Journal
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
Volume 6, Issue 9, Pages 12088-12095Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acssuschemeng.8b02423
Keywords
Cardanol; Bio-based; Polyol; Thiol-ene; Thiol-epoxy; Polyurethane
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Funding
- University of Akron
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Two novel bio-based polyols were synthesized from cardanol via thiol-ene/thiol-epoxy dual click-reactions. Compared with the cardanol-based polyols synthesized by the thiol-ene reaction, the cardanol-based polyols synthesized by thiol-ene/thiol-epoxy dual reactions have a higher hydroxyl number due to the additional secondary hydroxyl group generated from the thiol-epoxy reaction. The synthesized polyols were formulated with hexamethylene diisocyanate (HDI) trimers to prepare cardanol-based thermosetting polyurethane (PU) films. Thorough thermal and mechanical characterizations of the prepared PU films were carried out to study the structure-property relationship. An UV-aging test was conducted to characterize the color retention of the cardanol-based PU films. The thermal stability of cardanol-based PU films was improved after converting the phenolic hydroxyl to aliphatic hydroxyl. With increasing the hydroxyl number of cardanol-based polyols, the cross-link density, glass transition temperature, elastic modulus, tensile strength, and hardness of cardanol-based PU films were all improved. The results of this work confirmed that the utilization of thiol-ene/thiol-epoxy dual click-reactions is an effective approach to synthesize cardanol-based polyols with a relatively high hydroxyl number. The significance of this work is believed to broaden the usage of cardanol in different PU formulations and applications.
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