GB494168A - The manufacture of new vat dyestuffs - Google Patents

Abstract

Vat dyestuffs are manufactured by causing amines to react with 4-halogenquinazolines, the reactants being so chosen that a radicle of a vattable compound is present in the 2-position of the 4-halogenquinazoline or in the amine or both. Suitable vattable compounds are anthraquinones, anthraquinonebenzene- or naphthalene-acridones, pyrazolanthrones and thiazolanthrones, which may contain further substituents, e.g. halogen atoms or nitro, amino or aroylamino groups. The reaction may be effected by heating the reactants in the presence of solvents such as dichlorobenzene, nitrobenzene or phenol, preferably at about 100-210 DEG C. In examples the following compounds are reacted together: (1) a - aminoanthraquinone and 2 - phenyl-4 - chloroquinazoline; the product dyes cotton from a Bordeaux vat orange-yellow shades; 4-chloroquinazoline may be similarly reacted; (2) 1-amino-5-nitroanthraquinone and 2 - phenyl - 4 - chloroquinazoline; (3) 1-amino - 4 - anilidoanthraquinone and 2-phenyl - 4 - chloroquinazoline; the product may be sulphonated by dissolving it in weakly fuming monohydrate; 1 - amino - 4 - (41-aminophenyl) - aminoanthraquinone may be similarly reacted; (4) p-(4-chloro-2-quinazolyl)-benzoyl chloride (obtained by the action of phosphorus pentachoride on the acid obtained by oxidation of 2-(p-tolyl)-4-hydroxyquinazoline) and one or two molecular proportions of 1 - amino - 5 - benzoylaminoanthraquinone; in the former case the product may be further reacted with another amine; (5) 2-phenyl-4-chloroquinazoline and 4 - amino - 51 - chloroanthraquinone - 2 : 1 (N) - 11 : 21(N)-benzacridone; the product dyes cotton from a red-violet vat greenish-blue shades; (6) 2-(11 - nitro - 21 - anthraquinonyl) - 4 - chloroquinazoline and 4 - amino - 51 - chloroanthraquinone - 2 : 1(N) - 11 : 21(N) - benzacridone; the product dyes cotton from a Bordeaux vat dark blue shades, the nitro group being simultaneously reduced to amino; (7) 2-(21-thiazolanthronyl)-4-chloroquinazoline and 4-amino-51-chloroanthraquinone - 2 : 1(N) - 11 : 21\h (N)-benzacridone; the product dyes cotton from a Bordeaux vat green shades. 4 - Halogenquinazolines are obtainable by reacting anthranilic amide with a carboxylic acid chloride, which may contain a vattable residue, treating the product with alkali to effect ring closure to a 4-hydroxyquinazoline and treating this with phosphorus pentachloride. Reference is made to the production of 2-(11-nitro - 21 - anthraquinonyl) - 4 - chloroquinazoline from 1 - nitroanthraquinone - 2 - carboxylic acid chloride and anthranilic amide, and of 2 - (21 - thiazolanthronyl) - 4 - chloroquinazoline from thiazolanthrone -2 - carboxylic acid chloride and anthranilic amide. A sample has been furnished under Sect. 2 (5) of the product obtained from 2 : (11-nitro - 21 - anthraquinonyl) - 4 - chloroquinazoline and methylaniline. The product dyes cotton from a brown-red vat bluish red shades with simultaneous reduction of the nitro group to amino.