GB770784A - Process for the manufacture of water-soluble phthalocyanine derivatives - Google Patents

Abstract

Water soluble phthalocyanine derivatives containing quarternary ammonium groups are made by heating with an alkyl or aralkyl ester a phthalocyanine derivative of the formula P - (CH2NR1R2)n wherein P is substituted or unsubstituted metal or metal-free phthalocyanine, R1 is substituted or unsubstituted alkyl, cycloalkyl, aralkyl, or heterocyclic radical, R2 is substituted or unsubstituted alkyl, or R1 and R2 may be joined to form together with the nitrogen atom a closed ring, and n is a number greater than 1. Excess ester may be present as reaction medium and an organic solvent may be added. The above tertiary amine substituted phthalocyanines are made by heating chlormethyl or bromethyl phthalocyanines with secondary amines. The products may be used for dyeing or printing textiles, e.g. according to Specification 633,160. In examples, (1) a mixture of copper di- and tri-chlormethyl phthalocyanines is reacted with N - methylbenzylamine, morpholine, piperidine, diethylamine, or N - methylcyclohexylamine and the product is heated with dimethyl sulphate; (2) a mixture of di- and tri-chlormethyl copper phthalocyanines is reacted with morpholine or diethylamino and the with methyl p - toluene sulphonate; (3) a mixture of di- and tri - chlormethyl nickel phthalocyanines is reacted with morpholine and then with dimethyl sulphate; (4) a mixture of tri- and tetra - chlormethyl copper phthalocyanines is reacted with morpholine and then with methyl p - toluene sulphonate; (5) morpholine and dimethyl sulphate are reacted with tri-chlormethyl metal-free phthalocyanine, cobaltous tri-chlormethylphthalocyanine, tetra - chlormethyl copper tetra - 4 - phenyl - phthalocyanine, tetra - chlomethyl copper tetra - 4 - chlorphthalocyanine, and tetra - chlormethyl copper tetra 4 - (p - tolylmercapto) - phthalocyanine; (6) tri-chlormethyl copper phthalocyanine is reacted first with dimethylamine and then with dimethyl sulphate, benzyl chloride, or ethylene chlorhydrin. The abovementioned chlomethyl phthalocyanines are prepared by usual chlormethylation methods, e.g. according to Specifications 586,340, [Group IV] 681,917. Specification 587,636 [Group IV] also is referred to.