(Co)Polymerization of vinyl levulinate by cobalt-mediated radical polymerization and functionalization by ketoxime click chemistry

Imène Allaoua (1) , Beatriz Eleuterio Goi , Mona Obadia (1) , Antoine Debuigne (2) , Christophe Detrembleur (2) , Eric Drockenmuller (1)

1 IMP - Ingénierie des Matériaux Polymères
2 CERM - Centre d'Etude et de Recherche sur les Macromolécules

Vinyl levulinate is synthesized from levulinic acid by palladium-catalyzed vinyl exchange and is characterized by NMR and ESI-HRMS techniques. Homopolymerization of vinyl levulinate and random copolymerization with vinyl acetate by cobalt-mediated radical polymerization affords well-defined ketone functionalized poly(vinyl ester)s. The impact of temperature, solvent and theoretical degree of polymerization on monomer conversion and control of the polymerization is studied by H-1 NMR and size exclusion chromatography techniques. The ketoxime conjugation of O-benzylhydroxylamine with the pendant ketone functionality of poly(vinyl levulinate-co-vinyl acetate) is demonstrated.

Mots clés: POLYESTER MATERIALS; ACETATE; BIOMASS; COPOLYMERS; MONOMERS; ESTERS; CMRP

Domaines: Polymères; Matériaux

Imène Allaoua, Beatriz Eleuterio Goi, Mona Obadia, Antoine Debuigne, Christophe Detrembleur, et al.. (Co)Polymerization of vinyl levulinate by cobalt-mediated radical polymerization and functionalization by ketoxime click chemistry. Polymer Chemistry, 2014, 5, pp.2973-2979. ⟨10.1039/c3py01505j⟩. ⟨hal-00983418⟩