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Hydrolytic degradation and biomineralization of amine-cured epoxy resin based on glycidate

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Abstract

Amine-cured epoxy resins bearing ester moieties were synthesized, and their properties, hydrolytic degradation behavior, and biomineralization were investigated. Neopentyl glycol diglycidate (NPG) was used as the epoxide and was cured with diethylenetriamine (DETA) and isophoronediamine (IPD) at different ratios. The glass transition temperatures were controlled using the composition of DETA and IPD. The cured materials containing IPD units were tolerant to neutral water but were degraded under acidic and basic conditions. Degradation in the presence of lipase also proceeded in phosphate buffer, while degradation proceeded gradually in the absence of lipase. To demonstrate their potential application as degradable biomedical materials for bone and dental repair, composites containing hydroxyapatite (HA) were prepared by curing NPG and the amines in the presence of HA. Biological bone-like apatite was grown on an NPG-IPD-HA composite by immersion in synthetic biofluid, and the amount of bone-like apatite was greater than that on the glycidyl ether analog.

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Acknowledgements

We are thankful for the financial support from JSPS KAKENHI (grant number JP19K22212), the Adaptable and Seamless Technology Transfer Program through Target-driven R&D (A-STEP) from Japan Science and Technology Agency (JST) (grant number AS2621327M, and Nagase ChemteX Co., Inc.), and the kind advice from Mr. Tetsuya Hosomi of Nagase ChemteX Co., Inc.

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  1. Yoshimasa Matsumura

    Present address: Faculty of Engineering, Osaka Institute of Technology, Asahi-ku, Osaka, 535-8585, Japan

Authors and Affiliations

  1. Graduate School of Science and Engineering, Yamagata University, Yonezawa, Yamagata, 992-8510, Japan

    Bungo Ochiai, Yutaka Nakazawa, Yoshimasa Matsumura & Takahiro Kawai

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  1. Bungo Ochiai
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Ochiai, B., Nakazawa, Y., Matsumura, Y. et al. Hydrolytic degradation and biomineralization of amine-cured epoxy resin based on glycidate. Polym J 56, 409–417 (2024). https://doi.org/10.1038/s41428-023-00880-8

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