Enhancing mechanical properties of thermoplastic polyurethane elastomers with 1,3-trimethylene carbonate, epsilon-caprolactone and L-lactide copolymers via soft segment crystallization

Express Polymer Letters

Volumn 5, Issue 10, 2011, Pages 897-910

  Liow, S S ^a   Lipik, V T ^a   Widjaja, L K ^a   Venkatraman, S S ^a   Abadie, M J M ^a,b  

^a NANYANG TECHNOLOGICAL UNIVERSITY   (Singapore)

^b UNIV MONTPELLIER   (France)

Author keywords

Biodegradable polymers; Elastomers; Soft segment crystallinity; Strain recovery; Thermoplastic polyurethanes

Indexed keywords

EID: 79960962026     PISSN: 1788618X     EISSN: None     Source Type: Journal    
DOI: 10.3144/expresspolymlett.2011.88     Document Type: Article

References (32)

1. Lamba N. M. K., Woodhouse K. A., Cooper S. L.: Polyurethanes in biomedical applications. CRC Press, Boca Raton (1998).
2. Tuominen J., Kylmä J., Kapanen A., Venelampi O., Itävaara M., Seppälä J.: Biodegradation of lactic acid based polymers under controlled composting conditions and evaluation of the ecotoxicological impact. Biomacromolecules, 3, 445-455 (2002). DOI: 10.1021/bm0101522
3. Guelcher S. A.: Biodegradable polyurethanes: Synthesis and applications in regenerative medicine. Tissue Engineering Part B: Reviews, 14, 3-17 (2008). DOI: 10.1089/teb.2007.0133
4. Guan J., Sacks M. S., Beckman E. J., Wagner W. R.: Synthesis, characterization, and cytocompatibility of elastomeric, biodegradable poly(ester-urethane)ureas based on poly(caprolactone) and putrescine. Journal of Biomedical Materials Research, 61, 493-503 (2002). DOI: 10.1002/jbm.10204
5. Hassan M. K., Mauritz K. A., Storey R. F., Wiggins J. S.: Biodegradable aliphatic thermoplastic polyure - thane based on poly(ε-caprolactone) and L-lysine diisocyanate. Journal of Polymer Science Part A: Polymer Chemistry, 44, 2990-3000 (2006). DOI: 10.1002/pola.21373
6. Kylmä J., Seppälä J. V.: Synthesis and characterization of a biodegradable thermoplastic poly(ester'urethane) elastomer. Macromolecules, 30, 2876-2882 (1997). DOI: 10.1021/ma961569g
7. Ryynänen T., Nykännen A., Seppälä J. V.: Poly(CL/ DLLA-b-CL) multiblock copolymers as biodegradable thermoplastic elastomers. Express Polymer Letters, 2, 184-193 (2008). DOI: 10.3144/expresspolymlett.2008.23
8. Guan J., Sacks M. S., Beckman E. J., Wagner W. R.: Biodegradable poly(ether ester urethane)urea elastomers based on poly(ether ester) triblock copolymers and putrescine: Synthesis, characterization and cytocompatibility. Biomaterials, 25, 85-96 (2004). DOI: 10.1016/S0142-9612(03)00476-9
9. Hong Y., Guan J., Fujimoto K. L., Hashizume R., Pelinescu A. L., Wagner W. R.: Tailoring the degradation kinetics of poly(ester carbonate urethane)urea thermoplastic elastomers for tissue engineering scaffolds. Biomaterials, 31, 4249-4258 (2010). DOI: 10.1016/j.biomaterials.2010.02.005
10. Asplund J. O. B., Bowden T., Mathisen T., Hilborn J.: Synthesis of highly elastic biodegradable poly(urethane urea). Biomacromolecules, 8, 905-911 (2007). DOI: 10.1021/bm061058u
11. Skarja G. A.: The development and characterization of degradable, segmented polyurethanes containing amino acid-based chain extenders. PhD thesis, University of Toronto (2001).
12. Waletzko R. S., Korley L. T. J., Pate B. D., Thomas E. L., Hammond P. T.: Role of increased crystallinity in deformation-induced structure of segmented thermoplastic polyurethane elastomers with PEO and PEOPPO- PEO soft segments and HDI hard segments. Macromolecules, 42, 2041-2053 (2009). DOI: 10.1021/ma8022052
13. Albertsson A-C., Eklund M.: Synthesis of copolymers of 1,3-dioxan-2-one and oxepan-2-one using coordination catalysts. Journal of Polymer Science Part A: Polymer Chemistry, 32, 265-279 (1994). DOI: 10.1002/pola.1994.080320207
14. Domb A. J., Kumar N., Sheskin T., Bentolila A., Slager J., Teomim D.: Biodegradable polymers as drug carrier systems. in 'Polymeric biomaterials' (ed.: Dumitriu S.) Marcel Dekker, New York, 91-122 (2002).
15. Kricheldorf H. R., Rost S.: Biodegradable multiblock copolyesters prepared from ε-caprolactone, L-lactide, and trimethylene carbonate by means of bismuth hexanoate. Macromolecules, 38, 8220-8226 (2005). DOI: 10.1021/ma050439h
16. Pêgo A. P., Zhong Z., Dijkstra P. J., Grijpma D. W., Feijen J.: Influence of catalyst and polymerization conditions on the properties of 1,3-trimethylene carbonate and ε-caprolactone copolymers. Macromolecular Chemistry and Physics, 204, 747-754 (2003). DOI: 10.1002/macp.200390043
17. Shen Y., Shen Z., Zhang Y., Yao K.: Novel rare earth catalysts for the living polymerization and block copolymerization of ε-caprolactone. Macromolecules, 29, 8289-8295 (1996). DOI: 10.1021/ma9518060
18. Shen Y., Shen Z., Zhang Y., Huang Q., Shen L., Yuan H.: Random copolymerization of ε-caprolactone and tri - methylene carbonate with rare earth catalysts. Journal of Applied Polymer Science, 64, 2131-2139 (1997). DOI: 10.1002/(SICI)1097-4628(19970613)64:11<2131::AID-APP9>3.0.CO;2-K
19. Crescenzi V., Manzini G., Calzolari G., Borri C.: Thermodynamics of fusion of poly-(-propiolactone and poly-ε-caprolactone. Comparative analysis of the melting of aliphatic polylactone and polyester chains. European Polymer Journal, 8, 449-463 (1972). DOI: 10.1016/0014-3057(72)90109-7
20. Fischer E. W., Sterzel H. J., Wegner G.: Investigation of the structure of solution grown crystals of lactide copolymers by means of chemical reactions. Colloid and Polymer Science, 251, 980-990 (1973). DOI: 10.1007/BF01498927
21. Lipik V. T., Kong J. F., Chattopadhyay S., Widjaja L. K., Liow S. S., Venkatraman S. S., Abadie M. J. M.: Thermoplastic biodegradable elastomers based on ε-caprolactone and L-lactide block co-polymers: A new synthetic approach. Acta Biomaterialia, 6, 4261-4270 (2010). DOI: 10.1016/j.actbio.2010.05.027
22. Liow S. S., Widjaja L. K., Lipik V. T., Abadie M. J. M.: Synthesis, characterization and photopolymerization of vinyl functionalized poly (ε-caprolactone). Express Polymer Letters, 3, 159-167 (2009). DOI: 10.3144/expresspolymlett.2009.21
23. Dubois P., Jérôme R., Teyssié P.: Macromolecular engineering of polylactones and polylactides. 3. Synthesis, characterization, and applications of poly(iε-caprolactone) macromonomers macromonomers. Macromolecules, 24, 977-981 (1991). DOI: 10.1021/ma00005a002
24. Kowalski A., Duda A., Penczek S.: Kinetics and mechanism of cyclic esters polymerization initiated with tin(II) octoate, 1. Polymerization of ε-caprolactone. Macromolecular Rapid Communications, 19, 567-572 (1998). DOI: 10.1002/(SICI)1521-3927(19981101)19:11<567::AID-MARC567>3.0.CO;2-T
25. Kricheldorf H. R., Kreiser-Saunders I., Stricker A.: Polylactones 48. SnOct2-initiated polymerizations of lactide: A mechanistic study. Macromolecules, 33, 702-709 (2000). DOI: 10.1021/ma991181w
26. Drobny J. G.: Handbook of thermoplastic elastomers. William Andrew Publishing, New York (2007).
27. Kojio K., Furukawa M., Motokucho S., Shimada M., Sakai M.: Structure'mechanical property relationships for poly(carbonate urethane) elastomers with novel soft segments. Macromolecules, 42, 8322-8327 (2009). DOI: 10.1021/ma901317t
28. Korley L. T. J., Pate B. D., Thomas E. L., Hammond P. T.: Effect of the degree of soft and hard segment ordering on the morphology and mechanical behavior of semicrystalline segmented polyurethanes. Polymer, 47, 3073-3082 (2006). DOI: 10.1016/j.polymer.2006.02.093
29. Li Y., Ren Z., Zhao M., Yang H., Chu B.: Multiphase structure of segmented polyurethanes: Effects of hardsegment flexibility. Macromolecules, 26, 612-622 (1993). DOI: 10.1021/ma00056a010
30. Kajiyama T., MacKnight W. J.: Thermal properties of polyurethanes. Enthalpies and entropies of fusion. Polymer Journal, 1, 548-554 (1970).
31. Toki S., Sics I., Burger C., Fang D., Liu L., Hsiao B. S., Datta S., Tsou A. H.: Structure evolution during cyclic deformation of an elastic propylene-based ethylene'propylene copolymer. Macromolecules, 39, 3588-3597 (2006). DOI: 10.1021/ma0600106
32. Zhang Z., Grijpma D. W., Feijen J.: Triblock copolymers based on 1,3-trimethylene carbonate and lactide as biodegradable thermoplastic elastomers. Macromolecular Chemistry and Physics, 205, 867-875 (2004). DOI: 10.1002/macp.200300184