Reversible TAD Chemistry as a Convenient Tool for the Design of (Re)processable PCL-Based Shape-Memory Materials.
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.
Centre for Education and Research on Macromolecules (CERM), CESAM Research Unit, University of Liege (ULg), Building B6a, 4000, Liège, Belgium.
Thomas
T
Defize
Centre for Education and Research on Macromolecules (CERM), CESAM Research Unit, University of Liege (ULg), Building B6a, 4000, Liège, Belgium.
Raphaël
R
Riva
Centre for Education and Research on Macromolecules (CERM), CESAM Research Unit, University of Liege (ULg), Building B6a, 4000, Liège, Belgium.
Jean-Michel
JM
Thomassin
Centre for Education and Research on Macromolecules (CERM), CESAM Research Unit, University of Liege (ULg), Building B6a, 4000, Liège, Belgium.
Michaël
M
Alexandre
Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281 S4-bis, B-9000, Ghent, Belgium.
Niels Van
NV
Herck
Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281 S4-bis, B-9000, Ghent, Belgium.
Filip Du
FD
Prez
Centre for Education and Research on Macromolecules (CERM), CESAM Research Unit, University of Liege (ULg), Building B6a, 4000, Liège, Belgium.
Christine
C
Jérôme
D003432:Cross-Linking Reagents / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011091:Polyesters / Q000138:chemical synthesis* / Q000737:chemistry; D014230:Triazoles / Q000737:chemistry*
C000617023:1,2,4-triazoline-3,5-dione; D003432:Cross-Linking Reagents; D011091:Polyesters; D014230:Triazoles; C016240:polycaprolactone
Alder-ene reaction; TAD chemistry; shape-memory materials; solid-state plasticity; thermoreversible networks