GB884885A - New diazapolymethine dyestuffs, their production and use - Google Patents

Abstract

The invention comprises dyes of formula <FORM:0884885/IV (c)/1> where R is an alkyl group, X is H or an alkyl, aryl, alkylmercapto or arylamino group, Y is S or alkylimino, A the divalent radical of an amine or examine of which the amino group is attached to NR1R2R3 by way of an alkylene or arylene radical, R1 and R2 are H or alkyl, R3 is H, alky or aralkyl, R1, R2 and R3 may be attached directly or via a hetero atom and Z is the equivalent of an anion. The dyes may be made by coupling a diazo compound of the required heterocyclic amine with a compound of formula HANR2R3, or a quaternary salt thereof, or by reacting, as in Specification 858,181, a hydrazone of formula <FORM:0884885/IV (c)/2> in the presence of an oxidising agent, with an appropriate amine or enamine or quaternary salt, with subsequent quaternation where necessary. Representative of specified heterocyclic amines are 3 - amino - 5 - phenyl - 1,3,4 - triazole and 2 - amino - and 2 - amino - 5 - methyl - 1,3,4 - thiadiazole. Representative of specified hydrazones are 2,4 - dimethyl - 5 - phenyl - 1,2,4 - triazolone-and 3 - methyl - 5 - methylthio - 1,3,4 - thiadiazolone - 2 - hydrazones. Representative of specified amines and enamines are N,N - dimethyl - N1 - (3 - methylphenyl) - ethylene diamine, N,N - dimethyl - N1 - (2 - hydroxyethyl) - N1 - phenyl - 1,3 - diaminopropane, N - (2 - diethylaminoethyl) - N1 - phenyl - ine, N - butyl- N 2 - piperidinoethyl) - 3 - amino - 1 - methoxybenzene, 1 - (3 - aminopropyl) - 2 - phenylindole, (2 - phenyl - methylaminoethyl)- trimethylammonium hydroxide and N-(3-ethylphenylamino-2-hydroxypropylamino)-pyridinium hydroxide and salts thereof. Usual alkylating agents are specified. Z-may be derived from inorganic, organic or complex acids and may represent, e.g. bromide, trichlorozincate, tetrafluorborate, phosphate, acetate or oxalate. The dyes colour textiles made from polyacrylonitrile or poly-1,1-dicyano-ethylene or copolymers of acrylonitrile or 1,1-dicyanoethylene with other polymerisable compounds such as vinyl acetate, vinyl chloride and vinylidene chloride. Examples are provided of the preparation of the dyes and their use in colouring processes to give a variety of shades of red, blue, green and yellow.