Skip to main content
Log in

Removal of anionic dyes with glycidyl methacrylate-grafted polyethylene terephthalate (PET) fibers modified with ethylenediamine

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

In this work, the epoxy groups of poly (ethylene terephthalate) PET copolymers grafted with glycidyl methacrylate (GMA) were modified with ethylenediamine (EDA) to form exclusive adsorbent for removal of congo red (CR) and acid violet7 (AV-7) in the aqueous environment. The graft copolymers (GMA-g-PET) were synthesized with different grafting yield by a radical polymerization process with using benzoyl peroxide (Bz2O2) as radical initiator. Amination of GMA-g-PET fibers using EDA was studied in different solvents, and maximum yield (w/w %) was obtained in the toluene. The grafted and modified fibers were analyzed by CHNS organic elemental analyzer, scanning electron microscopy (SEM), Fourier transform infrared (FTIR) spectroscopy and nuclear magnetic resonance spectroscopy (13C-NMR). By SEM analysis, the morphological changes have been shown after grafting. The chemical changes after grafting and addition of EDA to the fibers have been proven with FTIR, NMR and elemental analysis. The thermal properties of the grafted and aminated fibers were researched with thermogravimetric analysis and differential scanning calorimeter analysis. The removal of dyes by the EDA-GMA-g-PET fibers was investigated in aqueous medium at different conditions. Optimum conditions of different parameters such as pH of medium, graft yield of GMA on the fibers, adsorption duration, initial concentration of dye molecules and effect of graft yield on amination reaction were examined. The optimum pH of CR and AV-7 removal was found 5 and 3, respectively. The removal yield was found about 100% for both dyes while initial concentration of dyes was changed from 10 to 400 mg/L. Adsorbed dyes with the fibers were desorbed with 1 M NaOH at room conditions.

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

Access this article

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

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11

Similar content being viewed by others

Availability of data and materials

The datasets used and/or analyzed during the current study are available from the corresponding author on reasonable request.

References

  1. X. Han, P. Tian, H. Pang, Q. Son, G. Ning, Y. Yu, H. Fang, RSC Adv. 4, 28119 (2014)

    Article  CAS  Google Scholar 

  2. M. Liu, J. Xu, B. Cheng, W. Ho, J. Yu, Appl. Surf. Sci. 332, 121 (2015)

    Article  CAS  Google Scholar 

  3. K.M. Gray, M.J. Walker, M.J.S. Burn, M. Mazur, K. Niedzwiedzka, K. Liszka, D. Thorburn Burnsc, J. Assoc. Public Anal. 44, 18 (2016)

    Google Scholar 

  4. B. Li, Y. Zhang, X. Zhou, Z. Liu, Q. Liu, X. Li, J. Alloys Compd. 673, 265 (2016)

    Article  CAS  Google Scholar 

  5. J. Fang, X. Huang, X. Ouyang, X. Wang, Chem. Eng. J. 270, 309 (2015)

    Article  CAS  Google Scholar 

  6. H. Kono, K. Ogasawara, R. Kusumoto, C. Zou, Y. Yang, S. Yang, Carbohydr. Polym. 152, 170 (2016)

    Article  CAS  PubMed  Google Scholar 

  7. X. Liu, W. Gong, J. Luo, C. Zou, Y. Yang, S. Yang, Appl. Surf. Sci. 362, 517 (2016)

    Article  CAS  Google Scholar 

  8. V.S. Munagapati, V. Yarramuthi, Y. Kim, K.M. Lee, D.S. Kim, Ecotoxicol. Environ. Saf. 148, 601 (2018)

    Article  CAS  PubMed  Google Scholar 

  9. R.A. Shawabkeh, M.F. Tutunji, Appl. Clay Sci. 24, 111 (2003)

    Article  CAS  Google Scholar 

  10. Q. Sun, L. Yang, Water Res. 37, 1535 (2003)

    Article  CAS  PubMed  Google Scholar 

  11. A. Miri, H.O. Shahraki Vahed, M. Sarani, Res. Chem. Intermed. 44, 6907 (2018)

    Article  CAS  Google Scholar 

  12. A.N. Soon, B.H. Hameed, Desalination 269, 1 (2011)

    Article  CAS  Google Scholar 

  13. J. Guo, D. Jiang, Y. Wu, P. Zhou, Y.J. Lan, Hazard Mater. 194, 290 (2011)

    Article  CAS  Google Scholar 

  14. L. Xu, L. Du, C. Wang, W. Xu, J. Membrane Sci. 409–410, 329 (2012)

    Article  Google Scholar 

  15. I.M. Bulai, E. Venturino, J. Math. Chem. 54, 1387 (2016)

    Article  CAS  Google Scholar 

  16. C. Li, H. Xia, L. Zhang, J. Peng, S. Cheng, J. Shu, S. Zhang, Res. Chem. Intermed. 44, 2231 (2018)

    Article  CAS  Google Scholar 

  17. K. Günay, M. Arslan, O. Bozkaya, Y. Aluç, Z. Gün Gök, Environ. Sci. Pollut. Res. 26, 31644 (2019)

    Article  Google Scholar 

  18. A. Murugesan, M. Divakaran, P. Raveendran, A.B.N. Nikamanth, K.J. Thelly, J. Polym. Environ. 27, 1007 (2019)

    Article  CAS  Google Scholar 

  19. C.F. Mok, Y.C. Ching, F. Muhamad, N.A.A. Osman, N.D. Hai, C.R.C. Hassan, J. Polym. Environ. 28, 775 (2020)

    Article  CAS  Google Scholar 

  20. A.A. Peláez-Cid, A.M. Herrera-González, M. Salazar-Villanueva, A.B. Hernández, J. Environ. Manag. 181, 269 (2016)

    Article  Google Scholar 

  21. E.T. Acar, S. Ortaboy, G. Atun, Chem. Eng. J. 276, 340 (2015)

    Article  CAS  Google Scholar 

  22. X. Yuan, S.P. Zhuo, W. Xing, C. Hon-You, D. Xiao-Dond, L. Xin-Mei, Y. Zi-Feng, J. Colloid Interface Sci. 310, 83 (2007)

    Article  CAS  PubMed  Google Scholar 

  23. G. McKay, J.F. Porter, G.R. Prasad, Water Air Soil Pollut. 114, 423 (1999)

    Article  CAS  Google Scholar 

  24. Y. Cui, B. Li, H. He, W. Zhou, C. Bangin, Q. Huodong, Chem. Res. 49, 483 (2016)

    Article  CAS  Google Scholar 

  25. M.S. Chiou, P.Y. Ho, H.Y. Li, Dyes Pigments 60, 69 (2004)

    Article  CAS  Google Scholar 

  26. M. Arslan, K. Günay, Polym. Bull. 76, 953 (2019)

    Article  CAS  Google Scholar 

  27. S.P.D. Monte Blanco, F.B. Scheufele, A.N. Módenes, F.R. Espinoza-Quiñones, P. Marin, A. Dimitrov Kroumov, C.E. Borba, Chem. Eng. J. 307, 466 (2017)

    Article  CAS  Google Scholar 

  28. M. Arslan, M. Yiǧitoǧlu, J. Appl. Polym. Sci. 110, 30 (2008)

    Article  CAS  Google Scholar 

  29. A.R. Nesic, V.V. Panic, A.E. Onjia, S. Velickovic, J. Colloids. Surf. A 476, 24 (2015)

    Article  CAS  Google Scholar 

  30. M. Arslan, K. Günay, Int. J. Polym. Mater. 68, 811 (2019)

    Article  CAS  Google Scholar 

  31. Z. Gün Gök, K. Günay, M. Arslan, M. Yiğitoğlu, Polym. Bull. 76, 6179 (2019)

    Article  Google Scholar 

  32. R. Coşkun, C. Soykan, M. Saçak, React. Funct. Polym. 66, 599 (2006)

    Article  Google Scholar 

  33. M. Arslan, Fiber Polym. 11, 325 (2010)

    Article  CAS  Google Scholar 

  34. N. Ünlü, K. Günay, M. Arslan, Polym. Plast. Technol. Eng. 59, 527 (2020)

    Google Scholar 

  35. E.L. Burton, M. Woodhead, P. Coates, T. Gough, J. Appl. Polym. Sci. 117, 2707 (2010)

    CAS  Google Scholar 

  36. S. Korpayev, C. Kavaklı, Ş Çolak, P.A. Kavaklı, Cellulose 25(1), 813 (2018)

    Article  Google Scholar 

  37. C. Liu, R. Bai, L. Hong, J. Colloid Interface Sci. 303, 99 (2006)

    Article  CAS  PubMed  Google Scholar 

  38. P. Akkaş Kavaklı, C. Kavaklı, N. Seko, T. Tamada, O. Güven, Radiat. Phys. Chem. 127, 13 (2016)

    Article  Google Scholar 

  39. Y.W. Awodi, A. Johnson, R.H. Peters, A.V. Popoola, J. Appl. Polym. Sci. 33, 2503 (1987)

    Article  CAS  Google Scholar 

  40. X. Yu, S. Tong, M. Ge, L. Wu, J. Zuo, C. Cao, W. Song, Carbohydr. Polym. 92, 380 (2013)

    Article  CAS  PubMed  Google Scholar 

  41. A. Noritake, M. Hori, M. Shigematsu, M. Tanahashi, Polym. J. 40, 498 (2008)

    Article  CAS  Google Scholar 

  42. Z. Gün Gök, M. İnal, O. Bozkaya, M. Yiğitoğlu, İ Vargel, J. Appl. Polym. Sci. 137(41), 49257 (2020)

    Article  Google Scholar 

  43. D. Das, R. Das, P. Ghosh, S. Dhara, A.M. Panda, S. Pal, RSC Adv. 3, 25340 (2013)

    Article  CAS  Google Scholar 

  44. F. Samperi, C. Puglisi, R. Alicata, G. Montaudo, Polym. Degrad. Stabil. 83(1), 3 (2004)

    Article  CAS  Google Scholar 

  45. S. Zulfiqar, M. Zulfiqar, M. Nawaz, C. McNeill, J.G. Gorman, Polym. Degrad. Stab. 30, 195 (1990)

    Article  CAS  Google Scholar 

  46. S. Chatterjee, S. Chatterjee, B.P. Chatterjee, A.K. Guha, Colloids Surf. A 299, 146 (2007)

    Article  CAS  Google Scholar 

  47. M.K. Purkait, A. Maiti, S. DasGupta, S. De, J. Hazard Mater. 145, 287 (2007)

    Article  CAS  PubMed  Google Scholar 

  48. A.M. Donia, A.A. Atia, W.A. Al-amrani, A.M. El-Nahas, J. Hazard Mater. 161, 1544 (2009)

    Article  CAS  PubMed  Google Scholar 

  49. C. Lei, M. Pi, W. Zhou, Y. Guo, F. Zhang, J. Qin, Chem. Phys. Lett. 687, 143 (2017)

    Article  CAS  Google Scholar 

  50. N.K. Amin, J. Hazard Mater. 165, 52 (2009)

    Article  CAS  PubMed  Google Scholar 

  51. G. Zengin, H. Ozgunay, E.M. Ayan, M.M. Mutlu, Pol. J. Environ. Stud. 21, 499 (2012)

    CAS  Google Scholar 

  52. M. Shirzad-Siboni, S.J. Jafari, M. Farrokhi, J.K. Yang, Environ. Eng. Res. 18, 247 (2013)

    Article  Google Scholar 

  53. P. Terangpi, S. Chakraborty, Appl. Water Sci. 7, 3631 (2017)

    Article  Google Scholar 

  54. M. Chahkandi, Mater. Chem. Phys. 202, 340 (2017)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors are grateful to Kırıkkale University for its contribution.

Funding

The experimental studies were carried out in the laboratories at Kırıkkale University.

Author information

Authors and Affiliations

Authors

Contributions

We warrant that all authors have contributed to the article. All authors took part in the planning of the study. Kübra Günay and Zehra Gün Gök took part in material synthesis and adsorption experiments. Ogün Bozkaya and Metin Arslan took part in the characterization and analysis of the synthesized material. Metin Arslan also took part in finding the necessary financial contributions. All authors took part in investigating and interpreting the results and writing the article.

Corresponding author

Correspondence to Ogün Bozkaya.

Ethics declarations

Conflict of interests

There are no conflicts to declare.

Ethical approval and consent to participate

Not applicable.

Consent to publish

This paper has not been published, submitted for publication or currently under evaluation for publication elsewhere. We would like this research study to be considered for publication in “Environmental Science and Pollution Research.”

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bozkaya, O., Günay, K., Arslan, M. et al. Removal of anionic dyes with glycidyl methacrylate-grafted polyethylene terephthalate (PET) fibers modified with ethylenediamine. Res Chem Intermed 47, 2075–2093 (2021). https://doi.org/10.1007/s11164-021-04398-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-021-04398-7

Keyword

Navigation