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Self-healing polymers based on eugenol via combination of thiol-ene and thiol oxidation reactions

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Abstract

Eugenol, a relatively cheap and abundant renewable resource, is used to design terminal diene compounds. Thiol-ene click reactions between the terminal diene intermediates and 1,6-hexanedithiol afford the corresponding oligomers with molecular mass of about 1.3 kDa. Finally, the oligomers and tricapto compound trimethylolpropane tris(3-mercaptopropionate) undergo thiol-oxidation reactions to form disulfide-crosslinked polymers. The brown polymers indicate self-healable behavior under UV light irradiation, presumably due to reversible reshuffling of weak disulfide bonds and/or reversible addition-dissociation reaction between benzoxazine and thiol groups.

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Acknowledgments

The work was financially supported by Natural Science Foundations of China (NO. 21264008, 21564004) and the 8th Foundation of Creativity and Study for College Students in Jiangxi Science Technology Normal University.

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Jiangxi Science & Technology Normal University, Fenglin Street, Nanchang, Jiangxi, 330013, People’s Republic of China

    Chuanjie Cheng, Xu Zhang, Xinghe Chen, Jin Li, Qinghua Huang, Zhongyu Hu & Yuanming Tu

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  1. Chuanjie Cheng
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  2. Xu Zhang
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  3. Xinghe Chen
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  4. Jin Li
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  5. Qinghua Huang
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  7. Yuanming Tu
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Correspondence to Chuanjie Cheng.

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Cheng, C., Zhang, X., Chen, X. et al. Self-healing polymers based on eugenol via combination of thiol-ene and thiol oxidation reactions. J Polym Res 23, 110 (2016). https://doi.org/10.1007/s10965-016-1001-x

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