SAD

CHEMICAL SYSTEMS LABORATORY TECHNICAL REPORT

ARCSL-TR-810564

EVALUATION OF REPLACEMENT RED SMOKE DYES

FOR I-N METHYLAMINOANTHRAQUINONE

by

F Ellen S. Vigus0 Albert Deiner

Munitions Division

CIL

October 1981

I' ~A US ARMY ARMAMENT RESEARCH AND DEVELOPMENT COMMAND

•"}[IIl•Che•mical Syrups Labonrv ID

LUJ Aberdwen Proving Ground, Marylad 21010

418T AVAILOWLE Copy- Approved for public relem; distibutlon unlmolted

I.• .11 12 I,..

Disclaimer

The findings in this report are not to be construed as an official Department of the Armypositior uniA,,ss so designated by other authorized documents.

Disposition

Destroy this report when it is no longer needed. Do not return it to the originator.

MýU

-* UNCLASSIFIEDSECURITY CLASSIFICATION OF THIS PAGE ("oin Date Entered)

REPORT DOCUMENTATION PAGE READ INSTRUCTIONSBEFORE COMPLETING FORM

2. GOVT ACCESSION No. 3. RECIPIENT'S CATALOG NUMBER

AkC-SL-TR-8 1ý054 0492e 7g~4,_TIIILEu(d SUWýa4 yf o peRLER0OD COVERED

EVALUATION OF REPLACEMENT RED.§MOKE DYES, chiaFOR IN METHYLAMINOANT'IRAQUINONE, o~~~9My~~

7. AUTHOP(s) 11. CONTRACT OR GRANT NUMSER(s)

9. PERFORMING ORGANIZATION NAME AND ADDRESS 10. PROGRAM ELEMENT. PROJECT, TASK

Commander/Director, Chemical Systems Laboratory AREA & WORK UNIT NUMBERS

ATTN-- DRDAR-CLN-DAberdeen Proving Ground, Maryland 21010 Project IA98772

11. CONTROLLI NG OFFICE NAME AND ADDRESS 22- REA1,PABL.ýCommander/Director, Chemical Systems Laboratory / Octebr J08 lJATTN:' DRDAR-CLJ-R C,111. NUMBER OF PAGES

Aberdeen Proving Ground, Maryland 21010 2014. MONITORING AGENCY4#M.&`A0V''ASS(if diff erent from. Controlling Office) IS. SECURITY CLASS. (of this report)

15 UNCLASSIFIEDr Da ýECLASSI PICATION4/OOWN4GRADING,

SCHEDULE NAIS. DISTRIBUTION STATEMENT (of this Report)

Approved for public release;' distribution unlimited.17. DISTRIBUTION STATEMENT (of the abstract entered In Block 20, i.: different froau Report)

IS. SUPPLEMENTARY NOTES

19. KEY WORDS (Continua on reverse side iflnecossary and identily b,- block namaber)

Red smoke dyes Pyrotechnics Toxicology1-N Methylamninoanthraquinone Sudan Red G FDA dyes9-Diethylaminorosindone M-1 8 grenadeO-Methoxyphenylazo-j3-naphthol

2&. AsSTrACT (cotimse onrewares ebb fneosewen and ideetlf, by block mumber)

A list of 114 dyes was compiled from a literature search for replacement red smo~kedyes for 1-N methylaminoanthraquinone. Two of the dyes reviewed (9-diethylanunorosindoneand O-mfethoxyphenylazo-B-naphthol) were found to meet the requirements for ise inpyrotechnics. There are insufficient toxicological data at this time to assess the I.ealth effectsof these dyes. •>

W') I a 14n3/ EBITIOW OF I uov es1 IBsOL9ETE UNCLASSIFIED

NEURTY CLAisIFICATION Of THIS PAGE (910on Date Rnterd

PREFACE

The work described in this report was authorized under Project I A98772, Engineering Studyto Determine Feasibility of Replacing Dye, Disperse Red 9. This work was started in N'ovember 1979and completed in May 1980.

The use of trade names in this report does not constitute an official endorsement orapproval of the use of such commercial hariware or software. This report may not be cited forpurposes of advertisement.

Reproduction of this document in whole or in part is prohibited except with permissionI of tWe Conimander/Director, Chemical Systems Laboratory, ATTN: DRDAR-CLJ-R, Aberdeen Proving"Ground, Maryland 21010. However, the Defense Technical Information Center and the NationalTechnical Information Service are authorized to reproduce the document for United States governmentpurposes.

_-. 3gJ

CONTENTS

Page

I INTRODUCTION ............. .............................. . 7

2 METHOD. 7 . .. .................... .. .7

3 RESULTS ........................................... . ..... 7

4 DISCUSSION OF RESULTS ................ .................... . 11

4.1 9-Diethylaminorosindone ........ .............................. 12

4.2 o-Methoxyphenylazo-p-naphthol ....... ....................... . 12

5 CONCLUSIONS AND RECOMMENDATIONS .................. 12

LITERATURE CITED ........ ................................ 13

SELECTED REFERENCES ........ ........................... .. 15

DISTRIBUTION LIST . ................ .......................... 17

r5

EVALUATION OF REPLACEMENT RED SMOKE DYESFOR I-N METHYLAMINOANTHRAQUINONE

S1. INTRODUCTION

The objective of this work was to compile a list of possbile replacement compounds for thedye currently employed to generate red smoke by pyrotechnic methods. The red dye now used is1-N methylaminoanthraquinone.

2, METHOD

A list of dyes used or tested for use in pyrotechnics was compiled by reviewing openliterature and reports available in the Technical Library of Chemical Systems Laboratory.

Representatives from dye manufacturing companies were consulted to determine whether anynew available dyes -ould be employed for use with pyrotechnic compositions.

The list of Food and Drug Administration dyes subject to certification (revised April 1, 1979)was reviewed for replacemeni dyes. These dyes are commercially available, and toxicological testinghas already been performed on each.

3. RESULTS

Table 1 lists the dyes from the open literature and from reports in the Technical Librarywhich have been used or tested for use in pyrotechnic smoke compositions.

Included with the list of dyes is the following.,

a.a. Manufacturer, if available.

b. Other names - commercial or chemical,

c. Colour Index (CI) number (Numbers before 10000 are no longet listed in the currentColour Index.)

Table 2 lists the Food and Drug Administration dyes reviewed. Current Colour Indexnumbers are noted.,

Consultations with dye manufacturers yielded one possible dye, Rhodamine B.

7

Table 1. aysUsedorTested fat onin PymwtdulCS

I Acetwnine Scarlet b Made by Du~ont 1,3

22

4. AD 779 2,'

S. Alpha-amino anthraqwflone 45

6 Amino Azobienzene

7 Amino azotoluene*n ,phthol 3

8 2-Amino biphenyl-13-naphthol

9 1 -Aznano-4-hydroy anthrfaquiflofe Celanthreue Red 3B 1, 3,4Madae by DuPont

10. Andine-1-hydroxy naphithalene-4-sulforiic acid 3

11I. Anilinc azo-o-naphithol 6

12. 5.Anilinobenzo (a) plenahine Rosinhiline GX. CI 828 1

13 o-Anulicne-i-hyd~oxy naphithalencJI-sufortic acid 3

i14. p-Aniiidine-i-hydroxy naphithaiene.44tiifoflic acid 3

iS o-Anisdine azo a-naphthol 6

16 o-Anwdine azo resorcinol6

17. 4-Anisole azo J-naphthol 2

18 Azo Red K 1858 7

IY l-(4.Benzamido-2,S-dimcthoxy pneiqyiazo)-2-naphthoi Fast Olue 33

I20. 1.{2.Biphenylazo)-2-naphthol Dry R~d X9848 I

21. Brillhant Red R Msde by Caco -7

i 22. 5-Bromo.2(S.7.dibroino3.oxo-3(2)ýifdolydinflC2)tidiU18Phtinfoni Cibia Violet B. Ci 1222 1*C1 73620 (Vat Dye)$

3 Calcolake Red D7

24 p-Chloroandine-Pnaphthol 1,3

25. p-Ch~or-c~anisidine-l-hydYoxyflaphthsleflc~a~fonkc acid 3

I26 4-Chior-2-anisole-rzoiPnaphthoI 2.,3

27 4-Chlor-2,5-dinmethoxybeflzene-4zo-PnaphthoI1,,

28. 5-Chloro-2<hydoxy-1.naphthylaz0)p-tdUoluei sulfonic acid Caicolake Red C I

29 5,5S.Chloro.6.6'.methylthifoindigo Sulfanthrene Red 3D1 1CI 1212

30. 44(p-Chlotophenylyazo)-N,N-dihydroxy ethyisniline 1

3.44p-CiPJorophenylazo)ýN-Cthyl.N.(2.hydroxytthyl) anilineI

32 Cresidine-l -hydroxy naphithalcle-4-suifofic acid 3

33 I ,S.Diamino anthraquinone 434. i,4-Dibentoylamino anthraquinoneI35. 2,4-)ciiioroaniiine-q-naphthol4

36. 2,S.Thchloroaani1ne4-naphthol 1,3

37 2,5.Diethoxyaflhinoonaphithol 1.3

38. 9-Dicthylaminto rcamdone 9.Dkthlsyian~n&71ilenyl-i4bfl (a) phenaclnone 1,2,5,7(MILD).36i4) 9-11

39 9. Diethylumino-7-p-tolyi-S-benzo (a&jhenxzuionef Rodridmte Y Ixional AD 1,7,9

40. N,N-.Diethyi-p,p'-nitropheiiylazolnilne I *

41 2,5.Dimcthoxybenzefle-IzoO-niaphthoI -CI 12156 (Solvent Red SOP ~ 1.2, 3

42. 1,5-Oimethyitinino antliraquinone 6

43. 1,8.Dimethyi-3,6-dichloro thioindigo 3

44. 4-(2.4-Dinitro phenylazo) phenolI

45. 6-Ethoxy-2.2mino-benzthiazoC.CthyI&Wiol 1.3

-46. S.Etiiyl-2-aniaole-azo.P-naphitholl 2

47. Federa Continental Red 3

See footnote at end of table.

Table 1. (Contd)

Dye' Reterence

48 Federal Independence Red *C1 12120 (Pigment Red 3)8 349 Federal Lincoln Red Chlorinated p-filmo phenylzao-2*naphttsol 1, 3

*C1 12085 (Pigment Red 4)850 Federal Signal Red B 3,751 Federal Smoke Red D 7

52 4-Hydruxy-34I2.4-djinethoxy phenylazo)- I -naphthalene Isulfonic acid

53 4-Hydroxy-3.jp-cthoxvphenylazvj-lI napthalene sulfonic acid

54 4-Hiydroxy-3-( 2-hydroxy-ni-iolylazo>, I -naphthalene sulfonic acid1

55 4-tiydroxy-3-( o-miethoxy-p-chloroph~riylazo) -I naphthalene Isulfonic acid

56 4-Hydroxy-3-(o-methoxyphenylazo)-I -naphthalene sulfonic acid Azo Eoiine GCl 114

57 24(2-Hydroxy-I1-naphthylavoflI naphthalene sulfortic acid Litho[ Red R. Cl 1891

*C1 15630 (CI Pigment Red 49)858 4-Hydroxy-3-phenmylazo- I -n~iphthalene sulfonic acidI

59 I -2-H> droxy-m-tolylazo)- 2.naphthol Oil BronzeI

60. Indophenol BW I61 1Indophenol RI. I62 Induline Base 5G Mixture of 2.3,7-trianilino-5phenylphenaziniui~ii

chlon&i and 2,3,7,8.tetraanilino.S-phenwi.

63 Isorosindurine 364 K1840(see references 3 and 14) Ammoniunm salt of Litho[ Red 7I Manufactured by Krebs65 Litho] Red Toner Manufactured by United 766 144-Methoxy arulino) phenylazo}.2-naphthol Vanamine Blue BDI

Made by General Dyestuff Corp67, l{2-Methoxy-4-nitrophenylazo)-2-naphthoI Naphthol Pink, Cl 117 168 o-Methoxyphenylazo.O.naphthol Sudan R, Federal Signal Red A, BMilliant Fat 1, 2, 3, 5, 6, 9, 12

Scarlet, Calco Oil Scarlet OBN, MIL.D-3 179,Cl 113Cl 12150 (Solvent Red 1)8

69 5.Methyl.2.anisole-azo-o-naphthol Cl 12155 (Solvent Ked 17) 8 270 4,4'.Methy1.6.6' -chlorothioiridigo Sulfat~threne Pink FFI

Made by DuPont*C1 73360 (Vat Red 1) 8

71 2-(Monobronio-2-oxo- I(2)-acenaphthylidiie-3(2)- Ciba Red R, C1 12291thianaphitherione *C1 73865 (Vat Dye)

8

72. a-Naphthylamine-0-naphthol Federal Red, Naphthylamine Bordeaux 3, 4,6, 8*Cl 12070 (CI Pigmnent Rcd 1)

73 Pl.Naphthylamnine-0-naphthol Azo Turkish Red 3,4,6

74114 1 -Naphthylazo)-2-naphthol Oil Red, Cl 82175 l-(2-Naphthylazo)-2-naphthol Sudan CB, C1 93176 1-Nitro-aceidone 1,3

77. l-(2-Nitro-o-tolylazo)-2-naphthol Toluidine Toner, Lithol Fast 1,4

78 2-(2-Oxo-1(2}acenaphthylidine).3(2)-thianaphtlsenone Sulfanthrene Scarlet Y, Cl 12281

OC1 73860 (Vat Red 45)79. Paranitroaiuline 1,1,13

80. Panrantroamline-diethylaniline 381. Para Red Toner Made by United 7

82. Paratoner Red 1,3, 14

82 Paratoner RT435D I I

*See Footnote at end of table 9

Table 1. (Coutd)

Dye Risfrencej

84. 144-Phenetlsyl phenylzo).2-naphthol I

85. p-Phenetidine-l-hydroxy naphlstilaene-44ulfonic &led 3

86. p-Phenewbne-0naphthol '3,6

87. p-Phenvlazo aniline hydwocholoride I

88 4-Plenyl zo3-hydroxy-2.saphthoac acid Calcolake 11tililant Red RI

89. 144Phenylazo qhenylazo).2-nsphthol Sudan 111, 0il Red, GI 248 1,4

90. Pyronine G *C1 45005 (Dale Dye) a4

91. Rlhodamnlne Rhodarnine 3. Rhodanse BEx 1,4, 14.6

C1 749 10.12,15

92. Phodamine 5GDN base 3I'93. Rhodamine 6GDNEx 3.4,.1094. RosinduLine 3

95 Rosindone True Rogindooe 1, 3.9F 9 Safraine T byxur of37daio21-dmt~--hn I

2,8-dmethlsy-5.0-tol~,iphenaznlium ChlorideCI 41,Mad byDuPont

97. Sodium salt of o-carboxylic acid of benzene- 3azo-0-naphithol-3:6-disuslphoruc acid

98. Sodruis salt of 4-spho-A-ruphthsalene-azo.p- 3

naphthol.-&sulphonic acid

99. SudanlIV Spirit Redl111 1,4.6.12

100. Tetrazotized benzidinc.0-naphthol 6

101. Tetrazotized o-dianisidine-o-naphthol 6

102 fetrazotized o-tolidine-ci-naphtlsol 6

103. Tetrazotized o-tolsdine-~naphthol 6

104. Thioindigo Dunndone Red B, C1 1207 1,6

*C1 73300 (Vat Red 41) 8

105 Xylident-0naphthol 3,6

106. I-Xylylazo-2-naphtlsol Calco Oil Scarlet 11, National 0OilScarlet 6G, Sudan 11, Sudan RedC1 12140 ýSolvcnt Orange 7)3

These are the new Colour Index numbers as best as can be ascertained from the ardormation available.

10

Table 2. US Food and Drug Administration Dyes

Dye Colour index number

1. FD&C #40 16035

2. FD&C #3 45430

"3, Citrus Red #2 121564. FD&C Red #4 14700

5. D&C Red #17 261006. D&C Red #31 15800:1

7., D&C Red #34 15880:1

8, D&C Red #39 13058

4., DISCUSSION OF RESULTS

Investigators1,4, 14 generally agree upon the following properties of dyes suitable for theproduction of colored smokes:

a. The molecular weight must not exceed 450.

b., The dye should be a member of one of the following series:' anthraquinone, azine, azo,quinoline, or xanthene..

c. The following groups must be absent:. sulfonic, hydrochloride, nitro, nitroso, quaternaryammonium, and oxonium.

d. The following groups may be present:, amino and substituted amino, alkyl, aryl, chloro,bromo, hydroxy, and alkoxy.

e. The dye must not have a tendency to undergo auto condensation. Of the dyes reviewed,

the following have these properties::

(1) Rhodamine B

(2) Sudan IV

(3) 1 Xylylazo-2-naphthol

(4) Citrus Red #2 (2,5 dimethyoxyphenylazo-2-naphthol)

(5) 9-Diethylaminorobiidone

(6) O-Methoxyphenylazo-B-naphthol

11

The first four dyes in the list have been shown to be mutagenic or carcinogenic in studiesreviewed in the Registry of Toxic Effects of Chemical Substances. 16 In addition, Rhodamine B waslisted as a potential health hazard in a report by Anson and Parent, 15 and Citrus Red tends to flameand decompose when disseminated. For these reasons, these dyes were eliminated from furtherconsideration.

The remaining two dyes, 9-diethylaminorosindone and o-methoxyphenylazo-p3-naphthol, have

been recommended by various investigators as replacement dyes for 1-N methylaminoanthraquinone.

4. 1 9-Diethylaminorosindone.

Until 1960, 9-diethylaminorosindone, a member of the azine class of dyes was one of thedyes specified for use in the Ml 8 colored-smoke hand grenade. The military specification for this dyewas MIL-D-3614 19 which replaced Army 96-111-100. According to Munro and Guion,9 9-diethyl-aminorosindone produced a red smoke comparable in quality and color to that produced by I-Nmethylaminoanthraquinone, Difficulties in obtaining the necessary starting materials and the difficultsynthesis for the rosindone dyes as compared to the anthraquinone dyes led to the phasing out ofrosindone dyes in favor of the anthraquinone dyes by the dye industry.

No present commercial supp.ier for 9-diethylaminorosindone was located during this study;'however, a former manufacturer, Buffalo Color and Chemical Corporation (National Aniline), locatedin their files a procedure for synthesizing the dye. However, interest in resuming manufacture of thedye was not officially expressed by the company.

No toxicological data 15-18 wt-re located for this dye.

4.2 O-Methoxyphenylazo-B-naphthol.

o-Methoxyphenylazo-3-naphthcl, a member of the azo class of dyes, has also been specifiedfor use in pyrotechnics (MIL-D-3719) and was used during World War II by the Germans and Italiansin pyrotechnic formulations. 12

A thorough study of this dye by Guion2 recommended that the dye be used as a replacementonly if 1-N-methylaminoanthraquinone or 9-diethylaminorosindone could not be used. The smokeproduced by this dye was considered by Guion 2 not of the same quality or hue as that produced by1-N mvthylaminoanthraquinone. In addition, the O-methoxyphenylazo-B-naphthol had a tendency toflame more readily when disseminated.

A commercial supplier for this dye, was located during the study. BASF WyandoteCorporation, markets o-methoxyphenylazo-3-naphthol under the name of Sidan Red G.

One report18 listed this dye as carcinogen, based on unpublished data which could not becorroborated. No other toxicologcal data were found for this dye.

5. CONCLUSIONS AND RE"COMMENDATIONS

Two of the 114 dyes revie wed for this study are recomme,.ded as candidates for replacement of1-N methylaminoanthraquinone. The dyes are 9-diethylaminorosindone and o-methoxyphenylaz,'-O-naphthol.

These dyes have been tes;led and used in pyrotechnics and produce acceptable red smoke.There are insufficient toxicological data at this time to assess the health effects of these dyes.

2- -

LITERATURE CITED

1. Finkelstein, L. Chemical Corps Technical Command Report Control No. 5020-12., History ofResearch and Development of the Chemical Warfare Service in World War!! (I July 1940-31 December 1945),Volume 12. 1 May 1948, UNCLASSIFIED Report,

2. Guion, T. H. Chemical Warfare Service Technical Command Informal Report T.C.I. R.No. 357. The Use of Dyc 2-Anisole-azo-beta-naphthol in Colored Smoke Grenades. 17 October 1945,UNCLASSIFIED Report.,

3. Magram, S. J., and Finkelstein, L. Chemical Warfare Service Technical CommandMemorandum Report T.D.M.R. No. 497. A Memorandum Report Colored Smoke Grenades, M16.1943., UNCLASSIFIED Report.

4. Heath, G. D., Chemical Defense Experimental Establishment Porton Report No. 2547.The Formation of Coloured Smoke Clouds., Part I., A Review of Suitable Organic Dyestuffs.20 September 1943. UNCLASSIFIED Report.,

5. Ellern, H., Military and Civilian Pyrotechnics, pp 151-159. Chemical Publishing Company,New York, New York, 1968.

6. Heath, G. D., Chemical Defense Experimental Establishment Porton Technical PaperNo. 147. The Production of Coloured Smokes by Explosive D;spersion. 12 January 1950.UNCLASSIFIED Report.

7., Munro, W, P. Chemical Warfare Service Technical Command Memo.-andum ReportT.D.M.R. 679. 6 Jun. 1943. UNCLASSIFIED Report.

8. Colour Index. 3d Ed. Lund Humphries, Bradford, Eng. 1971.

9., Munro, W., P., and Guion, T. H. Chemical Warfare Service Technical Command InformalReport T.C.I.R. 139., The Use of 9-Diethylamino Rosindone in Colored Smoke Grenades as a Substitutefor 1-Methyl Amino Anthraquinone. 10 June 1944. UNCLASSIFIED Repo,,.

10: Chemical Warfare Service Technical Command. Colored Signal Smokes. Chem. Engr.News 22, 1990 (1944).

11.. Kieffer, W. F., and Resko, J. M. Colored Signal Smokes. J. Chem. Ed., 22, 385 (1945).

12., Goldenscn, J., and Danner, C. F. Novel Foreign Chemical and Pyrotechnic Munitions.Chem, Engr. News 26, 1976 (1948).

13. Ray, A. B. Production of Colored Smoke Signals. Ind. Engr. Chem. 18, 10 (1926).

14. Li, Y., and Chiin, S. Colored Smokes from Synthetic Dyes. J. Ch-inese Chem. Soc. 2,205 (1934).

13

15. Anson, N. M., and Parent, P. A. Chemical Warfare Laboratories Technical Memorandum

47-6. Toxicity of Nine Dyes - A Literature Search. March 1959. UNCLASSIFIED Report.

16. Registry of Toxic Effects of Chemical Substances. 1977 Ed. Vol I and II. DHEW

Publication No. (NIOSH) 78-104-A. US Government Printing Office, Washington, DC.

17. Parent, P. A. Chemical Research and Development Laboratories Special Publication

CRDL 4-59. Biological Effects of Colored Smoke Ingredients. September 1964. UNCLASSIFIED

Report.

18. Tatyrek, A. F. Picatinny Arsenal Technical Memorandum 1674. The Health Hazards of

Certain Smoke Dyes in Current Use. September 1965. UNCLASSIFIED Report.

19. Military Specification. MIL-D-3614. Dye, 9-Diethylamino-7-phenyl-5-benzo (a)

Phenazinone (For Colored Smoke Mixtures). 18 October 1951.

14

SELECTED REFERENCES

Encyclopedia of Chemical Technology. 3d Ed., Vol 3. pp 378-386. John Wiley and Sons,

New York, New York. 1978.

Heath, G. D., and Whatley, W.E.B. Chemical Defense Experimental Establishment Porton

Technical Paper No. 197. The Use of Amino Azo Dyes for the Production of Coloured Smokes by

Explosive Means. UNCLASSIFIED Report.

Lubs, H. A. The Chemistry of Synthetic Dyes and pigments, pp 235-245. Hafner

Publishing Co., New York, New York. 1955.

Nelson, W. C. Wesleyan Pyrotechnics Research Report No. 1948-5 ETF 913-31. Colored

Smokes. 29 November 1974. UNCLASSIFIED Report.

Shidlovskiy, A. A. Principles of Pyrotechnics, pp 413-426. Mashinostroyeniye Press,

Moscow, USSR. 1973.

Swan, G. A., and Felton, D.G.I. The Chsinistry of Heterocyclic Compounds. Vol II.

pp 280-362. Interscience Publishers, Inc., New York, New York. 1957.

Venkataraman, K. The Chemistry of Synthetic Dyes. Vol II. pp 761-795. Academic

Press, Inc., New York, New York. 1952.

1

15 mwm~~h

DISTRIBUTION LIST 5

Names Copies Names Copies

CHEMICAL SYSTEMS LABORATORYDEPARTMENT OF THE ARMY

ATTN: DRDAR-CLF IATTN: DRDAR-CLJ-R 2 HQDA (DAMO-NCC)ATTN: DRDAR-CLJ-L 3 WASH DC 20310

ATTN: DRDAR-CLJ-M IATTNf DRDAR-CLJ-P 1 Deputy Chief of Staff for Research,ATTN: DRDAR-CLT-E I Development & Acquisition

ATTN: DRDAR-CLN 1 ATTN: DAMA-CSS-C I

ATTN: DRDAR-CLN-D 1 ATTN: DAMA-ARZ-D 1ATTN: DRDAR-CLN-S 3 Washington, DC 20310

ATTN: DRDAR-CLN-ST 2ATTN: DRDAR-CLW-C 1 US Army Research and StandardizationATTN: DRDAR-CLB-C I Group (Europe)ATTN: DRDýR-CLB-P 1 ATTN: DRXSN-E-SC

ATTN: DRDAR-CLB-PA 1 Rox 65, FPO New York 09510

ATTN: DRDAR-CLB-R I

ATTN: DRDAR-CLB-T 1 HQDA (DAMI-FIT)ATTN: DRDAR-CLB-TE I WASH, DC 20310

ATTN: DRDAR-CLY-A 1ATTN: DRDAR-CLY-R I CommanderATTN: DRDAR-CLR-I I DARCOM, STITEUR

ATTN: ORXST-STI

COPIES FOR AUTHOR(S): Box 48, APO New York 09710

Munitions Division 2RECORD SET: ATTN: DRDAR-CLN-A 1 Commander

US Army Science & Technology Center-

DEPARTMENT OF DEFENSE Far East Office

ATTN: MAJ BorgesDefenre Technical Information Center APO San Francisco 96328ATTN: DTIC-DDA-2 12

Cameron Station, Building 5 CommanderAlexandria, VA 22314 2d Infantry Division

ATTN: EAIDCOM

Director APO San Francisco 96224

Defense Intelligence AgencyATTN: DB-4G1 I CommanderWashington, DC 20301 5th infantry Division (Mech)

ATTN: Division Chemical Officer

Special Agent in Charge Fort Polk, LA 71459

ARO, 902d Military Intelligence GPATTN: IAGPA-A-AN 1 CommanderAberdeen Proving Ground, MD 21005 US Army Nuclear & Chemical Agency

ATTN: MONA-WE (LTC Pelletler)Commander 7500 Backlick Rd, Bldg 2073SED, HQ, 1NSCOM Springfield, VA 22150

ATTN: IRFM-SED (Mr. Joubert)Fort Meade, MD 20755

17

OFFICE OF THE SURGEON GENERAL Director

US Army Material Systems Analysis Activity

Commander ATTN: DRXSY-MP

US Army Medical Bloengineering Research ATTN: DRXSY-TN (Mr. Metz) 2

and Development Laboratory Aberdeen Proving Ground, MD 21005

ATTN: SGRD-UBD-AL

Fort Detrick, Bldg 568 Commander

Frederick, MD 21701 US Army Missile Command

Redstone Scientific Information Center

Headquarters ATTN: DRSMI-RPR (Documents)

US Army Medical Research and Redstone Arsenal, AL 35809

Development Command

ATTN: SGRD-PL 1 Director

Fort Detrick, MD 21701 DARCON Field Safety Activity

ATTN: DRXOS-C

Commander Charlestown, IN 47111

"USA Medical Research Institute of

Chemical Defense Commander

ATTN: SGRD-UV-L 1 US Army Natick Research andAberdeen Proving Ground, MD 21010 Development Command

ATTN: DRDNA-VR I

US ARMY HEALTH SERVICE COMMAND ATTN: DRDNA-VT I

Natick, MA 01760Superintenoent

Academy of Health Sciences US ARMY ARMAMENT RESEARCH AND

US Army DEVELOPMENT COMMAND

ATTN: HSA-CDH 1

ATTN: HSA-IPM 1 Commander

Fort Sam Houston, TX 78234 US Army Armament Research and

Development Command

US ARMY MATERIEL DEVELOPMENT AND ATTN: DRDAR-LCA-L I

READINESS COMMAND ATTN: DRDAR-LCE I

ATTN: DRDAR-LCE-C I

Commander ATTN: DRDAR-LCU I

US Army Materiel Development and ATTN: DRDAR-LCU-CE IReadiness Command ATTN: DRDAR-PMA (G.R. Sacco) I

ATTN: DRCLDC 1 ATTN: DRDAR-SCA-W I

ATTN: DRCSF-P I ATTN: DRDAR-TSS S

5001 Eisenhower Ave ATTN: DRCPM-CAWS-AM I

Alexandr 1 a, VA 22333 ATTN: DRCPM-CAWS-SI IDover, NJ 07801

Project Manager Smoke/Obscurants

ATTN: DRCPM-SMK 5 Director

Aberdeen Proving Ground, MD 21005 Ballistic Research Laboratory

ARRADCOM

Commander ATTN: DRDAR-TSB-SUS Army Foreign Science & Technology Center Aberdeen Proving Ground, MD 21005

ATTN: DRXST-MT3 I

220 Seventh St., NECharlottesville, VA 22901

18

US ARMY ARMAMENT MATERIEL READINESS Commander

COMMAND US Army TRADOC System Analysis Activity

ATTN: ATAA-SL

Commander White Sands Missk'Ie Range, NM 88002

US Army Armament Materiel

Readiness Command JS ARMY TEST & EVALUATION COMMAND

ATTN: DRSAR-ASN I

ATTN: DRSAP-PDM 1 CommanderATTN: DRSAR-SF 1 US Army Test & Evaluation Command

Rock Island, IL 61299 ATTN: DRSTE-CM-F

ATTN: DRSTE-CT-T

Commander Aberde , Proving Ground, MD 21005

US Army Dugway Proving Ground

ATTN: Technical Library Docu Sect 1 DEPARTMENT OF THE NAVY

Dugway, UT 84022

Commander

US ARMY TRAINING & DOCTRINE COMMAND Naval Explosive Ordnance Disposal Facility

ATTN: Army Chemical Officer (Code AC-3) I

Commandant Indian Head, MD 20640

US Army Infantry School

ATTN: NBC Division 1 Commander

Fort Benning, GA 31905 Naval Weapons CenterATTN: Technical Library (Code 343)

Commandant China Lake, CA 93555

USAMP&CS/TC&FMATTN: ATZN-CM-CDM 1 Ccmmander Officer

Fort McClellan, AL 36205 Naval Weapons Support Center

ATTN: Code 5042 (Dr. B.E. Douda)

Commande- Crane, IN 47522

US Army Infantry CenterATTN: ATSH-CD-MS-C 1 US MARINE CORPS

Fort Benning, GA 31905Director, Development Center

Commander Marine Corps Development and

US Army Infantry Center Educatior Command

Directorate of Plans & Training ATTN: Fire Power Division

ATTN: ATZB-DPT-PO-NBC Quantico, VA 22134

Fort Benning, GA 31905

DEPARTMENT OF THE AIR FORCE

Comma nderUSA Training and Doctrine Command HQ Foreign Technology Division (AFSC)

ATTN: ATCD-Z ATTN: TQTR

Fort Monroe, VA 23651 Wright-Patterson AFB, OH 45433

Commander HQ AFLC/LOWMM

USA Combined Arms Center and Wriqoit-Pattern;on AFB, OH 45433Fort Leavenworth

A"TN: ATZL-CA-COG I OUTSIDE AGENCIES

ATTN: ATZL-CAM-IM 1

Fort Leavenworth, KS 66027 Battelle, Columbus Laboratories

ATTN: TACTEC

505 King Avenue

Columbus, OH 43201

19

Toxicology Information Center, WG 1008

National Research Council

2101 Constitution Ave., NW

Washington, DC 20418

ADDITIONAL ADDRESSEE

CommanderUS Army Environmental Hygiene Agency

ATTN: Librarian, Bldg 2100

Aberdeen Proving Ground, MD 21010

Stimson Library (Documents)

Academy of Health Sciences

Bldg. 2J40

Fort Sam Houston, TX 78234

20