Abstract
Plant oil is one of the world’s most abundant renewable resources; however, its derived epoxies are low in thermal resistance and mechanical strength. In this work, a new chemical route referred to “competitive nucleophilic attack (CNA)” was discovered to achieve plant-oil-based epoxy with high thermal resistance and mechanical strength as well as many other unique properties comparable to those of diglycidyl ether of bisphenol A (DGEBA), one of the most popular petroleum-based epoxies. The CNA route was realized by using 10-undecenoic acid (UA), a plant-derived monomer, as a building block reacting with alicyclic oxirane chemicals, such as 4-ethenyl-7-oxabicyclo[4.1.0]heptanes (ECP), to achieve epoxy monomers with ether-bridged cycloaliphatic ring structure. A newly formed hydroxyl (NFH) is involved in the nucleophilic attack upon oxonium to compete with UA anion during the UA–ECP reaction. The resultant epoxy is UV-curable in a few seconds, possessing high tensile strength (∼48 MPa), high glass transiti...
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