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Molecules 2012, 17(12), 13891-13909; doi:10.3390/molecules171213891
Article

A Facile Synthesis of New Monoazo Disperse Dyes Derived from 4-Hydroxyphenylazopyrazole-5-amines: Evaluation of Microwave Assisted Dyeing Behavior

1,* , 2,3, 2 and 2
1 Natural Science Department, College of Health Science, Public Authority for Applied Education and Training, P.O. Box 14281, Fayha 72853, Kuwait 2 Chemistry Department, Faculty of Science, Kuwait University, P.O. Box 5969, Safat 13060, Kuwait 3 Dyeing, Printing and Textile Auxiliaries Department, Textile Research Division, National Research Centre, Dokki, Giza 12622, Egypt
* Author to whom correspondence should be addressed.
Received: 19 October 2012 / Revised: 14 November 2012 / Accepted: 16 November 2012 / Published: 23 November 2012
(This article belongs to the Section Organic Synthesis)
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Abstract

A series of new monoazo disperse dyes containing pyrazolopyrimidine moieties was synthesized by coupling malononitrile or 3-aminocrotononitrile with 4-hydroxy- benzenediazonium chloride. Treatment of the resulting products with hydrazine hydrate yields the corresponding 4-arylazoaminopyrazoles, which then react with either 2,4-pentanedione and enaminonitriles or aryl-substituted enaminoketones to give the target pyrazolopyrimidine monoazo disperse dyes. Structural assignments of the dyes were made using both NMR spectroscopic and X-ray crystallographic methods. A high temperature dyeing method, by microwave irradiation, was employed with polyester fabrics. Most of the dyed fabrics tested displayed moderate light fastness and excellent washing and perspiration fastness levels.
Keywords: aminopyrazoles; microwave irradiation; enaminone; disperse dyes; 2,4-pentanedione; enaminonitrile aminopyrazoles; microwave irradiation; enaminone; disperse dyes; 2,4-pentanedione; enaminonitrile
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Al-Etaibi, A.M.; El-Apasery, M.A.; Ibrahim, M.R.; Al-Awadi, N.A. A Facile Synthesis of New Monoazo Disperse Dyes Derived from 4-Hydroxyphenylazopyrazole-5-amines: Evaluation of Microwave Assisted Dyeing Behavior. Molecules 2012, 17, 13891-13909.

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