GB1079965A - Metallised mono-azo dyestuffs containing a sulphonamide-triazine residue - Google Patents

Abstract

The invention comprises metal-containing azo dyestuffs which are free from -SO3H and non-complex bonded carboxylic acid groups and have the formula <FORM:1079965/C4-C5/1> wherein A represents a radical of the benzene or naphthalene series in which X is in the o -position to the azo grouping, B represents the radical of a coupling component in which Y is in a position adjacent to the azo group, X represents -O- and/or -COO-, Y represents -O-, -COO-, -NH-, <FORM:1079965/C4-C5/2> <FORM:1079965/C4-C5/3> or <FORM:1079965/C4-C5/4> R represents a H atom or an alkyl or aryl radical; R1 represents a halogen atom; R2 represents unsubstituted or substituted alkyl or aryl, an ether group, a thioether group, or unsubstituted or substituted alkyl- or aryl-amino group, m represents an integer from 1 to 4; Me represents Cr or Co, and K is a cation. They may be obtained by (a) treating azo dyestuffs of the formula <FORM:1079965/C4-C5/5> wherein Q represents -OH, -COOH or -O-alkyl and is in the o -position relative to the azo group, and m1 is 1 or 2, or mixtures of different metallizable azo dyestuffs of this formula, with Cr or Co discharging agents; (b) treating a dyestuff of Formula (II) in admixture with a second dyestuff of the formula <FORM:1079965/C4-C5/6> in a similar manner; or (c) reacting a dyestuff of the formula <FORM:1079965/C4-C5/7> and a cyanuric acid halide of the formula <FORM:1079965/C4-C5/8> wherein "halogen" denotes a halogen atom, the starting components being free from sulphonic acid and carboxylic acid groups. The substituent R2 may be present in the starting components or it may be introduced into the metal-free or metal-containing dyestuffs at a later stage of the process. Specified coupling components include phenols, naphthols, acetoacetanilides, pyrazolones, aminopyrazoles, naphthylamines, pyrazolobenzimidazole, 3-hydroxy-thionaphthene, a benztriazole, 1,3-dihydroxy-isoquinoline and 4 - hydroxy - naphthalene-2 - methylene - sulphone - 1 - ether. Numerous examples are given for the production of the dyestuffs. The dyes are useful for dyeing or printing natural and regenerated protein fibres such as wool and silk, synthetic super-polyamide and superpolyurethane fibres, as well as polyacrylonitrile fibres.ALSO:Natural and regenerated protein fibres and polyacrylonitrile fibres are dyed or printed with dyes which are free from SO3H and non-complex bonded carboxylic acid groups and have the formula:- <FORM:1079965/D1-D2/1> wherein A represents a radical of the benzene or naphthalene series in which X is in the o-position to the azo group, B represents the radical of a coupling component in which Y is in a position adjacent to the azo group. X represents -O- and/or -COO- and Y represents -O-, -COO-, -NH-, <FORM:1079965/D1-D2/2> , <FORM:1079965/D1-D2/3> or <FORM:1079965/D1-D2/4> ; R represents H, alkyl or aryl; R1 represent halogen; R2 represents an unsubstituted or substituted alkyl or aryl group, an ether group, a thioether group or a unsubstituted or substituted alkyl- or arylamino group, m is 1 to 4; Me represents Cr or Co, and K is a cation. Specified fibres are wool, silk, synthetic superpolyamide and superpolyurethane fibres. An Example is given in which wool is dyed.