TY - JOUR
T1 - Beyond Diels-Alder
T2 - Domino reactions in furan-maleimide click networks
AU - van den Tempel, Paul
AU - van der Boon, Emiel O.
AU - Winkelman, Jozef G.M.
AU - Krasnikova, Antonina V.
AU - Parisi, Daniele
AU - Deuss, Peter J.
AU - Picchioni, Francesco
AU - Bose, Ranjita K.
N1 - Funding Information:
The authors declare the following financial interests/personal relationships which may be considered as potential competing interests: Francesco Picchioni reports financial support was provided by Nederlandse Organisatie voor Wetenschappelijk Onderzoek Utrecht.We are thankful for the financial support from the Nederlandse Organisatie voor Wetenschappelijk Onderzoek (NWO, Dutch Research Council) NWO grant number 731.015.418.
Publisher Copyright:
© 2023 The Authors
PY - 2023/5/2
Y1 - 2023/5/2
N2 - The furan-maleimide Diels-Alder chemistry has emerged as an important tool to design thermo-reversible click networks. This not only preserves the strong and robust properties of thermo-sets and rubbers, but also makes it possible to cleave crosslinks at non-degradative temperatures, or in other words to recycle them. In this work a new reaction is reported in furan-maleimide click networks, which is the Double-Diels-Alder reaction (DDA), also known as domino Diels-Alder. This forms extra linkages between Diels-Alder adducts and non-reacted furan groups and evidently leads to stronger materials, but also prevents efficient thermal (re)cycling. This work shows with nuclear magnetic resonance (NMR) characterization, differential scanning calorimetry (DSC) and rheology that the DDA reaction can occur both in intramolecular and intermolecular fashion, but also that it exhibits reversibility just like the regular Diels-Alder reaction. This reaction can be easily overlooked creating what at first sight might be inexplicable reactivity when analyzing the properties of furan-maleimide click networks.
AB - The furan-maleimide Diels-Alder chemistry has emerged as an important tool to design thermo-reversible click networks. This not only preserves the strong and robust properties of thermo-sets and rubbers, but also makes it possible to cleave crosslinks at non-degradative temperatures, or in other words to recycle them. In this work a new reaction is reported in furan-maleimide click networks, which is the Double-Diels-Alder reaction (DDA), also known as domino Diels-Alder. This forms extra linkages between Diels-Alder adducts and non-reacted furan groups and evidently leads to stronger materials, but also prevents efficient thermal (re)cycling. This work shows with nuclear magnetic resonance (NMR) characterization, differential scanning calorimetry (DSC) and rheology that the DDA reaction can occur both in intramolecular and intermolecular fashion, but also that it exhibits reversibility just like the regular Diels-Alder reaction. This reaction can be easily overlooked creating what at first sight might be inexplicable reactivity when analyzing the properties of furan-maleimide click networks.
KW - Click networks
KW - Diels-Alder
KW - Domino adducts
KW - Reversibility
UR - http://www.scopus.com/inward/record.url?scp=85151791500&partnerID=8YFLogxK
U2 - 10.1016/j.polymer.2023.125884
DO - 10.1016/j.polymer.2023.125884
M3 - Article
AN - SCOPUS:85151791500
SN - 0032-3861
VL - 274
JO - Polymer
JF - Polymer
M1 - 125884
ER -