Anthraquinone colorants

Anthraquinone colorants are characterized by the presence of the anthraquinone [84-65-1] (qv) nucleus ... 

Included in this grouping are D C Green No. 5 (13), a water-soluble sulfonate, D C Green No. 6 (14), an unsulfonated water-insoluble compound, and D C Violet No. 2 (29), a water-insoluble hydroxyanthraquinone. Anthraquinone color additives, in general, are light stable and have good physical and chemical properties for use in cosmetics (see Dyes, ANTHRAQUINONE). 

Production Capacity and Demand. The production capacity for each dye or dye intermediate has rarely been aimounced officially by the individual manufacturers. However, the world demand of anthraquinone colorants can be roughly estimated as in Table 13 and, more specifically, in Figure 13. Principal manufacturers of anthraquinone dyes and their intermediates are as follows ... 

There is a wide diversity of chemical structures of anthraquinone colorants. Many anthraquinone dyes are found in nature, perhaps the best known being alizarin, 1,2-dihydroxyanthraquinone, the principal constituent of madder (see Chapter 1). These natural anthraquinone dyes are no longer of significant commercial importance. Many of the current commercial range of synthetic anthraquinone dyes are simply substituted derivatives of the anthraquinone system. For example, a number of the most important red and blue disperse dyes for application to polyester fibres are simple non-ionic anthraquinone molecules, containing substituents such as amino, hydroxy and methoxy, and a number of sul-fonated derivatives are commonly used as acid dyes for wool. 

M.A. Ackacha, K. Polec Pawlak and M. Jarosz, Identification of anthraquinone coloring matters in natural red dyestuffs by high performance liquid chromatography with ultraviolet and electrospray mass spectrometric detection, J. Sep. Sci., 26, 1028 1034 (2003). 

CAS 4403-90-1 EINECS/ELINCS 224-546-6 Synonyms Alizarin cyanine green F 2,2 -(1,4-Anthraquinonylenediimino) bis (5-methylbenzenesulfonic acid) disodium salt 6,6 -(1,4-Anthraquinonylenediimino) di-m-toluenesulfonic acid disodium salt Benzenesulfonic acid, 2,2 -(1>4-anthraquinonylenediimino) bis (5-methyl)-, disodium salt Benzenesulfonic acid, 2,2 -[(9,10-dihydro-9,10-dioxo-1,4-anthracenediyl) diimino] bis (5-methyl)-, disodium salt Cl 61570 D C Green No. 5 2,2 -[(9,10-Dihydro-9,10-dioxo-1,4-anthracenediyl) diimino] bis (5-methylbenzenesulfonic acid) disodium salt Classification Anthraquinone color Empincal C28H2oN2Na208S2 Properties Grn. powd. sol. 0.5-1.0 g/100 ml water (21 C) si. sol. in acetone, alcohol, pyridine insol. in chloroform, toluene dull blue sol n. in cone. H2SO4, turning turquoise on dil. m.w. 622.58 m.p. 340 C... 

Classification Anthraquinone color Empirical C2iHi6NOeS Na Uses Colorant in hair dyes Acid violet 49 CAS 1694-09-3... 

CAS 81-48-1 EINECS/ELINCS 201-353-5 Synonyms D C Violet No. 2 N-(4-Hydroxy-1-anthraquinonyl)-4-methylaniline N-(4-Hydroxy-1-anthraquinonyl)-p-toluidine 1-Hydroxy-4-[(4-methylphenyl) amino]-9,10-anthracenedione 1-Hydroxy-4-(p-toluidino) anthraquinone Solvent violet 13 N-(p-Tolyl)-4-hydroxy-1-anthraquinonylamine Classification Anthraquinone color Empirical C21H15NO3... 

Classification Anthraquinone color Empirical C28H2oN2Na208S2 Formula C28H20N2O8S2 2Na Properties M.w. 622.57 Toxicology TSCA listed Uses Colorant in cosmetics, surgical sutures Manuf./Distrib. Aldrich http //www.sigma-aldrich.com... 

CAS 4403-90-1 EINECS/ELINCS 224-546-6 Synonyms Acid green 25 Alizarine cyanine green F Cl 61570 2,2 -[(9,10-Dihydro-9,10-dioxo-1,4-anthracenediyl) diimino] bis (5-methyl) benzenesulfonic acid disodium salt Classification Anthraquinone color Empirical C28H2oN2Na20sS2 Formula C28H20N2O8S2 2Na Properties Dullish blue-gm. m.w. 622.57 Toxicology Low skin toxicity may cause skin irritation and sensitivity TSCA listed Uses Colorant for pharmaceuticals and surgical sutures Use Level 0.6% max. (sutures)... 

Classification Anthraquinone color Empirical C21H15NO3 Properties Dull bluish violet m.w. 329.35 Toxicology LD50 (intratracheal, rat) 250 mg/kg TSCA listed... 

Classification Anthraquinone color Empirical C28H12CI2N2O4 Formula C28H12N2O4CI2 Properties M.w. 511.32 Toxicology LD50 (oral, rat) >10 g/kg, (oral, mouse) 1800 mg/kg, (skin, mouse) 25 g/kg mod. toxic by ing. mildly toxic by skin contact TSCA listed... 

The synthesis of anthraquinone colorants may effectively be envisaged as involving two general stages. The first stage involves the construetion of the anthraquinone ring system and in the second phase the anthraquinone nucleus is elaborated to produce the desired strueture. Frequently, the latter involves substitution reactions, but group interconversion and further cyclisation reaetions may also... 

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