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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
Received: 19 October 2012; in revised form: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

Al-Etaibi AM, El-Apasery MA, Ibrahim MR, Al-Awadi NA. A Facile Synthesis of New Monoazo Disperse Dyes Derived from 4-Hydroxyphenylazopyrazole-5-amines: Evaluation of Microwave Assisted Dyeing Behavior. Molecules. 2012; 17(12):13891-13909.

Chicago/Turabian Style

Al-Etaibi, Alya M.; El-Apasery, Morsy A.; Ibrahim, Maher R.; Al-Awadi, Nouria A. 2012. "A Facile Synthesis of New Monoazo Disperse Dyes Derived from 4-Hydroxyphenylazopyrazole-5-amines: Evaluation of Microwave Assisted Dyeing Behavior." Molecules 17, no. 12: 13891-13909.


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