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

Wen-Jing Li; Xiang-Qiang Pan; Jian Zhu; Zheng-Biao Zhang

doi:10.1007/s10118-023-2994-3

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

RESEARCH ARTICLE | Updated：2023-11-27

- Synthesis of Sulfur/Selenium-containing Polyester with Recyclability and Controllable Hydrophilicity and Glass Transition Temperature
- Chinese Journal of Polymer Science Vol. 41, Issue 12, Pages: 1836-1845(2023)
- Affiliations：
  
  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
- Author bio：
  
  panxq@suda.edu.cn (X.Q.P.)
  chemzhujian@suda.edu.cn (J.Z.)
- Funds：
- DOI：10.1007/s10118-023-2994-3
  CLC：
- Received：18 March 2023，
  
  Revised：2023-4-13，
  
  Accepted：28 April 2023，
  
  Online First：12 June 2023，
  
  Published：01 December 2023
- Accepted：
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Li, W. J.; Pan, X. Q.; Zhu, J.; Zhang, Z. B. Synthesis of sulfur/selenium-containing polyester with recyclability and controllable hydrophilicity and glass transition temperature. Chinese J. Polym. Sci. 2023, 41, 1836–1845

Wen-Jing Li, Xiang-Qiang Pan, Jian Zhu, et al. Synthesis of Sulfur/Selenium-containing Polyester with Recyclability and Controllable Hydrophilicity and Glass Transition Temperature[J]. Chinese Journal of Polymer Science, 2023, 41(12): 1836-1845.
Li, W. J.; Pan, X. Q.; Zhu, J.; Zhang, Z. B. Synthesis of sulfur/selenium-containing polyester with recyclability and controllable hydrophilicity and glass transition temperature. Chinese J. Polym. Sci. 2023, 41, 1836–1845 DOI： 10.1007/s10118-023-2994-3.

Wen-Jing Li, Xiang-Qiang Pan, Jian Zhu, et al. Synthesis of Sulfur/Selenium-containing Polyester with Recyclability and Controllable Hydrophilicity and Glass Transition Temperature[J]. Chinese Journal of Polymer Science, 2023, 41(12): 1836-1845. DOI： 10.1007/s10118-023-2994-3.

摘要

The synthesis of functional polyesters via ring-opening polymerization of chalcogen-containing bridged bicyclic lactones using alcohol as an initiator and organic base as a catalyst was designed. This polyester exhibits thermal recyclability

good thermostability

controllable hydrophilicity

and a defined glass transition temperature.

Abstract

We present a ring-opening polymerization of bridged cyclic lactone utilizing alcohol as the initiator and organic base as the catalyst. Bridged

-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

-butyrolactone derivative was successfully carried out under mild conditions

e.g.

using ethylene glycol as the initiator and a commercial catalyst [1

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 ZnCl

as a catalyst. PhSGBL and PhSeGBL could also be copolymerized with

-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

-CPBA (3-chloroperbenzoic acid)

which offered potential application in sustained drug release.

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