Reactivity of Vinyl Ethers and Vinyl Ribosides in UV-Initiated Free Radical Copolymerization with Acceptor Monomers

被引:18
作者
Pichavant, Loic [1 ]
Guillermain, Celine [1 ]
Coqueret, Xavier [1 ]
机构
[1] Univ Reims, CNRS, UMR 6229, Inst Chim Mol Reims, F-51687 Reims 2, France
关键词
ALTERNATING COPOLYMERIZATION; STEREOCHEMICAL EVIDENCE; POLYMERIZATION; SECONDARY; POLYMERS; ALLYL; PHOTOPOLYMERIZATION; PARTICIPATION; FUNCTIONALITY; DEPROTECTION;
D O I
10.1021/bm1005883
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The reactivity of various vinyl ethers and vinyloxy derivatives of ribose in the presence of diethyl fumarate or diethyl maleate was investigated for evaluating the potential of donor-acceptor-type copolymerization applied to unsaturated monomers derived from renewable feedstock. The photochemically induced polymerization of model monomer blends in the bulk state was monitored by infrared spectroscopy. The method allowed us to examine the influence of monomer pair structure on the kinetic profiles. The simultaneous consumption of both monomers was observed, supporting an alternating copolymerization mechanism. A lower reactivity of the blends containing maleates compared with fumarates was confirmed. The obtained kinetic data revealed a general correlation between the initial polymerization rate and the Hansen parameter OH associated with the H-bonding aptitude of the donor monomer.
引用
收藏
页码:2415 / 2421
页数:7
相关论文
共 53 条
[1]  
Anastas P.T., 1998, Green chemistry: theory and practice
[2]   2,3,5-TRI-O-BENZYL-D-RIBOSYL AND -L-ARABINOSYL BROMIDES [J].
BARKER, R ;
FLETCHER, HG .
JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (11) :4605-&
[3]  
Barton A.F. M., 1991, CRC HDB SOLUBILITY P
[4]  
Behr JB, 2002, EUR J ORG CHEM, V2002, P1256, DOI 10.1002/1099-0690(200204)2002:7<1256::AID-EJOC1256>3.0.CO
[5]  
2-R
[6]   Novel monovinyl methacrylic monomers containing secondary functionality for ultrarapid polymerization: Steady-state evaluation [J].
Berchtold, KA ;
Nie, J ;
Stansbury, JW ;
Hacioglu, B ;
Beckel, ER ;
Bowman, CN .
MACROMOLECULES, 2004, 37 (09) :3165-3179
[7]   POLYMERISATION OF UNSATURATED DERIVATIVES OF 1,2 - 5,6-DI-O-ISOPROPYLIDENE-D-GLUCOFURANOSE [J].
BLACK, WAP ;
DEWAR, ET ;
RUTHERFORD, D .
JOURNAL OF THE CHEMICAL SOCIETY, 1963, (SEP) :4433-&
[8]   Copolymerization of unsaturated glucono-δ-lactone derivatives [J].
Boltres, D ;
Schmalbruch, B ;
Buchholz, K .
MACROMOLECULAR CHEMISTRY AND PHYSICS, 2004, 205 (11) :1508-1518
[9]   Synthesis of allyl and alkyl vinyl ethers using an in situ prepared air-stable palladium catalyst. Efficient transfer vinylation of primary, secondary, and tertiary alcohols [J].
Bosch, M ;
Schlaf, M .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (13) :5225-+
[10]   Optimized synthesis of vinyl ether sugars and vinyl glycosides through transfer vinylation catalyzed by (4,7-Ph2-phen)Pd(OOCCF3)2 [J].
Bosch, Martin ;
Handerson, Sean ;
Schlaf, Marcel .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 2008, 27 (02) :103-112