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Updated: Jan 3, 2026

The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry
Published on: August 25, 2016
A broadly applicable cross-linker for aliphatic polymers containing C-H bonds
Mathieu L Lepage1, Chakravarthi Simhadri1, Chang Liu1
1Department ofChemistry, University of Victoria, Victoria, BC V8W-3V6, Canada.
Abstract:
Addition of molecular cross-links to polymers increases mechanical strength and improves corrosion resistance. However, it remains challenging to install cross-links in low-functionality macromolecules in a well-controlled manner. Typically, high-energy processes are required to generate highly reactive radicals in situ, allowing only limited control over the degree and type of cross-link. We rationally designed a bis-diazirine molecule whose decomposition into carbenes under mild and controllable conditions enables the cross-linking of essentially any organic polymer through double C-H activation. The utility of this molecule as a cross-linker was demonstrated for several diverse polymer substrates (including polypropylene, a low-functionality polymer of long-standing challenge to the field) and in applications including adhesion of low-surface-energy materials and the strengthening of polyethylene fabric.
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