Although polymerization of traditional vinyl monomers proceeds by chain addition with the creation of carbon-carbon bonds, some cyclic monomers bearing vinyl or exomethylene groups can be polymerized by a radical pathway through a ring-opening mechanism. Radical ring-opening polymerization (rROP) thus combines the advantages of both ring-opening polymerization and radical polymerization, that is the production of polymers having heteroatom and/or functional groups in the main chain together with the robustness, the ease of use and the mild polymerization conditions of a radical process. Cyclic ketene acetals (CKA) were reported by Bailey and coworkers in the 80s as suitable monomers for rROP. This monomer family was then extensively studied as a way to produce similar polymers to classic aliphatic polyesters, but through a radical pathway. This technique has been recently rejuvenated by the possibility to copolymerize CKA with classic vinyl monomers, leading to cleavable functions into the copolymer backbone. This led to a broad range of novel (bio)degradable materials suitable for a large scope of applications. We aim at using some biomass-based diols to prepare cyclic ketene acetal monomers that have the advantage to be polymerized by a radical mechanism. This will lead to new materials and it is also possible to copolymerize CKA with traditional vinyl monomers to introduce degradable biomass-based repeat units onto traditional polymer backbone. In both cases, this approach will decrease the petrochemical based monomer ratio. The introduction of a reasonable amount of biomass-based compound in many polymer matrixes aims at keeping the original properties of many materials but while decreasing their carbon footprint.

Degradable materials by the radical polymerization of cyclic ketene acetals

2019 Spring National Meeting

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