Soybean oil based thermoset networks via photoinduced CuAAC click chemistry

Abstract

A simple method based on photochemically induced copper(I)-catalyzed azide - alkyne cycloaddition click reaction (CuAAC) is developed for the preparation of thermoset networks from soybean oils as renewable resources. The incorporation of clickable azide and alkyne functionalities into epoxidized soybean oils is done by simultaneous ring-opening reactions between the epoxide group of soybean oils and sodium azide and propargyl alcohol, respectively. The obtained azide- and alkyne-functionalized soybean oils are easily transformed crosslinked networks via the photoinduced CuAAC reaction in ambient conditions. The introduction of additional multifunctional monomers in the formulation not only increases the crosslinking density but also improves the mechanical properties of the thermoset material obtained. In a comparison of the two formulations, the sample containing additional multifunctional monomers has a higher glass transition temperature, storage modulus and damping properties. (c) 2017 Society of Chemical Industry