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Synthesis of poly(L-lactide) and polyglycolide by ring-opening polymerization

Nature Protocols volume 2, pages 2767–2771 (2007)Cite this article

Abstract

This protocol describes the synthesis of poly(L-lactide) by ring-opening polymerization of L-lactide using tin(II) 2-ethylhexanoate catalyst as well as the synthesis of polyglycolide by ring-opening polymerization of glycolide. Ring-opening polymerization of cyclic diesters synthesized from α-hydroxycarboxylic acids gives high-molecular-weight polyester in high yield. Tin(II) 2-ethylhexanoate catalyst is the most common catalyst for ring-opening polymerization of diesters owing to its high reactivity and low toxicity. Purity of monomers and the amount of water and alcohol in the reaction system are significant factors for increasing molecular weight and conversion of polyesters. The molecular weight of the polyesters is also dependent on reaction temperature and reaction time. This protocol can be completed in 3 d for the synthesis of poly(L-lactide) and 2 d for the synthesis of polyglycolide.

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Figure 1
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Figure 5: Photographs of polymer products L-lactide and PLLA after re-precipitation.

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Acknowledgements

This work was supported by a Grant-in-Aid for General Scientific Research and by a Grant-in-Aid for the 21st Century COE Program 'KEIO LCC' from the Ministry of Education, Culture, Sports, Science, and Technology, Japan. This work was also supported by a US National Institutes of Health grant to A.G.M. (R01 DE15164) as well as by the US National Science Foundation through a CAREER Award to J.P.F. (no. 0448684) and the Arthritis Foundation through an Arthritis Investigator Award to J.P.F.

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Authors and Affiliations

  1. Department of Applied Chemistry, Keio University, Yokohama, 223-8522, Japan

    Sachiko Kaihara & Shuichi Matsumura

  2. Department of Bioengineering, Rice University, Houston, 77251, Texas, USA

    Antonios G Mikos

  3. Fischell Department of Bioengineering, University of Maryland, College Park, 20742, Maryland, USA

    John P Fisher

Authors
  1. Sachiko Kaihara
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  2. Shuichi Matsumura
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  3. Antonios G Mikos
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  4. John P Fisher
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Correspondence to John P Fisher.

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Kaihara, S., Matsumura, S., Mikos, A. et al. Synthesis of poly(L-lactide) and polyglycolide by ring-opening polymerization. Nat Protoc 2, 2767–2771 (2007). https://doi.org/10.1038/nprot.2007.391

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