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Synthesis and property of novel amino acid-based polymers by self-polyaddition of monomers containing both oxetanyl and carboxyl groups

Authors

  • Hiroto Kudo,

    1. Department of Materials and Life Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1, Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan
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  • Toshiki Ohshiro,

    1. Department of Materials and Life Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1, Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan
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  • Hiroyuki Atsumi,

    1. Department of Materials and Life Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1, Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan
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  • Ayako Kamio,

    1. Department of Materials and Life Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1, Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan
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  • Tadatomi Nishikubo,

    Corresponding author
    1. Department of Materials and Life Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1, Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan
    • Department of Materials and Life Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1, Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan
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  • Saeko Murakami

    1. Kanagawa Industrial Technology Center, 705-1, Shimoimaizumi, Ebina-Shi, Kanagawa 243-0435, Japan
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Abstract

A new synthetic strategy for polymers containing amino acids in the main chain was developed. Monomers N-oxetanylalanine (N-Oxe-Ala-COOH), N-oxetanylglutamic acid (N-Oxe-Glu-COOH), and N-oxetanyllysine (N-Oxe-Lys-COOH) containing both oxetanyl and carboxyl groups were synthesized, and self-polyaddition and self-copolyaddition of these monomers afforded the corresponding polymers containing amino acids in the main chain [poly(OxAla), poly(OxLys), poly(OxGlu), poly(OxAla-co-OxGlu), poly(OxGlu-co-OxLys), and poly(OxAla-co-OxLys)] with molecular weight in the range of 920–6620, in satisfactory yields. The physical properties, such as solubility, glass transition temperature, and thermal stability, were consistent with the amount of carboxyl groups at the chain ends. Biodegradability of the polymers was examined by the biochemical oxygen demand method; the decomposition ratios of poly(OxAla) and poly(OxAla-co-OxGlu) were about 60%, whereas that of poly(OxGlu) was nearly 100% after 28 days. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011

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