GB398161A - Anthracene and anthraquinone dyestuffs - Google Patents

Abstract

Thioindigoid dyes containing 2,1(S) anthracene or anthraquinone residues are prepared by treating an anthracene or anthraquinone-1-thioglycollic acid of the formul :-- <FORM:0398161/IV/1> wherein positions X or Y are occupied by halogen (particularly chlorine or bromine), nitro, sulpho, carboxy, hydroxy, amino, substituted hydroxy or amino and the anthracene or antrhaquinone nuclei may contain further substituents, with chlorsulphonic or a mixture of chlorsulphonic and sulphuric acids. When the substituent in X or Y is a substituted amino group the substituent in the amino group may form part of a ring structure attached to the anthracene or anthraquinone residue. According to the substituents present the products are vat or acid dyes, or suitably treated they may be applied by the methods described in Specification 377,740. In examples, (1) the lactam from 1-amino-2 : 5-dithioglycollic-anthraquinone (prepared according to Example 1 of Specification 398,162) is treated with chlorsulphonic acid at 20-25 DEG , to give a brown vat dye for cotton; the lactam ring may be hydrolysed by alkali and the product then applied to wool in the way described in Specification 377,740; if the above lactam employed as starting material is reduced by means of zinc dust and ammonia, and then the resulting anthracene compound treated as in (1) a brown vat dye is obtained: (2) the lactam from 1-amino-2,8-dithioglycollic-anthraquinone (prepared according to Specification 398,162) is treated with chlorsulphonic acid as in (1) to give a brown vat-dye: (3) similar treatment of the following derivatives of anthraquinone-1-thioglycollic acid is described or referred to:--5 amino-, 5-sulpho (both from the corresponding 1-mercapto derivatives and chloracetic acid), 5-chloro (from 5-aminoanthraquinone-1-thioglycollic acid by a Sandmeyer reaction), 5-o<1>-carboxyanilido (from the foregoing 5-chloro derivative and anthranilic acid), 5-hydroxy and 5-methoxy. It is stated that reaction proceeds smoothly, whereas treatment of those thioglycollic acids containing no substituent in positions X or Y leads to little, if any, condensation. The anthraquinone derivatives used as starting materials are prepared by the action of chloracetic acid on the corresponding mercaptans which are derived from substituted aminoanthraquinones or according to the processes of Specifications 10387/08, [Class 2, Acids and salts, Organic &c.], and 398,162.