GB763084A - Dyestuff compositions comprising tetra-aza-porphin compounds - Google Patents

Abstract

The invention comprises compositions comprising cobalt, tin, iron, or vanadium phthalocyanine and one or more tetra-aza-porphin compounds of the formula:- <FORM:0763084/IV(b)/1> where Me is cobalt, iron, tin, or vanadium, which may carry one or more hydroxy or acid groups, the aromatic ring may be substituted, the R's represent hydrogen or substituted or unsubstituted ethyl, cycloalkyl, aryl, or aralkyl radicals, R1 and R2 may form an alicyclic ring, the other pairs R3 and R4, R5 and R6 may form alicyclic or aromatic rings, provided that at least one of the porphins or the phthalocyanine contains an acid or acid halide substituent. The acid halide group may be hydrolysed during vatting, or before with e.g. caustic soda. The tetra-aza-porphins or phthalocyanines containing the acid or acid halide group may be made by general synthetic methods or by introducing acid or acid halide groups into tetra-aza-porphins or phthalocyanines not containing them by known methods, e.g. (a) sulphonation, (b) heating with lactones or polycarboxylic anhydrides or halogenated aliphatic acids or phosphorus tri- or oxy-chloride and Friedel-Crafts condensing agents, (c) heating with phosgene oxalyl chloride, or sulphonyl chloride in a diluent such as trichlorobenzene or aluminium chloride. The compositions may be made by mixing the ingredients with dispersing agents or by co-precipitation, by synthesis from appropriate mixtures of phthalocyanine or tetra-aza-porphin-forming ingredients, or by introduction of an acid or acid halide group by the above methods into part of a mass of phthalocyanine or tetra-aza-porphin. The products dye cotton and other cellulosic fibres blue shades. In examples, (1) cobalt phthalocyanine is milled with disodium dinaphthylmethane disulphonate and products obtained by partial sulphonation of (a) cobalt dicyclohexeno -dibenz-tetra-aza porphin (Specification 686,395), (b) cobalt tetramethyl-dibenz-tetra-aza-porphin (Specification 688,768), (c) cobalt monocyclohexeno - tribenz - tetra - aza-porphin, (d) cobalt dimethyl-tribenz-tetra-aza-porphin, the sulphonation in each case being to the point where the product is soluble in alkaline hydrosulphite but insoluble in caustic soda solution. Also in examples, (2) cobalt tetramethyl-dibenz-tetra-aza-porphine (or the hexamethyl-monobenz body) is milled with disodium dinaphthylmethane disulphonate and cobalt phthalocyanine monosulphonic acid sodium salt; (3) cobalt dicyclohexeno-dibenz-tetra-aza-porphin (or the tricyclohexeno-monobenz body) is milled with disodium dinaphthylmethane disulphonate and cobalt phthalocyanine monocarboxylic acid sodium salt: (4) cobalt phthalocyanine is milled with disodium dinaphthylmethane disulphonate and the product obtained by reacting cobalt dimethyl-tribenz-tetra-aza-porphin with g -butyrolactone or with phosphorus oxychloride in presence of ferric chloride.