Complexation of Disperse Dyes Derived from Thiophene with Cu, Co, Zn Metal and Their Application Properties on Polyester and Nylon 6.6 Fabrics

Ethyl-4-((4-chlorophenyl)carbamoyl)-2-((5-cyano-2-hydroxy-1,4-dimethyl-6-oxo-1,6-dihydro-pyridin-3-yl) diazenyl)-5-methylthiophene-3-carboxylate and ethyl-4-((4-chlorophenyl) carbamoyl)-2-((5-cyano-1-ethyl-2-hydroxy-4-methyl-6-oxo-1,6-dihydropyridin-3-yl)diazenyl)-5-methylthiophene-3-carboxylate disperse dyes were synthesised in this study by the coupling reaction of synthesised ethyl 2-amino-4-((4-chlorophenyl)carbamoyl)-5-methylthiophene-3-carboxylate with 6-hydroxy-1,4-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile and 1-ethyl-6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile. Metal complexation of the synthesised disperse dyes with copper, cobalt and zinc metals were carried out. The structure of the synthesised intermediate, coupling components, dyes and their complexes were elucidated by analytical techniques such as proton nuclear magnetic resonance (1H NMR), carbon 13 nuclear magnetic resonance (13C NMR), mass spectrometry (MS), fourier transform infra-red (FTIR), ultraviolet-visible spectroscopy as well as the determination of their melting points. The molar extinction coefficient of the dyes and their complexes ranges from 24,800 – 83,200 Lmol-1cm-1. The FTIR spectra of the synthesised dyes and their complexes showed the presence of cyano group in the range 2225 – 2229 cm-1, carbonyl group in the range 1640 – 1692 cm-1, hydroxyl group in the range 3310 – 3340 cm-1, azo group in the range 1398 – 1491 cm-1, stretching vibration of (N-H) in the range 3474 – 3478 cm-1 and stretching vibration of aromatic (C-H) in the range 2882 – 2989 cm-1. The dyeing performance of the dyes and their metal complex analogous were assessed on polyester and nylon 6.6 fabrics. The dyes and their complexes were found have good levelness, excellent fastness to perspiration and sublimation, good to excellent wash fastness and light fastness on both polyester and nylon 6.6 fabrics with different shades of violet and brown.