Access to new carbohydrate-functionalized polylactides via organocatalyzed ring-opening polymerization

被引：48

作者：

Miao, Yong ^{[1
,2
,3
,4
,5
]}

Rousseau, Cyril ^{[4
,5
]}

Mortreux, Andre ^{[1
,2
,3
,4
]}

Martin, Patrick ^{[4
,5
]}

Zinck, Philippe ^{[1
,2
,3
,4
]}

机构：

[1] Univ Lille Nord France, F-59000 Lille, France

[2] ENSCL, UCCS, CCM, F-59652 Villeneuve Dascq, France

[3] USTL, UCCS, CCM, F-59655 Villeneuve Dascq, France

[4] CNRS, UMR8181, F-59652 Villeneuve Dascq, France

[5] UCCS, IUT Bethune, F-62400 Bethune, France

来源：

POLYMER | 2011年 / 52卷 / 22期

关键词：

Organocatalysis; Star polymers; cyclodextrin; EPSILON-CAPROLACTONE; D-GLUCOSE; LACTIDE; CYCLODEXTRINS; ROUTE; NANOPARTICLES; INITIATORS; ACTIVATION; COPOLYMERS; CATALYSTS;

D O I：

10.1016/j.polymer.2011.08.040

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

The 4-dimethylaminopyridine (DMAP) catalyzed ring-opening polymerization of lactide using various carbohydrate initiators has been assessed for the functionalization of polylactide. Selectively protected glucose derivatives bearing a free primary alcohol (Gic-1r) and a free secondary alcohol (Glc-2r), glucose and cyclodextrin diol derivatives (Glc-diol and CD-diol), methyl-alpha-D-glucopyranoside (Glc-Me) and native beta-cyclodextrin (CD) were used as initiators. According to the solubility of the carbohydrate derivative, the polymerizations were conducted in chlorinated solvents and in the bulk. Relatively narrow distributions are obtained in high yields in the absence of side reactions, affording a 100% functionalization efficiency. The catalytic synthesis of new carbohydrate link-functionalized polylactides and carbohydrate core star polylactides is reported. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：5018 / 5026

页数：9

共 49 条

[1] Amphiphilic star copolymers containing cyclodextrin core and their application as nanocarrier [J].

Adeli, Mohsen ;

Zarnegar, Zohre ;

Kabiri, Roya .

EUROPEAN POLYMER JOURNAL, 2008, 44 (07) :1921-1930

[2] Recent developments in ring opening polymerization of lactones for biomedical applications [J].

Albertsson, AC ;

Varma, IK .

BIOMACROMOLECULES, 2003, 4 (06) :1466-1486

[3] Regioselective end-functionalization of polylactide oligomers with D-glucose and D-galactose [J].

Bernard, K ;

Degée, P ;

Dubois, P .

POLYMER INTERNATIONAL, 2003, 52 (03) :406-411

[4] 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

[5] 'Link-functionalized' and triblock polymer architectures through bifunctional organolanthanide initiators: A review [J].

Boffa, LS ;

Novak, BM .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1998, 133 (1-2) :123-130

[6] ''Link-functionalized'' polymers: An unusual macromolecular architecture through bifunctional initiation [J].

Boffa, LS ;

Novak, BM .

MACROMOLECULES, 1997, 30 (12) :3494-3506

[7] Monomer versus alcohol activation in the 4-dimethylaminopyridine-catalyzed ring-opening polymerization of lactide and lactic O-carboxylic anhydride [J].

Bonduelle, Colin ;

Martin-Vaca, Blanca ;

Cossio, Fernando P. ;

Bourissou, Didier .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (17) :5304-5312

[8] Recent advances in the controlled preparation of poly(α-hydroxy acids):: Metal-free catalysts and new monomers [J].

Bourissou, Didier ;

Moebs-Sanchez, Sylvie ;

Martin-Vaca, Blance .

COMPTES RENDUS CHIMIE, 2007, 10 (09) :775-794

[9] Aliphatic polyester polymer stars: synthesis, properties and applications in biomedicine and nanotechnology [J].

Cameron, Donald J. A. ;

Shaver, Michael P. .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (03) :1761-1776

[10] Lipase-catalyzed synthesis of methyl 6-O-poly(ε-caprolactone)glycopyranosides [J].

Cordova, A ;

Iversen, T ;

Hult, K .

MACROMOLECULES, 1998, 31 (04) :1040-1045

← 1 2 3 4 5 →