Mapping the characteristics of the radical ring‐opening polymerization of a cyclic ketene acetal towards the creation of a functionalized polyester
Abstract
Abstract Radical ring‐opening polymerization of cyclic ketene acetals is a means to achieve novel types of aliphatic polyesters. 2‐methylene‐1,3‐dioxe‐5‐pene is a seven‐membered cyclic ketene acetal containing an unsaturation in the 5‐position in the ring structure. The double bond functionality enables further reactions subsequent to polymerization. The monomer 2‐methylene‐1,3‐dioxe‐5‐pene was synthesized and polymerized in bulk by free radical polymerization at different temperatures, to determine the structure of the products and propose a reaction mechanism. The reaction mechanism is dependent on the reaction temperature. At higher temperatures, ring‐opening takes place to a great extent followed by a new cyclization process to form the stable five‐membered cyclic ester 3‐vinyl‐1,4‐butyrolactone as the main reaction product. Thereby, propagation is suppressed and only small amounts of other oligomeric products are formed. At lower temperatures, the cyclic ester formation is reduced and oligomeric products containing both ring‐opened and ring‐retained repeating units are produced at higher yield. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 4587–4601, 2009
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
Increasing interest in biodegradable polyesters and the versatility of RROP with respect to structures accessible via different monomers and their copolymerization with conventional vinyl monomers has changed the situation significantly.
“However, with the increasing interest in biodegradable polyesters and the versatility of RROP with respect to the structures accessible via very different monomers [25] and their copolymerization with conventional vinyl monomers [26 -34] has changed the situation significantly.”
From Ring-Opening Polymerization—An Introductory Review (2013) · cites this paper as [34]
Cites
Bailey, W. J., Ni, Z., & Wu, S. (1982) · Journal of Polymer Science Polymer Chemistry Edition · doi:10.1002/pol.1982.170201101 · Cited by 259 · see citing works
Weimer, M. W., Fr�chet, J. M. J., & Gitsov, I. (1998) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/(sici)1099-0518(19980430)36:6 · Cited by 222 · see citing works
Numata, K., Srivastava, R. K., Finne‐Wistrand, A., Albertsson, A., Doi, Y., & Abe, H. (2007) · Biomacromolecules · doi:10.1021/bm700537x · Cited by 133 · see citing works
Self-citationJin, S. Z., & Gonsalves, K. E. (1997) · Macromolecules · doi:10.1021/ma961590h · Cited by 114 · see citing works
Roberts, G. E., Coote, M. L., Heuts, J. P. A., Morris, L. M., & Davis, T. P. (1999) · Macromolecules · doi:10.1021/ma9813587 · Cited by 107 · see citing works
Free Radical Ring-Opening Polymerization
Bailey, W. J. (1985) · Polymer Journal · doi:10.1295/polymj.17.85 · Cited by 104 · see citing works
Jin, S. Z., & Gonsalves, K. E. (1998) · Macromolecules · doi:10.1021/ma9707289 · Cited by 101 · see citing works
Synthesis and Characterization of Copolymers of 5,6-Benzo-2-methylene-1,3-dioxepane and Styrene
Wickel, H., & Agarwal, S. (2003) · Macromolecules · doi:10.1021/ma034551w · Cited by 97 · see citing works
Wickel, H., Agarwal, S., & Greiner, A. (2003) · Macromolecules · doi:10.1021/ma025983u · Cited by 88 · see citing works
Synthesis and enzymatic degradation of 2‐methylene‐1,3‐dioxepane and methyl acrylate copolymers
Sun, L., Zhuo, R. ‐., & Liu, Z. (2003) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.10868 · Cited by 77 · see citing works
Detrembleur, C., Mazza, M., Lou, X., Halleux, O., Lecomte, P., Mecerreyes, D., Hedrick, J. L., & Jérôme, R. (2000) · Macromolecules · doi:10.1021/ma000488o · Cited by 73 · see citing works
Yuan, J.-Y., Pan, C.-Y., & Tang, B. Z. (2001) · Macromolecules · doi:10.1021/ma0004099 · Cited by 68 · see citing works
Ryner, M., Finne‐Wistrand, A., Albertsson, A., & Kricheldorf, H. R. (2001) · Macromolecules · doi:10.1021/ma0106898 · Cited by 64 · see citing works
Self-citationSrivastava, R. K., & Albertsson, A. (2005) · Macromolecules · doi:10.1021/ma0518508 · Cited by 64 · see citing works
Self-citationStudies on the Synthesis and Properties of Temperature Responsive and Biodegradable Hydrogels
Sun, L., Zhuo, R., & Liu, Z. (2003) · Macromolecular Bioscience · doi:10.1002/mabi.200300012 · Cited by 58 · see citing works
Highly Stereoselective Radical Cyclization of Haloacetals Controlled by the Acetal Center
Villar, F., Kolly‐Kovac, T., Equey, O., & Renaud, P. (2003) · Chemistry - A European Journal · doi:10.1002/chem.200390180 · Cited by 55 · see citing works
Klemm, E., & Schulze, T. G. (1999) · Acta Polymerica · doi:10.1002/(sici)1521-4044(19990101)50:1 · Cited by 52 · see citing works
He, T., Zou, Y.-F., & Pan, C.-Y. (2002) · Polymer Journal · doi:10.1295/polymj.34.138 · Cited by 47 · see citing works
Kobatake, S., & Yamada, B. (1996) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/(sici)1099-0518(19960115)34:1 · Cited by 43 · see citing works
Potential tissue implants from the networks based on 1,5-dioxepan-2-one and ε-caprolactone
Andronova, N., Srivastava, R. K., & Albertsson, A. (2005) · Polymer · doi:10.1016/j.polymer.2005.06.038 · Cited by 42 · see citing works
Self-citationFinne, A., & Albertsson, A. (2003) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.10682 · Cited by 38 · see citing works
Self-citationOdelius, K., & Albertsson, A. (2007) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.22466 · Cited by 37 · see citing works
Self-citationYuan, J., & Pan, C. (2002) · European Polymer Journal · doi:10.1016/s0014-3057(02)00023-x · Cited by 36 · see citing works
Wei, Y., CONNORS, E. J., Jia, X., & Wang, B. (1996) · Chemistry of Materials · doi:10.1021/cm950487o · Cited by 35 · see citing works
A new elimination with phase-transfer catalysis for cyclic ketene acetals
Bailey, W. J., & Zhou, L. (1991) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)74266-3 · Cited by 32 · see citing works
Star‐shaped and photocrosslinked poly(1,5‐dioxepan‐2‐one): Synthesis and characterization
Ryner, M., Valdre, A., & Albertsson, A. (2002) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.10304 · Cited by 29 · see citing works
Self-citationAn assessment of the copolymerization reaction between styrene and 2-methylene-1,3-dioxepane
Morris, L. M., Davis, T. P., & Chaplin, R. P. (2001) · Polymer · doi:10.1016/s0032-3861(00)00336-0 · Cited by 28 · see citing works
New functionalized polyesters to achieve controlled architectures
Finne‐Wistrand, A., & Albertsson, A. (2003) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.10805 · Cited by 28 · see citing works
Self-citationAlternating polyester/fluoroalkene copolymers: Combining high hydrophobicity with degradability
Borkar, S., Sen, A., & Shallenberger, J. R. (2005) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.21212 · Cited by 22 · see citing works
Choi, S., Lee, K., Kwon, S., & Kim, H. (2006) · The Journal of Supercritical Fluids · doi:10.1016/j.supflu.2005.11.023 · Cited by 22 · see citing works
Odelius, K., Finne‐Wistrand, A., & Albertsson, A. (2005) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.21192 · Cited by 22 · see citing works
Self-citationSynthesis and biodegradability evaluation of 2‐methylene‐1,3‐dioxepane and styrene copolymers
Xu, J. F., Liu, Z., & Zhuo, R. (2006) · Journal of Applied Polymer Science · doi:10.1002/app.25321 · Cited by 19 · see citing works
Zhu, P. C., Wu, Z., & Pittman, C. U. (1997) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/(sici)1099-0518(199702)35:3 · Cited by 15 · see citing works
Synthesis of poly(3‐vinyl‐1,4‐butyrolactone‐co‐acrylonitrile)
Shimidzu, T., Yoshikawa, M., Chiba, H., & Murakami, A. (1977) · Die Makromolekulare Chemie · doi:10.1002/macp.1977.021780706 · Cited by 10 · see citing works
Synthesis, isomerization, and polymerization of mixed phosphoranimines
White, M. L., & Matyjaszewski, K. A. (1996) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/(sici)1099-0518(19960130)34:2 · Cited by 9 · see citing works
Cationic 1,2-vinyl addition polymerization of cyclic ketene acetals initiated by conventional acids
Liu, Y., Keller, C. E., & Pittman, C. U. (1997) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/(sici)1099-0518(199712)35:17 · Cited by 8 · see citing works
Controlled free radical ring-opening polymerization and chain extension of the living polymer
Wei, Y., Connors, E. J., Jia, X., & Wang, C. (1998) · Journal of Polymer Science Part A: Polymer Chemistry · doi:10.1002/(sici)1099-0518(19980415)36:5
Flagged first, then by citations
1 of the 38 references couldn’t be matched to a known paper.
Cited by
Sorted by citations
Tardy, A., Nicolas, J., Gigmes, D., Lefay, C., & Guillaneuf, Y. (2017) · Chemical Reviews · doi:10.1021/acs.chemrev.6b00319 · Cited by 469 · see citing works
Ring-Opening Polymerization—An Introductory Review
Nuyken, O., & Pask, S. (2013) · Polymers · doi:10.3390/polym5020361 · Cited by 456 · see citing works
Agarwal, S. (2010) · Polymer Chemistry · doi:10.1039/c0py00040j · Cited by 263 · see citing works
Undin, J., Illanes, T., Finne-Wistrand, A., & Albertsson, A.-C. (2012) · Polymer Chemistry · doi:10.1039/c2py20034a · Cited by 97 · see citing works
Self-citationHedir, G. G., Bell, C. A., O’Reilly, R. K., & Dove, A. P. (2015) · Biomacromolecules · doi:10.1021/acs.biomac.5b00476 · Cited by 95 · see citing works
Undin, J., Finne‐Wistrand, A., & Albertsson, A. (2013) · Biomacromolecules · doi:10.1021/bm4004783 · Cited by 71 · see citing works
Self-citationControlling the synthesis of degradable vinyl polymers by xanthate-mediated polymerization
Bell, C. A., Hedir, G. G., O’Reilly, R. K., & Dove, A. P. (2015) · Polymer Chemistry · doi:10.1039/c5py01156f · Cited by 70 · see citing works
Guo, B., Finne‐Wistrand, A., & Albertsson, A. (2011) · Macromolecules · doi:10.1021/ma2009595 · Cited by 62 · see citing works
Self-citationInhibition of Marine Biofouling by Use of Degradable and Hydrolyzable Silyl Acrylate Copolymer
Zhou, X. C., Xie, Q., Ma, C., Chen, Z., & Zhang, G. (2015) · Industrial & Engineering Chemistry Research · doi:10.1021/acs.iecr.5b01819 · Cited by 55 · see citing works
Tardy, A., Honore, J., Siri, D., Nicolas, J., Gigmès, D., Lefay, C., & Guillaneuf, Y. (2017) · Polymer Chemistry · doi:10.1039/c7py00337d · Cited by 52 · see citing works
Undin, J., Finne‐Wistrand, A., & Albertsson, A. (2014) · Biomacromolecules · doi:10.1021/bm500689g · Cited by 50 · see citing works
Self-citationDing, D., Pan, X., Zhang, Z., Li, N., Zhu, J., & Zhu, X. (2016) · Polymer Chemistry · doi:10.1039/c6py01061j · Cited by 47 · see citing works
Undin, J., Plikk, P., Finne‐Wistrand, A., & Albertsson, A. (2010) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.24292 · Cited by 42 · see citing works
Self-citationSynthesis and Characterization of Backbone Degradable Azlactone-Functionalized Polymers
Carter, M. C. D., Jennings, J., Appadoo, V., & Lynn, D. M. (2016) · Macromolecules · doi:10.1021/acs.macromol.6b01212 · Cited by 40 · see citing works
Functional Degradable Polymers via Radical Ring‐Opening Polymerization and Click Chemistry
Maji, S., Zheng, M., & Agarwal, S. (2011) · Macromolecular Chemistry and Physics · doi:10.1002/macp.201100375 · Cited by 39 · see citing works
Synthesis of Rapidly Surface Eroding Polyorthoesters and Polyacetals Using Thiol–ene Click Chemistry
Herwig, G., & Dove, A. P. (2019) · ACS Macro Letters · doi:10.1021/acsmacrolett.9b00463 · Cited by 26 · see citing works
Ai, X., Pan, J., Xie, Q., Ma, C., & Zhang, G. (2021) · Polymer Chemistry · doi:10.1039/d1py00810b · Cited by 22 · see citing works
Herwig, G., Pérez‐Madrigal, M. M., & Dove, A. P. (2021) · Biomacromolecules · doi:10.1021/acs.biomac.0c01668 · Cited by 21 · see citing works
Radical Ring Opening Polymerization of Cyclic Ketene Acetals Derived From d -Glucal
Hardy, C., Levere, M. E., Kociok-Köhn, G. I., & Buchard, A. (2023) · ACS Macro Letters · doi:10.1021/acsmacrolett.3c00397 · Cited by 18 · see citing works
Endo, T., & Sudo, A. (2015) · ACS symposium series · doi:10.1021/bk-2015-1187.ch002 · Cited by 18 · see citing works
Kertsomboon, T., Agarwal, S., & Chirachanchai, S. (2020) · Macromolecular Rapid Communications · doi:10.1002/marc.202000243 · Cited by 18 · see citing works
Balaji, A., Bell, C. A., Houston, Z. H., Bridle, K. R., Genz, B., Fletcher, N. L., Ramm, G. A., & Thurecht, K. J. (2023) · Biomaterials · doi:10.1016/j.biomaterials.2023.122318 · Cited by 15 · see citing works
Functional and Highly Porous Scaffolds for Biomedical Applications
Tyson, T., Målberg, S., Wåtz, V., Finne‐Wistrand, A., & Albertsson, A. (2011) · Macromolecular Bioscience · doi:10.1002/mabi.201100166 · Cited by 12 · see citing works
Self-citationNúñez, B. B., Guillaneuf, Y., Grande, D., Carbonnier, B., & Droumaguet, B. L. (2024) · Polymer · doi:10.1016/j.polymer.2024.127332 · Cited by 8 · see citing works
Hiraguri, Y., & Aiba, S. (2014) · Journal of Macromolecular Science Part A · doi:10.1080/10601325.2014.916180 · Cited by 7 · see citing works
Núñez, B. B., Carbonnier, B., Grande, D., & Droumaguet, B. L. (2025) · Reactive and Functional Polymers · doi:10.1016/j.reactfunctpolym.2025.106284 · Cited by 3 · see citing works
Kinetic Features of Radical Ring-Opening Polymerization of Ketene Acetals
Zaremski, M. Y., & Aliev, E. E. (2024) · Polymer Science Series B · doi:10.1134/s156009042460147x · Cited by 3 · see citing works
Illanes, T. (2011) · KTH Publication Database DiVA (KTH Royal Institute of Technology) · Cited by 2 · see citing works
Кинетические особенности радикальной полимеризации кетенацеталей с раскрытием цикла
Заремский, М. Ю., & Aliev, E. E. (2024) · Высокомолекулярные соединения С · doi:10.31857/s2308114724020019
Deng, Y., Mehner, F., & Gaitzsch, J. (2026) · Elsevier eBooks · doi:10.1016/b978-0-323-95486-0.00202-7
- Authors
- Plikk, P., Tyson, T., Finne‐Wistrand, A., & Albertsson, A.
- Affiliations
- KTH Royal Institute of Technology (SE)
- Corresponding author
- Albertsson, Ann‐Christine
- Venue
- Journal of Polymer Science Part A: Polymer Chemistry
- Publisher
- Wiley
- Published
- 2009-08-04
- Volume
- 47
- Issue
- 18
- Pages
- 4587-4601
- ISSN
- 0887-624X (ISSN-L)
- 1099-0518
- OpenAlex
- W2120821284
- Cited by
- 31
- References
- 38
- Citations by year
- 2026: 1 · 2025: 1 · 2024: 3 · 2023: 2 · 2021: 2 · 2020: 1 · 2019: 1 · 2017: 2 · 2016: 2 · 2015: 4 · 2014: 3 · 2013: 2 · 2012: 1
- FWCI
- 1.13
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of Polymer Science Part A Polymer Chemistry (publishedVersion)
- Funders
- Swedish Foundation for Strategic Research (A302:139)
- Swedish Research Council (2005-6082, 2008-5538)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
- Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
- Physical Sciences › Chemistry › Organic Chemistry › Photopolymerization techniques and applications
- Keywords
- radical ring-opening polymerization, cyclic ketene acetals, aliphatic polyesters, reaction mechanism, temperature dependence, cyclization, oligomeric products
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review