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Polylactide Block Copolymers using Trimethylene Carbonate with Methoxyethoxy Side Groups for Dual Modification of Hydrophilicity and Biodegradability

Authors

  • Hiroharu Ajiro,

    1. Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamada-oka, Suita, Osaka 565-0871, Japan
    2. The Center for Advanced Medical Engineering and Informatics, Osaka University, 2-2 Yamada-oka, Suita, Osaka 565-0871, Japan
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  • Yoshikazu Takahashi,

    1. Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamada-oka, Suita, Osaka 565-0871, Japan
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  • Mitsuru Akashi,

    Corresponding author
    1. Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamada-oka, Suita, Osaka 565-0871, Japan
    2. The Center for Advanced Medical Engineering and Informatics, Osaka University, 2-2 Yamada-oka, Suita, Osaka 565-0871, Japan
    • Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamada-oka, Suita, Osaka 565-0871, Japan.
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  • Tomoko Fujiwara

    Corresponding author
    1. The University of Memphis, Department of Chemistry, 213 Smith Chemistry Building, Memphis, TN 38152, USA
    • The University of Memphis, Department of Chemistry, 213 Smith Chemistry Building, Memphis, TN 38152, USA
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Abstract

Novel block copolymers using the monomers 5-(2-methoxyethyoxymethyl)-5-methyl-[1,3]-dioxa-2-one (TMCM-MOE1OM) as a hydrophilic segment and lactides as a hydrophobic segment were designed in order to prepare controllable degradation polymers by dynamic polymer rearrangement based on the hydrophilicity. When the copolymer film contacted water, the hydrophobic polylactide (PLA) segments tend to be buried under the TMCM-MOE1OM segments due to the hydrophilicity of the methoxyethoxy groups. The copolymers were hardly degraded by both proteinase K and lipase, while both of their homopolymers, poly(trimethylene carbonate) and PLA, were degraded, which suggests that the rearrangement of the TMCM-MOE1OM segments at the outermost surface significantly improved the degradation ratio.

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