Verfahren zur Herstellung von quaternisierten Triazenverbindungen

The invention comprises water-soluble quaternary colour salts of triazene compounds of the formula wherein A represents an aryl radical which may contain substituents which do not dissociate acid in water, B represents an arylene radical which may contain substituents which do not dissociate acid in water, X represents a divalent radical which completes the nitrogen-containing ring to a five or six-membered ring, R and R1 independently of each other represent a low alkyl radical, Y represents an anion and n represents 0 or 1. Such salts are prepared by (a) coupling the diazonium compound of an amine of the formula A-N=N-B-NH2 with a compound of the formula to form a compound of the formula and reacting the latter with an ester of a low alkanol to obtain the desired colour salt or (b) reacting a diazoimino compound of the formula with an ester of a low alkanol in the presence of alkalie to form a compound of the formula and coverting the latter with further ester into the desired colour salt or (c) converting a compound of the formula with an ester of a low alkanol to a compound of the formula into the desired colour salt. In an example an orange colour salt is obtained by coupling diazotized 4-aminoazobenzene with 2,3-dihydro-2 - imino - 3 - methyl - 6 - methoxy - benzthiazole, treating the product with dimethyl sulphate and isolating the product as a zinc chloride double salt. Additional examples relate to the preparation of colour salts in which the heterocyclic moieties are derived from such compounds as 2-amino-3-ethyl-6-methoxy-benz-thiazolium chloride, 2 - amino - 3 - methyl-thiazolium methosulphate, 1,2 - dihydro - 1-methyl - 2 - iminopyridine and 1,2 - dihydro-1-imino - 2 - methyl - isoquinoline. Many additional starting materials are specified. The colour salts are particularly suitable for dyeing or printing polymeric and copolymeric polyacrylonitrile fibres.