GB399182A - Improvements in the manufacture and production of vat dyestuffs of the anthraquinoneacridone series - Google Patents

Abstract

4-Acylamino-Bz 2.3.5-trichloranthraquinone-2.1(N)-benzacridones are prepared by acylating the corresponding 4-amino derivatives, preferably in an organic diluent. Acylating agents specified are the halides and anhydrides of aromatic acids such as benzoic acid or its alkyl, alkoxy, halogen, cyano, or nitro derivatives, a - or b -naphthoic acids, anthracene and anthraquinone carboxylic acids, thiazolanthrone carboxylic acids, benzene and naphthalene dicarboxylic acids, diphenyl-, benzophenone-, diphenylether-, mono- and polycarboxylic acids, or of aliphatic or hydroaromatic mono- and polycarboxylic acids. The products equally dye viscose artificial silk and cotton and give fast even dyeings on mixed fabrics of these materials. The 4-amino-Bz. - 2.3.5-trichloranthraquinone-2.1-benzacridone is prepared advantageously by nitrating the trichloro derivative and reducing; or by condensing 4 - Bz. 2.3.5-tetrachloranthraquinone-2.1(N)-benzacridone with p-toluenesulphonamide and saponifying; or by chlorinating the 4-amino-Bz. 3.5-dichloro derivative in chlorsulphonic acid in presence of sulphur, or the 4-aminoderivative in acid solution in presence of sulphur; or by condensing 1-chloro-4-aminoanthraquinone with 1-amino-3.4.6-trichloro-2-benzoic acid followed by ring-closure. The Bz. 2.3.5-trichloranthraquinone - 2.1 - benzacridone is prepared by condensing 1-chloranthraquinone-2-carboxylic acid with 1-amino-2.4.5-trichlorbenzene or 1-chloranthraquinone with 2.3.5-trichloranthranilic acid, followed by ring-closure (cf. Specification 366,055); or by chlorinating the acridone or its Bz.3.5-dichloro derivative in acid solution and in presence of a halogen transferrer. Acylation with the following acids is described in examples: benzoic (dyes blue), p-chlorbenzoic (reddish blue), anthraquinone-2-carboxylic acid (grey-blue), oxalic (blue), terephthalic, isophthalic, diphenylcarboxylic, naphthoic, naphthalene-1.5-dicarboxylic, and anthraquinone-benzacridone-Bz.-carboxylic acids (violet, blue to green-blue shades), p-methoxybenzoic, p-ethoxybenzoic, and m-nitro-p-methylbenzoic (blue shades), 2.5-dichlorbenzoic and m-chlorbenzoic (violet shades), acetic, succinic, malonic, and propionic acids. The Provisional Specification contains a further example of the production of the 4-amino-Bz. 2.3.5-trichloro derivative by nitration and reduction.