Abstract
We report the synthesis of networked polymers based on the radical ring-opening polymerization of vinyloxiranes. First, the radical ring-opening polymerization of monofunctional 2-phenyl-3-vinyloxirane was investigated. Then, we synthesized di- and trifunctional vinyloxiranes and examined the networked polymer synthesis via the radical ring-opening homopolymerization or copolymerization of these monomers. The obtained networked polymers contained vinyl ether structures in the main chain, which was confirmed by infrared analysis. In addition, we examined the radical ring-opening copolymerization of difunctional vinyloxirane and monofunctional vinyloxirane or adamantane-substituted vinylcyclopropane. Thermal gravimetric analysis revealed that the network formation increased their thermal stabilities.
Similar content being viewed by others
Log in or create a free account to read this content
Gain free access to this article, as well as selected content from this journal and more on nature.com
or
References
Endo, T. Possibility to avoid shrinkage during polymerization—synthesis of monomers that expand on polymerization. Kobunshi 27, 108–111 (1978).
Errede, L. A. The chemistry of xylylenes. X. Some polymers and telomers of spiro-di-o-xylylene. J. Polym. Sci. 49, 253 (1961).
Cho, I. & Ahn, K. D. Polymerizations of substituted cyclopropanes. I. Radical polymerization of 1,1-disubstituted 2-vinylcyclopropanes. J. Polym. Sci. Polym. Chem. Ed 17, 3169 (1979).
Endo, T. & Bailey, W. J. Free radical ring-opening polymerization. J. Polym. Sci. Polym. Chem. Ed 13, 2525 (1975).
Bailey, W. J., Ni, Z. & Wu, S. R. Synthesis of poly-ε-caprolactone via a free radical mechanism. Free radical ring-opening polymerization of 2-methylene-1,3-dioxepane. Macromolecules 15, 711 (1982).
Bailey, W. J., Wu, S. R. & Ni, Z. Synthesis and free radical ring-opening polymerization of 2-methylene-4-phenyl-1,3-dioxolane. Macromol. Chem. 183, 1913 (1982).
Endo, T., Okawara, M., Bailey, W. J., Azuma, K., Nate, K. & Yokono, H. Photoinitiated ring-opening polymerization of 2-methylene-1,3-dioxepane. J. Polym. Sci. Polym. Lett. Ed 21, 373 (1983).
Cho, I. & Kim, J. B. Exploratory ring-opening polymerization. VIII. Radical ring-opening polymerization of 2-phenyl-3-vinyloxirane: a C-C bond scission polymerization of the epoxide ring. J. Polym. Sci. Polym. Lett. Ed 21, 433–436 (1983).
Endo, T. & Kanda, N. Syntheses of 2-phenyl-3-vinyloxirane derivatives that undergo radical ring-opening polymerization. J. Polym. Sci. Polym. Chem. Ed. 23, 1931–1938 (1985).
Koizumi, T., Moriya, O., Urata, Y., Nojima, Y. & Endo, T. Radical ring-opening polymerization behavior of halogenated phenyl-3-vinyloxiranes. J. Polym. Sci. A Polym. Chem. 31, 3489–3492 (1993).
Sugiyama, J., Kayamori, N. & Shimada, S. Free radical ring-opening polymerization of 1,1-Bis[(1-adamantyloxy)carbonyl]-2-vinylcyclopropane. Macromolecules 29, 1943–1950 (1996).
Castaldi, M. P., Gibson, S. E., Rudd, M. & White, A. J. P. A new approach to enantiopure C3-symmetric molecules. Chem. Eur. J 12, 138–148 (2006).
Pandey, P., Katsoulidis, A. P., Eryazici, I., Wu, Y., Kanatzidis, M. G. & Nguyen, S. T. Imine-linked microporous polymer organic frameworks. Chem. Mater. 22, 4974–4979 (2010).
Chiba, H., Kitazume, K., Yamada, S. & Endo, T. Synthesis and radical polymerization of adamantane-containing bifunctional vinylcyclopropane undergoing volume expansion on polymerization. J. Polym. Sci. A Polym. Chem 54, 39–43 (2016).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Competing interests
The authors declare no conflict of interest.
Rights and permissions
About this article
Cite this article
Maeda, S., Matsumoto, K. & Endo, T. Design of networked polymers based on radical ring-opening polymerization of vinyloxiranes. Polym J 49, 363–368 (2017). https://doi.org/10.1038/pj.2016.125
Received:
Revised:
Accepted:
Published:
Issue date:
DOI: https://doi.org/10.1038/pj.2016.125
This article is cited by
-
Methods and applications for epoxide C–C bond cleavage reactions
Nature Reviews Chemistry (2025)


