GB948837A - New azo dyestuffs containing disulphonimide groups and their metal complexes - Google Patents

Abstract

2 - Aminophenol - 4 - sulpho - (methanesulpho) -methylimide is prepared by reacting 2 - nitrophenol -4-sulphomethylamide with methane sulphochloride to give 2 - nitrophenol - 4 - sulpho -(methanesulpho) - methylimide and reducing this by catalytic hydrogenation; 2 - Aminophenol - 4 -sulpho - (methanesulpho) - isobutyl - and isopropyl -imides are also specified. 1 - Phenyl - 3 - methyl-5-pyrazolone - 31 -sulpho-(methanesulpho) -isopropylimide is prepared by reacting 3 - nitrobenzenesulpho - isopropylamide with methane sulphochloride and hydrogenating the product to give 3 - aminobenzene - sulpho -(methanesulpho) - isopropylimide, diazotizing this compound reacting the diazonium compound with sodium sulphite and saponifying the hydrazine -N - sulphonic acid obtained to give 3 -hydrazino - benzene - sulpho - (methanesulpho) -isopropylimide and reacting this with acetoacetamide. 1 - Amino - 2 - carboxybenzene - 5 - sulpho -(methanesulpho) - isopropylimide is prepared by reacting N - acetyl - anthranilic acid - 5 - sulpho-isopropylimide with methane sulphochloride and saponifying the product.ALSO:The invention comprises metallizable dyes of formula <FORM:0948837/C3/1> wherein A is the radical of a diazo component of the benzene series, X is a metallizable group or a substituent convertible into a metallizable group under metallizing conditions in ortho-position to the azo group, B is an azo component of the pyrazolone or naphthalene series coupling ortho to -OH and R and R1 are alkyl radicals containing up to 5 carbon atoms, which may be substituted; and chromium, copper and cobalt complexes thereof. The dyes are prepared by the usual coupling procedure using suitable components one of which contains a disulphonimide group and metallized by known methods using cobalt-, chromium- or copper-yielding agents. A preferred class of the dyes are those which are free of sulphonic acid and carboxylic acid groups not taking part in complex formation which are used to dye lacquers. In examples the following dyes are prepared and converted into their cobalt and chromium complexes: 2 - amino - phenol - 4 - sulpho - (methanesulpho)-methylimide --> 1 - phenyl - 3 - methyl - 5 - pyrazolone; 2 - aminophenol - 4 - sulpho - (methanesulpho) - isobutylimide--> b - naphthol; 2 - aminophenol - 4 - sulpho - (methanesulpho) - isopropylimide --> b - naphthol; 2 - amino - 4 - chlorophenol--> 1 - phenyl - 3 - methyl - 5 - pyrazolone - 31 - sulpho - (methanesulpho) - isopropylimide; 1 - amino - 2 - carboxy - benzene - 5 - sulpho - (methanesulpho)-isopropylimide--> 1 phenyl - 3 - methyl - 5 - pyrazolone.