Skip to main content
Log in

Effective removal of dyes from aqueous solutions using a novel antibacterial polymeric adsorbent

  • ORIGINAL PAPER
  • Published:
Journal of Polymer Research Aims and scope Submit manuscript

Abstract

Here, ethylenediamine-epichlorohydrin-trichlorophenol (EET) cross-linked polymer was synthesized and characterized by Fourier Transforms Infrared spectroscopy (FTIR), thermogravimetric analysis (TGA–DSC) and scanning electron microscopy (SEM). EET exhibited substantial antibacterial activity with inhibition zones of 38 and 64 mm against E. coli and S. aureus bacteria. Therefore, it was applied to treat methyl orange (MO) and rhodamine B (RB) dyes containing synthetic aqueous solutions under varying operation parameters. Notably, 10 and 15 mg of EET removed 98.72% of MO at pH 8 and 92.45% of RB at pH 3. Moreover, EET cross-linked polymer retained stable activities of about 98.6% over five consecutive recycling runs for MO dye. The EET demonstrated a fast adsorption rate and the adsorption data fits well with the pseudo-second-order for both dyes, suggesting chemisorption. Also, considering the correlation coefficient values, the experimental dataset fits suitably with Temkin equation for RB and Langmuir equation for MO. Thermodynamic evaluations for both dyes show spontaneity onto the cross-linked polymer.

Graphical abstract

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
Fig. 12

Similar content being viewed by others

References

  1. Ratnamala GM, Shetty KV, Srinikethan G (2012) Removal of remazol brilliant blue dye from dye-contaminated water by adsorption using red mud: equilibrium, kinetic, and thermodynamic studies. Water Air Soil Pollut 223(9):6187–6199

    CAS  Google Scholar 

  2. Gong R, Li M, Yang C, Sun Y, Chen J (2005) Removal of cationic dyes from aqueous solution by adsorption on peanut hull. J Hazard Mater 121(1–3):247–250

    CAS  PubMed  Google Scholar 

  3. Chequer FMD, de Oliveira GAR, Ferraz ERA, Cardoso JC, Zanoni MVB, de Oliveira DP (2013) Textile dyes: dyeing process and environmental impact. Eco-friendly Text Dye Finish 6:151–176

    Google Scholar 

  4. Jain R, Sikarwar S (2006) Photocatalytic and adsorption studies on the removal of dye Congo red from wastewater. Int J Environ Pollut 27(1–3):158–178

    CAS  Google Scholar 

  5. Koprivanac N, Kušić H (2009) Hazardous organic pollutants in colored wastewaters. Nova Science Publishers

  6. Mishra G, Tripathy M (1993) A critical review of the treatment for decolorization of dye wastewater. Colourage 40:35–38

    CAS  Google Scholar 

  7. Tahir H, Sultan M, Akhtar N, Hameed U, Abid T (2016) Application of natural and modified sugar cane bagasse for the removal of dye from aqueous solution. J Saudi Chem Soc 20:S115–S121

    CAS  Google Scholar 

  8. Hassanzadeh-Tabrizi SA, Motlagh MM, Salahshour S (2016) Synthesis of ZnO/CuO nanocomposite immobilized on γ-Al2O3 and application for removal of methyl orange. Appl Surf Sci 384:237–243

    CAS  Google Scholar 

  9. Moazami A, Montazer M, Dolatabadi MK (2018) Rapid discoloration of methyl orange in water by conductive cu/Cu2O/rGO modified polyester fabric. J Polym Environ 26(6):2502–2513

    CAS  Google Scholar 

  10. Xin Q, Fu J, Chen Z, Liu S, Yan Y, Zhang J, Xu Q (2015) Polypyrrole nanofibers as a high-efficient adsorbent for the removal of methyl orange from aqueous solution. J Environ Chem Eng 3(3):1637–1647

    CAS  Google Scholar 

  11. Oladipo AA, Ifebajo AO, Nisar N, Ajayi OA (2017) High-performance magnetic chicken bone-based biochar for efficient removal of rhodamine-B dye and tetracycline: competitive sorption analysis. Water Sci Technol 76(2):373–385

    CAS  PubMed  Google Scholar 

  12. Geng T-M, Wu D-Y, Huang W, Huang R-Y, Wu G-H (2014) Fluorogenic detection of Hg2+, Cd2+, Fe2+, Pb2+ cations in aqueous media by means of an acrylamide-acrylic acid copolymer chemosensor with pendant rhodamine-based dyes. J Polym Res 21(3):354–362

    Google Scholar 

  13. Imam SS, Babamale HF (2020) A short review on the removal of rhodamine b dye using agricultural waste-based adsorbents. AJOCS 7(1):25–37

    Google Scholar 

  14. Kadirvelu K, Karthika C, Vennilamani N, Pattabhi S (2005) Activated carbon from industrial solid waste as an adsorbent for the removal of rhodamine-B from aqueous solution: kinetic and equilibrium studies. Chemosphere 60(8):1009–1017

    CAS  PubMed  Google Scholar 

  15. Crini G, Lichtfouse E, Wilson LD, Morin-Crini N (2018) Adsorption-oriented processes using conventional and non-conventional adsorbents for wastewater treatment. In: Green Adsorbents for Pollutant Removal. Springer 23–71

  16. Saberi A, Alipour E, Sadeghi M (2019) Superabsorbent magnetic Fe3O4-based starch-poly (acrylic acid) nanocomposite hydrogel for efficient removal of dyes and heavy metal ions from water. J Polym Res 26(12):271–285

    CAS  Google Scholar 

  17. Munagapati VS, Yarramuthi V, Kim DS (2017) Methyl orange removal from aqueous solution using goethite, chitosan beads and goethite impregnated with chitosan beads. J Mol Liq 240:329–339

    CAS  Google Scholar 

  18. Kaushal M, Tiwari A (2010) Removal of rhodamine-B from aqueous solution by adsorption onto crosslinked alginate beads. J Dispers Sci Technol 31(4):438–441

    CAS  Google Scholar 

  19. Biçaak N, Şenkal BF (1998) Removal of nitrite ions from aqueous solutions by cross-linked polymer of ethylenediamine with epichlorohydrin. React Funct Polym 36(1):71–77

    Google Scholar 

  20. Sun C, Zhang X, Zhang Z, Zhang Y (2013) Color removal from dyeing wastewater by the polymer of epichlorohydrin- ethylenediamine. Adv Mater Res 752:1448–1451

    Google Scholar 

  21. Molinari R, Argurio P, Poerio T (2004) Comparison of polyethylenimine, polyacrylic acid and poly(dimethylamine-co-epichlorohydrin-co-ethylenediamine) in Cu2+ removal from wastewaters by polymer-assisted ultrafiltration. Desalination 162(1–3):217–228

    CAS  Google Scholar 

  22. Chunhui D, Xinyi Z, Xumin M (2020) The surface tunability and dye separation property of PVDF porous membranes modified by P(MMA-b-MEBIm-Br): effect of poly (ionic liquid) brush lengths. J Polym Res 29(79):1–11

    Google Scholar 

  23. Nendza M, Seydel JK (1990) Application of bacterial growth kinetics to in vitro toxicity assessment of substituted phenols and anilines. Ecotoxicol Environ Saf 19(2):228–241

    CAS  PubMed  Google Scholar 

  24. Michałowicz J, Duda W (2007) Phenols - sources and toxicity. Pol J Environ Stud 16(3):347–362

    Google Scholar 

  25. Oladipo AA, Gazi M (2015) Two-stage batch sorber design and optimization of biosorption conditions by Taguchi methodology for the removal of acid red 25 onto magnetic biomass. Korean J Chem Eng 32(9):1864–1878

    CAS  Google Scholar 

  26. Alkan M, Doğan M (2001) Adsorption of copper (II) onto perlite. J Colloid Interface Sci 243(2):280–291

    CAS  Google Scholar 

  27. Nakhjiri MT, Marandi GB, Kurdtabar M (2018) Effect of bis [2-(methacryloyloxy) ethyl] phosphate as a crosslinker on poly (AAm-co-AMPS)/Na-MMT hydrogel nanocomposite as potential adsorbent for dyes: kinetic, isotherm and thermodynamic study. J Polym Res 25:244–263

    Google Scholar 

  28. Alokour M, Yilmaz E (2019) Photoinitiated synthesis of poly (poly (ethylene glycol) methacrylate-co-diethyl amino ethyl methacrylate) superabsorbent hydrogels for dye adsorption. J Appl Polym Sci 136(26):47707–47724

    Google Scholar 

  29. Kennedy MV, Stojanovic BJ, Shuman JFL (1972) Chemical and thermal aspects of pesticide disposal. J Environ Qual 1:63–65

    CAS  Google Scholar 

  30. Segal L, Eggerton FV (1961) Infrared spectra of ethylenediamine and the dimethylethylenediamines. Appl Spectrosc 15(4):116–117

    CAS  Google Scholar 

  31. Jiao M, Yang K, Cao J, Diao Q, Zhang W, Yu M (2016) Influence of epichlorohydrin content on structure and properties of high-ortho phenolic epoxy fibers. J Appl Polym Sci 133(18):43375–43381

    Google Scholar 

  32. González MG, Cabanelas JC, Baselga J (2012) Applications of FTIR on epoxy resins-identification, monitoring the curing process, phase separation and water uptake. Infrared Spectrosc Sci Eng Technol 2:261–284

    Google Scholar 

  33. Zhan C, Chen F, Dai H, Yang J, Zhong M (2013) Photocatalytic activity of sulfated Mo-doped TiO2@fumed SiO2 composite: a mesoporous structure for methyl orange degradation. Chem Eng J 225:695–703

    CAS  Google Scholar 

  34. Oladipo AA, Ifebajo AO (2018) Highly efficient magnetic chicken bone biochar for removal of tetracycline and fluorescent dye from wastewater: two-stage adsorber analysis. J Environ Manag 209:9–16

    CAS  Google Scholar 

  35. Umpuch C, Sakaew S (2013) Removal of methyl orange from aqueous solutions by adsorption using chitosan intercalated montmorillonite. J Sci Technol 35(4):451–459

    Google Scholar 

  36. Li Q, Tang X, Sun Y, Wang Y, Long Y, Jiang J, Xu H (2015) Removal of rhodamine B from wastewater by modified volvariella volvacea: batch and column study. RSC Adv 5(32):25337–25347

    CAS  Google Scholar 

  37. Venkatraman BR, Gayathri U, Elavarasi S, Arivoli S (2012) Removal of rhodamine B dye from aqueous solution using the acid activated cynodon dactylon carbon. Der Chem Sin 3(1):99–113

    CAS  Google Scholar 

  38. Bazrafshan E, Zarei AA, Nadi H, Zazouli MA (2014) Adsorptive removal of methyl orange and reactive red 198 dyes by moringa peregrina ash. Indian J Chem Technol 21(2):105–113

    CAS  Google Scholar 

  39. Türkcan C, Uygun DA, Akgöl S, Denizli A (2014) Reactive red 120 and NI (II) derived poly (2-hydroxyethyl methacrylate) nanoparticles for urease adsorption. J Appl Polym Sci 131(2):39757–39764

    Google Scholar 

  40. Al-Ghouti MA, Da'ana DA (2020) Guidelines for the use and interpretation of adsorption isotherm models: a review. J Hazard Mater 393:1223834–1223856

    Google Scholar 

  41. Paiwei L, Xin D, Qilin Y, Zhenxi W, Shangxi Z, Meng C (2020) A novel modification method for polystyrene microspheres with dithizone and the adsorption properties for Pb2+. J Polym Res 27(195):1–10

    Google Scholar 

  42. Bahrudin NN, Nawi MA, Ismail WINW (2018) Physical and adsorptive characterizations of immobilized polyaniline for the removal of methyl orange dye. Korean J Chem Eng 35(7):1450–1461

    CAS  Google Scholar 

  43. Allouche F-N, Yassaa N, Lounici H (2015) Sorption of methyl orange from aqueous solution on chitosan biomass. Procedia Earth Planet Sci 15:596–601

    CAS  Google Scholar 

  44. Hou X-X, Deng Q-F, Ren T-Z, Yuan Z-Y (2013) Adsorption of Cu2+ and methyl orange from aqueous solutions by activated carbons of corncob-derived char wastes. Environ Sci Pollut Res 20(12):8521–8534

    CAS  Google Scholar 

  45. Robati D, Mirza B, Rajabi M et al (2016) Removal of hazardous dyes-BR 12 and methyl orange using graphene oxide as an adsorbent from aqueous phase. Chem Eng J 284:687–697

    CAS  Google Scholar 

  46. Allouche F-N, Yassaa N, Lounici H (2015) Sorption of methyl orange from aqueous solution on chitosan biomass. Procedia Earth Planet Sci 15:596–601

    CAS  Google Scholar 

  47. Umpuch C, Sakaew S (2013) Removal of methyl orange from aqueous solutions by adsorption using chitosan intercalated montmorillonite. Songklanakarin J Sci Technol 35(4):451–459

    Google Scholar 

  48. Bahrudin NN, Nawi MA, Ismail WINW (2018) Physical and adsorptive characterizations of immobilized polyaniline for the removal of methyl orange dye. Korean J Chem Eng 35(7):1450–1461

    CAS  Google Scholar 

  49. Thakur A, Kaur H (2017) Response surface optimization of Rhodamine B dye removal using paper industry waste as adsorbent. Int J Ind Chem 8(2):175–186

    CAS  Google Scholar 

  50. 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 2(1):2

    Google Scholar 

  51. Wang M, Fu J, Zhang Y et al (2015) Removal of rhodamine B, a cationic dye from aqueous solution using poly (cyclotriphosphazene-co-4, 4′-sulfonyldiphenol) nanotubes. J Macromol Sci Part A 52(2):105–113

    CAS  Google Scholar 

  52. Damiyine B, Guenbour A, Boussen R (2017) Rhodamine B adsorption on natural and modified moroccan clay with cetyltrimethylammonium bromide: Kinetics, equilibrium and thermodynamics. J Mater Environ Sci 8(3):860–871

    CAS  Google Scholar 

  53. Saini J, Garg VK, Gupta RK, Kataria N (2017) Removal of Orange G and Rhodamine B dyes from aqueous system using hydrothermally synthesized zinc oxide loaded activated carbon (ZnO-AC). J Environ Chem Eng 5(1):884–892

    CAS  Google Scholar 

Download references

Acknowledgements

We thank Dr. Fadwa Odeh (The University of Jordan, Chemistry Department) and Dr. Walhan Alshaer (The University of Jordan, Cell Therapy Center) for helping us to characterize our polymer. The authors acknowledge the suggestions, editing and professional support received during manuscript curation and revision from Associate Professor Akeem Oladipo (Chemistry Department of Eastern Mediterranean University).

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Faisal Suleiman Mustafa or Mustafa Gazi.

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

Mustafa, F.S., Güran, M. & Gazi, M. Effective removal of dyes from aqueous solutions using a novel antibacterial polymeric adsorbent. J Polym Res 27, 247 (2020). https://doi.org/10.1007/s10965-020-02227-w

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s10965-020-02227-w

Keywords

Navigation