Oxidized dihydrocarvone as a renewable multifunctional monomer for the synthesis of shape memory polyesters

Jennifer R. Lowe, William B. Tolman, Marc A. Hillmyer

Research output: Contribution to journalArticlepeer-review

51 Scopus citations

Abstract

The natural product dihydrocarvone, found in caraway oil, was oxidized to an epoxylactone on a multigram scale. The resulting epoxylactone was used as a multifunctional monomer and cross-linker in ring-opening polymerizations. Homopolymerization using diethylzinc and tin(II) 2-ethylhexanoate gave only low molecular weight oligomers (apparent Mn less than 2.5 kg/mol). Copolymerizations of ε-caprolactone and 0.3 to 50% of the epoxylactone gave flexible cross-linked materials on a multigram scale in a one-step synthesis. The gel fraction of these copolymers was determined. These copolymers showed near perfect shape memory properties even after repeated bending.

Original languageEnglish (US)
Pages (from-to)2003-2008
Number of pages6
JournalBiomacromolecules
Volume10
Issue number7
DOIs
StatePublished - Jul 13 2009

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