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

Polymer Degradation and Stability

Volumn 93, Issue 12, 2008, Pages 2089-2095

  Dai, Weifeng ^a   Huang, Hui ^a   Du, Zhengzhen ^a   Lang, Meidong ^a  

^a BEIJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

Author keywords

Biodegradation; PCL; Pendant N isopropylamide functional groups; Ring opening polymerization

Indexed keywords

ABS RESINS; ACIDS; ACRYLIC MONOMERS; AMIDES; BEARINGS (STRUCTURAL); BIOCHEMISTRY; BIODEGRADABLE POLYMERS; BIODEGRADATION; CHEMICAL REACTIONS; DEGRADATION; FUNCTIONAL GROUPS; MONOMERS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; POLYMERS; RING OPENING POLYMERIZATION; TIN;

ALIPHATIC POLYESTERS; CAPROLACTONE; CHLOROPEROXYBENZOIC ACIDS; CYCLOHEXANONE; DEGRADABILITY; FLEXIBLE FILMS; FUNCTIONALIZED; HYDROLYTIC DEGRADATIONS; INTRINSIC VISCOSITIES; ISOPROPYLACRYL AMIDES; MICHAEL REACTIONS; OXIDATION REACTIONS; PCL; PENDANT N-ISOPROPYLAMIDE FUNCTIONAL GROUPS; PHOSPHATE BUFFERS; RING-OPENING POLYMERIZATIONS; WEIGHT LOSSES;

FUNCTIONAL POLYMERS;

EID: 56249106568     PISSN: 01413910     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.polymdegradstab.2008.09.001     Document Type: Article

References (28)

1. Lang M.D., and Chu C.C. Functionalized multiarm poly(ε-caprolactone)s: synthesis, structure analysis and network formation. J Appl Polym Sci 86 (2002) 2296-2306
2. Tsuji H., and Horikawa G. Porous biodegradable polyester blends of poly(l-lactic acid) and poly(ε-caprolactone): physical properties, morphology, and biodegradation. Polym Int 56 (2007) 258-266
3. Lang M.D., Bei J.Z., and Wang S.G. Synthesis and characterization of polycaprolactone poly(ethylene oxide) polylactide tri-component copolymers. J Biomater Sci Polym E 10 (1999) 501-512
4. Miao H., Hao J.Y., Liu Y., and Deng X.M. Synthesis, crystallinity and degradation properties of biodegradable poly[(sebacic anhydride)-co-caprolactone] triblock copolymers. Polym Int 57 (2008) 316-323
5. Pitt C.G., Chasalow F.I., Hibionada Y.M., Klimas D.M., and Schindler A. Aliphatic polyesters. I. The degradation of poly(ε-caprolactone) in vivo. J Appl Polym Sci 26 (1981) 3779-3787
6. Woodward S.C., Brewer P.S., Moatamed F., Scjondler A., and Pitt C.G. The intracellular degradation of poly(ε-caprolactone). J Biomed Mater Res 19 (1985) 437-444
7. Huang M.H., Li S.M., and Vert M. Synthesis and degradation of PLA-PCL-PLA triblock copolymer prepared by successive polymerization of ε-caprolactone and dl-lactide. Polymer 45 (2004) 8675-8681
8. Lang M.D., Wong R.P., and Chu C.C. Synthesis and structural analysis of functionalized poly(ε-caprolactone)-based three-arm star polymers. J Polym Sci Part A Polym Chem 40 (2002) 1127
9. Yu J., and Wu P.Y. Crystallization process of poly(ε-caprolactone)-poly(ethylene oxide)-poly(ε-caprolactone) investigated by infrared and two-dimensional infrared correlation spectroscopy. Polymer 48 (2007) 3477-3485
10. Andronova N., Srivastava R.K., and Albertsson A.C. Potential tissue implants from the networks based on 1,5-dioxepan-2-one and ε-caprolactone. Polymer 46 (2005) 6746-6755
11. Tian D., Dubois P., and Jérôme R. Macromolecular engineering of polylactones and polylactides. 22. Copolymerization of ε-caprolactone and 1,4,8-trioxaspiro[4.6]-9-undecanone initiated by aluminum isopropoxide. Macromolecules 30 (1997) 2575-2581
12. Liu M.J., Vladimirov N., and Fréchet J.M. A new approach to hyperbranched polymers by ring-opening polymerization of an AB monomer: 4-(2-hydroxyethyl)-ε-caprolactone. Macromolecules 32 (1999) 6881-6884
13. Lecomte P., Riva R., Schmeits S., Rieger J., Butsele K.V., Jérôme C., et al. New prospects for the grafting of functional groups onto aliphatic polyesters. Ring-opening polymerization of α- or γ-substituted ε-caprolactone followed by chemical derivatization of the substituents. Macromol Symp 240 (2006) 157-165
14. Mahmud A., Xiong X.B., and Lavasanifar A. Novel self-associating poly(ethylene oxide)-block-poly(ε-caprolactone) block copolymers with functional side groups on the polyester block for drug delivery. Macromolecules 39 (2006) 9419-9428
15. 3-catalyzed ring-opening polymerizations of ε-caprolactone. Macromolecules 37 (2004) 6340-6345
16. Barrera D., Zylstra E., Lansbury P., and Langer R. Synthesis and RGD peptide modification of a new biodegradable copolymer: poly(lactic acid-co-lysine). J Am Chem Soc 115 (1993) 11010-11011
17. Tian D., Dubois P., Grandfils C., and Jérôme J. Ring-opening polymerization of 1,4,8-trioxaspiro[4.6]-9-undecanone: a new route to aliphatic polyesters bearing functional pendent groups. Macromolecules 30 (1997) 406-409
18. Detrembleur C., Mazza M., Lou X., Halleux O., Lecomte Ph., Mecerreyes D., et al. New functional aliphatic polyesters by chemical modification of copolymers of ε-caprolactone with γ-(2-bromo-2-methylpropionate)-ε-caprolactone, β-bromo-ε-caprolactone, and a mixture of β- and γ-ene-ε-caprolactone. Macromolecules 33 (2000) 7751-7760
19. Trollsås M., Lee V.Y., Mecerreyes D., LÖwenhielm P., MÖller M., Miller R.D., et al. Hydrophilic aliphatic polyesters: design, synthesis, and ring-opening polymerization of functional cyclic esters. Macromolecules 33 (2000) 4619-4627
20. Dwan'Isa J.P.L., Lecomte P., Dubois P., and Jérôme R. Hydrolytic and thermal degradation of random copolyesters of ε-caprolactone and 2-oxepane-1,5-dione. Macromol Chem Phys 204 (2003) 1191-1201
21. Nakayama A., Kawasaki N., and Arvanitoyannis I. Synthesis and degradability of a novel aliphatic polyester: poly(β-methyl-δ-valerolactone-co-l-lactide). Polymer 36 (1995) 1295-1301
22. Inokuma T., Hoashi Y., and Takemoto Y. 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 Am Chem Soc 128 (2006) 9413-9419
23. Yamagiwa N., Qin H.B., Matsunaga S., and Shibasaki M. Lewis acid-Lewis acid heterobimetallic cooperative catalysis: mechanistic studies and application in enantioselective aza-Michael reaction. J Am Chem Soc 127 (2005) 13419-13427
24. Fonseca M.T.H., and List B. Catalytic asymmetric intramolecular Michael reaction of aldehydes. Angew Chem Int Ed 43 (2004) 3958-3960
25. Kc R.B., Bhattarai S.R., Aryal S., Bhattarai N., Lee M.B., and Kim H.Y. Synthesis and characterization of amine-functionalized amphiphilic block copolymers based on poly(ethylene glycol) and poly(caprolactone). Polym Int 56 (2007) 518-524
26. Dubois P., Barakat T., Jérôme R., and Teyssié Ph. Macromolecular engineering of polylactones and polylactides. 12. Study of the depolymerization reactions of poly(epsilon-caprolactone) with functional aluminum alkoxide end groups. Macromolecules 26 (1993) 4407-4412
27. Grafahrend D., Calvet L., Salber J., Dalton P.D., Moeller M., and Klee D. Biofunctionalized poly(ethylene glycol)-block-poly(ε-caprolactone) nanofibers for tissue engineering. J Mater Sci Mater Med 19 (2008) 1479-1484
28. Gabelnick H.L. Advances in human fertility and reproductive endocrinology. Long acting steroid contraception vol. 2 (1983), Raven Press, New York p. 149