Skip to main content
SpringerLink
Log in

Synthesis and characterization of novel self-colored PET (polyethylene terephthalate) by step-growth polymerization containing dye based on 1,8-naphthalimide group

  • Published:
Fibers and Polymers Aims and scope Submit manuscript

Abstract

A novel self-colored polyethylene terephthalate (PET) was synthesized using a synthesized dye, 4-amino-N-propanoic acid-1,8-naphthalimide. For this purpose, the prepared naphthalimide dye was added upon the polycondensation step and then a self-colored PET was prepared by step-growth polymerization. The characterization of synthesized self-colored PET and naphthalimide dye were carried out using TLC, FTIR, 1HNMR, DSC, UV-visible and Fluorometery. Results indicated that, the novel fluorescent yellow-green PET with appropriate properties was obtained. The glass transition temperature of self-colored PET was 70 °C and it was measured by differential scanning calorimeter, which revealed that addition of dye to the chains of polymer did not affect the context of glass transition of polymer. UV-visible spectrum indicated that, 99 percent of dye was incorporated in polymer chains chemically. Furthermore, the intrinsic viscosity of self-colored PET was 0.556 dl/g and molecular weight of polymer was around 35000 (g/mol) and measured using the viscometer technique.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. A. Ziah, A. Shah, S. Lee, and J. Song, Polym. Bull., 72, 2797 (2015).

    Article  Google Scholar 

  2. X. Huang, C. Li, L. Zheng, D. Zhang, G. Guan, and Y. Xiao, Polym. Int., 58, 893 (2009).

    Article  CAS  Google Scholar 

  3. M. J. L. Tschan, E. Brule, P. Haquette, and C. M. Thomas, Polym. Chem., 3, 836 (2012).

    Article  CAS  Google Scholar 

  4. F. Amanizadeh, A. Naderi, Y. Jarestani, and N. Kaptan, Polym. Bull., 71, 1315 (2014).

    Article  CAS  Google Scholar 

  5. H. R. Kim and W. S. Song, Fiber. Polym., 7, 339 (2006).

    Article  CAS  Google Scholar 

  6. N. M. Abdullah and I. Ahmad, Fiber. Polym., 14, 584 (2013).

    Article  CAS  Google Scholar 

  7. N. Guo, D. Hu, H. Wang, R. Wang, and Y. Xiong, Polym. Bull., 70, 3031 (2013).

    Article  CAS  Google Scholar 

  8. S. Mallakpour and Z. Rafiee, Iran. Polym. J., 17, 217 (2008).

    CAS  Google Scholar 

  9. J. E. McIntyre in “Modern Polyesters Chemistry and Technology of Polyesters and Copolyesters” (J. Scheirs and T. E. Long Eds.), pp.1–24, Wiley-VCH, Weinheim, 2003.

    Google Scholar 

  10. D. Paszun and T. Spychaj, Ind. Eng. Chem. Res., 36, 1373 (1997).

    Article  CAS  Google Scholar 

  11. X. He, X. Zhou, K. Jia, D. Zhang, H. Shou, and X. Liu, Matter. Lett., 182, 367 (2016).

    Article  CAS  Google Scholar 

  12. M. Jou, K. Macario, C. Carvalho, R. Dias, M. Brum, F. Cunha, C. Ferreira, and I. Chanca, Int. J. Mass. Spectrom., 388, 65 (2015).

    Article  CAS  Google Scholar 

  13. A. M. Al-Sabagh, F. Z. Yehia, G. Eshaq, A. M. Rabie, and A. E. Elmetwally, Egypt. J. Pet., 25, 53 (2016).

    Article  Google Scholar 

  14. M. Mazloom, M. Rafizadeh, V. Haddadi-Asl, and M. Pakniat, Iran. Polym. J., 16, 587 (2007).

    CAS  Google Scholar 

  15. H. Shirali, M. Rafizadeh, and F. A. Taromi, J. Compos. Mater., 14, 301 (2014).

    Article  Google Scholar 

  16. R. D. Kale, A. Banerjee, and G. Katre, Fiber. Polym., 16, 54 (2014).

    Article  Google Scholar 

  17. S. R. Patil, A. S. Choudhary, and N. Sekar, Fiber. Polym., 16, 1068 (2015).

    Article  CAS  Google Scholar 

  18. A. Arcoria, A. Cerniani, R. D. Giorgi, M. Longo, and R. Toscanoa, Dyes Pigment., 11, 269 (1989).

    Article  CAS  Google Scholar 

  19. G. Montero, D. Hinks, and J. Hooker, J. Supercrit. Fluids., 26, 47 (2003).

    Article  CAS  Google Scholar 

  20. T. Harifi and M. Montazer, Dyes Pigment., 97, 440 (2013).

    Article  CAS  Google Scholar 

  21. K. Singha, Int. J. Text. Sci., 2, 1 (2013).

    Google Scholar 

  22. E. Alkaya and G. Demirer, J. Clean. Prod., 65, 595 (2014).

    Article  CAS  Google Scholar 

  23. H. Hicks and R. Dietmar, J. Clean. Prod., 15, 395 (2007).

    Article  Google Scholar 

  24. D. Chico, M. Aldaya, and A. Garrido, J. Clean. Prod., 57, 238 (2013).

    Article  Google Scholar 

  25. S. Xu, J. Chen, B. Wang, and Y. Yang, J. Clean. Prod., 112, 987 (2016).

    Article  CAS  Google Scholar 

  26. I. Grabchev, S. Seher, B. Rosica, and G. Vasilis, Eur. Polym. J., 43, 4297 (2007).

    Article  CAS  Google Scholar 

  27. C. Ugela, H. Ofenberg, and A. Caval, Eur. Polym. J., 21, 681 (1985).

    Article  Google Scholar 

  28. H. Soltani, A. Khosravi, K. Gharanjig, M. Khatibzadeh, M. Khorasani, and F. A. Taromi, Iran. Polym. J., 19, 491 (2010).

    Google Scholar 

  29. T. Konstantinova, A. Spireva, and T. Petkova, Dyes Pigment., 45, 125 (2000).

    Article  CAS  Google Scholar 

  30. I. Grabchev, S. Yordanova, S. Stoyanov, and I. Petkov, J. Chem. Article ID 793721 (2014).

    Google Scholar 

  31. I. Grabchev and J. M. Chovelon, Dyes Pigment., 77, 1 (2008).

    Article  CAS  Google Scholar 

  32. N. Georgiev, M. Dimitrova, Y. Todorova, and V. Bojinov, Dyes Pigment., 131, 9 (2016).

    Article  CAS  Google Scholar 

  33. S. Medel, P. Bosch, I. Grabchev, M. Torre, and P. Ramirez, Eur. Polym. J., 64, 241 (2016).

    Article  Google Scholar 

  34. J. Grabchev and J. Chovelon, Polym. Degrad. Stabil., 92, 1911 (2007).

    Article  CAS  Google Scholar 

  35. S. Chatterjee, S. Pramanik, S. Hossain, S. Bhattacharya, and S. Chandra, J. Photochem. Photobiol. A. Chem., 187, 64 (2007).

    Article  CAS  Google Scholar 

  36. J. Gan, K. Chen, C. Chang, and H. Tian, Dyes Pigment., 57, 21 (2003).

    Article  CAS  Google Scholar 

  37. V. Bojinov, G. Ivanova, J. M. Chovelonc, and I. Grabchev, Dyes Pigment., 58, 65 (2003).

    Article  CAS  Google Scholar 

  38. A. Khosravi, S. Moradian, K. Gharanjig, and F. A. Taromi, Dyes Pigment., 69, 79 (2006).

    Article  CAS  Google Scholar 

  39. V. Bojinov and T. Konstantinova, Sens. Actuators. B. Chem., 123, 869 (2007).

    Article  CAS  Google Scholar 

  40. H. Shaki, K. Gharanjig, S. Rouhani, and A. Khosravi, J. Photochem. Photobiol. A. Chem., 216, 44 (2010).

    Article  CAS  Google Scholar 

  41. T. Konstantinova, R. Lazarova, and V. Bojinov, Polym. Degrad. Stabil., 82, 115 (2003).

    Article  CAS  Google Scholar 

  42. E. Riordan and H. Blair, Polymer, 20, 196 (1979).

    Article  CAS  Google Scholar 

  43. I. Grabchev and V. Bojinov, Polym. Degrad. Stabil., 70, 147 (2000).

    Article  CAS  Google Scholar 

  44. S. Mallakpour and E. Hashemi, Polym. Bull., 65, 551 (2009).

    Article  Google Scholar 

  45. M. Okazaki, T. Tanaka, and S. Taniguchi, J. Synth. Org. Chem. Jpn., 14, 344 (1957).

    Article  Google Scholar 

  46. D. Yuan, R. G. Brown, J. D. Hepworth, M. Alexiou, and J. H. P. Tyman, J. Heterocycl. Chem., 45, 397 (2008).

    Article  CAS  Google Scholar 

  47. R. Pamios, J. Cifre, M. Martinez, and J. Torre, Colloid. Polym. Sci., 286, 1223 (2008).

    Article  Google Scholar 

  48. H. Chuah, D. L. Vien, and U. Soni, Polymer, 42, 7137 (2001).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Polymer Engineering and Color Technology, Amirkabir University of Technology (Polytechnic of Tehran), Tehran, 15875-4413, Iran

    Ehsan Zamani, Mehdi Rafizadeh, Alireza Khosravi & Milad Pilehkouhi

  2. Department of Chemical Engineering, Golestan University, Gorgan, 49138-15759, Iran

    Hanieh Shaki

Authors
  1. Ehsan Zamani
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hanieh Shaki
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mehdi Rafizadeh
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Alireza Khosravi
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Milad Pilehkouhi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hanieh Shaki.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zamani, E., Shaki, H., Rafizadeh, M. et al. Synthesis and characterization of novel self-colored PET (polyethylene terephthalate) by step-growth polymerization containing dye based on 1,8-naphthalimide group. Fibers Polym 18, 1431–1437 (2017). https://doi.org/10.1007/s12221-017-6795-6

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12221-017-6795-6

Keywords

Search

Navigation