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Citation: LIU Chao, YANG Changzhen, LI Weixue, ZHANG Yonglin, YAO Junshan, LEI Liangcai, LI Haiying. Synthesis of Novel Cyclic Poly(ε-caprolactone-co-γ-triethylsilyloxy-ε-caprolactone)[J]. Chinese Journal of Applied Chemistry, ;2014, 31(10): 1135-1142. doi: 10.3724/SP.J.1095.2014.30657 shu

Synthesis of Novel Cyclic Poly(ε-caprolactone-co-γ-triethylsilyloxy-ε-caprolactone)

1.
College of Chemistry and Materials Science, Liaoning SHIHUA University, Fushun 113001, China

Corresponding author: LI Haiying,
Received Date: 23 December 2013
Available Online: 18 February 2014
Fund Project: 国家自然科学基金资助项目(20974042) (20974042)

Design and synthesis of well-defined polymers are of the utmost importance for the reliable establishment of macromolecular structure-properties relationships. This work reports a novel strategy to synthesize cyclic random copolyesters with triethylsilyloxy groups. The ring-opening polymerization of a mixture of εCL and functional monomer γ-triethylsilyloxy-ε-caprolactone(γ-Et₃SiOεCL) was initiated by 2,2-dibutyl-2-stanna-1, 3-dioxepane(DSDOP) to obtain a precursor, i. e., a living cyclic copolyester(LCP(εCLcoγEt₃SiOεCL)). When the comonomers were converted completely, a fresh feed of α-(1-acryloyloxyethyl)-ε-caprolactone(αAEεCL) was added to the polymerization medium to achieve a living cyclic block copolyester, poly((εCLcoγEt₃SiOεCL)-b-(αAEεCL)). Finally, stable functional cyclic copolyester free of tin dialkoxides, i. e., cP(εCLcoγEt₃SiOεCL)(M_n,NMR=28500), was synthesized by intramolecular photo cross-linking of acrylic unsaturations in the proximity of the living cyclic chain under the irradiation of ultraviolet light. The structure and properties of the copolymers were characterized by size-exclusion chromatography(SEC), proton nuclear magnetic resonance spectroscopy(¹H NMR), and differential scanning calorimetry(DSC) technologies. The strategy herein disclosed has been successfully tested for the synthesis of functional cyclic copolyesters with high relative molecular mass in high efficiency.
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