Abstract
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 (<sup>1</sup>H NMR), carbon 13 nuclear magnetic resonance (<sup>13</sup>C 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<sup>-1</sup>cm<sup>-1</sup>. The FTIR spectra of the synthesised dyes and their complexes showed the presence of cyano group in the range 2225 – 2229 cm<sup>-1</sup>, carbonyl group in the range 1640 – 1692 cm<sup>-1</sup>, hydroxyl group in the range 3310 – 3340 cm<sup>-1</sup>, azo group in the range 1398 – 1491 cm<sup>-1</sup>, stretching vibration of (N-H) in the range 3474 – 3478 cm<sup>-1</sup> and stretching vibration of aromatic (C-H) in the range 2882 – 2989 cm<sup>-1</sup>. 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.
Highlights
Disperse azo dyes based on the 2-aminothiophene moieties are known to have excellent brightness of shade, they were established as a substitute to the more expensive anthraquinone dyes [1]
We report the synthesis of azo disperse dyes derived from ethyl 2-amino-4-[(4-chlorophenyl)carbamoyl]
Gallenkamp melting point apparatus (CD10127) was used for the melting point determination, Agilent Technologies Cary 630 fourier transform infra-red (FTIR) machine was employed for the determination of the infra-red spectra, the wavelength of maximum absorption of the dyes and their complexes were determined in acetone using Jenway 6405 UV-visible spectrophotometer, mass spectrometry was determined on Agilent Technologies 7890R GC system 5977A MSD, 1H and 13 nuclear magnetic resonance (13C NMR) were carried out on Bruker AMX 300 MHz spectrometer and Microsal light fastness tester model no 225 and Blue wool standards were employed for the assessment of the light fastness
Summary
Disperse azo dyes based on the 2-aminothiophene moieties are known to have excellent brightness of shade, they were established as a substitute to the more expensive anthraquinone dyes [1]. Most heterocyclic dyes of technical interest for application to textiles are derived from diazo components consisting of five-membered rings containing one sulphur heteroatom and to which a diazotisable amino group is directly attached [810]. Description and investigation on the synthesis and application properties of monoazo and bis-heterocyclic monoazo dyes based on thiophene ring have been reported by different researchers there are few researches on their complexation with metals [11,12,13]. We report the synthesis of azo disperse dyes derived from ethyl 2-amino-4-[(4-chlorophenyl)carbamoyl]-
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