[en] Modern-day thermosetting polymers should be designed with circular economy principles in mind, considering both their recyclability and end-of-life options. Covalent adaptable networks (CANs) have the potential to address the environmental challenges we face today as, in spite of being thermosets, they can be reprocessed by conventional thermoprocessing methods and are thus recyclable. While in the last years intensive efforts have been devoted to the preparation of CANs using sustainable sources, less attention has been paid to their end-of-life options in case they escape from plastic sorting. Herein, we report the development of a new type of dynamic bond, the N,O-acetal bond based on the coupling between CO2-based oxazolidone moieties and abundant, potentially biobased polyols. Computational and kinetic studies revealed that this bond underwent rapid dissociative exchange and, crucially, was also susceptible to hydrolytic degradation. We then prepared a range of thermoset materials endowed by double end-of-life features, i.e., CAN behavior and hydrolytic degradation. This was achieved by radical thiol-ene photo-cross-linking of a diallyl monomer bearing the N,O-acetal moiety with another alkene-functionalized monomer that did not bear this dynamic bond. CANs with tunable mechanical properties and hydrolytic degradation features were easily obtained by modulating the monomer compositions. The fast-photocuring of the N,O-functionalized monomer was then exploited for producing three-dimensional (3D) printed objects, offering the potential for on-demand hydrolytic behavior.
Research Center/Unit :
CESAM - Complex and Entangled Systems from Atoms to Materials - ULiège [BE] CERM - Center for Education and Research on Macromolecules - ULiège [BE]
Disciplines :
Materials science & engineering Chemistry
Author, co-author :
Caliari, Marco ; University of Liège [ULiège] - Complex and Entangled Systems from Atoms to Materials [CESAM] Research Unit - Center for Education and Research on Macromolecules [CERM] - Belgium ; University of the Basque Country - POLYMAT - Department of Polymers and Advanced Materials: Physics Chemistry and Technology - Donostia/SanSebastian - Spain
Teotonico, Jacopo; University of the Basque Country - POLYMAT - Department of Polymers and Advanced Materials: Physics Chemistry and Technology - Donostia/SanSebastian - Spain
Irigoyen, Mikel; POLYMAT and Department of Polymers and Advanced Materials: Physics, Chemistry and Technology, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel de Lardizábal, 3, 20018 Donostia-San Sebastián, Spain
Mujika, Anje; University of the Basque Country - POLYMAT - Department of Polymers and Advanced Materials: Physics Chemistry and Technology - Donostia/SanSebastian - Spain
Isolabella, Tommaso; University of Genoa & INFN - Physics Department - Italy
Mantione, Daniele; University of the Basque Country - POLYMAT - Department of Polymers and Advanced Materials: Physics Chemistry and Technology - Donostia/SanSebastian - Spain ; IKERBASQUE Basque Foundation for Science - Bilbao - Spain
Irusta, Lourdes ; University of the Basque Country - POLYMAT - Department of Polymers and Advanced Materials: Physics Chemistry and Technology - Donostia/SanSebastian - Spain
Grignard, Bruno ; University of Liège [ULiège] - Complex and Entangled Systems from Atoms to Materials [CESAM] Research Unit - Center for Education and Research on Macromolecules [CERM] - Belgium ; University of Liège [ULiège] - FRITCO2T Platform - Belgium
Vidal, Fernando ; University of the Basque Country - POLYMAT - Department of Polymers and Advanced Materials: Physics Chemistry and Technology - Donostia/SanSebastian - Spain
Detrembleur, Christophe ; University of Liège [ULiège] - Complex and Entangled Systems from Atoms to Materials [CESAM] Research Unit - Center for Education and Research on Macromolecules [CERM] - Belgium ; Walloon Excellence [ WEL] Research Institute - Wavre - Belgium
Sardon, Haritz ; University of the Basque Country - POLYMAT - Department of Polymers and Advanced Materials: Physics Chemistry and Technology - Donostia/SanSebastian - Spain
Language :
English
Title :
A material platform based on dissociative CO2-derived N,O- acetals for tunable degradation of 3D printable materials
Publication date :
20 August 2025
Journal title :
Journal of the American Chemical Society
ISSN :
0002-7863
eISSN :
1520-5126
Publisher :
American Chemical Society (ACS), United States
Volume :
147
Issue :
33
Pages :
30095–30106
Peer reviewed :
Peer Reviewed verified by ORBi
European Projects :
H2020 - 955700 - NIPU - SYNTHESIS, CHARACTERIZATION, STRUCTURE AND PROPERTIES OF NOVEL NONISOCYANATE POLYURETHANES
Funders :
F.R.S.-FNRS - Fund for Scientific Research EU - European Union
Funding text :
The authors thank for the financial support provided by the NIPU-EJD Project; this project has received funding from the European Union’s Horizon 2020 Research and Innovation Program under Marie Skłodowska−Curie Grant Agreement No. 955700. C.D. is FNRS Research Director and thanks FNRS for financial support in the frame of the CO2Switch Project under Grant T.0075.20. The authors acknowledge Grant TED2021-129852B-C22 funded by MCIU/AEI/ 10.13039/501100011033 and by the European Union NextGenerationEU/PRTR and Grant PID2022-138199NB- I00 funded by MCIU/AEI/10.13039/501100011033. D.M. thanks Ayuda RYC2021-031668-I funded by MCIN/AEI/ 10.13039/501100011033 and by EU NextGenerationEU/ PRTR.
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