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Synthesis and Characterization of Poly vinyl chloride–graft– ethylene glycol Graft Copolymers by “Click” Chemistry

Year 2017, Volume: 45 Issue: 1, 35 - 42, 01.03.2017

Abstract

Synthesis of poly vinyl chloride–g–ethylene glycol [poly VC–g–EG ] graft copolymers was carried out by me- ans of “click” chemistry of propargyl polyethylene glycol propargyl PEG and terminally azide polyvinyl chloride PVC–N3 . Primarily propargyl PEG was synthesized by the reaction of PEGs 3000 Da, 2000 Da, 1500 Da, 1000 Da, 600 Da, and 400 Da with propargyl chloride. PVC–N3 was obtained by reaction of purified PVC and sodium azide. By using PVC–N3 and propargyl PEG, poly VC–g–EG graft copolymers were synthesized. The primary parameters such as concentration, and time that influenced the reactions were assessed. The charac- terization of products was accomplished by using multi instruments and methods such as nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, gel permeation chromatography, elemental analysis, and fractional precipitation [non-solvent petroleum ether, mL /solvent THF, mL ] techniques.

References

  • H.C. Kolb, M.G. Finn, K.B. Sharpless, Click chemistry: diverse chemical function from a few good reactions, Angew. Chem. Int. Ed., 40 (2001) 2004–2021.
  • C.D. Hein, X.M. Liu, D. Wang, Click chemistry, a powerful tool for pharmaceutical sciences, Pharm. Res., 25 (2008) 2216–2230.
  • B. Kiskan, G. Demiray, Y. Yagci, Thermally curable polyvinyl chloride via click chemistry, J. Polym. Sci. Part A: Polym. Chem., 46 (2008) 3512–3518.
  • D.Y. Zhu, G.S. Cao, W.L. Qiu, M.Z. Rong, M.Q. Zhang, Self-healing polyvinyl chloride (PVC) based on microencapsulated nucleophilic thiol-click chemistry, Polymer, (69) 2015 1–9.
  • D. Tunc, B. Gacal, Y. Yagci, An amphiphatic thioxanthone-anthracene photoinitiator for free- radical polymerization, Turk. J. Chem., 37 (2013) 525–537.
  • J. Xu, J. Ye, S.Y. Liu, Synthesis of well-defined cyclic poly(N-isopropylacrylamide) via click chemistry and its unique thermal phase transition behavior, Macromolecules, 40 (2007) 9103–9110.
  • N. Stoeckel, P.C. Wieland, O. Nuyken, New syntheses of graft copolymers using the DPE-technique: ATRP graft copolymerization, Polym. Bull., 49 (2002) 243– 250.
  • T. Öztürk, M.N. Atalar, M. Göktaş, B. Hazer, One-step synthesis of block-graft copolymers via simultaneous reversible-addition fragmentation chain transfer and ring-opening polymerization using a novel macroinitiator, J. Polym. Sci. Part A: Polym. Chem., 51 (2013) 2651–2659.
  • D.F. Grishin, Synthesis of vinyl chloride homo- and copolymers under the conditions of controlled radical polymerization, Russ. J. Appl. Chem., 88 (2015) 361– 376.
  • N. Hadjichristidis, H. Iatrou, M. Pitsikalis, J. Mays, Macromolecular architectures by living and controlled/living polymerizations, J. Prog. Polym. Sci., 31 (2006) 1068–1132.
  • H. Wang, J.H. Dong, A.Y. Qiu, Z.W. Gu, Studies on properties and drug delivery systems of PTMC-b- PEG-b-PTMC block copolymers, J. Macromol. Sci. Part A: Pure Appl. Chem., A 35 (1998) 811–820.
  • M. Aydinli, M. Tutas, O.A. Bozdemir, Mechanical and light transmittance properties of locust bean gum based edible films, Turk. J. Chem., 28 (2004) 163–171.
  • R.S. Velichkova, D.C. Christova, Amphiphilic polymers from macromonomers and telechelics, Prog. Polym. Sci., 20 (1995) 819–887.
  • G. Riess, Micellization of block copolymers, Prog. Polym. Sci., 28 (2003) 1107–1170.
  • B. Gacal, H. Durmaz, M.A. Tasdelen, G. Hizal, U. Tunca, Y. Yagci, A.L. Demirel, Anthracene-maleimide-based Diels-Alder “click chemistry” as a novel route to graft copolymers, Macromolecules, 39 (2006) 5330–5336.
  • S. Pispas, N. Hadjichristidis, Aggregation behavior of poly(butadiene-b-ethylene oxide) block copolymers in dilute aqueous solutions: effect of concentration, temperature, ionic strength, and type of surfactant, Langmuir, 19 (2003) 48–54.
  • M. Göktaş, T. Öztürk, M.N. Atalar, A.T. Tekeş, B. Hazer, One-step synthesis of triblock copolymers via simultaneous reversible-addition fragmentation chain transfer (raft) and ring-opening polymerization using a novel difunctional macro-raft agent based on polyethylene glycol, J. Macromol. Sci. Part A: Pure Appl. Chem., 51 (2014) 854–863.
  • T. Öztürk, M. Göktaş, B. Savaş, M. Işıklar, M.N. Atalar, B. Hazer, Synthesis and characterization of poly(vinyl chloride-graft-2-vinylpyridine) graft copolymers using a novel macroinitiator by reversible addition- fragmentation chain transfer polymerization, e– Polymers, 14 (2014) 27–34.
  • M. Pawlak, E. Grygolowicz-Pawlak, G.A. Crespo, G. Mistlberger, E. Bakker, Pvc-based ion-selective electrodes with enhanced biocompatibility by surface modification with “click” chemistry, Electroanalysis, 25 (2013) 1840–1846.
  • B. Hazer, B. Erdem, R.W. Lenz, Styrene polymerization with some new macro or macromonomeric azoinitiators having peg units, J. Polym. Sci. Part A: Polym. Chem., 32 (1994) 1739–1746.
  • T. Öztürk, M. Yavuz, M. Göktaş, B. Hazer, One- step synthesis of triarm block copolymers by simultaneous atom transfer radical and ring-opening polymerization, Polym. Bull., 73 (2016) 1497-1513.
  • T. Öztürk, O. Kayğın, M. Göktaş, B. Hazer, Synthesis and characterization of graft copolymers based on polyepichlorohydrin via reversible addition- fragmentation chain transfer polymerization, J. Macromol. Sci. Part A: Pure Appl. Chem., 53 (2016) 362-367.

“Click” Kimyası ile Poli vinil klorür–graft–etilen glikol Graft Kopolimerlerin Sentezi ve Karakterizasyonu

Year 2017, Volume: 45 Issue: 1, 35 - 42, 01.03.2017

Abstract

Poli vinil klorür–g–etilen glikol [poli VC–g–EG ] graft kopolimerlerin sentezi propargil polietilen glikolün propargil PEG ve azit son uçlu polivinil klorürün PVC–N3 “click” kimyası vasıtasıyla gerçekleştirildi. Öncelikle propargil PEG, çeşitli molekül ağırlığındaki PEG’ler 3000 Da, 2000 Da, 1500 Da, 1000 Da, 600 Da ve 400 Da ile propargil klorürün tepkimesi sonucunda sentezlendi. PVC–N3, saflaştırılmış PVC ve sodyum azit tepkimesi ile elde edildi. Poli VC–g–EG ] graft kopolimerler, PVC–N3 ve propargil PEG kullanılarak sentezlendi. Derişim ve zaman gibi tepkimeyi etkileyen temel parametreler değerlendirildi. Ürünlerin karakterizasyonları nükleer manyetik rezonans spektroskopisi, Fourier transform infrared spektroskopisi, gel geçirgenlik kromatografisi, elemental analiz ve fraksiyonlu çöktürme [çözücü THF, mL /çöktürücü petroleum ether, mL ] gibi yöntemler kullanılarak incelendi

References

  • H.C. Kolb, M.G. Finn, K.B. Sharpless, Click chemistry: diverse chemical function from a few good reactions, Angew. Chem. Int. Ed., 40 (2001) 2004–2021.
  • C.D. Hein, X.M. Liu, D. Wang, Click chemistry, a powerful tool for pharmaceutical sciences, Pharm. Res., 25 (2008) 2216–2230.
  • B. Kiskan, G. Demiray, Y. Yagci, Thermally curable polyvinyl chloride via click chemistry, J. Polym. Sci. Part A: Polym. Chem., 46 (2008) 3512–3518.
  • D.Y. Zhu, G.S. Cao, W.L. Qiu, M.Z. Rong, M.Q. Zhang, Self-healing polyvinyl chloride (PVC) based on microencapsulated nucleophilic thiol-click chemistry, Polymer, (69) 2015 1–9.
  • D. Tunc, B. Gacal, Y. Yagci, An amphiphatic thioxanthone-anthracene photoinitiator for free- radical polymerization, Turk. J. Chem., 37 (2013) 525–537.
  • J. Xu, J. Ye, S.Y. Liu, Synthesis of well-defined cyclic poly(N-isopropylacrylamide) via click chemistry and its unique thermal phase transition behavior, Macromolecules, 40 (2007) 9103–9110.
  • N. Stoeckel, P.C. Wieland, O. Nuyken, New syntheses of graft copolymers using the DPE-technique: ATRP graft copolymerization, Polym. Bull., 49 (2002) 243– 250.
  • T. Öztürk, M.N. Atalar, M. Göktaş, B. Hazer, One-step synthesis of block-graft copolymers via simultaneous reversible-addition fragmentation chain transfer and ring-opening polymerization using a novel macroinitiator, J. Polym. Sci. Part A: Polym. Chem., 51 (2013) 2651–2659.
  • D.F. Grishin, Synthesis of vinyl chloride homo- and copolymers under the conditions of controlled radical polymerization, Russ. J. Appl. Chem., 88 (2015) 361– 376.
  • N. Hadjichristidis, H. Iatrou, M. Pitsikalis, J. Mays, Macromolecular architectures by living and controlled/living polymerizations, J. Prog. Polym. Sci., 31 (2006) 1068–1132.
  • H. Wang, J.H. Dong, A.Y. Qiu, Z.W. Gu, Studies on properties and drug delivery systems of PTMC-b- PEG-b-PTMC block copolymers, J. Macromol. Sci. Part A: Pure Appl. Chem., A 35 (1998) 811–820.
  • M. Aydinli, M. Tutas, O.A. Bozdemir, Mechanical and light transmittance properties of locust bean gum based edible films, Turk. J. Chem., 28 (2004) 163–171.
  • R.S. Velichkova, D.C. Christova, Amphiphilic polymers from macromonomers and telechelics, Prog. Polym. Sci., 20 (1995) 819–887.
  • G. Riess, Micellization of block copolymers, Prog. Polym. Sci., 28 (2003) 1107–1170.
  • B. Gacal, H. Durmaz, M.A. Tasdelen, G. Hizal, U. Tunca, Y. Yagci, A.L. Demirel, Anthracene-maleimide-based Diels-Alder “click chemistry” as a novel route to graft copolymers, Macromolecules, 39 (2006) 5330–5336.
  • S. Pispas, N. Hadjichristidis, Aggregation behavior of poly(butadiene-b-ethylene oxide) block copolymers in dilute aqueous solutions: effect of concentration, temperature, ionic strength, and type of surfactant, Langmuir, 19 (2003) 48–54.
  • M. Göktaş, T. Öztürk, M.N. Atalar, A.T. Tekeş, B. Hazer, One-step synthesis of triblock copolymers via simultaneous reversible-addition fragmentation chain transfer (raft) and ring-opening polymerization using a novel difunctional macro-raft agent based on polyethylene glycol, J. Macromol. Sci. Part A: Pure Appl. Chem., 51 (2014) 854–863.
  • T. Öztürk, M. Göktaş, B. Savaş, M. Işıklar, M.N. Atalar, B. Hazer, Synthesis and characterization of poly(vinyl chloride-graft-2-vinylpyridine) graft copolymers using a novel macroinitiator by reversible addition- fragmentation chain transfer polymerization, e– Polymers, 14 (2014) 27–34.
  • M. Pawlak, E. Grygolowicz-Pawlak, G.A. Crespo, G. Mistlberger, E. Bakker, Pvc-based ion-selective electrodes with enhanced biocompatibility by surface modification with “click” chemistry, Electroanalysis, 25 (2013) 1840–1846.
  • B. Hazer, B. Erdem, R.W. Lenz, Styrene polymerization with some new macro or macromonomeric azoinitiators having peg units, J. Polym. Sci. Part A: Polym. Chem., 32 (1994) 1739–1746.
  • T. Öztürk, M. Yavuz, M. Göktaş, B. Hazer, One- step synthesis of triarm block copolymers by simultaneous atom transfer radical and ring-opening polymerization, Polym. Bull., 73 (2016) 1497-1513.
  • T. Öztürk, O. Kayğın, M. Göktaş, B. Hazer, Synthesis and characterization of graft copolymers based on polyepichlorohydrin via reversible addition- fragmentation chain transfer polymerization, J. Macromol. Sci. Part A: Pure Appl. Chem., 53 (2016) 362-367.
There are 22 citations in total.

Details

Primary Language English
Journal Section Research Article
Authors

Nilgün Asan This is me

Publication Date March 1, 2017
Published in Issue Year 2017 Volume: 45 Issue: 1

Cite

APA Asan, N. (2017). Synthesis and Characterization of Poly vinyl chloride–graft– ethylene glycol Graft Copolymers by “Click” Chemistry. Hacettepe Journal of Biology and Chemistry, 45(1), 35-42.
AMA Asan N. Synthesis and Characterization of Poly vinyl chloride–graft– ethylene glycol Graft Copolymers by “Click” Chemistry. HJBC. March 2017;45(1):35-42.
Chicago Asan, Nilgün. “Synthesis and Characterization of Poly Vinyl chloride–graft– Ethylene Glycol Graft Copolymers by ‘Click’ Chemistry”. Hacettepe Journal of Biology and Chemistry 45, no. 1 (March 2017): 35-42.
EndNote Asan N (March 1, 2017) Synthesis and Characterization of Poly vinyl chloride–graft– ethylene glycol Graft Copolymers by “Click” Chemistry. Hacettepe Journal of Biology and Chemistry 45 1 35–42.
IEEE N. Asan, “Synthesis and Characterization of Poly vinyl chloride–graft– ethylene glycol Graft Copolymers by ‘Click’ Chemistry”, HJBC, vol. 45, no. 1, pp. 35–42, 2017.
ISNAD Asan, Nilgün. “Synthesis and Characterization of Poly Vinyl chloride–graft– Ethylene Glycol Graft Copolymers by ‘Click’ Chemistry”. Hacettepe Journal of Biology and Chemistry 45/1 (March 2017), 35-42.
JAMA Asan N. Synthesis and Characterization of Poly vinyl chloride–graft– ethylene glycol Graft Copolymers by “Click” Chemistry. HJBC. 2017;45:35–42.
MLA Asan, Nilgün. “Synthesis and Characterization of Poly Vinyl chloride–graft– Ethylene Glycol Graft Copolymers by ‘Click’ Chemistry”. Hacettepe Journal of Biology and Chemistry, vol. 45, no. 1, 2017, pp. 35-42.
Vancouver Asan N. Synthesis and Characterization of Poly vinyl chloride–graft– ethylene glycol Graft Copolymers by “Click” Chemistry. HJBC. 2017;45(1):35-42.

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