Cited by 31Advanced Polymer Synthesis and Characterizationbiodegradable polymer synthesis and propertiesPhotopolymerization techniques and applications

Mapping the characteristics of the radical ring‐opening polymerization of a cyclic ketene acetal towards the creation of a functionalized polyester

Plikk, Peter, Tyson, Therese, Finne‐Wistrand, Anna, Albertsson, Ann‐Christine·2009·Journal of Polymer Science Part A: Polymer Chemistry

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

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Crossref · 10.1002/pola.23511

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  • 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]

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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

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