Ring-opening polymerization of L -lactide using half-titanocene complexes of the ATiCl2Nu type: Synthesis, characterization, and thermal properties

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 51, Issue 5, 2013, Pages 1162-1174

  Saridis, Emmanuel ^a   Maroulas, Serafeim Dionysios ^a   Pitsikalis, Marinos ^a  

^a UNIVERSITY OF ATHENS   (Greece)

Author keywords

gel permeation chromatography; L lactide; ring opening polymerization; thermal properties; titanium mediated polymerization

Indexed keywords

BENZYL ALCOHOL; ETHOXY GROUP; IN-SITU FORMATIONS; INDENYL; KINETIC STUDY; KISSINGER METHODS; L-LACTIDE; LACTIDES; NARROW MOLECULAR WEIGHT DISTRIBUTIONS; PENTAMETHYLCYCLOPENTADIENYL; PLLA; POLYMERIZATION REACTION;

ACTIVATION ENERGY; CHLORINE COMPOUNDS; DECOMPOSITION; DIFFERENTIAL SCANNING CALORIMETRY; GEL PERMEATION CHROMATOGRAPHY; POLYMERS; SYNTHESIS (CHEMICAL); THERMODYNAMIC PROPERTIES; THERMOGRAVIMETRIC ANALYSIS; TITANIUM; TOLUENE;

POLYMERIZATION;

EID: 84872965192     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.26479     Document Type: Article

References (108)

1. (a), K. M. Nampoothiri, N. R. Nair, R. P. John, Bioresour. Technnol. 2010, 101, 8493-8501
2. (b), D. J. Darensbourg, O. Karroonnirum, Organometallics 2010, 29, 5627-5634
3. (c), R. P. John, K. M. Nampoothiri, A. Pandey, Proc. Biochem. 2006, 41, 759-763.
4. H. Abe, Macromol. Biosci. 2006, 6, 469-486.
5. (a), S. Inkinen, M. Hakkainen, A.-C. Albertsson, A. Södergard, Biomacromolecules 2011, 12, 523-532
6. (b), L.-T. Lim, R. Auras, M. Rubino, Progr. Polym. Sci. 2008, 33, 820-852.
7. (a), H. Tsuji, Y. Sugiura, Y. Sakamoto, L. Bouapao, S. Itsuno, Polymer 2008, 49, 1385-1397
8. (b), Y. Shen, K. J. Zhu, Z. Shen, K.-M. Yao, J. Polym. Sci. Part A: Polym. Chem. 1996, 34, 1799-1805
9. (c), K. Van Butsele, R. Jérôme, C. Jérôme, Polymer 2007, 48, 7431-7443.
10. M. Mazzeo, M. Lamberti, I. D'Auria, S. Milione, J. C. Peters, C. Pellecchia, J. Polym. Sci. Part A: Polym. Chem. 2010, 48, 1374-1382.
11. D. J. Darensbourg, O. Karroonnirum, Macromolecules 2010, 43, 8880-8886.
12. (a), J. M. Becker, R. J. Pounder, A. P. Dove, Macromol. Rapid Commun. 2010, 31, 1923-1937
13. (b), M. J. Stanford, A. P. Dove, Chem. Soc. Rev. 2010, 39, 486-494.
14. W.-W. Wang, W.-Y. Ren, L. Jiang, Y. Dan, J. Appl. Polym. Sci. 2010, 118, 2379-2388.
15. (a), H. Tsuji, K. Shimizu, Y. Sakamoto, A. Okumura, Polymer 2011, 52, 1318-1325
16. (b), V. D. Jahno, G. B. M. Ribeiro, L. A. dos Santos, R. Ligabue, S. Einfolt, M. R. W. Ferreira, K. F. Bombonato-Prado, J. Biomed. Mater. Res. Part A 2007, 83A, 209-215
17. (c), P. J. Dijkstra, H. Du, J. Feijen, Polym. Chem. 2011, 2, 520-527.
18. (a), M. H. Chisholm, Pure Appl. Chem. 2010, 82, 1647-1662
19. (b), B. G. G. Lohmeijer, R. C. Pratt, F. Leibfarth, J. W. Logan, D. A. Long, A. P. Dove, F. Nederberg, J. Choi, C. Wade, R. M. Waymouth, J. L. Hedrick, Macromolecules 2006, 39, 8574-8583
20. (c), F. Nederberg, E. F. Connor, M. Moeller, T. Glauser, J. L. Hedrick, Angew. Chem. Int. Ed. 2001, 40, 2712-2715
21. (d), B. J. O'Keefe, M. A. Hillmyer, W. B. Tolman, J. Chem. Soc. Dalton Trans. 2001, 15, 2215-2224
22. (e), O. Dechy-Cabaret, B. Martin-Vaca, D. Bourissou, Chem. Rev. 2004, 104, 6147-6176.
23. (a), A.-C. Albertsson, R. K. Srivastava, Adv. Drug Deliv. Rev. 2008, 60, 1077-1093
24. (b), K. Numata, R. K. Srivastava, A. Finne-Wistrand, A.-C. Albertsson, Y. Doi, H. Abe, Biomacromolecules 2007, 8, 3115-3125.
25. M. Básko, P. Kubisa, J. Polym. Sci. Part A: Polym. Chem. 2010, 48, 2650-2658.
26. H. R. Kricheldorf, M. Berl, N. Scharnagl, Macromolecules 1988, 21, 286-293.
27. (a), J. Dahlamann, G. Rafler, K. Fechner, B. Mehlis, Br. Polym. J. 1990, 23, 235-240
28. (b), H. Li, C. Wanh, F. Bai, J. Yue, H.-G. Woo, Organometallics 2004, 23, 1411-1415
29. (c), W. M. Stevels, M. J. K. Ankone', P. J. Dijkstra, J. Feijen, Macromolecules 1996, 29, 3332-3333
30. (d), W. M. Stevels, M. J. K. Ankone', P. J. Dijkstra, J. Feijen, Macromolecules 1996, 29, 6132-6138
31. (d), M. Save, M. Schappacher, A. Soum, Macromol. Chem. Phys. 2002, 203, 889-899
32. (e), M. Save, A. Soum, Macromol. Chem. Phys. 2002, 203, 2591-2603
33. (f), W. M. Stevels, M. J. K. Ankone', P. J. Dijkstra, J. Feijen, Macromol. Chem. Phys. 1995, 196, 1153-1161.
34. (a), K. Soga, T. Shiono, Prog. Polym. Sci. 1997, 22, 1503-1546
35. (b), C. Jenny, P. Maddox, Curr. Opin. Solid State Mater. Sci. 1998, 3, 94-103
36. (c), P. Corradini, G. Guerra, L. Cavallo, Acc. Chem. Res. 2004, 37, 231-241
37. (d), G. W. Coates, Chem. Rev. 2000, 100, 1223-1252
38. (e), C. S. Bajgur, S. Sivaram, Curr. Sci. 2000, 78, 1325-1335
39. (f), G. W. Coates, P. D. Hustad, S. Reinartz, Angew. Chem. Int. Ed. 2002, 41, 2236-2257
40. (g), R. Mülfaupt, Macromol. Chem. Phys. 2003, 204, 289-327.
41. (a), W. Kuran, Principles of Coordination Polymerization; Wiley: New York, 2001
42. (b), J. D. Scollard, D. H. McConville, N. C. Payne, J. J. Vittal, Macromolecules 1996, 29, 5241-5243
43. (c), H. Fuhrmann, S. Brenner, P. Arndt, R. Kempe, Inorg. Chem. 1996, 35, 6742-6745
44. (d), Y. Imanishi, K. Nomura, J. Polym. Sci. Part A: Polym. Chem. 2000, 38, 4613-4626
45. (e), G. Ricci, L. Porri, A. Giarrusso, Macromol. Symp. 1995, 89, 383-392
46. (f), A. Rodriguez-Delgado, W. R. Marriot, E. Y.-X. Chen, Macromolecules 2004, 37, 3092-3100
47. (g), S. Mourmouris, K. Kostakis, M. Pitsikalis, N. Hadjichristidis, J. Polym. Sci. Polym. Chem. Ed. 2005, 43, 6503-6514
48. (h), A. Touris, K. Kostakis, S. Mourmouris, V. Kotzabasakis, M. Pitsikalis, N. Hadjichristidis, Macromolecules 2008, 41, 2426-2438.
49. (a), T. K. Prakasha, R. O. Day, R. R. Holmes, J. Am. Chem. Soc. 1993, 115, 2690-2695
50. (b), Y. Nakayama, K. Watanabe, N. Ueyama, A. Nakamura, A. Harada, J. Okuda, Organometallics 2000, 19, 2498-2503
51. (c), Y. Takashima, Y. Nakayama, K. Watanabe, T. Itono, N. Ueyama, A. Nakamura, H. Yasuda, A. Harada, Macromolecules 2002, 35, 7538-7544
52. (d), Y. Takashima, Y. Nakayama, T. Hirao, H. Yasuda, A. Harada, J. Organomet. Chem. 2004, 689, 612-619.
53. M. D. Jones, M. G. Cavidson, G. Kociok-Kohn, Polyhedron 2010, 29, 697-700.
54. N. Petzetakis, M. Pitsikalis, N. Hadjichristidis, J. Polym. Sci. Part A: Polym. Chem. 2010, 48, 1092-1103.
55. D. Uhrig, J. W. Mays, J. Polym. Sci. Part A: Polym. Chem. 2005, 43, 6179-6222.
56. N. Hadjichristidis, H. Iatrou, S. Pispas, M. Pitsikalis, J. Polym. Sci. Part A: Polym. Chem. 2000, 38, 3211-3234.
57. (a), G. Karanikolopoulos, C. Batis, M. Pitsikalis, N. Hadjichristidis, Macromolecules 2001, 34, 4697-4705
58. (b), G. Karanikolopoulos, C. Batis, M. Pitsikalis, N. Hadjichristidis, Macromol. Chem. Phys. 2003, 204, 831-840.
59. A. Pietrangelo, M. A. Hillmyer, W. B. Tolman, Chem. Commun. 2009, 2736-2737.
60. J. Baran, A. Duda, A. Kowalski, R. Szymanski, S. Penczek, Macromol. Rapid Commun. 1997, 18, 325-333.
61. (a), K. A. Thakur, R. T. Kean, E. S. Hall, J. J. Kolstad, T. A. Lindgren, M. A. Doscotch, J. I. Siepmann, E. J. Munson, Macromolecules 1997, 30, 2422-2428
62. (b), M. T. Zell, B. E. Padden, A. J. Paterick, K. A. Thakur, R. T. Kean, M. A. Hillmyer, E. J. Munson, Macromolecules 2002, 35, 7700-7707.
63. (a), F. Hernández Sánchez, J. Mollina Mateo, F. J. Romero Colomer, M. Salmerõn Sánchez, J. L. Gõmez Ribelles, J. F. Mano, Biomacromolecules 2005, 6, 3283-3290
64. (b), J.-R. Sarasua, R. E. Prud'homme, M. Wisniewski, A. Le Borgne, N. Spassky, Macromolecules 1998, 31, 3895-3905
65. (c), T. Miyata, T. Masuko, Polymer 1998, 39, 5515-5521
66. (d), E. Zuza, M. Ugartemendia, A. Lopez, E. Meaurio, A. Lejardi, J.-R. Sarasua, Polymer 2008, 49, 4427-4432
67. (e), S. Iannace, L. Nicolais, J. Appl. Polym. Sci. 1997, 64, 911-919
68. (f), C. Migliaresi, A. De Lollis, L. Fambri, D. Cohn, Clin. Mater. 1991, 8, 111-118
69. (g), G. L. Baker, E. B. Vogel, M. R. Smith, Polym. Rev. 2008, 48, 64-84
70. (h), C. Nakafuku, S. Takehisa, J. Appl. Polym. Sci. 2004, 93, 2164-2173.
71. K. Jamshidi, S.-H. Hyon, Y. Okada, Polymer 1988, 29, 2229-2234.
72. (a), A. Celli, M. Scandola, Polymer 1992, 33, 2699-2703
73. (b), H. Cai, V. Dave, R. A. Gross, P. McCarthy, J. Polym. Sci. Part B: Polym. Phys. 1996, 34, 2701-2708.
74. D. Garlotta, J. Polym. Environ. 2002, 9, 63-84.
75. R. Auras, B. Harte, S. Selke, Macromol. Biosci. 2004, 4, 835-864.
76. E. W. Fischer, H. J. Sterzel, G. Wegner, Kolloid Z. Z. Polym. 1973, 251, 980-990.
77. (a), P. De Santis, A. Kovacs, Biopolymers 1968, 6, 299-306
78. (b), W. Hoogsten, A. R. Postema, A. J. Pennings, G. Brinke, P. Zugenmaier, Macromolecules 1990, 23, 634-642.
79. B. Kalb, A. J. Pennings, Polymer 1980, 21, 607-612.
80. (a), T. Miyata, T. Masuko, Polymer 1997, 38, 4003
81. (b), C. Alemán, B. Lotz, J. Puiggali, Macromolecules 2001, 34, 4795-4801
82. (c), S. Sasaki, T. Asakura, Macromolecules 2003, 36, 8385-8390.
83. J. Puiggali, Y. Ikada, H. Tsuji, B. Lotz, Polymer 2000, 41, 8921-8930.
84. T. Okihara, K. Okumura, A. Kawaguchi, J. Macromol. Sci. Phys. 2003, B42, 875-888.
85. (a), H. Tsuji, Y. Ikada, Polymer 1995, 36, 2709-2716
86. (b), H. Tsuji, Y. Ikada, Polymer 1996, 37, 595-601.
87. H. Zou, C. Yi, L. Wang, H. Liu, W. Xu, J. Therm. Anal. Calorim. 2009, 97, 929-935.
88. (a), F.-D. Kopinke, M. Remmler, K. Mackenzie, M. Moder, O. Wachsen, Polym. Degrad. Stab. 1996, 53, 329-342
89. (b), H. Nishida, T. Mori, S. Hoshihara, Y. Fan, Y. Shirai, T. Endo, Polym. Degrad. Stab. 2003, 81, 515-523
90. (c), I. C. McNeill, H. A. Leiper, Polym. Degrad. Stab. 1985, 11, 309-326.
91. K. I. Park, M. A. Xanthos, Polym. Degrad. Stab. 2009, 94, 834-844.
92. (a), D. Cam, M. Marucci, Polymer 1997, 38, 1879-1884
93. (b), Y. J. Fan, H. Nishida, Y. Shirai, T. Endo, Polym. Degrad. Stab. 2003, 80, 503-511
94. (c), Y. J. Fan, H. Nishida, Y. Shirai, T. Endo, Polym. Degrad. Stab. 2004, 84, 243-251
95. (d), Y. J. Fan, H. Nishida, T. Mori, Y. Shirai, T. Endo, Polymer 2004, 45, 1197-1205.
96. (a), Y. Aoyagi, K. Yamashita, Y. Doi, Polym. Degrad. Stab. 2002, 76, 53-59
97. (b), P. Kubisa, S. Penczek, Prog. Polym. Sci. 1999, 24, 1409-1437.
98. Y. J. Fan, H. Nishida, S. Hoshihara, Y. Shirai, Y. Tokiwa, T. Endo, Polym. Degrad. Stab. 2003, 79, 547-562.
99. (a), T. Ozawa, Bull. Chem. Soc. Jpn. 1965, 38, 1881-1886
100. (b), J. Flynn, L. A. Wall, J. Polym. Sci. Part B: Polym. Lett. 1966, 4, 323-328
101. (c), T. Ozawa, J. Therm. Anal. Calorim. 1970, 2, 301-324.
102. (a), H. E. Kissinger, J. Res. Natl. Bur. Stand. 1956, 57, 217-221
103. (b), H. E. Kissinger, Anal. Chem. 1957, 29, 1702-1712.
104. (a), S.-H. Lee, S. H. Kim, Y.-K. Han, Y. H. Kim, J. Polym. Sci. Part A: Polym. Chem. 2001, 39, 973-985
105. (b), S. Yang, J. Zhang, Q. Bo, D. Fang, J. Appl. Polym. Sci. 1993, 50, 1883-1889.
106. (a), Y. J. Fan, H. Nishida, Y. Shirai, T. Endo, Polym. Degrad. Stab. 2004, 84, 143-149
107. (b), H. Abe, N. Takahashi, K. J. Kim, M. Mochizuki, Y. Doi, Biomacromolecules 2004, 5, 1606-1614.
108. Y. J. Fan, H. Nishida, Y. Shirai, Polym. Degrad. Stab. 2003, 79, 547-562.