This study reports the adsorption of Cu(II) ion by 3-(2-aminoethylamino) propyldimethoxymethylsilane-modified terpolymers. Water-soluble poly(sodium 4-styrenesulfonate-co-maleic anhydride-co-acrylamide) [poly(NaSS-co-MA-co-AAm)] and poly(sodium 4-styrenesulfonate-co-maleic anhydride-co–N-isopropylacrylamide) [poly(NaSS-co-MA-co-NIPAM)] terpolymers were synthesized and then modified with silane to make them water-insoluble. 1H-NMR and FT-IR spectroscopy was used to study the chemical composition of the terpolymers. Also, acid number and viscosity of the polymers were determined. Cu(II) ion adsorption parameters (adsorbent dosage, contact time, pH and metal ion concentration) were studied, and the equilibrium data were evaluated using adsorption isotherm models; Freundlich isotherm gave the best fit. Cu(II) adsorption performance of poly(NaSS-co-MA-co-AAm) and poly(NaSS-co-MA-co-NIPAM) terpolymers was found to be 53.42 and 43.10%, respectively. The terpolymers can be used for removal of Cu(II) from aqueous media.
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Zhao G, Huang X, Tang Z, Huang Q, Niu F, Wang X (2018) Polymer-based nanocomposites for heavy metal ions removal from aqueous solution: a review. Polym Chem Uk 9(26):3562–3582
Wen J, Fang Y, Zeng G (2018) Progress and prospect of adsorptive removal of heavy metal ions from aqueous solution using metal–organic frameworks: a review of studies from the last decade. Chemosphere 201:627–643
Bilal M, Shah JA, Ashfaq T, Gardazi SMH, Tahir AA, Pervez A, Haroon H, Mahmood Q (2013) Waste biomass adsorbents for copper removal from industrial wastewater—a review. J Hazard Mater 263:322–333
Prasad M, Freitas H (2000) Removal of toxic metals from solution by leaf, stem and root phytomass of Quercus ilex L. (holly oak). Environ Pollut 110(2):277–283
Al-Saydeh SA, El-Naas MH, Zaidi SJ (2017) Copper removal from industrial wastewater: A comprehensive review. J Ind Eng Chem 56:35–44
A. Okudan, B.E. Ataoglu, O. Sengoz, G. Arslan, Cu(II) Sorption Performance of Novel Chitosan/Ter-(vinyl pivalate-maleic anhydride-N-tert-butylacrylamide) Microcapsules, J Polym Environ (2019) 1–10.
Akbari A, Arsalani N, Eftekhari-Sis B, Amini M, Gohari G, Jabbari E (2019) Cube-octameric silsesquioxane (POSS)-capped magnetic iron oxide nanoparticles for the efficient removal of methylene blue. Front Chem Sci Eng 13(3):563–573
Eftekhari-Sis B, Akbari A, Motlagh PY, Bahrami Z, Arsalani N (2018) Dye adsorption on cubic polyhedral oligomeric silsesquioxane-Based poly (acrylamide-co-itaconic acid) hybrid nanocomposites: kinetic, thermodynamic and isotherms studies. J Inorg Organomet Polym 28(5):1728–1738
Bahrami Z, Akbari A, Eftekhari-Sis B (2019) Double network hydrogel of sodium alginate/polyacrylamide cross-linked with POSS: Swelling, dye removal and mechanical properties. Int J Biol Macromol 129:187–197
Brusseau SGN, D’Agosto F, Magnet S, Couvreur L, Chamignon C, Charleux B (2011) Nitroxide-Mediated copolymerization of methacrylic acid and sodium 4-styrenesulfonate in water solution and one-pot synthesis of amphiphilic block copolymer nanoparticles. Macromolecules 44(14):5590–5598
Deng H-Y, Xu Y-Y, Zhu B-K, Wei X-Z, Liu F, Cui Z-Y (2008) Polyelectrolyte membranes prepared by dynamic self-assembly of poly (4-styrenesulfonic acid-co-maleic acid) sodium salt (PSSMA) for nanofiltration (I). J Membr Sci 323(1):125–133
Rivas B, Seguel G, Geckeler K (2002) Synthesis, characterization, and properties of polychelates of poly (styrene sulfonic acid-co-maleic acid) with Co(II), Cu(II), Ni(II), and Zn (II). J Appl Polym Sci 85(12):2546–2551
Rivas BL, Munoz C (2009) Synthesis and metal ion adsorption properties of poly (4-sodium styrene sulfonate-co-acrylic acid). J Appl Polym Sci 114(3):1587–1592
Matsumoto K, Hasegawa H, Matsuoka H (2004) Synthesis of sodium-polystyrenesulfonate-grafted nanoparticles by core-cross-linking of block copolymer micelles. Tetrahedron 60(34):7197–7204
Ghosh SK, De P, Khastgir D, De S (2000) Ionic thermoplastic elastomer based on the zinc salt of sulfonated maleated EPDM rubber. I. Effect of zinc stearate on melt‐flow behavior, and dynamic mechanical, dielectric, and physical properties. J Appl Polym Sci 78(4):743–750
Luo X, Goh SH, Lee SY, Huan CHA (1999) Spectroscopic studies of interactions in complexes of poly (1-vinylimidazole) with poly (styrenesulfonic acid) or the zinc salt of poly (styrenesulfonate). Macromol Chem Phys 200(4):874–880
Hasanzadeh R, Najafi Moghadam P, Samadi N (2013) Synthesis and application of modified poly (styrene‐alt‐maleic anhydride) networks as a nano chelating resin for uptake of heavy metal ions. Polym Adv Technol 24(1):34–41
Hasanzadeh R, Moghadam PN, Samadi N, Asri-Rezaei S (2013) Removal of heavy-metal ions from aqueous solution with nanochelating resins based on poly (styrene-alt-maleic anhydride). J Appl Polym Sci 127(4):2875–2883
Abd El-Rehim HA, Hegazy EA, El-Hag Ali A (2000) Selective removal of some heavy metal ions from aqueous solution using treated polyethylene-g-styrene/maleic anhydride membranes. React Funct Polym 43(1):105–116
Kawaguchi S, Kitano T, Ito K (1991) Infrared and ultraviolet spectroscopic studies on intramolecular hydrogen bonding in an alternating copolymer of isobutylene and maleic acid. Macromolecules 24(22):6030–6036
Samadi N, Ansari R, Khodavirdilo B (2017) Removal of Copper ions from aqueous solutions using polymer derivations of poly (styrene-alt-maleic anhydride). Egypt J Pet 26(2):375–389
Rivas BL, Seguel GV, Geckeler KE (2001) Poly(styrene-alt-maleic acid)–metal complexes with divalent metal ions. synthesis, characterization, and physical properties. J Appl Polym Sci 81(6):1310–1315
Rivas BL, Seguel GV, Ancatripai C (2000) Polymer-metal complexes: Synthesis, characterization, and properties of poly(maleic acid) metal complexes with Cu(II), Co(II), Ni(II), and Zn(II). Polym Bull 44(5):445–452
Chen JJ, Ahmad AL, Ooi BS (2013) Poly(N-isopropylacrylamide-co-acrylic acid) hydrogels for copper ion adsorption: equilibrium isotherms, kinetic and thermodynamic studies. J Environ Chem Eng 1(3):339–348
Chauhan GS, Kumar S, Kumari A, Sharma R (2003) Study on the synthesis, characterization, and sorption of some metal ions on gelatin- and acrylamide-based hydrogels. J Appl Polym Sci 90(14):3856–3871
Chen JJ, Ahmad AL, Ooi BS (2014) Thermo-responsive properties of poly(N-isopropylacrylamide-co-acrylic acid) hydrogel and its effect on copper ion removal and fouling of polymer-enhanced ultrafiltration. J Membrane Sci 469:73–79
Ju X-J, Zhang S-B, Zhou M-Y, Xie R, Yang L, Chu L-Y (2009) Novel heavy-metal adsorption material: ion-recognition P(NIPAM-co-BCAm) hydrogels for removal of lead(II) ions. J Hazard Mater 167(1):114–118
Morales DV, Rivas BL (2014) Poly (Acrylamide-co-Styrene Sodium Sulfonate) and Poly (2-Acrylamide-2-Methyl-1-Propanesulfonic Acid-co-Acrylic Acid) Resins with Removal Properties for Hg (II), Pb (II), Cd (II), and Zn (II). J Chil Chem Soc 59(2):2420–2426
Klumperman B (2010) Mechanistic considerations on styrene–maleic anhydride copolymerization reactions. Polym Chem-Uk 1(5):558–562
Tsuchida E, Tomono T (1971) Discussion on the mechanism of alternating copolymerization of styrene and maleic anhydride. Die Makromolekulare Chemie Macromol Chem Phys 141(1):265–298
Kim BK, Park SY, Park SJ (1991) Morphological, thermal and rheological properties of blends: Polyethylene/nylon-6, polyethylene/nylon-6/(maleic anhydride-g-polyethylene) and (maleic anhydride-g-polyethylene)/nylon-6. Eur Polymer J 27(4–5):349–354
Lucchesi C, Secrets P, Hirn C (1975) Standart method of chemical analysis. Krieger Publishing Company, New York
Kocak N, Sahin M, Arslan G, Ucan HI (2012) Synthesis of crosslinked chitosan possessing schiff base and its use in metal removal. J Inorg Organomet Polym 22(1):166–177
Travas-Sejdic J, Easteal A (2000) Study of free-radical copolymerization of acrylamide with 2-acrylamido-2-methyl-1-propane sulphonic acid. J Appl Polym Sci 75(5):619–628
Genies C, Mercier R, Sillion B, Petiaud R, Cornet N, Gebel G, Pineri M (2001) Stability study of sulfonated phthalic and naphthalenic polyimide structures in aqueous medium. Polymer 42(12):5097–5105
Akbari A, Arsalani N (2016) Organic–inorganic incompletely condensed polyhedral oligomeric silsesquioxane-based nanohybrid: synthesis, characterization and dye removal properties. Polym Plastics Technol Eng 55(15):1586–1594
Rivas BL, Seguel GV, Geckeler KE (2002) Synthesis, characterization, and properties of polychelates of poly(styrene sulfonic acid-co-maleic acid) with Co(II), Cu(II), Ni(II), and Zn(II). J Appl Polym Sci 85(12):2546–2551
Deng H, Xu Y, Zhu B, Wei X, Liu F, Cui Z (2008) Polyelectrolyte membranes prepared by dynamic self-assembly of poly (4-styrenesulfonic acid-co-maleic acid) sodium salt (PSSMA) for nanofiltration (I). J Membr Sci 323(1):125–133
Zhu Z, Yang X, He L-N, Li W (2012) Adsorption of Hg 2+ from aqueous solution on functionalized MCM-41. RSC Adv 2(3):1088–1095
Çelik S (2011) Poli (4-vinilpiridin) homopolimeri, maleik anhidrit ve n-izopropil akrilamid ile kopolimer ve terpolimerlerinin sentezi, karakterizasyonu ve özelliklerinin incelenmesi. Fen Bilimleri Enstitüsü, Gazi Üniversitesi Ankara
The authors are thankful to Selcuk University Research Foundation (project number: BAP-14201016) for funding the study.
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Okudan, A., Ozviran, E., Arslan, G. et al. Cu(II) sorption performance of silane-modified poly(NaSS-co-MA-co-AAm) and poly(NaSS-co-MA-co-NIPAM) terpolymers. Polym. Bull. 77, 5407–5421 (2020). https://doi.org/10.1007/s00289-019-03025-1
- Silane modification
- Water treatment