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Synthesis and Characterization of Polysulfone-based Graft Copolymer Possessing Quaternary Ammonium Salts via Photoiniferter Polymerization

Year 2018, Volume: 5 Issue: 1, 117 - 132, 01.09.2017
https://doi.org/10.18596/jotcsa.346590

Abstract

A well-defined polysulfone-based graft copolymers
containing quaternary ammonioum salts are successfully prepared by photoiniferter
method under mild conditions. The corresponding macroiniferter agent is
sequentially synthesized by chloromethylation and nucleophilic substitution
reaction between obtained chloromethylated polysulfone and sodium diethyl
dithiocarbamate. Upon UV irradiation, this macroiniferter enables the
successful grafting of 2-(dimethylamino)ethyl methacrylate onto the polysulfone
backbone in a controlled manner. After the successful synthesis of graft
copolymers, the tertiary amine groups in the side-chains are readily quaternized
using methyl iodide to get desired quaternary ammonioum salts containing graft
copolymers. 

References

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  • 2. Kroschwitz JI, Mark HF. Encyclopedia of polymer science and technology. Hoboken, N.J.: Wiley-Interscience; 2003.
  • 3. Dizman C, Ates S, Uyar T, Tasdelen MA, Torun L, Yagci Y. Polysulfone/clay nanocomposites by in situ photoinduced crosslinking polymerization. Macromolecular Materials and Engineering. 2011;296(12):1101-6.
  • 4. Dizman C, Uyar T, Tasdelen MA, Yagci Y. Synthesis and characterization of polysulfone/POSS hybrid networks by photoinduced crosslinking polymerization. Macromolecular Materials and Engineering. 2013;298(10):1117-23.
  • 5. Yagci Y, Tasdelen MA. Mechanistic transformations involving living and controlled/living polymerization methods. Progress in Polymer Science. 2006;31(12):1133-70.
  • 6. Dizman C, Tasdelen MA, Yagci Y. Recent advances in the preparation of functionalized polysulfones. Polymer International. 2013;62(7):991-1007.
  • 7. Van der Bruggen B. Chemical Modification of Polyethersulfone Nanofiltration Membranes: A Review. Journal of Applied Polymer Science. 2009;114(1):630-42.
  • 8. Yilmaz G, Toiserkani H, Demirkol DO, Sakarya S, Timur S, Torun L, et al. Polysulfone based amphiphilic graft copolymers by click chemistry as bioinert membranes. Materials Science and Engineering: C. 2011;31(5):1091-7.
  • 9. Dizman C, Ates S, Torun L, Yagci Y. Synthesis, characterization and photoinduced curing of polysulfones with (meth) acrylate functionalities. Beilstein journal of organic chemistry. 2010;6.
  • 10. Toiserkani H, Yilmaz G, Yagci Y, Torun L. Functionalization of polysulfones by click chemistry. Macromolecular Chemistry and Physics. 2010;211(22):2389-95.
  • 11. Ates S, Dizman C, Aydogan B, Kiskan B, Torun L, Yagci Y. Synthesis, characterization and thermally activated curing of polysulfones with benzoxazine end groups. Polymer. 2011;52(7):1504-9.
  • 12. Yilmaz G, Toiserkani H, Demirkol DO, Sakarya S, Timur S, Yagci Y, et al. Modification of polysulfones by click chemistry: amphiphilic graft copolymers and their protein adsorption and cell adhesion properties. Journal of Polymer Science Part A: Polymer Chemistry. 2011;49(1):110-7.
  • 13. Dizman C, Altinkok C, Tasdelen MA. Synthesis of self-curable polysulfone containing pendant benzoxazine units via CuAAC click chemistry. Designed Monomers and Polymers. 2017;20(1):293-9.
  • 14. Otsu T, Tazaki T. LIVING RADICAL POLYMERIZATION IN HOMOGENEOUS SYSTEM WITH PHENYLAZOTRIPHENYLMETHANE AS A THERMAL INIFERTER. Polymer Bulletin. 1986;16(4):277-84.
  • 15. Otsu T, Yoshida M, Tazaki T. A MODEL FOR LIVING RADICAL POLYMERIZATION. Makromolekulare Chemie-Rapid Communications. 1982;3(2):133-40.
  • 16. Tasdelen MA, Yagci Y. CHAPTER 3 Controlled/Living Radical Polymerization in the Presence of Iniferters. Fundamentals of Controlled/Living Radical Polymerization: The Royal Society of Chemistry; 2013. p. 78-111.
  • 17. Lalevee J, Blanchard N, El-Roz M, Allonas X, Fouassier JP. New photoiniferters: Respective role of the initiating and persistent radicals. Macromolecules. 2008;41(7):2347-52.
  • 18. Tasdelen MA, Durmaz YY, Karagoz B, Bicak N, Yagci Y. A new photoiniferter/RAFT agent for ambient temperature rapid and well‐controlled radical polymerization. Journal of Polymer Science Part A: Polymer Chemistry. 2008;46(10):3387-95.
  • 19. Tasdelen MA, Çiftci M, Uygun M, Yagci Y. Possibilities for photoinduced controlled radical polymerizations. Progress in controlled radical polymerization: mechanisms and techniques: ACS Publications; 2012. p. 59-72.
  • 20. Vankerckhoven C, Vandenbroeck H, Smets G, Huybrechts J. DITHIOCARBAMATE TELECHELIC POLYMERS - SYNTHESIS AND BLOCK COPOLYMERIZATION. Makromolekulare Chemie-Macromolecular Chemistry and Physics. 1991;192(1):101-14.
  • 21. Tasdelen MA, Kahveci MU, Yagci Y. Telechelic polymers by living and controlled/living polymerization methods. Progress in Polymer Science. 2011;36(4):455-567.
  • 22. Ishizu K, Ohta Y, Kawauchi S. Kinetics of hyperbranched polystyrenes by free radical polymerization of photofunctional inimer. Macromolecules. 2002;35(9):3781-4.
  • 23. Joung YK, Choi JH, Bae JW, Park KD. Hyper-branched poly (poly (ethylene glycol) methacrylate)-grafted surfaces by photo-polymerization with iniferter for bioactive interfaces. Acta biomaterialia. 2008;4(4):960-6.
  • 24. Watanabe J, Kano K, Akashi M. Bioconjugate polymer by photo-iniferter approach: Hydrophilic random or block copolymer-coated surface. Materials Science & Engineering C-Materials for Biological Applications. 2009;29(7):2287-93.
  • 25. Durmaz YY, Karagoz B, Bicak N, Yagci Y. Synthesis of block copolymers by combination of ATRP and photoiniferter processes. Polymer International. 2008;57(10):1182-7.
  • 26. Cakmak I. Synthesis of multiblock copolymers via macroiniferter. European Polymer Journal. 1998;34(10):1561-3.
  • 27. Acar MH, Yagci Y. STUDIES ON THE BLOCK COPOLYMERIZATION OF METHACRYLONITRILE AND HEXAFLUOROBUTYLMETHACRLATE USING PHENYLAZOTRIPHENYLMETHANE AS THERMAL INIFERTER. Journal of Macromolecular Science-Chemistry. 1991;A28:177-83.
  • 28. Temel BA, Amici J, Sangermano M, Yagci Y. Synthesis of H‐shaped complex macromolecular structures by combination of atom transfer radical polymerization, photoinduced radical coupling, ring‐opening polymerization, and iniferter processes. Journal of Polymer Science Part A: Polymer Chemistry. 2013;51(21):4601-7.
  • 29. Kwak J, Lacroix-Desmazes P, Robin JJ, Boutevin B, Torres N. Synthesis of mono functional carboxylic acid poly(methyl methacrylate) in aqueous medium using sur-iniferter. Application to the synthesis of graft copolymers polyethylene-g-poly(methyl methacrylate) and the compatibilization of LDPE/PVDF blends. Polymer. 2003;44(18):5119-30.
  • 30. Pan X, Tasdelen MA, Laun J, Junkers T, Yagci Y, Matyjaszewski K. Photomediated controlled radical polymerization. Progress in Polymer Science. 2016;62:73-125.
  • 31. Tasdelen MA, Yagci Y. Photochemical methods for the preparation of complex linear and cross-linked macromolecular structures. Australian Journal of Chemistry. 2011;64(8):982-91.
  • 32. Al‐Kaabi K, van Reenen AJ. Controlled radical polymerization of poly (methyl methacrylate‐g‐epichlorohydrin) using N, N‐dithiocarbamate‐mediated iniferters. Journal of applied polymer science. 2008;108(4):2528-34.
  • 33. Gacal B, Durmaz H, Tasdelen M, Hizal G, Tunca U, Yagci Y, et al. Anthracene-maleimide-based Diels-Alder" click chemistry" as a novel route to graft copolymers. Macromolecules. 2006;39(16):5330-6.
  • 34. Demirci G, Tasdelen MA. Synthesis and characterization of graft copolymers by photoinduced CuAAC click chemistry. European Polymer Journal. 2015;66:282-9.
  • 35. Tasdelen MA, Yagci Y, Demirel AL, Biedron T, Kubisa P. Synthesis and Characterization of Block-Graft Copolymers [poly (epichlorohydrin-b-styrene)-g-poly (methyl methacrylate)] by Combination of Activated Monomer Polymerization, NMP and ATRP. Polymer bulletin. 2007;58(4):653-63.
  • 36. Tasdelen MA, Moszner N, Yagci Y. The use of poly (ethylene oxide) as hydrogen donor in type II photoinitiated free radical polymerization. Polymer bulletin. 2009;63(2):173-83.
  • 37. Ates S, Tatar-Guner P, Yagci Y, Levent Demirel A. Synthesis and characterization of polysulfone-g-poly (2-alkyl-2-oxazoline) s. Designed Monomers and Polymers. 2013;16(2):137-44.
  • 38. Goracci G, Arbe A, Alegría A, García Sakai V, Rudić S, Schneider GJ, et al. Influence of Solvent on Poly(2-(Dimethylamino)Ethyl Methacrylate) Dynamics in Polymer-Concentrated Mixtures: A Combined Neutron Scattering, Dielectric Spectroscopy, and Calorimetric Study. Macromolecules. 2015;48(18):6724-35.
Year 2018, Volume: 5 Issue: 1, 117 - 132, 01.09.2017
https://doi.org/10.18596/jotcsa.346590

Abstract

References

  • 1. Ioan S. Functionalized polysulfones : synthesis, characterization, and applications, 2015.
  • 2. Kroschwitz JI, Mark HF. Encyclopedia of polymer science and technology. Hoboken, N.J.: Wiley-Interscience; 2003.
  • 3. Dizman C, Ates S, Uyar T, Tasdelen MA, Torun L, Yagci Y. Polysulfone/clay nanocomposites by in situ photoinduced crosslinking polymerization. Macromolecular Materials and Engineering. 2011;296(12):1101-6.
  • 4. Dizman C, Uyar T, Tasdelen MA, Yagci Y. Synthesis and characterization of polysulfone/POSS hybrid networks by photoinduced crosslinking polymerization. Macromolecular Materials and Engineering. 2013;298(10):1117-23.
  • 5. Yagci Y, Tasdelen MA. Mechanistic transformations involving living and controlled/living polymerization methods. Progress in Polymer Science. 2006;31(12):1133-70.
  • 6. Dizman C, Tasdelen MA, Yagci Y. Recent advances in the preparation of functionalized polysulfones. Polymer International. 2013;62(7):991-1007.
  • 7. Van der Bruggen B. Chemical Modification of Polyethersulfone Nanofiltration Membranes: A Review. Journal of Applied Polymer Science. 2009;114(1):630-42.
  • 8. Yilmaz G, Toiserkani H, Demirkol DO, Sakarya S, Timur S, Torun L, et al. Polysulfone based amphiphilic graft copolymers by click chemistry as bioinert membranes. Materials Science and Engineering: C. 2011;31(5):1091-7.
  • 9. Dizman C, Ates S, Torun L, Yagci Y. Synthesis, characterization and photoinduced curing of polysulfones with (meth) acrylate functionalities. Beilstein journal of organic chemistry. 2010;6.
  • 10. Toiserkani H, Yilmaz G, Yagci Y, Torun L. Functionalization of polysulfones by click chemistry. Macromolecular Chemistry and Physics. 2010;211(22):2389-95.
  • 11. Ates S, Dizman C, Aydogan B, Kiskan B, Torun L, Yagci Y. Synthesis, characterization and thermally activated curing of polysulfones with benzoxazine end groups. Polymer. 2011;52(7):1504-9.
  • 12. Yilmaz G, Toiserkani H, Demirkol DO, Sakarya S, Timur S, Yagci Y, et al. Modification of polysulfones by click chemistry: amphiphilic graft copolymers and their protein adsorption and cell adhesion properties. Journal of Polymer Science Part A: Polymer Chemistry. 2011;49(1):110-7.
  • 13. Dizman C, Altinkok C, Tasdelen MA. Synthesis of self-curable polysulfone containing pendant benzoxazine units via CuAAC click chemistry. Designed Monomers and Polymers. 2017;20(1):293-9.
  • 14. Otsu T, Tazaki T. LIVING RADICAL POLYMERIZATION IN HOMOGENEOUS SYSTEM WITH PHENYLAZOTRIPHENYLMETHANE AS A THERMAL INIFERTER. Polymer Bulletin. 1986;16(4):277-84.
  • 15. Otsu T, Yoshida M, Tazaki T. A MODEL FOR LIVING RADICAL POLYMERIZATION. Makromolekulare Chemie-Rapid Communications. 1982;3(2):133-40.
  • 16. Tasdelen MA, Yagci Y. CHAPTER 3 Controlled/Living Radical Polymerization in the Presence of Iniferters. Fundamentals of Controlled/Living Radical Polymerization: The Royal Society of Chemistry; 2013. p. 78-111.
  • 17. Lalevee J, Blanchard N, El-Roz M, Allonas X, Fouassier JP. New photoiniferters: Respective role of the initiating and persistent radicals. Macromolecules. 2008;41(7):2347-52.
  • 18. Tasdelen MA, Durmaz YY, Karagoz B, Bicak N, Yagci Y. A new photoiniferter/RAFT agent for ambient temperature rapid and well‐controlled radical polymerization. Journal of Polymer Science Part A: Polymer Chemistry. 2008;46(10):3387-95.
  • 19. Tasdelen MA, Çiftci M, Uygun M, Yagci Y. Possibilities for photoinduced controlled radical polymerizations. Progress in controlled radical polymerization: mechanisms and techniques: ACS Publications; 2012. p. 59-72.
  • 20. Vankerckhoven C, Vandenbroeck H, Smets G, Huybrechts J. DITHIOCARBAMATE TELECHELIC POLYMERS - SYNTHESIS AND BLOCK COPOLYMERIZATION. Makromolekulare Chemie-Macromolecular Chemistry and Physics. 1991;192(1):101-14.
  • 21. Tasdelen MA, Kahveci MU, Yagci Y. Telechelic polymers by living and controlled/living polymerization methods. Progress in Polymer Science. 2011;36(4):455-567.
  • 22. Ishizu K, Ohta Y, Kawauchi S. Kinetics of hyperbranched polystyrenes by free radical polymerization of photofunctional inimer. Macromolecules. 2002;35(9):3781-4.
  • 23. Joung YK, Choi JH, Bae JW, Park KD. Hyper-branched poly (poly (ethylene glycol) methacrylate)-grafted surfaces by photo-polymerization with iniferter for bioactive interfaces. Acta biomaterialia. 2008;4(4):960-6.
  • 24. Watanabe J, Kano K, Akashi M. Bioconjugate polymer by photo-iniferter approach: Hydrophilic random or block copolymer-coated surface. Materials Science & Engineering C-Materials for Biological Applications. 2009;29(7):2287-93.
  • 25. Durmaz YY, Karagoz B, Bicak N, Yagci Y. Synthesis of block copolymers by combination of ATRP and photoiniferter processes. Polymer International. 2008;57(10):1182-7.
  • 26. Cakmak I. Synthesis of multiblock copolymers via macroiniferter. European Polymer Journal. 1998;34(10):1561-3.
  • 27. Acar MH, Yagci Y. STUDIES ON THE BLOCK COPOLYMERIZATION OF METHACRYLONITRILE AND HEXAFLUOROBUTYLMETHACRLATE USING PHENYLAZOTRIPHENYLMETHANE AS THERMAL INIFERTER. Journal of Macromolecular Science-Chemistry. 1991;A28:177-83.
  • 28. Temel BA, Amici J, Sangermano M, Yagci Y. Synthesis of H‐shaped complex macromolecular structures by combination of atom transfer radical polymerization, photoinduced radical coupling, ring‐opening polymerization, and iniferter processes. Journal of Polymer Science Part A: Polymer Chemistry. 2013;51(21):4601-7.
  • 29. Kwak J, Lacroix-Desmazes P, Robin JJ, Boutevin B, Torres N. Synthesis of mono functional carboxylic acid poly(methyl methacrylate) in aqueous medium using sur-iniferter. Application to the synthesis of graft copolymers polyethylene-g-poly(methyl methacrylate) and the compatibilization of LDPE/PVDF blends. Polymer. 2003;44(18):5119-30.
  • 30. Pan X, Tasdelen MA, Laun J, Junkers T, Yagci Y, Matyjaszewski K. Photomediated controlled radical polymerization. Progress in Polymer Science. 2016;62:73-125.
  • 31. Tasdelen MA, Yagci Y. Photochemical methods for the preparation of complex linear and cross-linked macromolecular structures. Australian Journal of Chemistry. 2011;64(8):982-91.
  • 32. Al‐Kaabi K, van Reenen AJ. Controlled radical polymerization of poly (methyl methacrylate‐g‐epichlorohydrin) using N, N‐dithiocarbamate‐mediated iniferters. Journal of applied polymer science. 2008;108(4):2528-34.
  • 33. Gacal B, Durmaz H, Tasdelen M, Hizal G, Tunca U, Yagci Y, et al. Anthracene-maleimide-based Diels-Alder" click chemistry" as a novel route to graft copolymers. Macromolecules. 2006;39(16):5330-6.
  • 34. Demirci G, Tasdelen MA. Synthesis and characterization of graft copolymers by photoinduced CuAAC click chemistry. European Polymer Journal. 2015;66:282-9.
  • 35. Tasdelen MA, Yagci Y, Demirel AL, Biedron T, Kubisa P. Synthesis and Characterization of Block-Graft Copolymers [poly (epichlorohydrin-b-styrene)-g-poly (methyl methacrylate)] by Combination of Activated Monomer Polymerization, NMP and ATRP. Polymer bulletin. 2007;58(4):653-63.
  • 36. Tasdelen MA, Moszner N, Yagci Y. The use of poly (ethylene oxide) as hydrogen donor in type II photoinitiated free radical polymerization. Polymer bulletin. 2009;63(2):173-83.
  • 37. Ates S, Tatar-Guner P, Yagci Y, Levent Demirel A. Synthesis and characterization of polysulfone-g-poly (2-alkyl-2-oxazoline) s. Designed Monomers and Polymers. 2013;16(2):137-44.
  • 38. Goracci G, Arbe A, Alegría A, García Sakai V, Rudić S, Schneider GJ, et al. Influence of Solvent on Poly(2-(Dimethylamino)Ethyl Methacrylate) Dynamics in Polymer-Concentrated Mixtures: A Combined Neutron Scattering, Dielectric Spectroscopy, and Calorimetric Study. Macromolecules. 2015;48(18):6724-35.
There are 38 citations in total.

Details

Subjects Engineering, Chemical Engineering
Journal Section Articles
Authors

Mehmet Atilla Tasdelen 0000-0002-7012-7029

Serhat Oran

Publication Date September 1, 2017
Submission Date October 25, 2017
Acceptance Date November 19, 2017
Published in Issue Year 2018 Volume: 5 Issue: 1

Cite

Vancouver Tasdelen MA, Oran S. Synthesis and Characterization of Polysulfone-based Graft Copolymer Possessing Quaternary Ammonium Salts via Photoiniferter Polymerization. JOTCSA. 2017;5(1):117-32.