Blue acid

Other Names C.I. Acid Blue 89, trisodium salt Acid Blue Sh Acid Light Blue Acid Sky Blue Acilan Fast Navy Blue B Atul Acid Sulfon Blue B C.I. 13405 C.I. Acid Blue 89 Calcocid Wool Blue B Cirene Brilliant Blue B Eniacid Brilliant Blue B Fast Wool Blue B Hispacid Fast Blue B Russian Acid Blue Sulfonine Acid Blue B Sulphon Acid Blue B Tertracid Fast Flue SB CA Index Name 2,7-Naphtlialenedisulfonic acid, 4-hydroxy-5-[[4-[(4-methylphenyl)amino]-5-sulfo-l-naphthalenyl]azo]-, trisodium salt CAS Registry Number 10359-95-2 Merck Index Number Not listed Chemical Structure 

Chemical/Dye Class Azo Molecular Formula C27HigN30ioS3Na3 Molecular Weight 709.61 pH Range 11.0-12.0 

Physical Form Brown powder Solubility Soluble in water, ethanol Melting Point 250°C Synthesis Synthetic method  

Major Applications Wool dyeing, tints for polyester fibers, coloring metal oxide Safety/Toxicity No data available 

Van Beek, H. C. A. Heertjes, P. M. Houtepen, C. Retzloff, D. Formation of hydrazyl radicals and hydrazo compounds by photoreduction of azo dyes. J. Soc. Dyers Colourists 1971, 87, 87-92. 

---

Phthalocyanine Dyes. In addition to their use as pigments, the phthalocyanines have found widespread appHcation as dyestuffs, eg, direct and reactive dyes, water-soluble dyes with physical or chemical binding, solvent-soluble dyes with physical or chemical binding, a2o reactive dyes, a2o nonreactive dyes, sulfur dyes, and wet dyes. The first phthalocyanine dyes were used in the early 1930s to dye textiles like cotton (qv). The water-soluble forms Hke sodium salts of copper phthalocyanine disulfonic acid. Direct Blue 86 [1330-38-7] (Cl 74180), Direct Blue 87 [1330-39-8] (Cl 74200), Acid Blue 249 [36485-85-5] (Cl 74220), and their derivatives are used to dye natural and synthetic textiles (qv), paper, and leather (qv). The sodium salt of cobalt phthalocyanine, ie. Vat Blue 29 [1328-50-3] (Cl 74140) is mostly appHed to ceUulose fibers (qv). 

Spkit Blue [2152-64-9] Cl Solvent Blue 23 (Cl 42760), is one of the few dyes sulfonated as the leuco base. The degree of sulfonation depends on the conditions. Monosulfonated derivatives, commonly referred to as alkaU blues, eg. Cl Acid Blue 119 [1324-76-17, are used as thek barium or calcium salts in printing inks. Disulfonated compounds, eg. Cl Acid Blue 48 [1324-77-2] are employed as thek sodium or ammonium salts for blueing paper, whereas the trisulfonic derivatives or ink blues, eg. Cl Acid Blue 93 [28983-56A] are used in writing inks (qv). 

The starting materials of the aldehyde method may be sulfonated. For example. Cl Acid Blue 9 [2650-18-2] Cl Food Blue 2 (Cl 42090), is manufactured by condensing a-(A/-ethylanilino)-y -toluenesulfonic acid with o-sulfobenzaldehyde. The leuco base is oxidized with sodium dichromate to the dye, which is usually isolated as the ammonium salt. In this case, the removal of the excess amine is not necessary. However, this color caimot be used in the food sector because separation of the chromium compounds from the dye is difficult. An alternative method which gives food-grade Cl Acid Blue 9 (14) and dispenses with the use of sodium dichromate employs oxidative electrolysis of the leuco base (49). 

Other disazo dyes with good substantivity and high wet-fastness properties on polyamides are Acid Red 114 (40), made by coupling o-toHdine to phenol which is then coupled to G-acid, followed by reaction of the phenoHc hydroxyl group with -toluenesulfonyl chloride, and Acid Blue 113 (41) (metanilic acid — 1-naphthylamine — 8-anilino-1-naphthalenesulfonic acid). 

The largest volume acid blues are either of triphenyhnethane (TPM) or anthraquinone chemical constituency (see Dyes, anthraquinone). 

Premetallized Dyes. Although discovered in 1912, the 1 1 chromium complexes known as Palatine Fast (BASF) and Neolan (Ciba) dyes had httie practical use as wool dyes until 1920 when it was found that a strongly acidic dyebath (pH ca 2.0) (51) was requited to obtain satisfactory dyeing and acceptable fastness properties. Dyes of this type exemplified by Neolan Blue 2G [6370-12-3] (57) (Cl Acid Blue 158A Cl 15050) are stiU in use despite the damage to the wool caused by the strong acid in the dyebath. 

Among anthraquiaoae dyes (see Dyes, anthraquinone). Acid Blue 78 [6424-75-5] C2 H25BrN20 S -Na, or Alizarin Pure Blue B, is a wool dye. Bromamine acid [116-81-4] (l-amiao-4-bromoanthraquiaoae-2-sulfonic acid), C24HgBrNO S, is a useful dye iatermediate. A number of bromo anthraquiaoae, pyrathroae, and benzanthrone dyes are known. 

D C Blue No. 4 (11) Alphazurine FG Erioglaucine Cl Acid Blue 9 [6371-85-3] 42090 externally appHed dmgs only... 

The starting material is an acid dye, ie, Cl Acid Blue 45 which is prepared from 1,5-dihydroxyanthraquiaone by sulfonation followed by nitration and then reduction. 

Dyes with better wetfastness and better affinity in neutral or weakly acid bath have been developed by introducing more hydrophobic amines. Examples are Cl Acid Blue 129 [6397-02-0] (120) Cl 62058), Cl Acid Blue 126 [72152-61-5] (121) (130), and Cl Acid Blue 230 [12269-82-8] (122) Cl 62075). However, uniform leveling cannot be obtained with these dyes. 

Linking of two dye molecules is another method for improving wetfastness. An example is Cl Acid Blue 127 1 [12237-86 ] (123) (130), which is obtained by condensing two molecules of Cl Acid Blue 25 (118) with formaldehyde. Cl Acid Blue 127 is also exemplified by [6471-01-8] (124) Cl 61135). 

The shade may be varied by choosing amines. For aromatic amines, the steric effect of substituents in the ortho position reduces the conjugation of the anibno group with the anthraquinone moiety, and the result is a hypsochromic shift and brighter shade. Thus Cl Acid Blue 129 (120) has a more reddish and brighter shade than Cl Acid Blue 25 (118). Cycloalkylamines have a similat effect on the shade. Cl Acid Blue 62 [5617-28-7] (125) Cl 62045) is an example. 

Cl Acid Blue 40 (119) has a greener and somewhat duller shade than the parent dye (ie. Cl Acid Blue 25) (118), which is considered to be due to the electronic effect of the i ra-acetylamino group. 

Cl Acid Gieen 25 [4403-90-1] (3) (Cl 61570) was also invented in 1894. This dye shows improved wetfastness, and is prepared from leucoquinizarin by reaction with 2 moles of i)-toluidine in a similat manner to the preparation of Cl Acid Violet 43 (134). Wetfastness and leveling properties may be altered by choosing the substituents of arylamines. The introduction of alkyl groups into aromatic amines improves the wetfastness and affinity in neutral or weekly acid baths. Examples ate Cl Acid Blue 80 [4474-24-27] (131) (Cl 61585) and Cl Acid Gieen 27 [6408-57-7] (132) (Cl 61580). 

---