Synthesis of self-healing polymers precursors from available bio-renewable raw materials

A series of a new diglycidyl derivatives of aromatic amines containing a furan fragment was obtained. The synthetic scheme consists of two stages: reductive amination and epoxidation. We used industrially produced inexpensive amines and furfural as starting material. Diepoxides obtained are key components for development of epoxy binders capable of intrinsic self-healing based on the reversible Diels-Alder reaction between furan and maleimide. To demonstrate the possibility of self-healing, the Diels-Alder reaction adduct of one of the products with N-phenyl maleimide was isolated and characterized by 2D NMR spectroscopy. The reversibility of the reaction was confirmed by DSC experiment. (paper)