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

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