GB490017A - Improvements in the manufacture and production of dyestuffs - Google Patents

Abstract

Dyestuffs are manufactured by heating compounds of the general formula B-A-R (where B is the radicle of a cyclic compound having in o-position two halogen atoms, e.g. of the benzene, naphthalene, anthracene, anthraquinone, benzanthrone, azanthraquinone, azabenzanthrone or pyrene series, A is a simple linkage or an atomic bridge, e.g. of carbon, nitrogen or a non-metal of group VI of the periodic system or containing two or more of the said atoms, e.g. a carboxylic acid amide group such as -NHCO-, -CONH-, -NHCONH-, -NHCSNH- or -NHCO-CONH-, and R is the radicle of a vattable compound, e.g. of the indigo, thioindigo, anthraquinone or azanthraquinone series) with cuprous cyanide in the presence of a nitrogenous organic base, e.g. pyridine, quinoline or dimethylaniline, if desired in the presence of an additional diluent, e.g. nitrobenzene, alkylbenzenes, naphthalene and its derivatives, phenols, glycol or cyclohexanol, and advantageously in the presence of metals or metal compounds, e.g. copper and its compounds. The products are useful as vat dyestuffs and as body colours for the preparation of coatings, lacquers and varnishes. In examples: (1) anthraquinone-2-carboxylic acid 31 : 41-dibromanilide is heated with cuprous cyanide, pyridine and nitrobenzene; the product dyes cotton green shades from a brown vat; similar dyestuffs are obtained from 31 : 41-dihalogenanilides of other vattable carboxylic acids, e.g. of other anthraquinonecarboxylic acids or of anthraquinonecarboxylic acids in which the anthraquinone nucleus contains substituents or has other rings joined to it; (2) 1-(41-chloro-31-bromobenzoyl) - aminoanthraquinone is heated with cuprous cyanide, cuprous bromide and quinoline; the product dyes cotton green shades from a violet vat; similar dyestuffs are obtained from o-dihalogenaroyl derivatives of other aminoanthraquinones or of other vattable amines, or from compounds in which an o-dihalogenaryl radicle is attached to the carbon atom of an azole or pyrimidine ring in a vattable compound. o-Dihalogen compounds of the general formula given above are obtainable by condensing the halide of a carboxylic acid of a vattable compound, e.g. the chloride of an anthraquinone or anthraquinonebenzacridone carboxylic acid, with a dihalogenaniline; or by heating a vattable amine such as aminoanthraquinone with 3 : 4-dichloro- or -dibromobenzoyl chloride; or by reacting vattable carboxylic acid chlorides with o-dihalogen compounds by the Friedel-Crafts synthesis; or by reacting o-dihalogenbenzoyl chlorides with diaminoanthraquinones. The starting materials of the examples above are obtainable by reacting together, in the presence of nitrobenzene: (1) anthraquinone-2-carboxylic acid chloride and 3 : 4-dibromaniline; (2) 1 - aminoanthraquinone and 4 - chloro -3-bromobenzoyl chloride.