Chemical Compatibility of Poly(Lactic Acid): A Practical Framework Using Hansen Solubility Parameters

Poly(Lactic Acid): Synthesis, Structures, Properties, Processing, and Applications

Volumn , Issue , 2010, Pages 83-95

  Abbott, Steven ^a  

^a ABBOTT LABORATORIES   (United Kingdom)

Author keywords

PLA plasticizer, chemical compatibility with PLA reducing tendency for plasticizer to bleed out; Poly(lactic acid) chemical compatibility practical framework using Hansen solubility parameters; Polymer compatibility polymer blending with PLA, holding great promise for overcoming poor mechanical resilience

Indexed keywords

EID: 84865654385     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470649848.ch7     Document Type: Chapter

References (60)

1. T. Oishi, J. M. Prausnitz, Estimation of solvent activities in polymer solutions using a group-contribution method, Ind. Eng. Chem. Process Des. Dev. 1978, 17, 333-339.
2. R. Todeschini, V. Consonni, Handbook of Molecular Descriptors, Wiley-VCH, Weinheim, 2000.
3. S. H. Hilal, L. A. Carreira, S. W. Karickhoff, C. M. Melton, Estimation of gas-liquid chromatographic retention times from molecular structure, J. Chromatogr. A 1994, 662, 269-280.
4. P. J. Flory, Principles of Polymer Chemistry, Cornell University Press, New York, 1953.
5. C. M. Hansen, Hansen Solubility Parameters: A User's Handbook, CRC Press, Boca Raton, FL, 2007.
6. E. Stefanis, C. Panayiotou, Prediction of Hansen solubility parameters with a new group-contribution method, Int. J. Thermophys. 2008, 29, 568-585.
7. M. Belmares, M. Blanco, W. A. GoddardIII, R. B. Ross, G. Caldwell, S. H. Chou, J. Pham, P. M. Olofson, C. Thomas, Hildebrand and Hansen solubility parameters from molecular dynamics with applications to electronic nose polymer sensors, J. Comput. Chem. 2004, 25, 1814-1826.
8. S. J. Abbott, C. M. Hansen, HSPiP-Hansen Solubility Parameters in Practice, www.hansen-solubility.com 2008.
9. P. van deWitte, A. Boorsma, H. Esselbrugge, P. J. Dijkstra, J. W. A. van den Berg, J. Feijen, Differential scanning calorimetry study of phase transitions in poly(lactide)-chloroform- methanol systems, Macromolecules 1996, 29, 212-219.
10. P. van deWitte, et al., In situ analysis of solvent/nonsolvent exchange and phase separation processes during the membrane formation of polylactides, J. Appl. Polym. Sci. 1996, 61, 685-695.
11. P. van de Witte, et al., Phase separation processes in polymer solutions in relation to membrane formation, J. Membr. Sci. 1996, 117, 1-31.
12. P. van de Witte, et al., Phase transitions during membrane formation of polylactide. I. Amorphological study of membranes obtained from the system polylactide-chloroform-methanol, J. Membr. Sci. 1996, 113, 223-236.
13. P. van deWitte, et al., Metastable liquid-liquid and solid-liquid phase boundaries in polymer-solvent-nonsolvent systems, J. Polym. Sci. Part B 1997, 35, 763-770.
14. P. van de Witte, et al., A morphological study of membranes obtained from systems polylactide-dioxane-methanol, polylactide-- dioxane-water, and polylactide-N-methyl pyrrolidone-water, J. Polym. Sci. Part B 1996, 34, 2569-2578.
15. P. van deWitte, et al., Phase behavior of polylactides in solvent-nonsolvent mixtures, J. Polym. Sci. Part B 1996, 34, 2553-2568.
16. K. S. Anderson, K. M. Schreck, M. A. Hillmyer, Toughening polylactide, Polym. Rev. 2008, 48, 85-108.
17. R. E. Conn, J. J. Kolstad, J. F. Borzelleca, D. S. Dixler, L. J. FilerJr., B. N. LaDu, M. W. Pariza, Safety assessment of polylactide (PLA) for use as a food-contact polymer, Food Chem. Toxicol. 1995, 33, 273-283.
18. M. Mutsuga, U. Kawamura, K. Tanamoto, Migration of lactic acid, lactide and oligomers from polylactide food-contact materials, Food Addit. Contam. 2008, 25, 1283-1290.
19. E. Piorkowska, Z. Kulinski, A. Galeski, R. Masirek, Plasticization of semicrystalline poly(L-lactide) with poly(propylene glycol), Polymer 2006, 47, 7178-7188.
20. Z. Kulinski, et al., Plasticization of poly(L-lactide) with poly(propylene glycol), Biomacromolecules 2006, 7, 2128-2135.
21. X. Chen, K. H. Schilling,W. E. KellyJr.,U.S. Patent 5,908,918, 1998 (to Chronopol Inc.).
22. T. Matsumoto, H. Shinnumadate, S. Kumazawa, M. Kimura, U.S. Patent 7,351,785, 2008 (to Toray Industries, Inc. (Japan)).
23. Z. Ren, L. Dong, Y. Yang, Dynamic mechanical and thermal properties of plasticized poly(lactic acid), J. Appl. Polym. Sci. 2006, 101, 1583-1590.
24. N. Ljungberg, B. Wesslèn, Tributyl citrate oligomers as plasticizers for poly(lactic acid): thermo-mechanical film properties and aging, Polymer 2003, 44, 7679-7688.
25. R. Bhardwaj, A. K. Mohanty, Modification of brittle polylactide by novel hyperbranched polymer-based nanostructures, Biomacromolecules 2007, 8, 2476-2484.
26. T. Yokohara, M. Yamaguchi, Structure and properties for biomass-based polyester blends of PLA and PBS, Eur. Polym. J. 2008, 44, 677-685.
27. B. M. P. Ferreira, C. A. C. Zavaglia, E. A. R. Duek, Films of PLLA/PHBV: thermal, morphological, and mechanical characterization, J. Appl. Polym. Sci. 2002, 86, 2898-2906.
28. R. G. Sinclair, U.S. Patent 4,057,537, 1977, (to Gulf Oil Corporation).
29. Y. Li, H. Shimizu, Toughening of polylactide by melt blending with a biodegradable poly(ether)urethane elastomer, Macromol. Biosci. 2007, 7, 921-928.
30. K. S. Anderson, S. H. Lim, M. A. Hillmyer, Toughening of polylactide by melt blending with linear low-density polyethylene, J. Appl. Polym. Sci. 2003, 89, 3757-3768.
31. K. S. Anderson, M. A. Hillmyer, The influence of block copolymer microstructure on the toughness of compatibilized polylactide/polyethylene blends, Polymer 2004, 45, 8809-8823.
32. G. L. Baker, E. B. Vogel, M. R. SmithIII, Glass transitions in polylactides, Polym. Rev. 2008, 48, 64-84.
33. N. Wang, X. Zhang, X. Ma, J. Fang, Influence of carbon black on the properties of plasticized poly(lactic acid) composites, Polym. Degrad. Stabil. 2008, 93, 1044-1052.
34. S. Detriche, G. Zorzini, J. F. Colomer, A. Fonseca, J. B. Nagy, Application of Hansen solubility parameters theory to carbon nanotubes, J. Nanosci. Nanotechnol. 2008, 8, 1-11.
35. H. S. Kim, B. H. Park, J. S. Yoon, H. J. Jin, Preparation of biodegradable nanocomposites by incorporation of functionalized carbon nanotubes, Key Eng. Mater. 2006, 326-328, 1785-1788.
36. Y. Shimamura, A. Yamamoku, K. Tohgo, S. Tasaka, H. Araki, Mechanical properties of carbon nanofiber reinforced polylactic acid, Key Eng. Mater. 2007, 345-346, 1225-1228.
37. H. J. M. Hanley, C.D. Muzny, D. L. Ho, C. J. Glinka, E. Manias, A SANS study of organoclay dispersions, Int. J. Thermophys. 2001, 22, 1435-1448.
38. J. H. Chang, Y. U. An, G. S. Sur, Poly(lactic acid) nanocomposites with various organoclays. I. Thermomechanical properties, morphology, and gas permeability, J. Polym. Sci. Part B 2003, 41, 94-103.
39. J. H. Chang, Y. U. An, D. Cho, E. P. Giannelis, Poly(lactic acid) nanocomposites: comparison of their properties with montmorillonite and synthetic mica, Polymer 2003, 44, 3715-3720.
40. C. Thellen, C. Orroth, D. E. Froio, D. Ziegler, J. Lucciarini, R. Farrell, N. A. D'Souza, J. A. Ratto, Influence of montmorillonite layered silicate on plasticized poly(L-lactide) blown films, Polymer 2005, 46, 11716-11727.
41. Z. Yua, J. Yin, S. Yan, Y. Xie, J. Ma, X. Chen, Biodegradable poly(L-lactide)/poly(3-caprolactone)-modified montmorillonite nanocomposites: preparation and characterization, Polymer 2007, 48, 6439-6447.
42. H.Tian,H.Tagaya,Preparation, characterization andmechanical properties of the polylactide/perlite and the polylactide/montmorillonite composites, J. Mater. Sci. 2007, 42, 3244-3250.
43. D. Burgentzlé, J. Duchet, J. F. Gérard, A. Jupin, B. Fillon, Solvent-based nanocomposite coatings. I. Dispersion of organophilic montmorillonite in organic solvents, J. Colloid Interface Sci. 2004, 278, 26-39.
44. S. Bourbigot, G. Fontaine, S. Bellayer, R. Delobel, Processing and nanodispersion: a quantitative approach for polylactide nanocomposite, Polym. Test. 2008, 27, 2-10.
45. J. H. Shim, E. S. Kim, J. H. Joo, J. S. Yoon, Properties and morphology of poly(L-lactide)/clay composites according to the clay modification, J. Appl. Polym. Sci. 2006, 102, 4983-4988.
46. P. Bordes, E. Pollet, L. Avérous, Nano-biocomposites: biodegradable polyester/nanoclay systems, Prog. Polym. Sci. 2009, 34, 125-155.
47. G. Colomines, S. Domenek,V. Ducruet, A. Guinault, Influences of the crystallisation rate on thermal and barrier properties of polylactide acid (PLA) food packaging films, Int. J. Mater. Form. 2008, 1(1), 607-610.
48. R. Auras, B. Harte, S. Selke, Sorption of ethyl acetate and D-limonene in poly(lactide) polymers, J. Sci. Food Agric. 2006, 86, 648-656.
49. D. V. Plackett, V. K. Holm, P. Johansen, S. Ndoni, P. V. Nielsen, T. Sipilainen-Malm, A. Södergård, S. Verstichel, Characterization of L-polylactide and L-polylactide-polycaprolactone co-polymer films for use in cheese-packaging applications, Packag. Technol. Sci. 2006, 19, 1-24.
50. E. Almenar, H. Samsudin, R. Auras, B. Harte, M. Rubino, Postharvest shelf life extension of blueberries using a biodegradable package, Food Chem. 2008, 110, 120-127.
51. L. Bao, et al., Gas permeation properties of poly(lactic acid) revisited, J. Membr. Sci. 2006, 285, 166-172.
52. H. Tsuji, K. Ankara, Poly(L-lactide). IX. Hydrolysis in acid media, J. Appl. Polym. Sci. 2002, 86, 186-194.
53. C. M. Hansen, Polymer science applied to biological problems: prediction of cytotoxic drug interactions with DNA, Eur. Polym. J. 2008, 44, 2741-2748.
54. M. K. Lai, R. C. C. Tsiang, Microencapsulation of acetaminophen into poly(L-lactide) by three different emulsion solvent-evaporation methods, J. Microencapsul. 2005, 22, 261-274.
55. Y. Çirpanli, N.Ünlü, S.Çalis,A.AtíllaHincal, Formulation and in vitro characterization of retinoic acid loaded poly(lactic-coglycolic acid) microspheres, J. Microencapsul. 2005, 22, 877-889.
56. Y. Özalp, N. Özdemir, V. Hasirci, Vancomycin release from poly(D,L-lactide) and poly(lactide-co-glycolide) disks, J. Microencapsul. 2002, 19, 83-94.
57. X. Chen, C. P. Ooi, W. S. Lye, T. H. Lim, Sustained release of ganciclovir from poly(lactide-co-glycolide) microspheres, J. Microencapsul. 2005, 22, 621-631.
58. K. S. Soppimath, T. M. Aminabhavi, Ethyl acetate as a dispersing solvent in the production of poly(DL-lactide-co-glycolide) microspheres: effect of process parameters and polymer type, J. Microencapsul. 2002, 19, 281-292.
59. S. A. Elkheshen, M. A. Radwan, Sustained release microspheres of metoclopramide using poly(D,L-lactide-co-glycolide) copolymers, J. Microencapsul. 2000, 17, 425-435.
60. M. D. Blanco, R. L. Sastre, C. Teijón, R. Olmo, J. M. Teijón, 5- Fluorouracil-loaded microspheres prepared by spray-drying poly(D,L-lactide) and poly(lactide-co-glycolide) polymers: characterization and drug release, J. Microencapsul. 2005, 22, 671-682.