GB823053A - New trisazo-dyestuffs containing a thiazole residue and process for their manufacture - Google Patents

Abstract

The invention comprises dyestuffs of formula R3-N = N-R2-N = N-R1-N = N-R4 where R1 is a 1,3-dioxyaryl residue bound to each of the azo links #s to an OH group, R2 is a 1,11-diphenyl residue bound to the azo links in the 4,41-positions R3 is a residue of a yellow component and R4 is a benzene-thiazolyloxybenzene residue bound to the azo link #s-to the OH group. They may be made by coupling the dioxyaryl compound on one side with a diazo-azo-compound obtained by coupling a tetrazotized 4,4-diamino-1,11-diphenyl with the yellow component and, on the other side, with a diazo compound of a benzenethiazolyl-2-aminophenol. Preferably the heterocyclic diazo compound is coupled first. Couplings are advantageously effected in an alkaline medium. Specified dioxyaryl compounds are 1,3-dioxy-benzene and naphthalene. Specified diphenyls are 3,31-dimethyl-, -dimethoxy- and -dichloro-4,41-diamino-1,11-diphenyl and 4,41-diamino-1,11-diphenyl, the latter being preferred. Yellow components indicated and specified are acyl-, e.g. aceto-, acetylamino-benzenes, pyrazolones, e.g. 1-phenyl-3-methyl-5-pyrazolone, barbituric acids and 2-carboxyphenols, e.g. 6-chloro-5- and 6-methyl-1-phenol-2-carboxylic acid and especially salicylic acid. The thiazolyl compound preferably contains at least one group imparting solubility in water, e.g. COOH, SO3H and sulphonamide groups. Advantageously the thiazolyl compound contains an SO3H group and the aryl-thiazolyl group is pto the OH group. Preferred thiazolyl compounds are of formula <FORM:0823053/IV(c)/1> where R and R1 are benzene residues and OH is #sto NH2 one of which may be obtained by monosulphonating 2 - (31 - amino - 41 - oxyphenyl)-benzthiazole. The dyestuffs dye animal fibres such as wool, silk and leather but are particularly of use in dyeing or printing cellulosic materials such as cotton, linen and artificial silk or staple fibres of regenerated cellulose. The dyestuffs may be metallized in substance, in the dyebath or on the fibre with, e.g. copper, chromium, iron, nickel and cobalt compounds. Metallization may be effected and after-treatments applied in conventional fashion and Specifications 455,274, [Group IV] and 619,969 are referred to. Examples are provided illustrating the preparation of the dyestuffs and their use in dyeing cotton in brown shades before and after a coppering treatment; additional to certain of the above specified reactants the following components are used : 2 - (31 - amino - 41 - oxyphenyl) - 6 - methyl - and - methoxy - benzthiazole - x - sulphonic acid and 2 - (31 - amino - 41 - oxyphenyl)-benzthiazole. Specification 359,063, [Group IV], also is referred to.