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Synthesis of pH-responsive polyimide hydrogel from bioderived amino acid

Polymer Journal volume 53, pages 1223–1230 (2021)Cite this article

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Abstract

A series of biobased polyimides bearing a structure derived from a predetermined tetracarboxylic dianhydride was synthesized. By ionizing the COOH group of the side chain with potassium hydroxide, four kinds of polyimides were solubilized in water, and the water-soluble polyimides were cast onto films over an aqueous solution, leading to higher optical transparency than that of non-water-soluble polyimides. 1H nuclear magnetic resonance measurements of the polyimides revealed no residual reactants from the polymerization process or side-chain modification. Partial crosslinking of the water-soluble polyimide chains by condensation of the carboxylate side chain with an amino acid-based diamine such as 4-aminophenylalanine or 4,4′-diamino-α-truxillic acid induced the formation of polyimide hydrogels. The remaining COOK groups of the obtained hydrogel were protonated/deprotonated by changing the pH, accompanied by reversible shrinking and swelling.

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Acknowledgements

This work was financially supported by the Shibuya Science and Sports Culture Foundation and partially supported by the Japan Society for the Promotion of Science of Grant-in-Aid for Early-Career Scientists (21K14681) and Super Highways (Japan Science and Technology Agency), Japan.

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Authors and Affiliations

  1. Graduate School of Advanced Science and Technology, Japan Advanced Institute of Science and Technology, Ishikawa, Japan

    Kenji Takada, Takumi Noda, Takuya Kobayashi, Toyohiro Harimoto, Maninder Singh & Tatsuo Kaneko

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  1. Kenji Takada
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  2. Takumi Noda
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Correspondence to Kenji Takada or Tatsuo Kaneko.

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Takada, K., Noda, T., Kobayashi, T. et al. Synthesis of pH-responsive polyimide hydrogel from bioderived amino acid. Polym J 53, 1223–1230 (2021). https://doi.org/10.1038/s41428-021-00509-8

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