Patent GB-472790-A (GB)
Title: Manufacture of dyestuffs of the anthraquinone series
IPC: C09B5/34
Filed: 1937-01-11
Abstract: Anthraquinone-acridones containing at least once the grouping <FORM:0472790/IV/1> are obtained from an anthraquinone of the general formula <FORM:0472790/IV/2> wherein NH--R stands for the group <FORM:0472790/IV/3> one X stands for hydrogen and the other for a COOR group (OR being OH, O-alkyl or halogen), and which contains in the 4 or 5 position a further group NHR<1> (R<1> being identical with R or representing an anthraquinonyl or acyl radical) or which contains in another a -position of the naphthalene ring a further anthraquinonylamino radical, by treatment with a condensing agent which does not have a sulphonating action; if desired the product is subsequently carbazolized.  The starting materials are prepared by reacting such bodies as 1.4-diaminoanthraquinone (1 mol.) with 1 - chlornaphthalene - 2 - carboxylic acid ethyl ester (2 mols.). An anthraquinoneacridone so obtained containing an acylamino group, e.g. in 4-position, may be saponified and then condensed with an aromatic compound containing a reactive halogen atom, such as a -chloroanthraquinone, and the product so obtained may be carbazolized.  The new dyes may be halogenated, nitrated and subsequently reduced and if desired acylated.  In examples, (1) 1 - (a  - naphthylamino - b  - carboxylic acid ethyl ester) - 4 (or 5) - benzoylaminoanthraquinone (obtained by condensing 1-amino-4 (or 5)-benzoylaminoanthraquinone with 1-chlornaphthalene - 2 - carboxylic acid ethyl ester) or the corresponding acid is vatted to give a 4 - benzoylamino - 1 . a  - anthraquinonenaphthacridone which dyes cotton, greenish grey; the benzoyl radical may be replaced by 4<1>-chlorbenzoyl, 3<1>-methoxybenzoyl, phenoxyacetyl or furane-a -carboxyl.  Also in examples, (2) 1.5-(di - a  - naphthylamino - b  - carboxylic acid ethyl ester)-anthraquinone (prepared from 1.5-diaminoanthraquinone and 1-chlornaphthalene2-carboxylic acid ethyl ester) is vatted to produce a dinaphthacridone (grey tints on cotton); (3) the compound prepared from 4 : 4<1>-diamino-1 : 1<1>-dianthraquinonylamine and 2 mols. 1-chlornaphthalene-2-carboxylic acid ethyl ester is vatted and the diacridone so obtained (green tints) carbazolized by treatment with sulphuric acid, to give a product of the formula <FORM:0472790/IV/4> (olive tints); (4) 5-aminoanthraquinone-1 : 1<1> : 2 : 2<1>-naphthacridone (obtained by saponifying the corresponding benzoylamino compound) is boiled with 1-chloranthraquinone in nitrobenzene (brown-violet) and the product carbazolised by fusion with aluminium chloride (brown); (5) the dicarboxylic acid obtained by condensing 1.4-dichlornaphthalene with 1-aminoanthraquinone - 2 - carboxylic acid ethyl ester followed by saponification is condensed to the diacridone by heating in toluene with phosphorus pentachloride (red-brown); further examples describe the dyeing of cotton with the dyestuffs made as in (1) and (2) above.  The Specification as open to inspection under Sect. 91 describes the preparation of anthraquinone-2 : 2<1> . 1 : 1<1> - naphthacridone by treating with thionyl chloride in toluene 1-a -naphthylaminoanthraquinone - 2 - carboxylic acid, itself prepared by condensing 1-aminoanthraquinone-2-carboxylic acid ethyl ester with 1-chlornaphthalene, followed by saponification. This subject-matter does not appear in the Specification as accepted.