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Controlled/living ring-opening polymerization of ɛ-caprolactone catalyzed by phosphoric acid

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Abstract

The bulk ring-opening polymerization (ROP) of ɛ-caprolactone (ɛ-CL) by various phosphoric acids using phenylmethanol as the initiator was conducted. 1,1′-bi-2-Naphthol (BINOL)-based phosphoric acid was found to be an effective organocatalyst for ROP leading to polyesters at 90°C. The overall conversion to poly(ɛ-caprolactone) was more than 96% and poly(ɛ-caprolactone) with M w of 8400 and polydispersity index of 1.13 was obtained. 1H NMR spectra of oligomers demonstrated the quantitative incorporation of the protic initiator in the polymer chains and showed that transesterification reactions did not occur to a significant extent. The controlled polymerization was indicated by the linear relationships between the number-average molar mass and monomer conversion or monomer-to-initiator ratio. In addition, the present protocol provided an easy-to-handle, inexpensive and environmentally benign entry for the synthesis of biodegradable materials as well as polyesters for biomedical applications.

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Authors and Affiliations

  1. Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin, 150040, China

    ChunXia Chen, Rong Xu & Bin Li

  2. Post-doctoral Mobile Research Station of Forestry Engineering, Northeast Forestry University, Harbin, 150040, China

    ChunXia Chen

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  1. ChunXia Chen
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  2. Rong Xu
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  3. Bin Li
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Correspondence to Bin Li.

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Chen, C., Xu, R. & Li, B. Controlled/living ring-opening polymerization of ɛ-caprolactone catalyzed by phosphoric acid. Sci. China Chem. 55, 1257–1262 (2012). https://doi.org/10.1007/s11426-012-4586-x

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  • DOI: https://doi.org/10.1007/s11426-012-4586-x

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