Patent GB-953428-A (GB)
Title: Water-soluble azo-dyestuffs containing one or more thio-sulphuric acid groups and process for their manufacture
IPC: C09B62/82
Filed: 1960-04-25
Abstract: The invention comprises water-soluble dyes of formula F-[X-SSO3Me]n, where F is the residue of an azo dye derived from a diazo component of the benzene, naphthalene, diphenyl or diphenyl-ether series, X is a direct link or -CH2-, -SO2NHCH2CH2-, -SO2(Me)N-CH2CH2-, or -SO2N(C2H2CN)CH2CH2-, the XSSO3Me group being bound to the aromatic neucleus of the residue of the diazo component in a position other than ortho to the azo group of the residue F, Me is alkali metal or ammonium and n is 1-4 and the dyes may contain in the diazo and/or coupling component sulphonic acid groups and/or carboxylic acid groups and thiosulphuric acid groups may also be present in the coupling component residue. When the dye contains a basic grouping it may be obtained as an inner salt.  The dyes are made in conventional fashion from appropriate amines of formula H2N-arylene-[X-SSO3-H]n, and coupling components, diazotization being preferred at 0-5 DEG  C. Representative of specified diazo components are 3-amino-phenyl- and -benzyl-, 3-amino-4,6-dichlorobenzyl-, 5-aminonaphthyl - (1) - methyl -, 4 - amino-diphenyl - 41 - sulphonylamino - b  - ethyl - and 3 - (41 - aminobenzoylamino) - benzene sulphonylamino - b  - ethyl - thiosulphuric acid. Representative of specified coupling components are aniline, 2,5-dialkoxyaniline, dimethylaniline, diphenylamine, m-phenylenediamine, a -naphthylamine, phenol, 2-hydroxy-3-naphthoic acid, b -naphthol-sulphonic acids and 5 - aminonaphthyl - (1) - methylthiosulphuric acid.  Preferred coupling components are those in which the azo link enters in a position vicinal to a hydroxyl group, e.g. 2-naphthol, 1 - (31 - nitrophenyl) - 3 - methyl - 5 - pyrazolone, 2 - acetoacetylamino - 6 - ethoxy - benzothiazole, 4,41 - di - (acetoacetylamino) - 3,31 - dimethyl - diphenyl, benzoyl - acetylamino - 2,5 - dimethoxy - 4 - chlorobenzene and condensation products of copper- or nickel-phthalocyanine-sulphochlorides with aminophenyl-methyl-pyrazolones (see Specification 830,920),(21-hydroxy-31 - naphthoylamino) - 2 - methoxybenzene, (21 - hydroxycarbazole - 31 - carbonylamino) - 4 -chlorobenzene, (31 - hydroxy - diphenylene oxide - 21 - carbonylamino) - 2,5 - dimethoxy - benzene, 3 - acetoacetylaminobenzyl - thiosulphuric acid and 4-(21-hydroxy-31-naphthoyl-amino) - 3 - methyl - phenoxy - b  - ethyl - thiosulphuric acid.  The coupling components may also be reacted with partial condensation products of cyanuric chloride and aliphatic, or aromatic, amines containing thiosulphuric acid groups, e.g. 8-amino-2-naphthol, may be condensed with the reaction product of 1 mol. of cyanuric chloride with 1 or 2 mols. of b -amino-ethyl - thiosulphuric acid. Dyes containing amino groups may be diazotized and recoupled to form disazo dyes, and the condensation products from phthalocyanines are shown as having 3 or 4 azo groups.  The dyes colour wool, silk, leather, polyamides and polyurethanes, from an acid bath, in a wide variety of colours.  Examples are provided of the preparation of the dyes and their use in dyeing processes.  In Example (1) a disazo dye is made from J acid urea and in other examples various disazo dyes are made from diacetoacetylamino coupling components.  Specification 949,956 also is referred to.