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Introduction of Reversible Urethane Bonds Based on Vanillyl Alcohol for Efficient Self-Healing of Polyurethane Elastomers

Division of Semiconductor and Chemical Engineering, Chonbuk National University, Baekjedaero 567, Jeonju 54896, Korea
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Author to whom correspondence should be addressed.
Contributed equally to this work.
Academic Editors: Elisabete C.B.A. Alegria and Maximilian N. Kopylovich
Molecules 2019, 24(12), 2201; https://doi.org/10.3390/molecules24122201
Received: 4 April 2019 / Revised: 5 June 2019 / Accepted: 9 June 2019 / Published: 12 June 2019
(This article belongs to the Special Issue Mechanically Responsive Materials and Their Applications)
Urethane groups formed by reacting phenolic hydroxyl groups with isocyanates are known to be reversible at high temperatures. To investigate the intrinsic self-healing of polyurethane via a reversible urethane group, we synthesized vanillyl alcohol (VA)-based polyurethanes. The phenolic hydroxyl group of vanillyl alcohol allows the introduction of a reversible urethane group into the polyurethane backbone. Particularly, we investigated the effects of varying the concentration of reversible urethane groups on the self-healing of the polyurethane, and we proposed a method that improved the mobility of the molecules contributing to the self-healing process. The concentration of reversible urethane groups in the polyurethanes was controlled by varying the vanillyl alcohol content. Increasing the concentration of the reversible urethane group worsened the self-healing property by increasing hydrogen bonding and microphase separation, which consequently decreased the molecular mobility. On the other hand, after formulating a modified chain extender (m-CE), hydrogen bonding and microphase separation decreased, and the mobility (and hence the self-healing efficiency) of the molecules improved. In VA40-10 (40% VA; 10% m-CE) heated to 140 °C, the self-healing efficiency reached 96.5% after 30 min, a 139% improvement over the control polyurethane elastomer (PU). We conclude that the self-healing and mechanical properties of polyurethanes might be tailored for applications by adjusting the vanillyl alcohol content and modifying the chain extender. View Full-Text
Keywords: vanillyl alcohol; self-healing efficiency; mechanical property; reversible urethane bond vanillyl alcohol; self-healing efficiency; mechanical property; reversible urethane bond
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MDPI and ACS Style

Lee, D.-W.; Kim, H.-N.; Lee, D.-S. Introduction of Reversible Urethane Bonds Based on Vanillyl Alcohol for Efficient Self-Healing of Polyurethane Elastomers. Molecules 2019, 24, 2201.

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