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Self-healing high-performance thermosets utilizing the furan/maleimide Diels-Alder and amine/maleimide Michael reactions

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Abstract

The reaction of furfurylamine (FA) and 4,4′-bismaleimidodiphenylmethane (BMI) at a molar ratio of 2/1 generated a product (FABMI) mainly composed of 4,4′-bis(2-furfurylaminosuccinimido)diphenylmethane. Mixtures of FABMI, BMI and p-xylylenediamine (XDA) at FABMI/BMI/XDA molar ratios of 1/3/1, 2/4/1, 1/4/1 and 2/6/1 were prepolymerized at 120 °C, hot-pressed at 130–140 °C, and then annealed at 60 °C to produce cured products. The FT-IR analysis revealed that the Michael addition and Diels-Alder (DA) reactions occurred for all the cured products. FABMI-BMI-XDAs with relatively low feed FABMI mass fractions displayed excellent 5% mass loss temperatures higher than 400 °C. The cured product with the highest feed XDA mass fraction exhibited the highest flexural strength, modulus and strain at break among all the cured products. Onset temperatures of the endothermal retro DA reaction for the cured products were in the ranges of 140–150 °C. All the cured products were at least twice healed by the thermal treatment at 150 °C for 20 min and then 60 °C for 48 h.

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Acknowledgements

We thank Dr. Naozumi Teramoto of our department for his helpful suggestions.

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Authors and Affiliations

  1. Department of Life and Environmental Sciences, Faculty of Engineering, Chiba Institute of Technology, 2-17-1, Tsudanuma, Narashino, Chiba, 275-0016, Japan

    Kanami Yasuda, Kaito Sugane & Mitsuhiro Shibata

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  1. Kanami Yasuda
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Correspondence to Mitsuhiro Shibata.

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Yasuda, K., Sugane, K. & Shibata, M. Self-healing high-performance thermosets utilizing the furan/maleimide Diels-Alder and amine/maleimide Michael reactions. J Polym Res 27, 18 (2020). https://doi.org/10.1007/s10965-019-1986-z

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