A facile synthesis of new monoazo disperse dyes derived from 4-hydroxyphenylazopyrazole-5-amines: evaluation of microwave assisted dyeing behavior

Molecules. 2012 Nov 23;17(12):13891-909. doi: 10.3390/molecules171213891.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines* / chemical synthesis
  • Amines* / chemistry
  • Coloring Agents* / chemical synthesis
  • Coloring Agents* / chemistry
  • Coloring Agents* / radiation effects
  • Hydrazines / chemistry
  • Microwaves
  • Nitriles / chemistry
  • Pentanones / chemistry
  • Polyesters / chemistry
  • Pyrazoles* / chemical synthesis
  • Pyrazoles* / chemistry
  • Pyrimidines / chemistry

Substances

  • Amines
  • Coloring Agents
  • Hydrazines
  • Nitriles
  • Pentanones
  • Polyesters
  • Pyrazoles
  • Pyrimidines
  • hydrazine
  • acetylacetone
  • dicyanmethane
  • pyrimidine