Vitrimeric Epoxy-Amine Polyimine Networks Based on a Renewable Vanillin Derivative

Abstract

A series of bio-based polyimine vitrimers was obtained and characterized. A diimine-diglycidyl monomer (DIDG) was synthesized by condensing vanillin with 4,4′-oxydianiline (ODA) and further glycidylation with epichlorohydrin. This compound was cross-linked with three different Jeffamines (Jeff230, JeffD400, and JeffT403) with a different number of poly(propylene glycol) units in their structure and different functionalities. Trimethylolpropane triglycidyl ether (TMPTE) was added to the formulation to improve the thermal, mechanical, and thermomechanical properties. All of the materials prepared showed Tg's above 66 °C, good vitrimeric behavior being the maximum relaxation rate reached by the material prepared from JeffD400, which also allows the most extensive degradation when treated with an acidic aqueous solution. These polyimine vitrimers can entirely relax the stress in less than 10.5 min at 150 °C without any added catalyst. All of the materials prepared could be satisfactorily recycled up to 200 °C also presenting an excellent self-welding ability.