GB580351A - New dyestuffs of the anthraquinone series - Google Patents

Abstract

Acid dyestuffs of the anthraquinone series are prepared by reacting in an aqueous or alcoholic solution or in a mixture of these a 2 : 6- or 2 : 7-disulphonated 1-amino-4-halogen-anthraquinone with a monoacylamino-aniline of the general formula <FORM:0580351/IV/1> where R is hydrogen or a methyl group, in the presence of copper or a salt thereof and in the presence of an acid binding agent. Alternatively the above aniline compounds may be reacted with a 6- or 7-sulphonated 1-amino-2 : 4-dihalogenanthraquinone and the product treated with a sulphite. Amines mentioned include p-aminoacetanilide, m-aminoacetanilide p - amino - methyl - acetanilide, 3 - acetylamino-p-toluidine, 3-acetylamino-2 : 4-dimethylaniline, 3 - acetylamino - 4 - methyl - carboxy - aniline, 3-acetylamino-4-chloraniline, 2 : 6-dimethyl-3-acetylamino-aniline. Anthraquinone compounds mentioned include 6- or 7-sulphonated 1-amino-2 : 4-dibromanthraquinones or a mixture thereof, 6- or 7-sulphonated 1-amino-2 : 4-dichloranthraquinones or a mixture thereof, 2 : 6- or 2 : 7-disulphonated-1-amino-4-brom-anthraquinones or a mixture thereof, 2 : 6-or 2 : 7-disulphonated-1-amino-4-chlor-anthraquinones or a mixture thereof. In examples: (1) the sodium salt of 1-amino-4-bromanthraquinone-2 : 7-disulphonic acid is heated in aqueous alcoholic solution with p-amino-acetanilide in the presence of powdered copper and sodium bicarbonate. The 2 : 6-disulphonic acid may be used to produce a slightly less greenish blue. (2) The sodium salt of 1-amino-4-brom-anthraquinone is treated as in example 1 with acetylamino-4(methylcarboxy)-aniline. The 2 : 6-disulphonic acid may in this case also be used. (3) As in example (2) but using 3-acetylamino-4-methyl aniline instead of 3-acetylamino-4(methylcarboxy)-aniline. A mixture of the 2 : 6- and the 2 : 7-disulphonic acids may be used. (4) As in example (2) but using 3-acetylamino-4-chloraniline as the amine. The 4-bromanthraquinone may also be replaced by the 4-chlor compound. (5) The potassium salt of 1-amino-2 : 4-dibromanthraquinone-6-sulphonic acid is treated as in example (1) with 3-(methylacetylamino)-aniline and the monosulphonated dye so formed, treated with a solution of a sulphite. (6) The potassium salt of 1-amino-2 : 4-dibromanthraquinone-6-sulphonic acid is treated as in example (1) with 2 : 4-dimethyl-3-acetylamino-aniline and the product sulphonated by treatment with a sulphite. The same dyestuffs are obtained by condensing 2 : 4-dimethyl-3-acetylamino-aniline with the 2 : 6- or the 2 : 7-disulphonated-1-amino-4-halogenanthraquinones. The dyestuffs of this invention may be used for dyeing wool, hair-felt, silk, organic fibres of the nylon type, and leather in greenish blue shades. Specifications 412,270 and 551,881 are referred to.