Reversible TAD Chemistry as a Convenient Tool for the Design of (Re) processable PCL-Based Shape-Memory Materials
Defize, T.; Riva, R.ël.; Thomassin, J.-M.; Alexandre, M.ël.; Herck, N.V.; Prez, F.D.; Jérôme, C.
Macromolecular Rapid Communications 38(1)
ISSN/ISBN: 1521-3927 PMID: 27805739 DOI: 10.1002/marc.201600517
A chemically cross-linked but remarkably (re)processable shape-memory polymer (SMP) is designed by cross-linking poly(ε-caprolactone) (PCL) stars via the efficient triazolinedione click chemistry, based on the very fast and reversible Alder-ene reaction of 1,2,4-triazoline-3,5-dione (TAD) with indole compounds. Typically, a six-arm star-shaped PCL functionalized by indole moieties at the chain ends is melt-blended with a bisfunctional TAD, directly resulting in a cross-linked PCL-based SMP without the need of post-curing treatment. As demonstrated by the stress relaxation measurement, the labile character of the TAD-indole adducts under stress allows for the solid-state plasticity reprocessing of the permanent shape at will by compression molding of the raw cross-linked material, while keeping excellent shape-memory properties.