Synthesis, Spectral Property and Dyeing Assessment of Azo Disperse Dyes Containing Carbonyl and Dicyanovinyl Groups

Abstract

A series of azo disperse dyes having dicyanovinyl groups was synthesized by the Knoevenagel condensation with malononitrile from carbonyl substituted phenylazo disperse dyes which were prepared by conventional diazo coupling reaction of aniline derivatives as diazo components. A variety of coupling components such as anilines, an indole and a pyridone were used. The azo disperse dyes were evaluated for their spectral properties and dyeing assessment on the polyester fabrics. The azo disperse dyes containing dicyanovinyl groups showed bathochromic shifts and darker colors due to increased electron withdrawing strength in their azo components and extended conjugation by dicyanovinyl groups than their parent carbonyl substituted azo dyes. The dyes containing 2-acetylamino-5-methoxy substituent in the coupling component exhibited higher wavelength of maximum absorbance (λ max ) and significant negative solvatochromism than those of other dyes due to intramolecular hydrogen bonding.

Synthesis of Malononitrile-Condensed Disperse Dyes and Application on Polyester and Nylon Fabrics

“…Disperse dyes are substantially water-insoluble nonionic dyes which are applied to hydrophobic fibres (cellulose acetate, polyester, and nylon) from aqueous dispersions [1][2][3][4][5].…”

Synthesis of N-substituted arylhydrazones: applying to polyester fabric as disperse dyes

“…In the past few decades, disperse dyes from azo derivatives have gained importance and are widely used in various fields (Fadda and Abbas, 2016;Cinar et al, 2014;Yazdanbakhsh et al, 2009;Al-Qalafet al, 2013;Choi et al, 2013). These types of compounds have excellent coloration properties and are suitable for the dyeing of polyester fabrics (Patel, 2012).…”