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Synthesis of Sulfur/Selenium-containing Polyester with Recyclability and Controllable Hydrophilicity and Glass Transition Temperature

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Abstract

We present a ring-opening polymerization of bridged cyclic lactone utilizing alcohol as the initiator and organic base as the catalyst. Bridged γ-butyrolactone monomers (PhSGBL and PhSeGBL) were synthesized efficiently from commercially available 3-cyclohexene-1-carboxylic acid. Due to the ring strain of the bridged structure, ring-opening polymerization of this type of γ-butyrolactone derivative was successfully carried out under mild conditions, e.g., using ethylene glycol as the initiator and a commercial catalyst [1,5,7-triazabicyclo [4.4.0 dec-5-ene (TBD)] as the catalyst at 30 °C. The obtained polymer could be degraded to its monomer for recycling in the presence of ZnCl2 as a catalyst. PhSGBL and PhSeGBL could also be copolymerized with ε-caprolactone to tune the glass transition temperature. Additionally, the hydrophilicity of the obtained sulfur-containing polymers could be adjusted by selectively oxidizing the thioether side group to sulfone/sulfoxide, which offered a way to tune the hydrophilicity of polyester. On the other hand, the obtained selenium-containing compound could be degraded in the presence of m-CPBA (3-chloroperbenzoic acid), which offered potential application in sustained drug release.

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Acknowledgments

This work was financially supported by National Key Research and Development Program of China (No. 2022YFB3704905), and the Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institutions.

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Authors and Affiliations

  1. Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application, Department of Polymer Science and Engineering, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, China

    Wen-**g Li, **ang-Qiang Pan, Jian Zhu & Zheng-Biao Zhang

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  1. Wen-**g Li
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  2. **ang-Qiang Pan
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  3. Jian Zhu
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  4. Zheng-Biao Zhang
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Correspondence to **ang-Qiang Pan or Jian Zhu.

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Synthesis of Sulfur/Selenium-containing Polyester with Recyclability and Controllable Hydrophilicity and Glass Transition Temperature

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Li, WJ., Pan, XQ., Zhu, J. et al. Synthesis of Sulfur/Selenium-containing Polyester with Recyclability and Controllable Hydrophilicity and Glass Transition Temperature. Chin J Polym Sci 41, 1836–1845 (2023). https://doi.org/10.1007/s10118-023-2994-3

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  • DOI: https://doi.org/10.1007/s10118-023-2994-3

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