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Eco-friendly synthesis of biodegradable poly(ε-caprolactone) using L-lactic and glycolic acids as organic initiator

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Abstract

Biodegradable poly(ε-caprolactone) (PCL) was successfully synthesized by the green polymerization process that was conducted in the absence of heavy metal catalyst and toxic solvent. L-Lactic (LLA) and glycolic acids (GA) were utilized as green initiator for the bulk ring-opening polymerization (ROP) of ε-caprolactone (ε-CL). These organic initiators could produce PCL with number average molecular weight (Mn) in the range of 8.46 × 103–1.98 × 104 g/mol and molecular weight distribution (MWD) of 1.71–1.81. GA could produce higher molecular weight PCL than LLA under identical synthesis condition. The catalytic performance of these initiators in the ROP of ε-CL was completely investigated by the non-isothermal differential scanning calorimetry (DSC). From non-isothermal DSC kinetics analysis, the reactivity of GA was higher than LLA in the bulk ROP of ε-CL as supported by the lower values of activation energy (Ea) and frequency factor (A) of GA than LLA initiator. The polymerization mechanism for the ROP of ε-CL initiated by LLA and GA was proposed through the activated monomer mechanism.

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Acknowledgements

The authors wish to thanks the financial supports from Chiang Mai University (WP, PM), the Thailand Research Fund (TRF) (MRG6080164) (WL) and Office of the Higher Education Commission (OHEC) (WL). The Department of Chemistry and Materials Science Research Center, Faculty of Science, Chiang Mai University (CMU) and Faculty of Sciences and Agricultural Technology, Rajamangala University of Technology Lanna (RMUTL) are also acknowledged.

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Authors and Affiliations

  1. Faculty of Sciences and Agricultural Technology, Rajamangala University of Technology Lanna, Chiang Mai, 50300, Thailand

    Wanich Limwanich

  2. Department of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai, 50200, Thailand

    Puttinan Meepowpan, Montira Sriyai, Tawan Chaiwon & Winita Punyodom

  3. Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Chiang Mai University, Chiang Mai, 50200, Thailand

    Puttinan Meepowpan, Montira Sriyai & Winita Punyodom

  4. Graduate School, Chiang Mai University, Chiang Mai, 50200, Thailand

    Montira Sriyai & Tawan Chaiwon

  5. Center of Excellence in Materials Science and Technology, Chiang Mai University, Chiang Mai, 50200, Thailand

    Puttinan Meepowpan & Winita Punyodom

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  1. Wanich Limwanich
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  2. Puttinan Meepowpan
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Correspondence to Wanich Limwanich.

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Limwanich, W., Meepowpan, P., Sriyai, M. et al. Eco-friendly synthesis of biodegradable poly(ε-caprolactone) using L-lactic and glycolic acids as organic initiator. Polym. Bull. 78, 7089–7101 (2021). https://doi.org/10.1007/s00289-020-03401-2

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  • DOI: https://doi.org/10.1007/s00289-020-03401-2

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