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Curing of resveratrol-based trifunctional five-membered cyclic carbonate with various diamines and properties of the cured resins

Polymer Journal (2025)Cite this article

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Abstract

A trifunctional five-membered cyclic carbonate resin synthesized from resveratrol (Res-TC) was thermally cured with various diamines: trioxyethylene diamine (TODA), dioxyethylene diamine (DODA), m-xylene diamine (mXDA), pentamethylene diamine (PMDA), and Jeffamine ED-600. Thermogravimetric analysis (TGA) revealed that the cured Res-TC/TODA, Res-TC/DODA, Res-TC/mXDA, and Res-TC/PMDA were easily thermally decomposed, whereas the cured Res-TC/Jeffamine was relatively stable. Differential scanning calorimetry (DSC) indicated that the cured Res-TC/TODA and Res-TC/Jeffamine samples were rubbery, whereas the cured Res-TC/DODA, Res-TC/mXDA, and Res-TC/PMDA samples were glassy at room temperature. Tensile tests of the cured resin films revealed that Res-TC/TODA, Res-TC/DODA, and Res-TC/PMDA had high elastic moduli of approximately 1 GPa with moderate tensile strengths, whereas Res-TC/mXDA had low tensile strength, indicating that it was a brittle material. Cured Res-TC/Jeffamine was a very soft material with poor mechanical properties. An adhesion test of the metal substrates revealed that cured Res-TC/TODA adhered strongly to both aluminum and stainless steel. After treatment with enzymes such as lipase and protease, some cured resins exhibited greater water uptake than did those treated with pure water, indicating that the enzymes cleaved the network of the cured resins and gradually decomposed the materials.

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Funding

This work was financially supported by the Japan Society for the Promotion of Science (JSPS) KAKENHI Grant Number 21K05189.

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  1. Department of Biological & Environmental Chemistry, Kindai University, 11-6 Kayanomori, Izuka, Fukuoka, 820-8555, Japan

    Kozo Matsumoto, Takeo Mitoma, Iku Yamashita & Tatsuki Watanabe

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  1. Kozo Matsumoto
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  2. Takeo Mitoma
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Correspondence to Kozo Matsumoto.

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Matsumoto, K., Mitoma, T., Yamashita, I. et al. Curing of resveratrol-based trifunctional five-membered cyclic carbonate with various diamines and properties of the cured resins. Polym J (2025). https://doi.org/10.1038/s41428-025-01077-x

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