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Synthesis and spectral characterization of novel azomethine disperse dyes derived from pyrazolone moiety and their dyeing performance on polyester fabrics

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Abstract

A series of new azomethine dyes based on pyrazolone system have been synthesized via different routes. The solvatochromism for the dyes was evaluated with respect to spectroscopic properties in various solvents. The dyes were applied as disperse dyes on polyester fabrics and gave shade poor to excellent light fastness, washing, perspiration, sublimation, and rubbing fastness properties. Also the position of color in CIELAB coordinates (L*, a*, b*) and K/S value were investigated.

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References

  1. B. Peng, G. Liu, L. Liu, D. Jia, and K. Yu, J. Mol. Struct., 692, 217 (2004).

    Article  CAS  Google Scholar 

  2. P. N. Dhol, T. E. Achary, and A. Nayak, J. Ind. Chem. Soc., 52, 196 (1975).

    Google Scholar 

  3. F. R. Souza, V. T. Souaza, V. Ratzalaff, L. P. Borges, M. R. Olivera, and H. G. Bonacorso, Eur. J. Pharmacol., 45, 141 (2002).

    Article  Google Scholar 

  4. J. Singh and R. Tripathy, PCT Int. Appl., 138 (2001).

  5. M. Arnost, A. Pierce, E. Haar, D. Lauffer, J. Madden, K. Tanner, and J. Green, Bioorg. Med. Chem. Lett., 20, 1661 (2010).

    Article  CAS  Google Scholar 

  6. T. Arai, M. Nonogawa, K. Makino, N. Endo, H. Mori, T. Miyoshi, K. Yamashita, M. Sasada, M. Kakuyama, and K. Fukuda, J. Pharmacol. Exp. Ther., 324, 529 (2008).

    Article  CAS  Google Scholar 

  7. R. R. Venkat, V. Vijaykumar, and N. Suchetha Kumari, Eur. J. Med. Chem., 44, 3852 (2009).

    Article  Google Scholar 

  8. S. J. Ratnadeep, G. M. Priyanka, D. D. Santosh, K. D. Sanjay, and H. G. Charansingh, Bioorg. Med. Chem. Lett., 20, 3721 (2010).

    Article  Google Scholar 

  9. X. L. Rena, B. Hua, and H. Z. Yang, Arkivoc, 15, 59 (2005).

    Google Scholar 

  10. K. K. Ramanaumar, A. G. Raghavendra, V. Srilalitha, G. S. Narayana, and L. K. Ravindranath, Scientia Iranica, 19, 605 (2012).

    Article  Google Scholar 

  11. H. F. Rizk, M. A. El-Borai, G. B. El-Hefnawy, and H. F. El-Sayed, Chin. J. Chem., 27, 1359 (2009).

    Article  CAS  Google Scholar 

  12. M. C. Godoy, M. R. Fighera, F. R. Souza, A. E. Flores, M. A. Rubin, M. R. Oliveira, N. Zanatta, M. A. P. Martin, H. G. Bonacorso, and C. F. Mello, Eur. J. Pharmacol., 496, 93 (2004).

    Article  CAS  Google Scholar 

  13. S. Yokoyama, T. Sato, K. Kimura, N. Furutachi, and O. Takahashi, U. S. Patent, 5,026,867 (1991).

    Google Scholar 

  14. R. A. Clarke and N. J. Pitman, U. S. Patent, 4,092,104 (1978).

    Google Scholar 

  15. D. E. Machiele and N. Y. Rochester, U. S. Patent, 3,952,009 (1976).

    Google Scholar 

  16. G. H. Brown, B. Graham, P. W. Vettum, and A. Weissberger, J. Am. Chem. Soc., 73, 919 (1951).

    Article  CAS  Google Scholar 

  17. M. A. Elborai, E. A. Aly, M. Fahmy, and A. A. Gaber, Delta J. Sci., 17, 110 (1993).

    Google Scholar 

  18. W. Hansel, Arch. Pharm., 309, 900 (1976).

    Article  CAS  Google Scholar 

  19. W. G. Herkstroeter, J. Am. Chem. Soc., 95, 8686 (1973).

    Article  CAS  Google Scholar 

  20. D. P. Maier, G. P. Happ, and T. H. Regan, Org. Mass Spectrom., 2, 1289 (1969).

    Article  CAS  Google Scholar 

  21. N. G. Rossmann, B. Winnig, and W. Aeise, J. Prakt. Chem., 329, 767 (1987).

    Article  Google Scholar 

  22. A. Sammour, T. Zimaity, and M. El Borai, J. Prakt. Chem., 314, 612 (1972).

    Article  CAS  Google Scholar 

  23. A. Loria, U. S. Patent, 1,181,057 (1964).

  24. A. I. M. Koraiem, J. Praktische Chemie, 5, 695 (1984).

    Article  Google Scholar 

  25. H. F. Rizk, Bulg. Chem. Comm., 41, 241 (2009).

    CAS  Google Scholar 

  26. H. Wiley and S. Davies, J. Am. Chem. Soc., 76, 4931 (1954).

    Article  CAS  Google Scholar 

  27. L. Koike and K. Okawa, J. Chem. Soc., 57, 56 (1954).

    Google Scholar 

  28. T. L. Jacobs and R. C. Elderfield, Heterocycles., 5, 116 (1957).

    Google Scholar 

  29. G. B. Hefnawy, M. A. El-Borai, E. A. Aly, and A. A. Gaber, Indian J. Fiber Text. Res., 17, 87 (1992).

    Google Scholar 

  30. G. B. Hefnawy, M. A. El-Borai, E. A. Aly, and A. A. Gaber, Ind. J. Fiber Text. Res., 17, 160 (1992).

    Google Scholar 

  31. H. F. Rizk, M. A. EI-Badawi, S. A. Ibrahim, and M. A. El-Borai, Indian J. Org. Chem., 4, 115 (2007).

    Google Scholar 

  32. H. F. Rizk, M. A. EI-Badawi, S. A. Ibrahim, and M. A. El-Borai, J. Korean Chem. Soc., 154, 737 (2010).

    Article  Google Scholar 

  33. H. F. Rizk, M. A. EI-Badawi, S. A. Ibrahim, and M. A. El-Borai, Arabian J. Chem., 4, 25 (2011).

    Article  Google Scholar 

  34. Anonymous, “Standard Methods for the Determination of the Color Fastness of Textiles and Leather”, 5th Ed., The Society of Dyes and Colorists, Bradford, England, 1990.

    Google Scholar 

  35. M. Ghaharpour, A. Rashidi, and H. Tayebi, World Appl. Sci. J., 14, 1291 (2011).

    CAS  Google Scholar 

  36. J. Eluguero and R. Jacquier, Bull. Soc. Chim. France, 8, 2832 (1966).

    Google Scholar 

  37. S. B. Buyuktas, Synth. React. Inorg. Met-Org Chem., 24, 1179 (1994).

    Article  CAS  Google Scholar 

  38. George G. Guilbault, “Fluorescence: Theory, Instrumentation and Practice”, p.207, Edward Arnold Ltd., NewYork, 1967.

    Google Scholar 

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Correspondence to Mohamed A. El-Borai.

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El-Borai, M.A., Rizk, H.F., El-Hefnawy, G.B. et al. Synthesis and spectral characterization of novel azomethine disperse dyes derived from pyrazolone moiety and their dyeing performance on polyester fabrics. Fibers Polym 17, 729–737 (2016). https://doi.org/10.1007/s12221-016-5362-x

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  • DOI: https://doi.org/10.1007/s12221-016-5362-x

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