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Biodegradable Polymers from 5-Hydroxylevulinic Acid: 1. Synthesis and Characterization of Poly(5-hydroxylevulinic acid)

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Abstract

As an attempt to synthesize new biodegradable polymers from renewable cellulose resources, melt polycondensation of 5-hydroxylevulinic acid (5-HLA) was reported for the first time. The resulting product, poly(5-hydroxylevulinic acid) (PHLA), was synthesized and characterized with GPC, FTIR, 1H NMR and DSC. The in vitro degradation behaviors in phosphate-buffered saline (PBS) and in deionized water (DW) were also examined. The molecular weight of PHLA is not high (several 1,000s), but it possesses unordinary high glass transition temperature (as high as 120 °C). This is very different from existing aliphatic polyesters that usually have T gs lower than 60 °C. The high T g is attributed to the formation of inter- and/or intramolecular hydrogen bonds due to a characteristic keto–enol tautomerism equilibrium in the polymer structure. PHLA readily degraded hydrolytically in aqueous media.

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Acknowledgments

The authors thank the National Natural Science Foundation of China (20304012, 20406018, 20674067), the Prior Special Fund for National Basic Research Program of China (2004CCA05500), the Specialized Research Fund for Doctoral Program of China (20020335101) and Zhejiang Natural Science Foundation (No. Y404084) for financial supports.

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Authors and Affiliations

  1. The State Key Laboratory of Polymer Reaction Engineering, Department of Chemical and Biochemical Engineering, Zhejiang University, Hangzhou, 310027, China

    Linbo Wu, Yan Zhang, Hong Fan, Zhiyang Bu & Bo-Geng Li

  2. School of Biological and Chemical Engineering, Ningbo Insitute of Technology, Zhejiang University, Ningbo, 315100, China

    Yan Zhang

Authors
  1. Linbo Wu
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  2. Yan Zhang
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  3. Hong Fan
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  4. Zhiyang Bu
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  5. Bo-Geng Li
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Correspondence to Linbo Wu or Bo-Geng Li.

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Wu, L., Zhang, Y., Fan, H. et al. Biodegradable Polymers from 5-Hydroxylevulinic Acid: 1. Synthesis and Characterization of Poly(5-hydroxylevulinic acid). J Polym Environ 16, 68–73 (2008). https://doi.org/10.1007/s10924-008-0082-y

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  • DOI: https://doi.org/10.1007/s10924-008-0082-y

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