Indigo Dye

8/18/2019 Indigo Dye

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Indigo dyeFrom Wikipedia, the free encyclopedia

Indigo

NamesOther names2,2'-Bis(2,3-dihydro-3- oxoindolyliden , Indigotin

Identifiers!"# $%m&er 2- )-3

!h*+B !h*+B )) 2

!hem#pider ..//)

0mol interacti1e 3 Image4*!# n%m&er 52) //

5$II 67 B8 69 F

In!hI :sho;<#+I *# :sho;<

Properties!hemical form%la ! 6=> 6/ $ 2O2+olar mass 2=2?2. g@mol

https://en.wikipedia.org/wiki/CAS_Registry_Numberhttp://www.commonchemistry.org/ChemicalDetail.aspx?ref=482-89-3http://www.commonchemistry.org/ChemicalDetail.aspx?ref=482-89-3https://en.wikipedia.org/wiki/ChEMBLhttps://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL599552https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL599552https://en.wikipedia.org/wiki/ChemSpiderhttp://www.chemspider.com/Chemical-Structure.4477009.htmlhttp://www.chemspider.com/Chemical-Structure.4477009.htmlhttps://en.wikipedia.org/wiki/Jmolhttp://chemapps.stolaf.edu/jmol/jmol.php?model=c1ccc2c(c1)C(%3DO)%2FC(%3DC%5C3%2FC(%3DO)c4ccccc4N3)%2FN2https://en.wikipedia.org/wiki/RTECShttps://en.wikipedia.org/wiki/Unique_Ingredient_Identifierhttp://fdasis.nlm.nih.gov/srs/srsdirect.jsp?regno=1G5BK41P4Fhttp://fdasis.nlm.nih.gov/srs/srsdirect.jsp?regno=1G5BK41P4Fhttps://en.wikipedia.org/wiki/International_Chemical_Identifierhttps://en.wikipedia.org/wiki/Indigo_dyehttps://en.wikipedia.org/wiki/Simplified_molecular-input_line-entry_systemhttps://en.wikipedia.org/wiki/Indigo_dyehttps://en.wikipedia.org/wiki/Chemical_formulahttps://en.wikipedia.org/wiki/Molar_masshttp://www.commonchemistry.org/ChemicalDetail.aspx?ref=482-89-3https://en.wikipedia.org/wiki/ChEMBLhttps://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL599552https://en.wikipedia.org/wiki/ChemSpiderhttp://www.chemspider.com/Chemical-Structure.4477009.htmlhttps://en.wikipedia.org/wiki/Jmolhttp://chemapps.stolaf.edu/jmol/jmol.php?model=c1ccc2c(c1)C(%3DO)%2FC(%3DC%5C3%2FC(%3DO)c4ccccc4N3)%2FN2https://en.wikipedia.org/wiki/RTECShttps://en.wikipedia.org/wiki/Unique_Ingredient_Identifierhttp://fdasis.nlm.nih.gov/srs/srsdirect.jsp?regno=1G5BK41P4Fhttps://en.wikipedia.org/wiki/International_Chemical_Identifierhttps://en.wikipedia.org/wiki/Indigo_dyehttps://en.wikipedia.org/wiki/Simplified_molecular-input_line-entry_systemhttps://en.wikipedia.org/wiki/Indigo_dyehttps://en.wikipedia.org/wiki/Chemical_formulahttps://en.wikipedia.org/wiki/Molar_masshttps://en.wikipedia.org/wiki/CAS_Registry_Number


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"ppearance dark &l%e crystalline po;der ensity 6?6)) g@cm3

+elting point 3)/ to 3)2 A! (.3 to .3 AF==3 to == 8Boiling point decomposes#ol%&ility in ;ater ))/ Cg@ (at 2 A!

Hazards*5 classification ( #

2/.- =-)

-phrases 3=@3.@3#-phrases #2= -#3=

Related compounds

elated compo%ndsIndoxyl4yrian p%rpleIndican

*xcept ;here other;ise noted, data are gi1en formaterials in their standard state (at 2 A! :.. AFistorically, indigo;as a nat%ral dye extracted from plants, and this process ;as important economically &eca%se

&l%e dyes ;ere once rare? " large percentage of indigo dye prod%ced today E se1eral tho%sandtons each year E is synthetic ? It is the &l%e often associated ;ith &l%e eans?

Contents

• 6 5ses

• 2 $at%ral indigoes

o 2?6 9lant so%rces

o 2?2 *xtraction

o 2?3 !%lti1ation

o 2? >istory of nat%ral indigo

• 3 *ra of synthetic indigo

https://en.wikipedia.org/wiki/Densityhttps://en.wikipedia.org/wiki/Melting_pointhttps://en.wikipedia.org/wiki/Boiling_pointhttps://en.wikipedia.org/wiki/Aqueous_solutionhttps://en.wikipedia.org/wiki/Dangerous_Substances_Directive_(67/548/EEC)https://en.wikipedia.org/wiki/Dangerous_Substances_Directive_(67/548/EEC)https://en.wikipedia.org/wiki/List_of_R-phraseshttps://en.wikipedia.org/wiki/R36/37/38:_Irritating_to_eyes,_respiratory_system_and_skinhttps://en.wikipedia.org/wiki/List_of_S-phraseshttps://en.wikipedia.org/wiki/S26:_In_case_of_contact_with_eyes,_rinse_immediately_with_plenty_of_water_and_seek_medical_advicehttps://en.wikipedia.org/wiki/S36:_Wear_suitable_protective_clothinghttps://en.wikipedia.org/wiki/Indoxylhttps://en.wikipedia.org/wiki/Tyrian_purplehttps://en.wikipedia.org/wiki/Indicanhttps://en.wikipedia.org/wiki/Standard_statehttps://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477315345&page2=Indigo+dyehttps://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477315345&page2=Indigo+dyehttps://en.wikipedia.org/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validationhttps://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox#Referenceshttps://en.wikipedia.org/wiki/Organic_compoundhttps://en.wikipedia.org/wiki/Indigohttps://en.wikipedia.org/wiki/Indigohttps://en.wikipedia.org/wiki/Natural_dyehttps://en.wikipedia.org/wiki/Dyehttps://en.wikipedia.org/wiki/Chemical_synthesishttps://en.wikipedia.org/wiki/Jeanshttps://en.wikipedia.org/wiki/Jeanshttps://en.wikipedia.org/wiki/Indigo_dye#Useshttps://en.wikipedia.org/wiki/Indigo_dye#Natural_indigoeshttps://en.wikipedia.org/wiki/Indigo_dye#Plant_sourceshttps://en.wikipedia.org/wiki/Indigo_dye#Extractionhttps://en.wikipedia.org/wiki/Indigo_dye#Cultivationhttps://en.wikipedia.org/wiki/Indigo_dye#History_of_natural_indigohttps://en.wikipedia.org/wiki/Indigo_dye#Era_of_synthetic_indigohttps://en.wikipedia.org/wiki/Densityhttps://en.wikipedia.org/wiki/Melting_pointhttps://en.wikipedia.org/wiki/Boiling_pointhttps://en.wikipedia.org/wiki/Aqueous_solutionhttps://en.wikipedia.org/wiki/Dangerous_Substances_Directive_(67/548/EEC)https://en.wikipedia.org/wiki/List_of_R-phraseshttps://en.wikipedia.org/wiki/R36/37/38:_Irritating_to_eyes,_respiratory_system_and_skinhttps://en.wikipedia.org/wiki/List_of_S-phraseshttps://en.wikipedia.org/wiki/S26:_In_case_of_contact_with_eyes,_rinse_immediately_with_plenty_of_water_and_seek_medical_advicehttps://en.wikipedia.org/wiki/S36:_Wear_suitable_protective_clothinghttps://en.wikipedia.org/wiki/Indoxylhttps://en.wikipedia.org/wiki/Tyrian_purplehttps://en.wikipedia.org/wiki/Indicanhttps://en.wikipedia.org/wiki/Standard_statehttps://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477315345&page2=Indigo+dyehttps://en.wikipedia.org/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validationhttps://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox#Referenceshttps://en.wikipedia.org/wiki/Organic_compoundhttps://en.wikipedia.org/wiki/Indigohttps://en.wikipedia.org/wiki/Natural_dyehttps://en.wikipedia.org/wiki/Dyehttps://en.wikipedia.org/wiki/Chemical_synthesishttps://en.wikipedia.org/wiki/Jeanshttps://en.wikipedia.org/wiki/Indigo_dye#Useshttps://en.wikipedia.org/wiki/Indigo_dye#Natural_indigoeshttps://en.wikipedia.org/wiki/Indigo_dye#Plant_sourceshttps://en.wikipedia.org/wiki/Indigo_dye#Extractionhttps://en.wikipedia.org/wiki/Indigo_dye#Cultivationhttps://en.wikipedia.org/wiki/Indigo_dye#History_of_natural_indigohttps://en.wikipedia.org/wiki/Indigo_dye#Era_of_synthetic_indigo


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o 3?6 e1elopments in dyeing technology

3?6?6 Indigo ;hite

3?6?2 irect printing

o 3?2 !hemical properties

3?2?6 !hemical synthesis

3?2?2 Indigo deri1ati1es

• Indigo as an organic semicond%ctor

• #afety and the en1ironment

• = #ee also

• . eferences

• F%rther reading

• ) *xternal links

Uses

Indigo dye

4he primary %se for indigo is as a dye for cotton yarn, ;hich is mainly for the prod%ction of

denim cloth for &l%e eans? On a1erage, a pair of &l%e ean tro%sers reG%ires 3E62 g of indigo?#mall amo%nts are %sed for dyeing ;ool and silk?

Indigo carmine , or indigo, is an indigo deri1ati1e ;hich is also %sed as a colorant? "&o%t 2/million kg are prod%ced ann%ally, again mainly for &l%e eans? :6< It is also %sed as a food colorant,and is listed in the 5nited #tates as F H! Bl%e $o? 2?

https://en.wikipedia.org/wiki/Indigo_dye#Developments_in_dyeing_technologyhttps://en.wikipedia.org/wiki/Indigo_dye#Indigo_whitehttps://en.wikipedia.org/wiki/Indigo_dye#Direct_printinghttps://en.wikipedia.org/wiki/Indigo_dye#Chemical_propertieshttps://en.wikipedia.org/wiki/Indigo_dye#Chemical_synthesishttps://en.wikipedia.org/wiki/Indigo_dye#Indigo_derivativeshttps://en.wikipedia.org/wiki/Indigo_dye#Indigo_as_an_organic_semiconductorhttps://en.wikipedia.org/wiki/Indigo_dye#Safety_and_the_environmenthttps://en.wikipedia.org/wiki/Indigo_dye#See_alsohttps://en.wikipedia.org/wiki/Indigo_dye#Referenceshttps://en.wikipedia.org/wiki/Indigo_dye#Further_readinghttps://en.wikipedia.org/wiki/Indigo_dye#External_linkshttps://en.wikipedia.org/wiki/Indigo_carminehttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-Ullmann-1https://en.wikipedia.org/wiki/Indigo_dye#cite_note-Ullmann-1https://en.wikipedia.org/wiki/FD%26Chttps://en.wikipedia.org/wiki/FD%26Chttps://en.wikipedia.org/wiki/FD%26Chttps://en.wikipedia.org/wiki/Indigo_dye#Developments_in_dyeing_technologyhttps://en.wikipedia.org/wiki/Indigo_dye#Indigo_whitehttps://en.wikipedia.org/wiki/Indigo_dye#Direct_printinghttps://en.wikipedia.org/wiki/Indigo_dye#Chemical_propertieshttps://en.wikipedia.org/wiki/Indigo_dye#Chemical_synthesishttps://en.wikipedia.org/wiki/Indigo_dye#Indigo_derivativeshttps://en.wikipedia.org/wiki/Indigo_dye#Indigo_as_an_organic_semiconductorhttps://en.wikipedia.org/wiki/Indigo_dye#Safety_and_the_environmenthttps://en.wikipedia.org/wiki/Indigo_dye#See_alsohttps://en.wikipedia.org/wiki/Indigo_dye#Referenceshttps://en.wikipedia.org/wiki/Indigo_dye#Further_readinghttps://en.wikipedia.org/wiki/Indigo_dye#External_linkshttps://en.wikipedia.org/wiki/Indigo_carminehttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-Ullmann-1https://en.wikipedia.org/wiki/FD%26C


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Natural indigoes

Plant sources

" 1ariety of plants ha1e pro1ided indigo thro%gho%t history, &%t most nat%ral indigo ;aso&tained from those in the gen%s Indigofera , ;hich are nati1e to the tropics ? 4he primarycommercial indigo species in "sia ;as tr%e indigo ( Indigofera tinctoria , also kno;n as I.

sumatrana ? " common alternati1e %sed in the relati1ely colder s%&tropical locations s%ch as0apan's y%ky% Islands and 4ai;an is Strobilanthes cusia ? In !entral and #o%th "merica, the t;ospecies gro;n are I. suffruticosa (añil and dyer's knot;eed ( Polygonum tinctorum , altho%gh the

Indigofera species yield more dye?

Extraction

4he prec%rsor to indigo is indican , a colorless, ;ater-sol%&le deri1ati1e of the amino acidtryptophan ? Indican readily hydroly es to release J- - gl%cose and indoxyl ?Oxidation &yexpos%re to air con1erts indoxyl to indigo? Indican ;as o&tained from the processing of the

plant's lea1es, ;hich contain as m%ch as /?2E/? K of this compo%nd? 4he lea1es ;ere soaked in;ater and fermented to con1ert the glycoside indican present in the plant to the &l%e dyeindigotin ?:2< 4he precipitate from the fermented leaf sol%tion ;as mixed ;ith a strong &ase s%chas lye , pressed into cakes, dried, and po;dered? 4he po;der ;as then mixed ;ith 1ario%s others%&stances to prod%ce different shades of &l%e and p%rple?

Cultivation

Indigo ;as a ma or export crop that s%pported plantation sla1ery in colonial #o%th !arolina inthe 6 th cent%ry?:3<

4he demand for indigo in the 6)th cent%ry is indicated &y the fact that in 6 )., .,/// km 2 (2,.// sG mi ;ere dedicated to the c%lti1ation of indican-prod%cing plants, mainly in India? Bycomparison, the co%ntry of %xem&o%rg is 2, = km 2 ()) sG mi ?:6<

9easants in Bengal re1olted against %nfair treatment &y the *ast India !ompany traders@plantersin ;hat &ecame kno;n as the Indigo re1olt in 6 ), d%ring the British a of India ? In literat%re,the play Nil Darpan &y ina&andh% +itra is &ased on the sla1ery and forced c%lti1ation ofindigo in India?

History of natural indigo

Indigo, historical dye collection of the 4echnical 5ni1ersity of resden , 7ermany

https://en.wikipedia.org/wiki/Indigoferahttps://en.wikipedia.org/wiki/Tropicshttps://en.wikipedia.org/wiki/Indigofera_tinctoriahttps://en.wikipedia.org/w/index.php?title=Strobilanthes_cusia&action=edit&redlink=1https://en.wikipedia.org/wiki/Central_Americahttps://en.wikipedia.org/wiki/Indigofera_suffruticosahttps://en.wikipedia.org/wiki/Polygonum_tinctorumhttps://en.wikipedia.org/wiki/Polygonum_tinctorumhttps://en.wikipedia.org/wiki/Indicanhttps://en.wikipedia.org/wiki/Indicanhttps://en.wikipedia.org/wiki/Tryptophanhttps://en.wikipedia.org/wiki/Hydrolysishttps://en.wikipedia.org/wiki/Glucosehttps://en.wikipedia.org/wiki/Indoxylhttps://en.wikipedia.org/wiki/Oxidationhttps://en.wikipedia.org/wiki/Fermentation_(biochemistry)https://en.wikipedia.org/wiki/Glycosidehttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-2https://en.wikipedia.org/wiki/Indigo_dye#cite_note-2https://en.wikipedia.org/wiki/Sodium_hydroxidehttps://en.wikipedia.org/wiki/South_Carolinahttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-3https://en.wikipedia.org/wiki/Indigo_dye#cite_note-3https://en.wikipedia.org/wiki/Luxembourghttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-Ullmann-1https://en.wikipedia.org/wiki/Bengalhttps://en.wikipedia.org/wiki/East_India_Companyhttps://en.wikipedia.org/wiki/East_India_Companyhttps://en.wikipedia.org/wiki/Indigo_revolthttps://en.wikipedia.org/wiki/Indigo_revolthttps://en.wikipedia.org/wiki/British_Rajhttps://en.wikipedia.org/wiki/Indiahttps://en.wikipedia.org/wiki/Indiahttps://en.wikipedia.org/wiki/Nil_Darpanhttps://en.wikipedia.org/wiki/Nil_Darpanhttps://en.wikipedia.org/wiki/Dinabandhu_Mitrahttps://en.wikipedia.org/wiki/Dresden_University_of_Technologyhttps://en.wikipedia.org/wiki/Indigoferahttps://en.wikipedia.org/wiki/Tropicshttps://en.wikipedia.org/wiki/Indigofera_tinctoriahttps://en.wikipedia.org/w/index.php?title=Strobilanthes_cusia&action=edit&redlink=1https://en.wikipedia.org/wiki/Central_Americahttps://en.wikipedia.org/wiki/Indigofera_suffruticosahttps://en.wikipedia.org/wiki/Polygonum_tinctorumhttps://en.wikipedia.org/wiki/Indicanhttps://en.wikipedia.org/wiki/Tryptophanhttps://en.wikipedia.org/wiki/Hydrolysishttps://en.wikipedia.org/wiki/Glucosehttps://en.wikipedia.org/wiki/Indoxylhttps://en.wikipedia.org/wiki/Oxidationhttps://en.wikipedia.org/wiki/Fermentation_(biochemistry)https://en.wikipedia.org/wiki/Glycosidehttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-2https://en.wikipedia.org/wiki/Sodium_hydroxidehttps://en.wikipedia.org/wiki/South_Carolinahttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-3https://en.wikipedia.org/wiki/Luxembourghttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-Ullmann-1https://en.wikipedia.org/wiki/Bengalhttps://en.wikipedia.org/wiki/East_India_Companyhttps://en.wikipedia.org/wiki/Indigo_revolthttps://en.wikipedia.org/wiki/British_Rajhttps://en.wikipedia.org/wiki/Indiahttps://en.wikipedia.org/wiki/Nil_Darpanhttps://en.wikipedia.org/wiki/Dinabandhu_Mitrahttps://en.wikipedia.org/wiki/Dresden_University_of_Technology


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Indigo ;as %sed in India, ;hich ;as also the earliest ma or center for its prod%ction and processing? : < 4he I. tinctoria species ;as domesticated in India? : < Indigo, %sed as a dye, made its;ay to the 7reeks and the omans , ;here it ;as 1al%ed as a l%x%ry prod%ct? : <

Indigo is among the oldest dyes to &e %sed for textile dyeing and printing? +any "sian co%ntries,

s%ch as India, !hina, 0apan, and #o%theast "sian nations ha1e %sed indigo as a dye (partic%larlysilk dye for cent%ries? 4he dye ;as also kno;n to ancient ci1ili ations in +esopotamia , *gypt , Britain , +esoamerica , 9er%, Iran , and "frica?

India is &elie1ed to &e the oldest center of indigo dyeing in the Old World? It ;as a primarys%pplier of indigo to *%rope as early as the 7reco- oman era? 4he association of India ;ithindigo is reflected in the 7reek ;ord for the dye, indikón (LMNL PM, Indian ? 4he omanslatini edthe term to indicum , ;hich passed into Italian dialect and e1ent%ally into *nglish as the ;ordindigo?

!ake of indigo, a&o%t 2 cm

In +esopotamia, a neo-Ba&ylonian c%neiform ta&let of the se1enth cent%ry B! gi1es a recipe for the dyeing of ;ool, ;here lapis -colored ;ool ( uqnatu is prod%ced &y repeated immersion andairing of the cloth? Indigo ;as most pro&a&ly imported from India? 4he omans %sed indigo as a

pigment for painting and for medicinal and cosmetic p%rposes? It ;as a l%x%ry item imported tothe +editerranean from India &y "ra& merchants?

Indigo remained a rare commodity in *%rope thro%gho%t the +iddle "ges? " chemically identicaldye deri1ed from the ;oad plant ( Isatis tinctoria , ;as %sed instead? In the late 6 th cent%ry, the9ort%g%ese explorer Qasco da 7ama disco1ered a sea ro%te to India? 4his led to the esta&lishmentof direct trade ;ith India, the #pice Islands , !hina, and 0apan? Importers co%ld no; a1oid thehea1y d%ties imposed &y 9ersian , e1antine , and 7reek middlemen and the lengthy anddangero%s land ro%tes ;hich had pre1io%sly &een %sed? !onseG%ently, the importation and %se of indigo in *%rope rose significantly? +%ch *%ropean indigo from "sia arri1ed thro%gh ports in9ort%gal, the $etherlands, and *ngland? #pain imported the dye from its colonies in #o%th"merica? +any indigo plantations ;ere esta&lished &y *%ropean po;ers in tropical climates it;as a ma or crop in 0amaica and #o%th !arolina , ;ith m%ch or all of the la&or performed &yensla1ed "fricans and "frican "mericans? Indigo plantations also thri1ed in the Qirgin Islands ?

https://en.wikipedia.org/wiki/Indigo_dye#cite_note-k.26c-4https://en.wikipedia.org/wiki/Indigofera_tinctoriahttps://en.wikipedia.org/wiki/Indigofera_tinctoriahttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-k.26c-4https://en.wikipedia.org/wiki/Ancient_Greecehttps://en.wikipedia.org/wiki/Ancient_Romehttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-k.26c-4https://en.wikipedia.org/wiki/Southeast_Asiahttps://en.wikipedia.org/wiki/Silkhttps://en.wikipedia.org/wiki/Mesopotamiahttps://en.wikipedia.org/wiki/Ancient_Egypthttps://en.wikipedia.org/wiki/Ancient_Egypthttps://en.wikipedia.org/wiki/Prehistoric_Britainhttps://en.wikipedia.org/wiki/Mesoamericahttps://en.wikipedia.org/wiki/Mesoamericahttps://en.wikipedia.org/wiki/Peruhttps://en.wikipedia.org/wiki/Iranhttps://en.wikipedia.org/wiki/Latinhttps://en.wikipedia.org/wiki/Venetian_languagehttps://en.wikipedia.org/wiki/Venetian_languagehttps://en.wikipedia.org/wiki/Cuneiform_scripthttps://en.wikipedia.org/wiki/Lapis_lazulihttps://en.wikipedia.org/wiki/Isatis_tinctoriahttps://en.wikipedia.org/wiki/Portugalhttps://en.wikipedia.org/wiki/Vasco_da_Gamahttps://en.wikipedia.org/wiki/Maluku_Islandshttps://en.wikipedia.org/wiki/Iranhttps://en.wikipedia.org/wiki/Iranhttps://en.wikipedia.org/wiki/Levanthttps://en.wikipedia.org/wiki/Levanthttps://en.wikipedia.org/wiki/Jamaicahttps://en.wikipedia.org/wiki/Jamaicahttps://en.wikipedia.org/wiki/South_Carolinahttps://en.wikipedia.org/wiki/Virgin_Islandshttps://en.wikipedia.org/wiki/Virgin_Islandshttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-k.26c-4https://en.wikipedia.org/wiki/Indigofera_tinctoriahttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-k.26c-4https://en.wikipedia.org/wiki/Ancient_Greecehttps://en.wikipedia.org/wiki/Ancient_Romehttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-k.26c-4https://en.wikipedia.org/wiki/Southeast_Asiahttps://en.wikipedia.org/wiki/Silkhttps://en.wikipedia.org/wiki/Mesopotamiahttps://en.wikipedia.org/wiki/Ancient_Egypthttps://en.wikipedia.org/wiki/Prehistoric_Britainhttps://en.wikipedia.org/wiki/Mesoamericahttps://en.wikipedia.org/wiki/Peruhttps://en.wikipedia.org/wiki/Iranhttps://en.wikipedia.org/wiki/Latinhttps://en.wikipedia.org/wiki/Venetian_languagehttps://en.wikipedia.org/wiki/Cuneiform_scripthttps://en.wikipedia.org/wiki/Lapis_lazulihttps://en.wikipedia.org/wiki/Isatis_tinctoriahttps://en.wikipedia.org/wiki/Portugalhttps://en.wikipedia.org/wiki/Vasco_da_Gamahttps://en.wikipedia.org/wiki/Maluku_Islandshttps://en.wikipedia.org/wiki/Iranhttps://en.wikipedia.org/wiki/Levanthttps://en.wikipedia.org/wiki/Jamaicahttps://en.wikipedia.org/wiki/South_Carolinahttps://en.wikipedia.org/wiki/Virgin_Islands


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>o;e1er, France and 7ermany o%tla;ed imported indigo in the 6=th cent%ry to protect the local;oad dye ind%stry?

+an ;earing an indigo-dyed tagelm%st

Indigo ;as the fo%ndation of cent%ries-old textile traditions thro%gho%t West "frica? From the4%areg nomads of the #ahara to !ameroon , clothes dyed ;ith indigo signified ;ealth? Womendyed the cloth in most areas, ;ith the Ror%&a of $igeria and the +andinka of +ali partic%larly;ell kno;n for their expertise? "mong the >a%sa male dyers, ;orking at comm%nal dye pits ;asthe &asis of the ;ealth of the ancient city of 8ano , and they can still &e seen plying their trade

today at the same pits?: <

In 0apan, indigo &ecame especially important in the *do period , ;hen it ;as for&idden to %sesilk, so the 0apanese &egan to import and plant cotton? It ;as diffic%lt to dye the cotton fi&erexcept ;ith indigo? *1en today indigo is 1ery m%ch appreciated as a color for the s%mmer8imono R%kata, as this traditional clothing recalls $at%re and the &l%e sea?

In $orth "merica indigo ;as introd%ced into colonial #o%th !arolina &y *li a %cas 9inckney ,;here it &ecame the colony's second-most important cash crop (after rice ? :=< When Ben aminFranklin sailed to France in $o1em&er 6..= to enlist France's s%pport for the "merican

e1ol%tionary War , 3 &arrels of indigo ;ere on &oard the !eprisal , the sale of ;hich ;o%ld

help f%nd the ;ar effort?:.<

In colonial $orth "merica, three commercially important species arefo%ndS the nati1e I. caroliniana , and the introd%ced I. tinctoria and I. suffruticosa ?: <

$e;ton %sed TindigoT to descri&e one of the t;o ne; primary colors he added to the fi1e he hadoriginally named, in his re1ised acco%nt of the rain&o; in "ectiones #pticae of 6=. ? :)<

Beca%se of its high 1al%e as a trading commodity, indigo ;as often referred to as &l%e gold? :6/<

Era of synthetic indigo

https://en.wikipedia.org/wiki/Tagelmusthttps://en.wikipedia.org/wiki/Tuareg_peoplehttps://en.wikipedia.org/wiki/Saharahttps://en.wikipedia.org/wiki/Saharahttps://en.wikipedia.org/wiki/Saharahttps://en.wikipedia.org/wiki/Cameroonhttps://en.wikipedia.org/wiki/Cameroonhttps://en.wikipedia.org/wiki/Yoruba_peoplehttps://en.wikipedia.org/wiki/Nigeriahttps://en.wikipedia.org/wiki/Mandinka_peoplehttps://en.wikipedia.org/wiki/Malihttps://en.wikipedia.org/wiki/Hausa_peoplehttps://en.wikipedia.org/wiki/Hausa_peoplehttps://en.wikipedia.org/wiki/Kanohttps://en.wikipedia.org/wiki/Kanohttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-5https://en.wikipedia.org/wiki/Edo_periodhttps://en.wikipedia.org/wiki/Edo_periodhttps://en.wikipedia.org/wiki/Kimonohttps://en.wikipedia.org/wiki/Eliza_Lucashttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-6https://en.wikipedia.org/wiki/Benjamin_Franklinhttps://en.wikipedia.org/wiki/Benjamin_Franklinhttps://en.wikipedia.org/wiki/American_Revolutionary_Warhttps://en.wikipedia.org/wiki/American_Revolutionary_Warhttps://en.wikipedia.org/wiki/USS_Reprisal_(1776)https://en.wikipedia.org/wiki/Indigo_dye#cite_note-7https://en.wikipedia.org/wiki/Indigo_dye#cite_note-8https://en.wikipedia.org/wiki/Indigo_dye#cite_note-8https://en.wikipedia.org/wiki/Isaac_Newtonhttps://en.wikipedia.org/wiki/Primary_colorhttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-9https://en.wikipedia.org/wiki/Indigo_dye#cite_note-10https://en.wikipedia.org/wiki/Tagelmusthttps://en.wikipedia.org/wiki/Tuareg_peoplehttps://en.wikipedia.org/wiki/Saharahttps://en.wikipedia.org/wiki/Cameroonhttps://en.wikipedia.org/wiki/Yoruba_peoplehttps://en.wikipedia.org/wiki/Nigeriahttps://en.wikipedia.org/wiki/Mandinka_peoplehttps://en.wikipedia.org/wiki/Malihttps://en.wikipedia.org/wiki/Hausa_peoplehttps://en.wikipedia.org/wiki/Kanohttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-5https://en.wikipedia.org/wiki/Edo_periodhttps://en.wikipedia.org/wiki/Kimonohttps://en.wikipedia.org/wiki/Eliza_Lucashttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-6https://en.wikipedia.org/wiki/Benjamin_Franklinhttps://en.wikipedia.org/wiki/Benjamin_Franklinhttps://en.wikipedia.org/wiki/American_Revolutionary_Warhttps://en.wikipedia.org/wiki/American_Revolutionary_Warhttps://en.wikipedia.org/wiki/USS_Reprisal_(1776)https://en.wikipedia.org/wiki/Indigo_dye#cite_note-7https://en.wikipedia.org/wiki/Indigo_dye#cite_note-8https://en.wikipedia.org/wiki/Isaac_Newtonhttps://en.wikipedia.org/wiki/Primary_colorhttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-9https://en.wikipedia.org/wiki/Indigo_dye#cite_note-10


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9rod%ction of Indigo dye in a B"#F plant (6 )/

In 6 )., 6),/// tons of indigo ;ere prod%ced from plant so%rces? argely d%e to ad1ances inorganic chemistry , prod%ction &y nat%ral so%rces dropped to 6,/// tons &y 6)6 and contin%ed tocontract? 4hese ad1ances can &e traced to 6 = ;hen the 7erman chemist "dolf 1on Baeyer

&egan ;orking on the synthesis of indigo? >e descri&ed his first synthesis of indigo in 6 .(from isatin and a second synthesis in 6 / (from 2-nitro&en aldehyde ? (It ;as not %ntil 6 3that Baeyer finally determined the str%ct%re of indigo ?:66< 4he synthesis of indigo remainedimpractical, so the search for alternati1e starting materials at B"#F and >oechst contin%ed?0ohannes 9fleger :62< and 8arl >e%mann e1ent%ally came %p ;ith ind%strial mass prod%ctionsynthesis? :63< 4he synthesis of $-(2-car&oxyphenyl glycine from the easy to o&tain aniline

pro1ided a ne; and economically attracti1e ro%te? B"#F de1eloped a commercially feasi&leman%fact%ring process that ;as in %se &y 6 ).? In 2//2, 6.,/// tons of synthetic indigo ;ere

prod%ced ;orld;ide?

Developments in dyeing technology

Indigo ;hite (le%co-indigo

https://en.wikipedia.org/wiki/Organic_chemistryhttps://en.wikipedia.org/wiki/Adolf_von_Baeyerhttps://en.wikipedia.org/wiki/Adolf_von_Baeyerhttps://en.wikipedia.org/wiki/Isatinhttps://en.wikipedia.org/wiki/2-nitrobenzaldehydehttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-11https://en.wikipedia.org/wiki/Indigo_dye#cite_note-11https://en.wikipedia.org/wiki/BASFhttps://en.wikipedia.org/wiki/BASFhttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-history.evonik.com-12https://en.wikipedia.org/wiki/Indigo_dye#cite_note-history.evonik.com-12https://de.wikipedia.org/wiki/Karl_Heumannhttps://de.wikipedia.org/wiki/Karl_Heumannhttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-ingenious.org.uk-13https://en.wikipedia.org/wiki/Anilinehttps://en.wikipedia.org/wiki/Organic_chemistryhttps://en.wikipedia.org/wiki/Adolf_von_Baeyerhttps://en.wikipedia.org/wiki/Isatinhttps://en.wikipedia.org/wiki/2-nitrobenzaldehydehttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-11https://en.wikipedia.org/wiki/BASFhttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-history.evonik.com-12https://de.wikipedia.org/wiki/Karl_Heumannhttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-ingenious.org.uk-13https://en.wikipedia.org/wiki/Aniline


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Rarn dyed ;ith indigo dye

Indigo hite

Indigo is a challenging dye &eca%se it is not sol%&le in ;ater? 4o &e dissol1ed, it m%st %ndergo a

chemical change ( red%ction ? ed%ction con1erts indigo into T;hite indigoT (le%co-indigo ?When a s%&merged fa&ric is remo1ed from the dye&ath, the ;hite indigo G%ickly com&ines ;ithoxygen in the air and re1erts to the insol%&le, intensely colored indigo? When it first &ecame;idely a1aila&le in *%rope in the 6=th cent%ry, *%ropean dyers and printers str%ggled ;ithindigo &eca%se of this distincti1e property? It also reG%ired se1eral chemical manip%lations, somein1ol1ing toxic materials, and had many opport%nities to in %re ;orkers? In the 6)th cent%ry,*nglish poet William Words;orth referred to the plight of indigo dye ;orkers of his hometo;nof !ockermo%th in his a%to&iographical poem T4he 9rel%deT? #peaking of their dire ;orkingconditions and the empathy that he feels for them, he ;rote,

Doubtless$ I should ha%e then made common cause

&ith some 'ho perished haply perished too ) poor mistaken and be'ildered offering *nkno'n to those bare souls of miller blue

" preind%strial process for prod%ction of indigo ;hite, %sed in *%rope, ;as to dissol1e the indigoin stale %rine? " more con1enient red%cti1e agent is inc? "nother preind%strial method, %sed in0apan, ;as to dissol1e the indigo in a heated 1at in ;hich a c%lt%re of thermophilic , anaero&ic

&acteria ;as maintained? #ome species of s%ch &acteria generate hydrogen as a meta&olic prod%ct, ;hich con1ert insol%&le indigo into sol%&le indigo ;hite? !loth dyed in s%ch a 1at ;asdecorated ;ith the techniG%es of shibori (tie-dye , kasuri $ kata+ome , and tsutsugaki ? *xamples of clothing and &anners dyed ;ith these techniG%es can &e seen in the ;orks of >ok%sai and other

artists?

Direct printing

4;o different methods for the direct application of indigo ;ere de1eloped in *ngland in the 6 thcent%ry and remained in %se ;ell into the 6)th cent%ry? 4he first method, kno;n as 'pencil &l%e'

&eca%se it ;as most often applied &y pencil or &r%sh, co%ld &e %sed to achie1e dark h%es?"rsenic tris%lfide and a thickener ;ere added to the indigo 1at? 4he arsenic compo%nd delayedthe oxidation of the indigo long eno%gh to paint the dye onto fa&rics?

https://en.wikipedia.org/wiki/Solublehttps://en.wikipedia.org/wiki/Redoxhttps://en.wikipedia.org/wiki/Oxygenhttps://en.wikipedia.org/wiki/William_Wordsworthhttps://en.wikipedia.org/wiki/Thermophilehttps://en.wikipedia.org/wiki/Thermophilehttps://en.wikipedia.org/wiki/Anaerobic_digestionhttps://en.wikipedia.org/wiki/Hydrogenhttps://en.wikipedia.org/wiki/Shiborihttps://en.wikipedia.org/wiki/Kasurihttps://en.wikipedia.org/wiki/Kasurihttps://en.wikipedia.org/wiki/Katazomehttps://en.wikipedia.org/wiki/Tsutsugakihttps://en.wikipedia.org/wiki/Hokusaihttps://en.wikipedia.org/wiki/Hokusaihttps://en.wikipedia.org/wiki/Arsenic_trisulfidehttps://en.wikipedia.org/wiki/Solublehttps://en.wikipedia.org/wiki/Redoxhttps://en.wikipedia.org/wiki/Oxygenhttps://en.wikipedia.org/wiki/William_Wordsworthhttps://en.wikipedia.org/wiki/Thermophilehttps://en.wikipedia.org/wiki/Anaerobic_digestionhttps://en.wikipedia.org/wiki/Hydrogenhttps://en.wikipedia.org/wiki/Shiborihttps://en.wikipedia.org/wiki/Kasurihttps://en.wikipedia.org/wiki/Katazomehttps://en.wikipedia.org/wiki/Tsutsugakihttps://en.wikipedia.org/wiki/Hokusaihttps://en.wikipedia.org/wiki/Arsenic_trisulfide


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9ot of free e-dried indigo dye

4he second method ;as kno;n as '!hina &l%e' d%e to its resem&lance to !hinese &l%e-and-;hite porcelain? Instead of %sing an indigo sol%tion directly, the process in1ol1ed printing the insol%&leform of indigo onto the fa&ric? 4he indigo ;as then red%ced in a seG%ence of &aths of iron(II

s%lfate, ;ith air-oxidation &et;een each immersion? 4he !hina &l%e process co%ld make sharpdesigns, &%t it co%ld not prod%ce the dark h%es possi&le ;ith the pencil &l%e method?

"ro%nd 6 /, the 'gl%cose process' ;as de1eloped? It finally ena&led the direct printing of indigoonto fa&ric and co%ld prod%ce inexpensi1e dark indigo prints %nattaina&le ;ith the !hina &l%emethod?

#ince 2// , free e-dried indigo, or instant indigo, has &ecome a1aila&le? In this method, theindigo has already &een red%ced, and then free e-dried into a crystal? 4he crystals are added to;arm ;ater to create the dye pot? "s in a standard indigo dye pot, care has to &e taken to a1oidmixing in oxygen? Free e-dried indigo is simple to %se, and the crystals can &e stored indefinitely

as long as they are not exposed to moist%re ?:6 <

Chemical properties

Indigo

Indigo is a dark &l%e crystalline po;der that s%&limes at 3)/E3)2 A! (.3 E.3 AF ? It isinsol%&le in ;ater, alcohol , or ether , &%t sol%&le in +#O , chloroform , nitro&en ene, andconcentrated s%lf%ric acid? 4he chemical form%la of indigo is ! 6=> 6/ $ 2O2?

4he molec%le a&sor&s light in the orange part of the spectr%m (U max V =63 nm ?:6 < 4he compo%ndo;es its deep color to the con %gation of the do%&le &onds, i?e? the do%&le &onds ;ithin themolec%le are ad acent and the molec%le is planar? In indigo ;hite, the con %gation is interr%pted

&eca%se the molec%le is nonplanar?

Chemical synthesis

7i1en its economic importance, indigo has &een prepared &y many methods? 4he Baeyer-re;son indigo synthesis dates &ack to 6 2? It in1ol1es an aldol condensation of o-

nitro&en aldehyde ;ith acetone, follo;ed &y cycli ation and oxidati1e dimeri ation to indigo?4his ro%te is highly %sef%l for o&taining indigo and many of its deri1ati1es on the la&oratory

https://en.wikipedia.org/wiki/Iron(II)_sulfatehttps://en.wikipedia.org/wiki/Iron(II)_sulfatehttps://en.wikipedia.org/wiki/Freeze_dryinghttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-14https://en.wikipedia.org/wiki/Indigo_dye#cite_note-14https://en.wikipedia.org/wiki/Sublimation_(chemistry)https://en.wikipedia.org/wiki/Sublimation_(chemistry)https://en.wikipedia.org/wiki/Sublimation_(chemistry)https://en.wikipedia.org/wiki/Ethanolhttps://en.wikipedia.org/wiki/Ethanolhttps://en.wikipedia.org/wiki/Diethyl_etherhttps://en.wikipedia.org/wiki/Dimethyl_sulfoxidehttps://en.wikipedia.org/wiki/Chloroformhttps://en.wikipedia.org/wiki/Nitrobenzenehttps://en.wikipedia.org/wiki/Sulfuric_acidhttps://en.wikipedia.org/wiki/Chemical_formulahttps://en.wikipedia.org/wiki/Chemical_formulahttps://en.wikipedia.org/wiki/Carbonhttps://en.wikipedia.org/wiki/Hydrogenhttps://en.wikipedia.org/wiki/Nitrogenhttps://en.wikipedia.org/wiki/Oxygenhttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-15https://en.wikipedia.org/wiki/Double_bondhttps://en.wikipedia.org/wiki/Double_bondhttps://en.wikipedia.org/wiki/Baeyer-Drewson_indigo_synthesishttps://en.wikipedia.org/wiki/Baeyer-Drewson_indigo_synthesishttps://en.wikipedia.org/wiki/Iron(II)_sulfatehttps://en.wikipedia.org/wiki/Iron(II)_sulfatehttps://en.wikipedia.org/wiki/Freeze_dryinghttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-14https://en.wikipedia.org/wiki/Sublimation_(chemistry)https://en.wikipedia.org/wiki/Ethanolhttps://en.wikipedia.org/wiki/Diethyl_etherhttps://en.wikipedia.org/wiki/Dimethyl_sulfoxidehttps://en.wikipedia.org/wiki/Chloroformhttps://en.wikipedia.org/wiki/Nitrobenzenehttps://en.wikipedia.org/wiki/Sulfuric_acidhttps://en.wikipedia.org/wiki/Chemical_formulahttps://en.wikipedia.org/wiki/Carbonhttps://en.wikipedia.org/wiki/Hydrogenhttps://en.wikipedia.org/wiki/Nitrogenhttps://en.wikipedia.org/wiki/Oxygenhttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-15https://en.wikipedia.org/wiki/Double_bondhttps://en.wikipedia.org/wiki/Baeyer-Drewson_indigo_synthesishttps://en.wikipedia.org/wiki/Baeyer-Drewson_indigo_synthesis


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scale, &%t ;as impractical for ind%strial-scale synthesis? 0ohannes 9fleger :62< and 8arl >e%mann (de e1ent%ally came %p ;ith ind%strial mass prod%ction synthesis? :63< 4he first commercially

practical ro%te is credited to 9fleger in 6)/6? In this process, N -phenylglycine is treated ;ith amolten mixt%re of sodi%m hydroxide , potassi%m hydroxide , and sodamide ? 4his highly sensiti1emelt prod%ces indoxyl , ;hich is s%&seG%ently oxidi ed in air to form indigo? Qariations of this

method are still in %se today? "n alternati1e and also 1ia&le ro%te to indigo is credited to>e%mann in 6 ).? It in1ol1es heating N -(2-car&oxyphenyl glycine to 2// A! (3)2 AF in an inertatmosphere ;ith sodi%m hydroxide? 4he process is easier than the 9fleger method, &%t the

prec%rsors are more expensi1e? Indoxyl-2-car&oxylic acid is generated? 4his material readilydecar&oxylates to gi1e indoxyl, ;hich oxidi es in air to form indigo? :6< 4he preparation of indigodye is practiced in college la&oratory classes according to the original Baeyer- re;sen ro%te? :6=<

>e%mann's original synthesis of indigo

9fleger's synthesis of indigo

Indigo derivatives

#tr%ct%re of 4yrian p%rple

#tr%ct%re of indigo carmine?

4he &en ene rings in indigo can &e modified to gi1e a 1ariety of related dyest%ffs? 4hioindigo ,;here the t;o $> gro%ps are replaced &y # atoms, is deep red? 4yrian p%rple is a d%ll p%rple dyethat is secreted &y a common +editerranean snail? It ;as highly pri ed in antiG%ity? In 6)/), itsstr%ct%re ;as sho;n to &e =,='-di&romoindigo? It has ne1er &een prod%ced on a commercial

&asis? 4he related !i&a &l%e ( ,., ,. -tetra&romoindigo is, ho;e1er, of commercial 1al%e?Indigo and its deri1ati1es feat%ring intra- and intermolec%lar hydrogen &onding ha1e 1ery lo;sol%&ility in organic sol1ents? 4hey can &e made sol%&le %sing transient protecting gro%ps s%chas the tBO! gro%p , ;hich s%ppresses intermolec%lar &onding ?:6.< >eating of the tBO! indigores%lts in efficient thermal deprotection and regeneration of the parent >-&onded pigment?

https://en.wikipedia.org/wiki/Indigo_dye#cite_note-history.evonik.com-12https://en.wikipedia.org/w/index.php?title=Karl_Heumann&action=edit&redlink=1https://de.wikipedia.org/wiki/Karl_Heumannhttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-ingenious.org.uk-13https://en.wikipedia.org/wiki/Sodium_hydroxidehttps://en.wikipedia.org/wiki/Potassium_hydroxidehttps://en.wikipedia.org/wiki/Sodamidehttps://en.wikipedia.org/wiki/Sodamidehttps://en.wikipedia.org/wiki/Indoxylhttps://en.wikipedia.org/wiki/Indoxylhttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-Ullmann-1https://en.wikipedia.org/wiki/Indigo_dye#cite_note-16https://en.wikipedia.org/wiki/Thioindigohttps://en.wikipedia.org/wiki/Tyrian_purplehttps://en.wikipedia.org/wiki/Tyrian_purplehttps://en.wikipedia.org/w/index.php?title=Ciba_blue&action=edit&redlink=1https://en.wikipedia.org/wiki/Protecting_grouphttps://en.wikipedia.org/wiki/Tert-butyloxycarbonyl_protecting_grouphttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-17https://en.wikipedia.org/wiki/Indigo_dye#cite_note-17https://en.wikipedia.org/wiki/Indigo_dye#cite_note-17https://en.wikipedia.org/wiki/Indigo_dye#cite_note-history.evonik.com-12https://en.wikipedia.org/w/index.php?title=Karl_Heumann&action=edit&redlink=1https://de.wikipedia.org/wiki/Karl_Heumannhttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-ingenious.org.uk-13https://en.wikipedia.org/wiki/Sodium_hydroxidehttps://en.wikipedia.org/wiki/Potassium_hydroxidehttps://en.wikipedia.org/wiki/Sodamidehttps://en.wikipedia.org/wiki/Indoxylhttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-Ullmann-1https://en.wikipedia.org/wiki/Indigo_dye#cite_note-16https://en.wikipedia.org/wiki/Thioindigohttps://en.wikipedia.org/wiki/Tyrian_purplehttps://en.wikipedia.org/w/index.php?title=Ciba_blue&action=edit&redlink=1https://en.wikipedia.org/wiki/Protecting_grouphttps://en.wikipedia.org/wiki/Tert-butyloxycarbonyl_protecting_grouphttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-17


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4reatment ;ith s%lf%ric acid con1erts indigo into a &l%e-green deri1ati1e called indigo carmine (s%lfonated indigo ? It &ecame a1aila&le in the mid-6 th cent%ry? It is %sed as a colorant for food,

pharmace%ticals, and cosmetics?

Indigo as an organic semiconductor

Indigo and some of its deri1ati1es are kno;n to &e am&ipolar organic semicond%ctors ;hendeposited as thin films &y 1ac%%m e1aporation? :6 <

!afety and the environment

Indigo has a lo; oral toxicity, ;ith an / of /// mg@kg in mammals? :6< In 2//), large spills of &l%e dyes had &een reported do;nstream of a &l%e eans man%fact%rer in esotho ?:6)<

!ee also

Stone washing

From Wikipedia, the free encyclopedia

Stone-washed jeans

https://en.wikipedia.org/wiki/Indigo_carminehttps://en.wikipedia.org/wiki/Organic_semiconductorshttps://en.wikipedia.org/wiki/Organic_semiconductorshttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-18https://en.wikipedia.org/wiki/Median_lethal_dosehttps://en.wikipedia.org/wiki/Median_lethal_dosehttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-Ullmann-1https://en.wikipedia.org/wiki/Lesothohttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-st2009-19https://en.wikipedia.org/wiki/Indigo_carminehttps://en.wikipedia.org/wiki/Organic_semiconductorshttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-18https://en.wikipedia.org/wiki/Median_lethal_dosehttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-Ullmann-1https://en.wikipedia.org/wiki/Lesothohttps://en.wikipedia.org/wiki/Indigo_dye#cite_note-st2009-19


12/14

Ronald Reagan wearing stonewash denim associated with Western clothing , 1970s

!tone ashing is a textile man%fact%ring process %sed to gi1e a ne;ly man%fact%red clothgarment a ;orn-in (or ;orn-o%t appearance? #tone-;ashing also helps to increase the softnessand flexi&ility of other;ise stiff and rigid fa&rics s%ch as can1as and denim ?

4he process %ses large stones to ro%ghen %p the fa&ric &eing processed? 4he garments are placedin a large hori ontal ind%strial clothes ;asher that is also filled ;ith large stones? "s the ;ashcylinder rotates, the cloth fi&ers are repeatedly po%nded and &eaten as the t%m&ling stones ride%p the paddles inside the dr%m and fall &ack do;n onto the fa&ric?

" n%m&er of people and organi ations ha1e claimed to ha1e in1ented stone-;ashing? "ccordingto e1i #tra%ss H !o? , onald Freeland, an employee of the 7reat Western 7arment !ompany (later acG%ired &y e1i's , in1ented Tstone-;ashingT denim in the 6) /s? In1entor !la%deBlankiet has also &een credited ;ith ha1ing in1ented the techniG%e in the 6)./s ?:6< 4he eanscompany *d;in claims to ha1e in1ented the techniG%e in the 6) /s? :2<

!ontents

• 1 Stonewashed jeans

• " #cid-washed jeans

o " 1 $arly e%amples

o " " &ainstream pop'larity

https://en.wikipedia.org/wiki/Ronald_Reaganhttps://en.wikipedia.org/wiki/Western_clothinghttps://en.wikipedia.org/wiki/Textile_manufacturinghttps://en.wikipedia.org/wiki/Canvashttps://en.wikipedia.org/wiki/Denimhttps://en.wikipedia.org/wiki/Clothes_washerhttps://en.wikipedia.org/wiki/Levi_Strauss_%26_Co.https://en.wikipedia.org/wiki/Great_Western_Garment_Co.https://en.wikipedia.org/wiki/Stone_washing#cite_note-1https://en.wikipedia.org/wiki/Stone_washing#cite_note-1https://en.wikipedia.org/wiki/Edwin_(clothing_retailer)https://en.wikipedia.org/wiki/Stone_washing#cite_note-2https://en.wikipedia.org/wiki/Stone_washing#Stonewashed_jeanshttps://en.wikipedia.org/wiki/Stone_washing#Acid-washed_jeanshttps://en.wikipedia.org/wiki/Stone_washing#Early_exampleshttps://en.wikipedia.org/wiki/Stone_washing#Mainstream_popularityhttps://en.wikipedia.org/wiki/Ronald_Reaganhttps://en.wikipedia.org/wiki/Western_clothinghttps://en.wikipedia.org/wiki/Textile_manufacturinghttps://en.wikipedia.org/wiki/Canvashttps://en.wikipedia.org/wiki/Denimhttps://en.wikipedia.org/wiki/Clothes_washerhttps://en.wikipedia.org/wiki/Levi_Strauss_%26_Co.https://en.wikipedia.org/wiki/Great_Western_Garment_Co.https://en.wikipedia.org/wiki/Stone_washing#cite_note-1https://en.wikipedia.org/wiki/Edwin_(clothing_retailer)https://en.wikipedia.org/wiki/Stone_washing#cite_note-2https://en.wikipedia.org/wiki/Stone_washing#Stonewashed_jeanshttps://en.wikipedia.org/wiki/Stone_washing#Acid-washed_jeanshttps://en.wikipedia.org/wiki/Stone_washing#Early_exampleshttps://en.wikipedia.org/wiki/Stone_washing#Mainstream_popularity


13/14


14/14

the process &y soaking the eans in dil%ted &leach and some &each sand? #imple chlorine &leachand m%riatic acid ;ere readily a1aila&le at this time, as they ;ere %sed to sterilise s;imming

pools? :6/<

&ainstream pop'larity

%ring the early 6) /s, skinheads and p%nk rockers ;o%ld spatter &leach on their eans and &attle ackets for a mottled effect similar to camo%flage?:66< 4his early faded look, kno;n as sno;;ash, tended to retain the original dark &l%e dye aro%nd the seams and ;aist&and? One of thefirst companies to sell Tpre ;ashedT eans (as they ;ere then called , ;as 7%ess inc? in 6) 6? :62<

espite its association ;ith p%nk fashion , ho;e1er, the faded effect ;as copied &y manyindi1id%als not associated ;ith the s%&c%lt%re, ;ho dipped their eans in dil%ted &leach andem&ellished them ;ith metal st%ds, em&roidery and rhinestones ?:63<

4he modern process of acid ;ashing ;as patented in Italy &y the ifle eans company in

Fe&r%ary 6) =?:6 < 4hey accidentally t%m&led eans and p%mice stones ;etted ;ith a ;eaksol%tion of &leach in a ;ashing machine ;itho%t ;ater? "merican 7arment Finishers ("7F from4exas ind%striali ed the process in $orth "merica in 0%ne 6) = and offered it to e1i #tra%ss? :6 < #hortly after;ard, "7F impro1ed the techniG%e &y %sing 9otassi%m 9ermanganate instead of

&leach, achie1ing a more nat%ral a&raded look that is far less damaging to the cotton fi&ers? Other a&rading materials s%ch as mar&le sand or expanded glass foam ;ere also %sed as an alternati1eto p%mice stone (see stone-;ash ? #pecific areas of the eans, shirts and ackets ;ere also acid-;ashed &y spraying a sol%tion of &leach or potassi%m permanganate to sim%late a ;ear pattern?*xtremely pop%lar ;orld;ide from 6) = to the mid nineties, it is still %sed &y fashion designerstoday?:6=<

)ecline and re*i*al

"cid ;ash eans, ;orn ;ith fringe ackets or the 9erfecto motorcycle acket ;ere pop%larised &yhard rock , o%tla; co%ntry and hea1y metal &ands in the late 6) /s? Fans of hair metal fa1oredfrayed Tdestroyed denim,T and eans that had &een &leached almost ;hite? #no; ;ashed eans,;hich retained more of the original &l%e dye, remained pop%lar among gr%nge fans d%ring themid 6))/s, %ntil they ;ere e1ent%ally s%pplanted &y darker shades of denim associated ;ithhardcore p%nk and hip hop fashion ?:6.< "cid ;ashed eans made a come&ack in the late 2///samong teenage girls, d%e to a re1i1al of 6) /s and 6))/s fashions that contin%ed into the 2/6/s?
https://en.wikipedia.org/wiki/Stone_washing#cite_note-10https://en.wikipedia.org/wiki/Skinheadhttps://en.wikipedia.org/wiki/Punk_rockerhttps://en.wikipedia.org/wiki/Punk_rockerhttps://en.wikipedia.org/wiki/Bleachhttps://en.wikipedia.org/wiki/Battle_jackethttps://en.wikipedia.org/wiki/Camouflagehttps://en.wikipedia.org/wiki/Stone_washing#cite_note-11https://en.wikipedia.org/wiki/Guess_inc.https://en.wikipedia.org/wiki/Stone_washing#cite_note-12https://en.wikipedia.org/wiki/Stone_washing#cite_note-12https://en.wikipedia.org/wiki/Punk_fashionhttps://en.wikipedia.org/wiki/Rhinestonehttps://en.wikipedia.org/wiki/Stone_washing#cite_note-13https://en.wikipedia.org/wiki/Rifle_(fashion)https://en.wikipedia.org/wiki/Rifle_(fashion)https://en.wikipedia.org/wiki/Stone_washing#cite_note-14https://en.wikipedia.org/wiki/Stone_washing#cite_note-15https://en.wikipedia.org/wiki/Stone_washing#cite_note-16https://en.wikipedia.org/wiki/Fringe_jackethttps://en.wikipedia.org/wiki/Perfecto_motorcycle_jackethttps://en.wikipedia.org/wiki/Hard_rockhttps://en.wikipedia.org/wiki/Outlaw_countryhttps://en.wikipedia.org/wiki/Heavy_metal_musichttps://en.wikipedia.org/wiki/Hair_metalhttps://en.wikipedia.org/wiki/Grungehttps://en.wikipedia.org/wiki/Grungehttps://en.wikipedia.org/wiki/Hardcore_punkhttps://en.wikipedia.org/wiki/Hip_hop_fashionhttps://en.wikipedia.org/wiki/Stone_washing#cite_note-17https://en.wikipedia.org/wiki/1990s_fashionhttps://en.wikipedia.org/wiki/Stone_washing#cite_note-10https://en.wikipedia.org/wiki/Skinheadhttps://en.wikipedia.org/wiki/Punk_rockerhttps://en.wikipedia.org/wiki/Bleachhttps://en.wikipedia.org/wiki/Battle_jackethttps://en.wikipedia.org/wiki/Camouflagehttps://en.wikipedia.org/wiki/Stone_washing#cite_note-11https://en.wikipedia.org/wiki/Guess_inc.https://en.wikipedia.org/wiki/Stone_washing#cite_note-12https://en.wikipedia.org/wiki/Punk_fashionhttps://en.wikipedia.org/wiki/Rhinestonehttps://en.wikipedia.org/wiki/Stone_washing#cite_note-13https://en.wikipedia.org/wiki/Rifle_(fashion)https://en.wikipedia.org/wiki/Stone_washing#cite_note-14https://en.wikipedia.org/wiki/Stone_washing#cite_note-15https://en.wikipedia.org/wiki/Stone_washing#cite_note-16https://en.wikipedia.org/wiki/Fringe_jackethttps://en.wikipedia.org/wiki/Perfecto_motorcycle_jackethttps://en.wikipedia.org/wiki/Hard_rockhttps://en.wikipedia.org/wiki/Outlaw_countryhttps://en.wikipedia.org/wiki/Heavy_metal_musichttps://en.wikipedia.org/wiki/Hair_metalhttps://en.wikipedia.org/wiki/Grungehttps://en.wikipedia.org/wiki/Hardcore_punkhttps://en.wikipedia.org/wiki/Hip_hop_fashionhttps://en.wikipedia.org/wiki/Stone_washing#cite_note-17https://en.wikipedia.org/wiki/1990s_fashion

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