IMPORTANT EARLY SYNTHETIC DYES Chemistry Constitution Date Properties Compiled by Textile Conservation Interns Andrea Bowes Stephen Collins Shannon Elliott La Tasha Harris Laura Hazl ett Ester M~ th~ Muhammadin Razak Pugi Yosep Subagiyo Edited by Mary W. Ballard, Senior Textile Conservator Conservation Analytical Laboratory Smithsonian Institution 1991 Preface This notebook presents information on a limited number of important early synthetic dyes as recommended by the extensive work of Dr. Helmut Schweppe in the field of dye analysis. A great deal of the data has been abstracted from the well-known encyclopedia on dye structure and properties, the Colour Index, published jointly by the American Association of textile Chemists and Colorists and the Society of Dyers and Colourists. The purpose of this manual is as an aid to textile conservators in their laboratories. It is distributed by the Conservation Analytical Laboratory, Smithsonian Institution, with the kind permission of the American Association of Textile Chemists and Colorists. For a complete review of all known dye structures and chemical properties of dyes, the reader is referred to the master volumes of the Colour Index. Mary W. Ballard, editor Senior Textile Conservator, CAL Senior Member, AATCC October, 1991 TABLE OF CONTENTS I). Listing of Early Synthetic Dyes (by Colour Index Number) (in chronological order by color) II). Glossary of Terms III). Chemistry, Constitution, Date, and Properties Bibliography IV). Toxicity Information a). General Health Hazard Protective Equipment b). Accidental Contact Occurrence General Procedures c). Toxicity Manufacturers Listing d). Toxicity Bibliography V). Chemistry, Constitution, Date and Properties Dye Information Section (Arrange by Colour Index Number) Commercial Name: Colour Index Discoverer, year: Generic Name: C.I.Number: 1) Picric Acid Acid Dye 10305 (Woulfe,l771) 2) Martius Yellow C.I.Acid Yello... · 24 10315 (Ganahl, 1856) 3) Naphthol Ye11o~ S (BASF) C.I.Acid Yello~ 1 10316 (H.Caro, 1879) 4) Chrysoidine C.I.Basic Orange 2 11270 (H.Caro, 1875) 5) Metanil Yellow C.l.Acid Yellow 36 13065 , (C.Rumpff, 1879) 6) Orange IV C.I.Acid Orange 5 13080 (O.N.Witt, 1876) 7) Azo Flavine 3R C.I.Acid Orange 1 13090 (E. Knecht, 1880) 8) Archil Red C.l.Acid Red 74 13355 (Z.Roussin and A.F.Poirrier,1878) 9) Alizarin Yellow GGN C.!. Mordant 14025 (R.N1etzki. 1887) Yellow 1 10) Chrysoin C.1.Acid Orange 6 14270 (P.Griess, 1875) 11) Orange I C:I.Acid Orange 20 14600 (P.Griess,1876) 12) Naphthylamin Brown F C.I.Acid Brown 6 14625 (H.Caro, 1878) 13) Orange II C.I.Acid Orange 7 15510 (Z.Roussin, 1876) 14) Fast Red AV (BASF) C.1.Acid Red 88 15620 (H.Caro and Z.Roussin,1877) 15) Scarlet N for Silk C.1.Acid Red 9 15635 (Durand and Huguenin) 16) Croceine Orange G C.1.Acid Orange 12 15970 (P.Griess, 1878) 17) Fast Red E C. I.Acld Red 13 16045 (H.Caro, 1878) 18) Ponceau 3RO C. I. Acid Red 25 16050 (C. Rumpf!, 1882) 19) Ponceau G C. 1. Acid Orange 14 16100 (H. Baum, 1878) 20 ) Ponceau RR C. 1. Acid Red 26 16150 (H. Baum, 1878) 21 ) Fast Red B C.1.Acid Red 17 16180 (H . Baum, 1878) ..., 22) Amaranth C.1.Acid Red 27 16185 (H. Baum, 1878) 23) Orange GG C.1.Acid Orange 10 16230 (H. Baum, 1878) 24) Kristallponceau 6R C.1.Acid Red 44 16250 (M.Hoffmann, 1883) 25) Cochineal Red A C.1.Acid Red 18 16255 (H. Baum, 1878) 26) Ponceau 6R C.I.Acid Red 41 16290 (L.Limpach, 1882) 27) Fast Acid Magenta B C.1.Acid Red 33 17200 28) Amido Naphthol Red G C.1.Acid Red 1 18050 (M.L.B. 1902) 29) Azo Fuchsine 6 B C. 1.Acid Violet 7 18055 (M. L. B. 1902 ) 30) Flavazine L C.I.Acid Yellow 11 . 18820 (C.Mollenhoff,1892) , 31 ) Tartrazine C.1.Acid Yellow 23 19140 (H. Ziegler, 1884) 32) Amido Black 10B C.1.Acid Black 1 20470 (M.Hoffmann, 1891) 33) Vesuvine BA C.l.Basic Brown 1 21000 (C.Martlus, 1863) 34) Congo Red C. 1. Direct Red 28 22120 (P.Bottiger, 1884) 35) Brilliant Yellow C. 1. Direct Yellow 4 24890 (F. Bender and 0.Schultz,1886) 36) Cloth Scarlet C. 1. Acid Red 151 26900 (R.Nietzki, 1878) 37) Wool Red B C.1.Acid Red 115 27200 (R.KrUgener, 1879) 38) Cotton Scarlet C.1.Acid Red 73 27290 (L.Limpo.ch, 1882) 39) Auramine C. 1. Basic Yellow 2 41000 (Kern and Care, 1883) 40 ) Diamond Green B C. 1. Basis Green 4 42000 (0. Fischer, 1877) 41) Diamond Green G C. 1. Basic Green 1 42040 (Bindschedler and Busch, 1879) 42) Patent Blue V C.1.Acid Blue 3 42051 (Herrmann, 1888) 43) Light Green SF Bluish . C. 1. Acid Green 6 42075 (Ktlhler, 1879) 44) Magenta C. 1. Basic Violet 14 42510 (Natanson, 1856) 45) Methyl Violet C. 1. Basic Violet 1 42535 (Lauth, 1861) 46) Crystal Violet C. 1. Basic Violet 3 42555 (Kern and Caro, 1883) 47) Water Blue rN New C. r.Acid Blue 93 42780 (A. W. Hofman, 1858) 48) Victoria Blue R C.r.Basic Blue 11 44040 (Nachtvogel and Reingruber, 1892) 49) Victoria Blue B C.I.Basic Blue 26 44045 (Caro and Kern, 1883) 50) Rhodamine 6G C.I.Basic Red 1 45160 (Bernthsen, 1892) 51) Rhodamine B C.I.Basic Violet 10 45170 (C~resole, 1887) 52) Uranine A C.I.Acid Yellow 73 45350 (Baeyer, 1871) 53) Eosine A C.1.Acid Red 87 45380 (Caro 1971) 54) Erythrosine C.l.Acid Red 51 45430 (Kussmaul, 1876) 55) Ouinoline Yellow C.I.Acid Yellow 3 47005 (Jacobsen, 1882) 56) Safranine T C.l.Basic Red 2 50240 (Greville Williams, 1859) 57) Mauveine Basic Dye 50245 (~'. H. Perkin, 1856) 58) Nigrosine, watersoluble C.I.Acid Black 2 50420 (Coupier, 1867) 59) Methylene Blue C.l.Basic Blue 9 52015 (Caro, 1876) 60) Murexide Mordant Dye 56085 (Scheele, 1776) 61) Alizarin C.!. Mordant Red 11 58000 (C.Graebe and C.Liebermann, 1871) 62) Alizarin Red S C.I.Mordant Red 3 58005 (C.Graebe and C.Liebermann, 1871) 63) Alizarin Red PS Mordant Dye 58210 64) Alizarin Red SS C.I.Mordant Red 2 58260 (M.L.B:, 1886) 65) Indigo Carmine C.l.Acid Blue 74 73015 (Barth, 1740) 66) Prussian Blue C.l.Pigment Blue 27 77510 (Diesb~ch, 1704) Glossary AATCC: American Association of Textile Chemists and Colorists. Professional organization, located in Research Triangle Park, North Carolina. Designs and promulgates textile testing standards, published annually in AATCC Technical Manual. Numerical references compare to Grey Scales for chnages in color or Grey Scales for changes in staining: 5 (least) to 1 (most). Lightfastness of dye on fabric compare to standards 1 (lowest) to 8 (highest fastness). Carbonising: Operation in wool processing. Designed to removed vegetable impurities (burrs, etc.); occurs before dyeing. With woolen piece goods, fabric is immersed in 5% (wt/vol) H2S04' squeezed. dried at 600- 700C. then baked at 1100C for 5 minutes. Fabrics will contain about 6% H2S04' Decreases affinity of fabric for acid dyes. Crabbing: Operation in wool processing. Cloth under tension passes through boiling water and is quenched. Purpose is to prevent/correct cockling and distoriton of weave structure or pattern. particularly to plain weaves. Decatising: Steaming. Operation in wool processing. Dischargeability: Characteristic of certain dyestuffs, to be reduced (destroyed) and not to interfere with the shade of subsequent dye on a printed cloth. Dye Method: For wool fibers, yarns and fabrics. Refers to acidity required in dye bath condition for the successful application of the dye to the fiber: ( 1) Nearly neutral (pH 7.0-7.5) (2) Weakly acidic (pH 3.5-5.5) (3) Sulfuric acid (pH<3.5). Exhaustion: A postiive characteristic of a dye. refers to the transfer of the dye from the bath (dye liquor) into the fiber. Illuminating color: Dye not affected by the reducing agent used for a discharged dye. ISO: International Organization for Standardization. Professional organization • located in Geneva, Switzerland. Designs and promulgates (textile) testing methods. Test methods for the determination of fastness also use Grey Scales. Levelness: A positive characteristic of a dye. Refers to the overall evenness of shade througout the piece of c l oth or skein of yarn. Also used to indicate thoroughness of penetration into the material. i.e. in cross-section. Milling: Synonym for fulling. Operation in woolen processing. Designed to felt the cloth. increasing fullness and density. creating a pile. Potting: Operation in wool processing similar to crabbing. Fabric is wrapped around iron roller. submerged in a cold bath; bath is slowly raised to the boil. Used to obt ain bright finish and soft handle found in billiard cloths. SDC. Society of Dyers and Colourists. British professional organization. Devises and promulgates textile testing standards. First fastness data published in the Society' s Journal in 1884. Stovin~: A bleaching operation during wool processing. Involves the use of sulfur or sulfur dioxide. Bibliography Abrahart, E.N. Dyes and Their Intermediates. New York: Chemical Publishing, 1977 Allen, R.L. M. Colour Chemistry. New York: Appleton-Century-Crofts, 1971. Bird, C.L. The Theory and Practice of Wool Dyeing, 4th edition. Bradford, Yorkshire: Society of Dyers and Colourists, 1972. Colour Index. Volumes 1-4, 3rd edition. Bradford, Yorkshire: Society of Dyers and Colourists, 1971. Giles, C.H. A Laboratory Course in Dyeing, 3rd edition. Bradford, Yorkshire: Society of Dyers and Colourists, 1974 . Knecht, E., C. Rawson, and R. Loewenthal. Manual of Dyeing: For the Use of Practical Dyers.