Patent GB-902776-A (GB)
Title: Metal complexes of mixtures of monoazo-dyestuffs and process for their manufacture
Filed: 1959-04-30
Abstract: The invention comprises chromium complexes which contain one atom of metal bound to two molecules of different monoazo dyes one of which contains at least two sulphonic acid groups and the other is free from such groups and from carboxy groups not in ortho-position to the azo link.  The complexes are made by conventional methods.  The dyes may be derived from #s, #s1-dihydroxy-, #s-hydroxy-#s1-carboxy, #s-hydroxy-o1-alkoxy- or o-hydroxy-o1-amino-monoazo dyes or 1,1-chromium complexes thereof.  Preferred classes of complexes are those in which each of the dyes contains, in addition to the groups in ortho-position to the azo link, no further amino groups, those in which the dye containing the SO3H groups is of the formula is of the formula HO3S-R1(OH)-N = N-R2(OH)-SO3H where R1 and R2 are naphthol residues with OH vicinal to the azo link and those of formula R1(OH)-N = N-R2 where R1 is the residue of a benzene or naphthalene sulphonic acid, with OH ortho to the azo link, and R2 is the residue of a 1-naphthol sulphonic acid bound in the 2-position to the azo link of a 1-phenyl-5-pyrazolone sulphonic acid bound in the 4-position to the azo link.  Illustrative of specified diazo components which contain sulphonic acid groups are 2-aniline-1-carboxy and -1-hydroxy-4 and -5 sulphonic acids, 4-nitro- or -chloro-2-aminophenol-6-sulphonic acid, 2-aminophenol-4,6-disulphonic acid, 2-amino-1-naphthol-8-sulphonic acid, 6-bromo-1-amino-2-naphthol-4-sulphonic acid and 1-amino-2-naphthol-4-sulphonic acid and its 6-nitro derivatives. Representative of indicated coupling components containing sulphonic acid groups are 1-phenyl-3-methyl-5-pyrazolone-41-sulphonic acid, 1-[naphthyl-(21)]-3-methyl- 5-pyrazolone- 81-sulphonic acid, 1-aceto-acetylaminobenzene-4-sulphonic acid, 2-amino- or -hydroxy-naphthalene-4-,-5-,-6- or -7-sulphonic acids, 2-amino-5-naphthol-7-sulphonic acid, 2-phenylaminonaphthalene-31-sulphonic acid, 1-naphthol-3,6-disulphonic acid, 1-naphthol-3,6,8-trisulphonic acid and 2-naphthol-3,6-disulphonic acid.  Sulphonic acid group free diazo components are, for example, 5-chlor-2-aminobenzoic acid, 2-amino- 1-phenol- 4-sulphones and sulphon-ami des, 5-nitro or -chloro-2-aminophenol and 4-nitro-6-acetylamino-2-aminophenol. Sulphonic acid group free coupling components are, for example, p-tertiary amyl phenol, 4-methyl-2-acetylamino- 1-phenol, 1,3-diphenyl-5-pyrazolone, 1-(21-ethylphenyl-3-methyl-5-pyrazolone, 1-[naphthyl-(11)]- 3-methyl- 5-pyrazolone, 1-phenyl-5-pyrazolone-3-carboxylic acid phenylamide, 1-n-octyl-3-methyl-5-pyrazolone, hydroxyquinolines, barbituric acid, 6-methoxy-2-naphthylamine, 2-phenylaminonaphthalene, 1-acetylamino- 7-naphthol, 1-dimethyl-aminosulphonylamino- 7-naphthol, 5-chloro-1-naphthol and 2-naphthol.  The dyes are especially used for colouring materials of animal origin, e.g. silk, leather and particularly wool, but will also colour superpoly-amide and -urethane fibres. Numerous examples are provided of the preparation of the dyes and their use in dyeing wool in a variety of colour shades. Specifications 427,922, 428,070, 428,965, 431,598 and 434,835 are referred to.