title: Proton-transfer polymerization (HTP): converting methacrylates to polyesters by an N-heterocyclic carbene.
abstract: A new polymerization termed proton (H)-transfer polymerization (HTP) has been developed to convert dimethacrylates to unsaturated polyesters. HTP is catalyzed by a selective N-heterocyclic carbene capable of promoting intermolecular Umpolung condensation through proton transfer and proceeds through the step-growth propagation cycles via enamine intermediates. The role of the added suitable phenol, which is critical for achieving an effective HTP, is twofold: shutting down the radically induced chain-growth addition polymerization under HTP conditions (typically at 80-120 °C) and facilitating proton transfer after each monomer enchainment. The resulting unsaturated polyesters have a high thermal stability and can be readily cross-linked to robust polyester materials.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, CO 80523-1872 (USA).
authors.forename: Miao
authors.initials: M
authors.lastname: Hong
authors.forename: Eugene Y-X
authors.initials: EY
authors.lastname: Chen
mesh_terms: D002384:Catalysis; D008689:Methacrylates / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D011091:Polyesters / Q000737:chemistry*; D058105:Polymerization; D011522:Protons
chemical_list: D008689:Methacrylates; D011091:Polyesters; D011522:Protons; C030011:carbene; D008697:Methane
keywords: N-heterocyclic carbenes; organocatalysis; polyesters; polymerization; polymers