Polyester from dimethylketene and acetaldehyde: Direct copolymerization and β-lactone ring-opening polymerization
Marc Brestaz
INSA de Rouen, Laboratoire Polymères Biopolymères Surfaces, CNRS UMR 6270 & FR 3038, avenue de l'Université, BP8, 76801 Saint-Etienne du Rouvray Cedex, France
ARKEMA, Cerdato, 27470 Serquigny, France
Search for more papers by this authorCorresponding Author
Nicolas Desilles
INSA de Rouen, Laboratoire Polymères Biopolymères Surfaces, CNRS UMR 6270 & FR 3038, avenue de l'Université, BP8, 76801 Saint-Etienne du Rouvray Cedex, France
INSA de Rouen, Laboratoire Polymères Biopolymères Surfaces, CNRS UMR 6270 & FR 3038, avenue de l'Université, BP8, 76801 Saint-Etienne du Rouvray Cedex, FranceSearch for more papers by this authorClaude Bunel
INSA de Rouen, Laboratoire Polymères Biopolymères Surfaces, CNRS UMR 6270 & FR 3038, avenue de l'Université, BP8, 76801 Saint-Etienne du Rouvray Cedex, France
Search for more papers by this authorMarc Brestaz
INSA de Rouen, Laboratoire Polymères Biopolymères Surfaces, CNRS UMR 6270 & FR 3038, avenue de l'Université, BP8, 76801 Saint-Etienne du Rouvray Cedex, France
ARKEMA, Cerdato, 27470 Serquigny, France
Search for more papers by this authorCorresponding Author
Nicolas Desilles
INSA de Rouen, Laboratoire Polymères Biopolymères Surfaces, CNRS UMR 6270 & FR 3038, avenue de l'Université, BP8, 76801 Saint-Etienne du Rouvray Cedex, France
INSA de Rouen, Laboratoire Polymères Biopolymères Surfaces, CNRS UMR 6270 & FR 3038, avenue de l'Université, BP8, 76801 Saint-Etienne du Rouvray Cedex, FranceSearch for more papers by this authorClaude Bunel
INSA de Rouen, Laboratoire Polymères Biopolymères Surfaces, CNRS UMR 6270 & FR 3038, avenue de l'Université, BP8, 76801 Saint-Etienne du Rouvray Cedex, France
Search for more papers by this authorAbstract
Two ways to obtain aliphatic polyesters (PEs) from dimethylketene and acetaldehyde were investigated. On the one hand, a direct anionic copolymerization was carried out in toluene at −60 °C. The resulting polymer was mainly composed of PE units. On the other hand, a two-step process involving the synthesis of 3,3,4-trimethyl-2-oxetanone by [2+2] cycloaddition, followed by its ring-opening polymerization, with various initiators and solvents, led to the expected PE. Molecular weights up to 9000 g mol−1 (measured by nuclear magnetic resonance (NMR)), with narrow polydispersity around 1.2, were obtained. These polymers were found stable up to 274 °C under nitrogen and a broad and complex endothermic peak attributed to crystallinity was observed near 139 °C by differential scanning calorimetry (DSC). The crystallinity, measured by X-ray diffraction, was close to 0.45. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011
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