GB607956A - Manufacture of water-soluble anthraquinone derivatives - Google Patents

Abstract

Water-soluble anthraquinone derivatives are obtained by esterifying an anthraquinone-2-(b -oxyethyl)-thioether, containing in the 1-position a primary or secondary amino group and in the 4-position a primary or secondary amino group or a hydroxyl group, with a dicarboxylic acid or functional derivative thereof in such proportion that only one of the two carboxyl groups takes part in the esterification, and if necessary converting the esterification products into water soluble salts, e.g. alkali or ammonium salts. The anthraquinone-thioethers used as starting materials in the invention may contain in the 1 position a secondary amino group such as a methyl amino group, but preferably a primary amino group. The substituent in the 4-position may be a hydroxyl group or primary amino group, but advantageously a secondary alkylated or arylated, e.g. phenylated, amino group. There may be used 1-amino-4-phenylamino, 1-amino-4-(m-toluidino), 1-amino-4-(o-anisidino), 1-methylamino - 4 - (o - anisidino), 1 - amino - 4 - (p - aminophenyl) - amino, 1 - amino - 4 - methylamino, or 1 : 4-diamino-anthraquinone-2-(b -oxyethyl)-thioether. As esterifying agents there may be used carboxylic acids which form internal anhydrides or their acid halides, e.g. succinic, phthalic, quinolinic and maleic acid. The products can be used for dyeing and printing a wide variety of fibres of cellulose esters or cellulose ethers. In examples (1) 1 - amino - 4 - anilido - anthraquinone - 2 - oxyethylthioether is heated with maleic anhydride in pyridine to give a product the sodium salt of which dyes cellulose acetate strong blue tints; (2) as in (1), but using 1-amino-4-methylaminoanthraquinone-2-oxyethyl-thioether; (3) as in (1), but using 1-amino-4-oxy-anthraquinone-2-oxyethyl-thioether; (4) cellulose acetate is dyed with the product of (2). Specification 480,358 is referred to. Anthraquinone - 2 - (b -oxyethyl) - thioethers are obtained from the corresponding 2-halogen compounds by treating with sodium sulphide to produce a 2-mercapto group followed by treatment with glycol chlorhydrin. The Specification as open to inspection under Sect. 91 comprises also the use of other polybasic acids and functional derivatives thereof, such as purely inorganic acids, e.g. sulphuric or phosphoric acid, and the treatment of other anthraquinone oxyalkyl thioethers, e.g. 1-amino-4-phenylamino-anthraquinone-2-(b : a -dioxypropyl)-thioether and 1-amino-4-anilidoanthraquinone-2-oxyethyl-thioether. This subject-matter does not appear in the Specification as accepted.