End-group-catalyzed ring-opening polymerization of trimethylene carbonate

被引:34
作者
Mindemark, Jonas [1 ]
Hilborn, Jons [1 ]
Bowden, Tim [1 ]
机构
[1] Uppsala Univ, Dept Chem Mat, SE-75121 Uppsala, Sweden
关键词
D O I
10.1021/ma0629081
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
A controlled self-catalyzed polymerization reaction yielding well-defined heterotelechelic polymer chains and eliminating low molecular weight catalyst residues in the final polymer product were analyzed by utilizing a ternary amine. The molecular weights were kept relatively low for end-group analysis by Nuclear Magnetic Resonance spectroscopy (NMR) and linear correlation between the degree of polarization and monomer were found. NMR results show that the polydispersities remained low at high monomer conversions and longer reaction times after full conversion led to a larger molecular weight distribution. The results also show that the ternary amine catalyst are attached to the growing polymer chains that is shown by a downfield shift from 2.44 to 2.56 ppm. The benzoic acid ester of the ternary amine is found to be potent catalyst of Ring-Opening Polymerization (ROP).
引用
收藏
页码:3515 / 3517
页数:3
相关论文
共 33 条
[1]   Enzyme-catalyzed ring-opening copolymerization of 5-methyl-5-benzyloxycarbonyl-1,3-dioxan-2-one (MBC) with trimethylene carbonate (TMC): Synthesis and characterization [J].
Al-Azemi, TF ;
Harmon, JP ;
Bisht, KS .
BIOMACROMOLECULES, 2000, 1 (03) :493-500
[2]   Lipase-catalyzed ring-opening polymerization of trimethylene carbonate [J].
Bisht, KS ;
Svirkin, YY ;
Henderson, LA ;
Gross, RA ;
Kaplan, DL ;
Swift, G .
MACROMOLECULES, 1997, 30 (25) :7735-7742
[3]   Ethyl glucoside as a multifunctional initiator for enzyme-catalyzed regioselective lactone ring-opening polymerization [J].
Bisht, KS ;
Deng, F ;
Gross, RA ;
Kaplan, DL ;
Swift, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (07) :1363-1367
[4]   Studies on polymerization and ring formation. III. Glycol esters of carbonic acid [J].
Carothers, WH ;
Van Natta, FJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1930, 52 :314-326
[5]   First example of N-heterocyclic carbenes as catalysts for living polymerization:: Organocatalytic ring-opening polymerization of cyclic esters [J].
Connor, EF ;
Nyce, GW ;
Myers, M ;
Möck, A ;
Hedrick, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (06) :914-915
[6]   Biometal derivatives as catalysts for the ring-opening polymerization of trimethylene carbonate. Optimization of the Ca(II) salen catalyst system [J].
Darensbourg, Donald J. ;
Choi, Wonsook ;
Ganguly, Poulomi ;
Richers, Casseday P. .
MACROMOLECULES, 2006, 39 (13) :4374-4379
[7]   Controlled ring-opening polymerization of lactide and glycolide [J].
Dechy-Cabaret, O ;
Martin-Vaca, B ;
Bourissou, D .
CHEMICAL REVIEWS, 2004, 104 (12) :6147-6176
[8]   Ring-opening bulk polymerization of ε-caprolactone and trimethylene carbonate catalyzed by lipase Novozym 435 [J].
Deng, F ;
Gross, RA .
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 1999, 25 (1-3) :153-159
[9]   N-Heterocyclic carbenes:: Effective organic catalysts for living polymerization [J].
Dove, Andrew P. ;
Pratt, Russell C. ;
Lohmeijer, Bas G. G. ;
Culkin, Darcy A. ;
Hagberg, Eric C. ;
Nyce, Gregory W. ;
Waymouth, Robert M. ;
Hedrick, James L. .
POLYMER, 2006, 47 (11) :4018-4025
[10]   Thiourea-based bifunctional organocatalysis: Supramolecular recognition for living polymerization [J].
Dove, AP ;
Pratt, RC ;
Lohmeijer, BGG ;
Waymouth, RM ;
Hedrick, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (40) :13798-13799