Study of Diels–Alder reactions between furan and maleimide model compounds and the preparation of a healable thermo‐reversible polyurethane

ABSTRACT A study of the reactions between various furan and maleimide model compounds and the effects of reaction conditions was performed, allowing for a proper design and preparation of a thermo‐reversible polyurethane (PU) material crosslinked via Diels–Alder (DA) bonds. Thus, a linear polyurethane containing furan groups along the main chain was synthesized and crosslinked with a bismaleimide by means of DA reaction. The obtained thermoset exhibited thermo‐reversibility as evidenced by DSC and FTIR microscopy, providing the material recyclability and scratch healability. Optical microscopy, SEM and tensile analysis of a scratched PU film revealed that efficient scratch healing was enabled by heating at 110 °C for 30 min and subsequently keeping at room temperature for 24 h, resulting in an approximately 80% recovery of the pristine mechanical strength. This material is a promising candidate for the development of self‐healing coatings. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018 , 56 , 1806–1814