GB722543A - Fluorescent heterocyclic compounds - Google Patents

Abstract

Textile materials are brightened by treatment with sulphonated azoles of the formula <FORM:0722543/IV (c)/1> or <FORM:0722543/IV (c)/2> where R and R1 are aryl or aryl-vinyl groups, Y is O or S, n is 1 or 2 and m is 1, 2 or 3. Thus cotton may be treated with an aqueous solution of the sodium salt of sulphonated 1 : 4-di-(51-phenyl - oxazolyl - 21) - benzene or 1 : 4 - di - (51 - phenyl - thiazolyl - 21) - benzene, and wool with the sodium salt of sulphonated 2-styryl - 5 - phenyloxazole (with acetic acid) or 2 - b - naphthyl - 5 - phenylthiazole. A further example describes the treatment of perlon with the sodium salt of sulphonated 2-b -naphthyl-5-phenyloxazole and formic acid.ALSO:The invention comprises sulphonated azoles of the formul <FORM:0722543/IV (b)/1> and <FORM:0722543/IV (b)/2> where R and R1 are aryl or aryl-vinyl groups Y is O or S, n is 1 or 2 and m is 1, 2 or 3. These are prepared by treating aminoketones R-CO-CH2-NH2 with mono- or di-basic acids R-COOH or R-(COOH)2 or their halides or amides, ring-closing the resulting acylamino-ketones with a condensing agent to give oxazoles, if desired converting into thiazoles by means of phosphorus sulphide, and finally sulphonating. In the examples: (1) o -aminoacetophenone is condensed with terephthaloyl chloride to give terephthaloyl bis-N-phenacylamide, the latter ring-closed with sulphuric acid to 1 : 4-bis-(51-phenyl-oxazolyl-21)-benzene and finally sulphonated; (2) the bis-amide of (1) is treated with phosphorus pentasulphide to yield 1 : 4-bis-(51-phenyl-thiazolyl-21)-benzene and the latter sulphonated; (3) 2 : 5 - diphenyloxazole is sulphonated; (4) 2 : 5-diphenylthiazole is sulphonated; (5) o -cinnamoylamino-acetophenone is heated with sulphuric acid to give the sulphonic acid of 2 - styryl - 5 - phenyloxazole; (6) b -naphthoyl chloride and o -aminoacetophenone give o -(b -naphthoylamino)-acetophenone which is heated with sulphuric acid, yielding sulphonated 2-(b -naphthyl)-5-phenyloxazole; (7) 2-(b -naphthyl)-5-phenylthiazole is obtained in an analogous way and then sulphonated.ALSO:Soaps are brightened by addition of sulphonated azoles of the formula <FORM:0722543/III/1> where R and R1 are aryl-vinyl groups, y is O or S, n is 1 or 2 and m is 1, 2 or 3.