Functionalization of polyisoprene and polystyrene via reactive processing using azidoformate grafting agents, and its application to the synthesis of dioxaborolane-based polyisoprene vitrimers
Literature Information
Antoine Breuillac, Florent Caffy, Thomas Vialon, Renaud Nicolaÿ
Vitrimers incorporating dioxaborolane covalent links are permanent polymeric networks that combine the processability of thermoplastics with the thermomechanical and chemical resistance of thermosets. Transforming existing polymers into vitrimers via melt processing, a green and economical process, is a significant challenge that would greatly facilitate the development of these materials. In this study, we investigate the potential of azidoformate derivatives to functionalize and/or crosslink diene- and vinyl-based polymers with dioxaborolane moieties. To this aim, two functional azidoformate grafting agents were prepared, and their efficiency to functionalize polystyrene and polyisoprene via compression molding and reactive extrusion was assessed. Grafting yields superior to 50 and 75% could be obtained for polystyrene and polyisoprene, respectively. Polyisoprene was then transformed into a vitrimer by reactive extrusion, eitheir in the presence of a mono-azidoformate dioxaborolane and subsequent crosslinking with a bis-dioxaborolane, or in a single step using a bis-azidoformate dioxaborolane crosslinker. In particular, the latter appraoch allowed preparation of vitrimers that relax stress at elevated temperatures, show excellent creep resistance at room temperature and present good mechanical properties. While highly insoluble in THF, these vitrimers could be entirely de-crosslinked by selective diolysis of the dynamic dioxaborolane crosslinks, opening a simple and efficient route to chemical recycling of polyisoprene elastomers. The mechanical recycling of these vitrimers was also investigated over multiple cycles. Polyisoprene vitrimers could be efficiently recycled once, but their mechanical properties significantly dropped after the first recycling cycle, due to the oxidative degradation of the polyisoprene chains during reprocessing.
Recommended Journals
Related Literature
Disequilibrium effects in metal speciation by capillary electrophoresisinductively coupled plasma mass spectrometry (CE-ICP-MS); theory, simulations and experiments
Jeroen E. Sonke, Vincent J. M. Salters
DOI: 10.1039/B407162J
Activating lattice oxygen of single-layer ZnO for the catalytic oxidation reaction
Le Lin, Hao Wu, Rentao Mu, Qiang Fu
DOI: 10.1039/D3CP02580B
Recent advances in encapsulation of highly stable perovskite nanocrystals and their potential applications in optoelectronic devices
Zhengwei Cao, Feng Zhang, Jiaqi Liu, Cuihe Fan, Yukun Wu, Yuying Hao
DOI: 10.1039/D3CP00941F
The impact of intramolecular polydispersity on the self-assembly of ABn miktoarm star copolymers
Jiahao Shi, Xianbo Huang, Weihua Li
DOI: 10.1039/D3CP00994G
Calcium selective test strip for water and milk
L. F. Capitán-Vallvey, M. D. Fernández-Ramos, P. Álvarez de Cienfuegos Gálvez, F. Santoyo-González
DOI: 10.1039/B403231D
Immobilization of individual cells by local photo-polymerization on a chip
Hisataka Maruyama, Fumihito Arai, Toshio Fukuda, Tohoru Katsuragi
DOI: 10.1039/B415400M
Immunoassay for B. globigii spores as a model for detecting B. anthracis spores in finished water
Svetlana Farrell, H. Brian Halsall, William R. Heineman
DOI: 10.1039/B413652G
Optical calcium sensors: development of a generic method for their introduction to the cell using conjugated cell penetrating peptides
Abigail Webster, Steven J. Compton, Jonathan W. Aylott
DOI: 10.1039/B413725F
Screening of specific antigens for SARS clinical diagnosis using a protein microarray
Dan-Dan Lu, Su-Hong Chen, Shi-Meng Zhang, Min-Li Zhang, Wei Zhang, Xiao-Chen Bo, Sheng-Qi Wang
DOI: 10.1039/B415888A
Mechanistic insights for regulating the site occupancy, valence states and optical transitions of Mn ions in yttrium–aluminum garnets via codoping
Chong-Geng Ma
DOI: 10.1039/D3CP01548C
You might also like
What are the main uses of 1H-Indazole-6-carbonitrile (CAS: 141290-59-7)?
1H-Indazole-6-carbonitrile finds applications in pharmaceuticals, where it serve...
How should waste containing Dioctyl (2E)-2-butenedioate (CAS: 2997-85-5) be handled?
Waste containing Dioctyl (2E)-2-butenedioate (CAS: 2997-85-5) should be collecte...
What industries use Sodium [(1,2-benzoxazol-3-ylmethyl)sulfonyl]azanide (CAS: 68291-98-5)?
Sodium [(1,2-benzoxazol-3-ylmethyl)sulfonyl]azanide is primarily used in pharmac...
Are there alternatives to Dimethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,6-pyridinedicarboxylate (CAS: 741709-66-0) in synthesis?
Dimethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,6-pyridinedicarboxyla...
How should waste containing 2-Fluoro-6-hydrazinopyridine (CAS: 80714-39-2) be handled?
Waste containing 2-Fluoro-6-hydrazinopyridine (CAS: 80714-39-2) should be manage...
What is 6-Formyl-2-pyridinecarboxylic acid (CAS: 499214-11-8)?
6-Formyl-2-pyridinecarboxylic acid is an organic compound with the molecular for...
What is the market or research trend for 3-(3,4-dimethoxyphenyl)-2,5-dimethyl-N-(2-morpholin-4-ylethyl)pyrazolo[1,5-a]pyrimidin-7-amine (CAS: 900874-91-1)?
Research trends for this compound indicate a focus on its potential applications...
How is 9H-Tribenzo[b,d,f]azepine (CAS: 29875-73-8) typically synthesized?
9H-Tribenzo[b,d,f]azepine is typically synthesized via a multi-step process invo...
How is 1-Cyclopropyl-7-ethoxy-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid (CAS: 1797982-51-4) typically synthesized?
1-Cyclopropyl-7-ethoxy-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxyli...
How should waste containing Methyl 3-oxo-1,2,3,4-tetrahydro-6-quinoxalinecarboxylate (CAS: 671820-52-3) be handled?
Waste containing Methyl 3-oxo-1,2,3,4-tetrahydro-6-quinoxalinecarboxylate (CAS: ...
Source Journal
Polymer Chemistry

Polymer Chemistry welcomes submissions in all areas of polymer science that have a strong focus on macromolecular chemistry. Manuscripts may cover a broad range of fields, yet no direct application focus is required.














