Comprehensive study of the thermo-reversibility of Diels–Alder based PCL polymer networks

Defize, Thomas; Thomassin, Jean‐Michel; Alexandre, Michaël; Gilbert, Bernard; Riva, Raphaël; Jérôme, Christine

doi:10.1016/j.polymer.2015.11.055

Cited by 62 publications

(68 citation statements)

References 38 publications

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“…Crosslinked polymers containing furfuryl and maleimide groups have been reported as well as linear alternatives but the synthetic routes are susceptible toward irreversible side‐reactions (particularly the Michael‐addition which occurs when maleimides are reacted in the presence of free nucleophiles at elevated temperature) or they involve the use maleimides that are not readily commercially available or the perspective is different from ours focusing on other applications including shape memory materials . An elegant approach is presented by Defize et al . that study binary systems composed of furfuryl and maleimide end‐functionalized four‐arm star‐shaped polycaprolactones.…”

Section: Introductionmentioning

confidence: 99%

Polyurethane adhesives containing Diels–Alder‐based thermoreversible bonds

Turkenburg¹,

Bracht²,

Funke³

et al. 2017

J of Applied Polymer Sci

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A facile two‐step process is developed to obtain polyester urethanes that contain various concentrations of thermoreversible Diels–Alder adduct–based bonds for the development of adhesives. Besides linear systems thermoreversible networks have been included in the study. The reactions are verified using IR‐spectroscopy and gel permeation chromatography analysis. The material properties are characterized with solvent exposure tests, dynamic scanning calorimetry, microindentation and rheology and the potential for application as adhesives is tested with an elcometer. Material properties have been found highly tunable for the system, and high adhesive strengths (off‐scale) are found for polyester urethanes that are doped with an intermediate level Diels–Alder functional groups. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017, 134, 44972.

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Section: Introductionmentioning

confidence: 99%

Polyurethane adhesives containing Diels–Alder‐based thermoreversible bonds

Turkenburg¹,

Bracht²,

Funke³

et al. 2017

J of Applied Polymer Sci

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“…The reversibility of the network by formation/breaking‐up of the AE adducts was first studied by rheology measurements at 120 °C (Figure A). As it is expected for a conventional thermoreversible DA reaction, upon heating, a shift of the equilibrium toward the break‐up of the adducts is observed, leading to a decrease of the network cross‐linking rate down to a viscous liquid and thus to a remoldable material . In Figure A, the storage modulus ( G ′), loss modulus ( G ″), and tan δ were measured at 120 °C as a function of time in order to highlight the position shifts of the TAD–indole equilibrium.…”

Section: Resultsmentioning

confidence: 75%

“…In order to improve the blending in the mini‐extruder, a stoichiometric amount of PCL‐6Indole and MDI‐TAD powders was together grinded beforehand until a finely ground powder was obtained. The blending of the precursors was then carried out at 120 °C to confer on one hand enough chain mobility to PCL and on the other hand also to avoid a cross‐linking reaction by the AE reaction during extrusion, since this reaction between TAD and indole is supposed to be shifted toward the dissociation of the adduct at 120 °C, similar to the dissociation of the DA adduct between furan and maleimide . The temperature was kept below 150 °C to avoid the thermal degradation of MDI‐TAD.…”

Section: Resultsmentioning

confidence: 99%

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Reversible TAD Chemistry as a Convenient Tool for the Design of (Re)processable PCL‐Based Shape‐Memory Materials

Defize

Riva

Thomassin

et al. 2016

Macromol. Rapid Commun.

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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.

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“…It is often utilized for a biodegradable polymer plasticizer as a result of its linear structure. It has been found that due to the presence of the segment PCL, the fracture growth rate, ductility, and mechanical processability of the composite can be significantly improved, and overall strengthening and toughening can be achieved . Sun's team found that the new PHB‐based polyurethane polymer with PCL segment has better physicochemical properties, and the new polymer has better flexibility, lower crystallinity, and deformation recovery than PHB .…”

Section: Synthesis Of Polyhydroxyalkanoatesmentioning

confidence: 99%

Recent Progress in Polyhydroxyalkanoates‐Based Copolymers for Biomedical Applications

Luo

Liu

et al. 2019

Biotechnology Journal

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In recent years, naturally biodegradable polyhydroxyalkanoate (PHA) monopolymers have become focus of public attentions due to their good biocompatibility. However, due to its poor mechanical properties, high production costs, and limited functionality, its applications in materials, energy, and biomedical applications are greatly limited. In recent years, researchers have found that PHA copolymers have better thermal properties, mechanical processability, and physicochemical properties relative to their homopolymers. This review summarizes the synthesis of PHA copolymers by the latest biosynthetic and chemical modification methods. The modified PHA copolymer could greatly reduce the production cost with elevated mechanical or physicochemical properties, which can further meet the practical needs of various fields. This review further summarizes the broad applications of modified PHA copolymers in biomedical applications, which might shred lights on their commercial applications.

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Comprehensive study of the thermo-reversibility of Diels–Alder based PCL polymer networks

Cited by 62 publications

References 38 publications

Polyurethane adhesives containing Diels–Alder‐based thermoreversible bonds

Polyurethane adhesives containing Diels–Alder‐based thermoreversible bonds

Reversible TAD Chemistry as a Convenient Tool for the Design of (Re)processable PCL‐Based Shape‐Memory Materials

Recent Progress in Polyhydroxyalkanoates‐Based Copolymers for Biomedical Applications

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