New azo disperse dyes containing cyclohexanone ring for dyeing polyester and nylon fabrics

Abstract

Condensation of 2,4-diacarboethoxy-5-hydroxy-3-(4-methoxyphenyl)-5-methyl cyclohexanone (1) with equimolar amounts of hydrazine hydrate and phenyl hydrazine afforded the corresponding 2H-indazole-5-carboxylates 2a and 2b, respectively. Coupling of 2 with diazotized aromatic amines furnished the corresponding azo compounds 3a n. When compound 1 was subjected to the Japp-Klingemann reaction in alkaline medium with diazotized aromatic amines furnished the corresponding hydrazones 4a-g. The treatment of 4a-g with phenyl hydrazine in acetic acid allows the isolation of arylhydrazono derivatives 5a-g. The structures of the dyes were established using analytical and spectral data. Evaluation of the technical properties and color assessment of the dyes were done.

Keywords

• japp-klingemann reaction
• phenyl hydrazine
• indazole
• cyclohexane