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Oxygen inhibition in thiol–acrylate photopolymerizations
Abstract
The overall effects of oxygen on thiol–acrylate photopolymerizations were characterized. Specially, the choice of thiol monomer chemistry, functionality, and concentration on the extent of oxygen inhibition were considered. As thiol concentration was increased, the degree of oxygen inhibition was greatly reduced because of chain transfer from the peroxy radical to the thiol. When comparing the copolymerization of 1,6‐hexanediol diacrylate with the alkane‐based thiol (1,6‐hexane dithiol) to the copolymerization with the propionate thiol (glycol dimercaptopropionate), it was found that the propionate system was much more reactive and polymerized to a greater extent in the presence of oxygen. In addition, the functionality was considered where the glycol dimercaptopropionate was compared to a tetrafunctional propionate of similar chemistry (pentaerythritol tetrakis(mercaptopropionate)). Given the same thiol concentration, the higher functionality thiol imparted a faster polymerization rate, due to the increased polymer system viscosity, which limited oxygen diffusion and decreased the extent of overall oxygen inhibition. Thus, preliminary insight is provided into how thiol monomer choice affects the extent of oxygen inhibition in thiol–acrylate photopolymerization. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 2007–2014, 2006
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Cited by
Loessner, D., Meinert, C., Kaemmerer, E., Martine, L. C., Yue, K., Levett, P. A., Klein, T. J., Melchels, F. P. W., Khademhosseini, A., & Hutmacher, D. W. (2016) · Nature Protocols · doi:10.1038/nprot.2016.037 · Cited by 868
Strategies to Reduce Oxygen Inhibition in Photoinduced Polymerization
Ligon, S. C., Husár, B., Wutzel, H., Holman, R., & Liska, R. (2014) · Chemical Reviews · doi:10.1021/cr3005197 · Cited by 721
Photopolymerizable Biomaterials and Light-Based 3D Printing Strategies for Biomedical Applications
Yu, C., Schimelman, J., Wang, P., Miller, K. L., Ma, X., You, S., Guan, J., Sun, B., Zhu, W., & Chen, S. (2020) · Chemical Reviews · doi:10.1021/acs.chemrev.9b00810 · Cited by 579
Hoyle, C. E., & Bowman, C. N. (2010) · Angewandte Chemie · doi:10.1002/ange.200903924 · Cited by 293
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Metadata
- Authors
- O'Brien, A. K., Cramer, N. B., & Bowman, C. N.
- Venue
- Journal of Polymer Science Part A: Polymer Chemistry
- Publisher
- Wiley
- Published
- 2006-02-02
- Volume
- 44
- Issue
- 6
- Pages
- 2007-2014
- ISSN
- 0887-624X (ISSN-L)
- 1099-0518
- OpenAlex
- W2164664188
- Cited by
- 246
- References
- 0
- FWCI
- 5.58
- Type
- journal article
- Language
- en
- Open access
- closed
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- O'Brien, A. K., Cramer, N. B., & Bowman, C. N. (2006). Oxygen inhibition in thiol–acrylate photopolymerizations. Journal of Polymer Science Part A: Polymer Chemistry. https://doi.org/10.1002/pola.21304
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