GB493841A - Manufacture of mono-azo dyestuffs soluble in water - Google Patents

Abstract

Diazo compounds of the benzene series containing no free sulphonic or carboxylic groups are combined in an acid or alkaline medium with an aminohydroxynaphthalene of the formula <FORM:0493841/IV/1> or <FORM:0493841/IV/2> wherein R stands for a naphthalene nucleus which may contain further substituents but must not contain a sulphonic group and X and Y are hydrogen or alkyl, but excluding 1-amino-7-hydroxynaphthalenes in the case of compounds the formula (1). The products dye wool at 60-90 DEG C. In examples, the preparation of the following dyestuffs is described: (1) aniline --> 2-sulphethylamino-7 (or 6 or 8)-hydroxynaphthalene (red-brown tints on wool); (2) 1 - amino - 2 - methylbenzene --> 2 - sulphethylamino - 7 - hydroxynaphthalene; (3) 1 - aminobenzene - 3 - carboxylic acid methyl ester --> 2 - sulphethylamino (or sulphopropylamino) - 7 - hydroxynaphthalene (brown); (4) 1 - amino - 4 - methoxybenzene --> 2 - sulphomethylamino - 7 - hydroxynaphthalene (brown-red); (5) 1 - amino - 3 - chlorbenzene --> 2 - sulphethylmethylamino (or sulphethylethylamino) - 7 - hydroxynaphthalene (red); (6) 1 - amino - 4 - methoxybenzene --> 2 - sulphethylamino - 7 - hydroxynaphthalene (bordeaux-brown); (7) aniline (or o-toluidine or 1 - amino - 4 - chlorbenzene --> 2-sulphacetamino - 7 - hydroxynaphthalene (orange); (8) 4-aminoacetanilide --> 2 - sulphacetamino-7 - hydroxynaphthalene; (9) 3 - amino - 4 - methoxybenzene - 1 - sulphonic acid diethylamide --> 2 - sulphacetamino - 7 - hydroxynaphthalene; (10) 1 - amino - 4 - methoxybenzene or 1-aminobenzene-2-carboxylic acid methyl ester --> 1-sulphacetamino-7-hydroxy naphthalene; (11) aniline --> 2 - sulphacetomethylamino - 7 - hydroxynaphthalene; (12) 1 - amino - 4 - methoxybenzene --> 1 - sulphacetethylamino - 7 - hydroxynaphthalene; (13) aniline --> 2 - sulphacetamino - 8 - hydroxynaphthalene or 1-sulphacetamino-6-hydroxynaphthalene; (14) aniline --> 1-sulphopropionylamino-7-hydroxynaphthalene. The sulphoalkylamino-hydroxynaphthalenes are obtained by condensing an aminohydroxynaphthalene with a halogenalkylsulphonic acid. The sulphoacylamino-hydroxynaphthalenes are obtained by condensing an aminohydroxynaphthalene with a chloralkylcarboxylic acid chloride, followed by reaction with sodium sulphite.