Tensile behavior and dynamic mechanical analysis of novel poly(lactide/δ-valerolactone) statistical copolymers

Journal of the Mechanical Behavior of Biomedical Materials

Volumn 35, Issue , 2014, Pages 39-50

  Fernandez J ^a   Larranaga A ^a   Etxeberria, A ^b   Sarasua, J R ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

Copolymer; DMA; Lactide; Mechanical properties; Valerolactone; Caprolactone

Indexed keywords

COPOLYMERS; GLASS TRANSITION; MECHANICAL PROPERTIES; MECHANICAL TESTING;

CAPROLACTONE; DMA; DYNAMIC MECHANICAL ANALYSIS (DMA); ELASTOMERIC MATERIALS; HYDROLYTIC DEGRADATION; LACTIDES; MECHANICAL PERFORMANCE; STATISTICAL COPOLYMERS;

TERPOLYMERS;

COPOLYMER; ELASTOMER; LACTIDE CO DELTA VALEROLACTONE COPOLYMER; LACTONE; MONOMER; POLYLACTIDE; UNCLASSIFIED DRUG; BIOMATERIAL; DELTA-VALEROLACTONE; GLASS; POLYESTER; POLYMER; PYRONE DERIVATIVE;

ARTICLE; BIOMEDICINE; CHEMICAL ANALYSIS; DEGRADATION KINETICS; MECHANICS; PHYSICAL PARAMETERS; PRIORITY JOURNAL; RIGIDITY; STORAGE; TENSILE STRENGTH; CHEMISTRY; CRYSTALLIZATION; ELASTICITY; HYDROLYSIS; MATERIALS TESTING; MECHANICAL STRESS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRESSURE; TEMPERATURE; TIME;

BIOCOMPATIBLE MATERIALS; CRYSTALLIZATION; ELASTICITY; ELASTOMERS; GLASS; HYDROLYSIS; MAGNETIC RESONANCE SPECTROSCOPY; MATERIALS TESTING; POLYESTERS; POLYMERS; PRESSURE; PYRONES; STRESS, MECHANICAL; TEMPERATURE; TENSILE STRENGTH; TIME FACTORS;

EID: 84898810464     PISSN: 17516161     EISSN: 18780180     Source Type: Journal    
DOI: 10.1016/j.jmbbm.2014.03.013     Document Type: Article

References (50)

1. Aubin M., PrudD́homme R.E. Preparation and properties of poly(valerolactone). Polymer 1981, 22:1223-1226.
2. Bouyahyi M., Duchateau R. Metal-based catalysts for controlled ring-opening polymerization of macrolactones: high molecular weight and well-defined copolymer architectures. Macromolecules 2014, 47:517-524.
3. Brulé E., Gaillard S., Rager M.-N., Roisnel T., Guérineau V., Nolan S.P., Thomas C.M. Polymerization of racemic β-butyrolactone using gold catalysts: a simple access to biodegradable polymers. Organometallics 2011, 30:2650-2653.
4. Cao H., Han H., Li G., Yang J., Zhang L., Yang Y., Fang X., Li Q. Biocatalytic synthesis of poly(δ-valerolactone) using a thermophilic esterase from archaeoglobus fulgidus as catalyst. Int. J. Mol. Sci. 2012, 13:12232-12241.
5. Cheeseman M.A., Machuga E.J., Bayley A.B. A tiered approach to threshold of regulation. Food Chem. Toxicol. 1999, 37:387-412.
6. Cross E.D., Allan L.E.N., Decken A., Shaver M.P. Aluminum salen and salan complexes in the ring-opening polymerization of cyclic esters: controlled immortal and copolymerization of rac-beta-butyrolactone and rac-lactide. J. Polym. Sci., Part A: Polym. Chem. 2013, 51:1137-1146.
7. de Geus M., van der Meulen I., Goderis B., van Hecke K., Dorschu M., van der Werff H., Coning C.E., Heise A. Performance polymers from renewable monomers: high molecular weight poly(pentadecalactone) for fiber applications. Polym. Chem. 2010, 1:525-533.
8. Dobrzynski P., Li S., Kasperczyk J., Bero M., Gasc F., Vert M. Structure property relationships of copolymers obtained by ring-opening polymerization of glycolide and ε-caprolactone. Part 1. Synthesis and characterization. Biomacromolecules 2005, 6:483-488.
9. Fernández J., Larrañaga A., Etxeberria A., Wang W., Sarasua J.R. A new generation of poly(lactide/ε-caprolactone) polymeric biomaterials for application in the biomedical field. J. Biomed. Mater. Res. A. 2014, http://onlinelibrary.wiley.com/doi/10.1002/jbm.a.35036/abstract.
10. Fernández J., Etxeberría A., Sarasua J.R. Synthesis, structure and properties of poly(l-lactide-co-ε-caprolactone) statistical copolymers. J. Mech. Behav. Biomed. Mater. 2012, 9:100-112.
11. Fernández J., Meaurio E., Chaos A., Etxeberria A., Alonso-Varona A., Sarasua J.R. Synthesis and characterization of poly(l-lactide/ε-caprolactone) statistical copolymers with well resolved chain microstructures. Polymer 2013, 54:2621-2631.
12. Fernández J., Larrañaga A., Etxeberria A., Sarasua J.R. Effects of chain microstructures and derived crystallization capability on hydrolytic degradation of poly(l-lactide/ε-caprolactone) copolymers. Polym. Degrad. Stab. 2013, 98:481-489.
13. Freier T., Kunze C., Nischan C., Kramer S., Sternberg K., SaX M., Hopt U.T., Schmitz K.-P. In vitro and in vivo degradation studies for development of a biodegradable patch based on poly(3-hydroxybutyrate). Biomaterials 2002, 23:2649-2657.
14. Grijpma D.W., Pennings A.J. Polymerization temperature effects on the properties of l-lactide and ε-caprolactone copolymers. Polym. Bull. 1991, 25:335-341.
15. Grunova E., Kirillov E., Roisnel T., Carpentier J.F. Group 3 metal complexes of salen-like fluorous dialkoxy-diimino ligands: synthesis, structure, and application in ring-opening polymerization of rac-lactide and rac-beta-butyrolactone. Organometallics 2008, 27:5691-5698.
16. Hazer D.B., Ebru K., Hazer B. Poly(3-hydroxyalkanoate)s: diversification and biomedical applications: a state of the art review. Mater. Sci. Eng., C 2012, 32:637-647.
17. Helminen A.O., Korhonen H., Seppala J.V. Cross-linked poly(ε-caprolactone/d,l-lactide) copolymers with elastic properties. Macromol. Chem. Phys. 2002, 203:2630-2639.
18. Herbert I.R. Statistical analysis of copolymer sequence distribution. NMR Spectroscopy of Polymers 1993, 50-79. Blackie Academic & Professional, London, (Chapter 2). R.N. Ibbet (Ed.).
19. HiljanenVainio M., Karjalainen T., Seppala J. Biodegradable lactone copolymers.1. Characterization and mechanical behavior of epsilon-caprolactone and lactide copolymers. J. Appl. Polym. Sci. 1996, 59:1281-1288.
20. Hori Y., Yamaguchi A., Hagiwara T. Chemical synthesis of high molecular weight poly(3-hydroxybutyrate-co-4-hydroxybutyrate). Polymer 1995, 36(24):4703-4705.
21. Houk K.N., Jabbari A., Hall H.K., Alemán C. Why δ-valerolactone polymerizes and γ-butyrolactone does not. J. Org. Chem. 2008, 73:2674-2678.
22. Jeffery B.J., Whitelaw E.L., Garcia-Vivo D., Stewart J.A., Mahon M.F., Davidson M.G., Jones M.D. Group 4 initiators for the stereoselective ROP of rac-beta-butyrolactone and its copolymerization with rac-lactide. Chem. Commun. 2011, 47:12328-12330.
23. Jiang Z., Azim H., Gross R.A. Lipase-catalyzed copolymerization of ω-pentadecalactone with p-dioxanone and characterization of copolymer thermal and crystalline properties. Biomacromolecules 2007, 8:2262-2269.
24. Kasperczyk J., Li S., Jaworska J., Dobrzyński P., Vert M. Degradation of copolymers obtained by ring-opening polymerization of glycolide and -caprolactone: a high resolution NMR and ESI-MS study. Polym. Degrad. Stab. 2008, 93:990-999.
25. Kricheldorf H.R., Mang T., Jonte J.M. Polylactones.1. Copolymerization of glycolide and epsilon-caprolactone. Macromolecules 1984, 17:2173-2181.
26. Labet M., Thielemans W. Synthesis of polycaprolactone: a review. R. Soc. Chem. 2009, 38:3484-3504.
27. Thermodynamics of fusion of poly(beta-propiolactone) and poly(epsilon-caprolactone) comparative analysis of melting of aliphatic polylactone and polyester chains Eur. Polym. J. 1972, 8:449.
28. Lee C.W., Urakawa R., Kimura Y. Copolymerization of γ-valerolactone and β-butyrolactone. Eur. Polym. J. 1998, 34:117-122.
29. Lee S.H., Kim B.S., Kim S.H., Choi S.W., Jeong S.I., Kwon I.K., Kang S.W., Nikolovski J., Mooney D.J., Han Y.K., Kim Y.H. Elastic biodegradable poly(glycolide-co-caprolactone) scaffold for tissue engineering. J. Biomed. Mater. Res. A 2003, 66:29-37.
30. Li S., Dobrzynski P., Kasperczyk J., Bero M., Braud C., Vert M. Structure property relationships of copolymers obtained by ring-opening polymerization of glycolide and ε-caprolactone. Part 2. Influence of composition and chain microstructure on the hydrolytic degradation. Biomacromolecules 2005, 6:489-497.
31. Lizundia E., Petisco S., Sarasua J.R. Phase-structure and mechanical properties of isothermally melt- and cold-crystallized poly(l-lactide). J. Mech. Behav. Biomed. Mater. 2013, 17(242):251.
32. López-Rodriguez N., López-Arraiza A., Meaurio E., Sarasua J.R. Crystallization, morphology, and mechanical behavior of polylactide/poly(ε-caprolactone) blends. Polym. Eng. Sci. 2006, 46:1299-1308.
33. Lu X.L., Cai W., Gao Z.Y. Shape-memory behaviors of biodegradable poly(l-lactide-co-epsilon-caprolactone) copolymers. J. Appl. Polym. Sci. 2008, 108:1109-1115.
34. Martello M.T., Hillmyer M.A. Polylactide. Poly(6-methyl-ε-caprolactone)-polylactide thermoplastic elastomers. Macromolecules 2011, 44:8537-8545.
35. Martello M.T., Hillmyer M.A. Bulk ring-opening transesterification polymerization of the renewable δ-decalactone using an organocatalyst. ACS Macro Lett. 2012, 1:131-135.
36. Martin D.P., Williams S.F. Medical applications of poly-4-hydroxybutyrate: a strong flexible absorbable biomaterial. Biochem. Eng. J. 2003, 16:97-105.
37. Menard K.P. Dynamic Mechanical Analysis: A Practical Introduction 1999, CRC Press LLC, Boca Raton (Florida).
38. Moore T., Adhikari R., Gunatillake P. Chemosynthesis of bioresorbable poly(γ-butyrolactone) by ring-opening polymerization: a review. Biomaterials 2005, 26:3771-3782.
39. Na Y.-H., He Y., Asakawa N., Yoshie N., Inoue Y. Miscibility and phase structure of blends of poly(ethylene oxide) with poly(3-hydroxybutyrate), poly(3-hydroxypropionate), and their copolymers. Macromolecules 2002, 35(3):727-735.
40. Nakamura S., Doi Y., Scandola M. Microbial synthesis and characterisation of poly(3-hydroxybutyrate-co-4-hydroxybutyrate). Macromolecules 1992, 25(17):4237-4241.
41. Nakayama A., Kawasaki N., Maeda Y., Arvanitoyannis I., Aiba S., Yamamoto N. Study of biodegradability of poly(delta-valerolactone-co-l-lactide)s. J. Appl. Polym. Sci. 1997, 66:741-748.
42. Olsén P., Borke T., Odelius K., Albertsson A.C. ε-Decalactone: a thermoresilient and toughening comonomer to poly(l-lactide). Biomacromolecules 2013, 14:2883-2890.
43. Pajerski A.D., Lenz R.W. Stereoregular polymerisation of β-butyrolactone by aluminoxane catalysis. Makromol. Chem. Makromol. Symp. 1993, 73:7-26.
44. Pan P., Zhu B., Inoue Y. Enthalpy relaxation and embrittlement of poly(l-lactide) during physical aging. Macromolecules 2007, 40:9664-9671.
45. Poirier Y., Dennis D., Klomparens K., Somerville C.MPS: Set "C" as given name. Polyhydroxybutyrate, a biodegradable thermoplastic produced in transgenic plants. Science 1992, 256:520. (223).
46. Urayama H., Kanamori T., Kimura Y. Microstructure and thermomechanical properties of glassy polylactides with different optical purity of the lactate units. Macromol. Mater. Eng. 2001, 286:705-713.
47. 3. Macromolecules 1992, 25:37-44.
48. Woodruff M.A., Hutmacher D.W. The return of a forgotten polymer: polycaprolactone in the 21st century. Prog. Polym. Sci. 2010, 35:1217-1256.
49. Yoo Y.C., Kim H.Y., Jin F.L., Park S.J. Synthesis of poly(glycolide-caprolactone) copolymers for application as bioabsorbable suture materials. Macromol. Res. 2013, 21:687-692.
50. Zuza E., Ugartemendia J.M., López A., Meaurio E., Lejardi A., Sarasua J.R. Glass transition behavior and dynamics fragility in polylactides containing mobile and rigid amorphous fractions. Polymer 2008, 49:4427-4432.