Biobased and biodegradable imine vitrimers from epoxidized soybean oil as packaging

Abstract

A flexible and stretchable vitrimer was synthesized using exclusively biobased building blocks and following green chemistry principles. Epoxidized soybean oil (ESO), vanillin, the biobased diamine, Priamine®, and oleic acid were used to create a material that can replace fossil‐derived, non‐biodegradable packaging. Vanillin and Priamine® were used to develop a crosslinker that could react with the epoxide groups of ESO without the need for solvents, with a catalyst‐free synthesis that does not generate any waste or byproducts. Oleic acid was incorporated, to tune the properties of the final material, since it can react with ESO and control the crosslink density. The vitrimers produced in this work showed excellent reprocessability and recyclability. They possess the ability to be molded, and they can also strongly adhere on surfaces. Moreover, they exhibited oxygen and water vapor barrier comparable to low density polyethylene, while showing very low migration into food simulant, which position them as a promising material for flexible food and general packaging market. The vitrimers showed also the capability of biodegradation in seawater, providing a safe end of life in case of mismanagement.