Patent GB-784926-A (GB)
Title: Improvements in the production of triazine vat dyestuffs of the anthraquinone series
IPC: C09B1/467
Filed: 1956-03-28
Abstract: The invention comprises a process of producing vat dyes of the formula: <FORM:0784926/IV (b)/1> in which R and R1 represent vattable radicals of the anthraquinone series and Ar an aromatic radical or a heterocyclic radical of aromatic character which consists in saponifying a 2,6-diamino-4-Ar-triazine by means of caustic alkali to form the corresponding 2,6-dihydroxy-1,3,5-triazine, converting this in known manner with phosphorus or sulphur halides into the 2,6 - dihalogen - 1,3,5 - triazine and reacting the latter and 2 mol. of an aminoanthraquinone or a vattable derivative thereof, preferably in the same reaction medium and in presence of an acid-binding agent. The 2,6-diaminotriazines may be prepared by reaction of nitrile with dicyandiamide.  In examples: (1) benzonitrile is reacted with dicyandiamide in glycol monomethyl ether in presence of potassium hydroxide, and the product is boiled with caustic soda solution, and acidified with hydrochloric acid or carbon dioxide to give 4 - phenyl - 2,6 - dihydroxy - 1,3,5 - triazine, which is reacted with phosphorus pentachloride or oxychloride or give 4-phenyl-2,6-dichloro-1,3,5-triazine; this last is reacted with (a) 1-aminoanthraquinone; (b) 1,4-diamino-2-acetylanthraquinone; (c) 1 - amino - 5 - benzoyl-aminoanthraquinone; (d) a mixture of 1,4-diamino-2-acetylanthraquinone and 1-amino-anthraquinone or 1-amino-4 or 5-benzoylamino-anthraquinone.  Also in examples: (2) o-methoxybenzonitrile and o-chlorbenzonitrile are reacted with dicyandiamide as under (1) to prepare 4 - (21 - methoxyphenyl) - 2,6 - dihydroxy - 1,3,5 - triazine and 4 - (21 - chlorphenyl) - 2,6 - dihydroxy - 1,3,5 - triazine which are reacted respectively with 1-amino-4-methoxyanthraquinone and 1,4 - diamino - 2 -acetyl-anthraquinone.  Other anthraquinones specified contain alkylsulphonyl or sulphodialkylamide groupings or are anthraquinonebenzacridones, and nitriles specified include naphthonitriles, cyanopyridines, cyanoquinolines, cyanocarbazoles, cyanothiophenes, or cyanothiazoles and nitriles containing alkyl, aryl, aralkyl, alkoxy, aryloxy, alkylsulphonyl, arylsulphonyl, or sulphonamide groups or halogen atoms. Specifications 350,575, 372,123, 449,477 and 574,483, [all in Group IV], are referred to.ALSO:2,6-Dihalogen-1,3,5-triazines containing in 4-position an aryl or heterocyclic radical are made by the action of a phosphorus or sulphur halide on (1) the corresponding 2,6-dihydroxytriazines, obtained by saponification of (2) the corresponding 2,6-diamino-triazines, obtained by reaction of aryl or heterocyclic carboxylic nitriles with dicyandiamide.  In examples, benzonitrile, o-methoxybenzonitrile, and o-chlorbenzonitrile are each reacted with dicyandiamide in ethylene glycol monomethyl ether in presence of potassium hydroxide to give 2,6-diamino-4-phenyl, o-methoxyphenyl and o-chlorphenyl-1,3,5-triazines, which are hydrolysed with caustic soda to give 2,6-dihydroxy-4-phenyl, o-chlorphenyl and o-methoxyphenyl-1,3,5-triazines, which are reacted with phosphorus pentachloride or oxychloride to give the 2,6-dichlor-4-phenyl, o-methoxyphenyl, and o - chlorphenyl - 1,3,5-triazines. Specifications 350,575, 372,123, 449,477 and 574,483, [all in Group IV], are referred to.