Degradable Polystyrene via the Cleavable Comonomer Approach
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Abstract
Polystyrene (PS) is a major commodity polymer widely used in various applications ranging from packaging to insulation thanks to its low cost, high stiffness, and transparency as well as its relatively high softening temperature. Similarly to all polymers prepared by radical polymerization, PS is constituted of a C–C backbone and thus is not degradable. To confer degradability to such materials, the copolymerization of vinyl monomers with a cyclic monomer that could undergo radical ring-opening is an efficient method to introduce purposely cleavable bonds into the polymer backbone. Dibenzo[c,e]-oxepane-5-thione (DOT) is a cyclic thionolactone monomer known for its efficient copolymerization with acrylate derivatives but so far could not be incorporated into PS backbones. From a theoretical study combining density functional theory (DFT) and kinetic models using the PREDICI software, we showed that the modification of experimental conditions could overcome these limitations and that high molar mass degradable polystyrene ( M w close to 150 000 g·mol –1 ) could be prepared via statistical insertion of thioester groups into the polymer backbone. This copolymerization process is compatible with conventional free radical polymerization and reversible deactivation radical polymerization (RDRP) techniques such as nitroxide mediated polymerization (NMP). Thanks to favorable reactivity ratios allowing only a few mol % of thioester units to be randomly incorporated, there was no major modification of the thermal and mechanical properties of the PS. The degradation of such PS could be performed in tetrahydrofuran (THF) at room temperature (RT) in 1 h using 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as a base, leading to oligomers with M n close to 2000 g·mol –1 . We successfully demonstrate further applicability of these copolymerization systems for the phototriggered decomposition of PS in solution as well as the synthesis of cross-linked PS networks degradable into soluble side products.
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The rROP approach requires delicate design of the cyclic monomer to achieve high reactivity and to control the ratio of ring-opened and cyclic structures.
“However, the rROP approach requires delicate design of the cyclic monomer to achieve high reactivity and to control the ratio of ring-opened and cyclic structures.”
From Direct Radical Copolymerizations of Thioamides To Generate Vinyl Polymers with Degradable Thioether Bonds in the Backbones (2023) · cites this paper as [29]
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Self-citation
- Authors
- Gil, N., Caron, B., Siri, D., Roche, J., Hadiouch, S., Khedaioui, D., Ranque, S., Cassagne, C., Montarnal, D., Gigmes, D., Lefay, C., & Guillaneuf, Y.
- Affiliations
- Centre National de la Recherche Scientifique (FR)
- Aix-Marseille Université (FR)
- Aix Marseille Univ., CNRS, Institut de Chimie Radicalaire, UMR 7273, F-13397 Marseille, France
- Corresponding author
- Lefay, Catherine
- Guillaneuf, Yohann
- ORCID
- Venue
- Macromolecules
- Publisher
- American Chemical Society (ACS)
- Published
- 2022-07-19
- Volume
- 55
- Issue
- 15
- Pages
- 6680-6694
- ISSN
- 0024-9297 (ISSN-L)
- 1520-5835
- OpenAlex
- W4285795529
- Cited by
- 87
- References
- 62
- Citations by year
- 2026: 17 · 2025: 17 · 2024: 22 · 2023: 19 · 2022: 12
- FWCI
- 6.67
- Type
- journal article
- Language
- en
- Open access
- green
- doi.org
- Licence
- Locations
- Macromolecules (publishedVersion)
- ChemRxiv (acceptedVersion, cc-by-nc)
- HAL (submittedVersion, other-oa)
- Funders
- Agence Nationale de la Recherche (ANR-18-CE06-0014)
- Centre R?gional de Comp?tences en Mod?lisation Mol?culaire de Marseille
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
- Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
- Physical Sciences › Materials Science › Polymers and Plastics › Polymer composites and self-healing
- Keywords
- nitroxide-mediated polymerization, controlled radical polymerization, reactivity ratios, crosslinked polymer networks, density functional theory, kinetic modeling
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