; and thoir amino, halogon, and nitro derivatives areindexed thereunder. For instance, Laurent's Acid or what is ordinarilycalled l~naphthylamine-5-sulfonic acid is indexed by Chemical Abstractsunder 1-naphthalene-sulfonic acid, and called 5-amino-l-naphthalene-sulfonic add. In the decennial index, hydroxy was also considered asa substituent.
However, naphthol-sulfonic acids and phenol-sulfonic acids are nowrecognized by Chemical Abstracts as exceptions to their rule of assigningthe chief function to acids, and of allowing only one functional endingin the index name. So that while in the decennial index these -ol-sulfonic acids had their numbering start with the sulfonic group, nowthe numbering begins with the hydroxyl. For example, l-naphthol-4-sulfonic acid and 1-naphthol-S: 6-disulfonic acid. In case of amino- nitro-
14 INTRODUCTION
chloro- derivatives and the like, the positions are referred to the setnumbering of the index compound. Take H Acid,—this is viewed as aderivative of index compound l-naphthol-3:6-disulfonic acid by ChemicalAbstracts, and is named in their index as 8-amino-l-naphthol~3:6-disulfonic add, or in their inverted form as l-naphthol-3: 6-disulfonicacid, 8-amino-.
This numbering is quite different from the ordinary numbering ofl-amino-8-naphthol-3: 6-disulfonic acid for H Acid. The giving in thisbook of both nomenclatures will help in the using of Chemical Ab-stracts, and as a further aid in this direction the first letter of theindex compound as employed in Chemical Abstracts is italicized.
The rule of Chemical Abstracts regarding arrangement of substituents,reads as follows:—"The names of substituent radicals in the name of acompound are arranged in alphabetical order." This is an excellentpractice and should be universally adopted. In conformance with this,benzyl-ethyl-aniline is recommended, and not ethyl-benzyl-aniline.
In the naming of toluene derivatives, the usual custom has been tostart numbering from the CH3 group irrespective of other substituents.In Chemical Abstracts, the numbering starts from the chief function,and the order of the chief function is: "onium compounds, acid (car-boxylic first), acid halide, amide, imide, aldehyde, nitrile, ketone, alcohol,phenol, mercaptan, amine, imine, ether, sulfide (and sulfoxide and sul-fone)" So whenever sulfonic acid is present, the start of the numberingis with this group, except that the carboxylic group, being an acid radical,is of same order as sulfonic, and has been given precedence over thesulfonic radical. Instead of toluidine-sulfonic acid with the numberingbased on the CH3, Chemical Abstracts uses amino-o- (or m- or p-)toluene-sulfonic acid and starts the numbering with the sulfonic acidgroup. Toluidines start their numbering from the NH2 group, as it hasprecedence over CH3. Another divergence of the Chemical Abstractspractice from the ordinary numbering is the place of the numbersor letters in such terms as the following:
Ordinary Practice Chemical Abstracts PracticeNaphthalene-2:7-disulfonic Acid 2: 7-Naphthalenedisulfonic AcidToluene-p-sulfonic Acid p-Toluenesulfonic Acid
The custom of using hyphens to set off radicals and substituents fromeach other and from the parent compound is extensively used in thisbook for the sake of clearness, and as an aid to the eye and the mind.No one thinks of a complex organic chemical as a whole, but as a com-
INTRODUCTION 15
plex of various substituents around a central body; therefore thewriting of a long name like tetramethyldiaminodiphenymethane as oneword is very reprehensible and should be early abandoned. Otherwisethe careless practice of writing as two or more separate words thename of one chemical individual is bound to increase; already thislatter practice is gaining too much headway, as can be seen by aninspection of our trade or semi-technical journals.
The rule about hyphens as used here is to insert them betweenall radicals, and between the radicals and the parent body, exceptin the case of compound radicals, such as mcihylamino- (CH3NH~),tetraethyl-, disulfo?iic- and the like. Melhylamino should not be writtenmethyl-amino. While Chemical Abstracts does not employ hyphensin this broad way, yet the use of hyphens has been extended to thenames otherwise following Chemical Abstracts procedure.
It is clearly recognized that the nomenclature here used is not alwaysconsistent as between the scientific and common usage. For examplewhile 2-amino-l-phenol-4-sulfonic acid is listed as the principal nameof this intermediate, yet in the body of the tables the ordinarily usedsynonym o-amino~phenol-p-suljonic acid is given because of its quickrecognition. However, the movement to a more scientific nomen-clature such as used by Chemical Abstracts should be encouraged asmuch as possible, and such terms as o-cwiino-phcnol-p-sulfcmic acidshould be dropped gradually.
KEY TO PART I INTERMEDIATES AND DYE TABLES
The arrangement is alphabetical not only by chemical but by trivialor common names. Many trivial names are listed for intermediateswhich are not further considered. Dye tables and other data ac-company those intermediates which enter directly into the formationof the commonly used dyes.
Synonyms and trivial names are given for the intermediates, andthese synonyms and trivial names are listed not only under the ap-propriate intermediate but also separately in the alphabetical arrange-ment.
That chemical name called for by the Chemical Abstracts nomen-clature is to be found either as the principal name of each intermediateor among: its synonyms. This is distinguished by being followed bythe abbreviation C. A. nomen., except whon only one name is used foran intermediate, in which case this name is the one in common usageand is also that one sanctioned by Chemical Abstracts. In the indicesof Chemical Abstracts the names are alphabetically arranged under anumber of "parent compounds" which in ordinary usage are precededby the modifying radicals. As this book follows the ordinary usage,it was thought that it would be helpful to designate the Chemical Ab-stracts "parent compound," which is done by italicizing the firstletter of these "parent compounds" in those names following ChemicalAbstracts nomenclature.
The prefixes m-, o-, p-, a-, $- and the like are not considered in themain alphabetical arrangement. Hence /3-naphthol (beta-naphthol) isto be found under N.
The import statistics are not for each strictly individual dye mark,but represent a group identical to or closely resembling a given Schultzdye. These figures are arrived at by adding the total poundage of thesedyes arranged by Norton under each Schultz number in his book,Artificial Dyestuffs Used in U. S.
Unless otherwise marked, it is to be understood that only one mole-cule of each intermediate is a part of a dye. Furthermore, when morethan one molecule is employed of the intermediate heading a dye table,the name of this intermediate is entered under the Other Intermediatescolumn followed by the number of molecules involved.
A fuller consideration of these principles is to be found in the Intro-duction. See also abbreviations on page 5.
18
INTERMEDIATES
The intermediates are arranged alphabetically by their chemicalnames and by their trivial or common names, and they are accompaniedby the dye tables and other data. See Introduction, or page 18, forexplanation of this arrangement.
A Acidl:7-Dihydroxy-naphthalcnc-3:6-disulfonic Acid (not considered
herein)
Acenaphthenequinone (C. A. nomen.)
7: 8-Diketo-accnaphtheneCO-CO
FORMATION.—From acenaphthenc by oxidation
LITERATURE.—Cain, Intermediate Products (2d Ed.), 242
Dyes Derived from Acenaphthenequinone
Schultz
for Dye
907
90S
911
Ordinary Name andClans of Dye,
INDKJO GROUP DVIJSCibii Seiuld, CJ
Ciba Keel R
Ciba Onui&o (\
Statistics ofImport andManufacture
I '11.-22,2051 '20.-25,578I '14:— 1,001
V 14:-— 222
Other I ntcr m edict lasUwd and Notes
2-IIy(lroxy-iluo-naphthene
2-1 Iy< Iroxy-tl lioiuipl I-thono [Bromiuatioii]
5-A mino-2-1 iydroxy-tlnoiuiplithcnc
DyeAppli-cationClass
V
Y
Y
3-Acenaphthenol (C. A. nomcn.)
Sec, 3-IIydroxy-aconapl 11hone
20 DYES CLASSIFIED BY INTERMEDIATES
1-Acetamido-anthraquinone
oooNH.CO.CH3FORMATION.—From 1-amino-anthraquinone by action of acetic aihydride on solution in oleumLITERATURE.—Lange, Zwischenprodukte, #3124Dyes Derived from 1-Acetamido-anthraquinoneSchultzNumberfor Dye
813
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
IndanthreneCopper R
Statistics ofImport and
Manufacture
I'14:—1,268
Other IntermediatesUsed and Notes
1:6- (or 1:7-) Diacet-amido-anthraqumone
DyeApplicatiorClass
V
2 - A c e t a m i d o - a n t h r a q u i n o n e
C C •c o •
FORMATION.—From 2-amino-anthraquinone by action of acetic arhydride on oleum solution
LITERATURE.—Lange, Zwischenprodukte, #3121:
Dyes Derived from 2-Acetamido-anthraquinone
S c h u l t z
N u m b e r
f o r D y e
8 1 2
O r d i n a r y N a m e a n d
C l a s s o f D y e
A N T H R A Q U I N O N E A N D
A L L I E D D Y E S
I n d a n t h r e n e
O r a n g e R T
S t a t i s t i c s o f
I m p o r t a n d
M a n u f a c t u r e
1 1 4 : — 2 , 1 0 3
I ' 2 0 : - - 3 8 1
O t h e r I n t e r m e d i a t e s
U s e d a n d N o t e s
1 : 6 - ( o r 1 : 7 - ) D i a c e t -
a m i d o - a n t h r a q u i n o n e
D y e
A p p l i
c a t i o n
C l a s s
V
8 - A c e t a m i d o - l - n a p h t h o l » 3 : 6 - d i s u l f o n i c A c i d
S e e , A c e t y l - H A c i d
DYES CLASSIFIED BY INTERMEDIATES
Acetanilide
NH.COCH3
21
STATISTICS.—Manufactured 1917:—1,897,703 lbs.Manufactured 1918:—2,085,088 lbs.Manufactured 1919:—1,934,125 lbs.Manufactured 1920:—2,667,252 lbs.
FORMATION.—By heating aniline with glacial acetic acid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 52Lange, Zwischenprodukte, #117
USES.—For preparation of p-nitro-acetanilide, and for p-nitro-aniline
Aceto-acetic Ethyl Ester
CH3 . CO. CH2. CO. OC2 5 = C6Hio03 = 130
FORMATION.—By the reaction of dry sodium ethylate and dry ethylacetate
Schult»Numberfor Dye
19
22
2527
773
Dyes Derived
Ordinary Name andClass of Dye
PYRAZOLONE DYESFlavazine LFast Tight Yellow
Xylcne Yellow 3 G
Dianil Yellow 3 GDianil Yellow 2 II
ANTHRAQUINONE ANDALLIED DYES
Anthracene Yollow
from Aceto-acetic Ethyl Ester
Statistics ofImport andManufacture
I > 14 .—38,908I'20:—• 9,327
I ' 14:—23,074I '20:—77,782
I '14:— 4,04a
Other Intn mediatesUsed and Notes
AnilinePlienyl-hydrazinc-p-
sulfonic Acid2: 5-Dicliloro-phcnyl-
liydra-zinc-4-sulfonicAcid
Primulinc-sulfonic AcidPrimulinc-Rulfonic AcidPhcuyl-hydrazinc-p-sul-
fonic Acid
Pyrogallol
DyeAppli-cationClass
A
A
DD
M
yV-Acetyl-l-amino-8-naphthol-3: 6-disulfonic Acid
See, Acetyl-H Acid
22 DYES CLASSIFIED BY INTERMEDIATES
Acetyl-H Acid
iV-Acetyl-l-amino-8-naphthol-3:6-disulfonic Acid
8-Acetamido-l-naphthol-3: 6-disulfonic Acid (C. A. nomen.)
HO NH.CO.CH3
= C12HnNO8S2 =HO3S SO3H
STATISTICS.—Manufactured '20:—?
FORMATION.—From H acid by acetylation
Dyes Derived from Acetyl-H Acid
SchultzNumberfor Dye
42
66
Ordinary Name andClass of Dye
MONOAZO DYESAmido Naphthol
RcdG
Amido NaphtholRed 6 B
Statistics ofImport and
Manufacture
I '14:— 3,500M '17:— ?M 'IS:— ?M'19:— ?M'20.-132,637I '20:— 2,028
I '14:— 45,697M'lS:— ?M'19:— ?M'20:—142,567I '20:— 1,299
Other IntermediatesUsed and Notes
Aniline
2)-Amino-acetanilide
DytApplcatioClas
A
A
Acetyl-1: 4-naphthylene-diamine-6-sulfonic Acid
8-Acetamido-5-amino-2-naphthalenc-sulf onic Acid (C A. nomer
NH2
HO3S= C12H12N2O4S:
N H . C O . C H a
:280
FORMATION.—From mixture of l~naphthylamine-6-and-7-sulfonic aci(Cleve's Acids) by acetylation with glacial acetic acid, nitrati<with mixed acid, and reduction with iron.
LITERATURE.—Georgievics and Grandmougin, Dye Chemistry, 152
DYES CLASSIFIED BY INTERMEDIATES 23
Dyes Derived from Acetyl-1: 4-naphthylene-diamine-6-sulfonic
SchultzNumberfor Dye
273
274
Ordinary Name andClass of Dye
DISAZO DYESDiaminogcn Blue BB
Diaminogcn B
Statistics ofImport and
Manufacture
I '14:— 8,308M'17:— ?I '20:— 5,936I '14:—313,029I '20:— 18,120
Other IntermediatesUsed and Notes
a-NaphthylamineSchaeffcr's Acid[Saponification]a-NaphthylamineGanima Acid[Saponificaiion]
Acid
DyeAppli-cationClass
D
D
Acetyl-p-phenylenediamine
See, p-Amino-acctanilide (C. A. no?nen.)
o-Acid (of Claus and Voltz)
See, Croceine Acid
1:2:4 Acid
See, l~Amino-2-naphthol-4-sulfonic Acid
/3 Acid or Beta Acid
See, Anthraquinone-2-sulfonic Acid
8 Acid or Delta Acid
See, l-Naphthylamine-4: 8-disulfonic Acid and 2-Naphthyl-amine-7-sulf onic Acid
€ Acid or Epsilon. Acid
See, l-Naphthol-3: 8-disulfonic Acid
See, l-Naphlhylamine-3: 8-disulfonic Acid
and 1: 8-Dihydroxy-naphthalcne-3-sulfonic Acid (not con-
sidered herein)
f Acid or Zeta Acid
Naphthasultone-3-sulfonic Acid (not considered herein)
DYES CLASSIFIED BY INTERMEDIATES
X Acid or Lambda Acid
See, l-Naphthylamine-2-sulfonic Acid
/x Acid or Mu Acid
See, l-Naphthylam.ine-6-sulfonic Acid
P Acid or Rho Acid
See, Anthraquinone-1: 5-disulf onic Acid
X Acid or Chi Acid
See, Anthraquinone-1: 8-disulfonic Acid
Alen's a or Alen's Alpha Acid. {This is generally followed by the classof the compound, e.g., AUn's a Naphthylamine-disulfonic Acid)
See, Freund's Acid (l-Naphthylamine-3: 6-disulfonic Acid)
l-Nitro-naphthalene-3:6-disulfonic Acid (not consideredherein)
Alen's p or Alen's Beta Acid. (Generally followed by the class of thecompound, e.g., Alerts fi Naphthylamine-disulf onic Acid)
l-Naphthylamine-3:7-disulfonic Acid (not considered herein)
l~Nitro~naphthalene-3: 7-disulfonic Acid (not considered herein)
Alizarin
1:2-Dihydroxy-anthraquinone
a : /3-Dihydroxy-anthraquinone
CO 0 H
STATISTICS.—See #778 in following table
FOKMATION.—From sodium 2-anthraquinone-sulfonate by fusion withcaustic oda for 2-3 days at 200° C , in autoclave, and in presence ofpotassium chlorate
LITERATURE.—Schultz, Farbstofftabellen (1914 Ed.), #778
DYES CLASSIFIED BY INTERMEDIATES
SchultzNumberfor Dye
778
779
780
781
783787788
797
798
799
854
862
Dyes
Ordinary Name andClass of Dye
ANTHEAQUINONE ANDALLIED DYES
Alizarin
Alizarin Orange
Alizarin Red
Erweco Alizarin AcidRedBS
PurpurinAlizarin Bordeaux BAlizarin Cyanine R
Alizarin Garnet R
Alizarin Maroon W
Alizarin Cyanine G
Alizarin Viridinc DG
Alizarin BlueBlack B
Derived from Alizarin
Statistics ofImport and
Manufacture
I '14:—202,392M'17:— ?M'18:— ?M'19:— ?M'20 — ?I '20.— 8,575I '14:— 14,239M'19:— ?M'20:— ?I '20:— 500I '14:— 81,919M'17:— ?I '20:— 12,628
I '20.— 20I '20— 16,781
I '14— 720
I '20— 2,014
I '20:— 339
I '20— 11,397
I '14— 54,706I '20.— 28,802
Other IntermediatesUsed and Notes
[Nitration]
[Sulfonation]
[Sulfonation]
[Oxidation][Oxidation][Alizarin Bordeaux B,
Oxidation][1-Nitro-alizarin, Re-
duction][Crude Nitro-alizarin,
Reduction][Alizarin Cyanine R,
Arhidation][Alizarin Bordeaux B]p-Toluidine (2 mols)[Sulfonation][Purpurin]Aniline[Sulfonation]
DyeAppli-cationClass
M
M
M
M
MMM
M
M
M
M
M
Alpha = aNote.—This is not considered in the alphabetical arrangement,
e.g. alpha-N'aphthol is indexed as a-Naphthol under "N."However P-Naphthol is placed after a-Naphthol
Alpha-NaphtholSee, a-Naphthol under N,
26 DYES CLASSIFIED BY INTERMEDIATES
p-Amino-acetanilide (C. A. nomen.)
Acetyl-p-phenylene-diamine
N H . C O . C H 3
=C8Hi0N2O=150
NH2
STATISTICS.—Imported '14:—6,261 lbs.Manufactured'17:— ?Manufactured '18:—177,990 lbs.Manufactured ;19:— 62,567 lbs.Manufactured '20:— 97,275 lbs.
FORMATION.—From p-nitro-acetanilide by reduction with iron andacetic acid at not higher than 60° C.
LITERATURE.—Cain, Intermediate Products (2d Ed.), 89Lange, Zwischenprodukte, #558
Dyes Derived from p-Amino-acetanilide
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
61M O N O A Z O D Y E S
Victoria Violet I '14:— 52,365M'17M ' l SM'19I '20
M'20
-105,086- 2,082
64
65
Azo Acid Red BLanafuchsine
Azo Coralline L
I '14:— 78,305M'17M ' l SM'19I '20:—
M'20:—
M'17:—
15,272674
Chromotropic Acid[Saponification]
l-Naphthol-3: 6-disul-fonic Acid
R Acid
I J20:— 249M'20:— ?
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from p-Amino-acetanilide (continued)
27
SchultzNumberfor Dye
66
67
239
243
244
290
296
714
715
Ordinary Name andClass of Dye
MONOAZO DYES(continued)
Amino NaphtholRed 6B
Cliromoiropo 6B
DISAZO DYESAzotol C
Coomassie WoolBlack R
Coomassie WoolBlack S
Violet Black
Cotton Yellow G
SULFUH DYESThiophor Yellow
Bronze G
Thiocatechinc
Statistics ofImport and
Manufacture
I '14:— 45,697M'lS:— ?
I '20:— 1,299M'20:—142,567I '14:— 2,818M'17:— ?M'lS:— ?M'19:— 77,4S1M'20:— ?
M'lS:— ?M'19:— ?
I '14:— 31,472I '20:— 4,651
Other IntermediatesUsed and Notes
Acetyl-H Acid
Chromotropic Acid
?ft-Phcnylonc-diammc[Amino-chrysoidinc]
/3-Naphthola-NaphthylamincSchacffer's Salta-NaphthylamincB SaltNcvilc-Winthcr Acida-NaphthylamineSalicylic Acid (2 mols)p-Amino-acctanilide (2
mols)Phosgene
p-Phcnylcnc-diammeBcnzidine[Sulfur][Sulfur]
DyeA ppli-cationClass
A
A
MF
A
A
D
D
S
S
3-Amino-alizarin (C. A. nomen.)
/3-Amino-alizarin
OHCO.
CO
OHNH2
FORMATION.—From 3-nitro-alizarin by reduction.
28 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 3-Amino-alizarin
SchultzNumberfor Dye
S03
S04
SOS
S09
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Alizarin Blue WX
Alizarin Blue S
Alizarin Green X
Alizarin IndigoBlueS
Statistics ofImport and
Manufacture
I '14:—319,394M'19:— ?I '20:— 5,585I ;14:—117,850I '20:— 43,679I '14:—135,191I '20:— 4,254
Other IntermediatesUsed and Notes
3-Nitro-alizarin[Glycerol]
3-Nitro-alizarin[Glycerol]3-Nitro-alizarin[Glycerol; Oxidation]3-Nitro-alizarin[Glycerol; Oxidation]
DyeAppli-cationClass
M
M
M
M
4-Amino-#lizarin (C. A. nomen.)
a-Amino-alizarin
STATISTICS.—See #797 in following table
FORMATION.—From 4~nitro-alizarin by reduction with alkaline sulfides
LITERATURE.—Schultz, Farbstofftabellen (1914 Ed.), #797
Dyes Derived from 4-Amino-alizarin
fichultzNumbcifor Dye
797
805
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Alizarin Garnet B
Alizarin Green S
Statistics ofImport and
Manufacture
I 14:— 720
I'14:— 15,885
Other IntermediatesUsed and Notes
[This is 4-Amino-ali-zarin]
[Glycerol]
DyeAppli-cationClass
M
M
a-Amino-alizarin
See, 4-Amino-alizarin ( C A. nomen.)
DYES CLASSIFIED BY INTERMEDIATES 29
/3-Amino-alizarinSee, 3-Amino-alizarin (C A. nomen.)
2-Amino-5-(P-amino-phenyl)-^enzene-sulfonic Acid (C. A. nome?i.SO*H=1)
See, Benzidine-sulfonic Acid
P-(p-Amino-anilino)-phenol (C. A. nomen.)
See, 4-Amino-4/-hydroxy-diphcnylamiac
1-Amino-anthraquinone (C. A. nomen.)
a-Amino-anthraquinoneN H 'CO
FORMATION.—(1) From 1-nitro-anthraquinone by reduction with sodiumsulfide
(2) From anthraquinone-1-sulfonic acid (potassium salt) byheating with 10 per cent ammonia in an autoclave to 180-190°
LITERATURE.—Ullmann, Enzy. tech. Chemie. 1, 474Lange, Zwischcnproduktc, #3066, 3109, 3158
Dyes Derived from 1-Amino-anthraquinone
SchultzNumberfor Dye
814
824
826
830
834
870
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Algol Yellow W G
Algol Orange R
Indanthrene Red G
Indanthrcne Red R
Algol Gray B
Algol Corinth R
Statistics ofImport and
Manufacture
I '14:—5,185T *OO* A.I '14:— 51I'20:— 400
I '14:—2,099I '20:—6,595
I '14:—4,192I'20:— 840I'20:— 134
Other IntermediatesUsed and Notes
Bcnzoyl chloride
2-Ghloro-anthraquinonc
2: 6-Dichloro-anthraqui-nonc
1-Amino-anthraquinone(2 mols)
2:7-Dichloro-anthra-quinono
1-Amino-anthraqui-none (2 mols)
1-Chloro-anthraquinone[Nitration, Reduction]
2-Chloro-anthraquinone[Nitration, Reduction]Benzoyl chloride
Dye,A p pli-cationClass
V
V
V
V
V
30 DYES CLASSIFIED BY INTERMEDIATES
2-Amino-anthraquinone (C. A. nomen.)
/3~Amino-anthraquinone
= C1 4H9NO2=223
STATISTICS.—Manufactured '19:—?Manufactured '20:—?
FOKMATION.—From sodium anthraquinone-2-sulfonate by heating withammonia water in an autoclave at 200° C , preferably in the presenceof an oxidizing substance
LITERATURE.—Ullmann, Enzy. tech. Chemie, 1, 476Lange, Zwischenprodukte, #3107Cain, Intermediate Products (2d Ed.), 254
Dyes Derived from 2-Amino-anthraquinone
SchultzNumberfor Dye
810
811
825
837
838
846
Ordinary Name andClass of Dye
ANTHRAQXJINONE ANDALLIED DYES
HelidoneYellow 3 G N
Algol Yellow 3G
Algol Red B
Indanthrene Blue R
Indanthrene BlueRS
Indanthrene DarkBlue BT
II
II
III
IMI
M
Statistics ofImport and
Manufacture
'14:—'20:—
'14:—'20:—
'14:—'20:—'14:—
20,7442,515
1,604570
2,3994,151
500
'14:—187,379'17:—'20:—'20:—
?16,385
?
Other IntermediatesUsed and Notes
2-Aniino-anthraquinone(2 mols)
Phosgene2-Amino-anthraquinone
(2 mols)[Succinic acid]4-Bromo-N-methyl-
anthrapyridone2-Amino-anthraquinone
(2 mols)2-Amino-anthraquinone
(2 mols)[Alkaline Reduction][or Indanthrene Blue
R reduced]2-Amino-anthraqui-
none (2 mols)[Glycerol (4 mols)][or Benzanthrone-quin-
oline (2 mols)]
DyeAppli-cationClass
V
V
V
V
V
V
DYES CLASSIFIED BY INTERMEDIATES 31
SchultzNumberfor Dye
849
867
Dyes Derived from
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
(continued)Indanthrcnc Yellow
G
Indanthrcnc BrownB
2-Amino-anthraquinone (continued)
Statistics ofImport and
Manufacture
I '14:— 75,192M'19:— ?I '20:— 75,665
M'20:— ?I '14:— 6,175I '20.— 3,511
Other IntermediatesUsed and Notes
2-Amirio-antliraqumonc(2 mols)
2-Amiiio-antliraquinone(2 mols)
DyeAppli-cationClass
V
V
1:5- and 1:8-Amino-anthraquinone-sulfonic Acids
5-and 8-Amino-l-anthraquinone-sulfonic Acids (C. A. nomeri)
(HO3S) m NH2c o3 ) c
HO3S C 0
= 303
FORMATION.—Anthraquinonc is sulfonatcd to a mixture of 1: 5-and1:8-disulfonic acids, which are then partly amidated by treatmeniwith ammonia
LITERATURE.—Cain, Intermediate Products (2d Ed.), 252Ullmann, Enzy. tech. Chcmic, 1, 475Langc, Zwischcnproduktc, #3265
Dye Derived from 1: 5- and 1:8-Amino-anthraquinone-sulfonic Acids
SchultzNumberfor Dye
851
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Alizarin DirectBlueB
Statistics ofImport and
Manufacture
I '14:—10,201I '20:— 2,982
Other IntermediatesUsed and Notes
[Dibromination]Aniline[Sulfonation]
DyeAppli-cationClass
A
32 DYES CLASSIFIED BY INTERMEDIATES
Amino-azo-benzene
Phenyl-azo-aniline (C A. nomen.)
C TT "\T -I A7
S T A T I S T I C S . — I m p o r t e d ' 1 4 : — v e r y s m a l l
M a n u f a c t u r e d ' 1 7 : — 1 4 1 , 8 8 8 l b s .
M a n u f a c t u r e d ' 1 8 : — 1 7 1 , 5 9 4 l b s .
M a n u f a c t u r e d ' 1 9 : — 8 2 , 7 5 5 l b s .
M a n u f a c t u r e d ' 2 0 : — 1 5 2 , 3 1 0 l b s .
F O R M A T I O N . — T h e a m i n o - a z o - b e n z e n e i s p r e p a r e d f r o m a n i l i n e , b y
m o l e c u l a r r e a r r a n g e m e n t o f d i a z o - a m i n o - b e n z e n e , w h i c h i n t u r n i s
m a d e f r o m a n i l i n e a n d d i a z o - b e n z e n e c h l o r i d e ( d i a z o t i z e d a n i l i n e )
L I T E R A T U R E . — C a i n , I n t e r m e d i a t e P r o d u c t s ( 2 d E d . ) , 8 1
D y e s D e r i v e d f r o m A m i n o - a z o - b e n z e n e
SchultzNumberfor Dye
31
137
223
224
225
226
Ordinary Name andClass of Dye
MONOAZO DYESAmino-azo-benzeneSpirit Yellow
Fast YellowAcid Yellow
DISAZO DYESSudan III
Cloth Red G
Croceine AZ
Croceine B
Statistics ofImport and
Manufacture
M'17:— ?M'18:— 52,283M'19:— ?M'20:— ?I '14:— 37,378M'17:— ?M'18:— ?I '20:— 7,848M'20:— ?
I '14:— 2,409M '17:— ?M'18:— ?M'19:— ?M'20:— ?I '14:— 401
M'19:— ?M'20:— ?I '14:— 500
'20:— 100
Other IntermediatesUsed and Notes
[Oleum]
jS-Naphthol
Nevile-Winther Acid
l-Naphthol-3:6-disul-f onic Acid
l-Naphthol-4: 8-disul-f onic Acid
DyeAppli-cationClass
ss
A
ssMF
A
A
A
DYES CLASSIFIED BY INTERMEDIATES 33
Dyes Derived from Amino-azo-benzene (continued)
SchultzNumberfor Dye
227
228
229
279
606697
699
701
Ordinary Name andClass of Dye
DISAZO DYES(continued)
BrilliantCroccine M
Ponceau 5RErythrine P
Azo Acid Violet
Bcnzo Fast Scarlet
AZINE DYESIndamine BlueInduline (Spirit
Soluble)
Indulme (WaterSoluble)
ParaphenylcncBlue R
Statistics ofImport and
Manufacture
I '14:—125,137M'17:— ?M'18:— 84,643M'19:—157,509I '20:— 49M'20:—129,124I '14:— 2;SS0M'17:— ?•jv/rnq. ?iVJL JL!/ . II '14:— 150I '20:— 11M'20:— ?I '14:— 36,674M'19:— ?I '20:— 24,153
I '14:— 25,342M'17:— ?M'18:— 8,589M'19:—436,201M'20:—140,400I '14:— 29,177M'17:—1S3,739M'18:— 91,724M'19:—130,704I '20:— 500M'20:—168,048
Other IntermediatesUsed and Notes
G Acid
2-Naphthol-3:6:8-trisulfonic Acid
1: 8-Dihydroxy-naph-thalcnc-4-sulfonicAcid
J AcidPhosgene
Aniline (excess)Aniline (excess)
Aniline (excess)[Sulfonation]
7)-Phcnylene-diaminc
DyeAppli-cationClass
A
A
A
D
Bss
A
B
Amino-azo-benzene-disulfonic Acid
6-Amino-3:4'-azo-bis6enzene-sulfonic Acid (C. A. nomen.)
SO3H
= 357
ORMATION.—From amino-azo-benzene by sulfonation with oleum
34 DYES CLASSIFIED BY INTERMEDIATES
SckultzNumberfor Dye
247
251
Dyes Derived from
Ordinary Name andClass of Dye
DISAZO DYESDouble ScarletScarlet EC
Croccine Scarlet 0
Amino-azo-benzene-disulfonic Acid
Statistics ofImport and
Manufacture
I '14:— 39,522M'17:— ?M'18:— 74,203
M'20:— ?I '20:— 100
Other IntermediatesUsed and Notes
0-Naphthol
Croccine Acid
DyeAppli-cationClass
A
A
Amino-azo-benzene-sulfonic Acid
p-(p-Amino-phenyl-a2:o)-5enzene-sulfonic Acid ((7. A. nomen.)
= C12H11N3O3S = 277
FORMATION.—From amino-azo-benzene by sulfonation at low tempera-ture by means of oleum
SchultzNumberfor Dye
246
248249250
Dyes Derived from
Ordinary Name andClass of Dye
DISAZO DYESCloth Scarlet G
Fast Scarlet BCroceine Scarlet 3BMilling Orange
Ammo-azo-benzene-sulfonic Acid
Statistics ofImport and
Manufacture
I '14:— 9I '17:— ?I '18:— ?I '19:— ?I '20:— ?I '14:— 1,755I '14:— 9,613I '14:— 4,370
Other IntermediatesUsed and Notes
jS-Naphthol
Schacffer's AcidCroceine AcidSalicylic Acid
DyeAppli-cationClass
A
AAM
6-Amino-3: 4;-azo-bis6enzene-sulfonic Acid (C. A. nomen.)
See, Amino-azo-benzene-disulfonic Acid
DYES CLASSIFIED BY INTERMEDIATES
a-Amino-azo-naphthalene
4-(Naphthyl-azo)-l-naphthylamine (C. A. nomen.)
=C2oH15N3 =
35
H2N
FORMATION.—From a-naphthylaminc, this compound is prepared bymixing equal molecules of a-diazo-naphthalene chloride (froma-naphthylamine) and a-naphthylamine hydrochloride in coldaqueous solution.
SchultzNumberfor Dye
694
695
Dyes Derived
Ordinary Name andClass of Dye
AZINE DYESRose MagdalaFast Pink for SilkParaphcnylcne Violet
from a-Amino-azo-naphthalene
Statistics ofImport and
Manufacture
I '14:— 597
I '20:— 337
Other IntermediatesUsed and Notes
a-Naphtli5damine
7;-Phcnylenc-diamine
DyeAppli-cationClass
A
B
o-Amino-azo-toluene
p-(o-Tolyl-azo)-o-foluidine (C. A. nomen.)
CH3 CH3
=CuH1 5N3 — 225
STATISTICS.—Manufactured 1917:—14,355 lbs.Manufactured 1918*— ?
FORMATION.—From o-toluidine, by molecular rearrangement of diazo-amino-toluene, which in turn is made by the reaction of equalmolecules of o-toluidine and diazo-toluene chloride (diazotizedo-toluidine)
LITERATURE.—Cain, Intermediate Products (2d Ed.), 82.
36 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from o-Amino-azo-toluene
SchultzNumberfor Dye
68
149
230231
232
233
234235
236
Ordinary Name andClass of Dye
MONOAZO DYESSpirit Yellow RYellow Fat ColorFast Yellow R
DISAZO DYESCloth Red 3 GACloth Red 3B Extra
Sudan IV
Cloth Red B
Cloth Red GCroceine 3B
Cloth Red BWool Red B
Statistics ofImport and
Manufacture
I 14:— 251I 14:— 15I ' 2 0 : - 84I 14:— 51
M17:— 13,334M18:— 14,904M19:— ?M'20:— ?I 14:— 1,962M18:— ? *M19:— ?M '20:— ?I 14:— 554M19:— ?M;20:— ?I 14:— 14,293
M17:— ?M18:— ?M19:— ?MJ20:— ?
Other IntermediatesUsed and Notes
[This is amino-azo-toluene]
[Oleum]
Bronner's AcidEthyl-2-naphthyl-
amine-7-sulfonic Acid0-Naphthol
Nevile-Winther Acid
SchaefTer's Acidl-Naphthol-4: 8-disul-
fonic AcidRAcid
DyeAppli-cationClass
ss
A
MM
ssMF
M
MA
A
o-Amino-azo-toluene-sulfonic Acid
4-(4-Amino-m-tolyl-azo)-m-toluene-sulfonic Acid (C.A. nomen.)
CH-3 CH3
= C14H15N3O3S = 305
FOEMATION.—o-Amino-azo-toluene is sulfonated with oleum
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from o-Amino-azo-toluene-sulfonic Acid
37
SchultzNumberfor Dye
252253254
255
Ordinary Name andClass of Dye
DISAZO DYESCloth Scarlet JROrseilline BBBordeaux G
Croceinc Scarlet SBPonceau 6RB
Statistics ofImport and
Manufacture
I'14:—2,379I720:-- 154
Other IntermediatesUsed and Notes
0-NaphtliolNcvilc-Winther's AcidSchaeffer's Acid
Croceinc Acid
DyeAppli-cationClass
MAA
A
Amino-azo-xylene
4-(2: 4-Xylyl-azo)-2: 5-zylidine (C. A. nomen.)
H3C
H 3 C < ^ ^ > N 2 < ^ ) N H 2 = C16H19N3 = 253
CH3 CH3
FORMATION.—From xylidine, and by action of diazo-m-xylidine (2:4-xylidine) on p-xylidine (2: 5-xylidine)
LITERATURE.—Nolting and Forel, Ber. 18, 2668 (1885)Nictzki, Ber. 13, 471 (1880)Schultz, Chemie Steinkohlentcers 1, 137
Dyes Derived from Amino-azo-xylene
SchultzNurnberfor Dye
23723S
Ordinary Name a?idClass of Dye
DlbAZO I)YE«Bordeaux BXUnion Fast Claret
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
AcidH Acid
ymAppli-cationClass
AA
m -Amino~i&enzaldehyde
HCO
JNH2
38 DYES CLASSIFIED BY INTERMEDIATES
FORMATION.—Benzaldehyde is nitrated, resulting in a mixture of o- andra-nitro-benzaldehyde (20 and 80 per cent). The reduction iseffected and the o-derivative is removed by treating the crudenitration mixture with sodium hydrosulfite and hydrochloric acid,whereupon the o-derivative crystallizes out as the anhydro-derivative of o-amino-benzaldehyde. The solution contains them-amino-benzaldehyde, and it is used directly
LITERATURE.—Cain, Intermediate Products (2d Ed.), 144, 145Lange, Zwischenprodukte, #316-318
USES.—For preparation of m-Hydroxy-benzaldehyde
P-Amino-Aenz aldehyde
HCO
= C7H7NO =
KH2
FORMATION.—p-Nitro-toluene, in alcoholic solution, is run into a solu-tion of sulfu in caustic soda; and the mixture is heated under areflux condenser for l j hours, and then separated
LITERATURE.—Lange, Zwischenprodukte, #319-327Ullmann, Enzy. tech. Chemie, 2, 307
SchultzNumberfor Dye
129130
Dyes Derived
Ordinary Name andClass of Dye
MONOAZO DYES
Chromazone Red AChromazone Blue R
from p-Amino-benzaldehyde
Statistics ofImport and
Manufacture
114:—243
Other IntermediatesUsed and Notes
Chromotropic AcidChromotropic AcidEthyl-phenyl-hydrazine
DyeAppli-cationClass
MM
p-Amino-5enzaldehyde Ethyl-phenyl-hydrazone (C. A. nomen.)
See, p-Amino-benzylidine-ethyl-phenyl-hydrazone
l-Amino-4-benzamido-anthraquinone (C. A. nomen.)
See, l-Amino-4-benzoylamino-anthraquinone
DYES CLASSIFIED BY INTERMEDIATES
2-Amino-p-&enzene-disulfonic Acid (C. A. nomen.)
Aniline-2: 5-disulf onic Acid
SO3H
39
VSO3H
FORMATION.—The sodium salt of 4-chloro-3-nitro-benzene-sulfonate isboiled with sodium sulfite, resulting in formation of sodium 2-nitro-benzcne-disulfonate, which is reduced with iron and acetic acid toanilinc-2: 5-disulf onic acid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 49Lange, Zwischenprodukte, #957
USES.—For preparation of ethyl-m-amino-phenol
4-Amino-/zr-5enzene-disulfonic Acid (C. A. nomen.)Aniline-2: 4-disulfonic Acid
SO3H
= C6H7NO6S2 =
NH2
FORMATION.—-By heating sulfanilic acid (p-aniline-sulfonic acid) witholeum at 170-180° C.
LITERATURE.—Ann. 198, 17
Beilstein, Organische Chcmie (3 auf.) II, 571
Dye Derived from 4-Amino-m-^enzene-disulfonic Acid
SchultzNumberfor Dye
263
Ordinary Name andClass of Dye
DISAZO DYEJet Black R
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
a-NaphthylaminePhcnyl-a-naphthyl-
amine
DyeAppli-cationClass
A
/n-Amino-benzene-sulfonic Acid
See, Metanilic Acid
40 DYES CLASSIFIED BY INTERMEDIATES
p-Amino-benzene-sulfonic AcidSee, Sulfanilic Acid
Amino-benzenyl-o-amino-thio-cresol
See, Dehydro-thio-p-toluidine
m-Amino-^enzoic Acid
COOH
FORMATION.—m-Nitro-benzoic acid is reduced with iron and acetic acid
LITERATURE.—Ullmann, Enzy. tech. Chemie, 2, 333
Dyes Derived from m-Amino-benzoic Acid
SchultzNumberfor Dye
203204
486
Ordinary Name andClass of Dye
MONOAZO DYESYellow Fast-to-soapDiamond Yellow G
TETRAKISAZO DYEDirect Brown J
Statistics ofImport and
Manufacture
I '14:—3,640
Other IntermediatesUsed and Notes
DiphenylamineSalicylic Acid
m-Phenylcnc-diamine(3 mols)
m-Amino-benzoic Acid(2 mols)
DyeAppli-cationClass
MM
D
o-Axoino-benzoic Acid
See, Anthranilic Acid
l-Amino-4-benzoylamino-anthraquinone
l-Amino-4-benzamido-anthraquinone ( C A. nomen.)
no NH2
oC.Uw NH. COC6HB
DYES CLASSIFIED BY INTERMEDIATES 41
FORMATION.—By heating 1:4-Diamino-anthraquinone in a toluene ornitro-benzene solution with benzoyl chloride
LITERATURE.—Cf. Ullmann, Enzy. tech. Chemie, 1, 164
Bye Derived from l-Amino-4-benzoylamino-anthraquinone
SchultzNumberfor Dye
833
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Algol Olive R
Statistics ofImport and
Manufacture
I ?14:—13,334I '20:— 461
Other IntermediatesUsed and Notes
l-Bcnzoylamino-4-chloro-anthraq uinonc
[Chloro-sulfonic Acid]
DyeAppli-cationClass
V
p-Amino-benzyl-diethylamine
p-Amino-iVr:iVr-diethyl-6enzylaminc (C. A. nomen.)
CH2 .N.(C2H5)2
NH2
FORMATION.—p-Nitro-bcnzyl chloride is treated with 2 mols of dicthyl-amine in alcoholic solution at 100° C ; and the resulting p-nitro-benzyl-diethylaminc is reduced with SnCl2 and HCl to the p-amino-benzyl-dicthylaminc
LITERATURE.—Ber. 28, 1141
Cf. Lange, Zwischenprodukte, #255
Dye Derived from p-Amino-benzyl-diethylamine
SchultzNumberfor Dye
435
Ordinary Name andClass of Dye
TRISAZO DYEJanus Brown B
Statistics ofImport arid
ManufactureOther Intermediates
Used and Notes
a-Naphthylaminellesorcinol or ra-phcnyl-
ene-diaminc[or Chrysoidine]
DyeAppli-cationClass
B
42 DYES CLASSIFIED BY INTERMEDIATES
o-Amino-benzyl-dimethylamine
o-Amino-JV:iV-dimethyl-6enzylamine (C. A. nomen.)
CH2 .N(CH3)2
Q N H 2
FOKMATION.—o-Nitro-bcnzyl chloride is treated with 2 mols of dimethyl-amine in alcoholic solution at 100° C , and the resulting o-nitro-benzyl-dimethylamine is reduced with SnCl2 and HC1 to theo-amino-benzyl-dimethylamine
LITERATURE.—Cf. Ber. 28, 1141(7/. Lange, Zwischenprodukte, #250, 255
Dyes Derived from o-Amino-benzyl-dimethylamine
SchultzNumberfor Dye
74
75
Ordinary Name andClass of Dye
MONOAZO DYESTannin Orange
New Phosphinc G
Statistics ofImport and
Manufacture
I '14.-2,202I '20:— 349
I '14:— 500
Other IntermediatesUsed and Notes
p-Aminob enzyl-di-methylaminc
/3-Naphthol (2 mols)
p- Amino-b enzyl-di-methylamine
Resorcinol (2 mols)
DyeAppli-cationClass
B
B
p-Amino-benzyl-dimethylamine
p-Amino-AT:iV-dimethyl-&enzylarDine (C. A. nomen.)
CH2.NCCH3)2
NH2
FORMATION.—p-Nitro-benzyl chloride is treated with 2 mols of dimethyl-amine in alcoholic solution at 100° C ; and the resulting p-nitro-benzyl-dimethylamine is reduced with SnCl2 and HC1 to the p-amino-benzyl-dimethylamine
LITERATURE.—Ber. 28, 1141
Lange, Zwischenprodukte, ^255
DYES CLASSIFIED BY INTERMEDIATES 43
Dyes Derived from p-Amino-benzyl-dimethylamine
SchultzNumberfor Dye
74
75
Ordinary Name andClass of Dye
MONOAZO DYESTannin Orange R
New Pliospliinc G
Statistics ofImport and
Manufacture
I '14:—2,202I ;20:— 249
I'14:— 500
Other IntermediatesUsed and Notes
o-Amino-benzyl-di-methylamine
0-Naphthol (2 mols)
o-Amino-bcnzyl-di-methylamine
Ilcsorcinol (2 mols)
DyeAppli-cationClass
B
B
p-Amino-benzyl-ethyl-aniline-sulfonic Acid
See, Ethyl-sulfobenzyl-p-phenylene-diamine
p-Amino-benzylidene-ethyl-phenyl-hydrazone
Ethyl-phenyl-hydrazone of p-Amino-benzaldehyde
p-Amino-&enzaldehyde Ethyl-phenyl-hydrazone (C. A. nomen.)
HC:N.N<
NH2
FOKMATION.—^By condensation of ethyl-phenyl-hydrazine and p-amino-benzaldehyde
Dye Derived from p-Amino-benzylidene-ethyl-phenyl-hydrazone
SchultzNumberfor Dye
130
Ordinary Name andClass of Dye
MONOAZO DYEChromazone Blue It
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
Chromotropic Acid
DyeAppli-cationClass
M
44 DYES CLASSIFIED BY INTERMEDIATES
l-Amino-2-bromo-4-hydroxy-anthraquinone
4-Amino-3-bromo-l-hydroxy-anthraquinone (C A nomen.)
n0 NH2
FORMATION.—From l-amino-2:4-dibromo-anthraquinone by heatingwith monohydrate at 100-110°
LITERATURE.—Lange, Zwischenprodukte, #3314
Dye Derived from l-Amino-2-bromo-4-hydroxy-anthraquinone
SchultzNumberfor Dye
844
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Algol Blue 3G
Statistics ofImport and
Manufacture
I '14:—9,191I '20:—3,S96
Other IntermediatesUsed and Notes
l-Amino-2-bromo-4-hydroxy-anthraqui-none (2 mols)
DyeAppli-cationClass
V
4-Amino-3-bromo-l-hydroxy-anthxaquinone (C. A. nomen.)
See, l-Amino-2-bromo-4-hydroxy-anthraquinone
l-Amino-4-bromo-2-methyl-anthraquinone
aCO NH2
=C1 6H1 0BrNO2 =
FORMATION.—2-methyl-anthraquinone (which is obtained by the con-densation of toluene with phthalic anhydride) is nitrated andreduced. The resulting l-amino-2-methyl-anthraquinone is bromi-nated in a glacial acetic acid solution and the l-amino-4-bromo-2-methyl-anthraquinone is formed
LITERATURE.—Ullmann, Enzy. tech. Chemie, 1, 486Barnett, Anthracene and Anthraquinone, 80, 192, 229Cain, Intermediate Products (2d Ed.), 260
DYES CLASSIFIED BY INTERMEDIATES 45
Dyes Derived from l-Amino-4-bromo-2-methyl-anthraquinone
SchultzNumberfor Dye
859
SGO
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Cyananthrol 11
Cyananllirol G
Statistics ofImport and
Manufacture
I '14:—1S,7O2I '20:— 2,416
I '20:— 5,127
Other IntermediatesVied and Notes
/j-Toluidine[Sulfonation]
/;-Toluidine[Sulfonation]
DyeAppli-cationClass
A
A
Cl
l-Amino-6-chloro-anthraquinone
r o NH2
SchultzNumberfor Dye
827
Dye Derived from
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
IndanthrencBordeaux B extra
1 - Amino -6 - chloro - anthraquinone
Statistics ofImport and
Manufacture
I '14:—2S,72SI '20:— 4,050
Other Interim diatesUsed and Notes
1-Amino-G-ohloro-an-thraquinonc (2 mols)
2: 7-Dichloro-anthra-quinonc
DyeAppli-cationClass
V
2-Amino-6-chloro-6enzene-sulfonic Acid (C. A. nomen.)
3-Chloro-anilinc-2~sulfonic Acid
m-Chloro-anilinc-o-suKonic Acid
SOJI
5 — 207.5
FOEMATION.—By the reduction of m-chloro-nitro-benzcnc-o-sulfonicacid in the usual way.
46 DYES CLASSIFIED BY INTERMEDIATES
LITERATURE.—Beil. II, 571
Dye Derived from 2-Amino-6-chloro-benzene-sulfonic Acid
SchultzNumberjor Dye
131
Ordinary Name andClass of Dye
MONOAZO DYEPermanent Orange R
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
j8-Naphthol
DyeAppli-cationClass
CL
l-Amino-4-chloro-3-metbyl-benzene-6-sulfonic Acid
See, 2-Amino-5-chloro~p-foluene-sulfonic Acid (C A. nomen.
2-Amino-5-chloro-p-foluene-sulfonic Acid (C. A. nomen.SOzH—1)
2-Chloro-5-toluidine-4-sulfonic Acid (CHz=l)
l-Amino-4-chloro-3-methyl-benzene-6-sulfonic Acid
SO3H
NH2 _ C7H8C1NO3S = 221.5
CH3
STATISTICS.—Manufactured '20:—22,753 lbs
FORMATION.—From o-chloro-toluene-p-sulfonic acid (CHz=l) by nitra-tion and subsequent reduction
LITERATURE.—Lange, Zwischenprodukte, #1022
Dye Derived from 2-Amino-5-chloro-p-toluene-sulfonic Acid (S0sH=l)
SchultzNumberfor Dye
153
Ordinary Name andClass of Dye
MONOAZO DYELake Red C
Statistics ofImport and
Manufacture
I '14:—306,607M'19:— ?I '20:— 4,105
Other IntermediatesUsed and Notes
jS-Naphthol
DyeAppli-cationClass
CL
DYES CLASSIFIED BY INTERMEDIATES
4-Amino-chrysoidine (C.A. nomen.)
2:4:4'-Triamino-azo-benzene
H2N
~ 2 = C l 2 H l 3 N 5 = 2 2 7
47
FORMATION.—(1) p-Amino-acetanilide (acetyl-p-phenylene-diamine) isdiazotized and combined with m-phenylene-diamine, and then theacetyl group removed
(2) p-Nitro-aniline is diazotized and combined with m-phenylene-diamine, and the product reduced with sodium sulfide
LITERATURE.—Lange, Zwischenprodukte, #1765
Dye Derived from 4-Amino-chrysoidine
SchultzNumberfor Dye
239
Ordinary Name andClass of Dye
DISAZO DYEAzotol C
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
0-Naphthol
DyeAppli-cationClass
MF
2-Amino-p-cresol (011=1, C. A.nomen.)
m-Amino-p-cresol (CH$=1)
3-Amino-p-cresol (Eng. and Germ, nomen.
OH
/ ]NH2 _
CH3
_ 1 2 3
FORMATION.—(1) p-Cresol is nitrated and then reduced with SnC^ andHC1. (2) p-Toluidinc is treated with nitric and nitrous acids so asto form 2-nitro-p-cresol (OH = i ) , which is then reduced to theamino compound
LITERATURE.—Ber. 22, 348; 24,1960
Beil. II , 752
48 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from 2-Amino-p-cresol
SchultzNumberfor Dye
260
Ordinary Name andClass of Dye
DISAZO DYEErio-Chrome
Verdon
Statistics ofImport and
Manufacture
I '14:—8S2
Other IntermediatesUsed and Notes
Sulfanilic acid/3-Naphthol
DyeAppli-cationClass
ACr
3-Amino-p-cresol (Eng. andGer. nomen. CHz=l)
See, 2-Amino-p-cresol (OH =1, C. A. nomen.)
3-Amino-p-cresol (OH^l, C. A. nomen.)
6-Amino-p-cresol (CHZ = 1)
o-Amino-p-cresol (CHz—l: Ger. and English nomen.)
OH
FORMATION.—p-Toluidine is nitrated, and the 3-nitro-p-toluidinesulfate (NHz^l) therefrom is treated with NaNO2 in the coldand then boiled with dilute sulfuric acid, thus forming 3-nitro-p-cresol, which latter on reduction with SnCk and HCl gives 3-amino-p-cresol
LITERATURE.—Beil. II, 751, 753
Dye Derived from 3-Amino-p-cresol
SchultzNumberfor Dye
576
Ordinary Name andClass of Dye
XANTHONE DYERhodamine 3G
Statistics ofImport and
Manufacture
I '14:—19,568I ' 2 0 : - 855
Other IntermediatesUsed and Notes
Dimcthylamino - hy~droxy - benzoyl- ben-zoic acid
[Ethyl estcrification]
DyeAppli-cationClass
B
6-Amino-p-cresol (C Hz=1)See 3-Amino-p-cresol (OH ••--1, C. A. nomen.)
DYES CLASSIFIED BY INTERMEDIATES
m-Amino-Jp-cresol (CH3=1)
See, 2-Amino-p-cresol (OH =17 C. A. nomen)
o-Amino-p-cresol (CH3-1)
See, 3-Amino-p-cresol (OH =./, C. A. nomen)
2-Amino-p-cresol Methyl Ether (OCIIZ=1)
6-Methoxy-m-toluidine (C. A. nomen. NH2=1)
m-Amino-p-cresol Methyl Ether
3-Amino-4-cresol Methyl Ether
OCH3
49
CH3
FORMATION.—2-Nitro-p-cresol (OH = 1), obtained by action of nitrousand excess nitric acids upon p-toluidine, is methylated and reduced
LITERATURE.—Ber. 22, 348; 24, 960
Dyes Derived from 2-Amino-/>-cresol Methyl Ether (OCH3=1)
SchultzNumberfor Dye
9G
100
101
439
440
Ordinary Name andClass of Dye
MONOAZO DYESChrome Fast
Yellow GG
Eosamine B
Cocchnue B
TRISAZO DYESDirect Indigo Blue.
Direct IndigoBlue BK
Statistics ofImport and
Manvfacture
I '14:— 150I'20:— 500
I '14:—1,914I '20:—1,600
AM'18:— ?
Other IntermediatesUsed and Notes
Salicylic Acid
l-Naphthol-3: 8-disul-fonic Acid
R Acid
BcnzidineH Acid (2 mols)
BenzidinoGamma Acid (2 mols)
DyeAppli-cationClass
M
A
A
D
D
50 DYES CLASSIFIED BY INTERMEDIATES
m-Amino-£-cresol Methyl EtherSee, 2-Amino-p-cresol Methyl Ether (OCHZ = 1)
l-Amino-2:4-dibromo-anthraquinone
CO N H 2
f | Y J B r = Ci4H7Br2NO2 = 381
C 0 Br
FORMATION.—1-Amino-anthraquinone is treated in nitro-benzene solu-tion and at about 120-130° with an excess of bromine
LITERATURE.—Ullmann, Enzy. tech Chcmie, 1, 475Ger. Pat., 160,169
Dye Derived from l-Amino-2:4-dibromo-anthraquinone
SchultzNumberfor Dye
855
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Alizarin Pure Blue B
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
p-Toluidine[Sulfonation]
DyeAppli-cationClass
ACr
2-Amino-4: 6-dichloro-phenol
OH
_ 1 7 8
Cl
FORMATION.—4:6-Dichloro-2-nitro-phenol is reduced with tin andhydrochloric acid
LITERATURE.—Beil. I I , 727
Dye Derived from 2-Amino-4: 6-dichloro-phenol
SchultzNumberfor Dye
86
Ordinary Name andClass of Dye
MONOAZO DYEAzarine S
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
0-Naphthol
DyeAppli-cationClass
M
DYES CLASSIFIED BY INTERMEDIATES 51
4-Amino-l-diethylamino-benzene-3-thiosulfonic AcidSee, Diethyl-p-phenylene-diaminc'thiosulfonic Acid
^-Amino-diethyl-aniline
See, N: iVVDiethyl-p-phenylene-diamine (C A. nomen.)
^-Amino-diethyl-aniline-thiosulfonic Acid
See, Diethyl-p-phenylene-diamine-thiosulfonic Acid
^-Amino-iV: JV-diethyl-fcenzylamine ((7. A. nomen.)
See, p-Amino-benzyl-diethylamine
2-Amino-5-dimethylamino-i6enzene-thiosulfonic Acid (C. A,nomen.)
See, Dimethyl-p-phenylene-diam"ne-thiosulfonic Acid
m-Amino-dimethyl-anilineSee N: N Dimethyl-m-phenylene-diamine C. A. nomen.)
j!>-Amino-dimethyl-anilineSee, iV.'iV-Dimethyl-p-phenylene-diainme (C A. nomen.)
/>-Amino-diniethyl-aniline-thiosulfonic Acid
See, D'mcthyl-p-phenylcnc-diamine-thiosulfonic Acid
o-Amino-iV: N-dimethyl-6enzylainine (C. A. nomen.)
See, o-Amino-benzyl-dimethylamine
^-Amino-iV': iV-dimethyl-&enzylamine (C. A. nomen.)
See, p~Amino-benzyl-dimethylamine
4/-Amino-2:4-dinitro-diphenylamineN- 2:4-Pinitro~phenyl)-p-phcnylene-diamine (C A. nomen.)
NO2
^ =1C12H10N4O4=274
52 DYES CLASSIFIED BY INTERMEDIATES
FORMATION.—l-Ch'oro-2:4-dinitro-benzene is condensed with p-phenyl-ene-diamine
LITERATURE.—Lange, Zwischenprodukte, #1666
Dye Derived from 4/~Amino-2: 4-dinitro-diphenylamine
SchultzNumberfor Dye
727
Ordinary Name andClass of Dye
SULFUR DYEAuronal Black B
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
[Glycerol; S+Na,S]
DyeAppli-cationClass
S
o- Amino -diphenylamine
iV-Phenyl-o-phenylene-diamine (C. A, nomen.)
NH2
/ ~ " > = Ci2H12N2 r=r 184
FORMATION.—By reducing o-nitro-diphenylamine (from o-bromo-nitro-benzene and aniline) by heating with ammonium sulfide
LTTERATURE.—Lange, Zwischenprodukte, #1611Chem. Zeitung, 18, 1095Ber. 23, 1843
Dye Derived from o-Amino- diphenylamine
SchultzNumberfor Dye
668
Ordinary Name andClass of Dye
AZINE DYEFlavinduline 0
Statistics ofImport and
Many fact arc
J '14:—6G0
Other IntermediatesUt>ed and Notes
PI icnanthrenc-quinonc
DyeAppli-cationClass
B
£-Amino-diphenylamine
-ph nylene-diamine (C. A. nomen.)
= C12H12N2 = 184
DYES CLASSIFIED BY INTERMEDIATES 53
FORMATION.—This intermediate can be prepared by reducing OrangeIV, by means of sodium sulfide and sulfur. The Orange IVresults from the coupling of diazotized sulfanilic acid with di-phenylamine
LITERATURE.—Langc, Zwischenprodukte, #1611Cain, Intermediate Products (2d Ed.), 74
Dyes Derived from £-Amino-diphenyIamine
SchultzNumberfor Dye
687
922
Ordinary Name andClass of Dye
AZINE DYERosolan 0
ANILINE BLACKGROUP
Diphenyl Black
Statistics ofImport and
Manufacture
I '20:—1,083
I '14:—1,470M'19:— ?M'20:— ?
Other IntermediatesUsed and Notes
Anilineo-Toluidinc[Oxidation]
?;-A min o-diphcnyl-iUiiiiK* (x mols)
[Oxidation]
DyeAppli-cationClass
B
Special
^-Amino-diphenylamine-2-sulfonic Acid
2-Anilino-5-amino-I)cnzcnc-sulfonic Acid (C. A. nomen.)
SO3H
C C i 2 H i 2 N - ° 3 S = 2 G *
FORMATION.—p-Chloro-nitro-bcnzene is sulfonatcd to 2-chloro-5-nitro-benzene-sulfonate, which latter in presence of glycerol and sodiumcarbonate is condensed with aniline to form p-nitro-diphenylamine-2-sulfonic acid. This is reduced by iron and hydrochloric acid,resulting in p-amino-diphcnylaminc-2-sulfonic acid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 75Cf. Lange, Zwischenprodukte, #1646, 1647
USES.—For preparation of the Nerol Dyes
54 DYES CLASSIFIED BY INTERMEDIATES
a-(^-Amino-JVP-ethyl-anilino)-^~toluene-sulfonic Acid (C. A.nomen.)
, Ethyl-sulfobenzyl-p-phenylene-diamine
a-(4-Amino-i\T-ethyl-3-sulfomercapto-anilino)-J!>-^oluene-sulfonicAcid (C A. nomen.)
Ste, Ethyl-sulf obenzyl -p-phenylene-diamine-thiosulf onic Acid
^-Amino-ethyl-o-toluidine (C#3 = 1)
See, iV3-Ethyl-4-m-tolyene-diamine (C. A. nomen.
^-Amino-ethyl-o-foluidine
See, JN^-Ethyl-p-tolylene-diamine
Amino-G Acid1
2-Naphthylamine-6:8-disulfonic Acid
7-Amino-l: 3-naphthalene-disulfonic Acid (C. A. nomen.)
j8-Naphthylamine-Y-disulfonic Acid
/3-Naphthylamine-disulfonic Acid G
HO3S
H ° 3 S \ / \ / = C l ° H 9 N ° 6 S 2 = 3 ° 3
STATISTICS.—^Manufactured 1918:— ?Manufactured 1919:— ?Manufactured 1920:—894,624 lbs.
FORMATION.—From G acid, by heating the sodium salt with ammoniaand sodium bisulfite solution, in an autoclave under pressure
LITERATURE.—Lange, Zwischenprodukte, #2599Cain, Intermediate Products (2d Ed.), 209
1 Occasionally in the older literature, this 2-naphthylamine-6: 8-disulf onic Acidhas been called G Acid.
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Amino-G Acid
55
SchultzNumberfor Dye
178
270
271
272
Ordinary Name andClabh of Dye
MONOAZO DYECrumpsall Yellow
DISAZO DYESBiilhcint Cioteme 9B
Diaminc Blue 6G
Naphthol Black BBrilliant Black B
Statistics ofImport and
Manufacture
I '14 -—103,598M'19— ?I '20 — 50
Other IntermediatesUsed and Notes
Salicylic Acid
ArnlmeG and R Acids
1 -Ammo-2-naphtholethyl ether
0-Naphthol
a-NaphthylammeR Acid
DyeAppli-cationClass
A
A
D
A
l-Amino-4-hydroxy-anthraquinone
4-Ammo-l-hydroxy-anthraquinone (C. A. nomen.)
NH2
FORMATION.—(1) From quinazarin by heating with ammonia. (2) From1-amino-anthraquinone by heating with sulturic acid (66° Be.) andboric acid to 180-200° C.
LITERATURE.—Lange, Zwischenprodukte, #3253-3255
Dye Derived from l-Amino-4-hydroxy-anthraquinone
SchultzNumberfor Dye
818
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Algol Pink It
Statistics ofImport and
Manufacture
I '14— 126I '20 —1,368
Other IntermediatesUsed and Notes
Bcnzoyl chloride
DyeAppli-cationClass
V
56 DYES CLASSIFIED BY INTERMEDIATES
4-Amino-l-hydroxy-anthraquinone (C. A. nomen.)
See, l~Amino-4-hydroxy~anthraquinone
4-Amino-4'-hydroxy-dIphenylamine
p-(p-Amino-anilino)-phenol ( C A. nomen.)
= C l 2 H l 2 N 2 ° — 2 0 0
FORMATION.—From phenol and p-phenylene-diamine by oxidation atlow temperature
LITERATURE.—Lange, Zwischenprodukte, #1639-1643
Dye Derived from. 4-Amino-4'-hydroxy-diphenylamine
SchultzNumberfor Dye
732
Ordinary Name andClass oj Dye
SULFUR DYEAutogene Black
Statistics ofImport and
Manufacture
I '14:—7,495
Other IntermediatesUsed and Notes
Phenol[S2C12; S+Na^S]
DyeAppli-cationClass
s
2-Amino-7-hydroxy-diphenylenazine
See, 2-Amino-8-hydroxy-phenazine
2-Amino-4r-hydroxy-4-nitro-diphenylamine
4-Nitro-2-arnino-4/-hydroxy-diphenylamine
p-(2-Amino-4-nitro-anilino)-phenol (C A. nomen.)
NH2
O o N < f ~ V - N H — ( ^ " " N O H = C u H u N a O s = 245
FORMATION.—Chloro-dinitro-benzene is condensed with p-amino-phenol in presence of an acetate to 2: 4-dinitro-4'-hydroxy-di-phenylamine, which by partial reduction furnishes the above de-rivative.
LITERATURE.—Beil II, spL, 399; IV, spl, 397Lange, Zwischenprodukte, #1670Thorpe, Die. Chemistry, 2, 245
DYES CLASSIFIED BY INTERMEDIATES 57
Dyes Derived from 2-Amino-4'-hydroxy-4-nitro-diphenylamine
SchultzNumberfor Dye
726
730
736
Ordinary Name andClass of Dye
SULFUR DYES
Pyrogcne Direct BluePyrogene Blue
Pyrogene Black G
Thion Blue B
Statistics ofImport and
Manufacture
I '14:—10,934I '20:— 2,49S
I '14:— 8,725
I '14:— 7,353I '20:—11,855
Other IntermediatesUsed and Notes
[Alcohol; S+Na*S]
[S+Na^S; It is not cer-tain that the amino-hy-droxy - nitro - diphenyl-amine referred to isthe one with the posi-tions given above]
[CS2; S+Na2S]
DyeAppli-cationClass
S
s
s
2-Amino-8-hydroxy-phenazine
2-Amino-7-hydroxy-diphcnylenazine
8-Amino-2-phenazinol (C. A. nomen.)
H 0 ( X l X ) N H ! =
FORMATION.—l-Chloro-2:4-dinitro-benzenc condensed with p-amino-phenol, the product reduced, and the resulting diamino-hydroxy-diphenylamine oxidized in alkaline solution with manganese dioxide
LITERATURE.—Lange, Zwischcnprodukte, #1969Cain, Intermediate Products (2d Ed.), 83
Dye Derived from 2-Amino-8-hydroxy-phenazine
SchultzNumberfor Dye
739
Ordinary Name andClass of Dye
SULFUR DYEImmedial
Bordeaux GImmedial Maroon B
Statistics ofI'm port and
Manufacture
I '14:—15,496
Other IntermediatesUsed and Notes
[S+Na^S]
DyeAppli-cationClass
s
58 DYES CLASSIFIED BY INTERMEDIATES
5-Amino-2-hydroxy-fhionaphthene (C. A. numbering)
6-Amino-3-hydroxy-thionaphthene (German numbering)
orOH
= C 8 H T N O S = 1 6 5
FORMATION.—4-Acetarnido-2-amino-benzoic acid is diazotized, reactedfirst with potassium xanthate (C2H5O . CS . SK) and then withchloro-acetic acid, forming 4-acetamido-2-thioglycolic-benzoic acid,which by melting forms the desired 5-amino-2-hydroxy-thio-naphthene
LITERATURE.—Lange, Zwischenprodukte, #2166Ullmann, Enz. tech. Chemie, 3, 568
Dyes Derived from 5-Amino-2-hydroxy-thionaphthene
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
902
903
904
911
914
INDIGO GROUP DYESHelindone Brown 2R
Helindone Brown 5R
Helindone Brown G
Ciba Orange G
Helindone Orange D
I ;14:-~ 876I '20:— 1,778
I '14:—13,086I '20:— 2,200
I '14:— 222
I '20: 17
2-Isatin-anilide[Bromination; ? classi-
fication]
2-Isatm-anilide[Bromination]
Isatin[Bromination]
Acenaphthenequinone[Bromination]
5-Amino-2-hydroxy-thionaphthene (2 mols)[Bromination]
V
V
V
V
6-Amino-3-hydroxy-thionaphthene (German numbering)
See, 5~Amino-2~hydroxy-thionaphthene (C. A. numbering)
DYES CLASSIFIED BY INTERMEDIATES
l-Amino-4-methoxy-anthraquinone
•C(X
59
OCH3
FORMATION.—Probably by the nitration and subsequent reduction of1-methoxy-anthraquinone. The 1-methoxy-anthraquinone is ob-tained from 1-nitro-anthraquinone by heating with an alcoholicsolution of potassium methylate with exclusion of water
LITERATURE.—Cf. Barnett, Anthracene and Anthraquinonc, 169, 279,280, 287
SchultzNumberfor Dye
815
829
Dyes Derived from
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Algol Scarlet G
Algol Bordeaux 3B
l-Amino-4-methoxy-anthraquinone
Statistics ofImport and
Manufacture
I '20:—959
I '20:-— 61
Other IntermediatesUsed and Notes
Bcnzoyl chloride
l-Amino-4-mcllioxy-an-thraquinone (2 mols)
2: 6-Dichloro-anthra-quinone
DyeAppli-cationClass
V
V
l-Amino-2-methyl-anthraquinone
•CCXCH3 _ ,
FORMATION.—2-Methyl-anthraquinone is dissolved in sulfuric acidsolution and nitrated with sodium nitrate. The nitro compoundis then separated and reduced with sodium sulfi.de
LITERATURE.—Cain, Intermediate Products (2d Ed.) , 260Lange, Zwischenprodukte, #3209
60 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from l-Amino-2-methyl-anthraquinone
SchultzNumberfor Dye
868
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Cibanone Brown B
Statistics ofImport and
Manufacture
I '14:—399
Other IntermediatesUsed and Notes
[Sulfur]
DyeAppli-cationClass
V
3~Amino-4-methyl-diphenylamineSee, iV^Phenyl^-Tft-tolylene-diamine
IV-Amino-5-methyl-2-phenyl-thiazol-sulfonic Acid
See, Dehydro-thio-p-toluidine~sulfonic Acid
N- (3-Amino-4-methyl-phenyl) -^-toluene-sulf amide
3'-Ajnino~(p^oluene~sulfo)-p-toluide (C. A. nomen.)
(Example of m-amino-arylsulfamide)
N H . = C M H M N A S = 2 7 6
FORMATION.—3-Nitro-p-toluidine (NH2 = 1) is suspended in water,p-toluene-sulfochloride and soda added. The reaction productis purified by solution in dilute caustic soda and precipitation withhydrochloric acid. This nitro body is now reduced with zinc dustand hydrochloric acid to the amino-sulfamide
LITERATURE.—Lange, Zwischenprodukte, #1801Schultz-Heumann, Anilinfarben, 4, 2103Ger. Pat. 135,016
Dyes Derived from iNT-(3-Amino-4-inethyl-phenyl)-^-toluene-sulfamide
SchultzNumberfor Dye
92
Ordinary Name andClass of Dye
MONOAZO DYEMetachrome
Bordeaux R
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
Picramic Acid
DyeAppli-cationClass
M
DYES CLASSIFIED BY INTERMEDIATES 61
a-Amino-naphthalene
See, a-Naphthylamine
/3-Amino-naphthalene
See, /3-Naphthylamine
3-Amino-2:7-naphthalene-disulfonic Acid (C. A. nomen.)
See, Amino-R Acid
4-Amino-l: 5-7iaphthalene-disulfonic Acid (C. A. nomen.)
See, l-Naphthylamine-4: 8-disulfonic Acid
4-Amino-l: 6-naphthalene-disulfonic Acid (C. A. nomen.)
See, l-Naphthylamine-4: 6-andA: 7-disulfonic Acids
4-Amino-l: 7-naphthalene-disulfonic Acid (C. A. nomen.)
See, l-Naphthylamine-4: 6-andA: 7-disulfonic Acids
4-Amino-2:-7-naphthalene-disulfonic Acid (C. A. nomen.)
See, Freund^s Acid
5-Amino-l: 3-naphthalene-disulfonic Acid (C. A. nomen.)
See, l-Naphthylaminc-5: 7-disulfonic Acid
6-Amino-l: 3-naphthalene-disulfonic Acid (C. A. nomen.)
See, 2-Naphthylaminc-5: 7-disulfonic Acid
7-Amino-l: 3-naphthalene-disulfonic Acid (C A. nomen.)
See, Amino-G Acid
8-Amino-l: 6-napthalene-disulfonic Acid (C. A, nomen.)
See, l-Naphthylaminc-3:8-disulfonic Acid
l-Amino-naphthalene-4-sulfonic Acid
See, Naphthionic Acid
l-Amino-2-naphthalene-sulfonic Acid (C. A. nomen.)
See, l-Naphthylamine-2-sulfonic Acid
62 DYES CLASSIFIED BY INTERMEDIATES
2-Anuno-l-naphthalene-sulfonic Acid (C. A. nomen.)
See, 2-Naphthylamine-l-sulfonic Acid
4-Amino-l-naphthalene-sulfonic Acid (C. A. nomen.)
See, Naphthionic Acid
6-Amino-l-naphthalene-sulfonic Acid (C. A. nomen.)
See, Laurent's Acid
6-Anuno-2-naphthalene-sulfonic Acid (C. A. nomen)
See, l-Naphthylamine-6-sulfonic Acid
5-and-8-Amino-2-naphthalene-sulfonic Acids (C A. nomen.)
See, l-Naphthylamine-6-and~7-sulfonic Acids
6-Amino-2-naphthalene-sulfonic Acid (C A. nomen.)
See, Broenner's Acid
6-and-7-Amino-l-naphthalene-sulfonic Acids (C. A. nomen.)
See, 2-Naphthylamine~5~and-8~sulfonic Acids
7~Ainino-2-naphthalene-sulfonic Acid (C. A. nomen.)
See, 2-Naphthylamine-7~sulfonic Acid
8-Amino-l-naphthalene-sulfonic Acid (C. A. nomen.)
See, l-Naphthylamine-8-sulfonic Acid
8-Amino-l: 3: 6-naphthalene-trisulfonic Acid (C. A. nomen.)
See, l-Naphthylamine-4: 6: 8-trisulfonic Acid
8-Amino-l: 3:6-naphthalene-trisulfonic Acid (C. A. nomen.)
See, l-Naphthylamine-3: 6: 8-trisulfonic Acid
6-Amino-l-naphthol
OH
DYES CLASSIFIED BY INTERMEDIATES 63
FORMATION.—From l-amino-naphthalene-5-sulfonic acid by fusion withcaustic soda at 250°
LITERATURE.—Lange, Zwischenprodukte, #2335
Dye Derived from 5-Amino-l-naphthol
SchultzNumberfor Dye
187
Ordinary Name andClass of Dye
MONOAZO DYELanacyl Blue BB
Statistics ofImport and
Manufacture
I '14:—1,200
Other IntermediatesUsed and Notes
H Acid
DyeAppli-cationClass
A
Amino-naphthol 8
l-Amino-7-naphthol (not considered herein)
l-Aminc-8-naphthol-2:4-disulfonic Acid
8~Amino-l-7iaphthol-5: 7-disulfonic Acid (C. A. nomen.)
SS Acid or 2S Acid
Chicago Acid
Amino-naphthol-disulfonic Acid SS
HO NH2
—319
SO3H
STATISTICS.—Manufactured '19:— ?Manufactured ;20:— ?
FORMATION.—By caustic fusion at 180-190° of sodium l:8-naphtha-sultam-2:4-disulfonate (anhydride of l-amino-naphthalene-2:4: 8-trisulfonic acid), which in turn is made from 1-naphthylamine-4:8-disulfonic acid
64 DYES CLASSIFIED BY INTERMEDIATES
LITERATURE.—Cain, Intermediate Products (2d Ed.), 236
Lange, Zwischenprodukte, #2719
Thorpe, Die. Chemistry, 3, 641
Dyes Derived from l-Amino-8-naphthoI-2:4-disulfonic Acid
SchultzNumberfor Dye
419
422
424
Ordinary Name andClass of Dye
DISAZO DYESChicago Blue RW
Chicago Blue 4B
Chicago Blue 6B
Statistics ofImport and
Manufacture
I 14:— 15,176M'19:— ?I '20:— 150
I '14:— 8,269
I '14:—118,542M'19:— ?I '20:— 7,480
M'20:— ?
Other IntermediatesUsed and Notes
Dianisicline/3-Naphthol
Dianisidine1- Amino-8-naphthol-
4-sulfonic Acid
Dianisidine1 -Amino-S-naph thol-
2:4-disulfonic Acid(2 mols)
DyeAppli-cationClass
D
D
D
l-Amino-8-naphthol-3: 5-disulfonic Acid
8-Amino-l-naphthol-4: 6-disulfonic Acid (C. A. nomen.)
Amino-naphthol-disulfonic Acid B
B Acid
HO NH2
:C10H9NO7S2=:319
HO3S
FORMATION.—By sulfonation of l-amino-S-naphthol-S-suKonic acid
LITERATURE.—Amer. Pat. 606,437
Ger. Pat. A. F . 8626
DYES CLASSIFIED BY INTERMEDIATES 65
Dyes Derived from l-Amino-8-naphthol-3:5-disulfonic Acid
SchultzNumberfor Dye
216
389
466
Ordinary Name andClass of Dye
DISAZO DYESDomingo Blue
Black B
Eboli Blue B
TRISAZO DYEEboli Green CW
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
Anilinep-Nitro-anilmc
Tolidine1- Amino- 8- naphthol-
3: 5-disulfonic Acid(2 mols)
BcnzidineSalicylic AcidSulfanilic Acid
DyeAppli-cationClass
A
D
D
l-Amino-8-naphthol-3:6-disulfonic Acid
See, H Acid
l-Amino-8-naphthol-4: 6-disulfonic Acid
See, K Acid
2-Amino-8-naphthol-3: 6-disulfonic Acid
See, 2R Acid
7-Amino-l-naphthol-3:6-disulfonic Acid (C. A. nomen.)
See, 2R Acid
8-Amino-l-naphthol-3:5-disulf onic Acid (C A. nomen.)
See, K Acid
8-Amino-l-naphthol-3:6-disulfonic Acid (C. A. nomen.)
See, H Acid
8-Amino-l-naphthol-4:6-disulfonic Acid (C. A. nomen.)
See, l-Amino-8-naphthol-3: 5-disulf onic Acid
66 DYES CLASSIFIED BY INTERMEDIATES
8-Amino-l-naphthol-5: 7-disulfonic Acid (C. A. nomen.)
See, l-Amino-8-naphthol-2: 4-disulfonic Acid
Amino-naphthol-disulfonic Acid B
See, l~Amino-8-Naphthol-3: 5-disulfonic Acid
Amino-naphthol-disulfonic Acid H
See, H Acid
Amino-naphthol-disulfonic Acid K
See, K Acid
Amino-naphthol-disulfonic Acid RR
See, 2R Acid
Amino-naphthol-disulfonic Acid SS
See, l-Amino~8-naphthol-2: 4-disulfonic Acid
l-Amino-2-naphthol Ethyl Ether
Naphthylamine Ether
2~Ethoxy-l-naphthylamine ( C A. nomen.)
NH2
O. C2H5 — nxi
FOKMATION.—l-Nitro-2-naphthol ethyl ether is reduced in an alcoho]solution with iron turnings and hydrochloric acid
LITERATURE.—Lange, Zwischenprodukte, #2345, 2333
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from l-Amino-2-naphthol Ethyl Ether
67
SchultzNumberfor Dye
268
271
Ordinary Name andClass of Dye
DISAZO DYENaphthyl Blue
Black N
Diamine Blue 6 G
Statistics ofImport and
ManvfactureOther Intermediates
Used and Notes
l-Naphthylamme-4: 6-and 4: 7- disulfonicacids
a- Naphthylamine
Amino-G acid/3-Naphthol
DyeAppli-cationClass
A
D
l-Amino-2-naphthol-4-sulfonic Acid (C. A. nomen.)
1:2:4 Acid
NH2
C 0 O H -SO3H
239
STATISTICS.—Manufactured '18:—169,999 lbs.Manufactured '19:—837,384 lbs.Manufactured ;20:—971,370 lbs.
FORMATION.—/3-Naphthol is changed to the l-nitroso-£-naphthol,which is treated with sodium bisulfite. Upon acidification thefree sulfurous acid effects simultaneous reduction and sulfonation
LITERATURE.—Cain, Intermediate Products (2d Ed.), 233Langc, Zwischcnprodukte, #2507
Dyes Derived from l-Amino-2-naphthol-4-sulfonic Acid
SchultzNumberfor Dye
29
Ordinary Name andClass of Dye
MONOAZO DYESErio chrome Red B
Statistics ofImport and
Manufacture
I '14:— 5,491
Other IntermediatesUsed and Notes
3-Mcthyl-l-phcnyl-5-pyrazolone
DyeAppli-cationClass
ACr
68 DYES CLASSIFIED BY INTERMEDIATES
DyesSchultz
Numberfor Dye
ISO
181
Derived from l-Amino-2-naphthol-4-sulfonic Acid (continued)
Ordinary Name andClass of Dye
MONOAZO DYES(continued)
Erichrome BlueBlack B
Palatine ChromeBlack 6B
Salicine Black
Statistics ofImport and
Manufacture
I '14:— 57,000M'17:— 9,326M'18:— ?M'19:— ?I '20:— 20,317M'20:— 29,255
I '14:—248,721M'17:— ?M'18:—469,159M'19:—739,372I '20:— 2,001M'20:—
1,074,248
Other IntermediatesUsed and Notes
a-Naphthol
/3-Naphthol
DyeAppli-cationClass
ACr
ACr
l-Amino-2-naphthol-6-sulfonic Acid (C. A. nomen.)
NH2
HO3SOH
FORMATION.—Schaeffer's acid is treated with nitrous acid resulting inl-nitroso-2-naphthol-6-sulfonic acid. This latter is reduced withzinc and hydrochloric acid
LITERATURE.—Meldola, Chem. Soc. Trans. 39, 47 (1881)Thorpe, Die. Chemistry, 3, 637
SchultzNumberfor Dye
656
Dye Derived from l-Amino-2-naphthol-6-sulfonic Acid
Ordinary Name andClass of Dye
OXAZINE DYEAlizarin Green G
Statistics ofImport and
Manufacture
M'19:— ?
Other IntermediatesUsed and Notes
1: 2-Naphthoquinone-4-sulfonic acid
DyeAppli-cationClass
M
DYES CLASSIFIED BY INTERMEDIATES
l-Amino-5-naphthol-7-sulfonic Acid
5-Amino~l-?2aphthol~3-sulfonic Acid (C A. nomen.)
M Acid
NH2
HO3Sf A _ c10H9NO4S = 239
69
HO
FORMATION.—By fusing l-naphthylaminc-5:7-disulfonic acid withcaustic soda at 160-220°
LITERATURE.—Cain, Intermediate Products (2d Ed.) 234Thorpe, Die. Chemistry, 3, 638
SchultzNumberfor Dye
345
421
Dyes Derived from
Ordinary Name andClass of Dye
DISAZO DYESOxamine Maroon
Oxamine Blue B
l-Amino-5-naphthol-7-sulfonic Acid
Statistics ofImport and
Manufacture
I J14:—35,891I ;20:— 13
Other IntermediatesUsed and Notes
BenzidincSalicylic Acid
DianisidincNcvile-Winthcr's Acid
DyeAppli-cationClass
D
D
l-Amino-8-naphthol-4-sulfonic Acid
8-Amino-l-naphthol-5H3iilfonic Acid (C A. nomen.)
Amino-naphthol-sulfonic Acid H
S Acid
HO NH2
SO3H
STATISTICS.—Manufactured '20:— ?
FORMATION.—By caustic aocki fusion of l-naphthylamine-4: 8-disulfonicacid at 200-230°
70 DYES CLASSIFIED BY INTERMEDIATES
LITERATURE.—Cain, Intermediate Products (2d Ed.), 234
Thorpe, Die. Chemistry, 3, 638
Lange, Zwischenprodukte, #2524 et seq.
Dyes Derived from l-Amino-8-naphthol-4-sulfonic Acid
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
Manufacture
Other IntermediatesUsed and Notes
DyeAppli-cationClass
220
324
325
336
384
387
388
390
420
422
DISAZO DYES
Palatine Black
Chicago Blue 4R
Columbia Blue R
Benzo Cyanine R
Chicago Blue 2RDiamineBlueC2R
Columbia Blue G
Chicago Blue R
Benzo Cyanine B
Azidine Wool Blue B
Chicago Blue 4B
I '14:-I '20:-
I '14:-
I '14:-
I '14:-
I '14:-
I '14:-
-299,274200
- 1,199
- 3,071
201
- 23,877
- 7,094
I '14:- 201
I '14:— 8,269
a-NaphthylamineSulfanilic Acid
BenzidineCroceine Acid
Benzidinel-Naphthol-3: 8-disul-
fonic Acid
BenzidineHAcid
TolidineCroceine Acid
Tolidinel-Naphthol-3: 8-disul-
fonic Acid
Tolidinel-Amino-8-naphthol-
4-sulfonic Acid (2mols)
TolidineHAcid
DianisidineCroceine Acid
Dianisidinel-Amino-8-naphthol-
2: 4-disulfonic Acid
A
D
D
D
D
D
D
D
D
D
DYES CLASSIFIED BY INTERMEDIATES 71
Dyes Derived from l-Amino-8-naphthol-4:-sulfonic Acid (continued)
SchultzNumberfor Dye
423
425
465
478
Ordinary Name andClass of Dye
DISAZO DYES(continued)
Chicago Blue B
Benzo Cyanine 3B
TRISAZO DYEColumbia Black
Green D
Columbia Green
Statistics ofImport and
Manufacture
M'lS:— ?
I '14:— 1,001
I '14:— 45,162
I '20:— 7*555
Other IntermediatesUsed and Notes
Dianisidinel-Amino-8-naphthol-4-
sulfonic Acid (2 mols)
DianisidinePI Acid
BenzidineSalicylic AcidAniline
BenzidineSalicylic AcidSulfanilic Acid
DyeAppli-cationClass
D
D
D
l-Amino-8-naphthol-5-sulfonic Acid
8-Amino-l-naphthol-4-sulfonic Acid (C. A. nomen)
O H N H 2
FORMATION.—By heating l -naphthylamine-5: 8-disulfonic acid with
75 per cent caustic potash a t about 150°
L I T E R A T U R E . — G e r . Pa t . 75,055
Thorpe, Die. Chemistry, 3, 639
Langc, Zwischenprodukte, #2450
Dye Derived from l-Amino-8-naphthol-5-sulfonic Acid
SchultzNumberfor Dye
218
Ordinary Name andClass of Dye
DISAZO D Y ENigrophor BASF
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
p-Nitro-anilino2:5-Dichloro-aniline
DyeAppli-cationClass
MF
72 DYES CLASSIFIED BY INTERMEDIATES
2-Amino-l-naphthol-4-sulfonic Acid
OH
= Ci0H9NO4S = 239
FORMATION.—By heating 2~nitroso~l~naphthol with 35 per cent sodiumbisulfite solution
LITERATURE.—Schmidt, J. pr. Chem [II], 44, 531 (1891)Thorpe, Die. Chemistry, 3, 639
Dye Derived from 2-Amino-l-naphthol-4-sulfonic Acid
SchultzNumberfor Dye
657
Ordinary Name andClass of Dye
OXAZINE DYEAlizarine Green B
Statistics ofImport and
Manufacture
I ' 14:—551
Other IntermediatesUsed and Notes
1: 2- Naphthoquinone-4-sulfonic Acid
DyeAppli-cationClass
M
2-Amino-3-naphthol-6-sulfonic Acid
Amino-naphthol-sulfonic Acid R
3-Amino-2-naphthol-7-sulfonic Acid ( C A. nomen.)
HO3S
FORMATION.—From Amino-R acid (2-naphthylamine-3: 6-disulfonicacid) by caustic soda fusion at 240°
LITERATURE.—Lange, Zwischenprodukte, #2534Thorpe, Die. Chemistry, 3, 639
Dye Derived from 2-Amino-3-naphthol-6-sulfonic Acid
SchultzNumberfor Dye
185
Ordinary Name andClass of Dye
MONOAZO DYEAnthracene Chrome
Black
Statistics ofImport and
Manufacture
I '14:—51,577I '20:— 2,339
Other IntermediatesUsed and Notes
/3-Naphthol
DyeAppli-cationClass
M
DYES CLASSIFIED BY INTERMEDIATES 73
2-Amino-5-naphthol-7-sulfonic Acid
See, J Acid
2-Amino-8-naphthol-6-sulfonic Acid
See, Gamma Acid
3-Amino-2-naphthol-7-sulfonic Acid (C A. nomen.)
See, 2-Amino~3-naphthol-6-sulfonic Acid
5-Amino-l-naphthol-3-sulfonic Acid (C. A. nomen.)
See, l-Amino-5-naphthol-7-sulfonic Acid
6-Amino-l-naphthol-3-sulfonic Acid (C. A. nomen.)
See, J Acid
7-Amino-l-naphthol-3-sulfonic Acid (C. A. nomen.)
See, Gamma Acid
8-Amino-l-naphthol-4-sulfonic Acid (C. A. nomen.)
See, l-Amino-8~naphthol-5-sulfonic Acid
8-Amino-l-naphthol-5-sulfonic Acid (C. A. nomen.
See, l-Amino-8-naphthol-4-sulfonic Acid
Amino-naphthol-sulfonic Acid G
See, Gamma Acid
Amino-naphthol-sulfonic Acid J
See, J Acid
Amino-naphthol-sulfonic Acid R
See, 2-Amino-3-naphthol-6-sulfonic Acid
Amino-naphthol-sulfonic Acid S
See, l-Amino-8-naphthol-4-sulfonic Acid
Amino-naphthol-sulfonic Acid 7
See, Gamraa AcicJ
74 DYES CLASSIFIED BY INTERMEDIATES
/>-(2-Amino-4-nitro-anilino)-phenol (C A. nomen.)
See, 2-Amino-4'-hydroxy-4-nitro-diphenylamine
2-Amino-5-nitro-frenzene-sulfonic Acid (C. A. nomen. SO3H = 1)
p-Nitro-aniline-o-sulfonic Acid (NH2 = 1)
4-Nitro-aniline-2-sulfonic Acid (NH2 = 1)
SO3H
O2N
STATISTICS.—Manufactured 1918; amount not disclosed
FORMATION.—2-Chloro-5-nitro~benzene-sulfonic acid (by oleum sulfona-tion of p-chloro-nitro-bcnzene) is heated in an autoclave at 120-140°with alcoholic ammonia
LITERATURE.—Cain, Intermediate Products (2d Ed.), 56
Dyes Derived from 2-Amino-5-nitro-benzene-sulfonic Acid
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
132MONOAZO DYES
Lake Red P
133
458
EriochromcPhosphinc R
TRISAZO DYESCarbon Black
? 14:—60,345M ' 1 7 : — ?M ' 1 8 . — ?M ' 1 9 : — ?I '20:— 1,750
I '14:— 1,433
jS-Naphthol
Salicylic Acid
l-Naphthylamine-6-or-7-sulfonicAcid
m-Phenylene-diamineor m-Tolylene-dia-mine or 1: 3-Naph-thylene-diamine-6-sulfonic Acid
CL
ACr
D
DYES CLASSIFIED BY INTERMEDIATES
4-Amino-3-nitro-benzene-sulfonic Acid (C. A. nomen.)
o-Nitro-anilinc-p-sulfonic Acid
2-Nitro-aniline-4-sulfonic Acid
SO3H
75
STATISTICS.—Manufactured '17:— ?
FORMATION.—From chloro-benzene-p-sulfonic acid by nitration, fol-lowed by amidation with ammonia
LITERATURE.—Ullmann, Enzy. tech. Chemie, 1, 443
Dye Dsrived from 4-Amino-3-nitro-benzene-sulfonic Acid
SchultzNumberfor Dye
148
Ordinary Name andClass of Dye
MONOAZO DYEFast Orange 0
Statistics ofImport and
Manufacture
I '14:—1,250M'17:— ?
Other IntermediatesUsed and Notes
/3-Naphthol
DyeAppli-cationClass
CL
2-Amino-6-nitro-£-cresol (C. A. nomen. 011=1)
o-Nitro-o-amino-p-cresol
OH
O 2 N / \ N H 2
FORMATION.—The above cresol derivative is obtained by partiallyreducing the 2: 6-dinitro-p-cresol. This latter results either fromthe direct dinitration of p-cresol; or by the dinitration of p-tolui-dine, and subsequent hydrolysis with alkali
LITERATURE.—Ber. 15,1859
76 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from 2-Amino-6-nitro-£-cresol (OH=1)
SchultzNumberfor Dye
85
Ordinary Name andClass of Dye
MONOAZO DYEOmega Chrome
Black PV
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
Plieny 1-1 -naph thy 1-amine-S-sulfonic Acid
DyeAppli-cationClass
ACr
l-Amino-8-nitro-2-naphthol-4-sulfonic AcidNitro-1:2:4 Acid
O2N NH2
C 0 O H =SO3H
C10H8N2O6S —284
FORMATION.—From l-amino-2-naphthol-4-sulfonic Acid by nitration
LITERATURE.—Lange, Zwischenprodukte, #2688
Dyes Derived from l-Amino-8-nitro-2-naphthol-4-sulfonic Acid
SchultzNumberfor Dye
183
184
Ordinary Name andClass of Dye
MONAZO DYESEriochrome Black T
Eriochrome Black A
Statistics ofImport and
Manufacture
I '14:—129,550M'18:— ?M'19:— ?I '20:—2,624M'20:— ?
I '14:— 96,570M'17:— ?M'18:— ?M'19:—686,710I '20:— 14,262M'20:— ?
Other IntermediatesUsed and Notes
a-Naphthol
0-Naphthol
DyeAppli-cationClass
ACr
ACr
2-Amino-6-nitro-l-jphenol-4-sulfonic Acid (C. A. nomen. OH--
6-Nitro-2-amino-phenol-4-sulfonic Acid2-Nitro-6-amino-phenol-4-sulfonic Acid
-1)
DYES CLASSIFIED BY INTERMEDIATES 77
OH
O 2 N / \ N H 2
SO3H
FORMATION.—From phenol by sulfonation, dinitration and partialreduction with sodium sulfi.de
LITERATURE.—Cain, Intermediate Products (2d Ed.), 129
Lango, Zwischcnproduktc, #1130
Dye Derived from 2-Amino-6-nitro-phenol-4-sulfonic Acid
SchultzNumberfor Dye
159
Ordinary Name a?idClass of Dye
MONOAZO DYEAcid Alizarin
Black R
Statistics ofImport and
Manufacture
I '14:—16,800M'19:— ?I J20:— 439M'20:— ?
Other IntermediatesUsed and Notes
jS-Naphthol
DyeAppli-cationClass
M
6-Amino-5-nitroso-2-7iaphthalene-sulfonic Acid (C. A. nomen.)
See, l-Nitroso-2-naphthylamine-6-sulfonic Acid
m-Amino-phenol
OH
=CeH7NO =
FORMATION.—By the fusion of Metanilic Acid (3-amino-benzene-sulfonic acid) with caustic soda at about 280-290°
LITERATURE.—Ber. 32,2112-2124
Lange, Zwischenprodukte, #582-584
78 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from m-Amino-phenol
SchultzNumberfor Dye
90
923
Ordinary Name andClass of Dye
MONOAZO DYEChrome Brown P
ANILINE BLACKGROUP
Fuscamine
Statistics ofImport and
Manufacture
I '14:— 54,005M '19:— ?
I '20:— 1,600(M'20:—168,459)
Other IntermediatesUsed and Notes
Picramic Acid
?n-Ammo-phenol(x mols)
[Oxidation on hair]
DyeAppli-cationClass
M
Fur
jp-Amino-phenol
OH
NH2
STATISTICS.—Imported '14:— 10,631 lbs.Manufactured '17:— ?Manufactured '18:—113,428 lbs.Manufactured '19:—128,627 lbs.Manufactured '20:— 41,474 lbs.
FORMATION.—Phenol is treated with sodium nitrite in the cold and theresulting p-nitroso-phenol is reduced with sodium sulfide
LITERATURE.—Cain, Intermediate Products (2d Ed.), 117Lange, Zwischenprodukte, #585-589
Dyes Derived from ^-Amino-phenol
SchultzNumberfor Dye
14
84
Ordinary Name andClass of Dye
STILBENE DYEDiphenyl Chrysoine
MONOAZO DYEAzo Chromine
Statistics ofImport and
Manufacture
I '14:— 9,898
Other IntermediatesUsed and Notes
p-Nitro-toluene-o-sul-f onic Acid (2 mols)
Pyrogallol
DyeAppli-cationClass
D
M
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from j&-Amino-phenol (continued)
79
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
709
717
724
725
726
733
734
923
SULFUR DYESItalian Green
Vidal Black I
Immedial Black
Immedial DarkBrown A
Immedial Brown B
Pyrogene Direct BluePyrogcne Blue
Immedial Indonc
Pyrogene Yellow
ANILINE BLACK
GROUP
Ursol P
'14:— 298M'18:— ?I '20:— 2,603
I 14:— 7,495
I '14:— 54,696M'18:— ?
I '14:— 23,887M'18:— ?
I '14:— 10,934I '20:— 2,498
I '14:— 4,236
I '14:— 18,515I '20:— 2,701
I '14:— 54,005M'19:— ?I '20:— 1,600M'20:—168,459
[Sulfur, etc.]
[Na2S+S]
l-Chloro-2: 4-dinitro-benzene
[S+Na2S]
l-Chloro-2: 4-dinitro-benzene
[NaOH; S+Na2S]
l-Chloro-2: 4-dinitro-benzene
[Alcohol; S+Na2S]
o-Toluidine[S+Na2S]
p-Nitro-benzyl chloride
p-Amino-phenol(x mols)
[Oxidation]
S
S
Fur
4-Amino-l-i>henol-2:6-disulfonic Acid (011=1) (C. A. nomen.)
p-Amino-phcnol-a-disulfonic AcidOH
H O 3 S | / \ S O 3 H _ C J
N H 2
Note.—Position of the sulfonic groups not fully established.
80 DYES CLASSIFIED BY INTERMEDIATES
FORMATION.—Nitroso-dimethyl-aniline hydrochloride or nitroso-phenolis introduced into a solution of sodium bisulfite, and warmed toeffect solution. Then concentrated hydrochloric is added and theliquor boiled for two hours, using direct steam
LITERATURE.—Gcr. Pat . 65,236Boil. spl. I I , 492Lange, Zwischenprodukte, #1154
Dye Derived from 4-Amino-l-phenol-2: 6-disulfonic Acid
SchultzNumberfor Dye
15S
Ordinary Name andClass of Dye
MONOAZO DYEChrome Brown
RR
Statistics ofImport and
Manufacture
I '14:—7,241M'17:— ?I '20:—2,183
Other IntermediatesUsed and Notes
Pyrogallol
DyeAppli-cationClass
M
/j-Amino-phenol Ethyl Ether
See, p-Phenetidine
2-Amino-l-phenol-4-sulfonic Acid (C. A. nomen. OH=1)
o-Amino-phenol-p-sulfonic Acid
o n
SO3H
STATISTICS.—
= C 6 H 7 NO 4 S=189
Manufactured '18:— ?Manufactured 19:— ?Manufactured '20:— ?
FORMATION.—Chloro-benzene is sulfonated and nitrated. The chloro-body is then hydrolyzed to the phenol by boiling with caustic soda,and finally reduced to 2-amino-phenol-4-sulfonic acid by means ofsodium sulfide
LITERATURE.—Cain, Intermediate Products (2d Ed.), 129
DYES CLASSIFIED BY INTERMEDIATES 81
Dyes Derived from 2-Amino-l-phenol-4-sulfonic Acid
Schultz
XV VtlWjZrTfor Dye
154
155
156
157
Ordinary Name andClass of Dye
MONOAZO DYESAcid Alizarin
Brown BPalatine Chrome
Brown W
Acid AlizarinGarnet R
Acid AlizarinViolet N
Palatine ChromeViolet
Diamond Black PV
Statistics of
1 TripOTl aTl/ClManufacture
I '14:— 18,264M'17:— ?M'18:— ?M'19:— ?I '20:— 845M'20:— ?
I '20:— 201M'20:— ?
I '14:— 1,199M'19:— ?M'20:— ?
I '14:—285,074M'20:— ?
Other IntermediatesUsed and Notes
m-Phcnylene-diamine
Hcsorcinol
jS-Naphthol
1:5-Dihydroxy-naph-thalene
DyeAppli-cationClass
M
M
ACr
M
3-Amino-l-jf>henol-4-sulfonic Acid (C. A. nomen. OH=1.)
Amino-phenol-sulfonic Acid III
FORMATION.—^By fusion with caustic soda of the aniline-disulfonic acidprepared by sulfonation of mctanilic acid.
Note.—^Amino-phenol-sulfonic acid I I I is not 5-amino-phenol-2-sulfonic acid
LITERATURE.—Ber. 39, 3345
Lange, Zwischenprodukte, #942
82 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 3-Amino-l-phenol-4-sulfonic Acid
SchultzNumberfor Dye
339
481
Ordinary Name andClass of Dye
DISAZO DYEBrilliant Orange G
TEISAZO DYEAzo Corinth
Statistics ofImport and
Manufacture
I '14:—6,321M'17:— ?
Other IntermediatesUsed and Notes
BenzidineSalicylic Acid
TolidineNaphthionic AcidResorcinol
DyeAppli-cationClass
D
D
o-Amino-phenol-^-sulfonic AcidSee, 2~Amino-l-phenol-4-sulfonic Acid
Amino-phenol-sulfonic Acid IIISee, 3~Amino-l-phenol~4-sulfonic Acid (OH = 1)
Amino-phenol-sulfonic Acid IV3-Amino-l-phenol-6-sulfonic Acid (not considered herein)
Amino-phenol-sulfonic Acid V3-Amino-l-phenol-5-sulfonic Acid (not considered herein)
/>-(/>-Amino-phenyl-azo)-&enzene-sulfonic AcidSee, Amino-azo-benzene-sulfonic Acid
l-(/>-Amino-phenyl)-5-methyl-benzothiazole (C ^L nomen.)
See, Dehydro-thio-p-toluidine
IV-Amino-2-phenyl-5-methyl-thiazolSee, Dehydro-thio-p-toluidine
^-Amino-phenyl-toluthiazoleSee, Dehydro-thio-p4oluidine
(m-Amino-phenyl) -trimethyl-ammonium Chloride
Trimethyl-m-amino-phenyl-ammonium chloride
C1N(CH3)3
JNH2 ~ = 186.5
DYES CLASSIFIED BY INTERMEDIATES 83
FORMATION.—m-Nitro-aniline by heating in methanol (methyl alcohol)solution, with hydrochloric acid is transformed into m-nitro-phenyl-trimethyl-ammonium chloride (and m-nitro-dimethyl-aniline). The7?2-nitro-phenyl-trimethyl-ammonium chloride is dissolved in waterand reduced with zinc dust and hydrochloric acid
LITERATURE.—Lange, Zwischenprodukte, #549,564Green, Organic Coloring Matters (1908), 12
Dyes Derived from (m-Amino-phenyl)-trimethyl-ammonium Chloride
SchultzNumberfor Dye
60
222
240
435
Ordinary Name andClass of Dye
MONOAZO DYEAzo Phosphine GO
DISAZO DYESJanus Yellow G
Janus Red B
TRISAZO DYEJanus Brown B
Statistics ofImport and
Manufacture
I '14:— 50
I '14:—23250I '20:— 75S
I ' 1 4 : - 250I'20:— 176
Other IntermediatesUsed and Notes
Rcsorcinol
Resorcinolm-Nitro-anilinc
m-Toluidinc0-Naphthol
a-Naphthylamineor m-Toluidine
Anilinem-Phcnylcne-diamine
DyeAppli-cationClass
B
B
B
B
Amino-R Acid
2-Naphthylaminc-3: 6-disulfonic Acid
/3-Naphthylamine-disulfonic Acid R
j8-Naphthylamino-a-disulfonic Acid
3-Amino-2: 7-^aphthalcne-disulfonic Acid (C. A nomen.)
HO3SNH,SO3H
FORMATION.—By heating R salt with ammonia in an autoclave, inpresence of ammonium bisulfite
LITERATURE.—Cain, Intermediate Products (2d Ed.), 207Lange, Zwischenprodukte, #2594Thorpe, Die. Chemistry, 3, 604
84 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Amino-R Acid
SchultzNumberfor Dye
120
314
315
316
332
358
359
369
370
373
Ordinary Name andClass of Dye
MONOAZO DYESalmon Red
DISAZO DYESPyramine Orange 2R
Congo Orange R
Brilliant Congo G
Dianil Garnet BBenzo Fast Red
Brilliant DianolRedR
Diphenyl Red
Trypan Red
Brilliant Purpurin R
Brilliant Congo R
Congo Orange R
Statistics ofImport and
Manufacture
M'20:— ?
I '14:— 2,7S9
I '14:— 1,623I '20:— 75
I '14:— 5,985I '20:— 3,799
I '14:—14,305I '20:— 3,704
I '14:— 8,051
I '14.-19,133I '20:—11,129
I '14:— 7,027I '20:— 254
Other IntermediatesUsed and Notes
Dchydro-thio-m-xyli-dine
BenzidineNitro-m-phcnylene-
diamine
BenzidinePhenol[Etliylation]
BenzidineBroenner's Acid
BenzidineGamma Acid
Dichloro-benzidineAmino-R Acid (2 mols)
Benzidine-sulfonic AcidAmino-R Acid (2 mols)
TolidineNaphthionic Acid
TolidineBroenner's Acid
TolidinePhenol[Etliylation]
DyeAppli-cationClass
D
D
D
D
D
D
Medi-cinal
D
D
D
6-Amino-salicylic AcidCOOH
DYES CLASSIFIED BY INTERMEDIATES 85
STATISTICS.—Imported 14:— 9,188 lbs.
Manufactured 17:— ?Manufactured '18:— ?Manufactured 19:—37,769 lbs.Manufactured '20:— ?
FORMATION.—(1) From the corresponding nitro-salicylic acid by re-duction. (2) By reducing the azo-dye, benzene-azo-salicylic acid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 150
SchultzNumberfor Dye
275
276
277
492
550
Dyes Derived
Ordinary Name andClass of Dye
DISAZO DYESDiamond Black F
Diamond Green B
Anthracene AcidBlack DSF
TJBTRAKJSAZO DYEAnthracene Acid
Brown B
TRIPHENYL-METHANEDYE
Chrome Bordeaux
from 5-Amino-saIicylic Acid
Statistics ofImport and
Manufacture
I 14:—462,306M17:— ?M18:— ?M 19:—222,938I '20:— 2,226M'20:— ?
I 14:— S;622M18:— ?I '20:— 4,016
I 14:— 17,793
Other Intermediates"Used and Notes
a-NaphthylamineNevile-Winther Acid or
1 - n aph thol-5-sulf onicAcid
a-Naphthylamine1:8-Dihydroxy-naph-
thalene- 4- sulfonicAcid
l-Naphthykmine-6-and 7-sulfonic Acids,etc.
l-Naphthylamine-6-sul-fonic Acid (2 mols)
ra-Phenylene-diamineAmino- salicylic Acid
(2 mols)
Hydrol[Oxidation]
DyeAppli-cationClass
ACr
ACr
M
MACr
M
Amino-Schaefler's Acid
See, Brocnncr's Acid
86 DYES CLASSIFIED BY INTERMEDIATES
l-(4-Amino-?-sulfo-phenyl)-5-methyl-6enzothiazole (C. A. nomen.)
See, Dehydro-thio-p-toluidine-sulfonic Acid
4-Amino-4:5-sultam-l:3: 6-naphthalene-trisulfonic Acid (C. A.nomen.)
See, 1: 8-Naphthasultam-2: 4-disulfonic Acid
m-Amino-tetramethyl-/>': ^"-diamino-triphenyl-methaneN': N': N": iV"-Tetramethyl-m: p': p'^methenyl-trisaniline (C.
A. nomen.)
= C2aH27N3 = 345
N H 2
FORMATION.—m-Nitro-benzaldehyde and dimethyl-aniline are con-densed in the presence of acids or zinc chloride to m-nitro-tetra-methyl~p: p-diamino-triphenyl-methane, which by reduction givesthe m-amino-derivative
LITERATURE.—Schultz, Chcmie Steinkohlenteers (3 aufl.), 1, 115, 116.
Dye Derived from m-Amino-tetramethyl-^': ^''-diamino-triphenyl-methane
SchultzNumberfor D'ye
510
Ordinary Name andClass of Dye
TRIPHENYL-METHANEDYE
Azo Green
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
Salicylic Acid
DyeAppli-cationClass
M
4-Amino-m-foluene-sulfonic Acid (C. A. nomen. SOzH=l)
o-Toluidine-m-sulfonic Acid (CH3 = 1)
SO,H
JCH3
DYES CLASSIFIED BY INTERMEDIATES 87
FORMATION.—From o-toluidine acid sulfate by heating in an oven
LITERATURE.—Cain, Intermediate Products (2d Ed.), 57
Dyes Derived from 4-Amino-m-toluene-sulfonic Acid (SO3H=1)
SchultzNumberfor Dye
24
151
Ordinary Name andClass of Dye
PYRAZOLONE DYEPigment Fast
Yellow R
MONOAZO DYEOrange RO, T
Statistics ofImport and
Manufacture
I '14:—90,747M'17:— ?M'19:— ?I '20:— 20M'20:— ?
Other IntermediatesUsed and Notes
3-Methyl-l-phenyl-5-pyrazolone
DyeAppli-cationClass
CL
A
6-Amino-o-foluene-sulfonic Acid (C A. nomen. SOnH=l)p-Toluidinc-o-sulfonic Acid (CH3 = 1)
SO3H
H2N = C7H9NO3S:=187
STATISTICS.—Manufactured ;20:— ?
FORMATION.—From p-toluidine sulfate by heating in oven (bakingprocess)
LITERATURE.—Green, Organic Coloring Matters (1908), 22Langc, Zwischenproduktc, //839,237
Dyes Derived from 5-Amino-o-toluene-sulfonic Acid (SOzH
SchtdtzNumberfor Dye
150
152
Ordinary Name andClass of Dye
MONOAZO DYESFast Yellow N
Lithol Rubiue BPermanent Red 413
Statistics ofImport and
Manufacture
I '14:—101,395
I '20:— 2,983M'20:— ?
Other IntermediatesUsed and Notes
Diphcnylamine
3~Hydroxy-2-naphthoicAcid
= 1)Dye
Appli-cationClass
A
CL
'< DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 5-Amino-o-toluene-sulfonic Acid (continued)
SchultzNumberfor Dye
S52
SG5
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Alizarin DirectViolet R
Alizarin DirectGreen G
Statistics ofImport and
Manufacture
I '20:— 251
I '14:— 2,000I '20:— 31,851M'20:— ?
Other IntermediatesUsed and Notes
Quinizarin
Quinizarinp-Toluidine-3-sulfonic
Acid (2 mols)
DyeAppli-cationClass
A
ACr
3'-Amino-(/)-foluene-sulfo)-/)-toluide (C. A. nomen.)
See, iV-(3~Amino-4-mcthyl~phenyl)-p-toluene-sulfamide
4-(4-Amino-7n-tolyl-azo)-m-^oluene-sulfonic Acid (C. A. nomen.)
See, o-Amino-azo-toluene-sulfonic Acid
l-(4-Amino-m-tolyl)-3: 5-dimethyl-&enzothiazole (C A. nomen.)
See, Dchydro-thio-m-xylidine
l-(6-Amino-m-tolyl)-3: 5-dimethyl-&enzothiazole (C. A. nomen.)
See, iso-Dehydro-thiO'-m-xylidine
l-Amino-4: 5: 8-trihydroxy-anthraquinone8-Amino-l: 4: 5-trihydroxy-anthraquinone (C A. nomen.)
HO CO
FOUMATION.—4: 8-Dinitro-anthrarufm (p-dinitro-anthrarufin) is heatedwith sulfuric and boric acids at temperature of water bath, formingl-nitro-4: 5: 8-trihydroxy-anthraquinone. (At higher tempera-tures the 1: 4: 5: 8-tetrahydroxy-anthraquinone is formed.) Byreduction of the 1-nitro-dcrivative, the desired ammo-derivativeresults.
DYES CLASSIFIED BY INTERMEDIATES 89
LITERATURE.—Ger. Pat. 125,579; FrdL 6, 335; Chem. Zen. 1901, I I ,1189
Dye Derived from l-Amino-4: 5: 8-trihydroxy-anthraquinone
tichullzNumberfor Dye
823
Ordinary Name andClans of Dye
ANTHRAQUINONE ANDALUND DYJUS
Algol Violet B
Statistics ofImport and
Manufacture
I '20:—G9
Other IntermediatesUsed and Notes
Benzoyl chloride
DyeAppli-cationClass
V
Andresen's Acid
See, l-Naphthol-3: 8-disulfonic AcidThin trivial 7iame also applied to:—
2-Naphthylaminc-4: 7-disulfonic Acid
Anhydro-formaldehyde-aniline1:3: 5-Triphenyl-hcxahydro-$-friazme (C. A. nomen.)Formaniline
=C2 iH2 iN3 —315II2C CII2
II6Ce. N N . CIIs
Note.—Some of the older books give the formula as CeH^N
STATISTICS.- -Manufactured 1920, but in an undisclosed amount.
FORMATION. By condensation of aniline and formaldehyde
LITERATURE. -Beilstein, Organisehe Ohomio (3d auf.), 2, spl. 233
Cain and Thorpe, Synthetic Dyestuffs, 90
Dye Derived from Anhydro-formaldehyde-aniline
SchulizNumberfor Dye
511
, Ordinary N(Jtnr andClaxx of Dye
DYEPanifurliMncPunimngeuta
titatifitics ofImport and
Manufacture
M7U:--()5,O2GM'ltS:- ?M;M):— ?M72()-- ?
Other IntermediatesUsed and Notes
AnilineAniline hydro-chloride[Nitro-benzeue and
ferric chloride)
DyeAppli-cationClass
B
90 DYES CLASSIFIED BY INTERMEDIATES
Anhydro-formaldehyde-o-toluidine
N:CH2
FORMATION.—By condensation of o-toluidine and formaldehyde
SchultzNumberfor Dye
513
Dyes Derived from
Ordinary Name andClass of Dye
TRIPHENYL-METHANEDYE
New Fuchsine 0
Anhydro-formaldehyde-o-toluidine
Statistics ofImport and
Manufacture
I '14:—300M'18:— ?M'19:— ?M720:— ?
Other IntermediatesUsed and Notes
o-Toluidine0-Toluidine
hydrochloride[o-Nitro-toluene and
ferrous chloridel
DyAppcaticCla
B
STATISTICS.—Imported '14:— 4,553,028 lbs.Manufactured '17:—30,149,397 lbs.Manufactured '18:—25,867,488 lbs.Manufactured '19:—25,792,095 lbs.Manufactured '20:—41,259,142 lbs.
FORMATION.—Benzene is nitrated to nitro-benzene with mixed nitand sulfuric acid. The nitro-benzene is reduced to aniline wiiron turnings and hydrochloric acid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 40
Lange, Zwischenprodukte, #69-82
DYES CLASSIFIED BY INTERMEDIATES 91
SchultzNumberfor Dye
12
19
20
31
32
33
Dyes
Ordinary Name andClass of Dye
STILBENE DYEDiphcnyl
Citronine G
PYRAZOLONE DYESFlavazine LFast Light Yellow
Flavazine S
MONOAZO DYESAmino-azo-bcnzcneSpirit Yellow
Butter YellowOil Yellow
Chrysoidine
Derived from -
Statistics ofImport and
Manufacture
I '14:— 3S,908I '20:— 9,327
I '14:— 81,375I '20:— 1,500
M'17:— ?M'18:— 52,283M'19:— ?M '20:— ?
I '14:— 4,062M'17:— 33,180M'18:— 27,669M'19:— 31,156M'20:— 74,182
I '14:— 63,303M'17:—195,756M'18:—376,495M'19:—314,581M'20:—585,648
Aniline
Other IntermediatesUsed and Notes
Aniline (2 mols)Dinitro-dibenzyl-
disulfonic Acidor
Dinitro-distilbene-disulfonic Acid
orp-Nitro-toluene-o-sul-
fonic Acid (2 mols)
3-Methyl-l-p-sulfo-phenyl-5-pyrazolone
orPhenyl-hydrazine-p-
sulfonic AcidAceto-acetic Ethyl
Ester
l-p-Sulfophenyl-5-pyrazolone-3-car-boxylic Acid
orPhenyl-hydrazine-p-
sulf onic AcidOxal-acetic Ester
Aniline (2 mols)
Dimethyl-aniline
w-Phenylene-diamine
DyeAppli-cationClass
D
A
A
ss
ss
B
Dyes Derived from Aniline {continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
MONOAZO DYES(continued)
Chrysoidine R
Sudan G
Sudan IOil Orange
Ponceau 4 GBCroceine Orange
Orange G
Ponceau G
Chromotrope 2R
Fast AcidFuchsine B
I '14:—111,006M'17:— 58,115M'lS:—137,035M'19:--220,542M'20:—186,793I J20:— 1,102
m-Tolylene-diamine B
I '14:-M'17:-M'18:-M'19:-M'20:-
t:— 798
- 4,554- 32,45,- 29,670- 75,868-116,624
I '14:— 13,046M'17M ' l SM'19M'20
30,82417,27496,573
I '14:— 48,456M'17M'18M'19M'2OI '20
M'17:—M'19:—
-120,874- 100
I '14:M'17:M'18:M'19:M'20:
5,000???
?
R e s o r c i n o l
0 - N a p h t h o l
s s
ss
Scliaeffer's Acid
GAcid
RAcid
Chromotropic Acid
M'18:— ?M'19:— 26,699M'20:— 30,678
HAcid
DYES CLASSIFIED BY INTERMEDIATES 93
Dyes Derived from Aniline (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
42
45
5<S
124
125
126
127
MONOAZO DYES
(continued)Amiclo Naphtliol
lied G
Tolanc Red B, G
Azo Archil R
Brilliant Lake Red R
Alizarin Yellow R
I '14:—M'17:—M'18:—M'19:—I '20:—
3,500
2,028
Acctyl-II Acid A
Diazine Green S
Diazinc Black
Indoinc Blue RUnion Blue R
Methyl Indonc B
M '20:—132,637
I '14:— 31,674I '20:— 1,071
I '14:— 97,057M'17:—215,468M'IS:—385,910M'19:—130,424I '20:— 860M'20:— 83,334
I '14:— 1,340
K Acid
2 R Acid
3~Hydroxy-2-naphthoicAcid
Salicylic Acid[Nitration]
A
A
CL
M
I '14:—I '20:—
2,630701
I '14:— 15,353M'17:— ?M'18:— ?
M'17:— ?
0-Toluidinep-Tolylcnc-diaminc[or Safraninc]Dimethyl-aniline
o-Toluidincp-Tolylcnc-diamine[or Safraninc]Phenol
o-Toluidinep-Tolylcne-diaminc[or Safraninc]0-Naphthol
o-Toluidinep-Tolylene-diamine[or Safraninc][" Amino-naphtliols "]
B
B
B
B
94 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Aniline (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
128
182
215
216
217
219
241
242
270
MONOAZO DYES(continued)
Janus Gray B
Fast Sulf onViolet 5BS
Brilliant SulfonRedB
DISAZO DYESBlue Black N
Domingo BlueBlack B
Naphthol Blue Black
I '14:-I '20:-
4,8714,740
I '14:-- 2,653
Chrome PatentGreen N
Neutral Gray G
Sulfone Black G
Brilliant Croceine 9B
I '14:—431,027M'17:—620,218M'18:—
1,158,309M'19:—
1,877,860I '20:— 340M'20:—
2,608,864
o-Toluidinep-Tolylene-diamine[or Safranine], etc.
HAcidBenzene- (or Toluene-)
sulfonyl Chloride
K Acidp-Nitro-aniline
l-Amino-8-naphthol-3:5-disulfonic Acid
p-Nitro-aniline
HAcidp-Nitro-aniline
I '14:-M'19:-I '20:-
M'20:-
2,546
3,472
KAcidPicramic Acid
a-NaphthylamineGamma Acid
l-Naphthylamine-6-cm<27-sulfonic Acid
1:8-Dihydroxy-naphth-alene-4-sulfonic Acid
Amino-G AcidR and G Acids
DYES CLASSIFIED BY INTERMEDIATES 95
Dyes Derived from Aniline (continued)
SchultzNumberfor Dye
279
435
444
445
462
463
464
465
Ordinary Name andClass of Dye
DISAZO DYES(continued)
Benzo Fast Scarlet
TRISAZO DYESJanus Brown B
Crumpsall DirectFast Brown B
Crumpsall DirectFast Brown 0
Erie DirectBlack GX
Direct DeepBlack E, EW
Erie DirectBlack KX
Cotton Black E
Erie DirectGreen ET
Columbia BlackGreen D
Statistics ofImport and
Manufacture
I '14:— 36,674M'19:— ?I '20:— 24,153
I '14:—1,246,536
M'17:— ?M'18:— ?M'19:—
7,250,007M'20:—
7,736,994
I '14:—248,567M'19:— ?M'20:—
2,050,741
M'17:— ?M'18:— ?M'19:— 69,700M'20:— ?
Other IntermediatesUsed and Notes
J AcidPhosgene
Trimethyl-m-amino-phcnyl-ammoniumchloride or p-Amino-benzyl-dicthylamine
ct-Naphthylamine or?w-Toluidine
m-Phenylenc-diamine
BenzidineSalicylic AcidGamma Acid
BenzidineSalicylic AcidPhcnyl-gamma Acid
BenzidineH Acidm-Phcnylenc-diamine
BenzidineH Acidm-Tolylene-diamino
BenzidineH AcidPhenol
BenzidineSalicylic Acidl-Amino-8-Naphthol-
4-sulf onic Acid
DyeAppli-cationClass
D
B
D
D
D
D
D
D
96 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Aniline (continued)
SchultNumbeforDy
482
511
512
514
Ordinary Name andClass of Dye
TRISAZO DYES(continued)
Alizarin Yellow FS
TRIPHENYL-METHANEDYES
ParafuchsineParamagenta
FuchsineMagenta
Red Violet 5R
Statistics ofImport and
Manufacture
I '14:— 65,026M'18:— ?M'19:— ?M'20:— ?
I '14:— 87,102M '17:— 17,739M'18:—71,675M '19.-155,830I '20:— 189M'20.-284,285
I '14— 331I '20— 750
Other IntermediatesUsed and Notes
o-Toluidine andp-Toluidine
[or Fuchsine]Salicylic Acid (3 mols)
p-ToluidincAniline (2 mols)[Iron and nitro-benzcne
or arsenic Acid]or
p-Nitro-benzaldehydeAniline sulfate (2 mols)[Zinc chloride; ferrous
chloride]or
p: p'Diamino-diphenyl-methane or anhydro-formaldehyde-aniline
[Nitro-benzene and fer-ric chloride]
p-Toluidineo-Toluidine[Nitro-benzene, iron
and zinc chloride orarsenic acid]
[Magenta methylatedor ethylated]
oro-Toluidinep-Toluidine[Nitro-benzene, iron
and zinc chloride orarsenic acid]
[Methylation or ethyl-ation]
DyeAppli-cationClass
M
B
B
B
DYES CLASSIFIED BY INTERMEDIATES 97
Dyes Derived from Aniline (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
520
521
TKIPHENYL-METHANE^DYES (continued)
Light Blue SuperfineSpirit Soluble
Diphenylamine Blue
Spirit BlueBlue
I '14:— 2,149
524
525
Fuchsine SAcid Magenta
Red Violet 5RS
526 Acid Violet 4RS
M'17:M'lS:M'19:I '20:M'20:
50,5639
9
:— 723
I '14:-I '20:-M720:-
19,098• 524
535 Methyl Alkali Blue I '14M'18M'19I '20
:— 273
:— 29
[Para-rosanilinc tri-phcnylatcd]
orAniline (5 mols)p-Toluidine[Bcnzoic Acid]
[Magenta phenylated]or
Aniline (2-4 mols)o-Toluidinep-Toluidine[Bcnzoic Acid]
[Magenta sulfonated]or
o-Toluidincp-Toluidine[sulfonation]
[Magenta cthylatcd andsulfonated]
oro-Toluidinc??-Toluidine[Ethylation and
sulfonation]
[Magenta dimethylatcd,trisulfonated]
oro-Toluidinep-Toluidine[Dimcthylation, Tri-
sulfonation]
[Triphenyl-p-rosanilinesulfonated]
orp-ToluidineAniline (5 mols)[Sulfonation]
ss
A
98 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Aniline (continued)
SchultzNumberfor Dye
536
537
538
539
Ordinary Name andClass of Dye
TKIPHENYL-METHANEDYES
(continued)Alkali Blue
Methyl Blue for SilkMarine Blue B
Methyl BlueCotton Blue
Water BlueSoluble Blue
Statistics ofImport and
Manufacture
I '14:—286,751M'17:— ?M'18:— 43,184M'19:— 77,796I '20:— 6,778M'20:— 74,253
I '14:— 34,867M '18:— ?M'19:— ?I '20:— 2,395M'20:— ?
I '14:— 50,255
I '14:— 91,152M '18:— ?M'19:— 16,315I '20:— 1,387M'20:— 98,770
Other IntermediatesUsed and Notes
[Spirit BlueorTriphenyl-p-rosaniline+di-phenyl-rosanilinesulfonated]
oro-Toluidinep-ToluidineAniline (3-5 mols)[Sulfonation]
[Triphenyl-p-rosanilinemono- and di-sulfo-nated]
oro-Toluidinep-ToluidineAniline (4 mols)[Sulfonation]
[Triphenyl-p-rosanilinedi- and tri-sulfonatcd]
oro-Toluidinc2)-ToluidineAniline (4 mols)[Di-and Tri-sulfonation]
[Spirit Blue or Tri-ph enyl-p-rosanilinc+diphenyl-rosanilincdi- and tri-sulf onatcd]
oro-Toluidinep-ToluidineAniline (3-5 mols)[Di- and tri-sulfonation]
DyeAppli-cationClass
A
A
B
A
DYES CLASSIFIED BY INTERMEDIATES 99
Dyes Derived from Aniline {continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
540
TRIPHENYL-ME THANEDYES {continued)
Pacific Blue
541 Brilliant DianilBlue 6G
572XANTHONE DYES
Rhodaminc G
580 Fast Acid Violet B
606ACMDINE DYE
Phosphine
'14:-'20:-
2,648517
I '14:-M '19:-I '20:-
20,688
2,907
I '14:—168,175M'17M'18M'19I '20M'20
14,64819,259
[p-Rosanilinc+diamino-diphcnyl-methaneand sulfonation]
oro-Toluidinep-ToluidineDiamino-diphenyl-
methane[Sulfonation]
[/3-Naphthyl-rosanilinesulfonatcd]
or/3-Naphthylamine
(3 mols)o-Toluidinep-Toluidine[Disulfonation]
[Rhodamine B heatedwith aniline to re-move one C2H5 group]
orPhthalic anhydrideDiethyl-m-amino-
phenol (2 mols)
[Dichloro-fluoresceineand aniline or p-tol-
uidine; sulfonation]or
Aniline (2 mols)Phthalic AnhydrideResorcinol[PC1B; Sulfonation]
[Magenta by-product]or
p-Toluidinco-Toluidine
D
B
B
100 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Aniline (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
622OXAZINE DYES
Delphine Blue B M'17:— ?M'18:— ?M'19:— 43,827I '20:— 29,643M'20:— 76,719
630
640
646
Cyanazurine
Modern Azurine DH
Coreine AR
672AZINE DYES
Azo Carmine G I '14:— 17,500M'17:-M'18:-M'19:-I '20:-
M'20:• :— 196
673 Azo Carmine B I '20:— 549
Nitroso-dimethyl-aniline
Gallic Acid[Sulfonation]
or[Gallocyanine treated
with aniline; Sulfo-nation]
Nitroso-dimethyl-aniline
Gallamide[Reduction]
Gallic Acid MethylEster
Nitroso-dimethyl-aniline
GallamideNitroso-diethyl-aniline
or Diethyl-amino-azo- benzene
[Sulfonation]or
[Coreine RR; Sulfona-tion]
Aniline (3 mols)a-Naphthylamine[Disulfonation]
Aniline (3 mols)a-Naphthylamine[Trisulfonation]
M
M
M
M
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Aniline (continued)
101
SchultzNumberfor Dye
Ordinary Name andClass of Dye
AZINE DYES(continued)
Rosinduline 2G
Rosinduline G
Safranine
MethyleneViolet BN
Nigramino
Safranine MN
Brilliant RhodulineRed
Amethyst Violet
I '14:— 59,921M'17:— ?M ' 1 8 :M'19:-I '20:-
M'20:-
Statistics ofImport and
Manufacture
I J20:— 201
I '20:— 40
-106,591-131,042- 386-149,629
I '14:-M'17:-I '20:-
1,521?
33
I '14:-M'lS:-M'19:-M '20:
198???
Other IntermediatesUsed and Notes
Aniline (3 mols)a-Naphthylamine[Trisulfonation; heated
to 160°]
Aniline (2 mols)l-Mtroso-2-naphthyl-
amine-6-sulfonic Acid
p-Tolylcne-diamineo-Toluidine
Aniline (2 mols)Dimethyl-p-phenylene-
diamine[Oxidation]
Nitroso-dimethyl-aniline
Dimethyl-p-phcnylene-diamine
o- or p-Toluidine[Oxidation]
N3-Ethyl-4-m-tolylcne-diamine
Methyl-o-toluidine
D icthyl-p-ph cny lcnc-diamine
Diethyl-aniline[Oxidation]
102 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Aniline (continued)
Schultz-Numberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
687
693
AZINE DYES(continued)
Eosolane O
RosolaneMauve
Milling Bluo
696
697
698
Indamine Blue
Induline, SpiritSoluble
Nigrosine, SpiritSoluble
699 Induline, WaterSoluble
I '20:— 1,083
I '14:-I '20:
7963
I '14:— 3,082
'14:— 25,342M'17:— ?M'18:— 8,589M'19:—436,201M'20:—140,400
I '14:—186,595M'17:—302,706M'18:—314,151M'19:—346,167M'20:—919,242
I '14:— 29,177M'17:—183,739M ;18:— 91,724M '19:—130,704I '20:— 500
M'20.-168,048
p-Amino-diphcnyl- Bamine
o-Toluidine[Oxidation]
Toluidines (3 mols) B[Oxidation]
Aniline (3 mols) Ma-Naphthylamino
(2 mols)[Sulfonation]
orAniline (2 mols)Phenyl-a-naphthyl-
amine (2 mols)Phenol[Sulfonation]
Aniline (excess) BAmino-azo-benzcne
Aniline (excess) ssAmino-azo-benzcne
Aniline (excess)Nitro-benzene[Iron]
orAniline (excess)Nitro-phcnol
Aniline (excess)Amino-azo-benzcne[Sulfonation]
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from. Aniline (continued)
103
SchultzNumberfor Dye
700
702
719
729
851
857
Ordinary Name andClass of Dye
AZINE DYES
(continued)Nigrosine, Water
Soluble
Para Blue
SULFUR DYESThional Black
Kryogcnc PureBlueE
ANTHRAQUINONE ANDALLIED DYES
Alizarin DirectBlueB
Erweco AlizarinAcid Blue R
Statistics ofImport and
Manufacture
I '14:—398,112M'17:—
1,968,458M'18:—
1,191,343M'19:—
1,660,149I '20:— 501M'20:—
2,743,021
I '14:—• 16,865
I '14:-- 10,201I '20:— 2,982
Other IntermediatesUsed and Notes
Aniline (excess)Nitrobenzene[Iron; Sulfonation]
orAniline (excess)Nitro-phenol[Sulfonation]
Aniline (3-4 mols)o-Toluidinep-Toluidincp-Phenylcne-diaminc
or[Spirit Blue and p-
Phcnylcno-diamino]
p- (o- or m-)Nitro-ani-
linco-Nitro-phcnol (2 mols)[Na,S+S]
Aniline (2 mols)Dimcthyl-p-phenylenc-
diamine[Na«S+S]
or[Mctliylcnc Violet;
S, Na2S]
1:5- (and 1:8-) Amino-anthraquinonc-sul-fonic Acid
[Dibromination, Sulfo-nation]
Dinitro-anthraflavin-disulfonic Acid
Aniline (2 mols)[Sulfonation]
DyeAppli-cationClass
A
B
S
s
A
ACr
104 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Aniline (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
861
862
864
874
876
ANTHRAQUINONE ANDALLIED DYES
(continued)Anthraquinone
Blue SR
Alizarin BlueBlack B
AnthraquinoneGreen GX
INDIGO GROUP
DYESIndigo
Indigo MLBIndigo White
:— 917
I '14:— 54,706I '20:— 28,802
I '14:I '20:
1,7092,531
I '14:—8,507,359
M '17:—274,771M ' l S : —
3,083,888M>19:—
8,863,824I '20:—520,347
M'20:—18,178,231
Aniline (2 mols)Tetrabromo-1: 5-di-
amino-anthraquinone[Sulfonation]
Purpurin [or throughAlizarin, or 2-Anthra-quinone-sulfonic acid]
[Sulfonation]
1-Nitro-anthraquinone-6-sulfonic Acid
[Halogenation]p-Toluidine
Aniline (2 mols)[Chloro-acetic, Soda-
mide][or CS2, KCN, etc.]
Aniline (2 mols)[Chloro-acetic, Soda-
mide, Reduction][or CSs, KCN, etc.,
Reduction][or Indigo, Reduction]
ACr
M
ACr
V
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Aniline (continued)
105
SchultzNumberfor Dye
877
878
879
880
881
882
883
884
885
Ordinary Name andClass of Dye
INDIGO GROUP DYES(continued)
Indigotine
Indigotine P
Brom IndigoRathjen
Indigo MLB/RR
Helindone Blue BBIndigo RB
Dianthrene Blue 2BBromo IndigoCiba Blue 2B
Indigo MLB/5BCiba Blue G
Indigo MLB/6B'Indigo KG
Brilliant IndigoBASF/2B
Brilliant IndigoBASF/B
IM
M
M
IM
IM
IMM
IMI
II
II
M
I
II
Statistics ofImport andManufacture
'14'17
'18
'19
:— 19,329:—1,876,787
:—1,434,703
:—1,699,670
'20:— 5,512'20
'14'20
'14'17'20
'14'19'20
'14'20
'14'20'20
'14
'14'20
:—1,395,000
:— 53,610. ?
:— 6,856:— 14,100:— ?
:— 16,880:— ?:— 35,857
:— 1,356:— 1,008
:— 3,191:— 4,130:— ?
:•— 4,518
:— 8,175:— 3,503
Other IntermediatesUsed and Notes
Aniline (2 mo Is) etc.[or Indigo, Sulfonation]
Aniline (2 mols), etc.[or Indigo, Sulfonation]
Aniline (2 mols), etc.[or Iodigo, Bromination]
Aniline (2 mols), etc.[or Indigo, Bromination
Aniline (2 mols), etc.[or Indigo, Bromination'
Aniline (2 mols), etc.[or Indigo, Bromination
Aniline (2 mols), etc.[or Indigo, Bromination
Aniline (2 mols), etc.[or Indigo, Chlorination,
Bromination]
Aniline (2 mols), etc.ror Indigo, Chlorination]
DyeAppli-cationClass
A
A
V
V
V
V
V
V
V
106 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Aniline (continued)
SchultzNumberfor Dye
SS6
889
890
922
Ordinary Name andClass oj Dye
INDIGO GKOUP DYES(continued)
Brilliant IndigoBASF/G
Indigo Yellow 3G
Ciba Yellow G
ANILINE BLACKGROUP
Aniline Black
Statistics ofImport and
Manufacture
I '14:-- 12,057
I '14:—- 48
I '14:— 1,470M'19:— ?M'20:— ?
Other IntermediatesUsed and Notes
Aniline (2 mols), etc.[or Indigo, Chlorination,
Bromination]
Aniline (2 mols), etc.Benzoyl chloride[or Indigo, Benzoyl
chloride]
Aniline (2 mols), etc.Benzoyl Chloride[Bromination][or Indigo Yellow 3G,
Bromination]
Aniline (x mols)[Oxidation on fiber]
DyeAppli-cationClass
V
V
V
MF
Aniline-2: 4-disulfonic AcidSee} 4-Amino-m-benzene-disulfonic Acid
Aniline-2: 5-disulfonic AcidSee, 2-Amino-p-benzene-disulfonic Acid
Aniline-^-sulfonic AcidSee, Sulfanilic Acid
2-Anilino-5-amino-&enzene-sulfonic Acid (C A. nomen.)
See, p-Amino-diphenylamine-2-sulfonic Acid
4-(^-Anilino-anilino)-o-cresol ((7. A. nomen.)See, 4-Phenylamino-4/-hydroxy-(plieiiyl-3/-tolylamme)
)-phenol (C. A. nomen.)/See, 4-Phenylamino-4/-hydroxy-diphenylamine
DYES CLASSIFIED BY INTERMEDIATES 107
Anilino-benzene-sulfonic Acid (C. A. nomen.)
See, Diphenylamine-sulfonic Acid
8-Anilino-5-(j5>-hydroxy-anilino)-l-naphthalene-sulfonic Acid(C. A. nomen.)
See, 4-(p-Hydroxy~phenyl~amino)-l-phenylamino~naphtha-lene-8-sulfonic Acid
8-Anilino-l-naphthalene-sulfonic Acid (C. A. nomen.)
See, Phenyl-l-naphthylamine-8-sulfonic Acid
7-Anilino-l-7iaphthol-3-sulfonic Acid (C A. nomen.)
See, Phenyl-gamma Acid
m-Anilino-j&henol (C. A. nomen.)
See, m-Hydroxy-diphenylamine
2-Anilino-3-^seudoindolone (C. A. nomen.)
See, 2-Isatin Anilide
Aniline Salt
Note.—This is Aniline Hydrochloride.
See, Aniline
o-Anisidine
NH2
f jOCH 3 _ C 7 H f l N 0 = 123
STATISTICS.—Imported '14:—1,411 lbs.Manufactured '18:— ?Manufactured ;19:— ?Manufactured '20:— ?
FORMATION.—o-Nitro-anisole is reduced at 100-110° by means of iroand hydrochloric acid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 71
108 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from o-Anisidine
SchultzNumberfor Dye
93
94
95
96
259
Ordinary Name andClass of Dye
MONOAZO DYESPigment Purple ASudan R
Azo Eosine
Azo CochinealCochineal Scarlet B
Chrome FastYellow GG
DISAZO DYEPonceau 10 RB
Statistics ofImport and
Manufacture
I '14:— 99
I '14:—1,001M'18:— ?M'19:— ?
I '14:— 952
I '14:— 150I '20:— 500
I '14:— 201
Other IntermediatesUsed and Notes
/^Naphthol
Nevile Winther Acid
l-Naphthol-4:8-disulfonic Acid
Salicylic Acid
Sulfanilic AcidCroceine Acid
DyeAppli-cationClass
CL
A
A
M
A
Anthracene
178
STATISTICS.—Imported '14:—$37,240 in valueManufactured '17:— ?Manufactured '18:— 225,552 lbs.
Manufactured '19:—1,381,944 lbs.Imported '19:— 51,895 lbs.
Manufactured '20:— 711,258 lbs.Imported '20:— 648,095 lbs.
FORIMATION.—From coal-tar by extraction and purification
LITERATURE.—Cain, Intermediate Products (2d Ed.), 244
USES.—For manufacture of anthraquinone and anthraquinone deriva-tives
DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from Anthracene
109
SchultzNumberfor Dye
791
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
IndanthrcneOlive G
Statistics ofImport and
Manufacture
I J20:—11M'18:— ?
Other IntermediatesUsed and Notes
[Sulfur]
DyeAppli-cationClass
V
Anthrachrysone
1:3:5:7-Tetrahydroxy-anthraquinone
HO
CO 0 H
^0 — CuHsOe = 272
FORMATION.—From 3: 5-Dihydroxy-benzoic acid by heating with con-centrated sulfuric acid
LITERATURE.—Ullmann, Enzy. tech. Chemie, 1, 483Beil. I l l , 436; I I I spl. 312
Dyes Derived from Anthrachrysone
SchultzNumberfor Dyes
790
796
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Acid AlizarinBlue BB
Acid AlizarinGreen G
Statistics ofImport and
Manufacture
I '14:—26,642I '20:— 3,539
I '20:— 1,334
Other IntermediatesUsed and Notes
[Sulfonation, Nitration,Reduction, etc.]
[Sulfonation, Nitration,Sodium sulJide reduc-tion]
DyeAppli-cationClass
ACr
ACr
1:9-Anthradiol (C. A. nomen.)
See, 1-Hydroxy-anthranol
110 DYES CLASSIFIED BY INTERMEDIATES
Anthraflavic Acid2:6-Dihydroxy-anthraquinone (not considered herein)
Anthranilic Acid ((7. A. nomen. COOH^l)
o-Amino-benzoic Acid
COOH
STATISTICS.—Imported '14:— 106 lbs.Manufactured '17:— ?Manufactured '18:—11,826 lbs.Manufactured '19:—22,976 lbs.Manufactured '20:— ?
FORMATION.—Phthalic anhydride is melted and heated to 240°, where-upon ammonia gas is introduced, forming phthalimide. Thislatter is treated with sodium hypochlorite, forming anthranilicacid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 147Lange, Zwischenprodukte, #357-367, 1619
Dyes Derived from Anthranilic Acid
SchulteNumberfor Dye
200
201
202
Ordi ary Name andClass of Dye
MONOAZO DYESLake Red D
Pigment Scarlet G
Acid Alizarin Red BPalatine Chrome
RedB
Statistics ofImport and
Manufacture
I '14:— 2,428M'17:— ?M'18:— ?M'19:— ?M'20:— ?
M'17:— ?M'18:— ?M'19:— ?
I '14:— 7,374M'18:— ?M'19:—28,081I '20:— 1,342M'20:—67,817
Other IntermediatesUsed and Notes
0-Naphthol
Schaeffer's Acid
R-Acid
DyeAppli-cationClass
CL
CL
ACrCL
DYES CLASSIFIED BY INTERMEDIATES 111
Dyes Derived from Anthranilic Acid (continued)
SchulizNumberfor Dye
832
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
IndanthreneViolet RN
Statistics ofImport and
Manufacture
I '141—11,667I '20:— 49
Other IntermediatesUsed and Notes
Anthranilic Acid(2 mols)
1:5-Dichloro-anthraqui-none
DyeAppli-cationClass
V
Anthrano
See, 9-Anthrol
Anthraquinone
.CO.
STATISTICS.—Imported '14:— 29,850 lbs.
Manufactured '18:— ?
Manufactured '19:—294,260 lbs.
Manufactured '20:—539,619 lbs.
FOKMATION.—(1) From anthracene by appropriate oxidation means;for example, chromic acid. (2) From o-benzoyl-benzoic acid byaction of sulfuric acid. The o-benzoyl-benzoic acid is preparedby reacting together phthalic anhydride, benzene and aluminumchloride
LITERATUKE.—Cain, Intermediate Products (2d Ed.), 244Lange, Zwischenprodukte, #23, 648, 3065-3080
112 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from Anthraquinone
SchultzNumberCOT Dye
863
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
AnthraquinoneBlue Green BXO
Statistics ofImport an i
Manufacture
I'14:—6,552I'20:— 849
Other IntermediatesUsed and Note^
m
DyeAppli-cationClass
A
Note.—Most of the dyes listed in the class ''Anthraquinone and AlliedDyes" (Schultz, #758-878) are derived indirectly from anthraquinone.These dyes are, however, not tabulated under anthraquinone, but under thatintermediate from which directly derived.
Anthraquinone-1: 5-and-l: 8-disulfonic Acids
Rho Acid is trivial name for the 1:5-disulfonic Add
Chi Acid is trivial name for the 1:8-disulfonic Acid
SO3H HO3S n n SO3H
= C14H8O8S2 = 368
STATISTICS.—^The anthraquinone-1: 5-disulfonate was manufactured in1918, 1919, 1920 by one company. Amount was not disclosed
FORMATION.—Anthraquinone is sulfonated with strong oleum in thepresence of mercury or mercuric oxide to a mixture of the 1: 5- and1:8-disulfonic acids, which are separated by crystallization
LITERATURE.—Cain, Intermediate Products (2d Ed.), 252Lange, Zwischenprodukte, #3290-3293
USES.—The 1:5-acid is employed for making anthrarufin, 1:5-dichloro-anthraquinone, etc.
Anthraquinone-2:6-disulfonic Acid
a-Anthraquinone-disulfonic Acid
H ° 3 S C \ C O X ) S O 3 H= C14H8O8S2== 368
DYES CLASSIFIED BY INTERMEDIATES 113
FOKMATION.—From anthraquinone by heating with 45 per cent oleumto 160-170° C , dilution with water, neutralization with causticsoda and evaporation until the 2: 6 acid crystallizes out (2: 7 acidin mother liquor)
LITERATURE.—Cain, Intermediate Products (2d Ed.), 253Lange, Zwischenprodukte, #3290
Dyes Derived from Anthraquinone-2:6-disulfonic Acid
£ • § 1 " " S E X - "
785
786
ANTHRAQUINONE ANDALLIED DYES
Alizarin GIFlavopurpurin
Alizarine Red 3WS
Statistics ofImport and
Manufacture
I '14:—49,021
Other IntermediatesUsed and Notes
[Alkaline Fusion]
[Alkaline fusion,sulfonation]
DyeAppli-cationClass
M
M
Anthraquinone-2:7-disulfonic Acid
/3-Anthraquinone-disulfonic Acid
STATISTICS.—Manufactured ; 19:— ?
Manufactured '20:— ?
FORMATION.—From anthraquinone by heating with 45 per cent Oleum,dilution with water, neutralization with caustic soda, and evapora-tion until the 2: 6 disulfonic acid crystallizes out. The 2: 7 disul-fonic acid is then obtained (as sodium salt) by evaporating thismother liquor to dryness
LITERATURE.—Cain, Intermediate Products (2d Ed.), 253
Lange, Zwischenprodukte, #3290
114 DYES CLASSIFIED BY INTERMEDIATES
SchultzNumberfor Dye
784
Dye Derived from
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Alizarin SXIsopurpurin
Anthraquinone-2:7-disulfonic Acid
Statistics ofImport and
Manufacture
I '14:—14,273M'19:— ?I '20:— 49M'20:— ?
Other IntermediatesUsed and Notes
[Alkaline fusion]
DyeAppli-cationClass
M
a-Anthraquinone-disulfonic Acid
See, Anthraquinone-2: 6-disulfonic Acid
/3-Anthraquinone-disulfonic Acid
See, Anthraquinone-2: 7-disulfonic Acid
Anthraquinone-2-sulfonic Acid
Anthraquinone-jS-sulfonic Acid
j8 Acid or Beta Acid
Silver salt (Sodium derivative)
0-Sulfonic Acid
SO3H
STATISTICS.—^Manufactured 1918:— ?Manufactured 1919:— ?Manufactured 1920:— ?
FORMATION.—From anthraquinone by sulfonating with an equalweight of 45-50 per cent oleum and heating up to 160° C , diluting,neutralizing with caustic soda, and evaporating to crystallizationof the sodium salt ("Silver salt")
LITERATURE.—Cain, Intermediate Products (2d Ed.), 251Lange, Zwischenprodukte, #3156-3163
SchultzNumberfor Dye
778
779
780
781
783
787
788
797
798
799
854
862
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Alizarin
Alizarin Orange
Alizarin Red
Erweco AlizarinAcid Red BS
Purpurin
Alizarin Bordeaux B
Alizarin Cyaninc R
Alizarin Garnet R
Alizarin Maroon W
Alizarin Cyanine G
Alizarin Viridine DG
Alizarin BlueBlack B
Statistics ofImport and
Manufacture
I 14:—202,392M17:— ?M18:— ?M19:— ?I '20:— 8,575M'20:— ?
I 14:— 14,239M19:— ?I '20:— 500M'20:— ?
I 14:— 81,919M17:— ?I '20:— 12,628
I '20:— 20
I '20:— 16,781
I 14:— 720
I '20:— 2,014
I '20:— 339
I '20:— 11,397
I 14:— 54,706I '20:— 28,802
Other IntermediatesUsed and Notes
[Oxidation]
[Alizarin, Nitration]
[Alizarin, Sulfonation]
[Alizarin, Sulfonation]
[Alizarin, Oxidation]
[Alizarin, Oxidation]
[Alizarin Bordeaux B,Oxidation]
[4-Nitro-alizarin, Re-duction]
[Crude Nitro-alizarin,Reduction]
[Alizarin Cyanine R,Amidation]
[Alizarin Bordeaux B]p-Toluidine (2 mols)[Sulfonation]
[Purpurin]Aniline[Sulfonation]
DyeAppli-cationClass
M
M
M
M
M
M
M
M
M
M
M
M
116 DYES CLASSIFIED BY INTERMEDIATES
Anthraquinone-/3-sulfonic Acid
See, Anthraquinone-2-sulfonic Acid
2-Anthraquinone-urea Chloride
See, 2-Anthraquinonyl-urea Chloride
2-Anthraquinonyl-urea Chloride
2-Anthraquinone-urea Chloride
. CO. Cl
FORMATION.—From 2-Amino-anthraquinone in nitro-benzene solutionby action of phosgene at 50°
LITERATURE.—Lange, Zwischenprodukte, #3123
Dyes Derived from 2-Anthraquinonyl-urea Chloride
SchultzNumberfor Dye
835
836
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
HelindoneOrange GRN
HelindoneBrown 2GN
Statistics ofImport and
Manufacture
I '20:— 74
I '20:—15,238
Other IntermediatesUsed and Notes
2-Anthraquinonyl-ureachloride (2 mols)
2-Anthraquinonyl-urcachloride (2 mols)
Diamino-anthraqui-noncs, [various]
DyeAppli-cationClass
V
V
Anthrarufin
1:5-Dihydroxy-anthraquinone
CO. 0 H
HO
DYES CLASSIFIED BY INTERMEDIATES 117
STATISTICS.—Manufactured 1918:— ?Manufactured 1919:— ?Manufactured 1920:— ?
FORMATION.—This compound is obtained by the action of milk of limeon either anthraquinone-1: 5-disulfonic acid or on 1: 5-dinitro-anthraquinone
LITERATURE.—Cain, Intermediate Products (2d Ed.), 257Ullmann, Enzy. tech. Chemie, 1, 481Lange, Zwischenprodukte, #3269, 3272, 3287
Dye Derived from Anthrarufin
SchultzNumberfor Dye
858
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Alizarin Saphirol B
Statistics ofImport and
Manufacture
M'18:— ?M;19:— ?I '20:— 28,210M'20:— ?
Other IntermediatesUsed and Notes
[Sulfonation, Nitration,Reduction]
DyeAppli-cationClass
ACr
1-Anthrol (C. A. nomen.)a-Anthrol
1-Hydroxy-anthracene
OH
FORMATION.—Prom 1-anthracene-sulfonic acid by fusion with 5 partsof caustic soda at about 250°
LITERATURE.—Schmidt, Ber. 37, 66 (1904)Thorpe, Die. Chemistry, 1, 274; (1921 Ed.), 1, 352
Dye Derived from 1-Anthrol
SchultzNumberfor Dye
893
Ordinary Name andClass of Dye
INDIGO GROUP DYEAlizarin Indigo G
Statistics ofImport and
Manufacture
I'20:—1,596
Other IntermediatesUsed and Notes
Dibromo-isatin chloride
DyeAppli-cationClass
V
118 DYES CLASSIFIED BY INTERMEDIATES
9-Anthrol (C. A. nomen.)
9-Hydroxy-anthracene
Anthranol
OH
FORMATION.—Anthraquinone is reduced with tin in boiling glacialacetic acid solution, or with iron and ferrous chloride solution
LITERATUKE.—Cain, Intermediate Products (2d Ed.), 262Thorpe, Die. Chemistry, 1, 272; (1921 Ed.), 1, 349Lange, Zwischenprodukte, #3038-3040
Dyes Derived from 9-Anthrol
SchulizNumberfor Dye
763
764
765
872
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
IndanthreneDark Blue BO
IndanthreneViolet RT
IndanthreneGreen B
Leucol Brown B
Statistics ofImport and
Manufacture
I '14:—11,096I '20:—13,917
M'20:— ?
I '14:—72,251M'19:— ?I '20:— 6,765M'20:— ?
I '20:— 22
Other IntermediatesUsed and Notes
9-Anthrol (2 mols)[Glycerol (2 mols)]
9-Anthrol (2 mols)[Glycerol (2 mols),Halogcnation]
or[Indanthrene Dark BlueBO and Halogenation]
9-Anthrol (2 mols)[Glycerol (2 mols),
Nitration]or
[Indanthrene Dark BlueBO and Nitration]
DyeAppli-cationClass
V
V
V
V
Armstrong's Acid
See, Naphthalene-1: 5-disulfonic Acids
DYES CLASSIFIED BY INTERMEDIATES 119
Armstrong's 8 Acid
See, Naphthalene-1: 5-disulfonic Acid
Armstrong and Wynne's Acid
l-Naphthol-3-sulfonic Acid (not considered herein)
Armstrong and Wynne's Acid II
See, 2-Naphthylamine-5: 7-disulfonic Acid
5: 6'-A oxy-bis-o-foluidine (C. A. nomen.)
See, Diamino-azoxy-toluene
^-Azoxy-o-toluidine
See, Diamino-azoxy-toluene
B Acid
See, l-Amino-8-naphthol-3: 5-disuIfonic Acid
This trivial name also applied to
l-Amino-7-naphthol-3-sulfonic Acid
2: 3-Dihydroxy~naphthalene-6: 8-disulfonic Acid
Badische Acid
See, 2-Naphthylamine-8-sulfonic Acid
Baum's Acid
l-Naphthol-2-sulfonic Acid (not considered herein)
Bayer's Acid
See, Croceine Acid
See, 2-Naphthylamine-7-sulfonic Acid
Benzal-bisxylidine (C. A. nomen.)
Seey Diamino-dixylyl-phenyl-methane
120 DYES CLASSIFIED BY INTERMEDIATES
Benzaldehyde
HCO
STATISTICS.—Imported '14:— 20,475 lbs.Manufactured ' 17:—132,336 lbs.Manufactured '18:—360,591 lbs.Manufactured '19:—518,634 lbs.Manufactured '20:—702,543 lbs.
FOEMATION.—(1) From toluene by chlorination to benzylidine chloride,C6H5CHCI2, and by heating this with milk of lime under pressure.(2) From toluene by oxidation with manganese dioxide andsulfuric acid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 138Lange, Zwischenprodukte, #20-41
Dyes Derived from Benzaldehyde
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
495
TRIPHENYL-METHANE DYES
Malachite Green
499 Brilliant Green
I '14:—183,852M '17:—130,229M'18.-290,416M'19—560,301I '20— 100M'20:—654,237
I '14— 73,904M'18M'19I '20M'20
>— 25
502 Guinea Green BAcid Green 3BG
I '14— 49,971M'17— ?M'18 — ?M'19 — ?I '20M>20
Dimethyl-aniline(2 mols)
[Oxidation]
Diethyl-aniline (2 mols)[Oxidation]
Ethyl-sulfobenzyl-aniline (2 mols)
[Oxidation]
B
B
i— 278
DYES CLASSIFIED BY INTERMEDIATES 121
Dyes Derived from Benzaldehyde (continued)
SchultzNumberfor Dye
504
505
604
605
Ordinary Name andClass of Dye
TRTPHENYL-METHANEDYES (continued)
Light Green SFBluish
Light Green SFYellowish
ACRIDINE DYESAcridine Orange R
Benzoflavine
Statistics ofImport and
Manufacture
I J14:M'17:M'18:-
6,693??
I '14:— 71,462M ' 1 9 : - - ?I '20:— 7,490
M'20:— ?
I '14:— 600
Other IntermediatesUsed and Notes
Benzyl-methyl-aniline (2 mols)
[Sulfonation andOxidation]
Benzyl-ethyl-aniline (2 mols)
[Sulfonation andOxidation]
Dimethyl-m-phenylene-diamine (2 mols)
[Ammonia removal;Oxidation]
m-Tolylene-diamine(2 mols)
[Ammonia removal,Oxidation]
DyeAppli-cationClass
B
B
Benzaldehyde-disulfonic Acid
4-Formyl~m-6enzene-disulfonic Acid (C. A. nomen.)
H C O
SO3H
FORMATION.—Toluene is sulfonated wi th oleum to t he 2 : 4-disulfonicacid, which is then oxidized wi th manganese dioxide
L I T E R A T U R E . — L a n g e , Zwischenprodukte, #899
122 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from Benzaldehyde-disulfonic Acid
SchultzNumberfar Dye
579
Ordinary Name andClass of Dye
XANTHONE DYESSulfo Rhodamine BXylene Red B
Statistics ofImport and
Manufacture
I '14:—1,698
Other IntermediatesUsed and Notes
Diethyl-m-amino-phenol (2 mols)
{Oxidation]
DyeAppli-cationClass
A
Benzaldehyde-o-sulfonic Acid
o-Formyl-frenzene-sulfonic Acid (C A. nomen.)
HCO
FORMATION.—By heating o-chloro-benzaldehyde with Na2SO3 at around170-180° under pressure
LITERATURE.—Cain, Intermediate Products (2d Ed.), 146Lange, Zwischenprodukte, #504-506
Dyes Derived from Benzaldehyde-o-sulfonic Acid
SchultzNumberfor Dye
506
553
Ordinary Name andClass oj Dye
TRIPHENYL-METHANE DYES
Erioglaucine
EriochromeCyanine R
Statistics ofImport and
Manufacture
I '14:—66,526M'19:~ ?I '20:— 6,160M'20:— ?
I '14:— 2,249I '20:— 2,205
Other IntermediatesUsed and Notes
Ethyl-sulfobcnzyl-aniline
orBenzyl-ethyl-aniline
(2 mols) [and sulfona-tion]
[Oxidation]
o-Cresotic Acid (2 mols)[Oxidation]
DyeAppli-cationClass
A
ACr
DYES CLASSIFIED BY INTERMEDIATES 123
Benzamido- (C. A. nomen. for ft H&CO. N H)
See, Benzoylamino-
Note.—The C. A. name for this radical is the scientific one, and it is listedas an alternate, but in view of the widespread use of benzoylamino-, thelatter is given precedence at the present time.
l-Benzamido-4-chloro-anthraquinone (C. A. nomen.)
See, 1-Benzoylamino^-chloro-anthraquinone
7-meso-Benzanthren-7-one (C. A. nomen.)
See, Benzanthrone
Benzanthrone
7~meso-Benzanthren-7-one (C. A. nomen.)
STATISTICS.—Manufactured J19:— ?
Manufactured '20:— ?
FORMATION.—(1) From anthranol and glycerol by condensation bymeans of sulfuric acid. (Anthranol is made from anthraquinone.)(2) From anthracene in sulfuric acid solution, by addition of glyceroland heating to 100-110° C. until the anthracene disappears. Thereaction mass is then diluted with water, salted out and purified
LITERATURE.—Cain, Intermediate Products (2d Ed.), 262Lange, Zwischenprodukte, #3584
124 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Benzanthrone
SchvltzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Ustd and Notes
DyeAppli-cationClass
763
764
765
ANTHRAQUINONE ANDALLIED DYES
IndanthreneDark Blue BO
IndanthreneViolet RT
IndanthreneGreen B
I '14:— 11,096I ;20:— 13,917
I '14:—72,251M'19:— ?I '20:— 6,765M'20:— ?
Benzanthrone (2 mols)
Benzanthrone (2 mols)[Halogenation][or Indanthrene Dark
Blue BO and halo-genation]
Benzanthrone (2 mols)[Nitration][or Indanthrene Dark
Blue BO and Nitra-tion]
Benzanthrone-quinolinePhenanthroquinolinone (C A. nomen.)
O
FORMATION.—From 2-amino-anthraquinone and glycerol by warmingwith condensing agents, for example, sulfuric acid
LITERATURE.—Lange, Zwischenprodukte, #3596Ullmann, Enzy. tech. Chemie, 3, 314
Dye Derived from Benzanthrone-quinoline
SchultzNumberfor Dye
846
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Indanthrene DarkBlue BT
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
Benzanthrone-quino-line (2 mols)
DyeAppli-cationClass
V
DYES CLASSIFIED BY INTERMEDIATES
Benzene-azo-diethylaniline
See, p-Diethylamino-azo-benzene
Benzene-sulfonyl Chloride
SO2C1
= 176.5
125
FORMATION.—From benzene-sulfonic acid by treatment with phos-phorus pentachloride
LITERATURE.—Bucherer, Farbenchemie, 78, 150
Dye Derived from Benzene-sulfonyl Chloride
SchultzNumberfor Dye
182
Ordinary Name andClass of Dye
MONOAZO DYEFast SuLfon VioletBrilliant Sulfon
RedB
Statistics ofImport and
Manufacture
I '14:—4,871I '20:—4,740
Other IntermediatesUsed and Notes
H AcidAniline
DyeAppli-cationClass
A
Benzidine
H2N«
STATISTICS.—Imported '14:— 55,245 lbs.Manufactured '17:—1,766,582 lbs.Manufactured 718:—2,501,887 lbs.Manufactured '19:—1,319,629 lbs.Manufactured '20:—2,183,583 lbs.
FORMATION.—Nitro-benzene is reduced to hydrazo-benzene with zincor iron in presence of caustic soda; the hydrazo-benzene is re-arranged to benzidine by treatment with acid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 89Lange, Zwischenprodukte, #1204
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Benzidine
SchulteNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
MONOAZO DYESChicago Orange G
Diamond Flavine G
Dutch Yellow
DISAZO DYESPyramine Orange 3G
Congo Red
Diazo Black B
Glycine Red
Glycine Corinth
Orange TA
Congo Corinth G
I '14:— 23,089M'17:— ?M'18:— ?M'19:— ?M'20:— ?
:— 7,8630:— 396
I '14:— 20,629M'17:— ?M'18:—587,153M'19:—873,734M'20:—
1,502,630
I '14:— 62,854
p-Nitro-toluene-o-sulfonic Acid
Salicylic Acid
Salicylic Acid[Sodium sulfite]
Nitro-m-phenylene-diamine
m-Phenylene-diamine-disulfonic Acid
Naphthionic Acid(2 mols)
I '14:—M'17:—M'18:—M'19:—M'20:—
602??
??
'14:— 44,157M'17:— ?M'18.— ?M'19:—137,704M'20.-242,503
Laurent's Acid (2 mols)
a-Naphthyl-glycineNaphthionic Acid
a-Naphthyl-glycine(2 mols)
Naphthionic AcidCresol
Nevile Winther's AcidNaphthionic Acid
M
M
D
D
D
D
D
D
D
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Benzidine (continued)
127
SchultzNumberfor Dye
313
314
315
316
317
318
319
320
321
322
Ordinary Name andClass of Dye
DISAZO DYES(continued)
Congo Bubine
PyramineOrange Ml
Congo Orange G
Brilliant Congo G
PyramidolBrown BG
Benzidine Puce
Diamine Scarlet
^Bordeaux
Heliotrope 2B
TrisulfonViolet B
Statistics ofImport and
Manufacture
I '14:— 46,213M'17:— ?M'18:— ?I '20:— 2,601
I '14:— 2,789
I '14:— 1,623I '20:— 75
I '14:— 41,175I '20:— 11,340
I '14:— 1,335M'18:— ?M'19:— ?M'20:— ?
I '14:— 1,473I '20:— 60
I '14:— 1,124M'17:— ?M'18:— ?M'19:— ?I '20:— 7,927
M'20:— ?
Other IntermediatesUsed and Notes
Croceine AcidNaphthionic Acid
Nitro-m-phenylene-diamine
Amino-R Acid
PhenolAmino-R Acid[Ethylation]
Amino-R AcidBroenner's Acid
Resorcinol (2 mols)
0-Naphthol
PhenolG Acid[Ethylation]
Croccine Acid (2 mols)
Croccine Acidl-Naphthol-4: 8-
disulfonic Acid
0-Naphtholl-Naphthol-3:6:8-tri-
sulfonic Acid
DyeAppli-cationClass
D
D
D
D
D
MF
D
D
D
D
128 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Benzidine (continued)
SchultzNumberfor Dye
323
324
325
326
327
328
329
330
331
332
333
Ordinary Name andClass of Dye
DISAZO DYES(continued)
Dianil Blue R
Chicago Blue 4R
Columbia Blue R
Oxamine VioletOxydiamine Violet BF
Diamine Violet N
Diamine Black RODianol Black RW
Diamine Brown V
Zambesi Brown G
Alkali DarkBrown GV
Dianil Garnet BBenzo Fast Red
Diamine Black BHOxamine Black BHN
Statistics ofImport and
Manufacture
M'20:— ?
I 14:— 1,199
I 14:— 3,071
I 14:— 23,981I '20:— 732
I 14:— 18,263M19:— ?M'20:— 92,503
I 14:— 8,253
M19:— ?
I 14:— 4,028I '20:— 1,104
I 14:— 5,985I '20:— 3,799
I 14:—619,430M17:— ?M'18:— ?M19 :--485,046I '20:— 5,512M '20.-803,501
Other IntermediatesUsed and Notes
Chromotropic Acid(2 mols)
Croceine Acid1 -Amino-8-naphthol-4-
sulfonic Acid
l-Naphthol-3: S-disul-fonic Acid
l-Amino-8-naphthol-4-sulf onic Acid
J Acid (2 mols)
Gamma Acid (2 mols)
Gamma Acid (2 mols)
m-Phenylene-diamineGamma Acid
Gamma Acid2: 7-Naphthylene-diamine-sulfonic Acid
Nitroso-/3-naphtholGamma Acid
Gamma AcidAmino-R Acid
Gamma AcidHAcid
DyeAppli-cationClass
D
D
D
D
D
D
D
D
D
D
D
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Benzidine (continued)
SchultzNumberfor Dye
334
335
336
337
338
339
340
340 (1)
341
Ordinary Name andClass of Dye
DISAZO DYES
{continued)Diphenyl Blue
Black
NaphthamineBlack RE
Benzo Cyanine R
Diamine Blue BBBenzo Blue BB
Naphthamine Blue2B
Brilliant Orange G
Benzo Orange R
ChlorazolOrange 2R
Crumpsall DirectFast Red R
Statistics ofImport and
Manufacture
I '14:— 26,240
I '14:— 49,016
I '14:— 201
I '14:— 19,035M'17:—
1,445,059M'18:—
1,523,985M'19:—
1,380,335M'20:—
1,789,774
I '14:— 11,707I '20:— 400
I '14:— 6,321M717:— ?
I '14:— 1,073M'17:— ?M'lS:— 50,422M'19:— 42,807I '20:— 220M'20:— 86,210
M'17:— ?M'18:— ?M'19:— ?M'20:— ?
Other IntermediatesUsed and Notes
Ethyl-gamma AcidH Acid
Gamma AcidKAcid
H Acidl-Amino~8-naphthol-4-
sulfonic Acid
H Acid (2 mols)
K Acid (2 mols)
Salicylic Acid3-Amino-phenol-4-
sulfonic Acid
Salicylic AcidNaphthionic Acid
Salicylic Acid2~Naphthylamine-7-
sulfonic Acid
Salicylic AcidRSalt
DyeAppli-cationClass
D
D
D
D
D
D
D
D
D
130 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Benzidine (continued)
SchultzNumberfor Dye
342
343
344
345
346
347
348
349
350
351
Ordinary Name andClass of Dye
DISAZO DYES(continued)
Chrysamine G
Diamine FastRedF
Diamine Brown M
Oxamine Maroon
Oxamine Red
Diphenyl Brown RN
Diphenyl Brown BIS
Diamine Brown B
Alkali Yellow R
Cresotine Yellow G
Statistics ofImport and
Manufacture
I '14:— 608M'17:— 26,061M'18:— 28,846M'19:— 54,279I '20:— 9,810M'20:— 49,342
I '14:— 50,479M'19:— 56,864I '20:— 4,040M'20:—115,865
I '14:— 65,396M'18:— ?M'19:— 15,957M'20:—257,872
I '14:— 11,636I '20:— 848
I '14:— 13,471
I '20:— 24
I '14:— 1,74M'17:— ?M'18:— ?M'19:— ?M'20:— ?
Other IntermediatesUsed and Notes
Salicylic Acid(2 mols)
Gamma AcidSalicylic Acid
Salicylic AcidGamma Acid
Salicylic Acidl-Amino-5-naphthol-7-
sulf onic Acid
J AcidSalicylic Acid
Salicylic AcidMethyl-gamma Acid
Salicylic AcidDimethyl-gamma Acid
Salicylic AcidPhenyl-gamma Acid
Salicylic AcidDehydrothio-p-tolui-
dine-suHonic Acid
o-Cresotic Acid(2 mols)
DyeAppli-cationClass
D
D
D
D
D
D
D
D
D
D
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Benzidine {continued)
131
SchultzNumberfor Dye
352
353
354
438
439
440
441
442
443
444
445
Ordinary Name andClass of Dye
DISAZO DYES
{continued)Direct Violet R
Direct IndigoBlue BN
Direct Gray R
TRISAZO DYESMelogene Blue BH
Direct IndigoBlue A
Direct IndigoBlue BK
Diazo BlueBlack RS
Direct Black V
Direct IndoneBlueR
Crumpsall DirectFast Brown B
Crumpsall DirectFast Brown 0
Statistics ofImport and
Manufacture
I '14:— 661M'19:— ?
I '14:— 6,000
I '20:— 4,927
M'17:— ?M'18:— ?
M'18:— ?
M'19:— ?M'20:-~ ?
I '14.-145,738
Other IntermediatesUsed and Notes
m-Tolylene-diamineI: 7-Dihydroxy-6~naph-
thoie-3-sulfonic Acid
1: 7-Dihydroxy-6-naph-thoic-3-sulfonic Acid
H Acid
1: 7-Dihydroxy-6-naph-lhoic-3-sulfonic Acid(2 mols)
H Acid (2 mols)p-Xylidine
H Acid (2 mols)m-Amino-p-cresol
Methyl Ether
Gamma Acid (2 mols)m-Amino-p-cresol
Methyl Ether
H Acid (2 mols)a-Naphthylamine
Gamma Acida-Naphthylamine2 R Acid
a-NaphthylamineII Acid2 R Acid
Salicylic AcidAnilineGamma Acid
Salicylic AcidAnilinePhenyl-gamma Acid
DyeAppli-cationClass
D
D
D
D
D
D
D
D
D
D
D
132 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Benzidine {continued)
SchultzNumberfor Dye
446
447
448
449
462
463
464
465
Ordinary Name andClass of Dye
TRISAZO DYES(continued)
Benzo Olive
Benzo Gray S Extra
Diamine Bronze G
TrisulfonBrown B
Erie DirectBlack GX
Direct DeepBlack EW
Erie DirectBlack RX
Cotton Black E
Erie DirectGreen E T
Columbia BlackGreen D
Statistics ofImport and
Manufacture
I '14:— 1,149
I '14:— 802
I '14:— 4,495
I '14:— 16,781I '20:— 38,616
I '14:—1,246,536
M'17:— ?M'18:— ?M'19:—
7,250,007M'20:—
7,736,994
I '14:—248,567M'19:— ?M'20:—
2,050,741
M'17:— ?M'18:— ?M'19:— 69,700M'20:— ?
Other IntermediatesUsed and Notes
Salicylic Acida-NaphthylamineHAcid
Salicylic Acida-NaphthylamineNevile Winther's Acid
Salicylic AcidHAcidm-Phenylene-diamine
2 R AcidSalicylic Acidm-Phenylene-diamine
AnilineHAcidm-Phenylene-diamine
AnilineHAcidm-Tolylene-diamine
AnilineHAcidPhenol
Salicylic AcidAniline1: 8-Amino-naphthol-4-
sulfonic Acid
DyeAppli-cationClass
D
D
D
D
D
D
D
D
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Benzidine (continued)
133
SchultzNumberfor Dye
466
467
468
469
470
471
472
473
474
Ordinary Name andClass of Dye
TRISAZO DYES(continued)
Eboli Green
Diphenyl Green G
Diphenyl Green 3G
Chloramine Black N
ChloramineGreen B
Chloramine Blue 3G
ChloramineBlue HW
Diamine Black HW
Diamine Green BOxamine Green B
Statistics ofImport and
Manufacture
I '20:— 2,205
I '14:— 39,600M'19:— ?I '20:— 1,763M'20:— ?
I '14:— 1,675M'19:— ?
I '14:— 286M'19:— ?I '20:— 882
I '20:— 342
I '14:— 77,100M'17:— ?M'18:—295,147M'19:—305,854I '20:— 2,460M'20:—420,138
Other IntermediatesUsed and Notes
l-Amino-8-naphthol-3: 5-disulf onie Acid
Salicylic AcidSulfanilic Acid
PhenolH Acido-Chloro-p-nitro-
aniline
Salicylic AcidII Acid0-Chloro-p-nilro-
aniline
m-Phenylene-diamineH Acid2: 5-Dichloro-aniline
PhenolH Acid2: 5-Dichloro-aniline
H Acid (2 mols)2:5-Dichloro-aniline
Gamma AcidH Acid2: 5-Dichloro-aniline
Gamma AcidII Acidp-Nilro-aniline
PhenolH Acid7;-Nitro-aniline
DyeAppli-cationClass
D
D
D
D
D
D
1)
D
D
134 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Beuzidine (continued)
SchultzNumberfor Dye
475
476
477
478
479
480
489
490
Ordinary Name andClass of Dye
TKISAZO DYES(continued)
Diamine Green GOxamine Green G
BenzamineBrown 3GO
Congo Brown GNaphthamin*
4G
Columbia Green
Dianil Black
Congo Brown
TETEAKISAZO DYESHessian Brown BBN
Cotton Brown A
Statistics ofImport and
Manufacture
I '14:—- 7,329M'17:— ?M ;18:— 29,118M'19:—136,638I '20:— 1,332
M'20:— 53,292
I '14:— 16,988M'17:— ?M'18:— ?M'19:— ?M '20.-623,757
I '14:— 52,141e Brown M '17:— ?
M'18:— ?M'19:— ?I '20:— 443
M'20:—229,489
I '14:— 45,162M'18:— ?I '20:— 7,555
I '14:— 3,045
I '14:— 29,074
Other IntermediatesUsed and Notes
Salicylic AcidH Acidp-Nitro-aniline
Sulf anilic Acidm-Phenylene-diamineSalicylic Acid
Sulfanilic AcidResorcinolSalicylic Acid
Salicylic AcidSulfanilic Acidl-Amino-8-naphthol-4-
sulfonic Acid
Chromotropic AcidNaphthionic Acidm-Phenylene-diamine
ResorcinolSalicylic AcidLaurent's Acid
Sulfanilic Acid (2 mols)Hesorcinol (2 mols)
Naphthionic Acid(2 mols)
m-Phenylene-diamine(2 mols)
DYES CLASSIFIED BY INTERMEDIATES 135
Dyes Derived from Benzidine (continued)
SchultzNumberfor Dye
712
714
Ordinary Name andClass of Dye
SULFUR DYESKyrogene Yellow G
Thiophor YellowBronze G
Statistics ofImport and
Manufacture
I '14:— 1,126I '20:— 1,543
Other IntermediatesUsed and Notes
m-Tolylene-dithio-urea[Sulfur]
p-Phenylene-diaminep-Amino-acetanilide[Sulfur]
DyeAppli-cationClass
S
S
Benzidine-disulfonic Acid
6: e'-Diamino-mrm'-bi^enzene-sulfonic) Acid (C. A. nomen.)
4:4'-Diamino-diphenyl-3: 3'-disulfonic Acid
= C12H12N2O6S2 = 344
HO3S SO3H
FORMATION.—From benzidine sulfate by heating with 2 parts of sulfuricacid at about 210° for forty-eight hours
LITERATURE.—Cain, Intermediate Products (2d Ed.), 94Griess and Duisberg, Ber7 22, 2464 (1889)Cf. Griess, Ber., 14, 300 (1881)Cf. Farbenfabriken, Ger. Pat. 27954
Dyes Derived from Benzidine-disulfonic Acid
SchultzNumberfor Dye
360
459
460
Ordinary Name andClass of Dye
DISAZO DYEPyramine Orange R
TRISAZO DYESBenzo Black Blue G
Benzo Black Blue 5G
Statistics ofImport andManufacture
I '14:— 21,329I '20:— 7,821
I '14:— 602
Other IntermediatesUsed and Notes
Nitro~m-phenylcne-diamine
Ncvile-Winther's Acid(2 mols)
a-Naphthylamine
1:8-Dihydroxy-naph-thalene-4-sulfonic
Acid (2 mols)a-Naphthylamine
DyeAppli-cationClass
D
D
D
136 DYES CLASSIFIED BY INTERMEDIATES
Benzidine-sulfon-disulfonic Acid
4:4'-Diamino-diphenyl-2: 2'-sulfon-disulfonic Acid
2:7-Diamino-9-dioxide-? :?-dibenzothiophene-disulfonic Acid (C
A. nomen.)
2(SO3H)
= C12H10N2O8S3 = 406
FORMATION.—Benzidine sulfate is heated with 40 per cent oleum for
1 hour at 100° in an autoclave, and then at 150° until a sample
dissolves in hot water and does not give a yellow precipitate with
alkali
LITEBATUEE.—Lange, Zwischenprodukte, #1275
Dyes Derived from Benzidine-sulfon-disulfonic Acid
SchultzNumberfor Dye
361
Ordinary Name andClass of Dye
DISAZO DYESulfonazurine
Statistics ofImport and
Manufacture
I '14:—300
Other IntermediatesUsed and Notes
Plienyl-a-naphthyl-amine (2 mols)
DyeAppli-cationClass
D
Benzidine-sulfonic Acid
2-Amino-5-(p-amino-phenyl)-6enzene-sulfonic Acid (C. A. nomen
SO>H=1)
>NH2=Ci2Hi2N2O3S = 264
HO3S
DYES CLASSIFIED BY INTERMEDIATES 137
FORMATION.—From benzidine sulfate by evaporating to drynoss withdilute sulfuric acid (1J^ mols), and then heating in air bath atabout 170° for 24 hours
LITERATURE.—Ullmann, Enzy. tech. Chemie, 2, 318
Dyes Derived from Benzidine-sulfonic Acid
SchultzNumberfor Dye
359
491
Ordinary Name andClass of Dye
DISAZO DYETrypan ^ e ^
TETRAKISAZO DYEDianil Black PR
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
Amino-R Acid (2 mols)
Gamma Acid (2 mols)ra-Phcnylene-diaminc
(2 mols)
DyeAppli-cationClass
Medi-cinal
D
Benzoic Acid
COOH
= C7H6O2=:122
STATISTICS.—Imported '14:—352,201 lbs.
Manufactured '17:—219,210 lbs.
Manufactured ;18:—282,212 lbs.
Manufactured '19:—720,320 lbs.
Manufactured '20:—743,113 lbs.
FORMATION.—(1) From toluene by chlorination to benzo-trichloride,and hydrolysis with milk of lime. (2) From toluene by directoxidation with nitric acid
LITERATURE.—Ullmann, Enzy. tech. Chemie, 2, 325
e, Zwischenprodukte, #24, 59
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Benzoic Acid
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
509
520
521
770
782
TRIPHENYL-METHANE DYES
Chrome Green
Light Blue SuperfineSpirit Soluble
Diphenylamine Blue
Spirit BlueAniline Blue
I '14:— 2,149
I '14M'17M'18M'19I '20
M'20
50,563
:— 723
ANTHRAQUINONE ANDALLIED DYES
Alizarin Yellow A
Anthracene BrownAlizarin Brown
I '14:—115,586M'17M'18M'19I '20
M'20
40,4262,728
42,840
Hydrol[Oxidation]
Aniline (5 mols)p-Toluidine
or[p-Rosaniline tripheny-
lated]
Aniline (2-4 mols)o-Toluidinep-Toluidine
or[Fuchsine or Rosaniline
base phcnylated]
Pyrogallol
Gallic Acid
M
ss
ss
M
M
Benzo-trichloride
a-Trichloro-toluene (C. A. nomen.)
CC13
=C7H5C13 = 195.5
STATISTICS.—Imported ' 14:—very smallManufactured '18:— ?Manufactured '20;— ?
DYES CLASSIFIED BY INTERMEDIATES 139
FORMATION.—From toluene by treatment with chlorine, preferably inpresence of catalyst
LITERATURE.—Cain, Intermediate Products (2d Ed.), 19
Dyes Derived from Benzo-trichloride
SchultzNumberfor Dye
610
770
Ordinary Name andClass of Dye
QUINOLINE DYEQuinoline Red
ANTHBAQUINONE ANDALLIED DYES
Alizarin Yellow A
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
QuinaldincIsoquinoline
Pyrogallol
DyeAppli-cationClass
B
M
l-Benzoylamino-4-chloro-anthraquinone
l-Benzamido-4-chloro-anthraquinone (C A. nomen.)
CO NH.COC 6HS
o ^:C2iH12ClNO3 = 361.5
FORMATION.—By heating l-Amino-4-chloro-anthraquinonc with ben-zoyl chloride
LITERATURE.—Ullmann, Enzy. tech. Chcmie, 1, 164
Dye Derived from l-Benzoylamino-4-chloro-anthraquInone
SchultzNumberfor Dye
833
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Algol Olive R
Statistics ofImport and
Manufacture
I '14:— 13,334I '20:— 461
Other IntermediatesUsed and Notes
l-Bcnzoylamino-4-amino-anthraquinono
[Chloro-sulfonic acid]
DyeAppli-cationClam
V
140 DYES CLASSIFIED BY INTERMEDIATES
o-Benzoyl-6enzoic Acid
COOH
STATISTICS.—Manufactured 1920:— ?
FORMATION.—By condensation of phthalic anhydride and benzene inpresence of aluminum chloride
LITERATURE.—Heller, Zeit. angew. Chem., 19, 669 (1906)Heller, Ber., 41, 3631 (1908)Cain, Intermediate Products (2d Ed.), 249
USES.—For synthesis of anthraquinone
Benzoyl Chloride
COC1
STATISTICS.—Manufactured J17:—20,621 lbs.Manufactured '18:— 6,585 lbs.Manufactured '19:— ?Manufactured '20:—14,277 lbs.
FORMATION.—From benzoic acid by action of sulfuryl chloride
LITERATURE.—TJllmarjii, Enzy. tech. Chemie, 2, 329Lange, Zwischenprodukte, #42
Dyes Derived from Benzoyl Chloride
SchultzNumberfor Dye
814
815
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Algol Yellow WG
Algol Scarlet G
Statistics ofImport and
Manufacture
I '14:— 5,185I '20:— 4
I '20:— 959
Other IntermediatesUsed and Notes
1-Amino-anthraqui-none
l-Amino-4-methoxy-anthraquinone
DyeAppli-cationClass
V
V
DYES CLASSIFIED BY INTERMEDIATES 141
Dyes Derived from Benzoyl Chloride (continued)
chultzumber•r Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
ANTHRAQUINONE ANDALLIED DYES
(continued)Algol Red 5G
Algol Yellow R
Algol Pink R
Algol Red R
Algol BrilliantViolet 2B
Algol BrilliantOrange FR
Algol Violet B
Algol Corinth R
I '14:-I '20:-
I '14:—I '20:—M'20:—
I '14:—I '20:—
I '14:—I '20:—
1,33851
4,SS72,299
1261,368
2,3227,335
I '14:— 3,893I '20:— 827
I '14:-I '20:-
I '20:—
6,195482
69
I '20:— 134
1:4-Diamino-anthra-quinone
BonzoyJ chloride(2 mols)
1:5-Diamino-anthra-quinone
Benzoyl chloride(2 mols)
l-Amino-4~hydroxy-anthraquinone
1: 5-Diamino-anthra-quinone
Benzoyl chloride(2 mols)
[Oxidation]
Diamino-anthrarufinBenzoyl cliloride
(2 mols)
1:2: 4-Triamino-an-thraquinone (?)
l-Amino-4: 5:8-tri-hydroxy-anthraqui-none
1-Amino-anthraquinone2-Chloro-anthraquinone[Nitration, Reduction]
V
V
V
V
142 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Benzoyl Chloride (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
Manufacture
Other IntermediatesUsed and Notes
DyeAppli-cationClass
889
INDIGO GBOUPDYES
Indigo Yellow 3G
890 Ciba Yellow G I '14:— 48
Indigo or Phenyl-gly-cine or Phenyl-gly-cine-o-carboxylic acidor Thiocarbanilide orAniline or PhthalicAnhydride
Indigo or Phenyl-gly-cine or Phenyl-gly-cine-o-carboxylic acidor Thiocarbanilide orAniline or PhthalicAnhydride
[Bromination]
JV-Benzoyl-o-folidine
H3C CH3
== 316
STATISTICS.—Manufactured 1919:— ?
FORMATION.—Tolidine is heated in toluene solution with benzoylchloride under a reflux condenser
LITERATURE.—Lange, Zwischenprodukte, #1281
Dyes Derived from AT-Benzoyl-o-folidine
SchultzNumberfor Dye
104
Ordinary Name andClass of Dye
MONOAZO DYEBenzoyl Pink
Statistics ofImport and
Manufacture
Other IntermediatesUsed and Notes
Nevile-Winther's Acid
DyeAppli-cationClass
D
DYES CLASSIFIED BY INTERMEDIATES 143
[(N-Benzyl-anilino) -methylj-fcenzene-sulfonic Acid (C. A. nomen.)
See Dibenzyl-anjiine-sulfonic Acid
Benzyl Chloride
a-Chloro-foluene (C. A. nomen,)
CH2C1
= C7H7C1= 126.5
STATISTICS.—Imported '14:— 4,589 lbs.Manufactured '17:— 136,179 lbs.Manufactured'18:— 690,930 lbs.Manufactured '19:— 720,953 lbs.Manufactured '20:—1,246,412 lbs.
FORMATION.—From boiling toluene by passing in chlorine until thetheoretical amount (37.5%) has been absorbed
LITERATURE.—Cain, Intermediate Products (2d Ed.), 15Lange, Zwischenprodukte, #5
Dyes Derived from Benzyl Chloride
SchultzNumberfor Dye
517
523
586
Ordinary Name andClass of Dye
TRTPHENYL-METHANE DYES
Methyl Violet 5BBenzyl Violet
Fast Green
XANTHONE DYEChrysoline
Statistics ofImport and
Manufacture
I '14:— 22,387M'17:— ?I '20:— 3,313
I '14:— 14,347I '20:— 3,612
I '20:— 1,402
Other IntermediatesUsed and Notes
[Benzylation of MethylViolet]
orDimethyl-aniline
(3 mols)Phenol
m-Nitro-henzaldehydeDimethyl-aniline
(2 mols)Benzyl chloride (2 mols)[Sulf onation, Oxidation]
Phthalic AnhydrideKesorcinol (2 mols)
DyeApplir-cationClass
B
A
A
144 DYES CLASSIFIED BY INTERMEDIATES
Benzyl-ethyl-aniline
Ethyl-benzyl-aniline
A7-Ethyl-Ar-phenyl-&enzylamine (C A. nomen.)
STATISTICS.—Imports 1914:—small amountManufactured 1917:— ?Manufactured 1918:— ?Manufactured 1919:— ?Manufactured 1920:—159,636 lbs.
FORMATION.—From one part of ethyl-aniline and two parts of benzylchloride, by boiling under a reflux condenser for four hours
LITERATURE.—Cain, Intermediate Products (2d Ed.), 69
Dyes Derived from Benzyl-ethyl-aniline
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
505
506
508
TRIPHENTL-^IETHANEDYES
Light Green SFYellowish
Erioglaucine
Xylene Blue AS
I 14:— 71,462M'19: - - ?I '20:— 7,490M ;20:— ?
I 314:-M'19:-I '20:-MJ20:-
I '14:-I '20:
66,526
6,160
8,2385,573
Benzyl-ethyl-aniline(2 mols)
Benzaldehyde[Sulfonation; Oxidation]
Benzyl-ethyl-aniline(2 mols)
Benzaldehyde-o-sul-fonic acid
[Sulfonation; Oxidation]
Benzyl-ethyl-aniline(2 mols)
3-Methyl-benzalde-hyde-4:6-disulfonicAcid
[Oxidation]
DYES CLASSIFIED BY INTERMEDIATES 145
Dyes Derived from Benzyl-ethyl-aniline (continued)
SchultzNumberfor Dye
545
Ordinary Name andClass of Dye
TRIPHENYL-METHANEDYES
(continued)Patent Blue A
Statistics ofImport and
Manufacture
I '14:— 03,744M'18:— ?I '20:— 44,801
Other IntermediatesUsed and Notes
B enzyl-ethyl-aniline(2 mols)
m-Nitro-benzaldehydeor m-Hydroxy-benzal-dehyde
[Sulfonation; Oxidation
DyeAppli-cationClass
A
Benzyl-ethyl-aniline-disulfonic Acid
iV-Ethyl-iV-(29-sulfo-beDzyl)-metanilic Acid (C A. nomen.)
Note.—Position of sulfonic group in the benzyl radical is not fully de-
termined
STATISTICS.—Manufactured in 1919 and 1920 in undisclosed amounts
FORMATION.—B enzyl-ethyl-aniline is dissolved with cooling in two parts
of 20 per cent oleum, and is then treated with two and a half parts
of 80 per cent oleum, and the mixture warmed at 60° until the
sulfonation is complete
LITERATURE.—Cain, Intermediate Products (2d Ed.), 70
Lange, Zwischenprodukte, #1500
146 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from Benzyl-ethyl-aniline-disulfonic Acid
SchidtzNumberfor Dye
528
Ordinary Name andClass of Dye
TEEPHENYL-MEIHANE DYES
Fast AcidViolet 10B
Statistics ofImport and
Manufacture
I '14:— 12,919M'17:— ?M'18:~- ?M'19:— ?I '20:— 10,086M '20:— ?
Other IntermediatesUsed and Notes
Hydrol[Oxidation]
DyeAppli-cationClass
A
Benzyl-ethyl-aniline-sulfonic Acid*
See, Ethyl-sulfobenzyl-aniline
Benzyl-ethyl-^-phenylene-diainine-siilfoiiic Acid
See, Ethyl-sulfobenzyl-p-phenylene-diamine
3-Benzyliinino-4-inetliyl-diphenylamiiie
See, iV^Benzyl-iV^pheiiyl-^-m-tolyleiie-dianiine
Benzyl-methyl-aniline
Methyl-benzyl-aniline
iV-Methyl-iV-phenyl-6enzylamine (C A. nomen.)
FORMATION.—^From methyl-aniline and benzyl chloride by heatingtogether on a water bath for a few hours
LITERATURE.—Cain, Intermediate Products (2d Ed.), 69
1 The data and the dye table should have been placed here rather than under ethyl-sulf obenzyl-aniline- — The Author.
DYES CLASSIFIED BY INTERMEDIATES 147
SchultzNumberfor Dye
504
527
Dyes Derived
Ordinary Name andClass of Dye
TRIPHENYL-METHANE DYES
Light Green SFBluish
Acid Violet 4BN
from Benzyl-methyl-aniline
Statistics ofImport and
Manufacture
I 14:— 6,693M'17:— ?M'18:— ?
I 14:— 29,184I '20:— 23,335M'20:— ?
Other IntermediatesUsed and Notes
Benzyl-methyl-aniline(2 mols)
Benzaldehyde[Sulfonation; Oxidation]
Ketone[Sulfonation]
DyeAppli-cationClass
A
A
Benzyl-a-naphthylamine
N-Benzyl-l-naphthylamine (C. A. nomen.)
— Ci7Hi5N=233
FORMATION.—-a-Naphthylamine is heated in an autoclave with benzyl
chloride in the presence of a catalyst
LITERATURE.—Lange, Zwischenprodukte, #1363
Dye Derived from Benzyl-a-naphthylamine
SchultzNumberfor Dye
654
Ordinary Name andClass of Dye
OXAZINE DYENile Blue 2B
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
5-Diethylamino-2-nitroso-phenol
DyeAppli-cationClass
B
148 DYES CLASSIFIED BY INTERMEDIATES
iV3-Benzyl-iVi-phenyl-4-m-^olylene-diamine (C. A. nomen NH2—D
Phenyl-p-amino-benzyl-o-toluidine (CH3=1)
3-Benzylimino-4-metliyl-dipheiiylamiiie
NH.CH2-
CH3
FORMATION.—i-/tt-TolyIene-diamine hydrochloride is melted with ani-line at 220-270°, forming iV^phenyl-^wz-tolylene-diamine. Thislatter body upon being warmed with benzyl chloride with or with-out a diluent such as alcohol forms the benzyl-derivative desired
LITERATURE.—Lange, Zwischenprodukte, #1621, 1622, 1734
Dyes Derived from iNP-Benzyl-^-phenyM-m-tolylene-diamiiie
SchvZtzNumberfor Dye
684
684
684
Ordinary Name andClass of Dye
AZINE DYESRhoduline Violet
RLoduline Red B
Ehoduline Red G
Statistics ofImport and
Manufacture
I '14:— 2,751I '20:— 35
Other IntermediatesUsed and Notes
Xitroso-dimethyl-aniline
Xitroso-ethyl-aniline
Nitroso-ethyl-o-toluidine
DyeAppli-cationClass
B
B
B
Beta=0
Note.—This is not considered in the alphabetical arrangement, e.g.beta-Naphthol is indexed as p-Naphihol under "N". However £-Naphihol is placed after a-Naphtkol
Beta Acid
See, Anthraquinone-2-sulfonic Acid
Beta-Naphthol
See, j8-Naphthol under N
DYES CLASSIFIED BY INTERMEDIATES 149
Bi-compoundsSee, Di-compounds, e.g.,iox binitro-benzol (or -benzene), see
dinitr o-b enz ene
£:^'-Bis(diethylamino)-&enzohydrol (C. A. nomen.)See, ^rp'-Tetraethyl-diamino-benzohydrol
^:^'-Bis(diethylamino)-&enzophencne (C. A. nomen.)
See, p: p'-Tetraethyl-diamino-benzophenone
^:j>'-Bis(dimethylamino)-benzohydrol (C. A. nomen.)
See, Hydrol
^:^/-Bis(dimethylamino)-6enzophenone (C. A. nomen.)See, Ketone
3:5-Bis[jS-(5-hydroxy-7-sulfo-2-naphthyl)-carbamido]-/>-^oluene-sulfonic Acid (C. A. nomen.)See, Sulfo-m-tolylene-diamine-bis (carbonyl-amino-naphthol-
sulfonic Acid)
Broenner's AcidSee, page 152
1-Bromo-anthraquInoneBr
Y J =Ci4H7BrO2 = 287c o A ^
FORMATION.—From potassium salt of anthraquinone-1-sulfonic acid,by treatment with bromine and acid
LITERATURE.—Lange, Zwischenprodukte, #3083Dye Derived from 1-Bromo-anthraciuinone
SchultzNumberfor Dye
873
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
HelindoneBrown AN
Statistics ofImport and
Manufacture
I '14:— 2,831I '20-— 16,290
Other IntermediatesUsed and Notes
1-Br omo- anthraquinone(2 mols)
1:4-Diamino-anthra-quinone
DyeAppli-cationClass
V
150 DYES CLASSIFIED BY INTERMEDIATES
5-Bromo-2-hydroxyl-3-methy*-^hionaphthene (C. A. and Englishnumbering)
6-Bromo-3-hydroxyl-4-methyl-(l)-thionaphthene (German num-bering)
FORMATION.—4-Bromo-6-nitro-2-methyl~benzoic acid is reduced withN a & ; the amino-compound diazotized, and then treated withpotassium xanthogenate (potassium ethyl xanthate). The xantho-genate compound upon being treated with chloro-acetic acid formsbromo-methyl-phenyl-thioglycol-o-carboxylic acid
B r / N s . C H s . C O O H
KycooRCH3
This compound upon being fused with caustic alkali, forms thecarboxylic acid of 5-bromo-2-hydroxy-3-methyl-thionaphthene.The carboxylic acid decomposes, evolving CO2, when its solutionis acidified and warmed
LITERATURE.—Lange, Zwischenprodukte, #2169Georgievics and Grandmougin, Dye Chemistry, 433,437Ct Cain, Intermediate Products (2d Ed.), 158, 159
Dye
SckidteNumberfor Dye
910
Derived from 5-Bromo-2-hydroxyl-3-methyl-tluoiiaphthene
Ordinary Name andClass of Dye
INDIGO GROUP DYEHelindone Pink BN
Statistics ofImport and
Manufacture
I '14:— 41,699I '20:-— 17,162
Other IntermediatesUsed and Notes
5-Bromo-2-hydroxyl-3-methyl-thionaphthene(2 mols)
[Oxidation]
DyeAppli-cationClass
V
DYES CLASSIFIED BY INTERMEDIATES
I-Bromo-4-methylamino-anthraquinone
151
N H . CH3
FORMATION.—From l-methylamino-anthraquinone by treating itspyridine solution with bromine and warming on the water bath
LITERATURE.—Lange, Zwischenprodukte, #3190
Dye Derived from l-Bromo-4-methylamino-anthraquinone
SchultzNumberfor Dye
856
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Alizarin Astrol B
Statistics ofImport and
Manufacture
I '14:— 10,907I '20:— 15,518
Other IntermediatesUsed and Notes
p-Toluidine[Sulfonation][? Classification]
DyeAppli-cationClass
ACr
2-Bromo-l-methylamino-anthraquinone
CO
c c
NH.CH 3
iBr
FORMATION.—^From l-amino-2-bromo-anthraquinone by methylationwith dimethyl-sulfate
LITERATURE.—Lange, Zwischenprodukte, #3191
Dye Derived from 2-Bromo-l-methylamino-anthraquinone
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
839
ANTHRAQUINONE ANDALLIED DYES
Algol Blue K I '14:—150I '20:—218
2-Bromo-l-methyl-amino-anthraqui-none (2 mols)
152 DYES CLASSIFIED BY INTERMEDIATES
4-Bromo-iV-methyl-anthrapyridone
6-Bromo-3-methyl-3:7-pm'-7iaphthoquinoline-2(3): 7-dione (C.A.nomen.)
N.CHs
—340
FORMATION.—(1) From 1-methylamino-anthraquinone, by acetylationof amino group, and condensation to the JV-methyl-anthra-pyridone. Bromination of this latter compound in the 4 positionresults in 4-bromo-A^-methyl-anthrapyridone. (2) From 4-bromo-1-methylamino-anthraquinone by acetylation and closing the ring
LITERATURE.—Lange, Zwischenprodukte, #3609Georgievics and Grandmougin, Dye Chemistry, 464-465Ullmann, Enzy. tech. Chemie, 1, 192
SchultzNumberJor Lye
825
Dye Derived from
Ordinary Name andClass of Dye
ANTHRAQUINOXE AXDALLIED DYES
Algol Red B
4-Bromo-i^-methyl-anthrapyridone
Statistics ofImport and
Manufacture
I '14:— 2,399I '20:— 4,151
Other IntermediatesUsed and Notes
2-Amino-aiitliraqui-none
DyeAppli-cationClass
V
6-Bromo-3-methyl-3:7-^eri-naphthoquinoline-2(3): 7-dione (C. Anomen.)
See, 4-Bromo-AT-methyl-anthrapyridone
Broenner's Acid2-Naphthylamine-6-sulfonic Acid6-Amino-2-naphthalene-sulfonic Acid (C A. nomen.)
Naphthylamine-sulfonic Acid Br.)3-Naphthylamine-iS-sulfonic AcidAmino-Schaeffer's Acid
DYES CLASSIFIED BY INTERMEDIATES
1NH2 _ <
153
STATISTICS.—Imported '14:—2,316 lbs.Manufactured 18:— ?Manufactured ' 19:— ?Manufactured '20:— ?
FORMATION.—By heating the sodium salt of Sehaeffer's Acid with con-centrated ammonia in an autoclave at 180°
LITERATURE.—Cain, Intermediate Products (2d Ed.), 206Lange, Zwischenprodukte, #2371-2376Thorpe, Die. Chemistry, 3, 601
Dyes Derived from Broenner's Acid
SchultzNumberfor Dye
172
174
176
177
230
302
Ordinary Name andClass of Dye
MONOAZO DYESFast Brown 3B
Double BrilliantScarlet G
Double ScarletExtraS
Scarlet 2R
Chrome Yellow DMordant Yellow 0
DISAZO DYESCloth Bed 3G, 3GA
Hessian BrilliantPurple
Statistics ofImport and
Manufacture
I '14:— 1,477
I '14:—210,429M '17:— ?M'20:— ?
I '14:— 10,182M'17:— ?I '20:— 1,653
I '14:—129,651M'17:— ?M'18:— 32,011M'19:— ?I '20:— 1,389M '20:— ?
I '14:— 251
Other IntermediatesUsed and Notes
a-Naphthol
/3-Naphthol
Nevile-Winther's Acid
Salicylic Acidor
o-Cresotic Acid
o-Ainino-azo-toluene
Diamino-stilbene-disulf onic Acid
Broenner's Acid(2 mols)
DyeAppli-cationClass
A
A
A
M
M
D
154 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Broenner's Acid {continued)
SchuUzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
316
357
365
366
368
370
DISAZO DYES(continued)
Brilliant Congo G
Dianol Red B
Benzo Purpurin B
Diamine Red BDelta Purpurin 5B
Brilliant Purpurin4B
Brilliant Congo R
I '14:— 21,090M'17:— ?M'18:— ?M'19:~- ?
I '14:— 21,058M '17:— ?M '18:— ?I '20:— 1,896
I '14:— 6,634
I '14:— 19,133I '20:— 11,129
BenzidineAnoino-R Acid
Dichloro-benzidine DBroenner's Acid
(2 mols)
TolidineBroenner's Acid
(2 mols)
Tolidine D2-Naphthylamine-7-
sulf onic Acid
Tolidine DNaphthionic Acid
Tolidine DAmino-R Acid
CAcid
1: 5-Dihydroxy-naphthalene-2-sulfonic Acid
2-Naphthol-4: 8-disulfonic Acid
2-Naphthylamine-4:8-disulfonic Acid
(These intermediates not considered herein)
Carbazole
Dibenzo-pyrrole
Diphenylene-imide
H
DYES CLASSIFIED BY INTERMEDIATES
STATISTICS.—Imported ' 14:—very smallManufactured '18:— ?Manufactured '19:— ?Manufactured '20:— ?
FORMATION.—By extraction from coal-tar or crude anthracene
LITERATURE.—Ullmann, Enzy. tech. Chemie, 3, 274Lange, Zwischenprodukte, page 308
Dyes Derived from Carbazole
155
SchulteNumberfor Dye
748
Ordinary Name andClass of Dye
SULFUR DYEHydron Blue
Statistics ofImport and
Manufacture
I ;14:—296,723I '20:— 19,210M'20:— ?
Other IntermediatesUsed and Notes
p-Nitroso-phenol[S+Na*S]
DyeAppli-cationClass
V
Carbolic Acid
See, Phenol
Carbonyl Chloride
See, Phosgene
2-Carboxy-5-chloro-phenyl-thioglycolic Acid
See, 5-Chloro-phenyl-thioglycol-a-carboxylic Acid
iV-(Caxboxy-methyl)-anthranilic Acid (C. A. nomen.)
See, Phenyl-glycine-o-carboxylic Acid
2-(Carboxy-methyl-mercapto)-4-chloro-benzoic Acid (C A. nomm.)
See, 5-Chloro-phcnyl-thioglyco!-o-carboxylic Acid
Cassella's Acid
See, 2-Naphthol-7-sulfonic Acid
Cassella's Acid F
See, 2-Naphthylamine-7-sulfonic Acid
156 DYES CLASSIFIED BY INTERMEDIATES
Chi AcidSee, Anthraquinone-1: 8-disulfonic Acid
Chicago AcidSee, l-Amino-8~naphthol-2:4-disulf onic Acid
3-Chloro-aniline-2-sulfonic AcidSee, 2-Amino-6-chloro-benzene-sulfonic Acid
5-Chloro-o-anisidine (N
NH2
| | 0 C H 3 = C7H8C1XO = 157.5Cl
FORMATION.—1: 4~Dichloro-3-nitro-benzene is boiled with caustic potashand methyl alcohol and the resulting chloro-nitro-anisol is reducedwith iron and acetic acid
LITERATURE —J. Soc. Chem. Ind. 21, 610 (1902)U. S. Pat. 695,812Laaige, Zwischenprodukte, #1034
Dye Derived from 5-Chloro-o-anisidine
SchultzNumberfor Dye
97
Ordinary Name andClass of Dye
MONOAZO DYEChloranisidine
Scarlet
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
jS-Naphthol
DyeAwl'cationClass
MF
I-Chloro-anthraquinone (C. A. nomen.)a-Chloro-anthraquinone
nr\ Cl
>2 = 242.5
FORMATION.—From potassium anthraquinone-l^sulfonate by treatmentat 100° with chlorine and dilute hydrochloric acid
LITERATURE.—Lange, Zwischenprodukte, #3081, 3083, 3086
DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from 1-Chloro-anthraquinone
157
SchultzNumberfor Dye
834
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Algol Gray B
Statistics ofImport andManufacture
I '14:— 4,192I '20:— 890
Other IntermediatesUsed and Notes
1-Amino-anthraquinone[Nitration, Reduction]
DyeAppli-cationClass
V
2-Chloro-anthraquinone (<7. A. nomen.)
/3-Chloro-anthraquinone
= 242.5
FORMATION.—(1) From sodium anthraquinone-2-sulfonate in aqueoussolution, by adding hydrochloric acid, and by passing in chlorineuntil all the 2-chloro-anthraquinone is precipitated out. (2) Fromphthalic anhydride and chloro-benzene by first condensing in pres-ence of A1C13 to chloro-benzoyl-benzoic acid, and then by warmingwith sulfuric acid to 2-chloro-anthraquinone
LITERATURE.—Lange, Zwischenprodukte, 3082, 3083Ullmann, Enzy. tech, Chemie, 1, 472
Dyes Derived from 2-Chloro-anthraquinone
SchultzNumberfor Dye
824
828
870
Ordinary Name andClass of Dye
ANTHRAQTJINONE ANDALLIED DYES
Algol Orange R
IndanthreneBordeaux B
Algol Corinth R
Statistics ofImport and
Manufacture
I '14:— 51I '20:— 406
I '20:—2,741
I'29:— 134
Other IntermediatesUsed and Notes
1-Amino-anthraquinone
2-Chloro-anthraquinone(2 mols)
1:5-Diamino-anthra-quinone
1-Amino-anthraquinone[Nitration, Reduction]Benzoyl chloride
DyeAppli-cationClass
V
V
V
158 DYES CLASSIFIED BY INTERMEDIATES
l-Chloro-anthraquinone-2-carboxylic Acid
.CO. Cl
c o c r^ 286.5
FORMATION.—2-Methyl-l-nitro-anthjaquinone is treated with chlorine
in nitro-benzene solution, whereby the nitro group is substituted
by chlorine and the methyl group oxidized, thus forming 1-chloro-
anthraquinone-2-carboxylic acid
LITERATURE.—Lange, Zwischenprodukte, #3171
Ullmann, Enzy tech. Chemie, 1, 484
Dye Derived from l-Chloro-anthraquinone-2-carboxylic Acid
SchulizNumberfor Dye
831
Ordinary Name andClass of Dye
ANTHRAQUTNONE ANDALLIED DYES
IndanthreneRedBN
Statistics ofImport and
Manufacture
I '14:—6,056I ;20:—4,766
Other IntermediatesUsed and Notes
/3-Naphthylamine
DyeAppli-cationClass
V
o-Chloro-fcenzaldehyde
HCO
> = 140.5
STATISTICS.—Manufactured '20:— ?
FORMATION.—From o-chloro-benzyl alcohol by oxidation with nitric
acid in a sulphuric acid solution at about 40° C.
LITERATURE.—J. Soc. Chem. Ind. 18, 576 (1899)
Lange, Zwischenprodukte, #179-184
DYES CLASSIFIED BY INTERMEDIATES 159
SchultzNumberfor Dye
496
500
503
551
Dyes Derived
Ordinary Name andClass of Dye
TRIPHENYL-METHANE-DYES
Setoglaucine
Setocyanine 0
Night Green ANeptune GreenBrilliant Milling
Green B
EriochromeAzurol B
from o-Chloro-benzaldehyde
Statistics ofImport and
Manufacture
I J20:— 1,102
I 14:— 923I '20:— 1,102
I 14:— 40,868M19:— ?I '20:— 10,940M'20:— ?
I 14:— 21,060I '20:— 7,275
Other IntermediatesUsed and Notes
Dimethyl-aniline(2 mols)
[Oxidation]
Ethyl-o-toluidine(2 mols)
[Oxidation]
Ethyl-sulfobenzyl-ani-line (2 mols)
[Oxidation]
o-Cresotic acid (2 mols)[Oxidation]
DyeAppli-cationClass
B
B
A
ACr
2-Chloro-benzaldehyde-6-sulfonic Acid
3-Chloro-2-formyl-6enzene-sulfonic Acid (C. A. nomen.)
HCO
C1 _ c7H5C104S = 220.5
FOBMATION.—(1) 1: 3-Dichloro-2-benzaldehyde is treated with one molof sodium sulfite under pressure. (2) 3-Chloro-2-toluene-l-suKonicacid is oxidized with manganese dioxide and sulfuric acid
LITERATURE.—Lange, Zwlschenprodukte, #710
Dye Derived from 2-Chloro-benzaldehyde-6-sulfonic Acid
SchultzNumberfor Dye
554
Ordinary Name andClass of Dye
TRIPHENTL-METHANE DTE
Chrome Azurol S
Statistics ofImport and
Manufacture
I 14:— 2,469I '20:— 551
Other IntermediatesUsed and Notes
o-Cresotic Acid (2 mols)[Oxidation]
DyeAppli-cationClass
ACr
160 DYES CLASSIFIED BY INTERMEDIATES
?-Chloro-7-me5o-benzanthren-7-one (C. A. nomen.)
See, Chloro-benzanthrone
Chloro-benzanthrone
?-Chloro-7-m€so-6enzanthren-7-one (C. A. nomen.)
Cl= C17H9C1O =264.5
STATISTICS.—Manufactured J19:— ?
FORMATION.—From benzanthrone in acetic acid solution by treatmentwith chlorine
LITERATURE.—Addition #6719 to French Patent 349,531 of Oct. 1,1906
Dyes Derived from Chloro-benzanthrone
SchulizNumberjar Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
766
767
768
ANTHEAQTHNONE AXDALLIED DYES
IndanthreneViolet R
IndanthreneViolet 2R
IndanthreneViolet B
I '14:-M'19:-I J20:
1,590?941
I '14:— 68,419I J20:— 40,782
T20:—S4,165(?)
Chloro-benzanthrone(2 mols)
Chloro-benzanthrone(2 mols)
[Dichlorination][or Indanthrene Violet
R, chlorinated]
Chloro-benzanthrone(2 mols)
PDibromination][or Indanthrene Violet
R, brominated]
V
DYES CLASSIFIED BY INTERMEDIATES 161
Chloro-fcenzene (C. A, nomen.)
Monochlor-benzene
Cl
1 = 112.5
STATISTICS.—Manufactured 1917.-24,624,099 lbs.Manufactured 1918:—20,530,639 lbs.Manufactured 1919:— 4,116,666 lbs.Manufactured 1920:— 4,829,142 lbs.
FORMATION.—By passing chlorine through benzene in the presence ofa catalyst (iron) and at a relatively low temperature
LITERATURE.—Cain, Intermediate Products (2d Ed.), 6-11Lange, Zwischenprodukte, #2
Uses.—For technical preparation of o- and p-chloro-nitro-benzene,chloro-dinitro-benzcne, o-amino-phenol-p-sulfonic acid and manyother intermediates
l-Chloro-2:4-dinitro-fcenzene (C. A. nomen.)
2:4-Dinitro-chloro-benzene
Cl/ \ N O 2f J =C6H3C1N2O4 = 202.5
NO2
STATISTICS.—Manufactured 1917:—6,078,637 lbs.Manufactured 1918:— ?Manufactured 1919:—4,428,730 lbs.Manufactured 1920:—5,947,791 lbs.
FORMATION.—From chloro-benzene by dinitration with mixed nitricand sulphuric acids
LITERATURE.—Cain, Intermediate Products (2d Ed.), 14Lange, Zwischenprodukte, #723
162 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from l-Chloro-2:4-dinitro-benzene
SchultzNumberfor Dye
724
Tlo
726
727
73S
Ordinary Name andClass of Dye
SULFUK DYESImmedial Black
Immedial DarkBrown A
Immedial Brown B
Pyrogene DirectBlue
Pyrogene Blue
Auronal Black B
Cotton Black
Statistics ofImport and
Manufacture
14:— 54,696M I S : — ?
I 14:— 23,887M I S : — ?
I 14:— 10,934I '20:— 2,49S
Other IntermediatesUsed and Notes
p-Amino-phenol[S+Na«S]
p-Amino-phenol[NaOH; S+Na^S]
p-Amino-phenol[Alcohol;
p-Phen yl ene-diamine[Glycerol; S+Na^S]
Sulfanilic or Metanilicacid
[S+NaaS]
DyeAppli-cationClass
S
S
l-Chloro-2:6-dinitro-benzene-4-sulfonic Acid
See, 4-Chloro-3: 5-dinitro-benzene-sulfonic Acid
4-Chloro-3:5-dinitro-6enzene-sulfonic Acid (C. A. nomen.)
I-Chloro-2: 6-dinitro-ben^ene-4-sulfonic Acid
SO3H
O 2Nl J N O 22 O 7 S = 282.5
FORMATION.—34 Par t s of chloro-benzene are dissolved in a mixture of72 parts of monohydrate and 30 par ts of 2 5 % oleum, by aid of heat.When cold, there is added 26 parts of 8 7 % nitric acid which causesthe temperature t o rise to 40° where it is held for 2 hours. Thena further addition of oleum is made,—100 par ts of 60% followed b y40 parts of potassium nitrate, and the mixture heated for severalhours at 120-130°.
LITERATURE.—Lange, Zwischenprodukte, #1037
DYES CLASSIFIED BY INTERMEDIATES 163
Dye Derived from 4-Chloro-3:5-dinitro-benzene-sulfonie Acid
SchultzNumberfor Dye
542
Ordinary Name andClass of Dye
TRIPHENYL-METHANEDYE
Agalma Green B
Statistics ofImport and
Manufacture
I J14:— 2,294
Other IntermediatesUsed and Notes
HydrolMetanilic acid[Oxidation]
Appli-cationClass
A
3-Chloro-2-formyl-&enzene-sulfonic Acid (C. A. nomen.)
See, 2-Chloro-benzaldeliyde-6-sulfonic Acid
Chloro-H AcidSee, l~Chloro-8-naphthol-3: 6-disulf onic Acid
(4-Chloro-6-methoxy-3-methyl-phenyl-mercapto)-acetic Acid (C.A. nomen.)
See, 4-Chloro-6-methoxy-3-methyl-phenyl-thioglycolic Acid
^Chloro-e-methoxy-S-methyl-phenyl-tliioglycolic Acid
(4-Chloro-6-metlioxy-3-metliyl-phenyl-mercapto)-acetic Acid(C. A. nomen.)
S.CH2 .COOH
CH3O =Ci0HnClO3S=246.5
FOEMATION.—4-Chloro-6-methoxy-m-toluidine (NH2 = 1) is dissolvedin hydrochloric acid and diazotized. The diazo solution, warmedto 70°, is introduced into an alkaline solution of potassium xan-thate (C2H5O.CS.SK), the condensation product extracted andsaponified to the mercaptan. The mercaptan is reacted withchloro-acetic acid, forming the above thioglycolic acid
LITERATURE.—Ger. Pat. 245,544; 241,910Frdl. 10, 507, 502Lange, Zwischenprodukte, #1043, 688Cf. Georgievics and Grandmougin, Dye Chemistry, 436-7
164 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from 4-Chloro-6-metho^-3-methyl-phenyl-ttaoglycolicAcid
Schultzdumberfor Dye
920
Ordinary A a?ne andClass of Dye
LSDIGO GROUPDYE
HelindoneViolet BB
Statistics ofImport andManufacture
I '14 — 28,607I '20 — 16,882
Other IntermediatesUsed and Notes
4r-Chloro-6-methoxy-3-methyl-phenyl-thio-glycolic acid (2 mols)
[Chloro-sulfonic acid]
DyeAppli-cationClass
V
l-CMoro-8-naphthol-3:6-disulfonic Acid
8-Chloro-l-rcaphthol-3: 6-disulfonic Acid (C A. nomen.)
Chloro-H Acid
HO Cl
SO3H S2= 338.5
STATISTICS.—Manufactured ' 18:— ?
Manufactured ' 19:— ?Manufactured J20:— ?
FORMATION.—H acid is diazotized; and the yellow diazo body isfiltered off, mixed with 10 per cent hydrochloric acid, cooled to10°, and a solution of cuprous chloride added. This product isnow heated to complete the reaction, purified, and the chloro-bodyisolated. (Sandmeyer Reaction)
LITERATUKE.—Cain, Intermediate Products (2d Ed.), 238Lange, Zwischenprodukte, #2451, 2671Thorpe, Die. Chemistry, 3, 628
DYES CLASSIFIED BY INTERMEDIATES 165
Dyes Derived from l-Chloro-8-naphthol-3:6-disulfonic Acid]
SchultzNumberfor Dye
119
418
Ordinary Name andClass of Dye
MONOAZO DYEDiamine Rose
DISAZO DYEDiamine Brilliant
BlueG
Statistics ofImport and
Manufacture
I 14:— 5,269M18:— ?M19:— ?M;20:— ?
I 14:— 11,592I ;20:— 51
Other IntermediatesUsed and Notes
D eliydr o-thio-p-toluidine
Dianisidine1-Chloro-S-naphthol-
3: 6-disulfonic Acid(2 mols)
DyeAppli-cationClass
D
D
8-Chloro-l-naphthol-3: 6-disulfonic Acid (C. A. nomen.)
See, l-Chloro-8-naphthol-3: 6-disulfonic Acid
l-Chloro-8-naphthol-4-sulfonic Acid
8-Chloro-l-naphthol-5-sulfonic Acid (C. A. nomen.)
HO Cl
= C10H7ClO4S = 258.5
SO3H
FORMATION.—l-Chloro-naphthalene-4-sulfonic acid is nitrated and
reduced, forming l-chloro-8-naphthylamine-4-sulfonic acid; which
is diazotized and added slowly to a boiling hot solution of 10 per
cent sulfuric acid and the boiling continued until the nitrogen
evolution ceases
LITERATURE.—Eng. Pat., 12085 of 1898
Cf. Lange, Zwischenprodukte, #2451
166 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from l-Chloro-8-napIithol-4-sulfonic acid
SchultzNumberfor Dye
417
Ordinary Name andClass of Dye
DISAZO DYEChlorazol Blue R
Statistics ofImport andManufacture
I '14:— 10,151
Other IntermediatesUsed and Notes
Dianisidinel-Chloro-8-naphthol-5-
sulfonic Acid (2 mols)
DyeAppli-cationClass
D
l-Chloro-8-naphthol-5-sulfonic Acid
8-Chloro-l-naphthol-4-suKonic Acid (C A. nomen.)
HO
5 = 258.5
H O 3 S
FORMATION.—l-Chloro-naphthalene-5~sulfonic acid is nitrated andreduced, forming l-chloro-8-naphthylarnine-5-sulfonic acid; whichis diazotized and added slowly to a boiling hot solution of 10 percent sulfuric acid, and the boiling continued until the evolution ofnitrogen ceases.
LITERATURE.—Eng. Pat., 12085 of 1898Cf. Lange, Zwischenprodukte, #2451
SchultzNumberfor Dye
417
Dye Derived from "
Ordinary Name andClass of Dye
DISAZO DYEChlorazol Blue 3G
L-Chloro-8-naphthol-5-sulfonic acid
Statistics ofImport andManufacture
I '14:— 10,151
Other IntermediatesUsed and Notes
Dianisidinel-Chloro-8-naphthol-5-
sulfonic Acid (2 mols)
DyeAppli-cationClass
D
8-Chloro-l-naphthol-4-sulfonic Acid (C. i . nomen.)
See, l-Chloro-8-naphthol-5-sulfonic Acid
DYES CLASSIFIED BY INTERMEDIATES
8-Chloro-l-7iaphtliol-5-sulfonic Acid (C. A. nomen.)
See, l-Chloro-8-naphthol-4-sulfonic Acid
l-Chloro-3-nitro-6-aniline
See, 2-Chloro-4-nitro-aniline (C. A. nomen.)
2-Chloro-4-nitro-aniline (C. A. nomen.)
o-Chloro-p-rritro-aniline
l-Chloro-3-nitro-6-aniline
167
NH2
2 = 172.5
FORMATION.—p-Nitro-aniline is dissolved in concentrated hydrochloricacid or in sulfuric acid, ice added to cool under 0°, and chlorine isconducted into the solution under 0°, until the proper increase inweight has taken place
LITERATURE.—Lange, Zwischenprodukte, #724
o-Chloro-£-nitro-aniline
See, 2-Chloro-4-nitro-aniline ((7. A. nomen.)
SchultzNumberfor Bye
467
468
Dyes Derived
Ordinary Name andClass of Dye
FRISAZO DYESDiphenyl Green G
Diphenyl Green 3G
from 2-Chloro-4-nitro-aniline
Statistics ofImport and
Manufacture
I '20:— 2,205
Other IntermediatesUsed and Notes
BeruzidinePhenolHAcid
BenzidineSalicylic AcidHAcid
DyeAppli-cationClass
D
D
168 DYES CLASSIFIED BY INTERMEDIATES
2-Chloro-5-nitro-&enzaldehyde
HCO
: l = C7H4CINO3 = 185.5
FORMATION.—o-Chloro-benzaldehyde is dissolved in sulfuric acid, andnitrated cold with mixed acid
LITERATURE.—Beil., I l l , 16
Dye Derived from 2-Chloro-5-nitro-benzaldeliyde
SchultzNumberfor Dye
552
Ordinary Name andClass of Dye
TREPHENYL-METHANE "DYE
Chromal Blue G
Statistics ofImport and
Manufacture
I 14:— 1,335
Other IntermediatesUsed and Notes
o-Cresotic Acid (2 mols)[Oxidation]
DyeAppli-cationClass
M
2-Chloro-6-nitro-6enzaldehyde (C. A. nomen.)
o-Chloro-onitro-beiizaldeliyde
HCO
O 2 N / p i _ C7H4C1NO3 = 185.5
FORMATION.—This can be prepared from 2-chloro-6-nitro-benzyl bromideby action of strong nitric acid, or from 2-chloro-6-nitro-benzylalcohol by oxidation
LITERATURE.—Lange, Zwischenprodukte, #699Beil. I l l , , spl. 11
Bye Derived from 2-Chloro-6-nitro-benzaldehyde
SchuUzNumberfor Dye
887
Ordinary Name andClass of Dye
INDIGO GROUPDYES
Brilliant IndigoBASF/4G
Statistics ofImport and
Manufacture
I '20:— 1,207
Other IntermediatesUsed and Notes
2-CHoro-6-nitro-ben-zaldehyde (2 mols)
[Acetone; Bromination]
DyeAppli-cationClass
V
DYES CLASSIFIED BY INTERMEDIATES 169
o-CMoro-o-uitro-benzaldehyde
See, 2-Chloro-6-nitro-&enzaldehyde (C. A. nomen.)
o- and -Chloro-nitro-benzenes (C. A. nomen.)
o- a?id p-Nitro-chloro-benzenes
N0 2 N0 2
C 1 and I J = C6H4C1NO2 = 157.5
STATISTICS.— Mixed orth. paraManufactured 1917:— 602,192 lbs.Manufactured 1918:— ?Manufactured 1919:—2,520,991 lbs.Manufactured 1920:— 349,386 lbs. 959,405 lbs.
FORMATION.—Chloro-benzene, upon being nitrated, gives a mixture oabout 30 per cent of o-chloro-nitro-benzene and about 70 per centof p-chloro-nitro-benzene. The separation is carried out byalternate crystallization (of the p-compound) and fractionaldistillation
LITERATURE.—Cain, Intermediate Products (2d Ed.), 11-13Lange, Zwischenprodukte, #193, 194
USES.—o-Chloro-nitro-benzene is employed for preparation of o-nitro-anisole, which in turn leads to o-anisidine and dianisidine. I t isalso used for 4-chloro-3-rjitro-benzene-sulfonic acid
p-Chloro-nitro-benzene is employed for preparation of sub-stituted diphenylamines (Sulfur Dyes), and for 2-chloro-5-nitro-benzene-sulfonic acid
2-Chloro-5-nitro-5enzene-sulfonic Acid
SO3H
= C6H4C1NO5S = 237.5
STATISTICS.—Manufactured 1920:— ?
FORMATION.—By sulfonation of p-chloro-nitro-benzene with 10-12 percent oleum
170 DYES CLASSIFIED BY INTERMEDIATES
LITERATURE.—Cain, Intermediate Products (2d Ed.), 14USES.—For preparation of -i-nitro-aniline-2-sulfonic acid (p-nitro-
aniline-o-sulfonic acid)
4-Chloro-3-nitro-&enzene-sulfonic Acid
SO3H
= 237.5
FORMATION.—By sulfonation of o-chloro-nitro-benzene with 5 parts of30 per cent oleum
LITERATURE.—Cain, Intermediate Products (2d Ed.), 13USES.—For preparation of aniline-2: 5-disulfonic acid
(4-Chloro-2-nitro-phenyl-mercapto)-acetic Acid (C. A. nomen.)
See 4-Chloro-2-nitro-phenyl-thioglycolic Acid
4-CWoro-2-mtro-phenyl-ttaoglycolic Acid
(4-Chloro-2-nitro-phenyl-mercapto)-acetic Acid (C A. nomen.)
S.CH 2 .CO0H
INO2 _ C8H6C1NO4S = 247.5
FORI^ATION.—(1) 4-Chloro-2-nitro-phenyl-mercaptan is reacted withchloro-acetic acid in an alkaline solution. (2) Probably also by re-acting the nitro-derivative of p-dichloro-benzene (l:4-dichloro-3-nitro-benzene) with thioglycolic acid
LITERATURE.—Cf. Lange, Zwischenprodukte, #2171, 611, 1041, 674
Dye Derived from 4-Chloro-2-nitro-phenyl-thioglycolic Acid
SchvltzNumberfor Dye
921
Ordinary Name andClass of Dye
INDIGO GROUP DYESHelindone Grav BR,
2B
Statistics ofImport and
Manufacture
I '14:—470I '20:—508
Other IntermediatesUsed and Notes
4-Chloro-2-nitro~plienyl-thioglycolic acid (2mols)
[Chloro-sulfonic acid:Reduction]
DyeAppli-cationClass
V
DYES CLASSIFIED BY INTERMEDIATES 171
a-Chloro-^-nitro-foluene (C. A. nomen.)
See, p-Nitro-benzyl Chloride
(m-Ohloro-phenyl-mercapto)-acetic Acid (C A. nomen.)
See, m-Chloro-phenyl-thioglycolic Acid
m-Chloro-phenyl-thioglycolic Acid(m-Chloro-phenyl-mercapto)-acetic Acid (C. A. nomen.)
S.CH2 .COOH
= C8H7C1O2S = 202.5
FORMATION.—m-Chloro-aniline is diazotized, coupled with potassiumxanthate (C2H5O . CS. SK), hydrolyzed to the mercapto-derivative,and condensed with chloro-acetic acid
LITERATURE.—Cf. Lange, Zwischenprodukte, #688
Dye Derived from m-Chloro-phenyl-thioglycolic Acid
SchultzNumberfor Dye
917
Ordinary Name andClass of Dye
INDIGO GROUP DYESHelindone Red B
Statistics ofImport and
Manufacture
I 14:—100I '20:—200
Other IntermediatesUsed and Notes
m-Chloro-phenyl-thio-glycolic Acid (2 mols)
[Oleum Condensation]
DyeAppli-cationClass
V
5-Chloro-phenyl-thioglycol-o-carboxylic Acid2-Carboxy-5-chloro-phenyl-thioglycolic Acid2-(Carboxy-methyl-mercapto)-4-chloro-&enzoic Acid (C. A.
nomen.)
FOEMATION.—4-Chloro-anthranilic acid is diazotized, and reacted withpotassium ethyl xanthate, and then with chloro-acetic acid,resulting in the formation of the chloro-phenyl-thioglycol-o-carboxyacid
LITERATURE.—Lange, Zwischenprodukte, #2170; cf. #518
172 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from 5-Chloro-phenyl-thioglycol-o-caxboxylic Acid
SchultzNumberfor Dye
909
Ordinary Name andClass of Dye
INDIGO GROUP DYECiba Red B
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
5-Chloro-phenyl-tliio-glycol-o-carboxylicacid (2 mols)
DyeAppli-cationClass
V
a-Chloro-toIuene (C. A. nomen.)
See, Benzyl Chloride
2-Chloro-5-toluidine-4-sulfonic Acid (CH3=1)
See, 2-Amino-5-chloro-p-toluene-sulfonic Acid (C, A. nomen
SOzH-1)
(4-Chloro-o-tolyI-mercapto)-acetic Acid (C. A. nomen,)
See, 4-Chloro-2-tolyl-thioglycolic Acid
4-Chloro-2-tolyl-thioglycolic Acid
(4"Chloro-o-tolyl-mercapto)-acetic Acid (C. A. nomen.)
S.CH2COOH
Q C H , =
Cl
=216.5
FORMATION.—4^Chloro-o-toluidine (NH^^l) is diazotized, coupled
with potassium xanthate (C2H5O. C S . SK), hydrolyzed to the
mercapto-derivative, and condensed with chloro-acetic acid
LITEBATURE.—Lange, Zwischenprodukte, #688
Cf. Geogievics and Grandmougin, Dye Chemistry, 437
DYES CLASSIFIED BY INTERMEDIATES 173
Dye Derived from 4-Chloro-2-tolyl-thioglycolic Acid
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
918INDIGO GROUP DYEHelindone Red 3B I '14:— 27,874
I '20:— 4,3854-Chloro-2-tolyl-thio-
glycolic Acid (2 mols)[Oleum Condensation][There is some question
as to the Cl- andCH3- positions of thatchloro-tolyl-thiogly-colic acid used]
V
Chromogen ISee, Chromotropic Acid
Chromotrope AcidSee, Chromotropic Acid
Chromotropic Acid1: 8-Dihydroxy-naphthalene-3: 6-disulfonic Acid4: 5-Dihydroxy-2: 7-naphthalene-disulfonic Acid (C. A. nomen.)Chromotrope AcidChromogen I
HO OH
HO3S SO3H
STATISTICS.—Manufactured ' 18:— ?Manufactured '19:—164,654 lbs.Manufactured '20:—152,352 lbs.
FORMATION.—(1) From l-Naphthol-3: 6:8-trisulfonic acid by fusionof the sodium salt of this acid with caustic soda at 170-220°.(2) From H acid by heating with a dilute caustic soda solutionin an autoclave at about 265°
LITEEATURE.—Cain, Intermediate Products (2d Ed.), 232Lange, Zwischenprodukte, #2775, 2670
174 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Chromotropic Acid
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
40
57
61
67
114
129
130
171
MONOAZO DYESChromotrope 2R
Chromotrope 2B
Victoria Violet
Chromotrope 6B
Chromotrope 10B
Chromazone Red A
Chromazone Blue R
Chromotrope 8B
I '14:—JVT17:—M '18:—M'19:—M '20:—
5,00????
Aniline
I '14M'18M'19M'20
. «>
I '14:— 52,36£M'17M'18M'19:I '20;1 '20
105,0862,182
I '14:— 2,818M'17:— ?VI'18:— ?M'19:—77,481
M'20:— ?
19:— ?
I '14:— 24;
p-Nitro-aniline
p-Phenylene-diamineactually from
p-Nitro-aniline andReduction
orp-Ammo-acetanilide
and Saponification
p-A m m o-acetanilide
£'18:-
a-Napiithylamine
p-Amino-benzaldehyde
p-A mino-benzaldebydeIthyl-phenyl-liydra-zine
or2>-Amino-benzylidine-
ethyl-phenyl-hydra-zone
Naphthionic Acid
A
ACr
A
M
M
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Chromotropic Acid (continued)
175
SchidtzNumberfor Dye
292
323
379
380
415
479
777
Ordinary Name andClass of Dye
DISAZO DYESAcid Alizarine
Black I
Dianil Blue R
Dianil Blue 2EBenzo New Blue 2B
Dianil Blue B
Dianil Blue G
TRISAZO DYEDianil Black E
ANTHBAQUINONE ANDALLIED DYES
Chromogen I
Statistics ofImport and
Manufacture
M'20:— ?
I ;14:— 14,434
M'19:— ?M'20:— ?
Other IntermediatesUsed and Notes
p-Pheny lene-diam m eSalicylic Acid
BenzidineChromotropic Acid
(2 mols)
TolidineNevtte-Winther's Acid
TolidineChromotropic Acid
(2 mols)
DianisidineChromotropic Acid
(2 mols)
BenzidineNaphthionic Acidwz-Phenylene-diainine
[Oxidation on fiber]
DyeAppli-cationClass
M
D
D
D
D
D
ACr
Chrysazin1: 8-Dihydroxy-anthraqTiinone (not considered herein)
Chryseic Acid4-Nitro-l-naphthol (not considered herein)
Cincholepidine
See, Lepidine
Cleve's AcidSee, l-Naphthol-5-sulfonic AcidSee, l-Naphthylanune-6-sulfonic AcidSee, l-Naphthylamine-7-sulfonic Acid
176 DYES CLASSIFIED BY INTERMEDIATES
Cleves a Acid
See, Laurent's Acid (l-Naphthylamine-5-sulfonic Acid)
Cieve's p Acid
See, l-Naphthylamine-6-sulfonic Acid
Also applied to l-Nitro-naphthalene-6-sulfonic acid
Cieve's T Acid
l-Naphthylamine-3-sulfonic Acid (not considered herein)
Cieve's 5 Acid
See, l-Naphthylamine-7-sulfonic Acid
This trivial name also applied to
l-Nitro-naphthalene-7-sulfonic Acid (not considered herein)
Cieve's 6 Acid
See, l-NaphthyIamine-7-sulfonic Acid
This trivial name also applied to
l-Nitro-naphthalene-6-sulfonic Acid (not considered herein)
l-Nitro-naphthalene-7-suKonic Acid (not considered herein)
Cieve's Acids
See, l-Naphthylamine-6-and-7-sulfonic Acids
Cieve's a-Nitro-naphthalene-sulfonic Acid
l-Nitronapthalene-5-sulf onic Acid (not considered herein)
Cieve's 7-Nitro-naphthalene-sulfonic Acid
l-Nitro-naphthalene-3-sulfonic Acid (not considered herein)
Cieve's 5-Nitro-naphthalene-sulfonic Acid
l-Nitro-naphthalene-8-sulfonic Acid (not considered herein)
Cieve's 0-Nitro-naphthaIene-sulfonic Acid
l-Nitro-naphthalene-6-sulfonic Acid (not considered herein)
l-Nitro-naphthalene-7-sulfonic Acid (not considered herein)
DYES CLASSIFIED BY INTERMEDIATES
Cresol
177
Note.—C. A. practice is to start the numbering of cresols from the OHgroup unless there is present a substituent of uhigher order" as SOzH.European practice is generally to start numbering with CHZ
STATISTICS.—Imported '14:—245,835 lbs.Manufactured '19:— ?Manufactured '20:— ?
FORMATION.—Extracted from coal tar
LITERATTJKE.—Lange, Zwischenprodukte, #438-452
Dye Derived from Oresol
SchultzNumberfor Dye
311
Ordinary Name andClass of Dye
DISAZO DYEOrange TA
Statistics ofImport and
Manufacture
I '14:—602M'17:— ?M'18:— ?M'19:— ?M'20:— ?
Other IntermediatesUsed and Notes
BenzidineNaphthionic Acid
DyeAppli-cationClass
D
2:3-Cresotic Acid (C. A. nomen.)
See, o-Cresotic Acid
o-Cresotic Acid
o-Cresotinic Acid
2: 3-Cresotic Acid (C. A. nomen.)
o-Homo-salicylic Acid
COOH
178 DYES CLASSIFIED BY INTERMEDIATES
STATISTICS.—Imported 314:—very small
Manufactured '20:— ?
FORMATION.—By dissolving o-cresol in caustic soda, evaporating to a
dry powder; then by treating this powder with carbon dioxide
under pressure
LITERATURE.—Cain, Intermediate Products (2d Ed.), 153
Lange, Zwischenprodukte, #775
Dyes Derived from o-Cresotic Acid
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport andManufacture
Other IntermediatesUsed and Notes
DyeAppli-cationClass
177
351
392
395
551
552
MOXOAZO DYEChrome Yellow D
DISAZO DYESCresotine Yellow G
ToluyleneOrange G
Cresotine Yellow R
TRJPHESTYL-
METHANE DYESEriochrome
Azurol B
Chromal Blue G
I '14M'17M'18M'19:M '20;
I '14:-M'18:-M '19:-I '20:-M'20:-
1,748
; 9
67,022??
273?
I '20:—21,060
7,275
I '14:— 1,335
Broenner's Acid
Benzidineo-Cresotic Acid (2 mols
Tolidine4: 6-Diamino-m-
toluene-sulf onic Acid
Tolidineo-Cresotic acid (2 mols)
o- Chloro-benzaldehyde[or other halogen]
o-Cresotic Acid (2 mols)[Oxidation]
2-Chloro-5-nitro-ben-zaldehyde
o-Cresotic Acid (2 mols)[Oxidation]
M
D
D
D
ACr
M
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from o-Cresotic Acid (continued)
179
SchultzNumberor Dye
553
554
Ordinary Name andClass of Dye
TRIPHENYL-METHANEDYES {continued)
EriochromeCyanine R
Chrome Azurol S
Statistics ofImport and
Manufacture
I '14:— 2,249I '20:— 2,205
I '14:— 2,469I '20:— 551
Other IntermediatesUsed and Notes
Benzaldehyde-o-sulforricAcid
o-Cresotic Acid (2 mols)[Oxidation]
2-Chloro-benzaldehyde-6-sulfonic Acid
o-Cresotic Acid (2 mols)[Oxidation]
DyeAppli-cationClass
ACr
ACr
o-Cresotinic AcidSee, o-Cresotic Acid
Croceine Acid2-Naphthol-8-sulfonic Acid (C. A. nomen.)
Bayer's Acid
iS-Naphthol-sulfonic Acid B (of Schultz)
j3-Naphthol-a-sulfonic Acid (0/ Bayer & Co.'s Patents)
Croceine Sulfonic Acido-Acid (0/ Claus and Voltz)1
Rumpff AcidHO3S
C 0 O H - «STATISTICS.—Manufactured 1919:— ?
Manufactured 1920:— ?FORMATION.—/3-Naphthol is sulfonated at a low temperature, forming
mostly croceine acid, but accompanied by some Schaeffer's acid.They are generally separated by crystallization of their salts
LITERATURE.—Cain, Intermediate Products (2d Ed.), 225Lange, Zwischenprodukte, #2435-2439Thorpe, Die. Chemistry, 3, 625
1 Claus and Voltz incorrectly assigned to this acid the constitution, 2-naphthol-3-sulfonic acid,
180 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Croceine Acid
SchvltzNumberfor Dye
167
249
251
255
259
313
320
321
324
Ordinary Name andClass of Dye
MOXOAZO DYESCroceine Scarlet
3BX
DISAZO DYESCroceine Scarlet 3B
Croceine Scarlet 0
Croceine Scarlet SBPonceau 6 RB
Ponceau 10 RB
Congo Rubine
Bordeaux
Heliotrope 2B
Chicago Blue 4R
IMMMIM
I
I
II
I
IMMI
Statistics ofImport and
Manufacture
'14:—'17:—'IS:—'19:—'20:—'20:—
'14:—
'20:—
'14:—'20:—
'14:—
'14:—'17:—'IS:—'20:—
I '14:—M '18:—M'19:—M '20:—
II :
14:—20:—
14:—
3,10???650?
9,613
100
2,3791D4
201
46,213??
2,601
1,335???
1,47360
1,199
Other IntermediatesUsed and Notes
Naphthionic Acid
Amino-azo-benzene-sulfonic Acid
Amino-azo-benzene-disulfonic Acid
Aroino-azo-toluene-sulfonic Acid
Sulfanilic Acid6-Anisidine
BenzidineNaphthionic Acid
BenzidineCroceine Acid (2 mols)
Benzidinel-Naphthol-4:8-
disulfonic Acid
Benzidine1 - Amino-8-naphthol-4-
sulfonic Acid
DyeAppli-cationClass
A
A
A
A
A
D
D
D
D
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Croceine Acid (continued)
181
SchultzNumberfor Dye
384
420
Ordinary Name andClass of Dye
DISAZO DYES(continued)
Chicago Blue 2RDiamine Blue C2R
Azidine WoolBlueB
Statistics ofImport and
Manufacture
I '14:— 23,877
Other IntermediatesUsed and Notes
Tolidinel-Anrino-8-naphthol-4-
sulfooic Acid
Dianisidinel-Amino-S-naphthol-4-
sulfonic Acid
DyeAppli-cationClass
D
D
Croceine-sulfonic AcidSee, Croceine Acid
4> CumidineSee, Pseudocumidine (C A. nomen.)
Dahl's AcidSee, 2-Naphthylamine-5-sulfoDic Acid
Dahl's Acid IISee, l-Naphtliylamine-4:6-disulfonic Acid
DahTs Acid IIISee, l-Naphthylamine-4:7-disulfonic Acid
Dahl's Acidsl-Naphthol-4:6-and-4:7-disulfonic Acids (not considered herein)
Dehydro-thio-j)-toluidineIV-Amino-5-methyl-2-phenyl-thiazolAjDaino-benzenyl-a-amino-tliio-cresolp-Amino-phenyl-tolutMazolel-(2?-A.Tnino-pheiiyl)-5-inethyl-5enzotliiazole (C A. nomen.)
\
182 DYES CLASSIFIED BY INTERMEDIATES
FORMATION.—By heating together 3}4 parts of p-toluidine with 1 partof sulfur, gradually raising the temperature to the boiling point, andfinally fractionally distilling off the dehydro-thio-p-toluidine in avacuum
LITERATURE.—Cain, Intermediates (2d Ed.), 77Lange, Zmsehenprodukte, #2219-2223
Dyes Derived from Dehydro-thio-^-toluidine
SckuUzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used an$ Notes
DyeAppli-cationClass
117
118
119
614
618
MONOAZO DYESErica 2GN
GeranineBrilliant Geranine
I '14:M'19:I '20:-
1,171?337
I '14:— 18,917M'19:-- ?I '20:— 527
Diamine Rose
THIOBENZENYL DYESChromine G
Thioflavine T
I '14:—M'18:—M'19:—M'20:—
5,269??
I ' 1 4 : — 1,001
I ' 1 4 : — 3 5 , 2 2 4
I ' 2 0 : — 5,807
l - N a p h t h o l - 3 : 8 -
d i s u l f o r d c A c i d
l - N a p h t h o l - 4 : 8 - d i s u l -
f o n i c A c i d or 1 - N a p h -
t h o l - 3 - s u l f o n i c A c i d
or 1 : 8 - D i h y d r o x y -
n a p h t h a l e n e - 4 - s u l -
f o n i c A c i d
l - C h l o r o - 8 - n a p h t h o l -
3 : 6 - d i s u K o t d c A c i d
[Sul fur , M e t h y l a t i o n ,
S u l f o n a t i o n ]
[ M e t h y l a t i o n ]
D
D
D
D
B
Dehydro-thio-^-toluidine-sulfonic Acid
IV-Amino~5-methyl--2--phenyl4hiazol-sulfonic Acid
D T S {abbreviation for above in compounds, less NH2)
l-(4-Amino-?-sulfo-phenyl)-5-methyl-fcenzothiazole (C. A. nomen.)
C H s | \ C. . N H 2 = C 1 4 H i 2 N 2 O 3 S 2 = 3 2 0
DYES CLASSIFIED BY INTERMEDIATES 183
STATISTICS.—Manufactured ' 19:— ?Manufactured '20:—51,961 lbs.
FORMATION.—By sulfonation of the "primuline melt" (from p-toluidineand sulfur), and purification from the primuline-sulfonic acid alsoformed
LITERATURE.—Cain, Intermediate Products (2d Ed.), 78Lange, Zwischenprodukte, #2237Ullmaim, Enzy. tech. Cherrde, 3, 677
Dyes Derived from Dehydro-thio-^-toluidine-sulfonic Acid
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport andManufacture
Other IntermediatesUsed and Notes
DyeAppli-cationClass
16
17
18
51
190
193
STILBENE DYESCurcuphenine
Chlorophenine
Diphenyl FastYellow
I '14:— 10,2291,102
MONOAZO DYESNitrophenineThiazol Yelow R
Alkali BrownBenzo Brown 5R
Clayton Cloth RedStanley Red
I '14M'20
M'19:-M'20:-
I '14M'18M'19M'20
:— 423:— ?
?2,*987
:— 100
'.— ?. ?
Dehydro-tMo-p-tolui-dine-sulfonic Acid(2 mols)
p-Nitro-toluene-o-sul-fonic Acid (4 mols)
Dehydro~thio-p-tolui-dine-sulfonic Acid(2 mols)
p-Nitro-toluene-o-suL-f onic Acid (4 mols)
[Reduction]
D ehydro-thio-p-tolui-dine-sulfordc Acid(2 mols)
Dinitro-dibenzyl-disul-f onic Acid orDirdtro-stilbeiie-
disulf onic Acid
p-Nitro-aniline
7n-Phenylene-diamine
/3-Naphthol
D
D
D
D
A
184 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Dehydro-tMo-£-toluidine~sulfonic Acid (continued)
SchvltzNumberfor Dye
194
196
198
199
209
350
617
Ordinary Name andClass of Dye
MOXOAZO DYES
(continued)Rosophenine 10BThiazine Red R
Titan Red
Clayton YellowThiazol YellowMimosa C
Oriol YellowCotton Yellow R
DISAZO DYETerracotta FC
Alkali Yellow R
THIOBENZENYL DYEChloramine YellowDiamine Fast YellowColumbia Yellow
Statistics ofImport and
Manufacture
I '14:— 3,077M'19:— ?M'20:— ?
I '14:— 886M'19:— ?M'20:— ?
I '14:— 29,879M'lS:— ?M'19:— ?I '20:— 11,182M'20:— ?
I '14:— 13,416I '20:— 125M'20:— ?
I '14:— 551
I '14:—180,497M'17:— ?M'18:—123,816M'19:— 54,077I '20:— 4,810M'20:—100,248
Other IntermediatesUsed and Notes
Nevile-Winther's Acid
Schaeffer's Acid
Dehydro-thio-p-tolui-dine-sulfonic Acid(2 mols)
Salicylic Acid
NaphtMonic Acidm-Phenylene-diamine
BenzidineSalicylic Acid
[Oxidation]
DyeAppli-cationClass
D
D
D
D
D
D
D
Dehydro-thio-m-xylidine
IV-Amiao-2-phenyl-5:7: III-trimetiyl-thiazol
l-(4-Amino-m-tolyl-)-3:5-dimethyl-&erLzothiazole (C. A. nomen.)
CH3
DYES CLASSIFIED BY INTERMEDIATES
STATISTICS.—Manufactured '19:— ?
Manufactured '20:— ?
185
FORMATION.—From m-xylidine and sulfur by heating to the boilingpoint until there is no further evolution of hydrogen sulfide; and byseparating by distillation from the excess m-xylidine, and by solutionin 30% hydrochloric acid from the {so-dehydro-thio-m-xylidine
LITERATURE.—Lange, Zwischenprodukte, #2232Cain, Intermediate Products (2d Ed.), 80Anschutz and Schultz, Ber., 22, 582 (1889)Paul, Zeitsch. angew. Chem., 9, 679 (1896)
Dyes Derived from Dehydro-thio-m-xylidine
SchultzNumberfor Dye
120
121
122
Ordinary Name andClass of Dye
MONOAZO DYESSalmon Red
Erica B
Erica G
Statistics ofImport and
Manufacture
M'20:— ?
I '14:— 5,349I '20:-- 2,393M'19:— ?
I 14:— 2,370I '20:— 1,142M'18:— ?
Other IntermediatesUsed and Notes
Amino-R Acid
l-Naphthol-3:8-disulf onic Acid
GAcid
DyeAppli-cationClass
D
D
D
fso-Dehydro-thio-m-xylidine
l-(6-Amino-w-tolyl)-3: 5-dimethyl-6enzothiazole (C. A. nomen.)
= 268
FORMATION.—As a by-product in the manufacture of dehydro-thio -mxylidine (see dehydro-thio-m-xylidine)
LITERATURE.—See dehydro-thio-m-xylidine
Heumann, Aailinefarben, 4, 752
186 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from fso-Dehydro-thio-m-xylidine
SchultzNumberfor Dye
123
Ordinary Name andClass of Dye
MONOAZO DYEEmine Red
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
Schaeffer's Acid
DyeAppli-cationClass
A
Delta Acid
See, l-Naphthylamine-4: 8-disulfonic Acid
and 2-Naphthylamine-7-sulf onic Acid
1:6-(or 1:7-)Diacetamido-anthraquinone
H 3 C.OC.NH
r. NH.CO.CH3o\y\
I j =Ci8H1
FORMATION.—The above intermediate is obtained by reduction andacetylation of the easily soluble dinitro-anthraquinone, preparedfrom the crude dinitration product of anthraquinone.
LITERATURE.—Ger. Pat. 72,685, 198,048Lange, Zwischenprodukte, #3218
Dyes Derived from 1:SchuitzNumberfor Dye
812
813
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
IndanthreneOrange RT
IndanthreneCopper R
6-(or 1:7-)Diacetamido-anthraquinoneStatistics ofImport andManufacture
I '14:— 2,103I J20:— 382
I '14:— 1,268
Other IntermediatesUsed and Notes
2-Acetamido-anthraquinone
1-Acetamido-anthraquinone
DyeAppli-cationClass
V
V
DYES CLASSIFIED BY INTERMEDIATES 187
Diacetyl-o: o'-dinitro-benzidine
Diacetyl-3: 3'niinitro-benzidine (numbering from point of attach-ment)
2:2/-Dinitro-p:p/-biacetanilide (C. A. nombn. with numbering fromu chief function" or the acetamido groups)
O2N
H,COC.HN<
N02
>NH.COCH3 = <
FORMATION.—Benzidine is acetylated by boiling with acetic acid undera reflux, and the resulting diacetyl-compound is nitrated by dissolv-ing in 10 parts of nitric acid (sp. gr. 1.48) with cooling
LITERATURE.—Beil, IV, 964Brunner and Witt, Ber. 20, 1024 (1887)
Dye Derived from Diacetyl-o: o'-dinitro-benzidine
SchultzNumberfor Dye
715
Ordinary Name andClass of Dye
SULFUR DYEThiocatechine
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
[Sulfur and NasS]
DyeAppli-cationClass
S
£-(2:4-Diamino-anilino)-phenol (C. A. nomen.)
See, 2:4-Diamino-4/-hydroxy-diphenyla,mine
1:4-Diamino-anthraquinoue
CO,
co
NH2
NH2
FORMATION.—From l-nitro-4-amino-anthraquinone (derived from 1-amino-anthraquinone) by reduction with alkaline sodium sulfide
LITERATURE.—Lange, Zwischenprodukte, #3221, 3232, 3233Ullmann, Enzy. tech. Chemie, 1, 477
188 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from l:4-Diamino-anthraquinone
SchultzNumberfor Dye
816
873
Ordinary Xame andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Algol Red 5G
HelindoneBiwn AN
Statistics ofImport andManufacture
I '14 — 1,338I '20:— 51
I '14:— 2,831I '20:— 16,290
Other IntermediatesUsed and Notes
Benzoyl chloride(2 mols)
1-Bromo-anthraquinone(2 mols)
DyeAppli-cationClass
V
V
1:5-Diamino-anthraquinone
I | =Ci4H10N2O2 = 238AnnA/
H2X
FORMATION.—(1) From 1:5-dinitro-anthraquinone by reduction.(2) From 1:5-anthraquinone-disulfonic acid by treatment withammonia
LITERATURE.—Ullmann, Enzy. tech. Chemie, 1, 477Lange, Zwischenprodukte, #3109, 3115, 3222, 3265
Dyes Derived from 1: 5-Diamino-anthjaquinone
SchvUzNumberfor Dye
817
819
828
Ordinary Xame andClass of Dye
ANTHRAQUTSONE ANDALLIED DYES
Algol Yellow R
Algol Red R
IndantkreneBordeaux B
Statistics ofImport and
Manufacture
I '14:— 4,887I '20:— 2,299
M'20:— ?
I '14:— 2,322I '20:— 7,335
I '20:— 2,741
Other IntermediatesUsed and Notes
Benzoyl chloride(2 mols)
Benzoyl chloride(2 mols)
[Oxidation]
2-Chloro-anthraquinone(2 mols)
DyeAppli-cationClass
V
V
V
DYES CLASSIFIED BY INTERMEDIATES 189
Dyes Derived from l:5-Diamino-anthraquinone (continued)
SchultzNumberfor Dye
845
848
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
(continued)Indanthrene
Maroon B,
IndanthreneGray B
Statistics ofImport and
Manufacture
I '20:— 46
I '14:— 401I '20:— 2,639
Other IntermediatesUsed and Notes
1:5-Diamino-anthra-quinone (2 mols)
1:5-Diamino-anthra-quinone (2 mols ?)
DyeAppli-cationClass
V
V
Diamino-anthraquinones
(Probably a mixture of the 1:4, 1' 5 and 1:8)
cCSchultzNumberfor Dye836
Dyes DerivedOrdinary Name andClass of DyeANTHRAQUINONE ANDALLIED DYESHelindoneBrown 3GN
from. Diamino-anthraqumonesStatistics ofI?ri port andManvfactureI '20:— 15,238
Other IntermediatesUsed and Notes2-Anthraquinonyl-ureachloride (2 mols)
DyeAppli-cationClassV
4:8-Diamino-anthrarufinH2N co OHllw A.> XJ.2FORMATION.—1: 5-Dinitro-anthraquinone is partly reduced, giving 1: 5-dihydroxyamino-anthraquinone, which is then transformed intodiamino-anthrarunnLITERATURE.—Georgievics and Grandmougin, Dye Chemistry, 275
190 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 4:8-Diamino-anthrarufin
SckulizNumberfor Dye
820
821
Ordinary Name andClass of Dye
ANTKRAQTTINONE ANBALLIED DYES
Algol BrilliantViolet R
Algol BrilliantViolet 2B
Statistics ofImport and
Manufacture
I '14:— 12,784I '20:— 7,856
I '14:— 3,893I '20:— 827
Other IntermediatesUsed and Notes
Diamino-anthraruiSn(2 mols)
[Succinic Acid]
Benzoyl cMoride(2 mols)
DyeAppli-cationClass
V
V
Diamino-azoxy-toluene
p-Azoxy-o-toluidine
5: S'-Azoxy-bis-o-foluidine (C. A. nomen.)
= C14H16X4O = 256
NH2
FORMATION.—From 5-rdtro-o-toluidine (NH2 = 1) by reduction, usingzinc dust and caustic soda
LITERATURE.—Cain, Intermediate Products (2d Ed.), 99Lange, Zwischenprodukte, #1792
SchvMzNumberfor Dye
483
484
Dyes Derived
Ordinary Name andClass of Dye
TEISAZO DYESSt. Denis RedRosophenine 4B
Milling Scarlet B,S
from Diamino-azoxy-toluene
Statistics ofImport andManufacture
I '14:— 1,496I '20:— 550
Other IntermediatesUsed and Notes
Nevile-Winther's Acid(2 mols)
Nevile-Winther's AcidRAcid
DyeAppli-cationClass
D
A
DYES CLASSIFIED BY INTERMEDIATES
4:6-Diamino-m-benzene-disulfonic Acid (C. A. nomen.)
See, m-Phenylene-4iamine-disulfonic Acid
2:5-Diamino-benzene-sulfonic Acid (C. A. nomen.)
See, p-Phenylene-diamine-sulfonic Acid
6: 6'-Diamino-m: m'-bi(benzene-sulfonic) Acid (C. A. nomen.)
See, Benzidine-disulfonic Acid
2:2/-Diamino-5: S'-bi-m-toluene-sulfonic Acid (C. A. nomen.)
See, o-Tolidine-disulfonic Acid
1:4-Diamino-2:3-dibromo-anthraquinone
191
c C
NH2
g =(
FORMATION.—By brominating 1:4-diamino-anthraquinone, probably innitro-benzene solution. (The corresponding chloro-compound ismade by action of sulfuryl chloride)
LITERATURE.—Cf. Lange, Zwischenprodukte, #3334Barnett, Anthracene and Anthraqirinone, 170-175, 190-
231
Dyes Derived from l:4-Diamino-2:3-dibromo-anthraquinone
ScktdtzNumberfor Dye
847
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYE
Algol Green B
Statistics ofImport and
Manufacture
I '14:— 2,796I '20:— 527
Other IntermediatesUsed and Notes
l:4-Diairdno-2:3-di-bromo-anthraqui-none (2 mols)
DyeAppli-cationClass
V
192 DYES CLASSIFIED BY INTERMEDIATES
2:7-Diamino-9-dioxide-?: ?-<f ibenzothiophene-disulfonic(C. A. nomen.)
See, Benzidine-sulfon-disulfonic Acid
p: /-Diamino-diphenylamine
prp'-Imino-bisaniline (C A. nomen.)
>NH2 =Ci2H 1 3 N 3 =199
Acid
STATISTICS.—Imported '14:—very small amount
FORMATION.—Equal molecules of aniline and p-phenylene-diamine areoxidized at 0° by means of potassium permanganate to a blue in-damine, which is then reduced with zinc dust and hydrochloric acid
LITERATURE.—Nietzke, Ber., 16, 474Lange, Zwischenprodukte, #1636, 1753
Dye Derived from j&:j&'-Diamino-diplienylamine
SchuttzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
923
ANILINE BLACKGROUP
Furreine DB I '14:— 54,005 p.M'19:— ?I '20:— 1,600
M'20:—168,459
•: p'-DiaTTiin o-diphenyl-amine (x mols) (?)
[Oxidation on hair]
Fur
4:4'-Diamino-diphenyl-3: S'-disulf onic Acid
See, Benzidine-disulfonie Acid
jp:^'-Diainiiio-diphenylethylene-o: o'-disulfonic Acid
See, Diamino-stilbene-disulfonic Acid
p: ^'-Diamino-diphenyl-met&ane
p:p'-Methylene-bisaniline (C A. nomen.)
DYES CLASSIFIED BY INTERMEDIATES 193
STATISTICS.—Manufactured '20:— ?
FORMATION.—50 parts of anhydro-formaldehyde-aniline (from equalparts of aniline and 40 per cent formaldehyde), 100 parts of anilineand 70 parts of aniline salt are heated together on a water bath,condensing to the p: p'-diamino-diphenyl-methane
LITERATURE.—Schultz, Farbstofftabellen (1914), #511Lange, Zwischenprodukte, #1297
Dyes Derived from ^://-Diamino-diphenyl-raethane
SchvltzNumberfor Dye
298
511
540
Ordinary Name andClass of Dye
DlSAZO DTEMilling Red R
TRIPHENTL-METHANEDYES
ParafuchsineParamagenta
Pacific Blue
Statistics ofImport andManufacture
I 14 — 65,026M'18:— ?M'19:—• ?M'20:— ?
Other IntermediatesUsed and Notes
R Acid (2 mols)
AnilineNitro-benzene
Anilineo-Toluidinep-Toluidine[Sulfonation]
or[p-Rosaniline+Benzoicacid and sulfonation]
DyeAppli-cationClass
A
B
D
p: ^'-Diamino-diphenyl-sulfide
See, Thioaniline
4:4/-Diamino-diphenyl-2:2'-sulfon-disul£onic Acid
See, Benzidine-sulfon-disulfonic Acid
Diamino-diphenyl-urea-disulfonic Acid
5.5/-Ureido-bis(2-amino~?)enzene-sulfonic Acid) ( C A. nomen.)
H O 3 S v ^
-NH—CO—NH
194 DYES CLASSIFIED BY INTERMEDIATES
FORMATION.—24 Parts of 4-nitro-amino-benzene-3-sulfonic acid is dis-solved in water containing 5.5 parts of soda ash, and phosgeneconducted in until the reaction is completed, as indicated by testnot diazotizing. The dinitro-body is now reduced with iron
LITERATURE.—Lange, Zwischenprodukte, #1823.
Dye Derived from Diamino-diphenyl-urea-disulfonic acid
SchultzNumberfor Bye
297
Ordinary Name andClass of Dye
DISAZO DYEBenzo Fast
Pink2BL
Statistics ofImport andManufacture
I '14:— 3,252I '14:—- 1,226
Other IntermediatesUsed and Notes
Gamma acid (2 mols)
DyeAppli-cationClass
D
p: ^'-Diamino-ditolyl-amine
4:4/-Imino-bis-o-^oluidine (C A. nomen. NH2=il)
H3C CH3
) ^ ) = C14H17N2 = 227
FORMATION.—By semidine rearrangement of amino-azo-0-toluenewhereby the hydrochloride of amino-azo-0-toluene is dissolved insulfurous acid solution and reduced with zinc dust, the productpoured into 50 per cent sulfuric acid, boiled and crystallized
LITERATURE.—Barber and Sisley, Sur un noveau mode de formation dela p-diamino-diphenylamine
Bull. Soc. Chim. [3] 33, 1232-34 (1905)Chem. Centr. 1906 [1], 232
Dye Derived from ^i^'-Diamino-ditolyl-amine
SchvltzNumberfor Dye
295
Ordinary Name andClass of Dye
DISAZO DYEDiphenyl Fast Black
Statistics ofImport andManufacture
I J14:— 882
Other IntermediatesUsed and Notes
Gamma Acidw-Tolylene-diamine
DyeAppli-cationClass
D
DYES CLASSIFIED BY INTERMEDIATES
p: /-Diamino-ditolyl-methane
4:4'-Methylene-bis-o-2oluidine (C. A. nomen.)
H3C CH3
^ I 2 ^ ^ V - N H 2 =
195
FORMATION.—100 parts of anhydro-formaldehyde-aniline + 250 parts ofo-toluidine hydrochloride + 500 parts of o-toluidine are warmedtogether on a water bath; and after 12 hours the mass is made al-kaline and the aniline is distilled off with the aid of steam. (Theanhydro-formaldehyde-aniline is only used as a carrier for the for-maldehyde)
LITERATURE.—Lange, Zwischenprodukte, #1315, 1316
Dye Derived from j&:£'-Diamino-ditolyl-methane
Schultz
for Dye
513
Ordinary Name andClass of Dye
TRIPKENYL-METHANEDYE
New Fuchsine O
Statistics ofImport and
Manufacture
I '14:— 300M'18:— ?M'19:— ?'MJ20:— ?
Other IntermediatesUsed and Notes
o-Toluidineo-Nitro-toluene
DyeAppli-cationClass
B
Diamino-dixylyl-methane
Methylene-biszylidine (<7. A. nomen)
NH2CH3CH3
NH2CH3CH3
FORMATION.—From formaldehyde and xylidine in the presence of acondensing agent
196 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from Diamino-dixylyl-methane
SchvltzNumberfor Dye
299
Ordinary Name andClass of Dye
DISAZO DYECinnabax Scarlet BF
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
R Acid (2 mols)
DyeAppli-cationClass
CL
Diamino-dixylyl-phenyl-methane
Benzal-biszylidine (JO. A. nomen.)
NH2CHsCH3
NH2CH3CH3
FORMATION.—From benzaldehyde and xylidine in. the presence of acondensing agent
LITERATURE.—Lange, Zwischenprodukte, #1434
Dye Derived from Diamino-dixylyl-phenyl-methane
SchuUzNumberfor Dye
300
Ordinary Name andClass of Dye
DISAZO DYECotton PonceauCinnabar Scarlet G
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
R Acid (2 mols)
DyeAppli-cationClass
CL
Di-^-aroino-ethoxy-diphenyl
See, Ethoxy-benzidine
l:3-Diamino-2-hydroxy-benzene-5-sulfonic Acid
See, 2: 6-Diamino-l-phenol-4-suKonie Acid
DYES CLASSIFIED BY INTERMEDIATES
2:4-Diamino-4'-hydroxy-diphenylaminep-(2:4-Diamino-anilino)-phenol (C. A. nomen.)
= 2 1 5
197
NH2
FORMATION.—Molecular proportions of 4-chloro-l: 3-dinitro-benzeneand p-amino-phenol are heated to boiling in aqueous suspension withsomewhat more than theoretical amount of limestone. The heat-ing is done by direct steam in a vessel provided with a reflux con-denser. After all the chloro-nitro-benzene has disappeared, theliquid is cooled and the crystalline 2: 4-dinitro-4'-hydroxy-diphenyl-amine is separated and washed. This is then reduced to the de-sired 2:4-diamino-4/-hydroxy-diphenylamine
LITERATURE.—Cain, Intermediate Products (2d Ed.), 74Lange, Zwischenprodukte, #1670
Dye Derived from 2:
SchvltzNumberfor Dye
732
Ordinary Name andClass of Dye
SULFUR DYEAutogene Black
4-Diamino-4/-hydroxy-diphenylamine
Statistics ofImport and
Manufacture
I 14:— 7,495
Other IntermediatesUsed and Notes
Phenol[S.O, S+NasS]
DyeAppli-cationClass
S
a-Diamino-naphthalene1: 5-Diamino-naphthalene (not considered herein)
jS-Diamino-naphthalene1: 8-Diamino-naphthalene (not considered herein)
4:5-Diamino-2:7-naphthalene-disulfonic Acid (C. A. nomen.)
See, 1:8-Naphthylene-diamine-3: 6-disulfonic Acid
4:8-Diamino-2:6-naphthalene-disulfonic Acid (C. A. nomen.)See, 1: 5-Naphthylene-diamine-3: 7-disulfonic Acid
1:4-Diamino-2-naphthalene-sulfonic Acid (C. A. nomen.)See, 1:4~Naphthylene-diamine-2-sulfonic Acid
198 DYES CLASSIFIED BY INTERMEDIATES
2:7-Diajnino-naphthalene-sulfonic Acid (C. A. nomen.)
See, 2: 7-Naphthylene-diamine-sulfonic Acid
5:7-Diamino-2-naphthaIene-suUonic Acid (C. A. nomen.)
See, 1:3-Naphthylene-diamine-6-sulfonic Acid
6:8-Diamino-2-naphthalene~sulfonic Acid (C. A. nomen.)
See, 1: 4-N*aphthylene-diamine-6-sulfonic Acid
2:6-Diamino-l-phenol-4-sulfonic Acid (C. A. nomen. OH—1)
1: 3-Diamino-2-hydroxy-benzene-5-sulfonic Acid
OH
™ ! = 204
SO3]
FORMATION.—Phenol is sulfonated by dissolving in hot sulfurie acid,cooled, diluted, and then dinitrated, using nitric acid and heatingto boiling. The dinitro-phenol-sulfonate is then isolated, dissolvedin water, and reduced with ammonium sulfide, and the diamineprecipitated by acidification
LITERATURE.—Lange, Zwischenprodukte, #1137Cain, Intermediate Products (2d Ed.), 129, 130
Dyes Derived from 2
SchvltzNumberfor Dye
288
289
Ordinary Name andClass of Dye
DISAZO DYESAcid Alizarin
Black SEPalatine Chrome
Black F
Acid AlizarinBlack SN
Palatine ChromeBlackS
: 6-Diamino-l-phenol-4-sulfonic Acid
Statistics ofImport and
Manufacture
I '14:— 19,185I '20:— 34,302
M '17:— ?M'18:— ?M 19:— ?
Other IntermediatesUsed and Notes
0-Naphthol (2 mols)
/3-NaphtholSchaeffer's Acid
DyeAppli-cationClass
ACr
ACr
DYES CLASSIFIED BY INTERMEDIATES 199
Diamino-stilbene-disulfonic Acidp: p'-Diamino-diphenylethylene-a: o'-disulfonic Acid
DS (abbreviation for above in com/pounds, less 2-NH2)
4:4'-Diamino-2:2'-stilbene-disulfonic Acid (<7. A. nomen.)
SO3H HO3S
\ = CuHuNiOflS* = 370
STATISTICS.—Manufactured '17:— ?Manufactured ' 18:— ?Manufactured '19:—5,021 lbs.Manufactured '20.-142,227 lbs.
FORMATION.—From sodium salt of p-nitro-toluene-0-sulfonate by dis-solving in water and boiling with caustic soda until the color be-comes deep red. Then reduction is effected by adding zinc dustuntil the liquid is decolorized
LITERATURE.—Cain, Intermediate Products (2d Ed.), 98Lange, Zwischenprodukte, #1454
SckultzNumberfor Dye
301
302
303
304
305
Dyes Derived from
Ordinary Name andClass of Dye
DISAZO DYESHessian Purple N
Brilliant HessianPurple
Brilliant YellowPaper Yellow
Chrysophenine G
Hessian Yellow
L Diamino-stilbene-disulfonic Acid
Statistics ofImport andManufacture
I '14:— 465
I '14:—278,000M'17:— ?M'18:— 1,664M'19:— 48,723I '20:— 126M'20:— 91,218
I '14:—157,799M'17.— ?M'18:—41,663M'19:— 86,795I '20:— 3,661M'20:—247,202
Other IntermediatesUsed and Notes
jft-Naphthylamine(2 mols)
Broenner's Acid(2 mols)
Phenol (2 mols)
Phenol (2 mols)[Ethylation]
Salicylic Acid (2 mols)
DyeAppli-cationClass
D
D
DA
D
D
200 DYES CLASSIFIED BY INTERMEDIATES
3:5-Diamino-^-foluene-sulfonic Acid (C. A. nomen.
l-Tolylene-2: 6-diamine-4-sulfonic Acid
Toluylene-diamine-sulfonie Acid
l-Methyl-2: 6-diainino-benzene-4-sulfoiiic Acid
SO3H
CH3
FORMATION.—From o-nitro-toluene by sulfonation, nitration and re-duction
LITERATURE.—Lange, Zwisehenprodukte, #1096
Dyes Derived from 3:5-Diamino-p-toluene-sulfonic Acid
SchvltzNumberfor Dye
285
286
287
488
Ordinary Name andClass of Dye
DISAZO DYESTohiylene Brown G
Toluylene Yellow
ToluyleneOrange RR
TETHAKTSAZO DYEToluylene Brown R
Statistics ofImport and
Manufacture
I '14:— 5,485
I '14:— 500
I '14:— 201
Other IntermediatesUsed and Notes
m-Phenylene-diamine
Nitro-m-phenylene-diamine (2 mols)
j3-Naphthylamine(2 mols)
Naphthionic Acid(2 mols)
m-Phenylene-diamine(2 mols)
DyeAppli-cationClass
D
D
D
D
4:6-Diamino-m-^oluene-sulfonic Acid (C. A. nomen.
w-Tolylene-diamine-sulfonic Acid
7n-Toluyleneniiannne-suKonic Acid
l-Methyl-2:4-diamino-benzene-5-sulfonic Acid
SO3H
= 2 0 2
DYES CLASSIFIED BY INTERMEDIATES 201
STATISTICS.—Manufactured in 1918, 1919, 1920, but in undisclosedquantities
FORMATION.—By addition of m-tolylene-diamine sulfate to oleum, andheating the mixture for three hours on a water bath.
LITERATURE.—Cain, Intermediate Products (2d Ed.), 87Lange, Zwischenprodukte, #1096
Dyes Derived from 4: 6-Diamino-m-toluene-sulfonic Acid (SOZH = 1)
SchvltzNumberfor Dye
362
392
Ordinary Name andClass of Dye
DISAZO DYESToluylene Orange ROxydiamine
Orange R
Toluylene Orange G
Statistics ofImport and
Manufacture
I '14:— 25,908M'19:— ?I '20:— 1,653
I '14:— 67,022M'18:— ?M'19:— ?M'20:— ?I '20:-- 273
Other IntermediatesUsed and Notes
Tolidine4: 6-Diamino-m-
toluene-sulfonicAcid (2 mols)
Tolidineo-Cresotic Acid
DyeAppli-cationClass
D
D
Dianisidineo-Dianisidine
D (abbreviation for Dianisidine in compounds, without the 2-NH2
groups)
O O.CH 3
/ ~ ^ = Ci4Hi6N2O2 = 244
STATISTICS.—Imported '14:—10,656 lbs.Manufactured '17:—11,702 lbs.Manufactured ' 18:— ?Manufactured '19:—107,441 lbs.Manufactured ;20:— ?
FORMATION.—o-Nitro-anisole is reduced by zinc dust in presence ofcaustic soda and alcohol to hydrazo-anisole, which is rearranged todianisidine by being warmed with dilute sulfuric acid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 96I^ange, Zwischenprodukte, ^1204
202 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Dianisidine
SchultzNumberfor Dye
Ordinary Name andClass of Dye
DISAZO DYESBenzopurpurin 10B
Diazurine B
Azo Violet
Dianisidine Blue
Azophor Blue D
Azophor Black S
Trisulfon Blue B
Benzoazurine G
Benzoazurine 3G
Congo Blue 2B
Direct Violet BB
I '14:M'18:M'19:M'20:I '20:
Statistics ofImport and
Manufacture
47,768??
41,2652,205
I '14:-
I '14:—
140
813
I '14:— 7S,699M'18M'19I '20M'20
-150,589- 287-237,328
I '20:— 201
I '14:— 4,396
Other IntermediatesUsed and Notes
Naphthionic Acid(2 mols)
l-Naphthylamine-6-sulf onic Acid (2 mols)
0-Naphthol (2 mols)
Naphthionic AcidNevile-Winther's Acid
/3-Naphthol (2 mols)
[Stable tetrazo-dianisoleused with p-nitro-aniline]
[Stable tetrazo-dianisolemixed with diazo m-nitro-aniHne, etc.]
l-Naphthol-3:6:8-trisulfonic Acid
i8-Naphthol
Nevile-Winther's Acid(2 mols)
l-Naphthol-5-sulfonic(2 mols)
It AcidNevile-Winther's Acid
1:7-Dihydroxy-naph-thalene-4-sulfonicAcid
w-Tolylene-diamine
DyeAppli-cationClass
D
D
D
ME
MF
D
D
D
DYES CLASSIFIED BY INTERMEDIATES 203
Dyes Derived from Dianisidine {continued)
SchulizNumberfor Lye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
414
415
416
417
418
419
420
421
422
DISAZO DYES{continued)
Indazurine B
Dianil Blue G
Brilliant Azurine 5G
Chlorazol Blue3G or R
Diamine BrilliantBlueG
Chicago Blue RW
Azidine Wool Blue B
Oxamine Blue B
Chicago Blue 4B
M'19:-
M'20:-
I '14:-I '20:-
22,3241,563
I '14:— 10,151
I '14:-I '20:-
I '14:-M'19:-I '20:-
M'20:-
11,59251
15,176?351
I '14:-I '20:-
I '14:-
35,89113
8,269
1:7-Dihydroxy-naph-thalene-4-sulfonic Acid
RAcid
Chromotropie Acid(2 mols)
1:8-Dihydroxy-naph-thalene-4-sulfonic Acid(2 mols)
l-Chloro-8-naphthol-5-sulf onic Acid (2 mols)
orl-Chloro-8-naphthol-4-
sulf onic Acid (2 mols)
l-Chloro-8-naphthol-3:6-disulf onic Acid(2 mols)
l-Amino-8-naphthol-2:4-disulfonic Acid
iS-Naphthol
Croceine Acidl-Amino-8-naphthol-
4-sulfonic Acid
l-Amino-5-naphthol-7-suKonic Acid
Nevile-"Wlnther's Acid
l-Amino-8-naphthol-2:4-disulfonic Acid
l-Amino-8-naphthol-4-sulf onic Acid
204 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Dianisidine (continued)
SchultzNumberfor Dye
423
424
425
426
427
428
429
430
455
Ordinary Name andClass of Dye
DISAZO DYES(continued)
Chicago Blue B
Chicago Blue 6B
Benzo Cyanine 3B
Diamine Pure BlueBenzaminePure
Blue
Indazurine GM
Direct Blue B
Indazurine BB
Indazurine 5GM
TRISAZO DYESColumbia Black B
M'18:— ?
I '20:M '20:
Statistics ofImport arid
Manufacture
k—118,5423:— ?
7,480?
I '14:— 1,001
I '14:M '17:M'18 :M'19:
'20:M J20:
I '14:M'17:M'18:I '20:
12,881??
192,350652
223,100
21,42114,823
?7,055
I '14:—165,727
Other IntermediatesUsed and Notes
l-Amino-8-naphthol-4-sulf onic Acid (2 mols)
l-Amino-8-naphthol-2:4-disulfonic Acid(2 mols)
H Acidl-Ainino-8-naphthol-4-
sulf onic Acid
H Acid (2 mols)
1:7-DIhydroxy-2-napli-thoic-4-sulfonic Acid
Nevile-Winther's Acid
1:7-DIhydroxy-6-naph-thoic-3-sulf onic Acid
Nevile-Winther's Acid
1:7-Dmydroxy-2-naph-thoic-4-sulf onic Acid
RAcid
1:7-Dihydroxy-2-naph-thoic-4-sulf onic Acid
H Acid
2 R Acidm-Tolylene-diamine
(2 mols)
DyeAppli-cation
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Dianisidine (continued)
205
SchultzNumberfor Dye
456
457
Ordinary Name andClass of Dye
TRISAZO DYES(continued)
Congo Fast Blue BBenzo Fast Blue B
TrisulfonBrown GG
Statistics ofImport and
Manufacture
I '14:—100,495I '20:— 1,821
I '14:— 7,562I '20:— 38,411
Other IntermediatesUsed and Notes
a-Naphthylaminel-Naphthol-3: 8-disul-
fonic Acid
2 R AcidSalicylic Acidm-Phenylene-diamine
DyeAppli-cationClass
D
D
Dibenzo-pyrroleSee, Carbazole
Dibenzyl-aniline-sulfonic (disulfonic) Acid[(iVr-Benzyl-anilino)-methyl]-6enzene-sulfonic Acid (C A. nomen.)
C6H5. CH2—N—CH2. C6H4. SO3H
FORMATION.—Aniline, benzyl chloride and sodamide are mixed togetherand then heated up on water bath until ammonia is all off, resultingin the formation of dibenzyl-aniline. This latter is then sulfonated
LITERATURE.—Lange, Zwischenprodukte, #1561
Dye Derived from Dibenzyl-aniline-sulfonic (disulfonic) Acid
SchultzNumberfor Dye
531
Ordinary Name andClass of Dye
TRIPHENYL-METHANEDYE
Eriocyanine A
Statistics ofImport and
Manufacture
I '14:— 25,091I '20:— 8,223
Other IntermediatesUsed and Notes
Tetramethyl-p: p'-dia-roino-benzohydrol-sulfonic Acid
[Oxidation]
DyeAppli-cationClass
A
206 DYES CLASSIFIED BY INTERMEDIATES
5:7-Dibromo-2-chloro-3-pseudoindolone (C. A. nomen.)
See, 5:7-Dibromo-isatin Chloride
5:7-Dibromo-isatin Chloride
5: 7-Dibromo-2-chloro-3-23Seudoindolone (C A. nomen.)
Br N
( Y CB r
C . Cl = C8H2Br2ClNO = 323.5
FORMATION.—Isatin is gently wanned with bromine in concentratedsulfuric acid, giving 5:7-dibromo-isatin, which is then wannedwith phosphorus pentachloride and benzene
LITERATURE.—Ullmann, Enzy. tech. Chemie, 6, 526Lange, Zwischenprodukte, #2122
Dyes Derived from 5:7-Dibromo-isatin Chloride
SchvltzNumberfor Dye
893
895
Ordinary Name andClass of Dye
INDIGO GROUP DYESAlizarin Indigo G
Alizarin Indigo ZR
Statistics ofImport and
Manufacture
I '20:— 1,596
I '20:— 3,514
Other IntermediatesUsed and Notes
1-Anthrol
a-Naphthol
DyeAppli-cationClass
V
V
2:6-DicMoro-aniline
NH2
FORMATION.—From 2:5-dichloro-nitro-benzene by reduction with ironand hydrochloric acid
LITERATURE.—Cain, Intermediate Products (2d Ed.)> 50
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 2:5-Dichloro-aniline
207
SchultzNumberfor Dye
218
469
470
471
472
Ordinary Name andClass of Dye
DISAZO DYENigrophor BASF
TEISAZO DYESChloramine
Black N
ChloramineGreen B
ChloramineBlue 3G
ChloramineBlueHW
Statistics ofImport andManufacture
I '14:— 39,600M'19:— ?I '20:— 1,763M '20:— ?
I '14:— 1,675M'19:— ?M'20:— ?
I '14:— 286M'19:— ?I '20:— 882
Other IntermediatesUsed and Notes
l-Amino-8-naphthol-5-sulf onic Acid
p-Nitro-aniline
Benzidinem-Phenylene-diamineHAcid
BenzidinePhenolHAcid
BenzidineH Acid (2 mols)
BenzidineGamma AcidHAcid
DyeAppli-cationClass
MF
D
D
D
D
1:5-Dichloro-anthraquinone
Cl
Y J =C1 4H6Cl2O2=277
FORMATION.—Sodium 1: 5-anthraquinone-disulfonate in dilute hydro-
chloric acid is heated to boiling and treated with a solution of
sodium chlorate
LITERATOBE.—Cain, Intermediate Products (2d Ed.), 250Lange, Zwischenprodukte, #3083, 3086Ullmann, Enzy. tech. Chemie, 1, 472
208 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from l:5-Dichloro-anthraquinone
SchultzNumberfor Dye
832
Ordinary Name andClass of Dye
ANTHRAQTJINONE ANDALLIED DYES
IndanthreneViolet RN
Statistics ofImport and
Manufacture
I '14:— 11,667I '20:— 49
Other IntermediatesUsed and Notes
Anthranilic Acid(2 mols)
DyeAppli-cationClass
V
2:6-Dichloro-anthraquinone
X ? -0
FORMATION.—2:6-Anthraquinon.e-disulforue acid is treated withchlorine
LITERATURE.—Ullmann, Enzy. tech. Chemie, 1, 472Cf. Ber., 37, 4706Lange, Zwischenprodukte, #3164, 3165
Dyes Derived from 2:6-Dichloro-anthraquinone
SchultzNumberfor Dye
826
829
Ordinary Name andClass of Dye
ANTHH A QUINONE ANDALLIED DYES
Indanthiene Red G
Algol Bordeaux 3B
Statistics ofImport andManufacture
I '20:— 61
Other IntermediatesUsed and Notes
1-A miTi o-anthraquiaone(2 mols)
l-Amino-4-metlioxy-anthjaquinoiie (2 mols)
DyeAppli-cationClass
V
V
2:7-Dichloro-anthraqvdnone
= C l 4 H 6 C l 2 ° 2 = 2 7 7
DYES CLASSIFIED BY INTERMEDIATES 209
FORMATION.—From anthraquinone-2:7-disulfonic acid by treatmentwith hydrochloric acid and sodium chlorate; or better from 9:10-dichloro-anthracene-2: 7-disulfonic acid by treatment with the samereagents
LITERATURE.—Ullmann, Enzy. tech. Chemie, 1, 472Lange, Zwischenprodukte, #3165
Dyes Derived from 2:7-Dichloro-anthraquinone
SchvltzNumberfor Dye
827
830
Ordinary Name andClass of Dye
ANTHRAQTJINONE ANDALLIED DYES
IndanthreneBordeaux B extra
Indanthrene Red R
Statistics ofImport andManufacture
I '14:— 28,728I '20:— 4,056
I '14:— 2,099I '20:— 6,595
Other IntermediatesUsed and Notes
l-Amino-6-chloro-an-thraquinone (2 mols)
1-Amino-anthraquinone(2 mols)
DyeAppli-cationClass
V
V
2:5-Dichloro-benzaldehyde
HCO
FORMATION.—From 2-chlor-5-mtro-benzaldehyde by the substitutionof the nitro group by chlorine
LITERATURE.—Lange, Zwischenprodukte, #669Beil, III , 13
Dyes Derived from 2:5-Dichloro-benzaJdehyde
SchulteNumberfor Dye
497
501
Ordinary Name andClass of Dye
TRIPHENTL-METHANEDYES
New Fast Green 2BVictoria Green 3B
Glacier BlueBrilliant Glacier
Blue
Statistics ofImport and
Manufacture
I '14:— 44,595
I '14:— 2,495
Other IntermediatesUsed and Notes
Dimethyl-aniline(2 mols)
[Oxidation]
Methyl-o-toluidine(2 mols)
[Oxidation]
DyeAppli-cationClass
B
B
210 DYES CLASSIFIED BY INTERMEDIATES
o: o'-Dichloro-benzidine
2: 2'-Dichloro-benzidine (C. A. nomen. NH2=1)
3: 3'-Dichloro-benzidine (Usualnumbering, 'point of attachment = 1)
Cl Cl
= CiaHioCljNa = 253
FORMATION.—(1) By chlorinating of diacetyl-benzidine, and hydrolyz-ing product. (2) By reducing o-chloro-nitro-benzene in alkalinesolution with zinc, and rearranging with acid the o: o'-dichloro-hydrazo-benzene formed (similar to benzidine formation from nitro-
benzene)
LITERATURE.—Cain, Intermediates (2d Ed.), 94Lange, Zwischenprodukte, #1229, 1230
Dyes Derived from o: o' Dichloro-benzidine
SchuLtzNumberfor Dye
356
357
358
Ordinary Name andClass of Dye
DISAZO DYESDianol Red 2B
Dianol Red B
Brilliant Dianol RedR extra
Diphenyl Red
Statistics ofImport arid
Manufacture
I '14:— 4,422I '20:— 17,632
I '14:— 14,305I '20:— 3,704
Other IntermediatesUsed and Notes
Naphthionic Acid(2 mols)
Broenner's Acid(2 mols)
Amino-R Acid(2 mols)
DyeAppli-cationClass
D
D
D
2:5-Dichloro-4~(4: 5-dihydro-5-keto-3-methyl-l-pyrazolyl)-6en-zene-sulfonic Acid (C. A. nomen,)
See, l-(2 /: S^Dic
2:5-Dichloro-nitro-benzene
NO2
DYES CLASSIFIED BY INTERMEDIATES 211
FOKMATION.—By nitration of p-dichloro-benzene with mixed acidLITERATURE.—Cain, Intermediate Products (2d Ed.), 14
Lange, Zwischenprodukte, #674
USES.—For preparing 2: 5-dichloro-aniline
3:6-Dichloro-£hthalic Acid
COOH
C I / N C O O H
V C 1= C8H4CI2O4 — 235
STATISTICS.—Imported '14:—very smallManufactured '18:— ?
FORMATION.—(1) From dichloro-naphthalene tetrachloride, by oxida-tion with nitric acid. (2) From phthalic anhydride dissolved inoleum by chlorination in presence of iodine, and by separation fromthe isomers formed at the same time
LITERATURE.—Lange, Zwischenprodukte, #992Cain, Intermediate Products (2d Ed.), 165
Dyes Derived from 3:6-Dichloro-phthalic Acid
tSchuiteNumberfor Dye
584
593
Ordinary Name andClass of Dye
XANTHONE DYESFast Acid
BlueR
Phloxine P
Statistics ofImport and
Manufacture
I '14:— 3,022I '20:— 130
I '14:— 2,244M'17:— ?M'18:— ?M '19:— ?M'20:— ?
Other IntermediatesUsed and Notes
Resorcinol (2 mols)p-Phenetidine (2 mols)[PC15; Sulfonation]
or[Tetrachloro-fluores-ceine and p-phene-tidine; Sulfonation]
Resorcinol (2 mols)[Bromination]
or[Dichloro-fluoresceine
brominated]
DyeAppli-cationClass
A
A
212 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 3
SchultzNumberfor Dye
594
595
Ordinary Name andClass of Dye
XANTHONE DYES(continued)
Cyanosine, SpiritSoluble
Rose Bengal
: 6-Dichloro-phthalic Acid (continued)
Statistics ofImport and
Manufacture
I '14:— 2,277M'20:— ?
Other IntermediatesUsed and Notes
Resorcinol (2 mols)[Bromination, methyla-
tion]or
[Phloxine P methylester]
Resorcinol (2 mols)[Iodation]
or[Dichloro-fiuoresceine
iodated]
DyeAppli-cationClass
A
A
l-(2:5-Dichloro-4-snlfo-phenyl)-3-methyl-5-pyrazolone
2: 5-Dichloro-4-(4 roniihydr o-5-ket o-3-methyl-l-py r azoly 1) -&en-
zene-sulfonic Acid (C. A. nwnen.)
Cl
N
C 1
2C—C • CH3
FORMATION.—^2:5-Dichloroaniline-4-sulfonic acid is diazotized and re-
duced to 2:5-dichloro-phenyl-hydrazirie-4-sulfonic acid, which latter
body by condensation with ethyl acetoacetate forms the above
pyrazolone derivative
LITERATURE.—Cain, Intermediate Products (2d Ed.), 170
Cf. Lange, Zwischenprodukte, #138
DYES CLASSIFIED BY INTERMEDIATES 213
Dye Derived from l-(2:5-Dichloro-4-sulfo-phenyl)-3-methyl-5-pyrazolone
SchultzNumberfor Dye
22
Ordinary Name andClass of Dye
PYRAZOLONE DYEXylene YeUow 3G
Statistics ofImport and
Manufacture
I 14:— 23,074I '20:— 77,782
Other IntermediatesUsed and Notes
Sulfanilic Acid
DyeAppli-cationClass
A
jp-Diethylamino-azo-benzeneBenzene-azo-diethylanilineiV":iV-Diethyl-p-plienylazo-aniline (C. A. nomen.)
)N 2 <Q)N(C2H 5 ) 2 = Ci6Hi9N3=253
FORMATION.—By coupling diazo-benzene chloride (diazotized aniline)with diethyl-aniline
LITERATURE.—Ullmann, Enzy. tech. Chemie, 2, 80
Dyes Derived from ^-Diethylamino-azo-benzene
SchultzNumberfor Dye
641
646
Ordinary Name andClass of Dye
OXAZINE DYESCoreine ERCoelestine Blue B
Coreine Alt
Statistics ofImport and
Manufacture
I 14:— 1,320I J20:— 44
Other IntermediatesUsed and Notes
Gallamide
GaJlamideAniline[Sulfonation]
or[Coreine E.R, Aniline,
Sulfonation]
DyeAppli-cationClass
M
M
^-Diethylamino-benzoyl Chloride
COC1
= 211.5
214 DYES CLASSIFIED BY INTERMEDIATES
FORMATION.—(1) p-Amino-benzoic acid is ethylated, and then treatedwith phosphorus pentachloride to form the desired acid chloride.(2) Diethyl-aniline is subjected to the action of phosgene first atordinary temperatures until no more gas is absorbed, and then aftermelting the crystalline mass first obtained. The product is mixedwith water and the excess of diethyl-aniline removed by acetic acid.The acid chloride is formed by treatment with phosphorus penta-chloride
LITERATURE.—Cain, Intermediate Products (2d Ed.), 148
Dye Derived from ^-Diethylamino-benzoyl Chloride
SchultzNumberfor Dye
534
Ordinary Name andClass of Dye
TRIPHENYL-METHA2STEDYE
Acid Violet 7B
Statistics ofImport and
Manufacture
I '14:— 21,665I '20:— 51
Other IntermediatesUsed and Notes
iV-Methyl-diphenyl-amine (2 mols)
DyeAppli-cationClass
A
3-Diethylamino-^-cresol (C. A.nomen.0H=l)
Diethyl-wz-amino-p-cresol (OH=1)
OH
Q N ( C 2 H 5 ) 2 = C n H
CH3
FORMATION.—From diethyl-o-toluidine by sulfonation in the cold with
oleum and caustic soda fusion of the sulfonic acidLITERATURE.—Mohlau, Klimmer and Kahl, Zeit. Farb. Chem., 1902
316Lange, Zwischenprodukte, #815
Dye Derived from 3-Diethylamino-^-cresol (OH=1)
SckultzNumberfor Dye
620
Ordinary Name andClass of Dye
OXAZINE DYECapri Blue GON
Statistics ofImport andManufacture
T 14:— 128
Other IntermediatesUsed and Notes
Nitroso-dimethyl-ani-line
DyeAppli-cationClass
B
DYES CLASSIFIED BY INTERMEDIATES
Diethyl-m-amino-jfr-cresol (OH=1)
See, 3-Diethylamino-p-cresol (C A, nomen. OH=1)
5-Diethylaznino-2-nitroso-£henol (C. A. nomen.)
Nitroso-diethyl-m-amino-phenol
OH
215
FORMATION.—Diethyl-m-amino-phenol (which can be prepared by sul-fonating diethyl-aniline and then fusing the sulfonic acid to pro-duce the diethyi-m-amino-phenol) is dissolved in hydrochloric acid,cooled with ice to 0° C , and sodium nitrite solution introduced
LITERATURE.—Lange, Zwischenprodukte, #906
Dyes Derived from 5-Diethylamino-2-nitroso-phenol
SchultzNumberfar Dye
653
654
Ordinary Name andClass of Dye
OXAZINE DYES
Nile Blue A
Nile Blue 2B
Statistics ofImport and
Manufacture
I '14:— 1,518I '20:— 1,241
Other IntermediatesUsed and Notes
a-Naphthylamine
Benzyl-a-naphthyl-amine
DyeAppli-cationClass
B
B
m-Diethylamino-^henol (C. A. nomen.)
Diethyl-m-amino-phenol
OH
J N ( C 2 H 5 ) 2
STATISTICS.—Manufactured ' 18:— ?Manufactured '19:— ?Manufactured '20:— ?
FORMATION.—Diethyl-aniline is sulfonated with oleum, and the re-sulting diethyl-aniline-m-sulfonic acid fused with caustic soda
LITERATURE.—Cain, Intermediate Products (2d Ed.), 122Lange, Zwischenprodukte, #603-606, 2263
216 DYES CLASSIFIED BY INTERMEDIATES
SchuUzNumberfor Dye
570
572
573
574
579
581
Dyes Derived
Ordinary Name andClass of Dye
XANTHONE DYESRhodamine S
Rhodamine G
Rhodamine B
Rhodamine 3B
Sulfo Rhodamine BXylene Red B
Fast Acid Eosine GFast Acid
Phloxine A
from m-Diethylamino-phenol
II
II
IMMMMI
I
II
Statistics ofImport andManufacture
'14:-'20:-
'14:-'20:-
'14:-'17:-'18:-'19:-'20:-'20:-
'14:-
'14:-'20:-
- 600- 273
- 2,648- 517
- 59,354- ?- ?- ?- ?- 24,709
- 1,698
- 650- 5,234
Other IntermediatesUsed and Notes
Diethyl-m-amin o-phenol (2 mols)
[Succinic Anhydride]
Phthalic AnhydrideDiethyl-m-amino-
phenol (2 mols)Aniline [Removes one
C2H5 group]or
[Rhodamine B heatedwith Aniline Salt]
Phthalic AnhydrideDiethyl-m-amino-
phenol (2 mols)
Phthalic AnhydrideDiethyl-m-amino-
phenol (2 mols)[Ethyl esterification]
or[Rhodamine B
ethylated]
Benzaldehyde-di-sulfonic Acid
Diethyl-m-amino-phenol (2 mols)
[Oxidation]
Phthalic AnhydrideDiethyl-m-ainino-
phenol (2 mols)or
[Rhodamine B, sulfo-nated]
DyeAppli-cationClass
A
B
B
B
A
A
DYES CLASSIFIED BY INTERMEDIATES 217
Diethyl-anilineN: N-Diethyl-aniline (C. A. nomen.)
N(C2H5)2
STATISTICS.—Imported 14:—very small quantityManufactured 17:— 3,955 lbs.Manufactured 18:—48,048 lbs.Manufactured 19:—30,000 lbs.Manufactured '20:—180,542 lbs.
FORMATION.—Aniline is heated in an autoclave with ethyl alcohol inthe presence of a catalyst, for example, hydrochloric acid, hydro-bromic acid, or iodine
LITERATURE.—Cain, Intermediate Products (2d Ed.), 68Lange, Zwischenprodukte, #128
Dyes Derived from Diethyl-aniline
SchvlizNumberfar Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
499
TRIPHENYL-METHANEDYES
Brilliant Green
507
518
Xylene Blue VS
Ethyl VioletEthyl Purple
I 14:— 73,904M 1 8 : — ?M19:— ?I '20:— 25
M'20:— ?
I 14:— 2,130I '20:— 27,254
I 14:— 51,933
Diethyl-aniline (2 mols)Benzaldehyde[Oxidation]
Diethyl-aniline (2 mols)3-Methyl-benzalde-
hyde-4:6-disulfonicAcid
[Oxidation]
Tetraethyl-diamino-benzophenone
orDiethyl-aniline (3 mols)Phosgene
orTetraethyl-diamino-
diphenyl-methane
B
218 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Diethyl-aniline {continued)
SchidtzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cation
530
543
544
686
TBIPHENYL-METHANEDYES (continued)
Acid Violet 6BFonnyl VioletGuinea Violet
Patent Blue V
Cyanine B
AZINE DYEAmethyst Violet
I '14:—161,624M'17M'18M'19I '20
M'20- 3,925-144,207
-196,228- ?
I '14M'17M'18I '20:— 36,420
'14:-'20:-
8,39824
Ethyl-sulfobenzyl-aniline (2 mols)
[Formaldehyde, Oxida-tion}
Diethyl-aniline (2 mols)w^Nitro-benzaldehyde
or m-Hydroxy-benzaldehyde
[Sulfonation, Oxidation]
Diethyl-aniline (2 mols)m-Nitro-benzaldehyde
or m-Hydroxy-benzaldehyde
[Sulfonation, Oxidation]or
[Patent Blue Oxidized]
Diethyl-p-phenylene-diamine
AniHne or p-Toluidine[Oxidation]
Diethyl-aniline-m-sulfonic Acid
N: iV-Diethyl-metanilic Acid (C. A. nomen.)
= C10H15NO3S =
FORMATION.—From diethyl-aniline by sulfonation with oleum
LITERATURE.—Cain , Intermediate Products (2d Ed. ) , 122Lange, Zwischenprodukte, #631
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Diethyl-aniline-m-sulfonic Acid
219
SchultzNumberfor Dye
59
Ordinary Name andClass of Dye
MONOAZO DYEWool Violet S
Statistics ofImport and
Manufacture
I '14:— 308M'18:— ?M'19:— ?
Other IntermediatesUsed and Notes
2:4-Dinitro-ardline
DyeAppli-cationClass
A
N: N-Diethyl-metanilic Acid (C. A. nomen.)
See, Diethyl-aniline-m-sulfonic Acid
N: iV-Diethyl-^-nitroso-aniline (C. A. nomen.)
See, p-Nitroso-diethyl-aniline
N: iV-Diethyl-^-phenylazo-aniline (C. A. nomen.)
See, p-Diethylamino-azo-benzene
N: iV'-Diethyl-m-plienylene-diamine (C. A. nomen.)
s-Diethyl-m-phen^ lene-diamine
HNC2H5
JNH. C2H5 = C l o H i e N 2 ~ 1 6 4
FORMATION.—Probably by heating resorcinol with ethylamine in thepresence of a dehydrating agent
LITERATURE.—Cf. Green, Organic Coloring Matters (1908), 37.Cf. Calm, Ber., 16, 2792 (1883)
Dye Derived from JV: iNT-Diethyl-m-phenylene-diamine
SchultzNumberfor Dye
678
Ordinary Name andClass of Dye
AZENE DYEFast Neutral
Violet B
Statistics ofImport and
Manufacture
MJ17:— ?
Other IntermediatesUsed and Notes
Nitroso-dimethyl-aniline
DyeAppli-cationClass
B
220 DYES CLASSIFIED BY INTERMEDIATES
N: JV-Diethyl-p-jphenylene-diamine (C. A. nomen.)
p-Amino-diethy 1-an iline
N(C2H5)2
NH2
FORMATION.—Diethyl-aniline is converted into p-nitroso-diethyl-anilineby nitrous acid, which by reduction with zinc dust and hydrochloricacid yields the p-amino-diethyl-aniline
LITERATURE.—Cf. Lange, Zwischenprodukte, #561-563
Dye Derived from N: iV-Diethyl-/>-phenylene-diamine
SchultzNumberfor Dye
686
Ordinary Name andClass of Dye
AZINE DYEAmethyst Violet
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
Diethyl-anilineAniline or p-Toluidine[Oxidation]
DyeAppli-cationClass
A
s-Diethyl-m-phenylene-diamine
See, N: iV'-Diethyl-m-phenylene-diamine
Dietlayl-^-phenylene-diannne-thiosiilfonic Acidp-Amino-diethyl-aniline-thiosulfonic Acid
4-Anainc)-lHiiethylamino-benzene-3-thiosuifonic Acid
2-Amino-5-diethylamino-6enzene-thiosulfonic Acid (C. A. nomen.)
N(C2H5)2
FORMATION.—12 parts of the zinc chloride double salt of diethyl-p-phenylene-diamine are dissolved in 90 parts of water, treated witha solution of 25 parts of aluminum sulfate and 20 parts of sodiumthiosulfate in 70 parts of water, and finally oxidized with 3 parts ofpotassium bichromate dissolved in 30 parts of water
LITERATURE.—Lange, Zwischenprodukte, #931, 932
DYES CLASSIFIED BY INTERMEDIATES 221
Dye Derived from Diethyl-^-phenylene-diamine-thiosulfonic Acid
SchultzNumberfor Dye
666
Ordinary Name andClass of Dye
TKLAZINE DYEIndochromogen S
Statistics ofImport andManufacture
Other IntermediatesUsed and Notes
1:2-Naphthoquinone-4: 6-disulfonic Acid
DyeAppli-cationClass
M
3:4-Dihydro-3:4-diketo-l:7-naphthalene-disulfonic Acid (C A.nomm.)
See, 1: 2~Naphthoquinone-4:6-disulfonic Acid
3:4-Dihydro-3:4-diketo-l-naphthalene-sulf onic Acid (C. A.nomen.)
See, 1: 2-Naphthoquinone-4-sulfonic Acid
£-(4 '• 5-Dihydro-5-keto-3-methyl-l-pyrozolyl)-6enzene-snlf onicAcid (C. A. nom&n.)
See, 3-Methyl-l-(p-sulfo-phenyl)-5-pyrazolone
1:2-Dihydroxy-anthraquinone
See, Alizarin
1:5-Dihydroxy-anthraquinone
See, Anthranifin
2:4-Dihydroxy-benzoic Acid
See, j8-Resorcylic Acid (C A. nomen.)
3:5-Dihydroxy-benzoic Acid
See, a-Resorcylic Acid (C A. nomen)
m-Dihydroxy-benzoic Acid
See, a-Resorcylic Acid (C. A. nomen.)
1:7-Dihydroxy-2-carboxy-naphthalene-4-sulfonic Acid
See, 1: 7-Dihydroxy-2-naphthoic-4r-sulfonic Acid
222 DYES CLASSIFIED BY INTERMEDIATES
1: 7-Dihydroxy-6-carboxy-naphthalene-3-sulfonic Acid
See, 1: 7-Dihydroxy-6-naphthoic-3-sulfonic Acid
Diliydroxy-£-methyl-coumariii
See, 7:8-Dihydroxy-4-methyl-coumarin (C. A. nomen.)
7:8-Dihydroxy-4-methyl-couinarin (C. A. nomen.)
Dihydroxy-0-methyl-coumarin
HO
FORMATION.—From pyrogallol and acetoacetic ethyl ester
LITEKATUEE.—J. pr. Ch. (2) 26, 68Ber., 16, 2127 (1883)
SchvtizNumberfor Dye
773
Dye Derived from
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYE
Anthracene Yellow
7:8-Dihydroxy-4-methyl-coumarin
Statistics ofImport and
Manufacture
I J14:— 4,046
Other IntermediatesUsed and Notes
[Bromination]
DyeAppli-cationClass
M
1: S-Dihydrosy-naphthalene
1:5-NaphthaJenediol (C A. nomen.)
OH
HO
STATISTICS.—Manufactured '19:—Manufactured '20:—
DYES CLASSIFIED BY INTERMEDIATES 223
FOBMATION.—By caustic soda fusion of sodium naphthalene-1: 5-disul-fonate or of sodium l-naphthol-5-sulfonate
LITERATURE.—Cain, Intermediate Products (2d Ed.), 230Lange, Zwischenprodukte, #2392Thorpe, Die. Chemistry, 3, 646
Dye Derived from l:5-Dihydroxy-naphthalene
SchultzNumberfor Dye
157
Ordinary Name andClass of Dye
MONOAZO DYEDiamond Black PV
Statistics ofImport and
Manufacture
I '14:—285,074
Other IntermediatesUsed and Notes
o-Amino-phenol-p-sulf onic Acid
DyeAppli-cationClass
M
2:7-Dihydroxy-naphthalene
2: 7-Naphthalenediol (C. A. nomen.)
H ° C O ° H =
FORMATION.—By caustic soda fusion of F acid (2-naphthol-7-sulfonicacid)
LITERATURE.—Lange, Zwischenprodukte, #2401Green, Organic Coloring Matters (1908), 54Thorpe, Die. Chemistry, 3, 647
Dyes Derived from 2:7-Dihydroxy-naphthalene
SchulizNumberfor Dye
3
655
Ordinary Name andClass of Dye
NITROSO DYEDioxine
OXAZINB DYEMuscarine
Statistics ofImport and
Manufacture
Other IntermediatesUsed and Notes
[Nitrous Acid]
Nitroso-dimethyl-aiuline
DyeAppli-cationClass
M
B
224 DYES CLASSIFIED BY INTERMEDIATES
1:7-Dihydroxy-naphthalene-2-carboxylic-4-sulfonic Acid
See, 1:7-Dihydrox>'-2-naphthoic-4-sulfonic Acid
1: T-Dihydroxy-naphthalene-e-caxboxylic-S-sulfonic Acid
See, 1: 7-Dihydroxy-6-naphthoic-3-siilfonic Acid
1:8-Dihydroxy-naphthalene-3:6-disulfonic Acid
See, Chromotropic Acid
4:5-Dihydroxy-2:7-naphthalene-disulfonic Acid (C. A. norntn.)
See7 Chromotropic Acid
1:7-Dihydroxy-naphtlialene-4-siilfonic Acid
4:6-Dihydroxy-l-naphthalene-sulfonic Acid (C. A. nomen.)
HO
OH
s o j a
FORMATION.—From 1 hydroxy-naphthaIene-2-carboxylic-4: 7-disulfonicacid by fusion -with alkalis, whereby first a sulfonic group is replacedby hydroxyl and then at a higher temperature carbon dioxide issplit out
LITERATURE.—Lange, Zwischenprodukte, #2617, 2618Thorpe, Die. Chemistry, 3, 650
Dyes Derived from l:7-Dihydroxy-naphthalene-4-sulfonic Acid
SchuUzNumberfor Dye
413
414
Ordinary Same andClass of Dye
DISAZO DYESDirect Violet BB
Indazurine B
Statistics ofImport and
Manufacture
I '14:— 4,396
Other IntermediatesUsed and Notes
Dianisidin.6m-Tolylene-diamine
DiardsidineRAcid
DyeAppli-cationClass
D
D
DYES CLASSIFIED BY INTERMEDIATES 225
1:8-Dihydroxy-naphthalene-4-sulfonic Acid
Dihydroxy-naphthalene-sulfonic Acid S
S Acid
4: 5-Dihydroxy-l-naphthalene-sulfonic Acid (C. A. nomen.)
HO OH
= Ci0H8O5S =
STATISTICS.—Imports '14:—2,178 lbs.
FORMATION.—(1) From l-naphthol-4: 8-disulfonic acid by fusion withcaustic soda, preferably in an autoclave. (2) From 1-naphthyl-amine-4:8-disulfonic acid by fusion with caustic soda, in an auto-clave. (3) From l-amino-8-naphthol-4-sulfonic acid by heatingwith sodium sulfite
LITERATURE.—Cain, Intermediate Products (2d Ed.), 230Lange, Zwischenprodukte, #2621, 2622
Dyes Derived from l:8-Dihydroxy-naphthalene-4-sulfonic Acid
SchvltzNumberfor Dye
Ordinary Name andClass oj Dye
Statistics ofImpo?t andManufacture
Other IntermediatesUsed and Notes
DyeAppli-cationClass
63
71
118
146
147
MONOAZO DYESAzo Acid Blue
Azo Fuchsine B
Brilliant Geranine
Azo Fuchsine G
Azo Fuchsine 6B
I '14:-I ;20:-
45,0989,222
I '14:-M19:-I '20:-
I 14:-I' 20:-
18,917
527
17,8193,694
I 1 4 : — 13,206M17:— ?M18:— ?
Dimethyl-p-phenylene-diamine
orp-Nitro-aniline [Reduc-
tion and alkylation]
Toluidine
Dehydro-thio-p-toluidine
Sulfanilic Acid
Sulfanilic Acid (?)
A
D
226 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from l:8-Dihydroxy-naphthalene-4:-siilfonic(continued)
Acid
SchidtzNumberfor Dye
229
242
262
276
416
452
460
Ordinary Nanne andClass oj Dye
DISAZO DYESAzo Acid Violet
Sulfon Black G
Victoria Black B
Diamond Green B
BrilliantAzurine 5G
TEISAZO DYESBenzo Indigo Blue
Benzo BlackBlue5G
II
M
I
IMI
II
I
Statistics ofImpoit andManufacture
'14:—'20:—'20:—
'14:—
'14:—'18:—'20:—
'14:—'20:—
'14:—
150119
557
8,622
4,061
22,3241,563
602
Other IntermediatesUsed and Notes
Amino-azo-benzene
Anilinel-Naphthylamine-6-
and 7-sulfonic Acids[Cleve's Acids]
Sulfanilic Acida-Naphthylamine
Ammo-salicylica-Naphthylamine
Dianisidine1:8-Dihydroxy-naph-
thalene-4-suJfonicAcid (2 mols)
Tolidinea-Naphthylamine1:8-Dihydrox3r-naph-
thalene-4-s ulf onicAcid (2 mols)
Benzidine-disulfonic-Acid
a-Naphthylamine1: 8-Dihydroxy-naph-
thalene-4-sulfonicAcid (2 mols)
DyeAppli-cationClass
A
A
A
ACr
D
D
D
4:5-Dihydroxy-l-naphthalene-sulfonic Acid (C. A. nomen.)
See, 1:8-Dihydrox3"-rLaphthalene-4-sulfonic Acid
4:6-Dihydroxy-l-naphthalene-sulfonic Acid (C. A. nomen.)
See, 1:7-Dihydrox}r-rLaphthalene-4-sulfonic Acid
DYES CLASSIFIED BY INTERMEDIATES 227
Dihydroxy-naphthalene-sulfonic Acid SSee, 1: 8-Dihydroxy-naphthalene-4-sulfonic Acid
Dihydroxy-naphthoic Acid L2: 6-Dihydroxy-3-naphthoic Acid (not considered herein)
Dihydroxy-naphthoic Acid S1: 7-Dihydroxy-6-naphthoic Acid (not considered herein)
1: 7-Dihydroxy-2-naphthoic-4-sulfonic Acid1: 7-Dihydroxy-naphthalene-2-carboxylic-4-sulfonic Acid
1: 7-Dihydroxy-2-carboxy-naphthalene-4-sulfonic Acid
1: 7-Dmydroxy-4-sulfo-2-7iaphthoic Acid (C. A. nomen.)
OH
= C l l H 8 O 7 S =
FORMATION.—l-Hydroxy-2-naphthoic acid is disulfonated with 4 partsof 20 per cent oleum, the product isolated and fused with causticsoda at 190-200°
LITERATURE.—Cain, Intermediate Products (2d Ed.), 242Lange, Zwischenprodukte, 2677
Dyes Derived from l:7-Dihydroxy-2-naphthoic-4-sulfonic Acid
SchvltzNumberfor Dye
396
399
427
429
430
Ordinary Name andClass of Dye
DISAZO DYES
Indazurine RM
Indazurine TS
Indazurine GM
Indazurine BB
Indazurine 5GM
Statistics ofImport andManufacture
Other IntermediatesUsed and Notes
TolidineNevile-Winther's Acid
TolidineGamma Acid
DianisidineNevile-Winther's Acid
DianisidineR Acid
DianisidineHAcid
DyeAppli-cationClass
D
D
D
D
D
228 DYES CLASSIFIED BY INTERMEDIATES
1: 7-Diliydroxy-6-naphthoic-3-sulfonic Acid
1: 7-Dibydroxy-naphthalene-6-carboxylic-3-sulfonic Acid
1: 7-Dihydroxy~6-carboxy-naphthalene-3-sulforjic Acid
Xigrotic Acid
Nigrotinic Acid
3: 5-Dihydroxy-7-sulfo-2-waphthoic Acid {C. A. nomen.)
OH
HOHOOC SO3H
= CnH8O7S =
FORMATION.—2-Hydroxy-3-naphthoic acid is disulfonated with 4 parts
of 24 per cent oleum at 125-150° for from two to three hours, the
product isolated, and fused with 2 parts of caustic soda at about
210-220° and then at 230-240°
LITERATURE.—Cain, Intermediate Products (2d Ed.), 241
Lange, ZTvischenprodukte, #2678
Dyes Derived from l:7-Diliydroxy-6-naphthoic-3-sulfoiiic Acid
SchvJUzNumberfor Dye
352
353
354
397
Ordinary Name andClass of Dye
DISAZO DYES
Direct Violet R
Direct IndigoBlue BN
Direct Gray R
Direct Blue R
Statistics ofImport and
Manufacture
I '14:— 661M'19:— ?
I '14:— 6,000
I J20:— 4,927
MJ17:— ?
Other IntermediatesUsed and Notes
Benzidinem-Tolylene-diamine
BenzidineH Acid
Benzidine1:7-Dihydroxy-6-napli-
thoic-3-sulf onic Acid(2 mols)
TolidineNevile-Winther's Acid
DyeAppli-cationClass
D
D
D
D
DYES CLASSIFIED BY INTERMEDIATES 229
Dyes Derived from l:7-Dihydroxy-6-naphthoic-3-sulfonic Acid(continued)
SchvltzNumberfor Dye
398
428
Ordinary Name andClass oj Dye
DISAZO DYES{continued)
Direct Gray B
Direct Blue B
Statistics ojImport andManufacture
I '14:— 21,421MJ17:— 14,823MJ18:— ?I '20:— 7,055
Other IntermediatesUsed and Notes
Tolidine1:7-Dihydroxy-6-napL.-
thoic-3-sulfonic Acid(2 mols)
DianisidineNevile-Wintlier's Acid
DyeAppli-cationClass
D
D
1:2-Dihydroxy-naphthoquinone
See, Naphthazarin
5:6-Dihydroxy-l: 4-naphthoquinone
See, Naphthazarin
5:6-Dihydroxy-a-naphthoquinone
See, Naphthazarin
1:7-Dihydroxy-4-sulfo-2-naphthoic Acid (C. A. nomen.)
See, 1: 7~Dihydrox^-2-naphthoic^-sulfonic Acid
3:5-Dihydroxy-7-sulfo-2-/iaphthoic Acid (C. A. nomen.)
See, 1: 7-Dihydroxy-6-naphthoic-3-sulfonic Acid
Dihydroxy-tartaric Acid
Dioxy-tartaric Acid
C:(OH)2.COOH
C:(OH)2.COOH
230 DYES CLASSIFIED BY INTERMEDIATES
FORMATION.—By oxidation of tartaric acid with strong nitric acid inpresence of oleum
LITERATURE.—Cain, Intermediate Products (2d Ed.), 168
Dyes Derived from Dihydroxy-tartaric Acid
Sckultz
for Dye
23
Ordinary Xame andClass of Dye
PYRAZOLOXE DYETartrazine
Statistics ofImport and
Manufacture
I '14:—272,477M'17:— ?M '18:— ?M'19:— ?I '20:— 47,877M '20:—701,722
Other IntermediatesUsed and Notes
Phenyl-hydrazine-p-sulfonic Acid (2 mols)
DyeAppli-cationClass
A
3:6-Dihydroxy-9-jcanthene-proprionic Acid, 7-Lactone (C. A.nomen.)
See, Resorcinol-suecinein
p-(ft-DimethylaTnfno-anilino)-jhenol (C. A. nomen.)
See, 4-Dimethylamino-4'-bydrox\r-diphenylamine
Diniethylarnino-azo-benzene-disulf onic Acids
5-DimethyIamino-o: p/-azo-bis(l!>enzene-sulfonic Acid) (C. A.nomen. for I)
6-Dimethylamino-m: p'-azo-bisCbenzene-sulfonic Acid) (C A.nomen. for II)
HO3S
= 385
DYES CLASSIFIED BY INTERMEDIATES 231
FORMATION.—The compound represented by "Formula I " is preparedby coupling diazotized sulfanilic acid with dimethyl-aniline-m-sulfonic acid (prepared by sulfonating dimethyl-aniline). The iso-meric compound represented in all probabiKty by "Formula I I , "is made by direct sulfonation of dimethylamino-azo-benzene bymeans of oleum
LITERATURE.—Ger. Pat. 80434, Methods (b) and (a). Frdl. 4, 490
Cf. Ullmann, Enzy. tech. Chemie, 2, 81
Dye
SchvlizNumberfor Dye
628
Derived from Dunethylamino-azo-benzene-disulfonic Acids
Ordinary Name andClass of Dye
OXAZINE DYEGallocyanine MS
Statistics ofImport andManufacture
I '20:— 22
Other IntermediatesUsed and Notes
Gallic Acid
DyeAppli-cationClass
M
/>-Dimethylamino-benzaldehyde
HCO
0-N(CH3)2FORMATION.—Dimethyl-aniline is changed into dimethylamino-benzylalcohol by treatment with hydrochloric acid and formaldehyde.This is then oxidized by adding nitroso-dimethyl-aniline directlyto the crude alcohol, resulting in the formation of dimethylamino-benzylidene-amino-dimethyl-aniline, (CH3)2N.C6H4.CH: N.CeH-N(CH3)2. This latter by treatment with nitrous acid or formalde-hyde forms pure p-dimethylamino-benzaldehydeLITERATURE.—Ullmann, Enzy. tech. Chemie, 2, 307Lange, Zwischenprodukte, #333-335
232 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from />-Dimethylamino-benzaldehyde
SchultzNumberfor Dye
529
564
Ordinary Name andClass of Dye
TEIPHENYL-METHAXEDYE
Acid Violet 6B
Naphthalene GreenV
Statistics ofImport and
Manufacture
I '14:— 22,144I '20:— 9,291
Other IntermediatesUsed and Notes
Ethyl-sulfobenzyl-aniline (2 mob)
[Oxidation]
Dimethyl-anilinewi-Xylene
DyeAppli-cationClass
A
A
^-Dimethylamino-benzoyl Chloride
OCC1
= C9Hi0ClXO = 183.5
X(CH3)2
FORMATION.—From dimethyl-aniline by action of phosgene
LITERATURE.—Beil., 2, 1271
Dye Derived from ^-Dimethylamino-benzoyl Chloride
SchuttzNumberfor Dye
533
Ordinary Name andClass of Dye
TRIPHENTL-METHANEDYE
Acid Violet 7BX
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
Methyl-diphenylamine-sulfonic Acid (2 mols)
DyeAppli-cationClass
A
Diinetliylainino-benzoyl-inethyl-aaiiline
DimethylarnincHbenzcHmethyl-aniliiie (Schultz nomen.)
2>-Dimethylajiiino-xVrmethyl-benzanilide (<7. A. nomen.)
(CH3)2N
CH3
CO.X —254
DYES CLASSIFIED BY INTERMEDIATES 233
FORMATION.—Dimethyl-aniline reacting with phosgene forms p-di-methylamino-benzoyl chloride, which latter unites with methyl-aniline to form the p-dimethylamino-benzoyl-methyl-aniline
LITERATURE,—Cf. Ger. Pat. 41751, 44077Cf. Georgievics and Grandmougin, Dye Chemistry, 174
Dye Derived from Dimethylamino-benzoyl-methyl-aniline
SchultzJSwtnoerfor Dye
493
Ordinary Name andClass of Dye
DlPHENYL-METHANEDYE
Auramine
Statistics ofImport andManufacture
I '14:-449,276M'17:— ?M'18:— 45,634M'19:—127,567M'20:— ?I '20:— 74,414
Other IntermediatesUsed and Notes
Dimethyl-aniline
DyeAppli-cationClass
B
-^: JV-cHmethyl-metanilic Acid (C. A.nomen.)
See, p: pr - Tetramethyl - diamino - diphenylmethane - sulfonicAcid
5- Dimethylamino- a- (p- dimethylamino- phenyl)- a- hydroxy- o-^oluene-sulfonic Acid (C. A. nomen.)
See, pip'-Tetramethyl-diamino-benzohydrol-sulfonic Acid
(Dimethylamino-hydroxy-benzoyl) -benzoic Acid
o-(4-Dunethylamino-2~hydroxy-benzoyl)-&enzoic Acid (C A. no-men.)
OH
" C O Y S - C J I N O - 2 8 5CUOil <. >±X (Cxi3J2
FORMATION.—By condensing phthalic anhydride and ?n-dimethylainino-phenol
234 DYES CLASSIFIED BY INTERMEDIATES
LITERATURE.—Georgievics and Grandmougin, Dye Chemistry, 232
Lange, Zwischenprodukte, #1394, 1395 (Note Lange9 s
formula is at variance with structure given above, which,
however, corresponds to the generally accepted for?nula)
Dyes
SchultzNumberfor Dye
575
576
577
578
Derived from (Dimethylamino-hydroxy-benzoyl)benzoic
Ordinary Xame andClass of Dye
XANTHONE DYESRhodine 12GM
Rhodamine 3G
Rhodine 2G
Rhodamine 12GF
Statistics ofImport and
Manufacture
I '14:— 19,568I '20:— 855
Other IntermediatesUsed and Notes
Resorcinol MethylEther
[Ethyl esterification]
3-Amino-p-cresol[Ethyl esterificationj
Ethyl-m-amino-phenol[Ethyl esterification]
Resorcinol[Formaldehyde;
esterification]
Acid
DyeAppli-cationClass
B
B
B
B
4-Dimethylamino-4/-hydroxy-diplienylaraine
p-(p-Dimcthylamino-anilino)-phenol (C A. nomen.)
-No.-(CH3)2N
FORMATION.—(1) Dimethyl-p-phenylene-diamine is heated with thehydrochloride of p-nmino-ph pn ol. (2) Dimethyl-p-phenylene-diamine and phenol are simultaneously oxidized and the productcarefully reduced
LITERATURE.—Lange, Zwischenprodukte, #1644
e, Swefelfarbstoffe, 145, 157
DYES CLASSIFIED BY INTERMEDIATES 235
Dye Derived from 4-Dimethylamino-4;-hydroxy-diplienylamiiie
SchvltzNumberfor Dye
728
Ordinary Name andClass of Dye
SULFUE DYEImmedial Sky Blue
Statistics ofImport and
Manufacture
M'17:— ?
Other IntermediatesUsed and Notes
[S+Na*S]
DyeAppli-cationClass
S
l-Dimetliylamino-S'-methoxy-benzophenone {C. A, nomen.)
Methoxy-dimethylamino-benzophenone
FORMATION.—10 parts of m-methoxy-benzanilide, 14 parts of dimethyl-aniline and 7 parts of phosphorus oxychloride are heated togethercarefully on the water bath at 90°. The melt is treated with 50parts of water and 5 parts of hydrochloric acid, and the yellow brownsolution warmed to 70-80° until the color has disappeared, whichindicates the completion of the splitting off of the aniline. Morewater is now added, the precipitate filtered, washed, dried, andcrystallized from two parts of alcohol. From the filtrate anilineand dimethyl-aniline can be recovered
LITERATURE.—Lange, Zwischenprodukte, #1383
Dye Derived from 4-Dimethylamino-3'-methoxy-benzoplienone
SchultzNumberfor Dye
547
Ordinary Nome andClass oj Dye
TlUPHENYL-METHANEDYE
Ketone Blue 4BN
Statistics ofImport andManufacture
Other IntermediatesUsed and Notes
Methyl-diphenylamine[Sulfonation]
DyeAppli-cadonClass
A
^-Dimethylaanino-i\T-methyl-6enzanilide (C. A. nomen.)
See, Dimethylamino-benzoyl-methyl-aniline
23G DYES CLASSIFIED BY INTERMEDIATES
2-Diinethylainiiio-8-naphthol-6-siilfonic Acid
See, Dimethyl-gamma Acid
7-Dimethylairrino-l-naphthol-3-sulfoiiic Acid (C. A. nomen.)
See, Dimethyl-gamma Acid
5-Dimetfoylamino-2-iiitffoso-£-cresol (OH=1,C. A. nomen.)
Nitroso-dimethyl-m-amino-p-cresol (OH =1)
OH
( C H ^ x i ^ / =
CH3
FORMATION.—3-DimethyIamino-p-cresol (OH = 1) [which can be ob-tained by decomposing diazo-dimethyl-o-toluidine in an acid solu-tion] is dissolved in hydrochloric acid, cooled to 0° C , and nitrosifiedwith aqueous solution of sodium nitrite
LITERATURE.—Lange, Zwisehenprodukte, #1089
Dye Derived from S-Dinietliylanuno-2-nitroso-^-cresol
" S ^ Ordinary Xa^earul I g g ^ gfor Dye | Class oj Dye | Ma^ujacture
621OXAZINE DYE |
Cresyl Blue 2BS 1!
Other IntermediatesUesd and Notes
p-Phenylene-diamine
DyeAppli-cationClass
B
m-Dimethylamino-^henol (C A. nomen.)
t7Z-Hydrox3r-dimeth}rl-aniline
Dunethyl-wz-amino-phenol
OH
) N C C H O .
FORMATIOX.—By caustic soda fusion of dimethyl-aniline-m-sulfonicacid, prepared by sulfonating dimethyl-aniline with oleum
LITERATURE.—Lange, Zwischenprodukte, #603-606, 2263
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from m-Dimethylamino-phenol
237
%& **%£$%."*
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
568
569
570
XANTHONE DYESPyronine G
Acridine Red B
Rhodamine S I '14:—I '20:—
600273
m-Dimethylainino-phenol (2 mols)
[Oxidation]
m-Dimethylamino-phenol (2 mols)
[Oxidation]or
[Oxidation of PyronineGwithKMnO4]
m-Dimethylairdno-phenol (2 mols)
[Succinic Anhydride]
B
B
Dimethyl-aniline
iV:iV-Dimethyl-aniline ( C A. nomen.)
N(CH3)2
STATISTICS.—Imported J14:— 48,642 lbs.
Manufactured ' 17:—2,847,093 lbs.
Manufactured '18:—4,263,458 lbs.
Manufactured '19:—3,559,654 lbs.
Manufactured J20:—5,447,107 lbs.
FOR]&ATTON.—By heating aniline and methanol (methyl alcohol) in an
autoclave in the presence of sulfuric acid
LITERATURE.—Cain, Intermediate Products (2d Ed. ) , 62
Lange, Zwischenprodukte, #129
238 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Dimethyl-aniline
Schult?Numberfor Dye
32
124
138
493
495
496
497
Ordinary Name andClass of Dye
MOXOAZO DYESButter YellowOil Yellow
Diazine Green S
HelianthineMethyl Orange
AUEAMINESAuramine
TRIPHEXYL-METH4JSEDYES
Malachite Green
Setoglaucine 0
New Fast Green 2BVictoria Green 3B
Statistics ojImport aridManufacture
I '14:— 4,062M'17:—33,180M'18:—27,669M'19:— 31,156M'20:— 74,182
I '14:— 1,340
I '14:— 500M'18:— ?M'19:— ?M'20:— ?
I '14:—449,276M'17:— ?M'18:— 45,634M'19:—127,567I '20:— 74,414
M'20:— ?
I '14:—183,852M'17:—130,229M '18:—290,416M'19:—560,301I '20:— 100
M'20:—654,237
I '20:— 1,102
I '14:— 44,595
Other IntermediatesUsed and Notes
Aniline
p-Tolylene-diamineo-ToluidineAniline or a-Toluidine
orSafranine
Sulf anilic Acid
Dimethylamino-benzo-methylaniline
Dimethyl-aniline(2 mols)
Benzaldehyde[Oxidation]
Dimethyl-aniline(2 mols)
o-Chloro-benzaldehyde[Oxidation]
Dimethyl-aniline(2 mols)
2:5-Dichloro-benzalde-hyde
[Oxidation]
DyeAppli-cationClass
ss
B
A
B
B
B
B
DYES CLASSIFIED BY INTERMEDIATES 239
Dyes Derived from Dimethyl-aniline (continued)
SchultzNumberfor Dye
Oi dinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
510
TRIPHENYL-METHANEDYES (continued)
Azo Green
515 Methyl Violet
516 Crystal Violet
517 Methyl Violet 5BBenzyl Violet
519 Methyl Green
I '14:—255,063M17:—375,107M'18:—632,196M'19:—574,436
:— 3,312M'20:—600,873
I '14:— 51,872M'17:—M'18:—M'19:—I '20:—M'20:—
???
2,919?
I '14:— 22,387I '20:— 3,313M'17:— ?
Dimethyl-aniline(2 mols)
m-Nitro-benzaldehydeSalicylic Acid[Oxidation]
Dimethyl-aniline(3 mols)
[Phenol][Oxidation]
Ketoneor
Dimethyl-aniline(3 mols)
Phosgeneor
Hydrol[Oxidation]
[Benzylation of MethylViolet]
orBenzyl-chlorideDimethyl-aniline
(3 mols)[Phenol]
[Methyl Chloride ofMethyl Violet]
orDimethyl-aniline
(3 mols)[Phenol and Methyl
Chloride]
M
B
B
B
B
240 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Dimethyl-aniline (continued)
SchvJtzX umberjor Dye
523
5G4
659
660
661
Ordinary Xame andClahs of Dye
TRIPHEXYL-METHANEDYES {continued)
Fast Green
NaphthaleneGreen V
THIAZIXE DYESMethylene Blue
Methylene Green 0
Thionine Blue G 0
Statistics ofImport and
Many fact we
I '14:— 14,347I '20:— 10,461
I J14:— 22,144I '20:— 9,291
I ' 14:—185,958M '17:—268,435M'IS:—312,572M319:—465,992I '20:— 2,053M'20:—577,264
I' 14:— 30,812M'lS:— ?M'19:— 2,435I '20:— 1,049
I '14:— 18,618I '20:— 330
Other IntermediatesUsed and Xotes
7?z-Xitro-benzaldeh3TdeDimethyl-aniline
(2 mols)Benzyl-chloride
(2 mols)[Sulfonation, Oxidation]
p-Dimethylarxiino-benzaldehyde
m-Xylene
Dimethyl-aniline(2 mols)
[Naa&Os, etc.]or
Nitroso-dimethyl-aniline
pNTa2S2O3, etc.]or
Dimethyl-p-phenylenediamine
Psa2S2O3, etc.]
Dimethyl-aniline(2 mols)
[Naa&Os, Nitration]or
Nitroso-d i methyl-aniline
[Naf&Os, etc.; Nitra-tion]
orDimethyl-p-phenylene-
diamine[Na^Os, etc.; Nitra-
tion]or
[Methylene Bluenitrated]
Ethyl-methyl-aniline[Nas&Os, etc.]
DyeAppli-cationClass
A
A
B
B
B
DYES CLASSIFIED BY INTERMEDIATES 241
N: N-Dimethyl-p: /-azo-bisaniline (<7. A. nomen.)
See, Dimethyl-p: p'-diamino-azo-benzene
2:2/-Dimethyl-l: r-Manthraquinone (C. A. nomen.)
2: 2/-Dimethyl-l: l'-dianthraquinonyl
FORMATION.—l-Amino-2-methyl-anthraquinone is dissolved in sulfuricacid and sodium nitrite added. The isolated and dried diazoniumsulfate is stirred into acetic anJiydride, and copper powder added.Nitrogen is evolved and the combination takes place, forming thebianthraquinone derivative
LITERATURE.—Lange, Zwischenprodukte, #3491-3493Cain, Intermediate Products (2d Ed.), 261
Dyes Derived from 2:2'-Dimethyl-l: l'-bianthraquinone
SchvltzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
760
761
762
ANTHRAQUINONE ANDALLIED DYES
IndanthreneGold Orange G
Pyranthrone
IndanthreneGold Orange R
IndanthreneScarlet G
I '14:— 20,092I '20:— 7,617
I '14:— 50,496I '20:— 35,338
I '14:—I '20:—
99399
[2 mols H2O removed]
[2 mols H2O removed,Chlorinationl
[or Pyranthrone 760,chlorinated]
[2 mols H2O removed,Bromination]
[or Pyranthrone 760,brominated]
242 DYES CLASSIFIED BY INTERMEDIATES
Dimethyl-^: ^'-diamino-azo-benzene.V: JV-Dimethyl-p: p'-azo-bisaniline (C. A. nomen.)
X X XH2 =Ci4Hi6X4 =(CH3)2X
FORMATION.—(1) By coupling of diazotized p-nitro-aniline with dimethyl-aniline and subsequent reduction with sodium sulfide.(2) By coupling of diazotized p-amino-acetanilide with dimethyl-aniline and splitting off of acetyl group
LITERATURE.—Heumann, Anilinfarben, 3, 1467; 4, 1026Cf. Lange, Zwischenprodukte, #1760
Dye Derived from Dimethyl-^: y-diamino-azo-benzene
SchulizNumber1 or Dye
239
Ordinary Name andClass of Dye
DISAZO DYEAzotol C
Statistics ofImport andManufacture
Other IntermediatesUsed and Notes
jS-Naphthol
DyeAppli-cationClass
MF
4:4/-Dimethyl-diamino-3:3'-ditolyI-methaneDimethyl-diamino-di-o-tolyl-methane4:4/-Methylene-bis(AT-meth3i-o-toluidine) (C. A, nomen,)
CHs.HX, j j XH . CH3
FORMATION.—By condensing formaldehyde and two molecules ofmethyl-o-toluidine
LITERATURE.—Cain, Intermediate Products (2d Ed.), 104Lange, Zwischenprodukte, #1318
Dye Derived from 4:4'-Diinethyl-(iiainiiio-3:3'-ditolyl-inethane
SckultsNumberfor Dye
494
Ordinary Name andClass of Dye
AUTUMTNTISAuramine G
Statistics ofImport and
Manufacture
I 14:— 1,902
Other IntermediatesUsed and Notes
[Sulfur, Ammoniumchloride, etc.}
DyeAppli-cationClass
B
DYES CLASSIFIED BY INTERMEDIATES 243
Dimethyl-diamino-di-o-tolyl-methane
See, 4:4/-Dimeth3'l-diamino-3: 3'-ditolyl-methane
2:2-Dimethyl-l: r-dianthraquinonyl
See, 2: 2'-Dimethyl-l: l'-&ianthraquinone (C. A. nomen.)
Dimethyl-gamma Acid
2~Dimethylamino-8-naphthol-6-sulfonic Acid
7~Dimethylamino-l-naphthol-3-sulfonic Acid (C A. nomen.)
HO
N(CH3)2 _ Cl2H13NO4S = 267HO3S
FOKMATION.—G acid is heated with dimethylamine in an autoclavearound 200°, the dimethylamino-G acid thus obtained is fused withcaustic soda at 210-220°, and the dimethyl-gamma acid isolated
LITERATURE.—Lange, Zwischenprodukte, #2550
Dyes Derived from Dimethyl-gamma Acid
SchultzNumberfor Dye
206
348
393
Ordinary Name andClass of Dye
MONOAZO DYEDiphenyl
CatecMne G
DISAZO DYESDiphenyl
Brown BN
DiphenylBrown 3GN
Statistics ofImport and
Manufacture
I 14:— 8,642
I '14:— 13,471
M'20:— ?
Other IntermediatesUsed and Notes
p-Nitro-toluene-o-sulf onic Acid
p-Phenylene-diamine[Diphenyl Orange RR1
Salicylic AcidBenzidine
Salicylic AcidTolidine
DyeAppli-cationClass
D
D
D
N: iV-Dimethyl-£-mtroso-ajiiline (C. A. nomen.)
See, p-Nitroso-dimethyl-aniliAe
244 DYES CLASSIFIED BY INTERMEDIATES
N: JV-Dimethyl-m-£henylene-diamine (C. A. nomen.)
w-Amino-dimethvl-aniline
FORMATION.—Dimethyl-aniline is nitrated "with mixed acid, and them-nitro-dimethyl-aiiiline separated from the para isomer. Them-derivative is novr reduced to dimethyl-??2~phen3'lene-diamine
LITERATURE.—Green, Organic Coloring Matter (1908), 32
Dyes Derived from N: iV-Dimethyl-m-phenylene-diamine
Ordinary Xame and \ *£$»$ | Otker InterrnediatesCl f D u | i d d A
i S S . y £ $ $ |forDye1, Class of Dye Manufacture | isedandAotes
DyeAppli-cationClass
603
604
ACRIDINE DYES ' 'Acridine Orange NO I J14:— 2,336i Dimethyl-m-phenylene-
, I J20:— l,92n| diamine (2 mols)i [Formaldehyde, Oxida-| i tion, etc.]! I
i Dimethyl-wi-phenylene-I diamine (2 mols)I Benzaldehyde' [Ammonia removal;
Oxidation]
Acridine Orange R
B
B
N: iV-Dimethyl-^-phenylene-diamine (C. A. nomen.)
y)~Amino
N(CH 3 ) 2
STATISTICS.—Imported ' 14:—very smallManufactured 717:— ?Manufactured ' 18:— ?Manufactured ?20:—314,931
DYES CLASSIFIED BY INTERMEDIATES 245
FORMATION.—Dimethyl-aniline by action of nitrous acid forms nitroso-dimethyl-aniline, which by reduction with zinc dust and hydro-chloric acid furnishes dimethyl-p-phenylene-diamine
LITERATURE.—Lange, Zwischcnprodukte, #561-563
Dyes Derived from N: iV-Dimethyl-^-phenylene-diamine
SchultzNumberfor Dye
62
63
619
627
659
660
661
Ordinary Name andCalss of Dye
MONOAZO DYESAzogalleine
Azo Acid Blue
INDOPHENOLIndophenol
OXAZINE ANDTHIAZINE DYES
Modem Cyanine
Methylene Blue
Methylene Green 0
Thionine Blue G 0
Statistics ofImport and
Manufacture
I '14:— 45,09SI '20:— 4,485
M '18*:— ?M '19.-126,611
I '14:—185,958M'17:—268,435M'18:—312,572M'19:-HJ:65,992I '20:— 2,053M'20:—577,264
I '14:— 30,812M'18:— ?M'19:— 2,435I '20:— 1,047
I '14:— 18,618I '20:— 2,030
Other IntermediatesUsed and Notes
Pyrogallol
1:8-Dihydroxy-naph-thalene-4-sulf onic Acid
a-Naphthol[Oxidation]
Nitroso-dimethyl-aniline
Gallamide
Dimethyl-aniline[Na2S2O3, etc.]
Dimethyl-aniline[Na^^Os, etc.][Nitration]
or[Methylene Blue
nitrated]
Ethyl-m ethyl-aniline[Na^Os, etc.]
DyeAppli-cationClass
M
M
V
M
B
B
B
246 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from N: N-Dimethyl-^-phenylene-diaroine (.continued)
SchultzNumberfor Dye
669
670
680
681
683
690
729
731
Ordinary Name andClass of Dye
AZINE DYESNeutral Violet
Neutral Red
MethyleneViolet BN
Methylene Gray 0New Fast Gray
Safranine MN
Diphene Blue RMetaphenylene
BlueR
SULFUR DTESKrvogene Pure
BlueR
Thiophor Indigo C J
Statistics ofImport and
Manufacture
M'18:— ?
I '14:— 1,521M'17:— ?I '20:— 33
I '14:— 29,507M'17:— ?M'lS:— 16,746M'19:— 2S,458I '20:— 509M'20:— 31,620I '14:— 198M'18:— ?M'19:— ?M'20:— ?
I 720:— 3,124
Other IntermediatesUsed and Notes
Dimethyl-p-phenylene-diamine (2 mols)
m-Phenylene-diamine
m-Tolylene-diamine
Aniline (2 mols)[Oxidation]
Dimethyl-p-phenylene-diamine (2-|-mols)
[Oxidation]
Anilineo- or p-Toluidine[Oxidation]
st/m-Di-p-tolyl-m-phenylene-diamine
[Oxidation]
Aniline (2 mols)[S+NaaS]
or[Methylene Violet;
a-Naphthol[S+Na*S]
DyeAppli-cationClass
B
B
B
B
B
B
S
S
N: AT»IHinethyl .phftny1ftnft.-di>rninft-thingii7fnrii>. Acidp-Amino-dimethyl-aniliiie-thiosulfonic Acid
!~Aii3ino-4^imetbyIamino-bei]Lzene-2~thiosuIfoiiic Acid2-Amino-OKiimethylaniino-6€rizene-thiosulfoiiic Acid (C.
rumen.)
DYES CLASSIFIED BY INTERMEDIATES
N(CH,)a
247
HOsS.Sl
NH2
FORMATION.—10 parts of dimethyl-p-phenylene-diamine sulfate are dis-solved in 100 parts of water and cooled to 0°, and a cold solution of5.5 parts of potassium bichromate in 60 parts of water and 18 partsby volume of 50 per cent acetic acid, is introduced quickly duringagitation. To the crystal mass is now added at once a solution of22 parts of sodium thiosulfate and 27 parts of aluminum sulfatein 70 parts of water, and the mixture agitated at 10-20°. Uponcooling to 0° the desired product separates out
LITERATURE.—Lange, Zwischenprodukte, #931
Dyes Derived from i^iiST-Dimethyl-^-phenylene-cnainine-thiosulfoiiicAcid
SchidtzNumberfor Dye
661
664
665
667
Ordinary Name andClass of Dye
THIAZINE DYESThionine Blue G O
Lenco-galloThionine DH
Urania Blue
Brilliant AlizarinBlueG
Indochromine T
Statistics ofImport andManufacture
I '14:— 18,618I '20:— 2,030
I '14:— 132
I '14:— 19,481M'19:— ?I '20:— 3,214M'20:— ?
Other IntermediatesUsed and Notes
Ethyl-methyl-aniline
Gallic Acid
N: #'-Di-2-naphthyl-7n-phenylene-diamine
1:2-Naphthoquinone-4: 6-disulfonic Acid
DyeAppli-cationClass
B
M
A
M
N: iV'-Di^-naphthyl-m-phenylene-diamine
24S DYES CLASSIFIED BY INTERMEDIATES
FORMATION.—108 parts of m-phenylene^liamine, 432 parts of £-naphtholand 2-3 parts of iodine are heated together at 200° and finallyat 260°. The melt is powdered, and washed successively withdilute caustic soda, hydrochloric acid, water, alcohol, and ether.The residue is crj'stallized from aniline. Yield good
LITERATURE.—Lange, Zwischenprodukte, £2875, 2876
Dyes Derived from Ar:iV/-Di-2-naphthyl-m-phenyleiie-diamine
SchultzNumberJor Dye
665
Ordinary Name andClass of Dye
Statistics ofImport and
Manufacture
THIAZINE DYE JUrania Blue . I '14 :— 132
1 AZIXE DYE *692 Xaphtbazine Blue I '14:— 6,261
I '20:— 2/249
Other Intermediatessed and Notes
Dimethyl-p-phenylene-diamine- thiosulfonicAcid
Nitroso-dimethyl-aniline
DyeAppli-cationClass
2:4-Dirritro-aniline (C. A. nomen.)7w-Dinitro-anilineXH2
< <xo2 _4 — 1 8 3
XO2
FORMATION.—Aniline is condensed with phthalic acid, and the phthal-anil dinitrated. Upon heating the latter product with anilineunder pressure the 2:4-dinitro-aniline is split off
LITERATURE.—Lange, Zwischenprodukte, #539Dyes Derived from 2:4-Dinitro-aniline
SchultzNumberjor Dye
59
Ordinary Name andClass oj Dye
MONOAZO DYEWool Violet S
Statistics ofImport ond
Manufacture
I '14:— 308MJ18:— ?M '19:— ?
Other IntermediatesUsed and Notes
Diethyl-aniline-?n-sulf onic Acid
DyeAppli-cationClass
A
DYES CLASSIFIED BY INTERMEDIATES 249
m-Dinitro-aniline
See, 2:4-Dinitro-aniline (C. A. nornen.)
p-(2:4-Dinitro-anilino)-phenol (C. A. nomen.)
See, 2:4-Dinitro-4/-hydroxy-diphenylamine
4:8-Dinitro-anthrachrysone-2:6-disulfonic Acid
OH
>W3-»-»- . fi. TT "VT /~\ rj COO\fX v_yi4JJL6lN 2 ^ 1 6 ^ 2 O i i
H O " " " ' N O 2
F O R M A T I O N . — A n t h r a e h r y s o n e i s s u l f o n a t e d a n d n i t r a t e d
L I T E R A T U R E . — G r e e n , O r g a n i c C o l o r i n g M a t t e r s ( 1 9 0 8 ) , # 5 5 4 a n d # 5 5 7
D y e D e r i v e d f r o m 4 : 8 - D i n i t r o - a n t h r a c h r y s o n e - 2 : 6 - d i s u l f o n i c A c i d
SchultzNumberfor Dye
796
Ordinary Name andClass oj Dye
ANTHRAQUINONE ANDALLIED DYE
Acid AlizarinGreen G
Statistics ofImport andManufacture
I '20:— 1,334
Other IntermediatesUsed and Notes
[Sodium sulfidereduction]
DyeAppli-cationClass
ACr
1:5-Dinitro-anthraflavic-3:7-disulfonic Acid
. C O N ° 2
c o ) 0 ^ H
NO2
FORMATION.—By the sulfonation and nitration of anthraflavic acid(which is prepared by heating m-hydroxy-benzoic acid with sul-furic acid at 190° C.)
LITERATURE.—Thorpe, Die. Chemistry, 1, 84
Cf. Bucherer, Lehrbuch des Farbenchemie, 339 (1914)
250 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from l:5-Dinitro-anthraflavic-3:7-disulfonic Acid
SchxdtzNumbe,for Dye
857
Ordinary Name andClass of Dye
ANTHEAQUTN'ONE ANDALLIED DYES
Erweco AlizarinAcid Blue R
Statistics ofImport andManufacture
Other IntermediatesUsed and Notes
Aniline (2 mols)[Sulfonation}
DyeAppli-cationClass
ACr
Dinitro-anthraquinone(1: o-and 1: S-Dinitro-anthraquinones)
0 2 N
STATISTICS.—Manufactured '19:— ?
FORMATION".—The mixed compounds are obtained from anthraquinone,by nitration in sulfurie acid solution, and by pouring the nitrationproduct into ^vater
LITERATURE.—Cain, Intermediate Products (2d Ed.), 253
Dyes Derived from Dinitro-anthxaquinone
SchuUz1
Numberfor Dye
Ordinary Name andClass of Dye
SiaiistiGs ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
749
790
801
802
SULFTB DYEAnthraquinone Black
AynraA QOK ONE ANDALLIED DYES
AnthraceneBlue
AnthraceneBlue WGG
AnthraceneBlue WG new
I 'U:— 26,642I '20:— 3,539
I '20:— 1,500
[S+Na*SJ
[Sulfonation, Oxidation]
[Oxidation]
[Oxidation]
S
ACr
M
M
DYES CLASSIFIED BY INTERMEDIATES 251
1:5-Dinitro-anthraquinone
CO N ° 2
•—O14X1IV S c W02N
STATISTICS.—Manufactured '20:— ?
FORMATION.—From anthraquinone in sulfuric acid solution by nitra-tion with HNO3 or NaNO3. The mixed 1: 5 and 1:8 dinitro-anthraquinones are recovered by pouring the nitration mixture intowater. By extraction of the mixed dinitro-compounds with ace-tone or alcohol, the 1: 5-dinitro-anthraquicone is left behind
LITERATUBE.—Cain, Intermediate Products (2d Ed.), 253Lange, Zwischenprodukte, #3218
Dyes Derived from l:5-Dinitro-anthraquinone
SchuiizNumberfor Dye
749
800
853
Ordinary Name andClass of Dye
SULFUR DYEAnthraquinone Black
ANTHRAQUINONE ANDALLIED DYES
AnthraceneBlue WG
AnthraquinoneViolet
Statistics ofImport andManufacture
I '14:— 54,812I '20:— 2,049
I '14:— 1,202I '20:— 1,649
Other IntermediatesUsed and Notes
[S+Na^S]
[Oxidation]
p-Toluidine (2 mols)[Sulfonation]
DyeAppli-cationClass
s
M
ACr
m-Dinitro-benzene
NO2
STATISTICS.—Imported '14:— 164,650 lbs.Manufactured '17:—2,333,192 lbs.Manufactured '18:—4,115,269 lbs.Manufactured '19:—2,280,282 lbs.Manufactured '20:—3,380,il2 lbs.
252 DYES CLASSIFIED BY INTERMEDIATES
FORMATION.—By nitration of nitro-benzene or of benzene, using mixedacid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 32Cf. Lange, Zwi^ehenprodukte, #543
USES.—For the manufacture of m-nitro-aniline and ?n-phenylene-diamine
2:2'-Dinitro-j>: £'-biacetanilide
See, Diacetyl-o: o'-dinitro-benzidine
2:4-Dinitro-chloro-benzene
See, l-Chloro-2: 4-dinitro-benzene (C. A. nwnenS)
Dinitro-^-cresol
OH 1
• i = C7H6X0O5 — 198
CH».
FORMATION.—Probably by the dinitration of p-cresol
LITERATURE.— Cf. Thorpe, 2, 165Cf. Lange, Schwefelfarbstoffe, 132, 381
Dye Derived from Dinitro-^-cresol
for Dye ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
t SULFUR DTE725 Immedial Dark
Brown AImmedial Brown B
I '14:— 23,SS7 [S+Na*S]M'18:— ?
Dinitro-dibenzyl-disulfonic Acid
2:2r-Ethylene-bis(o-nitro-?>enzene-sulfonic Acid) (C. A. nomenS)
SO3H HO3S
= 4 3 2
DYES CLASSIFIED BY INTERMEDIATES 253
FORMATION.—12 parts of sodium p-nitro-toluene-sulfonate are dissolved
in 50 parts of hot water, and treated with 100 parts of sodium
hypochlorite solution (2 per cent HOC1) and 50 parts of caustic
soda solution (40°) at 70°. At end of reaction, cooled with ice to
40° and after crystallizing several hours, the product is filtered off.
LITERATURE.—Lange, Zwischenprodukte, #1460
Dyes Derived from Dinitro-dibenzyl-disulfonic Acid
SchultzNumberfor Dye
10
12
18
Ordinary Name andClass of Dye
STILBENE DYESMikado YellowStilbene Yellow
DiphenylCitronine G
Diphenyl FastYellow
Statistics ofImport and
Manufacture
I '14:— 85,795M'18:— ?M'20:— ?
I '14:— 10,229
I '20:— 1,102
Other IntermediatesUsed and Notes
Dinitro-dibenzyl-disul-fonic Acid (2 mols)
Aniline
Dehydrothio-toluidine-sulf onic Acid (2 mols)
or Primulin e-sulf onicAcid (2 mols)
DyeAppli-cationClass
D
D
D
2: S-Dinitro-diphenylamine-S': 4-disulfonic Acid
3: 5-Dinitro-3': 4-imino-bis(&enzene-sulfonic Acid) (C. A. nomen.)
NO2 SO3H
NH = Ci2H9N3OioS2=419
NO2
FORMATION.—By reaction of l-chloro-2:6-dinitro-benzene-4-sulfonic
acid and metanilic acid in presence of sodium acetate
LITERATURE.—Lange, Zwischenprodukte, #1712
Cf. Schultz, Farbstofftabellen, #542
5i DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from 2:5-Dinitro-diphenylamine-3':4-disulfonic Acid
Other IntermediatesUsed and Notes
AgaJma Green B 11 '14.— 2,294
DyeAppli-cationClass
2:4-DMtaro-diphenylamine-3'-sxilfonic Acid
*Y-(2:4-Dinitro-phenyi)-w2etanilic Acid (C. A. nornen.)
_X0 2 SO3H
02X<^ V - X H - = C12H9N3O7S = 339
FORMATION.—From chloro-dinitro-benzene and metanilic acid
LITERATURE.—Lange, Z^ischenprodukte, #1673Cf. Schultz, FarbstofftabeUen (1914), #738
Dye Deriyed from 2:4-Dinitro-diphenylamine-3'-sulfonic Acid
SchulUNumberfor Dye
738
Ordinary Name andCkssofDye
SULFUR DYECotton Black
Statistics ofImpoi t andManufacture
Other IntermediatesUsed and Notes
[S+NasS]
DyeAppli-cationClass
S
2:4-Dinitro-diphenyIaznine-4/-sxilfonic Acid
^"-(2:4-Dinitro-phenyl)-5iilfanilic Acid ((7. A. nomen.)
NO,
N H ^ ~ ^ S O C = 339
FORMATION.—From chloro-dinitro-benzene and sulfanilic Acid
LITERATURE.—Lange, Zwischenprodukte, #1673Cf. Schultz, FarbstofftabeUen, #738
DYES CLASSIFIED BY INTERMEDIATES 255
Dye Derived from 2:4-Dinitro-diphenylamine-4/-sulfonic Acid
SchultzNumberfor Dye
738
Ordinary Name andClass of Dye
SULFUR DYECotton Black
Statistics ofImpott endManufacture
Other IntermediatesUsed and Noies
[S+Na*S]
DyeAppli-cotionClass
S
2:4-Dinitro-4'-hydroxy-(Hphenylamine
p-(2:4-Dinitro-anilino)-phenol (C. A. nomen.)
NO2
O2N< •NH 5 —275
STATISTICS.—Manufactured 1919 but amount not disclosed
FORMATION.—From chloro-dinitro-benzene and p-amino-phenol byboiling molecular proportions in an aqueous suspension withslightly more than the theoretical amount of limestone
LITERATURE.—Cain, Intermediate Products (2d Ed.), 73Lange, Zwischenprodukte, #1670
Dyes Derived from 2:4-Dinitro-4'-hydroxy-diphenylamine
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
724
725
726
SULFUR DYESImmedial Black
Immedial DarkBrown A
Immedial Brown B
Pyrogene Direct BluePyrogene Blue
14:— 54,696M18:— ?
14:— 23,887M'18:— ?
[NaOH;
I 14:— 10,934 [Alcohol; S+Na*S]I '20:— 2,498
3:5-Dinitro-3': 4-imino-bis(6enzene-sulfonic Acid) (C. A. nomen.)
See, 2: 5-Dimtro-diphenylamine-3': 4-disulfonic Acid
25G DYES CLASSIFIED BY INTERMEDIATES
1:5-and 1:8-Dinitro-naphthaJenes
02N X0 2
and I | 1 =C10H6X2O4 = 218
STATISTICS.—Imported '14:—very small amount
Manufactured 'IS:— ?
Manufactured '19:— ?
FORMATION.—From a-nitro-naphthalene by nitration
LITERATURE.—Cain, Intennediate Products (2d Ed.), 170
Dyes Derived from 1:5- and 1:8-Dinitro-naphthalenes
for Dye
774
775
776
ANTHRAQUDTONE ANDALLIED DYES
Alizarin Black
Alizarin DarkGreen W
Printing Black forWool
Manufacture
I '14:—205,439I '20:— 17,421
Other IntermediatesUsed and Notes
[Oxidation]
Phenol[Oxidation]
[Reduction]
DyeAppli-cationClass
M
M
A
1:5-Dinitro-naphthalene
a-Dinitro-naphthalene
NO2
FORMATION.—a-Nitro-naphthalene is nitrated, resulting in formationof 1:5 and 1:8-<iinitro-naphthalenes ia the proportion of about
DYES CLASSIFIED BY INTERMEDIATES 257
1:2. This crude product is washed with water and dried, and
then extracted first with carbon disulfide to remove nitro-naph-
thalene, and second with acetone to remove the 1:8 isomer,—
leaving behind the 1: 5 isomer. (See 1: 8-dinitro-naphthalene)
LITERATURE.—Cain, Intermediate Products (2d Ed.), 170
Lange, Zwischenprodukte, #2315
SchultzNumberfor Dye
745
789
Dyes Derived
Ordinary Name andClass of Dye
SULFUR DYEMelanogene Blue
ANTHRAQUINONE ANDALLIED DYES
AnthraceneBlue WR
from 1:5-Dinitro-naphthalene
Statistics ojImport and
Manufacture
I 14:—107,778I '20:-103,913M'20:— ?
Other IntermediatesUsed and Notes
[S+Na*S]
[Oxidation]
DyeAppli-cationClass
S
M
1:8-Dinitro-naphthalene
/3-Dinitro-naphthalene
02N N02
FORMATION.—a-Nitro-naphthalene is nitrated, resulting in the formation
1: 5 and 1:8-dinitro-naphthalenes in the proportion of about 1: 2.
The nitration mass upon cooling deposits most of the 1: 5-isomcr,
and upon pouring this filtrate into water the 1:8-isomer is pre-
cipitated, which can be purified by crystallization from benzene.
(See 1:5-dinitro-benzene)
LITERATURE.—Cain, Intermediate Products (2d Ed.), 170
Lange, Zwischenprodukte, #2315
258 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from l:8-Dinitro-naphthalene
for Dye j
1740 I
741 i!
742
743 l
!750
SULFUR DYESFast Black B
Fast Black BS
Printing Blue forWool
Kryogene Brown A
Kryogene Brown A, G
Stotisttcs ofImport and
Manufacture
I '14:— 10,313
Other Inter medic iesUsed and Notes
[Na/>S; Alkalies]or
[Fast Black B; Alkalies]
[NaaS,NaHSO*,NaOH]
[NaaS,NaHSO»,NaOH;S+NaaS]
[NaHSO3; S+NasS]
DyeAppli-cationClcss
S
S
S
S
S
a-Dinitro-naphthalene
See, 1:5-Dinitro-naphthalene
jS-Dinitro-naphthalene
See, 1:8-Dinitro-naphthalene
7-Dinitro-naphthalene
1:3-Dinitro-naphthalene (not considered herein)
5-Dimtxo-naphthalene
1: 6-Dinitro-naphthalene (not considered herein)
2:4-Dinitro-phenol
OH
= C«H4N"2O5 = 184
STATISTICS.—Manufactured '20:
DYES CLASSIFIED BY INTERMEDIATES 259
FORMATION.—From chloro-dinitro-benzene by boiling with sodium
carbonate solution
LITERATURE.—Cain, Intermediate Products (2d Ed.), 113Lange, Zwischenprodukte, #577, 1121
Dyes Derived from 2:4-Dinitro-phenol
SchultzNumberfor Dye
720
721
722
723
Ordinary Name andClass of Dye
SULFUR DYESSulfur Black
Sulfur BlackThio Cotton Black
Auronal Black
Autogene Black EEB
Statistics ofImport and
Manufacture
I '14:—4,923,981 (?)
M'17:—9,298,631
M'18:—12,385,130
M'19:—14,504,770
I '20:— 662M'20:—
16,305,037
I '14:— 50,879
Other IntermediatesUsed and Notes
[S+NaaS]
[p-Amino-phenol-sulfonic Acid]
[S+Na,S]
[S+NaaS]
DyeAppli-cationClass
S
S
S
S
N-(2:4-Dinitro-phenyl)-metanilic Acid (C. A. nomen.)
See} 2:4-Dinitro-diphenylamine-3/-sulfonic Acid
^-(2:4-Dinitro-phenyl)-^-^henylene-diamine (C. A. nomen,)
See 4'-Amino-2:4-dinitro-diphenylamine
iV-(2:4-Dinitro-phenyl)-sulfanilic Acid (C. A. nomen.)
See 2:4-Dinitro-diphenylamine-4'~sulfonic Acid
260 DYES CLASSIFIED BY INTERMEDIATES
Dinitro-stilbene-disulfonic Acid
4: 4'-Dinitro-$tilbene-2: 2'-disulfonic Acid (C. A. nomen.)
SO3H HO3S
0 aX =430
STATISTICS.—Manufactured '19:— ?
FORMATION'.—p-Xitro-toluene-sulfonic acid is dissolved in weak caustic
soda solution and oxidized with sodium hypochlorite solution. If
the product contains dinitro-dibenz^l-disulfonic acid, it is again
oxidized with sodium hypochlorite in caustic Soda solution.
LITERATURE.—Cain, Intermediate Products (2d Ed.), 39Lange, Zwischenprodukte, #1453
Dyes Derived from Dinitro-stttbene-disulfonic Acid
Ordinary Xame and 'Class of Dye
Statistics ofImport andManufacture
\Othei Intermediates
Used and Notes
DyeAppli-cationClass
10
11
12
13
18
1 STILBENE DTESMikado YellowStilbene Yellow
]IMikado Orange
1 Chloraminej Orange G
DiphenylCitronine G
I '14:— 85,795M'18:— ?M'20:— ?
I '14:— 26,010M'17:— ?M'18:— ?M'19:— ?M'20:— 38,287
Polychromine B I '14:— 16,113Diphenyl Orange KR;M' 18:— ?
Diphenyl FastYellow
I '14:— 10,229I '20:— 1,102
Dinitro-stilbene-disul-fonie Acid (2 mols)
Dinitro-stilbene-disul-fonic Acid (2 mols)
[Reduction]
Aniline (2 mols)
p-Phenylene-diamine(2 mols)
Dehydrothio-toluidine-sulfonic Acid (2 mols)
or Primuline-sulfonicAcid (2 mols)
D
D
D
DYES CLASSIFIED BY INTERMEDIATES 2(
2:4-Dinitro-tfoluene (C. A. nomen.)
mJDinitro-toluene
CH3
/\$O2 _ C7H6N2O4 = 182
NO2
STATISTICS.—Imported '14:—547,701Manufactured '18:— ?Manufactured ' 19:—746,266Manufactured '20:—1,847,191
FORMATION.—From toluene by nitration with mixed acid
LITERATUEE.—Cain, Intermediate Products (2d Ed.), 34
Lange, Zwischenprodukte, #789
USES.—For manufacture of m-tolylene-diamine
Diphenylamine
\ = Ci2HuN = 169
STATISTICS.—Imported ' 14:—81,137
Manufactured '17:— ?
Manufactured '18:— ?
Manufactured '19:— ?
Manufactured '20:— ?
FORMATION.—By heating aniline and aniline hydrochloride togclhiin an autoclave, provided with a replaceable acid-proof enamolUlining
LITERATURE.—Cain, Intermediate Products (2d Ed.), 72
Lange, Zwischenprodukte, #1598-1600
2G2 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Diphenylamine
Sckuliz
134
135
136
139
140
141
142
150
203
Ordinary Name andClass of Dye
MONOAZO DYESMetanil Yellow
Metanil Yellow,Brominated
Acid YellowMGS, GG
Orange IV
Azoflavine RSCurcumeine
Azo Yellow 3G
Brilliant Yellow SCurcumine
Fast Yellow X
Yellow Fast To Soap
Statistics ofImport and
Manufacture
I '14.-284,606M'17:— ?M'18:— ?M'19:—477,143I '20:— 8,456
M '20:—629,437
I '14:— 19,020
I '20:— 608
I '14:— 39,869I '20:— 5,225
I '14:—114,689M'17:— ?M '18:— ?M '19:— ?I '20:— 4,818M'20:— ?
I '14:— 9,934
Other IntermediatedUsed and Notes
Metanilic Acid
Metanilic Acid[Bromination]
Metanilic Acid[Sulfonation]
Sulfanilic Acid
Sulfanilic Acid[Nitration]
Sulfanilic Acid[Nitration]
Sulfanilic Acid[Sulfonation]
p-Toluidine-o-sulfonicAcid
TO-Arnino-benzoic Acid
Appli-cationClass
A
A
A
A
A
A
A
A
M
Diphenylamine-sulfonic AcidAnilino-&en2ene-suKonic Acid (C. A, nornen.)
-XH-
DYES CLASSIFIED BY INTERMEDIATES 263
FORMATION.—By sulfonation of diphenylamine, and purification from
the disulfonate formed simultaneously
LITERATURE.—Schultz, Die Chemie des Steinkohlentheers (3 aufl.), 1 ,181
Lange, Zwischenprodukte, #1615-1617
SchuhzNumberfor Dye
538
Dyes Derived from Diphenylamine-sulfonic Acid
Ordinary Name andClass of Dye
TRIPHENYL-METHANEDYE
Methyl BlueCotton. Blue
Statistics ofImport and
Manufacture
I '14:— 50,255
Other IntermediatesUsed and Notes
Diphenylamine-sulfonicAcid (3 mols)
DyeAppli-cationClass
B
Diphenylene-imide
See, Carbazole
Diphenyl-methyl-amine
See} iV-Methyl-rfiphenylamine (C, A. nomen.)
Diphenyl-naphthyl-methane
1-Naphthyl-diphenyl-methane (C. A. nomen.)
— C23H18 '==: 294
FORMATION.—From benzo-hydrol by heating with naphthalene andP2O5 at 140°-145° for some hours
LITERATURE.—A. Lehne, Ueber die Condensation von Benahydrol undNaphthalin, Ber, 13, 358 (1880)
Richter, Lex. d. Kohlenstoff Verbindungen, 4193
204 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from Diphenyl-naphthyl-methane
SchidtzNumb*jorDye
Statistics ojDve Import andDye j ^anufacture
DlPHENYlr-NAPHTHYL- iMETHANE DYE |
565 Acid Blue B, Wool Blue G
I '14:—1SO,423! I '20:— 1,852!M'2O:— ?
Other IntermediatesUsed and Notes
[Sulfonation]
DyeAppli-cationClass
N: A^-Diphenyl-m-^henylene-diajnine (C A. nomen.)
s-Diphenyl-77z-phenylene-diamine
•HN—/N—NH-
FORMATION.—From resorcinol and aniline by heating together in presence
of calcium chloride and a little zinc chloride at 210°
LITERATURE.—Green, Organic Coloring Matters (1908), 3 7
Cf. Schultz, Farbstofftabellen, #689
Dyes Derived from N: AT-Diphenyl-m-phenylene-diamine
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
267
267
689
DISAZO DYESPhenylene Black
Anthracite Black
A23NB DTEIndaziiieM
I '14M '17I '20
:— 99— ?— 220
l-Naphthylamine-4: 7-disulfonic Acid
a-NaphthylandiiB
Freund's Acida-Naphthylamine
NitroscKJim ethylaniline(1 and 2 mols)
B
DYES CLASSIFIED BY INTERMEDIATES
Diphenyl-thiourea
See, Thio-carbanilide (C. A. nomen.)
Disulfo Acid C
2-Naphthylamine-4: 8-disulfonic Acid (not considered herein)
Disulfo Acid E
See, l-Naphthol-3:8-disulfonic Acid
Disulfo Acid F
2-Naphthylamine-3: 7-disulfonic Acid (not considered herein)
Disulfo Acid S
See, l-Naphthylamine-4: 8-disulfonic Acid
N: N'-(p:p'-T)itolyl)-2: 7-naphthylene-diamine
265
H3C •NH-, —NH
FORMATION.—By heating 2: 7-dihydroxy-naphthalene with p-toluidine
and p-toluidine hydrochloride
LITERATURE.—Green, Organic Coloring Matters (1908), 38
Lange, Zwischenprodukte, #2886
Dye Derived from N: AT-C£:£'-Ditolyl)-2:7-naphthylene-diamine
SchvltzNumberfor Dye
677
Ordinary Name andClass of Dye
AZINB DYEBasle Blue R
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
Nitroso-dimethyl-aniline
DyeAppli-cationClass
B
206 DYES CLASSIFIED BY INTERMEDIATES
iVi^-Coco'-DitolylJ-m-phenylene-diainiiie (C. A. nomen.)
Di-o-tolyl-m-phen3iene-diamine
CH3 H.3C
2 = 288
FORMATION.—Presumably by heating resorcinol with o-toluidine inpresence of con Jensing agent. Cf. Di-p-tolyl-?rc-phenylene-diamine
LITERATURE.—Uilmann, Enity. tech. Chemie, 9, 63
Dye Derived from iVr^-Coio'-Ditolyy-m-phenylene-diainine
SchulizNumberfor Dye
691
Ordinary Name andClass of Dye
AZINE DYEMetaphenylene
BlueB
Statistics ofImport and
Manufacture
I '14:— 50
Other IntermediatesUsed and Notes
Nitroso-dimethyl-aniline
DyeAppli-cationClass
B
(C. A. nomen.)
Di-p-tolyl-m-phenylene-diamine
= 288
FORMATION.—From resorcinol, p-toluidine, and p-toluidine hydro-chloride by heating together in presence of calcium chloride and alittle zinc chloride
LITERATURE.—Uilmann, Enzy. tech. Chemie, 9, 63
Green, Organic Coloring Matters (1908) 7 37
DYES CLASSIFIED BY INTERMEDIATES 267
Dye Derived from N: AT-(£:/-Ditolyl)-m-phenylene-diamine
SchultzNumberfor Dye
690
Ordinary Name andClass of Dye
AZINE DYEDiphene Blue RMetaphenylene
Blue It
Statistics ofImport and
ManufactureOther Intermediates
Used ahd Notes
I '20:— 3,124 Dimethyl-p-phenylene-diamine
DyeAppli-cc tionClass
B
D SSee, Diamino-stilbene-disulfonic Acid
D TSee} Dehydro-thio-p-toluidine-sulfonic Acid
Ebert and Merz a Acid
See, Naphthalene-2: 7-disulfonic Acid
Ebert and Merz /3 Acid
Naphthalene-2: 6-disulfonic Acid (not considered here)
Epsilon Acid
See, l-Naphthol-3: 8-disulfonxc Acid
See, l-Naphthylamine-3: 8-disulfonic Acid
and 1:8-Dihydroxy-naphthalene-3-sulfonic Acid (not con-sidered herein)
Erdxnann's /i Acid
See, l-Naphthylamine-6-sulfonic Acid
Ethoxy-benzidine
Di-p-amino-ethoxy-diphenyl
2-Ethoxy-6en2iidiiie (C. A. nomen. NH^^l)
H5C2O
^ T = 228
2G8 DYES CLASSIFIED BY INTERMEDIATES
FORMATION.—Aniline is diazotized and coupled with phenol-p-sulfonicacid and the product ethylated with ethyl bromide, thus forming,—benzene-azo-phenetole-sulfonic acid. This is t h e n reduced in anaqueous solution with zinc dust and caustic soda followed byacidification with hydrochloric acid, resulting i n preparation ofethoxy-benzidine-sulfonic acid which is heated in a n autoclave withwater (at 170°) to split out the sulfonic acid group
LITERATURE.—Weinberg, Ber. 20, 3171Lange, Zwischenprodukte, #1224, 1249Heumann, Anilinfarben 4, 380
Dyes Derived from Etkoxy-benzidine
SchultiNumberfor Dye
401
402
403
404
Ordinary A ome endClass of Dye
DISAZO DYESDiamine Blue 3R
Diamine Blue BlackE
Diamine Black BO
Diamine Yellow N
Statistics ofImport arid
Manufacture
M'17:— ?I '20:— 313
Other IntermediatesUsed and Notes
Nevile-Winther's Acid(2 mols)
2-Naphthol-3:7-disul-fonic Acid
Gamma Acid
Gamma Acid (2 mols)
Salicylic AcidPhenol[Ethylation]
DyeAppli-cationClass
D
D
D
D
5-Ethoxy-2-hydroxy-^hionaphthene-l-carboxylic Acid (C. A.nomen.)
6-Ethoxy-3-hydroxyr-l-thionaphthene-2-carboxylic Acid (Germannumbering)
COOH
DYES CLASSIFIED BY INTERMEDIATES 269
FOKMATION.—5-Hydroxy-o-toluidine (amino-p-cresol) is acetylated toprotect the amino group, and then ethylated with diethyl-sulfatefor example. The resulting 2-acetamido-4-ethoxy-toluene isoxidized with potassium permanganate to 2-acetamido-4-ethoxy-benzoic acid. The acetyl group is split off by boiling with causticsoda, acid added, and the amino group diazotized with sodiumnitrite, and reacted with potassium xanthate. This xanthatecompound, upon being" treated with sodium chloro-acetate andcaustic soda, yields 5-ethoxy-phenyl-thioglycol-o-carboxylic acid.This latter heated with caustic soda condenses to 5-ethoxy-2-hydroxy-thionaphthenc-1-carboxylic acid. The successive reactionsteps are as follows:—
. COCH3. COCH3I J C H 3
. CS . OC2H5 ^ C 2 H 5 o / \ s . CH2 . COOH
C2H5O CH.COOH
LITERATURE.—Lange, Zwischenprodukte, #2167, 2168Georgievics and Grandmougin, Dye Chemistry, 437
Dyes Derived from 5-Ethoxy-2-hydroxy-thionaphthene-l-carboxylicAcid
SchulUNumberfor Bye
913
915
Ordinary Name andClass of Dye
INDIGO GROUP DYESHelindone Orange R
Helindone FastScarlet R
Statistics ofImport andManufacture
I '14:— 14,511I '20:— 3,155
I '14:— 4,302I '20:— 3,748
Other IntermediatesUsed dnd Notes
5-Ethoxy-2-h y d r 0 x y-thionaphthene-1-car-boxylic Acid (2 mols)
5-Ethoxy-2-h y d r 0 x y-thionaphthene-1-car-boxylic Acid (2 mols)
[Bromination]
DyeAppli-cationClass
V
V
270 DYES CLASSIFIED BY INTERMEDIATES
3-Etfcoxy~4'-methyl-diphenylamine (C A. nomen.)
3-Ethoxy-phenyl-4M;olyl-ainine
C2H5O
FORMATION.—100 parts of w-hydroxy-phenyl-p-tolyl-amine, 20.5 partsof caustic soda solution. (40° ?), 200 parts of alcohol, and 75 parts ofethyl chloride are heated together in an autoclave at 110-120° for7-8 hours
LITERATURE.—Lange, Zwischenprodukte, #1624, 1625
Dye Derived from S-Ethoxy-d'-methyl-diphenylamine
SchultzNumberfor Dye
548
Ordinary Name andClass of Dye
TRIPHENYL-METHANEDYE
Acid Violet 6BN
Statistics ofImpoi t and
Manufacture
I '14:— 6,861I '20:— 5,582
Other IntermediatesUsed and Notes
Ketone[Sulfonation]
DyeAppli-cationClass
A
2-Ethoxy-l-naphtliylamiiie (C. A. nomen.)
See, l-Anxino-2-naphthol Ethyl Ether
3-Et±iylainino-4-methyl-diplienylaniine
See, ^-Ethyl-iV^phenyl^m-tolylene-diamine
7-Ethylamino-2-naphthaIene-sulfonic Acid (C. A. nomen.)
See, Ethyl-2-naphthylamine-7-sulfonic Acid
2-Et3aylamino-8-naphtliol-6-stilf onic Acid
See, Ethyl-gamma Acid
7-Ethylamino-l-naphthol-3-sulfonic Acid (C. A. nomen.)
See, Ethyl-gamma Acid
DYES CLASSIFIED BY INTERMEDIATES 271
Ethyl-amino-naphthol-sulfonic Acid 7
See, Ethyl-gamma Acid
m-Ethylamino-/>henol (C. A. nomen.)
Ethyl-m-amino-phenol
OH
/NH. C2H5
FORMATION.—Ethyl-aniline is sulfonated with 23 per cent oleum, the
sodium ethyl-aniline-m-sulfonate isolated and fused with caustic
potash for ten hours at 200-220°
LITERATURE.—Cain, Intermediate Products (2d Ed.), 120
Lange, Zwischenprodukte, #593-595
SchultzNumberfor Dye
571
577
Dyes Derived
Ordinary Name andClass oj Dye
XANTHONE DYESRhodamine 6G
Rhodine 2G
from m-Ethylamino-phenol
Statistics ojImport a'nd
Manufacture
I '14:— 37,515I >20:— 8,574
Other IntermediatesUsed and Notes
m-Ethylamino-phenol(2 mols)
Phthalic anhydride[Ethyl esterification]
Dimethylamino - hy-droxy - benzoyl - ben-zoic Acid
[Ethyl esterification]
DyeAppli-cationClass
B
B
iV-Ethyl-«niline (C. A. nomen.)
Ethyl-aniline
NH.C2H5
272 DYES CLASSIFIED BY INTERMEDIATES
STATISTICS.—Manufactured '17:— ?Manufactured 18:— ?Manufactured '19:—195,161Manufactured '20:— ?
FORMATION.—By heating aniline hydrochloride and ethyl alcoholtogether in an autoclave
LITERATURE.—Cain, Intermediate Products (2d Ed.), 67Lange, Zwischenprodukte, #93
USES.—For preparation of ethyl-methyl-aniline and benz^l-ethyl-aniline
a-(iV-ethyl-anilino)-^-toluene-sulfonic Acid (C A. nomen.)
See, Ethyl-sulfobenjzyl-aniline
Ethyl-benzyl-aniline
See, Benzyl-ethyl-aniline
Ethyl-benzyl-aniline-sulf onic Acid
See, Ethyl-sulfobenzyl-aniline
2:2'-Ethylene-bis (5-nitro-benzene-sulfonic Acid) (C. A. nomen.)
See, Dinitro-dibenz3i-disulfonic Acid
Ethyl-F Acid
See, Ethyl-2-naphthylamine-7-sulfonic Acid
Ethyl-gamma Acid
2-Ethylamino-8-naphthol-6-sulfonic Acid
Ethylamino-naphthol-sulfonic Acid y
7-Ethylamino-l-naphthol-3-sulfonic Acid (C. A. nomen.)
[HO
HO A 1 J K H *C 2 H 5 = Ci2H13NO4S = 267
DYES CLASSIFIED BY INTERMEDIATES 273
FORMATION.—G acid (2-naphthol-6: 8-disulfonic acid) is heated with
ethylamine in an autoclave at about 200°. The ethylamino-G acid
thus obtained is fused with caustic soda at 210-220°, and the ethyl-
gamma acid isolated
LITERATURE.—Lange, Zwischenprodukte, #2550
Dye Derived from Ethyl-gamma Acid
SchultzNumberfor Dye
334
Ordinary Name andClass of Dye
DISAZO DYEDiphenyl Blue Black
Statistics ofImport and
Manufacture
I 14:— 26,240
Othtzr IntermediatesUsed and Notes
HAcidBenzidine
DyeAppli-cationClass
D
6-Ethylmercapto-2-hydroxy-^hionaphthene-l-carboxylic Acid (C
A. nomen.)
5-Ethylthio-2~hydroxy-thionaphthene-l-carboxylic Acid
6-Ethylthio-3-hydroxy-l-thionaphthene-2-carboxylic Acid (Ger-man numbering)
C C O O H or C2RS CH.COOH
— 254
FORMATION.—4-Acetamido-anthranilic acid is diazotized and treated
with potassium xanthate. This xanthatc compound is reacted
with chloro-acetic acid and then hydrolyzed to split the acetyl
group from the 4-amino radical. This amino group is now diazo-
tized and reacted with potassium xanthate. This second xanthate
compound is treated with ethyl-sulfate, resulting in the formation of
5-ethylmercapto-phenyl-thioglycol-o-carboxylic acid. This latter,
upon being heated with caustic soda, condenses to 5-ethylmercapto-
274 DYES CLASSIFIED BY INTERMEDIATES
2-hydroxy-thionaphthene-l-carboxylic acid. The successive re-action steps are as follows:—
CH3CO. CH3CO.
CH3CO. H N / \ s . CH2. COOHI J C O O H
. CS. OC2H5
. CH2 . COOH
CsHsO.SC.Sf' X,S.CH2.COOHI J C O O H
S.CH2.COOHCOOH
: . C O O H
(Y
LITERATURE.—Georgievics and Grandmougin, Dye Chemistry, 436-437Lange, Z^ischenprodukte, #2175
Dye Derived from 5-Et]iylmercapto-2-hydroxy-thioiiaphthene-l-carboxylic Acid
° Z Ordinary Name andClass of Dye
Statistics ofImport arid
ManufactureOther Intermediates
sed and Notes
DyeAppli-cationClass
J INDIGO GROUP DYES916 I Helindone Scarlet S I '14:— 5,515
I '20:— 565-Ethylmercapto-2-hy-
droxy-thionaphthene1-carboxylic Acid (2mols)
(C. A. nomen.)
Ethyl-methyl-aniline
Methyl-ethyl-aniline
FORMATION.—From ethyl-aniline by methylation, or from methyl-aniline by ethylation
LITERATURE.—Beil. II, 334
DYES CLASSIFIED BY INTERMEDIATES 275
Dye Derived from Ethyl-methyl-aniline
SchultzNumberfor Dye
661
Ordinary Name andClass 0} Dye
THIAZINE DYEThionine Blue GO
Statistics ofImport andManufacture
I '14:— 18,618I '20:— 2,030
Other IntermediatesUsed and Notes
Dimethyl-p-phenylene-diamine - thiosulfonicAcid
[Oxidation, etc.]or
Nitroso-dimethyl-aniline
[Reduction, Oxidation,Na^Os, etc.]
orDimethyl-p-phenylene-
diamine[Na2S2O3, Oxidation,
etc.]or
Dimethyl-aniline[Naa^Os, etc.]
DyeAppli-cationCloss
B
Ethyl-a-naphthylamine
iV-Ethyl-1-naphthylamine (C. A. nomen.)
STATISTICS.—Imported '14:—1,102 lbs.
FOKMATION.—By treating a-naphthylamine with ethyl bromide
LITERATURE.—Limpricht, Ann. 99, 117 (1856)
Friedlaender and Welmans, Ber. 21, 3124 (1888)
Bamberger and Helwig, Ber. 22, 1315 (1889)
Thorpe, Die. Chemistry, 3, 587
276 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Ethyl-a-naphthyl-amine
Schidtz'Number
1S6
55S
Ordinary Name andClass oj Dye
MONOAZO DYELanacyl Violet B
DlPHENYL-XAPHTHYL-METHAXE-DYE
Victoria Blue R
Statistics ofImport andManufacture
I '14:— 3,628M'17:— ?M'lS:— ?
I '14:— 4171I '20:— 97
Other Intermediatessed and Notes
HAcid
Hydrol or Ketone
DyeAppli-cationClass
A
B
Ethyl-2~naphthyla-mine-7-sulfonic AcidEthyl-F AcidEthyl-j3-naphthylamine-5-sulfonic Acid7-Ethylamino-2-7iaphthalene-suIfonic Acid (C. A. nomen.)
HO3S; ;NH.C2H5 _ ,
FORMATION.—By eth\rlation of 2-naphtbyIamine-7-sulfonic acid bymeans of an ethyl halide or sodium ethyl sulfate, in an autoclaveat 100-110° C. for several hours
LITERATURE.—Lange, Zwischenprodukte, #2385Dyes Derived from Ethyl-2-naphthylamiiie-7-sulfoiiic Acid
SchultzNumberfor Dye
231
371
372
Ordinary Name andClass of Dye
DISAZO DYESCloth Red 3B
Extra
Roseazurine G
RosazurineB
Statistics ofImport andManujactwe
I '14:— 15I ;20:— 84
Other IntermediatesUsed and Notes
fl-Aroino-azo-toluene
Tolidine2-Naphthylamine-7-
sulfonic Acid
TolidineEthyl-2-naphthyl-
amine-7-sulf onic Acid(2 mols)
DyeAppli-cationClass
M
D
D
DYES CLASSIFIED BY INTERMEDIATES 277
Ethyl-jS-naphthylamine-5-sulfonic AcidSee, Ethyl-2-naphthylamine-7-sulfonic Acid
iV-Ethyl-^-nitroso-aniline (C. A. nomen.)
See, p-Nitroso-ethyl-aniline
i\T~Ethyl-4-nitroso-o-£oluidine (C. A. nomen. NHR =1)
See, Nitroso-ethyl-o-toluidine
N-Ethyl-iV-phenyl-&enzylamine {C. A. nomen.)
See, Benzyl-ethyl-aniline
Ethyl-phenyl-hydrazine
a-Ethyl-a-phenyl-Aydrazine (C A. nomen.)
C2H5
*.NH2 =C8H1 2N2 = 136
FORMATION.—Phenyl-hydrazine is treated with metallic sodium toform the sodium compound, from which by means of ethyl iodidethe ethyl-phenyl-hydrazine is prepared
LITERATURE.—Thorpe, Die. Chemistry, 3, 53
Dye Derived from Ethyl-phenyl-hydrazine
SchultzNumberjor Dye
130
Ordinary Name andClass of Dye
MONOAZO DYEChromazone Blue R
Statistics ofImport and
ManufactureOihei Intermediates
Used and Notes
p-Amino-benzaldehydeChromotropic Acid
DyeAppli-cationClass
M
. nomen.)
Phenyl-p-amino-ethyl-o-toluidine
3-Ethylamino-4-methyl-diphenylamine
NH-
JNH.C2H5
CH3
278 DYES CLASSIFIED BY INTERMEDIATES
FORMATION.—JV^Phenyl-^m-tolylene-diamine (q.v.) is heated for ten
hours with ethyl bromide at 150-175°
LITERATURE.—Ger. Pat. 87,667, Frdl. IV, 85
Beilstein, Organische Chemie (3 auf.), IV spl. 400
Lange, Zwischenprodukte, #1750, 1755, referring to the
same patent, gives a different formula
Dye Derived from i^-Ethyl-iSTi-phenyl^-m-toIylene-diainine
SchvlteNumberfor Dye
684
Ordinary Name andClass of Dye
AZINE DYEBrilliant Rhoduline
Red
Statistics ofImport and
ManufactureOther Intermediates
sed and Notes
Nitroso-ethyl-o-toluidine
DyeAppli-cationClass
B
Ethyl-sulfobenzyl-aniline
Benz^^l-ethyl-aniline-sulfonic Acid
Ethyl-benzyl-aniline-sulfonic Acid
a-(i\T-Ethyl-anilino)-p-toluene-suhconic Acid (C. A. nomen.)
. N . = 291
STATISTICS.—Manufactured 1919 and 1920, but in undisclosed quantities
FORMATION.—By sulfonation of benz^l-ethyl-aniline with 20 per centoleum at 40-50°
LITERATURE.—Cain, Intermediate Products (2d Ed.), 69
Cf. Lange, Zwischenprodukte, #1500
DYES CLASSIFIED BY INTERMEDIATES 279
Dyes Derived from Ethyl-sulfobenzyl-aniline
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport andManufacture
Other IntermediatesUsed and Notes
DyeAppli-cationClass
50
502
503
506
529
530
662
MONOAZO DYEAzo Cardinal G
TRIPHENYL-METHANE
DYESGuinea GreenAcid Green 2BG
M'14:— ?
Night Qreen ANeptune GreenBrilliant Milling
Green B
Erioglaucine
Acid Violet 6B
Acid Violet 6BFormyl VioletGuinea Violet
THIAZINE DYE
Thiocarmine R
I '14:— 49,971M'17:— ?M'18:—M'19:—I '20:—
M'20:—
??278
I '14:-M'19:-I '20:-M320:-
I '14:-M'19:-I '20:-
M'20:
40,868
10,940
66,526
6,160
I '14.-161,624M'17M'18M'19I '20
M'20- 3,925-144,207
I '14:— 1,399
p-Nitro-aniline
Ethyl-sulfobenzyl-aniline (2 mols)
Benzaldehyde[Oxidation]
Ethyl-sulfobenzyl-aniline (2 mols)
o-Chloro-benzaldehyde[Oxidation]
Ethyl-sulfobenzyl-aniline (2 mols)
Benzaldehyde-0-sulf onic Acid
[Oxidation]
Ethyl-sulf ob enzyl-aniline (2 mols)
Dimethyl-p-amino-benzaldehyde
[Oxidation]
Diethyl-anilineEthyl-sulfobenzyl-
aniline (2 mols)[Oxidation]
Ethyl-sulf ob enzyl-p-phenylene-diamine
etc.]
280 DYES CLASSIFIED BY INTERMEDIATES
iV-Ethyl-i^-(^-sulfo-benzyl)-metanilic Acid (C. A. nomen.)
See, Benzyl-ethyl-anftine-disulfonic Acid
Ethyl-sulfobenzyl-^-phenylene-diamine
Benjzyl-ethyl-p-phen}iene-diamine-sulfonic Acid
p-Amino-benzyl-ethyl-aniline-sulfonic Acid
a-(p-Amino-A'-ethyl-anilino)-p-toluene-sulfonic Acid (C A.nomen.)
y~K = 3 0 6
FORMATION.—Ben^yl-ethyl-ardline-sulfonic acid is changed into therdtroso-derivative with nitrous acid, and this latter is reduced withsulfite
LITERATURE.—Lange, Zwischenprodukte, #1499, 929Cf. Cain, Intermediate Products (2d Ed.), 69
Dye Derived from Ethyl-sulfobemiyl-^-phenylene-diainine
SchuLttNumberj or Dye
662
Ordinaly Name andClass of Dye
THIAZIXB DYEThocannine R
Statistics ofImport and
Manufacture
I '14:— 1,399
Other IntermediatesUsed and Notes
Ethyl-sulfobenzyl-aniline
[Na^Oa, etc.]
DyeAppli-cationClass
A
Et^Lyl-sulfobenzyl-^-phenylene-diamine-tidostilfonic Acid
a-(4-Amino-Ar-ethyl-3-sulfomercapto-ardlino)-p^oluene-sulfonicAcid (C. A. nomen.)
CJEL-—X—CH
NHs
S.SO3H
DYES CLASSIFIED BY INTERMEDIATES 281
FORMATION.—Ethyl-sulfobenzyl-p-phenylene-diamine is dissolved indilute hydrochloric acid, zinc chloride solution and sodium thio-sulfate solution added; and then oxidized quickly with solution ofsodium bichromate
LITERATURE.—Lange, Zwischenprodukte, #1501
Dye Derived from Ethyl-sulfobenzyl-^-phenylene-diamine-thiosulfonicAcid
SchultzNumberfor Dye
667
Ordinary Name andClass of Dye
THIAZINE DYEBrilliant Alizarin
BlueIndochromine T
Statistics ofImport and
Manufacture
I '14:— 19,481M'19:— ?I '20:— 3,214M'20:— ?
Other IntermediatesUsed and Notes
1:2-Naphthoquinone
DyeAppli-cationClass
M
6-Ethylthio-2-hydroxy-thionaphthene-l-carboxylic Acid
See, 5-Ethylmercapto-2-hydroxy-thionaphthene-l-carboxylicAcid (C A. nomen.)
6-Ethylthio-3-hydroxy-l-thionaphthene-2-carboxylic Acid (Ger-man numbering)
See, S-Ethylmercapto^-hydroxy-thionaphthene-l-carboxylicAcid (C A. nomen.)
JV-Ethyl-o-*oluidine (C. A. nomen.)
Ethyl-o-toluidine
HNC2H5
FORMATION.—From o-toluidine hydrochloride and ethyl alcohol ^byheating together in an autoclave at about 200°. The crude productcontains considerable o-toluidine, which can be removed as sulfateby adding just sufficient sulfuric acid to combine with it; allowingto cool, and centrifugating
LITERATURE.—Cain, Intermediate Products (2d Ed.), 71Lange, Zwischenprodukte, #128
282 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 2V-Ethyl-o-toluidine
SchultzNumberfor Dye
500
546
663
Ordinary Name andClass of Dye
TKIPHENYL-METHANEDYES
Setocyanine 0
Cyanol
THIAZINE DTENew Methylene Blue
N
Statistics ofImport and
Manufacture
I >14:— 923I '20:— 1,102
I ' 14 : - 40,015I '20:— 7,954
I '14:— 30,392I 320:— 513
Other IntermediatesUsed and Notes
Ethyl-o-toluidine(2 mols)
o-Chloro-benzaldehyde[Oxidation]
Ethyl-o-toluidine(2 mols)
m-Hydroxy-benzalde-hyde
[Sulfonation, Oxidation]
Ethyl-o-toluidine(2 mols)
[Nitroso-derivative,Nas&Oa, etc.]
orp-Amino-etliyl-o-
toluidine[Na2S2O3, etc.]
DyeAppli-cationClass
B
A
B
iV-Ethyi-p-*oluidine (C. A. nomen.)
Ethyl-p-toluidine
HNC2H5
FORMATION.—From p-toluidine hydrochloride and ethyl alcohol byheating together in an autoclave and purification of resultingproduct
LITERATURE.—C/. Cain, Intermediate Products (2d Ed.), 71Lange, Zwischenprodukte, #128Ger. Pat. 21,241, Frdl. 1, 21
DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from N-Ethyl-^-toluidine
283
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
Manufactw eOther Intermediates
Used and Notes
DyeAppli-cationClass
671AZINE DYE
Induline Scarlet I '14:— 198I '20:— 154
a-Naphthylamine
iV*~Ethyl-4-m-folylene-diamine (C. A. nomen. NH2=1)
p-Amino-ethyl-o-toluidine
NH2
W . C 2 H 5 — CoHuNTi —150
FOKMATION.—From 5-nitro-ethyl-o-toluidine (NH2 = 1) [4-nitro-ethyl-o-toluidine (CH3==1)] by reduction with zinc dust and hydro-chloric acid
LITERATURE.—Beilstein, Organische Chemie (3 auf.), IV, 601J. Chem. Soc, 67, 247
Dye Derived from iV3-Ethyl-4-m-tolylene-diamine
SchultzNumbeifor Dye
684
Ordinary Name andClass of Dye
AZINE DYEBrilliant Rhodulinc
Red
Statistics ofImpoi * and
Manujactu. eOther Intermediates
Used and Notes
Methyl-o-toluidineAniline
DyeAppli-cationClass
B
JN^-Ethyl-^-^olylene-diamine (C. A. nomen.)
p-Amino-ethyl-o-toluidine
NH.C 2 H 5
Q O H , _
NHS
= C 9 H u N 2 =150
284 DYES CLASSIFIED BY INTERMEDIATES
FORMATION.—From 4-nitroso-ethyl-o-toluidine (NHR= 1) by reductionwith SnCl2+HCl
LITERATURE.—Beil. II, 609
Dye Derived from JV^-Ethyl-^-tolylene-diamine
SchvltzNumberJor Dye
663
Ordinary Name andClass oj Dye
THIAZINE DYENew Methylene Blue
N
Statistics ofImport andManufacture
I '14:— 30,392I '20:— 513
Other IntermediatesUsed and Notes
Ethyl-o-toluidine[Na SsOs]
DyeAppli-cationClass
B
Ewer and Pick's Acid
See, Naphthalene-1:6-disulfonic Acid
FAcid
See, 2-Naphthol-7-sulfonic Acid
See, 2-Naphthylamine-7-sulfonic Acid
2-Naphthylamine-3: 7-disulfonie Acid (not considered herein)
2-Amino-7-naphthol-3-sulfonic Acid (not considered herein)
2: 7-Dihydrox5r-naphthalene-3-sulfonic Acid (not considered herein)
Formaniline
See, Anhydro-formaldehyde-aniline
4-Formyl-m-&enzene-disulfonic Acid (C. A. nomen.)
See, Benzaldehyde-disulfonic Acid
o-Formyl-frenzene-sulfonic Acid (C. A. nomen.)
See, Benzaldehyde-o-sulfonic Acid
4-Formyl-6-methyl-m-benzene-disulfonic Acid
See, 3-methyl-benzaldehyde-4: 6-disulfonic Acid
Jorsling's Acid I
See, 2-Naphthylamine-8-sulfonic Acid
DYES CLASSIFIED BY INTERMEDIATES
Forsling's Acid II
See, 2-Naphthylamine-5-sulfonic Acid
Freund's Acid
l-Naphthylamine-3: 6-disulfonic Acid
4-Amino-2: 7-naphthalene-disulfonic Acid (C A. nomen.)
a-Naphthylamine-a-disulfonic Acid
A16n's a Acid
NH2
285
HO3S SO3H
STATISTICS.—Imported '14:—5,246 lbs.Manufactured ' 18:— ?Manufactured ' 19:— ?
FORMATION.—Naphthalene is heated with five parts of concentratedsulfuric acid for about 8 hours at 160-200°, the mixture is cooledand two parts of 50 per cent nitric acid are added. After reactingfor some time the nitration mass is diluted and reduced with iron
LITERATURE.—Cain, Intermediate Products (2d Ed.), 195Thorpe, Die: Chemistry, 3, 592Lange, Zwischenprodukte, #2591
Dyes Derived from Freund's Acid
SchultzNumbet
Bye
266
267
Ordinary Name andClass of Dye
DISAZO DYESNaphthylamine
Black D
Anthracite Black
Statistics ofImport and
Manufacture
I '14:—152,141M'17:— ?M'18:— 29,724M'19:— ?I '20:— 1,687M'20:— ?
I '14:-- 99M'17:— ?I '20:— 220
Oihei Intermedic tesUsed and Notes
a-Naphthylamine(2 mols)
a-NaphthylamineDiphenyl-m-phenylene-diamine
DyeAppli-cationClass
A
A
286 DYES CLASSIFIED BY INTERMEDIATES
G Acidl
2-Naphthol-6: 8-disulfonic Acid (C A. nomen.)
j3-Naphthol-]5-disulfonic Acid
/3-Naphthol-Y-disulfonic Acid
/3-Naphthol-disulfonic Acid G
/3-Naphthol-disulfonic Acid 7
YAcid
HO3S
HO3S0 H =
STATISTICS.—Imported 14':—11,624 lbs.Manufactured'18:— ?Manufactured '19:—732,192 lbs.Manufactured '20:—1,446,605 lbs.
FORMATION.—Sulfonation of /S-naphthol and separation from the Racid simultaneously formed
LITERATURE.—Cain, Intermediate Products (2d Ed.), 227Thorpe, Die. Chemistry, 3, 627Lange, Zwischenprodukte, #2659-2661
Dyes Derived from G- Acid
SchultzNumberfor Dye
38
Ordinary Name andClass of Dye
MONOAZO DYESOrange G
Statistics ofImport and
Manufacture
I '14:— 48,456M'17:— ?M'18:— ?M'19:— ?I '20:— 100
M'20:—120,874
Other IntermediatesUsed and Notes
Aniline
DyeAppli-cationClass
A
1 Occasionally in the old literature G acid is used to mean Gamma acid (or2-Amino-8-naphthol-6-sulfonic acid), or 2-Naphthylamine-6:8-disulfonic acid, or1:7-Dihydroxy-naphthalene-3-sulfonic acid.
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from G Acid (continued)
287
SchultzNumberfor Dye
113
122
169
227
270
319
566
Ordinary Name andClass oj Dye
MONOAZO DYES(continued)
Crystal Ponceau
Erica G
Cochineal Red A
DISAZO DYESBrilliant Croceine M
Brilliant Croceine 9B
Diamine Scarlet B
DlPHENYL-NAPHTHYL-METHANE DYE
Wool Green S
Statistics ofImport andManufacture
I 14:— 628
I 14:— 2,370M18:— ?I '20:— 1,142
I 14:— 32,645M17:— ?M18:— ?M19:—231,519M'20:—288,945
I 14:—125,137M17:— ?M18:— 84,643M19:—157,509I '20:— 49M'20:—129,124
I 14:— 41,175I '20:— 10,565
I 14:— 60,073M17:— ?M19:— ?I '20:—127,764M '20:—212,362
Other IntermediatesUsed and Notes
a-Naphthylamine
Dehydro-thio-ra-xyli-dine
Naphthionic Acid
Amino-azo-beiizene
Amino-G AcidAnilineRAcid
BenzidinePhenol[Ethylation]
Hydrol
DyeAppli-cationClass
A
D
A
A
A
D
A
Gallamic AcidSee, Gallamide (C. A. nomen.)
Gallamide (C. A. nomen.)Gallamic AcidGallic Acid Amide
288 DYES CLASSIFIED BY INTERMEDIATES
CO.NH*
FORMATION.—From tannin by boiling with strong solution of am-monium sulfite and aqueous ammonia until the excess of ammoniahas been driven off. The amide crystallizes out upon cooling
LITERATURE.—Green, Organic Coloring Matters (1908), 46Lange, Zwischenprodukte, #1546
Dyes Derived from Gallamide
SchulizNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
627
630
637
638
641
646
OXAZINE DYESModern Cyanine
Cyanaznrine
Gallamine Blue
Amido GallainliieBlue
Coreine RRCoelestine Blue B
Coreine AR
I '14:I '20:
Nitroso-dimethyl-anilineDimethyl-p-phenylene-
diamineReduction]
Nitroso-dimethyl-anilineAniline[Reduction]
2,756 Nitroso-dimethyl-aniline16,446
Nitroso-dimethyl-aniline[Ammonia, Reduction]
1,320 Nitroso-diethyl-anilineI '20:— 44 or Diethylamino-azo-
benzene
Nitroso-diethyl-ardlineor Diethylamino-azo-
benzeneAniline[Sulfonation]
or[Coreine RR; Aniline;
Sulfonation]
M
M
M
M
M
M
DYES CLASSIFIED BY INTERMEDIATES
Gallanilic Acid
See, Gallanilide (C. A. nomen.)
Gallanilide (C. A. nomen.)
Gallanilic Acid
Gallic Acid Anilide
CO—NH
289
H
STATISTICS.—Manufactured '19:—Manufactured '20:—
FORMATION.—From tannin by heating with aniline
LITERATURE.—Green, Organic Coloring Matters (1908), 46Cf. Lange, Zwischenprodukte, #1546
Dye Derived from Gallanilide
SchultzNumberfor Dye
639
Ordinary Name andClass of Dye
OXAZINE DYEGallanilic Violet R, B
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
Nitroso-dimethyl-(ordiethyl-) aniline
DyeAppli-cationClass
M
Gallic Acid
3:4: 5-Trihydroxy-benzoic Acid
COOH
STATISTICS.—Imported '14:—61,644 lbs.Manufactured regularly, but in amounts that are not
yearly disclosed
290 DYES CLASSIFIED BY INTERMEDIATES
FORIMATION.—From nut galls (Chinese or Aleppo) by action of ferments
or acids, and subsequent extraction and crystallization
LITERATURE.—Green, Organic Coloring Matters (1908), 46
Lange, Zwischenprodukte, #1112
Dyes Derived from Gallic Acid
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
599
601
622
624
625
626
XANTHONE DYESGalleine
Coeruleine S
OXAZINE DYESDelphine Blue B
Modern Violet N
Chrome Heliotrope
Gallocyanine
I '14:— 15,404M'19:— ?
'20:— 5,075M'20:— ?
I '14:—M'19:—I '20:—
3,404
9,392
M'17:— ?M'18:— ?M'19:— 43,827I '20:— 29,643M '20:— 76,719
I '20:— 5,688
I '14:— 78,253M'17:— ?M '18:—435,460M'19:—365,243I '20:— 12,414M'20:— 70,169
Phthalic AnhydrideGallic Acid (2 mols)
Phthalic AnhydrideGallic Acid (2 mols)[Dehydration]
or[Galleine dehydrated]
Nitroso-dimethylanilineAniline[Sulfonation]
or[Gallocyanine, Aniline,
Sulfonation]
Nitroso-dimethylaniline[CO2 split off]
or[Gallocyanine heated]
Nitroso-methyl-aniline[Reduction]
Nitroso-dimethylaniline
M
M
M
M
M
M
DYES CLASSIFIED BY INTERMEDIATES 291
Dyes Derived from Gallic Acid (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
628
629
631
632
633
634
635
OXAZINE DYES(continued)
Gallocyanine MS
Gallogreen DHModern Blue
Chromocyanine V
Ultra Violet LGP
Indalizarine R
Indalizarine Green
Blue 1900 TCModern Violet
I '20:— 22 Dimethylamino-azo-benzene-disulfonicAcid
orNitroso-dimethyl-
aniline[Sulfonation; Oxidation]
Nitroso-dimethyl-aniline
[Formaldehyde, Reduc-tion]
or[Gallocyanine, Formal-
dehyde, Reduction]
M'18:-MJ19:-I '20:-M'20:-
I '14:
??
1,287?
4,368
I '20:— 551
I '20:— 1,933
Nitroso-dimethyl-aniline
[Sulfonation]or
[Gallocyanine, Sulfites]
Nitroso-dimethyl-aniline (2 mols)
Gallic Acid (2 mols)
Nitroso-dimethyl-aniline
[Sulfonation]
Nitroso-dimethyl-aniline
[Sulfonation; Nitration]or
[Indalizarine nitrated]
Nitroso-dimethyl-aniline
[Reduction]
292 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Gallic Acid (continued)
SchultzNumberfor Dye
642
643
644
645
664
Ordinary Name andClass of Dye
OXAZINB DYES(continued)
Phenocyanine TC
Phenocyanine TV
Ultracyanine B
Gallazine A
THIAZINE DYELeuco-gallo
Thionine DH
Statistics ofImpart and
Manufacture
I '20:— 4,740
MJ17:— ?I '20:— 1,543
Other IntermediatesUsed and Notes
Nitroso-dimethyl-aniline
Resorcinolor
[Gallocyanine, Resorci-nol]
Nitroso-dimethyl-aniline
Resorcinol[Sulfonation]
or[Phenocyanine sulfo-
nated]
Nitroso-dimethyl-aniline
Resorcinol [AlkalineCondensation]
or[Gallocyanine; Resorci-
nol; Alkaline Con-densation]
Nitroso-dimethyl-aniline
Schaeffer's Acid[Oxidation]
or[ G a l l o c y a n i n e ,
Schaeffer's AcidOxidation]
Dimethyl-p-phenylene-diamine-thiosulfonicAcid
DyeAppli-cationClass
M
M
M
M
M
DYES CLASSIFIED BY INTERMEDIATES 293
Dyes Derived from Gallic Acid (continued)
SchultzNumberfor Dye
772
782
Ordinary Name andClass of Dye
ANTHRAQTJINONE ANDALLIED DYES
Galloflavine W
Anthracene BrownAlizarin Brown
Statistics ofImport and
Manufacture
I '14:— [838I '20:— 24
I '14:—115,586M/17:— ?M'18:— ?M'19:— 40,426I '20:— 2,728M'20:— 42,840
Other IntermediatesUsed and Notes
Gallic Acid (2 mols)
Benzoic Acidor Phthalic Anhydride
DyeAppli-cationClass
M
M
Gallic Acid Amide
See, Gallamide (C. A. nomen.)
Gallic Acid Anilide
See, Gallanilide (C. A. nomen.)
Gallic Acid Methyl Ester
CO.OCHs
OH
FOKMATION.—From gallic acid by heating with methanol (methylalcohol) and hydrochloric acid
LITERATURE.—Green, Organic Coloring Matters (1908), 40
294 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Gallic Acid Methyl Ester
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
Manufacture
Other IntermediatesUsed and Notes
DyeAppli-cationClass
636
640
OXAZINE DYES
Prune
Modern Azurine DH
I '14:— 3,197 Nitroso-dimethyl-anilineI '20
3,4,418
Nitroso-dimethyl-anilineAniline
M
M
Gamma Acid
2-Amino-8-naphthol-6-sulfonic Acid
Amino-naphthol-sulfonic Acid 7
Amino-naphthol-sulfonic Acid G
G Acid (occasionally in old literature)
7-Amino-l-naphthol-3-sulfonic Acid (C. A. nomen.)
H O
=:Ci0H9NO4S = 239HO3S
STATISTICS.—Manufac tured J 18:— ?
Manufac tured ;19:—155,025 lbs.
Manufac tured '20:—418,456 lbs.
FORMATION.—£-Naph tho l is sulfonated to R and G acids, and these
two /3-naphthol-disulfonic acids are separated. The sodium salt
of G acid is hea ted in an autoclave with ammonia and sodium
bisulfite solution to form amino-G acid (2-naphthylamine-6:8-
disulfonic acid). This la t ter is fused in an autoclave with caustic
soda, t h u s forming gamma acid.
L I T E R A T U R E . — C a i n , In te rmedia te Products (2d Ed. ) , 236
Lange, Zwischenprodukte, #2546
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Gamma Acid
295
SchultzNumberfor Dye
241
245
274
295
297
327
328
329
330
331
332
Ordinary Name andClass of Dye
DISAZO DYESNeutral Gray G
Nyanza Black B
Diaminogene BB
Diphenyl Fast Black
Benzo FastPink 2BL
Diamine Violet N
Diamine Black HODianol Black RW
Diamine Brown V
Zambesi Brown G
Alkali DarkBrown GV
Dianil Garnet BBenzo Fast Red
IMIM
II
I
II
IMM
I
M
II
II
Statistics ofImport aridManufacture
14:—19:—'20:—'20:—
2,546?
3,472?
14:—313,629'20:— 18,120
14:—
14:—'20:—
14:—19:—'20:—
14:—
19:—
14:—'20:—
14:—'20:—
882
3,2521,226
18,263?
92,503
8,253
?
4,0281,104
5,9853,799
Other IntermediatesUsed and Notes
Anilinea-Naphthylarnin
p-Nitro-anilineq-Naphthylamin e[p-Nitro-aniline reduced
after coupling]
Acetyl-1:4-naphthy-lene-diamine-6-sul-f onic Acid
a-Naphthylamin
p: p'-Diamino-ditolyl-amine
m-Tolylene-diamine
Diamino-diphenyl-urea-disuKonic Acid
Gamma Acid (2 mols)
BenzidineGamma Acid (2 mols)
BenzidineGamma Acid (2 mols)
Benzidine7n-Phenylene-dianrine
Benzidine2:7-Naphthylene-dia-
mine-sulf onic Acid
BenzidineNitroso-jS-naphthol
BenzidineAmino-R Acid
DyeAppli-cationClass
D
D
D
D
D
D
D
D
D
D
D
296 DYES CLASSIFIED BY INTERMEDIATES
SchultzNumberfor Dye
333
335
343
344
399
402
403
436
437
Dyes Derived
Ordinary Name andClass of Dye
DISAZO DYES(continued)
Diamine Black BHOxamine Black BHN
i
NaphthamineBlack RE
Diamine Fast Red F
Diamine Brown M
Indazurine TS
Diamine BlueBlack E
Diamine Black BO
TKISAZO DYESColumbia Black FF
Iso-DiphenylBlack R
from Gamma
Statistics ofImport and
Manufacture
I '14:—619,430M'17:— ?M'18:— ?M'19 :—485,046I '20:— 5,512M'20:—803,501
I '14:— 49,016
I '14:— 50,479M'19:— 56,864I '20:— 4,040M'20:—115,865
I J14:— 65,396M'lS:— ?M'19:— 15,959M'20:—257,872
I '14:—102,997M'18:— ?M'19:— ?I '20:— 23,350M'20:— ?
Acid (continued)
Other IntermediatesUsed and Notes
BenzidineHAcid
BenzidineKAcid
BenzidineSalicylic Acid
BenzidineSalicylic Acid
Tolidin1:7-Dihydroxy-2-naph-
thoic-4-sulfonic Acid
Ethoxy-benzidine2-Naphthol-3:7-disul-
f onic Acid
Ethoxy-benzidineGamma Acid (2 mols)
l-Naphthylamine-6-and 7-sulf onic Acids
m-Phenylene-diaminep-Phenylene-diamine
Resorcinolp-Phenylene-diaminem-Phenylene-diamine
DyeAppli-cationClass
D
D
D
D
D
D
D
D
D
DYES CLASSIFIED BY INTERMEDIATES 297
Dyes Derived from Gamma Acid (continued)
SchultzNumberfar Dye
Ordinary Name andClass oj Dye
Statistics ofImport andManufacture
Other IntermediatesUsed and Notes
DyeAppli-cationClass
440
442
444
461
472
473
491
TRISAZO DYES(continued)
Direct IndigoBlue BK
Direct Black V
Cr umpsall DirectFast Brown B
Coomassie UnionBlacks
Chloramine Blue HW
Diamine Black HW
TETRAKISAZO DYEDianil Black PR
I 14:—145,738
I '20:-- 342
Benzidinera-Amino-p-cresol
Methyl EtherGamma Acid (2 mols)
Benzidine2R Acida-Naphthylamine
BenzidineSalicylic AcidAniline
1:4-Naphthylene-dia-mine-2-suLfonic Acid
m-Phenylene-(or Toly-lene-) diamine orResorcinol (2 mols)
Benzidine2: 5-Dichloro-anilineHAcid
Benzidinep-Nitro-anilineHAcid
Benzidine sulf onic AcidGamma Acid (2 mols)m-Phenylene-diamine
(2 mols)
G R Acid
See, l -Naphthol-3: 6-disulfonic Acid
298 DYES CLASSIFIED BY INTERMEDIATES
H Acid
l-Amino-8-naphthol-3: 6-disulfonic Acid
Amino-naphthol-disulfonic Acid H
8-Amino-l~naphthol-3: 6-disulfonic Acid (C. A. nomen.)
HO NH2
HO3S SO3H
STATISTICS.—Imported '14:— 96,296 lbs.Manufactured '17:—3,089,273 lbs.Manufactured '18:—3,837,534 lbs.Manufactured '19:—2,883,228 lbs.Manufactured '20:—5,180,993 lbs.
FORMATION.—Naphthalene is trisulf onated with oleum, and then nitratedand reduced with iron, resulting in the formation of Koch acid orl-naphthylamine-3:6: 8-trisulfonic acid. This latter is now fused inan autoclave with caustic soda, forming H acid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 237Lange, Zwischenprodukte, #2720-2724Thorpe, Die. Chemistry, 3, 641
SchultzNumberfor Dye
41
182
186
Dyes
Ordinary Name andClass of Dye
MONOAZO DYESFast Acid
Fuchsine B
Fast Sulf onViolet 5BS
Brilliant Sulf onRedB
Lanacyl Violet B
Derived from 1
Statistics ofImport andManufacture
M'18:— ?M'19:— 26,699M'20:— 30,678
I '14:— 4,871I '20:— 4,740
I '14:— 3,628M'17:— ?M'18:— ?
H Acid
Other IntermediatesUsed and Notes
Aniline
AnilineBenzene-(or Toluene-)
sulf 0 chloride
Ethyl-a-naphthylamine
DyeAppli-cationClass
A
A
A
DYES CLASSIFIED BY INTERMEDIATES 299
Dyes Derived from H Acid (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport andManufacture
Other IntermediatesUsed and Notes
DyeAppli-cationClass
187
188
189
217
261
264
333
MONOAZO DYES(continued)
Lanaeyl Blue BB
Tolyl Blue SRSulfon Acid Blue R
Sulf on Acid Blue B
'14:— 4,200
14:— 45,038M'17:— ?M'18:— ?M'19:— ?M'20:—454,185
'14:— 35,560M'17:— ?M'19:— ?M'20:— ?
DISAZO DYESNaphthol Blue BlackAgalma Black 10B
I '14:—431,027M'17:—620,218M'18:—
1,158,309M'19:—
1,877,860I '20:— 840M'20:—
2,608,864
5-Amino-l-naphthol
Phenyl-1-naphthyl-amine-8-sulf onic Acid
Tolyl-1-naphthylamine-8-sulfonic Acid
p-Nitro-anilineAniline
Buffalo Black 10B
Fast Sulf onBlack F
M '17:-M'18:-M'19:-M'20:-
M'19:— ?I '20:— 2,204M'20:— ?
Diamine Black BHOxamine Black BHN M
I '14:—619,430'17:— ?
M'18:— ?M'19:—485,046I '20:— 5,512M'20:—803,501
Sulf anilic Acida-Naphthylamine
Naphthionic AcidjS-Naphthol
BenzidineGamma Acid
D
300 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from H Acid {continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
334
336
337
353
381
382
383
386
390
DISAZO DYES(continued)
Diphenyl Blue Black
Benzo Cyanine E
I '14:— 26,240
:— 201
Diamine Blue 2BBenzo Blue 2B
Direct IndigoBlue BN
Azo Black Blue B, R
Azo Mauve B
Naphthazurine B
Diamine Blue BXBenzo Blue BX
I '14:— 19,035M'17:—
1,445,059M'18:—
1,523,985
1,380,335M'20:—
1,789,774
I '14:— 6,000
BenzidineEthyl-gamma Acid
Benzidinel-Amino-8-naphthol-4-
sulf onic Acid
BenzidineH Acid (2 mols)
Benzo Cyanine B
M'17:— ?M'20:— ?
I '14:— 4,782
I '14:— 1,740M'17:— ?M'18:— ?M'19:— 92,214I '20:— 4,520
M'20:— 90,147
I '14:— 201
Benzidine1:7-Dihydroxy-6-naph-
thoic-3-sulfonic Acid
Tolidinem-Hydroxy-diphenyl-
amine
a-NaphthylamineTolidine
Tolidine/3-Naphthylamine
TolidineNevile-Winther's Acid
Tolidinel-Amino-8-naphthol-4-
sulf onic Acid
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from H Acid (continued)
301
SchuUzNumberfor Dye
391
425
426
430
438
439
441
443
446
Ordinary Name andClass of Dye
DISAZO DYES(continued)
Diamine Blue 3BBenzo Blue 3B
Benzo Cyanine 3B
Diamine Pure BlueBenzamine Pure
Blue
Indazurine 5 GM
TBISAZO DYESMelogene Blue BH
Direct Indigo Blue A
Diazo Blue Black RS
Direct IndoncBlue R
Benzo Olive
Statistics ofImport and
Manufacture
I '14:— 1,365M'17:— 14,533M'18:— 99,645M'19:—182,940I '20:— 1,124M'20:—136,S91
I '14:— 1,001
I '14:— 12,881M'17:— ?M'18:— ?M'19:—192,350I '20:— 662M'20:—223,100
M'17:— ?M'18:— ?
M'18:— ?
M'19:— ?M'20:— ?
I '14:— 1,149
Other IntermediatesUsed and Notes
TolidineH Acid (2 mols)
Dianisidinel-Amino-8-naphthol-4-
sulfonic Acid
DianisidineH Acid (2 mols)
Dianisidine1:7-Dihydroxy-2-naph-
thoic-4-sulf onic Acid
Benzidinep-XylidineH Acid (2 mols)
H Acid (2 mols)Benzidinem-Amino-p-cresol
Methyl Ether
Benzidinea-NaphthylamineH Acid (2 mols)
Benzidinea-Naphthylamine2 R Acid
BenzidineSalicylic Acida-Naphthylamine
DyeAppli-cationClass
D
D
D
D
D
D
D
D
D
302 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from H Acid (continued)
SchultsNumberfar Dye
Ordinary Name andClass of Dye
Statistics ofImport andManufacture
Other IntermediatesUsed and Notes
DyeAppli-cationClass
448
462
463
464
467
468
469
470
TEISAZO DYES(continued)
Diamine Bronze G
Erie DirectBlack GX
Direct. DeepBlack EW
I '14:— 4,495
I '14:—1,246,536
M'17:— ?
M'19:—
M'20:
Erie DirectBlack RX
Cotton Black E
Erie DirectGreen ET
Diphenyl Green G
Diphenyl Green 3G
Chloramine Black N
Chloramine Green B
BenzidineSalicylic Acidm-Phenylene-diamine
BenzidineAnilinem-Phenylene-diainine
7,250,007
'7,736,994
I '14:—248,567M'19:— ?M '20:—
2,050,741
M'17:— ?M'18:— ?M'19:— 69,700M'20:— ?
I '20:— 2,205
I '14:— 39,600M'19:— ?I '20:— 1,76;
I '14:— 1,675M'19:— ?M'20:— ?
BenzidineAnilinew-Tolylene-diamine
BenzidineAnilinePhenol
Benzidineo-Chloro-p-nitro-anilinePhenol
Benzidineo-Chloro-p-nitro-aniHneSalicylic Acid
Benzidine2:5-DicUoro-anilinem-Phenylene-diamine
Benzidine2:5-Dichloro-anilinePhenol
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from H Acid (continued)
303
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ojImpoii and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
471
472
473
474
475
TRISAZO DYES(continued)
Chloramine Blue 3G
ChloramineBlue HW
Diamine Black HW
Diamine Green BOxamine Green B
Diamine Green GOxamine Green G
I '14:-M'19:-I '20:-
286
882
I '20:- 342
I '14:— 77,100M'17:— ?M'18:—295,147M '19:—305,854I '20:— 2,460M'20:-420,138
I '14:— 7,329M'17:— ?M'18:— 29,118M'19:—136,638I '20:— 1,332
M '20:— 53,292
Benzidine D2: 5-Dichloro-anilineH Acid (2 mols)
Benzidine D2: 5-Dichloro-anilineGamma Acid
Benzidine Dp-Nitro-anilineGamma Acid
Benzidine Dp-Nitro-anilinePhenol
Benzidine Dp-Nitro-anilineSalicylic Acid
Histazarin
2: 3-Dihydroxy-anthraquinono (not considered herein)
o-Homo-salicylic Acid
See, o-Cresotic Acid
ji-Hydrazine-6enzene-sulfonic Acid (C. A. nomen.)
See, Phenyl-hydrazine-p-sulfonic Acid
a-Hydro-juglone
1:4: 5-Trihydroxy-naphthalene (not considered herein)
304 DYES CLASSIFIED BY INTERMEDIATES
HydrolTetramethyl-diamino-benzohydrol
p: p'-Bis(dimethylamino)-&enzohydrol (C. A. nomen.)
Michler's Hydrol
H
/ ~ \ N (CH3)2 = C17BWS"2O = 270
OH
STATISTICS.—Manufactured '20:
FORMATION.—Dimethyl-aniline
-88,583 lbs.
is condensed with formaldehyde inpresence of hydrochloric acid, and the resulting product is oxidizedwith lead peroxide; or the corresponding ketone (tetramethyl-diamino-benzophenone) is reduced with zinc
LITERATTJEE.—Cain, Intermediate Products (2d Ed.), 102-3Lange, Zwischenprodukte, #1358
Dyes Derived from Hydrol
SchultzNumberfar Bye
Ordinary Name andClass of Dye
Statistics ofImport andManufacture
Other IntermediatesUsed and Notes
DyeAppli-cationClass
498
509
516
TRIPHENYL-METHANE
D Y E S
Turquoise Blue
Chrome Green
Crystal Violet
I '14:-I '20:
1,5411,407
'14:— 51,872M ' 1 7 : — ?M ' 1 8 : — ?M ' 1 9 : —I '20:—
M ' 2 0 : —
p-Nitro-toluene[Oxidation]
Benzoic Acid[Oxidation]
Dimethyl-aniline[Oxidation]
B
M
B
?2,919
?
528 Fast Acid Violet 10B I '14:— 12,919M ' 1 7 : — ?M ' 1 8 : — ?M ' 1 9 : — ?I '20:— 10,086
M ' 2 0 : — ?
Benzyl-ethyl (me thyl) -aniliri e-disulf onic Acid
[Oxidation]
A
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Hydrol (continued)
305
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
542
549
550
558
559
562
563
564
TRISAZO DYES(continued)
Agalma Green B I '14:— 2,294
Chrome Violet
Chrome Bordeaux
DlPHENYL-NAPHTHYL-METHANE DYES
Victoria Blue R,
Victoria Blue B
I '14:— 51
I '14:-I '20:-
4,17197
I '14:—127,769M'17M'18M'19I '20
M'20>:— 4,171
Fast Acid Blue B
New Patent Blue B
I '14:— 33,251I '20:— 6,478
I '14:-I '20:-
59.1,814
Naphthalene Green V I '14:— 22,144I '20:— 9,291
4-Chloro-3: 5-dinitro-benzene-sulfonic Acid
Metanilic Acidor
Dinitro-diphenylamine-disulf onic Acid
Salicylic Acid[Oxidation]
Amino-salicylic Acid[Oxidation]
Ethyl-a-naphthylamine[Oxidation]
Phenyl-a-naphthyl-aminc
[Oxidation]
l-Naphththylamine-2-sulf onic Acid
[Oxidation]
Naphthionic Acidor
Laurent's Acid[Substitution of -NH2by -SOsNa and Oxida-
tion]
Naphthaleneor
Naphthalene-2:7-disulf onic Acid
306 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Hydrol (continued)
SchullzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport andManufacture
Other IntermediatesUsed ,and Notes
DyeAppli-cationClass
566
567
652
DlPHENYL-NAPHTHYL"METHANE DYES
(continued)Wool Green S
Chrome Blue
OXAZINE DYENew Fast Blue F
I '14:— 60,073M'17:— ?M'19:— ?I >20:—127,764M'20:—212,362
I '14:— 2,502
GAcid
l-Hydroxy-2-naphthoicAcid
[Oxidation]
Nitroso-dimethyl-aniline
/3-Naphtholor
[Meldola's Blue]
M
B
3-Hydroxy-acenaphthene
4-Hydroxy-acenaphthene (German numbering)
3-Acenaphthenol (C. A. nomen.)
CH2-CH2
FORMATION.—From 3-amino-acenaphthene by diazotizing and thenboiling to hydrolyze the diazo group
LITERATURE.—Lange, Zwischenprodukte, #2957Frdl. 10, 544
Dye Derived from 3-Hydroxy-acenaphthene
SchultzNumberfor Dye
894
Ordinary Name andClass of Dye
INDIGO GROUP DYESAlizarin Indigo B
Statistics ofImport and
Manufacture
I 14:— 402I '20:— 291
Other IntermediatesUsed and Notes
2-Isatin Anilide
DyeAppli-cationClass
V
DYES CLASSIFIED BY INTERMEDIATES
4-Hydroxy-acenaphthene (German numbering)
See, 3-Hydroxy-acenaphthene
1-Hydroxy-anthracene
See, 1-Anthrol (C A. nomen.)
9-Hydroxy-anthracene
See, 9-Anthrol (C A. nomen.)
1-Hydroxy-anthranol
l-Hydroxy-9-anthrol
a-Hydroxy-anthranol
1: 9-Anthradiol (C A. nomen.)
OH
OH
307
H
FORMATION.—1-Hydroxy-anthraquinone is reduced with hydrosulfiteand alkali or with stannous chloride and hydrochloric acid
LITERATURE— Ger. Pat. 242,053; Frdl. 10, 532Barnett, Anthracene and Anthraquinone
Dye Derived from 1-Hydroxy-anthranol
SchuUzNumberfor Dye
896
Ordinary Name andClass of Dye
INDIGO GROUP DYESHclindone Blue 3GN
Statistics ofImport and
Manufacture
I '14:— 622I '20:-— 2,527
Other IntermediatesUsed and Notes
2-Isatin Anilide
DyeAppli-cationClass
V
a-Hydroxy-anthranol
See, 1-Hydroxy-anthranol
l-Hydroxy-9-anthrol
See, 1-Hydroxy-anthranol
308 DYES CLASSIFIED BY INTERMEDIATES
m-Hydroxy-benzaldehyde
FORMATION.—From m-amino-benzaldehyde by diazotizing the amino-group and then boiling until the nitrogen evolution ceases
LITERATURE.—Cain, Intermediate Products (2d Ed.), 145Lange, Zwischenprodukte, #461
Dyes Derived from m-Hydroxy-benzaldehyde
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
543
544
545
546
TEIPHENYL-METHANE
DYES
Patent Blue V
Cyanine B
Patent Blue A
Cyanol
I 314:—196,228M317:— ?M' lS :— ?I '20:— 36,420
I '14:-I '20:-
8,39824
I '14:-M'18:-I '20:— 44,801
63,744?
I ' 1 4 : -
I ' 2 0 : -
4 0 , 0 1 5
7 , 9 5 4
D i e t h y l - a n i l i n e (2 m o l s )[Sulf o n a t i o n , O x i d a t i o n ]
D i e t h y l - a n i l i n e (2 m o l s )[ S u l f o n a t i o n , O x i d a t i o n ]
or
[ O x i d a t i o n of P a t e n tB l u e ]
B e n z y l - e t h y l - a n i l i n e(2 m o l s )
[ S u l f o n a t i o n , O x i d a t i o n ]
E t h y l - o - t o l u i d i n e(2 m o l s )
[ S u l f o n a t i o n , O x i d a t i o n 1
A
m - H y d r o x y - d i m e t h y l - a n i l i n e
See, 7 n - D i m e t h y l a m i n o - p h e n o l ( C . A. nomen.)
DYES CLASSIFIED BY INTERMEDIATES
m-Hydroxy-diphenylamine
Phenyl-ra-amino-phenol
m-Anilino-phenol (C. A. nomen.)
HO
^ -NH
309
FORMATION.—(1) From resorcinol by heating with aniline and zincchloride at 280-290°. (2) From m-amino-phenol by heating withaniline hydrochloride in an autoclave at 210-215°
LITERATURE.—Cain, Intermediate Products (2d Ed.), 55Lange, Zwischenprodukte, #1613
Dyes Derived from m-Hydroxy-diphenylamine
SchultzNumberfor Dye
381
658
Ordinary Name andClass of Dye
DISAZO DYEAzo Black Blue B, R
OXAZINE DYEFast Black
Statistics ofImport andManvfacturc
I '14:— 1,960I '20:— 2,S83
Other IntermediatesUsed and Notes
TolidineH Acid
Nitroso-dimeiliyl-aniline
DyeAppli-cationClass
D
B
iV-(3-Hydroxy-4-keto-l(4)-naphthylidene)-sulfanilic Acid (C. A.nomen,)
See, j3-Hydroxy-naphthoquinonyl-aniline-p-bulfonic Acid
l-Hydroxy-naphthalene-2-carboxylic Acid
See, l-Hydroxy-2-naphthoic Acid (C. A. nomen.)
2-Hydroxy-naphthalene-3-carboxylic Acid
See, 3-Hyclroxy-2-naphthoic Acid (C. A. nomen.)
Hydroxy-naphthalene-sulfonic Acids
See, Naphthol-sulfonic Acids
310 DYES CLASSIFIED BY INTERMEDIATES
l-Hydroxy-2-naphthoic Acid (C. A. nomen.)
l-Hydroxy-naphthalene-2-carboxylic Acid
a-Oxy-naphthoic Acid
a-Naphthol-carboxylic Acid
OH
S
FORMATION.—a-Naphthol is converted into sodium a-naphtholate, andtreated with the theoretical amount of carbon dioxide under pressureand at 120-145°
LITERATURE.—Cain, Intermediate Products (2d Ed.), 240Lange, Zwischenprodukte, #775, 2308
Dye Derived from l-Hydroxy-2-naphthoic Acid
SchvltzNumber*or Dye
567
Ordinary Name andClass of Dye
DlPHENTL-NAPHTHYL-METHANE DYES
Chrome Blue
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
Hydrol[Oxidation]
DyeAppli-cationClass
M
2-Hydroxy-3-naphthoic Acid
See, 3-Hydroxy-2-naphthoic Acid (C. A. nomen.)
3-Hydroxy-2-naphthoic Acid (C. A. nomen.)
2-Hydroxy-3-naphthoic Acid
2-Hydroxy-naphthalene-3-carboxylic Acid
/3-Oxy-naphthoic Acid
/?-Naphthol-carboxylic Acid
OH
DYES CLASSIFIED BY INTERMEDIATES 311
STATISTICS.—Imports '14:—2,359 lbs.Manufactured '19:— ?Manufactured '20:— ?
FORMATION.—/3-Naphthol is converted into the sodium /3-naphtholate,and treated with the theoretical amount of carbon dioxide underpressure and at 200-250°
LITEKATUEE.—Cain, Intermediate Products (2d Ed.), 241
Lange, Zwischenprodukte, #775, 2308
Dyes Derived from 3-Hydroxy-2-naphthoic Acid
SchultzNumberfor Dye
45
152
179
Ordinary Name andClass oj Dye
MONOAZO DYESBrilliant Lake
RedR
Lithol Rubine BPermanent Red 4B
Lake Bordeaux B
Statistics ofImport and
Manufacture
I '14:— 31,674I '20:— 1,071
I '14:—101,395M'19:— ?I '20:— 2,983M'20:— ?
Other IntermediatesUsed and Notes
Aniline
p-Toluidine-o-sulfonicAcid
2-Naphthylamine-l-sul-fonic Acid
DyeAppli-cationClass
CL
CL
CL
]3-Hydroxy-naphthoquinone
1:2-Dihydroxy-naphthalene (not considered herein)
/3-Hydroxy-naphthoquinonyl-aniline-^-sulfonic Acid
A7'-(3-Hydroxy-4-keto-l(4)-naphthylidene)-sulfanilic Acid (C. A.
-o O3H
312 DYES CLASSIFIED BY INTERMEDIATES
FORMATION.—The potassium salt of 1: 2-naphthoquinone-4-sulfonic
acid is condensed with the sodium salt of sulfanilic acid, splitting
off a sulfonic group and furnishing the /3-hydroxy-naphthoquinonyl-
aniline-p-sulfonic acid
LITERATURE.—Lange, Schwefelfarbstoffe, 393,139
Lange, Zwischenprodukte, #2870, 2871Schultz, Farbstofftabellen, #747
Dye Derived from /5-Hydroxy-naphthoquinonyl-aniline-^-sulfonicAcid
SchultzNumberfor Dye
747
Ordinary Name andClass of Dye
SULFUR DYEThional Brown G
Statistics ofImport and
Manufacture
I '14:— 110I '20:— 43,219
Other IntermediatesUsed and Notes
[S+Na*S]
DyeAppli-cationClass
s
4-(^-Hydroxy-phenyl-amino)-l-phenylamino-naphthalene-8-sulfonic Acid
8-Anilino-5-(p-hydroxy-anilino)-l-?zaphthalcne-sulfonic Acid (C.
A. nomen.)
HO3S NH-
NH OH
FORIMATION.—By condensation of phenyl-l-naphthylamine-8-sulfonic
acid and p-amino-phenol
LITERATURE.—Lange, Schwefelfarbstoffe, 425
DYES CLASSIFIED BY INTERMEDIATES 313
Dye Derived from 4-(^-Hydroxy-phenyl-amino)-l-phenylamino-naph-thalene-8-sulfonic Acid
SchultzNumberfor Dye
746
Ordinary Name andClass of Dye
SULFUR DYEThional Green BKatigene Green
Statistics ofImport and
Manufacture
I '14:— 63,929I '20:-- 14,370
Other IntermediatesUsed and Notes
[NasS+S]
DyeAppli-cationClass
S
2-Hydroxy-tfhionaphthene (C. A. and English nomen.)
3-Hydroxy-l-thionaphthene (German numbering)
Thioindoxyl
CH2 or I | CH =
FORMATION.—Thiosalicylic acid with chloro-acetic acid gives phenyl
thioglycolic-o-carboxylic acid:
[S .CH 2 .COOH
ICOOH
This body, by heating with a little water and caustic soda, closes
up the second ring and forms 2-hydroxy-thionaphthene-l-carboxylic
acid, which in warm acid solution decomposes, losing CO2 and form-
ing 2-hydroxy-thionaphthene
LITERATURE.—Lange, Zwischenprodukte, #2148-2163
Georgievics and Grandmougin, Dye Chemistry, 432-434
Schultz, Farbstofftabellen (5 auf.), #912
Cain, Intermediate Products (2d Ed.), 159
314 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 2-Hydroxy-thionaphthene
SchultzNumberfor Dye
899
900
900
901
905
906
907
908
912
919
Ordinary Name andClass of Dye
INDIGO GROUP DYESCiba Gray G
Ciba Violet 3B
Thio Indigo Violet K
Ciba Violet B
Thio IndigoScarlet R
Thio IndigoScarlet G
Ciba Scarlet G
Ciba Red R
Thio Indigo Red B
Ciba Bordeaux B
I
I
II
I
I
II
I
II
II
Statistics ofImport and
Manufacture
'14:—
'14:—
'14:—'20:—
'20:—
'20:—
'14:—'20:—
'14:—
'14:—'20:—
'14:—'20:—
675
2,667
20,83618,287
270
1,291
22,26525,578
1,001
1,102275
8991,786
Other IntermediatesUsed and Notes
2-Isatin anilide[Bromination]
2-Isatin anilide[Bromination]
2-Isatin anilide[Bromination]
2-Isatin anilide[Bromination]
Isatin
Isatin[Bromination]
Acenaphthenequinone
Acenaphthenequinone[Bromination]
2-Hydroxy-thionaph-thene (2 mols)
2-Hydroxy-thionaph-thene (2 mols)
[Bromination]or
[Bromination of ThioIndigo Red R]
DyeAppli-cationClass
V
V
V
V
V
V
V
V
V
V
3-Hydroxy-thionaphthene
See, 2-Hydroxy-thionaphthene
DYES CLASSIFIED BY INTERMEDIATES 315
2-Hydroxy-Aionaphthene-l-carboxylic Acid (C. A, nomm.)
3-Hydroxy-(l)-thionaphthene-2-carboxylic Acid (German num-bering)
Thioindoxyl-carboxylic Acid
C. COOH = C9H6O3S = 194
FORMATION.—From phenyl-thioglycol-o-carboxylic acid through closingof the side chain upon fusion with caustic soda. (The carboxylicgroup is very easily split off with the formation of 2-hydroxy-thionaphthene.) Cf. 2-hydroxy-thionaphthene
LITERATURE.—Cain, Intermediate Products (2d Ed.), 159Lange, Zwischenprodukte, #2148-2163
USES.—See 2-hydroxy-thionaphthene
I Acid
See, J Acid
p: ^'-Imino-bisaniline (C A. nomen.)
See, p: p'-Diamino-diphenylamine
4:4/-Imino-bis-o-foluidine (C. A. nomen. NHz=l)
See, p: p'-Diamino-ditolyl-amine
Indanthrene
See, Indanthrone
Indanthrene-sulfonic Acid
See, Indanthrone-sulfonic Acid
316 DYES CLASSIFIED BY INTERMEDIATES
Indanthrone
Dianthraquinone-dihydroazine
Indanthrene (C. A. nomen.)
)—NHxO C X .
FORMATION.—Anthraquinone is sulfonated with oleum to 2-anthraqui-none-sulfonic acid, which upon being heated in an autoclave withammonia forms 2-amino-anthraquinone. This latter by the actionof alkali at 200-300° is converted to indanthrone
LITERATURE.—Georgievics and Grandmougin, Dye Chemistry, 449-450Barnett, Anthracene and Anthraquinone, 342Schultz, Farbstofftabellen (1914 Ed.), #837
Dyes Derived from Indanthrone
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
837
838
840
841
842
ANTHKAQUINONE ANDALLIED DYES
IndanthreneBlueR
IndanthreneBlue RS
IndanthreneBlue
IndanthreneBlue 2GS
IndanthreneBlue GCD
I '14:— 500
'14:—187,379M'17:— ?I '20:— 16,385M'20:— ?
I '14:— 6,120I '20:— 551
I '14:— 10,163I '20:— 500
I '14:—478,980M'19:— ?I '20:—147,620
[This is indanthrone]
[Reduction]
[Oxidation]
m
[Dichlorination]
V
V
V
V
V
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Indanthrone (continued)
317
SchultzNumberfor Dye
843
850
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
(continued)Indanthrene
Blue GC
IndanthrencBlue WB
Statistics ofImport andManufacture
I '14:— 1,499I >20:— 4,700
I '14:— 32,957I '20:— 2,998
Other IntermediatesUsed and Notes
[Dibrominationl
[?]
DyeAppli-cationClass
V
V
Indanthrone-sulfonic Acid
Indanthrene-sulfonic Acid (C. A. nomen.)
/ \ / C 0
FORMATION.—(1) From 2-amino-anthraquinonc-sulfonic acid by fusionwith caustic alkali at 200-300° C. (2) By sulfonating indan-throne (obtained by alkaline fusion of 2-amino-anthraquinone)
LITERATURE.—Barnett, Anthracene and Anthraquinone, 352Thorpe, Die. Chemistry, 3, 101 et seq.
Dye Derived from Indanthrone-sulfonic Acid
SchultzNumberfor Dye
840
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
IndanthreneBlue
Statistics ofImport andManufacture
I '14:— 6,120I '20:— 1,702
Other IntermediatesUsed and Notes
DyeAppli-cationClass
V
318 DYES CLASSIFIED BY INTERMEDIATES
IndigoNote.—Indigo is of course a dye and not an intermediate. However
because of their close mutual connection, it was considered worth while tolist together the dyes derived directly from indigo. All of these dyes arealso classified by the various intermediates that are used for the manufactureof indigo, namely:—
L Phenyl-glytine (2 mols)
2. Phenyl~glycine-o-carboxylic Acid (2 mols)
S. Thiocarbanilide (2 mols)
4- Aniline {2 mols)
5. Phthalic anhydride (2 mols)
SckultzNumberfor Dye
874
876
877
878
Dyes
Ordinary Name andClass of Dye
INDIGO GEOUP DYESIndigo
Indigo MLBIndigo White
Indigotine
Indigotine P
Derived from
Statistics ofImport andManufacture
I '14:—8,507,359
M'17:—274,771M'18:—
3,083,888M'19:—
8,863,824I '20:—520,347M'20:—
18,178,231
I '14:— 19,329
' 1,876,787M'18:—
1,434,703M'19:—
1,699,670I '20:— 5,512M'20:—
1,395,000
Indigo
Other IntermediatesUsed and Notes
[Reduction]
[Sulfonation]
[Sulfonation]
DyeAppli-cationClass
V
V
A
A
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Indigo (continued)
SchultaNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
879
880
881
882
883
884
885
886
889
890
INDIGO GROUP DYES(continued)
Brom IndigoRathjen
Indigo MLB/RR
Helindone Blue BBIndigo RB
DianthreneBlue 2B
Bromo Indigo FBCiba Blue 2B
Indigo MLB/5BCiba Blue G
Indigo MLB/6BIndigo KG
Brilliant IndigoBASF/2B
Brilliant IndigoBASF/B
Brilliant IndigoBASF/G
Indigo Yellow 3G
Ciba Yellow G
I 14:— 53,610M'20:— ?
14:— 6,856M17:— 14,100I '20:— 3,691M'20:— ?
I 14:— 16,880M19:— ?I '20:— 35,857
I 14:-I '20:-
I 14:-I '20:-M'20:-
1,3561,008
3,1914,130
I 14:— 4,518
I 14:-I '20:-
8,1753,503
I 14:— 12,057
I 14.— 48
[Bromination]
[Bromination]
[Bromination]
[Bromination]
[Bromination]
[Chlorination, Bromina-tion]
[Chlorination]
[Chlorination, Bromina-tion]
Benzoyl Chloride
Benzoyl ChloridePromination]
Indigo Red
See, Indirubin
320 DYES CLASSIFIED BY INTERMEDIATES
Indirubin (C A. nomen.)
Oxindole-[A3'2']-pseudoindoxylIndigo Red
H
<x> ~\/\co/FORMATION.—By reaction of indoxyl on isatin in the " indoxyl melt"LITERATURE.—Georgievics and Grandmougin, Dye Chemistry, 410Ger. Pat. 192,682; Frdl. 9, 533Dye Derived from IndirubinSchultzNumberfor Dye
897
Ordinary Name andClass of Dye
INDIGO GROUP DYESCiba Heliotrope B
Statistics ofImpart and
ManufactureOther Intermediates
Used and Notes
[Bromination]
DyeAppli-cationClass
V
Indoxyl (C. A. nomen.)
3-Hydroxy-indole
(XNHNCH2 or CH =
FORMATION.—From phenyl-glycme by fusion with sodamide
LITERATURE.—Lange, Zwischenprodukte, #2057-2084
Dye Derived from Indoxyl
SchultzNumberfor Dye
897
Ordinary Name andClass of Dye
INDIGO GROUP DYESCiba Heliotrope B
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
Isatin[Bromination]
DyeAppli-cationClass
V
DYES CLASSIFIED BY INTERMEDIATES 321
Isatin (C. A. nomen.)
2-Hydroxy-3-pseudoindolone
( X .
NH \CO or C.OH = (
STATISTICS.—Imported '14:—very smallManufactured '20:— ?
FORMATION.—From indoxyl by oxidation
LITERATURE.—Lange, Zwischenprodukte, #1815, 2023, 2110-2116
Dyes Derived from Isatin
SchultzNumberfor Dye
897
898
904
905
906
Ordinary Name andClass of Dye
INDIGO GROUP DYESCiba Heliotrope B
Helindonc Violet D
Helindone Brown G
Thio IndigoScarlet R
Thio IndigoScarlet G
2-Isatin Anilide
a-Isatin Anilide
Isatin-2-phenylimide
Statistics ofImport and
Manufacture
I '14.— 13,080I '20.— 2,200
I '20.— 370
I '20:— 1,291
Other IntermediatesUsed and Notes
Indoxyl[Bromination]
7-Methyl-indoxyl[Bromination]
5-Amino-2-hydroxy-thionaphthene
[Bromination]
2-Hydroxy-thionaph-thene
2-Hydroxy-thionaph-thene
[Bromination]
2-Anilino-3-pseudoindolone (C A. nomen.)
( i4HioNtO = 222
DyeAppli-cationClass
V
V
V
V
V
322 DYES CLASSIFIED BY INTERMEDIATES
FORMATION.—Aniline is condensed with carbon disulfide to thiocarbani-
lide (CeEU. NH)2 CS, which is treated in solution with potassium
cyanide and lead carbonate, resulting in the formation of the
corresponding cyanide. This cyanide is reacted with yellow am-
monium sulfide (containing NH4.S.S.NH4), and a thioamide is
formed:
. N . / N H
> o - c = s
This compound upon being heated with sulfuric acid gives a good
yield of 2-isatin anilide
LITERATURE.—Lange, Zwischenprodukte, #2132-2134Georgievics and Grandmougin, Dye Chemistry, 413
Dyes Derived from 2-Isatin Anilide
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
894
896
899
900
900
901
INDIGO GROUP DYESAlizarin Indigo B
Helindone Blue 3GN
Ciba Gray G
Ciba Violet 3B
Thioindigo Violet K
Ciba Violet B
I '14:-I '20:-
I '14:-I '20:-
402291
6222,527
=:— 675
I '14:— 2,667
I '14:-I '20:-
20,83618,287
3-Hydroxy-acenaph-thene
1-Hydroxy-anthranol
2-Hydroxy-thionaph-thene
[Brom iiiation]
2-Hydroxy-thionaph-thene
[Bromination]
2-Hydroxy-thionaph-thene
[Bromination]
2-Hydroxy-thionaph-thene
[Bromination]
V
V
V
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 2-Isatin Anilide (continued)
323
SchultzNumberfor Dye
902
903
Ordinary Name andClass of Dye
INDIGO GROUP DYES(continued)
Helindone Brown 2R
Helindone Brown 5R
Statistics ojImport and
Manufacture
I '14:— 876I '20:— 1,778
Other IntermediatesUsed and Notes
5-Amino-l-hydroxy-thionaphthene
[Bromination]
5-Amino-l-hydroxy-thionaphthene
[Bromination]
DyeAppli-cationClass
V
V
a-Isatin Anilide
See, 2-Isatin Anilide
Isatin-2-phenylimide
See, 2-Isatin Anilide
Isoanthraflavic Acid
2: 7-Dihydroxy-anthraquinone (not considered herein)
Iso-7 Acid
See, J Acid
Iso-naphthazarin
2: 3~Dihydroxy-l: 4-naphthoquinone (not considered herein)
Isoquinoline
N
STATISTICS.—Imported '14:—very small
324 DYES CLASSIFIED BY INTERMEDIATES
FORMATION.—Isoquinoline is extracted from coal-tar or prepared bysynthetical means
LITERATURE.—Lange, Zwischenprodukte, #1997
Dye Derived from Isoquinoline
SchultzNumberjor Dye
610
Ordinary Name andClass of Dye
QUINOLINE DYEQuinoline Red
Statistics ofImport andManufacture
Other IntermediatesUsed and Notes
Benzo-trichlorideQuinaldine
DyeAppli-cationClass
B
J Acid
2-Amino-5-naphthol-7-sulfonic Acid
Amino-naphthol-sulfonic Acid J
6-Armno-l-naphthol-3-sulfonic Acid (C. A. nomen.)
I Acid
Iso-7 Acid
STATISTICS.—Imports J14:—1,153 lbs.
Manufactured '20:— ?
FORMATION.—j3-Naphthylamine is disulfonated to a mixture of 2-naphthylamine-5:7-disulfonic acid and 2-naphthylamine-6:8-disulfonic acid. The latter is amino-G acid and is a step in thepreparation of gamma acid. The former is fused with caustic sodain an autoclave to form J acid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 235
Lange, Zwischenprodukte, #2542
Thorpe, Die. Chemistry, 3, 640
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from J Acid
SchultzNumberjot Dye
Ordinary Name andClass of Dye
Statistics ojImport and
ManufactureOther Intermediates
Used and Notes
279
326
346
385
DISAZO DYESBenzo Fast Scarlet '14:— 36,674
M'19:— ?I '20:— 24,153
Oxamine VioletOxy Diamine Violet
BF
Oxamine Red
Oxamine Blue 4R
I '14:— 23,981I '20:— 732
I '14:— 11,636I '20.— 848
I '14:— 573M'20:— ?
J Acid (2 mols)PhosgeneAniline or
Toluidine orXylidine orjS-Naphthylamine orAmino-azo-benzene
(2 mols)
BenzidineJ Acid (2 mols)
BenzidineSalicylic Acid
TolidineNevile-Winther's Acid
D
D
Juglone
5-Hydroxy-l: 4-naphthoquinone (not considered herein)
K Acid*
l-Amino-8-naphthol~4: 6-disulfonic Acid
Amino-naphthol-disulfonic Acid K
8-Amino-l-naphthol~3: 5-disulfonic Acid (C. A. nomen.)
HO N H 2
HO3S= C10H9NO7S2 =
1 K acid is also occasionally used as trivial name for 1:-- Dihydroxy-naphthalene-3: 5-disulfonic acid.
326 DYES CLASSIFIED BY INTERMEDIATES
FOKMATION.—Naphthalene is disulfonated to the 1: 5 acid, and thenfurther sulfonated to the 1:3: 5-trisulfonic acid. This trisulfonicacid while still in the sulfonation mixture is diluted with a little ice,and cooled, and it is then nitrated cold with the theoretical amountof mixed acid. I t is reduced with iron, forming 1-naphthylamine-4:6 : 8-trisulfonic acid, which upon being fused with caustic sodain an autoclave yields the K acid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 239Lange, Zwischenprodukte, #2728Thorpe, Die. Chemistry, 3, 642
Dyes Derived from K Acid
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
43
215
219
335
338
MONOAZO DYETolane Red B, G
DISAZO DYESBlue Black N
Chrome PatentGreen N
JSTaphthamine BlackRE
Naphthamine Blue2B or 3B
I '14:— 2,653
I '14:— 49,016
I '14:— 11,707I '20:— 400
Aniline
Anilinep-Nitro-aniline
AnilinePicramic Acid
BenzidineGamma Acid
Benzidine orToHdine
K Acid (2 mols)
A
ACr
D
Kalle's Acid
l-Naphthylamine-2:7-disulfonic Acid (not considered herein)
DYES CLASSIFIED BY INTERMEDIATES
Ketone
Tetramethyl-diamino-benzophenone
p: p'-Bis(dimethylamino)-6enzophenone (C A. nomen.)
Michler's Ketone
Ketone Base
(CH 3 ) 2 N<^>—CO—/~^>N(CH 3 )2 = CITHMNJO = 268
STATISTICS.—Imported ' 14:—small amountManufactured ' 17:— ?Manufactured '18:— 73,208 lbs.Manufactured '19:—281,057 lbs.Manufactured '20:— 90,664 lbs.
FORMATION.—From dimethyl-aniline by reaction with phosgene
LITERATURE.—Cain, Intermediate Products (2d Ed.), 103Lange, Zwischenprodukte, #1382
327
SchultzNumberfor Dye
493
516
522
Dyes
Ordinary Name andClass of Dye
ATJBAMINESAuramine
TKIPHENYL-METHANEDYES
Crystal Violet
Victoria Blue 4R
Derived fron\ "
Statistics ofImport and
Manufacture
I 14:—449,276MT7:— ?M'18:— 45,634M19:—127,567I '20:— 74,414M'20:— ?
I 14:— 51,872M17:— ?M18:— ?M19:— ?I '20:— 2,919M'20:— ?
I 14:— 9,599I '20:— 152
Ketone
Other IntermediatesUsed and Notes
[Ammonium chlorideand Zinc chloride]
Dimethyl-aniline
Methyl-phenyl-a-naphthylamine
DyeAppli-cationClass
B
B
B
328 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Ketone (continued)
SchultzNumberfor Dye
527
548
558
559
561
566
607
Ordinary Name andClass oj Dye
TmPHENYL-METHANEDYES
{continued)Acid Violet 4BN
Acid Violet 6BN
DlPHENYT/-NAPTHYL-METHANE DYES
Victoria Blue R
Victoria Blue B
Acid Violet 5BNS
Wool Green S
ACEIDINE DYERheonine
Statistics ofImport andManufacture
I '14:— 60,073M'17:— ?M'19:— ?I '20:—127,764M'20:—212,362
I '14:— 19,704
Other IntermediatesUsed and Notes
I '14:— 29,184I '20:— 23,335
I '14:— 6,861I '20:— 5,582
I '14:— 4,171I '20:— 97
I '14:—127,769M'17:— ?M'18:— ?M'19:— ?I J20:— 11,782M'20:— ?
I '14:— 1,896 MethyHEthyl-) phenyl-/?-naphthylamine
Benzyl-methyl-aniline
3-Ethoxy~4'-methyl-diphenylamine
[Sulfonation]
Ethyl-a-naphthylamine
Phenyl-a-napthyl-amine
/3-Naphthol[Sulfonation]
m-Phenylene-diaTnin e
DyeAppli-cationClass
6-Keto-l-(^-sulfo-phenyl)-3-A2-y^razoline-carboxylic Acid (C. A.nomen.)See, l-(p-S\ilfo-pheiiyl)-5-pyrazoloiie-3-carboxylic Acid
Koch's AcidSee, l-Naphthylamine-3:6:8-trisulfonic Acid
DYES CLASSIFIED BY INTERMEDIATES 329
L Acid
See, l-Naphthol-5-sulfonic Acid (C. A. nomen.)See Laurent's Acid2:6-Dihydroxy-naphthalene-3-carboxylic Acid (not con-
sidered herein)
Lambda Acid or X Acid
See, l-Naphthylaminc-2-sulfonic Acid
Landschoft and Meyer's Acidl-Naphthylamine-2: 5-disulfonic Acid (not considered here)
Laurent's a Acidl-Nitro-naphthalene-5-sulfonic Acid (not considered herein)
Laurent's Acid
l-Naphthylamine-5-sulfonic Acida-Naphthylamine-sulf onic Acid L5-Axnino-l-naphthalene-sulfonic Acid (C A. nomen.)Naphthalidine-sulfonic AcidNaphthalidinic AcidCleve's a AcidL AcidLaurent's Naphthalidinic Acid
NH2
C10H9NO3S =
HO3S
riSTics.—Imported '14:— 2,832Manufactured '18:— ?Manufactured ' 19:— ?Manufactured 720:—294,352
.MATioN.—(1) From a-naphthylamine by sulfonation with oleum.(2) From a-naphthalene-sulfonic acid by nitration reduction andseparation from the l-naphthylamine-8-sulfonic acid also formed
ERATURE.—Cain, Intermediate Products (2d Ed.), 190Lange, Zwischenprodukte, #2360-2Thorpe, Dict Chemistry, 3 ; 590
330 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from. Laurent's Acid
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Siatisiics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
53
162
265
308
364
480
563
MONOAZO DYEArchil Substitute
3VN
Brilliant FastRedG
DISAZO DYESSulfoncyanine
Black B
Diazo Black B
Benzopurpurin 6B
TRISAZO DYECongo Brown R
DlPHENYL NAPHTHYL-METHANE DYE
New Patent Blue B
I '14:-M'17:-M '18:-M'19:-M'20:-
69,590????
:— 62,854
I '14:—I '20:—
9,1714,743
I '14:— 3,041
I '14:I '20:-
59,1,814
p-Nitro-aniline
^-Naphthol
a-Naphthylamine or1-Naphthylamine-6- and 7-sulfonicAcids
Phenyl-1-naphthyl-amine-8-sulfonic Acid
Laurent's Acid (2 mols)Benzidine
Laurent's Acid (2 mols)Tolidine
BenzidineResorcinolSalidylic Acid
Hydrol[Substitution of NH2 by
SO3H; Oxidation]
Laurent's Naphthalidinic Acid
See, Laurent ' s Acid (l-Naphthylamine-5-sulfonic Acid)
DYES CLASSIFIED BY INTERMEDIATES
Lepidine (C. A. nomen.)
4-Methyl-quinoline (N = l)
7-Methyl-quinoline
Cincholepidine
331
CH3
FORMATION.—(1) From cinchonine by distillation with caustic potash,(2) By saturating a mixture of methylal [CH2(OCH3)2] and acetonewith gaseous hydrochloric acid, and then, heating this with anilineand concentrated hydrochloric acid
LITERATURE.—Thorpe, Die. Chemistry, 4, 478
Dye Derived from Lepidine
SchultzNumberfor Dye
611
Ordinary Name andClass of Dye
QUINOLINE DYEQuinoline Blue
Statistics ofImport andManufacture
Other IntermediatesUsed and Notes
Quinoline[Amyl-iodide]
DyeAppli-cationClass
Photo-graphy
^-Leucaniline
See, Triamino-triphenyl-methane
Leuco-iso-naphthazarin
1:2:3:4-Tetrahydroxy-naphthalene (not considered herein)
Leuco-naphthazarin
1:2: 5: 8-Tetrahydroxy-naphthalene (not considered herein)
Leucotrope
Benzyl-dimethyl-phenyl-ammonium Chloride (not consideredherein)
332 DYES CLASSIFIED BY INTERMEDIATES
Liebman and Studer's Acid
l-Naphthol-7-sulfonic Acid (not considered herein)
MAcid
See, l-Aniino~5-naphthol-7-sulfonic Acid
l-(or 2-)Mercapto-anthraquinone
SH
= C14H8O2S = 240
FORMATION.—By forming mercapto-benzoyl-benzoic acid and thenclosing the ring
LITERATURE.—Barnett, Anthracene and Anthraquinone, 183, 184Lange, Zwischenproduckte, #3143-3147, 3527
Dye Derived from l-(or 2-)Mercapto-anthraquinone
SchultzNumberfor Dye
869
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Algol Brown B
Statistics ofImport and
Manufacture
I '14:— 1,596I '20:— 4,727
Other IntermediatesUsed and Notes
DyeAppli-cationClass
V
o-Mercapto-benzoic Acid (<7. A. nomen.)
See, Thio-salicylic Acid
Mesidine (C A. nomen.)
2:4:6-Trimethyl-aniline
NH2
H3
DYES CLASSIFIED BY INTERMEDIATES 333
FORMATION.—By the nuclear methylation of aniline, whereby anilinehydrochloride is heated with methanol (methyl alcohol) underpressure at 300-350°. There is formed, in addition to mesidine,p- and o-toluidine, m-xylidine, etc.
LITERATURE.—Ullmann, Enzy. tech. Chemie, 8, 30
Dye Derived from Mesidine
SchultzNumberfor Dye
583
Ordinary Name andClass of Dye
XANTHONE DYEAcid Rosamine A
Statistics ofImport and
Manufacture
I '14:— 50I '20:— 141
Other IntermediatesUsed and Notes
Mesidine (2 mols)Resorcinol (2 mols)Phthalic Anhydride[PC15; Sulfonation]
or[Dichloro-fluoresceine;
Mesidine (2 mols);Sulfonation]
DyeAppli-cationClass
A
Meta=mNote.—This is not considered in the alphabetical arrangement, e.g.
meta-Phenylene-diamine is indexed as m-Phenylene-diamine under "P."However m-Phenylene-diamine precedes p-Phenylene-diamine
Metanilic Acid (C. A. nomen.)
m-Amino-benzene-sulfonic Acid
m-Sulfanilic Acid
SO3H
STATISTICS.—Manufactured '17:— ?Manufactured '18:—249,922 lbs.Manufactured 19:—453,137 lbs.Manufactured '20:—499,304 lbs.
FORMATION.—By sulfonating nitro-benzene with oleum, and reductionwith iron
334 DYES CLASSIFIED BY INTERMEDIATES
LITERATURE.—Cain, Intermediate Products (2d Ed.), 47Lange, Zwischenprodukte, #619, 620
Dyes Derived from Metanilic Acid
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport andManufacture
Other IntermediatesUsed and Notes
DyeAppli-cationClass
134
135
136
210
256
257
258
542
MONOAZO DYESMetanil Yellow
Metauil YellowBrominated
Acid YellowMGS, GG
DISAZO DYESCotton Orange R
Sulf on Black 3B
Sulfoncyauine
Naphthalene AcidBlack 4B
I '14:—284,606M'17:— ?M'18:— ?M'19 :—477,143I '20:— 8,456M '20:—629,437
Diphenylamine
I '14:— 16,459I '20:— 51
I '14:—145,694M'17: ?M'18:— ?M'19:— ?I '20:— 18,327M'20:— ?
I '14:— 7,994
TRIPHENYL-METEANEDYE
Agalma Green B I '14:— 2,294
Diphenylamine[Bromination]
Diphenylamine[Sulfonationj
PrimiiliD e-sulf omc Acidm-Phenylene-diamine-disulfonic Acid
a-NaphthylaminePhenyl-1-naphthyl-
amine-8-sulf onic Acid
a-Naphthylamine orl-Naphthylamine-6-and 7-sulf onic Acids
Phenyl- or Tolyl-1-naphthylamine-8-sulf onic Acid
1 -Naphthylamine-6-and 7-sulf onic Acids
a-Naphthylamine
4-Chloro-3:5-dinitro-benzene-sulf onic Acid
Hydrol
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Metanilic Acid (continued)
335
SchultzNumberfor Dye
738
Ordinary Name andClass of Dye
SULFUR DYECotton Black
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
l-Chloro-2: 4-dinitro-benzene
[S+Na*S]
DyeAppli-cationClass
S
Methoxy-dimethylamino-benzophenone
See, 4-Dimethylamino~3-methoxy-benzophenonenomen.)
6-Methoxy-m-toluidine (C. A. nomen. NH2=1)
See, 2-Amino-p-cresol Methyl Ether
1-Methylamino-anthraquinone
(C A.
FORMATION.—1-Chloro-anthraquinone is reacted with p-toluene-sulfon-methyl-amide (CH3 . C6H4. SO2 . NH . CH8), splitting off HC1 andforming l-(p-toluene-sulfon-methyl-amino)-anthraquinone. Thislatter readily decomposes in presence of sulfuric acid, forming1-methylamino-anthraquinone
LITERATURE.—Lange, Zwischenprodukte, #3113, 3115, 3117, 3118,3476Barnett, Anthracene and Anthraquinone, 197, etc.
Dye Derived from 1-Methylamino-anthraquinone
SchultzNumberfor Dye
866
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYE
Leucol DarkGreen B
Statistics ofImport and
Manufacture
I '20:— 120
Other IntermediatesUsed and Notes
DyeAppli-cationClass
V
336 DYES CLASSIFIED BY INTERMEDIATES
2-Methylamino-8-naphthol-6-sulfonic Acid
See, Methyl-gamma Acid
7-Methylamino-l-waphthol-3-sulfonic Acid (C. A. nomen.)
See, Methyl-gamma Acid
JV-Methyl-aniline
Methyl-aniline
HNCH3
z=rC7H9N=107
FORMATION.—By heating aniline and methanol (methyl alcohol) in thepresence of sulfuric acid in an autoclave; or by heating anilinehydrochloride and methanol in an autoclave
LITERATURE.—Cain, Intermediate Products (2d Ed.), 61Lange, Zwischenprodukte, #92
USES.—For preparation of ethyl-methyl-aniline and for benzyl-methyl-aniline
2-Methyl-anthraquinone (C. A. nomen.)
£-Methyl-anthraquinone
oco- =C15H10O2 =
FORMATION.—Phthalic anhydride is dissolved in toluene, and heatedwith AICI3 whereby p-toluyl-o-benzoic acid is formed, which latter,upon being dissolved in oleum and heated, forms the 2-methyl-anthraquinone
LITERATURE.—Cain, Intermediate Products (2d Ed.), 259Heller and Sehiilke, Ber. 41, 3632 (1908)Cf. Elbs, J. pr. Chem. [II] 33, 318 (1886)Cf. Limpricht and Wiegand, Ann. 311, 178 (1900)
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 2-Methyl-anthraquinone
337
SchultzNumberfor Dye
759
792
795
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Anthraflavone G
Cibanone Orange R
Cibanone Yellow R
Statistics ofImport and
Manufacture
I '14:— 7,143I '20:— 2,354
I '20:— 6,125
I '14:— 298I '20:— 14,032
Other IntermediatesUsed and Notes
2-Methyl-anthraqui-none (2 mols)
[Sulfur]
[Sulfur]
DyeAppli-cationClass
V
V
V
0-Methyl-anthraquinoneSee, 2-Methyl-anthraquinone3-Methyl-benzaldehyde-4:6-disulfonic Acid4-Formyl-6-methyl-m-6enzene-disulfonic Acid (C A. nomen.)CHOHO3sUSO3HFORMATION.—Probably by oleum sulfonation of m-tolualdehyde(m-tolualdehyde can be made by oxidation of m-xylene)LITERATURE.—Thorpe, Die Chemistry, 5, 516Cf. Lange, Zwischenprodukte, #784Dyes Derived from 3-Methyl-benzaldehyde-4:6-disulfonic Acid
SchultzNumberfor Dye507508
Ordinary Name andClass of DyeTRIPHENYL-METHANJDDYESXylene Blue VSXylene Blue AS
Statistics ofImport andManufactureI '14:— 2,130I '20:— 27,254I '14:— 8,238I '20:— 5,573
Other IntermediatesUsed and Notes
Diethyl-aniline (2 mols)[Oxidation]Benzyl-ethyl-aniline(2 mols)[Oxidation]
DyeAppli-cationClassAA
338 DYES CLASSIFIED BY INTERMEDIATES
Methyl-benzanthrone
9-Methyl-7-meso-benzanthrenone (C A. nomen.)
H3C
FORMATION.—By condensation of 2-methyl-anthrone with glycerol andsulfuric acid at about 120° C.
LITERATURE.—Barnett, Anthracene and Anthraquinone, 324Fr. Pat. 407,593Cf. Ger. Pat. 209,351. Frdl. 9, 836
Dyes Derived fronx Methyl-benzanthrone
SchulizNumberfor Dye
793
794
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Cibanone Blue 3G
Cibanone Black B
Statistics ofImport andManufacture
I '14:— 2,802
Other IntermediatesUsed and Notes
[Sulfur]
[Sulfur]
DyeAppli-cationClass
V
V
l-Methyl-2:4-diamino-benzene-5-sulfonic AcidSee, 4:6-Diamino-m-foluene-sulfonic Acid (C. A. nomen.
l-Methyl-2:6-diamino-benzene-4-sulfonic AcidSee, 3:5-Diamino-p-foluene-sulfonic Acid (C. A. nomen.
JV-Methyl-diphenylamine (C. A. nomen.)Diphenyl-methyl-amine
DYES CLASSIFIED BY INTERMEDIATES 339
FORMATION.—From diphenylamine by heating with hydrochloric acidand methanol (methyl alcohol) in an autoclave at 250°
LITERATURE.—-Cain, Intermediate Products (2d Ed.), 73
Dyes Derived from iV-Methyl-diphenylamine
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport andManufacture
Other IntermediatesUsed and Notes
DyeAppli-cationClass
532
534
547
TRIPHENYL-METHANEDYES
Alkali Violet 6B
Acid Violet 7B
Ketonc Blue 4BN
:— 3,020
I '14:— 21,665I '20:— 51
Tetraethyl-diamino-benzophenone
[Sulfonation]
Diethyl-p-amino-benzoyl Chloride
iV-Methyl-diphenyl-amine (2 mols)
Methoxy-dimethyl-amino-benzophenone
[Sulfonation]
A
A
N-Methyl-diphenylamine-sulfonic Acid
• N — < ( ~ y \ SO3H = Ci3H13NO3S = 263
C H 3
FORMATION.—By sulfonation of methyl-diphcnylamine
LITERATURE.—Beils te in , Organische Chemie (3 auf.), II spl., 324
Dye Derived from N-Methyl-diphenylamine-sulfonic Acid
SchultzNumberfor Dye
533
Ordinary Name andClass of Dye
TRIPHENYL-METHANEDYE
Acid Violet 7BN
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
p-Dimethylamino-benzoyl chloride
iV-Methyl-d i p h e n y 1-amine-sulfonic Acid(2 mols)
DyeAppli-cationClass
A
340 DYES CLASSIFIED BY INTERMEDIATES
^:£'-Methylene-bisaniline (C. A. nomen.)
See, p.'p'-Diamino-diphenyl-methane
^:/>'-Methylene-bis(iV:iSr-diet3iyl-aniliiie) (C. A. nomen.)
See, p: p'-Tetraethyl-diaimno-diphenyl-methane
^:£'-Methylene-bis(iV: iV-dimethyl-aniline) (C. A. nomen.)
See, p: p'-Tetramethyl-diamino-diphenyl-methane
4:4/-Metbylene-bis(iV-niethyl-o-/olui(iine) (C. A. nomen.)
See, 4:4/-Dimethyl-diamino-3: S'-ditolyl-methane
4: ^-Methylene-bis-o-Zoluidine (C. A. nomen.)
See, p: p'-Diamino-ditolyl-methaae
Methylene-bisjcylidine (C. A. nomen.)
See, Diamino-dixylyl-methane
Methyl-ethyl-aniline
See, Ethyl-methyl-aniline
Methyl-gamma Acid
2-Methylamino-8-naplithol-6-sulfonic Acid
7-Methylamino-l-naphtliol~3-sulfoiuc Acid (C. A. nomen.)
HO
H O 3 s ( Y ) N H * C H 3 = CnH.NO.S = 253
FORMATION.—G salt (Sodium salt of 2-naphthol-6:8-disulfonic acid)is heated in aja autoclave with methylamine; and the resulting2-methylamino-naphthalene-6: 8-disulfonic acid is fused with causticsoda in an autoclave, forming methyl-gamma acid. (See Gammaacid)
,—Lange, Zwischenprodukte, #2550
DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from Methyl-gamma Acid
341
SchultzNumberjor Dye
347
Ordinary Name andClass of Dye
DISAZO DYEDiphenyl Brown RN
Statistics ofImport arid
ManufactureOther Intermediates
Used and Notes
BenzidineSalicylic Acid
DyeAppli-cationClass
D
7-Methyl-indoxyl
C H a N HCH2 =
FORMATION.—o-Toluidine is reacted with chloro-acetic acid, formingo-tolyl-glycine. This body upon fusion with sodamide will in allprobability form 7-methyl-indoxy. (There is no direct referencein the literature to 7-methyl-indoxyl)
LITERATURE.—Lange, Zwischenproduktc, #241
Dye Derived from 7-Methyl-indoxyl
SchultzNumberfor Dye
898
Ordinary Name andClass of Dye
INDIGO GROUP DYEHelindone Violet D
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
Isatin[Bromination]
DyeAppli-cationClass
V
9-Methyl-7-meso-&enzanthrenone (C. A. nomen.)
See, Methyl-benzanthrone
N-Methyl-^-nitroso-aniline (C. A. nomen.)
See, p-Nitroso-methyl-aniline
342 DYES CLASSIFIED BY INTERMEDIATES
Methyl-phenyl-a-naphthylamine
iV-Methyl-iV-phenyl-1-naphthylamine (C A. nomen.)
FORMATION.—Phenyl-a-naphthylamine is methylated by heating with
methanol (methyl alcohol) and hydrochloric acid under pressure
LITERATURE.—Schultz, Chemie des Steinkohlentheers (3 aufl. 1900)
1,117
SchultzNumberfor Dye
522
Dye Derived from
Ordinary Name andClass of Dye
TRIPHBNYL-METHANEDYE
Victoria Blue 4R
Methyl-phenyl-a-naphthylamine
Statistics ofImport and
Manufacture
I '14:— 9,599I '20:— 152
Other IntermediatesUsed and Notes
Ketone
DyeAppli-cationClass
B
Methyl-(Ethyl-)phenyl-j3-naphthylamine
iV-Methyl-(Ethyl-)iVr-phenyl-2-naphthylamine (C. A. nomen.)
CH3
FORMATION.—Phenyl-^-naphthylamine is methylated by heating in
an autoclave with methanol (methyl alcohol) and hydrochloric
acid
LITERATURE,—Lange, Zwischenprodukte, #2897
DYES CLASSIFIED BY INTERMEDIATES 343
Dye Derived from Methyl-(Ethyl-) phenyl-0-naphthylamine
SchultzNumberfor Dye
561
Ordinary Name andClass of Dye
DlPHENYL-NAPHTHYL-METHANE DYE
Acid Violet 5BNS
Statistics ofImport and
Manufacture
I '14:— 1,896
Other IntermediatesUsed and Notes
Ketone[Sulfonation]
DyeAppli-cationClass
A
3-Methyl-l-phenyl-5-£yrazolone (C. A. nomen.)
l-Phenyl-3-methyl-5-pyrazolone
N-
OC NN
H 2 C — C . C H 3
STATISTICS.—Imported '14:—449 lbs.
FORMATION,—By heating the reaction product of phenyl-hydrazineand aceto-acetic ethyl ester
LITERATURE.—Lange , Zwischenprodukte. #138
Dyes Derived from 3-Methyl-l-phenyl-5-pyrazolone
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport andManufacture
Other IntermediatesUsed and Notes
DyeAppli-cationClass
21
24
26
28
29
PYRAZOLONE DYESPigment Chrome
Yellow L
Pigment FastYellow R
Dianil Yellow R
Pigment FastYellow G
Eriochrome Red B
M'19:— ?I '20:— 170
I '14:— 5,491
Toluidine
o-Toluidine-m-sulfonicAcid
Prim uline-sulf onicAcid
p-Sulfo-anthranilicAcid
l-Amino-2-naphthol-4-sulfonic Acid
CL
CL
D
CL
CL
344 DYES CLASSIFIED BY INTERMEDIATES
2-Methyl-quinoline
See, Quinaldine (C. A. nomen.)
4-Methyl-quinoline (N=l)
See, Lepidine (C. A. nomen.)
a-Methyl-quinoline
See, Quinaldine (C A. nomen.)
7-Methyl-quinoline
See, Lepidine (C. A. nomen.)
Methyl Resorcinol
See, Resorcinol Methyl Ether
3-Methyl-l-(^-sulfo-phenyl)-5-pyrazolone
l-(p-Sulfophenyl)-3-methyl-5-pyra2!olone
p-(4:5-Dihydro-5-keto-3-methyl-l-py razolyl)-&enzene-sulf onic
Acid (C. A. nomen.)
OC N 1 0 1 0 2 4
H2C—C. CH3
FORMATION.—(1) By sulfonating 3-methyl-l-phenyl-5-pyrazolone by
heafcing with 4 parts of 30 per cent oleum. (2) By heating phenyl-
hydrazine-p-sulfonic acid with aceto-acetic ethyl ester in 50 per
cent acelic acid solution for few hours
LITERATURE.—Cain, Intermediate Products (2d Ed.), 169Lange, Zwischenprodukte, #138
DYES CLASSIFIED BY INTERMEDIATES 345
Dyes Derived from 3-Methyl-l-(^-sulfo-phenyl)-5-pyrazolone
SchultzNumberfor Dye
19
27
Ordinary Name andClass of Dye
PYKAZOLONE DYESFlavazine LFast Light Yellow
Dianil Yellow 2R
Statistics ofImport andManufacture
I '14:— 38,908I '20:— 9,327
Other IntermediatesUsed and Notes
Aniline
Primuline-sulfonic Acid
DyeAppli-cationClass
A
D
N-Methyl-o-foluidine (C. A. nomen. NHRMethyl-o-toluidine
HN—CH3
STATISTICS.—Manufactured ' 19:— ?
FORMATION.—(1) By heating o-toluidine, methanol (methyl alcohol)and hydrochloric acid in an autoclave. (2) By condensing o-toluidine and formaldehyde, and reducing to methyl-o-toluidine
LITERATURE.—Cain, Intermediate Products (2d Ed.), 60, 70C/. Lange, Zwischenprodukte, #128
Dyes Derived from AT-Methyl-o-toluidine
SchultzNumberfor Dye
•494
501
684
Ordinary Name andClass of Dye
AURAMINE DYEAuramine G
TRIPHENYL-METHANEDYE
Glacier BlueBrilliant Glacier
Blue
AZINE DYEBrilliant Rhoduline
Eed
Statistics ofImport and
Manufacture
I '14:— 1,902
I '14:— 2,495
Other IntermediatesUsed and Notes
Methyl-o-toluidine (2mols)
[Formaldehyde, sulfur,ammonium chloride,etc.]
Methyl-o-toluidine (2mols)
2:5-Dichloro-benzalde-hyde
[Oxidation]
iV^-Ethyl-4-m-tolylene-diamine
Aniline
DyeAppli-cationClass
B
B
B
346 DYES CLASSIFIED BY INTERMEDIATES
Michler's HydrolSee, Hydrol
Michler's Ketone or BaseSee, Ketone
Monochloro-benzene1
See, Chloro-benzene
Monoethyl-aniline1
See, Ethyl-aniline
Monomethyl-aniline1
See, Methyl-aniline
Mononitro-chloro-benzene1
See, Chloro-nitro-benzene
Monosulfonic Acid PSee, 2-Naphthol-7-sulfonic Acid
Monosulfo Acid Hl-Amino-8-naphthol-3-sulfonic Acid (not considered herein)
Mu AcidSee, l-Naphthylamine-6-sulfonic Acid
Myrbane OilSee, Nitro-benzene
Naphtha-See also, Naphtho-
a-Naphthahydroquinone1:4-Dihydroxy-naphthalene (not considered herein)
i^-Naphthahydroquinone1:2-Dihydroxy-naphthalene (not considered herein)
1 " Mono " is superfluous and is consequently not recommended.
DYES CLASSIFIED BY INTERMEDIATES 347
Naphthalene (C. A. nomen.)
Naphthalin
Note.—Naphthalene is a crude and not an intermediate as a rule
— CioHs —128
STATISTICS.— Refined NaphthaleneManufactured Imported
Calendar Year 1917:—35,342,911 lbs. 267,057 lbs." 1918:—33,701,779 lbs. 2,795 lbs." 1919:—17,625,235 lbs. 7,650 lbs.
" 1920:—30,230,734 lbs. 3,697,562 lbs.
FORMATION.—From coal tar by extraction and purification
LITERATURE.—Thorpe, Die. Chemistry, 3, 560
Dyes Derived from Naphthalene
SchultzNumberfor Dye
564
758
Ordinary Name andClass of Dye
DlPHENYL-NAPHTHYL-METHANE DYE
NaphthaleneGreen V
ANTHRAQUINONE ANDALLIED DYES
Sirius Yellow G
Statistics ofImport and
Manufacture
I 714:— 22,144I '20:— 9,291
Other IntermediatesUsed and Notes
Hydrol
Phthalic anhydride
DyeAppli-cationClass
A
CL
1: 5-Naphthalenediol (C. A. nomen.)
See, 1:5-Dihydroxy-naphthalene
2:7-Naphthalenediol (C. A, nomen.)
See, 2: 7-Dihydroxy-naphthalene
48 DYES CLASSIFIED BY INTERMEDIATES
Naphthalene-1:5- and 1:6-disulfonic Acids
'he 1:5 acid is also called:
Armstrong's AcidArmstrong's 8 Acid
Naphthalene-7-disulfonic Acid of Armstrong and Wynne
Naphthalene-5-disulfonic Acid of Beilstein and Schultz
'he 1: 6-acid is also called:Ewer and Pick's Acid
Naphthalene-? : /3-disulfonic Acid of Armstrong and Wynne
Naphthalene-7-disulfonic Acid of Beilstein and Schultz
SO3H SO3H
omd ^n^l I I =Ci0H8O6S2 = 288
HO3S
ORMATION.—The above acids are prepared by sulfonation of naphtha-lene with five parts of 23 per cent oleum at 60°; or with five partsof ordinary sulfuric acid (66°) using first one part at 180° to form the/3-sulfonic acid and then four parts at 95-100° for 20-24 hours
If the 1: 5-acid alone is wanted the conditions of sulfonation arevaried slightly, generally starting with the a-sulfonic acid. Theseparation is effected by crystallizing out the 1: 5 acid or its sodiumsalt from the diluted sulfonation product
ITERATUKE.—Cain, Intermediate Products (2d Ed.), 176, 177Thorpe, Die. Chemistry, 3, 575
SES.—The mixed acids are used for the preparation of 1-naphthyl-amine-3: 8- and 4: 8-disulfonic acids, and the separation then made
The 1: 5-acid is used for making naphthalene-1: 3: 5-trisulfonicacid
Naphthalene-2:7-disulfonic Acid
a-Naphthalene-disulfonic Acid (of Ebert and Merz)
Ebert and Merz a Acid
DYES CLASSIFIED BY INTERMEDIATES 349
STATISTICS.—Manufactured 1918, 1919, 1920 in undisclosed quantitiesFORMATION.—Sodium 2-naphthalene-sulfonate is further sulfonated by
dissolving in about two parts of monohydrate or a larger amountof 66° sulfuric acid, and heating to 180° for 6-8 hours. There isformed principally naphthalene-2: 6- and 2: 7-sulfonic acids, andthe separation is effected through the calcium salts, the 2:6 saltbeing less soluble
LITERATURE.—Lange, Zwischenprodukte, #2442Ger. Pat. 61,730Thorpe, Die. Chemistry, 3, 577
Dyes Derived from Naphthalene-2:7-disulfonic Acid
SchultzNumberfor Dye
564
Ordinary Name andClass of Dye
DlPHENYL-NAPHTHYL-METHANE DYE
NaphthaleneGreen V
Statistics ofImport and
Manufacture
I '14:— 22,144I '20:— 9,291
Other IntermediatesUsed and Notes
Hydrol[Oxidation]
DyeAppli-cationClass
A
Naphthalene-? : /3-disulfonic Acid of Armstrong and WynneSee, Naphthalene-1: 6-disulfonic Acid
Naphthalene-7-disulfonic Acid of Armstrong and WynneSee, Naphthalene-1: 5-disulf onic Acid
Naphthalene-5-disulfonic Acid of Beilstein and SchultzSee, Naphthalene-1:5-disulf onic Acid
Naphthalene-7-disulfonic Acid of Beilstein and Schultz
See, Naphthalene-1:6-disulfonic Acid
a-Naphthalene-disulfonic Acid of Ebert and MerzSee, Naphthalene-2: 7-disulfonic Acid
Naphthalene-1:3:5-trisulfonic Acid
SO8H
OA TT :==: C10H.8O9S3 '==:-368
350 DYES CLASSIFIED BY INTERMEDIATES
FORMATION.—By sulfonation of naphthalene-1: 5-disulfonic acid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 179Thorpe, Die. Chemistry, 3, 578
USES.—For preparation of l-naphthylamine-4: 6: 8-trisulfonic acid
Naphthalene-1:3:6-trisulfonic Acid
Trisulfonic Acid
SO3H
= C l o H 8 ° 9 S 3 = 3 6 8
FORMATION.—By sulfonating naphthalene for some hours at 180° with24 per cent oleum, or preferably by sulfonating sodium naphtha-Iene-j3-sulfonate at a low temperature with forty per cent oleum
LITERATURE.—Cain, Intermediate Products (2d Ed.), 181Lange, Zwischenprodukte, #2662Thorpe, Die. Chemistry, 3, 578
USES.—For preparation of l-naphthol-3:6-disulfonic acid and 1-naph-thylamine-3:6: 8-trisulfonic acid. The latter acid is the last stepprior to the manufacture of H acid (l-amino-8-naphthol-3: 6-di-sulfonic Acid)
Naphthalic Acid
Naphthalene-1:8-dicarboxylic Acid (not considered herein)
Naphthalidam
See, a-Naphthylamine
Naphthalidine
See, a-Naphthylamine
Naphthalidine-sulfonic Acid
SeeT Laurent's Acid
DYES CLASSIFIED BY INTERMEDIATES 351
Naphthalidinic Acid
See, Laurent's Acid
Naphthalin
See, Naphthalene
Naphthapyrogallol
1:2: 3-Trihydroxy-naphthalene (not considered herein)
a-Naphthaquinol
1:4-Dihydroxy-naphthalene (not considered herein)
0-Naphthaquinol
1:2-Dihydroxy-naphthalene (not considered herein)
1:2-Naphthaquinone
See, 1: 2-Naphthoquinone (C. A. nomen.)
a-Naphthaquinone
1:4-Naphthoquinone (not considered herein)
jS-Naphthaquinone
See, 1:2-Naphthoquinone
1:8-Naphthasultam-2:4-disulfonic Acid
4-Amino-4: 5-sultam-l: 3: 5-naphthalene-trisulfonic Acid (C. A,nomen.)
SO2-NH
SO3H — c10H7NO8S3=365
SO3H
FORMATION.—The acid sodium l-naphthylamine-4:8-disulfonate is sul-fonated with two parts of 40 per cent oleum, and wanned to 80-90°.This warming is continued until a sample no longer diazotkes anddoes not form a dye with diazotized sulf anilic acid
352 DYES CLASSIFIED BY INTERMEDIATES
LITERATURE.—Cain, Intermediate Products (2d Ed.), 201
USES.—For preparation of l-amino-8-naphthol-2:4-disulfonic Acid
Naphthazarin (C. A. nomen.)
5: 6-Dihydroxy-l: 4-naphthoquinone
5: 6-Dihydroxy-a-naphthoquinone
1: 2-Dihydroxy-naphthoquinone
Oxy-juglone
FORMATION.—Crude dinitro-naphthalene (a mixture of 1:5- and 1: 8-dinitro-naphthalene) is treated with oleum and sulfur
LITERATURE.—Georgievics and Grandmougin, Dye Chemistry, 333Cf. Lange, Zwischenprodukte, #2759Schultz, Farbstofftabellen (1914), #774Thorpe, Die. Chemistry, 3, 656, 569
Dyes Derived from Naphthazarin
SchvXizNumberfor Dye
774
775
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Alizarin Black
Alizarin DarkGreen W
Statistics ofImport and
Manufacture
I '14:—205,439I '20:— 17,421
Other IntermediatesUsed and Notes
[NaHSO3]
Phenol
DyeAppli-cationClass
M
M
1:2-jS-Naphthazoledione (C. A. nomen.)
See, jS-Naphthisatin
DYES CLASSIFIED BY INTERMEDIATES 353
o-Naphthionic Acid
See, l-Naphthylamine-2-sulfonic Acid
Naphthionic Acid
Naphtholic Acid
Piria's Acid
l-Naphthylamine-4-sulfonic Acid
l-Amino-naphthalene-4-sulfonic Acid
4-Amino-l-naphthalene-sulfonic Acid ( C A. numbering)
Note.—C. A. nomenclature is Naphthionic Acidy but C. A. numbers-om the -SOzH group, instead of from -NHz group, as is the usual procedure
NH2
= Ci0H9NO3S =
TATISTICS.—Manufactured ' 17:— ?Manufactured '18:—1,462,216 lbs.Manufactured '19:—2,008,189 lbs.Manufactured '20:—3,773,191 lbs.
OKMATION.—By "baking" a-naphthylaminc and sulfuric acid plus alittle oxalic acid in pans in an oven
ITERATUBE.—Cain, Intermediate Products (2d Ed.), 189Lange, Zwischenproduktc, #2359Thorpe, Die. Chemistry, 3, 590
Dyes Derived from Naphthionic Acid
chultzumber•r Dye
52
91
Ordinary Name andClass of Dye
MONOAZO DYES
Archil Substitute V
Anthracyl ChromeGreen AD
Statistics ofImport and
Manufacture
I '14:— 4,596M'18:— ?I '20:— 3,316
Other IntermediatesUsed and Notes
p-Nitro-aniline
Picramic Acid
DyeAppli-cationClass
A
ACr
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Naphthionic Acid (continued)
SchultzNumberfor Dye
160
161
163
164
165
166
167
Ordinary Name andClass of Dye
MONOAZO DYES(continued)
NaphthylamineBrown
Fast Brown N
Fast Red A
Azo Rubine
Fast Red VR
Azo Red A
Fast Red E
Croceine Scarlet 3BX
Statistics ofImport and
Manufacture
I J14:— 68,281M'17:— ?M'18:-— ?M'19:— ?M320:— ?
I '14:— 46,359M'17:—191,424M'18:—242,215M'19:—267,582I '20:— 948M'20:-433,989
I '14:—230,763M'17:—197,621M'18:— 79,779M'19:—187,264I '20:— 1,102M'20:-470,949
I '14:— 20,714M'17:— ?M'18:— ?M'19:— ?I '20:— 6,290M'20:— ?
I '14:— 2,473M'17:— ?M'18:— ?M'19:— ?M'20:— ?
I '14:— 13,101M'17:— ?M'18:— ?M'19:— ?I '20:— 651M'20:— ?
Other IntermediatesUsed and Notes
a-Naphthol
/3-Naphthol
Nevile-Winther's Acid
l-Naphthol-5-sulfonicAcid
l-Naphthol-3: 6-disul-fonic Acid
Schaeffer's Acid
Croceine Acid
DyeAppli-cationClass
ACr
A
A
ACr
A
A
A
DYES CLASSIFIED BY INTERMEDIATES 355
Dyes Derived from Naphthionic Acid (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport andManufacture
Other IntermediatesUsed and Notes
168
169
170
171
209
213
264
307
MONOAZO DYES(continued')
Amaranth
CochinealRed A
Ponceau 6R
Chromotrope 8B
DISAZO DYESTerra Cotta FC
Fast Brown
Fast SulfonBlack F
Congo Red
I '14:— 86,067M'17:— 66,069M'18:— 73,539M'19:— 294,416I '20:— 110M'20:—204,958
I '14:— 32,645M'17:— ?M'18:— ?M'19:—231,519M'20:—288,945
M'18:— ?
I '14:— 551
I '14:-M'17:-M'18:-M'19:-M'20:-
3,206????
I '20.— 2,204M'20:— ?
I '14:— 20,629M'17:— ?M'18:—587,153M'19:—873,734M'20:—
1,502,630
R Acid
G Acid
2-Naphthol-3: 6:8-trisulfonic Acid
Chromotropic Acid
Primuline orDehydro-thio-toluidine-sulfonicAcid
m-Phenylene-diamine
ResorcinolNaphthionic Acid
(2 mols)
HAcid/3-Naphthol
BcnzidineNaphthionic Acid
(2 mols)
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Naphthionic Acid (continued)
Ordinary Name andClass oj Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
DISAZO DYES(continued)
Glycine Red
Orange TA
Congo Corinth G
Congo Rubine
Benzo Orange R
Dianol Red 2B
Benzo Purpurin 4B
BrilliantPurpurin 4B
I '14:—M'17:—M'18:—M'19:—M'20:—
602????
I '14:— 44,157M'17:—- ?M'18:— ?M'19:—137,704M'20:—242,50:
I '14:— 46,213M'17.— ?M'18:— ?I '20:— 2,601
I '14:— 1,073M'17:— ?M'18:— 50,422M'19:— 42,807I '20:— 220M '20:— 86,210
I '14:— 4,422I '20:— 17,632
I '14:—351,712M'17:— ?M'18:—356,522M'19:—288,021I '20:— 3,492M'20:—617,629
I '14:— 6,634
Benzidine Da-Naphthyl-glycine
Benzidine DCresol
Benzidine DNevile-Winther's Acid
BenzidineCroceine Acid
BenzidineSalicylic Acid
Dichloro-benzidineNaphthionic Acid
(2 mols)
TolidineNaphthionic Acid
(2 mols)
Tolidine DBroenner's Acid
DYES CLASSIFIED BY INTERMEDIATES 357
Dyes Derived from Naphthionic Acid (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DISAZO DYES(continued)
Brilliant Purpurin R
Congo 4RCongo Red 4R
Congo Corinth B
Benzopurpurin 10B
Azo Violet
TRISAZO DYESDianil Black R
Azo Corinth
TETRAKISAZO DYESBenzo Brown B
Toluylene Brown R
I ' 1 4 : — 8 , 0 5 1
M ' 1 8 : — ?
2 , 1 9 6
4 7 , 7 6 8
I '14*M'19:-
I ' 1 4 : —
M'18 :«
M ' 1 9 : -
I ' 2 0 :
M ' 2 0 :
2,20541,265
I '14:M'20:-
4389
I ' 1 4 : — 2 0 1
T o l i d i n e
A m i n o - R A c i d
T o l i d i n e
R e s o r c i n o l
T o l i d i n e
N e v i l e - W i n t h e r ' s A c i d
D i a n i s i d i n e
N a p h t h i o n i c A c i d
( 2 m o l s )
D i a n i s i d i n e
N e v i l e - W i n t h e r ' s A c i d
B e n z i d i n e
C h r o m o t r o p i c A c i d
m - P h e n y l e n e - d i a m i n e
T o l i d i n e
R e s o r c i n o l
3 - A m i n o - l - p h c n o l - 4 -
s u K o n i c A c i d
m - P h c n y l e n c - d i a m i n e
(3 m o l s )
N a p h t h i o n i c A c i d
(2 m o l s )
3 : 5 - D i a m i n o - p - t o l u e n e -
s u l f o n i c A c i d
m - P h e n y l e n e - d i a m i n e
(2 m o l s )
N a p h t h i o n i c A c i d
(2 m o l s )
358 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Naphthionic Acid (continued)
SchultzNumberfor Dye
490
563
Ordinary Name andClass of Dye
TETRAKISAZO DYES{continued)
Cotton Brown A
DlPHENYL-NAPHTHYL--METHANE DYE
New Patent Blue B
Statistics ofImport andManufacture
I '14:— 29,074
I '14:— 595I '20:— 1,814
Other IntermediatesUsed and Notes
Benzidinem-Phenylenc-diamine
(2 mols)Naphthionic Acid
(2 mols)
Hydrol[Substitution of NH2 by
SO3H; Oxidation]
DyeAppli-cationClass
D
A
/3-Naphthisatin
2-Naphthisatin
1: 2-/3-Naphthazoledione (C A. nomen. for ketoform)
1:2-Diketo-l: 2-dihydro-/3-naphthindole
CO—CO CO—C.OH
- N H —N= C12H7NO2 =
FORMATION.—/3-Naphthylamine is reacted with glyoxal sodium bisul-fite compound forming /3-naphthindol-sulfonate
<CH
NH
. SO3Na
By adding acetic acid and sodium nitrite to a solution of this latterbody in warm water, there results isonitroso-naphthoxindole
. C : N . O HC10HX >CO , which upon being boiled with sulfuric acid
\forms the jS-naphthisatin
LITERATURE.—Beilstein, Organische Chemie (2 auf.) II, 624; I I spl.342Cf. Lange, Zwischenprodukte, #2965
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from /3-Naphthisatin
359
SchultzNumberfor Dye
891
892
Ordinary Name andClass of Dye
INDIGO GROUP DYESCiba Green G
Helindone Green G
Statistics ofImport and
Manufacture
I '14:— 119
I '20:— 1,248
Other IntermediatesUsed and Notes
/3-Naphisatin (2 mols)[Bromination]
/3-Naphthisatin (2 mols)[Bromination]
DyeAppli-cationClass
V
V
2-Naphthisatin
See, jS-Naphthisatin
1-Naphthol/See, a-Naphthol
2-NaphtholSee, /3-Naphthol
a-Naphthol1-Naphthol (C A. nomen.)
OH
STATISTICS.—Imported '14:—405,578 lbs.Manufactured '17:— 72,329 lbs.Manufactured '18:—136,723 lbs.Manufactured '19:—135,025 lbs.Manufactured '20:— ?
FORMATION.—(l)Naphthalene is sulfonated cold to a-naphthalene-sulfonic acid, which is then fused with caustic soda to form thea-naphthol. (2) a-Naphthylamine hydrochloride or sulfate ishydrolyzed to a-Naphthol by heating with water in an autoclave
LITERATURE.—Cain, Intermediate Products (2d Ed.), 212Lange, Zwischenprodukte, #2269-2271Thorpe, Die. Chemistry, 3, 614
360 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from a-Naphthol
SchidtsNumberfor Dye
105
144
160
172
ISO
183
Ordinary Name andClass of Dye
NITRO DYESMartius Yellow
Naphthol Yellow S
MONOAZO DYESSudan Brown
Orange I
XaphthylamineBrown
Fast Brown N
Fast Brown 3B
Erio Chrome BlueBlack B
Erio Chrome Black T
Statistics ofImport andManujacture
I '14:— 3,295I '20:— 26
I '14:—251,222M'17:— ?M'18:— ?M'19:— ?M'20:— ?
M'17:— ?M '18:— ?M'19:— ?
I '14:— 8,30;M'17:— ?M'18:— ?M'19:— ?I '20M'20
1,32314,684
I '14:— 68,281M'17:— ?M'18:— ?M'19:— ?M'20:— ?
I '14:— 1,477
I '14:-M'17:-M'18:-M'19:-I '20:-M'20:-
I '14:-M'18:-M'19:-I '20:-M'20:-
57,0009,326
- 20,371- 29,255
-129,550
- 2,624
Other IntermediatesUsed and Notes
[Dirutration]
[Dinitration, Sulf ona-tion]
a-Naphthylamine
Sulfanilic Acid
Naphthionic Acid
Broenner's Acid
l-Amino-2-naphthol-4-sulfonic Acid
Nitro-l-amino-2-napli-thol-4-sulfonic Acid
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from a-Naphthol (continued)
301
SchultzNumberjor Dye
212
214
619
731
895
Ordinary Name andClass of Dye
DISAZO DYESFast Brown GAcid Brown G
Fast Brown 0
INDOPHENOL DYEIndophenol
SULFUR DYEThiophor Indigo CJ
INDIGO GROUP DYEAlizarin Indigo 3H
Statistics ofImport and
Manufacture
I '14:— 17,407I '20:— 485
I '14:— 2,000
M'17:— ?M'18;— ?M19:—126,611M'20:— ?
I '20:— 3,514
Other IntermediatesUsed and Notes
Sulfanilic Acid (2 mols)
Xylidinc-sulfonic Acid(2 mols)
Nitroso-dimethyl-anilinc orDimethyl-p-phenylenc-diamine
Dimcthyl-p-phenylcnc-diaminc
[S+Na*S]
Dibromo-isatinChlorido
DyeA ppli-cntlonClass
A
A
V
S
V
0-Naphthol
2-Naphthol (C A. nomen.)
(^ J J 0 H = CioH80 = 144
STATISTICS.—Imported '14:— 1,264,525 lbs.Manufactured '17:— 5,952,772 lbs.Manufactured '18:— 5,254,637 lbs.Manufactured ;19:— 4,916,416 lbs.Manufactured '20:—11,920,714 lbs.
FORMATION.—Naphthalene is sulfonated to /^naphthalene-sulfonie acid;this is fused with caustic soda, and the resulting /5-naphlhol isisolated and purified
LITERATURE.—Cain, Intermediate Products (2d Ed.), 212Thorpe, DicT Chemisiry, 3, G14; 623
362 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from /3-Naphthol
SchidtzNumberj or Dye
2
36
46
56
72
73
74
76
86
93
Ordinary Name andClass of Dye
NITROSO DYEGambine YFast Printing Green
MOXOAZO DYESSudan IOil Orange
7n-NitranilineOrange
Paranitraniline Red
Pigment Orange R
Pigment FastRedHL
Lithol FastScarlet R
Helio Fast Red RL
Tannin Orange R
Sudan II
AzarineS
Pigment Purple ASudan R
Statistics ojImport arid
Manufacture
I '14:— 4,554M'17:— 32,455M'18:—29,670M'19:— 75,868M'20:—116,624
I »14:—4:9,847M'17:— ?M'18:— ?M'19:— ?M'20:— ?
I '14:— 49,708M'17:— ?M'18:— ?M'19:— ?I '20:— 1,001M'20:— ?
I '14:— 2,202I '20:— 347
I '14:— 501M'17:— 27,595M'18:— 23,692M'19:— ?M'20:—170,658
I '14:— 99
Other IntermediatesUsed and Notes
[Nitroso-derivative]
Aniline
m-Nitro-aniline
p-Nitroaniline
p-Nitro-o-toluidine
m-Nitro-p-toluidine
o- and p-Amino-benzyl-dimetKyl-amine
Xylidine
2-Amino-4: 6-dichloro-pbenol
o-Anisidine
DyeAppli-cationClass
M
ss
MF
MF
CLMF
CL
B
ss
M
CL
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from /?-Naphthol {continued)
363
SchultzNumberfor Dye
97
98
99
106
115
126
131
132
145
Ordinary Name andClass of Dye
MONOAZO DYES{continued)
ChloranisidineScarlet
Naphthol PinkNitrosamine
PinkBX
Tuscaline Orange G
Carmine NaphthGarnet
Autol Red RL
Azo Turkish Red
Indoin Blue RUnion Blue R
Permanent Orange R
Lake Red P
Orange II
Statistics ofImport and
Manufacture
I '14:— 99
I '14:— 6,505M'17:— ?M'18:— ?M'19:— ?M '20:— ?
I '14:— 15,353
I '14:— C0,345M'17:— ?M'18:— ?M'19:— ?I '20:— 1,750
I '14:—128,877M'17:—712,586M'18:—916,890M'19:—
1,133,925I '20:— 2,265M'20:—
1,850,341
Other IntermediatesUsed and Notes
Chloro-anisidinc
p-Nitro-o-anisidine
m-Nitro-o-anisidine
ct-Napl ithylamine
jft-Naphthylamino
Safr&nineor
m-Toly lenc-diamin eo-ToluidiixeAniline
2-Amino-C-chloro-bcn-zene-sulfonic Acid
p-*Nitro-anilino-o-sul-f onic Acid
Sulfanilic Acid
DyeA ppli-catlonClass
MF
MF
CLMF
CL
MF
B
CL
CL
A
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 0-Naphthol (continued)
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOthei Intermediates
Used and Notes
DyeAppli-cationClass
MONOAZO DYES(continued)
Fast Orange 0
Orange T and RO
Lake Red C
Acid AlizarinViolet N
Palatine ChromeViolet
Acid AlizarinBlack R
Fast Red A
Brilliant Fast Red G
Lithol Red R
I 14:-— 1,250M'17:— ?
I 14:— 90,747M'17:— ?M19:— ?I '20:— 20M'20:— ?
I '14:—306,607M'19:— ?I '20:— 4,105M'20:-- ?
I '14:— 1,199M'19:— ?M'20:— ?
14:— 16,800M'19:— ?I '20:— 439M'20:— ?
I '14:— 46,359M17:—191,424M18:—242,215M19:—267,582I '20:— 948M'20:—433,989
I 14:—281,963M 17:— ?M18:—353,104M19:—269,169M'20:— ?
o-Nitro-aniline-p-sulfonic Acid
o-Toluidine-m-sulfonicAcid
2~Chloro-5-toluidine-4-sulfonic Acid
o-Amino-phenol-p-sul-fonic Acid
2-Amino-6-nitro-l-phenol-4-sulfonicAcid
Naphthionic Ac'd
Laurent's Acid
2-Naphthylamine-l-sulfonic Acid
CL
CL
ACr
M
A
CL
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from /?-Naphthol {continued)
365
SchulizNumberjor Dye
174
175
181
184
185
193
200
223
Ordinary Na?ne andClass oj Dye
MONOAZO DYES(continued)
Double BrilliantScarlet
Ponceau for Silk
Palatine ChromeBlack 6B
Salicine Black U
Erio ChromeBlack A
Anthracene ChromeBlack
Clayton Cloth RedStanley Red
Lake Red D
DISAZO DYESSudan III
Statistics ojImport and
Manufacture
I '14:—210,429M'17:— ?M'20:— ?
I '14:— 727
I '14:—248,721M'17:— ?M'18:—469,159M'19:—739,372M'20:— 2,001M'20:—
1,074,248
I '14:— 96,570M'17:— ?M'18:— ?M'19:—686,700I '20:— 14,262M'20:— ?
I '14:— 51,577I '20:— 2,339
I '14:— 100M'18:— ?M'19:— ?M'20:— ?
I '14:— 2,428M'17:— ?M'18:— ?M'19:— ?M'20:— ?
I '14:— 2,409M'17:— ?M'18:— ?M'19:— ?M'20:— ?
Other IntermediatesUsed and Notes
Broenner's Acid
2-Naphthylamine-8-and 5-sulfonic Acids
l-Amino-2-naphthol-4-sulfonic Acid
Nitro-l-amino-2-naph-thol-4-sulfonic Acid
2-Amino-3Jnaphthol-6-gulfonic Acid
Dchydro-thio-p-toluidine-sulfonicAcid
Anthranilic Acid
Amino-azo-benzene
DyeAppli-cationClass
A
A
ACr
ACr
M
A
CL
S3MF
366 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from jS-Naphthol (continued)
SchidtsNumberfor Dye
232
239
240
246
247
252
260
264
Ordinary Name andClass of Dye
DISAZO DYES(continued)
Sudan IV
Azotol C
Janus Red B
Cloth Scarlet G
Double ScarletScarlet EC
Cloth Scarlet R
Erio ChromeVerdon A
Fast Sulf on Black F
Statistics ojImport arid
Manufacture
I '14:M'17:-M'18:-M'19:-M'20:-
5113,33414,904
?
I '14I '20
:— 250:— 176
I '14M'17:3VT18:M'19;M'20:-
I '14:-M'17:-M'18:-M'19:-M'20:-
:— 9:— ?:— ?:— ?
:— ?
39,522
74,203
I '14:— 882
M'19:I '20:M'20:-
?2,204
Other IntermediatesUsed and Notes
DyeAppli-cationClass
o-Amino-azo-toluene
Amino-chrysoidineor
p-Amino-acetanilide andm-phenylene-diamine
ori\T-Dimethyl-p: p'-dia-
mino-azo-benzene
m-Amino-phenyl-tri-methyl-ammoniuinChloride
??2-Toluidine
A m in o-azo-benzene-sulf onic Acid
Amino-azo-benzene-disulfonic Acid
o-Ainino-azo-toluene-sulf onic Acid
Sulfanilic Acidm-Amino-p-cresol
Naphthionic AcidHAcid
DYES CLASSIFIED BY INTERMEDIATES 367
Dyes Derived from /3-Naphthol (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
DISAZO DYES(continued)
Diamine Blue 6G
Acid AlizarineBlack SE
Palatine ChromeBlack F
Acid AlizarineBlack SN
Palatine ChromeBlack S
Benzidine Puce
Trisulf on Violet B
Trisulfon Blue R
Milling Scarlet 4RAcid Anthracene
Red3B
Diazurine B
Statistics ofImport and
Manufacture
I '14:— 19,185I '20:— 34,302
M'17:M'18:-M'19:-
I '14:— 1,124M'17:— ?M'18:— ?M'19:— ?I '20:— 7,927M'20:— ?
911I '14:—M'19:— ?M'20:— ?
I '14:— 18,330I '20:— 2,336
Other IntermediatesUsed and Notes
Amino-G Acidl-Amino-2-naphthol
Ethyl Ether
2:6-Diamino-phenol-4-sulfonic Acid
0-Naphthol (2 mols)
2: 6-Diamino-phenol-4-sulfonic Acid
SchaelTer's Acid
Benzidinej3-Naphthol (2 mols)
Benzidinel-Naphthol-3: G
sulf onic Acid
l-Naphthol-3: 6: 8-tri-sulf onic Acid
Tolidine
o-Tolidine-disulfonicAcid
i8-Naphthol (2 mols)
Dianisidinel-Naphthylamine-6-
sulf onic Acid (2 mols)/3-Naphthol (2 mols on
fiber)
368 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from /3-Naphthol (continued?)
SchultzNumberfor Dye
408
409
419
434
566
649
650
Ordinary Name andClass oj Dye
DISAZO DYES(continued)
Dianisidine Blue
Trisulf on Blue C
Chicago Blue RW
Coomassie NavyBlue
DlPHENYL-NAPHTHYL-METHANE DYE
Wool Green S
OXAZINE DYESNew Blue RMeldola's BlueCotton Blue
New Blue B
Statistics ojImport and
Manufacture
:— 240
I '14:— 813
I '14:— 15,176M'19:— ?I '20:— 351M'20:— ?
I '20:— 42,357
I '14:— 60,073M'17:— ?M'19:— ?I '20:—127,764M'20:—212,362
I '14:— 32,509M'17:— ?M'18:— 22,613M'19:— ?I '20:— 5,240M'20:— ?
Other IntermediatesUsed and Notes
Dianisidine0-Naphthol (2 mols)
Dianisidinel-Naphthol-3: 6:8-
trisulfonic Acid
Dianisidinel-Amino-8-naphthol-
2:4-disulfonic Acid
1:4-Naphthylene-dia-mine-2-sulfonic Acid
RAcid
Ketone[Sulfonation]
Nitroso-dimethyl-aniline
Nitro so-dimetliyl-aniline (2 mols)
DYES CLASSIFIED BY INTERMEDIATES 369
SchullzNumberfor Dye
651
652
Dyes Denvec
Ordinary Name andClass oj Dye
OXAZINE DYES{continued)
New MethyleneBlue GG
New Fast Blue F
; from /3-Naphthol {continued)
Statistics ofImport arid
Manufacture
I '14:— 2,502
Other IntermediatesUsed and Notes
Nitroso-dimethyl-aniline
[Dimethyl-amine,Oxidation]
or[Meldola's Blue, Di-
methyl-amine, Oxi-dation]
Nitroso-dimethyl-aniline
Hydrolor
[Meldola's Blue;Hydrol]
DyeAppli-cationClass
B
B
a-Naphthol-carboxylic Acid
See, l-Hydroxy-2-naphthoic Acid
/3-Naphthol-carboxylic Acid
See, 3-Hydroxy-2-naphthoic Acid
l-Naphthol-3:6-disulfonic Acid (C. A. nomen.)
R G Acid
G R Acid
a-Naphthol-disulfonic Acid R G
OH
HO3S SO3H = CioH807S2 =
STATISTICS.—Manufactured '19:— ?Manufactured '20:— ?
370 DYES CLASSIFIED BY INTERMEDIATES
FORMATION.—(1) By fusing sodium naphthalene-l:3:6-trisulfonatewith half its weight of caustic soda and half its weight of water inan autoclave. (2) By diaaotizing l-naphthylamine-3: 6-disulfonicacid and adding to boiling dilute sulfuric acid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 218Lange, Zwischenprodukte, #2636Thorpe, Die. Chemistry, 3, 619
Dyes Derived from l-Naphthol-3:6-disulfonic Acid
SchiltzNumberJor Dye
64
81
109
165
225
Ordinary Name andClass of Dye
MONOAZO DYESAzo Acid Red BLanafuchsine
Palatine Scarlet ABrilliant Cochineal
2R
Palatine Red A
Azo Red A
DISAZO DYESCroceine AZ
IMMMIM
I
IMJLVxM
II
Statistics ofImport andManufacture
'14:—'17:—'18:—'19:—'20:—'20:—
'14:—
'14:—MQ.'19t—
'14:—'20:—
78,305??
15,272674?
7,510
3009i
500100
Other IntermediatesUsed and Notes
p-Amino-acetanilide
m-Xylidine
a-Naphthylamine
Naphthionic Acid
A min o-azo-benzene
DyeAppli-cationClass
A
A
A
A
A
l-Naphthol-3:8-disulfonic Acid (C. A. nomen.)
Andresen's Acid€-Acid or Epsilon Acida-Naphthol-e-disulfonic AcidDisulfo Acid E
HO3S OH
SO H — C10H8O7S2=304
DYES CLASSIFIED BY INTERMEDIATES 371
STATISTICS.—Manufactured '20:— ?
FOKMATION.—Heat a solution of the acid sodium salt of 1-naphthyl-
amine-3: 8-disulfonic acid in an autoclave for 5 hours at 180°
LITERATURE.—Cain, Intermediate Products (2d Ed.), 219Lange, Zwischenprodukte, #2638, 2639Thorpe, Die. Chemistry, 3, 619
Dyes Derived from l-Naphthol-3:8-disulfonic Acid
SchultzNumberfor Dye
100
117
121
325
387
451
456
Ordinary Name andClass o/ Dye
MONOAZO DYESEosamine B
Erica 2 GN
Erica B
DISAZO DYESColumbia Blue R
Columbia Blue G
TRISAZO DYESCongo Fast Blue E
Congo Fast Blue BBenzo Fast Blue B
II
IMI
IMI
I
I
IMI
II
Statistics ofImport andManufacture
1 4 : -'20:—
1 4 : -1 9 : -'20:-
1 4 : -1 9 : -'20:-
1 4 : -
1 4 : -
1 4 : -1 8 : -'20:-
1,914• 1,600
1,171
• 337
• 5,349• ?- 2,393
• 3,071
- 7,094
- 4,449- ?- 723
14:—100,495'20:- - 1,821
Other IntermediatesUsed and Notes
m-Amino-p-cresol-methyl ether
Dehydro-thio-p-tolui-dine
D ehydr o-thio-m-xylidine
Benzidinel-Amino-S-naphthol-4-
sulfonic Acid
Tolidinel-Ammo-8-naphthol-4-
sulfonic Acid
Tolidinca-Naphthylaminel-Naphthol-3:8-disul-
fonic Acid (2 mols)
Dianisidinea-Naphthylaminel-Naphthol-3: 8-disul-
fonic Acid (2 mols
DyeAppli-cationClass
A
D
D
D
D
D
D
372 DYES CLASSIFIED BY INTERMEDIATES
l-Naphthol-4:8-disulfonic Acid (C. A. nomen.)
Schoellkopf s Acid
a-Naphthol-disulfonic Acid Sch
a-Naphthol-5-disulfonic Acid
a-Naphthol-disulfonic Acid S
SAcid
HO3S OH
SO3H
STATISTICS.—Manufactured '19:— ?
FORMATION.—From l-naphthylamine-4: 8-disulfonic acid by diazotizingand running this diazo solution into dilute sulfuric acid. Thislatter is now boiled to complete the decomposition
LITERATURE.—Cain, Intermediate Products (2d Ed.), 219Lange, Zwischenprodukte, #2647Thorpe, Die. Chemistry, 3, 620
Dyes Derived from l-Naphthol-4:8-disulfonic Acid
SchultzNumberjor Dye
80
95
110
118
226
235
321
Ordinary Name andClass oj Dye
MONOAZO DYESWool Scarlet R
Azo CochinealCochineal Scarlet B
Buffalo Rubine
Geranine
DISAZO DYESCroceine B
Croceine 3B
Heliotrope 2B
Statistics ofImport and
Manufacture
I '14:— 39,888
I '14:— 952
I '14:— 18,917M'19:— ?I '20:— 527
M'19:— ?M'20:— ?
I '14:— 1,473I '20:— 60
Other IntermediatesUsed and Notes
Xylidine
0-Anisidiiie
a-Naphthykmine
Dchydro-tlrio-p-toluidine
Amino-azo-benzene
Amino-azo-toluene
BenzidineCroceine Acid
DyeAppli-cationClass
A
A
A
D
A
A
D
DYES CLASSIFIED BY INTERMEDIATES
2-Naphthol-3: 6-disulfonic Acid
See, R Acid
2-Naphthol-3:7-disulfonic Acid (C. A. nomen.)
£-Naphthol-5-disulfonic Acid
/3-Naphthol-disulfonic Acid F
373
HO3SSO H
FORMATION.—2-Naphthol-7-sulfonic acid is heated with 66° sulfuricacid for a considerable time at 120°
LITERATURE.—Lange, Zwischenprodukte, #2653, 2654Thorpe, Die. Chemistry, 3, 627
Dye Derived from 2-Naphthol-3:7-disulfonic Acid
SchultzNumberfor Dye
402
Ordinary Name andClass of Dye
DISAZO DYEDiamine Blue
Black E
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
Ethoxy-b enzidineGamma Acid
DyeAppli-cationClass
D
2-Naphthol-6:8-disulfonic Acid
Seef G Acid
a-Naphthol-5-disulfonic Acid
See, l-Naphthol-4: 8-disulfonic Acid
a-Naphthol-€-disulfonic Acid
See, l-Naphthol-3: 8-disulfonic Acid
a-Naphthol-disulfonic Acid GR
See, l-Naphthol-3: 6-disulfonic Acid
a-Naphthol-disulfonic Acid RG
See, l-Naphthol-3: 6-disulfonic Acid
374 DYES CLASSIFIED BY INTERMEDIATES
a-Naphthol-disulf onic Acid S
See, l-Naphthol-4:8-disulfonic Acid
a-Naphthol-disulfonic Acid Sch
See, l-Naphthol-4:8-disulfonic Acid
j3-Naphthol-a-disulf onic Acid
See, R Acid
£-Naphthol-j3-disulfonic Acid
See, G Acid
0-Naphthol-7-disulfonic Acid
See, G Acid
/S-Naphthol-5-disulfonic Acid
See, 2-Naphthol-3:7-disulfonic Acid
0-Naphthol-disulfonic Acid C
2-NTaphthol-4: 8-disulfonic Acid (not considered herein)
£-Naphthol-disulf onic Acid P
See, 2-Naphthol-3: 7-disulfonic Acid
jS-Naphthol-disulf onic Acid G
See, G Acid
j3-Naphthol-disulf onic Acid R
See, R Acid
Naphtholic Acid
See, Naphthionic Acid
l-Naphthol-4-sulf onic Acid
See, Nevile-Winther's Acid
DYES CLASSIFIED BY INTERMEDIATES
l-Naphthol-5-sulfonic Acid (C. A. nomen.)
L Acid
Cleve's Acid
a-Naphthol-sulfonic Acid C
a-Naphthol-sulfonic Acid L
OH
375
HO3S
STATISTICS.—Imported '14:—25,126 lbs.Manufactured 18:— ?Manufactured ' 19:— ?Manufactured '20:— ?
FOKMATION.—(1) From naphthalene-1: 5-disulfonic acid by fusion withcaustic soda. (2) From l-naphthylamine-5-sulfonic acid by diazo-tizing, and boiling the diazo solution with dilute sulfuric acid
LITERATXJEE.—Cain, Intermediate Products (2d Ed.), 218Lange, Zwischenprodukte, #2422-2424Thorpe, Die. Chemistry, 3, 617
Dyes Derived from l-Naphthol-5-sulfonic Acid
SchultzNumberfor Dye
78
108
164
Ordinary Name andClass of Dye
MONOAZO DYESCochineal Scarlet 4R
Double Ponceau R
Fast Red VR
Statistics ofImport andManufacture
I >14:— 20,714M'17:— ?M'18:— ?M'19:-~ ?I ' 2 0 : - 6,290M'20:— ?
Other IntermediatesUsed and Notes
Xylidine
a-Naphthylamine
Naphthionic Acid
DyeAppli-cationClass
A
A
ACr
376 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from l-Naphthol-5-sulfonic Acid (continued)
SchultzNumberfor Dye
275
411
Ordinary Name andClass of Dye
DISAZO DYESDiamond Black F
Benzoazurine 3G
Statistics ofImport and
Manufacture
I '14:—462,306M'17:— ?M'18:— ?M'19:—222,938I '20:— 2,226M'20:— ?
I '20:— 201
Other IntermediatesUsed and Notes
Ammo-salicylic Acida-Naphthylamine
Dianisidinel-Naphthol-5-sulfonic
Acid (2 mols)
DyeAppli-cationClass
ACr
D
2-Naphthol-l-sulfonic Acid
Tobias Acid
(Falsely called 0-naphthyl-sulfuric Acid)
SO3H
C 0 O H
STATISTICS.—Manufactured in 1918, 1919, 1920 in indeterminate
amounts
FOBMATION.—By sulfonating /3-naphthol with
per cent sulfuric acid at about 40°
parts of 90-92
LITERATURE.—Cain, Intermediate Products (2d Ed.), 222
Lange, Zwischenprodukte, #2427
Thorpe, Die. Chemistry, 3, 624
USES.—For preparation of 2-naphthylamine-l-sulfonic acid
2-Naphthol-6-sulfonic Acid
See, Schaeffer's Acid
DYES CLASSIFIED BY INTERMEDIATES 377
2-Naphthol-7-sulfonic Acid (C. A. nomen.)
0-Naphthol-5-sulfonic Acid
/3-Naphthol-sulfonic Acid F
FAcid
Monosulfonic Acid F
Cassella's Acid
H 0 3 S | 0 0 ° H = c i ° H 8 a s = 2 2 4
STATISTICS.—Imported '14:—1,996 lbs.Manufactured '18:— ?Manufactured '19:— ?Manufactured '20:— ?
FOKMATION.—By fusing sodium naphthalene-2:7-disulfonate withcaustic soda solution in an autoclave
LITERATURE.—Cain, Intermediate Products (2d Ed.), 224Lange, Zwischenprodukte, #2434Thorpe, Die. Chemistry, 3, 625
Dyes Derived from 2-Naphthol-7-sulfonic Acid
SchultzNumberfor Dye
56
Ordinary Name andClass oj Dye
MONOAZO DYEParanitraniline Red
Statistics ofImport and
Manufacture
I '14:— 49,847M'17:— ?M'18:— ?M'19:— ?
Other IntermediatesUsed and Notes
p-Nitro-aniline[0-Naphthol]
DyeAppli-cationClass
MF
2-Naphthol-8-sulfonic Acid
See, Croceine Acid
a-Naphthol-sulfonic Acid d
l-Naphthol-8-sulfonic Acid (not considered herein)
378 DYES CLASSIFIED BY INTERMEDIATES
a-Naphthol-sulfonic Acid C
See, l-Naphthol-5-sulfonic Acid
a-Naphthol-sulfonic Acid L
See, l-Naphthol-5-sulfonic Acid
a-Naphthol-sulfonic Acid NW
See, Nevile-Winther's Acid
a-Naphthol-sulfonic Acid S
l-Naphthol-8-sulfonic Acid (not considered herein)
/9-Naphthol-a-sulfonic Acid of Armstrong and Schultz
See, Schaeffer's Acid
/S-Naphthol-a-sulfonic Acid (of Bayer & Co.'s patents)
See, Croceine Acid
j5-Naphthol-j8-sulfonic Acid
See, Schaeffer's Acid
iS-Naphthol-7-suIf onic Acid
2-Naphthoi-5-sulfonic Acid (not considered herein)
0-Naphthol~S-sulf onic Acid
See, 2-Naplitliol-7-siilfoiiic Acid
/5-Naphthol-sulf onic Acid B
See, Croceine Acid
0-Naphthol-sulfonic Acid F
See, 2-Naphtiiol-7-fiulfonic Acid
0-Naphthol-sulf onic Acid S
See, Schaeffer's Acid
DYES CLASSIFIED BY INTERMEDIATES
/3-Naphthol-sulfonic Acid Schaeffer
See, Schaeffer's Acid
379
l-Naphthol-3: 6:8-trisulfonic Acid (C. A. nomen.)
HO3S OH
SO3H = 384
STATISTICS.—Imported '14:—6,443 lbs.Manufactured '18:— ?Manufactured '19:— ?Manufactured '20:— ?
FORMATION.—From l-naphthylamine-3: 6: 8-trisulfonic acid by diazo-tizing in the presence of a large excess of sulfuric acid and thenboiling and purifying
LITERATURE.—Cain, Intermediate Products (2d Ed.), 221Lange, Zwischenprodukte, #2785, 2786Thorpe, Die. Chemistry, 3, 621
SchultzNumberjor Dye
322
378
409
Dyes Derived from
Ordinary Name andClass of Dye
DISAZO DYESTrisulfon Violet B
Trisulfon Blue R
Trisulf on Blue B
l-Naphthol-3
Statistics ojImport and
Manufacture
I '14:— 1,124M'17:— ?M'18:— ?M'19:— ?I '20:— 7,927M'20:— ?
I '14:— 911M'19:— ?M'20:— ?
I '14:— 813
6:8-trisulfonic Acid
Other IntermediatesUsed and Notes
Bcnzidine/J-Naphthol.
Tolidine0-Naphthol
Dianisidine/J-Naphthol
DyeAppli-cationClass
D
D
D
380 DYES CLASSIFIED BY INTERMEDIATES
2-Naphthol-3:6:8-trisulfonic Acid (C. A. nomen.)
/S-Naphthol-trisulfonic Acid
HO3S
HO3SOHSO3H
— 384
STATISTICS.—Manufactured '19:— ?
FORMATION.—From /3-naphthol by sulfonation with 2 parts of con-centrated sulfuric acid at 70-80°, then with 2 more parts of concen-trated sulfuric acid at 120°, and finally with 2 parts of 40 per centoleum at 150°
LITERATURE.—Cain, Intermediate Products (2d Ed.), 229Lange, Zwischenprodukte, #2792Thorpe, Die. Chemistry, 3, 628Ullmann, Enzy. tech. Chemie, 8, 351
SchidtzNumberfor Dye
170
228
Dyes Derived from
Ordinary Name andClass of Dye
MONOAZO DYEPonceau 6R
DISAZO DYEPonceau 5B,Erythrine P
2-Naphthol-3
Statistics ofImport and
Manufacture
I '14:— 2,880M'17:— ?M'18:— ?
• 6:8-trisulfonic Acid
Other IntermediatesUsed and Notes
Naphthiordc Acid
Amino-az o-benzene
DyeAppli-cationClass
A
A
/3-Naphthol-trisulfonic Acid
See, 2-Naphthol-3:6:8-trisulfonic Acid
a-Naphthol-trisulfonic Acid S
l-Naphthol-2:4: 8-trisulfonic Acid (not considered herein)
Naphtho-picric Acid
2:4: 5-Trinitro-l-naphthol (not considered herein)
DYES CLASSIFIED BY INTERMEDIATES 381
1: 2-Naphthoquinone (C. A. nomen.)
0-Naphthaquinone
1:2-Naphthaquinone
= 0
FORMATION.—From Orange II as follows: Sulfanilic acid is diazotizedand coupled with /3-naphthol to form Orange II. This azo dye isreduced with stannous chloride to l-amino-2-naphthol, which isoxidized with sodium bichromate and sulfuric acid to /?-naphtho-quinone
LITERATURE.—Thorpe, Die. Chemistry, 3, 654Lange, Zwischenprodukte, #23, 648, 2408
Dye Derived from 1:2-Naphthoquinone
SchultzNumberfor Dye
667
Ordinary Name andClass oj Dye
THIAZINE DYEBrilliant Alizaiin
BlueGIndochromine T
Statistics ofImport and
Manufacture
I '14 — 19,481M'19— ?I '20.— 3,214M '20 — ?
Other IntermediatesUsed and Notes
Ethyl-sulfobcnzyl-p-phenylene-diamine-tlriosulfonic Acid
DyeAppli-cationClass
M
1:2-Naphthoquinone-4:6-disulfonic Acid
/3-Naphthoquinone-4:6-disulfonic Acid
3:4-Dihydro-3:4-diketo-l: 7-naphthalene-disulfonic Acid (<7. A.nomen.)
0
HO3S—i=0 _ — 318
SO3H
382 DYES CLASSIFIED BY INTERMEDIATES
FORMATION.—l-Nitroso~2-naphthol-6-sulfonic acid is treated with bi-
sulfite forming l-amino-2-naphthol-4: 6-disulfonic acid. This latter
body is now oxidized with nitric acid under 15°, resulting in 1:2-
naphthoquinone-4: 6-disulfonic acid
LITERATURE.—Ullmann, Enzy, tech. Chemie, 8, 358
Cf. Lange, Zwischenprodukte, #2408
Thorpe, Die. Chemistry, 3, 657
Dyes Derived from 1:
SchultzNumberfor Dye
666
667
Ordinary Name andClass of Dye
THIAZINE DYESIndochromogen S
Brilliant AlizarinBlueG
Indochromine T
2-Naphthoquinone-4:6-disulfonic Acid
Statistics ofImport and
Manufacture
I '14:— 19,481M'19:— ?I '19:— 3,214M'20:— ?
Other IntermediatesUsed and Notes
Diethyl - p - phenylene-diamine-thiosulfonic-Acid
Dimethyl-p-phenylene-diamine-thiosulfonicAcid
DyeAppli-cationClass
M
M
/S-Naphtlioquinone-4:6-disulfonic Acid
See, 1:2-Naphthoquinone-4:6-disulfonic Acid
1:2-Naphthoquinone-4-sulfonic Acid
/3-Naphthoquinone-4-sulfonic Acid
3:4-Dihydro-3:4-diketo-l-naphthalene-sulfonic Acid (C. A.nomen.)
O
Q M = 0 = C W S A S =
SO;
DYES CLASSIFIED BY INTERMEDIATES 35
FORMATION.—2-Amino-l-naphthol-4-sulfonic acid or l-amino-2-napthol-4-sulfonic acid is oxidized with nitric acid
LITERATURE.—Ullmann, Enzy. tech. Chemie, 8, 358Thorpe, Die. Chemistry, 3, 657Cf. Lange, Zwischenprodukte, #2631
SchullzNumberfor Dye
656
657
Dyes Derived from
Ordinary Name andClass oj Dye
OXAZINE DYES
Alizarin Green G
Alizarin Green B
1: 2-Naphthoquinone~4-sulf onic Acid
Statistics ofImport and
Manufacture
M'19:— ?
I '14:— 551
Other IntermediatesUsed and Notes
l-Amino-2-naphthol-6-sulfonic Acid
2-Amino-l-naphtliol-4-sulfonic Acid
DyeApphcatioiClas*
M
M
/3-Naphthoquinone-4~sulfonic Acid
See, 1: 2-Naphthoquinone-4-sulf onic Acid
Naphtho-resorcin
1: 3-Dihydroxy-naphthalcne (not considered herein)
Naphthoyl-benzoic Acid
o-l-Naphthoyl-fcenzoic Acid ( C A. nomen.)
—CO.OH _ p TT n _
FORMATION.—From phthalic anhydride and naphthalene by heatingtogether in the presence of benzene and aluminium chloride
LITERATURE.—Lange, Zwischenprodukte, #2812Schultz, Farbstofftabellen (1914), #758
384 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from Naphthoyl-benzoic Acid
SchuUzNumberfor Dye
758
Ordinary Name andClass of Dye
ANTHEAQUINONB ANDALLIED DYES
Sirius Yellow G
Statistics ofImport andManufacture
Other IntermediatesUsed and Notes
DyeAppli-cationClass
CL
Naphthsultam-disulfonic Acid Sl~Naphthylamine-2:4:8-trisulfonic Acid (not considered herein)
1-NaphthylamineSee, a-Naphthylamine
2-NaphthylamineSee} /3-Naphthylamine
a-Naphthylamine1-Naphthylamine (<7. A. nomen.)a-Amino-naphthaJeneNaphthalidamNaphthalidine
NH2
STATISTICS.—Imported '14:— 112,226 lbs.Manufactured '17:—3,516,686 lbs.Manufactured '18:—2,671,601 lbs.Manufactured '19:—1,552,828 lbs.Manufactured '20:—5,177,547 lbs.
FORMATION.—Naphthalene is mononitrated, using mixed acid, and theresulting a-nitro-naphthalene is reduced with iron and hydrochloricacid to a-naphthylamine
LITERATURE.—Cain, Intermediate Products (2d Ed.), 181Lange, Zwischenprodukte, #2262Thorpe, Die. Chemistry, 3, 586
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from a-Naphthylamine
SchultzNumberfor Dye
105
106
107
108
109
110
111
112
113
114
Ordinary Name andClass of Dye
MONOAZO DYESSudan Brown
Carmine NaphthGarnet
Autol Red RL
Sulfamine Brown A
Double Ponceau R
Palatine Red A
Buffalo Rubino
Fast Red BT
Fast Red BBordeaux B
Crystal Ponceau
Chromotrope 10B
Statistics ofImport and
Manufacture
M' 17:— ?MIS:— ?M'19:— ?
I 14:— 6,565M17:— ?M18:— ?M19:— ?M'20:— ?
I 14:— 132M18:— ?M19:— ?I '20:— 2,630M'20:— ?
I 14:— 300M18:— ?M10:— ?
M'17:— ?M18:— ?M'19:— ?
I 14:— 25,821M17:—120,595M18:—200,415M19:—161,862I '20:— 7,882M'20:—217,406
I 14:— 628
M19:— ?
Other IntermediatesUsed and Notes
a-Naphthol
/3-Naphthol
Nitroso-jft-naphthol
l-Naplitliol-5-sulfonicAcid
l-Naphtlu>l-3:6-disul-fonic Acid
l-Naphthol-4: 6-disuJ-fonic Acid
Schacffor's Acid
RAcid
GAcid
Chromotropic Acid
DyeApplicationClass
S3
CL
M
A
A
A
A
A
A
A
386 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from a-Naphthylamine (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediaies
Used and Notes
DyeAppli-cationClass
218
220
241
243
244
245
256
257
258
261
DISAZO DYESNigrophorBASF
Palatine Black A
Neutral Gray G
Coomassie WoolBlack R
Coomassie WoolBlack S
Nyanza Black B
Sulf on Black 3B
Sulfoncyanine
Naphthalene AcidBlack 4B
Buffalo Black 10B
I '14:-I '20:
I '14:-M'19:-I '20:-M'20:-
M'lS:-M'19:-
-299,274- 200
2,546
3,*472
I '14:—145,694M'17:— ?M'18:— ?M'19:— ?I '20:— 18,327M'20:— ?
I '14:— 7,994
M'19:M'20:
l-Amino-8-naphthol-5-sulfonic Acid
2: 5-Dichloro-aniline
l-Amino-8-naphthol-4-sulfonic Acid
Sulfanilic Acid
AnilineGamma Acid
Aeetyl-p-phcnylene-diamine
Schaeffer's Acid
Acetyl-p-phenylcne-diamine
RAcid
p-Nitro-aniline[Reduced]
Gamma Acid
Metanilic AcidPhenyl-1 -naphthyl-
aminc-8-sulfonic Acid
Metanilic AcidPhcnyl- or Tolyl-
1 -naphthylaminc-8-sulfonic Acid
Metanilic Acid1-Naphthyl amine-6-
and 7-sulfonic Acids
Sulfanilic AcidHAcid
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from a-Naphthylamine (continued)
SchultzNumberfor Dye
262
263
265
266
267
267
268
269
Ordinary Name andClass of Dye
DISAZO DYES(continued)
Victoria Black B
Jet Black
SulfoncyanineBlack B
Naphthyl amineBlack D
Anthracite Black
Phenylene Black
Naphthyl BlueBlack N
Naphthol Black 6B
Statistics ofImport and
Manufacture
I '14:— 557
I '14:— 09,590MT7:— ?M'18:— ?M'19:— ?M'20:— ?
I '14:—152,141M'17:— ?M'18:— 29,724M'19:—I '20:—M 720:—
?1,687?
I '14:—M '17:—I '20.—
99?220
I '14:—120,512I '20:— 1,500M'20:— ?
Other IntermediatesUsed and Notes
Sulfanilic Acid1:8-Dihydroxy-naph-
thalcne-4-sulfonicAcid
Aniline-2:4-disulfonicAcid
Phcnyl-a-naphthyl-amine
Laurent's AcidPhenyl-1-naphthyl-
aininc-8-sulfonic Acid
Frcund's Acida-Naplitliylainine
(2 inols)
Fround's AcidDiphcnyl-m-phcnylone-
diamine
l-Naphthylamino-4: 7-disulfonic Acid
Diphenyl-m-phcnylcne-diamino
l-Naphthylamine-4: 6-ancZ4: 7-disulfonicAcids
l-Amino-2-naphtholEthyl Ether
l-Naphthyiaminc-4:6-and 4:7-disulfonicAcids
RAcid
388 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from a-Naphthylamine (continued)
SchidtsNumberjor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
272
273
274
275
276
278
290
382
DISAZO DYES(continued)
Naphthol Black BBrilliant Black B
Diaminogen Blue BB
Diaminogen B
Diamond Black F
I '14:—103,598M'19:— ?
'20:— 50
Diamond Green B
Biebrich PatentBlack
Violet Black
Azo Mauve B
I '14:-M '17:-I '20:-
8 ,308
5,936
I '14:—-313,629I '20:— 18,120
I '14:—462,306M'17:— ?M'18 :— ?M'19:—222,938I '20:— 2,226
M'20:— ?
I '14:M ' 1 8 :I '20:— 4,061
8,622?
M ' 1 7 : -
M ' 2 0 : -
A m i n o - G A c i d
R A c i d
A c e t y l - 1 : 4 - d i a m i n o -
n a p h t h a l e n e - 6 - s u l -
f o n i c A c i d
S c h a e f f e r ' s A c i d
A c e t y l - 1 : 4 - d i a m i n o -n a p h t h a l e n e - 6 - s u l -f o n i c A c i d
G a m m a A c i d
A m i n o - s a l i c y l i c A c i dJNTevi le-Winther ' s A c i d
or l - N a p h t h o l - 5 -s u l f o n i c A c i d
A m i n o - s a l i c y l i c A c i d1 : 8 - D i h y d r o x y - n a p h -
t h a l e n e - 4 - s u 1 f o n i cA c i d
l ~ N a p l i t h y l a m i n e - 6 -and 7 - su l fon i c A c i d se t c .
N e v i l e - W i n t h e r ' s A c i d
p - P h e n y l e n e - d i a m i n e or
A m i n o - a c e t a n i l i d e
T o l i d i n eH A e i d
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from a-Naphthylamine (continued)
SchultzNumberfor Dye
432
435
441
442
443
446
447
450
Ordinary Name andClass of Dye
DISAZO DYES(continued)
Diamine CutchNaphthylene Violet
TRISAZO DYESJanus Brown B
Diazo BlueBlack RS
Direct Black V
Direct IndoneBlue R
Benzo Olive
Benzo Gray S
Benzo Black Blue R
Statistics ofImport and
Manufacture
M'19:— ?M'20:— ?
I 14:—145,738
I '14:— 1,149
I 14:— 802
Other IntermediatesUsed and Notes
1:5-Naphtliylcno-dia-minc-3:7-disulfonicAcid
a-Naphthylamine(2 mols)
Trimethyl-m-amino-phcnyl-ammoniumChloride
Anilinem-Phcnylcnc-diamino
orp-Amino-benzyl-
diethyl-amineResorcinolm-Phenylenc-diamine
BenzidinoH Acid (2 mols)
Benzidino2R AcidGamma Acid
Benzidino2R AcidH Acid
BenzidineSalicylic AcidII Acid
BenzidinoSalicylic AcidNovilc-Winthcr'a Acid
TolidineNcvilc-Winthcr's Acid
(2 mob)
DyiApplccdioClos
D
B
D
D
D
D
D
D
390 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from a-Naphthylamine (continued)
SchtdisNumberfor Dye
451
452
456
459
460
653
671
672
673
Ordinary Name andClass of Dye
TEISAZO DYES(continued)
Congo Fast Blue R
Benzo Indigo Blue
Congo Fast Blue BBenzo Fast Blue B
Benzo Black Blue G
Benzo Black Blue 5G
OXAZINE DYENile Blue A
AZINE DYESInduline Scarlet
Azo Carmine G
Azo Carmine B
Statistics ofImport and
Manufacture
I '14:M'19:I '20:
4,449
723
'14:'20:
-100,495- 1821
I '14:— 602
I '14:-I '20:
1,5181,241
I '14I '20
I '14:M'17;M'18:M'19:I '20M'20
:— 198:-- 154
:— 17,500. 9
:— 196
I '20:— 549
Other IntermediatesUsed and Notes
Tolidinel-Naphthol-3: 8-disul-
fonic Acid (2 mols)
Tolidine1:8-DIhydroxy-naph-
thalene-4-sulfonicAcid (2 mols)
Dianisidinel-Naphthol-3: 8-disul-
f onic Acid
Benzidine-disulfonicAcid
Nevile-Winther's Acid(2 mols)
Benzidine-disulfonicAcid
1:8-Dihydroxy-naph-thalene-4-s u If o n i cAcid (2 mols)
5-Diethylamino-2-nitroso-phenol
Ethyl-p-toluidine
Aniline (3 mols)CDisulfonation]
Aniline (3 mols)[Trisulfonation]
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from a-Naphthylamine (continued)
391
SchultzNumberfor Dye
674
693
694
Ordinary Name andClass of Dye
AZINE DYES(continued)
Rosinduline 2G
Milling Blue
Rose MagdalaFast Pink for Silk
Statistics ofImport and
Manufacture
I '20:— 201
I '14:— 3,082
I '14:— 597
Other IntermediatesUsed and Notes
Aniline (3 inols)[Trisulfonation, heated
to 160°]or
[Azo Carmine B heatedto 160°]
Aniline (3 mols)a-Naphthylamine
(2 mols)[Sulfonation]
a-Amino-azo-naph-thalcne
DyeAppli-cationClass
M
j3-Naphthylamine
2-Naphthylamine (C. A. nomen)
/3-Amino-naphthalene
C C r
STATISTICS.—Impor ted '14:—11,204 lbs.Manufactured ' 17:— ?Manufactured 18:—31,317 lbs.Manufactured 19:—99,597 lbs.Manufactured '20:— ?
F O R M A T I O N . — F r o m /3-naphthol by heating in an autoclave with am-monium sulfite and ammonia.
L I T E R A T U R E . — C a i n , Intermediate Products (2d Ed. ) , 187Lange, Zwischenprodukte, #2262Thorpe , Die. Chemistry, 3, 598
392 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from /3-Naphthylamine
SchvltsNumberfor Dye
115
116
281
282
287
301
383
433
Ordinary Name andClass of Dye
MONOAZO DYESAzo Turkish Red
Sul famine Brown B
DISAZO DYESAzidine Fast
Scarlet 4BS
Azidine FastScarlet 7BS
Toluylene OrangeRR
Hessian Purple N
Naphthazurine B
Coomassie Black B
Statistics ofImport and
Manufacture
I '14:— 500
I '14:— 465
I '14:— 4,782
Other IntermediatesUsed and Notes
0-Naphthol
Nitroso-jS-naphthol[Sodium bisulfite]
o-ToluidineSulfo-m-tolylene-dia-
mine-bis(carbonyl-amino-n apht h o 1-sulfonic Acid)
/3-Naphthylainine(2 mols)
Sulfo-m-tolylene-dia-mine-bis (carb onyl-amino-naphth. ol-sulf onic Acid)
j8-Naphthylamine(2 mols)
3: ^Diamino-p-toluene-sulfonic Acid
i8-Naplithylamine(2 mols)
Diamino-stilbene-disul-f onic Acid
TolidineHAcid
1:4-Naphthylene-dia-mine-2-sulfonic Acid
R Acid
DyeAppli-cationClass
MF
M
D
D
D
D
D
A
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from |S-Naphthylamine {continued)
SchultzNumberfor Dye
541
831
Ordinary Name andClass of Dye
TRIPHENYL-METHANEDYE
Brilliant DianilBlue 6G
ANTHRAQUINONE DYEIndanthrene Red BN
Statistics ofImport and
Manufacture
I '14:— 6,056I '20:— 4,7G6
Other InfermedialasUsed and Notes
/?-Naphthylaminc(3 mols)
Aniline0-Toluidin.cp-Toluidino[Disulfonaiion]
or/3-Napliiliylaminc
(3 mols)[Rosaniiinc; DLsulfoiui-
nation]
1-Chloro-anthraqiu-nonc-2-carboxylicAcid
3!
DyeApplcatioi
B
l-Naphthylamine-3:6-disulfonic Acid
See, Freund's Acid
l-Naphthylamine-3:8-disulfonic Acid
a-Naphthylamine-e-disulfonic Acid
€ Acid or Epsilon Acid
8-Amino-l: 6-naphthalenc-disulfonic Acid (C. A. no men.)
HO3S NH2
STATISTICS.—Manufactured in 1919 and 1920 but in undisclosed quantties
FOBMATION.—Naphthalene-1:5- and 1:6-disulfonic acids are nitrateand reduced, resulting in l-naphthylaminc-3: 8- and 4: 8-disulfoniacids. The separation is effected by crystallizing out the aci(sodium salt of l-naphthylamine-3: 8-disulfonic acid
394 DYES CLASSIFIED BY INTERMEDIATES
LITERATUKE —Cain, Intennediate Products (2d Ed.), 196Lange, Zwischenprodukte, #2575, 2576Thorpe, Die. Chemistry, 3, 592
l-Naphthylamine-4: 6- and 4:7-disulfonic Acidsa-Naphthylamine-disulfonic Acids D
Dahl's Acids II and I I I (respectively)
4-Amino-l: 6-naphthalene-disulfonic Acid (C. A, nomen.)
4-Amino-l: 7-naphthalene-disulfonic Acid (C. A. nomen)
NH2 NH2
andrrr\ci\ I 1 ana \ \ I = C i o H 9 N 0 6 S 2 — 303
3O3H
(Acid I I ) (Acid I I I )
STATISTICS.—Manufactured '20:— ?
FORMATION.—From naphthionic acid by sulfonation w i t h 25 per cent
oleum
LITERATURE.—Cain , Intermediate Products (2d Ed. ) , 198Thorpe, Die. Chemistry, 3, 593, 594Lange, Zwischenprodukte, #2577-2582
Dyes Derived from l -Naphthylamine-4 :6- and 4 :7-disul fonic Acids
SchidtsNumberfar Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates- Used and Notes
DyeAppli-cationClass
267
268
269
MONOAZO DYES
Apollo Red B
DISAZO DYESPhenylene Black
Naphthyl BlueBlack N
Naphthol Black 6B
I '14:— 904
I '14:-M'17:-I '20:-
99
220
I 14:—120,512I '20:— 1,500M'20:— ?
p-Nitro-aniline
a-NaphthylamineDipheny-w-phenylene-
diamine[4:7 Acid only]
a-Naphthylaminel-Amino-2-naphthol
Ethyl Ether
a-NaphthylamineR Acid
DYES CLASSIFIED BY INTERMEDIATES 395
l-Naphthylamine-4:8-disulfonic Acid
d Acid or Delta Acid
Schoellkopf s Acid
Disulfo-acid S
4-Amino-l: 5-naphthalene-disulfonic Acid ( C A. nomen.)
a-Naphthylamine~£-disulfonic Acid
a-Naphthylamine-disulfonic Acid S
S Acid
HO3S NH2
STATISTICS.—Manufactured in 1919 and 1920 in undisclosed amounts
FORMATION.—When naphthalene-1: 5- and 1: 6-disulfonic acids arenitrated and reduced, there is formed a mixture of 1-naphthylamine-3:8- and 4: 8-disulfonic acids. See under l-naphthylamine-3:8-disulfonic acid. The 4:8-acid is also made by sulfonating 1-naphthylamine-8-sulfonic acid with three parts of 10 per centoleum.
LITERATURE.—Cain, Intermediate Products (2d Ed.), 200Lange, Zwischenprodukte, #2575, 2583-2585Thorpe, Die. Chemistry, 3, 594
USES.—For making l-amino-8-naphthol-4-sulf onic acid, l:8-dihydroxy-naphthalene-4-sulfonic acid, and 1:8-naphthasultam-2:4-disulfonicacid
l-Naphthylamine-6:7-disulfonic Acid
5-Amino-l: 3-naphthalene-disulfonic Acid ( C A. nomen.)
HO3S
396 DYES CLASSIFIED BY INTERMEDIATES
FORMATION.—By sulfonation of the acetyl derivative of 1-naphthyl-amine-5-sulfonic acid or of a-naphthylamine
LITERATURE —Cain, Intermediate Products (2d E d ) , 200Lange, Zwischenprodukte, #2586Thorpe, Die. Chemistry, 3, 594
USES.—For preparation of l-amino-5-naphthol-7-suIfonic acid
2-Naphthylamine-3:6-disulfonic Acid
See, Amino-R Acid
2-Naphthylamine-5:7-disulfonic Acid
6-Amino-l: 3-?iaphthalene-disulfonic Acid (C. A. nomen.)
i8-Naphthylamine-disidfordc Acid II of Armstrong and Wynne
Armstrong and Wynne's Acid I I
H ° 3 S i i ] N H 2 =i ] C10H9NO6S2 = 303
HOsS
STATISTICS.—Manufactured in 1919 and 1920 in undisclosed amounts
FORMATION.—By sulfonation of either 2-naphthylamine-5-S"ulfonic acid,or jS-naphthylamine, or 2-naphthylamine-7-sulfonic acid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 208Lange, Zwischenprodukte, #2598Thorpe, Die. Chemistry, 3, 605
USES.—For preparation of J acid (2-amino-5-naphthol-7-sulfonic acid)
2-Naplithylamine-6:8-disulfonic Acid
See, Amino-G Acid
a-Naphthylamine-a-disulf onic Acid
See, FreunxTs Acid
DYES CLASSIFIED BY INTERMEDIATES 397
a-Naphthylamine-j3-disulfonic Acid
l-Naphthylaminc-3: 7-disulf onic Acid {not considered herein)
a-Naphthylamine-5-disulfonic Acid
See, l-Naphthylaminc-4: 8-disulfonic Acid
a-Naphthylamine-e-disulfonic Acid
See, l-Naphtliylaminc-3: 8-disulfonic Acid
a-Naphthylamine-disulfonic Acids D
See, l-Naphthylaminc-4: 6- and 4: 7-disulfonio Acids
a-Naphthylamine-disulfonic Acid S
See, l-Naphthylamine-4: 8-disulfonic Acid
/3-Naphthylamine-a-disulfonic Acid
See, Amino-R Acid
iS-Naphthylamine-7-disulfonic Acid
See, Amino-G Acid
/3 -Naphthylamine-5-disulfonic Acid
2-Naphthylamino-2: 7-disulf onic Acid {not considered herein)
/3-Naphthylamine-disulfonic Acid II of Armstrong and Wynne
See, 2-Naphthylaminc-5: 7-disulf onic Acid
/3-Naphthylamine-disulfonic Acid C
2-Naphthylaminc-4: 8-disulfonic Acid {not considered herein)
0-Naphthylamine-disulfonic Acid F
2-Naphthylamine-3: 7-disulf onic Acid {not considered herein)
/3-Naphthylamine-disulfonic Acid G
See, Amino-G Acid
398 DYES CLASSIFIED BY INTERMEDIATES
0-Naphthylamine-disulf onic Acid R
See, Amino-R Acid
Naphthylamine Ether
See, l-Amino-2-naphthol Ethyl Ether
l-Naphthylamine-2-sulf onic Acid
X Acid
0-Naphthionic Acid
l-Amino-2-naphthalene-sulfonic Acid (C. A. nomen.)
NH2
= CioH9N03S=223
STATISTICS.—Manufactured '18:— ?Manufactured ' 19:— ?
FORMATION.—By heating naphthionic acid and naphthalene in a panfitted with a stirrer and reflux condenser, at the boiling point ofnaphthalene (217°) for few hours
LITERATURE.—Cain, Intermediate Products (2d Ed.), 189Thorpe, Die. Chemistry, 3, 589Lange, Zwischenprodukte, #2352-2355
SchuttsNumberfor Dye
562
Dye Derived from
Ordinary Name andClass of Dye
DlPHENYL-NAPHTHTIr-METHANE
DYEFast Acid Blue B
l-Naphthylamine-2-sulfonic Acid
Statistics ofImport and
Manufacture
I >U:— 33,251I '20:— 6,478
Other IntermediatesUsed and Notes
Hydrol[Oxidation]
DyeAppli-cationClass
A
l-Naphthylamine-4-sulf onic Acid
See, Naphthionic Acid
DYES CLASSIFIED BY INTERMEDIATES 399
l-Naphthylamine-5-sulfonic AcidSee, Laurent's Acid
l-Naphthylamine-6-sulfonic Acid1
a-Naphthylamine-jft-sulfonic Acida-Naphthylamine-/3-sulfonic Acid ClCleve's jS AcidCleve's AcidErdmann's /x Acid or ix Acid
5-Amino-2-naphthalene-sulfonic Acid (C. A. nomen.)
NH2
HO3S1 = Ci0H9NO3S=223
STATISTICS.—Imported '14:—5,493 lbs.Manufactured ' 18:— ?Manufactured ' 19:— ?Manufactured '20:— ?
FOBMATION.—From napththionic acid by heating with sulfuric acid at120-130°
LITERATURE.—Lange, Zwischenprodukte, 2363Thorpe, Die. Chemistry, 3, 591Cf. Cain, Intermediate Products (2d Ed.), 192
Dyes Derived from l-Naphthylamine-6-sulfonic Acid
SchultzNumberfor Dye
406
492
Ordinary Name andClass of Dye
DJSAZO DYEDiazurine B
TETRAKISAZO DYEAnthracene Acid
Brown B
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
l-Naphthylamine-6-sulf onic Acid (2 mols)
DianisidinejS-Naphthol (2 mols on
fiber)
l-Naphthylamiae-6-sulf onic Acid (2 mols)
Ammo-salicylic Acid(2 mols)
m-Phenylene-diamine
DyeAppli-cationClass
DJ
M|ACr
• See l-Naphthylamine-6- and 7-sulfonic Acids, page 400
400 DYES CLASSIFIED BY INTERMEDIATES
l-Naphthylamine-6- and 7-sulfonic Acids
Cleve's Acids
Naphthylamine-sulfonic Acids Cleve
a-Naphthylamine-sulf onic Acids Cl
5-and 8-Amino-2-naphthalene-sulfonic Acids ( C . 4 . nomen.)
NH2
HO3Sand
H M C 0 -
FORMATION.—Naphthalene is sulfonated hot to /3-naphthalene-sul-fonic acid, this latter in sulfuric acid solution is nitrated cold withmixed acid. The excess acidity is removed with ground limestone(CaCO3), and the nitro-compounds reduced with iron borings anda little acetic acid to a mixture of l-naphthylamine-6-and-7-sulf onicacids
LITERATURE.—Cain, Intermediate Products (2d Ed.), 192Lange, Zwischenprodukte, #2363, 2364Thorpe, Die. Chemistry, 3, 591
Dyes Derived from l-Naphthylamine-6- and 7-sulfonic Acids
SchutisNumberfor Dye
242
257
Ordinary Name andClass oj Dye
DISAZO DYESSulfon Black G
Sulfoncyanine
Statistics ofImport and
Manufacture
I '14:—145,694M'17:— ?MJ18:— ?M'19:— ?I J20:— 18,325M'20:— ?
Other IntermediatesUsed and Notes
Aniline1:8-Dihydroxy-naph-
thalene-4-sulfonicAcid
Metanilic AcidPheQyl-orTolyl-
1-naphthylamine-8-sulf onic Acid
DyeAppli-cationClass
A
A
DYES CLASSIFIED BY INTERMEDIATES 401
Dyes Derived from l-Naphthylamine-6- and 7-sulf onic Acid (continued)
SchultzNumberjor Dye
Ordinary Name andClass of Dye
DISAZO DYES(continued)
Naphthalene AcidBlack 4B
SulfoncyanineBlack B
AnthraceneAcid Black
Biebrich PatentBlack
TEISAZO DYESColumbia Black
FF
Carbon Black
:— 7,704.
I '14:— 09,590M'17:— ?M'18:— ?M'19:— ?M'20:— ?
I J14:— 17,793
Statistics ofImport and
Manufacture
I '14:—402,997M'18:— ?M'19:— ?
'20:— 23,350M'20:— ?
Other IntermediatesUsed and Notes
Mctanilic Acida-Naplithylamino
Laurent's AcidPlionyl-1-naphthyl-
ammc-8-sulfonic Acid
Amino-salicylic Acid,etc.
ct-Naplithylaininc, etc.
p-Phcnylcnc-diaminoGamma Acidm-Phcnylcnc-diamino
??-Phcnylonc-diamiiio-Hulfonic Acid fromp-nitro-an iliuo-o-sul-fonic Acid
m-Phcnylcnc-(or Toly-lenc-)-diamino or1:3-naphthyleno-dia-mine-C-sulfonic Acid(2 mob)
DyeA ppU-cationClass
l-Naphthylamine-7-sulfonic Acida-Naphthylamine-0-sulfonic Acid
Cleve's 6 AcidCleve's 8 AcidCleve's Acid
See, l-Naphthylamine-6- and 7-sulf onic Acids
402 DYES CLASSIFIED BY INTERMEDIATES
l-Naphthylamine-8-sulfonic Acid
8-Amino4-naphthalene-sulfonic Acid (C A. nomen.)
a-Naphthylamine-sulfonic Acid S
S Acid
Peri Acid
Schoellkopf s Acid
HO3S
STATISTICS.—Manufactured J19:— ?Manufactured '20:—562,939 lbs.
FORMATION.—Naphthalene is sulfonated at 60° to a-naphthalene-sulfonic acid and then nitrated below 40° to l-nitro-naphthalene-8-sulfonic acid, which latter upon reduction with iron furnishes t h el-naphthylamine-8-sulfonic acid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 193Lange, Zwischenprodukte, #2365Thorpe, Die. Chemistry, 3, 591
USES.—For manufacture of l-naphthylamine-4: 8-disulfonic acid
2-Naphthylamine-l-sulfonic Acid
Tobias Acid
2-Amino-l-naphthalene-sulfonic Acid (C A. nomen.)
SO3H
' = 2 2 3
STATISTICS.—^Manufactured '18:— ?Manufactured '19:— 84,260 lbs.Manufactured '20:—325,036 lbs.
DYES CLASSIFIED BY INTERMEDIATES 403
FORMATION.—Sodium 2-naphthol-l-sulfonate (from 0-naphthol andsulfuric acid at 40°) is heated with ammonium hydrogen sulfiteand ammonia in an autoclave at from 100° to 150°
LITERATURE.—Cain, Intermediate Products (2d Ed.), 205Lange, Zwischenprodukte, #2367Thorpe, Die. Chemistry, 3, 601
Dyes Derived from 2-NaphthyIamine-l-sulfonic Acid
SchultzNumbenJor Dye
173
179
Ordinary Name andClass oj Dye
MONOAZO DYESLithol Red E,
Lake Bordeaux B
Statistics ofImport and
Manujactvn e
I '14:—2S1,963M'17:— ?M'18:—353,104M '19:—-269,169M'20:~- ?
Other IntermediatesUsed and N"otes
/3-Naphthol
3-Hydroxy-2-naph-thoic Acid
DyeAppli-cotionClass
CL
CL
2~Naphthylamine-5-sulfonic Acid
i3-Naphthylamine-7-sulfonic Acid
iS-Naphthylamine-sulfonic Acid D
Dahl's Acid
Forsling's Acid II
See, 2-Naphthylamine-5- and 8-sulfonic Acids
2-Naphthylamine-5- and 8-sulfonic Acids i
6~ and 7-Amino-l-?iaphthalenc-sulfonic Acids (C. A. nomen.)
HO3S
CO- —STATISTICS.—Imported '14:—23,265 lbs. for the 2-naphthylamine-8-sulfonic Acid1 Sec 2-Naphthylamine-5-sulfonic Acid and 2-Naphtfiylamino-S-sulfonic Acid,
404 DYES CLASSIFIED BY INTERMEDIATES
FORMATION.—By sulfonation of /3-naphthylamine
LITERATURE.—Cain, Intermediate Products (2d Ed.), 205Lange, Zwischenprodukte, #2368-2370, 2380-2383Thorpe, Die. Chemistry, 3, 601, 603
Dye Derived from 2-Naphthylamine-5- and 8-sulfonic Acids
Schult2Numberjor Dye
175
Ordinal y Name andClass of Dye
MONOAZO DYEPonceau for Silk
Statistics ofImport and
Manufacture
I '14:— 727
Other IntermediatesUsed and Notes
0-Naphthol
DyeAppli-cationClass
A
2~Naphthylamine-6-sulf onic Acid
See, Broenner's Acid
2-Naphthylamine-7-sulfonic Acid
/?-Naphthylamine-5-sulfonic Acid
jS-Naphthylamine-sulfonic Acid F
FAcid
Delta Acid
BayerJs Acid
Cassella's Acid F
7-Amino-2-naphthalene-sulfonic Acid (C. A, nomen.)
FORMATION.—Sodium 2-naphthol-7-sulfonic acid (from caustic sodafusion of naphtlialene-2:7-disulfonic acid) is heated with am-monium acid sulfite solution and ammonia water in an autoclaveat 100° to 150°
LITERATURE.—Cain, Intermediate Products (2d Ed.), 207Lange, Zwischenprodukte, #2377-2379Thorpe, Die, Chemistry, 3, 602
DYES CLASSIFIED BY INTERMEDIATES 405
Dyes Derived from 2-Naphthylamine-7-sulfonic Acid
SchultzNumberJor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
Manvfacture
Other IntermediatesUsed and Notes
DyeAppli-cationClass
340
366
367
371
DISAZO DYESChlorazol Orange 2R
Diamine Red BDeltapurpurin 5B
Diamine Red 3BDeltapurpurin 7B
Rosazurine G
'14:— 21,058M'17:— ?M'18:— ?I '20:— 1,896
BcnzidineSalicylic Acid
TolidincBrocimcr's Acid
Tolidine2 -Naphthylarninc-7-sul-
sulfoiric Acid (2 mols)
TolidincEthyl-2-naphthyl-
aminc-7-sulf onic Acid
D
D
D
D
2-Naphthylamin.e-8-sulfonic Acid
i3-Naphthylamine-a-sulfonic Acid
Badische Acid
Forsling's Acid I
See, 2-Naphthylamine-5 and -8-sulfonic Acids
a-Naphthylamine-/3-sulfonic Acid
See, l-Naphthylamine-6-sulfonic Acid
a-Naphthylamine-5-sulfonic Acid
See, l-Naphthylamine-7-sulfonic Acid
Naphthylamine-sulfonic Acid Br
See, Broenner's Acid
a-Naphthylamine-/3-sulfonic Acid Cl
See, l-Naphthylamine-6-sulfonic Acid
406 DYES CLASSIFIED BY INTERMEDIATES
a-Naphthylamine-sulf onic Acids Cl
See, l-Naphthylamine-6-and! 7-sulfonic Acids
Naphthylamine-sulfonic Acids Cleve
See, l-Naphthylamine-6-and 7-sulfonic Acids
a-Naphthylamine-sulfonic Acid L
See, Laurent's Acid
a-Naphthylamine-sulfonic Acid S
See, l-Naptohylamine-8-sulfonic Acid
/3-Naphthylamine-a-sulfonic Acid
See, 2-JSTaphthylamine-8-sulfonic Acid
/3-Naphthylamine-i3-sulfonic Acid
See, Broenner's Acid
jS-Naphthylamine-r-sulf onic Acid
See, 2-Naphthylamine-5-sulfonic Acid
j3-Naphthylamine-5-sulf onic Acid
See, 2-Naphthylamine-7-sulfonic Acid
j8-Naphthylamine-sulfonic Acid D
See, 2-Naphthylamine-5-sulfonic Acid
/3-Naphthylamine-sulfonic Acid F
See, 2-Naphthylamine-7-suKonic Acid
l-Naphthylaroine-3:6:8-trisulfonic Acid
Koch's Acid
8-Amino-l: 3: 6-naphthalene-trisulfonic Acid (C A. nomen.)
HO3S NH2
/ V=C10H9NO9S3 =
DYES CLASSIFIED BY INTERMEDIATES 407
STATISTICS.—Manufactured '17:— ?Manufactured '18:— ?Manufactured '19:—1,418,560 lbs.Manufactured '20:—3,921,950 lbs.
FORMATION.—Naphthalene is sulfonated to naphthalene-1: 3:6-trisul-fonic acid, using oleum; and this trisulfonic acid is nitrated cold,and then reduced with iron
LITERATURE.—Cain, Intermediate Products (2d Ed.), 202Lange, Zwischenprodukte., #2747, 2748Thorpe, Die. Chemistry, 3, 595
USES.—For preparation of H acid (l-Amino-8-naphthol-3: 6-disulfonicacid)
l-Naphthylamine-4:6: 8-trisulfonic Acid
8-Amino-l: 3: 5-naphthalene-trisulfonic Acid (C. A. nomen.)
HO3S NH
HO3S' X ) = C l o H 9 N O j S 3 = 3 8 3
FORMATION.—Sodium naphthalenc-1: 5-disulfonate is sulfonated tonaphthalene-1:3:5-trisulfonic acid, and this is nitrated cold, andthen reduced with iron
LITERATURE.—Cain, Intermediate Products (2d Ed.), 202Lange, Zwischenprodukte, #2750Thorpe, Die. Chemistry, 3, 596
USES.—For preparation of K acid (l-amino-8-naphthol-4: 6-disulfonicacid)
2-Naphthylamine-3:6:8-trisulfonic Acid
7-Amino-l: 3: 6-naphthalenc-trisulfonic Acid (C A. nomen.)
HO3S
HO 3s l I J sO 3 H = C i o
408 DYES CLASSIFIED BY INTERMEDIATES
FORMATION.—By sulfonation of amino-G acid (as potassium or sodiumsalt of 2-naphthylamine-6:8-disulfonic acid) with 40 per centoleum at 80-90° and finally at 120-130°. The amino-G acid ismade by amidation of G salt or by sulfonating /5-naphthylamine
LITERATURE.—Cain, Intermediate Products (2d Ed.), 210Lange, Zwischenprodukte, #2757Thorpe, Die. Chemistry, 3, 606
USES.—For making 2R acid (2-Amino-8-naphthol-3: 6-disulfonic Acid)
4-(Naphthyl-azo)-l-naphthylamme (C. A. nomen.)See, o-Amino-azo-naphthalene
1-Naphthyl-diphenyl-methane (C. A. nomen.)See, Diphenyl-naphthyl-methane
1:5-Naphthylene-diamine-3:7-disulfonic Acid4:8-Diamino-2: 6-naphthalene-disulfonic Acid (C A. nomen)
NH2
FORMATION.—Naphthalene-2:6-disulfonic acid (from sulfonation ofnaphthalene) is dissolved in sulfuric acid and nitrated at 20-30°.The resulting 1: 5-dinitro~naphthalene-3: 7-disulfonic acid is saltedout and reduced
LITERATURE.—Cain, Intermediate Products (2d Ed.), 178Lange, Zwischenprodukte, #2700Thorpe, Die. Chemistry, 3, 613
Dyes Derived from 1:5-Naphthylene-diamine-3:7-disulfonic Acid
SchtdtzNumberjor Dye
431
432
Ordinary Name andClass of Dye
DISAZO DYESDiamine Golden
YeUow
Diamine CutchNaphthylene Yiolet
Statistics ofImport andManufacture
I 14:— 300I '20:— 49
Other IntermediatesUsed and Notes
Phenol (2 mols)[Ethylation]
a-Naphthylamine(2 mols)
DyeAppli-cadonClass
D
D
DYES CLASSIFIED BY INTERMEDIATES
1:8-Naphthylene-diamine-3:6-disulfonic Acid
4: 5-Diamino-2: 7-naphthalene-disulfonic Acid (C. A. nomen.)
400
H2N NH2
H0 3 s — 318
FORMATION.—Naphthalene-2:7-disulfonic acid (from sulfonation ofnaphthalene) is dissolved in strong sulfuric acid and is then di~nitrated warm with strong nitric acid and sodium nitrate. Thedinitro-acid is reduced
LITERATURE.—Lange, Zwischenprodukte, #2704Cf. Cain, Intermediate Products (2d Ed.), 178Thorpe, Die. Chemistry, 3, 613
Dyes
SchultzNumberjor Dye
55
Derived from 1: 8-Naphthylene-diarnine-3:6-disulfonic Acid
Ordinary Name andClass of Dye
MONOAZO DYEBrilliant Archil C
Statistics ofImport and
Manufacture
I '14:— 401
Other 1rUenncdialesUsed and Notes
p-Nitro-aniline
DyeAppli-cationClass
A
1:3-Naphthylene-diamine-6-sulfonic Acid
5: 7-Diamino-2-waphthalenC'-sulfonic Acid (C. A. nomen.)
HO3S
NH2
NH2 = <
FORMATION.—l-Naphthylamine-3: 6-disulfonic acid (by nitration andreduction of naphthalenc-2:7-disulfonic acid) is heated withammonia in an autoclave at 160-180°
LITERATURE.—Lange, Zwischenprodukte, #2483Thorpe, Die. Chemistry, 3, 612Cf. Cain, Intermediate Products (2d Ed.), 195
410 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from 1:3-Naphthylene-diamine-6-sulfonic Acid
SchultzNumberfor Dye
458
Oidinary Name andClass of Dye
TRISAZO DYECarbon Black
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
1:3-Naphthylene-dia-mine-6-sulf onic Acid(2 mols)
p-Nitro-aniline-0-sul-fonic Acid
l-Naphthylamine-6- or7-sulfonic Acid
DyeAppli-cationClass
D
1:4-Naphthylene-diamine-2-sulfonic Acid
1:4-Diamino-2-naphthaIene-sulfonic Acid (C. A. nomen.)
NH2
FORMATION.—^By reduction of the azo derivatives of l-naphthylamine-2-sulf onic acid
LITERATXJKE.—Cf. Thorpe, Die. Chemistry, 3, 611, 612
Dyes Derived from 1:4-Naphthylene-diamine-2-sulfonic Acid
SchultzNumberfor Dye
433
434
461
Ordinary Name andClass of Dye
DISAZO DYESCoomassie Black B
Coomassie NavyBlue
TRTSAZO DYECoomassie Union
Black
Statistics ofImport and
Manufacture
I '20:— 42,357
Other IntermediatesUsed and Notes
RAcid£-Naphthylamine
RAcidjS-Naphthol
Gamma Acidm~Phenylene- (or Toly-
lene-)diamine orResorcinol (2 mols)
DyeAppli-cationClass
A
A
D
DYES CLASSIFIED BY INTERMEDIATES
1:4-Naphthylene-diamine-6-sulf onic Acid
5: 8-Diamino-2-naphthalene-sulfonic Acid (C. A. nomen.)(Acetyl-compound used)
411
HO3S= Ci0H10N2O3S =
NH2
FORMATION.—A mixture of l-naphthylamine-6-(ancJ 7-)sulfonic acids(Cleve's Acids) is acetylated with glacial acetic acid, the excess ofacetic acid distilled off, and the acetylated acids dissolved in 5 partsof sulfuric acid. These acids are nitrated with mixed acid contain-ing 43 per cent nitric acid, cooled, diluted with ice and water, andsalted out with about 2 parts of salt. The sodium l-acetamido-4-nitro-6-(and 7-)sulfonates are now reduced hot with iron and someacetic acid. The acetyl-compound is isolated and used as such,the acetyl-group being split off after coupling
LITERATURE.—Cain, Intermediate Products (2d Ed.), 210Lange, Zwischenprodukte, #2486Thorpe, Die. Chemistry, 3, 612
Dyes Derived from 1:4-Naphthylene-diamine-6-sulfonic Acid
SchultsNumberfor Dye
273
274
Ordinary Name andClass of Dye
DISAZO DYEDiaminogen Blue BB
Diandnogen B
Statistics ofImport and
Manufacture
I '14:— 8,308M'17:— ?I '20:— 5,936
I '14:—313,629I '20:— 18,120
Other IntermediatesUsed and Notes
a-NaphthylamineSchaeffer's Acid
a-NaphthylamineGamma Acid
DyeAppli-cationClass
D
D
2:7-Naphthylene-diamine-sulfonic Acid
2: 7-Diamino-naphthalene-sulfonic Acid (C. A. nomen.)
=C10H10N2O3S =
412 DYES CLASSIFIED BY INTERMEDIATES
FORMATION.—Probably by first sulfonating the 2: 7-dihydroxy-naphtha-lene and then by action of ammonia on the 2: 7-dihydroxy-naphtha-lene-sulfonic acid
LITERATURE.—Ger. Pat. 79780, 80070; Frdl. 4, 948, 949Cf. Thorpe, Die. Chemistry, 3, 610, 611, 650
Dye Derived from 2
SchidtzNumberfor Dye
330
Ordinary Name andClass of Dye
DISAZO DYEZambesi Brown G
: 7-Naphthylene-diamine-sulfonic Acid
Statistics ofImport and
Manufacture
I '14:— 4,028I '20:— 1,104
Other IntermediatesUsed and Notes
BenzidineGamma acid
DyeAppli-cationClass
D
o-Naplithylene-diamine-£-sulfonic Acid
1:2-Naphthylene-diamine-6-sulf onic Acid (not consideredherein)
o-Napthylene-diamine-7-sulf onic Acid
1:2-Naphthylene-diamine-5~sulfonic Acid (not consideredherein)
o-NaphthyIene-diamine-5-sulfonic Acid
l:2-Naphthylene-diamine-7-sulfonic Acid (not consideredherein)
a-Naphthyl-glycine
iV-(l-Naphthyl)-fiflycine (C. A. nomen.)
NH.CHoCOOH
FORMATION.—From a-naphthylamine by reaction with chloro-aceticacid
LITERATURE.—Lange, Zwischenprodukte, #2264Ger. Pat. 79861 of 1893
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from a-Naphthyl-glycine
413
SchultzNumbefor Dye
309
310
Ordinary Name andClass of Dye
DISAZO DYESGlycine Red
Glycine Corinth
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
BenzidineNaphthionic Acid
Benzidenea-Naphthyl-glycine
(2 mols)
DyeAppli-cationClass
D
D
/3-Naphthyl-sulfuric Acid
See, 2-Naphthol-l-sulfonic Acid
Nevile-Winther's Acid
l-Naphthol-4-sulfonic Acid (C A. nomen.)
NWAcid
a-Naphthol~sulfonic Acid NW
OH
STATISTICS.—Manufactured '18:—340,074 lbs.Manufactured '19:—344,449 lbs.Manufactured '20:—561,929 lbs.
FORMATION.—From the sodium salt of naphthionic acid by hydrolyzingthe amino group
LITERATUEB.—Cain, Intermediate Products (2d Ed.), 217Thorpe, Die. Chemistry, 3, 617Lange, Zwischenprodukte, #2415-2421
414 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Nevile-Winther's Acid
SchultzNumberfor Dye
77
94
104
163
176
194
195
224
233
253
Ordinary Name andClass of Dye
MONOAZO DYESAzo Coccine 2R
Azo Eosine
Benzoyl Pink
Azo Rubine
Double Scarlet SScarlet 2R
Rosophenine 10BTMazine Red R
Rosophenine SG
DISAZO DYESCloth Red G
Cloth Red B
OrseUline BB
Statistics ofImport and
Manufacture
I 14:— 1,001M'18:— ?M19:— ?
I '14:—230,763M17:—197,621M18:—79,779M19:—187,264I '20:— 1,102M '20:^470,949
I 14:— 10,182M17:— ?I '20:— 1,653
r 14:— 3,077M19:— ?M'20:— ?
M18:— ?M19:— ?M'20:— 19,639
I 14:— 401M19:— ?M'20:— ?
I 14:— 1,962M18:— ?M19:— ?M'20:— ?
Other IntermediatesUsed and Notes
Xylidine
o-Anisidine
Benzoyl-o-tolidine
Naphthionic Acid
Broenner's Acid
Dehydrothio-p-tolui-dine-sulfonic Acid
Primuline
Amino-azo-benzene
Amino-azo-toluene
Amino-azo-toluene-siil-fonic Acid
DyeAppli-cationClass
A
A
D
A
A
D
D
A
M
A
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Nevile Winther's Acid (continued)
415
SchultzNumberfor Dye
Ordinary Name andClass oj Dye
DISAZO DYES(continued)
Diamond Black F
Violet Black
Azo AlizarinBordeaux W
Congo Corinth
Anthracene Red
Congo Corinth B
Azo Blue
Dianil Blue 2RBenzo New Blue 2B
Oxamine Blue 4R
Statistics ofImport and
Manufacture
I '14:—462,306M'17:— ?M'18:— ?M'19:—222,938I '20:— 2,226M 320:— ?
I '14:— 44,157M'17:-M'18:-M'19:-M'20:-
-137,704-242,503
I '14:-M'19:-I '20:-M'20:-
3,873
104
I '14:— 2,196M'19:— ?
I '14:—M'19:—M'20:—
498
I '14:— 14,434
I '14:— 573M'20:— ?
Other IntermediatesUsed and Notes
a-NaphthylamineAmino-saHcylic Acid
a-Naphthylaminep-Phenylene-diamine
or Amino-acet-anilide
Salicylic Acidp-Phenylene-diamine
BenzidineNaphthionic Acid
o-Nitro-benzidineSalicylic Acid
TolidineNaphthionic Acid
TolidineNevile-Winther's Acid
(2 mols)
TolidineChromotropic Acid
TolidineJ Acid
416 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Nevile-Winther's Acid (continued)
SchultzNumberfor Dye
386
396
397
401
407
410
412
421
427
428
Ordinary Name, andClass of Dye
DISAZO DYES{continued)
Diamine Blue BXBenzo Blue BX
Indazurine RM
Direct Blue R
Diamine Blue 3R
Azo Violet
Benzoazurine G
Congo Blue 2B
Oxamine Blue B
Indazurine GM
Direct Blue B
Statistics ofImport and
Manufacture
I '14:— 1,740M '17:— ?M '18:— ?M '19:— 92,214I '20:— 4,520M '20:— 90,147
M'17:— ?
I '14:— 78,699M'18:— ?M '19:—150,589I '20:— 287M'20:—237,328
I '14:— 35,891I '20:— 13
I '14:— 21,421M'17:— 14,823M'18:— ?I '20:— 7,055
Other IntermediatesUsed and Notes
TolidineH Acid
Tolidine1:7-Dihydroxy-2-naph-
thoic-4-sulf onic Acid
Tolidine1:7-Dihydroxy-6-naph-
thoic-3-sulfonic Acid
Ethoxy-benzidineNevile-Winther's Acid
(2 mols)
DianisidineNaphthionic Acid
DianisidineNevile-Winther's Acid
(2 mob)
DianisidineR Acid
Dianisidinel-Ainino-5-naphthol-7-
sulf onic Acid
Dianisidine1:7-Dihydroxy-2-naph-
thoic-4-sulf onic Acid
Dianisidine1:7-Dihydroxy-6-naph-
thoic-3-sulf onic Acid
DyeAppli-cationClass
D
D
D
D
D
D
D
D
D
D
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Nevile-Winther's Acid (continued)
417
SchulizNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
447
450
459
483
484
TRISAZO DYESBenzo Gray S
Benzo Black Blue R
Benzo Black Blue G
I '14:— 802
St. Denis RedRosophenine 4B
Milling Scarlet B
I '14:-I '20:-
1,496550
BenzidineSalicylic Acida-Naphthylamino
Tolidinea-NaphthylamineNevile-Winther's Acid
(2 mols)
B enzidine-disulf onicAcid
a-NaphthylamineNevile-Winther's Acid
(2 mols)
Diamino-azoxy-tolucneNevile-Winthcr's Acid
(2 mols)
Diamino-azoxy-tolucncR Acid
D
D
D
D
Nigrotic Acid
See, 1: 7-Dihydroxy-6-naphthoic-3-sulfonic Acid
Nigrotinic Acid
See, 1: 7-Dihydroxy-6-naphthoic-3-sulfonic Acid
N i t r o - l : 2 : 4 A c i d
See, l-Amino-8-nitro-2-naphthol-4-sulfonic Acid
j^-Nitro-acetanilide
N H . C O C H 3
N O ,
418 DYES CLASSIFIED BY INTERMEDIATES
STATISTICS.—Manufactured '17:— ?Manufactured '18:—541,552 lbs.Manufactured '19:—669,658 lbs.Manufactured '20:—569,728 lbs.
FORMATION.—Aniline is acetylated to acetanilide, which is dissolved i nsulfuric acid and then nitrated with mixed acid in the cold
LITERATURE.—Cain, Intermediate Products (2d Ed.), 53
USES.—For the manufacture of p-nitro-aniline and acetyl-p-phenylene-diamine (p-amino-acetanilide)
Nitro-alizarin, crude
Ci4H7NO6=285
FORMATION.—Alizarin is dissolved in sulfuric acid and nitrated
Dye Derived from Nitro-alizarin, crude
SchultzNumberfor Dye
798
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Alizarin Maroon W
Statistics ofImport and
Manufacture
I '20:— 2,014
Other IntermediatesUsed and Notes
[Reduction]
DyeAppli-cationClass
M
3-Nitro-alizarin (C. A. nornen.)
j3-Nitro-alizarin
1:2-Dihydroxy-3-nitro-anthraquinone
STATISTICS.—liefer to the dye, Alizarin Orange, which is 3-nitro-alizarin
FORMATION.—From alizarin by nitration of its boric ester
LITERATURE.—Schultz, Farbstofftabellen (1914), #779Lange, Zwischenprodukte, #3341Georgievics and Grandmougin, Dye Chemistry, 268
DYES CLASSIFIED BY INTERMEDIATES 419
Dyes Derived from 3-Nitro-alizarin
SchulizNumberfor Dye
Ordinary Name andClass of Dye
Statistics ojImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
779
803
804
808
809
ANTHRAQUINONB ANDALLIED DYES
Alizarin Orange
Alizarin Blue WX
Alizarin Blue S
Alizarin Green X
Alizarin IndigoBlueS
— 14,239— ?— 500
M'20:— ?
I '14:M'19:
I '14M'19I '20
I '14I '20
I '14I '20
—319,394— ?— 5,585
—117,850— 43,679
—135,191—- 4,254
[This is 3-nilro-alizarin]
3-Ami no-alizarin[Glyccrol]
3-Amino-alizarin[Glyccrol]
3-Ami no-alizarin[Glyccrol; Oxidation]
3-Amino-alizarin[Glyccrol; Oxidation]
M
M
M
M
M
4-Nitro-alizarin (C. A. nomen.)
a-Nitro-alizarin
•OCX O H
0 H =
NO 2
F O R M A T I O N . — T h i s compound is made by ni t ra t ion of alizarin in weak
oleum solution, or by nitrat ion of t he methyl , benzoyl, or arsenic
ester of alizarin
LITERATURE.—Georgiev ics and Grandmougin, D y e Chemistry , 2G8
Schultz, Farbstofftabellen (1914), #779
420 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 4-Nitro-alizarin
SchultzNumberfor Dye
797
805
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Alizarin Garnet R
Alizarin Green S
Statistics ofImport and
Manufacture
I '14:— 720
I '14:-- 15,885
Other IntermediatesUsed and Notes
[Reduction]
Nitro-benzene[Reduction; Glycerol]
DyeAppli-cationClass
M
M
a-Nitro-alizarinSee, 4-Nitro-alizarin
0-Nitro-alizarinSee, 3-Nitro-alizarin
6-Nitro-m-amino-benzene-sulfonic AcidSee, 6-Nitrometanilic Acid (C A. nomen.)
o-Nitro-o-amino-^-cresolSee, 2-Amino-6-nitro-p-cresol (C A. nomen. OH = 1)
2-Nitro-6-amino-l-phenol-4:-sulfonic AcidSee, 2-Amino-6-nitro-l-phenol-4-sulfonic Acid
6-Nitro-2-amino-l-phenol-4:-sulfonic AcidSee, 2-Amino-6-nitro-l-phenol-4-sulfonic Acid
m-Nitro-aniline
NH2
STATISTICS.—^Imported j14:— 3,527 lbs.Manufactured 17:—228,279 lbs.Manufactured 18:—630,802 lbs.Manufactured 19:— 68,600 lbs.Manufactured ;20:— ?
DYES CLASSIFIED BY INTERMEDIATES 421
FORMATION.—Benzene is nitrated with mixed acid to dinitro-benzene,
and this body is reduced with sodium sulfide
LITERATURE.—Cain, Intermediate Products (2d Ed.), 51
Lange, Zwischenprodukte, #537, 542
Dyes Derived from m-Nitro-aniline
SchultzNumberfor Dye
46
47
48
49
222
408
Ordinary Name andClass of Dye
MONOAZO DYESra-Nitraniline Orange
Orange III
Alizarin Yellow GG
Prague AlizarinYellow G
DISAZO DYESJanus Yellow G
Azophor Black S
Statistics ofImpoi t and
Manufacture
M'18:— ?
I ' 14:—144,761MJ17:—
1,452,622M'18:—
2,233,208M'19:—163,170M'20:—211,580
I '14:— 2,250I '20:— 758
Other IntermediatesUsed and Notes
0-Naphthol
R Acid
Salicylic Acid
0-Resorcylic Acid
Resorcinolm-Amino-phenyl-tri-
methyl-ammoniumChloride
m-Nitro-aniline (? mols)Dianisidine
DyeAppli-cationClass
MF
A
M
M
B
D
^-Nitro-aniline
NO2
422 DYES CLASSIFIED BY INTERMEDIATES
STATISTICS.—Imported '14:— 771,682 lbs.
Manufactured ' 17:—1,724,008 lbs.
Manufactured ' 18:—1,320,064 lbs.
Manufactured ' 19:—1,310,658 lbs.
Manufactured '20:—2,138,492 lbs.
FORMATION.—(1) Aniline is acetylated to acetanilide, which is t h e n
nitrated with mixed acid to p-nitro-acetanilide. T h e la t ter c o m -
pound is hydrolyzed by boiling with caustic soda to p-ni tro-ani l ine.
(2) p-Chloro-nitro-benzene is heated with ammonia under p r e s s u r e
LITERATURE.—Cain , Intermediate Products (2d Ed . ) , 51
Lange, Zwischenprodukte, #533, 538-541
Dyes Derived from ^-Nitro-aniline
SchvltzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
50
51
52
53
54
55
56
MONOAZO DYESAzo Cardinal G
NitrophenineThiazol Yellow R
Archil Substitute V
Archil Substitute3VN
Apollo Red B
Brilliant Archil C
Paranitraniline Red
M'18:— ?
I '14M'20
:— 423:— ?
:— 904
I '14:-I '20:
401100
Ethyl-sulfobenzyl-aniline
Dehydrothio-toluidine-sulf onic Acid
Naphthionic Acid
Laurent's Acid
l-Naphthylainiiie-4: 6-and -4: 7-disulfordcAcids
1:8-Naplithyleiie-dia-mine-3:6-disulfonicAcid
D
A
A
A
I '14M'17M'18M J19JVT20
:— 49,847: ?
:— ?
:— ?
M F
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from jfr-Nitro-aniline (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
57
58
61
63
215
216
217
MONOAZO DYES(continued)
Chromotrope 2B
Alizarin Yellow R
Victoria Violet
I '14:M'18:-M'19:-M'20:-
7,970???
Azo Acid Blue B
DISAZO DYESBlue Black N
Domingo BlueBlack B
Naphthol Blue BlackAgalma Black 10B
I '14:— 97,059M' 17:—215,468M'18:—385,910M '19:—130,424I '20:— 860M'20:— 83,334
I '14:— 52,365M'17:— ?M;18:— ?M'19:—105,086I '20:— 2,182M'20:— ?
I '14:— 45,09SI '20:— 4,4S5
Chromotropio Acid
Salicylic Acid
Chromotropic Acid[RcducUon]
I '14:- 2,653
I '14:—431,027M'17:—620,218M'18:—
1,158,309M'19:—
1,877,860I '20:— 840M'20:—
2,608,864
1:8-Dihydroxy-uaph-thalcnc-4-sulfonicAcid
[Methylation]
Anilinel-Amino-8-napliil iol-
4: 6-disulfonic Acid
Anilinel-Amino-8-naphtl lol-
3:5-disulfonic Acid
AnilineH Acid
424 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from j>-Nitro-aniline (continued)
SchvltzNumberfor Dye
218
221
245
408
473
474
475
719
Ordinary Name andClass of Dye
DISAZO DYES
{continued)NigrophorBASF
Anthracene AcidBrown G
Nyanza Black B
Azophor Blue DAzophor Black S
TRISAZO DYESDiamine Black HW
Diamine Green BOxamine Green B
Diamine Green GOxamine Green G
SULFUR DYEThional Black
Statistics ofImport and
Manufacture
MJ17:— ?M'18:— ?I '20:— 225
I '20:— 342
I '14:— 77,100M'17:— ?M '18:—295,147M'19:—305,854I '20:— 2,460M'20:-^20,138
I '14:— 7,329M'17:— ?M'18:— 29,118M'19:—136,638I '20:— 1,332M'20:— 53,292
I '14:— 16,865
Other IntermediatesUsed and Notes
2: 5»Dichloro-anilinel-Amino-8-naphthol-5-
sulf onic Acid
Sulfanilic AcidSalicylic Acid
a-NaphthylamineGamma Acid[p-Nitro-aniline reduced
after coupling]
Dianisidine
BenzidineGamma AcidHAcid
BenzidinePhenolHAcid
BenzidineSalicylic AcidHAcid
o-Nitro-phenol[Na*S plus S]
oro-Nitro-phenol (2 mols)Aniline[Na^S plus S]
DyeAppli-cationClass
M F
ACr
D
D
D
D
D
S
DYES CLASSIFIED BY INTERMEDIATES 425
2-Nitro-aniline-4-sulfonic Acid (NH2=1)
See, 4~Amino-3-nitro-benzene-sulfonic Acid (C. A. nomen.)
4-Nitro-aniline-2-sulfonic Acid (NH2=1)
See, 2-Amino-5-nitro-benzene-sulfonic Acid ( C A. nomen.SOiH-1)
4-Nitro-aniline-3-sulfonic Acid
See, 6-Nitro-metanilic Acid (C. A. nomen.)
o-Nitro-aniline-j&-sulfonic Acid (NH2=1)
See, 4-Amino-3-nitro-benzene-sulfonic Acid (C A, nomen.)
^-Nitro-aniline-o-sulfonic Acid (NH2=1)
See, 2-Amino-5-nitro-benzene-sulfonic Acid ( C A. nomenSOzH-1)
4-Nitro-o-anisidine (C. A. nomen. NIh=l)
p-Nitro-o-anisidine
NH 2
/ N 0 C H 3
NO2
_ C 7 H 8 N 2 O 3 = 168
FORMATION.—o-Anisidine is acetylated, then nitrated, and saponifiedby heating with 70 per cent sulfuric acid. The resulting mixtureof 4- and 5-nitro-o-anisidines, is separated by crystallization from40 per cent sulfuric acid
LITERATURE.—Lange, Zwischenprodukte, #911
Dye Derived from 4-Nitro-o-anisidine
SchultzNumberfor Dye
98
Ordinary Name andClass of Dye
MONOAZO DYESNaphthol PinkNitrosamine
PinkBX
Statistics ofImport and
Manufacture
I '14:— 99
Other IntermediatesUsed and Notes
0-Naphtkol
DyeAppli-cationChaw
MF
426 DYES CLASSIFIED BY INTERMEDIATES
5-Nitro-o-anisidine (C. A. nomen. NH2=1)
m-Nitro-0-anisidine
2
OOCH3O s N l ^ :C7H8N2O3 =
FORMATION.—o-Anisidine is acetylated, then nitrated, and saponifiedby heating with 70 per cent sulfuric acid. The resulting mixtureof 4- and 5-nitro-o-anisidines is separated by crystallization from40 per cent sulfuric acid
LITERATURE.—Lange, Zwischenprodukte, #911
Dye Derived from 5-Nitro-o-anisidine
SchultzNumberfor Dye
99
Ordinary Name andClass of Dye
MONOAZO DYETuscaline Orange G
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
0-Naphthol
DyeAppli-cationClass
CLMF
m-Nitro-o-anisidine (NH%=1)
See, 5-Nitro-o-anisidine (C. A. nomen.
/>-Nitro-o-anisidine
See, 4-Nitro-o-anisidine (C. A. nomen. NH2-I)
o-Nitro-anisole
OCH3
STATISTICS.—Manufactured 718:— ?Manufactured '19:— ?Manufactured '20:—273,327 lbs.
FORMATION.—(1) From o-nitro-phenol by methylation. (2) Fromo-chloro-nitro-benzene by action of methanol (methyl alcohol) andcaustic
DYES CLASSIFIED BY INTERMEDIATES 427
LITERATURE.—Cain, Intermediate Products (2d Ed.), 96Cf. Lange, Zwischenprodukte, #578
USES.—For preparation of dianisidine
l-Nitro-anthraquinone-6-sulfonic Acid
5-Nitro-2-anthraquinone~sulfonic Acid (C. A. nomen.)
, . . N0 2<xFORMATION.—When anthraquinone-2-sulfonate of sodium is nitratedwith a mixture of equal parts of "fuming" nitric acid and sulfuricacid (66°) there arises a mixture of the a-nitro and /3-nitro-an-thraquinone-sulfonic acid which can be separated by dilution,whereupon the a-acid is precipitated. The a-acid is undoubtedlyl-nitro-anthraquinone-6-sulfonic acidLITERATURE.—Claus, Ber. 15, 1515 (1882)Cf. Lange, Zwischenprodukte, #3160, 3263Dye Derived from l-Nitro-anthraquinone-6-sulfonic AcidSchultzNumberfor Dye864
Ordinary Name andClass of DyeANTHKAQUINONE ANDALLIED DYESAnthraquinoneGreen GXStatistics ofImport andManufactureI '14:—- 1,709I '20:— 2,531
Other IntermediatesUsed and NotesAniline[Halogonation]p-Toluidine
DyeAppli-cationClassACr
5-Nitro-2-anthraquinone-sulfonic Acid (C. A. nomen.)
See, l-Nitro-anthraquinone-6-sulfonic Acid
m-Nitro-&enzaldehyde
CHO
= C 7 H 6 N O 3 = 1 5 1
428 DYES CLASSIFIED BY INTERMEDIATES
STATISTICS.—Imported ' 14:—very smallManufactured ; 17:— ?Manufactured '18:— ?Manufactured '20:— ?
FOKMATION.—From benzaldehyde by nitration at not above 30-35'(Twenty per cent o-nitro-derivative also formed)
LITEKATURE.—Cain, Intermediate Products (2d Ed.), 144Lange, Zwischenprodukte, #296
Dyes Derived from m-Nitro-benzaldehyde
SchidtzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeApplicatioiClasi
510
523
543
544
545
TRIPHENYL-METHANEDYES
Azo Green
Fast Green
Patent Blue V
Cyanine B
Patent Blue A
I 14:— 14,347I '20:— 10,461
I 14:—196,228M17:— ?M18:— ?I '20:— 36,420
I 14:— 8,398I '20:— 24
I 14:—- 63,744M18:— ?I '20:— 44,801
Dimethyl-aniline(2 mols)
Salicylic Acid[Oxidation]
Dimethyl-aniline(2 mols)
Benzyl Chloride (2 mols)[Sulfonation, Oxidation]
Diethyl-aniline (2 mols)[Sulfonation, Oxidation]
Diethyl-aniline (2 mols)[Sulfonation, Oxidation]
Benzyl-ethyl-aniline(2 mols)
[Sulfonation, Oxidation]
M
A
A
o-Nitro-fcenzaldehyde
HCO
Q H O , =
DYES CLASSIFIED BY INTERMEDIATES 429
STATISTICS.—Manufactured '18:— ?
FOKMATION.—When benzaldehyde is nitrated, there results about 20per cent of the o-nitro- and about 80 per cent of the m-nitro-derivative. The nitration product is poured into water, and theoily o-derivative is separated from the solid w-compound bypressing
LITERATURE.—Cain, Intermediate Products (2d Ed.), 143Lange, Zwischenprodukte, 22, 37, 38, 40, 181, 254, 275,
278, 289-302
SchultzNumberfor Dye
875
Dye Derived
Ordinary Name andClass of Dye
INDIGO GROUP DYEIndigo Salt T
from o-Nitro-benzaldehyde
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
[Acetone; NaOH]
DyeAppli-cationClass
Print-ing
^-Nitro-benzaldehyde
CHO
= C7H5NO3 =
STATISTICS.—Imported 714:—very small
FORMATION.—From p-nitro-toluene by oxidation
LITERATURE.—Lange, Zwischenprodukte, #275, 303-312
Dye Derived from ^-Nitro-benzaldehyde
SchultzNumberfor Dye
511
Ordinary Name andClass of Dye
TRIPHENYL-METHANEDYE
ParafuchsineParamagenta
Statistics ofImport and
Manufacture
I '14:— 65,026M'18:— ?M'19:— ?M'20:— ?
Other IntermediatesUsed and Notes
Aniline (Sulfate)(2 mols)
[Zinc chloride; ferrouschloride]
DyeAppli-cationClass
B
430 DYES CLASSIFIED BY INTERMEDIATES
Nitro-benzene
Myrbane Oil
NO2
STATISTICS.—Imported '14:— 1,502,205 lbs.
Manufactured 17:—42,975,655 lbs.Manufactured 18:—38,250,332 lbs.Manufactured 19:-^2,544,017 lbs.Manufactured '20:—53,244,008 lbs.
FOEMATION.—From benzene by nitration with mixed acid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 20Lange, Zwischenprodukte, #264r-268
Dyes Derived from Nitro-benzene
SchultzNumberfor Dye
511
512
Ordinary Name andClass of Dye
TRIPHENYL-METHANEDYES
ParafuchsineParana agenta
MagentaFuchsine
Statistics ofImport and
Manufacture
I '14:— 65,026M'18:— ?M19:— ?M'20:— ?
I '14:— 87,102M'17:— 17,739M'18:— 71,675M'19:—155,830I '20:— 189M'20 :—284,285
Other IntermediatesUsed and Notes
Aniline (2 mols)p-Toluidine
orp :p/-Diamino-dipheiiyl-
methane orAnhydro-formalde-hyde-aniline
Aniline and anilinB hy-drochloride
[Ferric chloride]
Anilineo-Toluidinep-Toluidine[Iron and zinc chloride]
DyeAppli-cationClass
B
B
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Nitro-benzene (continued)
431
SchultzNumberfor Dye
698
700
718
805
Ordinary Name andClass of Dye
AZINE DYESNigrosine, Spirit
Soluble
Nigrosine, WaterSoluble
SULFUR DYESt. Denis Black
ANTHRAQUINONE ANDALLIED DYES
Alizarin Green S
Statistics ofImport and
Manufacture
I '14:—186,595M ' 17:—-302,706M'18:—-314,151M'19:—346,167M'20:—919,242
I '14:—398,112M'17:—
1,968,458M'18:—
1,191,343M'19:—
1,660,149I '20:— 501
M'20:—2,743,021
I '14:— 15,885
Other IntermediatesUsed and Notes
Aniline (excess)[Iron]
Aniline (excess)[Iron, Sulfonation]
p-Phenyleno-diaminePhenol[fcCl,, S, N*S]
4-Amino-alizarin.[Reduction; glycorol]
DyeAppli-cationCla83
ss
A
S
M
3-Nitro-benzidine (C. A. nomen.
See, o-Nitro-fcenzidine
o-Nitro-benzidine
3-Nitro-&enjzidine (C. A. nomen.
N0 2
= C l * H n N 8 ° 2 — 2 2 9
STATISTICS.—^Manufactured ' 19:— ?
FORMATION.—By nitration of benzidine in sulfuric acid solution
432 DYES CLASSIFIED BY INTERMEDIATES
LITERATURE.—Green, Organic Coloring Matters (1908), 41Eng. Pat. 13475 of 1892Lange, Zwischenprodukte, #1220
Dye Derived from o-Nitro-benzidine
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediate*
Used and Notes
355DISAZO DYE
Anthracene Red I '14:—M'19:—I '20:—M'20:—
3,873
104
Salicylic AcidNevile-Winther's Avul
^-Nitro-benzyl Chloride
a-Chloro-p-nitro-toluene (C. A. nomen.)
CH2C1
= C7H6C1NO2 = 171.5
NO2
FORMATION.—(1) By passing chlorine into p-nitro-toluene185-190°. (2) By dropping benzyl chloride intoacid cooled to -15° C.
LITERATURE.—Ann. 185, 271
Ber. 6, 1056Cf. Lange, Zwischenprodukte, #250
Dye Derived from ^-Nitro-benzyl Chloride
SchultzNumberfor Dye
734
Ordinary Name andClass of Dye
SULFUR DYEPyrogene Yellow
Statistics ofImport and
Manufacture
I '14:— 18,515I '20:— 2,701
Other IntermediatesUsed and Notes
p-Ammo-phenol[S+Na^S]
DYES CLASSIFIED BY INTERMEDIATES
o- and ^-Nitro-chloro-benzenes
See, o- and p-Chloro-nitro-benzenes (C A. nomen.)
Nitro-diphenylamine-sulfonic Acid
433
FORMATION.—Diphenylamine in sulfuric acid solution is heated with
20 per cent oleum at 80-100°, and is then nitrated with nitric
acid at 50-80°, resulting in formation of " nitrated diphenylamine-
sulfonic acid"
LITERATURE.—Lange, Die Schwefel-farbstoffe, 145
Dye Derived from Nitro-diphenylamine-sulfonic Acid
SchultzNumberfor Dye
737
Ordinary Name andClass of Dye
SULFUR DYECotton BrownSulfine Brown
Statistics ofImport and
Manufacture
I '14:— 2,206
Other IntermediatesUsed and Notes
[S+Na*S]
DyeAppli-cationClass
S
3-Nitro-flavopurpurin (C. A. nomen.)
0-Nitro-flavopurpurin
3-Nitro-l: 2: 6-trihydroxy-anthraquinone
0 HCO
FORMATION.—By nitration of flavopurpurin
LITERATURE.—Ger. Pat. 54,624, Frdl. 2, 122
434 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 3-Nitro-flavopurpurin
SchvltzNumberfor Dye
806
807
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Alizarin Black P
Alizarin Black S
Statistics ofImport and
Manufacture
I '14:—229,500
I '14:—259,991
Other IntermediatesUsed and Notes
[Glycerol]
[Glycerol]
DyeAppli-cationClass
M
M
jS-Nitro-flavopurpurin
See, 3-Nitro-flavopurpurin
6-Nitro-metanilic Acid (C. A. nomen.)
4-Nitro-aniline-3-sulf onic Acid
6-Nitro-77i-amino-benzene-sulfonic Acid
SO3H
= C6H6N2O5S = $
FORMATION.—Sodium metanilate is acetylated, dissolved in sulfuric acidand nitrated with mixed acid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 56
USES.—For preparation of mtro-?ra-phenylene-diamine
Nitro-phenol crude
OH OH
and =C6H5NO3 =
N0 2
STATISTICS.—Manufactured '17:— ?Manufactured'18:— ?Manufactured '19:— ?
FORMATION.—From phenol by nitration with nitric acid
ain, Intermediate Products (2d Ed.), I l l
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Nitro-phenol crude
435
SchulizNumberfor Dye
698
700
Ordinary Name andClass oj Dye
AZINE DYESNigrosine, Spirit
Soluble
Nigrosine, WaterSoluble
Statistics ofImport and
Manufacture
I 14:—186,595M'17:—362,706M18:—314,151M' 19:—346,167M'20:—919,242
I '14:—398,112M'17:—
1,968,458M'18:—
1,191,343M19:—
1,660,149I '20:— 501M'20:—
2,743,021
Other IntermediatesUsed and Notes
Aniline (excess)
Aniline (excess)[Sulfonation]
DyeAppli-cationClass
ss
A
o-Nitro-^henol
OH
STATISTICS.—Imported '14:—very smallManufactured '17:— 58,128 lbs.Manufactured '18:—143,277 lbs.Manufactured '19:— 18,373 lbs.Manufactured '20:— ?
FORMATION.—(1) Phenol is nitrated with nitric acid, resulting in anoily mixture of o- and p-nitro-phenol. The o-derivative is separatedby distillation and purified by steam distillation. (2) o-Chloro-nitro-benzene is hydrolyzed to the o-nitro-phenol by boiling withcaustic soda
LITERATURE.—Cain, Intermediate Products (2d Ed.), I l lLange, Zwischenprodukte, #574-577
436 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from o-Nitro-phenol
SchulizNumberfor Dye
719
Ordinary Name andClass of Dye
SULFUR DYEThional Black
Statistics ofImport and
Manufacture
I >14:— 16,865
Other IntermediatesUsed and Notes
p-(o- or m-)Nitro-aniline
[N^S+S]or
p-(o- or ??i-)Nitro-aniline
Anilineo-Nitro-phenol (2 mols)[Na^S+S]
DyeAppli-cationClass
S
STATISTICS.—Imported '14:— 4,780 lbs.Manufactured '17:—413,216 lbs.Manufactured 18:—192,259 lbs.Manufactured '19*— 76,191 lbs.Manufactured '20*—125,693 lbs.
FORMATION.—(1) Phenol is nitrated with nitric acid to an oily mixtureof o- and p-nitro phenol, from which the o-isomer is removed bydistillation. The residue upon being extracted with hot wateryields the p-isomer, which crystallizes out from the aqueous extractupon cooling. (2) p-Chloro-nitro-benzene is hydrolyzed to thep-nitro-phenol by boiling with caustic soda
LITEBATDBE.—Cain, Intermediate Products (2d Ed.;, I l l
Lange, Zwischenprodukte, #574-576
DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from />-Nitro-phenol
437
SchultzNumberfor Dye
709
Ordinary Name andClass of Dye
SULFUR DYEItalian Green
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
[Sulfur, etc.]
DyeAppli-cationClass
S
4-Nitro-m-phenylene-diamine
NH2
NH2 =C6H7N3O2 =
FORMATION.—5-Amino-2-nitro-benzene-sulfonic Acid (4-nitro-aniline-3-sulfonic acid) is heated in an autoclave with 25 per cent ammoniawater for three hours at 170-180°
LITERATURE.—Cain, Intermediate Products (2d Ed.), 86Dyes Derived from 4-Nitro-m-phenylene-diamine
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
Manufacture0 fh er hi tcrmediates
Used avd Notes
DyeAppli-cationClass
191
286
306
314
360
MONOAZO DYEPyramine Yellow R
DISAZO DYESToluylcne Yellow
Pyramine Orange 3G
Pyramine Orange 2R
Pyramine Orange R
I '14:-I '20:
I '14:-
I '14:I '20:-
5,727100
5,485
7,863396
I '14:— 2,789
I '14:-I '20:-
21,3297,821
Primulinc-sulfonic Acid
3:5-Diamino-p-toluene-sulfonic Acid
Nitro-m-plienylene-diamine (2 mols)
Bcnziclincm-Phcnylcnc-diamine-
disulfonic Acid
BenzidincAmino-R Acid
Benzidine-disulfonicAcid
Nitro-m-phenylene-diamine (2 mols)
D
D
D
D
438 DYES CLASSIFIED BY INTERMEDIATES
(o-Nitro-phenyl-mercapto)-acetic Acid (C. A. nomen.)
See, o-Nitro-phenyl-thioglycolic Acid
o-Nitro-phenyl-thioglycolic Acid
(o-Nitro-phenyl-mercapto)-acetic Acid (C A. nomen.)
S.CH2.COOH
FOKMATION.—o-Chloro-nitro-benzene in hot alcoholic solution is treatedwith thioglycolic acid and caustic soda solution, and then boiledfor two hours under a reflux condenser
LITERATURE.—Lange, Zwischenprodukte, #611
Dye Derived from o-Nitro-phenyl-thioglycolic Acid
SchultsNumberfor Dye
921
Ordinary Name andClass of Dye
INDIGO GROUP DYESHelindone Gray 2B
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
0-Nitro-pb.enyl-thio-glycolic Acid (2 mols)
[Chloro-sulfonic Acid;Reduction]
DyeAppli-cationClass
V
Nitroso-diethyl-m-amino-phenol
See, 5-Diethylamino-2-nitroso-phenol (C. A. nomen.)
^-Nitroso-diethyl-aniline
iV:iV-Diethyl-p-rdtroso-aniline (C. A. nomen.)
=C10H14N2O = 178
DYES CLASSIFIED BY INTERMEDIATES
STATISTICS.—Imported '14:—very small
FORMATION.—From diethyl-aniline by action of nitrous acid
LITERATURE.—Lange, Zwischenprodukte, #531
Dyes Derived from ^-Nitroso-diethyl-aniline
430
SchultzNumberfor Dye
639
641
646
Ordinary Name andClass of Dye
OXAZINE DYESGallanilic Violet R, B
Coreine RRCoelestine Blue B
Coreine AR
Statistics ofImport andManufacture
I '20:— 100
I '14:— 1,320I '20:- 44
Other IntermediatesUsed and Notes
Gallanilide
Gallamide
GallamideAniline[Sulfonation]
or[Coreine RR, Aniline,
Sulfonation]
DyeAppli-cationClass
M
M
M
Nitroso-dimethyl-m-amino-^-cresol
See, 5-Dimethylamino-2-nitroso-p~crcsol (C. A. nomen.)
j)-Nitroso-dimethyl~aniline
i\T:iV-Dimethyl-p-nitroso-aniline (C. A. nomen.)
N(CH3)2
STATISTICS.—Manufactured '17:— 96,166 lbs.Manufactured '18:—851,821 lbs.Manufactured J19:—592,663 lbs.Manufactured '20:—155,986 lbs.
FORMATION.—From dimethyl-aniline by action of nitrous acid upon acold solution of the hydrochloride
LITERATURE.—Lange, Zwischenprodukte, #531
440 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from jfr-Nitroso-dimethyl-aniline
SchultzNumberfor Dye
Ordinary "Same andClass of Dye
619
620
622
623
624
626
627
INDOPHENOL
Indophenol
OXAZINE ANDTHIAZIXE DYES
Capri Blue G O N
Delphine Blue B
Pyrogallol-Cyanine-Sulfonic Acids
Modern Violet X
Galloeyanine
Modern Cyanine
Statistics ofImport and
Manufacture
M'17:— ?M'18:— ?M'19:—126,61M '20:— ?
:— 128
M'17:— ?M'lS:— ?M719.— 43,827MJ20:— 76,719I '20:— 29,643
I '20:— 5,688
I '14:— 78,25iM'17:— ?M'18:~435,460M'19:—365,243I '20:— 12,414M'20:— 70,169
Other IntermediatesUsed and Notes
a-Naplitliol
3-Diethylamino-p-cresol (OH=*1)
Gallic AcidAniline[Sulfonation]
or[Aniline on Galloeya-
nine, Sulfonation]
PyrogaUol-5-sulfonicAcid
Gallic Acid[CO2 removed by heat]
or[Galloeyanine heated]
Gallic Acid
GallamideDimethyl-p-phenylene-
diamine[Reduction]
or"Galloeyanine; Di-
methyl-p-phenylene-diamine; Reduction]
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from ^-Nitroso-dimethyl-aniline (continued)
441
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediate
Used and Notes
DyeAppli-cationClass
628
629
630
631
632
633
634
635
636
OXAZINB ANDTHIAZINB DYES
(continued)Gallocyanine MS
Gallogreen DHModern Blue
Cyanazurine
Chromocyanine Y
Ultraviolet LGP
Indalizarino R
Indalizarine Green.
Blue 1900 TCModern Violet
Prune
M'18:-M'19:-I '20:-
M '20:-
??
1,289?
I '14:—• 4,308
I '20:— 551
I '20:— 1,933
I '14:I '20:
3,1974,418
Gallic Acid[Sulfonation]
or[Leuco-gallocyardne sul-
fonated; oxidized]
Gallic Acid[Formaldehyde]
or[Formaldehyde on
Gallocyanine]
GallamideAniline[Reduction]
Gallic Acid[Sulfonation]
or[Sulfite on Gallo-
cyanine]
Gallic Acid (2 mols)Nitroso-dimethyl-ani-
line (2 mols)
Gallic Acid[Sulfonation]
Gallic Acid[Sulfonation; Nitration
or[Nitration of Indaliza-
rine]
Gallic Acid[Reduction]
Gallic Acid MethylEster
442 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from ^-Nitroso-dimethyl-aniline (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
637
638
639
640
642
643
644
645
647
OXAZINE -ANDTHIAZINB DYES
(continued)Gallamine Blue
Amido GallamineBlue
Gallanilic Violet R , B
Modern Azurine DH
Phenocyanine TC
Phenocyanine TV
I '14:— 2,756I '20:— 16,446
I '2 :— 100
I '20:— 4,740
M'17:— ?I '20:— 1,543
Ultracyanine B
Gallazine A
Nitroso Blue MRResorcine Blue
Gallamide
Gallamide[Ammonia; Reduction]
Gallanilide
Gallic Acid MethylEster
Aniline
Gallic AcidResorcinol
Gallic AcidResorcinol[Sulfonation]
or[Phenocyanine sulfo-
nated]
Gallic AcidResorcinol
or[Gallocyanine;
Resorcinol]
Gallic AcidSchaeffer's Acid[Oxidation]
or[Gallocyanine,
Schaeffer's, Oxidation]
Resorcinol
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from ^-Nitroso-dimethyl-aniline (continued)
443
SchultzNumberfor Dye
649
650
651
652
655
658
659
660
Ordinary Name andClass of Dye
OXAZINB ANDTHIAZINB DYES
(continued)New Blue RMeldola's BlueCotton Blue
New Blue B
New MethyleneBlue GG
New Fast Blue F
Muscarine
Fast Black
Methylene Blue
Methylene Green 0
Statistics ofImport and
Manufacture
I '14:— 32,509M'17:— ?MIS:— 22,613M'19:— ?I '20:— 5,240M'20:— ?
I '14:— 2,502
I '14:— 1,960I '20:— 2,883
I '14:—185,958M '17:—268,435M'18:—312,572M'19:—465,992I '20:— 2,053
M'20:—577,264
I '14:— 30,812M'18:— ?M'19:— 2,435I '20:— 1,047
Other IntermediatesUsed and Notes
/3-Naphthol
/3-NaphtholNitroso-dimethyl-
aniline (2 mols)
/3-Naphthol[Dimethyl-amine,
Oxidation]or
[Meldola's Blue, Di-methyl-amine, Oxida-tion]
0-NaphtholHydrol
or[Meldola's Blue, Hydrol]
2: 7-Dihydroxy-naph-thalene
m-Hydroxy-diphenyl-amine
Dimethyl-aniline[Naa&Os, etc.]
Dimethyl-aniline[Na2S2O3 etc.; Nitration]
or[Methylene Blue
nitrated]
DyoAppli-cationClass
B
B
B
B
B
B
B
B
444 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from ^-Nitroso-dimethyl-aniline (continued)
SchultzNumberfor Dye
661
670
676
677
678
681
682
684
685
689
Ordinary Name andClass of Dye
OXAZINE ANDTHIAZINE DYES
(continued)Thionine Blue GO
AZINE DYESNeutral Red
Neutral Blue
Basle Blue B,
Fast NeutralViolet B
Methylene Gray 0New Fast Gray
Nigramine
Rhoduline Violet
Tannin Heliotrope
Indazine M
II
M
I
M
IMMMI
M
II
II
Statistics ofImport andManufacture
'14:-'20:-
'18:-
'14:-
'17:-
'14:-'17:-'18:-'19:-'20:-'20:-
'14:-'20:-
'14:-'20:-
- 18,618- 2,030
- ?
- 615
- ?
- 29,507?
- 16,746- 28,458
9- 31,620
- 2,75135
- 1,398249
Other IntermediatesUsed and Notes
Ethyl-methyl-aniline[Nas&Oa, etc.]
m-Tolylene-diamine[Oxidation]
i\^Phenyl-/5-naphthyl-amine
N: i\r-Ditolyl-2: 7-napht hyl ene-diamine
N: iV;-Diethyl-m-phenylene-diamine
[Boiling with alcohol]
Aniline
JV^PhenyW-m-toly-lene-diamine
oriV^Benzyl-JV^phenyW-
m-tolylene-diamine
Xylidine
Nitroso-dimethyl-ani-line (1 and 2 mols)
Diphenyl-m-phenylene-diancdne
DyeAppli-cationClass
B
B
B
B
B
B
B
B
B
B
DYES CLASSIFIED BY INTERMEDIATES 445
Dyes Derived from ^-Nitroso-dimethyl-aniline (continued)
SchultzNumberfor Dye
691
692
703
704
705
Ordinary Name andClass of Dye
AZINE DYES(continued)
MetaphenyleneBlueB
Naphthazine Blue
Rubramine
Indamine 3R
Indamine 6R
Statistics ofImport andManufacture
I '14:—
I '14:—I '20:—
50
6,2612,249
I '14:— 66,170I '20:— 9,681
Other IntermediatesUsed and Notes
N: N'-Di-o-tolyl-m-phcnylene-diamine
N:2V'-Di-2-naphthyl-?n-phenylene-diaminc
[Sulfonation]
o-Toluidinep-Toluidine
o-Toluidine
o-Toluidinep-Toluidine
DyeAppli-cationClass
B
A
B
B
B
^-Nitroso-ethyl-anilineiV-Ethyl-p-nitroso-aniline (C. A. nomen.)
NH.C2H5
FORMATION.—From ethyl-aniline by action of nitrous acid on the solu-tion in strong alcoholic hydrochloric acid
LITERATURE.—Cf. Lange, Zwischenprodukte, #529Dye Derived from ^-Nitroso-ethyl-aniline
ScttuitzNumberfor Dye
684
Ordinary Name andClass of Dye
AZINE DYERhoduline Red B
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
iV1-Phenyl-4-m-tolylene-diamine
oriV^Benzyl-iV^phenyl-
4-m-tolylene-diamine
DyeAppli-cationClass
B
446 DYES CLASSIFIED BY INTERMEDIATES
^-Nitroso-ethyl-o-toluidine
JV-Ethyl-4-nitroso-o-foluidine (C. A. nomen. NHR=1)
NH.C2H5
/\CHZ =C9Hi2N2O =
NO
FORMATION.—From ethyl-o-toluidine in an alcoholic solution of hydro-chloric acid, by action of NaNO2 solution in the cold
LITERATURE.—Beilstein, Organische Chemie (3d aufl.), II, spl., 248Cf. Lange, Zwischenprodukte, #529
Dyes Derived from Nitroso-ethyl-o-toluidine
SchultzNumberfor Dye
684
684
Ordinary Name andClass of Dye
AZINE DYESRhoduline Red G
Brilliant RhodulineRed
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
W-Phenyl-i-m-tolylene-diamine
ori^-Benzyl-iV^-phenyl-
4-m-tolylene-diamine
JV^-Ethyl-^^phenyl-^-m-tolylene-diamine
DyeAppli-cationClass
B
B
^-Nitroso-methyl-aniline
iV-Methyl-p-nitroso-aniline (C. A. nomen.)
NH.CHs
FORMATION.—^From methyl-aniline by action of nitrous acid on thesolution in strong alcoholic hydrochloric acid
LITERATURE.—Lange, Zwischenprodukte, #529
DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from ^-Nitroso-methyl-aniline
447
SchultzNumberfor Dye
625
Ordinary Name andClass of Dye
OXAZINE DYEChrome Heliotrope
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
Gallic Acid[Reduction]
DyeAppli-cationClass
M
l-Nitroso-2-naphthol (C. A. nomen.)
a-Nitroso-j3-naphthol
N . O HNO ||
STATISTICS.—Manufactured in 1918 and 1919, but in undisclosedquantities
FOBMATION.—From /3-naphthol by action of nitrous acidLITERATURE.—Cain , Intermediate Products (2d Ed.)j 216
Lange, Zwischenprodukte, #2330
Dyes Derived from l-Nitroso-2-naphthol
SchultzNumberJor Dye
2
107
116
331
Ordinary Name andClass of Dye
NITROSO DYEGambinc Y
MONOAZO DYESSulfamine Brown A
Sulfamine Brown B
DISAZO DYESAlkali Dark
Brown GV
Statistics ofImport and
Manufacture
I '14:— 132M 'IS:— ?M'19:— ?I '20:— 2,630M'20:— ?
Other IntermediatesUsed and Notes
[This is l-Nitroso-2-naphthol]
a-Naphthylamine
/?-Naplithylamine
BenzidineGamma Acid
DyeAppli-cationClass
M
M
M
D
U8 DYES CLASSIFIED BY INTERMEDIATES
l-Nitroso-2-naphthylamine-6-sulfonic Acid
6-Ammo-5-nitroso-2-naphthalene-sulfonic Acid (C A. nomen.)
NO
FORMATION.—One part of l-nitroso-2-naphthol-6-sulfonic acid (nitroso-Schaeffer's Acid) is heated with one part of 25 per cent ammoniafor three hours at 60°
LITERATURE.—Lange, Zwischenprodukte, #2479
Dye Derived from l-Nitroso-2-naphthylamine-6-sulfonic Acid
SchultzNumberfor Dye
675
Ordinary Name andClass of Dye
AZINE DYERosinduline G
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
Aniline (2 mols)
DyeAppli-cationClass
A
^-Nitroso-^henol
OH
= C6H5NO2=123
NO
STATISTICS.—Imported J14:—very small amountManufactured '17:— ?Manufactured '18:— ?Manufactured '19:—155,273Manufactured '20:—167,855
FOBMATION.—From phenol by action of nitrous acid in the cold
LITERATURE.—Cain, Intermediate Products (2d Ed.), I l lLange, Zwischenprodukte, 573
DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from ^-Nitroso-phenol
SchultzNumberfor Dye
748
Ordinary Name andClass of Dye
SULFUR DYE
Hydron Blue
Statistics ofImport and
Manufacture
I '14 —296,723I '20.— 19,210
M'20:— ?
Oth< r hiU rmvthaU &Used and Nol(,s
Carbiizolo
449
DyeA impli-cationClfHH
4-Nitroso-resorcinol
O H
H = C 6 H 5 N O 3 = 1 3 9
N O
FORMATION.—Resorc inol is dissolved in alcohol, one molecule of caust icsoda added, and then gradually one molecule of isoamyl ni t r i te isintroduced with cooling
LITERATURE.—Bei l s te in , Organische Chemie (3d Ed . ) , II, 923
Dye Derived from 4-Nitroso-resorcinol
SchultzNumberJor Dye
648
Ordinary Name andClass of Dye
OXAZINE D Y EIris Blue
Statistic* ofImport and
ManufactureOther Int<tnudiali« ' A ppli-
Lhcd and Notts I (ationCUlHH
Rosoroinol[Bromination)
2-Nitro-m-folualdehyde (C. A. nomen.)
o-Nitro-tolylaldehyde
HCO
O o H . = '
450 DYES CLASSIFIED BY INTERMEDIATES
FORMATION.—m-Tolylaldehyde is nitrated, and then the two isomeric
nitro-compounds separated by distillation under reduced pressure
LITERATURE.—Lange, Zwischenprodukte, #758, 759
Ger. Pat. 113,604 Frdl. 6, 128
Dye Derived from 2-Nitro-m-tolualdehyde
Schvltz Ordinary xame and Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
INDIGO GROUP DYESSS Indigo MLB/T I '14:— 10,730
I '20:— 8272-Nitro-m-tolualdehyde
(2 mols)[Acetone, NaOH]
o-Nitro-foIuene (C. A. nomen.)
0-Xitro-toluol
CH3
] i X 0 * =CrH 7 NO 2 =137
STATISTICS.—Imported '14:— 42,482 lbs.
Manufactured '17:—1,002,822 lbs.
Manufactured J18:—1,240,499 lbs.
Manufactured ' 19:—1,366,599 lbs.
Manufactured '20:—2,173,279 lbs.
FORMATION.—Toluene is nitrated with mixed nitric and sulfuric acidsto a mixture of o- and p-nitro-toluenes. The separation is effectedby means of fractional distillation and freezing—the o-isomer beingdistilled off and the p-body separated as a solid by cooling thestill residue
LITERATURE.—Cain, Intermediate Products (2d Ed.), 32
Lange, Zwischenprodukte, #230-233
DYES CLASSIFIED BY INTERMEDIATES 451
Dyes Derived from o-Nitro-toluene
SchultzNumberfor Dye
513
Ordinary Name andClass of Dye
TRIPHENYL-METHANEDYE
New Fuchsine 0
Statistics ofImport and
Manufacture
I '14:— 300M 'IS:— ?M'19:— ?M'20:— ?
Other IntermediatesUsed and Notes
Anhydro-formaldehyde-o-toluidine orDiamino-o-di-tolyl-methane
o-Toluidine
DyeAppli-cationClass
B
^-Nitro-foluene (C. A. nomen.)
p-Nitro-toluol
= C7H7NO2=137
NO2
STATISTICS.—Imported '14:—very small
Manufactured '17:—567,314 lbs.
Manufactured '18:—670,645 lbs.
Manufactured '19:—1,263,056 lbs.
Manufactured '20:—2,004,089 lbs.
FORMATION.—Toluene is nitrated with mixed nitric and sulfuric acids
to a mixture of 0- and p-nitro-toluene. The separation is effected
by means of fractional distillation and freezing,—the o-isomer
being distilled off and the p-body separated as a solid by cooling
the still residue
LITERATURE.—Cain, Intermediate Products (2d Ed.), 32
Lange, Zwischenprodukte, #230-233
452 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from ^-Nitro-toluene
Schultz 'Numbe,for DyeS
andvClas*
Statistics ofImport arid
Manufacture
Other IntermediatesUsed and Notes
498
TRIPHENYL-METHANE
DYETurquoise Blue I '14:-
I J20:-1,5411 Hydrol or1,407' 4:4 /-Tetraethyl-
diamino-benzoliydrol
DyeAppli-cationClass
B
5-Nitro-o-fo luene-sul fonic Acid (C. A. nomen. >
p-Xi t ro - to luene-o-su l fon ic Ac id
S O 3 H
O2^
STATISTICS.—Manufactured ;20:— ?
FORMATION.—From p-nitro-toluene by sulfonation with oleum
LITERATURE.—Cain, Intermediate Products (2d Ed.), 34
Lange, Zwischenprodukte, #837
Dyes Derived from 5-Nitro-o-toluene-sulfonic Acid
10
Ordinary Same andClJsofDye
STILBEXE D Y E S
Sun YellowDirect Yellow R
Statistics ofImport and
Manufacture
Mikado YellowStilbene Yellow
, I '14:—232,6SSM'17:—420,685M J18:—307,702M719:—4iO,924
1 I '20:— 1,404M J20:—348,S49
, I 'U:— 85,795M 1 8 : — ?M J 1 9 : — ?
Other IntermediatesUsed and Notes
p-Nitro-t oluene-o-sul-fonic Acid (4 mols)
[Alkalies]
p-Nitro-toluene-o-sul-fonic Acid (4 mols)
[Alkalies; Oxidation]
DyeAppli-cationClass
D
D
DYES CLASSIFIED BY INTERMEDIATES 453
Dyes Derived from 5-Nitro-o-toluene-sulfonic Acid (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
STILBENE DYES(continued)
Mikado OrangeChloramine
Orange G
Diphenyl Citronine G
I J14:— 26,010M'17:— ?M'18:— ?M'19:— ?M'20:— 38,2S7
Polychromine BDiphenyl Orange RR M
Diphenyl Chrysoine
Chicago Orange G
Curcuphenine
Chlorophenine
Statistics ofImport and
Manufacture
I '14:— 16,11318:— ?
I '14:— 9,898
Other IntermediatesUsed and Notes
p-Mtro-toluene-o-sul-ionic Acid (4 mols)
[Alkalies; Oxidation]
p-Nitro-toluene-o-sul-fonic Acid (2 mols)
Aniline (2 mols)
p-Nitro-toluene-o-sul-fonic Acid (2 mols)
p-Phenylene-diamine(2 mols)
p-Nitro-toluene-o-sul-fonic Acid (2 mols)
p-Amino-phenol(2 mols)
[Ethylation]
Benzidine
p-Ni tro-toluene-o-sul-fonic Acid (4 mols)
Dehydro-thio-p-tolui-dine-sulf onic Acid(2 mols)
p-Nitro-toluene-o-sul-f onic Acid (4 mols)
Dehydro-thio-p-tolui-dine-sulfonic Acid(2 mols)
[Reduction]
454 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 5-Nitro-o-toluene-sulfonic Acid (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
205
206
207
MONOAZO DYESDiphenyl Chrysoine
RR
Diphenyl CatechineG
Diphenyl FastBrown G
I '14:— S,642
I '14:— 992
p-Xitro-toluene-o-sul-fonic Acid (2 mols)
p-Phenylene-diamine(2 mols)
Phenol[Ethylation]
p-Xitro-toluen e-o-sul-fonic Acid (2 mols)
p-Phenylene-diamine(2 mols)
Dimethyl-gamma Acid
p-Nitro-toluene-0-sul-fonic Acid (2 mols)
p-Phenylene-diamine(2 mols)
Phenyl-gamma Acid
D
D
^-Nitro-toluene-o-sulfonic Acid (CHZ=1)
See, 5-Xitro-o-toluene-sulfonic Acid (C. A. nomen. SOJEI
2-Nitro-^-foluidine (C. A. nomen.
m-Nitro-p-toluidine (CH3 = 1)
N H 2
CH 3
STATISTICS.—^Imported '14:—10,513 lbs.Manufactured '17:— ?Manufactured ' 18:—24,415 lbs.Manufactured 19:—58,454 lbs.Manufactured '20:—71,197 lbs.
DYES CLASSIFIED BY INTERMEDIATES
FORMATION.—From acetyl-p-toluidine by nitration
LITERATURE.—Cain, Intermediate Products (2d Ed.), 58Lange, Zwischenprodukte, #790
Dye Derived from 2-Nitro-^-toluidine (iV#2=-0
455
SchulteNumberjor Dye
73
Ordinary Name andClass of Dye
MONOAZO DYEPigment Fast
RedHLLithol Fast Red RLLithol Fast Scarlet
Statistics ojImport and
Manufacture
I 14:— 49,708M'17:— ?M'18:— ?M'19:— ?I '20:— 1,001M'20:— ?
Other IntermediatesUsed and Notes
/3-Naphthol
DyeAppli-cationClass
CL
3-Nitro-£-foluidine (C.A.nomen.
o-Nitro-p-toluidine (CHz—1)
STATISTICS.—20,737 lbs. imported in fiscal year 1914
FORMATION.—From dinitro-toluene by partial reduction, using iron andsulfur dioxide
LITERATURE.—Lange, Zwischenprodukte, #536, 539, 790, 791
5-Nitro-o-tfoluidine (C. A. nomen. NH2 =1)
p-Nitro-o-toluidine (CH3 = 1)
NH2
STATISTICS.—Imported '14:—30,642 lbs.Manufactured '20:— ?
456 DYES CLASSIFIED BY INTERMEDIATES
FOR?V£ATION.—From o-toluidine by nitration
LITERATURE.—Cain, Intermediate Products (2d Ed.), 5&Lange, Zwischenprodukte, y790
Dyes Derived from 5-Nitro-o-toluidine (NH2 =1)
SckvltzNumberfor Dye
8
72
Ordinary Name andClass of Dye
NITRO DYEPigment Chlorine
MONOAZO DYEPigment Orange R
Statistics ofImport arid
Manufacture
M'19:— ?M720:— ?
Other IntermediatesUsed and Notes
5-Xitro o-toluidine(2 mols)
/9-Xaphthol
DyeAppli-cationClass
CL
CLMF
m-Nitro-^-toluidine (CHZ=1)
See, 2-Nitro-p-toluidine (C. A. nomen. NH2~1)
o-Nitro-^-tolnidine (CiJ3=i)
See, 3-Nitro-p-toluidine (C. A. nomen.
^-Nitro-o-toluidine (CHZ=1)
See, 5-Nitro-o-toluidine (C. A. nomen.
o-Nitro-toluol
See, o-Nitro-toluene (C. A. nomen.)
£-Nitro-toluol
See, p-Nitro-toluene (C. ^i. nomen.)
o-Nitaro-toIylaldehyde
See, 2-Nitro-m-tolualdehyde (C A. nomen.)
3-Nitro-l: 2: S-taihydroxy-anthraquinone
See, 3-Nitro-flavopurpurin (C. A. nomen.)
DYES CLASSIFIED BY INTERMEDIATES 457
NWAcid
See, Nevile-Winther's Acid
Ortho=o
Note.—This is not considered in the alphabetical arrangement, e.g.,orlho-Toluidine is indexed as o-Toluidine under "T." However, o-Toluidine precedes p-Toluidine
Oxy-compounds
See, Hydroxy-compounds
Oxy-juglone
See, Naphthazarin
a-Oxy-naphthoic Acid
See, l-Hydroxy-2-naphthoic Acid
/3-Oxy-naphthoic Acid
See, 3-Hydroxy-2-naphthoic Acid
a-Oxy-naphthoic-sulf onic Acid
l-Hydroxy-2-napMhoic-4-sulfonic Acid {not considered herein)
/3-Oxy-naphthoic-sulf onic Acid L
2-Hydroxy-3-naphthoic-6-sulfonic Acid {not considered herein)
/3-Oxy-naphthoic-sulf onic Acid S
2-Hydroxy-3-naphthoic-8-sulfordc Acid {not considered herein)
Note,—This is not considered in the alphabetical arrangement, e.g., para-Nitro-aniline is indexed as p-Nitro-aniline under "N." However, p-Nitro-aniline follows m-Nitro-aniline
458 DYES CLASSIFIED BY INTERMEDIATES
Peri AcidSee, l-Naphthylamine-8-sulfonic Acid
Peri-naphthylene-diamine1: 8-Naphthylene-diamine (iiot considered herein)
PhenanthraquinoneSee, Phenanthrene-quinone
Phenanthrene-quinone (C. .4. nomen.)
9:10-Dihydro-9:10-diketo-phenanthrene
Phenanthraquinone
0 0
= 208
FORMATION.—From phenanthrene by oxidation with sodium bichromateand sulfuric acid
LITERATURE.—Lange, Zwischenprodukte, ^648Green, Organic Coloring Matters (1908), 65
SchuiizNumberfor Dye
668
Dye Derived
Ordinary Xame andClass of Dye
AZINB DYEFlavinduline 0
from Phenanthrene-quinone
Statistics ofImport arid
Manufacture
I 14:— 660
Other IntermediatesUsed and Notes
o-Amm o-diphenyl-amine
DyeAppli-cationClass
B
Phenanthroquinolinone (C. A. noynen.)
See, Benzanthrone-quinoline
^-Phenetidine (C A. nomen.)
p-Amino-phenol Ethyl Ether
NH2
DYES CLASSIFIED BY INTERMEDIATES 459
STATISTICS.—Imported '14:—125,524 lbs.Manufactured ' 17:— ?Manufactured '18:— ?Manufactured '19:— ?
FOKMATION.—From p-amino-phenol by ethylation of the hydroxyl.Before ethylation the amino group is protected; for example, byforming the benzylidine compound by treatment of the p-amino-phenol with benzaldehyde
LITERATURE.—Lange, Zwischenprodukte, #590
Dye Derived from ^-Phenetidine
SchultzNumberfor Dye
584
Ordinary Name andClass of Dye
XANTHONE DYEFast Acid Blue R
Statistics ofImport and
Manufacture
I '14:— 4,022I '20:— 130
Other IntermediatesUsed and Notes
p-Phenetidine (2 mols)3:6-Dichloro-plithalic
AnhydrideResorcinol (2 mols)[PC15; Sulfonationl
DyeAppli-cationClass
A
Phenol ((7. A. nomen.)
Carbolic Acid
= C6H6O=94
STATISTICS.—Imported '14:— 10,108,781 lbs.Manufactured '17:— 64,146 499 lbs.Manufactured '18:—106,794,277 lbs.Manufactured '19:— 1,543,659 lbs.Manufactured '20:— ?
FORMATION.—(1) By distillation from coal tar. (2) By synthesis frombenzene, in which case the benzene is suKonated to benzene-sulfonicacid, which is then fused with caustic soda
LITERATURE.—Cain, Intermediate Products, 104Lange, Zwischenprodukte, #142-145
400 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Phenol
SchultzNumberfor Dye
5
125
205
303
304
315
319
373
Ordinary Name andClass of Dye
NITRO DYEPicric Acid
MONOAZO DYESDiazine Black
DiphenylChrysoine RR
DISAZO DYESBrilliant YellowPaper Yellow
Chrysophenine G
Congo Orange G
Diamine Scarlet B
Congo Orange R
Statistics ofImport and
Manufacture
M'19:— ?M '20:— ?
I '14:— 2,630I '20:— 701
I '14:-27S,000M'17:— ?M'lS:— 1,664M'19:— 4S,723I '20:— 126M'20:— 91,218
I '14:—157,799M'17:— ?M'18:— 41,663M'19:— 86,795I '20:— 3,661
M'20:—247,202
I '14:— 1,623I '20:— 75
I '14:— 41,175I '20:— 10,565
I '14:— 7,027I '20:— 254
Other IntermediatesUsed and Notes
p-Tolylene-diamineo-ToluidineAniline or
o-Toluidineor
[Safranine]
p-Nitro-toluene-o-sul-fonic Acid
p-Phenylene-diairrine
Diarmn o-stilbene-disuKonic Acid
Phenol (2 mols)
Diamino-stilbene-disuL-fonic Acid
Phenol (2 mols)[Ethylation]
BenzidineAmino-R Acid[Ethylationl
BenzidineGAcid
TolidineAmino-R Acid[Ethylation]
DyeAppli-cationClass
B
B
D
DA
D
D
D
D
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Phenol {continued)
461
SchultzNumberfor Dye
404
431
464
467
470
474
515
Ordinary Name andClass of Dye
DISAZO DYES(continued)
Diamine Yellow N
Diamine GoldenYellow
TBISAZO DYESErie Direct
Green ET
Diphenyl Green G
Chloramine Green B
Diamine Green BOxamine Green B
TRIPHENYL-METHANEDYES
Methyl Violet
Statistics ofImport and
Manufacture
M'17:— ?I '20:— 313
M'17:— ?M'18:— ?M'19:—• 69,700M'20:— ?
I '20:— 2,205
I '14:— 1,675M19:— ?M'20:— ?
I 14:— 77,100M'17:— ?M'18:—295,147M'19 :—305,854I '20:— 2,460M'20:-420,138
I 14:—255,063M17:—375,107M18:—632,196M19:—574,436I '20:— 3,312
M'20:—600,873
Other IntermediatesUsed and Notes
Ethoxy-benzidineSalicylic Acid[Ethylation]
1:5-Naphthylene-dia-rnine-3:7-disulfonicAcid
Phenol (2 mols)[Ethylation]
BenzidineHAcidAniline
BenzidineHAcido-Chloro-p-nitro-
aniline
BenzidineHAcid2: 5-Dichloro-aniline
BenzidineHAcidp-Nitro-aniline
Dimethyl-aniline(3 mols)
DyeAppli-cationClass
D
D
D
D
D
D
B
462 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Phenol {continued)
SchidtzNumberjor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
Manufacture
517
TRIPHENYL-METHANEDYES
(continued)Methyl Violet 5BBenzyl Violet
519
555
556
693
718
Methyl Green
Aurine
Red Coralline
AZINE DYEMilling Blue
SULFUB DYESSt. Denis Black B
I '14:— 22,3S7M'17:— ?
'20:— 3,313
I '14:-M'18:-I '20:-
7S4
336
I '14:— 3,082
Other IntermediatesUsed and Notes
[Benzylation of MethylViolet]
orDimethyl-aniline
(3 mols)Benzyl Chloride
[Methyl Chloride ofMethyl Violet]
orDimethyl-aniline
(3 mols)[Methyl Chloride]
Phenol (3 mols)[Heated with oxalic and
sulfuric acids]
[Aurine treated withammonia]
orPhenol (3 mols)[Heated with oxalic and
sulfurie acid; treatedwith ammonia]
Aniline (2 mols)Phenyl-a-iiaphthyl-
amine (2 mols)[Sulfonation]
p-Phenylene-diamineNitro-benzene
DyeAppli-cationClass
B
B
CL
CL
M
DYES CLASSIFIED BY INTERMEDIATES 463
Dyes Derived from Phenol (continued)
iSchultzNumberfor Dye
732
775
Ordinary Name andClass of Dye
SULPUE DYES(continued)
Autogene Black
ANTHEAQUINONE ANDALLIED DYES
Alizarin DarkGreen W
Statistics ofImport and
Manufacture
I 14:— 7,495
Other IntermediatesUsed and Notes
4-Amino-4/-hydroxy-diphenylamine
or2: 4-Diamino-4'-hy-
droxy-diphenylamine[S2CI2; S+Na^S]
Naphthazarinor
Dirdtro-naphthalene
DyeAppli-cationClass
S
M
Phenyl-^-amino-benzyl-o-toluidine (CH3=1)
See, ^-Benzyl-JV^phenyl^-m-tolylene-diamine
Phenyl-/>-amino-ethyl-o-toluidine (CH3 =1)
See, N^Ethyl-N^phenyM-m-tolylene-diamine
4-Phenylamino-4/-hydroxy-diphenylamine
p-(p-Anilino-anilino)-phenol (C. A. nomen.)
= 276
FOEMATION.—(1) From p-amino-diphenylamine and phenol by oxida-tion in acid solution and then reduction of the indophenol.(2) From diphenylamine and p-amino-phenol (p-nitroso-phenol)by oxidation and then reduction of the indophenol
LITEEATUEE.—Cain, Intermediate Products (2d Ed.), 76Lange, Zwischenprodukte, #1721Lange, Schwefelfarbstoffe, 161
464 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from l-Phenylamino^'-hydroxy-diphenylainine
SchultzNumberfor Dye
735
Ordinary Name andClass of Dye
SULFUR DYEPyrogene Indigo
Statistics ojImport and
Manufacture
I '14:— 22,661
Other IntermediatesUsed and Notes
[S+NaaS]
DyeAppli-cationClass
S
l-Phenylairdno^'-liydroxy-Cphenyl-S'-tolylainiiie)
4-(p-Anilino-anilino)-o-cresol (C. A. nomen. OH = 1
CH3
•XH
N.—From p-amino-diphenylamine and o-cresol by oxidationand subsequent reduction of the indophenol formed
LITERATURE.—Lange, Zwischenprodukte, #1721
Dye Derived from 4-Phenylaj3ciino-4'-hydroxy-(phenyl-3A-tolylaniine)
Numt Ordinary Name andfor Dye Cla^sofDye
SULFUR DYE735 Pyrogene Indigo
Statistics ofImport and
Manufacture
I 314:— 22,661
Other IntermediatesUsed and Notes
[S+NaaS]
DyeAppli-cationClass
s
2-Phenylamino-8-iiaphthol-6-sulf onic Acid
See, Phenyl-gamma Acid
Phenyl-m-amino-phenol
See, m-Hydroxy-diphenylamine
Phenyl-^-amino-o--toluidine
See, iY^Phenyl-^r-m-tolylene-diamine
DYES CLASSIFIED BY INTERMEDIATES 465
Phenyl-azo-aniline (C. A. nomen.)
See, Amino-azo-benzene
m-Phenylene-diamine
N H 2
J N H 3
STATISTICS.—Manufactured '17:-—220,956 lbs.Manufactured '18:—641,299 lbs.Manufactured '19:—609,789 lbs.Manufactured '20:—658,313 lbs.
FORMATION.—From m-dinitro-benzene by reduction with iron andhydrochloric acid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 85Lange, Zwischenprodukte, #550
Dyes Derived from m-Phenylene-diamine
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
33MONOAZO DYES
Chrysoidine Y
88
89
Acid AnthraceneBrown R
MetachromeBrown B
I '14:— 63,303M'17:—195,756W18:—376,495M'19:—314,581M'20:—585,648
I '14:— 33,053M'17:— ?M'19:~- ?I ' 20:— 1,400M'20:— ?
I '14:— 1,001M'17:— ?M'18:—349,961MJ19:— ?M'20:—192,914
Aniline B
Picramic Acid[Substituted phenylene-diamine-suHonic Acids]
Picramic Acid
ACr
M
466 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 7n-Phenylene-diamine (continued)
SchultzNumberfor Dye
154
190
208
209
239
283
285
329
Ordinary Name andClass of Dye
MONOAZO DYES(continued)
Acid AlizarineBrown B
Palatine ChromeBrown W
Alkali BrownBenzo Brown 5B,
DISAZO DYESLeather BTown
Terracotta FC
AzotolC
Bismarck Brown
Toluylene Brown G
Diamine Brown V
I '14:— 18,264M'17:— ?M'lS:— ?M'19:— ?I '20:—M'20:—
M'19:—M '20:—
Statistics ofImport and
Manufacture
845
?2,987
I '14:— 500M'19:— ?MJ20:— ?
I '14:— 551
Other IntermediatesUsed and Notes
o-A m in o-phenol-p-sulfonic Acid
Dehydro-thio-p-tolui-dine-sulfonic Acid
or
I '14:— 35,020M'17:—309,857M 'IS:—378,208M'19:^12,574M'20:—514,218
M'19:— ?
Primuline
?>-Phenylene-diamme(2 mols)
Primuline or Dehydro-thio-p-toluidine-sulf onic Acid
Naphthionic Acid
p-Amino-acetanilidej3-Naphthol
ifl-Phenylene-diaTnin e(3 mols)
3:5-Diamino-2>-toluene-sulfonic Acid
BenzidineGamma Acid
DyeAppli-cationClass
M
D
B
MF
B
D
D
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from m-Phenylene-diamine (continued)
467
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
TRISAZO DYESJanus Brown B
Columbia Black FF
Isodiphenyl Black R
Diaminc Bronze G
Trisulfon Brown B
Trisulf on Brown G
Trisulfon. Brown GG
I 14:—402,997M18:— ?M19:— ?I '20:— 23,350MJ20:— ?
:— 4,449
I 14:— 16,781I '20:— 38,616
I 14:— 1,323
I 14 — 7,562I '20:— 38,411
Trimethyl-m-amino-phenyl-arnmoniumChloride orp •Amino-benzyl-di-ethylamine
a-Naphthylamine orm-Toluidine
Aniline
l-Naphthylamine-6-cmd7-sulfonic Acids
p-Phenylene-diamineGamma Acid
p-Phenylene-diamineGamma AcidRcsorcinol
BcnzidineSalicylic AcidH Acid
BenzidincSalicylic Acid2R Acid
TolidineSalicylic Acid2R Acid
DianisidineSalicylic Acid2R Acid
468 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from m-Phenylene-diamine {continued)
SchultzNumberfor Dye
458
461
462
469
476
479
Ordinary Name andClass of Dye
TRISAZO DYES{continued)
Carbon Black
Coomassie UnionBlack
Erie Direct Black GXDirect Deep
Black EW
Chloramine Black N
Benzamine Brown3GO
Dianil Black R
Statistics ofImport and
Manufacture
I '14:—1,246,53C
M'17:— ?M'lS:— ?M'19:—
7,250,007M'20:—
7,736,994
I '14:— 39,600M'19:— ?I '20:— 1,763M'20:— ?
I '14:— 16,9SSM'17:— ?M'18:— ?
M'20:—623,757
Other IntermediatesUsed and Notes
p-Phenylene-diamine-sulfonic Acid (from p-nitro-aniline-o-sul-fonic Acid)
l-Xaphthykmine-6 (7)-sulf orric Acid
??2-Phenylene-diamine(2 mols)
1:4-Xaphthylene-dia-mine-2-sulf onic Acid
Gamma AcidTn-Phenylene-diaTnine
(2 mols)
BenzidineAnilineHAcid
BenzidineH Acid2:5-Dichloro-aniline
BenzidineSulfanilic AcidSalicylic Acid
BenzidineNaphthionic AcidChromotropic Acid
DyeAppli-cationClass
D
D
D
D
D
D
DYES CLASSIFIED BY INTERMEDIATES 469
Dyes Derived from m-Phenylene-diamine (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
485
486
487
488
490
491
492
TETRAKISAZO DYES
Benzo Brown G
Direct Brown J
Benzo Brown B
Toluylene Brown ~R
I '14:— 41,905M'17:— ?M'18:— ?M 1 9 : — 83,506I '20:— 2,286M'20:—109,648
I '14:— 3,640
I '14M'20
:— 438• ?
I ' 1 4 : — 2 0 1
Cotton Brown A I ' 1 4 : — 2 9 , 0 7 4
Dianil Black PR
Anthracene AcidBrown B
S u l f a n i U c A c i d (2 m o l s )
m - P h e n y l e n e - d i a m j n e
(3 m o l s )
m - A m i n o - b e n z o i c A c i d(2 m o l s )
m - P h e n y l e n e - d i a i n i n e
(3 m o l s )
N a p h t h i o n i c A c i d(2 m o l s )
m - P h e n y l e n e - d i a m i n e
(3 m o l s )
N a p h t h i o n i c A c i d(2 m o l s )
3 : 5 - D i a m i n o - p - t o l u e n e -
s u l f o n i c A c i dm - P h e n y l e n c - d i a m i n e
(2 m o l s )
B e n z i d i n eN a p h t h i o n i c A c i d
(2 m o l s )m - P h e n y l e n e - d i a m i n e
(2 m o l s )
B e n z i d i n e - s u l f o n i c A c i dG a m m a A c i d (2 m o l s )m - P h e n y l e n e - d i a m i n e
(2 m o l s )
A m i n o - s a l i c y l i c A c i d
(2 m o l s )
l - N a p h t h y l a m i n e - 6 - s u l -
f o n i c A c i d (2 m o l s )
470 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from m-Phenylene-diamine {continued)
SchultzNumberfor Dye
607
669
Ordinary Name andClass of Dye
ACRIDINE DYERheonine
AZINE DYENeutral Violet
Statistics ofImport and
Manufacture
I '14:— 19,704
Other IntermediatesUsed and Notes
Ketone
Dimethyl-p-phenylene-diamine (2 mols)
[Oxidation]
DyeAppli-cationClass
B
^-Phenylene-diamine
Note.—In a number of cases where p-phe?iylene-diamine was apparentlyused, actually its acetyl-derivative p-amino-acetanilide, or even p-nitro-aniline, was employed; and after the first coupling, the second amino groupwas then freed and diazoiized. Here both compounds are generallyindexed.
NH2
NH2
— C6H8N2 =
STATISTICS.—Imported '14:— 11,088 lbs.
Manufactured '17:—272,056 lbs.Manufactured '18:—215,148 lbs.Manufactured '19:—234,332 lbs.Manufactured '20:— ?
FORMATION.—(1) From amino-azo-benzene by reduction. (2) From p-nitro-aniline by reduction
LITERATURE.—Cain, Intermediate Products (2d Ed.), 87
Lange, Zwischenprodukte, #552-555
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from ^-Phenylene-diamine
471
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
13
61
205
206
207
208
290
291
STILBENE DYEPolychromine BDiphenyl Orange RR M
I '14:— 16,113:— ?
MONOAZO DYESVictoria Violet I '14:— 52,365
M'17:— ?M'18:~~ ?M'19:—105,086I '20:— 2,182M'20:— ?
Diphenyl ChrysoineRR
Diphenyl CatechineG
Diphenyl FastBrown G
DISAZO DYESLeather Brown
Violet Black
Azo AlizarinBordeaux W
I '14:- 8,642
I '14: 992
I '14M'19M'20
:— 500:— ?:— ?
p-Phenylene-diamine(2 mols)
p-Nitro-toluene-o-sul-foDic Acid (2 mols)
Chromotropic Acid[The p-Phenylene-dia-
mme from p-Nitro-aniline or p-Amino-acetanilide]
p-Phenylene-diamine(2 mols)
p-Nitro-toluene-0-sul-fonic Acid (2 mols)
Phenol[Ethylation]
p-Phenylene-diamine(2 mols)
p-Nitro-toluene-o-sul-f onic Acid (2 mols)
Dimethyl-gamma Acid
p-Phenylenc-diamine(2 mols)
p-Nitro-toluene-o-sul-fonic Acid (2 mols)
Phenyl-gamma Acid
p-Phenylene-diamine(2 mols)
w-Phcnylene-diamine
Nevile-Winther^s Acida-Naphthylamine
Salicylic AcidNevile-Winther's Acid
472 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from ^-Phenylene-diamine (continued)
SchvltzNumberor Dye
292
436
437
621
695
701
702
713
714
718
Ordinary Name andClass of Dye
DISAZO DYES(continued)
Azo AlizarinBlack I
TRISAZO DYESColumbia Black FF
Isodiphenyl Bkck R
OXAZIXE DYECresyl Blue 2BS
Azrs"E DYESParaphenylene
Violet
Paraph enyleneBlue R~
Para Blue
SULFUR DYESThiophor Bronze 5G
Thiophor YellowBronze C
St. Denis Black B
Statistics ofImport and
Manufacture
I J14:—402,997M'lS:— ?M'19:— ?I '20:— 23,350^l '20:— ?
I J20:— 337
M'19:— ?
Other IntermediatesUsed and Notes
Salicylic AcidChromotropic Acid
l-Naphthylamine-6-anrf-7-sulfonic Acids
Gamma Acid?w-Phenylene-diamine
Gamma AcidResorcinolw-Phenylene-diamine
5-Dimethylamino-2-nitroso-p-cresol
a-Amino-azo-napli-thalene
Amino-azo-benzene
Aniline (3-4 mols)o-Toluidinep~Toluidine
or[Spirit Blue]
[p-Amino-acet-black][Sulfur]
p-A m in o-acetanilideBenzidine[Sulfur]
PhenolNitro-benzene[S2CI2, S, Na^S]
DyeAppli-cationClass
M
D
D
B
B
B
B
S
S
s
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from ^-Phenylene-diamine (continued)
473
SchultzNumberfor Dye
727
923
Ordinary Name andClass of Dye
Auronal Black B
ANILINE BLACKGROUP
Ursol D, DB
Statistics ofImport and
ManufactureOther Intermediates
Ut>ed and Notes
l-Chloro-2:4-dinitro-benzene
[Glycerol; S+Na^S]
[Oxidation on hair]
DyeAppli-cationClass
S
Fur
m-Phenylene-diamine-disulfonic Acid
4: 6-Diamin.o-m-benzene-disulfonic Acid (C A. nomen.
NH2
= C6H8N2O6S2=268
SO3H
FOEMATION.—From ra-phenylene-diamine hydrochloride by treating itwith five parts of 40 per cent oleum, heating at 100° for severalhours, then at 120° for 6-10 hours
LITERATURE.—Lange, Zwischenprodukte, #1146, 1147Green, Organic Coloring Matters (1908), 36
Dyes Derived from m-Phenylene-diamine-disulfonic Acid
SchultzNumberfor Dye
192
210
306
Ordinary Name andClass 0] Dye
MONOAZO DYESCotton Orange G
DISAZO DYESCotton Orange R
Pyramine Orange 3G
Statistics ofImport and
Manufacture
I 14:— 1,877
I '14:— 16,459I '20:— 51
I ' 1 4 : - 7,863I '20— 396
Other IntermediatesUsed and Notes
Primuline
Primuline-sulfonic AcidMetanilic Acid
BenzidineNitro-m-phenylene-
diamine
DyeAppli-cationClass
D
D
D
474 DYES CLASSIFIED BY INTERMEDIATES
^-Phenylene-diamine-sulfonic Acid
2: 5-Dtamino~&enzene-sulfonic Acid (C A. nomen.)
Note.—As a rule this compound is not used as such, being formed as the
azo derivative in the dye molecule from the reduction of the azo derivative of
p-nitro-aniline-o-sulfonic add
NH2
{ 1SO3H = :
NIL
FORMATION.—From p-nitro-aniline-o-sulfonic acid by reduction
LITERATURE.—Lange, Zwischenprodukte, #920-924
SchultzNumberfor Dye
458
Dye Derived from
Ordinary Name andClass of Dye
TRISAZO DYECarbon Black
^-Phenylene-diamine-sulfonic Acid
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
l-Naphthylaminc-6(7)-sulf onic Acid
w-Phenylene-(Toly-lene-)diamine or1:3-Naphthylcne-diamine-6-sulfonicAcid (2 mols)
DyeAppli-cationClass
D
Phenyl-gamma Acid
2-Phenylamino-8-naphthol-6-sulfonic Acid
7-Anilino-l-naphthol-3-sulfonic Acid (C A. nomen.)
HO
HO3s = 315
DYES CLASSIFIED BY INTERMEDIATES 4 75
FORMATION.—From gamma acid (2-amino-8-naphthol-6-sulfonic acid)
by heating with aniline and aniline hydrochloride at 160°
LITERATURE.—Lange, Zwischenprodukte, #2846-2847
Dyes Derived from Phenyl-gamma Acid
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManvfactureOther Intermediates
Used and Notes
DyeAppli-cationClass
207
349
445
MONOAZO DYEDiphenyl Fast
Brown G
DISAZO DYESDiamine Brown B
TRISAZO D Y ECrumpsall Direct
Fast Brown 0
I '14:— 992
I '20:— 24
p-Nitro-toluene-o-sul-fonic Acid
p-Phenylene-diamine
BcnzidineSalicylic Acid
BenzidineSalicylic AcidAniline
D
D
D
Phenyl-glycine
iV-Phenyl-tflycine ( C A. nomen.)
N H . C H 2 . C O O H
STATISTICS.—Manufactured '17:— ?
Manufactured '19:— ?
Manufactured '20:— ?
FORMATION.—By action of chloro-acetic acid on aniline
L I T E R A T U R E . — C a i n , Intermediate Products (2d Ed . ) , 153
Langc, Zwischenprodukte, #96-109, 111
476 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Phenyl-glycine
SchultcX umberfor Dye
874
876
877
878
879
SSO
Ordinary Xnnie andCla<*> of Dye
INDIGO GROUP DYESIndigo
Indigo MLBIndigo White
Indigotine
Indigotine P
Brom IndigoRathjen
Indigo MLB, RR
Helindone Blue BBIndigo RB
I
MM
MiIM
i
IM
M
M
IM
1
ii
iM
i
IM' I
/Statistics ofImpoit andManufacture
'14
'17'IS
'19
:—S,507,359
:—274,771:—3,0S3,SSS
:—S,S63,824
'20—520,347'20
'14'17
'IS
'19
"20'20
'14'20
'14717'20
MT20
;18,178,231
:— 19,329:—1,S76,7S7
:—1,434,703
:—1,699,670
:— 5,512•1,395,000
:— 53,640:— ?
:— 6,S56:— 14,100:— 3,691:— ?
Other IntermediatesUsed and Notes
Phenyl-glycine (2 mols)[Sodamide]
Phenyl-glycine (2 mols)[Sodamide, Reduction]
or[Indigo, Reduction]
Phenyl-glycine (2 mols),etc.
or[Indigo, Sulfonation]
Phenyl-glycine(2 mols), etc.
or[Indigo, Sulfonation]
Phenyl-glycine(2 mols), etc.
or[Indigo, Bromination]
Phenyl-glycine(2 mols), etc.
or[Indigo, Bromination]
DyeAppli-cationClass
V
V
A
A
V
V
DYES CLASSIFIED BY INTERMEDIATES 477
Dyes Derived from Phenyl-glycine {continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
INDIGO GROUP DYES(continued)
Dianthrene Blue 2BBromo Indigo FBCiba Blue 2B
Indigo MLB/5BCiba Blue G
Indigo MLB/6BIndigo KG
Brilliant IndigoBASF/2B
Brilliant IndigoBASF/B
Brilliant IndigoBASF/G
Indigo Yellow 3G
I '14:M'19:I '20:
I '14:I '20:
I '14:-I '20:-M'20:
Statistics ofImport and
Manufacture
16,880
35,857
1,3561,008
3,1914,130
I '14:— 4,518
I '14:I '20:
8,1173,503
I 14:— 12,057
Other IntermediatesUsed and Notes
Phenyl-glycine(2 mols), etc.
or[Indigo, Bromination]
Phenyl-glycine(2 mols), etc.
or[Indigo, Bromination]
Phenyl-glycine(2 mols), etc.
or[Indigo, Bromination]
Phenyl-glycine(2 mols), etc.
or[Indigo, Chlorination,
Bromination]
Phenyl-glycine(2 mols), etc.
or[Indigo, Chlorination]
Phenyl-glycine(2 mols), etc.
or[Indigo, Chlorination,
Bromination]
Phenyl-glycine(2 mols), etc.
Benzoyl chlorideor
[Indigo, Benzoylchloride]
47S DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Phenyl-glycine (continued)
Fchult: si, - \- J Statistics of
for Dye ^ yc Manufacture
INDIGO GEOCP DYE{continued)
890 ' Ciba Yellow G I '14:— 4S! i
>i1 j
!
Other IntermediatesUsed and Notes
Phenyl-glycine(2 inols), etc.
Benzoyl chlorideor
[Indigo, Benzoylchloride, Bromina-tion]
DyeAppli-cationClass
V
Phenyl-glycine-o-carboxylic Acid
A'-(Carbox\*-methyl)-anthranilic Acid (C. A. nomen.)
COOH
V
FORSCATION.—Phthalic anhydride is coaverted through phthalimideinto anthranilic acid. This latter by reaction with chloro-aceticacid form? the phony 1-glycine-o-earboxy acid
.—Lange, Zwischenprodukte, ?379, 383-393
Dyes Derived from Phenyl-glycine-o-carboxylic Acid
for Dy* Cla** <* D^c Manufacture
INDIGO GROUP DYESS74 Indigo I '14:—
, ; 8,507,359! M17:—274,771
M '18:—i 3,083,888jM '19:—! 8,863,824
i 11 '20:—520,347!M*20:—
J , 18,178,23!
Other IntermediatesUsed and Notes
Phenyl-glycme-a-ca«r-boxylic Add (2 mols)
[Sodarnide]
DyeAppli-cationClass
V
DYES CLASSIFIED BY INTERMEDIATES 479
Dyes Derived from Phenyl-glycine-o-carboxylic Acid (continued)
SchultzNumberfor Dye
876
877
878
879
880
881
Ordinary Name andClass of Dye
INDIGO GROUP DYES{continued)
Indigo MLBIndigo White
Indigotine
Indigotine P
Bromo IndigoRathjen
Indigo MLB/RR
Helindone Blue BBIndigo RB
Manthrene Blue 2BBromo Indigo FBCiba Blue 2B
IM
M
M
IM
I
Statistics ofImport and
Manufacture
1417:
18:
19:
'20:'20:
14:-M'20:-
IMIM
IMI
14:-17:-'20:-'20:-
14:19:'20:
— 19,329—1,876,787
—1,434,703
—1,699,670— 5,512—1,395,000
- 53,610- ?
- 6,856- 14,100- 3,691- ?
- 16,880- ?— 35,857
Other IntermediatesUsed and Notes
Phenyl-glycine-o-car-boxylic Acid (2 mols)
[Sodamide, Reduction]or
[Indigo, Reduction]
Phenyl-glycine-o-car-boxylic Acid (2 mols),etc.
or[Indigo, Sulfonation]
Phenyl-glycine-o-car-boxylic Acid (2 mols),etc.
or[Indigo, Sulfonation]
Phenyl - gly cine - o - car-boxylic Acid (2 mols)etc.
or[Indigo, Bromination]
Phenyl - gly cine - o - car-boxylic Acid (2 mols)",etc.
or[Indigo, Bromination]
Phenyl - glycine - o - car-boxylic Acid (2 mols),etc.
or[Indigo, Bromination]
Dy,Appli-cationClass
V
A
A
V
V
V
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Phenyl-glycine-o-carboxylic Acid (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
INDIGO GROUP DYES(continued)
Indigo MLB/5BCiba Blue G
Indigo MLB/6BIndigo KG
Brilliant IndigoBASF/2B
Brilliant IndigoBASF/B
Brilliant IndigoBASF/G
Indigo Yellow 3G
I '14:-I '20 >
I '14:-I '20:-M'20:-
I '14 >
Statistics ofImport and
Manufacture
4,3561,002
3,1914,130
4,518
I '14:-I '20:-
8,17,3,503
I '14:— 12,057
Other IntermediatesUsed and Notes
Phenyl - glycine - o - car-boxylic Acid (2 mols),etc.
or[Indigo, Bromination]
Phenyl - glycine - o - car-boxylic Acid (2 mols),etc.
or[Indigo, Bromination]
Phenyl - glycine - o - car-boxylic Acid (2 mols),etc.
or[Indigo, Chlorination,
Bromination]
Phenyl - glycine - o - car-boxylic Acid (2 mols),etc.
or[Indigo, Chlorination]
Phenyl - glycine - o - car-boxylic Acid (2 mols)etc.
or[Indigo, Bromination,
Chlorination]
Phenyl - glycine - o - car-boxylic Acid (2 mols),etc.
Benzoyl chlorideor
[Indigo, Benzoylchloride^
DyeAppli-cationClass
DYES CLASSIFIED BY INTERMEDIATES 481
Dyes Derived from Phenyl-glycine-o-carboxylic Acid (continued)
SchultzNumberfor Dye
890
Ordinary Name andClass of Dye
INDIGO GROUP DYES(continued)
Ciba Yellow G
Statistics ofImport and
Manufacture
V 14:— 48
Other IntermediatesUsed and Notes
Phenvl - glycine - o - car-boxylic Acid (2 mols),etc.
Bcnzoyl chloride[Bromination]
or[Indigo Yellow 3G,
Brominationl
DyeAppli-cationClass
V
Phenyl-hydrazine-^-sulfonic Acid
p-Hydrazino-frenzene-sulfonic Acid (C. A. nomen.)
N H . N H 2
SO3H
STATISTICS.—Manufactured '20:—441,117 lbs.
FOKMATTON.—(1) Sulfanilic acid is diazotized and then reduced withsodium bisulfite. (2) Aniline is diazotized and reduced withsodium bisulfite, forming phenyl-hydrazinc, which is then sulfonatedwith 66° sulfuric acid at 100°
LITEEATURE.—Cain, Intermediate Products (2d Ed.), 49Lange, Zwischenprodukte, #629
SchultzNumberfor Dye
19
20
Dyes Derived from Phenyl-hydrazine-£-sulfonic Acid
Ordinary Name andClass of Dye
PYRAZOLONE DYESFlavazine LFast Light Yellow
Flavazine S
Statistics ofImport and
Manufacture
I '14:— 38,908I '20:— 9,327
I '14:— 81,375I '20:— 1,500
Other IntermediatesUsed and Notes
Aniline[Ethyl Aceto-acetatc]
Aniline[Ethyl Oxal-acetate]
DyeAppli-cationClass
A
A
482 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Phenyl-hydrazine-^-sulfonic Acid {continued)
SchultzNumberjor Dye
23
27
Ordinary Name andClass of Dye
PYRAZOLONE DYES(continued)
Tartrazine
Dianil Yellow 2R
Statistics ofImport and
Manufacture
I '14:—272,477M'17:— ?M'18:— ?MJ19:— ?I '20:— 47,877M;20:—701,722
Other IntermediatesUsed and Notes
Phenyl-hydrazine-p-sulfonic Acid (2 mols)
Dihydroxy-taTtaricAcid
orSulfanilic Acid[Ethyl Oxal-acetate]
Primuline-sulfonic Acid[Ethyl Aceto-acetate]
DyeAppli-cationClass
A
D
l-Phenyl-3-methyl-5-pyrazolone
See, 3-Methyl-l-phenyl-5-pyraz"olone
Phenyl-a-naphthylamine
iV-Phenyl-1-mphthylamine (C A, nomen.)
NH-
STATISTICS.—^Manufactured '17:—Manufactured '18:—Manufactured'19:—Manufactured '20:—
FOKMATION.—From a-naphthylamine hydrochloride and aniline byheating together
LITERATURE.—Cain, Intermediate Products (2d Ed.), 187Cf. Lange, Zwischenprodukte, #2827Thorpe, Die. Chemistry, 3, 587
DYES CLASSIFIED BY INTERMEDIATES
SchultzNumber}or Dye
263
361
559
693
Dyes Derived
Ordinary Name andClass of Dye
DISAZO DYESJet Black R
Sulfonazurine
DlPHENYL-NAPHTHYL-METHANE DYE
Victoria Blue B
AZINE DYEMilling Blue
Prom Phenyl-a-naphthylamine
Statistics ofImport andManufacture
I '14:— 300
I '14:—127,769M'17:— ?M'18:— ?M'19:— ?I }20:-~ 11,782
M'20:— ?
I 14:— 3,082
Other IntermediatesUsed and Notes
Aniline-2:4-disuIfonicAcid
a-Naphthylamine
B enzidine-sulf on-disul~fonic Acid
Phenyl-a-naphthyl-amine (2 mols)
Ketoneor
Hydrol
Aniline (2 mols)Phenyl-a-naphthyl-
amine (2 mols)Phenol[Sulfonation]
DyeAppli-cationClass
A
D
B
M
Phenyl-0-naphthylamine
iV-Phenyl-2-naphthylamine (C A. nomen.)
—NH—-
FORMATION.—From i3-naphthol and aniline (or hydrochloride) byheating together in an open vessel to around 200°
LITERATURE.—Lange, Zwischenprodukte, #2827Thorpe, Die. Chemistry, 3, 599
484 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from Phenyl-i3-naphthylamine
SchultzNumberfor Dye
676
Ordinary Name andClass of Dye
AZINE DYENeutral Blue
Statistics ofImport and
Manufacture
I '14:— 615
Other IntermediatesUsed and Notes
Nitroso-dimethyl-aniline
DyeAppli-cationClass
B
Phenyl-l-naphthylamine-8-sulfonic Acid
8-AniMno-l-naphthalene-sulfonic Acid (C. A. nomen.)
Phenyl-peri Acid
HO3S NH
STATISTICS.—Imported '14:—9,139 lbs.Manufactured '18:— ?Manufactured 19:— ?Manufactured '20:— ?
FORMATION.—l-Naphthylamine-8-sulfonic acid, aniline, and anilinehydrochloride are heated together in an autoclave
LITERATURE.—Cain, Intermediate Products (2d Ed.), 194
Dyes Derived from Phenyl-l-naph.tliylamine-8-sulfonic Acid
SchultzNumberfor Dye
85
188
Ordinary Name andClass of Dye
MONOAZO DYEOmega Chrome
Black PY
Tolyl Blue SRSulfon Acid Blue R
Statistics ofImport and
Manufacture
I '14:— 45,038M '17:— ?M318:— ?MJ19:— ?M '20:-454,185
Other IntermediatesUsed and Notes
2-A TTiirt 0-6-nitro-p-cresol
HAcid
DyeAppli-cationClass
ACr
A
DYES CLASSIFIED BY INTERMEDIATES 485
Dyes Derived from Phenyl-l-naphthylamine-8-sulfonic Acid (continued)
SchultzNumberfor Dye
256
257
265
Ordinary Name andClass of Dye
DISAZO DTESSulf on Black 3B
Sulfoncyanine
SulfoncyanineBlack B
Statistics ofImport and
Manufacture
I ' 14:—145,649M'17:— ?M'18:— ?M'19:— ?I '20:— 18,327
M'20:— ?
I '14:— 69,590M'17:— ?M'18:— ?M'19:— ?M'20:— ?
Other IntermediatesUsed and Notes
Metanilic Acida-Naphthylamine
Metanilic Acida-Naphthylamine
Laurent's Acida-Naphthylamine or
l-Naphthylamine-6-and 7~su]f onic Acids
Di/eAppli-cationClass
A
A
A
iV-Phenyl-o-phenylene-diamine ((7. A. nomen.)
See, o-Amino-diphenylamine
AT-Phenyl-^-phenylene-diamine (C. A. nomen.)
See, p-Ammo-diphenylannne
JVi-Phenyl-4-m-folylene-diarnine (C. A. nomen. NH2=1)
Phenyl-p-amino-o-toluidiae (CH3=1)
3-Amiao-4-metliyl-diphenylamine
NH
= 013^4^2=198
FORMATION.—^From m-tolylene-diamine hydrochloride by melting withaniline at 220-270°
LITERATUEE.—Lange, Zwischenprodukte, #1621, 1622
486 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from iV1-Phenyl-4-m-tolylene-diaDaine
SchulteNumberfor Dye
684
684
684
Ordinary Name andClass of Dye
AZESTE DYESHhoduline Violet
Rhoduline Red B
Rhoduline Red G
Statistics ofImport andManufacture
I '14:— 2,751I '20:— 35
Other IntermediatesUsed and Notes
Mtroso-dimethyl-aniline
Kitroso-ethyl-aniline
Mtrosoethyl-o-toluidine
Appli-cationClass
B
B
B
Phosgene (C. A, nomen.)
Carbonyl Chloride
\ c i
= CC12O=99
STATISTICS.—Imported J14:—very smallManufactured in recent years in undisclosed quantities
FORMATION.—From cMorine and carbon monoxide, in presence of acatalyst, for example, a suitable charcoal
LITERATURE.—LTlmanu, Enzy. tech. Chemie, 3, 498
Dyes Derived from Phosgene
SchultzNumberfor Dye
279
296
Ordinary Name andClass of Dye
DISAZO DYESBenzo Fast Scarlet
Cotton Yellow G
Statistics ofImport end
Manufacture
I '14:— 36,674M'19:— ?I '20:— 24,153
I '14.— 31,472I '20:— 4,651
Other IntermediatesUsed and Notes
J Acid (2 mols)AnilineAmino-azo-benaene
Acetyl-p-phenylene-diamine (2 mols)
Salicylic Acid (2 mols)
DyeAppli-cationClass
D
D
DYES CLASSIFIED BY INTERMEDIATES 487
Dyes Derived from Phosgene (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
516
518
810
TRIPHENYL-METHANEDYES
Crystal Violet
Ethyl VioletEthyl Purple
ANTHRAQUINONE ANDALLIED DYES
Helidone Yellow3GN
'14:— 51,872M'17:— ?M'18:— ?M'19:— ?I '20:— 2,919M'20:— ?
I '14:— 51,933
I '14:— 20,744I '20:— 2,515
Dimethyl-aniline(3 mols)
B
Diethyl-aniline (3 mols)
2-Amino-anthraqui-none (2 mols)
B
Phthalic Anhydride
O = C 8 H 4 O 3 = 148
STATISTICS.—Imported 14:— 63,574 lbs.
Manufactured 17:—138,857 lbs.Manufactured 18:—227,414 lbs.Manufactured 19:—290,677 lbs.Manufactured '20:—796,210 lbs.
FORMATION.—(1) Naphthalene is oxidized with air in presence of acatalyst. (2) Naphthalene is oxidized by means of sulfur trioxidein presence of mercury.
LITERATURE.—Cain, Intermediate Products (2d Ed.), 162
488 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Phthalio Anhydride
Sekultz Qr(iinari/ Name and
571XANTHONE DYES
Rhodamine 6G
572 Rhodamine G
573 I Rhodamine B
574
580
Rhodamine SB
Past Acid Yiolet B
Statistics ofImport and
Manufacture
I '14:— 37,515I '20:— 8,574
I '14:-I '20:-
2,648217
I J14:— 59,354M317:-M '18:-MJ19:-I '20:-M J20:-
24,709?
I '14:— 20,6S8I '20:— 2,907
M'19:— ?
Other IntermediatesUsed and Notes
Ethyl-Tft-amino-phenol(2 mols)
[Ethylation]
Diethyl-772-amino-phenol (2 mols)
Aniline [removes oneC2H5 group]
or[Heating of Rhodamine
B with aniline salt]
Diethyl-m-amino-phenol (2 mols)
orResorcinol (2 mols)[PC15; diethyl-amine]
Diethyl-wz-amino-phenol (2 mols)
[Ethyl esterification]or
[Ethyl ester of Rhoda-mine B]
Resorcinol (2 mols)Aniline or
p-Toluidine (2 mols)[PC15; sulfonation]
or[Dichloro-fluoresceine
and Aniline orp-Toluidine; sul-fonation]
DyeAppli-cationClass
B
B
B
B
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Phthalic Anhydride (continued)
489
SchultzNumberfor Dye
Ordinary Name andClass of Dye
XANTHONE DYES(continued)
Fast Acid Eosine GFast Acid Phloxine A
Fast AcidViolet A2R
Acid Rosamine A
UranineFluoresceine
Chrysoline
Eosine
I '14:I '20:-M'20:-
Statistics ofImport and
Manufacture
I '14:-I '20:-
I '14:-I '20:
6505,234
8752,679
• ?
5 0
1 4 1
I ; 1 4 : — 2 , 2 7 3
M ' 1 7 : — ?
M ' 1 9 : — ?
I ' 2 0 : — 1 0
I ' 2 0 : — 1 , 4 0 2
I ' 1 4 : — 9 4 , 5 2 8
M ' 1 7 : — 6 8 , 4 9 6
M ' 1 8 : — 1 6 1 , 1 5 3
M ' 1 9 : — 1 2 1 , 3 0 3
I ' 2 0 : — 2 9 6
M ' 2 0 : — 8 5 , 4 8 9
Other Intermediates
Used and Notes
D i e t h y l - m - a m i n o ~
p h e n o l ( 2 m o l s )
[ S u l f o n a t i o n ]
or
[ R h o d a m i n e B , s u l f o -
n a t e d ]
R e s o r c i n o l ( 2 m o l s )
o - T o l u i d i n e ( 2 m o l s )
[ P C l s , S u l f o n a t i o n ]
or
[ D i c h l o r o - f l u o r e s c e i n e
and o - t o l u i d i n e ,
S u l f o n a t i o n ]
R e s o r c i n o l ( 2 m o l s )
M e s i d i n e ( 2 m o l s )
[ P C 1 5 , S u l f o n a t i o n ]
or
[ D i c h l o r o - f l u o r e s c e i n e
and m e s i d i n e , s u l f o -
n a t i o n ]
R e s o r c i n o l ( 2 m o l s )
R e s o r c i n o l ( 2 m o l s )
B e n z y l C h l o r i d e
R e s o r c i n o l ( 2 m o l s )
[ B r o m i n e ]
or
[ T e t r a b r o m o - f l u o r e -
s c e i n e ]
Dye
Appli-
cation
Class
490 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Phthalic Anhydride {continued)
SchvltzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
588
589
590
591
592
599
XANTHONE DYES(continued)
Eosine Spirit Solubl.Methyl Eosine
Eosine S
Eosine BNAcid Eosine
Erythrosine G
Erythrosine B
Galleine
I '14:-M'20:-M'20:-
'14:-'20:-
M'20:-
2,315??
20,1431,132
I '14:—
I '14:-M'17:-M'18:-M'19:-I r20:-M720:-
I '14:-M'19:-I '20:-M'20,
Resorcinol (2 mols)[Bromine; Methyl
esterincation]or
99
4,35050,
1,636
6,874
15,404
7,469
Eosine methyl ester]
Resorcinol (2 mols)[Bromine; Ethyl
esterification]or
[Eosine ethyl ester]
Resorcinol (2 mols)Promination, Nitra-
tion]or
[Dibromo-flTioresceinenitrated]
Resorcinol (2 mols)[Iodation]
or[Diiodo-fluoresceine]
Resorcinol (2 mols)[Iodation]
or[Tetraiodo-fluoresceine]
Gallic Acid (2 mols)or
Pyrogallol (2 mols)
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Phthalic Anhydride (continued)
491
SchultzNumberfor Dye
600
601
612
613
758
782
874
Ordinary Name andClass of Dye
XANTHONE DYES(continued)
Coeraleine B
Coeruleine S
QUINOLINE DYESQuinoline Yellow
Spirit Soluble
Quinoline YellowWater Soluble
ANTHRAQUINONE ANDALLIED DYES
Sirius Yellow G
Anthracene BrownAlizarin Brown
INDIGO GROUP DYESIndigo
Statistics ofImport and
Manufacture
MM
IMI
II
II
IMMMIM
I
MM
M
M
I
'19:'20:
'14:'19:'20:
'14:'20:
'14:'20:
— ?— ?
— 3,404— ?— 9,392
— 79,553— 205
— 15,354— 34,440
'14:—115,586'17:'18:'19:'20:'20:
'14:
'17'18.
'19'
'20
— ?— ?— 40,426— 2,728— 42,840
—8,507,359—274,771——3,083,888
8,863,824—18,178,231
'20:—520,347
Other IntermediatesUsed and Notes
Resorcinol (2 mols)[Dehydration]
or[Fluoresceine
dehydrated]
Gallic Acid (2 mols)or
Pyrogallol (2 mols)[Dehydration]
or[Galleine dehydrated]
Quinaldine
Quinaldine[Sulfonation]
Naphthalene
Gallic Acid
Phthalic Anhydride(2 mols)
DyeAppli-cationClass
M
M
ss
A
CL
M
V
492 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Phthalic Anhydride (continued)
SchultzNumberJOT Dye
S76
877
878
879
880
881
882
883
Ordinary Name andClass oj Dye
INDIGO GROUP DYES{continued)
Indigo MLBIndigo White
Indigotine I '14M'17
M ' l S
M'19
M'20
I '20;
Indigotine P
Brom IndigoRath j en
Helindone Blue BBIndigo RB
Dianthrene Blue 2BBromo Indigo FBCiba Blue 2B
Indigo MLB/5BCiba Blue G
Indigo MLB/6BIndigo KG
Statistics ofImport and
Manufacture
:— 19,329
1,876,787
1,434,703
' 1,699,670
1,395,000:— 5,512
I '14M'20
:— 53,610:— ?
I '14M'17I '20M720
I 14:-MJ19:-I '20:-
I '14:-I '20-
I '14:-I '20:-
M'20:-
:— 6,856:— 14,100:— 3,691
16,880
35,857
1,3561,008
3,1914,130
Other IntermediatesUsed and Notes
Phthalic Anhydride(2 mols)
[Reduction]
Phthalic Anhydride(2 mols)
[Sulfonation]
Phthalic Anhydride(2 mols)
[Sulfonation]
Phthalic Anhydride(2 mols)
[Bromination]
Phthalic Anhydride(2 mols)
[Bromination]
Phthalic Anhydride(2 mols)
PBromination]
Phthalic Anhydride(2 mols)
promination]
Phthalic Aiihydride(2 mols)
[Bromination]
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Phthalic Anhydride (continued)
493
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
884
885
886
890
INDIGO GROUP DYES(continued)
Brilliant IndigoBASF/2B
Brilliant IndigoBASF/B
Brilliant IndigoBASF/G
Indigo Yellow 3G
Giba Yellow G
I '14:— 4,518
I '14:I '20:
8,1753,503
I '14:— 12,057
I '14: 48
Phthalic Anhydride(2 mols)
[Chlorination, Bromina-tion]
Phthalic Anhydride(2 mols)
[Chlorination]
Phthalic Anhydride(2 mols)
[Chlorination, Bromina-tion]
Phthalic Anhydride(2 mols)
Benzoyl Chloride
Phthalic Anhydride(2 mols)
Benzoyl Chloride[Bromination]
Phthalimide
f T N H =
STATISTICS.—Manufactured in 1920 in undisclosed amountFORMATION.—By treatment of molten phthalic anhydride with gaseous
ammoniaLITERATURE.—Cain, Intermediate Products (2d Ed.), 147USES.—For preparation of anthranilic acid
Piria's AcidSee, Naphthionic Acid
494 DYES CLASSIFIED BY INTERMEDI TES
Picramic Acid
OH
NO2
STATISTICS.—Manufactured '17:— ?Manufactured '18:—235,652 lbs.Manufactured '19:—150,458 lbs.Manufactured '20:—138,350 lbs.
FORMATION.—From picric acid by reduction, using sodium hydrogensulfide or sodium sulfide
LITERATURE.—Cain, Intermediate Products (2d Ed.), 117
Dyes Derived from Picramic Acid
SchtdtzNumberfor Dye
88
89
90
91
92
219
Ordinary Name andClass of Dye
MONOAZO DYESAcid Anthracene
Brown B,
MetachromeBrown B
Chrome Brown P
Anthracyl ChromeGreen D
MetachromeBordeaux R
DIRAZO DYEChrome Patent
Green N
Statistics ofImport and
Manufacture
I '14:— 33,053M'17:— ?M'19:— ?I '20:— 1,400M'20:— ?
I '14:— 1,001M'17:— ?M'18:—349,961M'19:— ?M '20:—192,914
I '14:— 4,596M'18:— ?I '20:— 3,316
Other IntermediatesUsed and Notes
m-Phenylene-diamine-[sulf onic Acids]
m-Phenylene-diamineor
m^Tolylene-diamineor
Chloro-m-phenylene-diamine
m-A mino-phenol
Naphthionic Acid
3-Amino-4-methyl-phenyl-p-tolyl-sul-famide
AnilineKAcid
DyeApplication"Class
ACr
M
M
ACr
M
ACr
DYES CLASSIFIED BY INTERMEDIATES 495
Picric Acid
OH
STATISTICS.—Manufactured in 1919 and 1920 in an indeterminateamount for dyeing purposes. Prior to 1919 it was made in verylarge quantities for explosive uses
FORMATION.—Phenol is sulfonated and then trinitrated
LITERATURE.—Cain, Intermediate Products (2d Ed.), 114Lange, Zwischenprodukte, #1116-1121Schultz, Farbstofftabellen (1914), #5
USES.—For the manufacture of picramic acid. I t is also a dye, Schultz #5
Primuline-sulfonic Acid (Sodium Salt)
(This is the "Primuline" of commerce)
(Primuline "base" is the unsulfonated product)
STATISTICS.—See #616 in following table
FORMATION.—p-Toluidine and sulfur are heated together, resulting in amixture of primuline base and p-dehydro-thio-p-toluidine, knownas primuline "melt." This can be separated by vacuum distilla-tion. However it is generally sulfonated, using 23 per cent oleum,and then separated by the greater solubility of the ammonium saltof the primuline-sulfonic acid
LITERATURE.—Schultz, Farbstofftabellen, #616Wahl, Organic Dyestuffs, 299Thorpe, Die. Chemistry, 4, 386
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Primuline-sulfonic Acid
SchultzNumberfor Dye
18
25
26
27
190
191
192
195
197
Ordinary Name andClass of Dye
STILBENE DYEDiphenyl Fast
Yellow
PYRAZOLONE DYESDianil Yellow 3G
Dianil Yellow R
Dianil Yellow 2R
MONOAZO DYESAlkali BrownBenzo Brown 5R
Pyramine Yellow R
Cotton Orange G
Rosophenine SG
Tniazine Red G
Statistics ofImport arid
Manufacture
I '14:— 10,229I '20:— 1,102
M'19:— ?M'20:— 2,9S7
I '14:— 5,727I '20:— 100
I '14:— 1,877
M'18:— ?M'19:— ?M'20:— 19,639
I '14:— 4,861M '18:— ?M'19:— 11,886M '20:— 13,988
Other IntermediatesUsed and Notes
Primuline-sulfonicAcid (2 mols)
Dinitro-dibenzyl-disul-fonic Acid orDinitro-stilbene-di-sulfonic Acid
[Ethyl aceto-acetate]
3-Methyl-l-phenyl-5-pyrazolone
3-Methyl-l-p-sulfo-phenyl-5-pyrazolone
orPhenyl-hydrazine-p-
sulf onic Acid[Ethyl aceto-acetate]
m-Phenylene-diamine
Nitro-m-phenylene-diamine
771-Phenylene-diamine-disulfonic Acid
Nevile-Winther's Acid
Schaeffer's Acid
DyeAppli-cationClass
D
D
D
D
D
D
D
D
D
DYES CLASSIFIED BY INTERMEDIATES 497
Dyes Derived from Primuline-sulfonic Acid (continued)
SchultzNumberfor Dye
198
199
209
210
615
616
Ordinary Name andClass of Dye
MONOAZO DYES(continued)
Clayton YellowThiazol Yellow
Oriol YellowCotton Yellow R
DISAZO DYESTerra Cotta FC
Cotton Orange R
THIOBENZENYL DYESThioflavinc S
Primuline
IMMMI
IMI
I
II
IMMI
IMMMMI
Statistics ofImport andManufacture
'14:—'18:—'19:—'20:—'20:—
'14:—'20:—'20:—
'14:—
'14:—'20:—
'14:—'19:—'20:—'20:—
'14:—'17:—'IS:—
29,879???
11,182
13,416?125
551
16,45951
4,948??675
67,97672,46172,788
;19:—271,33S'20:—183,179'20:— 441
Other IntermediatesUsed and Notes
Deliydrotliio-p-tolui-dine-sulfonic Acid(2 mols)
orPrimuline (2 mols)
Salicylic Acid
m-Phenylene-diamineNaphthionic Acid
m-Phenylene-diamine-disulfonic Acid
Mctanilic Acid
[Methylation]
DyeAppli-cationClass
D
D
D
D
D
D
Pseudocumidine (C. A. nomen.)
i/'-Cumidine
2 :4 : 5-Trimethyl-anilme
1:2:4-Trimethyl-5-amino-bcn25cne
NH2
CH3
498 DYES CLASSIFIED BY INTERMEDIATES
STATISTICS.—Imported '14:— 6,617 lbs.Manufactured '17:— ?Manufactured ' 18:— ?Manufactured '19:— ?Manufactured '20:—28,405 lbs.
FORMATION.—Xylidine hydrochloride is digested with methanol(CH3OH) in an autoclave at 280-300° and the product convertedto nitrates and crystallized. The sparingly soluble nitrates areseparated and washed, and treated with alkali to convert to bases,which are a mixture of xylidines and cumidines. The bases arethen fractionally distilled, and that fraction coming over at 225-245° is allowed to crystallize and is pressed to remove oily products.It consists largely of pseudocumidine
LITERATUBE.—Thorpe, Die. Chemistry, 2, 177 (1912 Ed.); or 2, 434(1921 Ed.)
Lange, Zwischenprodukte, #1061
Dye Derived from Pseudocumidine
SchvltzNumberfor Dye
83
Ordinary Name andClass of Dye
MONOAZO DYEPonceau 4E
Statistics ofImport and
Manufacture
I '14.— 3,557M'17:— ?M'18:— ?M'19:— 24,152M'20:— ?
Other IntermediatesUsed and Notes
RAcid
DyeAppli-cationClass
A
Purpurin (C. A. nomen.)
1:2:4-Trihydroxy-aoithraquiaoiie
OH
DYES CLASSIFIED BY INTERMEDIATES 499
FORMATION.—From alizarin by oxidation with manganese dioxide and
sulfuric acid
LITERATURE.—Lange, Zwischenprodukte, #3129, 3271Barnett, Anthracene and Anthraquinone
Dyes Derived from Purpurin
SchultzNumberfor Dye
783
862
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Purpurin
Alizarin BlueBlack B
Statistics ofImport and
Manufacture
I '14:— 54,706I '20:— 28,802
Other IntermediatesUsed and Notes
Aniline[Sulfonation]
DyeAppli-cationClass
M
M
Pyrogallic Acid
See, Pyrogallol
Pyrogallol (C. A. nomen.)
1:2:3-Trihydroxy-benzene
Pyrogallic Acid
OH
) S 5 - <
STATISTICS.—Imported '14:—24,964 lbs.
Manufactured regularly, but amounts not disclosed
FORMATION.—From gallic acid by heating in an autoclave in presence ofwater
LITERATURE.—Lange, Zwischenprodukte, #958
Green, Organic Coloring Matters (1908), 45
500 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Pyrogallol
Schvltz!Number;•for Dye
62
84
158
599
601
769
770
773
Ordinary Name andClass of Dye
MONOAZO DYEAzo Galleine
Azo Chromine
Chrome Brown RR
XANTHONE DYESGalleine
Coeruleine S
AXTHRAQUINOXE ANDALLIED DYES
Alizarin Yellow C
Alizarin Yellow A
Anthracene Yellow
IMI
IMIM
IMI
I
Statistics ofImport and\fanujaeiure
'14:—'17:—720:—
514:—J19:—J20:—J20:—
'14:—'19:—'20:—
'14:—
7,2419
2,183
15,404?
5,075?
3,404
9,392
4,046
Other IntermediatesUsed and Notes
Dimethyl-p-phenylene-diamine
p-Amino-phenol
4-Aniino-l-phenol-2: 6-disulfonic Acid
Phthalic AnhydridePyrogallol (2 mols)
Phthalic AnhydridePyrogallol (2 mols)[Dehydration]
or[Galleine dehydrated]
[Acetic Acid]
Benzoic Acidor
Benzo trichloride
[Aceto-acetic EthylEster; Bromination]
DyeAppli-cationClass
M
M
M
M
M
M
M
M
PyrogaUol-5-sulfonic Acid
3:4:5-Trihydroxy-&enzene-sulfonic Acid (C. A. nomen.)
OH
OH
DYES CLASSIFIED BY INTERMEDIATES 501
FORMATION.—1: 3-Dichloro-2-hydroxy-benzene-5-sulfonic acid (as po-tassium salt) is fused with concentrated caustic potash solution at150-160°
LITERATURE.—Lange, Zwisehenprodukte, #959
Ger. Pat., 203,145; Frdl. 9, 247
Dyes Derived from Pyrogallol-5-sulfonic Acid
SchultzNumberfor Dye
623
Ordinary Name andClass of Dye
OXAZINE DYEPyrogallol-cyanine-
sulf onic Acid
Statistics ojImport and
ManujactureOther Intermediates
Used and Notes
Nitroso-dimcthyl-aniline
DyeAppli-cationClass
M
Quinaldine (C. A. nomcn.)
2-Methyl-quinoline
a-Methyl-quinolinc
= CIOHBN =
STATISTICS.—Manufactured '19:— ?
Manufactured '20:— ?
FORMATION.—By condensing aniline and piaracetaldehydc cither cold,or hot,—in the latter case using hydrochloric acid and aluminum orzinc chloride to catalyze the reaction
LITERATURE.—Cain, Intermediate Products (2d Ed.), 84
Lange, Zwischenproduktc, #2000-2002
502 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Quinaldine
SchvltzNumberfor Dye
610
612
613
Ordinary Name andClass of Dye
QUINOLINE DYESQuinoline Red
Quinoline YellowSpirit Soluble
Quinoline YellowWater Soluble
Statistics ofImport and
Manufacture
I '14:— 79,553I '20:— 205
I '14:— 15,354I '20:— 34,440
Other IntermediatesUsed and Notes
Benzo-trichlorideIsoquinoline
Phthalic Anhydride
Phthalic Anhydride[Sulfonation]
DyeAppli-cationClass
B
ss
A
Quinizarin (C. A. nomen.)
1:4-Dihydroxy-anthraquinone
FORMATION.—From anthraquinone by oxidation with sulfuric acid inpresence of boric acid
LITERATURE.—Lange, Zwischenprodukte, #3233, 3260, 3268, 3270,3274,3276,3314,3351
Cain, Intermediate Products (2d Ed.), 255
Dyes Derived from Quinizarin
SchvltzNumberfor Dye
852
852
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Alizarin Irisol D
Alizarin DirectViolet R
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
y-Toluidine[SuHonation]
4-Toluidine-3-sulfonicAcid
DyeAppli-cationClass
A
A
DYES CLASSIFIED BY INTERMEDIATES 503
SchultzNumberfor Dye
865
865
Dyes Derived
Ordinary Name andClass of Dye
ANTHRAQUINOSTE ANDALLIED DYES
(continued)Alizarin Cyanine
Green E
Alizarin DirectGreen G
from. Quinizarin {continued)
Statistics ofImport and
Manufacture
I 14:— 2,000I '20:— 31,851
M'20:— ?
Other IntermediatesUsed and Notes
p-Toluidine (2 mols)[Sulfonation]
4-Toluidine-3-sulfonieAcid (2 mols)
DyeAppli-cationClass
ACr
ACr
Quinoline
STATISTICS.—Imported 14:—very small
Manufactured ' 19:— ?
FORMATION.—(1) By extraction from coal-tar. (2) By synthesisthrough the heating together of aniline, nitrobenzene, glycerol andsulfuric acid for some time, first at 125° and then at 180°
LITERATURE.—Lange, Zwischenprodujtte, #1995Thorpe, Die. Chemistry, 4, 468
Dye Derived from Quinoline
SchultzNumberfor Dye
611
Ordinary Name andClass of Dye
QUINOLINE DYEQuinoline Blue
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
Lepidine[Amyl iodide]
DyeAppli-cationClass
Photo-graphy
504 DYES CLASSIFIED BY INTERMEDIATES
RAcid
2-Xaphthol-3: 6-disulfonic Acid (C A. nomen.)
j^Xaphthol-disulfonic Acid R
£-Xaphthol-a-disulfonie Acid
Note.—R Acid is occasionally applied to other naphthalene derivatives,e.g., 2-amino-3-naphthol-6-$ulfonic acid, 2-naphthylamine-S: 6-disulfonicacid} 2:3-dihydroxy-nai)hthale7w-6-mlfonic Acid
HO3SOHSO3H
STATISTICS.—Imported '14:— 46,267 lbs.Manufactured '18:— 712,033 lbs.Manufactured ' 19.—1,008,007 lbs.Manufactured '20:—1,250,674 lbs.
FORMATION.—From /3-naphthol by disulfonation, and separation, fromthe G acid simultaneously formed
LITERATURE.—Cain, Intermediate Products (2d Ed.) , 226Lange, Zwisehenprodukte, #2651, 2652Thorpe, Die. Chemistry, 3, 626
SchultzNumberfor Dye
39
47
65
Dyes
Ordinary Name andClass of Dye
MOXOAZO DYESPonceau G
Orange III
Azo Coralline L
Derived from
Statistics ofImport and
Manufacture
M '17:— ?
M'17:— ?M'18:— ?
I '20:— 249:U'2O:— ?
R Acid
Other IntermediatesUsed and Notes
Aniline
jS-Xaphthol
p-Amino-acetanilide
DyeAppli-cationClass
A
A
A
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from R Acid (continued)
505
SchultzNumberfor Dye
82
83
101
112
168
202
236
Ordinary Name andClass of Dye
MONOAZO DYES(continued)
Ponceau R, 2RScarlet R, 2R
Ponceau 4R
Coccinine B
Fast Red BBordeaux B
Amaranth
Acid Alizarin Red BPalatine Chrome
RcdB
DISAZO DYESCloth Red BWool Red B
Statistics ofImport and
Manufacture
I '14:— 35,259M'17:—633,429M'18:—
1,189,054M '19:—552,680M'20:—
1,286,002
I '14:— 3,557M'17:— ?M'18:— ?M'19:— 24,152M'20:— ?
I '14:— 25,821M'17:—120,595M'18:—200,415M'19:—161,862I '20:— 7,882M'20:—217,406
I '14:— 86,067M'17:— 66,069M'18:— 73,539M'19:—294,416I '20:— 110M'20:—204,958
I '14:— 7,374M'18:— ?M'19:— 28,081I '20:— 1,342M'20:— 67,817
I '14:— 14,293M'17:— ?M'18:— ?M'19:— ?M'20:— ?
Other IntermediatesUsed and Notes
Xylidine
Pseudocumidine
m-Amino-p-cresolMethyl Ether
a-Naphthylamine
Naphthionic Acid
Anthranilic Acid
o-Amino-azo-toluene
DyeAppli-cationClass
A
A
A
A
A
ACrCL
A
506 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from R Acid (continued)
SchultzNumberfor Dye
238
244
2G9
270
272
298
299
300
341
412
Ordinary Name andClass of Dye
DISAZO DYES(continued)
Union Fast Claret
Coomassie WoolBlackS
Naphthol Black GB
Brilliant Croceine 9B
Naphthol Black BBrilliant Black B
Milling Red R
Cinnabar Scarlet BF
Cinnabar Scarlet GCotton Ponceau
Crumpsall DirectFast Red R
Congo Blue 2B
Statistics ofImport and
Manufacture
M18:— ?M'19:— ?
I '14:—120,512I '20:— 1,500M'20:— ?
I '14:—103,598M'19:— ?I '20:— 50
M '17:— ?M'18:~- ?M'19:— ?M'20:— ?
Other IntermediatesUstd and Notes
Amino-azo-xylene
Acetyl-p-phenylene-diamine
a-Naphthylamine
l-Naphthylamine-4: 6-and -4: 7-disulfonicAcids
a-Naphthylamine
Amino-G AcidAnilineG Acid or R Acid
Amino-G Acida-Naphthylamine
Diaroino-diphenyl-methane
R Acid (2 mols)
Diamino-dixylyl-methane
R Acid (2 mols)
Diamino-dixylyl-phenyl-methane
R Acid (2 mols)
BenzidineSalicylic Acid
DianisidineNevile-Winther's Acid
DyeAppli-cationClass
A
A
A
A
A
A
CL
CL
D
D
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from R Acid (continued)
507
SchultzNumberfor Dye
414
429
433
434
484
Ordinary Name andClass of Dye
DISAZO DYES(continued)
Indazurine B
Indazurine BB
Coomassie Blade B
Coomassie NavyBlue
TRISAZO DYEMilling Scarlet B
Statistics ofImport and
Manufacture
I '20:-— 42,357
Other IntermediatesUsed and Notes
Dianisidine1:7-Dihydroxy-naph-
thalene-4-s u 1 f o n i cAcid
Dianisidine1:7-Dihydroxy-2-naph-
thoic-4 sulfonic Acid
1:4-Naphthylene-dia-mine-2-sulfonic Acid
jS-Naphthylamine
1:4-Naphthylene-dia-mine-2-suKonic Acid
0-Naphthol
Diamino-azoxy-tolueneNevile-Winther's Acid
DyeAppli-cationClass
2R Acid
2-Amino-8-naphthol-3:6-disulfonic Acid
Amino-naphthol-disulfonic Acid RR or 2R
7-Amino-l-naphthol-3: 6-disulfonic Acid (C. A. nomen.)
HO
H O 3 S I I J S O 3 H
FORMATION.—From sodium 2-naphthylamine-3: 6: 8-trisulfonate byfusion with caustic soda at 220-260°
LITERATURE.—Cain, Intermediate Products (2d Ed.), 239Lange, Zwischenprodukte, #2734
)8 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 2R Acid
'chvltz
44
442
443
449
453
454
455
457
Ordinary Name andClass of Dye
MOXOAZO DYEAzo Archil R
TRISAZO DYESDirect Black V
Direct IndoneBlueR
Trisulfon Brown B
Columbia Black R
Trisulfon Brown G
Columbia Black B
TrisulfonBrown GG
Statistics ofImport and
Manufacture
I '14:—145,73S
I '14:— 16,781I '20:— 38,616
I '14:— 1,307
I '14:— 1,323
I '14:—165,727
I '14:— 7,562I '20:— 38,411
Other IntermediatesUsed and Notes
Aniline
Benzidinea-NaphthylamineGamma Acid
Benzidinea-NaphthylamineHAcid
BenzidineSalicylic Acidm-Phenylene-diamine
Tolidinem-Tolylene-diamine
(2 mols)
TolidineSalicylic Acidm-Phenylene-diamine
Dianisidinem-Tolylene-diamine
(2 mols)
DianisidineSalicylic Acid7n-Phenylene-diamine
DyeAppli-cationClass
A
D
D
D
D
D
D
D
Red Acid
l:5-Dihydrox>^naphthalene-3:7-disulfoiiic Acid (not consideredherein)
Resorcine
See, Resorcinol (C. A. nomen.)
DYES CLASSIFIED BY INTERMEDIATES
Resorcinol (C. A. nomen.)
Resorcine
509
STATISTICS.—Imported '14:— 61,624 lbs.Manufactured ' 17:— ?Manufactured ' 18:— 2,087 lbs.Manufactured '19:— 96,397 lbs.Manufactured '20:—139,315 lbs.
FORMATION.—Benzene is disulfonated with oleum, and the resultingbenzene-m-disulfonic acid is fused with a large excess of causticsoda
LITERATURE.—Cain, Intermediate Products (2d Ed.), 130
Dyes Derived from Resorcinol
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
11
35
60
75
NITROSO DYESolid Green O
STILBENE DYEMikado OrangeChloramine
Orange G
MONOAZO DYESSudan G
Azo Phosphine GO
New Phosplrine G
I '14:— 26,010M'17:— ?M'18:— ?IVT19:— ?MJ20:— 38,287
I '14:-
I '14:-
798
50
I '14:— 500
[Dinitroso Derivative]
2>-Nitro-tolucnc-o-sul-fonic Acid (4 mols)
[Resorcinol as reducingagent]
Aniline
m-Amino-phcnyl-tri-methyl-ammoniumChloride
Amino-benzyl-^dimethyl-ainme
M
D
ss
B
B
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Besorcinol (continued)
SchultzNumberfor Dye
143
155
211
213
222
317
374
376
435
Ordinary Name andClass of Dye
MONOAZO DYES(continued)
ChrysoineTropaeoline
Acid AlizarinGarnet R
DISAJZO DYESResorcine Brown
Fast Brown
Janus Yellow G
PyramidolBrown BG
Congo 4RCongo Red 4R
Pyramidol Brown T
^HISAZO DYESJanus Brown B
Statistics ofImport and
Manufacture
I '14:— 6,252M'17:— ?M'18:— ?M'19:— ?M'20:— ?
I '20:— 201M'20:— ?
I '14:— 13,189M'17:— ?M'18:— ?M'19:— ?I '20:— 2,484M'20:— ?
I 714:— 3,206M'17:— ?
MJ19:— ?M '20:— ?
I 14:— 2,250I '20:— 758
M'18:— ?
Other IntermediatesUsed and Notes
Sulfanilic Acid
a-A m\ T) o-plienol-p-sulf onic Acid
w-XylidineSulfanilic Acid
NaplithAoiiic Acid(2 mols)
m-Nitro-anilinem-Amino-phenyl-tri-
methyl-amnioniiLniChloride
BenzidineResorcinol (2 mols)
TolidineNaphthionic Acid
TolidineResoTcinol (2 mols)
p-Amino-benzyl-diethyl-arnine
a-Naphtkylarniae
DyeAppli-cationClass
A
M
A
A
B
D
D
D
B
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Resorcinol (continued)
511
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
TRISAZO DYES(continued)
Isodiphenyl Black R
Coomassie UnionBlacks
Congo Brown GNaphthamine
Brown 4G
Congo Brown R
Azo Corinth
TETRAKISAZO DYEHessian Brown BBN
XANTHONE DYESRhodamino B
I 14:— 52,141M17M18M19I '20M'20
- 443-229,489
I 14:— 3,045
Rhodamine 12 GF
I '14:— 59,354M17:— ?M18:— ?M'19:~ ?I '20:— 24,709M'20:-~ ?
p-Phenylene-diamine(2 mols)
Gamma Acid
1: 4-lSTaphthylene-dia-mine-2-sulf onic Acid
Gamma AcidResorcinol (2 mols)
BenzidineSulf anilic AcidSalicylic Acid
BenzidineLaurent's AcidSalicylic Acid
TolidineNaphthionic Acid3-Amino-phenol-4-sul-
f onic Acid
BenzidineSulf anilic Acid (2 mols)Resorcinol (2 mols)
Phthalic AnhydrideResorcinol (2 mols)[Phosphorus penta-
chloridc; diethyl-anaine]
Dimethylamino-hy-droxy-benzoyl-benzoic Acid
[Formaldehyde;esterincation]
D
D
D
D
D
B
B
512 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Resorcinol (continued)
for Dye,
Statistics of 'Import and ,
Manufacture iOther Intermediates
Used and Notes
XANTHONE DYES S |(continued) t \
Fast Acid Violet B «I '14:— 2O,6SS Phthalic AnhydrideM '19:— ? ! Resorcmol (2 mols)I '20:— 2,907 Aniline or p-tol-
uidine (2 mols)[PC15; sulfonation]
Fast Acid VioletA2R I '14:— 875 Phthalic AnhydrideI '20:— 2,679 Resorcinol (2 mols)
o-Toluidine (2 mols)[PC15; sulfonation]
Phthalic AnhydrideResorcmol (2 mols)Mesidine (2 mols)[PC15; Sulfonation]
3:6-Dichloro-phthalicAcid
Resorcinol (2 mols)p-Phenetidine (2 mols)[PC15; Sulfonation]
Phthalic AnhydrideResorcinol (2 mols)
Acid Rosamine A
Fast Acid Blue R
I '14:' I '20:
I '14:-I '20:-
50141
4,022130
franineFluoresceine
Chrysoline
Eosine
I '14:— 2,273
'20:— 10
I '20:— 1,402
I '14:M'17:M'18:-M'19:I '20:-M'20:-
- 94,52S- 68,496-161,153-121,303- 296- 85,489
Phthalic AnhydrideResorcinol (2 mols)Benzyl Chloride
Phthalic AnhydrideResorcinol (2 mols)[Bromination]
or[Fluoresceine
brominated]
DyeAppli-cationClass
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Resorcinol (continued)
513
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
XANTHONE DYES(continued)
Eosine Spirit SolubleMethyl Eosine
Eosine SP
Eosine BNAcid Eosine
Erythrosine G
Erythrosine B
Phloxine P
I J14:-M;20:-
2,315?
I '14:-I '20:-M'20:
20,1431,132
I '14:— 99
I '14:-M'17:-M'18:-M'19:-I '20:-
4,350505
1,636
96,874
I '14:-- 2,244M'17:— ?
M'20:—
Phthalic anhydrideResorcinol (2 mols)[Bromination, methyla-
tion]or
[Eosine methyl ester]
Phthalic AnhydrideResorcinol (2 mols)[Bremination, ethyla-
tion]or
[Eosine ethyl ester]
Phthalic AnhydrideResorcinol (2 mols)[Bromination, nitration]
or[Dibromo-fluoresceine
dinitratcd]
Phthalic AnhydrideResorcinol (2 mols)[Iodation]
or[Fluoresccine iodated]
Phthalic AnhydrideResorcinol (2 mols)[Iodation]
or[Fluoresceine iodated]
3: 6-Dichloro-phthalicAcid
Resorcinol (2 mols)[Bromination]
ss
A
514 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Resorcinol (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport arid
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
XAOTHONE DYES(continued)
Cyanosine SpiritSoluble
Rose Bengal
Phloxine
Rose Bengal B
Cyanosine B
Coemleine B
OXAZINE DYESPhenocyanine TC
I '14M'20
:— 2,277
I '14:
I '14:M'17:-M'lS:-M'19:-
1,020
1,354
?
M'19:-M '20:-
I '20:— 4,740
3: 6-Dichloro-phthalicAcid
Eesorcinol (2 mols)[Bronaination, methyla-
tion]or
[Phloxine methyl ester]
3: 6-Dichloro-phthalicAcid
Resorcinol (2 mols)[Iodation]
Tetrachloro-phthalicAcid
Resorcinol (2 mols)[Bronaination]
Tetrachloro-phthalicAcid
Resorcinol (2 mols)[Iodation]
Tetrachloro-phthalicAcid
Resorcinol (2 mols)[Ethylation]
or[Phloxine ethylated]
Phthalic AnhydrideResorcinol (2 mols)[Dehydration][Fluoresceine
dehydrated]
Mtroso-dimethyl-aniline
Gallic Acidor
[GaUocyanine]
ss
M
M
DYES CLASSIFIED BY INTERMEDIATES 515
Dyes Derived from Resorcinol (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOthar Intermediates
Used and Notes
DyeAppli-cationClass
643
644
647
648
OXAZINE DYES(continued)
Phcnocyanine T V
Ultracyanine B
Nitroso Blue MRResorcine Blue
Iris Blue
M'17I '20:- 1,543
Nitroso-dimethyl-aniline
Gallic Acid[Sulfonation]
or[Gallocyanine;
Sulfonation]
Nitroso-dimethyl-aniline
Gallic Acid[Allcaline Condensation]
or[Gallocyanine alkaline
condensation withresorcinol]
Nitroso-dimethyl-aniline
Nitroso-resorcinol[Bromination]
M
M
MF
Resorcinol Methyl Ether
Methyl-resorcinol
m-Methoxy-phenol ( C A. nomen.)
JOCHs
FORMATION.—From resorcinol by methyla t ion
LITERATURE.—Ul lmann , Enzy. tech. Chemie, 9, 490
516 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from Resoreinol Methyl Ether
SchultzNumberfor Dye
575
Ordinary Kane aM j fJ^aSClass of Dye Manufacture
!XANTHOXE DYE
Rhodine 12 GM 1
!
Other IntermediatesUsed and Notes
Dimethylamino-liy-droxy-b e n z o y l -benzoic Acid
[Ethyl esterification]
DyeAppli-cationClass
B
Resorcinol-succinein3:6-Dihydrox3'-9-xanthene-propionic Acid; y-Lactone (C. A
nomen.)
HO—( \-O-f X , - O H _
CH. O
CH2. CO
FORMATION-.—^From resoreinol and succinic acid (or its anhydride) byheating together at about 200° C.
LITERATURE.—Cohen, Theoretical Organic Chemistry (1918 Ed.), 461
Dye Derived from Resorcinol-succinein
" t a w I S 2 £
XANTHONE DYE570 Rhodamine S I JU:— 600
I '20:— 273
Other IntermediatesUsed and Notes
[Dimethyl-amine2mols]
DyeAppli-cationClass
a-Resorcylic Acid (C. A. nomen.)
3:5-Dihydroxy-benzoic Acid7n-Dihydrox^r-ben2oic Acid
COOH
DYES CLASSIFIED BY INTERMEDIATES 517
FORMATION.—From 3: 5-disulfo-benzoic acid by caustic soda fusion
LITERATURE.—Lange, Zwischenprodukte, #881
Ullmann, Enzy. tech. Chemie, 2, 345
Dye Derived from a-Resorcylic Acid
SchultzNumberfor Dye
771
Ordinary Name andClass of Dye
ANTHRAQTJINONE ANDALLIED DYES
Resoflavine W
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
a-Resorcylic Acid(2 mols)
[Oxidation]
DyeAppli-cationClass
M
j3-Resorcylic Acid (C. A. nomen.)
2:4-Dihydroxy-benzoic Acid
=C 7 H 6 O 4 =154
FORMATION.—By heating resorcinol with a solution of potassium bi-carbonate under reflux
LITERATURE.—Ullmann, Enzy. tech. Chemie, 2, 345Bistrzycki and Kostanecki, Ber. 18, 1984 (1885)
Dye Derived from /3-Resorcylic Acid
SchultzNumberfor Dye
49
Ordinary Name andClass of Dye
MONOAZO DYEPrague Alizarin
Yellow G
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
m-Nitro-aniline
DyeAppli-cationClass
M
RG Acid
See, l-Naphthol-3: 6-disulfonic Acid
518 DYES CLASSIFIED BY INTERMEDIATES
Rho AcidSee, Anthraquinone-1: 5-disulfonic Acid
Eumpff AcidSee, Croeeine Acid
S AcidSee, l-Amino-S-naplithol-4-sulfonic Acid
See, 1: S-Diliydruxy-napLtLalene-4-?ulfonic Acid
Sit, l-Naplithylarnint-S-sulfunic Acid
tfte, l-Xaphthylamine-4: S-di<ulfunic Acid
1-XapLtbol-S-tulfonie Acid (not considered herein)
1: S-DiLydruxy-napLtLalene-2:4-disulfonic Acid (notconsidered herein)
1: 7-DiLydrox\"-naphthalene-6-carbosylic Acid (not con-
Note.—The use of S as a trivial name is very confusing and should beai aided
2S Acid
See, l-Amino-S-naplithol-2:4-disulfonic Acid
Salicylic Acid0-Hydroxy-beiizGic Acid
COOH
OH =C:H £O 3=13S
Technical U. S. P.11s. lbs.
STATISTICS.—Manufactured '17:-— 960,339 2,495,285Manufactured 'IS:—1,395,630 3,270,462Manufactured ' 19:—3,467,055 2,619,726Manufactured '20:—3^914,163 2,663,494
FORMATION.—PLenol is treated -with caustic soda, dried and powdered;and tLt-n >ul)jtct(-d to aetiun of carbon dioxide under pressure andat lU>-l-i:r
DYES CLASSIFIED BY INTERMEDIATES 519
LITERATURE.—Cain, Intermediate Products (2d Ed.), 149Lange, Zwischenprodukte, £145, 471—£75, 479
Dyes Derived from Salicylic Acid
for Dye
48
58
96
102
103
133
177
MONOAZO DYESAlizarin Yellow GG
Alizarin Yellow R
Chrome FastYellow GG
Diamond Flavine G
Dutch Yellow
EriochromePhospMne R
Chrome Yellow DMordant Yellow 0
Manufacture
I '14:—144,761M'17:—
1,452,622M'18:—
2,233,208M'19:—163,170M'20:—211,5S0
I '14:— 97,059M'17:—215,46SM '18:—385,910M'19:—130,424I '20:— 860M'20:— S3,334
I '14:— 150I '20:— 500
I '14:— 23,0S9M '17:— ?
M'19:— ?M'20:— ?
I '14:— 1,433
I '14:—129,651M'17:— ?M'18:— 32,011M'19:— ?I '20:— 1,389M'20:— ?
Other IntermediatesUsed and Xotes ]
mOsitro-aniline
p-Nitro-anilineor
Aniline [with nitrationafter coupling]
o-Anisidineor
m-Amino-p-cresolMethyl Ether
Benzidine
Benzidine[Sodium sulfite]
p-Nitro-aniline-o-sulf onic Acid
Broenner's Acid
DyeAppli-cation
M
M
M
M
M
ACr
M
520 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Salicylic Acid (continued)
SchultzNumberfor Dye
178
199
204
221
250
291
292
294
296
305
339
Ordinary Name andClass of Dye
MONOAZO DYES(continued)
Crumpsall Yellow
Oriol YellowCotton Yellow R
Diamond Yellow G
DISAZO DYESAnthracene Acid
Brown G
Milling Orange
M'17M'18I '20
Azo AlizarinBordeaux W
Azo AlizarinBlack I
Anthracene Yellow CFast Mordant
Yellow
Cotton Yellow G
Hessian Yellow
Brilliant Orange G
Statistics ofImport and
Manufacture
I '14:-I '20:-M'20:
13,416125
:— ?:— ?:— 225
I 'U:— 4,370
I '14:I '20:
I '14:-I '20:-
3,678
31,4724,651
I '14:—M'17:—
6,321?
Other IntermediatesUsed and Notes
Amino-G Acid
Dehydrothio-p-tolui-dine-sulfonic Acid
orPrimuline
m- or p-Amino-benzoicAcid
Sulfanilic Acidp-Nitro-aniline
Ammo-azo-benzene-sulfonic Acid
p-Phenylene-diamineNevile-Winther's Acid
p-Phenylene-diamineChromotropic Acid
Thio-anilineSalicylic Acid (2 mols)
p-Amino-acetanilide(2 mols)
Salicylic Acid (2 mols)Phosgene
Diamino-stilbene-disul-f onic Acid
Salicylic Acid (2 mols)
Benzidine3 -Amino-phenol-4-
sulfonic Acid
DYES CLASSIFIED BY INTERMEDIATES 521
SchultzNumberfor Dye
340
340
341
342
343
344
345
346
Dyes Derived
Ordinary Name andClass of Dye
DI-SAZO DYES(continued)
Benzo Orange R
Chlorazol Orange 2R
Cnunpsall DirectFast Red R
Chrysamine G
Diamine FastRedF
Diamine Brown. M
Oxamine Maroon
Oxamine Red
from Salicylic
Statistics ofImport and
Manufacture
I '14:— 1,073M'17:— ?M'18:— 50,422M'19:— 42,807I '20:— 220M'20:— 86,210
M'17:— ?M'18:— ?M'19:— ?M'20:— ?
I '14:— 608M'17:— 26,061M'18:— 28,846M'19:— 54,279I '20:— 9,810M'20:— 49,342
I '14:— 50,479M'19:— 56,864I '20:— 4,040M'20:—115,865
I '14:— 65,396M'18:— ?M'19:— 15,959M'20:—257,872
I '14:— 11,636I '20:— 848
Acid (continued)
Other IntermediatesUsed and Notes
BenzidineNaphthionic Acid
Benzidine2-Naphthylamine-7-
sulfonic Acid
BenzidineRSalt
BenzidineSalicylic Acid
(2 mols)
BenzidineGamma Acid[Acid coupling]
BenzidineGamma Acid[Alkaline coupling]
Benzidinel-Amino-5-naphthol-7-
sulf onic Acid
BenzidineJ Acid
DyeAppli-cationClass
D
D
D
D
D
D
D
D
522 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Salicylic Acid (continued)
SchultzNumberfor Dye
347
348
349
350
355
393
394
404
444
445
446
Ordinary Name andClass of Dye
DISAZO DYES(continued)
Diphenyl Brown RN
Diphenyl Brown BN
Diamine Brown B
Alkali Yellow R
Anthracene Red
Diphenyl Brown3GN
Ckrysamine R
Diamine Yellow N
TRISAZO DYESCrumpsall Direct
Fast Brown B
Crumpsall DirectFast Brown 0
Benzo Olive
Statistics ofImport and
Manufacture
I '14:— 13,471
I '20:— 24
I '14:— 3,873M'19:— ?I '20:— 104M'20:— ?
M'20:— ?
I '14:— 6,261M'20:— ?
M'17:— ?I '20:— 313
I '14:— 1,14
Other IntermediatesUsed and Notes
BenzidineMethyl-gamma Acid
BenzidineDimethyl-gamma Acid
BenzidinePhenyl-gamma Acid
BenzidineDehydrothio-p-tolui-
dine-sulf onic Acid
o-Nitr o-b enzidineNevile-Winther's Acid
TolidineDimethyl-gamma Acid
TolidineSalicylic Acid (2 mols)
Ethoxy-b enzidinePhenol[Ethylation]
BenzidineAnilineGamma Acid
BenzidineAnilinePhenyl-gamma Acid
Benzidineq-NaphthylammeH Acid
DyeAppli-cationClass
D
D
D
D
ACr
D
D
D
D
D
D
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Salicylic Acid (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
447
448
449
454
457
465
466
468
475
TRISAZO DYES(continued)
Benzo Gray S
Diamine Bronze G
TrisulfonBrown B
TrisulfonBrown G
TrisulfonBrown GG
Columbia BlackGreen D
Eboli Green
Diphenyl Green 3G
Diamine Green GOxamine Green G
:— 802
:— 4,495
I '14:— 16,781I '20:— 38,616
I '14:— 1,323
I '14:— 7,562I '20:— 38,411
I '14:— 7,329M'17:— ?M'18:— 29,118M'19:—136,638I '20:— 1,332M'20:— 52,292
Benzidinea-NaphthylamineNevile-Winther's Acid
Benzidinem-Phenylene-diamineHAcid
BenzidinewvPhenylene-diamine2R Acid
TolidineTtt-Phenylene-rH a/mine2R Acid
Dianisidinem-Phenylene-diamine2R Acid
Benzidinel-Amino-8-naphthol-4-
sulf onic AcidAniline
BenzidineSulfanilic Acidl-Amino-8-naphthol-
3:5-disulfonic Acid
BenzidineHAcido-Chloro-2>-nitro-
aniline
BenzidineH Acid2>-Nitro-aniline
524 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Salicylic Acid (continued)
SckultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
476
477
478
480
482
510
TEISAZO DYES(continued)
Benzamine Brown3GO
Congo Brown GNaphthamine
Brown 4G
Columbia Green
Congo Brown R
Alizarin Yellow FS
I '14:— 16,988M'17:— ?M'18:— ?M'19:— ?M'20:—623,757
I '14:— 52,141M'17:-M'18:-MJ19:-I '20:-M'20:
- 443-229,489
I '14:-M'18: -I '20:-
45,162
7,555
I '14:— 3,045
TRIPHENTL-METHANEDYES
Azo Green
BenzidineSulf anilic Acidm-Phenylene-diamine
BenzidineSulfanilic AcidResorcinol
BenjzidineSulfanilic Acidl-Amino-8-naphthol-4-
sulfonic Acid
BenzidineLaurent's AcidResorcinol
Aniline ando-Toluidinep-ToluidineSalicylic Acid (3 mols)
or[FucLsine and
Salicylic Acid]
m-Amino-tetramethyl-p ^ ' - d i a m i n o - t r i -phenyl-methane
or fromm-Nitro-benzaldehyde
and dimethyl-aniline(2 mols)
[Oxidation]
D
D
D
D
M
M
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Salicylic Acid (continued)
525
SchultzNumberfor Dye
549
557
Ordinary Name andClass of Dye
TRIPHENYL-METHANEDYES
(continued)Chrome Violet
Chrome Violet
Statistics ofImport and
Manufacture
I '14:— 51
I '14:— 220M 'IS:— ?
Other IntermediatesUsed and Notes
Hydrol[Oxidation]
Salicylic Acid (3 mols)[Formaldehyde and
sulfuric Acid]
DyeAppli-cationClass
M
M
Schaeffer's a Acid
l-Naphthol-2-sulfonic Acid (not considered herein)
Schaeffer's Acid*
Schaeffer's /3 Acid
2-Naphthol~6-sulfonic Acid (C. A. nomen.)
/3-Naphthol-sulfonic Acid S
/3-Naphthol-sulfonic Acid Schaeffer
/3-Naphthol-a-sulfonic Acid of Armstrong and Schultz
/3-Naphthol-/3-sulfonic Acid
HO3S0 H =
STATISTICS.—Manufactured '17:—13108,049 lbs.2
Manufactured '18:— 169,383 lbs.Manufactured '19:— 146,111 lbs.Manufactured '20:— 475,243 lbs.
FORMATION.—By sulfonation of jS-naphthol, and separation from theCroceine acid formed simultaneously
1 Schaeffer's Acid is very occasionally used when referring to l-Naphthol-2-sulfonicacid, but this is more properly known as Schaeffer's a acid.
2 Includes Croceine Acid.
526 DYES CLASSIFIED BY INTERMEDIATES
LITERATTJBB.—Cain, Intermediate Products (2d Ed.), 223Lange, Zwischenprodukte, #2430-2432Thorpe, Die. Chemistry, 3, 624
SchultzNumberfor Dye
4
37
70
79
111
123
166
Dyes Derivec
Ordinary Name andClass of Dye
MONOAZO DYESNaphthol Green
Ponceau 4GBCroceine Orange
Brilliant Orange 0
Brilliant Orange RXylidine Orange RR
Fast Red BT
EmineRed
Fast Red E
I fromL Schaeffer's Acid
Statistics ofImport and
Manufacture
IMMMIM
IMMMM
IMMMM
IMMMM
MMM
IMi.VJLMMM
'14:—'17:—'18:—'19:—'20:—'20:—
'14:—'17:—'18:—'19:—'20:—
'14:—'17:—'18:—'19:—'20:—
'14:—'17:—'18:—'19:—'20:—
'17:—'18:—'19:-
'14:—J17.'18:—'19:—'20:—
19,14675,85022,46534,646
100?
13,046?
30,82417,27496,573
21,480????
4,204?
18,9097
??
2,473????
Other IntermediatesUsed and Notes
[Nitroso-Derivative]
Aniline
Toluidine
Xylidine
a-Naphthylamine
Isodehydrothio-m-xylidine
Naphthionic Acid
DyeAppli-cationClass
A
A
A
A
A
A
A
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Schaeffer's Acid (continued)
527
SchultzNumberjor Dye
196
197
201
234
237
243
248
254
273
289
293
Ordinary Name andClass of Dye
MONOAZO DYES(continued)
Titian Red
Thiazine Red G
Pigment Scarlet G
DISAZO DYESCloth Red G
Bordeaux BX
Coomassie WoolBlack R
Fast Scarlet B
Bordeaux G
DiaminogeneBlue BB
Acid AlizarinBlack SN
Palatine ChromeBlack S
Milling Red G
Statistics ofImport and
Manufacture
I '14:— 886M'19:— ?M'20:— ?
I 14:— 4,861M18:— ?M19:— 11,886M'20:— 13,988
M17:— ?M18:— ?M19:— ?
I 14:— 554
I 14:— 1,755
I 14:— 8,308M17:— ?I '20:— 5,936
M17:— ?M18:— ?M19:— ?
I 14:— 69I '20:— 20C
Other IntermediatesUsed and Notes
D ehy dro-thio-p-tolui-dine-sulfonic Acid
Primuline
Anthranilic Acid
o-Amino-azo-toluene
Amino-azo-xylene
Acetyl-p-phenylene-diamine
a-Naphthylamine
Amino-azo-benzene-sulf onic Acid
Amino-azo-toluene-sulf onic Acid
Acetyl-1:4-naphthyl-ene-diamine-6-sul-f onic Acid
a-Naphthylamine
2: 6-Diamino-l-phenol-4-sulfonic Acid
/3-Naphthol
ThioanilineSchaeffer's Acid
(2 mols)
DyeAppli-cationClass
D
D
CL
M
A
A
A
A
D
ACr
A
528 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Schaeffer's Acid (continued)
SchultzNumberjor Dye
645
Ordinary Name andClass of Dye
OXAZINE DYEGallazine A
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
Nitroso-dimethyl-aniline
Gallic Acid[Oxidation]
DyeAppli-cationClass
M
Schoellkopf's Acid
See, l-Naphthol-4: 8-disulfonic Acid
l-Naphthylamine-4:8-disulfonic Acid
l-Naphthylamine-8-sulfonic Acid
Also used for l-Naphthol-8-sulfonic Acid, which is nothere indexed, but the intermediate generally referred tois (fiat one listed first above
Semi-naphthalidam
1:5-Diamino-naphthaleDe (not considered herein)
Siver Salt (Sodium derivative)
See, Anthraquinone-2-sulfonic Acid
SS Acid or 2S Acid
See: l-Amino-8-naphthol-2:4-disxdfonic Acid
m-Sulf anilic Acid
See, Metanilic Acid
Sulfanilic Acid (C. A. nomen. SOzH=l)
p-Amino-benzene-sulfonic acid
Aniline-jp-sulfonie acid
SOsH
NH2
DYES CLASSIFIED BY INTERMEDIATES
STATISTICS.—Imported '14:— 4,477 lbs.Manufactured '17:—1,184,412 lbs.Manufactured '18:—1,247,478 lbs.Manufactured '19:—1,023,861 lbs.Manufactured J20:—1,796,838 lbs.
FORMATION.—From aniline by heating with sulfuric acid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 47Lange, Zwisehenprodukte, #615-620
Dyes Derived from Sulfanilic Acid
529
SchultzNumberfor Dye
22
23
138
139
140
141
Ordinary Name andClass of Dye
PYRAZOLONE DYESXylene Yellow 3G
Tartrazine
MONOAZO DYESHelianthineMethyl Orange
Orange IV
Azoflavine RSCurcumeine
Azo Yellow 3G
Statistics ofImport and
Manufacture
I '14:— 23,074I '20:— 77,782
I '14:—272,477M'17:— ?M'18:— ?M'19:— ?I '20:— 47,877M '20:—701,722
I '14:— 500M'18:— ?M'19:— ?M'20:— ?
I '14:— 19,020M'19:— ?I '20:— 608
I 14:— 39,869I '20:— 5,225
I '14:—114,689M'17:— ?M'18:— ?M'19:— ?I '20:— 4,818M'20:— ?
Other IntermediatesUsed and Notes
l-(2:5-Dichloro-4-sulfo-phenyl) -3-methyl-5-pyrazolone
p-Phenyl-hydrazine-sulf onic Acid
Dimethyl-aniline
Diphenylamine
Diphenylamine[Nitration]
Diphenylamine[Strong nitration]
DyeAppli-cationClass
A
A
A
A
A
A
530 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Sulfanilic Acid (continued)
SchultzNumberfor Dye
142
143
144
145
146
147
211
Ordinary Name andClass of Dye
MONOAZO DYES(continued)
Brilliant Yellow SCurcumine
ChrysoineTropoeoline
Orange I
Orange II
Azo Fuchsine G
Azo Fuchsine 6B
DISAZO DYESResorcine Brown
I 14:—
I 14:—M17:—M18:—M19:—M'20:—
I 14:—M17:—M18:—M'19:—I '20:—
Statistics ofImport and
Manufacture
9,934
6,252
8,305?
1,323M'20:— 14,684
r 14:—128,877M17:—712,586M18:—916,890M19:—
1,133,925I '20:— 2,265M'20:—
1,850,341
I 14:— 17,819I '20:— 3,694
I 14:— 13,206M17:— ?M18:— ?
I 14:— 13,189M17:— ?M18:— ?M19:— ?I '20:— 2,484M'20:— ?
Other IntermediatesUsed and Notes
Diphenylamine[Sulfonation]
Resorcinol
a-Naphthol
jS-Napnthol
1:8-Dihydroxy-naph-thalene-4-sulfonicAcid
1:8-Dihydroxy-naph-thalene-4-sulfonic
Acid[? Classification]
m-XylidineResorciaol
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Sulfanilic Acid (continued)
531
SchultzNumberfor Dye
212
220
221
259
2C0
261
2G2
4GG
476
Ordinary Name andClass of Dye
MONOAZO DYES{continued)
Fast Brown GAcid Brown G
Palatine Black ABuffalo Black PY
Anthracene AcidBrown G
Ponceau 10 RB
EriochromeVerdone A
Buffalo Black 10B
Victoria Black B
TRTSAZO DYESEboli Green
Benzamino Brown3 GO
Statistics ofImport and
Manufacture
I 14:— 17,407I '20:— 485
I 14:—299,274I '20:— 200
M17:— ?M18:— ?I '20:— 225
I 14.— 201
I 14:— 882
M17:— ?M18:— ?M 1 9 : ~ ?M'20:— ?
I 14:— 557
I 14:— 16,988M17:— ?M18:— ?M19:— ?M'20:—623,757
Other IntermediatesUsed and Notes
a-NaphtholSulfanilic Acid (2 mols)
l-Amino-8-naphthol-4-sulfonic Acid
a-Naphthylamine
p-Nitro-anilineSalicylic Acid
o-AnisidineCroceine Acid
ra-Amino-p-cresoliS-Naphthol
a-NaphthylamineHAcid
a-Nai >hthylamine1:8-Dihydroxy-naph-thalcnc-4-sulf onic Acic
BcnzidincSalicylic Acidl-Amino-8-naphthol-
3: 5-disulf onic Acid
Benzidinem-Phcnylcne-diamineSalicylic Acid
DyeAppli-cationClass
A
A
ACr
A
ACr
A
A
D
D
532 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Sulfanilic Acid (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intennediates
Used and Notes
DyeAppli-cationClass
477
478
485
489
738
MONOAZO DYES(continued)
Congo Brown GNaphthamine Brown M
4G
I '14:— 52,14117:— ?
M'18:— ?M'19:— ?I '20:— 443
M'20:—229,4S9
Columbia Green
TETBAKISAZO DYESBenzo Brown G
I '14:— 45,162VI'18:— ?I '20:— 7,555
I '14:— 41,905M'17:— ?M'18:— ?M'19:— 83,506I '20:— 2,286M '20:—109564S
Hessian Brown BBN
SULFUR DYECotton Black
BenzidineResorcinolSalicylic Acid
BenzidineSalicylic Acidl-Amino-8-naphthol-4-
sulf onic Acid
m-Phenylene-diamine(3 mols)
Sulfanilic Acid (2 mols)
BenzidineResorcinol (2 mols)Sulfanilic Acid (2 mols)
l-Chloro-2: 4-dinitrobenzene
[S plus
D
D
^-Sulfo-anthranilic Acid (C. A. nomen.)
2-Amino-4-sulfo-benzoic AcidP-ATD i no-p-sulfobenzoic Acid
COOH
_ 217
DYES CLASSIFIED BY INTERMEDIATES 533
FORMATION.—o-Nitro-toluene is sulphonated with oleum. The resulting
o-nitro-toluene-p-sulfonic acid is converted into the sodium salt
and heated with a 40 per cent caustic soda solution at 90-95°
LITERATURE.—Lange, Zwischenprodukte, #855
Dye Derived from ^-Sulfo-ajrthranilic Acid
SchultzNumberfor Dye
28
Ordinary Name andClass of Dye
PYRAZOLONE DYEPigment Fast
Yellow G
Statistics ofImport and
Manufacture
MJ19:— ?I J20:— 170
Other IntermediatesUsed and Notes
3-Methyl-l-phenyl-5-pyrazolone
DyeAppli-cationClass
CL
Sulfo-naphthalic Acid
Naphthalene-1-sulfonic Acid (not considered herein)
/3-Sulfonic Acid
See} Anthraquinone-2-sulfonic Acid
l-(/>-Sulfo-phenyl)-3-methyl-5-pyrazolone
See, 3-Methyl-l-(p-sulfo-phenyl)-5-pyrazolone
l-(^-Sulfo-phenyl)-5-p3n:azolone-3-caxboxylic Acid
Tartrazinogen-sulfonic Acid
5-Keto-l-(p-sulfo-phenyl)-3-A2-pyrazoline-carboxylic Acid (C. A.
nomen.)
O3H
OC
H2C
N
-C.COOH
534 DYES CLASSIFIED BY INTERMEDIATES
FORMATION.—By condensation of phenyl-hydrazine-p-sulfonic acid andethyl oxalacetate
LITERATURE.—Cain, Intermediate Products (2d Ed.), 168LaDge, Zwischenprodukte, #138
Dye Derived from l-(^-Sulfo-phenyl)-5-pyrazolone-3-carboxylic Acid
SchvltzNumberfor Dye
20
Ordinary Name andClass of Dye
PYEAZOLONE DYEFlavazine S
Statistics ofImport and
Manufacture
I '14:— 81,375I '20:— 1,500
Other IntermediatesUsed and Notes
Aniline
DyeAppli-cationClass
A
Sulfo-m-tolylene-diamine-bis-(carbonyl-ainino-naphthol-sul--fonic Acid)
SuKcKm-tolylene^iajniaeHiicarbonyl-dihydroxy-dinaphthylamine-
disulfonic Acid
3:5-Bis[i3-(5-hydroxy-7-sulfo-2-napbtriyl)-carbamido]-p4olTiene-
sulfonic Acid (C. A. nomen.)
CH3
. C O . H N / N N H . C O .
SOaH
FORMATION.—^By condensation of tolylene-diamine-suKonic acid
(CH3:NH2:NH2:SO3H=1:2:6:4) with two molecules of J acid
(2-amino-5-naplithol-7-STilfonic acid), by means of phosgene
(COCI2)
LITERATURE.—Ger. Pat. 236,594, Frdl. 10, 904Lange, Zwischenprodukte, #2912
DYES CLASSIFIED BY INTERMEDIATES 535
Dyes
SchultzNumberfor Dye
280
281
282
Derived from Sulfo-m-tolylene-diamine-bis-(carbonyl-amino-naphthol-sulfonic Acid)
Ordinary Name andClass of Dye
DISAZO DYESAzidine Fast
Scarlet GGS
Azidine FastScarlet 4BS
Azidine FastScarlet 7BS
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
o-Toluidine (2 mols)
o-Toluidine/3-Naphthylamine
/3-Naphthylamine(2 mols)
DyeAppli-cationClass
D
D
D
Tartrazinogen-sulf onic Acid
See, l-(p-Sulfo-phenyl)-5-pyrazolone~3-carboxylie Acid
2:4:6:8-Tetrabromo-l: 5-diamino-anthraquinone
Br r;o N H 2
V J B r =CMHJJrJN'j0j=554
H2N t V ^
FORMATION.—By bromination of 1: 5-diamino-anthraquinone
LITERATURE.—Scholl and Berblinger, Ber. 37, 4180 (1904)Barnett, Anthracene and Anthraquinone, 229Cf. Lange, Zwischenprodukte, #3231, 3404, 3405
Dye Derived from 2:4:6:8-Tetrabromo-l:5-diamino-anthraquinone
SchultzNumberfor Dye
861
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
AnthraquinoneBlue SR
Statistics ofImport and
Manufacture
I '20:— 917
Other IntermediatesUsed and Notes
Aniline (2 mols)[Sulfonation]
DyeAppli-cationClass
ACr
536 DYES CLASSIFIED BY INTERMEDIATES
Tetrachloro-phthalic Acid
Cl
Cll yCOOH ~C8H2C14O4=302
STATISTICS.—Imported '14:—1,102 lbs.
FORMATION.—Phthalic anhydride is warmed for some hours at 200° with6 parts of antimony pentachloride, and chlorine is conductedthrough the molten mass for from 8 to 12 hours
LITERATURE.—Lange, Zwischenprodukte, #1184
Dyes Derived from Tetrachloro-phthalic Acid
SchultzNumberfor Dye
596
597
598
Ordinary Name andClass of Dye
XANTHONE DYESPhloxine
Rose Bengal B
Cyanosine B
Statistics ofImport and
Manufacture
I '14:— 1,020
I '14:— 1,354M'17:— ?M'18:— ?M'19:— ?
Other IntermediatesUsed and Notes
Hesorcinol (2 mols)[Bromination]
Hesorcinol (2 mols)[Iodation]
Resorcinol (2 mols)[Bromination;
Ethylation]or
[Phloxine ethylated]
DyeAppli-cationClass
A
A
ss
pi ^'-Tetraethyl-diamino-benzohydrol
p: p'-Tetraethyl-diamino-diphenyl-carbinol
p:p'-Bis(diethylamino)-benzohydrol (C A. nomen.)
H
i N < ^ ^ C - < ^ ) > N ( C 2 H 5 ) 2 =C21:
DYES CLASSIFIED BY INTERMEDIATES 537
FORMATION.—Diethyl-ardline is condensed with formaldehyde in thepresence of hydrochloric acid to tetraethyl-diamino-diphenyl-methane. This body is now oxidized to the hydrol with leadperoxide
LITERATURE.—Lange, Zwischenprodukte, #1354
SchultzNumberfor Dye
498
Dye Derived from p
Ordinary Name andClass of Dye
TRIPHENYL-METHANEDYE
Turquoise Blue
^'-Tetraethyl-diamino-benzohydrol
Statistics ofImport and
Manufacture
I '14:— 1,541I '20:— 1,407
Other IntermediatesUsed and Notes
p-Nitro-toluene[Oxidation]
DyeAppli-cationClass
B
p: ^'-Tetraethyl-diamino-benzophenone
p: p'-Bis(diethylamino)-&enzophenone (C. A. nomen.)
—CO = C2iHo8N2O = 324
FORMATION.—By condensation of diethyl-aniline (2 mols) and phosgene(carbonyl chloride)
LITERATURE.—Lange, Zwischenprodukte, #1382
Dyes Derived from ^:^'-Tetraethyl-diamino-benzoplienoiie
SchultzNumberfor Dye
518
532
560
Ordinary Naine andClass oj Dye
TRIPHENYL-METHANEDYES
Ethyl VioletEthyl Purple
Alkali Violet 6B
DlPHENYL-NAPHTHYL-METHANE DYE
Night Blue
Statistics ofImport and
Manufacture
I '14:— 51,933
I '14:— 3,020
I '14:— 361M'19:— ?I '20:— 11
Other IntermediatesUsed and Notes
Diethyl-aniline
Methyl-diphenyl-amine
[Sulfonation]
y-Tolyl-a-naphthyl-andne
DyeAppli-cationClass
B
A
B
538 DYES CLASSIFIED BY INTERMEDIATES
p: j>'-Tetraethyl-diamino-diphenyl-carbinol
See, p: p'-Tetraethyl-diamino-benzohydrol
p: /-Tetraethyl-diamino-diphenyl-methane
p: p'-Methylene-bis-[iV:iV-diethyl-aniline] (C. A. nomen.)
= C2iH30N2 = 310
FORMATION.—By condensation of diethyl-aniline with formaldehydein the presence of hydrochloric acid
LITERATURE.—C/. Cain, Intermediate Products (2d Ed.), 102Cf. Lange, Zwischenprodukte, #1301
Dye Derived from p: ^'-Tetraethyl-dianiino-diphenyl-methane
SchultzNumberfor Dye
518
Ordinary Name andClass of Dye
TRIPHENYL-METHANEDYE
Ethyl VioletEthyl Purple
Statistics ofImport and
Manufacture
I '14:— 51,933
Other IntermediatesUsed and Notes
Diethyl-aniline
DyeAppli-cationClass
B
1:3:5:7-Tetrahydroxy-anthraquinone
See, Anthrachrysone
Tetramethyl-diamino-benzohydrol
See, Hydrol
p: ^'-Tetramethyl-diamino-benzohydrol-sulf onic Acid
5-Dimethylamino-a-(p-dimethylamino-phenyl)-a-hydroxy-o-folu-ene-sulfordc Acid (C. A. nomen.)
(CH3)2N<
H0
SO3H
HN(CH3)2 — Ci7H22N2O4S = 350
DYES CLASSIFIED BY INTERMEDIATES 539
FORMATION.—Tetramethyl-diamino-diphenyl-methane (from condensa-
tion of dimethyl-aniline and formaldehyde) is dissolved in mono-
hydrate and sulfonated with 25 per cent oleum at 110°. This
methane-sulfonic acid is now oxidized with lead peroxide to the
hydrol derivative
LITERATURE.—Ger. Pat. 88085; Frdl. 4, 219
Cain, Intermediate Products (2d Ed.), 102
Lange, Zwischenprodukte, #1312
Georgievics and Grandmougin, Dye Chemistry, 208
Dye Derived from Tetramethyl-diamino-benzohydrol-sulfonic
SchultzNumberfor Dye
531
Ordinary Name andClass of Dye
TRIPHENYL-METHANEDYE
Eriocyanine A
Statistics ofImport and
Manufacture
I '14:— 25,091I '20:— 8,223
M'20:-~ ?
Other IntermediatesUsed and Notes
Dibenzyl-aniline-sul-fonic [or disulfonic}Acid
[Oxidation]
Acid
DyeAppli-cationClass
A
Tetramethyl-diamino-benzophenone
See, Ketone
p: //-Tetramethyl-diamino-diphenyl-methane
p: p'-Methylene-bis-[iV: i\r-dimethyl-aniline] (C. A. nomen.)
) = 254
STATISTICS.—Manufactured '20:— ?
FORMATION.—From dimethyl-aniline (2 mols) by condensing with
formaldehyde in the presence of hydrochloric acid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 102
Lange, Zwischenprodukte, #1301
540 DYES CLASSIFIED BY INTERMEDIATES
Dyes
SchultzNumberfor Dye
493
603
Derived from p: ^-Tetramethyl-diamino-diphenyl-methane
Ordinary Name andClass of Dye
ATJRAMINESAuramine
ACRIDINE DYEAeridine Orange NO
Statistics ofImport and
Manufacture
I '14:—449,276M'17:— ?M'18:— 45,634M'19:—127,567I '20:— 74,414
M'20:— ?
I '14:— 2,336I '20:— 1,925
Other IntermediatesUsed and Notes
[Sulfur and ammonia]
[Dinitration, Reduc-tion]
[Ammonia Removal,Oxidation]
DyeAppli-cationClass
B
B
p: j)'-Tetramethyl-diamino-diphenylmethane-sulf onic Acid
6-(p-Dimethylamino-benzyl)-iV: iV-dimethyl-metanilic Acid (C.A.nomen.)
HO3S
/ " " N N (CH3)2 = C17H22N2O3S = 334
FORMATION.—By sulfonation of tetramethyl-diamino-diphenylmethane;or by condensation of dimethyl-metanilic acid and dimethyl-anilinewith formaldehyde
LITERATURE.—Lange, Zwischenprodukte, #1312
Cain, Intermediate Products (2d Ed.), 102Georgicvics and Grandmougin, Dye Chemistry, 208
USES.—For preparation of prp'-tetramethyl-diamino-benzohydrol-sul--fonic acid
N':N': N": JV'-Tetramethyl-m: pr: '-methenyl-trisaniline {C.A.nomen.)
See, m-Amino-tetramethyl-p': p^-diamino-triphenyl-methane
DYES CLASSIFIED BY INTERMEDIATES 541
a-Tetranitro-naphthalene
From 1:5-Dinitro-naphthalene
/3-Tetranitro-naphthalene
1:3:6: 8-Tetranitro-naphthalene (not considered herein)
Y-Tetranitro-naphthalene
1:3:5: 8-Tetranitro-naphthalene (not considered herein)
5-Tetranitro-naphthalene
1: 2: 5: 8-Tetranitro-naphthalene (not considered herein)
Thioaniline
p: p'-Thio-bisaniline (C A. nomen,)
p: p'-Diamino-diphenyl-sulfide
"VTTT ____ f^\ TT "XT C< ___ C\ -\ £»>I\ JC12 L/12-tt i2iN 2U A1D
FORMATION.—^From aniline by heating with sulfur in presence of leadoxide
LITERATURE.—Meyer-Jacobson, Organische Chemie (1902), II, 1, 476
Dyes Derived from Thioaniline
SchultzNumberJor Dye
293
294
Ordinary Name andClass of Dye
DISAZO DYES
Milling Red G
Anthracene Yellow CFast Mordant
Yellow
Statistics ofImport and
Manufacture
I '14:— 699I '20:— 200
I '14:— 3,678I '20:— 887
Other IntermediatesUsed and Notes
Schaeffer's Acid(2 mols)
Salicylic Acid (2 mols)
DyeAppli-cationClass
A
AACr
p: /-Thio-bisaniline (C. A. nomen.)
See, Thioaniline
542 DYES CLASSIFIED BY INTERMEDIATES
Thio-carbanilide (C. A. nomen.)
Diphenyl-thiourea
N H . CS . NH = Ci3Hi2N2S = 228
STATISTICS.—Manufactured ' 17:— ?Manufactured '18:—1,326,236 lbs.Manufactured '19:—2,268,375 lbs.Manufactured '20:—2,226,807 lbs.
FORMATION.—From aniline by action of carbon disulfide
LITERATURE.—Ullmann, Enzy. tech. Chemie, 6, 304
Dyes Derived from Thio-carbanilide
SchultzNumberfor Dye
874
876
877
Ordinary Name andClass of Dye
INDIGO GROUP DYESIndigo
Indigo MLBIndigo White
Indigotine
Statistics ofImport and
Manufacture
I '14:—8,507,359
M'17:—274,771M'18:—
3,083,888M'19:—
8,863,824I '20:—520,347M'20:—
18,178,231
I '14:— 19,329M'17:—
1,876,787M'18:—
1,434,703M'19:—
1,699,670I '20:— 5,512M'20:—
1,395,000
Other IntermediatesUsed and Notes
Thio-carbanilide(2 mols)
[KCN, etc.]
Thio-carbanilide(2 mols)
[KCN, etc.; Reduction]or
[Indigo Reduced]
Thio-carbanilide(2 mols), etc.
or[Indigo Sulf onated]
DyeAppli-cationClass
V
V
A
DYES CLASSIFIED BY INTERMEDIATES 543
Dyes Derived from Thio-carbanilide (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
878
879
880
881
882
883
884
885
INDIGO GROUP DYES(continued)
Indigotine P
Brom IndigoRath j en
Helindone Blue BBIndigo RB
Dianthrene Blue 2BBromo Indigo FBCiba Blue 2B
Indigo MLB/5BCiba Blue G
Indigo MLB/6BIndigo KG
Brilliant IndigoBASF/2B
Brilliant IndigoBASF/B
I '14:— 53,610M'20:— ?
I '14:— 6,856M'17:— 14,100I '20:— 3,691M'20:— ?
I '14:— 16,880M'19:— ?I '20:— 35,857
I '14:-I '20:-
I '14:-I '20:-M'20:-
1,3561,008
Thio-carbanilide(2 mols), etc.
or[Indigo Sulf onated]
Thio-carbanilide(2 mols), etc.
or[Indigo Brominated]
Thio-carbanilide(2 mols), etc.
or[Indigo, Brominated]
Thio-carbanilide(2 mols), etc.
or[Indigo, Brominated]
Thio-carbanilide(2 mols), etc.
or[Indigo, Brominated]
3,1914,130
I '14:— 4,518
I '14:-I '20:-
8,1753,503
Thio-carbanilide(2 mols), etc.
or[Indigo, Brominated]
Thio-carbanilide(2 mols), etc,
or[Indigo, Chlorinated
Brominated]
Thio-carbanilide(2 mols), etc.
or[Indigo Chlorinated]
544 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Thio-carbanilide (continued)
SchultzNumberfor Dye
886
889
890
Ordinary Name andClass of Dye
INDIGO GKOUP DYES(continued)
Brilliant IndigoBASF/G
Indigo Yellow 3G
Ciba Yellow G
Statistics ofImport and
Manufacture
I '14:— 12,057
I '14:— 48
Other IntermediatesUsed and Notes
Thio-carbanilide(2 mols), etc.
or[Indigo Chlorinated,
Brominated]
Thio-carbanilide(2 mols), etc.
Benzoyl Chlorideor
[Indigo, BenzoylChloride]
Thio- carbanilide(2 mols), etc.
Benzoyl Chloride[Bromination]
or[Indigo Yellow 3G,
Brominated]
DyeAppli-cationClass
V
V
V
Thio-indoxylSee, 2-Hydroxy-thionaphthene
Thio-indoxyl-carboxylic AcidSee, 2-Hydroxy-thionaphthene-l-carboxylic Acid
o-Thiol-benzoic AcidSee, Thio-salicylic Acid
Thio-salicylic Acido-Mercapto-&enzoic Acid (C. A. nomen.)
o-Thiol-benzoic Acid
Thiophenol-o-carboxylic Acid
COOH
M S H =C7H6O2S = 154
DYES CLASSIFIED BY INTERMEDIATES 545
FORMATION.—(1) From o-chloro-benzoic acid by reaction with potas-sium hydrogen sulfide. (2) From anthranilic acid by diazotizingand then running into a solution of sodium polysulfide and sodiumhydroxide
LITERATURE.—Cain, Intermediate Products (2d Ed.), 151Lange, Zwischenprodukte, #507-510
SchultzNumberfor Dye
912
919
Dyes Derived
Ordinary Name andClass of Dye
INDIGO GROUP DYESThio Indigo Red B
Ciba Bordeaux B
from Thio-salicylic Acid
Statistics ofImport and
Manufacture
I 'U:— 1,102I '20:— 275
I '14:— 899I '20:— 1,786
Other IntermediatesUsed and Notes
Thio-salicylic Acid(2 mols)
[Chloro-acetic Acid2 mols; etc.]
Thio-salicylic Acid(2 mols)
[Chloro-acetic Acid2 mols; etc.jBromi-nation]
or[Thio Indigo Red,
brominated]
DyeAppli-cationClass
V
V
Tobias Acid
See, 2-Naphthylamine-l-sulfonic Acid
Also applied to, 2-Naphthol-l-sulfonic Acid
Tolidine
See, o-Tolidine
o-Tolidine (C. A. nomen.)
Tolidine
E3C
546 DYES CLASSIFIED BY INTERMEDIATES
STATISTICS.—Imported '14:— 5,874 lbs.Manufactured ' 17:— ?Manufactured ' 18:— ?Manufactured '19:—143,012 lbs.Manufactured '20:—375,905 lbs.
FORMATION.—From o-nitro-toluene by reduction with zinc dust andhydrochloric acid, and conversion of the hydrazo-toluene intotolidine by boiling with hydrochloric acid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 95Lange, Zwisehenprodukte, #1204, 1216
Dyes Derived from o-Tolidine
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
338
362
363
DISAZO DYESNaphthamine
Blue 3BI '14:— 11,707I '20:— 400
Toluylene Orange ROxy Diamine Orange M
I '14:— 25,908- ?
I '20:— 1,653
Benzopurpurin 4B
364
365
366
Benzo Purpurin 6B
Benzopurpurin B
Diamine Red BDeltapurpurin 5B
I '14:—351,712M'17:— ?M'18:—356,522M'19.-288,021I '20— 3,492
M'20—617,629
I '14— 9,171I J20:— 4,743
I '14— 21,090M'17:— ?M'18:— ?M'19:— ?
I ' 14— 21,058M ' 1 7 — ?M'18:— ?I ' 20— 1,896
K Acid (2 mols)
4: 6-Diamino-m-tolu-ene-sulf onic Acid(2 mols)
Naphthionic Acid(2 mols)
D
D
Laurent's Acid (2 mols)
Broenner's Acid(2 mols)
2-Naphthylarmn e-7-snJfonic Acid
Broenner's Acid
D
D
D
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from o-Tolidine (continued)
547
SchultzNumberfor Dye
367
368
369
370
371
372
373
374
375
376
377
378
Ordinary Name andClass of Dye
DISAZO DYES(continued)
Diamine Eed 3BDeltapurpurin 7B
Brilliant Purpurin4B
^Brilliant Purpurin R
Brilliant Congo R
Rosazurine G
Rosazurine B
Congo Orange R
Congo 4RCongo Red 4R
Congo Corinth B
Pyramidol Brown T
Azo Blue
TrisulfonBlueR
r
I
II
II
M
IM
IMM
IMM
Statistics ofImport andManufacture
14:—
'14:—
'14:—'20:—
'14:—'20:—
'18:—
'14:—'19:—
'14:—'19:—'20:—
'14:—'19:—'20:—
6,634
8,051
19,13311,129
7,027254
?
2,196?
198??
911??
Other IntermediatesUsed and Notes
2-Naphthykmine-7-sulfonic Acid (2 mols)
Naphthionic AcidBroenner's Acid
Amino-R AcidNaphthionic Acid
Amino-R AcidBroenner's Acid
Ethyl-2-naphthyl-amine-7-sulf onic Acid
2-Naphthylarnine-7-sulfonic Acid
Ethyl-2-naphthylamine-7-suKonic Acid(2 mols)
Amino-R AcidPhenol[Ethylation]
Naphthionic AcidResorcinol
Naphthionic AcidNevile-Winther's Acid
Resorcinol (2 mols)
Nevile-Winther's Acid(2 mols)
l-Naphthol-3:6:8-trisulf onic Acid
0-Naphthol
DyeAppli-cationClass
D
D
D
D
D
D
D
D
D
D
D
D
548 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from o-Tolidine (continued)
SchultzNumberjor Dye
379
380
381
382
383
384
385
386
387
388
Ordinary Name andClass of Dye
DISAZO DYES{continued)
Dianil Blue 2RBenzo New Blue 2B
Dianil Blue B
Azo Black Blue B,H
Azo Mauve B
Naphthazurine B
Chicago Blue 2B,Diamine Blue C2R
Oxamine Blue 4R
Diamine Blue BXBenzo Blue BX
Columbia Blue G
Chicago Blue R
Statistics ofImport and
Manufacture
I '14:— 14,434
M'17:— ?M'20:— ?
I '14:— 4,782
I '14:— 23,877
I '14.— 573M'20:— ?
I '14:— 1,740M'17:— ?M'18:— ?M'19:— 92,214I '20:— 4,520M'20:— 90,147
I '14:— 7,094
Other IntermediatesUsed and Notes
Chromotropic AcidNevile-Winther's Acid
Chromotropic Acid(2 mols)
HAcidm-Hydroxy-diphenyl-
amine
HAcida-Naphthylamine
HAcid/3-Naphthylamine
Croceine Acidl-Amino-8-naphthol-4-
sulfonic Acid
J AcidNevile-Winther's Acid
Nevile-Winther's AcidHAcid
l-Naphthol-3:8-disulfonic Acid
l-Amino-8-naphthol-4-sulfonic Acid
l-Amino-8-naphthol-4-sulfonic Acid (2 mols'
DyeAppli-cationClass
D
D
D
D
D
D
D
D
D
D
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from o-Tolidine (continued)
549
SohultzNumberfor Dye
389
390
391
392
393
394
395
396
397
398
Ordinary Name andClass of Dye
DISAZO DYES(continued)
Eboli Blue B
Benzo Cyanine B
Diamine Blue 3BBenzo Blue 3B
Toluylene Orange G
Diphenyl Brown3GN
Chrysamine R
Cresotine Yellow E
Indazurine RM
Direct Blue R
Direct Gray B
Statistics cjImport and
Manufacture
I '14:— 201
14:— 1,365M17:— 14,533M18:— 99,645M19:—182,946I '20:— 1,120
M'20 :—136,891
I 14:— 67,022M18:— ?M19:— ?I J20:— 273
M'20:— ?
M'20:— ?
I 14:-M32O:-
6,261?
M17:— ?
Other IntermediatesUsed and Notes
l-Anuno-8-naplitliol-3:5-disulfonic Acid(2 mols)
HAcidl-Amino-8-naplitliol-4-
sulf onie Acid
H Acid (2 mols)
4: 6-Diamino-m-tolu-ene-sulf onic Acid
o-Cresotic Acid
Salicylic AcidDimethyl-gamma Acid
Salicylic Acid (2 mols)
o-Cresotic Acid(2 mols)
1: 7-Dihydroxy-2-naplithoic-4-sulf onic Acid
Nevile-Wintlier's Acid
1:7-DLhydroxy-6-iiaplithoic-3-sulfonic Acid
Nevile-Winther's Acid
1:7-Dihydroxy-6-naph-thoic-3-sulfonic Acid(2 mols)
DyeAppli-cationClass
550 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from o-Tolidine (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
399
450
451
452
453
454
481
DISAZO DYES(continued)
Indazurine GS
TRISAZO D Y E SBenzo Black Blue R
Congo Fast Blue R
Benzo Indigo Blue
Columbia Black R
Trisulf on Brown G
Azo Corinth
I ?14:-M'19:-I '20:-
4,449
723
I '14:— 1,307
I '14:- 1,323
1:7-Dihydroxy-2-naph-thoic-4-sulfonic Acid
Gamma Acid
a-NaphthylamineNevile-Winther's Acid
(2 mols)
a-Naphthylaminel-Naphthol-3: 8-disul-
fonic Acid (2 mols)
a-Naphthylamine1:8-Dihydroxy-naph-
thalene-4-sulfonicAcid (2 mols)
2 R Acidm-Tolylene-diamine
(2 mols)
2 R AcidSalicylic Acidm-Phenylene-diamine
Naphthionic AcidResorcinol3-Amin o-l-phenol-4-
sulf onic Acid
o-Tolidine-disulfonic Acid
2:2 / -Diamino-5: 5'-bi-m-Zoluene-sulfonic Acid (C. A. nomen.)
H3C CH 3
^ ^ - < ^ ) > N H 2 = C u H 1 6 N 2 O c S 2 = 3 7 2
HO3S SO3H
DYES CLASSIFIED BY INTERMEDIATES 551
FORMATION.—From tolidine sulfate by heating with 2 parts of sulfuricacid at 210° from 36 to 48 hours
LITERATUEE.—Cain, Intermediate Products (2d Ed.), 96Lange, Zwischenprodukte, #1269-1271
Dye Derived from o-Tolidine-disulfonic Acid
SchultzNumberfor Dye
400
Ordinary Name andClass of Dye
DISAZO DYEMilling Scarlet 4RAcid Anthracene
Red3B
Statistics ofImport and
Manufacture
I '14:— 18,330I '20:— 2,336
DjeOther Intermediates Appli-
Used and Xotes cationClass
£-Naphthol (2 mols) } A
^-Toluene-sulfochloride
See, p-Toluene-sulfonyl Chloride (C. A. nomen.)
^-Toluene-sulfonyl Chloride (C. A. nomen.)
p-Toluene-sulfochloride
SO2C1
=: 190.5
STATISTICS.—Imports '14:—small amountManufactured ' 17:— ?Manufactured '18:— ?Manufactured '19:—58,932 lbs.Manufactured '20:— ?
FORMATION.—Toluene is sulfonated with oleum giving a mixture ofo- and p-toluene-sulfonic acids, which are converted to sodiumsalts and dried, and then treated with PCl^+Cl, resulting in o- andp-toluene-sulfonyl chlorides. The POOs formed is first distilledoff and then the mass cooled, whereupon the p-toluene-sulfonylchloride crystallizes out
LITERATURE.—Thorpe, Die. Chemistry, 4, 606
BieL, II, 132
552 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from j5-Toluene-sulfonyl Chloride
Schvltz Quinary Xame and/ < £ & Class of Dye
1S2MONOAZO DYE
Fast Sulfon VioletBrilliant Sulfon
RedB
Statistics ofI?nport andManufacture
I '14:— 4,871I '20:— 4,740
Other IntermediatesUsed and Notes
HAcidAniline
Appli-cationClass
A
Toluidines, mixed
Mixed Toluidines
CH3
STATISTICS.—Imported '14:— 108,835 lbs.
Manufactured '171—1,366,321 lbs.Manufactured '18:— 308,667 lbs.Manufactured '19:— 806,210 lbs.Manufactured '20:—1,145,361 lbs.
FORMATION.—Toluene is nitrated using mixed acid, and the mixture ofo- and p-nitro-toluenes is reduced with iron and hydrochloric acid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 57Lange, Zwischenprodukte, #234-240
Dyes Derived from Toluidines, mixed
SchvltzNumberfor Dye
21
Ordinary Name andClass of Dye
PYBAZOLOXE DTEPigment Chrome
Yellow L
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
3-Methyl-l-phenyl-5-pyrazolone
DyeAppli-cationClass
CL
DYES CLASSIFIED BY INTERMEDIATES 553
SckultzNumberfor Dye
70
71
688
Dyes Derived from Toluidines,
Ordinary Name andClass oj Dye
MONOAZO DYES
Brilliant Orange 0
Azo Fuchsine B
AZINE DYERosolaneMauve
Statistics ojImport and
Manufacture
I '14:— 21,480M'17:— ?M'lS:— ?M'19:— ?M'20:— ?
I '14:— 796I '20:— 3
mixed (continued)
Other IntermediatesUsed and Notes
Schaeffer's Acid
1:8-Dihydroxy-naph-thalene-4-sulf onic Acid
AnilineToluidines (3 mols)
DyeAppli-cationClass
A
A
B
m-ToluidineNote.—C. A. numbering begins with iV£f2, while German and English
numbering generally start from CHz
NH2
STATISTICS.—Imported '14:—945 lbs.Manufactured '20:— ?
FORMATION.—m-Nitro-benzaldehyde is chlorinated to m-nitro-benzyli-dine chloride (C6H4 . NO2 • CHC12), which by reduction with zincat low temperatures, forms m-toluidine
LITERATURE.—Ber. 13, 677; 15, 2011; 18, 3398Dyes Derived from m-Toluidine
SchultzNumberfor Dye
240
Ordinary Name andClass oj Dye
DISAZO DYEJanus Red B
Statistics ofImport and
Manufacture
I '14:— 250I '20:— 176
Other IntertncdiatesXJsed and Notes
m-Amino-phenyl-tri-methyl-ammoniumChloride
0-Naphthol
DyeAppli-cationClass
B
554 DYES CLASSIFIED BY INTERMEDIATES
SchultzNumberfor Dye
435
Dyes Derived
Ordinary Name andClass of Dye
TRISAZO DYEJanus Brown B
from m-Toluidine {continued)
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
m-Amino-phenyl-tri-methyl-ammoniuinChloride
Anilinem-Phenylene-diamine
DyeAppli-cationClass
B
o-Toluidine
Note.—C. A. numbenng begins with NH%, while German and Englishnumbering generally starts from CHz
C7H9N =
STATISTICS.—Imported 14:— 656,320 lbs.Manufactured '17:— 336,985 lbs.Manufactured 18:— 638,874 lbs.Manufactured 19:—1,002,982 lbs.Manufactured ;20:—1,302,097 lbs.
FORMATION.—Toluene is nitrated to a mixture of o- and p-nitro-toluenes,which are separated. The o-nitro-toluene is reduced with ironand hydrochloric acid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 57Lange, Zwischenprodukte, #234-240
Dyes Derived from o-Toluidine
SchultzNumberfor Dye
68
69
Ordinary Name andClass of Dye
MONOAZO DYESSpirit Yellow R
Chrysoidine R
Statistics ofImport and
Manufacture
M19:— ?M'20:— ?
Other IntermediatesUsed and Notes
o-Toluidine (2 mols)
m-Tolylene-diamine
DyeAppli-cationClass
ss
B
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from o-Toluidine (continued)
555
SchultzNumberfor Dye
124
125
126
127
128
Ordinary Name andClass of Dye
MONOAZO DYES(continued)
Diazine Green S
Diazine Black
Indoine Blue RUnion Blue R
Methyl Indoine B
Janus Gray B
Statistics ofImport and
Manufacture
I '14:— 1,340
I '14:— 2,630I '20:— 701
I '14:— 15,353M'17:— ?M'lS:— ?
MJ17:— ?
Other IntermediatesUsed and Notes
p-Tolylene-diamineAniline or2d mol o-Toluidine[Preceding used as
Safranine]with
Dimethyl-aniline
p-Tolylcne-diamineAniline or2d mol o-Toluidine[Preceding used as
Safranine]with
Phenol
p-Tolylene-diamineAniline or2d mol o-Toluidine[Preceding used as
Safranine]with
0-Naphthol
p-Tolylene-diamineAniline or2d mol o-Toluidine[Preceding used as
Safranine]with
t' Amino-naphthols''
p-Tolylene-diamineAniline or2d mol o-Toluidine[Preceding used as
Safranine][Other intermediate
unknown]
DyeAppli-cationClass
B
B
B
B
B
556 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from o-Toluidine (continued)
SchultzNumberfor Dye
280
2S1
482
512
513
514
Ordinary Name andClass oj Dye
DISAZO DYESAzidine Fast
Scarlet GGS
Azidine FastScarlet 4BS
TBISAZO DYEAlizarin Yellow
FS
TRIPHENYL-METHANEDYES
MagentaFuchsine
New Fuchsine 0
Red Violet 5R
Statistics ojImport arid
Manufacture
I '14:-M '17:-M'18:-M' 19:-I '20:-
M'20:-
I '14M'18MJ19M'20
I '14:-I '20:-
- 87,102- 17,739- 71,675-155,830- 189-284,285
:— 300
331750
Other IntermediatesUsed and Notes
o-Toluidine (2 mols)Sulfo-m-tolylene-dia-
mine-bis (carbonyl-amino-naphtliol-sul-fonic Acid)
ft-Naphthylamin eSulfo-TTz-tolylene-dia-
mine-bis(carbonyl-amino-naplithol-sul-fonic acid)
Aniline andp-Toluidine [as
Fuchsine]Salicylic Acid (3 mols)
Anilinep-Toluidine[Arsenic Acid or
Nitro-benzene]
Anhydro-formalde-hyde-o-toluidine orDiamino-o-ditolyl-methane
[o-Nitro-toluene, etc.]
Anilinep-Toluidine[Mtro-benzene, etc., or
Arsenic Acid][Methylation or ethyl-
ation]or
[Magenta methylatedor ethylated]
DyeAppli-cationClass
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from o-Toluidine (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
521
TRIPHENYL-METHANEDYES
{continued)Spirit BlueAniline Blue
524 Fuchsine SAcid Magenta
525 Red Violet 5RS
526 Acid Violet 4RS
536 Alkali Blue
I '14:— 50,563M'17:—M'18:—MJ19:—I '20:—M'20:—
?
?
?723
I '14:— 19,098I '20:— 524
M'20:— ?
I '14:—286,751M'17:— ?M'18:— 43,184M'19:— 77,796I '20:— 6,778
M'20:— 74,253
Aniline (3-4 mols)p-Toluidine[Benzoic Acid]
or[Magenta phenylated]
Anilinep-Toluidine[SuKonation]
or[Magenta sulf onated]
Anilinep-Toluidine, etc.[Ethylation Sulf ona-
tion]or
[Red Violet 5R,sulfonated]
Anilinep-Toluidine[Dimcthylation,
TrisuKonation]or
[Magenta dimetliylated,trisulfonated]
p-ToluidineAniline (3-4 mols)[Sulfonation]
or[Spirit Blue sulfonated]
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from o-Toluidine (continued)
SchultzNumberfor Dye
537
538
539
540
541
582
606
Ordinary Name andClass of Dye
TRIPHENTL-METHANEDYES (continued)
Methyl Blue for SilkMarine Blue
Methyl BlueCotton Blue
Water BlueSoluble Blue
Pacific Blue
Brilliant DianilBlue 6G
XANTHONE DYEFast Acid Violet
A2R
ACRTDIKE DYEPhosphine
IMMI
Statistics ofImport and
Manufacture
14:—18:—19:—'20:—
M'20:—
I
IMMI
14:—
14:—18:—19:—'20:—
M '20:—
II
14:—'20:—
M'20:—
IMMMI
34,867??
2,395?
50,255
91,152?
16,3151,387
98,770
8752,679?
14.-168,17517:—18:—19:—'20:—
M'20:—
??
14,64819,259
?
Other IntermediatesUsed and Notes
Aniline (4 mols)2>-Toluidine[Sulfonation]
Aniline (4 mols)p-Toluidine[Di- and trisulf onation]
p-ToluidineAniline (3-4 mols)[Di- and tri-sulf onation]
or[Spirit Blue di- and tri-
sulfonated]
Anilinep-ToluidineDiamino-diphenyl-
methane[Sulfonation]
ft-Naphthylamine(3 mols)
Aniline2>-Toluidine[Disulfonation]
Phthalic AnhydrideResorcinol (2 mols)o-Toluidine (2 mols)[PC15, Sulfonation]
p-ToluidineAniline[Magenta by-product]
DyeAppli-cationClass
A
B
A
D
B
A
B
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from o-Toluidine (continued)
559
SchultzNumberfor Dye
679
683
687
702
703
704
705
733
888
Ordinary Name andClass of Dye
AZINE DYESSafranine
Salfranine MN
Rosolane 0
Para Blue
Rubramine
Indamine 3R
Indamine 6R
STJLFTJE DYEImmedial Indone
INDIGO GEOTJP DYEIndigo MLB/T
Statistics ofImport and
Manufacture
I '14:— 59,921M'17:— ?M'18:—106,591M'19:—131,042I '20:— 386M'20:—149,629
I '14:— 198M'18:— ?M'19:— ?M'20:— ?
I '20:— 1,083
I '14:— 66,170I '20:— 9,681
I '14:— 4,236
I '14:— 10,730I '20:— 827
Other IntermediatesUsed and Notes
p-Tolylene-diamineAniline oro-Toluidine (extra
mol)
Dimethyl-p-phenylene-rlmiminft
Aniline[Oxidation]
o-Amino-diphenylamineAniline[Oxidation]
Aniline (3-4 mols)p-Toluidinep-Phenylene-diamine
or[Spirit Blue, p-Pheny-
lene-diamine]
Nitroso-dimethyl-aniline
p-Toluidine
Nitroso-dimethyl-aniline
Nitroso-dimethyl-aniline
p-Toluidine
p-Amino-phenol[S+Na*S]
o-Toluidine (2 mols)[Chloro-acetic, soda-
mide, etc.]
DyeAppli-cationClass
B
B
B
B
B
B
B
S
V
.-,60 DYES CLASSIFIED BY INTERMEDIATES
p-Tolwdine
Xote.—C. A. numbering begins with XH2, while German and Englishhnmbaing generally starts from
/ \
: H 3
STATISTICS.—Imported 14:— 24,686 lbs.Manufactured 17:—223,778 lbs.Manufactured 18:—205,852 lbs.Manufactured 19:—575,841 lbs.Manufactured '20:—894,169 lbs.
FORMATION.—Toluene is nitrated to a mixture of o- and p-nitro-toluenes,which are separated. The p-nitro-toluene is reduced with ironand hydrochloric acid
LITERATURE.—Cain, Intermediate Products (2d Ed . ) , 58Lange, Zwischenprodukte, #234-240, 261
Dyes Derived from ^-Toluidine
SchultzNumberfor Dye
4S2
511
512
Ordinary Xame andClass of Dye
TRISAZO DYESAlizarin Yellow FS
TRIPHENYI/-METHANEDYES
ParafuehsineParamagenta
MagentaFuchsine
Statistics ofImport and
Manufacture
I 14:— 65,026M18:—• ?M19:— ?M'20:— ?
I 14:— 87,102M17:— 17,739M IS:— 71,675M19:—155,830I '20:— 189M'20:—284,285
Other IntermediatesUsed and Notes
Aniline ando-Toluidine [or
Magenta]Salicylic Acid (3 mols)
Aniline (2 mols)[Nitro-benzene and iron
or Arsenic Acid]
Anilineo-Toluidine[Nitro-benzene, etc.; or
Arsenic Acid]
DyeAppli-cationClass
M
B
B
DYES CLASSIFIED BY INTERMEDIATES 561
Dyes Derived from ^-Toluidine (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cation
514
520
521
524
525
526
TRIPHENYL-METHANEDYES (continued)
Red Violet 5R I '14:—I '20:—
331750
Light Blue SuperfineSpirit Soluble
Diphenylamine Blue
Spirit BlueAniline Blue
I '14:— 2,149
I '14:— 50,563M'17:— ?M'18:—M'19:—I '20:—M'20:—
??723
Fuchsine SAcid Magenta
Red Violet 5RS
I '14:— 19,098I '20:— 524M'20:— ?
Acid Violet 4RS
Anilineo-Toluidine[Nitro-benzcne, etc.;
or Arsenic Acid][Methylation or ethyla-
tion]or
[Magenta methylatedor ethylated]
Aniline (5 mols)[Benzoic Acid]
Aniline (3-4 mols)o-Toluidine[Benzoic Acid]
or[Magenta phenylatcd]
Anilineo-Toluidine[Sulfonation]
or[Magenta sulfonated]
Anilineo-Toluidine[Ethylation, Sulfona-
tion]or
[Red Violet 5Rsulfonated]
Anilineo-Toluidine[Dimethylation, Tri-
sulfonation]or
[Magenta methylated,sulfonated]
502 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from ^-Toluidine {continued)
Schultz Ordinary xame andSumher Class of Dyefor Dye J *
Statistics ofImport and
Manufacture
535
536
537
53S
539
540
541
TRIPHEXYL-METHANDYES
{continued)Methyl Alkali Blue
Alkali Blue
Methyl Blue for SilkMarine Blue
Methyl BlueCotton Blue
Water BlueSoluble Blue
Pacific Blue
Brilliant DianilBlue6G
I '14M'18M'19I '20
:— 27;
:— 2\
I '14:—286,75M '17:— ?M '18:— 43,184M'19:—77,796I '20:— 6,771
M'20.— 74,253
I '14.— 34,867M'18:— ?M'19:— ?I '20:— 2,395
M'20:— ?
I '14:— 50,255
I '14:— 91,152M'18:— ?M '19:— 16,31I '20:— 1,387
M '20:— 98,770
Other IntermediatesUsed and Notes
Aniline (5 mols)[Sulfonation]
o-ToluidineAniline (3 -4 mols)[Sulfonation]
0-ToluidineAniline (4 mols)[Sulfonation]
o-ToluidineAniline (4 mols)[Di- and tri-sulf onation
o-ToluidineAniline (3-5 mols)[Di- and tri-sulf onation]
or[Spirit Blue Sulf onated]
Anilineo-ToluidineDiamino-dipnenyl-
methane[Sulfonation]
iS-Naphthylamine(3 mols)
Anilineo-Toluidine[Disulfonation]
DyeAppli-cationClass
B
D
DYES CLASSIFIED BY INTERMEDIATES 563
SchultzNumberfor Dye
580
606
616
683
686
702
703
Dyes Derived
Ordinary Name andClass of Dye
XANTHONE DYEFast Acid Violet B
ACRIDINE DYEPhosphine
THIOBENZENYL DYEPrimuline
AZINE DYESSafranine MN
Amethyst Violet
Para Blue
Hubramine
from />-Toluidine (continued)
Statistics ofImport and
Manufacture
I '14:— 20,688M'19:— ?I '20:— 2,907
I '14:—168,175M '17:— ?M'18:— ?M'19:— 14,648I '20:— 19,259
M'20:— ?
I '14:— 67,976M'17:— 72,461M '18:— 72,778M'19:—271,338I '20:— 441
M '20:—183,179
I '14:— 198M'18:— ?M'19:— ?M'20:— ?
Other IntermediatesUsed and Notes
Phthalic anhydrideResorcinol (2 mols)p-Toluidine (2 mols) or
Aniline (2 mols)[PCI5, Sulfonation]
Anilineo-Toluidine or
2d mol Aniline[Magenta by-product]
p-Toluidine (4 mols)[Sulfur, Sulfonation]
Dimethyl-p-phenylene-diamine
Aniline[Oxidation]
Diethyl-p-phcnylene-diamine
Diethyl-aniline[Oxidation]
Aniline (3-4 mols)o-Toluidinep-Phenylene-diamine
or[Spirit Blue and p-
Phenylenc-diamine]
Nitroso-dimethyl-aniline
o-Toluidine
DyeAppli-cationClass
A
B
D
B
D
B
B
5&4 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from j5>-Toluidine (continued)
Schultz'
for Dye' of Dye
AZIXE DYE(continued)
705 I Indamine 6R
ANTHRAQUINONE ANDALLIED DYES
S52 Alizarin Irisol D, R
S53
S54
855
856
859
860
864
AnthraquinoneViolet
Alizarin ViridineDG,FF
Alizarin PureBlueB
Alizarin Astrol B
Gyananthrol R
Cyananthrol G
AnthraquinoneGreen GX
Statistics ofImport and
Manufacture
I '14:— 66,170I '20:— 9,681
I '20:— 401
I '14:-I '20:-
1,2021,649
I J20:— 11,397
I '14:I '20:
I '14:-I '20:-
10,90715,518
1S,7922,416
I '14:-I '20:-
1,7092,531
Other IntermediatesUsed and Notes
Nitroso-dimethyl-aniline
o-Toluidine
Quinizarin[Sulfonation]
1:5-Dinitro-anthraqui-none
[Sulfonation]
Anthraquinone-2-sul-fonic Acid
[Sulfonation][Or through Alizarin
Bordeaux from Aliz-arin]
l-Amino-2:4-dibromo-antliraquinone
[Sulfonation]
l-Bromo-4-methyl-amino-antliraquinone
[Sulfonation]
l-Amino-4-bromo-2-methyl-anthraquinone
[Sulfonation]
l-Amino-4-bromc-(chloro)-2-methyl-an-thraquinone, etc.
[Sulfonation]
1-Nitro-anthraquinone-6-sulf onic Acid
Aniline
DyeAppli-cation
ACr
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from ^-Toluidine (continued)
565
SchultzNumberjor Dye
865
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
(continued)Alizarin Cyanine
Green E
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
Quinizarinp-Toluidinc (2 mols)[Sulfonation]
DyeAppli-cationClass
ACr
o-Toluidine-m-sulfonic Acid
See, 4-Amino-m-toluene-sulfonic Acid (C. A. nomen.)
/>-Toluidine-o~sulfonic Acid
See, 5-Amino-o-toluene-sulfonic Acid (C. A. nomen.)
8-^-Toluino-l-naphthalene-sulfonic Acid (C. A. nomen.)
See, p-Tolyl-l-naphthylamme-8-sulfonic Acid
m-Toluylene-diamine
See, m-Tolylene-diamine
o: ^-Toluylene-diamine
See, m-Tolylcne-diamine
Toluylene-diamine-sulfonic Acid
See, 3: 5-Diamino-p-toluene-sulfonic Acid (C. A. nomen.)
m-Toluylene-diamine-sulfonic Acid
See, 4: 6-Diamiixo-m-tolucne-sulfonic Acid (C. A. nomen.)
/>-(o-Tolyl-azo-)-o-toluidine (C. A. nomen.)
See, o-Amino-azo-toluene
566 DYES CLASSIFIED BY INTERMEDIATES
4-m-Tolylene-bis(thiourea) (C. A. nomen.)
See, m-Tolylene-dithiourea
4-m-Tolylene-diamine (C. A. nomen.)
See7 m-Tolylene-diamine
m-Tolylene-diamine
4-7n-Tolylene-diamine (C. A. nomen.
m-Toluylene-diamine
o: p-Toluylene-diainine
Note.—English and Germans often start numbering from
NH:
= C7HioN2=122
STATISTICS.—Imported J14:—135,383 lbs.Manufactured '17:—302,596 lbs.Manufactured '18:—612,163 lbs.Manufactured '19:—139,544 lbs.Manufactured '20:—689,036 lbs.
FORMATION.—From ;?i-dinitro-toluene by reduction with iron and hydro-chloric acid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 86
Dyes Derived from m-Tolylene-diamine
SchuhNumberfor Dye
34
Ordinary Name andClass of Dye
MONOAZO DYESChrysoidine R
Statistics ofImport and
Manufacture
I '14:—111,006M'17:— 58,115M '18:—137,035M '19:—220,542I '20:— 1,102M'20:—186,793
Other IntermediatesUsed and Notes
Aniline
DyeAppli-cationClass
B
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from m-Tolylene-diamine (continued)
567
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
69
284
295
352
413
453
455
458
MONOAZO DYES(continued)
Chrysoidine R
DISAZO DYESVesuvine BBismarck Brown II
Diphenyl FastBlack
Direct Violet R
Direct Violet BB
TRISAZO DYESColumbia Black R
Columbia Black B
Carbon Black
I '14:—171,133M' 17 :—262,600M' 18 :—295,080M'19:—631,308M'20:—484,929
I '14:— 882
I '14:— 661M'19:— ?
I '14:— 4,396
I '14:— 1,307
I '14:—165,727
o-Toluidine
m-Tolylene-diamine(3 mols)
Gamma Acidp: p'-diamino-ditolyl-
amine
Benzidine1:7-Dihydroxy-6~naph-
thoic-3-sulfonic Acid
Dianisidine1:7-Dihydroxy-naph-
thalene-4-sulfonicAcid
Tolidine2R Acidm-Tolylene-diamine
(2 mols)
Dianisidine2R Acidm-Tolylene-diamine
(2 mols)
p-Phenylene-diamine-sulf onic Acid
[from p-Nitro-aniline-o-eulf onic Acid]
l-Naphthylamine-6(7)-sulf onic Acid
m-Tolylene-diamine(2 mols)
568 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from m-Tolylene-diamine (continued)
SchultzNumberfor Dye
Ordinary Name andClass of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
461
463
602
605
670
710
711
TRISAZO DYES(continued)
Coomassie UnionBlack
Erie DirectBlack RX
Cotton Black E
ACRIDINE DYES
Acridine Yellow
Benzoflavine
AZINE DYE
Neutral Red
I '141—248,567M'19:— ?M'20:—
2,050,741
I '14-M'19:-
1,913?
1:4-Naphthylene-dia-mine-2-sulf onic Acid
Gamma Acidm-Tolylene-diamine
(2 mols)
BenzidineAnilineHAcid
m-Tolylene-diamine(2 mols)
[Formaldehyde, Am-monia removal,Oxidation]
I '14:— 600
MJ18:— ?
SULFUR DYE
Immedial Yellow D
Immedial Orange N
I '14:— 13,400
I '14:— 500
m-Tolylene-diamine(2 mols)
Benzaldehyde[Ammonia removal,
Oxidation]
Nitroso-dimethyl-aniline or
Dimethyl-p-phenylene-diamine
[Oxidation]
[Sulfur]
[Sulfur]
DYES CLASSIFIED BY INTERMEDIATES
^-Tolylene-diamine (C. A. nomen. NHt=l)
p-Toluylene-diamine
Note.—English and Germans often start numbering with CHz
569
NH2
C^| CH3 n n vrI O7XI10JN2
H2
122
STATISTICS.—Manufactured '20:— ?
FORMATION.—By reduction of amino-azo-toluene (from 0-toluidine)
with zinc dust and hydrochloric acid
LITERATURE.—Nietzki, Ber. 10, 1158
Green, Organic Coloring Matters (1908), 37
Dyes Derived from ^-Tolylene-diamine
JSchultz
for Dye
124
125
126
Ordinary Name andClass of Dye
MONOAZO DYES
Diazine Green S
Diazine Black
Indoine Blue R
Statistics ojj. lYtporz ana
Manvfacture
I '14:— 1,340
I '14:— 2,630I '20:— 701
I '14:— 15,353M'17:— ?M'18:— ?
Other IntermediatesUsed and Notes
o-ToluidineAniline or o-Toluidine[or Safranme]Dimethyl-aniline
o-ToluidineAniline or o-Toluidine[or Safranino]Phenol
o-ToluidineAniline or o-Toluidine[or Safranme]jS-Naphthol
DyeAppli-cationClass
B
B
B
570 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from />-Tolylene-diamine {continued)
SchultzNumberfor Dye
127
128
679
Ordinary Name andClass of Dye
MONOAZO DYES(continued)
Methvl Indone B
Janus Gray B
AZINE DYESafranine
M '17:—
Statistics ofImport and
Manufacture
I '14:— 59,920M '17:M'18:-M'19:-I '20:-
M '20:-
-106,591-131,042- 386-149,629
Other IntermediatesUsed and Notes
0-ToluidineAniline or o-Toluidine[or Safranine][" Amino-naphthols "]
o-ToluidineAniline or o-Toluidine[or Safranine]etc.
o-ToluidineAniline or
2d mol o-Toluidine
DyeAppli-cationClass
B
B
B
l-ToIylene-2:6-diamine-4-sulfonic Acid
See, 3 : 5-Diamino-p-toluene-siilfoinc Acid (C. A. nomen.)
m-ToIylene-diamine-sulfonic Acid
See, 4:6-Diajnino-m-toluene-siilfonic Acid ( C A, nomen.)
m-Tolylene-dithiourea
4-m-Tolylene»bis[thiourea] (C. A. nomen.)
N H . C S . N H 2
X H . C S . NH» = C9Hi2N4S2=240
DYES CLASSIFIED BY INTERMEDIATES 571
FORMATION.—By heating m-tolylene-diamine thiocyanate several hourson a water bath
LITERATURE.—Lange, Zwischenprodukte, #801
Dyes Derived from m-Tolylene-dithiourea
SchultzNumberjor Dye
712
716
Ordinary Name andClass of Dye
SULFUR DYESKryogene Yellow G
Kryogene Yellow R
Statistics ofImport and
Manufacture
I '14:— 1,126I '20:— 1,543
I 14:— 4,804
Other IntermediatesUsed and Notes
Bcnzidine[Sulfur]
[Sulfur]
DyeAppli-cationClass
S
S
/>-Tolyl- a-naphthylamine
iV-p-Tolyl-1-naphthylamine (C. A. nomen)
FORMATION.—From a-naphthylamine hydrochloride and p-toluidine
by heating together to about 280°
LITERATURE.—Cain, Intermediate Products (2d Ed.), 186
Dye Derived from />-Tolyl-a-naphthylamine
SchultzNumberfor Dye
560
Ordinary Name andClass of Dye
DlPHENYL-NAPHTHYL-METHANE DYE
Night Blue
Statistics ofImport and
Manufacture
I 14:— 361M'19:— ?I '20:— 11
Other IntermediatesUsed and Notes
Tetraethyl-diamino-benzophenone
DyeAppli-cationClass
B
!2 DYES CLASSIFIED BY INTERMEDIATES
^-Tolyl-l-naphthylamine-8-sulfonic Acid
S-p-Tolumo-l-rcaphthalene-sulfonic Acid (C. A. nomen.)
Tolyl-peri Acid
HO3S
CAUSTICS.—Imports '14:—1,097 lbs.Manufactured '18:— ?Manufactured '19:— ?Manufactured '20:— ?
)RMATION.—From l-naphthylamine-8-sulfonic acid and p-toluidineb}r heating together in an autoclave
TERATURE.—Cain, Intermediate Products (2d Ed.), 195Lange, Zwischenprodukte, #2859
Dyes Derived from ^-Tolyl-l-naphthylamine-8~sulfonic Acid
I*2 Ordinary Name andClass of Dye
89
157
MONOAZO DYESulf on Acid Blue B
DISAZO DYESulfoncyanine
Statistics ofImport and
Manufacture
I '14:— 35,560M '17:— ?M '19:— ?M '20:— ?
I '14:—145,694M '17:— ?M'18:— ?M'19:— ?I '20:— 18,327
M'20:— ?
Other IntermediatesUsed and Notes
HAcid
Metanilic Acida-Naphthylamine
DyeAppli-cationClass
A
Tolyl-peri Acid
See, 2>*Tolyl-l-naphthylajnine-8-sulfonic Acid
DYES CLASSIFIED BY INTERMEDIATES
1:2:4-Triamino-anthraquinone
CO
573
NH2
FORMATION.—1:4-Diamino-anthraquinone is diacetylated, and then
nitrated with nitric acid of sp. gr. 1.5. By reduction of the nitrated
product the 1: 2:4-triamino-anthraquinone is prepared
LITERATURE.—Lange, Zwischenprodukte, #3333
Dye Derived from l:2:4-Triamino-anthraquinone
SchultzNumberfor Dye
822
Ordinary Name andClass of Dye
ANTHRAQUINONE ANDALLIED DYES
Algol BrilliantOrange FR
Statistics ofImport and
Manufacture
I J14:— 6,195I >20:— 482
Other IntermediatesUsed and Notes
Benzoyl Chloride
DyeAppli-cationClass
V
Triamino-triphenyl-methane
Tris(p-amino-phenyl)-?nethane (C A. nomen.)
p-Leucaniline
H2N< >NH2
FORMATION.—(1) From para-rosaniline by reduction with zinc. (2) From
corresponding nitro-compounds by reduction
LITERATITRE.—Beilstein, Orgardsche Chemie (3d Ed.), 4,1194
•4 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from Triamino-triphenyl-methane
rJlvltZimberr Dye
511
Ordinary Name andClass of Dye
TBIPHENTL-METHAXEDYE
ParafuchsineParamagenta
Statistics ofImport andManufacture
I '14:— 65,026M'18:— ?M'19:— ?M'20:— ?
Other IntermediatesUsed and Notes
(Oxidation)
Appli-cationClass
B
a-Trichloro-toluene
See, Benzo-tricHoride
3:4:5-Trihydroxy-benzoic Acid
See, Gallic Acid
Trimethyl-m-aoiiino-phenyl-aminoniiini Chloride
See, (w-Amin(>phenyl)4rimethyl-aminoiiium Chloride
a-Trinitro-naphthalene
1:3:5-Trinitro-naphthalene (not considered herein)
/3-Trinitro-naphthaJene
1:3:8-Trinitro-naphthalene (not considered herein)
7-Trinitxo-naphthaleiie
1:4:5-Trinitro-naphthalene (not considered herein)
5-Trinitro-naphthalene
1:2:5-Trinitro-naphthaJene (not considered herein)
l:3:5-TriphenyI-hexahydro-s-triazine (C. A. nomen.)
See, Aiihydro-formaldehyde-aniline
DYES CLASSIFIED BY INTERMEDIATES
Tris(^-amino-phenyl)-methane (C. A. nomen.)
See, Triamino-triphenyl-methane
575
Trisulfonic Acid
See, Naplithalenc-1: 3: 6-trisulfonic Acid
5: 5'-Ureido-bis(2-amino-benzene-sulfonic Acid) (C. A. nomen.)
See, Diamino-diphenyl-urea-disulfonic Acid
m-Xylene (C. A. nomen.)
m-Xylol
JCH3
FORMATION.—This occurs in commercial crude xylol as the most abun-dant constituent, and is separated from its isomers by treating thecrude xylol with a limited quantity of sulf uric acid, and by hydroly-sis of the sulfonatc formed
LITERATURE.—Green, Organic Coloring Matters (1908 Ed.), 5
Dye Derived from m-Xylene
SchultzNumberfor Dye
564
Ordinary Name andClass of Dye
TLUPIIENYL-METHANEDYE(?)
Naphthalene GreenV
Statistics ofI in'port and
Manufacture
I '14:— 22,144I '20:— 9,291
Other IntermediatesUsed and Notes
p-Dimethylamino-benzaldehyde
Dimethyl-aniline
DyeAppli-cationClass
A
576 DYES CLASSIFIED BY INTERMEDIATES
XylidineThe crude mixture contains the following isomers:-
NH3
CH3
CH3
NH2
32 4-xylidine(m-4-xyhdme)
H3C
2 5-xyhdine(p-xylidme)
NH2
2 6-xylidine(m-2-xylidine)
(C A nomen(CHl)
2 3-xyhdine(o-3-xylidine)
Q
CH33 4-xyhdine(o-3 -xylidine)
(C A Tiotnen. NHz=l)(CHl)
STATISTICS.—Imported '14:— 21,836 lbs.Manufactured '17:-^25,873 lbs.Manufactured '18:—534,834 lbs.Manufactured '19:—386,635 lbs.Manufactured '20:—1,054,476 lbs.
FORMATION.—Xylene is nitrated with mixed acid, preferably cold.The mixed nitro-xylenes are then reduced with iron and hydro-chloric acid
LITERATURE.—Cain, Intermediate Products (2d Ed.), 58Lange, Zwischenprodukte, #742-747
Dyes Derived from Xylidine
SchvltzNumberfor Dye
76
77
78
Ordinary Name andClass of Dye
MONOAZO DYESSudan II
Azo Coccine 2R,
Cochineal Scarlet 4R
Statistics ofImport and
Manufacture
I '14:— 501M'17:— 27,595M'18:— 23,692M'19:— ?M;20:—170,658
Other IntermediatesUsed and Notes
/3-Naphthol
Nevile-Wlnther's Acid
l-Naphthol-5-sulfonicAcid
DyeAppli-cationClass
S3
A
A
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Xylidine (continued)
577
SckultzNumberfor Dye
Ordinary Name andClas* of Dye
Statistics ofImport and
ManufactureOther Intermediates
Used and Notes
DyeAppli-cationClass
79
80
82
685
MONOAZO DYES(continued)
Brilliant Orange RXylidine Orange 2R
Wool Scarlet R
Ponceau R
AZINB DYETannin Heliotrope
I '14:— 4,204M'17:— ?M'18:— 18,909M'19:— ?M'20:— ?
I '14:— 39,8
'14:— 35,259M'17:—633,429M'18:—
1,189,054M'19:—552,680M'20:—
1,286,002
I '14:— 1,398I '20:— 249
SchaefTer's Acid
l-Naphthol-4: 8-disul-f onic Acid
R Acid
Nitroso-dimethyl-aniline
A
A
B
2:4-Xylidine (C. A. nomen. NH2=1)
m-Xylidine
N H
= C 8 H u N = :0
CH 3
STATISTICS.—Manufactured '20:—but amoun t not disclosed
FORMATION.—By separation from commercial xylidine as ace ta te
LITERATUBE.—Cain , Intermediate Products (2d Ed . ) , 59
578 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 2:4-Xylidine
SchultzNumberjor Dye
81
82
211
Ordinary Name andClass of Dye
MONOAZO DYESPalatine Scarlet ABrilliant Cochineal
Ponceau 2RScarlet 2R
DISAZO DYEResorcine Brown
Statistics ofImport and
Manufacture
:— 7,510
I '14:— 35,259M'17:—633,M '18:—
1,189,054M'19:—552,680M ' 2 0 : -
1,286,002
I '14:— 13,189M'17:— ?M'18:—M'19:—I '20:—
M '20:—
??
2,484?
Other IntermediatesUsed and Notes
l-Naphthol-3:6-disul-fonic Acid
R Acid429 [Only small part of total
production from m-xylidinc]
Sulfanilic AcidResorcinol
DyeAppli-cationClass
2: 6-Xylidine (C. A. nomen. NH>2=1)
p-Xylidine(CH3=JO
H3C
FORMATION.—Crude xylidine is treated with sufficient glacial acetic
acid to cause the m-xylidine acetate to crystallize out . T h e mother
liquor is mixed with hydrochloric acid, and after a few days the
p-xylidine hydrochloride is separated
LITERATURE.—Cain, Intermediate Products (2d Ed. ) , 59
Lange, Zwischenprodukte, #742-747
DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from 2:6-Xylidine
579
SchultzNumberfor Dye
438
Ordinary Name andClass of Dye
TBISAZO DYEMelogene Blue BH
Statistics ofImport and
Manufacture
M '17:— ?M'18:— ?
Other IntermediatesUsed and Notes
BenzidineH Acid (2 mols)
DyeAppli-cationClass
D
m-Xylidine
See, 2: 4-Xylidine (C. A. nomen.)
m-4-Xylidine
See, 2: 4-Xylidine (C A. nomen.)
/>-Xylidine
See, 2: 5-Xylidine {C. A. nomen.)
Xylidine-sulfonic Acid
C6H2. NH 2 . (CH3)2. SO3H = = 201
FORMATION.—^Probably by sulfonation of either crude or purified
xylidine with sulf uric acid in a vacuum or in a current of an indiffer-
ent gas
LITERATURE.—Thorpe, Die. Chemistry, 5, 797, 798
Junghahn, Ber. 35, 3747-3767 (1902)
SchultzNumherfor Dye
214
Dye Derived
Ordinary Name andClass of Dye
DISAZO DYEFast Brown 0
from Xylidine-sulfonic Acid
Statistics ofImport and
Manufacture
I '14:— 2,000
Other IntermediatesUsed and Notes
Xylidine-sulfonic Acid(2 mols)
a-Naphthol
DyeAppli-cationClass
A
580 DYES CLASSIFIED BY INTERMEDIATES
4-(2:4-Xylyl-azo)-2:5-xylidine (C. A. nomen.)
See, Amino-azo-xylene
Y Acid
See, G Acid
Yellow Acid
l:3-Dihydroxy-naphthalene-5:7-disulfonic Acid (not consideredherein)
Zeta Acid
Naphthasultone-3-sulfonic Acid (not considered herein)
F O R M U L A I N D E X O F I N T E R M E D I A T E S
The formulas are indexed here for the 487 intermediates for whichdata and tables are listed. Only one chemical name is given, but onthe pages referred to there are enumerated the various trivial names andsynonyms.
The arrangement of the formulas follows that of the 1920 ChemicalAbstracts (C. A. 14, 4557) where "The arrangement of symbols informulas is alphabetical except that in carbon compounds C alwayscomes first, followed immediately by H." "The arrangement of theformulas is also alphabetical except that the number of atoms of anyspecific kind influences the order of compounds/7 e.g., all compoundswith C6 come before those with C7, thus CcHsCl precedes C7HcClNO2.This is likewise true for all the other atoms, and consequently we findC7H6C1NO2 before C7H9N, and C8H2Br2ClNO before C8H2C14O4.
I t is believed that a formula index affords the easiest and surest wayto find an organic compound, and it is for this reason that this indexis given. This is paiticularly true of intermediates where often manynames are used for the same chemical individual.
CClaO
CeHsClWuC«HsClN2O7S
CeHsClaNOaC6H3N3O7CeEUCINO*CaEUClNOsS
CeEUNaOs
CaHsCKhSCeHaClaNCaHtClaNOCeHsNOa
CaHsNOs
CaHsNsOiCeHsNaOsCaHaClNOjS
CeHaNaOa
PAGEPhosgene 486Dihydroxy-tartaric Acid 229l-Chloro-2 4-dmitro-bonzeno 1614-Chloro-3 5-dmitro-bcnzeno-
bulfonic Acid 1622 5-Dichloro-nitro-benzono 210Picric A( id 495o-and p-Chloro-nitro-bonzonea 1092-Chloro-5-nitro-bonzo no-sul-
f onic Acid4-Chloro-3-nitro-b( nzono-sul-
f onic Acidtn-Dinitro-benzono2 4-Dinitro-phonolChloro-benzone2-Chloro-4-nitro-amhneBonzene-sulf onyl Chloride2 5-Dichloro-amhno2-Ammo-4 6-diohloro-phenolNitro-bonzenop-Nitroso-phonolNitro-phonol, crudeo-Nitro-phonolp-Nitro-phenol4-Nitro80-rG3orcinol2 4-Dinitro-anilinePicramic Acid2-Ammo-6-chloro-bonzene-8ul-
f onic Acid»7i-Nitro-anilinep-Nitro-anilme2-Amino-5-mtro-bonzonc-sul-
fonic Acid4-Amino-3-nitro-benzonc-sul-
fonic Acid6-Nitro-motanihc Acid
109
170251258161107125200504304484J44*5436449248494
45420421
74
75434
CoHsNaOiS
CJIsNaOoSa
CeHioOsCai^ClNOs
C7EUCI2O
PAGECoHcNaOeS 2-Ammo-6-nitro-phenol-4-
sulf onic Acid 77CcHoO Phenol 459CeHoOa llosorcinol 509CeHeOs Pyrogallol 499CeHeOoS Pyrogallol-5-sulfonic Acid 500CaH7N Anxlmo 90CaH7NO m-Amino-phenol 77
p-Armno-phcnol 78CeHyNOaS Motamhc Acid 333
Jjulfanihc Acid 528CetfrNTQiS 2-Amino-phonol-4-sulfonic
Acid 803-Amino-phenol-4-sulfomc
Acid 81C«H7NOoSa 2-Amino-p-bonzono-disulfonic
Acid 394-Amino-m-bonzono-disul-
fonic Acid 39CaH7NO7Sa 4-Arnino-phcnol-2 C-disul-
fonic Acid 79CaEhNsOa 4-Nitro-m-phenylono-diamino 437CoIisNa w-Phonylono-diamino 405
7)-Phonylene-diamme 470CoIIsNaOaS p-Phonylono-diaimne-sulfonic
474AndP lieny 1-hy drazinc-p-sulf onic
A( id 4812 O-Diannno-l-phonol-4-aul-
fonic Acid 198m-Phonylone-di amino-disul-
fonio Acid 473Aooto-acetic Ethyl Ester 212-Chloro-5-mtro-benzaldehydo 1682-Chloro-6-nitro-benzaldchydo 1682 5-Dichloro-benzaldehyde 209
5 8 1
582 FORMULA INDEX OF INTERMEDIATES
C7H6C1O
C7H6C1NO2CHNOC 7 6 2 5CTHCOC7HflO2
C7HGO2SC7HCO3C H O
C7HCO4SCrHeOEC7H6O7S2C7H7CIC7H C1OSC7H7NOC7H7NO2
C7H7NO3
C7H7NO4C7H7NO6S
CrHaCINOCvHaClNOsS
CTHSNSOC7H8N2O2
C7H8N2O3
C7H8OC7HaO2C7H0N
CTHQNO
CTHQNOSS
C7HioN2
C7HioN2OsS
CsH-BrzClNO
C8H4CI2O4CH4O3C8H5NO2
C8H6C1NO4S
sflOSCSHTCIOS
C«H7NOC*H7NOS
Benzoyl Chlondeo-Chloro-benzaldehyde2-Chloro-benzaldehyde-G-sul-
f onic AcidBcnzo-trichlondew-Nitro-bcnzaldehydeo-Nitro-benzaldehydep-Nitro bcnzaldehvdcp-Nitro-benzyl Chloride2 4-Dimtro-toIucnoDimtro-p cresolBenzaldehydeBeii7oic Acidwi-Hydroxy-benzaldehj doThio-sahcyhc AcidSalicylic Acida-RehOicyhc Acid/S Resorcvhc AcidBen/caldehydc-o-sulfomc AcidGallic AcidBenzaldehydc-disulfonic AcidBenzyl Chlondep-Toluenc-sulfonyl Chloridem-Ammo-benzaldohj dep-Amino-ben7aldehydom Ammo-benzoic AcidAnthranihc Acido-Nitro-toluenep-Nitro-tohicne5-Ammo-sahcylic 4.cido-Nitio-amsoleGallamide5-Nitro-o-toluene-sulfoiuc
Acidp-Sulfo-anthramhc Acid5-Chloro-o-anisidme2-Annno-5-chloi o-p tolucne-
sulfomc Acidp-NitrofeO-methyl-anihno2-Niti o-p-toluidme3-Nitro-p-i oluidme5-Nitro-o-tokudino2-Amino-G-mtro-p-crcsol4-Nitr o-o-ani aid me5-Nitro-o-amsidmoCresolResorcmol Methyl EtherJV-Methyl-amlmeToluidincs (mixed)m-Toluidinoo-Toluuhnep-T oluidme2-Annno-p-cresol3-Amino-p-( icsolo-Anisidine4-Annno-m-toluone-sulfonic
Acid5-Amino-o-toluone-aulfonic
Acidm-Tolylenc-diammcp-Tolylene-diammo3 5-Diammo-p-toluone-sul-
fomc Acid4 6-Diirnino-m-toluene-sul-
fonic Acid5 7-Dibromo-isatm ChlorideTetrachloro-phlhahc A( id3 G-Dichloro-plithahe AcidPhthahc AnhydrideIsatmPhthahmide4-Chloro-2-mtro-phf»nyl-
thioglycohc Acid2-Hyrlroxy-thionaphthenem-Chloro plu nyl-thioslycolic
AcidIndoxyl5-Amino-2-hydroxy-thionaph-
thene
PAGE140158
15913842742S42943226125212013730S5445185lf5171222 SO12114 3551
373840
110450451
SI-42G2S7
452532150
4044045445515575
4254201775153 30552553554500
4748
107
80
r S 7
500
200
2002005,3 (>2114S7J21493
170313
171320
58
C8H7NO3C8H7NO4S
CsHaNaOsCsHsOs
CsH8O75S2
CsHoN
C8H0NOCsHoN02CsHioC8HioN20
CsHnN
CsHnNO
CaHuNOaSCaIIi2N2
C8Hi2N2O3S2
CsIIoOsS
CoII7BrOS
C8Il7C104S
C0II7N
C«HoC102S
COHDNOC»HoN04
CBIIIOCINO
C0II11NO
CBH12N2O2
CeHj2N 12CalliaN
CDITi4N2
3oErnCiivr2
C10II6N2O4
CioITe02Ciollc04C10H0O&S
CioHoOaSa
PAGE2-Nitro-m-tolualdehyde 449o-Nitro-phenyl-thioglycoho
Acid 438p-Nitro-acetanihde 417o-Cresotic Acid 177Gallic Acid Methyl Ester 2933-Methyl-benzaldehyde-4 G-
disulfonic Acid 337Anhydro-formaldehyde-o-
tolmdme 90Acetanihde 21Phcnyl-glycme 475w-Xylene 575p-Amino-acetamlide 26p-Nitroso-dnnethyl-anihno 4 307>-Nitroso-oih'sl-anihno 445Dirnethyl-amlme 237iV-Ethyl-inilmo 271JV-Methyl-o-toluidino 345X> hdine 5702 4-Xyhdine (NH2 = 1) 5772 5-Xj hdme (NH<> = 1) 5782-Arnmo-p-ci esol Methyl
Ether 40m Dimethylamino-phenol 230m-Ethvlimiiio-phcnol 271p--Phenetidmo 458Xyhdine-sulfonic Acid 579N iV-Diinethyl-m-phcnylcne-
diim me 244N 2V"-Dimethyl-p-plieny]one-
dinmme 244F t h\ 1-phenyl-liydi azine 277JZV JV-Dinicthyl-7)-phenylene-
diamine-tlnosulfonic Acid 2402-H ydroxy-thionaphthcne-1-
caiboxvhc Acid5-B r om o-2-l i y d r oxy 1-3-m 0 tl ly 1-
thionaphthcno5-Chloro-phenyl-thioglycol-
o-caibo^cyhc AcidIsoquinohnoQumolmo4-Chloi o-2-Toly 1-thioglycohc
Acid7-Methyl-mdoxylPhenyl-glycmo-o-carboxyhc
Acidp-Dimethylannno-benzoyl
Chlondep-Dimethylammo-benzalde-
hvdep-Nitroso-ethyl-o-tolindino5-Dimethy lununo-2-m troso-
75-creHolm-Tolylone-ditlnourcaAT-Ethyl-JV-niothyl-anilmoA^-Ethyl-o-toluidinoA^-13thyl-p-toluidinoMesidmcPseudocumidmoo-Amino-ben/yl-djmethylainmo 42p-Ammo-bcn/yl-diniethyl-
amineA^-Ethyl-4-m-tolyk ne-dia-
minuA^-Ethyl-p-t olylcno-diamine(m-Annr o-phenyl)-ti lmothyl-
ammonium Chlondo1 5-Dmitro-naphtlialcno
315
150
171323503
172341
478
232
231440
230570274281282332497
42
28,3
1 5-and 1 8-Dimtio-naphtlia-loncH
1 8-Dinitro-naphtlialcno1 2-NaphthoqumonoNaphtha/ann1 2-Naphthoqmnon(i-4~Hul-
fonic Acid1 2-Naphthoq\nnonc-4 C-
disulfomc Acid
82250
25G257381352
382
381
FORMULA INDEX OF INTERMEDIATES 583
PAGEC10H7CIO4S l-Cbloro-8-naphthol-4-sulfonic
Acid 1GIl-Chloro-8-naphthol-5-suifomc
Acid 16CCioH7Ci07S2 l-Chloro-8-naphthol-3 6-
disulfonic Acid 16-iC10H7NO2 l-Nitroso-2-naphthol 44'CioH7N08S3 1 8-Naphthasultam-2 4-di-
sulfonic Acid 35!CioH8 Naphthalene 317CioHaChNaOiS l-(2 5-Dichloro-4-sulfo-phcn-
yl)-3-methyl-5-pyrazolone 212C10H8N2O4S l-Nitroso-2-naphthylannnc-
6-sulfomc Acid 418CioHsNaOeS l-Ammo-8-mtro-2-naphthol-
4-sulfonic Acid 76l-(p Sulfo-phenyl)-5-pyrazo-
lone-3-carboxyhc Acid 533CioH80 a-Naphthol 359
/9-Naphthol 3(>1C10H8O2 1 5-Dihydroxy-naphthalenc 222
2 7-Dihydroxy-naphth ilenc 223CioHgOi 7 S-Dihydroxy-4-methyl-
coumann 222CioHaOiS Croccme Acid 179
l-Naphthol-5-sulfomc Acid 372-Naph.thol-l-3ulfomc Acid 37b2-Naphthol-7-sulfomc Acid 377Nevile-Wmther s Acid 413Sch leffcr'g Acid 525
CioHsO&S 1 7-Dihydioxy-na,phihalcne-4-sulfomc Acid 221
1 8-Dihj. droxy-naphthalcne-4-sulfomc Acid 225
C10II8O0S2 Naphthalenc-1 5-disulfomcAcid 348
Naphthalcnc-1 G-disulfonicAcid 318
Naphthalenc-2 7-disulfomoAcid 348
CioIIsOS. G Acid 280l-Naphlhol-3 0-disulfomo
Acid 309l-Naphthol-3 8-diaulfonio
Acid 370l-Naphtliol-4:8-disulf 01110
Acid 3722-Naphthol-3 7-disulfomc
Acid 373R Acid 504
CioHsOsSa Chroinodopic Acid 173CioIIaOoba Naphth ilc nc-1 3 5-lnsul-
fonic Acid 349Niiphlhaleno-1 3 G-tnaul-
fonic Acid 350CioHsOioSa l-Naphthol-3 G 8-tnsulfomt
Acid 3792-Naphthol-3 G 8-LriHulforuc
Acid 380C10H9N Lopichne 331
a-Nciphthylannno 381/5-NaphthyLiti)ino 391Quinaldmc 501
C10H0NO 5-Ainmo-l-nuphthol 02C10H9NO3S Biocnnor s Aeid 152
Laurent's Acid 32<)Naphthiomo Acid 6r)$l- Japhthyla1Inlnc-2-sulfonlo
Acid 39Sl-NaphtliyIammc-6-sulfoinc
Acid 300, 400l-Naphthylanuno-7-sutfomc
Acid 400, 4011-Naphthylammc-S-sulfomc
Acid 4022-Naphthvlammc-l-sulfonic
Acid 4022-NaphthyKmine-5-8ulfonic
Acid 403
CioIIoNOfiS2
C10IIBNO7S2
C10II0NO0S3
PAGE2-NaphthyIamine-7-suIfonic
Acid 4042-Naphthylamine-8-sulfonic
Acid 403, 405l-Ammo-2-naphthol-4-sulfonic
Acid 67l-Amino-2-naphthol-6-sulfonic
Acid 68l-Ammo-5-naphthol-7-sulfomc
Acid 69l-Amino-8-n iphthol-4-sulfonic
Acid 69l-Anuno-8-naphthol-5-sulfonic
Acid 712-Ainino-l-naphthol-4-sulfonic
Acid 722-Amino-3-naphthol-6-sulfonic
Acid 72Gamma Acid 294J Acid 324Aimno-G Acid 54Ammo-R Acid 83Treund's Acid 285l-Naphthylamine-3 8-disuI-
fonic Acid 3931-N aphthy 1 imme-4 6-disul-
fomc Acid 3941-N aphthy lamine-4 7-disul-
fonic Acid 394l-Naphthylamme-4 S-dibul-
fonic Acid 395l-Naphthylamine-5 7-disul-
fonic Acid 3952-Naphthylainine-5 7-disul-
fonic Acid 396l-Anni)o-S-naphthol-2 4-di-
sulf onic Aoid 631-Anuno-S naphthol-3 5-di-
Hulfonic Acid 64II Acid 208K Acid 3252 11 Add 507l-Naphthvlamino-3 G 8-
tnsulfoDU Acid 4061-Niphthj 1 umm-4 G 8-
trisxilfonic Acid 4072-Naphthylammc~3 6 fc>-
tnaulfonic Acid 4073-Mct hyl-l-phenyl-5-pyra-
/olono 3131 3-Naphthylc nc-diammc-6-
auHonic Acid 4091 1-Napht hj 1< nc-diannnc-2-
Hulfonio Acid 4101 4-N aphthy lonc-diaminc-G-
eulfomc Acid 4112 7-Naphthylpne-diammc-
sulfonic Acid 4113-Mothyl-l-(27-aulfophenyl)-
5-pyiazolone 3441 5-N aphthy lcnc-diammc-
3 7-diauHomc Acid 4081 8-Nnphthylone-diaminc-
6 0-diaulf0111c AcidCh] 409
10343S
215217215
218
219
220L olli 0N2O 3S2 Diethy 1-p-phenylonc-dian unc-
thiuHulfomc Acid 220
/10II11CIO3S 4-CWoro-6-mcthoxY-3-mc thyl-phonyl-thioRljcolic Acid
J10II14N2O 73-NitiOBo-dicthyl-amlme5-Dicthvlammo-2-nitroao-
ph( nolDicihyl-anihncm-Dioi hylammo-phcnolDiothyl-anilinc-w-sulfomc
AcidN iV'-Diethyl-m-phenylene-
diaminoN iV'-Diethyl-j^-phenylenc-
diamine
d o I I u N^IOIIIBNO
IOIIIBNOSS
584 FORMULA INDEX OF INTERMEDIATES
CnHsOjCUHSOTS
C11H10O3S2
C11H10O4SC11H11NO4SCnHnClNOCnHnNOC H NC12H7NO2Ci-EUNCi2H9N3OCHNO
C12H10CI2N2Ci2HioN2OfiS
C12H10N4O4isio
C12H11NCiaHuNOC12H11NOOCi2HnNO3SCHNOSCi2iiNOCuHuN.Ci2HnN3O2CisHuNaOiCiaHuNiOaS
CI2H12N2O
GaHwNaOiS
Ci2H12N2O«Ci2HI2N2SCVH13NGJHWNO
Ci2Hx»NO3S
CisHxaNaCuHuNOiCiaH12N2SCiaHuNCiaH13NOsS
PAGEl-Hydroxy-2-naphthoic Acid 3103-Hydroxy-2-naphthoic Acid 3101, 7-Dmydroxy-2-naphth.oic-
4-sulfonic Acid 2271 7-Dihydroxy-6-naphthoic-
3-sulf omc Acid 2285-Ethvlmercapto-2-hydroxy-
thionaphthene-1-carboxykcAcid 273
5-Eth oxy-2-hydroxy-thionapn-thene-l-carbo\yhc Acid 268
Methyl-gamma Acid 340p-Diethylamino-benzoyl
Chloride 2133-Diethylamino-p-cresoI 214p-Amino-benzyl diethylamme 41Acenaphthenequinone 19-Napbthisatm 358
Carbazole 1542-Ammo8-hydroxy-phena7ine 572 4-Dinitro-4'-hydroxy-
diphenylamine 2552 4-Dimtro diphenylamine-
3'-sulfonic Acid 2542 4-Dimtro-diphenylamme-
4/-sulfonic Acid 2542 5 Dimtro diphenylamine-
3 4 disulfonic Acid 253o 0 -Dichloro-bpnzidine 210Nitro-diphenylarmne-sulfonic
Acid 433Benzidine sulfon-disulfonic
Acid 1364 -Amino-2 4-dinitro di-
phenylamme 513-Hydro\y-acenaphthene 306Diphenylamine 261m-Hydroxy-diphenylatnino 309a-Naphthyl-glycme 412Diphenylarmne-aulfonic Acid 262Acetyl-H Acid 22Ammo-azo-benzene 320-Nitro-benzidme 4312-Amino-4'-hydroxy-4-nitro
diphenylamine 56Amino-azc-benzene-sulfonic
Acid 34Armno-azc-benzene-disulfonic
Acid 33o-Amino-diphenylamine 52p-Amino-diphenylamino 52Benzidme 1254-Amino-4'-hy dioxy-diplieny 1-
atnme 56p-Amino-diphenylamine-2-
sulfomc Acid 53Benzidine-sulfomc Acid 136Acetyl-1 4-naphthylene dia-
mine-6-sulfonic Acid 22Benzidine-di8iilfonic Acid 135Thioanihne 541Ethyl-a-naphthylamme 275l-Amino-2-naphthol Ethyl
Ether 66Ethyl-2-naphthylannne-7-sul-
fonic Acid 276Dimethyl-gamma Acid 243Ethyl-gamma Acid 272j> p'-Diamino-diphenylamine 1922 4~Diamino-4'-hydroxy-di-
phenylarrune 1974-Anuno-chry8Oidine 47Gallanilide 289Tbiocarbarnb.de 542iV-Methyl-diphonylamino 338JV-Methyl diphenylamme-
sulfomc Acid 339p p'-Diamino-diphenyl-
methane 192
Ci4HaBr4N2O2
Ci4HoN206Ci4H«N2Oi4S2C14H6N2O16S2
Ci4H7ClO2
CX4H7NO6
C14H7NO7C14H7NO7SCnHsBrNO 3
CuHaClNOiC14H8O2CuH8O2SCulUQi
CHHSOSSCwHsOeCHOS
Ci4H»NO2
CuHsNCUCHHBNOS
CuIhNObSCuHioCuHioNsOCi4HioN802
i4HioO14H10O2
C14H10O3'14H11N3O2
C14H1SN2O882
uHiaNsSC14H14N 2O eS2
PAGEiV -Phenyl- -m-tolylene-
diamine 485Diamino-diphenyl-urea-disul-
fomc Acid 1932 4 6 8-Tetrabromo-l 5-
diamino-anthraqumone 5351 5 Dichloro-anthraquinone 2072 6-Dichloro-anthraquinone 2082 7-Dichloro-anthraquinone 208Dmitro-anthraquinones 2501 5-Dimtro-anthraq\iinone 2511 5-Dimtro-anthraflavic-3 7-
disulfonic Acid 2494 8-Dmitro-anthrachrysone-
2 6-disulfonic Acid 2491-Bromo-anthraquinone 149l-Anuno-2 4-dibromo-anthra-
quinone 501-Chloro-anthraquinone 1562-Chloro-anthraquinone 157Nitro-ahzann {crude) 4183-Nitroalizann 4184-Nitro-ahzarin 4193-Nitro-flavopurpunn 433l-Nitro-anthraquinone-6-
sulfonic Acid 427l-Amino-2-bromo-4-hydroxy-
anthraquinone 441 4-Diamino-2 3-dibromo-
anthraquinone 191l-Ammo-6-chloro-anthra-
qvanone 45Anthraquinone 111Pbenanthrene-qumone 458l-(or 2-)Mercapto-anthra-
qumone 332Alizarin 24Anthrarufin 116Quimzann 502Purpurm 498Anthraquinone-2-sulfomc Acidl 14Anthrachrysonc 109Anthraqmnone-1 5 and 1 8-
disulfonic Acids 112Anthraquinone-2 6-disulfonic
Acid 112Anthraquinone-2 7-disulfonic
Acid 1131-Amino-anthraquinone 292-Amino-antbraqiunone 30l-Ammo-4-hydroxy-anthra-
qumone 553-Amino-alizaTin 274-Amino-ahzann 28l-Amino-4 5 8-tnhydroxy-
anthraqumone 881 5-and 1 8-Amino-antlira-
quinone sulfomc Acids 31Anthracene 1082-Isatin Anihde 321Diamino-anthraquinones 1891 4-Diamino-anthraqumone 1871 5-Dianamo-anthraqumono 1884 8-Diammo-anthrarufin 189Dmitro-stilbene-disulfonio
Acid 2601-Anthrol 1179-Anthrol 1181-Hydioxy-anthranol 307o-Benzoyl-benzoic Acid 1401 2 4-Tnammo-anthra-
quinone 573Denydro-thio-p toluidme-
sulfomc Acid 182Dinitrc~dibcn7yl-di8\ilfomo
Acid 252Dehydro-thio-p-toluidme 181Diamino-stilbenc-disulf omc
Acid 199
FORMULA INDEX OF INTERMEDIATES 585
C14H15N Benzyl-methyl-anilino 14C14H16N3 o-Ammo-a7o-toluene 3C14H15N3O3S o-Ammo-azo-toluenc sulfomc
Acid 3C14H15N3O8S2 Dimethvlamino-azo-benzene-
disulfomc Acids 23C14H16N2 o-Tohdine 54C14H16N2O 4-Dimethylamino-4'-hydroxy-
diphenylamme 234Fthoxy-bcnzidme 20'
C14H16N2O2 Dianisidine 20C14H16N2O2S JV-(3-Ammo~4-methyl-phenyl)-
p-toluenc-sulf amide 0(C14H16N2O6S2 o-Tohdme-disulfoino Acid 55(Ci4HicN4 Dimethyl-p p'-dianuno-azo-
bemene 242CMHISN<0 Diammo-17 ox>-toluene 19C14H17N3 p p-Diammo-ditolyl-amino 194C16H7CIO4 1-Chloro-anthi aquinone-2-
carboxylic Acid 158C16H8CINO3 2-Anthraquinonyl-urea
Chloride IKl-Amino-4-bromo-2-methyl-
anthraquinonel-Bromo-4-methylamino-
anthraqumone 1512-Bromo-l-methylammo-
anthraqiunone 1512-Methyl-anthraqumono 336l-Ammo-2-methy l-anthri-
quinone 59l-Methylammo-anthraquinone335l-Anuno-4-methoxy-antlira-
quinone 59Benzyl-ethyl aniline 1443-Ethoxy-4'-methyl-diplienyl-
amme 27027S145
C15H10O2C16H11NO2
C16H11NO3CisHnNCieHnNOC1CHX7NO3SCi5HnNO«S2C15H17N3
C15II18N2O3SC16H18N2O6S3
C10H10N2O2CHNOC16H11NCHSCK5H12O6CieHisN
CHH13NO4SC1BH14N4O6
C16H16N2S
Ci«Hi8N2O
Ci7H«ClOCi7HioBrN02
Ethyl-sulf obenz 1-anihneBenzyl ethvl-anihno-disul-
fonic Acidp-Amino-bcnzyhdene-ethyl-
phenyl-hydrazone 43p p'-Diammo-ditolyl-methane 195iV -Et hyl-iV1~phenyl-4-7n-
tolyleno-diammo 277rthyl-sulfobenzyl-p-phcny-
lene-diamine 280
2803202020
3115164S24S348447418723318418523523237
213100152
y o b y p p h 3 lene-diannnc-thiosulfonicAnd
Indirubin1-Aoetamido-anthraquinono2-Acctuniido-anthraqiunone/3-H\ droxy-naphthoquinonjl-
amlme-p-sulf onic A cidRosorcmol-suocmeinPhcnyl-a-naphthylammoPhenvl-jS-naphthylammcPhcnvH-naphthylaimnc-S-
sulfomc AcidPhenyl gamma AcidDiacetyl-o o'-dinitro-ben/i-
dine(Dimethylamino-hydroxy-
benzoyl)-bc nzoic AoidDphydro-tliio-ra-xylidinciso-Dehydro-thio-w-xyhdme4-Dimethylamino-3 '-mcthoxy
benzophenoneDimethylamino-bcnzoyl-
methyl-amhneAmmo-a7o-xvlene7)-DicthyIammo-azo-bcnzeneChloro-bcnzanthrone4-Bromo-JV-methyl-anlhra-
pyndopo
PAQBC17H10O Benzanthrone 123C17H16N Bcnzyl-a-naphthylaimne 147
Methyl-phcnyl-a-naphthyl-amine 312
Mcthy 1-phcny l-j9-naphthyl-anunc 342
p-Tolyl-a-naphthy]aminc 571CITHUNOSS p-Tolyl-l-naphthylannn( -S-
sulfomc Acid 572C17H20N2O Ivetono 327C17H22N3 Diamino-dixylyl-mcthane 105
4 4/-Din\cUiyl-di iinmo-3 3 -ditolyl-moth.uio 212
p p'-retramcthyl-diamino-diphcnyl-mcthaiic 539
C17H22N2O Hydrol 01C17H22N2O3S p p'-retramothyl-dnimino-
diphenyl-ixiethane-Hulf 0111cAcid 510
C17H22N2O4S p p'-Tctramcthyl-diaimno-benzoliydrol-**\ilion\c Acid 538
Ci8Hi2O Mothyl-ben7 uithronc 338C18H12O3 Naphthoyl-ben/oic Acid 3b JC18H14N2O4 1 b-(or 1 7-)Diacotanndo-
anthraqumone 18GC18H10N2 N A -Diphcnyl-w-phcnylenc-
diamine 2G44 Ph( nylamino-4'-hydroxy-
diphcnylamino 403C1BH18N2O 4-Phenylamino-4'-hvdi oxy-
(phcnyl-3'-tolylanniH) 464C10H10N3 Tnamino-tnphcnyl-mctliano 57 iC20H11NO Benzanthrono-quinohnt 124C20II15N3 a-Amino a o-naphthalcno 5C20HK1NO3S Dibenzyl-anihnc-BiiKoxiK Acid 205C20H20N2 JV Bcnzyl-iV -pbcn 1-4-m-
tolvlcne-dianuno 14.SN Nf-{o o'-Di1olvl)-rn-
phf nyknc-duumne 200N N'(p p'-Ditolyl)-?/!-
phcnyU ne-diamine 2bOC2iIIi2ClNO3 l-Bcnzoylannno-4-cliloi o-an-
thi aqmnonc 1V)C21H14N2OS l-Annno-4-bon7oylammo-
antliiaqumono 40JV-Bcn7oyl-o-tolidino 112Anhj dro-fornnaldohydo-nnihna bi)
C21H28N2O 2 V -rl otraothyl-diamino-bon-/ophcnonc 537
C21II30N2 p p'-Tc trap thy 1-diammo-di-plienyl-methano 538
p. p'-lotrac<hyl-di immo-bi n-7ohydiol 530
C22H18N3O4S 4-(p-IIydroxy-phtnyl-amiiio)-1-phonylanuiio-iJaplit halon< -8-sulfonic Acid «H2
2sHi8 Dipheiiyl-naphlhyi-inclluiiu 203Diamino-dixyiyl-phcnyl-nu -
thane 100C23H27N3 m-Animo-toirainothvl-p' P '-
diammo-triplu nj. I-nu thunc bOwI Na 2V N'-(p p'-Ditol>l)-2 7-
naphthyleno-diunnnc 2(J5i2ttH2oN3 N Jv'-Di-2-nuphlhyl-m-
phony]cn(-diammo 217C28H14N2O4 Indanthrono •ilOC28HHN2O7S Indanthrono-sulfonic A( id 317
Pnmulmo-aulfonic Acid (bo-dium Salt) 405
—-- Pnmuhno-sulfomc Acid 495C2BH24N4O1383 Sulfo-wi-tolylone-diainino-biH-
(earbonyl-ammo-naph1 hol-sulfomo Acid) 531
2 2'-Dimethyl-l l'-bumthra-quinono 211
P A R T I I
G L O S S A R Y O F D Y E N A M E S
AND
P A G E I N D E X O F S C H U L T Z N U M B E R S
G L O S S A R Y O F D Y E N A M E S
'he number of dye names in use is very large. Norton, in Artificial'stuffs Used in U. S., lists almost six thousand in his index wheren a number of individual marks are grouped together under thereviation V.M. (Various Marks).'he list of dyes in stock in the German dye factories on August 15,3, the so-called Reparation Dyes, embrace over seven thousand•ks.hroughout Germany, Switzerland, United States, France and Eng-, there are probably twelve thousand different dye marks in use,Ly of these being for the same chemical compound of the same orifferent degrees of purity.bis glossary is based largely upon the list given in the index of Dr.tnas H. Norton's Artificial Dyestuffs Used in the U. S., which isby permission. A number of corrections have been made to this
and a great number of additions. These additions comprise alllames first given in Schultz's Farbstofftabellen, and many more fromJUS sources. However, a number of the separate marks for ao. name are often here listed on the same line to save space,le new American and English names that have arisen during thefew years have not been included, due to difficulty of adequatelying them.lis glossary copies Norton in assigning Schultz numbers followed byrs to dyes closely related to a given Schultz Dye. Norton's prac-regarding dyes of unknown composition is also used, the numbersemployed being the same as given in Norton. Hence ready refer-can be made to Norton's book for statistical information con-
ng these dyes of unknown composition, which could not be classi-m these tables. Some of Norton's dyes of unknown compositionbeen identified and the proper Schultz number assigned.Lder Serial Number Column those numbers without any letterced refer to Schultz Numbers; those with a prefix of A, S, or Uto Azo, Sulfur or unclassified dyes of unknown composition.is used for Various Marks as applied to dye names, and Var.
s various manufacturers and is employed rather than list a con-ible number of manufacturers for a given dye.
589
590 GLOSSARY OF DYE NAMES
The following abbreviations are used for manufacturers.A Actien-Gesellschaft fur Anilin-Fabrikation, BerlinAW A. Wiescher & Co., Successors, Haeren, BelgiumB Badische Anilin- und Soda-Fabrik, LudwigshafenBrAlizCo. British Alizarin Co.BD British Dyes, Ltd., HuddersfieldBK Leipziger Anilinfabrik Beyer & Kegel, FurstenbergBy Farbenfabriken vorm. F. Bayer & Co., LeverkusenByCo Bayer & Co., Rensselaer, N. Y.C Leopold Cassella & Co., Frankfort on the MainCICo . . . . Clayton Aniline Co., Clayton near ManchesterCDCo. . .Central Dyestuff Co., Newark, N . J.CG Chemikalienwerk Griesheim, Griesheim on the MainCJ "Carl Jager Anilinfarbenfabrik, DiisseldorfCR Clauss & Co. (formerly Claus & R6e), Clayton near ManchesterCV Colne Vale Chemical Co., Milnsbridge near HuddersfieldDH Farbwerke vorm. L. Durand, Huguenin & Co., Germany and
FranceFA Farbwerk Ammersfoort, Ammersfoort, NetherlandsG Geigy, BaselGrE Chemische Fabrik GriesheimJElektron, Offenbach on the MainH Read Holliday & Sons, HuddersfieldH&M... .Heller & Merz Co., Newark, N. J .I Gesellschaft ftir chemische Industrie, BaselK Kalle & Co., Biebrich on the RhineKi Kinzlberger & Co., in PragueL Farbwerk Mulheim vorm. A. Leonhardt & Co., MtilheimLev Levenstein, Ltd., Crumpsall ValeM Farbwerke vorm. Meister Lucius & Bruning, HochstNF NiederlandeseheFarben-und Chemikalienfabrik Delft, Delft.P SociSte Anonyme desMatieres colorantesetproduits chimiques
St. Denis (formerly A. Poirrer), St. DenisQ Imports of Unknown SourceS Chemische Fabrik vorm. Sandoz & Co. BaselSch Schoellkopf Aniline & Chemical Works, Buffalo, now National
Aniline & Chemical Co.tM Chemische Fabriken vorm. Weiler-ter-Meer, UerdingerWB W. Beckers Aniline and Chemical Works, BrooklynWD Wtilfing Dahl & Co., Barmen
Note, Within the past few years many of these companies have consolidated orchanged names.
GLOSSARY OF DYE NAMES 591
Name
Acetyl Red GXAcetylene Blue 3 BAcetylene Blue b BAcid Alizarin BlaclAcid Alizarin Black RAcid Alizarin Black brAcid Aluann BUck bNAcid Ahzann Black bllAcid Ahzann Biown BAcid Alizarin BlueAcid Ahzann Blue BB GRAcid Ah/ann GarnetAcid Ah/ann Gainct RAcid Ali/ann Green B GAcid Ah/ann Gieen 3 GAcid Aluann Hod BAcid Ahzann Violet NAcid Ahzann Yellow GGWAcid Anthi icene BiownAcid Ant hi accne Brown M IAcid Anthi accne Biown PGAcid Antln \ccne Biown RAnd Anthracene Biown
RH WAcid Antln accne Brown
WSGAcid Anth ac*ene Red ^ BAcid Antln uencRcdSBL GAcid BlackAcid Black AOAnd Black ASAcid Blacl 10 BAcid Black b BAAcid Black 4 BDAcid Black BRAcid Black BRAcid Black DAcid Blacl EAcid Black EWAcid Black G 1IA HASAcid Black IIAcid Black IvBAndBla<kMAcid Black MAcid Black MAcid Black SOAcid Black 32Acid Blac k 203 \Acid Black 2195Acid BlueAcid BlueAcid BlueAcid Blue greenishAcid Blue BAcid Blue 7 BAcid Blue BA C DRSAcid Blue LAcid Blue EXAcid Blue OGAcid Blue AGAcid Blue PNAcid Blue RAcid Blue RAcid Blue 5 RAcid Blue RBrAcid Blue VAcid Blue YAcid Blue 466Acid Blue 22244Acid Blue 23579Acid Blue BlackAcid Brilliant Red 2 BAcid Brown
Manufacturer
BGGMMMMCV13MMMIMMMByBvB\B>ByByBvP\AWIoWBCCIGtMIBvQ1SQB\BlvIISHIvBIvAWH<ScMIvIvSsQAWSIvIvQAWSQAWAWMSsAWByC
SerialNo
UOOUbisUb49
1503 502SS2 SO2ssa15470070015515579179(a20220415(88SSaSSa8bSSaSSa
400400a217e217e2( )o217217e217e2(0c2bJ217e
A1412< 9c217c217o2<0c
A115217o21 Oe217o2(0c217o217e54 ic539
U 401U301
5( 55( 5b515c513e5G5b
U301IH01
51 ic5Hc5b5b54 ic5b2543543c
UiOO51 5b5( 5b
A531A146XJ273
Name-
And Brown GAnd Brown RAcid Brown RNAcid Brown SRAnd Biown VAnd Biown YAcid Chr )inc Black GAnd Cl lomeBlick I GAnd Chi ome BUck RHAnd Chrome BUck RHVcid Chrome Black RHNAnd Chi one Black WSA< id Chr >me BUck 1551Acid C hi ome BlueAcid Chi ome Blue (reddish)And Chi ome Red BAnd Chioi io Blue BAcid Chrome Blue * G\nd Chi ome Red NAcid Chroi le Blue 2 RAcid Chi ome Blue 5 R\ad C lnooc Violet RAnd ConnthAnd Comilh 240 SAcid Cresol Black 119GAcid CrimsonAnd Crimson D\ id Cyamne BPAcid Daik GreenAcid EosinoAnd Tosine CA GAnd Eosine 3 GAnd Fosinc I new LBA id Eosine L 27314 bPAnd 1 osinc 11 $2Vnd Eosine 13389And Tast Blue SBAc id rant BlucbRAnd 1 ast Giee n b BAcid 1 ast ViolotAcid FuchsmeAcid GreenA id Gree n\cid GreenAnd Green (V M )And Giecn 2 A B 2 BAAnd Grcon2 BAcid Green (B BW\ndGrcen2 BGAcid Gucn GAcid CrcenGGAcid IndigounoAcid Kraft BiownAcid MagentaAnd MJ,( enl i4cid Ma c nta 6 BAcid Magenta B PAcid M igc nta TCNSAcid Magenta GAnd Magenta 0Acid Magenta SAnd Magenta &Acid Magenta 2Acid Magenta Ciyst ils IAcid Milling Black BAnd Milling Red GAcid Milling ScarletAcid Navy Blue SIAc id Olive 27( IAcidol Azo Viole t RAcidol A7O Violot SAcidol I ast Violot A 2 RAcidol Violet BR
Manu-facturer
tMBKIvGKIPIByByGBlvByCVIvAWByC VByCVByBvBvtMGGiESQAIBCJBIvaWBWBAWAW"ItMWDCtMPtMKByBBv CU SehCVGGrEGMABGrliGVCV
GICoAWKtMtMtMtM
Soi lalNo
212212a212a212a212a212
Al47aA117A11SAblOAllSaA149A723U302A5J2U209A724U200A725U207U20SU210U522U002U501
lbba100a705b505b590500a590a590a500a590a590ft189188
A5UU551
521501502a505505a502a502504502505505877U9152452 It521524521521524r>2\52152 \52420529*484
A5.KTJ39*A512A513ASHTJ523
592 GLOSSARY OF DYE NAMES
NameManu-fac-turer
SerialNo. Name
Manu-fac-turer Serial
No.
Acid Phosphine RAcid Pure Blue RAcid Pure Blue RCAcid PurpleAcid Red2B, 4BAcid Red 6 BFAcid Red CBAcid Red FLAcid Red GAcid Red GAcid Red3GAcid Red RAcid Red 4 RAcid Red SAcid Red 3 SAcid Red C19Acid Red 1622Acid Red 1642Acid Red 1645Acid Rhodamine BAcid Rhodamine 3 BAcid Rhodamine BGAcid Rhodamine GAcid Rhodamine RAcid Rosamine A.-Acid RubineAcid Scarlet GAcid Scarlet 2 RAcid Scarlet SGAcid Silk Black RAcid Silver Black RAcid Silver GravAcid Sky BlueAzo VioletAcid Violet (V. M.)Acid Violet BAcid Violet BBAcid Violet 2 BAcid Violet 4 BAcid Violet 4 BAcid Violet 5 BAcid Violet 5 BAcid Violet 6 BAcid Violet 6 BAcid Violet 6 BAcid Violet 7 BAcid Violet 7 BAcid Violet 7 BAcid Violet SBAcid Violet 4 BCAcid Violet 5 BFAcid Violet 4 BLAcid Violet 4 BLOAcid Violet 4 BLOOAcid Violet 4 BLOOFAcid Violet 4 BNAcid Violet 6 BNAcid Violet 6 BNAcid Violet 6 BXAcid Violet 7 BNAcid Violet 7 BNAcid Violet 6 BNBAcid Violet 6 BNGAcid Violet 3 BNOAcid Violet 6 BNOAcid Violet 6 BNOOAcid Violet 4 BNSAcid Violet 5 BNSAcid Violet 4 BSAcid Violet 6 BSAcid Violet BSCAcid Violet 4 BVAcid Violet BW
CRGGBK
IKSKKAWKKKKKBBBBBMCJAByAWBy.etc,CBKB, KHBy,KVar.AW, ByG, KA, ByG, tMHAWB.H.IKrMBBKBB,IB,MI.WDtMBBKSSKAWBy
606d•TJ603U604U774U304U47SU775U694U304U776U304U304U304A536U304U304U304U304U304U92U93U94U95U955S3524U777U77SU779A150A150U7S0A535407530a530a530a534a530530530530a52953054S527534530a527a530530a530a530a530a53052754854S530527533527530530a530a530a527561530548530a530a527a
[Acid Violet C 2 B , C l O B . . .Acid Violet C l O BAcid Violet DAcid Violet H BAcid Violet H WAcid Violet K B . . . 'Acid Violet N F D SAcid Violet N GAcid Violet P WAcid Violet RAcid Violet R ,Acid Violet RAcid Violet 4 RAcid Violet 4 RAcid Violet 4 RAcid Violet 4 R NAcid Violet 4 R SAcid Violet R XAcid Violet SAcid Violet S BAcid Violet 1704Acid Violet 2405Acid Violet 4746Acid Violet 10471Acid Violet 10475Acid Violet 18502Acid Violet 2644frAcid Violet B lueAcid Violet R e dAcid Wool B l a c kJAcid YellowAcid Yellow A CAcid Yellow DAcid Yellow F XAcid Yellow GTA c i d Y e l l o w GAcid Yellow G GAcid Yellow G FAcid Yellow L RAcid Yellow M G SAcridine Golden Y e l l o w . . .Acridine Golden Yel low
54666AAcridine Golden Ye l low, G,
G G . WAcridine OrangeAcridine Orange N O O , N O .Acridine Orange R,Acridine Red BAcridine Yellow ,Afghan Yellow G XAgalma Black 4 B XAgalma Black 10 B X , 10 B .Agalma Black 201211Agalma Black G r e e n TAgalma Green BAlgol Blue GAlgol Blue 3 GAlgol B l u e KAlgol Blue 3 I t , 3 R PAlgol Bordeaux 3 BAlgol Brilliant O r a n g e F R . .Algol Brilliant R e d 2 BAlgol Brilliant V io le t 2 B . . .Algol Brilliant V io le t R . . . .Algol Brown BAlgol Brown RAlgoi Corinth RAlgol Da rk G r e e n BAlgol GrayAlgox Gray B , B BAlgol Green BI Algol Olive R
LD HLLLLB DBBBBBB yB yB yB yB yB yB yB yB yB yB yB yB yB yB yB yB y
530a530a561a534a527a530a534a530a530a527a530a530a530a527a534a530a526534a561a530a530a530a530a534a534a534a561a
U781U7S2
217h137137139137137137136137137136602a
602a
6026036036045696029
217a217217a217b542844a844839821829822819821820869869a870847a834834847833
GLOSSARY OF DYE NAMES 593
NameManu-fac-turer Serial
No.Name
Manu-fac-turer
SerialNo.
I Orange R>lPinkRIRedBIRedBB, FF!Red2G, 3 G1 Red 5 GIRed, FF, R1 Scarlet G1 Violet B1 Yellow 3 G1 Yellow 6 GL1 Yellow R1 Yellow WF.WG....tdine Blackidine Black Midine Deep Biown 3 Rtdine Orange M:dine Yellow Yrin Orangexin pasterin powder.
rin 11 ABrin D 1M0rinD 1149rin D 1399rin DCRrin GDrinGGXrin GIrin Irin IBrin IPin ITi W SlWSinRGin RVTin Sin SDGin SXin SXGDin V 1,V 2 Ain Win 11 Xin XGPin XPin 744, 1140in Astrol B, Gin Azurine D 3 R. . .in Black (V.M.)in Black (V.M.)in Black ABin Black ACin Black B, 3 BLnBlackSBLn Black DES, EN..in Black ENTin Black IAin Black Pn Black Rn BlackSn Black S, SEu Black SET, SN...n Black SNTn Black SR.WR...n Blue (V.M.)n Blue A, ASn Blue An Blue Bn Blue BB, DBn Blue BR, BR 3 G.
ByByByByByByByByByBy
IIHH*HBr.Ali;Co.
Br.Ali;Co.
Q, etc.ByMMMMB
IMBy,MByMMB
MBBBByBvByByMByMBCAW, CVMByAWMMByMMBMMMBCByMMMBy
82481SS25819816a816819815823811811a817814
U744U744U745779
U746U748778
778
78077S77877S778806a7S47S5a785778778778778780785784a784b78578478477878077S785a7S5a778856
U401774774b774b806a774b774b806a806a774b806806a774807807807774803a803a803803a803a I
Alizarin Blue C 2 G. . . .Alizarin Blue CWRB,
CWRRAlizarin Blue DHG GM, ~ .Alizarin Blue D 2 R, D 4 RAlizarin Blue GR, GW...Alizarin Blue GWDS, HJAlizarin Blue IIXAlizarin Blue JRAlizarin Blue NFA, NHNAlizarin Blue NSAlizarin Blue NSGAlizarin Blue SAlizarin Blue SAEAlizarin Blue SAPAlizarin Blue SAWSAAlizarin Blue SBAlizarin Blue SRMAlizarin Blue WGAlizarin Blue WXAlizarin Blue 942Alizarin Blue (violet shadeAlizarin Blue (violet shade)Alizarin Blue BlackAlizarin Blue Black B •Alizarin Blue Black BAlizarin Blue Black BAlizarin Blue Black B, 3 B.Alizarin Blue Black B, 3 B.Alizarin Blue Black GT. . .Alizarin BordeauxAlizarin Bordeaux B, BD..Alizarin BiownAlizarin Brown B, D3GO, GAlizarin Brown DR, N, RR.[Alizarin Brown 0Alizarin Claret RAlizarin Claret Red DB . . .Alizarin Claret Red DG...Alizarin Chrome Blue T...Alizarin Chrome Brown DCAlizarin Chrome Brown DBAlizarin Crimson DB.Alizarin Crimson DGAlizarin Chrome Green A. .Alizarin Cyanine G, 2 G, 3 GAlizarin Cyanine RAlizarin Cyanine WRR. . ..Alizarin Cvanine Green E
(&V.M.)Alizarin Cyanole BAlizarin Dark Blue DR, S..Alizarin Dark Gieen W . . ..Alizarin Direct Blue BAlizarin Direct Blue EBAlizarin Direct Blue ESB...Alizarin Direct Blue ESR...Alizarin Direct Cyanine FA.Alizarin Direct Green CG, GAlizarin Direct Violet EMizarin Direct Yellow DR.alizarin Direct Yellow DS..Alizarin Fast Blue DGLAlizarin Fast Brown DB. ..Alizarin Fast Brown D 3 R.Alizarin Fast Biown 3 R . . .Alizarin Fast Gray DBL. ..Alizarin Fast Orange DO...Alizarin Fast Red D 244. ..Alizarin Fast Scarlet D 6 BSAlizarin Fast Scarlet D S BSAlizarin GarnetAlizarin Garnet R
MMMByByByByBvByVar.ByByByMM
BMS
cCV, M
yMB
srMM
MMSMMMM
ByByBy
By
MBMMMMMMMMMMMMMMMMMMAWM
799
788803a803a803a803aS03a852803a788803a80485885S804804a804S03803801a803aS03a862774a8028G2862862774a787787782782782782797
U405U406803b
U402U403U407U408260799788788
8C5851804b775851851a851a851a
U409865852
U410U411U412U413U4HU435U416U417U418U419U420797797
594 GLOSSARY OF DYE NAMES
NameManu-fac-turer
SerialNo. Name
Manu-fac-turer
Alizarin GrayAlizarin Gray GAlizarin Green BAlizarin Green BBAlizarin Green CE, CK.. .Alizarin Green C, CGAlizarin Gieen DGN, DMAAlizarin Green GAlizarin Green 3 G, SAlizarin Green SAlizarin Green SP 4Alizarin Green S"WAlizarin Green V, VDAlizarin V 3 WAlizarin Green WBAlizarin Green XAlizarin Indigo BAlizarin Indigo GAlizarin Indigo 3 IIAlizarin Indigo Blue S. .. .Alizarin Indigo Green B....Alizarin Indifeo Violet B....Alizarin Trisol D, RAlizarin LukeAlizarin Light Red D 8 BWAlizarin Milling Black 8 B.Alizarin Maroon WAlizarin OrangeAlizarin Orange A •Alizarin Orange DG,DN,GHAlizarin Orange RAlizarin Pure Blue B. . .Alizarin P\ire Blue DPH. . .Alizarin Pure Yellow DHS..Alizarin Red (V.M.)Alizarin Red (yellow)Alizarin Red D4B, DlOB, DGAlizarin Red GAlizarin Red IWSAlizarin Red SWB, SWBB .Alizarin Red SWR, WB ....Alizarin Red SXAlizarin Red 3 WSAlizarin Red YCAAlizarin Rose GWGAlizarin Rubinol 5 G, RAlizarin Saphirol B, SE ....Alizarin Sky Blue BAlizarin Uianol 12 BAlizarin Uranol RAlizarin Violet (V.M.)Alizarin Violet BLAlizarin Violet DHAlizarin Viridine DG, FF...Alizarin Violet NAlizarin Yellow AAlizarin Yellow CAlizarin Yellow CYAlizarin Yellow DGG, D 3 GAlizarin Yellow DOG, DOO,
DRAlizarin Yellow FFAlizarin Yellow FSAlizarin Yellow GAlizarin Yellow GGAlizarin Yellow 5 GAlizarin Yellow GGWAlizarin Yellow OAlizarin Yellow TLAlizarin Yellow 3 RNAlizarin Yellow RWAlkali Azurine GAlkali Black
CMWDMgWDMBByMByBMB
PByBy%AWBM, etc.BMBy
MByMMMMBBBMBr.Aliz,
ByMBBByMMWBDHSBy,I,MI,MMMVar.MMWD
774dU421657805SOSaSG5805056S05SOSSOSa805SOSa77S805SOSS94S93S95809894a894bS52
U7S3U422774c79S770779779779S55
U423U424780780a7S0a7SG7807807S0784780785
U784850a85S855
U211U2125995995998545997707694848
4848482484S484858a585858410
U538
Alkali Blue.
Alkali BlueAlkali Blues, green shades.Alkali Blues, red shades...Alkali Blue (V.M.)Alkali Blue (for printing ink'Alkali Blue IIIAlkali Blue IV AAlkali Blue 2 ASAlkali Blue AWG, A W R . .Alkali Blue AWRGAlkali Blue 2 BAlkali Blue 2 BAlkali Blue 3 BAlkali Blue 4 BAlkali Blue 5 BA•Alkali Blue BK 2Alkali Blue 5 BLAlkali Blue 7 BOOAlkali Blue DAlkali Blue H 5 BKOOO..Alkali Blue HEOOOAlkali Blue HHRROOO.. .Alkali Blue IAlkali Blue MNAlkali Blue NAlkali Blue RAlkali Blue 3 R, 5 R, C R .Alkali Blue RM, R R M . . .Alkali Blue 2Alkali Blue 1756Alkali Blue 1757Alkali Blue 11408Alkali Brilliant Blue GAlkali BrownAlkali Dark Brown GVAlkali Fast Green 3 GAlkali Fast Yellow.lkali Green. D.lkali Orange GTlkali Rubinelkali Violet
Ukali Violet ASAlkali Violet 6 BUkali Violet 6 BOUkiili Violet LRUkali Violet 421Ukali YellowUkali Yellow RUpha Black 6 BNUpha Black JC ,Upha Chrome Blue AUpha Chrome Brown 0 GAUpha Chrome Brown N . . .Upha Chrome Green 6 B . . .Upha Chrome Orange RK,Upha Chrome Red 3 B . . . .Upha Chrome Yellow C. . .Uphanol Black (V.M.)Uphanol Blue (V.M.)AmaranthiVmaranthAmaranth BAmaranth. DAmaranth DE.maranth SA.methy.st Violet.mido Acid Black B, 4 B, BS|.mido-azo-benzeno.mido Az'o Black.mido-azo-tolueno.mido Black A 2 G
ByCoH&MVar.SchSchCG, tMAMMMMA, BM . t MS. tMI , MBKBGrEAGiEGrEGrEAMB
tMMMKKBWDWDWD
WD
WDKMBBrrAWWDCVCVCVCVCVCVCVCVCVccC, etc.CDCocBKBtMKAVar.MCDCoM
GLOSSARY OF DYE NAMES 595
Name
Aimdo Black 10 BAmido Blat k 4024Amido Blue BAmido Blue GGRAmido Daik Bottle Green BAnndo Gall imine BlueAmido Naphthol Bl lek 4 BAmido Naphthol BHck RIvAmido Naphthol Red 2 BAmido Naphthol Red fa BAmido Naphthol Red GAmido Red BLAmido Yellow FAmmo Blac k 1 BAmine Black 10 BAmmo Black IBMAmine Black S 4 BAmine Black SIAmine Black Green BAmmo RedAniline Bl ickAniline Bl usk 1500SAniline Bluo Spirit SolubleAniline Blue BAniline Blue 2 BAniline Blue 3 B RNAniline Blue B410Aniline Red BAniline YellowAniline YellowAnthosme BAnthosme 3 BAnthosme 5 BAnthracene A< id Black
(VM)Anthracene \cidBluc (V M )Anthracene Acid BtownAnthracene Acid Biown BAnthracene Acid Brown G ItAnthracene Acid GreenAnthracene Acid Red 3 BAnthiacenc Blacl FlAnthracene BlueAnthracene Blue 3 GAnthracene Bluo SWGAnthracene Blue SWGG
SWRAnthracene Blue SW\Anthracene Blue WB WGAnthracene Blue WGGAnthraecno Blue WNAnthiacenc Blue WR W 3 RAnthraeone Blue WG newAnthracene Blue Blaek
(VM)Anthiacenc BrownAntht icene Brown G ItAnthracene Blown R1IAnthracene Brown VVAnthracene Biown SWAnthracene Chromate Brow n
(VM)Anthracene Chrornate GreenFFAnthracene Chromafc YellowAnthracene Chrome Bluo
(V Tu)Anthracene Chrome Blick
(VM)Anthracene Chrome Black
IT exAnthracene Chrome BrownAnthracene Chrome Green
Manu-fac-turer
MMMMMDHMMMMMMMAAAAAAAVarBVartMAtMCGIBQBBBC etcCM CCGCVarMBBBBBBBBCBBy11ByBCCcccccc
SerialNo
217217f
U425U42t>U427
b3SA414A415
(ibafafa12
A41bA417UblUfa5U(bUb7UfbUlOU70<)22)225-1521521521521512
b0
U07U9SU99277
A311221492221
lit 50355
U12SOObOO x700a790a700SOOS01700a7b)S02181a7S27S2a7S2782a782
A318805
A322
A3131S51S5
AmA325
Name
Anthricene Chrome lted(VM)
Anthiacone Dark Bluo WAnthiacene Direct GiecnAnthneenc ltcdAnthiacene Red WBAnthracene Red 10430Anthracene VioletAnthracene YellowAnthricene Yellow (V M )Anthracene Yellow CAntluoccno Yellow Cniht loone Y low G
Vnlhivcnc. Yellow RN 3 ltNAnthnchromc Red AAntlnaute BlaekAnthracyimno S SRAnthiacyl Blue SWRAnthiacyl Chrome1 Blue 2 BAn1 hr ic> 1 Chrome Plue I3>Anthrics 1 Chrome Biovt n D\ntl nt\ IChronieGieenA DAnthnflwone GAnthi uiol Gieen BAnthrnquinonc Blick\nthraqumone Blue bitAnthiaquinonc Blue Gicen
BXOAnthnqumone Green
GXNO GXAnthrtquinone VioletAnthraiubine 395Apollo Rod BApollo Re d GAichil Substitute VAichil Substitute 3 VNArtificial Silk Black RArtificial bilk Bla< k GAuxaeme GAurammoAurimme GVuia nnc GAuummc NAair unine OAurammc ()OAuranunc OO 3 OO 1Aut innnc OODAu umnt OOPAuratnine OEAAu umm 2 3112Aurammc baseAui moAuro r wine KitUuonal Bliuk
AuionalBUek *A 4 AAuronal Blaek 4 A 4 C* r> OAm c n il Bla( k BAurond Block N 2 KAuron il Blaek 5Auronal Blue DAuronal Green TAAu: onal Or inp;e RAuronal Orango SAuiophoqphme G 4 GAustrian BlackAutogene BlackAutogenc Bliek ELBAutol Red BLAutolRcdRL RIPA/ wine SA/idme Blue B BAI GA/!idinc Blue S BAzidme Blue BA.N
Manu-fac-turer
CBCBv.IBIIByCBy etcBlvIMIccvtMtMWDWDBWDBBBBBKGGPPByByByVnrI B(M C*SBy, I0KH K1]\Is.1J ( (CM1M(rtMtMtMtMtNltMtMtMAQPPBBMCTCJCjr
SonalNo
A?2<>7<)0b
U2713r>53P53r>55«)<)77 i177a2<)l2<)t77 hir>hb
A5012(7027
A72(>\52lA 525
1511)1
750U510
740bOl8638(»4SrJ
U3055t51525i
U2K)U215
41)149 i40149440*49 J40 i49 \49 i49 i49 i49 549 i555<KWc722722a72-u727722722a
SI V7SI {Ssuosno(K)(Ja
U78573272 ii()(iH(\
410i91410
596 GLOSSARY OF DYE NAMES
NameManu-
fac-turer Serial
No.Name
Manu-fac-turer
Azidine Blue BXAzidine Blue 24574Azidine Bordeaux GAzidine Dark BrownAzidine Fast Orange ES..Azidine Fast Scarlet 4 BS.Azidine Fast Sacrlet 7 BS.Azidine Fast Scarlet E 4 BAzidine Fast Scarlet GGS.Azidine Oiange GAzidine Sky Blue FFAzidine Yellow CPAzidine Wool Blue BAzo Acid Black B 15Azo Acid Black 3 BLAzo Acid Black RAzo Acid Black TL II... .Azo Acid BlueAzo Acid Blue BAzo Acid Blue BAzo Acid Blue 2 G....Azo Acid Brown 26049Azo Acid Magenta GAzo Acid Red BAzo Acid Red 5 BAzo Acid Red BAAzo Acid RubineAzo Acid Rubine (V.M.). .Azo Acid Rubine 2 BAzo Acid "VioletAzo Acid Violet A 2 B, ALAzo Acid YellowAzo Alizarin Black IAzo Alizarin Bordeaux W.Azo Alizarin Brown IAzo Archil RAzo Black OAzo Black Blue B, RAzo BlueAzo BordeauxAzo Brown VAzo Cardinal GAzo CarmineAzo CarmineAzo Carmine BAzo Carmine BXAzo Carmine GAzo Carmine GXAzo Cerise M, 1618Azo Chrome Blue BAzo Chrome Blue RAzo ChromineAzo Coccine 2 RAzo CochinealAzo CorallineAzo Coralline LAzo CorinthAzo Crimson LAzo Crimson SAzo EosineAzo Fast Blue (V.M.)Azo Fast VioletAzo Flavine CXAzo Flavine FF, 3 GAzo Flavine GX, 3 RAzo Flavine 3 RAzo Flavine 2 RNH, RX...Azo Flavine RSAzo Flavine SAzo Flavine SGRAzo Fuchsine BAzo Fuchsine 6 BAzo Fuchsine G, 4 Q,,.,..
CJCJCJCJCJCJCJCJCJCJCJCJCJMMMMMK,MSByByMMMMWDKVar.l y
A*DHDH
MGrEBy, etc.SchMABVarBBBBKk'GA
WDGrE
lyBy, etc,CCBBBtMBBBBBy|yBy
386410313A454A4552812S2A456280392424304420A418A419A420A42163636363aA15164b6464a64163163168229229141292291A15244A422381377112160a50673672673673672672A3S9164163b847795656548165A15394A329A332141a141a141a140141a140141141a71147146
Azo Fuchsine GNAzo GalleineAzo GreenAzo Indigine 6 BAzo Indigine SAzo Indigine 419, 420A.zo Magenta 6 BXAzo Magenta GAzo Magenta RSAzo Mauve BAzo Merino BlackAzo Milling Yellow 5 G. .Azomine Black FFAzomine Fast Yellow AL.Azomine Milling Black N.Azomine Yellow GAzomine Yellow RAzo Orange RubineAzo Orscille 2 BAzo Orseille RAzo OrseillineAzophor Black SAzophor Blue DAzophor Orange MNAzo Phosphine GOAzo Red AAzoRhodine2 BAzo RubineAzo Rubine (V.M.)Azo Rubine AAzo Rubine SAzo Rubine SAzo R\ibine SGAzo Rubine WBAzotol CAzo Turkish RedAzo VioletAzo Wool Black (V.M.)...Azo Wool Blue (V.M.)Azo ^ ool Violet (V.M.)...[Azo Wool Violet 415Azo YellowAzo YellowAzo YellowAzo Yellow 3 A, 3 ANAzo Yellow A 5 WAzo Yellow 3 GAzo Yellow IAzo Yellow 3 YAzure BlueAzuie Blue A, ASIAzurinr BAzure Blue O, VSBasic Black TESBasic Blue BABasic Blue RBasic Gray ,Basic Green Z ,Basic Kraft Brown Y 2Basic VioletBenzamine Azo Blue G. . ..Benzamine Brown 3 GBcnzamino Brown 3 GO....Benzamine Pure BlueBenzamine Violet GBenzidino PureBenzine BlackBenzine BlueBenzo Azo Red BBenzoazurine (V.M.)Benzoazurine GBenzoazurine GBenzoazurine G f.,. T.
ByAWAWKBCVBGrECGrECVCVCVQ&CAFAMMMMC,ASSchC, etct,MGrESAWBCGrE
CcKK, MVar.&chtMSchtMItMKK
KKAWDHQB
WDWDWDWDWDMCCWDKA, etc.By.CGS, etc,
598 GLOSSARY OF DYE NAMES
Name
Bismarck Brown YSBismarck Brown 53Bismarck Brown 1568Black (V M )Black (V M )Black AJBlack BHBlack CBRBlack CEBlack C 2 NBlack DXBlack EBlack HBBlack MBlack NBlack NSABlack RW XBlack soluble in fatsBlack soluble in oilBlack Base BBBlack Base SBlack Black 0Blue (V M )Blue ASBlue 3 BBBlue BSBlue 5 BSBlue BS 3 BBBlue BSJBlue BSRBlue CABlue CVBlue DBBlue DRBlue DSBlue JBBlue NBlue PCNBlue PCVBlue RRBlue 3 RBlue RSBlue 25Blue 26Blue 214Blue 1900 TCBlue 16519Blue 27071Blue for silk RNBlue (greenish) spirit solubleBlue Black BBlue Black NBlue Black 0Blue Black for Half Wool GBlue Crystals 3035Blue Residue BW 6 MBoma Black BHBoma Black BHXBoma PinkBoma Yellow BBFBordeauxBordeaux extraBordeaux BBordeaux BLABordeaux BRBordeaux BXBordeaux COVBordeaux GBordeaux GBordeaux RBordeaux SBordeaux 5005Bordeaux Black
Manu-fac-turer
tMSchCVCJHPAWPHPHBAWHHPHGCBBMHSGrEPtMGiEGrEGrEIAWQ
csDHGGrEtMPSbBDHLByPMMKMByKKAWAWAWAWAWSchVartMBKByABy, MBKBK,KABIvQ
SenilNo
2832842S3
U494U749
700aU553
698U749
098U749U101U55iU749U749
700iU749U005U277U102UlOiU42SU750U695U502
539U521U503U504U505U053U700U701U7oOU27SUb96
697UbOOU500U525
5 $7bUO97Ub9SU104
035U5HU217537b521210b21 "52Mb
U218UK)0u*ioU 556U557U55SU559
16S320112}2011223732025411211210S112
U792
Name
Brilliant Acid Blue ABnlhant Acid Blue B, FF, LBnlhant Acid Blue VBnlhint Aeid Blue 25601Bnlhant Acid Canmno B
BOOBrilliant Acid Green 6 BBrilliant Acid Rod GBnlhant Ahzann BlueBrilliant Alizarin Blue D 3 GBnlhant Alizarin Blue D 6 GBnlhant Alizarin Blue DRIBrilliant Alizarin Blue R &
(VM)Bnlhant Aluarin Blue ItBnlhint Alizarin Blue 3 RBnlhant Alizarin GreenBnlhant AnthrazuroiBnlhant Arelul CBrilliant Azo Acid Blue 3 GBnlhint Azuie Blue VSBnlhant Azunno B, R, 5 RBnlhant Azunne 5 GBrilliant Benzo Blue 6 BBnlhint Benzo Gieen BBrilliant Benzo Violet BBnlh int Benzo \ lolet 2 RBnlh mt Bciuo I ast Violet
2 itLBnlhant Benzo Fast Violet
BLBnlh int BlackBnlhant BlickBBrilliant Blick 3 B, GBnlhant Blue ABrilliant Bluo GBnlhint Bluo GGBrilliant Blue 217Brilliant Blue 2SbBrilliant Bordeaux feDBnlhant Brown 205Bnlh mt Carmine CIBnlh int Carr nne GGbrilliant C untune IBrilliant Chrome Blue PBnlhint C hioinc Violet BDBnlhint Cloth. BluoBnlhant C oc lane il 2 RBnlhant Conj o G5nlhant C on o Ririlli mt Congo Itinlh mt Congo It*nlliaul Congo Bluo BJnlhant Congo Blue 5 RJiilliuil Congo Violet Itinllumt Copper Blue BWinlhant Coppc r Blue GW-inlhant Cotton Bluo N3 nlhant ( rouino (V M )kilhant Croccmo 3 B, MOO3 nlhant Crottinc 9 B3 nib. int Croccine 3 BA3nlhant Crocome MD1 nlhant Croc me NZ•nlhant Crimson•nlhant Crimson Niiilhint Delplnno Blue B
Bnlhant Delplnno Blue BS,VS
brilliant Dianil Blue b Ginlhant Di inol Red Itinlliwit Diazino Bluo 1230
Bnlhant Double Seat lot
Manu-fac-turer
A, ByByBySGrEByKVarMMMByCRByWDBCSKByBy.A.LByByByByByByVarB etcBCVsCVQQAQBT*BsByKcA LA, LBySAAAAABycBycByGrEMMMKSMLWKBK
SerialNo
545545c543545c66b
503U312
607bO7007007607007607057a
U1055503b
U313410a41b424
A207A20SA209A20bA206a
272272272
U725UbOOU72bU79*U704
AlU79(5U106U107U10S
b2(>lS()aSI
3Lb370570370U75U74U75U7(>U7722722727022722711110$10*
U3H622541
U315170b
GLOSSARY OF DYE NAMES 597
Name Manu-fac-turer
By etcByGrEW BByByByByBvByByByBKByByByByByBvByByBvByByByByByByByByByByByByByByByByGByByByByAByByByByByByByByByByByByByByByByByByByByByByByByByByByBy
SerialNo
411410385410459460450337391386419A154
A4424.155A156
487490485a485485a4S5a190485a
A157A158A159A160A161A162A163A164390425336
A165A166A167A168AflliA169456456a456a451A170
A171A172A173A174A175A176A177A17SA179A180A181
340a297332332343332
A183279279279279327327a296a296296a
Name Manu-fac-turer
GrFByByAByAByByByBvByByByBvByi kBKBKBKByByByByByByAWHIByA etcA etcBy etcA etcABKGrEQByByByByByByByByBvCRByByPIIIIIIIIKKKKByA, etcCAICV etctMSell
SerialNo
6054,196A197U71
A198U72
A199A20OA201A202
447A1844.185A186A1S7A188410410477194452379379
A189446340
A190365a365365a365a365363364405363363363363
A191A192A203A204A193A194
319A195
426517326326a104
A661U651Ub52
503A6G2
517517517541
XJ308TJ309A392
278A205
283283283283284284283
)azunne 3 G>azunne R>azunne 3 R>azunne WB> Black Blue G> Black Blue 5 G> Black Blue R> Blue 2 B> Blue 3 B> Blue BX) Blue RW) Bordeaux 6 B) Brilliant Blue 2 GDIs> Bronze E> Bronze GC> Brown B> Brown BX) Brown D 3 G> Brown G>Brown5G 2GC 3GC> Brown MC NBX> Brown 5 R> Brown RC, TR> Chrome Black Blue BChrome Biown B
> Chrome Brown BS> Chrome Brown G> Chrome Brown 5 G> Chrome Brown R> Copper Blue B> Copper Blue 2 BCyamne BCyamne 3 B
> Cyamne RDark BrownDark Green BDark Green GGDeep Black SSFast BlackFast Black LFast Blue B BNFast Blue FRL 2 GLFast Blue 4 GL 2 LFast Blue RFast Bordeaux 6 BLFast Brown 3 GLFast Brown RLFast Eosine BLFast GrayFast Gray BLFast Heliotrope BLFast Heliotrope 4 BIFast Heliotrope 5 RHTast Heliotrope 2 RLFast Orange 2 RLFast Orange SFast Orange WSFast Pink 2 BLFast RedFastRed8BL9BLDFast Red FCFast Red GL LFast Rubine BLFast ScaTlet (V M )Fast Scarlet 4BS 5BSFast Scarlet 8 BS
3NFast Scarlet GSFast Violet NCFast Violet RFast Yellow 4 GLFast Yellow 5 GLFast Yellow RL
Benzoflavine OBenzoform Blue BBenzoform Brown RBenzoform Orange GBenzoform Orange GBenzoform Red GBenzoform Red GBenzoform Red 2 GFBenzoform Scarlet BBenzoform Yellow RBenzo Gray SBenzo Green BBBenzo Green CBenzo Green FFBenzo Green TFGBenzo Green GBenzoin Blue 5 GN, RHBenzoin Brilliant Blue GDNBenzoin Brown CBenzoin Fast Red AEBenzo Indigo BlueBenzo New Blue 2 BBenzo New Blue 5 BBenzo New Red 4 BBenzo OliveBenzo Orange RBenzo Pure Yellow FFBenzopurpunnBenzopurpurmBenzopurpunnBenzopurpunn AMBenzopurpurm BBenzopurpunn 4 BBenzopurpurin 6 BBenzopurpurm 10 BBenzopurpunn 4 BMBenzopurpunn 4 BNBenzopurpunn 4 BPBenzopurpunn 4 BXBenzo Red 10 BBenzo Red 12 BBenzo Rhoduline Red BBenzo Rhoduline Red 3 BBenzo Rubine HWBenzo Rubine SCBenzo ScarletBenzo Scarlet BCBenzo Sky BlueBenzo VioletBenzo Violet OBenzo Violet Rtenzoyl Pinkienzyl Black Bienzyl Blue BBenzyl Bordeaux B 17619Benzyl Green BBenzyl RedBenzyl VioletBenzyl Violet 4 B, 6 B 10 B3enzyl Violet 5 BNBetamine Blue 8 BBiebnch Acid Blue GBiebnch Acid Blue Vhebnch Acid Violet RBiebrich Patent BlackBismarck Acid BrownBismarck Brown • •Bismarck Brown (V M )""ismarck Brown EL.ismarck Brown Ghsmarck Brown RBismarck Brown 2 R 2 RVBis.marck Brow n Y
598 GLOSSARY OF DYE NAMES
Name
Bismarck Brown YSBismarck Brown 53Bismarck Brown 156SBlack (V M )Black (V M )Black AJBlack BHBlack CBRBlack CEBlack C 2 NBlack DXBlack EBlack HBBlack MBlack NBlack NSABlack RW, XBlack soluble in fatsBlack soluble in oilBlack Base BBBlack Base SBlack Black 0Blue (V M )Blue ASBlue 3 BBBlue BSBlue 5 BSBlue BS 3 BBBlue BSJBlue BSRBlue CABlue CVBlue DBBlue DRBlue DSBlue JBBlue NBlue PCNBlue PCVBlue RRBlue 3 RBlue R&Blue 25Blue 2t>Blue 214Blue 1900 TCBlue Ib519Blue 27071Blue for silk RNBlue (greenish) spirit solubleBlue Black BBlue Black NBlue Black 0Blue Black for Half Wool GBlue Crystals 3035Blue Residue BW 6 MBoma Black BIIBoma Black BHXBoma PinkBoma Yellow BBFBordeauxBordeaux extraBordeaux BBordeaux BLABordeaux BRBordeaux BXBordeaux COVBordeaux GBordeaux GBordeaux RBordeaux SBordeaux 5005Bordeaux Black
Manu-fac-turer
tMSchCVCJHPAWPHPHBAWHHPHGCBBMHSGrEPtMGiEGrEGrEIAWQQJ£O&DHGGrEtMPSbBDHLByPMMKMByIvIvAWAWAWAWAWSenVartMBKByABv MBKBK,KABKQ
SerialNo
2832S42S3
UlOiU749
700aU553
698U749
(>93U749U101U554U749img
700dU74<)UbO5U277U102U103U42SU750U(>05U502
5.30U521U503U501U505UG53U5"5r)U700U701U7r)0U27i>U690
007XT()()()U50bU525
5*7bU097UbOSU1U1
(>B<3U511U217r>37br)2L2(><)b2152()0b
TJ21SIH09v noU5515U557U5r)bU559
108320112?201122B7320251112112lbS112
U792
Name
Bi llliant Acid Blue ABrilliant Acid Blue B, FF, LBrilliant Acid Blue VBrilliant Acid Blue 25601Brilliant \cid Carmine B,
BOOBrilliant Acid Green b BBrilliant Acid Red GBi llliant Alizaim BlueBrilliant Ah?aim Blue D 3 GBulhant Alizarin Blue D b GBi llliant Alizarin Blue DillBrilliant Alizarin Blue R &
(VM)Bulhant Alizarin Blue RBrilliant Ah/arin Blue 3 RBulhant Aluaun GreenBrilliant AnthrazurolBrilliant Atelul CBulhant Azo Acid Blue 3 GBulhant Azuie Blue VSBulhant A-sunne B, R 5 RBulhant Azuune 5 GBulhant Bcnzo Blue b BBrilliant Bcnzo Green BBrilliant Benzo Violet BBrilliant Be nzo Violet 2 RBulhant Bcnzo Fast Violet
2 RLBulhant Benzo Fast Violet
BLBrilliant BlackBrilliant BI ick BBulhanfc Blaek 3 B, GBrilliant Blue ABrilliant Blue GBulhant Bluo GGBulhinb Bluo 217Bulhant Blue 28bBrilliant Bordeaux foDBulhant Brown 205Bulh mt Carmine GLBulh mt Can une GGBulhant Canmnc IBrilliant Chronic Blue PBulharit C hiome Violet BDBnlhint Cloth BluoBrilliant C oc lun< il 2 RBulhant Conj,o GBulhant C onto RBulh mt Congo RHulh mt Congo RBulhant Congo Blue BJtilhnnl Congo Blue 5 Uiulliunt Congo Vi >lot iiinlhant <. upper Blue BWJnlhftiit Copper Bluo GWbrilliant Cotton Bluo Nbulhant ( roctmti (V M )Brilliant Croccmo 3 B, MOObrilliant Ciot uno 0 BBulhant Croeuno 3 BA•Jrilhunt Croceino MDBrilliant Crocunt NZBulhant CrimsonBrilliant Crimson NBnlh mt Dolplimo Bluo BBulhant Delphme Blue BS
VSBrilliant Dianil Blue t> Giulhant ftianol Rod RBnlh mt Diazino Bluo 1230Julhunl Double beailoL
Manu-fac-turer
A ByByBySGrEByKVarMMMByCRByWDBCSKByBy,A,LByByByByByByVarB, etcBCVsCVQQAQBnBbByKCA LA, LBysAAAAABycBycByGrEMMMIvSMLWIvBK
SerialNo
545545c543545c66b
503U312
667(>b7(>b70b7667b(>7Cb7()57a
U1055503b
U313410a41b424
A207A208A209A200A20(>a
272272272
U725uoooU72bU79BU791
AlU705U100U107U10S
(>2(>W)alS()a81
3U>370370370U7BU71U75U7liU775iS2272272702272272271GB10*
U311622511i5S
U315170b
GLOSSARY OF DYE NAMES 599
Name
nt Fast Blacknt Fast Bluent Fast Blue Bnt Fast Blue 3 BXnt Fast Blue 2 Gnt Fast Blue 4 Gnt Fast Red Gnt Fast Red Pnt Geranine Bnt Glacier Bluent Greennt Green Bnt Green 0 Bnt Green BNnt Green Dnt Green PNDnt Green Snt Hessian Purpleat Indigo Bat Indigo BDnt Indigo 2 B BBDat Indigo 4 Gat Indigo G GDDat I ake Red Rat Lanafuchsine1)it Milling Bluc(V M )at Milling Blue Bit Milling Green Bat Naphthol Blueat Orange Git Orange 0it Orange Rit Or&eilleit Oi seille Cit Patent Blue Ait Patent Blue Ait Phosphmeit Phosphme G 5 Git Pinkit Ponceau 5 Rit Pure L ellow 6 Git Purpunn 4 Bit Purpunn 10 Bit Pui punn Rit Red R pasteit Rhoduhn Red Bit Rhoduhn Violetit Safranme Git Safranme Rit Scarlet (V M )it Scarlet ALit Scarlet NY 47it Scarlet Rit Scarlet 2 Rit Scarlet 3 Rit Scarlet 4 R 4 RSPt Scarlet 141113it Sky Blue 5 Bit Sky Blue fa Bt Sky Blue GLt Sky Blue 5 Gt Sky Blue 8 Gt Sulfonazurme Rt Sulfon Red B 5 Bt Victoria Blue RBtWool Blue B FFR Gt Yellowt Yellowt Yellowt Yellow C
Manu-fac-turer
IAWByByByByBByByIVartMtMCGrECJLBBBBBMCCKCCA ByMM.etcCCKMIISByByA ByAA etcByByASchCMBBKtM&chtMBByByByByBySIByByVartMSch
SerialNo
UG54A 539A210A211A2124J13162
A214US5014994054994994994994993028boSS5SS48S7S8G43
TJ2S0U2S1U316
503U2S2
33970795555
U31754560Gb606571a169
U219368368a36915
6S4bGS4a679684
U2S3A424U109A443A515
109A516U110U220
424U221
5ilU223
361a182559b562a
U224303142303
Name
Brilliant Yellow SBromofluoresceic Acid A 3 GBromofluoresceic Acid BA
BLBromofluoresceic Acid Crys
talsBromo Indigo FBBromo Indigo RathjenBromo Motanil YellowBrownBrown A. 167SBrown GCBrown PCCBrown YBiown PCCBrown 43Brown 359Brown 37104Buffilo Black ADBuffalo Black 2 BBuffalo Black 4 BBuffalo Black S B 10 BBuffilo BlickEABuffalo Black NBBuffalo Black PYBuffalo Black RBuffalo Chrome Blank BWNBuff ilo Cj cinmo R 3 RBuffalo Direct Blue GBuffalo Direct Cardinal 7 BBuffalo Direct Crimson BBuffalo Direct Garnet RBuffalo Direct Orange RBuffalo Direct Orange YBuffalo Direct Red 4 BBuffalo Direct Violet 4 RBuffalo Direct Yellow CGBuffalo Direct Yellow CRRBuff ilo Fast Blue BBuffalo Fast Blue RBuffalo Fast Crimson GBuffalo Fast Crimson RBuffalo Fast Fuchfaine BBuffalo Flamme BBuffalo Flamine GBuff xlo RubmeButter YellowCachou (V M )Cachou de La\ alCalcutta Black DCalcutta BlueCalcut a Blue 2Caledon Blue IICaledon GreenCaledon PurpleCaledon VioletCandle BlueCandle VioletCanelle ALCapri Blue GONCapri Green BNCarbazole Wool GreenCarbide BlackGaibide Black E, EX SXCarbide Tast Black GrCarbide Violet VCarbmdol Blue RCarbon Black (V M )Caibon Black 4 BC irdinal 3 BCardinal Red JCarmine Blue ACarmine special
Manu-fac-turer
B etcMMMByPBKBGDHHGSLevHSchSchSchSchSch&chSchSchSchSchSchSchSchSchSchSchSchSchSchSohSch&chSchSchSchSchSchSchA etclevpHSS
KKBBy LICIIIIKMHHAWP
SerialNo
142587b5S7b5S7b8S1879135
U479UlllUfO7U596
283UbO7U700
2S3b28326627226020120S2172202612752574104053133123623923633753423941891S86466
1479495
11032
U731700
U751626
U701842765763766
U318U319
600620020a
U2S4462f462f462f462g74b458272512161
U560U592
600 GLOSSARY OF DYE NAMES
Name
Carmine Blue VCarmine Brilliant BlueCarmine Naphth Garnet. ..CarmoisineCarmoisine BCarmoisine 3 BCarmoisine 6 B, RCarmoisine L, WSCarpet Red B, BT, RCarthamine 6 A, BCashmere Black 3 BNCashmere Black MCSCashmere Black VCashmere Blue TGCelestial BlueCelestine Blue BCerasine Brown ANCerasine Dark Red I, IICerasine Orange GCerasine Red 56 I, 56 II...Ceres Blue 4Ceres Brown 3Ceres Brown 4Ceres Orange 3Ceres Red 3Ceres Red 6Cerise DX, DIVCerise MCerise NCerofiavineCerotine Scarlet GChicago Blue BChicago Blue 4 BChicago Blue 6 BChicago Blue RChicago Blue 2 RChicago Blue 4 RChicago Blue RWChicago Blue newChicago Orange GChicago Red 111China BlueChinaldine YellowChloramine Black BHChloramine Black BHChloramine Black EXD, FFChloramine Black HWChloramine Black NChloramine Blue 2 BChloramine Blue 3 BChloramine Blue 3 GChloramine Blue BXRChloramine Blue HWChloramine Brilliant Red 8 B|Chloramine Brown GChloramine Dark Green B..Chloramine Fast Red F, FFChloramine Fast Yellow B.Chloramine Green BChloramine Green GChloramine OrangeChloramine Orange GChloramine Pure BlueChloramine Red B, 3 BChloramine Red S B, S BS.Chloramine Sky Blue AconcChloramine Sky Blue 6 B, FFChloramine VioletChloramine Violet NChloramine Violet RChloramine YellowChloramine Yellow DB, FFChloramine Yellow G
Manu-fac-turer
KAWDHA, Sl y
KtM
WD
CCcByUII y
tMCBCJAA
SSSSSSSssssrs
fy
ss
isrByBy.etc.ty
SerialNo.U320
U561106163163163a163a163
U321573a
A215A733A216A217U541641
U2S5223a35223
U225.U226U227U22SU229U230512512512
U112• 34b423422424388384324419422a15
A612539613469333469a473469337471a471386472358
A218470a3436174704751111
471b319358426424
A220327
A221617617617
Chloramine Y e l l o w GG,HW,M
Chloramine Yellow M.Chloramine Yellow RCChloranisidine ScarletChloranthrene Yellow GChlorantine Blue BBChlorantine Brown BBChlorantine Brown R . . . . . •Chlorantine Brown 15521...Chlorantine Brown 15895...Chlorantine Fast Blue RL. .Chlorantine Lilac BChlorantine Lilac BBChlorantine Orange T R . . . •Chlorantine Orange 11323..Chlorantine Pure BlueChlorantine RedChlorantine Violet BBChlorantine Yellow JJChlorazol Blue GBDSChlorazol Blue 3 GChlorazol Blue R • • • •Chlorazol BriUiant Blue 3 B,
Chlorazol Brilliant Blue 14 B,
Name
pihlorazol Brilliant BordeauxRH -. -A
Jhlorazol Brilliant Green GChlorazol Brown GChlorazol Brown M.Chlorazol Brown MASChlorazol Catechine BChlorazol Drab RH. . . .. . • • •Chlorazol Fast Blue RH.. . . .Chlorazol Fast Bordeaux B.
Ihlorazol Fast Red 10 B . . •Jhlorazol Fast Scarlet RH. .Chlorazol Fast Yellow A . . -Chlorazol Fast Yellow AF. .Chlorazol Fast Yellow AG..Chlorazol Fast Yellow BS. .Chlorazol Fast Yellow R . . .
ihlorazol Green BIhlorazol Green G
Jhlorazol Orange 2 KChlorazol Red AChlorazol Sky Blue F F . . . . .Chlorazol Sky Blue FFS . . . .Chlorazol Violet BChlorazol Violet 3 BChlorazol Violet R
ihlorophenineIhocolate Brown
Jhocolate Brown GChocolate Brown RChromal Blue G, G C . . . . . .Chromal Dark Blue K . . . . .Chromal Fast Brown G . . . .Chromal Fast Brown R . . . .Chromanil Black BFChromanil Black FFChromanil Blue RChromanil Brown 2 GJhromazine Blue GChromazone Blue R,Chromazone Red (new), A. .Chrome Acid BlackChrome Acid Black RSIChrome Azurol SChrome Black
Jhrome Black BA
Manu-fac-turer
SerialNo.
a r
i
i
iiHHH
HHHHHHHHHHHHHHHHHHHHHHHHHCICoAWBBGGGGAAAAMGGI
GWDQ
61761761797
849A663A664A665A666A667
451A668A669A670A671A672
358A673
617417417
417
417a
417aA734A738A735A736A737A739A740A741A742A743A744A745A746A747A748A749
474A750
340A751A752A753A754A755A756
17U568U113U114
552552a
U608U609
A2A3A4A5
XJ429130129
XJ655U656
554275a
A765
GLOSSARY OF DYE NAMES 601
Name
- Black A- Black DFi Black DrBlack TPP G
»Black Ia Black LVi Black M ZBlack 2841
i Black 5700GsBluo> Blue ATX5 Blue B>Bluo2B IBX) Blue G> Blue RBlueRBlue RXBlue Black BBouloauxBrownBrown CSBTOWH PBrown RRBrown RVVBrown 414Brown 2813Deep Black ADeep Black ADeep Black GDeep Black GFast BlackFast Bl ick AFast Black BFast Black FFast Black F1 ast Black FWFast Black P4BPast Black PFFast Black PONFast Black PTFast Black PVFast Black PWBTPast Black PWKllFast Black 12172Fast Blue BFast Blue 4 BFast Blue RFast Blue 1336GFast Brown AFast Brown BCFast Brown GFast Brown ItFast Brown TPFast Brown TVFast Biown VFast Brown 12081Fast Brown lr>82*Fast Cyamnc GFaBt Garnet BLFast Green GI ast Green GLFast Green 1G39 IFast Orange ItFast Orange RDFast Pure Blue B\Fast Red GFast Violet BPast Yellow BNFast Yellow GPast Yellow 2 GFast Yellow GG"ast Yellow GA 0
Manu-fac-turer
CGAWMAWHKHKIIByBWBBKQAWWBBKBvAWKPGGlevKGtMGtMGCGIAIAACGAIICGBAIIIIIAByIIIIIAIIIrByiAICGAAII
SenalNo
275a275a
A425275a275a
U322275a
U322275<i507lf)3bG2Gl(3bK)3b16*599lG3b
Ui2355015ba15Sa90
158158158a158a275b275275b275275181c275cAG275275cA7AS181cA9157181181181c
XJ115U78
Uf57Ub58AG74A(>75AG7GA10
U2S1AG77AG70A078AG80AG81U79
A(82Ab8*A084A(8r)U232
551All
AC8G177d()Ga9G9Ga90a
Name
Chrome Fast Yellow R 2 RChrome Gallus Brown RRChrome GreenChrome Green (V M )Chrome Green CChrome Green GChrome HeliotropeChrome Leather Black EChrome Leather Black EChrome Leather Black LChrome Leather Black EAChrome Leather Bla k IChrome Leather Black MChrome Leather Brown RChrome Orange GitChrome Patent Green NChrome Red 2593Chrome VioletChtome VioletChrome Violet Brown 9457Chrome Violet b for print
ingChrome YellowChromo YellowChrome Yellow D DFChrome Yellow G GGChrome Yellow ItChrome Yellow RChrome Yellow SM 2501Chxomine GChromme RRChrornine BlueChromino Blue BChromine Brown ItChromme Brown VChromine Fast Blue SChrornine Violet 2 ItChromocitromne ItChi oniocyaninc B VChromo cne IChromogeno Violet BChromopurpunn IIChromotropc 2 BChromotrope G BChromotrope 8 BChromotrope 10 BChromotrope DWChromotrope I 4 BChromotrop< 2 RChromotrope SChromoxane Blue RChromoxane Violot 5 BChryaamme GChrysamme KCkryaamiiK ItChrysobauneChrysobanno ItChrysoidineChrysoidim AChryaoidin AltChrysoulme G2TChrysoidim. VChrysoidine GSChrysoidmc ^ NChrysoidmc ItChrysoidinc RChrysoidine 3 ItChrysoidinc RDChrysoidine ItLChrysoidine KGChrysoidine ItL ltl EChrysoidine T baseChrysoidine Y
Manu-fac-turer
AGByKKLDHBBy<aBWDBySByKKByGKGByIBySAWByKIvSAAWAWAWAWAWDHDHMMDHMMUMMMMMByByBy etcSBy ItMtMVarBtMPBItMVarC DHb(hCVPBBVar
SerialNo
177lr>Sa509
U324U324U515
625U11GU2S3U702U117U542V2UXJ70 5U2r>
219TJ325
540557
U32G557177177Q177177e177o177
AV)iG1461 la
U5G2Ur>0*U5(HU5()5U5(HiU507
ltt)aGU777
UliOU507
57G7
17111457a
Ib44057a
U2JGU237
H2342J0410 te30 U3ii43i3ii3340034i43t34Ha.33,
602 GLOSSARY OF DYE NAMES
Name
Chrysoidme 2 YChrysoidme 46803Chrysoidme BaseChrysoidme crystalsChrysomeChrysolanne AChrysolineChrysophenmeChrysophenme GChrysophenme GOOChrysophenme R WChrysophenme IIIChrysophemne 190Ciba Blue BCiba Blue 2 B 2 BDCiba Blue G G 2 BCiba Bordeaux BCiba Gray B GCiba Green GCiba Heliotrope BCibanone Black B BG 2 GCibanone Blue 3 GCibanone Brown B VCibanone Green GCibanone Olive B GCibanone Orange RCibanone It ellow RCiba Orange GCiba Pink RCiba Red RCiba Red BCiba Red GCiba Scarlet GCiba Violet BCiba Violet 3 BCiba Violet RCiba Yellow GCinnabar Scarlet BFCinnabar Scarlet G, RCitronme GOOCitronme GOOO 2 ROOOOClaret NY Z 1413Claret Lake BLClaret RedClaret RedClaret Red B BOClaret Red SSClaret Red XClayton Cloth RedClayton 1 ellowCloth Blue 17C9 1770Cloth Fast Blacl BCloth Fast Blue BCloth Fast Blue GTBCloth Fast Blue RCloth Fast Red RCloth Red BCloth Red BCloth Red BBCloth Red B 2BCloth Red 3 BCloth Red BACloth Red BCCloth Red BOCloth Red GCloth Red GCloth Red GACloth Red 3 GACloth Red GFL GTCloth Red OCloth Red 17G9 25S6Cloth Scarlet C GCloth Scarlet R
Manu-fac-turer
tMAKSchVartMG S PI.SVarLByAWKIIIIIIIIIIIIIIIIIIIIIIIIBKBIvLGrEBByBHMBMCICoCICo2IIIIIByGiE IvKWDByAByGrEByBy GrEAAAMKKK
SenalNo
333*3333
143U526586304304304304a304304SSO8S188291089989189779 i793S68792a792b792795911910a90S909906907901900901890299300141140
misU23SU119A757112aU120112a
19*19STJ327UG59693UbGl25748423323G
A39423G2312362.u3a23b22423423423023423GA394246252
Name
Cloth Scarlet 2584Cloth Yellow RCocceine OiangeCoccine 2 BG 3 BGCoccinme BCochinealCochineal Red ACochineal Scarlet BCocluneal Scarlet 4 RCoerulem BCoerulem ICoerulem MS powderCoerulem SCoeiulem SL powderCoerulem SWColumbia BlackColumbia Black BColumbia Black EAColumbiaBlacklT FB T2BColumbia Black RColumbia Black WAColumbia Black Green DColumbia Blue G GMColumbia Blue RColumbia Bordeaux BColumbia Brow n MColumbia Brown RColumbia Catechme 3 BColumbia Catechme GColumbia Catechme OColumbia Catechme RColumbia Fast Black DColumbia Fast Black FFColumbia Fast Black GColumbia Fast Black VColumbia Fast Blue 2 GColumbia Fast Blue RColumbia Fast Red FColumbia Fast Scarlet 4 BColumbia GreenColumbia Green B 3 B, GColumbia Orange RColumbia Violet RColumbia \ ellowColumbo Blue 4 RCoomassie Acid Blue RCoomassie Black BCoomassie Blue BlackCoomassie Navy BlueCoomassie Is avy Blue 2 RNXCoomassie Union BlacksCoomassie Wool Black DCoomassie Wool Black SCoomassie Wool Black RConcentrated Blue BBConcentrated Cotton Blue
B, 2CongoCongo 4 RCongo Blue 2 BCongo Blue 3 BCongo BrownCongo Brown GCongo Brown RCongo CormtD BCongo Corinth GCongo Fast Blue BCongo Fast Blue R3ongo Magenta2ongo Magenta 3616Uongo Orange GDongo Orange RCongo Orange R, RG
Manu-fac-turer
KGrEPAMPBWDch
MBDHB etcBDB,ByA y
AAAAAAAAAAAAAAAAAAAAAAAAAAAABDI evLevLevBDLevLevlevLevHMAAVarA Le\A LevVarVarAAKKVarA LBy
SerialNo
U327aA458227a16710181b169957S
000G01601601601601436455455a43b4534r>5a4653S7325U80A12A13U81U82US3U84US6U87US8TJ89A1GA17343279478478A14A15617
U6631884*32174*4252461260244243
U752539307374412391477477490375312456451A395
A395315373373
GLOSSARY OF DYE NAMES
NameManu-fac-turer Serial
No.Name
Manu-fac-turer
Congo RedCongro Red 4 B ,Congo Red 4 R ,Congo RubineCongo Rubino GCongo Rubino ZCongo Rubine 8714Coreinc AR, ABCoioine 2 RCorioflavine G,GG,GOOO,RCoriphosphino OS, OXCorvan Black BGCorvaR "Black TCorvolino BTCotton BlackCotton BlackCotton Black (V. M.)Cotton Black 3 BCotton Black BGXCotton Black BNXCotton Black BTCotton Black CC, CTCotton Black CKCotton Black BCotton Black GBCotton Black GS, RSCotton Black PFCotton Black RWCotton Black UGCotton Black V, YCotton Black 4Cotton BlueCotton BluoCotton Bluo (V. M.)Cotton Blue BCotton Blue BCBCotton Bluo BCBCotton Blue BRCotton Blue BSJCotton Bluo CCCotton Blue GCotton Bluo NCotton Blue OOOCotton Bluo R, RNCotton Bluo 5190Cotton Blue Doublo cone...Cotton BrownCotton Brown (V. M.)Cotton Brown BCotton Brown BCotton Brown CNPCotton Brown CRCotton Brown FSCotton Brown 4 GCotton Brown MCotton Brown O, 2 RCotton Brown 3 RCotton Brown RNCotton Brown TCotton Brown VCotton Brown 100, 137, 153Cotton Corinth GCotton Cutch 21 ACotton Dark Green B, N. ..Cotton Dark Green 138....Cotton Fast Red 4 BSP, 4 BXCotton GreenCotton Green A, 88 A,
105 A, BCotton Groen DCotton Green 2 GCotton Marine BlueCotton Milling Black
VarSchByVarSBKCGDHD1IGrE
BBSWDKBBBLevKBKSBBKLevBWDLevKCGaGrEKMB§BKWDCKLevBLevKSKLevBkB
LevB.GrELovKLovBKLovSLKB
307307374313313313313UK)041GOOoUOlieA00A70U1214G2c738A39GA71A72A73402c462cA39G463A3904G2cA754G2hA39G4G20A74538049538aU32SU49053SaU32S53,SaU328539G49538a049538a539737490U329490aU122490a490aU320400aU329490aU123490aU329400a312A732U330U7323G3U331U733A714U51GU332U124
Cotton OliveCotton OrangeCotton OrangoCotton OrangeCotton Orange (V. M.)Cotton Orange FB, GIv. . . .Cotton Oiangc GCotton Orange RCotton Orange RR, R 2 O. .Cotton Orange 10737 ....Cotton Orange Brown(V.M.)Cotton Pink BCotton PonceauCotton Puro Bluo BCotton Purple 5 BNCotton RedCotton RedCotton Hod ACotton Rod 05 A, 201 ACotton Red BCotton Rod 4 BCotton Red 4 BCotton Red 8 BNCotton RubinoCotton RubyCotton ScarletCotton ScarlotCotton ScarletCotton Scarlot NP, NPX...Cotton Violet 43 ACotton Violot 2 BCotton Violet 5 BCotton Violet RCotton Violet XCotton YellowCotton Yellow CIICotton Yellow GCotton Yellow GI, GXCotton Yellow R,Crosol Black (V. M.)"Vesotino Yellow GJrcsotine Yellow GOOCrosotino Yellow RCrosyl Blue BBS, URN....Crosyl Fast Violet 2 BCrimson BBTCrimson Benino GCroccino AZCroeoino BCroccine 3 BCroccino OrangeCroocine Orange GSroceino Orange RCrocoino Orange X3roeeine Orango YCrocohio Scarlet (V. M.). . .3roecine Scarlet 3 BSioccine Scarlot 7 B, S B. . .Croccine Scarlet 10 BSroeeine Scarlet 8 BLCroeoino Scarlot 2 BXCroccino Scarlot 3 BXroccine Scarlet MOiroccino Scarlet MOOiroceino Scarlot MOOirocoino Scarlot Oirocdno Scarlot OOCross Dyo Black (V. M.)...Iross Dye Blue FRJross Dyo Brown 2 D!ross Dyo Brown 4 RIrops Dye Drab NJross Dyo Green G
LovK
LovKB, SBKILovBBKABBtMCLovSBGrECGBLovBK§LovQQItLov
?BBBGrEGrE.MGrEGrELByAWCR«USohVarVnrSchCSohK
ByBy, KWDSohWDKKHIIIIHIIII
604 GLOSSARY OF DYE NAMES
NameManu-fac-turer Serial
No.Name
Manu-fac-turer
Cross Dye Yellow D... .Cross Dye Yellow RCross Dye Yellow YCrumpsall Direct Fas t
Brown BCrumpsall Direct F a 8 t
Brown OCrumpsall Direct Fast Red RCrumpsall YellowCrystal OrangeCrystal Orange 2 GCrystal PonceauCrystal Ponceau 6 RCrystal ScarletCrystal Scarlet 6 RCrystal VioletCrystal Violet 5 BOCrystal Violet 6 BCrystal Violet CVCrystal Violet 484Cumidine ScarletCupranil Brown RCupranil BrownCupranil Brown GCupranil Brown 12366Cupranil Brown 15596Cupranil Brown 15903CurcumeineCurcumeine GGCurcumeine SCurcumineCurcumine L, LCCurcumine 8000CurcuphenineCurch. BrownCurch. Brown DCutch Brown RCutch Brown 11759Cyanthracene Blue 3 B.. .Cyanthracene Blue 2 BL.. .Cyanthracene Yellow S. •..Cyanthrol BGA, G, 3 GO. .Cyananthrol R, RBCyananthrol RBA, RBX..Cyananthrol RXO, RBY...CyanazurineCyanine BCyanine BFCyanine BlueCyanine BlueCyanogen Blue 13623...Cyanol (V. M.)Cyanol Green (V. M.)Cyanol Fast Green B...Cyanosine BCyanosine spirit solubleCyprus Green BDark Navy Blue 2935...Dark Purple (printing paste)Deep Black DDeep Fat Black ColorDelphine Blue BDeltapurpurinDeltapurpurin 3 BDeltapurpurin 5 BDeltapurpurin 7 BDevelop BlackDevelop Black NZDeveloped Black BDeveloped Black BHDeveloped Black NDeveloped Black RDeveloped Black W
HHHLevLevLevLevVarB.etc.A,BKWDcVarA 'BISchIIIIIA, BKBKAtM.GGLCICoAWMSCVCVCVBBBBDHA, MACVtMCccIM.K.SALevLevtMAS,ByAWVarLevWD
AWAWAWAW
S178S179S180444
44534117S
383S
113113
U543U2S6
516516516516516
83A6S9A687A688A690A690A690
140140140142142
916
A540A426A7]<5A601U727U728U729
860859859859630544544544a
U527UC04
546566b566598594
A19537a
U736U528
U 2622366366a366367333d333d
XJ570333
U571XJ572U573
Developed Blue G GDeveloped B r o w n MDeveloped Green FDiamine Aldehyde B l u e . . .D iamine Aldehyde Scar le t .Diamine Azo BlueDiamine Azo B o r d e a u x B . .D iamine Azo Scar le t ( V . MDiamine Black (V. M. ) • • •Diamine Black B HDiamine Black B ODiamine Black H WDiamine Black R ODiamine Blue B l a c k EDiamine B lue (V. M. )Diamine B lue 2 BDiamine Blue 3 BDiamine Blue B XDiamine Blue C 2 RDiamine Blue 6 GDiamine Blue 3 RDiamine Blue R W . • • •Diamine Br i l l ian t B lue G . . .D iamineBr i l l i an tBordeauxRDiamine Bri l l iant R u b i n e . . .Diamine Bri l l iant S c a r l e t . . .D iamine Br i l l ian t V i o l e t . . .Diamine Bronze GDiamine Brown (V. M - ) . . .Diamine Brown BDiamine Brown MDiamine Brown VDiamine Ca tech ine ( V . M . ) .D iamine Ca tech ine G . . •Diamine C u t c hDiamine D a r k Blue B . . .Diamine D a r k Green NDiamine F a s t B lack (V.M.)Diamine F a s t B lue (V. M . ) .Diamine F a s t B o r d e a u x . . . .D iamine F a s t B r o w n (V.M.)Diamine F a s t G r a y . . • • • • • •D iamine F a s t Orange (V.M.)Diamine F a s t R e d F & (V.M.)Diamine F a s t Scarlet (V.M.)Diamine F a s t Violet (V.M.)Diamine F a s t Yellow (V.M.)Diamine F a s t Yellow 3 G . .D iamine GoldDiamine Golden Y e l l o w . . . .D iamine G r a y GDiamine Green (V. M . ) . . . .D iamine Green BDiamine Green GDiamine Hel io t rope (V. M.)f a m i n e J e t B lack (V. M . ) .
>iamine N e r o n ( V . M . )aJiamine N e w BlueDiamine Ni t razo l B r o w n G.Diamine Ni t razo l Green1 Diamine Ni t r azo l O r a n g e . . .Diamine Orange (V. M . ) . . .D iamine P u r e BlueDiaminera l Blue (V. M. ) . . .^ i amine ra l B r o w n GJ i a m i n e R e d (V. M. )Diamine R e d B'Diamine R e d 3 BDiamine Rose (V. M. )f a m i n e Rose F F BDiamine Scarle t (V. M. )Diamine Scarle t H SDiamine Sky B lue F F
A WA WA WCcccccccccccccccccccccccccccccs€cccccccccccccccccccccccccccccccAAccccc
GLOSSARY OF DYE NAMES
NameManufac-turer
SerialNo. Namo
Manu-fac-t urcr
Diamine Sky Blue (V.M.) .Diaraine Violet NDiamine Violet Red B. . ..Diamine Yellow (V.M.)...Diamine Yellow CPDiamine Yellow NDiaminogen (V.M.)Diaminogen Blue (V.M.). .Diaminogen Blue BB, NA.Diaminogen Sky Blue N. .Diamond BlackDiamond Black AF, CY,
EA, ETDiamond Black FDiamond Black FBDiamond Black GADiamond Black GAFDiamond Black P 2 B, PV,
PVTDiamond Blue RDiamond Blue Black EB. .Diamond Bordeaux RDiamond Flavine GDiamond GreenDiamond Green BDiamond Green BDiamond Green BXDiamond Green G, GF, GNDiamond Green 3 G....Diamond Green SS.....Diamond Green special. . . .Diamond MagentaDiamond Magenta IDiamond Phosphine (V.M.)Diamond Red BHDiamond Red GDiamond Violet BBDiamond Yellow GDianil Black PRDianil Black RDianil Blue BDianil Blue GDianil Blue RDianil Blue 2 RDianil Crimson BDianil Garnet BDianil Yellow 3 GDianil Yellow RDianil Yellow 2 RDianisidine BlueDianol Black (V.M.)Dianol Black BHDianol Black EDianol Black EXDianol Black RO, RWDianol Blue 402Dianol Brilliant Blue GDianol Brown CDFBDianol Brown LFDianol Fast Red KDianol Fast Red FGDianol Green BDianol Orange 217 ADianol Orange BrownDianol Orange Brown X...Dianol Red BDianol Red 2 BDianthrene Blue 2 BDiazanil BBDiazanil Scarlet BDiazanil Scarlet 6 BDiazine BlackDiazine Black H
CCCCCCCCCCVarBy
ugyByBy
TMMMMMMMMMMMLevLevLevLevLevLevLevLevLevBDBDLevL.vLevBDLevLevMMMKSen
A36S327
A369A370
304404274273273
A373275275275275275275
157164a1S1
A22210227049527649549927(5276276
U128U129609b
A223A224U5772044914793S0415323379
A427332252627408436a436a436a436a328424a424b356a356a279343474356b356o356357356881273
A428A429125333
Diazine Black 1401Diazine Green SDiazo Black B, OB, OT...Diazo Black 11Diazo Black 10020Diazo Black B1IADDiazo Black BHNDiazo Black BHN(Diazo Blue XDiazo Blue Black RSDiazo Bordeaux 7 BDiazo Brilliant BlackDiazo Brilliant Black B. . .Diazo Brilliant Orange GRDiazo Brilliant Scarlet B. .Diazo Brilliant Scarlet 3 BDiazo Brilliant Scarlet 6 BDiazo Brilliant Scarlet 2 BLDiazo Brilliant Scarlet 5 BLDiazo Brilliant Scarlet BGDiazo Brilliant Scarlet G. .Diazo Brilliant Scarlet PR.Diazo Brilliant Scarlet PR.Diazo Brilliant Scarlet S 4 BDiazo Brown. GDiazo Brown 3 GDiazo Brown (jGDiazo Brown NilDiazo Brown 3 RBDiazo Fast BlackDiazo Flint Blaok BHX.. .Diazo Fast Black G[Diazo Fast Black MG'Diazo Fast Black SD. . .Diazo Fast Black V . . . .Diazo Fast Bordoaux BL...Diazo Fast Groen GE...Diazo Fast Rod 7 BL.. . .Diazo Fast Violet BLDiazo Fant Violet 3 RLDiazo Fast Yellow GDiazo Fast Yollow 2 GDiazogeno BlackDiazogono Black ABT)iazogono Black ADOiazogonc Black N^iazogono Bluo 11)iazogono Blue 2 R, 4585.."•iazogono Bluo RDiazogeno Garnet BB
)iazogono Had 8 B>iazo Indigo Bluo BR>iazo Indip;o Bluo 2 KL, 3 RLMazomino Hod L'iazo Olivo G•iazophenyl Black X,Hazophonyl Bluo BCHazo Pure Bluo 3 GL'iazo Rubino B'iazo Skv Bluo 3 GLiazo Sky Bluo B•iazurino B>ichroino Brownicyanino•imethyl-indigo'ioxine)ipbeno Blue Bioh^ne Bluo Itiphenylamine Blueipheny 1 Black•iphonvl Black L•iphenyl Black RC)iphenyl Blue 3 BC
KKByByBKSByW BByByBy
BvByByByByByByByByByWDByByByByByByByByByByByByByByByByByByByAWAWAWAWAWKAWAWAWBy
GByBy
M¥MAAnnMGGG
606 GLOSSARY OF DYE NAMES
NameManu-facturer
GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGHHAW4WKQKIByCGItSKBySPByKCVKISHKK
SerialNo
A618A620Abl9A02133434834839334S347449206617ISa1414
20512
4633A622Ab23A6244625462b295207
A627343
A62SIS18
A0294b746b
A62946713a13
35S35S
A634A635U753442a
A5oOA5-1U335442a
U335A69242o9333a
1335142aL335
A2G0442aTJ3354424261
TJ335442a
U3354693442a42Sa
U336XJ336
Name Manu-fac-turer
QI1BKQKIAWSCGKIIWBICVIHByLevILKKLGLIILQKSSIAWKKKILKIKAByBy&ByIAWKByKIIIISKIKtMGrEIPI
SerialNo
428a428428a379b42 Sa
U336428a428a428a428a
U336397428a337
U336428a428a428a428a455455b42Sb
A502U337XJ337A503
457A636A504
486344
A505344a
U337A717A718A694A552U33SU340U339A695344
U341478b
U342A20462a462
U343463
A696A553U344U345A262U346
392c343343a
A698U704U347
279U348
617o617c398681354
Diphem 1 Blue BECDipbenj 1 Blue BTCDiphenjl Blue BBECDiphenjl Blue 2 RDiphenjl Blue BlackDiphenyl Brown BBNCDipbenj 1 Brown BN BVC!Diphenjl Brown 3 GN
3 GNCDiphenj 1 Brown GSDiphenyi Brown RNDiphenj 1 Brown TBDiphenyl Catechme GDipbenyl Cblonne Yellow FFDipbenj 1 Cblonne Y eilow G
229Dipbenyl Chrysome G, GCDipbenj 1 Chrjsoine 3 GNDiphem 1 Cbrysome RRDipbenyl Citronine GDipbenj 1 Dark Green BCDiphenj 1 Deep Black GCDipbenj 1 Deep Black GNDipbenj 1 Deep Black GWCDipbenj 1 Deep Black \ NDiphem 1 Deep Black VPDipbenj 1 Fast BlackDiphenjl Fast Brown G,
GNC ..Dipbenyl Fast Gray BCDipbenj 1 Fast RedDipbenj 1 Fast Violet BCDiphenj 1 Fast Yellow extnDipbenyl Fast Yellow GDipbenyl Green BCDiphenyl Green GDipbenj 1 Green 3 GDipbenj 1 Green 3 GC, 3 GFDiphem 1 Green KGWDiphenjl Orange GGDipbenj 1 Orange RRDipbenyl Red 8 B SCDiphen\ 1 Red 1S4 340Dipbenj 1 Scarlet 3 BDiphenyl \iolet B\CDisulphine Blue 47073 DSDirect Black (\ M )Direct Blac*. 4BCDirect Black CDirect Black DDirect Black DDirect Black DBDirect Black EDirect Black FBSDirect Black FBSDirect Black GDirect Black S GDnect Black 3 RDirect Black RCDirect Black RODirect Black TDirect Black VDirect Black VTDirectBlack WC 3899 3919Direct Black 7o65Direct Black 8o35Direct Black 14714Direct Black 33336Direct BiueDirect Blue (V M )Direct Biue A
Direct Blue ABDirect Blue BDnect Blue 3 BDirect Blue 5 BDirect Biue 5 BDirect Blue 7 B 12 B BK,
FFDirect Blue BXDirect Blue C GDirect Blue 3 GDirect Blue GNDirect Blue GRC N 2 B R
5RDirect Blue RDnect Blue RWDirect Blue WBBDirect Blue X 2 BDirect Blue 30Direct Blue 7079Direct Blue 13108 13503Direct Blue 51096Direct Blue Black BDirect Blue Black 313Direct Biilhant Blue 8 B[Direct BrownDirect Brown (V M )Direct Brown B, HDirect Brown GDirect Brown 2 GDirect Brown 3 GNCDirect Brown HBDirect Brown J JJB JPDirect Brown MDirect Brown NDirect Brown RWDirect Brown TBDirect Catecbine GDirect Catecbine 30Direct Chrome Black 14722Direct Chrome BrownDirect Cotton Blue GS RDBDirect Cotton GrajDirect Cotton G een 2 BDirect Cutcb GGDirect Dark Brown MDoct Dark GreenDirect Dark Green SDirect Dark \ lolet BEDirect Deep Black EDirect Deep Black EDirect Deep Black EWDirect Deep Black NTSDirect Deep Black RWDirect Fast Black BDirect Fast BlueDirect Fast Blue FFBDirect Fast Brown C GBDirect Test Brown GGDirect Fast Gray RNDirect Fast Orange 16710Direct Fast Red FDirect Fast Red 17727 25420Direct Fast Scarlet (V M )Direct Fast Scarlet 4 BSDirect Fast Scarlet 4 BS
8BSDirect Fast Scarlet SEDirect Fast \ loiet 3654Direct Fast YellowDirect Fast Yellow 00, RDirect Gray BDirect Gray B JDirect Gray R
GLOSSARY OF DYE NAMES GOT
Name
reenreen Breen Breen Creen Green Green 3 GG Yreen KGDreen Ureen 10865reen 9753, 34267ldigo Blue Aldigo Blue BKldigo Blue BNidone Blue IIavy Blueavy Blue Brange BR Grange Grange Hrange Rrange Rrange 6 Rrange 1901range 6693ore Bluenrple NededBed3BedNed 215, 1725ifranme Barlct ABarlet Barlet 3 BaTlet FBiy Bluecy Blue Bcy Blue FPiy Blue 22wy Blue 13108s.y Blue, greenishLolot BLolet BBLolet RLolet RLolet Rlolet RRiolet3C53 4561lolet 11508lolot 12932 18510ellow (V M )ellow Bellow BKellow Cellow CAellow CRellow EGOOellow Fellow G GBE GRellow Gellow 2 Gellow 6 Gellow GOOellow MCellow PCellow PIellow Rellow Rellow 2 Rrellow TOellow V
Manu-fac-turer
ICGT SCGCGICGSGfeIIgKIvS
G
KLBKICGKI SDHSK
ISBKWBSsHCGSKCGIKAKSIIIGrESoliKLKSGrEG
By GrEGrESohAW
SerialNo478aA44447SaAtlA41(>475478aA41747SaAJ1S47Ha4 404 1035 i44*tmoUJ19tf)2b302lib3b2llaAr)0l5302b*02bU101U307bJ07bAbOOUS00U705U70UU1S0A700420A719A720A70042441 *ji41 iA440H *aAWKA45041 in01)<>KUb0o
A4G000b304b9b9fA4009d9hA4610617bOo
Direct Yollow WllDirect Yollow ZBind Vllow 212Dncct \cll(w 10i0r>Donimgo Ah/aim lihu k 1'Doming > Ah/atm Hla< 1 («DoinniKo Ali/ann Bhu HDoming ) Ali/tuiti H ttl< ut(Doming) ]ihulc4(2I<Domingo Bluo llln k HDoming >Vi 1< t A•Double llulhant h(atl< IDoublo Pone can RDouble) 1'OIK oau 2 RDoublo Pont < an 1 RDoublo Sunk 1Doublo Sciulo< oxtia S[Dra/ahno Ali/aunDra/alino Blade BI1Dra7rtlmo Hlu< 10 liDia/ahno Bin 2 Bl IDiaznhno Bluo CVDia/almo Blw IDra/ahno Blu< 1 1Diazalmo Bluo 1 8Diazahno lUuo \{\ IiDia/ahno Bluo VVViDrazahno Bluo Blade llWlDraahno Iioulouirc 0 HOmzulmc HiiHmnfc YdlowDrazahno Biown ( »i 1\DLa/ahno Biown 1 LDrazahno Biovm (rDraralnio Biown * (Jdrazahno Brown 4 JDra/ahi\( Urowix 1<Oalmo Chlonno Y<J11OW (Dra7ahno Diamond ViokLBBDra/ahno TaHt liluo 4 CJ h"Jm/ahno I mi («tav3i a/ah no I aHt R< dia/ahiu I aHi Rod 1ta/almo 1 aHl dl >w Bla/ahno ( arnoi BBlaruluui ( amoi I Ita/ahno ( tiuin BXramltno Indigo Hluora/alm< Now Rodra/alinu Now Rod 10 Branihno OmrtKO I Lta/almo Oran/ufo U•ra/aliuo Orango 11•nwalmo Rod 1'raraluio Rod 1 Lra/ahno Hod 1 V)razaln)o Soarlot B•ui/almo Hky Bluo 11>ia/£ilmo Violet 1)*ra/almo Violot NI X*•razalmo Violot VBTaralmo Yollow Rrazalmo Yollow Rra7almo Yollow H'ra/anno Yollow i'uranthrono Bluo C C'uranthrono Blue R9'uranthrono Yollowurmdono Blue 4 Bunndono liluo 5 Burmdono Bluo (I Bunndono Red B»urlndone Hod N
STaxm-iao-(UK IWBO( Ko
NT ot iBvByBvAI<vAWAWAWAWAWAWKAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWMAWAWM>»nBOm>BD 1
N< i uiiNoU >Hi<)U)ll>A >o,A OsA >0'iA >UUaA *!0-Ml»«Ul/l10SA >/lA- U iA t»»21717(1A 1A >>A r>dA >7A riSA M)I! T>2A »«mA »(UA <HA »(UA >(HA .(K>AA(10A >(»7Ar>HHA >(M>Ar>70Ar>7lA »72Ar»7 \A 571A >rt*A i/iiA »77A »7SA »/0A »S()A »S1A »s.>A SiA SIA >SftA >S0A »S7A iHUA »t)()A A)]AM);AM) iA Ml \A »wr*AMNtA »07Ut itAWKIAf»OHH \2HIHH\\)KKlHH28HI012017
608 GLOSSARY OF DYE NAMES
NameManu-fac-turer
BDFALLGGGGGGGGGGGGGGGAAVarVarB,ByBMBBBtMGLevBBBBBBBA, etc.SAA, LevSAASchSchSchSchSchSchSchSchSchSchSchGGGGGGGGGGGGGGGG
SerialNo.
905103389466720G
S141S142S143S144S145S146S147S148S149S150S151S152S153S1541231005875875S7a5S7a5875905S7a589588587275
U130U131U132U133U134U135U136121121121122122a122117462463463477a4773444S8464474464311
A63SA639U612U6135515541S4183180180a181
A640A641A642553
U614
NameManu-fac-turer
Durindone Scarlet RDutch YellowEboli Blue BEboli GreenEclipse Black CEclipse Brown BEclipse Brown GCEclipse Brown REclipse Fast Brown BC..Eclipse Fast Brown GC..Eclipse Fast Brown 3 GC.Eclipse Fast Brown 4 REclipse FastDarkBrownBCEclipse Fast Red Brown. .Eclipse Fast Red Brown EEclipse Phosphine GGC..Eclipse Phospliine RRC..Eclipse Yellow GEclipse Yellow 3 GEmine RedEosamine B, GEosineEosine (V. M.)Eosine AEosine AGEosine AG, A3 G, BBEosine BN, BNLEosine CA, WEosine S, SPEosine Spirit SolubleEosine (yellowish) 701....EraBlackJErgane Yellow GErgane Yellow RErgane Yellow WErganone Blue BErganone Blue GErganone Gray BErganone Violet RErica BErica BBErica BNErica GErica GErica GNErica 2 GNErie Direct Black G, GX..Erie Direct Black RErie Direct Black RXErie Direct Brown GBErie Direct Brown GRErie Direct Brown 3 RB...Erie Direct Brown RFt 2 RFErie Direct Green ETErie Direct Green MTErie Direct Green WTErie Orange 2 RErioazurine BCEriocarmine 2 BCEriochromal Brown EB....Eriochromal Gray 5 GEriocbrome Azurol B, BC..Eriochrome Aaural SEriocbrome Black AEriochrome Black TEriochrome Blue BlackB,BCEriochrome Blue Black G. .Eriochrome Blue Black R. .Eriochrome Brown RCEriochrome Brown SDEEriochrome Brown VEriochrome Cyanine R, RCEriochrome Geranol R
Eriochrome Green H.Eriochrome Green L.Eriochrome Green MEriochrome Green O....Eriochrome Olive G. ...Eriochrome Phosphine REriochrome Red AW, B.Eriochrome Verdon A, SEriochrome Violet B....Eriochrome Violet 2 BL.Eriochrome Yellow 2 G.Eriochrome Yellow 3 G.Eriochrome Yellow GR.Eriochrome Yellow S. ..Eriocyanine A, AC, R...Erio Fast Blue SWRErioflavine SXEriofloxine 6 BEriofloxine 2 GErioglaucineErioglaucine A, AP, EP, XErioglaucine 49141. . .Erio Green BErio Green NErio Green Supra.. . .Eriorubine BErio Violet BCErio Violet RLCErioviridine BErweco Alizarin Acid Blue RErweco Alizarin Acid Red BfErythrine7 BErythrine CErythrine PErythrine RRIrythrosineErythrosine A~"!rythrosine BIrythrosine G-Jthyl Acid Blue RREthyl Acid Violet S 4 BXXEthyl Blue BEthyl PurpleEthyl VioletEthyl VioletEthyl Violet 8682Euchrysine (V.M.)Euchrysine RR, GG, GNX,GRNTEuchrysine NX, RT, RRDEuchrysine 3R, 3 RXExcelsior BlackExcelsior Lake Scarlet (V.M."Excelsior Scarlet GExcelsior Scarlet 3 R ,Export Blue 1504ast Acid Blue'ast Acid Blue BFast Acid Blue 3 BFast Acid Blue RFast Acid Blue RHFast Acid Eosine GFast Acid Fuchsine BFast Acid Green RHFast Acid Magenta GFast Acid Marine BlueHBBX'ast Acid Navy Blue GRI..'ast Acid Phloxine A'ast Acid Red A'ast Acid Red EB, EGG...'ast Acid Red RH'ast Acid Violet ,
GGGGGGGGGGGGGGGGGGGGGHGGGGGGGRWCoRWCoBCBBMMM.etc.B,LBBBB, etc.B, GM, IBBBBAWCMMB
MBIMMLHAW.C
GLOSSARY OF DYE NAMES 609
Name
.cid Violettod Violet A 2 Rtod Violet Btod Violet Btod Violet 3 Btod Violet 10 Btod Violet ERRtod Violet Rtod Violet R, RBEtod Violet RGEtod Violet RXtod Violet 416Vcid Yellow (V M )tod Yellow RBEVeid Yellow RHSlackBlackSlack BSlack BSSlack NSlue31ue AOOOOBlueBBlueBBlue BB[Slue 3 BBBlueOBlue RBlue RDBlue ZBlue 62105Bordeaux BBordeaux GBrilliant Acid CarmineBnlnant Black 12349BrownBrownBrown 3 BBrown GBrown GSBrown NBrown 0Chrome BlackChrome BlackChrome Black KChrome Blue PRCotton Blue C GOCotton YellowDiiect Yellow 22090Cosine LGrarnct 5 B3 ray BSray RGBurrcen BGrrccn CRIn en bluishenc Blue 1ene Green GGlene Violet Bene Violet Renc Yellow-Lea t her Yellow 2G855[ ight GreenLight Orange GLight Yellow G, 2 G,GGNLight Yellow 3 GLight Yellow RGMordant Black THMordant Blue BVtordant Blue BMordant Blue R
Manufac-turer
MByMKByBKMMHKCMIIGLBBBtMGrEAAWGGrEMB KAGABKBKGrEIAByAAG1*MAWHBKQIWD833AWGrLGGtMByByAWAWAWAWAV*ByBYByByISByMLevMM
SerialNo
5S25825(25S0
IH5352b
U1J9IH5J
5S0 i5S25S0i
U35 4UU()
1371U022
058740711100600t>)Ob0)7( )0
U(2*( )0b009(0)019
u m0102*(»a2 *(>a( ()C
U()00172213172212
U( 251(0211
U57S275a
IHS1HSO1115 ISUrll
301b500b
U57)0S10S1
U52052 352 i
U5S2U5S3U5S4U5S5U5S0U2 3O
52 kt3810
Ul<1010a
275U7 37A4 3OA431
Name
Past Mordant Yellow1 ast Moidani, Yellow G1 a,st Navy BlueI a,st Navy Blue APist Navy Blue BNNOO,
RZOOI nst Neutr il Violet B1 ast Orange I GI nst Ot vn^L O1 ait P ipc-i Yellow GL ast Punclast, Pink BN GN1 dht Pink f oi silk1 ast Ponceau LFast Punting GreenPast Printing Yellow Rraat Red A1 ist Hed ATast RedrxstRcdPast Red A1 ast Red ANSXPast Red AV1 ibt Rod B1 ast Red BNI ist Red BTI ist Red CJPast Red ETast Rod IBS1 ist Red NS1 ast Red OI ast Red &lastRcl VRPast Russian Green1 nst S ul( r Blue A RI ast Scarlet B1 wtSdiletBlast b(atktBX:lnstS<ailct BXGI ast Straw \ ellow V1 ast SuK< n BlackI ist Sulf nBliukTI ast buK< n Violet 5 BS1 ast Sulfon Violot 4 R1 ast Lduylcnc RedI ast \i(torm Violet S4B1 ast Vi ilot It1 ast We ol Blue I1 ast Wool bcarlct 4 RPast Yollowlast Y( How PYla«t YclbwGRI ant \ilbwN1 ftHt Y How RI ast Y( 11 w SI ant Yellow YI iwt " ellow 951 ant VioletPlava/me I 3 GL1 Iava7inc LI lava/mo S1 lava/mo T1 lavinduhno II OI lavophosphme G 4 G, It1 lavopurpunnI luoicflcemeI ( rmyl Violet (V M )1 raiHO1 i ( nch BlueI rr iuh Kod1 ucliHinc1 uchsine ASVI uohsine B
Manu-fac-turer
VarBKGiBGrl?cIMCOAWIDIIByKByVarBVarVarWBBB ByB etcBBy etcBVarBByMSehBvWDAWBKBBAW&SsGrTGiLAWAWBIvVarlevtMPKBKCBQMMMMBMVarCPQP etcVarPtM
SerialNo
29429464964964907S
5148U492
U5S0G94C04
A2652
U240lblA77Lb8lblIb6A78lbl1121121111631C6A79KS101Ml104
U515049
U1U218UH2
Ul4iA(01
2012(11S21S2T>8uOld
A(>02U5S1U1S2
1 *71*71*71501491*714913702020a192020a
608009d7S5585530
U595US02U593
512512512
610 GLOSSARY OF DYE NAMES
Name
Fuchsme IFuchsme MBFucksine NBFuchsine Sruchsxne TRFulling Orange 1G700Fur Black DMTur Gray 279o3Furreine DBFuscamineGallamme BlueGallamhc Violet II BGallazme AGallazolBlue4GGallemeGalleme JRG pasteGalleineSR bW WGallocyanmeGallocyanme DGallocyanine DHGallocyanme FGallocyanine MSGallonavine WGallo Green DHGallop hemn PGallo Violet DGallo Violet DFGallo Sky Blue BGambine YGeramne 2B GGeranium BGentiana Violet BGentianine AGlaoier BlueGloria Black NGlvcine CorinthGlycme RedGolden BrownGolden OrangeGray NOGray Blue 0095Green AGreen BXGreen GGreen HDGreen PLXGreen VGWGreen 21Green 24.1Green 15825Green Crystals DllaGreen Crystals EGreen Crystals TGreen Crystals MGreen Crystals XGreen Crystals YDGreen Crystals HaGreen residueGreen residue DGrela Red RGuernsey Blue OGuinea Black 3 BLGuinea Bordeaux BGuinea Bordeaux 6 BGuinea Bordeaux BLGuinea Brown RGuinea Brown 2 RGuinea Carmine BGuinea Carmine DGuinea Cyanme LBGuinea Cyanme LGGuinea Cyanme LRGuinea Fast Green B
Manufacturer
GrEtMSchBfeckIByByIG ByDHDIIGB> etcGB\arBIBDHBDHByByHBjfc>AGIByIviAByfeIv11AWIvII15BSoHIvtMHtMKHIvIvKGrEMAAAAAAAAAAA
SerialNo
512512513524512250a
U241U212
923923017C 39G15
UG2G509509509G2bG2b(2GG2602S772629CpSa
IJ243U214
OU2118U46r9b501U2453103092Sb145C9ba
U35740 )a
U:>S7XJ3 >4
49 uU144U707UsO-j
40 mU35b
40540)105
Ui )b405
XJ J5(>U irr)U ir5U507
5iq115UGXJ7"UbU9
U10A22A 23Ull1312TI13503
Name
Guinea Fast Green 3 BGuinea Fast Green 2 GGuinea Fast lted BL'Guinea 1 ast Red 4 BLiGuinca last lted 2 ItGuinea I aat Violet ALGuinea Fast Violet 10 BGuinea GreenGuinea Green B GGuinea Green 2 GGuinea Red 4 RGuinea VioletGuinea Violet 4 B 6 BGuinea Violet S 4 BHalf Wool Blue 3 RHalf Wool Green b3bl6Half Wool Green 63S16 N 5Hansa Gteen GHansa Rubme GHansa Rubme OIlansa Yellow GHansa Yellow 5 GHansa Yellow RHat Black (V M )Hat Black A 4 ANHat Black BHat Black L, SHavana Brown SHehantkmeHehantlnne G GG GFF, RHelgoland Black BHHeligoland Black FFNXHeligoland Blue G BHelgoland Blue RWHclindonc Black RRGIlehndone Blue BBHelindone Blue 3 GNHelmdone Blue 3 ItHelindone BiownHelmdone Broun ANIlehndone Bro n CRIlehndone Bro"\\n GIlehndone Bro-wn 3 GNHelindone Brown 2 RHelmdone Brov. n 5 RHelindone Fast Scarlet CII hndone last Starlet R RCIlehndone Giay 2 B BRHelmdone C reen GIlchndono Printing Black
2 RGIJohndone Oian e DHe Undone Orange GRNJfchndone Orange ItHelmdone PinkHelmdone Pink AN, BNIlehndone Red BHelmdone Red 3 BHelmdone Scarlet SHelmdone VioletHelmdone Violet B BBHehndono Violet DHolmdone Violet RIlehndone Yellow CGIlehndone Yellow GG vatHelmdone Yellow 3 GNHelmdone Yellow RNHeho Bordeaux BLHeho Fast Blue BLHeho Fast RedHeho Fast Red RL TRLHeho Fast Rubenne RLHeho Fast Violet AL
Manufac-turer
AAAAAAAVarAAAVarAABvLLMMMMMMCGrEAGrECBGGGGGMMMUMMMMMMMMMMMMMMMMMMMMMMMMMMMMByByByByByBy
SctialNo
U15UlbU17UlbU19U20U21502502505A2453053Oo530U240
U519U520U437U43SU439
28U441U442A376U508U22
U50SU2S7
13814143G43b424
A453921880896896a904a873904a90483G902903907915921892921a9148-*591191001001701801b020020808020blOa810810810a
A2G68587373
A268A269
GLOSSARY OF DYE NAMES 611
Name
Helio Tast Yellow 8 GLHelio Red RMHelio Red RMTHeliotrope 2 BHessian Brilliant PurpleHessian Brown BBNHessian Past Red FHessian Purple NHessian YellowHoffmans VioletHomophosphme GHomophosphine 00Hydranthrene Brilliant Cop
per DHydranthrene Dark BlueHydranthrene Olive RHydranthrene Yellow AG
ARHydrazme Yellow 00Hydrazme Yellow SOHydrazol BlackHydiazol Black RHydrazol Chrome Black CliHydrazol Chrome Black DBHydron Blue (V M )Hydron Blue G RHydron Brown (V M )Hydron Olive GHydron VioletHydron Yellow GHylidme Ponceau 2 RHyhdine Ponceau 2 RImmedial Black (V M )Immedial Blue (V M )Immedial Boide IUX GImmedial Brilliant Blnck BImmedml Brilliant Caibon
r, FGImmedial Brilliant Green GImmedial Brown (V M )Immedial Carbon (V M )Immedial CutchImmedial Cutch (V M )Immedial Dark Brown
(V M)Immedial Dark Gxeen BImmedial Deep Gieen GImmedial Direct Blue(V M )Immedial Green (V M )Immedial Green BluoImmedial Indo eno (V M )Immedial Indone (V M )Immedial Indono Violot BImmedial KhakiImmedial Maroon BImmedial New Blue GImmedial Olive (V M )Immedial Orange C, NImmedial Purple CImmedial Sky BluoImmedial Violet CImmedial Yellow (V M )Immedial Yellow Olive(V M)Imperial Green GIImperial Scailct 3 BImperial Yellow RIndahzann I J RIndalizann GreenIndamme i RIndamine 0 RIndamine BlueIndanthrene
Manufacturer
ByByByALByLLLBy TLPLL
GiTGrlAWAWAWAWCCCCCGtMGCCccccccccccccccGccccc0cccccByByByDIIDIICGCGM13
SerialNo
A270A271A272
321>024S031 *5013055U( 000001370*
7J1S10All 2
All *AGO*A(04AGO;AOOb
7 IS71874 SA7lbb7tSe71Sd
U027U5*2
72172 ta7*0720720SG9725720870S71725S73S74:S7r>740740S7G7337* *aS777*9S78S79711SSO728SSL710SS2
A27*247
7bCrt*0*4704705096837
Name
Indanthrene NNIndantlnene BlackIndanthrene Blaek B BBIndantluene Bluo 3 GIndantl tene Blue GCIndanlhicne Blue GCDInlmthrcne Blue GGS
GGSIEnd mthrene Blue GG SPIndmtl renoBlue 3 GPIndunthrene Blue RInd mil lene Blue RSInd xnthtenc Blue WBIndanthrene Blue WRIndantluene Bluo Green BIndmlhrene Bordeaux BIndmthrene Boiden.ux B
e\traIndantluene BiownIndanthrene Biown BIndantlnene Claret BIn lanthteno Cluet B extriIndun tin one Coppei ItIndmthrene Daik Blue BDIn 1 uUhiene Daik Blue BOIndanthienc Dark Blue BPIndanthrene last Blue RRIndanthrene Gold Oian ,e GIn lantlnene Gol 1 Or inge ItIn lantlnene Gold Orange RSInlintluene Gold Oiange
2 RT.Ind mtl lone Gray B BPIndunth one Guen BIndantlnene Mtuoon RIndanthrene Olive GIndanthrene Orange RTIndanthrene Pink BIndanthrcno Red BNInd an fch tene Red GIndanthreno Red ItIndanthrcno Rod Brown RIndanthrene Red Violet RRNIndanthreno Scarlet G, GSIndanthrene Violot BIndanthreno Violot KIndanthrene Violot ltNIndantincno Violet RRIndantlneno Violot ltlIndanlhieno Violet Yellow
G PIndantl reno Yellow G GPIndn/ino MIndnzurmo BIndazunno BBIndazuuno GMIndnmrine 5 GMIndzuurinc RMInduzunno ISIndia Ro e 17285Indian RedIndian Yellow (V M )Indian Yellow G GNIndian Yellow ItIndigene ItIndigene Blue BBIndigene Blue ItIndigoIndgio pnwloIndigo powderIndigo solutionIndifeo TBPInd go G
Manu-facturer
BBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBC
IGCByAWIIVarVarVarMByB
SerialNo
873a7G8a768a840843842841841840S37838850850a705a82882780780782S8278137G37G3840S37a7G07017017G18487(584579181287 *b83182G830873o873d7027087G0832767704840a849089411429427430390390
U0G7U028
141b141140097
A701A702874874874874874888
612 GLOSSARY OF DYE NAMES
NameManu-fac-turer Seiial
No.Name
Manu-fac-turer
Indigo 7 GIndigo KB pasteIndigo KGIndigo MLBIndigo MLB 2 BIndigo MLB 4 BIndigo MLB 5 BIndigo MLB 6 BIndigo MLBR, MLBRR. ..Indigo MLBTIndigo MLB Vat IIndigo NCIndigo RBIndigo TIndigo Acid Blue AIndigo Blue NIndigo Blue 275Indigo Carmine Blue BG...Indigo Extract A, AN 4Indigo Salt TIndigo Yellow 3 GIndigo WhiteIndigotineIndi&otine PIndigotine 500Indo CarbonIndochromineIndochromine RR, TIndochromine Black EXD..Indochromogen SIndocyanine B, 2 RFIndocyanine BIndoineIndoine BlueIndoine Blue RIndophenolIndo Violet BFIndulineIndulineInduline BInduline 2 BInduline B AInduiineDB, NInduline NN ,Induline NBLInduline RNInduline SInduline WLXInduline 1768, 1778Induline 10350Induline 38724, 38725Induline Black base 5789. .Induline Red (V. M.)Induline Scarlet (Iris Blue)Induline Spirit Soluble....Induline Water Soluble. . .Ingrain BlackIngrain Black 4 BInk Blue BJTBNOOInk Blue BJTNOInk Blue BNOOIntensive Blue BIris BlueIrisamineIrisamine GIrisamine G exIsamine Blue (V. M.)Isodiphenyl Black RIsopurpurinItalian GreenJanus Brown BJanus Gray BJanus Red B
KMMMMMMMMrCJABKBVaTBAC8SAGWDSchBDHAVarVar??tMB¥BKHKKBVatVarHHGrEGrEGrEllCCscGMMM
8748818838748808818828838798S88768748S0888545874874U2387787588987687787887774 S067667667a666705a699c126126126619U24699697699699697699699699699697699699697699700699a671697699A759A758U509U50DU5095G2648576576576U288437784709435128240
Janus YellowJanus Yellow GJapan BlackJapan Black BJapan Black MJapan Black MBGJapan Black MF"asmineasmine high coneJaune Me*tanile BromGJet Black APXi et Black RJet Black RRJute Black BJute Black IJute Black RNTJute Coal Black SKatigene Black (V. M.)....Katigene Black Brown BW.Katigene Black Brown GN.Katigene Black Brown R...Katigene Blue Black 4 BPAKatigene Brilliant Black B,FGKatigene Brilliant Green 3 GKatigene Brown 2 RKatigene Brown VKatigene Chrome Blue 5 G.Katigene Cutch BKatigene Deep Black BKatigene Direct Blue B....Katigene Direct Blue RF...Katigene GreenKatigene Green 2 B, 4 B,F2G, MICKatigene IndigoKatigene Indigo BKatigene Indigo GKatigene Indigo 3 GTKatigene Khaki GKatigene Olive GNKatigene Olive Brown R...Katigene Red Brown RKatigene Red Brown 3 R—Katigene Violet BKatigene Violet 3 RKatigene Yellow GKatigene Yellow GGKatigene Yellow GRKatigene Yellow Brown GGKatigene Yellow Brown GRKatigene Yellow Brown 9 RKatigene Yellow Brown RLKetone Blue 4 BNKetone Fast Violet 10 BKitonBlue NKitonBlue VKiton Fast Green VKiton Fast Orange GKiton Red 6 BKiton Red GKiton Fast Violet 10 BKiton Violet 12 BKiton Fast Yellow 3 GKiton Fast Yellow RKiton Yellow GKiton Yellow GGKraft Brown LKraft Brown basic YZKryogene Black BNXKryogene Black TBO, TG .Kryogene Black TGE, TGOKryogene Black TGO...,
MBBBBBGGPB
llBytMBByByByByByBy
ByByByByByByByByByBy
ByByByByByByByByByByByByByByByByByByByM
I
I
I
I
IIIIBBBBBB
GLOSSARY OF DYE NAMES 613
Name
Kryogene Blue BNOKryogene Brown AKryogene Brown A, GKryogene Brown GXKryogene Brown R B,
RBNXXKryogene Brown RXXKryogene Direct Blue BKryogene Direct Blue 3 BKryogene Direct Blue
BNAGXKryogene Direct Blue G, GOKryogene Green GXKryogene Pure Blue RKryogene Red Brown GRXXKryogene Violet 3 RXKryogene YellowIvryogene Yellow G, GGKryogene Yellow RLacquer Black RLake Black CLake Black PLake Blue ABIILake Blue ABOIILake Blue AVLake Blue AVOLake Blue ILake Blue RTLake Bordeaux BLake Purple S PLake RedLake Red CLake Red DLake Red PLake ScarletLake Scarlet Red DLake Yellow 28227Lanacyl Blue B BBLanacyl Violet B BTLanafuchame (V M)Leather Black (V M )Leather Black BOLeather Black CRLeather Black ILeather BlackLeather Black RLeather BUck TLeather Black 3553Leather BlownLeather BrownLeather Brown GGI eather Brown IXLeather Brown RLeather Flavinc 9118Leather Flavi no 9118 ..Leather Gold 5902Leather Olive 71930Leather OrangoLeather Orange BLeather Orange BYLeather Red 0Leather Yellow ALeather Yellow 1G TULeather Yellow GLeather Yellow 2 G 3 GLeather Yellow GC GS, MLeather Yellow GNLeather Yellow NLLeather Yellow 0Leather Yellow PLeather Yellow R TGLeather Yellow 1BRLeather Yellow 582Sa
Manu-fac-turer
BBBBBBBBBBBBBBBBACGMMMMBBKMBVarMMMCMByCCccBBIKtMMGrEGrDKByTcvIISBKASehLevLevMGiEQVarCOGrCAWBKMtMQtML
SerialNo
753743750750751751a753754753752754a729751b754b712712710U25
U2S9UO30U143U1UUli5UWbU150U1S*
179U157
1531532001*2
A377A4*5U217
187ISO04
U290U158U159U077U*58U5 ir)II147U511
20SU*5)U2182H*a2SiaOOOgOOOcr
UtKlTJ20211
U7*8U7S9U14S
000000000000GOO00000bGOO600000000GOO
Name
Lemon Yellow RLeueo Gallo rhionme DHLeucol Dark Green BLeucol Brown BLight BlueLight Blue GIi ht Blue Superfine Spirit
bolubleI lght Green A ex coneLight Green 2 ALight Green 2 G coner lght Green SFLi ht Green SFLight Gieen SF BluishLight Green SF YellowishLight Green SF YellowishI lght Green SLLight Green YellowishLilac PCLilac PCLiquid Oil Black NLissome GreenLithol Claiet BLithol I a-st Orange Rr ithol Fast Scarlet B G RNLithol I ast bcarlet RLithol Red 3 B GG, 3Gr ithol Red RLithol Red RG RSLithol Rubine B BN G RGMagentaMagenta AMagenta ABMagenta BMagenta 1ABSMagenta L, SMagenta IPMagenta (acetate)Magenta crystalsMagenta eiyatals 3Magenta ciystals IIMilaelute GreenMalachite G reen (V M )Malachite Groan BaseMarine Blue BMaune Blue RRMaroonMai ion C")iduMi sRid AX GX\Tiirtius \ (HowMai tiUH Yellow 7UMartma Yellow 0740Ma,uvoMelanogene BlueMchinthermo BIIMclanlheurie IIIMolanthe unc HOMdanLheunc 11818, 12700Molanthormo Blaek BllMo Idol i H BlueM( lclola s Blue 3 ItM< logouc Blue BIIMere (rme Wool Si arlot 5 BMerecrol Brown i ItMencrol Oiange 2 RMeridian Black ALMeudian Blaek ANMetachromo Blue BMctaehtoine Blue GMotaelnonxe Blue Bliok 2 BMetacliromc Blue Black 2 BXMctachrome Bordeaux RMetachromo Brown B
Manu-fac-turer
KDHByBytMtMMtMtMBBBBBQ
DIIGtMHBBBBBBBBVarBBCHBtMBVartMtMVaiVarVaiItMBy§A BIvGBKP etcMIIIIISsIIIIIIs.sAAAAAA
SerialNo
U3G0664866872521539520503518505504505504505505505505
U509U6*lU536
50bA SOAS2
73a73
17 *a173173a1525125125125125125125125125125125124954054955*751251210*
6G6
0S87i533 *c*2S***c0400404*8
U75GU754U755U708U700U27U28U20U30
9289
614 GLOSSARY OF DYE NAMES
Name
Metachrome Brown BLMetachrome Brown BRLMetachrome Olive BMetachrome Olive Bi own GMetachrome Orange RMetachrome Orange 3 RMetachrome Red GMetachrome Violet BMetachrome Violet 2 RMetachrome Yellow RA.Metannne BrownMetanil YellowMetanil Yellow (V M )Metanil Yellow BrominatedMetanil Red 3 BMeta-Nitramline OrangeMeta-phenylene Blue B 2 BMeta-phenylene Blue RMethyl Alkah BlueMethyl Alkali Blue PureMethyl BlueMethyl BlueMethyl Blue MBSMethyl Blue for silkMethyl EosmeMethyl Gallus BlueMethyl GreenMethyl Indone BMethyl Lyons BlueMethyl OrangeMethyl Silk Blue (new)Methyl Soluble Blue 3 SMethyl VioletMethyl Violet BMethyl Violet BBMethyl Violet 3 BMethyl Violet 4 BMethyl Violet 5 BMethyl Violet 5 BMethyl Violet 6 BMethyl Violet 6 BMethyl Violet 7 BMethyl Violet base 7 BMethyl Violet B BBMMethyl Violet 3 BHNMethyl Violet BIA 2 BIAMethyl Violet 2 BP 3 BIA,
5 BIAMethyl Violet 2 BN 6 BNMethyl Violet 4 BOOATNMethyl Violet DBMethyl Violet IB IBAMethyl Violet N, NY 147Methyl Violet R 3 RMethyl Violet 5 RMethyl Violet 5 RAMethyl Violet RIAMethyl Violet 5 ROMethyl Violet 129Methyl Violet baseMethyl Violet base BBMethyl Violet base 74418Methylene BlueMethylene Blue AN, BBMethylene Blue BMethylene Blue 2 BMetb> lene Blue BAMethylene Blue BEXMethylene Blue 2 BDMethylene Blue BGMeth> lene Blue BGMothylene Blue BGNMethj lene Blue BX
Manu-fac-turer
AAAAAAAAAASVar\arPByMCCB etcItMA CGrEGrEMBGP etcCGtM etcGB etcVarVarVartMMtMBy, etctMBMBy tMBKMtMtMtMtMGrEtMByBM.tMVartMtMBKBKHVarBVarVartMBABtMBA
SerialNo
U31U32A25A20
58U33U34U35LHGA27
U710134134135
A27440
691G905355355375385375375S8
TJ63251912753713S537
U1G0515515515515515517515517515517517515515515515515515515515515515515515515515515515515515659663659659659659659659059059G59
Name
Methylene Blue DMethylene Blue DBBM,
DDBMMethylene Blue FKIIMethylene Blue GMethylene Blue HGGMethylene Blue LMethylene Blue MDMethylene Blue MDXMeth> lene Blue MEDZMethylene Blue MNXMethj lene Blue 3 RMethylene Blue &Methylene Blue VNMethylene Blue 1574GMethylene Blue 52067Methylene Gray ND 0Methylene GreenMetlii lene Green B BXMethj lene Green BXMethylene Green GMethylene Green N, 0Methylene Green PMethyJene Green 1 WMethylene Green 247Methylene Heliotrope 0Methylene SZOMethylene VioletMethylene Violet BMethylene Violet BNMethylene Violet 2 RMethylene Violet 3 RAMethylene Yellow IIMikado Brown 2 B MMikado Golden Yellow 6 G
SGMikado Orange (V M )Mikado Orange 4 RCMikado Orange 4 ROMikado YellowMilling BlueMilling Blue BCMilling Blue GRMilling Blue 2 RMilling Blue 5 RMilling Brown GMilling Brown BWMilling Green DB DSMilling OrangeMilling Orange GMilling Orange GMilling Orange JNMilling Orange ROMilling Orange 88Milling RedMilling Red GMilling Red 4 BAMilling Red 6 BAMilling Red GAMilling Red RMilling Scarlet B GMilling Scarlet BSMilling Scarlet 4 RMilling Yellow (V M)Milling Yellow 3 GMilling Yellow GAMilling Yellow 3 GOMilling Yellow H HG.H3GMimosaMimosa C R Z 2Mineral BlueModern Azurme DHModern Blue
Manu-fac-turer
I
MKIBKBBMBMCRBPtMMIs. SBKSMG IGKMDHVarDHMHKMLLL etcAA,LKKAMALLAWWDAWDLWDACAAAWDMCICoMCAACVMGGcDHDH
SerialNo
659
659659659659659659659059603059659603659659G816606606606606606606006606876596S06&06S0080680618111011111110
693693
U 37A436U38
U521503523b250TJ39
A27525058
250U40293493U41U42298400b484400
A378U43U44177177c198198
XJ291640629
GLOSSARY OF DYE NAMES
Name
Modern CyanmoModern VioletModern Violet NMonochrome Black FMonochrome Black Blue GMonochrome Blue 5 RMonochrome Brown BXMonochrome Brown GMonochrome Brown VMordant Blue 13707Mordant Yellow GD, GS, RMordant Yellow GTSMordant Yellow OMordant Yellow 3 RMuscarmeNako Blue Black BNako Black DBB ONako Brown B DR, 3 GANako Brown 3 GN P, RHNako Gray B 6 BNako Yellow 0NankinNaphthalene \cid Black 4 BNaphthalene Black DNaphthalene Black 12 BNaphthalene Blue BNaphthalene Blue DLNaphthalene GreenNaphthalene Green VNaphthamme Black RENaphthamine Blue (V M )Naphthamme Blue 2 B 3 BNaphthamine Bnlhant Blue
GNaphthamineBnlli mtBlue3Naphthamme BiovsnNaphthamine Brown 4 GNaphthamine Deep Black
HWNaphthamino Direct Black
(V M)Naphthamine Direct Blue
BXRNaphthamine Direct Blue
ERNaphthamine Direct Blue
2 R 3 RNaphthamino Ducct Blue
3G92Naphthamine Direct Green
AGNaphthamine Fast Black
(V M)Naphthamine Fast Black
KSNaphthamino Fast Bor-
deaux BGNaphthamme Fast Scailet
(V M)Naphthamine Green (VM)Naphthamine Orange (V M )Naphthamine Red 3605 HNaphthamine ScarletNaphthamine Violet BENaphthamine Violet RNaphthamine Yellow (V M )Naphthamine Yellow R, XNaphthazine BluoNaphthazine Navy Blue 15GNaphthazurme B BANaphthazunne 3703Naphthochrome Violet RNapathof orm Black 3930
Manu-fac-turer
DHDHDHByBygyBy¥BBMBDIIMMMMMMtMByHIIMMMM IKKKKKKIv
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SerialNo
G276*5621
t m oU250U251U2521125 5U254A703
17748
1775b
05 r>023 x92 5a92 5a02 U92 5a02 5a(>06g2«5S
U75S217
A157
511r)043 3533833b
370a570a477a477
335a
45b
A 599
A399
A 599
A 509
A100
U5b2
U3b3
KKKis.KKKKKWDWDGrEKIK
U5G4A401A402
UiG552(5327b
9a9a
GO 2(>02a5853b 5
U078U3G6
Name
N iphthogene Blue BNaphthogone Blue 2 RNaphthogene Blue 4 RNaphthogene Blue 6 RNaphthogenc Indigo Blue RNaphthogenc Pure Blue 4 BNaphthol Black (V M )Naphthol Black (V M )Naphthol Black ANaphthol Black BN iphthol Black 2 BNaphthol Black 3 BNaphthol Black 0 BNaphthol Black BRN iphthol Black CR, MB, N,
I RNaphthol Black greenishNaphthol BlueNaphthol Blue 2 RNaphthol Blue Black (V M )Naphthol Blue Black MN iphtlu 1 Blue Black 0 B1ST iphthol Daik Green GNaphthol GicenNaphthol Green BNaphthol Or ingeNaphthol PinkNaphthol Red (V JM )Naph th ) lRedGRNaphthol Red SNaphthol YellowNaphthol Y( How SNaphthol Yellow SLNaphthol Yellow SLC SLZNaphthylununo Black DNaphthylaimncBlackCV M )Naphthylaimne Black 4 AN,
4 BNaphthylamine Black 10 BNaphthylamino Black 4 BlvNaphthy'amino Red 5 BMNaphthylan me Black B 2 NNaphthylamino Black 0 BNNaphtha laimnc Black BOONaphthylamino Black 4 BXNaphthylanune. Black CSR
GSBNaphthylamino Black FNaphthylan inc Black NANaphlhylatnmeBlackNbBNNaphthylamino Black SXNaphthylamine Blac k2002,
200 JNaphthyl innno Bluo BlackNaphthylamino Blue 2 BNaphthylamino Bluo 3 BNaphthyl imino BrownNaphthyJanuno Grcon TNaphthyhuninebkvB] t DDNaphtliylanune YellowNaphthyl Blue Black NlNaphthylono VioletNavy BluoNavy Blue DNavy B l u e F .Navy Blue GR, 5 RNavy Bluo 17184..Navy Bluo SMNavy Bluo TNootolyl Black BNeotolyl Black BBNootolyl Black 4 BNeotolyl Black TL
Manu-fac-
turer
AAAAAACIvIvCByCVC KtM
KKCtMVarBvBlvCtMB y , CVai
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VarB ByMC , KC.Iv
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KCKK15BvNFKCCCI bAWCVKPAWMMMM
616 GLOSSARY OF DYE NAMES
Name
ISeotorjl Black VLNeptune Blue B .Neptune Blue BG, BGN,KeptuneBlueBR BTE RNeptune Blue BXXNeptune Brown RXIseptune GreenIs eptune Green SAX SiiL.
SG\Iserazme (V M)Nerol Bfterol2 BNerol BLNerol 2 BLNerol \LNeutral BlueJSeutral Blue RNeutral Blue 3 RNeutral GrayNeutral Gray GNeutral RedNeutral \ioletNeutral \ lolet O _Isew \cid Chrome Black RNew Chrome Black PKNew Blue B G2s ew Blue RNew Blue RR RGNew Claret BNew Claret PNew Claret RNew CoccineISew Direct Blue SNew Ethjl Blue BSNew Ethyl Blue RSNew Fast Blue F HNew Fast Blue R RSNew Fast GrayIsew Fast Green 2 BNew Fast Pink F"New Fast Straw YellowNew Fuchsme ONew Fuchbine SNew Magenta 0New Magenta 0New Meth\ lene Blue (V M )New Meth} lene Blue FNew Methjlene Blue GGNew Methjlene Blue NN\New NigrosmeNew Patent Blue BNew Patent Blue GANew Phosphine GNew Pobchromine FBNew Toluylene Brown 00ISew Toluylene Brown ONew Toluylene Brown Ri\ew Victoria Black BNew Victonal Blue BNew Yellow for CottonNiagara Black Blue RNiagara Blue B 2BNiagara Blue 4 BNiagara Blue 6 BNiagara Blue BRNiagara Blue GW,HW RWNiagara Blue RNiagara Fast Red FDNiagara Violet 2 BNiagara \iolet 3 RNicholson Blue 4 BNight Blue
Manu-fac-turer
MBBBBBBBCAAAAACAWMACCMAWCVC etcVarBBBBAL.MMByIByIBiAWMGrEGrEMCByCB\WBjByCGGrEGrEGrEByByWDSchSchSchSchSchSchSchSchSchSchPB,I S
SerialNo
U454545543545ao45
U161503503
U293A32A33A34A35A36676676
U455221241670669
U456A607
275a650649649A83A8oA86169
U36SU457U4oS
6o26o2a681497652
A608513513513512663663651663700563545b75
616A465A464A466
262558304441337426424386336326343326327536o60
Name
Night Green ANigrammeNigrophorNigrosmeNigiosmeNigrosme (V M)Nigrosme (V M )Nigrosme spirit solubleNigrosme water solubleNigrosines from aniline (m-
dulmes)Nigrosines from nitrobenzo]Nile Blue A B, RNile Blue 2 Bm Nitraniline OrangeNitro Azomine Green FNitrophenmeNTitrosamme Pink BXFNitroso Blue MRNitrosamme RedNyan2a Black BOil Black (V M )Oil Black (V M )Oil Black 6 BOil Black 6 GOil Black HGOil BHck 11410 39694Oil BlueOil Blue Black 114Oil Brown BGOil Color BrownOil Color CanaryOil Color \ ellowOil OrangeOil Orange (V M )Oil Orange AROil Orange LGOil Orange ROil Orange 3 ROil Orange 2311Oil Red (V M)Oil Red BOil Red GOil Red 7327Oil YellowOil \ ellow (V M)Oil bellow AOil \ ellow GOil \ ellow ROil Yellow 2338Oil \ ellow 2G25Oil \ ellow 26S1Oil Yellow 7869Old GoldOleate Green OOmega Chrome Cyanme ROmega Chrome Red BOmega Chrome Black PVOpal BlueOpaline Blue ROrange 4LOrange DOrange GOrange GOrange 2 GOrange GCOrange GDOrange GRXOrange GSOrange GTOrange NOrange NAOrange PC
Manu-fac-turer
tMCGBVarVarVarVar\arVarSchSchBBMCVCICoBMBACJIvBBBHB&KHHHVarKKIBBSchBBCJVarSchBBSchSchSchQQSssMISchBVarKHKLBHByIGrEDH
SerialNo
50368221869870069870069S70069970005365446
A730519S
64756
245U495U369U163U164U165U759U166U370U371U760U761U762
36U372U372
36aU167U168
36U373U169U170U496
32U374
31U171U172
36a326832a
US04U805U711U712
85521
U679Ho37a38
139a38
139a144a37
13970
13979a
145a
GLOSSARY OF DYE NAMES
Name
Orange ROrange 2 ROrange ROOrange ROOrange SOrange TOrange TAOrange XOrange IOrange IIOrange IIIOrange IVOiange 13Orange 14Orange 67 (V M )Orange 227Orange 23981Orange Cryst ilsOrange Ciystals 2 GOrange Red pureOrchil RCEPOrchil OPAGOrchil RPIIOnol YellowOnol Yellow ECOraeilhne BVOrtho Black 3 BOrtho Cyanme BOrtho Cyanine 6 GOxamme Acid Brown GOxamme Black AOxamme Black BBOxamme Black BHN BHXOxamme Black BBNXOxamme BHek BR1XOxamme Black RNOxamme BlueOxamme Blue A AXOxamme Blue BOxamine Bluo 3 B, BG
GNX, 3 11Oxamine Blue 4 IIOxamine Bnllunt Rod BXOxamine Brilliant Violet RXOxcimme Brown AOxamine Brown GOxanimo Brown 3 GOxamine Brown GROxamine Brown GXOxaramc Brown 3 GXOxamine Brown R, RGOxamine Claret BOxamine Copper Blue RROxamme Copper Blue RRXOxamme Dark Blue BGXOxamine Dark Blue BGEOxamine Dark Blue BRRXOxamme Dark Blue ROxamine Dark Brov n GOxamine Dark Brown ROxamine I aat Blur 0 VXOxamine Fast Blue RROxamme Fast Pmk BXOxamine Fast Red FOxamine Green COxamine Green B, BXOxamine Green G, GXOxamine Light Blue BOxamine Light Blue GXOxamine I lght Brown GOxamine Light Brown ROxamine I lght Green BOxamine Light Greea G
Manu-fac-turer
VarKBByBK tMA etcHVarVarPVarSSc
AWWDAAAAGGByAAABBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBB
SerialNo
151139a151a
A277144151311S7J,141:11547
1305be5Sc3b3(>b58c3Sss
174UlbU47U*9ion1992>5A37A3bA39AS7ASSASJ*3 5
A00A)lA0242141042142113S5A03A04A05A90A07A08A<)9
A100344
A10]A102A103A105A101A107A10(>AlOfeA109A110A1UA112
US475474475
All iAmA115AllbA117A11S
Name
O\amine Light Green 3 GOxamine MaroonOxaminc Pure Blue 6 B,
G BO 6 BXXOxaminc RedO\ unine Red J B BNXOxumine VioletOvimme Yellow AO\ inane \ ellow 3 GOxy At id Red b BOOvy Chlor uol Blue BOxy Diammc Bl ick (V M )Oxy Diaimne Blue (V M )Oxy Dicumne Brown (V M )Oxy Diamme Caibon (VM)Oxy Diaminc Orange (V M )Oxy Diamme Red fc>Oxy Diamme Violet (V M )Ovy Diaminc YellowOxy Diuninopen (V M )Oxyehrome Blick IOxv chrome Blue Bl ick BGOOxycluotne Brown VOxichrome Biown VAOx chio nc Brown VNOxyehrome \cllow D(Jxychiomc Yellow DGOx\chiome \cllow 2 GlOxyphemnc A C, GG, RPicihc BluePalitinc IJUck A 4 BP ilatine BUck 3 GX MZ
sr brMP ilatine Chrome Bl ickP iHtine Chrome Black 0 B
6BXPalatine Chrome BHck VPalatine Chiomo Black SPalatine Chrome Blue l BP il \line Chrome Bluo W 2 BPalatine Chrome Brown "5 GPalatine Chiomo Blown
GGTXP ildtmc Chromo Brown
GGX, RP il itme Chromo Brown WP ilatine Chromo Bi own WNPalatine Chiomo Biowu
WNRPalatine Chromo Brown
WNR1XPalaiiuo CJiromo Green GPalatine Chtomc C»iccn GXPalatine Chronic Re I BPalatine Chromo Red RPal ihnt, Chronic \iolctPilitmo I lght Yellow RPalatine Orange RPalai me Red APalatine Scat let APalatine Scar lot G i 1U HPalalimtoPanama Black 3 G, RPaper Blue 0 GPapor Blue MDPaper Blue ClUiPaper Bluo 33598P iper Blues green HIHKICSPnpci Blues ted shadesPipci Biown BBPnp<r Biown BTPaper Hi own 111Paper 1 uut Boide mx B
Manu-fac-turer
BBBBBBBBGrEHCCCCCccccGrLGrEGrEGrEGrEGtEGrEGrECICoHBBBBBBBBB
BBBBBBBBBBBBBBBBbehSchMBSbchSchBBBBy
618 GLOSSARY OF DYE NAMES
NameManu-fac-turer
SerialNo. Name
Manu-fac-turer
Paper Green DPaper Orange CRPaper Orange residue. ...Paper Red OPaper Scarlet (V.M.)Paper YellowPaper YellowPaper Yellow G, GGX?RRXPaper Yellow 3 GXPaper Yellow 3 RXXPara Black BPara BluePara Brilliant Orange GPara Brown GKPara Brown RKPara Brown SCPara Diamine Black (V.M.)Para Green 2 BLPara-FuchsinePara MagentaPara Orange GPara YellowParamineParanitraniline RedParaphenylene Blue RParaphenylene VioletParaphosphine (V. M.)Para RedParatol Chrome Yellow L. .Paratol Fast Yellow GParatol Lake Red KPParatol Lake Red LCParatol Lake Red LPParatol Scarlet 3 B, 3 BX..Parazole Brown RK.Paris VioletParis Violet 3 B, 6 B, 3 BA.Paris Violet 4 BA, 4 R, 90..Patent Alizarin Black DEB,
DFF, DFFAPatent Black (V. M.)Patent BluePatent Blue APatent Blue AEPatent Blue BPatent Blue L, LE, NOPatent Blue VPatent Blue V newPatent Blue J 3, JI, WE. ..Patent Marine BluePatent Marine Blue LER...Patent Phosphine G, GG,
M, RPatent Phosphine 19332Pegu Brown GPeii Wool Blue BPermanent Blue GRPermanent Orange RPermanent RedPermanent Red B, 2 B, R,
4RPermanent Red 4 BPersian Red RDPhenamine Blue GPhenanthrene Chrome BluePhenochrome YellowPhenocyanine TC, R, VS...Phenocyanine TVPhenylamine Black 4 B....Phenyl Crimson SPhenylene BlackPhenylene BluePhiladelphia Yellow 2 G.. .
KKKWDKVarWDBBBByCGBy§ByVarHByAWBVarWDWDCVarMMMMMMKPPPMCVarMA, MMVarMMMMIILCCGAAAABBKDHDHByCVPBKA
U375U37GU377307U37S303303a303a303303aA278702A2S2A279A280A2S1A3SSA2S3511"511A2»4U5S8U17856701695U29450U400U461U4152U4G3U404U405TJ379515515515S07aU295543545545543543543543543a543543bGOG60 GoA51187U493131152152a152U179A129U680U380642643A2S5A731267649606
PhloxinePhloxineB, GA, HMPhloxine PPhoenix Brown DPhosphine (V. M.)Phosphine APhosphine AR, GGPhosphine GPhosphine GOPhosphine LM, OPhosphine LB, PHLBPhosphine 3 RPhosphine RSPhosphine 12901Picric AcidPigment BlackPigment Black BPPigment ChlorinePigment Chrome Yellow L.Pigment Fast Red HLPigment Fast Yellow G ....Pigment Fast Yellow RPigment Orange RPigment Purple APigment Scarlet GPigment Scarlet 3 BPinachrornePinacyanolPinkPinkBPink MPink ColorPluto Black APluto Black BSPluto Black CFPluto Black FPluto Black GPluto Black SSPluto Brown GGPluto Brown NBPluto Brown RPluto Milling Black BPluto Orange GPlutoform Black 3 GLPolar Orange GSPolar Red 3 BPolar Red GPolar Red RPolar Red RSPolar Yellow GPolar Yellow 2 GPolar Yellow RPolar Orange RCPolychromine ACPolychromine BPolyphenyl Black B VCPolyphenyl Black GNCPolyphenyl Blue GCPolyphenyl Blue GFPolyphenyl Brilliant Blue3 GPolyphenyl Fast Red BC...Polyphcnyl Orange RC....Polyphenyl Yellow 3 GC...Ponceau (V. M.)Ponceau BOPonceau GPonceau 4 GBPonceau KPonceau Xt, 2RPonceau 3 RPonceau 4 RPonceau 4 RPonceau 5 R. r
DH,MMBAVarGrEtMSKMGrEAIIPBBMMMMMMMMMMMKIH
%ByByByByByBy
GGGGGGGGGGGGGGGGGGKAMA, etc.IVarVarP
GLOSSARY OF DYE NAMES 619
Name
Ponceau 6 RPonceau 3 RBPonceau 4 RBPonceau 6 RBPonceau 10 RBPonceau RL, 2 RL, 3 RL,
2RLHPonceau 2 RLPonceau SPonceau SPJPonceau S 2 RPonceau W 3 ItPonceau XPonceau 12402Ponceau for SilkPonceau (free from arsenic)Potting Black BPrague Alizarin Yellow GPnmal BlackPrimazme Yellow GPnmulmePrimulme APnmulme (V M )Pnmulme YellowPrinting Black for WoolPrinting Blue for WoolPunting Yellow (greenish)Prune 516Prune purePure Blue AIPure Blue DS DSGPure Blue RTPuie Soluble BluePure Yellow DGPurpunn (synthetic)Pyrarmdol Brou n BGPyramidol Brown TPyramine Orange 2GXPyramine Orange 3 GPyramme Orange RPyramine Oiinge RRPyramine Orange RlPyramine Yellow GXS,
GXSCPyramme Yellow GXSPPyramme Yellow R, RXPyrarolc Orange GPyi azoic Oras p,e RPyi o allol-cy anme aulphon-
IC acidsPyrogenc Black GPyrogono BluePyrogene Blue RR, 2 RNPyrogenc Blue Green BPyrogenc Brown DPyrogenc Brown GPyrogeno Brown GXPyrogeno Brown ORPyrogene Brown ORRPyrogeno Brown 4 RPyrogono Cutch DRPyrogeno Cutch 2 GOPyrogene Cutch 2 RPyrogeno Dark Green BPyrogeno Deep Black C, D GPyrogene Direct BluePyrogene Direct Blue green
shadePyrogeno Direct Blue, red
shadePyrogene Direct Blue RLPyrogone Green GPyrogene Green 2 G
Manu-fac-turer
B, MAAAAAByAPBPBKIP.KWDIKiABVarB, MVarAW.ByBBKLevSIHBKCKBFAFABBBBBBBBSsDIIII CIIIIIIIIIIIIIIIIIII
SerialNo
17024724925525982a82
247albOb82
It ObS2b
17 117582c18449
U50AHO
(>10bib016010a770742
U3S26*60*6539"H9r>395 30
U S37S*m370302a*00toO3143G2304iOt101402
A7220237*0720720740
Slr)r>Sl%SI 57Slri88159SlbOfelOlbl62SI 0374072072072072072074b709
Name
Pyrogene Green 3 GPyrogenc IndigoPyrogenc Indigo CL 5 G GLPyroxene Indigo R RRPyio enc Olive 3 GPyrogene Oiantoe RPyrogene Yellow M O 3 RPyiol Brown GPyrol Brown 00181Pyrol Brown (yellowish)Pyronme GPyiophosphine CQueuilton Substitute VQueicitton Substitute WBLQuinolmc BluoQuinohne RedQuinolmc 'i ellowQumolmc YellowQuinohne YellowQuinohne YellowQumohnc YellowQuinohne YellowQuinohne YellowQuinohno YellowQuinohne Yellow KT NQuinohne Yellow OQumolme Yellow PQuinolmc Yellow 0272Qumohne Yellow, spirit eol-
ubloQumohne Yellow watei sol-
ubleRadial Yellow GRapid Filler Gio( n IlUpidFiltei Rod IRaven Black HSSSRed (V M)Red PCRed PCRed 2 SRed Blue BSRRed BrownRed CorallineR,cd for Leather ORed for I either RRod T ike RLRid Take RMTR( d VioletRed Violit 5RRed Violc t 5 RSReddish BrownRenol Black BUNK(nol Black Sr STR< nol Blue BRonol BordeauxRonol Bulhant YellowRenol Brown MB, RARenol Dark Grcon NOONGRenol Fast Red 4 BRenol Green BRenol Light Blue ARenol Light Blue GRonol Light Blue GR( nol Orange 3 APRenol RedRenol Yellow 3 RRenola-mme Black BHNRoHofJnvin Wltosomn BlueHcsoroin BrownResoTCin Brown GResorcin Brown QVResorcm Dark Brown
Manu-fac-turer
IIIIIIILLLI, ByWDBBGAAAWBByCIMSByMBIVarVarBMMIICJDHGPGiEbMAByBytMBBKtMtMtMtMtMtMtMtMtMtMGtMG tMtMtMG tMBMVarGGBK
SerialNo
740735735735740
S1017*1
S135S130S135508
U547U184U183
011blO012013G1261}01}013013bl2(>H01B012012C1201330
U167U108U704U497UbOOU042
483aU513
lOOo55b
U469UbO
U250U257
514514525
XJ384402b4(>2b410
A517ao*344
Ar)18A519
475A 520A 058A521
302aA522
0333771047211211211213
620 GLOSSARY OF DYE NAMES
Name
Resorcin YellowRheonineRheonine AL, GDRhine BlueRhodamine ALRhodamine BRhodamine SBRhodamine BNRhodamine BSPRhodamine GRhodamine 3 GRhodamine 5 GRhodamine 5 GRhodamine 6 GRhodamine 12 GFRhodamine 6 GNRhodamine SRhodamine SRhodamine SPRhodamine RRhodamine 6302Rhodamine Scarlet GRhodine 2 GRhodine 12 GMRhoduline Blue 6 G .•••••Rhoduline Heliotrope 3 B.Rhoduline Orange N, NO.Rhoduline Red B, GRhoduline VioletRhoduline Yellow 6 GRoccellineRoccelline FSRoccelline MBRoccelline SRosanthrene AWLRosanthrene BRosantbrene CBRosanthrene RRosanthrene Bordeaux B..Rosanthrene Orange 16754Rosanthrene Violet SR....Rosazeine BRosazeine B 5Rosazeine 6 GRosazurine BRosazurine GRose(V.M.)Rose BengalRose BengalRose Bengal BRose Bengal BRose Bengal NRose Bengal NTORose MagdalaRoseine BRosindulineRosinduline 2 BRosinduline GRosinduline 2 GRosolaneRosolane B, ORosolane O, T, RRosophenine 4 BRosophenine 10 BRosophenine SGRubineRubine NRubine NRubramineRussian Leather Red R...Russian RedSaba Phosphine G, GGSafranine
Manu-fac-turer
SchBBQBVar
B
VarB
VarBB.ByIBQ
TkByUByC,FAHtMG,tMIIIIIMMMA, ByA, ByCJVarG,MB,LK,MCBDHSKKKKPMMCICoCICoCICoAABCGACsVar
SerialNo.
143607607631572a573574573573572576576a572a571578571570570570572a572a57Gb577575
TJ25SU259603a6S40S4618a161161161161
A704A705A706A7O7A70SA709A710
573IT471U472
372371
U498595597597597595595694512674673675674688687687483194195512512
U189703512512606679
Name
Safranine (V. M.)Safranine BSafranine 6 BSafranine F FSafranine FSafranine FBSafranine 3VINSafranine OSafranine T, TKSafranine YSafranine Ziafranine 1081
Safranine bluish .Safranine (blue shade)St. Denis Black BSt. Denis RedSalicine Black (V. M.) . .Salicine Black K, LR, SSalicine Black U , U L . . .Salicine Blue BSalicine Bordeaux R. . . .Salicine Brown (V. M.)Salicine Dark Green CSSalicine Green CPSalicine Orange 2 RSalieine Orange 2541, 2542..Salieine Red BSalicine Red GSalicine Violet RSalicine Yellow (V. M.) . . . .Salmon RedScarlet
carlet (V. M.)Scarlet ABScarlet 6 BScarlet BNScarlet CScarlet ECScarlet GAScarlet GRCL, MScarlet GXScarlet 15 NScarlet PScarlet PO, 2 PRScarlet R, 2 RScarlet R, 2 RIcarlet 2 R
Scarlet 2 RScarlet 3 R, 6 Rr 2 RCL,
3 RCLScarlet 3 RScarlet 4 RScarlet 4 RScarlet 6 R crystalsScarlet RDScarlet 4 RI, 2 RIIScarlet 4 RZScarlet S 2 RScarlet S 3 RScarlet 2 SRMScarlet X, X XScarlet 50Scarlet 231, 243Scarlet 1610Scarlet 7214Scarlet 53446Scarlet (yellow shade) 17413Scarlet (yellow shade) 24211Scarlet for silk SScarlet residueSeal Brown WSella Brilliant Yellow PSella Flavine G
Manu-fac-turer
VarVarSch
l y
BBMBSchKKhPPKKKKKKKKKKKKKKACDCoCGrEGrEBBMKBKKMVarKtMMBP,tMBKHAWMBBBKHCJKBABBPKPGG
SerialNo.679679680679679679683679679679679679680679718483181b181b181A403A404A405276A407A408A409A410A411A412177b120174247A475A476A131196a247A132174aU385A133U3S5U385174a82U385176174a8383176a223bS2d106b174aA134A135A136TJ38516976aU385A137U61A138A139247cXJ385•U594U643TJ644
GLOSSARY OF DYE NAMES
Name Manu-fac-turer
IAGGGtMBBKQGrEGrEGrEQByBKKMBKQCABtMtMSAAIIIIIIICsQGrEGrEGrEQQMCQMQQByCoVarH&MVarGrECGPGrEKGrEBtMMGrEtMtMGBBBSG
SerialNo.
U(5S253950049 G500539a537559539539a539a539a539537550
U38GU473
G13US11
7007007585G
A523424A44A44a
UG84UG83UG85UG8GUG88UG87UG89U29GG99G99099099G99
US12U813U474
495499
1U814
137537539537539539539539539539539539539539539539539539 c6464U190
006U645
NameManu-fac-turer
Sepia Black FW, 1499SSerge BlueSetooyanine OSetoglaucine OSctopalineSilk BlueSilk Blue BSilk Blue BSilk Blue BSilk Blue BJBNOOSilk Blue BS3BB, BT5BOO
BTRSilk Blue BTB, BTllSilk Blue 4 RSilk Blue 4Silk Blue 5770Silk Gray CB, 281Silk Wool Black 3 BSilk Yellow NSilk Yellow NSilvor Gray N. . . .•Silver Gray PSinus Yellow GSitara Fast Red RLSitara Orange XSky Blue FFOSolaminc Blue BSolamino Roil.SolliKenc Blue Green BSoliigene Blue Green 1G444.Solligene CutchSolligene CyanineSolfigono Deep Black (V.M.)Solfigene Deep Black 14717.Solfigene Gieen GGSolid Blue (V. M.)Solid Blue 3 RSolid Blue RXSolid Blue SBAOOOOSolid Blue SBSOOOSolid Blue Base SBXBX. ..Solid BrownSolid Brown KFSolid Brown OSolid Green (V. M.)Solid Green 3 GSolid Green OSolid Red BSolid Yellow GSoluble BlueSoluble BlueSoluble BlueSoluble Blue (V. M.)Soluble Blue AOOOOSoluble Blue B, BCBIISoluble Blue BLSE, 3 BS...Soluble Blue BS 3B B, BSJ.Soluble Blue C 2, C 3, C 5,
CXSoluble BIUO'ELOOO '.!'."!Soluble Blue HA, IN, 4 R,
TB, TLSoluble Blue 5 RSoluble Blue RMSoluble Blue base SBXR. . .Soluble Blue crystalsSoluble Blue (greenest shade)Soluble Navy BlueSorbin RedSorbin Red XSpecial Blue GSpecial Phosphine GSpirit Black
Spirit Black (V.M.)Spirit BlueSpirit Blue BVESpirit Blue RSpirit Blue, green shades. ..Spirit Blue, red shadesSpirit NigrosineSpirit Nigrosine LM, VSpirit YellowSpirit Yellow RStanley RedSteam Green GStilbene YellowStilbcnc Yellow 3 GStilbene Yellow 3 GStilbono Yellow 2 GP,
3 GPX, GXStilbene Yellow RXStilbene Yellow 5912Straw Blue GSudan G, 2 G!Sudan RSudan ISudan IISudan IIISudan IVSudan BrownSudan Brown SSulfamine Brown ASulfamine Brown BSulfaniline Brown O, R. . ..Sulfine Blue BSulfine Blue RRSulfine BrownSulfine BrownSulfine Brown B, GSulfo Blacks B, 2 BSulfo Green B, CSulfo Rhodamine BSulfo Rosazeine BSulfo Rosazcinc GSulfogenc Brown G, DSulfolino GSulfolino GSulfoline RSulfon Acid Black N 2 B. ..ISulfon Acid Blue BISulfon Acid Blue RSulfon Add Green BSulfon Black 3 BSulfon Black GSulfon Blue RSulfon Orange G,5GSulfon Violet RSulfon Yellow 5 G, RSulfonazurineSulfoncyanineSulfoncyanine BB, GR,, 5 R,
SRSulfoncyanino G, GR, 5 E,
5 RTSulfoncyanine Black B, 2 BSulfoncyanino Black BB,
GR.Sulfur BlackSulfur BlackSulfur BlackSulfur Black A, AW, AWL.Sulfur Black B, 2 B, 4B. . .Sulfur Black 2 B, BR, BRH,
GFSulfur Black FAG, FTSulfur Black H, JBL
CJVarPMSchSchWDHL,tMCICoBVarCICoCllBBBByAAAAA, etc.A, etc.ASchWDWDKCGCGCGCGIINFMMMAWKAWByByByByByByByByByByByVarBByByBVarWDAAAKAA
622 GLOSSARY OF DYE NAMES
NameManu-fac-turer
KALevKKAAAABKKAKAAAAABKKALevLevAAAAIAALevLevKKAAAAAAAALevLevAAAKKSAAAAAKSAKAAAIHHHHVarSGByByA
SerialNo.
720720720720720720SIS2S3
S123S83S4S83S6S7S8S9S10
S124S83Sll
S168S1C9S12S13S14S15
S165S16S17
S170S171S84S84SISS19S20S21S22S23S24S25S172S173S26S28S29S85SS5S167S3OS31S32S33S34
U388712S35
U388S36S37S38S166363405304d304999
U263U264A45
NameManu-
fac-turer
Sulfur Black KCB, MASulfur Black T, TFA, T G . .Sulfur Black TRSulfur Black TS, 5274, 5276Sulfur Black 5285, 52S9Sulfur Black 108583Sulfur Black Brown NSulfur Black Brown NRSulfur Blue BSulfur Blue BESulfur Blue BG, CHLSulfur Blue DSulfur BlueGSulfur Blue LSulfur Blue PRSulfur Blue RSulfur Blue 2 RSulfur Blue 4 RSulfur Blue RRSulfur Blue USulfur Brilliant Green GIC..Sulfur Bronze 136Sulfur Bronze 158Sulfur Brown CL 4 RSulfur Brown GSulfur Brown 2 GSulfur Brown 6 GSulfur Brown MSulfur Brown OSulfur Brown OBSulfur Brown 527Sulfur Brown 731Sulfur Brown (bluish)Sulfur Brown (reddish)Sulfur Catechu GSulfur Catechu RSulfur Corinth BSulfur Corinth CLBSulfur Green 2 BKSulfur Green 4 BKSulfur Green GSulfur Green 4 GKSulfur Green 309Sulfur Green 330Sulfur Indigo BASulfur Indigo CLSulfur Indigo CLGGSulfur Indigo Blue RCLSulfur Indigo Blue 827Sulfur OliveSulfur Olive BSulfur Red Brown 2 R K . . .Sulfur Red Brown 6 R K . . .Sulfur Violet RSulfur Violet YSulfur Yellow ESSulfur Yellow GSulfur Yellow GSulfur Yellow GSulfur Yellow 4 GSulfur Yellow ISulfur Yellow RSulfur Yellow RSultan 5 BSultan 10 BSultan Orange DSSultan Yellow HSun YellowSun Yellow G, GS, R RSun Yellow 3 GCSupramine Brown RSupramine Yellow RTabora Black X
Tannin HeliotropeTannin Orange RTannin Orange RTartrazineTartrazine G, X, X XTerra Cotta FCTerra Cotta 2 RN, R G N . . .Tetracyanol ATetracyanol SFVThiazine BlueThiazine Brown RThiazine Red GThiazine Red RThiazine Yellow G, 3 G, GLThiazol Yellow GThiazol Yellow GRThiazol Yellow R , R HThiocarbqne NNGThiocarmine RThio CatechineThio Cotton BlackThioflavine (V. M.)Thioflavine OIOThioflavine SThioflavine TThioflavine 654Thiogene Black BB, 5 B . . .Thiogene Black M, MA,
MMThiogene Black ML, M Z . . .Thiogene Blue RLThiogene Blue RThiogene Blue 2 RThiogene Cyanine BThiogene Cyanine GThiogene Dark Red GThiogene Deep Blue B R . . .Thiogene Deep BlueThiogene Green BLThiogene Green GThiogene Green GGThiogene Green GLThiogene Khaki NTMogene New Blue JLThiogene Olive Green GGNThiogene Orange RThiogene Violet VThiogene Yellow GGThiogene Yellow 5 GThiogene Brown GThiogene Brown GGThiogene Brown GCThiogene Brown GRThiogene Brown G 2 R . . . .Thiogene Brown RThiogene Brown SThio Indigo Brown GThio Indigo Brown 2 RThio Indigo Orange RThio Indigo Pink 247, 2475.Thio Indigo Pink Rose BW.Thio Indigo Red BThio Indigo Red 3 BThio Indigo Rose AN, BN. .Thio Indigo Scarlet GThio Indigo Scarlet RThio Indigo Scarlet S, 6086.Thio Indigo Violet 2 BThio Indigo Violet KThio Indigo Yellow 3 G N . .Thional Black GThional Brilliant Green 29..Thional Brown
CCsVarBGGCCGBBBffBDBBCPWDCKS,CCKM
MMMMMMMMMMMMMMMMMMMMMMMMMMMMKKKKKKKKKKKK
GLOSSARY OF DYE NAMES
NameManu-fac-turer
SerialNo. Name
Manu-fac-turer
Thional Brown GThional Dark Green GN..Thional GreenThional Green GGThional Red BrownThion Black (V. M.)ThionBlueBThion Brown (V. M.)Thion Dark Blue BOThion Direct BlueThionine Blue GOThionine Blue 00, 3 O....Thion Green 2 GThion Green 829Thion Navy Blue (V. M.) .Thionol BlackThionol Black S, XXThionol Yellow GRThion Orange (V. M.)Thion Purple 0Thion VioletThion Violet BlackThion Yellow (V. M.)Thion Yellow 2 GThion Yellow 5 GThiophenol Black TThiophor Black WLNThiophor Blue BThiophor Bronze 5 GThiophor Dark Brown B..Thiophor Deep Green CG.Thiophor Indigo CJThiophor KhakiThiophor Orange OThiophor Yellow RThiophor Yellow Bronze GThiophor Yellow OliveThio Vesuvine BBThioxine Black ABOOOO.Thioxine Black ABBOOOOThioxine Black 3 BOOO. .Thioxine Black GB, 1151,
3705Thioxine Brown 5 GThioxine Brown 2 GRTitan Como 2 BTitan Como RTitan Fast Black BTitan OrangeTitan RedTitan Scarlet YTitan Yellow G, YTolamine VioletTolaneRedB, GToluidine BlueToluylene Black GOOToluylene Brown GToluylene Brown RToluylene Fast Brown 2 RToluylene-Fast Brown 3 GToluylene Fast Orange GLToluylene OrangeToluylene Orange GToluylene Orange GOO...Toluylene Orange RToluylene Orange RR... .Toluylene Red 00, RT ...Toluylene YellowToluylene Yellow 00Tolyl Black B, BB,BG...,Tolyl Blue 5 RTolyl Blue SBTolyl Blue SR
SSsssKKKKKA, MAKKKLevLevLevKKKKKKKICJCJCJCJCJCJCJCJCJCJCJGrEGrEGrEGrEGrEGrEHHHHHHH,BDKB,MGrEGrEGrE
VarGrE,SMGrEGrEGrEGrEMMMM
74774674674674772073(5S86S87736a601661SS8S89S90719720198S91S92S93720S96S94S95720720
S127713
S128S129731
S130S131S132714
Sl32aU815
720720720720
S133S134:A761A7G2A763A764
190196198
U69043
659 aA477
285488
XJ260U265
392d392392392287287358286286265257189188
Tolyl Blue ST, 7656Tonka Brown GSTriazol Blue B ,Triazol Blue BOOTriazol Blue BBOO ,Triazol Blue 4 BOOTriazol Blue R ,Triazol Blue 3242 ,Triazol Bordeaux BTriazol Brown GOOA....Triazol Brown GOOOTriazol Brown HROTriazol Brown SOOO.Triazol Dark Blue BHOOOTriazol Dark Blue
BHPOOOOTriazol Dark Blue BHTOOOTriazol Dark Blue BOOTriazol Dark Blue 3 GTriazol Dark Blue ROO....Triazol Fast Red LTriazol Faat Yellow 2
GOOOOTriazol Green BTriazol Green BPOOTriazol Green GPOOTriazol Pure Blue 3 BTriazol Pure Blue 11Triazol Red BTriazol Violet RTriazol Violet RRTriazol Yellow NBPOO....Trisulf on Blue BTrisulfon Blue 3 GTrisulf on Blue RTrisulf on BrownTrisulfon Brown A, B, MB.Trisulfon Brown GTrisulfon Brown GGTriaulfon Violet BTropasoline (V. M.)Tropseoline 00Trypan BlueTrypan RedTurmeric Yellow 000Turquoise BlueTurquoise Blue B, BB, G...Tuscaline Orange GTypophor Blaok FBTypophor Brown FRTypophor Black F 3 RTypophor Brown FBTypophor Rod FGTypophor Yellow FRTypophor Yellow F 3 RUltra Flavine SDUltra Orange RUltra Violet BUltra Violet FKNUltra Violet LGPUltra Violet MOUltra Violet 943Ultraoyanine BUnion Acid Black Bli, GH.Union BlackUnion Black BRNUnion Black SOJUnion Blue HUnion Blue RUnion Blue RUnion Blue (V. M.)Union Fast ClaretUnion Red B
MGrEGrEGrEGrEGrEGrEGrEGrEGrEGrEGrEGrE
GrEGrEGrEGrEGrEGrE
GrEGrEGrEGrEGrEGrEGrEGrEGrEGrESSssssssC, etc.HMM
i-BBBBBBBSSsKssKsIIcsAsMKCLevK
624 GLOSSARY OF DYE NAMES
Name
Union Red BSUniversal Black BUrania BlueUranmeUranme AUranme NUrsolUrsol AUrsol ADFUrsol DUrsol DBUrsol DFUrsol GGUrsol PUrsol PPUrsol Gray ALVarnish BlackVarnish Black 5 RVesuvine (V M )VictonaVictoria Black BVictona Blue BVictona Blue B baseVictoria Blue BE, BS, BSSVictona Blue RVictona Blue 4 RVietona Blue BaseVictona Blue Base 61272Victona Brilliant Blue BVictona Fast Violet BVictona Fast Violet 2 RVictona GreenVictona Green BFVictona Green 4833, 4S34Victona Green BaseVictoria Navy Blue LVictona Pure Blue BVictona Scarlet RVictona Scarlet 2 R, 4 RVictona Scarlet 3 RVictona Violet (V M )Victona \ ellowVidal Black IVigoureux Brown IVigoureux Past Black TVigoureux Green BViolamine BViolamine 3 BViolamine RViolet 2 BViolet 6 BViolet DVViolet NXViolet 9 0, 300 XEViolet 5539GViolet Base 2 BViolet Base 5747Violet BlackViolet CrystalsViolet CrystalsViolet Crystals 5 BO, 6 BOViolet Crystals 0Violet Crystals 142 SViolet Direct VRViolet Modern NViolet Neutral 0Violettine 3 RVmdanthrene BVitoline Yellow 5 G, RVulcan Blue BOVulcan Blue GWater BlueWater Blue MX
Manu-fac-turer
wbA, etcBMAAAAAAAAAQGBy\ar\arBVarVarSHMByByVarBB>B tMByBMtMMVarMPMMCMMMK tMQQAWPHQBKBSKIMKGDHMAWBtMLevLevC.etcQ
SerialNo
A412bU2b7
6G55S5585585923923923923923923923923923923
U54SUS162b41692b25595o9559558522559a559a559b
TJ26SU269
497a497a497a497a
TJ270559
A439169
A44061
134717
XJ477159a
U299580584582516a517516a516a516a516a516a51ba290516516516516516
A660624516a
U591705606
U740U741
539539
Name
Water Blue S 2 KWood Red 40 FWool Black (V M )Wool Black (V M )Wool Black (V M )Wool Black b A CANWool Black B 2BWool Black BWool Black BBWool Black 3 BWool Black 4 B 6 B, 4 BCWool Black 4 BWool Black 10 BWool Black 4 BrL, G BS,
4 BXWool Black CD CLWool Black DWWool Black G GR, GRFWool Black 6 GWool Black GGWool Black HNWool Black LRWool Black MXWool Black NWool Black NNWool Black N 4 BWool Black NCWool Black NPWool Black NPWool Black NRWool Black SGWool Black VWool Black 9904Wool Black (greenish)Wool BlueWool BlueWool Blue (V M )Wool Blue (V M )Wool Blue BWool Blue 2 B 5 B, GWool Blue 2 BXWool Blue G, 2 G, G 446 NWool Blue MWool Blue NWool Blue R, RXWool Blue RWool Blue 5 RWool Blue SWool Blue SWool Blue 2 SWool Blue SBWool Blue SDOO, SLOOWool Blue SRWool Blue TBWool Blue 1092Wool Blue Black 2019Wool Brown MC, P, SVR,
UB 2S08Wool Canary ODWool Cense SRWool Claret 21 BWool Claret Red 87 B, 211,
357Wool Fast Black BFool Fast Blue BLTool Fast Blue BL
Wool Fast Blue GLWool Fast Blue LWool Fast Orange GWool Fast Yellow GWool Fast Yellow 5 GXWool Fast Yellow WG"Wool Green (V M )
Manu-fac-turer
A&chIvLevtMAKAWLevAItMAIvBKAGtMtMIvQMIBy3vByCGIvGrEBKIvcQKLevAWAAKAWByAl y
KKAWBByKAKKHKLevLevBBByByIBBBBK
SerialNo
539lbb
U390220b220b217g220b
U39O272c220b220272c2l7g220
U3902(>9220b
Ub4b217217g
U390220b
A441272c
A301U3<)0AS02
272cU390
272cU390
269U300moo
53bbU391
505a5(i55b55b5a
U3915b2b56256 5a5b2b538
um538b
U391562b530d562
U391565a
U392U393U765U394U742U743U200U201U271U272U693U202U203U204U205U395
GLOSSARY OF DYE NAMES 625
Name
reenreen Breen BSreen Sreen SAK, 16437reenSCt Black 3 B3dd (V M)jd CdCSdG3d K 10 BXdL MC, SOCdSBd7742ailetarlet (V M ) .arlet 5 Barlet Railet RRarlet 4 Rarlet 3 RBDiet Bolet RDiet SDiet SLHowHow AT D GHow LDV, RllowSllowTHow 1501>CJB-IEosine5 BGRmEHnYDonilue AS ASL BSUue VSast Green Blght Yellowight Yellow 2 G
Manu-fac-turer
tMQByBKVarIGAKCsKBBKCGBKKLevH&chBBKBQKBKSchKKGGKIPHHHHHHSssVarK S
SerialNo
566a5b6566566566a566220cIb8b236236bIb8b
A14OA141
168bb4
168bU39b
bObbOc80
A14280a
A14359a
U39759
U39S23
U399U309
1432*
U39900bCOb590a
U770U770
284aU771U772
5085075042222
Name
Xylene Light Yellow RXylene Light Yellow RXylene Red BXylene YellowXylene Yellow 3 GXj hdine Orange RRXylidinc Scailct\ ellow (V M )\ ellow (V M )Yellow CPY ellow FYYellow NlYellow Nrbellow PCYellow 11Yellow 2 SYellow (for feathers)Yellow Black MYellow last-To boapYellow Tat ColorYellow Groen 0 BZambesi Black BZambesi Black 2 BAZambesi Black BHZambesi Black BRZambesi Black OTAZambesi Black DZambesi Black FZambesi Black OBAZambesi Black RZambesi Black VZambesi Black VMZambesi Bordeaux 7 BZambesi BrownZambesi Brown G 2 GZambesi Brown 4 RZambesi Pure Blue 4 BZambesi Red BZambesi Red 4 BZambesi Red 0 BZambesi Red 8 BZambesi Rubine BZambesi beat lot 6 BZambesi Seatlet 2 BLZambesi Seailot FRZambeHi Scarlet PR
Manu-fac-turer
KSbTvBK.lMSdiCJ1Lev11BKQDIIwpWDBKPBBKAAAAAAAAAAAAAAAAAAAAAAAA
SenalNo
2222
579111179S2
Ur>00lUd1 illl1777*
171-S7U817UbOl
Hid1*7
U5 i()U18S
20*(>S
IHSQAUiA17A1SA49Ar>*Ar>()Ar>lAr»l:Ar>2Ar)r)Ar>bAr>7**0**()* *()ll271bAr>SAWA(H)A01A(i2AOJA(nA(io
L G E I N D E X O F S C H U L T Z N U M B E R S F O R D Y E S
Ls the Glossary of Dye Names refers only to Schultz numbers, by look-in this index for the Schultz number, there can be found the pages
which any dye is tabulated.?his procedure was adopted for the reason that a given dye, eharac-zed by a Schultz number, will be known under very many names.5h names are listed in the Glossary but could not all be placed in theles without unnecessarily enlarging this book.
dtziber Page1 5092 362,4473 2234 5265 4606 3607 3608 4569 4520 253, 260, 4521 260, 453, 5092 91, 253, 260, 4533 200, 453, 471.4 78, 4535 126, 4536 183, 453,7 183, 4538 183, 253, 260, 4969 21, 91, 345, 48110 91, 481, 53411 343, 55212 21, 213, 529,3 230, 482, 52914 87, 34315 21, 49616 343, 496.7 21, 345, 482, 49018 343, 53319 67, 34310 Not classified\1 32, 9112 91, 23813 91, 46514 92, 56615 92, 50916 92, 36217 92, 52618 92, 28619 92, 50410 92, 174LI 92, 29812 22, 93L3 93, 326L4 93, 50815 93, 311L6 362, 421L7 421, 504L8 421, 519L9 421, 517>0 279, 42211 183, 42252 353, 422>3 330, 422
SchultzNumber
54555657585960616263646566676869707172737475767778798081828384858687
90919293949596979899100101102103104105106
Page394, 422409, 422362, 377, 422174, 42393, 423, 519219, 248S3, 50926, 174, 423, 471245, 500225, 245, 42326, 37026, 50422, 2727, 17436, 554554, 567526, 553225, 553362, 456362, 45542, 43, 36242, 43, 509362, 576414, 576375, 576526, 577372, 577370, 578505, 577, 578498, 50578, 50076, 48450, 362Not classified465, 494465, 49478, 494353, 49460, 494108, 362108, 414108, 37249, 108, 519156, 363363, 425363, 42649, 37149, 505126, 519126, 519142, 414360, 385363, 385
627
SchultzNumber
107108109110111112113114115116117118119120121122123124125126127128129130131132133134135136137138139140141142143144145146147148149150151152153154155156157158159
Page385, 447375, 3S5370, 385372, 385385, 526385, 505287, 385174, 385363, 392392, 447182, 371182, 225, 372165, 18284, 185185, 371185, 287186, 52693, 238, 555, 56993, 460, 655, 56993, 363, 565, 50993, 555, 57094, 555, 67038, 17438, 43, 174, 27746, 36374, 36374, 519262, 334262, 334262, 33432238, 529202, 529202, 529202, 529202, 530510, 630360, 530363, 630225, 530225, 53075, 3043687, 26287, 36487, 31146, 36481, 46681, 61081, 36481, 22380, 50077, 364
628 PAGE INDEX OF SCHULTZ NUMBERS FOR DYES
SchultzNumbei
160161162163164165166167168169170171172173174-175176177178179180181182183184185186187188189190191192193194195196197198199200201202203204205206207208209210211212213214215216217218219220221222223224225226227228229230231232233234235236237
Page354, 360354, 364330, 364354, 414354, 375354, 370354, 526180, 354355, 505287, 355355, 380174, 355153, 360364, 403153, 365365, 404153, 414153, 178, 51955, 520311, 40368, 36068, 36594, 125, 298, 55276,36076, 36572, 365276, 29863, 299299, 484299, 572183, 466, 496437, 496473, 496183, 365184, 414414, 496184, 527496, 527184, 497184, 497, 520110, 365110, 527110, 50540, 26240, 520454, 460, 471243, 454, 471454, 471, 475466, 471184, 355, 466, 497334, 473, 497510, 530, 578361, 531355, 510361, 57994, 326, 42365, 94, 42394, 299, 42371, 207, 386, 42494, 326, 49470, 386, 531424, 520, 53183, 421, 51032, 36532, 41432, 37032, 37233, 28733, 38033, 22636, 15336. 27636, 36636, 41436, 52736, 37236, 50537, 527
SchultzNumber Page238 37, 506239240241242243244245
27, 47, 242, 366, 466S3, 366, 55394,295,38694, 226, 40027, 386, 52727, 386, 506295, 386, 424
246 34, 366247 34, 366248 34, 527249 34, 180250 34, 520251 34, 180252 37, 366253 37, 414254 37, 527255 37, 180256 334, 386, 485257 334, 386, 400, 485, 572258 334, 3S6, 401259 108, 180, 531260 48, 366, 531261 299, 3S6, 531262 226, 387, 531263 39, 387, 483264 299, 355, 3(56265 330, 387, 401, 485266 2S5, 3S7267 204, 264, 285, 387, 387,
394268 67, 387, 394269 387, 394, 506270 55, 94, 2S7, 506271 55, 67, 3G7272 55, 388, 506273 23, 3S8, 411, 527274 23, 295, 388, 411275 85, 376, 388, 415276 85, 226, 388277 85,401278 38S, 401279 33, 95, 325, 4SG280 535, 550281 392, 535, 556282 392, 535283 4«6284 567285 200, 466286 200, 437287 200, 392288 198, 367289 19S, 3I>7, 527290 27, 3SS, 415, 471291 415, 471, 520292 175, 472, 520293 527, 541294 520, 541295 194, 205, 567296 27, 486, 520297 194, 295298 193, 506299 196, 506300 196, 506301 199,392302 153,199303 199,460304 199,460305 199, 520306 126, 437, 473307 126, 355308 126,330309 120, 356, 413310 126,413311 126, 177, 356312 126, 356, 415313 127, ISO, 356314 84, 127, 437
SchultzNumber Page315 84, 127, 460316 84, 127, 154317 127, 510318 127, 367319 127, 287, 460320 127, ISO321 127, 180, 372322 84, 127, 367, 379323 128, 175324 70, 128, 180325 70, 128, 371326 128, 325327 128, 295328 128, 295329 128, 295, 466330 128, 295, 412331 128, 295, 447332 84, 128, 295333 128, 296, 299334 129, 273, 300335 129, 296, 326336 70, 129, 300337 129, 300338 129, 326, 546339 82, 129, 520340 129, 129, 356, 405,
521, 521341 129, 506, 521342 130,521343 130, 296, 521344 130, 296, 521345 69, 130, 521346 130, 325, 521347 130, 341, 522348 130, 243,522349 130, 475, 522350 130, 184,522351 130, 178352 131, 228, 567353 131, 228, 300354 131, 22S355 415, 432, 522356 210, 356357 154, 210358 84, 210359 84, 137360 135,437361 136, 483362 201, 546363 356, 546364 330, 546365 154, 546366 154, 405, 546367 405, 547368 154, 356, 547369 84, 357, 547370 84, 154, 547371 276, 405, 547372 276, 547373 84, 460, 547374 357, 510, 547375 357,415,547376 510, 547377 415, 547378 367, 379, 547379 175, 415, 548380 175, 548381 300, 309, 548382 300, 388, 548383 300, 392, 548384 70, 181, 548385 325, 415, 548386 300, 410, 548387 70, 371, 548388 70, 548389 65, 549390 70, 300, 549391 301, 549
PAGE INDEX OF SCHULTZ NUMBERS FOB DYES 629
SchultzNumber Page392 178, 201, 549393 243, 522, 549394 522, 549395 178, 549396 227, 416, 549397 228, 416, 549398 229, 549399 227, 296, 550400 3b7, 551401 2b8, 416402 2b8, 206, 373403 2G8, 296404 268, 461, 522405 202, 357406 202, 3b7, 399407 202, 3r>7, 416408 202, 202, 202, 368, 421,
424409 202, 308, 379410 202, 41b411 202, 376412 202, 41b, 506413 202, 224, 567414 203, 221, 507415 17r>, 203416 203, 22b417 166, 16b, 203418 105, 203419 64, 203, 368420 70, lbl, 203421 60, 203, 416422 64, 70, 203423 71, 204424 64, 204425 71, 204, 301426 204, 301427 204, 227, 416428 204, 229, 416429 204, 227, 507430 204, 227, 301431 10b, 461432 3S0 408433 392, 410, 507434 308, 410, 507435 41, Si, 95, 389,467, 510,
554436 206, 401, 467, 472437 296, 4b7, 472, 511438 131, 301, 479439 49, 131, 301440 49, 131, 207441 131, 301, 3b9442 131, 297, 3b0, 508443 131, 301, 380 508444 95, 131, 207, 522445 95, 131, 475, 522446 132, 301, 3S0, 522447 132, 3S0, 417, 52 J448 132, 302, 4(>7, 523449 132, 467, 508, 523450 389, 417, 5r>0451 371, 390, 550452 22b, 300, 550453 508, 550, 567454 467, 508, 523, 550455 204, 508, 5b7456 205, 371, 390457 205,467,508,52 5458 74, 401, 410, 468, 474,
567459 135, 300, 417460 135, 226, 300461 297, 410, 468, 511, 568462 95, 132, 302, 468463 95, 132, 302, 5t>8464 95, 132, 302, 4bl465 71, 95, 132, 523466 65, 133, 523, 531
SchultzNumber467468469470471472473474475476477478479480481482483484485486487488489490491492493494495496497498499500501502503504505506507508509510511
512513514515516517518519520521522523524525526527528529530531532533534535536537538539540541542543
Page133, 167, 302, 461133, 167, 302, 523133, 207, 302, 4bS133, 207, 302, 461133, 207, 303133, 207, 297, 303133, 297, 303, 424133, 303, 424 4bl134, 303, 424, 523134, 468, 524, 531134, 511, 524, 53271, 134, 524 532134, 175, 357, 468134 330, 511, 52482, 357, 511 55090, 524 55b 560100 417190, 417, 507409 53240, 400357, 4b9200, 357, 469134,511 532131, 358, 469137, 297, 46985, 390 400233, 26b 327, 540242 345120, 238159 23b209 23S304 452 537120 217159, 282209 345120 270150, 270121, 147121 1U122 144, 279217, 337144 33713b, 301;SO, 239 128 52489, 06, 103, 429, 430,
5bO, 57406, 430, 556, 50000, 195, 451, 55090, 550 5012*0, 401230 30i, 327, 4b714? 239 402217, 4b7, 537, 538230, 46207, 138, 50107, 138, 557, 501327, 342143, 240, 42807, 557, 5«197, 557, 50197 557, 501147, 328140 $04232, 279218, 270205, 539339, 537232, 339214, $3907, 56298, 557, 56298, 558, 50298, 203, 558, 50208, 5r>». 56209, 193, 55b, 56299, 393, 55H, 502163, 254, 305, 33421b, 308, 42b
SchultzNumber544545546547548549550551552553554555556557558559560561562563564
565566567568569570571572573574575576577578579580581582583584585586587588589590591592593594595596597598599600601602603604605606607608609610611612613614615616617618619620
Page218, 308, 428145, 308, 428282, 308235, 339270, 328305, 52585, 305159, 178168, 178122, 179159, 179462402525270, 305, 32S305, 328, 483537, 57132b, 343305, 398305, 33C, 358232, 240, 305, 347.
349, 5752012b7, 306, 328, 368300, 310237237210, 237, 510271, 4b809, 216, 488210, 488, 511210, 488234, 5164b 234234, 2712H, 511122, 21600, 488, 512, 563210, 4b9ibO, 512, 558MS, 489, 512211, 459, 512489, r>12143, 489, 512489, 512400, 513490, 513400, 513490, 513490, 513211, 513212, 514212, 514514, 536514, 536514, 536200, 400, 500401, 514200, 491, 500568244, 540121, 244121, 56800, 558, 56332b, 470Aoi classifiedNot cla88%fied139, 324, 502331, 503191 502491, 502182497407, 503184Ib2245, 301, 440*214, 440
30 PAGE INDEX OF SCHULTZ NUMBERS FOB DYES
-huUzumber Page621 236,472622 100, 290, 440623 440, 501624 290, 440625 290, 447626 290, 440627 245, 288, 440628 231, 291, 441629 291, 441630 100, 28S, 441631 291, 441632 291, 441633 291, 441634 291, 441635 291, 441636 294, 441637 288, 442638 288, 442639 289, 439, 442640 100, 29 i, 442641 213, 288, 439842 292, 442, 514643 292, 442, 515644 292, 442, 515645 292, 442, 528646 100, 213, 288, 439647 442, 515648 449, 515649 368, 443650 368, 443651 369, 443652 306, 369, 443653 215, 390654 147, 215655 223, 443656 68, 383657 72, 383658 309, 443659 240, 245, 443660 240, 245, 443661 240, 245, 247, 275, 444662 279, 280663 282, 284664 247, 292665 247, 248666 221, 382667 247, 281, 381, 382668 52, 45S669 246, 470670 246, 444, 568671 283, 390672 100, 390673 100, 390674 101, 391675 101, 448676 444, 484677 265, 444671 219, 444679 101, 559, 570680 101, 246681 246, 444682 101, 444683 101, 246, 333, 559, 563684 101, 148, 278, 283, 34 5
444, 445, 446, 446,486, 486, 486
444, 577101, 218, 220, 56353, 102, 559102, 553264, 444246, 267266, 445248,445102, 391, 462, 48335, 39135, 47233, 102
SchultzNumber Page
697 33, 102698 102, 431, 435699 33, 102700 103, 431, 435701 33,472702 103, 472, 559, 563703 445, 559, 563704 445, 559705 445, 559, 564706 Not classified707 Not classified708 Not classified709 79, 437710 568711 568712 135, 571713 472714 27, 135, 472715 27, 187716 571717 79718 431, 462, 472719 103, 424, 436720 259721 259722 259723 259724 79, 162, 255725 79, 162, 252, 255726 57, 79, 162, 255127 52, 162, 473728 235729 103,246730 57731 246, 361732 56, 197, 463733 79, 559734 79, 432735 464, 464736 57737 433738 162, 254, 255, 335, 532739 57740 258741 258742 258743 258744 Not classified745 257746 313747 312748 155,449749 250,251750 258751 Not classified752 Not classified753 Not classified754 Not classified755 Not classified756 Not classified757 Not classified758 347, 384, 491759 337760 241761 241762 241763 118,124764 118, 124765 118, 124766 160767 160768 160769 500770 138, 139, 500771 517772 293773 21, 222, 500774 256,352
SchultzNumber
775776777778779780781782783784785786787788789790791792793794795796797798799800801802803804805806807808809810811812813814815816817818819820821822823824825826827828829830831832833834835836837838839840841842843844845846847848849850851852
Page256, 352, 46325617525, 11525, 115, 41925, 11525, 115138, 293, 49125, 115, 49911411311325, 11525, 115257109, 250109337338338337109, 24925, 28, 115, 42025, 115, 41825, 11525125025028, 41928, 41928, 420, 43143443428, 41928, 41930, 4873020, 18620, 18629, 14059, 140141, 1S8141, 18855, 141141, 188190141, 190141, 57389, 14129, 15730, 15229, 20845, 209157, 18859, 20829, 209158, 393111, 20841, 13929, 157116116, 18930, 31630, 316151316, 3173163163174418930, 1241911893131731, 10388, 502, 502, 564
GE INDEX OF SCHULTZ NUMBERS FOR DYES 631
Page51, 5645, 115, 5640, 56451, 50403, 250175, 5645, 56404, 5355, 104, 115, 4991204, 427, 5648, 503, 503, 5053510329, 141, 157Vot classified1849, 18804, 318, 476, 478, 491,542
04, 318, 476, 479, 492,542
L05, 318, 476, 479, 492,542
SchultzNumber
878879880881
882883884885886887888889890891892893894;895
Page105, 318, 476, 479, 492,
543105, 319, 476, 479, 492,
543105, 319, 476, 479, 492,105, 319, 477, 479, 492,
543105, 319, 477, 480, 492,
543105, 319, 477, 480,492,
543105, 319, 477, 480, 493,
543105, 319, 477, 480, 493,
543100, 319, 477, 480, 493,
544168450, 559106, 142, 319, 477, 480,
493, 544106, 142, 319, 478, 481,359359117, 206306, 322206, 361
SchultzNumber
896897898899900QAi9U JL902903904905906907908909910911912913914915916917918919920921922923
Page307, 322320, 320, 321321, 341314, 322314, 322, 322314, 32258, 32358, 32358, 321314,321314, 32119, 31419, 31417215019, 58314, 54526958269274171173314, 545104170, 43853, 10678, 79, 192, 473