GB860584A - Diazacyanine dyestuff cations - Google Patents

Abstract

The invention comprises cations of formula: <FORM:0860584/IV(c)/1> where D is an atomic bridge to effect a thiazole or benzthiazole ring, R1 is an aliphatic-radicle of 1-5 C atoms, R2 is H or an aliphatic or aromatic radicle, R3 is H or an alkyl radicle of 1-4 C atoms, A is a divalent aliphatic, aromatic or aliphatic-aromatic radical which may also contain hetero atoms and Z is an amino group. They may be made in conventional fashion e.g. by treating thiazolones -(2) or their mineral acid salts which have been alkylated at the nitrogen atom with aromatic amines capable of coupling, in aqueous solution at pH7-2 and at 0-50 DEG C with oxidising agents, such as atmospheric oxygen, hydrogen peroxide, hypochlorites, perborates, persulphates, ferric, cupric, mercuric and ceric salts or ferricyanides, and the cations precipitated in the form of salts with inorganic or organic anines by acidification, or by coupling an appropriate diazotised 2-aminothiazole with one of the above amines and the product alkylated at 10-130 DEG C, preferably 30-80 DEG C. Representative of hydrazones specified are 3-methyl-4-phenyl-, 3-methyl-benz-, 3-methyl-6-methoxybenz-, 3-methyl-6-chlor-benz- and 3-methyl-6-phenyl-and-acetyl - amino - benz - thiazolone - (2)-hydrazones. Specified coupling amines include N, N-dimethyl-N1-phenyl-and N, N-di-beta-hydroxyethyl-N1methyl- N1 - phenyl - ethylene diamine, N, N-dimethyl-N1-beta-hydrox ethyl-N1-phenyl-1, 3 - diaminopropane, N, N-dimethyl- N1-ethyl1 N1-phenyl- 1, 3-diaminopropanol-2, N-butyl- N-beta-piperidinoethyl- 3-amino-1-methylbenzene, N-(beta-diethylaminoethyl) - diphenylamine, 1-(gamma-aminopropyl)-1, 2, 3, 4-tetrahydroquinoline. Other values specified for 2 include di-ethyl-and methylpropyl-amino, pyrrolidino and morpholino. Representative of specified diazotisable thiazoles are 2-aminothiazole and its 4-phenyl-, thiazoles are 2-aminothiazole and its 4-phenyl-, 5-nitro-and-cyano-and 4, 5-dimethyl-derivatives and 2-amino-6-methyl- and -ethoxy- and 2-amino- 4-methyl- 6-chlorbenzthiazoles. Representative of further values indicated for A are: <FORM:0860584/IV(c)/2> and hydroxybutylene. The rings of the cations may be substituted by mainly neutral substituents e.g. alkyl, aryl, alkyl-, aryl- and acylamino, alkoxy, alkylsulphonyl, sulphonic acid dialkylamide, carboxylic acid ester and amide, cyano and halogen groups. Specified alkylating-agents are methyl bromide, ethyl chloride, dimethyl sulphate, diethyl sulphate and methylpara-toluene sulphonate. The dyestuff neutral or acid salts dye cotton mordanted with tannic acid, cellulose acetate, linear polyamides, urethanes and esters and polymers or copolymers of acrylonitrile or dicyanoethylene. Examples are provided of the preparation of the dye cations and their use, as salts, e.g. bromide, sulphate, phosphate, trichlorzincate and methosulphate, in dyeing polyacrylonitrile fibres in blue shades. Specifications 786,929 and 787,369 are referred to.