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Dyeing, color fastness and antimicrobial properties of some mono and disazo disperse dyes derived from thiazole moiety

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Abstract

Three series of mono and disazo disperse dyes were synthesized from 2-amino-4-(pyridin-3-yl) thiazole. The structure of the synthesized dyes was confirmed by elemental analysis, ultraviolet-visible, infrared, proton and carbon nuclear magnetic resonance and mass spectroscopy. The dyeing parameters, perspiration, wash and light fastness of eighteen azo disperse dyes on polyester have been investigated. Application of these dyes on polyester fabric gave yellow to reddish hues for mono azo derivatives and reddish to dark brown hues for disazo derivatives with fair to moderate light fastness and moderate to good wash and perspiration fastness grade. In addition, the synthesized dyes were screened for their antimicrobial activities against some gram positive, gram negative bacteria and fungi. Some of the prepared dyes gave excellent results against most of the tested organisms.

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References

  1. M. Z. Rehman, C. J. Anwar, and S. Ahmed, Bull. Korean Chem. Soc., 26, 1771 (2005).

    Article  Google Scholar 

  2. K. K. Vijaya Raj, B. Narayana, and B. V. Ashalatha, Eur. J. Med. Chem., 42, 425 (2007).

    Article  CAS  Google Scholar 

  3. B. X. Jiang and H. Gu, Bioorg. Med. Chem. Lett., 8, 363 (2000).

    CAS  Google Scholar 

  4. E. Medime and G. Capan, II Framaco., 49, 449 (1994).

    Google Scholar 

  5. F. Bordi, P. L. Catellani, and G. Morinha, II Framaco., 44, 795 (1989).

    CAS  Google Scholar 

  6. R. Lesyk, O. Vladzimirska, and S. Holota, Eur. J. Med. Chem., 42, 641 (2007).

    Article  CAS  Google Scholar 

  7. M. Kaeriyama, S. Suga, A. Hashimoto, and S. Sakai, Jpn. Kokai Tokkyo Koho (1983). CODEN: JKXXAF JP 58157794 A 19830919 Showa. CAN 100:103397 AN 1984:103397.

    Google Scholar 

  8. N. Kobayashi, K. Ueda, N. Itoh, S. Suzuki, G. Sakaguchi, A. Kato, A. Yukimasa, A. Hori, Y. Kooriyama, H. Haraguchi, K. Yasui, and Y. Kanda, PCT Int. Appl. (2008) 2. CODEN: PIXXD2 WO 2008133273 A1 20081106 CAN 149:534229 AN 2008:1339943.

    Google Scholar 

  9. K. Shankaran, K. L. Donelly, S. K. Shah, R. N. Guthikonda, M. MacCoss, J. L. Humes, S. G. Pacholok, S. K. Grant, T. M. Kelly, and K. K. Wong, Bioorg. Med. Chem. Lett., 14, 4539 (2004).

    Article  CAS  Google Scholar 

  10. A. A. Mandrugin, T. P. Trofimova, V. M. Fedoseev, S. Y. Proskuryakov, L. I. Shtein, A. N. Proschin, and A. N. Pushin, Pharm. Chem. J., 41, 640 (2007).

    Article  CAS  Google Scholar 

  11. T. Castaö, A. Encinas, C. Pérez, A. Castro, N. E. Campillo, and C. Gil, Bioorg. Med. Chem., 16, 6193 (2008).

    Article  Google Scholar 

  12. H. Li, C. S. Raman, P. Martásek, V. Král, B. S. S. Masters, and T. L. Poulos, J. Inorg. Biochem., 81, 133 (2000).

    Article  CAS  Google Scholar 

  13. S. Knapp, D. Vocadlo, Z. Gao, B. Kirk, J. Lou, and S. G. Withers, J. Am. Chem. Soc., 118, 6804 (1996).

    Article  CAS  Google Scholar 

  14. G. E. Whitworth, M. S. Macauley, K. A. Stubbs, R. J. Dennis, E. J. Taylor, G. J. Davies, I. R. Greig, and D. J. Vocadlo, J. Am. Chem. Soc., 129, 635 (2007).

    Article  CAS  Google Scholar 

  15. T. K. Ritter and C. H. Wong, Tetrahedron Lett., 42, 615 (2001).

    Article  CAS  Google Scholar 

  16. G. H. Elgemeie, M. H. Helal, E. M. Abbas, and E. A. Abdel Mowla, Pigment & Resin Technology, 31, 365 (2002).

    Article  CAS  Google Scholar 

  17. K. A. Bello, Dyes Pigments, 42, 294 (1999).

    Google Scholar 

  18. A. D. Town, Dyes Pigments, 42, 3 (1999).

    Article  Google Scholar 

  19. N. Amishiro, S. Nagamura, E. Kobayashi, K. Gomi, and H, Saito, J. Med. Chem., 42, 669 (1999).

    Article  CAS  Google Scholar 

  20. B. Cote, E. Martins, R. Frenette, R. Friesen, and Y. Ducharma, US 2002156105, [CA (2002); 137:325412].

  21. J. Cochran, S. Nanthacumar, E. Harrington, and J. Wang, PCT Int. Appl. (2002) (to Astrazeneca AB); [CA 2002; 138:14054].

    Google Scholar 

  22. K. Yamaguchi, M. Yada, T. Tsuji, Y. Hatanaka, K. Goda, and T. Kobori, Bioorg & Med. Chem. Lett., 9, 957 (1999).

    Article  CAS  Google Scholar 

  23. H. F. Rizk, M. A. EI-Badawi, S. A. Ibrahim, and M. A. ElBorai, Indian J. Org. Chem. (TSI), 4, 115 (2007).

    Google Scholar 

  24. H. F. Rizk, M. A. El-Borai, G. B. El-hefnawy, and H. F. Elsayed, Chin. J. Chem., 27, 1359 (2009).

    Article  CAS  Google Scholar 

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

    Google Scholar 

  26. H. F. Rizk, M. A. EI-Badawi, S. A. Ibrahim, and M. A. El-Borai, Arabian J. Chem., 4, 37 (2011).

    Article  CAS  Google Scholar 

  27. Anon; Standard Metods Forte Deterimination of the Color Fastness of Textiles and Leather, 5th ed., Society of Dyes and Colorists publication, Bradford, England, 1990.

    Google Scholar 

  28. T. G. Pridham, L. A. Lindenfelser, O. L. Shotwell, F. Stodola, R. G. Benedict, C. Foley, P. W. Jacks, W. J. Zaumeyer, and W. H. Perston, Mitchell J. W. Phytopathology, 46, 568 (1956).

    CAS  Google Scholar 

  29. G. Hallas and J. H. Choi, Dyes Pigments, 40, 99 (1999).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Tanta University, 31527, Tanta, Egypt

    M. A. El-Borai, H. F. Rizk, G. B. El-Hefnawy, H. F. El-Sayed & S. A. Ibrahim

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  1. M. A. El-Borai
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  2. H. F. Rizk
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  3. G. B. El-Hefnawy
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  4. H. F. El-Sayed
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  5. S. A. Ibrahim
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Correspondence to M. A. El-Borai.

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El-Borai, M.A., Rizk, H.F., El-Hefnawy, G.B. et al. Dyeing, color fastness and antimicrobial properties of some mono and disazo disperse dyes derived from thiazole moiety. Fibers Polym 14, 2061–2068 (2013). https://doi.org/10.1007/s12221-013-2061-8

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  • DOI: https://doi.org/10.1007/s12221-013-2061-8

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