Design of cross-linked semicrystalline poly(ε-caprolactone)-based networks with one-way and two-way shape-memory properties through diels-alder reactions
Abstract
Cross-linked poly(ε-caprolactone) (PCL)-based polyesterurethane (PUR) systems have been synthesized through Diels-Alder reactions by reactive extrusion. The Diels-Alder and retro-Diels-Alder reactions proved to be useful for enhancing the molecular motion of PCL-based systems, and therefore their crystallization ability, in the design of cross-linked semicrystalline polymers with one-way and two-way shape-memory properties. Successive reactions between α,ω-diol PCL (PCL(2) ), furfuryl alcohol, and methylene diphenyl 4,4'-diisocyanate straightforwardly afforded the α,ω-furfuryl PCL-based PUR systems, and subsequent Diels-Alder reactions with N,N-phenylenedimaleimide afforded the thermoreversible cycloadducts. The cross-linking density could be modulated by partially replacing PCL-diol with PCL-tetraol. Interestingly, the resulting PUR systems proved to be semicrystalline cross-linked polymers, the melting temperature of which (close to 45 °C) represented the switching temperature for their shape-memory properties. Qualitative and quantitative measurements demonstrated that these PUR systems exhibited one-way and two-way shape-memory properties depending on their cross-linking density.
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Semicrystalline polymers were one of the easily processed, produced and cross-linked polymers favoring their implementation in the production of cross-linked networks with 2W properties.
“Semicrystalline polymers were one of the easily processed, produced and cross-linked polymers favoring their implementation in the production of cross-linked networks with 2W properties [89].”
From Shape-memory polymers for multiple applications in the materials world (2016) · cites this paper as [89]
In 2011 Raquez et al. reported the production of thermoreversible crosslinked PCL-based PUR networks by reactive extrusion technology, characterized by 1W- and 2W-shape-memory properties.
“In this context, in 2011 Raquez et al. reported the production of thermoreversible crosslinked (PCL)-based PUR networks by reactive extrusion technology, which was characterized by 1W- and 2W-shape-memory properties [89].”
From Shape-memory polymers for multiple applications in the materials world (2016) · cites this paper as [89]
Thermally activated SMPs are formed by two active phases having a thermal transition at a determined temperature (Ttrans), the fixity phase and the switch phase, which can be covalently attached during the synthesis.
“Thermally activated SMPs are formed by two active phases having a thermal transition at a determined temperature (Ttrans) [12], the fixity phase and the switch phase [13, 14], which can be covalently attached during the synthesis [15, 16].”
From Biodegradable poly(ester-urethane) incorporated with catechin with shape memory and antioxidant activity for food packaging (2017) · cites this paper as [16]
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- Authors
- Raquez, J., Vanderstappen, S., Meyer, F., Verge, P., Alexandre, M., Thomassin, J., Jérôme, C., & Dubois, P.
- Affiliations
- University of Mons (BE)
- University of Liège (BE)
- Corresponding author
- Raquez, Jean‐Marie
- Venue
- Chemistry – A European Journal
- Publisher
- Wiley
- Published
- 2011-07-08
- Volume
- 17
- Issue
- 36
- Pages
- 10135-10143
- ISSN
- 0947-6539 (ISSN-L)
- 1521-3765
- OpenAlex
- W1969194929
- Cited by
- 133
- References
- 42
- Citations by year
- 2026: 2 · 2025: 10 · 2024: 5 · 2023: 2 · 2022: 13 · 2021: 12 · 2020: 11 · 2019: 10 · 2018: 10 · 2017: 13 · 2016: 12 · 2015: 9 · 2014: 7 · 2013: 9 · 2012: 8
- FWCI
- 6.54
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Chemistry - A European Journal (publishedVersion)
- PubMed (publishedVersion)
- Dépôt institutionnel de l'Université libre de Bruxelles (Université Libre de Bruxelles) (submittedVersion)
- Open Repository and Bibliography (University of Liège) (submittedVersion)
- PolyPublie (École Polytechnique de Montréal) (submittedVersion)
- Funders
- Fonds De La Recherche Scientifique - FNRS
- Topics
- Physical Sciences › Materials Science › Polymers and Plastics › Polymer composites and self-healing
- Physical Sciences › Materials Science › Polymers and Plastics › Polymer crystallization and properties
- Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
- Keywords
- polycaprolactone, polyester polyurethane, shape memory polymers, two-way shape memory, Diels-Alder reaction, retro-Diels-Alder reaction, crosslink density, furfuryl alcohol, reactive extrusion, crystallization
- MeSH terms
- Crystallization, Elasticity, Polyesters, Polyurethanes
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