Patent GB-518690-A (GB)
Title: The manufacture of vat dyestuffs
IPC: C09B5/34
Filed: 1938-09-02
Abstract: 518,690. Dyes. I.G. FARBENINDUSTRIE AKT.-GES.Sept. 2, 1938, No. 25776. Convention date, Sept. 4, 1937. [Classes 2 (iii) and 15 (ii)] Anthraquinone-2.1 (N)-1<1>.2<1> (N)-6'-aminobenzene acridones or anthraquinone-2.1 (S)- 11.21-(S)-61-aminobenzene thioxanthones are condensed with anthraquinone-#-carboxylic acid halides, preferably chlorides, in presence of a suitable solvent such as nitrobenzene. Acid halides specified are those of nitro- or amino-anthraquinone carboxylic acids, and the acridone or thioxanthone ring may be substituted by halogens, methoxy, or phenyl groups, or the acyl residue by amino or acylamino groups. The products are soluble in the hydrosulphite vat, dye vegetable fibres red to violet shades, and in the rongalite-potash-print they print cotton and artificial silk. In examples, (1) anthraquinone-2.1 (N)-1<1>.2<1> (N)-31-chloro- .6<1>-aminobenzene-acridone is reacted with (a) 1-aminoanthraquinone-2-carboxylic acid chloride, (b) -1-nitroanthraquinone-2-carboxylic acid chloride, (c) 1-amino-4-nitroanthraquinone-2- carboxylic acid chloride, followed by reduction of the nitro group, and benzoylation, (d) anthraquinone-2-carboxylic acid chloride ; (2) anthraquinone-6<1>-aminobenzene-acridone is reacted with 1-aminoanthraquinone-2-carboxylic acid chloride ; (3) anthraquinone-2.1 (N)- 11.2<1>-(N)-3<1>.4<1>-dichloro - 6<1> - amino benzeneacridone is reacted with 1-aminoanthraquinone- 2-carboxylic acid chloride ; (4) anthraquinone- 2.1 (N)-1<1>.2<1>(N)-3<1>-phenoxy-6<1>-amino-benzeneacridone is reacted with 1-aminoanthraquinone- 2-carboxylic acid chloride ; (5) anthraquinone 2.1-(S)-1<1>.2<1>-(S)-3<1>.4<1> - dichloro - 6<1> - aminobenzene-thioxanthone is reacted with 1-aminoanthraquinone-2-carboxylic acid chloride. Anthraquinone - 2.1 (N) - 1<1>.2<1> (N) - 3<1> - chloro (or 3<1>.4<1>-dichloro) - 6<1> - aminobenzene - acridone is made by reacting the corresponding 3<1>.6<1>-dichlor (or 3<1>.4<1>.6<1>-trichlor) body with p-toluene-sulphamide, followed by saponification with sulphuric acid. Anthraquinone - 61 - aminobenzene - acridone is made similarly from the 6<1>-chlor body, or by reduction of anthraquinone-6<1>-nitrobenzacridone, which is obtained from 1-chloranthraquinone-2-carboxylic acid and m-nitranifine in the usual way. The acridones and thioxanthones generally are stated to be made by exchange of a 6<1>-halogen atom for amino or for an amide residue, followed by saponification, or by reduction of a 6<1>-nitro group. Anthraquinone 2.1 (S) - 1<1>.2<1>(S) 3<1>.4<1> - dichloro - 6<1> aminobenzene-thioxanthone is obtained by reacting anthraquinone-2.1 (S)- 1<1>.2<1> - (S) - 31.41.61 - trichlorbenzene - thioxanthone with p-toluenesulphamide, followed by saponification. Anthraquinone - 2.1 (S) - 1<1>.2<1> - (S) - 3<1>.4<1>.6<1>- trichlorbenzene-thioxanthone is obtained from 1-chloranthraquinone-2-carboxylic acid and 2.3.5 - trichlorphenyl-mercaptan. 2.3.5. - Trichlorhenyl - mercaptan is obtained by reduction of the sulphochloride of 2.3.5.- trichlorbenzene-1-sulphonic acid, which is obtained from 2.4-dichloraniline-6-sulphonic acid by diazotization and transformation of the diazo body by Sandmeyer reaction. The Specification as open to inspection under Sect. 91 refers broadly to the use of vattable monocarboxylic acid halides as acylating agents and further specifies 2-phenylanthraquinone-Bz.4-carboxylic acid pyrazoleanthrone-2-carboxylic acid and carboxylic acids of indigoid compounds. It also refers to the reaction of anthraquinone-2.1 (N)-1<1>.2<1> (N)- 3<1>-chloro-6<1>-aminobenzene-acridone with 1.9- pyrazoleanthrone-2-carboxylic acid, or 2-phenylanthraquinone-4<1>-carboxylic acid, or the reaction product from 1 mol. isophthalic acid dichloride and 1 mol. 1-amino-5-benzoylaminoanthraquinone. This subject-matter does not appear in the Specification as accepted.