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“Click” Kimyası ile Poli Epiklorhidrin–G–Etilen Glikol Graft Kopolimerlerin Sentezi ve Karakterizasyonu

Year 2017, Volume: 7 Issue: 1, 47 - 54, 01.01.2017

Abstract

Poli epiklorhidrin-g-polietilen glikol [poli ECH-g-EG ] graft kopolimerlerin sentezi “click” kimyası metodu ile rapor edilmektedir. Bu amaçla, epiklorhidrin ECH , H2SO4 ile katyonik halka-açılması polimerizasyonu üzerinden polimerleştirildi. Propargil polietilen glikol-1000 propargil PEG-1000 , propargil klorür ve 1000 Da molekül ağırlığına sahip polietilen glikolün PEG reaksiyonu ile sentezlendi. Poliepiklorhidrin azit PECH-N3 , poliepiklorhidrin ve sodyum azidin reaksiyonu ile elde edildi. PECH-N3 ve propargil PEG-1000 kullanılarak poli ECH-g-EG graft kopolimerler nispeten yüksek verimle sentezlendi. Ürünler, fraksiyonlu çöktürme [çözücü THF, mL /çöktürücü petrol eteri, mL ] ile saflaştırıldı; nükleer manyetik rezonans spektroskopisi, Fourier transform infrared spektroskopisi, gel geçirgenlik kromatografisi, elemental analiz ve termogravimetrik analiz cihazları kullanılarak karakterize edildi. Polimer sentezi için kullanılan bu metot basit, etkili, çevre dostu ve düşük enerji tüketimine sahiptir

References

  • Al-Kaabi, K., van Reene, AJ. 2008.Controlled radical polymeri- zation of poly(methyl methacrylate-g-epichlorohydrin) using N,-N-dithiocarbamate-mediated iniferters. J. Appl. Polym. Sci., 108:2528–2534.
  • Asan, N., Öztürk, T. 2016. Synthesis and characterization of poly (vinyl chloride–graft–ethylene glycol) graft copolymers by “click” chemistry. Hacettepe J. Bio. Chem., (submitted).
  • banaszczyk, MG., Lollo, CP., Kwoh, DY., Phillips, AT., Amini, A., Wu, DP., Mullen, PM., Coffin, CC., brostoff. SW., Carlo, DJ. 1999. Poly-l-lysine-graft-peg comb-type polycation copolymers for gene delivery. J. Macromol. Sci. Part A, 36:1061–1084.
  • Coulembier, O., Degee, P., Hedrick, JL., Dubois, P. 2006. From controlled ring-opening polymerization to biodegradable aliphatic polyester: Especially poly(beta-malic acid) derivatives. Prog. Polym. Sci., 31:723–747.
  • Degirmenci, M., Hizal, G., Yagci, Y. 2002. Synthesis and characterization of macrophotoinitiators of poly(epsilon- caprolactone) and their use in block copolymerization. Macromolecules, 35:8265-8270.
  • Guerrouani, N., Mas, A., Schue, F. 2010. MgH2/PEG initiating system for ring opening polymerization of lactone and lactide. e-Polymers, 24:no pp given. Table 1. ether-mL). Code HA-1 HA-2 HA-3 HA-4 HA-5
  • Öztürk, T., Göktaş, M., Savaş, b., Işıklar, M., Atalar, MN., Hazer, b. 2014. 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, 14:27-34.
  • Öztürk, T., Hazer, b. 2010. Synthesis and characterization of a novel macromonomer initiator for reversible addition fragmentation chain transfer (raft). Evaluation of the polymerization kinetics and gelation behaviors. J. Macromol. Sci. Part A, 47:265–272.
  • Öztürk, T., Atalar, MN., Göktaş, M., Hazer, b. 2013. 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, 51:2651–2659.
  • Pawlak, M., Grygolowicz-Pawlak, E., Crespo, GA., Mistlberger, G., bakker, E. 2013. PVC-based ion-selective electrodes with enhanced biocompatibility by surface modification with “click” chemistry. Electroanalysis, 25:1840–1846.
  • Riess, G. 2003. Micellization of block copolymers. Prog. Polym. Sci., 28:1107–1170.
  • Song, ZM., Zhu, WX., Song, JR., Wei, P., Yang, FY., Liu, N., Feng, RL. 2015. Linear-dendrimer type methoxy-poly (ethylene glycol)-b-poly (epsilon-caprolactone) copolymer micelles for the delivery of curcumin. Drug. Del., 22:58–68.
  • Stoeckel, N., Wieland, PC., Nuyken, O. 2002. New syntheses of graft copolymers using the DPE-technique: ATRP graft copolymerization. Polym. Bull., 49: 243–250.
  • Xu, J., Ye, J., Liu, SY. 2007. Synthesis of well-defined cyclic poly(N-isopropylacrylamide) via click chemistry and its unique thermal phase transition behavior. Macromolecules, 40:9103–9110.
  • Velichkova, RS., Christova, DC. 1995. Amphiphilic polymers from macromonomers and telechelics. Prog. Polym. Sci., 20:819–887.
  • Wu, b., Lenz, RW., Hazer b. 1999. Polymerization of methyl methacrylate and its copolymerization with caprolactone catalyzed by isobutylalumoxane catalyst. Macromolecules, 32:6856–6859.
  • Zhu, DY., Cao, GS., Qiu, WL., Rong, MZ., Zhang, MQ. 2015. Self-healing polyvinyl chloride (pvc) based on microencapsulated nucleophilic thiol-click chemistry. Polymer, 69:1–9.
  • Zhang, X., Pan, S-R., Hu, H-M., Wu, G-F., Feng, M., Zhang, W., Luo, X. 2008. Poly(ethylene glycol)-block- polyethylenimine copolymers as carriers for gene delivery: Effects of PEG molecular weight and PEGylation degree. J. Biomed. Mater. Res. Part A, 84:795-804.

Synthesis and characterization of poly epichlorohydrin-graft-ethylene glycol graft copolymers by "click" chemistry

Year 2017, Volume: 7 Issue: 1, 47 - 54, 01.01.2017

Abstract

Synthesis of poly epichlorohydrin-g-ethylene glycol [poly ECH-g-EG ] graft copolymer was reported by means of "click" chemistry. For this purpose, epichlorohydrin ECH was polymerized by using H2SO4 via cationic ring-opening mechanism. Propargyl polyethylene glycol-1000 propargyl PEG-1000 was synthesized by the reaction of polyethylene glycol PEG with 1000 Da and propargyl chloride. Terminally azide polyepichlorohydrin PECH-N3 was obtained by reaction of poly epichlorohydrin PECH and sodium azide. By using PECH-N3 and propargyl PEG-1000, poly ECH-g-EG graft copolymers were synthesized. The graft copolymers were relatively obtained in high yield. The characterization 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, thermogravimetric analysis, and fractional precipitation [solvent THF, mL /non–solvent petroleum ether, mL ] techniques. This method which is used for polymer synthesis is simple, effective, eco-friendly and has low energy consumption.

References

  • Al-Kaabi, K., van Reene, AJ. 2008.Controlled radical polymeri- zation of poly(methyl methacrylate-g-epichlorohydrin) using N,-N-dithiocarbamate-mediated iniferters. J. Appl. Polym. Sci., 108:2528–2534.
  • Asan, N., Öztürk, T. 2016. Synthesis and characterization of poly (vinyl chloride–graft–ethylene glycol) graft copolymers by “click” chemistry. Hacettepe J. Bio. Chem., (submitted).
  • banaszczyk, MG., Lollo, CP., Kwoh, DY., Phillips, AT., Amini, A., Wu, DP., Mullen, PM., Coffin, CC., brostoff. SW., Carlo, DJ. 1999. Poly-l-lysine-graft-peg comb-type polycation copolymers for gene delivery. J. Macromol. Sci. Part A, 36:1061–1084.
  • Coulembier, O., Degee, P., Hedrick, JL., Dubois, P. 2006. From controlled ring-opening polymerization to biodegradable aliphatic polyester: Especially poly(beta-malic acid) derivatives. Prog. Polym. Sci., 31:723–747.
  • Degirmenci, M., Hizal, G., Yagci, Y. 2002. Synthesis and characterization of macrophotoinitiators of poly(epsilon- caprolactone) and their use in block copolymerization. Macromolecules, 35:8265-8270.
  • Guerrouani, N., Mas, A., Schue, F. 2010. MgH2/PEG initiating system for ring opening polymerization of lactone and lactide. e-Polymers, 24:no pp given. Table 1. ether-mL). Code HA-1 HA-2 HA-3 HA-4 HA-5
  • Öztürk, T., Göktaş, M., Savaş, b., Işıklar, M., Atalar, MN., Hazer, b. 2014. 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, 14:27-34.
  • Öztürk, T., Hazer, b. 2010. Synthesis and characterization of a novel macromonomer initiator for reversible addition fragmentation chain transfer (raft). Evaluation of the polymerization kinetics and gelation behaviors. J. Macromol. Sci. Part A, 47:265–272.
  • Öztürk, T., Atalar, MN., Göktaş, M., Hazer, b. 2013. 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, 51:2651–2659.
  • Pawlak, M., Grygolowicz-Pawlak, E., Crespo, GA., Mistlberger, G., bakker, E. 2013. PVC-based ion-selective electrodes with enhanced biocompatibility by surface modification with “click” chemistry. Electroanalysis, 25:1840–1846.
  • Riess, G. 2003. Micellization of block copolymers. Prog. Polym. Sci., 28:1107–1170.
  • Song, ZM., Zhu, WX., Song, JR., Wei, P., Yang, FY., Liu, N., Feng, RL. 2015. Linear-dendrimer type methoxy-poly (ethylene glycol)-b-poly (epsilon-caprolactone) copolymer micelles for the delivery of curcumin. Drug. Del., 22:58–68.
  • Stoeckel, N., Wieland, PC., Nuyken, O. 2002. New syntheses of graft copolymers using the DPE-technique: ATRP graft copolymerization. Polym. Bull., 49: 243–250.
  • Xu, J., Ye, J., Liu, SY. 2007. Synthesis of well-defined cyclic poly(N-isopropylacrylamide) via click chemistry and its unique thermal phase transition behavior. Macromolecules, 40:9103–9110.
  • Velichkova, RS., Christova, DC. 1995. Amphiphilic polymers from macromonomers and telechelics. Prog. Polym. Sci., 20:819–887.
  • Wu, b., Lenz, RW., Hazer b. 1999. Polymerization of methyl methacrylate and its copolymerization with caprolactone catalyzed by isobutylalumoxane catalyst. Macromolecules, 32:6856–6859.
  • Zhu, DY., Cao, GS., Qiu, WL., Rong, MZ., Zhang, MQ. 2015. Self-healing polyvinyl chloride (pvc) based on microencapsulated nucleophilic thiol-click chemistry. Polymer, 69:1–9.
  • Zhang, X., Pan, S-R., Hu, H-M., Wu, G-F., Feng, M., Zhang, W., Luo, X. 2008. Poly(ethylene glycol)-block- polyethylenimine copolymers as carriers for gene delivery: Effects of PEG molecular weight and PEGylation degree. J. Biomed. Mater. Res. Part A, 84:795-804.
There are 18 citations in total.

Details

Primary Language Turkish
Journal Section Research Article
Authors

Temel Öztürk This is me

Hıdır Ayyıldız This is me

Ergül Meyvacı This is me

Melahat Göktaş This is me

Publication Date January 1, 2017
Published in Issue Year 2017 Volume: 7 Issue: 1

Cite

APA Öztürk, T., Ayyıldız, H., Meyvacı, E., Göktaş, M. (2017). “Click” Kimyası ile Poli Epiklorhidrin–G–Etilen Glikol Graft Kopolimerlerin Sentezi ve Karakterizasyonu. Karaelmas Fen Ve Mühendislik Dergisi, 7(1), 47-54.
AMA Öztürk T, Ayyıldız H, Meyvacı E, Göktaş M. “Click” Kimyası ile Poli Epiklorhidrin–G–Etilen Glikol Graft Kopolimerlerin Sentezi ve Karakterizasyonu. Karaelmas Fen ve Mühendislik Dergisi. January 2017;7(1):47-54.
Chicago Öztürk, Temel, Hıdır Ayyıldız, Ergül Meyvacı, and Melahat Göktaş. “‘Click’ Kimyası Ile Poli Epiklorhidrin–G–Etilen Glikol Graft Kopolimerlerin Sentezi Ve Karakterizasyonu”. Karaelmas Fen Ve Mühendislik Dergisi 7, no. 1 (January 2017): 47-54.
EndNote Öztürk T, Ayyıldız H, Meyvacı E, Göktaş M (January 1, 2017) “Click” Kimyası ile Poli Epiklorhidrin–G–Etilen Glikol Graft Kopolimerlerin Sentezi ve Karakterizasyonu. Karaelmas Fen ve Mühendislik Dergisi 7 1 47–54.
IEEE T. Öztürk, H. Ayyıldız, E. Meyvacı, and M. Göktaş, “‘Click’ Kimyası ile Poli Epiklorhidrin–G–Etilen Glikol Graft Kopolimerlerin Sentezi ve Karakterizasyonu”, Karaelmas Fen ve Mühendislik Dergisi, vol. 7, no. 1, pp. 47–54, 2017.
ISNAD Öztürk, Temel et al. “‘Click’ Kimyası Ile Poli Epiklorhidrin–G–Etilen Glikol Graft Kopolimerlerin Sentezi Ve Karakterizasyonu”. Karaelmas Fen ve Mühendislik Dergisi 7/1 (January 2017), 47-54.
JAMA Öztürk T, Ayyıldız H, Meyvacı E, Göktaş M. “Click” Kimyası ile Poli Epiklorhidrin–G–Etilen Glikol Graft Kopolimerlerin Sentezi ve Karakterizasyonu. Karaelmas Fen ve Mühendislik Dergisi. 2017;7:47–54.
MLA Öztürk, Temel et al. “‘Click’ Kimyası Ile Poli Epiklorhidrin–G–Etilen Glikol Graft Kopolimerlerin Sentezi Ve Karakterizasyonu”. Karaelmas Fen Ve Mühendislik Dergisi, vol. 7, no. 1, 2017, pp. 47-54.
Vancouver Öztürk T, Ayyıldız H, Meyvacı E, Göktaş M. “Click” Kimyası ile Poli Epiklorhidrin–G–Etilen Glikol Graft Kopolimerlerin Sentezi ve Karakterizasyonu. Karaelmas Fen ve Mühendislik Dergisi. 2017;7(1):47-54.