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

Hatem E. Gaffer, Mohamed A. E. Khalifa, Shaima F. El-Bially, Mohamed A. Metwally

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

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DOI: http://dx.doi.org/10.20450/mjcce.2010.176

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