共 34 条
Synthesis of block and end-functionalized polyesters by triflimide-catalyzed ring-opening polymerization of ε-caprolactone, 1,5-dioxepan-2-one, and rac-lactide
被引:35
作者:
Makiguchi, Kosuke
Kikuchi, Seiya
Satoh, Toshifumi
Kakuchi, Toyoji
[1
]
机构:
[1] Hokkaido Univ, Grad Sch Chem Sci & Engn, Sapporo, Hokkaido 0608628, Japan
关键词:
cationic polymerization;
polyesters;
ring-opening polymerization;
N-HETEROCYCLIC CARBENES;
ORGANOCATALYTIC LIVING POLYMERIZATION;
ORGANIC CATALYSTS;
CYCLIC ESTERS;
CATIONIC-POLYMERIZATION;
PHOSPHAZENE BASES;
ACID;
COMBINATION;
LACTONES;
D O I:
10.1002/pola.26631
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 ring-opening polymerization (ROP) of cyclic esters, such as epsilon-caprolactone, 1,5-dioxepan-2-one, and racemic lactide using the combination of 3-phenyl-1-propanol as the initiator and triflimide (HNTf2) as the catalyst at room temperature with the [monomer]0/[initiator]0 ratio of 50/1 was investigated. The polymerizations homogeneously proceeded to afford poly(epsilon-caprolactone) (PCL), poly(1,5-dioxepan-2-one) (PDXO), and polylactide (PLA) with controlled molecular weights and narrow polydispersity indices. The molecular weight determined from an 1H NMR analysis (PCL, Mn,NMR=5380; PDXO, Mn,NMR=5820; PLA, Mn,NMR=6490) showed good agreement with the calculated values. The 1H NMR and matrix-assisted laser desorption ionization time-of-flight mass spectrometry analyses strongly indicated that the obtained compounds were the desired polyesters. The kinetic measurements confirmed the controlled/living nature for the HNTf2-catalyzed ROP of cyclic esters. A series of functional alcohols, such as propargyl alcohol, 6-azido-1-hexanol, N-(2-hydroxyethyl)maleimide, 5-hexen-1-ol, and 2-hydroxyethyl methacrylate, successfully produced end-functionalized polyesters. In addition, poly(ethylene glycol)-block-polyester, poly(-valerolactone)-block-poly(epsilon-caprolactone), and poly(epsilon-caprolactone)-block-polylactide were synthesized using the HNTf2-catalyzed ROP. (c) 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 24552463
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页码:2455 / 2463
页数:9
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