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Synthesis of Cardanol-Based Polyols via Thiol-ene/Thiol-epoxy Dual Click-Reactions and Thermosetting Polyurethanes Therefrom

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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… Click to show full abstract

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...

Keywords: based polyols; thiol ene; thiol epoxy; cardanol based; ene thiol

Journal Title: ACS Sustainable Chemistry & Engineering
Year Published: 2018

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