Oxidized dihydrocarvone as a renewable multifunctional monomer for the synthesis of shape memory polyesters.
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 M(n) 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.
Lowe
Jennifer R
JR
Department of Chemistry, University of Minnesota, 207 Pleasant Street SE, Minneapolis, Minnesota 55455-0431, USA.
Tolman
William B
WB
Hillmyer
Marc A
MA
D002208:Caproates; D000081005:Cyclohexane Monoterpenes; D007783:Lactones; D008968:Molecular Conformation; D039821:Monoterpenes / Q000737:chemistry*; D010084:Oxidation-Reduction; D018583:Pliability; D011091:Polyesters / Q000138:chemical synthesis*; D058105:Polymerization; D014001:Tin; D015032:Zinc
D002208:Caproates; D000081005:Cyclohexane Monoterpenes; D007783:Lactones; D039821:Monoterpenes; D011091:Polyesters; C419565:2-ethylhexanoic acid tin(II) salt; C121056:caprolactone; D014001:Tin; C006923:carvone; D015032:Zinc