Synthesis, characterization and degradability of the novel aliphatic polyester bearing pendant N-isopropylamide functional groups

被引:8
作者
Dai, Weifeng [1 ]
Huang, Hui [1 ]
Du, Zhengzhen [1 ]
Lang, Meidong [1 ]
机构
[1] E China Univ Sci & Technol, Sch Mat Sci & Engn, Minist Educ, Key Lab Ultrafine Mat, Shanghai 200237, Peoples R China
基金
中国国家自然科学基金;
关键词
Biodegradation; Ring-opening polymerization; PCL; Pendant N-isopropylamide functional groups;
D O I
10.1016/j.polymdegradstab.2008.09.001
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 synthesis, characterization, and degradability of the novel aliphatic polyester bearing pendant N-isopropylamide functional group are reported for the first time. 2-(N-Isopropyl-2-carbamoylethyl)cyclohexanone (CCH) was first synthesized by the Michael reaction of N-isopropylacrylamide with cyclohexanone and was subsequently converted into 6-(N-isopropyl-2-carbamoylethyl)-epsilon-caprolactone (CCL) by the Baeyer-Villiger oxidation reaction using 3-chloroperoxybenzoic acid (mCPBA) as the oxidant. Finally, the novel functionalized poly(epsilon-caprolactone) bearing the pendant N-isopropylamide functional groups, poly(6-(N-isopropyl-2-carbamoylethyl)-epsilon-caprolactone-co-epsilon-caprolactone)s (poly(CCL-co-CL)), were carried out successfully by bulk ring-opening polymerization of CCL and epsilon-CL initiated by Sn(OCt)(2). Poly(CCL-co-CL) were characterized by H-1 NMR, C-13 NMR, SEC and DSC. The copolymer containing 9.1 mol% CCL formed flexible films and was used to study its degradability. A phosphate buffer (pH = 7.4) with temperature 37 degrees C was adopted to proceed the degrading study all through. Compared with poly(epsilon-caprolactone), the hydrolytic degradation of poly(CCL-co-CL) was much faster, which is confirmed by the weight loss and change of intrinsic viscosity. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2089 / 2095
页数:7
相关论文
共 28 条
[1]   Potential tissue implants from the networks based on 1,5-dioxepan-2-one and ε-caprolactone [J].
Andronova, N ;
Srivastava, RK ;
Albertsson, AC .
POLYMER, 2005, 46 (18) :6746-6755
[2]   SYNTHESIS AND RGD PEPTIDE MODIFICATION OF A NEW BIODEGRADABLE COPOLYMER - POLY(LACTIC ACID-CO-LYSINE) [J].
BARRERA, DA ;
ZYLSTRA, E ;
LANSBURY, PT ;
LANGER, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (23) :11010-11011
[3]   New functional aliphatic polyesters by chemical modification of copolymers of ε-caprolactone with γ-(2-bromo-2-methylpropionate)-ε-caprolactone, γ-bromo-ε-caprolactone, and a mixture of β- and γ-ene-ε-caprolactone [J].
Detrembleur, C ;
Mazza, M ;
Lou, X ;
Halleux, O ;
Lecomte, P ;
Mecerreyes, D ;
Hedrick, JL ;
Jérôme, R .
MACROMOLECULES, 2000, 33 (21) :7751-7760
[4]   MACROMOLECULAR ENGINEERING OF POLYLACTONES AND POLYLACTIDES .12. STUDY OF THE DEPOLYMERIZATION REACTIONS OF POLY(EPSILON-CAPROLACTONE) WITH FUNCTIONAL ALUMINUM ALKOXIDE END-GROUPS [J].
DUBOIS, P ;
BARAKAT, I ;
JEROME, R ;
TEYSSIE, P .
MACROMOLECULES, 1993, 26 (17) :4407-4412
[5]   Hydrolytic and thermal degradation of random copolyesters of ε-caprolactone and 2-oxepane-1,5-dione [J].
Dwan'Isa, JPL ;
Lecomte, P ;
Dubois, P ;
Jérôme, R .
MACROMOLECULAR CHEMISTRY AND PHYSICS, 2003, 204 (09) :1191-1201
[6]   Catalytic asymmetric intramolecular Michael reaction of aldehydes [J].
Fonseca, MTH ;
List, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (30) :3958-3960
[7]  
GABELNICK HL, 1983, ADV HUMAN FERTILITY, V2, P149
[8]   Biofunctionalized poly(ethylene glycol)-block-poly(ε-caprolactone) nanofibers for tissue engineering [J].
Grafahrend, Dirk ;
Calvet, Julia Lleixa ;
Salber, Jochen ;
Dalton, Paul D. ;
Moeller, Martin ;
Klee, Doris .
JOURNAL OF MATERIALS SCIENCE-MATERIALS IN MEDICINE, 2008, 19 (04) :1479-1484
[9]   Synthesis and degradation of PLA-PCL-PLA triblock copolymer prepared by successive polymerization of ε-caprolactone and DL-lactide [J].
Huang, MH ;
Li, SM ;
Vert, M .
POLYMER, 2004, 45 (26) :8675-8681
[10]   Thiourea-catalyzed asymmetric Michael addition of activated methylene compounds to α,β-unsaturated imides:: Dual activation of imide by intra- and intermolecular hydrogen bonding [J].
Inokuma, Tsubasa ;
Hoashi, Yasutaka ;
Takemoto, Yoshiji .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (29) :9413-9419