Polylactides—Methods of synthesis and characterization

Advanced Drug Delivery Reviews

Volumn 107, Issue , 2016, Pages 3-16

  Pretula, Julia ^a   Slomkowski, Stanislaw ^a   Penczek, Stanislaw ^a  

^a CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

Author keywords

Polycondensation of lactic acid; Polylactide characterization; Polylactides; Polymerization of lactides

Indexed keywords

ANIONIC POLYMERIZATION; BIOCOMPATIBILITY; CATIONIC POLYMERIZATION; CHARACTERIZATION; FUNCTIONAL POLYMERS; LACTIC ACID; MOLAR MASS; POLYCONDENSATION; POLYESTERS; POLYMERIZATION;

BIOCOMPATIBLE POLYMER; CRYSTALLINITIES; LACTIDE POLYMERIZATION; LACTIDES; MEDICAL IMPLANTS; METHODS OF SYNTHESIS; POLY LACTIDE; POLYMERIZATION PROCESS;

RING OPENING POLYMERIZATION;

BIOMATERIAL; DRUG CARRIER; LACTIC ACID; METAL ALKOXIDE; METAL OXIDE; MONOMER; POLYLACTIC ACID; POLYLACTIDE; POLYMER; UNCLASSIFIED DRUG; POLYESTER;

BIOCOMPATIBILITY; BIODEGRADABILITY; CATALYST; CHEMICAL ANALYSIS; CHEMICAL PROCEDURES; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DRUG DELIVERY SYSTEM; IMPLANT; INTERMETHOD COMPARISON; MECHANICAL PROPERTY; MOLECULAR WEIGHT; ORGANOCATALYST; PHYSICAL PARAMETERS; POLYCONDENSATION; POLYMERIZATION; PRIORITY JOURNAL; PURIFICATION; REVIEW; SOLUBILITY; SYNTHESIS; THERMAL PROPERTY; CHEMISTRY;

LACTIC ACID; POLYESTERS; POLYMERIZATION;

EID: 84976495261     PISSN: 0169409X     EISSN: 18728294     Source Type: Journal    
DOI: 10.1016/j.addr.2016.05.002     Document Type: Review

References (113)

1. [1] Drumright, R.E., Gruber, P.R., Henton, D.E., Polylactic acid technology. Adv. Mater. 12 (2000), 1841–1846.
2. [2] Gandini, A., Lacerda, T.M., From monomers to polymers from renewable resources: recent advances. Prog. Polym. Sci. 48 (2015), 1–39.
3. [3] Vert, M., Doi, Y., Hellwich, K.-H., Hess, M., Hodge, P., Kubisa, P., Rinaudo, M., Schué, F., Terminology for biorelated polymers. Pure Appl. Chem. 84 (2012), 377–410.
4. [4] Hazer, D.B., Kilicay, E., Hazer, B., Poly(3-hydroxyalkanoate)s: diversification and biomedical applications, a state of the art review. Mater. Sci. Eng. C32 (2012), 637–647.
5. [5] Hamad, K., Kaseem, M., Yang, H.W., Deri, F., Ko, Y.G., Properties and medical applications of polylactic acid: a review. Express Polym Lett 9 (2015), 435–455.
6. [6] Woodruff, M.A., Hutmacher, D.W., The return of a forgotten polymer—polycaprolactone in the 21st century. Prog. Polym. Sci. 35 (2010), 1217–1256.
7. [7] Kunduru, K.R., Basu, A.T., Zada, M.H., Domb, A.J., Castor oil-based biodegradable polyesters. Biomacromolecules 16 (2015), 2572–2587.
8. [8] Benninga, H., History of Lactic Acid Making. 1990, Kluwer Acad. Publishers, Dordrecht, 478 (p. 366).
9. [9] Wessermel, K., Arpe, H.-J., Industrial Organic Chemistry. 2008, VCH, Weinheim, 481 (p. 303).
10. [10] Matsutani, M., Kimura, Y., PLA synthesis. from the monomer to the polymer. Jiménez, A., Peltzer, M., Ruseckaite, R., (eds.) Poly(Lactic Acid) Science and Technology: Processing, Properties, Additives and Applications, 2015, The Royal Society of Chemistry, Cambridge, 353 (Chapter 1).
11. [11] Wee, Y.-J., Kim, J.-N., Ryu, H.-W., Biotechnological production of lactic acid and its recent applications. Food Technol. Biotechnol. 44 (2006), 163–172.
12. [12] Hartmann, M.H., High molecular weight polylactic acid polymers. Kaplan, D.L., (eds.) Biopolymers from Renewable Resources, 1998, Springer.
13. [13] Polymers of lactic acid. Kharas, G.B., Sanches-Riera, F., Severson, D.K., Mobley, D.P., (eds.) Plastics from Microbes, 1994, Hanser/Gardner Publications, Inc., 93.
14. [14] Van Ness, J.H., Hydroxy carboxylic acids. Kirk-Othermer Encyclopedia of Chem. Tech., third ed., 1981, J. Wiley & Sons, New York (13:80).
15. [15] Köhn, F.E., Van Den Berg, J.W.A., Van De Ridder, G., Feijen, J., The ring-opening polymerization of D,L-lactide in the melt initiated with tetraphenyltin. J. Appl. Polym. Sci. 29 (1984), 4265–4277.
16. [16] Moon, S.-I., Lee, C.-W., Taniguchi, I., Miyamoto, M., Kimura, Y., Melt/solid polycondensation of L-lactic acid: an alternative route to poly(L-lactic acid) with high molecular weight. Polymer 42 (2001), 5059–5062.
17. [17] Papaspyrides, C.D., Vouyiouka, S.N., (eds.) Solid State Polymerization, 2009, Wiley, 294.
18. [18] Ajoka, U., Enamoto, K., Suzuki, K., Yamaguchi, A., Basic properties of polylactic acid produced by the direct condensation polymerization of lactic acid. Bull. Chem. Soc. Jpn. 68 (1995), 2125–2131.
19. [19] Lim, L.-T., Auras, R., Rubiro, M., Processing technologies of poly(lactic acid). Prog. Polym. Sci. 33 (2008), 820–852.
20. [20] Witzke, D.R., Introduction to Properties, Engineering, and Prospects of Polylactide Polymers. (PhD thesis), 1997, Michigan State University, East Lansing, MI.
21. [21] Hartman, M.H., High molecular weight polylactic acid polymers. Kaplan, D.L., (eds.) Biopolymers from Renewable Resources, 1998, Springer-Verlag, Berlin/Heidelberg, 367–411.
22. [22] Dechy-Cabaret, O., Martin-Vaca, B., Borissou, D., Controlled ring-opening polymerization of lactide and glycolide. Chem. Rev. 104 (2004), 6147–6176.
23. [23] Degée, P., Dubois, P., Jérôme, R., Bulk polymerization of lactides initiated by aluminum isopropoxide. 2. Macromol. Chem. Phys. 198 (1997), 1973–1984.
24. [24] Degée, P., Dubois, P., Jérôme, R., Bulk polymerization of lactides initiated by aluminum isopropoxide. 3. Macromol. Chem. Phys. 198 (1997), 1985–1995.
25. [25] Lewiński, J., Horeglad, P., Wójcik, K., Justyniak, I., Chelation effect in polymerization of cyclic esters by metal alkoxides: structure characterization of the intermediate formed by primary insertion of lactide into the Al―OR bond of an organometallic initiator. Organometallics 24 (2005), 4588–4593.
26. [26] Wu, J., Pan, X., Tang, N., Lin, C.-C., Synthesis, characterization of aluminum complexes and the application in ring-opening polymerization of L-lactide. Eur. Polym. J. 43 (2007), 5040–5046.
27. 27Al NMR spectroscopy to studies of mechanisms of cyclic esters polymerization. Polimery 27 (2007), 722–729.
28. [28] Yoo, J.Y., Kim, Y., Ko, Y.S., Ring-opening polymerization behavior of L-lactide catalyzed by aluminum alkyl catalysts. J. Ind. Eng. Chem. 19 (2013), 1137–1143.
29. [29] Dubois, P., Jerome, R., Teyssie, P., Aluminum alkoxides—a family of versatile initiators for the ring-opening polymerization of lactones and lactides. Makromol. Chem. Macromol. Symp. 42/43 (1991), 103–116.
30. [30] Duda, A., Penczek, S., Mechanism of aliphatic polyester formation. Steinbüchel, A., Doi, Y., (eds.) Biopolymers, Vol. 3b: Polyesters II. Properties and Chemical Synthesis, 2002, Wiley-VCH, Weinheim, 371–429.
31. [31] Kowalski, A., Duda, A., Penczek, S., Polymerization of L,L-lactide initiated by aluminum isopropoxide trimer or tetramer. Macromolecules 31 (1998), 2114–2122.
32. [32] Duda, A., Penczek, S., Thermodynamics, kinetics and mechanisms of cyclic esters polymerization. Scholz, C., Gross, R.A., (eds.) ACS Symp. Ser. 764, Polymers from Renewable Resources, 2000, ACS, 160–198.
33. [33] Dobrzynski, P., Initiation process of L-lactide polymerization carried out with zirconium(IV) acetylacetonate. J. Polym. Sci. A Polym. Chem. 42 (2004), 1886–1900.
34. [34] Kowalski, A., Libiszowski, J., Majerska, K., Duda, A., Penczek, S., Kinetics and mechanism of ε-caprolactone and L,L-lactide polymerization coinitiated with zinc octoate or aluminum acetylacetonate: the next proofs for the general alkoxide mechanism and synthetic applications. Polymer 48 (2007), 3952–3960.
35. [35] Kowalski, A., Duda, A., Penczek, S., Kinetics and mechanism of cyclic esters polymerization initiated with tin(II) octoate, 1. Polymerization of ε-caprolactone. Macromol. Rapid Commun. 19 (1998), 567–572.
36. [36] Majerska, K., Duda, A., Penczek, S., Kinetics and mechanism of cyclic esters polymerisation initiated with tin(II) octoate, 4—influence of proton trapping agents on the kinetics of epsilon-caprolactone and L,L-dilactide polymerization. Macromol. Rapid Commun. 21 (2000), 1327–1332.
37. [37] Jaacks, V., Mathes, N., Formation of macrozwitterions in the polymerization of β-lactones initiated by tertiary amines. 2nd Communication on Macrozwitterions. Makromol. Chem. 131 (1970), 295–303.
38. [38] Mathes, N., Jaacks, V., Formation of macrozwitterions in the polymerization of β-propiolactone initiated by betaine. 4th Communication on Macrozwitterions. Makromol. Chem. 142 (1971), 209–225.
39. [39] Kazanski, K.S., Ptisyna, N.V., New functional poly(ethylene oxide)s: synthesis and application. Makromol. Chem. 190 (1989), 255–265.
40. [40] Corley, L.S., Vogl, O., Biela, T., Michalski, J., Penczek, S., Slomkowski, S., Optically active zwitterions. Makromol. Chem. Rapid Commun. 1 (1980), 715–718.
41. [41] Corley, L.S., Vogl, O., Biela, T., Penczek, S., Słomkowski, S., Kinetics of zwitterion formation from β-propiolactone and tertiary phosphines. Makromol. Chem. Rapid Commun. 2 (1981), 47–50.
42. [42] Biela, T., Penczek, S., Slomkowski, S., Vogl, O., Kinetic determination of stereoselectivity in the anionic polymerization of α-ethyl-α-phenyl-β-propiolactone. Makromol. Chem. 184 (1983), 811–819.
43. [43] Ishikawa, T., Superbases for Organic Synthesis: Guanidines, Amidines, Phosphazenes and Related Organocatalysts. 2009, John Wiley & Sons, 326.
44. [44] Boileau, S., Illy, N., Activation in anionic polymerization: why phosphazene bases are very exciting promoters. Prog. Polym. Sci. 36 (2011), 1132–1151.
45. [45] Jones, G.O., Chang, Y.A., Horn, H.W., Acharya, A.K., Rice, J.E., Hedrick, J.L., Waymouth, R.M., N-heterocyclic carbene-catalyzed ring opening polymerization of ε-caprolactone with and without alcohol initiators: insights from theory and experiment. J. Phys. Chem. B 119 (2015), 5728–5737.
46. [46] Chang, Y.A., Waymouth, R.M., Ion pairing effects in the zwitterionic ring opening polymerization of δ-valerolactone. Polym. Chem. 6 (2015), 5212–5218.
47. [47] Basko, M., Kubisa, P., Cationic polymerization of L,L-lactide. J. Polym. Sci. A Polym. Chem. 48 (2010), 2650–2658.
48. [48] Kamber, N.E., Jeong, W., Waymouth, R.M., Pratt, R.C., Lothmeijer, B.G.G., Hedrick, J.L., Organocatalytic ring-opening polymerization. Chem. Rev. 107 (2007), 5813–5840.
49. [49] Kowalski, A., Libiszowski, J., Duda, A., Penczek, S., Polymerization of L,L-dilactide initiated by tin(II) butoxide. Macromolecules 33 (2000), 1964–1971.
50. [50] Illy, N., Guegan, P., Boileau, S., Barbier, V., Winnik, M.A., Penelle, J., Phosphazene base: an anionic polymerization promotor. Fifth Young European Scientists Workshop, 2014 (Cracow, Poland).
51. [51] Kubisa, P., Penczek, S., Cationic activated monomer polymerization of heterocyclic monomers. Prog. Polym. Sci. 24 (1999), 1409–1437.
52. [52] Shibaseki, Y., Sanada, H., Yokai, M., Sanda, F., Endo, T., Activated monomer cationic polymerization of lactones and the application to well-defined block copolymer. Synthesis with seven-membered cyclic carbonate. Macromolecules 33 (2000), 4316–4320.
53. [53] Kricheldorf, H.R., Dunsing, R., Polylactones, 8. Mechanism of the cationic polymerization of L,L-dilactide. Makromol. Chem. 187 (1986), 1611–1625.
54. [54] Basko, M., Kubisa, P., Mechanism of propagation in the cationic polymerization of L,L-lactide. J. Polym. Sci. A Polym. Chem. 46 (2008), 7919–7923.
55. [55] Basko, M., Kubisa, P., Polyester oligodiols by cationic AM copolymerization of L,L-lactide and ε-caprolactone initiated by diols. J. Polym. Sci. A Polym. Chem. 45 (2007), 3090–3097.
56. [56] Basko, M., Kubisa, P., Cationic copolymerization of ε-caprolactone and L,L-lactide by an activated monomer mechanism. J. Polym. Sci. A Polym. Chem. 44 (2006), 7071–7081.
57. [57] Xia, C.C., Rong, X.U., Bin, L.I., Controlled/living ring-opening polymerization of ε-caprolactone catalyzed by phosphoric acid. Sci. China Chem. 55 (2012), 1257–1262.
58. [58] Basko, M., Bednarek, M., Synthesis of functionalized polylactide by cationic activated monomer polymerization. React. Funct. Polym. 72 (2012), 213–220.
59. [59] Gadzinowski, M., Sosnowski, S., Biodegradable/biocompatible ABC triblock copolymer bearing hydroxyl groups in the middle block. J. Polym. Sci. A Polym. Chem. 41 (2003), 3750–3760.
60. [60] Kowalski, A., Duda, A., Penczek, S., Kinetics and mechanism of cyclic esters polymerization initiated with tin(II) octoate. 3. Polymerization of L,L-dilactide. Macromolecules 33 (2000), 7359–7370.
61. [61] Borda, J., Keki, S., Bodnar, I., Nemeth, N., Zsuga, M., New potentially biodegradable polyurethanes. Polym. Adv. Technol. 17 (2006), 945–953.
62. [62] Takizawa, K., Nulwala, H., Hu, J., Yoshinaga, K., Hawker, C.J., Molecularly defined (L)-lactic acid oligomers and polymers: synthesis and characterization. J. Polym. Sci. A Polym. Chem. 46 (2008), 5977–5990.
63. [63] Weidner, S.M., Trimpin, S., Mass spectrometry of synthetic polymers. Anal. Chem. 82 (2010), 4811–4829.
64. [64] Dorgan, J.R., Janzen, J., Knauss, D.M., Hait, S.B., Limoges, B.R., Hutchinson, M.H., Fundamental solution and single-chain properties of polylactides. J. Polym. Sci. B Polym. Phys. 43 (2005), 3100–3111.
65. [65] Macdonald, R.T., McCarthy, S.P., Gross, R.A., Enzymatic degradability of poly(lactide): effects of chain stereochemistry and material crystallinity. Macromolecules 29 (1996), 7356–7361.
66. 13C CP-MAS NMR studies of the crystallinity and morphology of poly(L-lactide). Macromolecules 29 (1996), 8844–8851.
67. [67] Kasperczyk, J.E., Microstructure analysis of poly(1actic acid) obtained by lithium tert-butoxide as initiator. Macromolecules 28 (1995), 3937–3939.
68. 1H solution NMR study of poly(lactide). Macromolecules 30 (1997), 2422–2428.
69. [69] Coudane, J., Ustariz-Peyret, C., Schwach, G., Vert, M., More about the stereodependence of DD and LL pair linkages during the ring-opening polymerization of racemic lactide. J. Polym. Sci. A Polym. Chem. 35 (1997), 1651–1658.
70. [70] Bero, M., Dobrzynski, P., Kasperczyk, J., Synthesis of disyndiotactic polylactide. J. Polym. Sci. A Polym. Chem. 37 (1999), 4038–4042.
71. [71] Bero, M., Kasperczyk, J., Jedlinski, Z.J., Coordination polymerization of lactides. 1. Structure determination of obtained polymers. Makromol. Chem. 191 (1990), 2287–2296.
72. [72] Södergård, A., Stolt, M., Properties of lactic acid based polymers and their correlation with composition. Progr. Poly. Sci. 27 (2002), 1123–1163.
73. [73] Gadzinowski, M., Sosnowski, S., Slomkowski, S., Poly(L,L-lactide) and poly(L,L-lactide-co-glycolide) microparticles by dialysis. E-Polymers, 2005, article number 084 ( http://www.degruyter.com/view/j/epoly).
74. 2. J. Polym. Sci. B Polym. Phys. 50 (2012), 1383–1393.
75. [75] Bibi, G., Jung, Y., Lim, J.C., Kim, S.H., A fast approach to stereocomplex formation of high molecular weight polylactide using supercritical dimethyl ether. Polymer (Korea) 39 (2015), 453–460.
76. [76] De Santis, P., Kovacs, A.J., Molecular conformation of poly(S-lactic acid). Biopolymers 6 (1968), 299–306.
77. [77] Kalb, B., Pennings, A.J., General crystallization behaviour of poly(L-lactic acid). Polymer 21 (1980), 607–612.
78. [78] Hoogsteen, W., Postema, A.R., Pennings, A.J., Brinke, G., Zugenmaie, P., Crystal structure conformation and morphology of solution-spun poly(L-lactide) fibers. Macromolecules 23 (1990), 634–642.
79. [79] Kobayashi, J., Asahi, T., Ichiki, M., Oikawa, A., Suzuki, H., Watanabe, T., Fukada, E., Shikinami, Y., Structural and optical properties of poly lactic acids. J. Appl. Phys. 77 (1995), 2957–2973.
80. [80] Puiggali, J., Ikada, Y., Tsuji, H., Cartier, L., Okihara, T., Lotz, B., The frustrated structure of poly(l-lactide). Polymer 41 (2000), 8921–8930.
81. [81] Cartier, L., Okihara, T., Ikada, Y., Tsuji, H., Puiggali, J., Lotz, B., Epitaxial crystallization and crystalline polymorphism of polylactides. Polymer 41 (2000), 8909–8919.
82. [82] Zhang, J., Duan, Y., Sato, H., Tsuji, H., Noda, I., Yan, S., Y., O., Crystal modifications and thermal behavior of poly(L-lactic acid) revealed by infrared spectroscopy. Macromolecules 38 (2005), 8012–8021.
83. [83] Wasanasuk, K., Tashiro, K., Hanesaka, M., Ohhara, T., Kurihara, K., Kuroki, R., Tamada, T., Ozeki, T., Kanamoto, T., Crystal structure analysis of poly(L-lactic acid) α form on the basis of the 2-dimensional wide-angle synchrotron X-ray and neutron diffraction measurements. Macromolecules 44 (2011), 6441–6452.
84. [84] Sosnowski, S., Poly(L-lactide) microspheres with controlled crystallinity. Polymer 42 (2001), 637–643.
85. [85] Pawlak, T., Jaworska, M., Potrzebowski, M.J., NMR crystallography of α-poly(L-lactide). Phys. Chem. Chem. Phys. 15 (2013), 3137–3145.
86. [86] Kawai, T., Rahman, N., Matsuba, G., Nishida, K., Kanaya, T., Nakano, M., Okamoto, H., Kawada, J., Usuki, A., Honma, N., Nakajima, K., Matsuda, M., Crystallization and melting behavior of poly(L-lactic acid). Macromolecules 40 (2007), 9463–9469.
87. [87] Zhang, J., Tashiro, K., Tsuji, H., Domb, A.J., Disorder-to-order phase transition and multiple melting behavior of poly(l-lactide) investigated by simultaneous measurements of WAXD and DSC. Macromolecules 41 (2008), 1352–1357.
88. [88] Eling, B., Gogolewski, S., Pennings, A.J., Biodegradable materials of poly(L-lactic acid)—1. Melt-spun and solution-spun fibres. Polymer 23 (1982), 1587–1593.
89. [89] Cocca, M., Lorenzo, M.L.D., Malinconico, M., Frezza, V., Influence of crystal polymorphism on mechanical and barrier properties of poly(Llactic acid). Eur. Polym. J. 47 (2011), 1073–1080.
90. [90] Okihara, T., Tsuji, M., Kawaguchi, A., Katayama, K., Tsuji, H., Hyon, S.H., Ikada, Y., Crystal structure of stereocomplex of poly(L-lactide) and poly(D-lactide). J. Macromol. Sci. Part B Phys. 30 (1991), 119–140.
91. [91] Cartier, L., Okihara, T., Lotz, B., Triangular polymer single crystals: stereocomplexes twins and frustrated structures. Macromolecules 30 (1997), 6313–6322.
92. [92] Pan, P., Yang, J., Shan, G., Bao, Y., Weng, Z., Cao, A., Yazawa, K., Inoue, Y., Temperature-variable FTIR and solid-state 13C NMR investigations on crystalline structure and molecular dynamics of polymorphic Poly(L-lactide) and poly(L-lactide)/poly(D-lactide) stereocomplex. Macromolecules 45 (2011), 189–197.
93. [93] Chen, W., Reichert, D., Miyoshi, T., Helical jump motions of poly(L-lactic acid) chains in the α phase as revealed by solid-state NMR. J. Phys. Chem. B 119 (2015), 4552–4563.
94. [94] Tsai, C.C., Wu, R.J., Cheng, H.Y., Li, S.C., Siao, Y.Y., Kong, D.C., Jang, G.W., Crystallinity and dimensional stability of biaxial oriented poly(lactic acid) films. Polym. Degrad. Stab. 95 (2010), 1292–1298.
95. [95] Fischer, E.W., Sterzel, H.J., Wegner, G., Investigation of the structure of solution grown crystals of lactide copolymers by means of chemical reactions. Kolloid Z. Z. Polym. 251 (1973), 980–990.
96. [96] Saeidlou, S., Huneault, M.A., Li, H., Park, C.B., Poly(lactic acid) crystallization. Prog. Polym. Sci. 37 (2012), 1657–1677.
97. [97] Jamshidi, K., Hyon, S.H., Ikada, Y., Thermal characterization of polylactides. Polymer 29 (1988), 2229–2234.
98. [98] Abe, H., Kikkawa, Y., Inoue, Y., Doi, Y., Morphological and kinetic analyses of regime transition for poly[(S)-lactide] crystal growth. Biomacromolecules 2 (2001), 1007–1014.
99. [99] Dorgan, J.R., Janzen, J., Clayton, M.P., Hait, S.B., Knauss, D.M., Melt rheology of variable L-content poly(lactic acid). J. Rheol. 49 (2005), 607–619.
100. [100] Flory, P.J., Theory of crystallization in copolymers. Trans. Faraday Soc. 51 (1955), 848–857.
101. [101] Baur, V.H., Einfluss der sequenzlangenverteilung auf das schmelz-ende von copolymeren. Makromol. Chem. 98 (1966), 297–301.
102. [102] Ahmed, J., Zhang, J.X., Song, Z., Varshney, S.K., Thermal properties of polylactides: effect of molecular mass and nature of lactide isomer. J. Therm. Anal. Calorim. 95 (2009), 957–964.
103. [103] Tsuji, H., Ikada, Y., Stereocomplex formation between enantiomeric poly(lactic acid)s. XI. Mechanical properties and morphology of solution-cast films. Polymer 40 (1999), 6699–6708.
104. [104] Biela, T., Duda, A., Penczek, S., Enhanced melt stability of star-shaped stereocomplexes as compared with linear stereocomplexes. Macromolecules 39 (2006), 3710–3713.
105. [105] Törmälä, B., Biodegradable self-reinforced composite materials; manufacturing structure and mechanical properties. Clin. Mater. 10 (1992), 29–34.
106. [106] Grijpma, D.W., Nijenhuis, A.J., van Wijk, P.G.T., Pennings, A.J., High impact strength as-polymerized PLLA. Polym. Bull. 29 (1992), 571–578.
107. [107] Fambri, L., Pegoretti, A., Fenner, R., Incardona, S.D., Migliaresi, C., Biodegradable fibres of poly(L-lactic acid) produced by melt spinning. Polymer 38 (1997), 79–85.
108. [108] Jacobsen, S., Fritz, H.G., Plasticizing polylactide—the effect of different plasticizers on the mechanical properties. Polym. Eng. Sci. 39 (1999), 1303–1310.
109. [109] Engelberg, I., Kohn, J., Physicomechanical properties of degradable polymers used in medical applications—a comparative-study. Biomaterials 12 (1991), 292–304.
110. [110] Perego, G., Cella, G.D., Bastioli, C., Effect of molecular weight and crystallinity on poly(lactic acid) mechanical properties. J. Appl. Polym. Sci. 59 (1996), 37–43.
111. [111] Grijpma, D.W., Pennings, A.J., (Co)polymers of L-lactide. 2. Mechanical properties. Macromol. Chem. Phys. 195 (1994), 1649–1663.
112. [112] Tsuji, H., Ikada, Y., Hyon, S.-H., Kimura, Y., Kitao, T., Stereocomplex formation between enantiomeric poly(lactic acid). VIII. Complex fibers spun from mixed solution of poly(D-lactic acid) and poly(L-lactic acid). J. Appl. Polym. Sci. 51 (1994), 337–344.
113. [113] Endres, H.-J., Siebert-Raths, A., Engineering Biopolymers; Markets, Manufacturing, Properties, and Applications. 2011, Carl Hanser Verlag, München, 674 (Chapter 5).