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

Isaac Oluwatobi Abolude; Kasali Ademola Bello; Peter Obinna Nkeonye; Abdulraheem Giwa

doi:doi:10.11648/j.ajset.20210603.11

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

Isaac Oluwatobi Abolude, Kasali Ademola Bello, Peter Obinna Nkeonye, Abdulraheem Giwa

Published in American Journal of Science, Engineering and Technology (Volume 6, Issue 3)

Received: 29 June 2021 Accepted: 22 July 2021 Published: 2 August 2021

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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 (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.

Published in	American Journal of Science, Engineering and Technology (Volume 6, Issue 3)
DOI	10.11648/j.ajset.20210603.11
Page(s)	45-58
Creative Commons	This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.
Copyright	Copyright © The Author(s), 2024. Published by Science Publishing Group

Keywords

Disperse Dyes, Complexes, Polyester, Nylon 6.6, Fastness Properties

References

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[2]	Hallas, G. and Towns, A. D. (1997). Dyes derived from aminothiophenes. Part 3: application of some disperse dyes derived from 2-aminothiophenes to hydrophobic fibres. Dyes and Pigments, (33), 215-228.
[3]	Towns, A. D. (1999). Developments in azo disperse dyes derived from heterocyclic diazo components. Dye and Pigments, (42), 3-28.
[4]	Maradiya, H. R. (2001). Synthesis of azobenzo[b]thiophene derivatives and their dyeing performance on polyester fibre. Turkish Journal of Chemistry, (25), 441-450.
[5]	Aspland, J. R. (1993). A Series on Dyeing, Chapter 9: The Structure and Properties of Disperse Dyes and Related Topics, Text. Chem. Col., 25 (1), 21–25.
[6]	Adedokun, A. A. (2011). Synthesis of Disperse Dyes from 2-aminothiophenes and their Dyeing Performance on Synthetic Fabrics. Ph. D Thesis submitted to the Department of Textile Science and Technology, Ahmadu Bello University, Zaria, pp 1-122.
[7]	Oni, O., Bello, K. A. and Shibdawa, M. A. (2019). Synthesis, Characterization and Application of Monoazo Disperse Dyes Derived From 4-Aminobenzaldehyde and 4-Amino-3-Nitro-Benzadehyde as Diazo Components on Polyester. IOSR Journal of Applied Chemistry, 12 (3-1), 36-46.
[8]	Maradiya, H. R. and Patel, V. S. (2002). Thiophene based monoazo disperse dyes for polyester fabric. Journal of the Serbian Chemical Society, 67 (1), 17–25.
[9]	Patel, P. M. and Wadia, D. N. (2008). Synthesis and Application of Acid Dyes Based on 3-(4-Aminophenyl)-5-benzylidene-2-substituted phenyl-3, 5-dihydroimidazol-4-one. Egyptian Journal of Chemistry, 5 (1), 987-996.
[10]	Bashandy, M., Mohammed, F., El-Molla, M., Sheier, M. and Bedair, A. (2016). Synthesis of Novel Acid Dyes with Coumarin Moiety and Their Utilization for Dyeing Wool and Silk Fabrics. Open Journal of Medicinal Chemistry, 6, 18-35. doi: 10.4236/ojmc.2016.61002.
[11]	Alaa S. A. and Tarek H. A. (2006). Novel azo disperse dyes derived from aminothiophenes: Synthesis and UV-visible studies. Dyes and Pigments, 70 8-17.
[12]	Metwally, M. A., Abdel-Galil, E., Metwally, A. and Amer, F. A. (2012). New azodisperse dyes with Thiazole, thiophene, pyridone and pyrazolone moiety for dyeing polyester fabrics. Dyes and pigments, 92 (3), 902-908.
[13]	Karci F. and Karci F. (2012). Synthesis and tautomeric structures of some novel thiophene-based bis-heterocyclic monoazo dyes. Journal of Molecular Structure, 1024, 117 – 122.
[14]	Khalid, J. A., Ahmed, K. A. and Ali, M. T. (2016). Synthesis of some transition metal complexes with new heterocyclic thiazolyl azo dye and their uses as sensitizers in photo reactions. Journal of Molecular Structure 1108, 378–397.
[15]	Giles, C. H. (1974). A laboratory Course in Dyeing”, The Society of Dyers and Colourists, Bradford, pp 15–37.
[16]	AATCC (1999). Technical Manual, American Association of Textile Chemists and Colorists, 75, 311, North Carolina, USA.

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Isaac Oluwatobi Abolude, Kasali Ademola Bello, Peter Obinna Nkeonye, Abdulraheem Giwa. (2021). Complexation of Disperse Dyes Derived from Thiophene with Cu, Co, Zn Metal and Their Application Properties on Polyester and Nylon 6.6 Fabrics. American Journal of Science, Engineering and Technology, 6(3), 45-58. https://doi.org/10.11648/j.ajset.20210603.11

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Isaac Oluwatobi Abolude; Kasali Ademola Bello; Peter Obinna Nkeonye; Abdulraheem Giwa. Complexation of Disperse Dyes Derived from Thiophene with Cu, Co, Zn Metal and Their Application Properties on Polyester and Nylon 6.6 Fabrics. Am. J. Sci. Eng. Technol. 2021, 6(3), 45-58. doi: 10.11648/j.ajset.20210603.11

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AMA Style

Isaac Oluwatobi Abolude, Kasali Ademola Bello, Peter Obinna Nkeonye, Abdulraheem Giwa. Complexation of Disperse Dyes Derived from Thiophene with Cu, Co, Zn Metal and Their Application Properties on Polyester and Nylon 6.6 Fabrics. Am J Sci Eng Technol. 2021;6(3):45-58. doi: 10.11648/j.ajset.20210603.11

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@article{10.11648/j.ajset.20210603.11,
  author = {Isaac Oluwatobi Abolude and Kasali Ademola Bello and Peter Obinna Nkeonye and Abdulraheem Giwa},
  title = {Complexation of Disperse Dyes Derived from Thiophene with Cu, Co, Zn Metal and Their Application Properties on Polyester and Nylon 6.6 Fabrics},
  journal = {American Journal of Science, Engineering and Technology},
  volume = {6},
  number = {3},
  pages = {45-58},
  doi = {10.11648/j.ajset.20210603.11},
  url = {https://doi.org/10.11648/j.ajset.20210603.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajset.20210603.11},
  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 (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.},
 year = {2021}
}

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TY  - JOUR
T1  - Complexation of Disperse Dyes Derived from Thiophene with Cu, Co, Zn Metal and Their Application Properties on Polyester and Nylon 6.6 Fabrics
AU  - Isaac Oluwatobi Abolude
AU  - Kasali Ademola Bello
AU  - Peter Obinna Nkeonye
AU  - Abdulraheem Giwa
Y1  - 2021/08/02
PY  - 2021
N1  - https://doi.org/10.11648/j.ajset.20210603.11
DO  - 10.11648/j.ajset.20210603.11
T2  - American Journal of Science, Engineering and Technology
JF  - American Journal of Science, Engineering and Technology
JO  - American Journal of Science, Engineering and Technology
SP  - 45
EP  - 58
PB  - Science Publishing Group
SN  - 2578-8353
UR  - https://doi.org/10.11648/j.ajset.20210603.11
AB  - 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.
VL  - 6
IS  - 3
ER  -

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Author Information

Isaac Oluwatobi Abolude

Department of Polymer and Textile Engineering, Ahmadu Bello University, Zaria, Nigeria
Kasali Ademola Bello

Department of Polymer and Textile Engineering, Ahmadu Bello University, Zaria, Nigeria
Peter Obinna Nkeonye

Department of Polymer and Textile Engineering, Ahmadu Bello University, Zaria, Nigeria
Abdulraheem Giwa

Department of Polymer and Textile Engineering, Ahmadu Bello University, Zaria, Nigeria

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APA Style

Isaac Oluwatobi Abolude, Kasali Ademola Bello, Peter Obinna Nkeonye, Abdulraheem Giwa. (2021). Complexation of Disperse Dyes Derived from Thiophene with Cu, Co, Zn Metal and Their Application Properties on Polyester and Nylon 6.6 Fabrics. American Journal of Science, Engineering and Technology, 6(3), 45-58. https://doi.org/10.11648/j.ajset.20210603.11

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ACS Style

Isaac Oluwatobi Abolude; Kasali Ademola Bello; Peter Obinna Nkeonye; Abdulraheem Giwa. Complexation of Disperse Dyes Derived from Thiophene with Cu, Co, Zn Metal and Their Application Properties on Polyester and Nylon 6.6 Fabrics. Am. J. Sci. Eng. Technol. 2021, 6(3), 45-58. doi: 10.11648/j.ajset.20210603.11

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AMA Style

Isaac Oluwatobi Abolude, Kasali Ademola Bello, Peter Obinna Nkeonye, Abdulraheem Giwa. Complexation of Disperse Dyes Derived from Thiophene with Cu, Co, Zn Metal and Their Application Properties on Polyester and Nylon 6.6 Fabrics. Am J Sci Eng Technol. 2021;6(3):45-58. doi: 10.11648/j.ajset.20210603.11

Copy | Download

@article{10.11648/j.ajset.20210603.11,
  author = {Isaac Oluwatobi Abolude and Kasali Ademola Bello and Peter Obinna Nkeonye and Abdulraheem Giwa},
  title = {Complexation of Disperse Dyes Derived from Thiophene with Cu, Co, Zn Metal and Their Application Properties on Polyester and Nylon 6.6 Fabrics},
  journal = {American Journal of Science, Engineering and Technology},
  volume = {6},
  number = {3},
  pages = {45-58},
  doi = {10.11648/j.ajset.20210603.11},
  url = {https://doi.org/10.11648/j.ajset.20210603.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajset.20210603.11},
  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 (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.},
 year = {2021}
}

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TY  - JOUR
T1  - Complexation of Disperse Dyes Derived from Thiophene with Cu, Co, Zn Metal and Their Application Properties on Polyester and Nylon 6.6 Fabrics
AU  - Isaac Oluwatobi Abolude
AU  - Kasali Ademola Bello
AU  - Peter Obinna Nkeonye
AU  - Abdulraheem Giwa
Y1  - 2021/08/02
PY  - 2021
N1  - https://doi.org/10.11648/j.ajset.20210603.11
DO  - 10.11648/j.ajset.20210603.11
T2  - American Journal of Science, Engineering and Technology
JF  - American Journal of Science, Engineering and Technology
JO  - American Journal of Science, Engineering and Technology
SP  - 45
EP  - 58
PB  - Science Publishing Group
SN  - 2578-8353
UR  - https://doi.org/10.11648/j.ajset.20210603.11
AB  - 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.
VL  - 6
IS  - 3
ER  -

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