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Updated: Sep 22, 2025

The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry
Published on: August 25, 2016
Cascading Retro-Diels-Alder Cycloreversion and Sydnone-Maleimide Based Double 1,3-Dipolar Cycloaddition for
Jeremy J Intemann1, Wei Huang1,2, Zhian Jin1
1Department of Materials Science and Engineering, University of Washington, Seattle, Washington, 98195-2120, United States.
Abstract:
A new approach to polymer cross-linking is investigated using a cascading cycloreversion of a maleimide-furan adduct and a double 1,3-dipolar cycloaddition between a sydnone and maleimide. The cross-linking proceeds quantitatively above 63 °C, despite the polymer possessing no observable glass transition temperature. The resulting polymer network possesses a high thermal stability (>300 °C) due to the irreversibility of the sydnone-maleimide cycloaddition, which releases CO2 during the cross-linking, driving the reaction. The rigid three-dimensional structure of the bis-maleimide-sydnone cycloadduct produced local free volumes in films, decreasing the dielectric constant of the material.
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