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

被引:37
作者
Allaoua, Imene [1 ]
Goi, Beatriz Eleuterio [2 ]
Obadia, Mona M. [1 ]
Debuigne, Antoine [2 ]
Detrembleur, Christophe [2 ]
Drockenmuller, Eric [1 ,3 ]
机构
[1] Univ Lyon 1, IMP, UMR CNRS 5223, F-69622 Villeurbanne, France
[2] Univ Liege ULg, Dept Chem, Ctr Educ & Res Macromol, B-4000 Liege, Belgium
[3] Inst Univ France, Paris, France
关键词
POLYESTER MATERIALS; ACETATE; BIOMASS; COPOLYMERS; MONOMERS; ESTERS; CMRP;
D O I
10.1039/c3py01505j
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
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.
引用
收藏
页码:2973 / 2979
页数:7
相关论文
共 40 条
[1]   Polymeric micelles for the pH-dependent controlled, continuous low dose release of paclitaxel [J].
Alani, Adam W. G. ;
Bae, Younsoo ;
Rao, Deepa A. ;
Kwon, Glen S. .
BIOMATERIALS, 2010, 31 (07) :1765-1772
[2]   Synthesis of levulinic acid-glycerol ketal-ester oligomers and structural characterization using NMR spectroscopy [J].
Amarasekara, Ananda S. ;
Hawkins, Steven A. .
EUROPEAN POLYMER JOURNAL, 2011, 47 (12) :2451-2457
[3]   Preparation of a xanthate-terminated dextran by click chemistry:: Application to the synthesis of polysaccharide-coated nanopartides via surfactant-free ab initio emulsion polymerization of vinyl acetate [J].
Bernard, Julien ;
Save, Maud ;
Arathoon, Benoit ;
Charleux, Bernadette .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2008, 46 (08) :2845-2857
[4]   Technology development for the production of biobased products from biorefinery carbohydrates-the US Department of Energy's "Top 10" revisited [J].
Bozell, Joseph J. ;
Petersen, Gene R. .
GREEN CHEMISTRY, 2010, 12 (04) :539-554
[5]   Cobalt-mediated radical polymerization (CMRP) of vinyl acetate initiated by redox systems:: Toward the scale-up of CMRP [J].
Bryaskova, Rayna ;
Detrembleur, Christophe ;
Debuigne, Antoine ;
Jerome, Robert .
MACROMOLECULES, 2006, 39 (24) :8263-8268
[6]   Lipase-mediated enantioselective acylation of alcohols with functionalized vinyl esters: acyl donor tolerance and applications [J].
Chenevert, Robert ;
Pelchat, Nicholas ;
Morin, Pierre .
TETRAHEDRON-ASYMMETRY, 2009, 20 (10) :1191-1196
[7]   Chemical routes for the transformation of biomass into chemicals [J].
Corma, Avelino ;
Iborra, Sara ;
Velty, Alexandra .
CHEMICAL REVIEWS, 2007, 107 (06) :2411-2502
[8]   Synthesis of end-functional poly(vinyl acetate) by cobalt-mediated radical polymerization [J].
Debuigne, A ;
Caille, JR ;
Jérôme, R .
MACROMOLECULES, 2005, 38 (13) :5452-5458
[9]   Cobalt-mediated radical polymerization of acrylonitrile:: Kinetics investigations and DFT calculations [J].
Debuigne, Antoine ;
Michaux, Catherine ;
Jerome, Christine ;
Jerome, Robert ;
Poli, Rinaldo ;
Detrembleur, Christophe .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (25) :7623-7637
[10]   Mechanistic insights into the cobalt-mediated radical polymerization (CMRP) of vinyl acetate with cobalt(III) adducts as initiators [J].
Debuigne, Antoine ;
Champouret, Yohan ;
Jerome, Robert ;
Poli, Rinaldo ;
Detrembleur, Christophe .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (13) :4046-4059