Patent GB-357195-A (GB)
Title: Improvements in the manufacture and production of vat dyestuffs
IPC: C09B49/12
Filed: 1930-04-17
Abstract: Vat dyes.-Anthraquinone thioxanthone or acridone carboxylic acids are converted, for example by treatment in the form of their halides with aromatic amines in a solvent, into acid amides which are vat dyes. According to examples, (1) anthraquinone 2 : 1-(N) benzacridone-6-carboxylic chloride is treated with 1-amino-anthraquinone, 1-amino-4-methoxyanthraquinone, 1-amino-5-benzoylaminoanthraquinone to give the corresponding acid amides; (2) anthraquinone 2 : 1 (N) benzacridone-41-carboxylic chloride is treated with 1-amino-5-benzoylaminoanthraquinone; (3) 2 : 1 (N)-anthraquinone-6-carboxylic chloride b -b 1-naphthacridone is treated with 1-aminoanthraquinone, and 1-amino-5-benzoylaminoanthraquinone; (4) 2 : 1-(N) - anthraquinone-11 : 21 - (N) - naphthacridone - 61-carboxylic acid chloride is treated with 1-amino-4 - methoxyanthraquinone; (5) 2 : 1 - (S) - anthraquinonebenzthioxanthone-6-carboxylic chloride is treated with aniline, 1-aminoanthraquinone, benzidine, 1-amino-4-methoxyanthraquinone, 1-amino-5-benzoylaminoanthraquinone, 1 - amino - 5 - chloranthraquinone, and 1 : 5-diamino-anthraquinone; (6) 2 : 1-(S)-anthraquinonethioxanthone-Bz-4- carboxylic chloride is treated with 1-aminoanthraquinone; (7) 2 : 1-(S)-anthraquinonethioxanthone-Bz-2-carboxylic acid is treated with 1-amino-5-benzoylaminoanthraquinone, and 1-amino-4-benzoylaminoanthraquinone; (8) 3 : 2-(S)-thioxanthoneanthraquinone-Bz-2-carboxylic chloride is treated with 1-aminoanthraquinone-1-amino-5-benzoylaminoanthraquinone; (9) 1 : 2-(S)-anthraquinonethioxanthone-Bz-2-carboxylic chloride is treated with 1 - amino - 5 - benzoylaminoanthraquinone; and (10) 2 : 1-(S)-anthraquinonethioxanthone-6-carboxylic chloride is treated with 4-amino-N-methyl-pyrimidoneanthrone; all to give the corresponding acid amides.  Anthraquinone acidone and thioxanthone-carboxylic chlorides.-2 : 1-(N)-anthraquinone benzacridone-6-carboxylic chloride is obtained by condensing the benzyl ester of 1-chloranthraquinone-6-carboxylic acid with anthranilic acid, ring closing and heating with thionyl chloride; 2 : 1-(N)-anthraquinonebenzacridone-41-carboxylic chloride is obtained by condensing 1-chloranthraquinone-2-carboxylic acid with p-aminobenzoic acid ring closing, and treatment with thionyl chloride; 2 : 1-(N)-anthraquinone-b -b 1-naphthacridone-6-carboxylic acid is obtained by condensing 2-amino-naphthalene-3-carboxylic ethyl ester with 1-chloranthraquinone-6-carboxylic benzyl ester, ring closing, and treatment with thionyl chloride; 2 : 1-(N)-anthraquinone-11 : 21 - (N) - naphthacridone - 61 - carboxylic acid chloride is obtained by condensing 1-chloranthraquinone-2-carboxylic acid with 2-aminonaphthalene-6-carboxylic acid, simultaneously closing the ring (see Specification 260,588, [Class 2 (iii), Dyes &c.], and treating with thionyl chloride; 2 : 1 - (S) - anthraquinonebenzthioxanthone - 6 - carboxylic acid chloride is obtained by condensing 1-chloranthraquinone-6-carboxylic acid with thiosalicylic acid, ring closing, and treating with phosphorus pentachloride; the corresponding Bz-4- and Bz-2-carboxylic chloride are obtained by treating 1-chloranthraquinone-2-carboxylic acid with p- and o-mercaptobenzoic acids respectively, ring closing, and treatment with thionyl chloride; 3 : 2-(S)-thioxanthoneanthraquinone-Bz-2-carboxylic chloride is obtained by condensing 2-chlor-3-anthraquinone carboxylic acid with thiosalicylic acid, ring closing, and treating with thionyl chloride; 1 : 2 - (S) - anthraquinonethioxanthone - Bz - 2-carboxylic chloride is obtained by condensing 1-cyano-2-bromoanthraquinone with o-mercaptobenzoic acid, saponifying the cyano group and treating with phosphorus pentachloride.  1-Nitro-, 1-amino, and 1-chlor-anthraquinone-6-carboxylic acids are obtained by nitrating anthraquinone-2-carboxylic acid in concentrated sulphuric acid, reducing, and treating with chlorine in solvents.