Cyclic Ketene Acetal Monomer Useful for the Development of Degradable Polymers

Cyclic ketene acetals (CKAs), such as 2-methylene-1,3-dioxepane (MDO), are monomers that can yield polyesters through radical ring-opening polymerization (rROP). Due to their ability to copolymerize with a broad range of vinyl monomers, CKAs have gained interest as a strategy to introduce highly degradable ester linkages into vinyl polymers. ^1,2) Consequently, CKAs are expected to play a key role in developing polymers for biomedical applications, including therapeutic materials, as well as for addressing the issue of environmental accumulation of plastic waste. In the rROPs of CKAs, ring-retaining reactions can compete with rROP, but MDO is known to exhibit a high ring-opening efficiency due to its larger ring size. ³⁾

Related Products

M3746

2-Methylene-1,3-dioxepane

D6519

Dibenzo[c,e]oxepine-5(7H)-thione

O0714

Oxepane-2-thione

References

• 1) 100th Anniversary of Macromolecular Science Viewpoint: Degradable Polymers from Radical Ring-Opening Polymerization: Latest Advances, New Directions, and Ongoing Challenges
  • T. Pesenti, J. Nicolas, ACS Macro Lett. 2020, 9, 1812.
• 2) Current Standing on Radical Ring-Opening Polymerizations of Cyclic Ketene Acetals as Homopolymers and Copolymers with One Another
  • Y. Deng, F. Mehner, J. Gaitzsch, Macromol. Rapid Commun. 2023, 44, 2200941.
• 3) Synthesis of Poly-ϵ-caprolactone via a Free Radical Mechanism. Free Radical Ring-Opening Polymerization of 2-Methylene-1,3-dioxepane
  • W. J. Bailey, Z. Ni, S.-R. Wu, J. Polym. Sci. Polym. Chem. Ed. 1982, 20, 3021.

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