For renewably sourced and sustainable polymers to replace petroleum based materials, polymer chemical diversity is required to create new polymers with different glass transition temperatures, mechanical properties, and degradation behavior, for example. Six-membered lactone monomers that are functionalized at the delta-position with a methoxy-ether linkage as a pendant group can be synthesized through the catalytic upgrading of hydroxymethylfurfural (HMF) and phenols that can be produced through woody biomass. A library of these functionalized delta-hexalactones (FDHLs) were synthesized with pendant groups that have different numbers of aromatic rings, ring fusion, and saturation. This system probed how pendant group structure affects polymerization behavior and polymer thermal properties. Ring opening polymerization was performed with 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) catalyst to generate polymers that followed typical equilibrium polymerization kinetics for ring opening polymerization. The size of the pendant group affected the required TBD catalyst loading to cause the polymerization to proceed past initiation and to propagate a polymer chain. The polymers with a phenol pendant group (poly(PDHL)) and a 2-phenylphenol pendant group (poly(2-PhPDHL)) could be polymerized to appreciable molecular weights and yielded glass transition temperatures of 6 and 40 °C, respectively.

Woody biomass derivable polyesters with selectable pendant groups

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ACS Fall 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.