GB613982A - Manufacture of dyestuffs - Google Patents

Abstract

New dyestuffs are made by treating compounds of the anthraquinone series and related types as hereinafter defined which carry one or more chloromethyl or bromomethyl groups by known methods for replacing the chlorine or bromine atoms of the chloromethyl or bromomethyl groups by quaternary ammonium groups. The compounds of the anthraquinone series and related types referred to in this Specification are the coloured compounds which may be represented by the formula <FORM:0613982/IV (c)/1> wherein A and B may be the same or different and may be carbon, nitrogen or sulphur atoms which form part of one or more ring systems condensed with one or both of the phenylene nuclei X and Y, or may be oxygen atoms, and wherein the phenylene nuclei X and Y may carry further substituents other than sulphonic or carboxylic acid grops, or may carry rings condensed with two adjacent carbon atoms of X or Y, provided than when the number of aromatic and quinonoid rings in the condensed ring systems is less than 6 then a heterocyclic ring which forms part of the condensed ring system must carry at least one pendent aryl nucleus free from sulphonic or carboxylic acid groups connected directly, or X or Y or any of the condensed rings must carry at least one pendent aryl nucleus (free from sulphonic or carboxylic acid groups) connected through an -O-, -S-, -NH, -NH-CO- or -CO-NH- linkage. Examples of starting materials which may be used in this invention include mono- and bis(chloromethyl) - acedianthrone, bis - (chloromethyl) - dibenzanthrone, bis - (chloromethyl)-isodibenzanthrone, chloromethyl-indanthrone, the chloromethyl derivative of 8 : 17-di-p-toluidinoindanthrone, the bis-chloromethyl derivative of 2 : 8-diphenyl-11 : 21(N) : 51 : 61(N)-anthraquinonedithiazole and bis - (chloromethyl)-1 : 4-dianilino-, 1 : 4-di-p-toluidino-and 1 : 4-di-m-xylidino-anthraquinone, bis-(chloromethyl)-perylene-3 : 4 : 9 : 10-tetracarboxy-di-)phenylimide). The starting materials for use in this invention may be made by reacting the compounds of the anthraquinone series and related types with dichloro- or dibromodimethyl ether in the presence of a condensing agent such as for example sulphuric acid. An example of suitable methods is heating the chloro- or bromo-methyl derivative with a tertiary amine, for example, pyridine, tri-ethylamine, dimethylcyclohexylamine. In examples, pyridine is reacted with the chlormethyl derivatives of (1) dibenzanthrone; (2) isodibenzanthrone; (3) acedianthrone; (4) 8.17 - di - p - toluidinoindanthrone; (5) 1.4-dianilinoanthraquinone; (6) perylene-3.4.9.10-tetracarboxy-di-(phenylimide); (7) 1.4-bis-(m - chlormethylbenzoylamino) anthraquinone. Also in examples: (8) triethylamine is reacted with the chlormethyl derivatives of acedianthrone or perylene-3.4.9.10-tetracarboxy-di-(phenylimide), and (9) dimethylcyclohexylamine is reacted with bis-(chlormethyl)-acedianthrone.