GB367793A - Improvements in and relating to the production of anthraquinone-naphthacridone derivatives - Google Patents

Abstract

Anthraquinone naphthacridone derivatives.--One or both the halogen atoms in a 5 : 8-dihalogenanthraquinone-2 : 1 (b ) - naphthacri - done are replaced by amino-, alkylamino, acyclic, or monocyclic acylamino- or acylimino groups the acyl groups being subsequently removed, if desired, by hydrolysis. The treatment with the amine or amide can be carried out in one or more stages and with one or more amines or amides. Amines which may be used are ammonia or primary or secondary aliphatic amines, and amides are simple or substituted, including imides. Diluents, catalysts, and acid absorbers may be present in the condensation, and hydrolysis may be effected by means of sulphuric acid. Amino- or alkylamino groups in the products may be benzoylated. The products dye cotton and other fibres from the vat, or in some cases they may be used for dyeing acetyl cellulose, and in others, either before or after sulphonation, for dyeing wool. In examples 5 : 8-dichloranthraquinone-2 : 1-(b )-naphthacridone (prepared as follows:--2-(4<1>-methylbenzoyl) - 3 : 6-dichlorobenzoic acid is ring-closed by means of oleum and the resulting solution treated with chlorine to give 1 : 5 : 8-trichloro-2-methylanthraquinone. This is oxidized by an acid-manganese dioxide mixture to the 2-carboxylic acid derivative, the latter condensed with one mol. of b -naphthylamine, and the product ring-closed by means of acetic anhydride in nitrobenzene) is condensed with (1) phthalimide (dyes mauve); this product may be hydrolysed by means of concentrated sulphuric acid to 5 : 8-diamino-2 : 1 (b )-naphthacridone (dyes cotton greenish-blue), and the latter on benzoylation dyes redder shades; (2) methylamine (dyes blueish-red shades); (3) p-toluenesulphonamide (dyes pale violet); (4) benzamide (dyes violet).