GB420743A - Improvements in the manufacture and production of dyestuffs - Google Patents

Abstract

Dyes are prepared by reacting ammonia or primary or secondary amines with compounds of the general formula <FORM:0420743/IV/1> (wherein R1, R2, R3 and R4 stand for hydrogen, or alkyl, cycloalkyl, aryl or aralkyl radicles, X stands for an oxygen or sulphur atom and Y for an oxygen or sulphur atom or two chlorine atoms) with elimination of Y and formation of linkage between the carbon atom to which Y is attached and the nitrogen atom of the nitrogenous compound, which reaction is carried out in the presence of water if cyclic amines are used. Starting materials comprise aminated xanthones, xanthiones, thioxanthones, thioxanthiones and their keto chlorides which may be substituted in the amino groups by alkyl, aralkyl, aryl and cycloalkyl groups. Suitable primary and secondary amines are methyl-, mono- or dipropyl-amines, ethanolamine, cyclohexylamine, aniline, naphthylamine or piperidine; instead of ammonia agents supplying this may be used, for example urea. Condensing agents such as zinc chloride may be present, and reaction temperatures of 0--100 DEG C. may be employed. In examples: (1) 3.6-tetramethyldiaminoxanthone chloride (prepared from the xanthone or xanthione and phosphorus oxychloride or phosgene) is condensed with gaseous or aqueous ammonia; paper is dyed yellow. The corresponding dimethyldiphenyl-, dimethyldibenzyl-, dimethyldicyclohexyl-derivatives may be similarly treated; (2) 3.6 p - diethyldiamino - 2.7 - dimethylxanthone chloride (prepared similarly to (1) above) is condensed in water with cyclohexylamine (dyes greenish - yellow); 3.6 - tetramethyldiamino-, 3.6-diethyldimethyldiamino-xanthone chlorides or 3.6-diethyldiaminothioxanthone chloride may be similarly reacted to give dyes; (3) 3.6-tetramethyldiaminothioxanthione is heated with zinc chloride and ammonium chloride, or this starting material first reacted with phosphorus oxychloride or phosgene and the product with ammonia; it dyes paper yellow-orange; (4) 3.6 - tetramethyl - (or tetraethyl -) diamino - xanthone chloride is condensed with aniline in aqueous solution (dyes reddish-orange); (5) 3.6-tetramethyldiaminothioxanthone chloride is condensed in aqueous solution with cyclohexylamine (dyes reddish-yellow). Xanthones and xanthiones used as starting materials may be prepared according to British Specification 314,826, [Class 2 (iii)], while the corresponding thioxanthones and thioxanthiones are obtainable analogously from tetraalkyldiaminothioxanthenes (German Specification 65739). British Specification 320,345, [Class 2 (iii)], also is referred to.