Versatile catalytic systems based on complexes of zinc, magnesium and calcium supported by a bulky bis(morpholinomethyl)phenoxy ligand for the large-scale immortal ring-opening polymerisation of cyclic esters

被引:200
作者
Poirier, Valentin [1 ]
Roisnel, Thierry [1 ]
Carpentier, Jean-Francois [1 ]
Sarazin, Yann [1 ]
机构
[1] Univ Rennes 1, CNRS, UMR 6226, F-35042 Rennes, France
关键词
GROUP-3; METAL-COMPLEXES; EPSILON-CAPROLACTONE; LACTIDE POLYMERIZATION; POLY(TRIMETHYLENE CARBONATE); AMINOTROPONIMINATE CALCIUM; MOLECULAR-STRUCTURE; ALUMINUM COMPLEXES; BETA-BUTYROLACTONE; RACEMIC LACTIDE; POLY(LACTIDE);
D O I
10.1039/b917799j
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A new heteroleptic ethyl-zinc complex stabilized by a chelating bis(morpholinomethyl) phenoxy ligand has been synthesised and shown to be a highly potent initiator for the immortal ring-opening polymerisation (ROP) of lactide and beta-butyrolactone, being able to convert up to 50 000 equiv. of monomer in the presence of up to 1000 equiv. of an alcohol as transfer agent. Two related heteroleptic complexes of magnesium and calcium have also been prepared. These complexes are stable in solution, even in the presence of large amounts of alcohol, and constitute effective catalysts for the immortal ROP of lactide under mild conditions.
引用
收藏
页码:9820 / 9827
页数:8
相关论文
共 67 条
[1]   SYNTHESIS, STRUCTURE, AND SPECTROSCOPIC PROPERTIES OF COPPER(II) COMPOUNDS CONTAINING NITROGEN SULFUR DONOR LIGANDS - THE CRYSTAL AND MOLECULAR-STRUCTURE OF AQUA[1,7-BIS(N-METHYLBENZIMIDAZOL-2'-YL)-2,6-DITHIAHEPTANE]COPPER(II) PERCHLORATE [J].
ADDISON, AW ;
RAO, TN ;
REEDIJK, J ;
VANRIJN, J ;
VERSCHOOR, GC .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1984, (07) :1349-1356
[2]   IMMORTAL POLYMERIZATION - POLYMERIZATION OF EPOXIDE AND BETA-LACTONE WITH ALUMINUM PORPHYRIN IN THE PRESENCE OF PROTIC COMPOUND [J].
AIDA, T ;
MAEKAWA, Y ;
ASANO, S ;
INOUE, S .
MACROMOLECULES, 1988, 21 (05) :1195-1202
[3]   Syndiotactic-Enriched Poly(3-hydroxybutyrate)s via Stereoselective Ring-Opening Polymerization of Racemic β-Butyrolactone with Discrete Yttrium Catalysts [J].
Ajellal, Noureddine ;
Bouyahyi, Miloud ;
Amgoune, Abderramane ;
Thomas, Christophe M. ;
Bondon, Arnaud ;
Pillin, Isabelle ;
Grohens, Yves ;
Carpentier, Jean-Francois .
MACROMOLECULES, 2009, 42 (04) :987-993
[4]  
Albertsson AC, 2002, ADV POLYM SCI, V157, P1
[5]   Recent developments in ring opening polymerization of lactones for biomedical applications [J].
Albertsson, AC ;
Varma, IK .
BIOMACROMOLECULES, 2003, 4 (06) :1466-1486
[6]   SIR97:: a new tool for crystal structure determination and refinement [J].
Altomare, A ;
Burla, MC ;
Camalli, M ;
Cascarano, GL ;
Giacovazzo, C ;
Guagliardi, A ;
Moliterni, AGG ;
Polidori, G ;
Spagna, R .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1999, 32 :115-119
[7]   Highly active, productive, and syndiospecific yttrium initiators for the polymerization of racemic β-butyrolactone [J].
Amgoune, A ;
Thomas, CM ;
Ilinca, S ;
Roisnel, T ;
Carpentier, JF .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (17) :2782-2784
[8]   Ring-opening polymerization of lactide with group 3 metal complexes supported by dianionic alkoxy-amino-bisphenolate ligands: Combining high activity, productivity, and selectivity [J].
Amgoune, A ;
Thomas, CM ;
Roisnel, T ;
Carpentier, JF .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (01) :169-179
[9]   Yttrium complexes as catalysts for living and immortal polymerization of lactide to highly heterotactic PLA [J].
Amgoune, Abderramane ;
Thomas, Christophe M. ;
Carpentier, Jean-Francois .
MACROMOLECULAR RAPID COMMUNICATIONS, 2007, 28 (06) :693-697
[10]   IMMORTAL POLYMERIZATION - POLYMERIZATION OF EPOXIDE CATALYZED BY AN ALUMINUM PORPHYRIN ALCOHOL SYSTEM [J].
ASANO, S ;
AIDA, T ;
INOUE, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (17) :1148-1149