Skip to main content
Log in

Synthesis and characterization of poly(ethylene terephthalate) fibers grafted with N-(hydroxymethyl) acrylamide by free radical: its application in elimination of Congo red

  • Original Paper
  • Published:
Polymer Bulletin Aims and scope Submit manuscript

Abstract

In this study, firstly, N-(hydroxymethyl) acrylamide (HMAAm) was grafted on poly(ethylene terephthalate) fibers (PET) by utilizing benzoyl peroxide (Bz2O2) as an initiator. The alteration in graft percentage with the polymerization time, temperature, concentration of initiator and monomers were investigated. For grafting experiments, the optimum temperature, duration for grafting and initiator concentration were found be 85 °C, 4 h and 0.008 M, respectively, and the maximum grafting yield was determined to be 25% at these conditions. After grafting, the morphological and chemical changes on the grafted fibers were examined scanning electron microscopy and Fourier-transform infrared spectroscopy. The thermal properties of the obtained PET fibers were examined with differential scanning calorimeter analysis. In addition, the water absorption capacities of the grafted fibers obtained at optimal conditions were investigated and it was found the maximum percentage of water retention reached 56%. Removal of Congo red (CR) with the grafted fibers was performed using a batch process. The effects of different parameters such as pH, grafting yield of HMAAm, adsorption time and CR concentration on the sorption capacity of the grafted fibers were investigated. The optimal pH for adsorption of CR was found to be 2, and the adsorption process reached equilibrium in 4 h. The amount of adsorbed CR molecules increased with the increment in the grafting yield up to 17%, and the graft copolymers adsorbed CR with 5.62 mg/g efficiency when the initial CR concentration was 80 ppm. The PET-g-HMAAm fibers synthesized in this study can be obtained easily and inexpensively, and the constructed fibers could be used to remove ionic substance from aqueous solution.

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

References

  1. Chen H, Zhao J (2009) Adsorption study for removal of Congo red anionic dye using organo-attapulgite. Adsorption 15:381–389. https://doi.org/10.1007/s10450-009-9155-z

    Article  CAS  Google Scholar 

  2. Chiou MS, Ho P, Ho Y, Li HY (2004) Adsorption of anionic dyes in acid solutions using chemically cross-linked chitosan beads. Dyes Pigments 60(1):69–84. https://doi.org/10.1016/S0143-7208(03)00140-2

    Article  CAS  Google Scholar 

  3. Gong R, Ding Y, Li M, Yang C, Liu H, Sun Y (2005) Utilization of powdered peanut hull as biosorbent for removal of anionic dyes from aqueous solution. Dyes Pigments 64(3):187–192. https://doi.org/10.1016/j.dyepig.2004.05.005

    Article  CAS  Google Scholar 

  4. Neamtu M, Yediler A, Siminiceanu I, Macoveanu M, Kellrup A (2004) Decolorization of disperse red 354 azo dye in water by several oxidation processes-a comparative study. Dyes Pigments 60(1):61–68. https://doi.org/10.1016/S0143-7208(03)00129-3

    Article  CAS  Google Scholar 

  5. Abdullah AZ, Salamatinia B, Kamaruddin AH (2009) Application of response surface methodology for the optimization of NaOH treatment on oil palm frond towards improvement in the sorption of heavy metals. Desalination 244:227–238. https://doi.org/10.1016/j.desal.2008.06.004

    Article  CAS  Google Scholar 

  6. Arslan M, Günay K (2017) Synthesis and characterization of PET fibers grafted with binary mixture of 2-methylpropenoic acid and acrylonitrile by free radical: its application in removal of cationic dye. Polym Bull 74:1221–1236. https://doi.org/10.1007/s00289-016-1773-5

    Article  CAS  Google Scholar 

  7. Aboua KN, Yobouet YA, Yao KB, Gona DL, Trokourey A (2015) Investigation of dye adsorption onto activated carbon from the shells of Macore fruit. J Environ Manag 156:10–14. https://doi.org/10.1016/j.jenvman.2015.03.006

    Article  CAS  Google Scholar 

  8. Küçükosmanoğlu M, Gezici O, Ayar A (2006) The adsorption behaviors of methylene blue and methyl orange in a diaminoethane sporopollenin-mediated column system. Sep Purif Technol 52:280–287. https://doi.org/10.1016/j.seppur.2006.05.005

    Article  CAS  Google Scholar 

  9. Wan Ngah WS, Teong LC, Hanafiah MAKM (2011) Adsorption of dyes and heavy metal ions by chitosan composites: a review. Carbohydr Polym 83:1446–1456. https://doi.org/10.1016/j.carbpol.2010.11.004

    Article  CAS  Google Scholar 

  10. Mittal H, Ray SS (2016) A study on the adsorption of methylene blue onto gum ghatti/TiO2 nanoparticles-based hydrogel nanocomposite. Int J Biol Macromol 88:66–80. https://doi.org/10.1016/j.ijbiomac.2016.03.032

    Article  CAS  PubMed  Google Scholar 

  11. Jiang F, Dinh DM, Hsieh YL (2017) Adsorption and desorption of cationic malachite green dye on cellulose nanofibril aerogels. Carbohydr Polym 173:286–294. https://doi.org/10.1016/j.carbpol.2017.05.097

    Article  CAS  PubMed  Google Scholar 

  12. Arslan M, Günay K (2018) Synthesis of amine-functionalized methacrylic acid-g-poly(ethylene terephthalate) fiber and its Congo red removal ability. Polym Bull 75:1701–1713. https://doi.org/10.1007/s00289-017-2121-0

    Article  CAS  Google Scholar 

  13. Gün Gök Z, Günay K, Arslan M, Yiğitoğlu M (2019) Removing of congo red from aqueous solution by 2-hydroxyethyl methacrylate-g-poly(ethylene terephthalate) fibers. Polym Bull 76:6179–6191. https://doi.org/10.1007/s00289-019-02721-2

    Article  CAS  Google Scholar 

  14. Miluski P, Kochanowicz M, Zmojda J, Dorosz D (2017) Luminescent properties of Tb3+-doped poly(methyl methacrylate) fiber. Chin Opt Lett 15:70602. https://doi.org/10.3788/COL201715.070602

    Article  Google Scholar 

  15. Wang Y, Yin Z, Li H, Gao G, Zhang X (2017) Friction and wear characteristics of ultrahigh molecular weight polyethylene (UHMWPE) composites containing glass fibers and carbon fibers under dry and water-lubricated conditions. Wear 380–381:42–51. https://doi.org/10.1016/j.wear.2017.03.006

    Article  CAS  Google Scholar 

  16. Arslan M, Günay K (2019) Application of 4-VP-g-PET fibers and its N-oxide derivative as an adsorbent for removal of cationic dye. Polym Bull 76:963–965. https://doi.org/10.1007/s00289-018-2400-4

    Article  CAS  Google Scholar 

  17. Arslan M, Günay K (2018) Synthesis and use of PET fibers grafted with 4-vinyl pyridine and 2-methylpropenoic acid for removal of rhodamine B and methylene blue from aqueous solutions. J Polym Sci Appl 1:3

    Google Scholar 

  18. Arslan M (2011) Immobilization horseradish peroxidase on amine-functionalized glycidyl methacrylate- g-poly(ethylene terephthalate) fibers for use in azo dye decolorization. Polym Bull 66(7):865–879. https://doi.org/10.1007/s00289-010-0316-8

    Article  CAS  Google Scholar 

  19. Patel MV, Raval DK, Patel RG, Patel VS (1992) Synthesis, optimization and characterization of graft copolymers from Leucaena glauca seed gum and methylmethacrylate. Carbohydr Polym 17(2):115–120. https://doi.org/10.1016/0144-8617(92)90104-X

    Article  CAS  Google Scholar 

  20. Coşkun R, Soykan C, Saçak M (2006) Adsorption of copper (II), nickel (II) and cobalt (II) ions from aqueous solution by methacrylic acid/acrylamide monomer mixture grafted poly (ethylene terephthalate) fiber. Sep Purif Technol 49:107–114. https://doi.org/10.1016/j.seppur.2005.09.002

    Article  CAS  Google Scholar 

  21. Dafader NC, Rahman N, Majumdar SK, Khan MMR, Rahman MM (2018) Preparation and characterization of iminodiacetate group containing nonwoven polyethylene fabrics and its application in chromium adsorption. J Polym Environ 26:740–748. https://doi.org/10.1007/s10924-017-0991-8

    Article  CAS  Google Scholar 

  22. Yiğitoğlu M, Arslan M (2009) Selective removal of Cr(VI) ions from aqueous solutions including Cr(VI), Cu(II) and Cd(II) ions by 4-vinyl pyridine/2-hydroxyethylmethacrylate monomer mixture grafted poly(ethylene terephthalate) fiber. J Hazard Mater 166(1):435–444. https://doi.org/10.1016/j.jhazmat.2008.11.075

    Article  CAS  PubMed  Google Scholar 

  23. Temoçin Z, Yiğitoğlu M (2009) Studies on selective uptake behavior of Hg(II) and Pb(II) by functionalized poly(ethylene terephthalate) fiber with 4-vinyl pyridine/2-hydroxyethylmethacrylate. Water Air Soil Pollut 210:463–472. https://doi.org/10.1007/s11270-009-0271-x

    Article  CAS  Google Scholar 

  24. Monier M, Abdel-Latif DA (2013) Modification and characterization of PET fibers for fast removal of Hg(II), Cu(II) and Co(II) metal ions from aqueous solutions. J Hazard Mater 250–251:122–130. https://doi.org/10.1016/j.jhazmat.2013.01.056

    Article  CAS  PubMed  Google Scholar 

  25. Arslan M (2010) Kinetics of graft copolymerization of acrylamide and 2-hydroxyethylmethacrylate monomer mixture onto poly(ethylene terephthalate) fibers. Korean J Chem Eng 27(3):991–998. https://doi.org/10.1007/s11814-010-0125-7

    Article  CAS  Google Scholar 

  26. Temoçin Z, Yiǧitoǧlu M (2009) Studies on the activity and stability of immobilized horseradish peroxidase on poly(ethylene terephthalate) grafted acrylamide fiber. Bioprocess Biosyst Eng 32:467–474. https://doi.org/10.1007/s00449-008-0266-9

    Article  CAS  PubMed  Google Scholar 

  27. Chen KS, Ku YA, Lin HR, Yan TR, Sheu DC, Chen TM (2006) Surface grafting polymerization of N-vinyl-2-pyrrolidone onto a poly(ethylene terephthalate) nonwoven by plasma pretreatment and its antibacterial activities. J Appl Polym Sci 100:803–809. https://doi.org/10.1002/app.23111

    Article  CAS  Google Scholar 

  28. Hebeish A, Shalaby SE, Bayazeed AM (1978) Graft copolymerization of 2-methyl-5-vinyl pyridine to poly(ethylene terephthalate) fibres using a post-radiation technique. J Appl Polym Sci 22(11):3335–3342. https://doi.org/10.1002/app.1978.070221127

    Article  CAS  Google Scholar 

  29. Arslan M, Yigitoglu M, Sanli O, Ünal HI (2003) Kinetics of swelling assisted grafting of 4-vinyl pyridine onto poly(ethylene terephthalate)fibers using a benzoyl peroxide initiator. Polym Bull 51(3):237–244. https://doi.org/10.1007/s00289-003-0212-6

    Article  CAS  Google Scholar 

  30. Gün Gök Z, Günay K, Arslan M, Yiğitoğlu M, Vargel İ (2019) Coating of modified poly(ethylene terephthalate) fibers with sericin-capped silver nanoparticles for antimicrobial application. Polym Bull. https://doi.org/10.1007/s00289-019-02820-0

    Article  Google Scholar 

  31. Shi L, Liu Y, Wang L (2010) solvent effects in the polyethylene terephthalate surface modification by cold argon plasma-induced grafting polymerization of methacrylic acid. J Appl Polym Sci 117:1460–1468. https://doi.org/10.1002/app.32018

    Article  CAS  Google Scholar 

  32. Rahman N, Dafader NC, Shakhawat Hossen M, Alam MF, Kabir M, Rakibul Hasan M (2016) Gamma ray induced grafting of binary monomers (acrylic acid/methyl methacrylate) onto polyethylene (PE) films for heavy metal adsorption. J Mater Environ Sci 7:4096–4104

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Metin Arslan.

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

Arslan, M., Günay, K., Gün Gök, Z. et al. Synthesis and characterization of poly(ethylene terephthalate) fibers grafted with N-(hydroxymethyl) acrylamide by free radical: its application in elimination of Congo red. Polym. Bull. 78, 1535–1550 (2021). https://doi.org/10.1007/s00289-020-03168-6

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00289-020-03168-6

Keywords

Navigation