Synthesis of a Sustainable and Bisphenol A-Free Epoxy Resin Based on Sorbic Acid and Characterization of the Cured Thermoset |
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| Authors: | Jonas M Breitsameter Nikita Reinhardt Matthias Feigel Olaf Hinrichsen Klaus Drechsler Bernhard Rieger |
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| Affiliation: | 1. Wacker-Chair of Macromolecular Chemistry, TUM School of Natural Sciences, Technical University of Munich, 85748 Lichtenbergstr. 4, Garching, Germany;2. Chair of Carbon Composites, TUM School of Engineering and Design, Technical University of Munich, 85748 Boltzmannstr. 15, Garching, Germany;3. Chair I of Technical Chemistry, TUM School of Natural Sciences, Technical University of Munich, D-85748 Lichtenbergstr. 4, Garching, Germany |
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| Abstract: | In the present study, an epoxy compound, 1,2-epoxy-6-methyl-triglycidyl-3,4,5-cyclohexanetricarboxylate (EGCHC) synthesized from sorbic acid, maleic anhydride, and allyl alcohol is proposed. Using commodity chemicals, a bio-based carbon content of 68.4 % for the EGCHC resin is achieved. When cured with amine hardeners, the high oxirane content of EGCHC forms stiff cross-linked networks with strong mechanical and thermal properties. The characterization of the epoxy specimens showed that EGCHC can compete with conventional epoxy resins such as DGEBA. A maximum stiffness of 3965 MPa, tensile strength of 76 MPa, and Tg of 130 °C can be obtained by curing EGCHC with isophorone diamine (IPD). The cured resin showed to be decomposable under mild conditions due to the ester bonds. The solid material properties of EGCHC expose its potential as a promising bisphenol A, and epichlorohydrine free alternative to conventional petroleum-based epoxies with an overall high bio-based carbon content. |
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| Keywords: | bio-based materials epoxy thermosets sorbic acid thermo-mechanical properties |
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