Fibers and Polymers

, Volume 19, Issue 3, pp 670–681 | Cite as

Synthetic Fiber Dyeing with New Pyrazole Disperse Dyes and Their Colorimetric and Fastness Properties

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Abstract

A series of disazo pyrazole disperse dyes were synthesized and reported at our previous work. These 8 synthesized disazo pyrazole disperse dyes (3a-3h) were applied to poly(lactic acid) (PLA), poly(ethylene terephthalate) (PET), and polyamide 6.6 fibers. Their colorimetric and color fastness properties were investigated. All studied fibers dyed with these synthesized dyes exhibited yellow-red shades. 3c (p-Cl), 3e (m-Cl), and 3h (o-Cl) disazo disperse dyes, having auxochrome -Cl, led to the lowest color yield values for all three studied fibers. The same dyes resulted in higher color strength with darker shades on the PET and PLA fabrics in comparison PA 6.6 fabrics. 3a (p-NO2), 3b (p-OCH3), 3d (m-NO2), 3f (o-NO2), and 3g (o-OCH3) disazo disperse dyes can be recommended for PLA and PET dyeing from the color point of view leading to medium to heavy depth of shades. The wash, alkaline and acidic perspiration, dry and wet rub, water and sea water fastness levels of PLA, PET, and PA 6.6 samples dyed with 3a-3h dyes were generally quite high and in the commercially acceptable range with few exceptions. Dyed PLA fabrics displayed better sublimation fastness levels than dyed PET and PA 6.6 fabrics. Synthesized disperse dyes resulted in high light fastness performance on especially PET and PLA fibers. Light fastness level was better for dyed PET samples by comparison with dyed PLA and PA 6.6 fabrics.

Keywords

Disperse dyes Pyrazole dyes Fastness Exhaustion Color properties 

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References

  1. 1.
    A. S. Shawali, J. Adv. Res., 1, 255 (2010).CrossRefGoogle Scholar
  2. 2.
    J. K. Wood, “The Chemistry of Dyeing”, 2nd ed., pp.75–77, Gurney & Jackson Corp., London, United Kingdom, 1926.Google Scholar
  3. 3.
    J. Suesat and P. Suwanruji in “Dyeing and Fastness Properties of Disperse Dyes on Poly(lactic acid) Fiber” (P. J. Hause Ed.), Chap.16, pp.351–372, InTech Publishing, Thailand, 2011.Google Scholar
  4. 4.
    C. E. Pellew, “Dyes and Dyeing”, p.264, Mcbride, Nast & Co., New York, 1913.Google Scholar
  5. 5.
    S. M. Burkinshaw, D. S. Jeong, and T. I. Chun, Dyes Pigment., 97, 374 (2013).CrossRefGoogle Scholar
  6. 6.
    E. Bagdatli and N. Öcal, J. Heterocyclic Chem., 49, 1179 (2012).CrossRefGoogle Scholar
  7. 7.
    M. Banchero, Color. Technol., 129, 2 (2013).CrossRefGoogle Scholar
  8. 8.
    M. A. Metwally, E. Abdel-Galil, A. Metwally, and F. A. Amer, Dyes Pigment., 92, 902 (2012).CrossRefGoogle Scholar
  9. 9.
    E. Karapinar and I. Aksu, J. Text. Eng., 20, 17 (2013).CrossRefGoogle Scholar
  10. 10.
    F. Karci and E. Bakan, J. Mol. Liq., 206, 309 (2015).CrossRefGoogle Scholar
  11. 11.
    G. Feng, H. F. Qian, G. Bai, Y. C. Liu, and L. L. Hu, Dyes Pigment., 129, 54 (2016).CrossRefGoogle Scholar
  12. 12.
    T. De Meyer, I. Steyaert, K. Hemelsoet, R. Hoogenboom, V. Van Speybroeck, and K. De Clerck, Dyes Pigment., 124, 249 (2016).CrossRefGoogle Scholar
  13. 13.
    Y. M. El-Kholy, S. A. Abdel-Hafiz, and S. H. Ahmed, J. Soc. Dyers Color., 114, 45 (1998).CrossRefGoogle Scholar
  14. 14.
    M. H. Helal, G. H. Elgemeie, and D. M. Masoud, Pigm. Resin. Technol., 37, 402 (2008).CrossRefGoogle Scholar
  15. 15.
    H. Z. Shams, Y. A. Youssef, F. A. Mohamed, M. M. El-Zawahry, M. H. Helal, and E. A. El-Kharadly, Pigm. Resin. Technol., 38, 372 (2009).CrossRefGoogle Scholar
  16. 16.
    H. F. Rizk, M. A. El-Badawi, S. A. Ibrahim, and M. A. El-Borai, J. Kor. Chem. Soc., 54, 737 (2010).CrossRefGoogle Scholar
  17. 17.
    H. F. Rizk, M. A. El-Badawi, S. A. Ibrahim, and M. A. El-Borai, Arab. J. Chem., 4, 37 (2011).CrossRefGoogle Scholar
  18. 18.
    F. Mohamed and Y. A. Youssef, Pigm. Resin. Technol., 41, 49 (2012).CrossRefGoogle Scholar
  19. 19.
    M. H. Helal, Pigm. Resin. Technol., 30, 296 (2001).CrossRefGoogle Scholar
  20. 20.
    G. H. Elgemeie, M. H. Helal, and H. M. El-Sayed, Pigm. Resin. Technol., 32, 100 (2003).CrossRefGoogle Scholar
  21. 21.
    A. M. Al-Etaibi, N. A. Al-Awadi, M. A. El-Apasery, and M. R. Ibrahim, Molecules, 16, 5182 (2011).CrossRefGoogle Scholar
  22. 22.
    A. M. Al-Etaibi, M. A. El-Apasery, M. R. Ibrahim, and N. A. Al-Awadi, Molecules, 17, 138 (2012).Google Scholar
  23. 23.
    A. Deeb, F. Yassine, N. Aouf, and W. Shehta, Int. J. ChemTech. Res., 6, 719 (2014).Google Scholar
  24. 24.
    H. Shaki, K. Gharanjig, and A. Khosravi, Biotechnol. Progr., 31, 1086 (2015).CrossRefGoogle Scholar
  25. 25.
    H. F. Rizk, S. A. Ibrahim, and M. A. El-Borai, Dyes Pigment., 112, 86 (2015).CrossRefGoogle Scholar
  26. 26.
    J. Witherington, V. Bordas, D. Haigh, D. M. B. Hichey, R. J. Ife, A. D. Rawlings, B. P. Slingsby, D. G. Smith, and R. W. Ward, Bioorg. Med. Chem. Lett., 13, 1581 (2003).CrossRefGoogle Scholar
  27. 27.
    S. Chimichi, M. Boccalini, M. M. M. Hassan, G. Viola, F. Dall’Acqua, and M. Curini, Tetrahedron, 62, 90 (2006).CrossRefGoogle Scholar
  28. 28.
    B. Yang, Y. Lu, C. J. Chen, J. P. Cui, and M. S. Cai, Dyes Pigment., 83, 144 (2009).CrossRefGoogle Scholar
  29. 29.
    A. M. Farag, K. A. K. Ali, T. M. A. El-Debbs, A. S. Mayhoub, A. E. Amr, N. A. Ebdel-Hafez, and M. M. Abdulla, Eur. J. Med. Chem., 45, 5887 (2010).CrossRefGoogle Scholar
  30. 30.
    V. Kumar, R. Aggarwal, P. Tyagi, and S. P. Singh, Eur. J. Med. Chem., 40, 922 (2005).CrossRefGoogle Scholar
  31. 31.
    K. S. Gudmundsson, B. A. Johns, Z. Wang, E. M. Turner, S. H. Allen, G. A. Freeman, F. L. Boyd, C. J. Sexton, D. W. Selleseth, K. R. Moniri, and K. L. Creech, Bioorg. Med. Chem., 13, 5346 (2005).CrossRefGoogle Scholar
  32. 32.
    K. I. Kobrakov, M. K. Feoktistov, G. S. Stankevich, V. I. Zvolinskii, K. M. Bormasheva, I. K. Moiseev, V. Y. Orlov, R. S. Begunov, and O. Y. Yakovleva, Fibre. Chem., 41, 73 (2009).CrossRefGoogle Scholar
  33. 33.
    H. Z. Shams, R. M. Mohareb, M. H. Helal, and A. E. Mahmoud, Molecules, 16, 6271 (2011).CrossRefGoogle Scholar
  34. 34.
    S. Malladi, A. M. Isloor, S. Isloor, and D. S. Akhila, Arab. J. Chem., 6, 335 (2013).CrossRefGoogle Scholar
  35. 35.
    Ç. Karabacak, T. Tilki, B. Ö. Tuncer, and M. Cengiz, Res. Chem. Intermed., 41, 1985 (2015).CrossRefGoogle Scholar
  36. 36.
    F. Karci, Color. Technol., 121, 275 (2005).CrossRefGoogle Scholar
  37. 37.
    M. H. Elnagdi, M. M. M. Sallam, H. M. Fahmy, S. A. M. Ibrahim, and M. A. M. Elias, Helv. Chim. Acta, 59, 551 (1976).CrossRefGoogle Scholar
  38. 38.
    M. E. Elnagdi, G. E. Elgemeie, and F. A. E. Abd-Elaal, Heterocycles, 23, 3121 (1985).CrossRefGoogle Scholar
  39. 39.
    D. Karst and Y. Yang, J. Appl. Polym. Sci., 96, 416 (2005).CrossRefGoogle Scholar
  40. 40.
    DyStar Textilfarben GmbH & Co. Deutschland KG, “IngeoTM Fiber Coloration Pack”, DyStar Plc., 2004.Google Scholar
  41. 41.
    O. Avinc, J. Bone, H. Owens, D. Phillips, and M. Wilding, Color. Technol., 122, 157 (2006).CrossRefGoogle Scholar
  42. 42.
    O. Avinc, Text. Res. J., 81, 1049 (2011).CrossRefGoogle Scholar
  43. 43.
    O. Avinc, Text. Res. J., 81, 1158 (2011).CrossRefGoogle Scholar
  44. 44.
    B. L. Deopura, R. Alagirusamy, M. Joshi, and B. Gupta, “Polyesters and Polyamides”, 1st ed., pp.41–60, Woodhead Publishing Series in Textiles, Elsevier, Cambridge, England, 2008.CrossRefGoogle Scholar
  45. 45.
    O. Avinc, D. Phillips, and M. Wilding, Color. Technol., 125, 288 (2009).CrossRefGoogle Scholar
  46. 46.
    A. Khoddami, O. Avinc, and S. Mallakpour, Prog. Org. Coat., 67, 311 (2010).CrossRefGoogle Scholar
  47. 47.
    O. Avinc, R. Day, C. Carr, and M. Wilding, Text. Res. J., 82, 975 (2012).CrossRefGoogle Scholar
  48. 48.
    O. Avinc and A. Khoddami, Fibre. Chem., 41, 68 (2010).CrossRefGoogle Scholar
  49. 49.
    O. Avinc, H. Owens, J. Bone, M. Wilding, D. Phillips, and D. Farrington, Fiber. Polym., 12, 893 (2011).CrossRefGoogle Scholar
  50. 50.
    J. F. Dawson, J. Soc. Dyers Color., 99, 183 (1983).CrossRefGoogle Scholar
  51. 51.
    J. Lunt and J. Bone, AATCC Rev., 1, 20 (2001).Google Scholar
  52. 52.
    T. Nakamura, K. Ishii, H. Kubokawa, K. Mogi, and R. R. Bommu, “An Overview on Dyeing Properties of Polylactic Acid (PLA) Fiber”, Proc. AATCC Int. Conf. Exhib., 2001.Google Scholar

Copyright information

© The Korean Fiber Society and Springer Science+Business Media B.V., part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of Fashion Design, Higher Vocational School of UlubeyUsak UniversityUsakTurkey
  2. 2.Department of Chemistry, Faculty of Science-ArtsPamukkale UniversityDenizliTurkey
  3. 3.Department of Textile Engineering, Engineering FacultyPamukkale UniversityDenizliTurkey

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