Research Article
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Year 2019, , 365 - 372, 20.10.2019
https://doi.org/10.18596/jotcsa.606191

Abstract

References

  • 1. Barth C, Goncalves MC, Pires ATN, Roeder J, Wolf BA. Asymmetric polysulfone and polyethersulfone membranes: effects of thermodynamic conditions during formation on their performance. Journal of Membrane Science. 2000;169(2):287-99.
  • 2. Watanabe S, Kobayashi A, Kakimoto M-A, Imai Y. Synthesis and characterization of new aromatic polyesters and polyethers derived from 1,2-bis(4-hydroxyphenyl)-1,2-diphenylethylene. 1994;32(5):909-15.
  • 3. Hickner MA, Ghassemi H, Kim YS, Einsla BR, McGrath JE. Alternative Polymer Systems for Proton Exchange Membranes (PEMs). Chemical Reviews. 2004;104(10):4587-612.
  • 4. Noshay A, Robeson LM. Sulfonated Polysulfone. Journal of Applied Polymer Science. 1976;20(7):1885-903.
  • 5. Park JY, Acar MH, Akthakul A, Kuhlman W, Mayes AM. Polysulfone-graft-poly(ethylene glycol) graft copolymers for surface modification of polysulfone membranes. Biomaterials. 2006;27(6):856-65.
  • 6. Yoon K, Hsiao BS, Chu B. Formation of functional polyethersulfone electrospun membrane for water purification by mixed solvent and oxidation processes. Polymer. 2009;50(13):2893-9.
  • 7. Higuchi A, Shirano K, Harashima M, Yoon BO, Hara M, Hattori M, et al. Chemically modified polysulfone hollow fibers with vinylpyrrolidone having improved blood compatibility. Biomaterials. 2002;23(13):2659-66.
  • 8. Dizman C, Tasdelen MA, Yagci Y. Recent advances in the preparation of functionalized polysulfones. Polymer International. 2013;62(7):991-1007.
  • 9. Dizman C, Demirkol DO, Ates S, Torun L, Sakarya S, Timur S, et al. Photochemically prepared polysulfone/poly(ethylene glycol) amphiphilic networks and their biomolecule adsorption properties. Colloids and Surfaces B-Biointerfaces. 2011;88(1):265-70.
  • 10. Kolb HC, Finn MG, Sharpless KB. Click chemistry: Diverse chemical function from a few good reactions. Angewandte Chemie-International Edition. 2001;40(11):2004-21.
  • 11. Binder WH, Sachsenhofer R. 'Click' chemistry in polymer and materials science. Macromol Rapid Commun. 2007;28(1):15-54.
  • 12. Tron GC, Pirali T, Billington RA, Canonico PL, Sorba G, Genazzani AA. Click chemistry reactions in medicinal chemistry: Applications of the 1,3-dipolar cycloaddition between azides and alkynes. Medicinal Research Reviews. 2008;28(2):278-308.
  • 13. Tasdelen MA, Yagci Y. Light-Induced Click Reactions. Angewandte Chemie-International Edition. 2013;52(23):5930-8.
  • 14. Ciftci M, Kahveci MU, Yagci Y, Allonas X, Ley C, Tar H. A simple route to synthesis of branched and cross-linked polymers with clickable moieties by photopolymerization. Chemical Communications. 2012;48(82):10252-4.
  • 15. Murtezi E, Ciftci M, Yagci Y. Synthesis of clickable hydrogels and linear polymers by type II photoinitiation. Polymer International. 2015;64(5):588-94.
  • 16. Gustafsson J, Ljusberg-Wahren H, Almgren M, Larsson K. Submicron particles of reversed lipid phases in water stabilized by a nonionic amphiphilic polymer. Langmuir. 1997;13(26):6964-71.
  • 17. Nishikawa T, Nishida J, Ookura R, Nishimura SI, Wada S, Karino T, et al. Honeycomb-patterned thin films of amphiphilic polymers as cell culture substrates. Materials Science & Engineering C-Biomimetic and Supramolecular Systems. 1999;8-9:495-500.
  • 18. Acik G, Altinkok C. Polypropylene microfibers via solution electrospinning under ambient conditions. 2019;136(45):48199.
  • 19. Geyik C, Ciftci M, Demir B, Guler B, Ozkaya AB, Gumus ZP, et al. Controlled release of anticancer drug Paclitaxel using nano-structured amphiphilic star-hyperbranched block copolymers. Polymer Chemistry. 2015;6(30):5470-7.
  • 20. Seleci M, Seleci DA, Ciftci M, Demirkol DO, Stahl F, Timur S, et al. Nanostructured Amphiphilic Star-Hyperbranched Block Copolymers for Drug Delivery. Langmuir. 2015;31(15):4542-51.
  • 21. Haraguchi K, Farnworth R, Ohbayashi A, Takehisa T. Compositional effects on mechanical properties of nanocomposite hydrogels composed of poly(N,N-dimethylacrylamide) and clay. Macromolecules. 2003;36(15):5732-41.
  • 22. Trossarelli L, Meirone M. Solution properties of poly(N,N‐dimethylacrylamide). Journal of Polymer Science. 1962;57(165):445-52.
  • 23. Lu D, Jia Z, Monteiro MJ. Synthesis of alkyne functional cyclic polymers by one-pot thiol–ene cyclization. Polymer Chemistry. 2013;4(6):2080-9.
  • 24. Toiserkani H, Yilmaz G, Yagci Y, Torun L. Functionalization of Polysulfones by Click Chemistry. Macromolecular Chemistry and Physics. 2010;211(22):2389-95.

Synthesis of Polysulfone Based Amphiphilic Graft Copolymers by a ‘Grafting to’ Approach

Year 2019, , 365 - 372, 20.10.2019
https://doi.org/10.18596/jotcsa.606191

Abstract

Synthesis
of amphiphilic polysulfone graft copolymers by ‘‘Click’’ chemistry is
described.  First, a commercial PSU was
chloromethylated to give chloro-funtional PSU (PSU-Cl). Subsequently, chloride
groups were converted into azide moieties by nucleophilic substitution.
Hydrophilic poly(N,N-dimethylacrylamide) (PDMA) side chains were then attached
via a “grafting to” approach by using copper-catalyzed azide–alkyne
cycloaddition (CuAAC). Precursor polymer and the final amphiphilic copolymers were characterized by 1H
NMR, FT-IR, GPC and contact angle measurements.

References

  • 1. Barth C, Goncalves MC, Pires ATN, Roeder J, Wolf BA. Asymmetric polysulfone and polyethersulfone membranes: effects of thermodynamic conditions during formation on their performance. Journal of Membrane Science. 2000;169(2):287-99.
  • 2. Watanabe S, Kobayashi A, Kakimoto M-A, Imai Y. Synthesis and characterization of new aromatic polyesters and polyethers derived from 1,2-bis(4-hydroxyphenyl)-1,2-diphenylethylene. 1994;32(5):909-15.
  • 3. Hickner MA, Ghassemi H, Kim YS, Einsla BR, McGrath JE. Alternative Polymer Systems for Proton Exchange Membranes (PEMs). Chemical Reviews. 2004;104(10):4587-612.
  • 4. Noshay A, Robeson LM. Sulfonated Polysulfone. Journal of Applied Polymer Science. 1976;20(7):1885-903.
  • 5. Park JY, Acar MH, Akthakul A, Kuhlman W, Mayes AM. Polysulfone-graft-poly(ethylene glycol) graft copolymers for surface modification of polysulfone membranes. Biomaterials. 2006;27(6):856-65.
  • 6. Yoon K, Hsiao BS, Chu B. Formation of functional polyethersulfone electrospun membrane for water purification by mixed solvent and oxidation processes. Polymer. 2009;50(13):2893-9.
  • 7. Higuchi A, Shirano K, Harashima M, Yoon BO, Hara M, Hattori M, et al. Chemically modified polysulfone hollow fibers with vinylpyrrolidone having improved blood compatibility. Biomaterials. 2002;23(13):2659-66.
  • 8. Dizman C, Tasdelen MA, Yagci Y. Recent advances in the preparation of functionalized polysulfones. Polymer International. 2013;62(7):991-1007.
  • 9. Dizman C, Demirkol DO, Ates S, Torun L, Sakarya S, Timur S, et al. Photochemically prepared polysulfone/poly(ethylene glycol) amphiphilic networks and their biomolecule adsorption properties. Colloids and Surfaces B-Biointerfaces. 2011;88(1):265-70.
  • 10. Kolb HC, Finn MG, Sharpless KB. Click chemistry: Diverse chemical function from a few good reactions. Angewandte Chemie-International Edition. 2001;40(11):2004-21.
  • 11. Binder WH, Sachsenhofer R. 'Click' chemistry in polymer and materials science. Macromol Rapid Commun. 2007;28(1):15-54.
  • 12. Tron GC, Pirali T, Billington RA, Canonico PL, Sorba G, Genazzani AA. Click chemistry reactions in medicinal chemistry: Applications of the 1,3-dipolar cycloaddition between azides and alkynes. Medicinal Research Reviews. 2008;28(2):278-308.
  • 13. Tasdelen MA, Yagci Y. Light-Induced Click Reactions. Angewandte Chemie-International Edition. 2013;52(23):5930-8.
  • 14. Ciftci M, Kahveci MU, Yagci Y, Allonas X, Ley C, Tar H. A simple route to synthesis of branched and cross-linked polymers with clickable moieties by photopolymerization. Chemical Communications. 2012;48(82):10252-4.
  • 15. Murtezi E, Ciftci M, Yagci Y. Synthesis of clickable hydrogels and linear polymers by type II photoinitiation. Polymer International. 2015;64(5):588-94.
  • 16. Gustafsson J, Ljusberg-Wahren H, Almgren M, Larsson K. Submicron particles of reversed lipid phases in water stabilized by a nonionic amphiphilic polymer. Langmuir. 1997;13(26):6964-71.
  • 17. Nishikawa T, Nishida J, Ookura R, Nishimura SI, Wada S, Karino T, et al. Honeycomb-patterned thin films of amphiphilic polymers as cell culture substrates. Materials Science & Engineering C-Biomimetic and Supramolecular Systems. 1999;8-9:495-500.
  • 18. Acik G, Altinkok C. Polypropylene microfibers via solution electrospinning under ambient conditions. 2019;136(45):48199.
  • 19. Geyik C, Ciftci M, Demir B, Guler B, Ozkaya AB, Gumus ZP, et al. Controlled release of anticancer drug Paclitaxel using nano-structured amphiphilic star-hyperbranched block copolymers. Polymer Chemistry. 2015;6(30):5470-7.
  • 20. Seleci M, Seleci DA, Ciftci M, Demirkol DO, Stahl F, Timur S, et al. Nanostructured Amphiphilic Star-Hyperbranched Block Copolymers for Drug Delivery. Langmuir. 2015;31(15):4542-51.
  • 21. Haraguchi K, Farnworth R, Ohbayashi A, Takehisa T. Compositional effects on mechanical properties of nanocomposite hydrogels composed of poly(N,N-dimethylacrylamide) and clay. Macromolecules. 2003;36(15):5732-41.
  • 22. Trossarelli L, Meirone M. Solution properties of poly(N,N‐dimethylacrylamide). Journal of Polymer Science. 1962;57(165):445-52.
  • 23. Lu D, Jia Z, Monteiro MJ. Synthesis of alkyne functional cyclic polymers by one-pot thiol–ene cyclization. Polymer Chemistry. 2013;4(6):2080-9.
  • 24. Toiserkani H, Yilmaz G, Yagci Y, Torun L. Functionalization of Polysulfones by Click Chemistry. Macromolecular Chemistry and Physics. 2010;211(22):2389-95.
There are 24 citations in total.

Details

Primary Language English
Subjects Polymer Science and Technologies
Journal Section Articles
Authors

Mustafa Ciftci 0000-0003-1858-0691

Publication Date October 20, 2019
Submission Date August 19, 2019
Acceptance Date August 29, 2019
Published in Issue Year 2019

Cite

Vancouver Ciftci M. Synthesis of Polysulfone Based Amphiphilic Graft Copolymers by a ‘Grafting to’ Approach. JOTCSA. 2019;6(3):365-72.