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Self-healing epoxy networks based on cyclodextrin–adamantane host–guest interactions

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Abstract

An aminated β-cyclodextrin (NCD) with an amine substitution degree of 16.4 was prepared through the thiol–ene reaction of allylated β-cyclodextrin and cysteamine hydrochloride. The thermal curing reactions of sorbitol polyglycidyl ether (SPE) with NCD, Jeffamine® ED-600 (JA, an aliphatic polyether amine), and adamantylamine (NAD) with a feed epoxy/NH2 ratio of 1:1 and feed NH2 molar ratios of NCD/JA/NAD = 1/1/1 and 1/2/1 produced epoxy-amine networks. The FT-IR and gel fraction measurements for the cured products revealed that polymer networks were formed by the reaction of epoxy and amino groups. The cured product with a higher JA content showed lower glass transition temperature (Tg), tensile strength, and tensile modulus results than those of the cured product with a lower JA content. Compared with the product with lower JA, the product with higher JA exhibited self-healing properties upon treatment at 60 °C. The self-healing driven by the NCD/NAD host–guest interaction was demonstrated as the self-healed sample returned to its original state after immersion in an ethanol solution of NAD. Moreover, the corresponding SPE/NCD/JA and SPE/JA/NAD cured products did not exhibit self-healing capacity.

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Acknowledgements

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

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  1. Department of Applied Chemistry, Faculty of Engineering, Chiba Institute of Technology, 2-17-1, Tsudanuma, Narashino, Chiba, 275-0016, Japan

    Kaito Sugane, Yuji Maruoka & Mitsuhiro Shibata

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  1. Kaito Sugane
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Sugane, K., Maruoka, Y. & Shibata, M. Self-healing epoxy networks based on cyclodextrin–adamantane host–guest interactions. J Polym Res 28, 423 (2021). https://doi.org/10.1007/s10965-021-02790-w

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