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Synthesis of comb-type amphiphilic graft copolymers derived from chlorinated poly(ɛ-caprolactone) via click reaction

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Abstract

This work refers to the synthesis of a series of novel chlorinated poly(ɛ-caprolactone) (PCL) for further functionalization of PCL. For this aim, chlorine gas was passed through into the chloroform solution to obtain chlorinated polycaprolactone. The chlorine contents in chlorinated PCL were between 0.9 and 1.6 mol%. The molecular weights of the polymers (M n) changed from 4853 to 9497 g/mol. As the amount of passing chlorine gas increases, the molecular weight of the chlorinated PCL was found to decrease. Pendant chloride groups of PCL were reacted with sodium azide to prepare PCL with pendant azide groups (PCL-N3). Poly-(ethylene glycol) methyl ether (mPEG) was reacted with propargyl chloride to achieve alkynyl mPEG (mPEG-alkyn). Click reaction was then carried out by the reaction between PCL-N3 and mPEG-alkyn to obtain PCL-g-PEG comb-type amphiphilic graft copolymer. Interestingly, SEM images of the PCL-g-PEG comb-type amphiphilic graft copolymers showed the highly microporous structure. The resulting products were characterized by 1H NMR, FT-IR, gel-permeation chromatography, SEM, surface tension, contact angle and water uptake measurements, differential scanning calorimeter and thermogravimetric analyses techniques.

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Acknowledgments

This work was supported by Bülent Ecevit University Research Fund (#BEU-2012-10-03-13), TUBITAK (Grant # 211T016) and TUBITAK 2211—A National Scholarship Programme for Timur Şanal (PhD Student).

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  1. Department of Chemistry, Bülent Ecevit University, 67100, Zonguldak, Turkey

    Timur Şanal, İzzet Koçak & Baki Hazer

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  1. Timur Şanal
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  2. İzzet Koçak
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  3. Baki Hazer
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Correspondence to Baki Hazer.

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Şanal, T., Koçak, İ. & Hazer, B. Synthesis of comb-type amphiphilic graft copolymers derived from chlorinated poly(ɛ-caprolactone) via click reaction. Polym. Bull. 74, 977–995 (2017). https://doi.org/10.1007/s00289-016-1757-5

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