Metal-Complex Dyes for Polypropylene

In the synthesis of the heterocyclic dye 28 [83156-84-7] [49], 2-amino-4-chloro-phenol is diazotized. A solution of 1 -mcthylimidazo 1,5 pyridinc in 10% HC1 is then added dropwise to the diazotation mixture while maintaining the pH at 4—5 with sodium acetate solution. The resulting azo dye is isolated by vacuum filtration and consists of a brown powder that dyes nickel-modified polypropylene fibers in greenish blue shades. 

Wool and Polyamide Dyes. Water-soluble formazan complexes having sulfonamide, alkylsulfonyl, or sulfonic acid groups possess a high affinity to nitrogen-containing fibers. As with acid dyes, they can be used to dye wool and polyamide in neutral to weakly acid baths. Commercial dyes of this type are C.I. Acid Blue 267 and 297, and the 1 2 cobalt complex C.I. Acid Black 180, 13710 [11103-91-6] (29). 

Synthesis of the copper complex31 [167780-70-3] (H, Na salt) involves coupling of a diazonium compound with a hydrazone [54] 2-(3-amino-4-hydroxyphe-nylsulfonamido)chlorobenzene is dissolved in hot water, to which dilute NaOH solution is then added. After addition of sodium nitrite, the solution is cooled to -5 °C and then added to a well-stirred mixture of HC1, water, and ice. The diazonium salt suspension is neutralized with NaHC03 and combined with the weakly acidic solution of the hydrazone formed with 2-hydrazino-5-sulfobenzoic acid and benzaldehyde in water. The reaction mixture is kept at 0-10 °C, and at pH 10-12 by dropwise addition of diluted NaOH. When the coupling is complete, the pH of the formazan solution is reduced to 8 with HC1, a dilute aqueous solution of copper tetraaminosulfate is added and the solution is stirred for several hours. The copper complex 31 is precipitated at 85-90 °C with NaCl, then filtered and dried. The resulting powder colors wool in clear, fast blue tones. 

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