GB406008A - Improvements in the manufacture and production of vatdyestuffs - Google Patents

Abstract

Vat dyes are prepared by treating with acylating agents derived from organic carboxylic acids amino derivatives of pyridino compounds containing more than three but not more than nine condensed rings and at least one keto group, the following grouping being present therein: <FORM:0406008/IV/1> wherein two vicinal X's are members of a six-membered isocyclic ring, the other X's representing hydrogen, carbon atoms which form part of further condensed isocyclic rings, or the desired amino group or groups, or by treating halogen derivatives of pyridino compounds of the said type with carboxylic acid amides, at least one reaction component being vattable. Suitable pyridino compounds are pyridinoanthraquinone, pyridinobenzanthrones, pyridinoanthanthrones and pyridinopyranthrones; acylating agents suitable comprise carboxylic acid halides (or acid amides) of isocyclic, heterocyclic or hydroaromatic compounds, for example of benzene, naphthalene, anthraquinone, benzanthrone, pyridine, or quinoline; especially valuable dyes are those derived from yellow to red reacting components such as anthraquinone, anthanthrone, dibenzpyrenequinone, ms-benzdianthrone, which dyes yield shades fast to light and weather. In examples (1) amino - 2 (N) . 3 - pyridinoanthraquinone (prepared by reduction of the nitro derivative obtained by nitration in sulphuric acid) is benzoylated (dyes yellow); (2) 3-amino-2 (N) . 1 - pyridinoanthraquinone (prepared by heating the 3-bromo derivative in an autoclave with ammonia) is condensed with anthraquinone - 2 - carboxylic acid chloride (yellow shades), 1 - aminoanthraquinone - 2 - carboxylic acid, anthraquinone - 1 - carboxylic acid, a mixture of iso- and terephthalic acids (red shades); 1 - amino - 2 (N) . 3 - pyridinoanthraquinone (prepared by acting on the 1-chloro derivative with ammonia in the presence of copper) may be similarly condensed; (3) 3 - bromo - 2 (N) . 1 - pyridinoanthraquinone is condensed with benzamide and m-methoxybenzamide; (4) monaminopyridinoanthanthrone (prepared by nitration and reduction) is benzoylated (red-brown shades). The Provisional Specification relates to the condensation of aminopyridino compounds with acylating agents, or halogenpyridino compounds with acid amides, wherein in either case at least one reaction component must be capable of being vatted. Ms-anthradianthrone derivatives are mentioned as starting materials, and the term "acid amides" includes sulphonic acid amides. A further example is included wherein 3-bromo-2.1-pyridinoanthraquinone is condensed with p-toluenesulphonamide. Specification 349,059 is referred to.