Dyeing performance on polyester fibers and DFT investigation of newly synthesized 2-arylazo-dioxoisoindolinecyanoacetamide derivatives

Abstract

AbstractA series of aryl-diazinyl-cyanoacetamide (2a–l) were prepared by coupling the appropriate diazotized arylamines with dioxoisoindoline cyanaoacetamide (1). Also, the cyclization of azo derivatives (2f, 2h, and 2j) with chloroacetonitrile to yield the pyrazole derivatives (5f, 5h, and 5j) was studied. Moreover, compound 2d reacts with malononitrile to afford compound (6e). In a similar manner compound, 2d reacts with hydroxylamine to afford the sole product tetrazine derivative 8d. All the newly synthesized compounds were fully characterized by both analytical and spectral analyses. The geometries of the azo and hydrazo tautomeric forms were optimized at the B3LYP/6-311G level of theory. The dyeing performance of the synthesized dyes on polyester fibers has been assessed. Most of the dyes showed a good affinity to polyester fibers. No details regarding the synthesis and dyeing performance of such dyes are reported before in the literature.Keywords: Azo disperse dyespolyester fiberscyanoacetamidedyeingdyeing performance Disclosure statementNo potential conflict of interest was reported by the authors.