One-pot synthesis of lactide-styrene diblock copolymers via catalytic immortal ring-opening polymerization of lactide and nitroxide-mediated polymerization of styrene

ChemSusChem

Volumn 3, Issue 5, 2010, Pages 579-590

  Poirier, Valentin ^a   Duc, Michel ^b   Carpentier, Jean Franåois ^a   Sarazin, Yann ^a  

^a CNRS   (France)

^b TOTAL   (France)

Author keywords

Binary catalysis; Block copolymers; Polymers; Ring opening polymerization; Zinc

Indexed keywords

BINS; BIOCOMPATIBILITY; BIODEGRADABLE POLYMERS; BIOGRAPHIES; BIOLOGICAL MATERIALS; BLOCK COPOLYMERS; CATALYSTS; POLYMERIZATION; POLYMERS; STYRENE; ZINC;

ATOM EFFICIENCY; BINARY CATALYSIS; CATALYTIC SYSTEM; NITROXIDE MEDIATED POLYMERIZATION; ONE-POT SYNTHESIS; POLYMER MATERIALS; SEQUENTIAL PROCEDURES; TRANSFER AGENTS;

RING OPENING POLYMERIZATION;

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; NITROGEN OXIDE; NITROXYL; POLYESTER; POLYLACTIDE; POLYSTYRENE DERIVATIVE; SOLVENT;

ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS;

CATALYSIS; INDICATORS AND REAGENTS; NITROGEN OXIDES; POLYESTERS; POLYSTYRENES; SOLVENTS;

EID: 77954784242     PISSN: 18645631     EISSN: 1864564X     Source Type: Journal    
DOI: 10.1002/cssc.201000021     Document Type: Article

References (85)

1. R. E. Drumright, P. R. Gruber, D. E. Henton, Adv. Mater. 2000, 12, 1841-1846.
2. A.-C Albertsson, I. K. Varma, Adv. Polym. Sci. 2002, 157, 1-40.
3. A.-C Albertsson, I. K. Varma, Biomacromolecules 2003, 4, 1466-1486.
4. A. Corma, S. Iborra, A. Velty, Chem. Rev. 2007, 107, 2411-2502.
5. M. Okada, Prog. Polym. Sci. 2002, 27, 87-133.
6. S. Mecking, Angew. Chem. 2004, 116, 1096-1104.
7. S. Mecking, Angew. Chem. Int. Ed. 2004, 43, 1078-1085.
8. W. H. Wong, D. J. Mooney, Synthetic Biodegradable Polymer Scaffolds (Eds.: A. Atala, D. J. Mooney), Birkhauser, Boston, 1997.
9. M. H. Hartmann, Biopolymers from Renewable Resources (Ed.: D. L. Kaplan), Springer, Berlin, 1998, pp. 367-411.
10. K. E. Uhrich, S. M. Cannizzaro, R. S. Langer, K. M. Shakesheff, Chem. Rev. 1999, 99, 3181-3198.
11. Y. Ikada, H. Tsuji, Macromol. Rapid Commun. 2000, 21, 117-132.
12. B. M. Chamberlain, M. Cheng, D. R. Moore, T. M. Ovitt, E. B. Lobkovsky, G. W. Coates, J. Am. Chem. Soc. 2001, 123, 3229-3238.
13. C. K. Williams, L. E. Breyfogle, S. K. Choi, W. Nam, V. G. Young Jr., M. A. Hillmyer, W. B. Tolman, J. Am. Chem. Soc. 2003, 125, 11350-11359.
14. V. Poirier, T. Roisnel, J.-F. Carpentier, Y. Sarazin, Dalton Trans. 2009, 9820-9827.
15. T. M. Ovitt, G. W. Coates, J. Am. Chem. Soc. 2002, 124, 1316-1326.
16. N. Nomura, R. Ishii, Y. Yamamoto, T. Kondo, Chem. Eur. J. 2007, 13, 4433-4451.
17. C.-X. Cai, A. Amgoune, C. W. Lehmann, J.-F. Carpentier, Chem. Commun. 2004, 330-331.
18. A. Amgoune, C. M. Thomas, T. Roisnel, J.-F. Carpentier, Chem. Eur. J. 2006, 12, 169-179.
19. N. Ajellal, D. M. Lyubov, M. A. Sinenkov, G. K. Fukin, A. V. Cherkasov, C. M. Thomas, J.-F. Carpentier, A. A. Trifonov, Chem. Eur. J. 2008, 14, 5440-5448.
20. H. Y. Ma, J. Okuda, Macromolecules 2005, 38, 2665-2673.
21. H. Y. Ma, T. P. Spaniol, J. Okuda, Angew. Chem. 2006, 118, 7982-7985.
22. H. Y. Ma, T. P. Spaniol, J. Okuda, Angew. Chem. Int. Ed. 2006, 45, 7818-7821.
23. For the recent pioneering of metal-free organic ROP initiators, see: N. E. Kamber, W. Jeong, R. M. Waymouth, R. C. Pratt, B. G. G. Lohmeijer, J. L. Hedrick, Chem. Rev. 2007, 107, 5813-5840.
24. D. Bourissou, S. Moebs-Sanchez, B. Martín-Vaca, C. R. Chim. 2007, 10, 775-794.
25. For reviews on the development of discrete metal-based initiators for the ROP of LA, see for example: B. J. O'Keefe, M. A. Hillmyer, W. B. Tolman, J. Chem. Soc., Dalton Trans. 2001, 2215-2224.
26. O. Dechy-Cabaret, B. Martin-Vaca, D. Bourissou, Chem. Rev. 2004, 104, 6147-6176.
27. J. Wu, T.L. Yu, C.-T. Chen, C.-C. Lin, Coord. Chem. Rev. 2006, 250, 602-626.
28. C. A. Wheaton, P. G. Hayes, B. J. Ireland, Dalton Trans. 2009, 4832-4846.
29. S. C. Schmidt, M. A. Hillmyer, Macromolecules 1999, 32, 4794-4801.
30. Y. Wang, M. A. Hillmyer, Macromolecules 2000, 33, 7395-7403.
31. A. S. Zalusky, R. Olayo-Valles, J. H. Wolf, M. A. Hillmyer, J. Am. Chem. Soc. 2002, 124, 12761-12773.
32. R.-M. Ho, Y.-W. Chiang, C.-C. Tsai, C.-C. Lin, B.-T. Ko, B.-H. Huang, J. Am. Chem. Soc. 2004, 126, 2704-2705.
33. J. Rzayev, M. A. Hillmyer, Macromolecules 2005, 38,3-5.
34. A. Amgoune, C. M. Thomas, E. Balnois, Y. Grohens, P. J. Lutz, J.-F. Carpentier, Macromol. Rapid Commun. 2005, 26, 1145-1150.
35. F.-Y. Tzeng, M.-C. Lin, J.-Y. Wu, J.-C. g Kuo, J.-C. Tsai, M.-S. Hsiao, H.L. Chen, S. Z. D. Cheng, Macromolecules 2009, 42, 3073-3085.
36. When initially comparing a simple polyolefin and a related (multi)block copolymer of identical length with a small content of biodegradable polyester, the degradation of the bioresourced segment in the copolymer eventually yielded polyolefin fragments of much smaller size and different morphologies than the simple homopolymer: G. Swift, R. Baciu, Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 2007, 48, 586-587.
37. A. S. Zalusky, R. Olayo-Valles, C. J. Taylor, M. A. Hillmyer, J. Am. Chem. Soc. 2001, 123, 1519-1520.
38. K.-H. Lo, W.-H. Tseng, R.M. Ho, Macromolecules 2007, 40, 2621-2624.
39. M.-L. Shueh, Y.-S. Wang, B.-H. Huang, C.-Y. Kuo, C.-C. Lin, Macromolecules 2004, 37, 5155-5162.
40. For the preparation of copolymers of styrene and lactide and their arrangement into original microstructures, see for instance: W.-H. Tseng, P.-Y. Hsieh, R.M. Ho, B.-H. Huang, C.-C. Lin, B. Lotz, Macromolecules 2006, 39, 7071-7077.
41. H. Mao, M. A. Hillmyer, Macromol. Chem. Phys. 2008, 209, 1647-1656.
42. J. Rzayev, Macromolecules 2009, 42, 2135-2141.
43. L. Zhao, M. Byun, J. Rzayev, Z. Lin, Macromolecules 2009, 42, 9027-9033.
44. Others methodologies include: the reverse sequence, that is, the preparation of an end-functionalized PS macroinitiator by ATRP for the subsequent ROP of LA, see for instance ref. [19c] or: A. Likhitsup, A. Parthiban, C. L. L. Chai, J. Polym. Sci. Part A 2008, 46, 102-116; the post-polymerization modification of functionalized polystyrene followed by ROP of LA: see Ref. [20d].
45. P. Dubois, R. Jérôme, P. Teyssié, Macromolecules 1991, 24, 977-981.
46. I. Barakat, P. Dubois, R. Jérôme, P. Teyssié, J. Polym. Sci. Part A 1993, 31, 505-514.
47. I. Barakat, P. Dubois, R. Jérôme, P. Teyssié, E. Goethals, J. Polym. Sci. Part A 1994, 32, 2099-2110.
48. I. Barakat, P. Dubois, C. Grandfils, R. Jérôme, J. Polym. Sci. Part A 1999, 37, 2401-2411.
49. J. L. Eguiburu, M. J. Fernandez-Berridi, F. P. Cossio, J. San Román, Macromolecules 1999, 32, 8252-8258.
50. C. J. Hawker, D. Mecerreyes, E. Elce, J. Dao, J. L. Hedrick, I. Barakat, P. Dubois, R. Jérôme, W. Volksen, Macromol. Chem. Phys. 1997, 198, 155-166.
51. R. Jabbar, A. Graffe, B. Lessard, M. Marić, J. Appl. Polym. Sci. 2008, 109, 3185-3195.
52. C. J. Hawker, G. G. Barclay, A. Orellana, J. Dao, W. Devonport, Macromolecules 1996, 29, 5245-5254.
53. C. J. Hawker, G. G. Barclay, J. Dao, J. Am. Chem. Soc. 1996, 118, 11467-11471.
54. C. J. Hawker, J. L. Hedrick, E. E. Malmstrom, M. Trollss, D. Mecerreyes, G. Moineau, P. Dubois, R. Jérôme, Macromolecules 1998, 31, 213-219.
55. D. Mecerreyes, G. Moineau, P. Dubois, R. Jérôme, J. L. Hedrick, C. J. Hawker, E. E. Malmstrçm, M. Trollsas, Angew. Chem. 1998, 110, 1306-1309.
56. D. Mecerreyes, G. Moineau, P. Dubois, R. Jérôme, J. L. Hedrick, C. J. Hawker, E. E. Malmstrçm, M. Trollsas, Angew. Chem. Int. Ed. 1998, 37, 1274-1276.
57. TEMPO-OH and hydroxyl-functionalized alkoxyamines were also used to prepare diblock copolymers of e-caprolactone with styrene or 4-vinylpyridine following the same methodologies: E. Yoshida, Y. Osagawa, Macromolecules 1998, 31, 1446-1456.
58. Z. Li, G. Lu, J. Huang, J. Appl. Polym. Sci. 2004, 94, 2280-2285.
59. C.-H. Lu, C.-F. Huang, S.-W. Kuo, F.-C. Chang, Macromolecules 2009, 42, 1067-1078.
60. P. Dubois, R. Jérôme, P. Teyssié, Makromol. Chem. Macromol. Symp. 1991, 42-43, 103-116.
61. M. J. Stanford, A. P. Dove, Macromolecules 2009, 42, 141-147.
62. S. Asano, T. Aida, S. Inoue, J. Chem. Soc. Chem. Commun. 1985, 1148-1149.
63. T. Aida, Y. Maekawa, S. Asano, S. Inoue, Macromolecules 1988, 21, 1195-1202.
64. H. Sugimoto, T. Aida, S. Inoue, Macromolecules 1990, 23, 2869-2875.
65. S. Inoue, J. Polym. Sci. Part A 2000, 38, 2861-2871.
66. E. Martin, P. Dubois, R. Jérôme, Macromolecules 2000, 33, 1530-1535.
67. Y.-C. Liu, B.-T. Ko, C.-C. Lin, Macromolecules 2001, 34, 6196-6201.
68. M.-L. Hsueh, B.-H. Huang, C.-C. Lin, Macromolecules 2002, 35, 5763-5768.
69. Y. Ning, Y. Zhang, A. Rodriguez-Delgado, E. Y.-X. Chen, Organometallics 2008, 27, 5632-5640.
70. A. Amgoune, C. T. Thomas, J.-F. Carpentier, Macromol. Rapid Commun. 2007, 28, 693-697.
71. C. Guillaume, J.-F. Carpentier, S. M. Guillaume, Polymer 2009, 50, 5909-5917.
72. M. Helou, O. Miserque, J.-M. Brusson, J.-F. Carpentier, S. M. Guillaume, Chem. Eur. J. 2008, 14, 8772-8775.
73. M. Helou, O. Miserque, J.-M. Brusson, J.-F. Carpentier, S. M. Guillaume, Adv. Synth. Catal. 2009, 351, 1312-1324.
74. M. Helou, O. Miserque, J.-M. Brusson, J.-F. Carpentier, S. M. Guillaume, ChemCatChem, in press.
75. T. J. Woodman, Y. Sarazin, G. Fink, K. Hauschild, M. Bochmann, Macromolecules 2005, 38, 3060-3067.
76. M. Bochmann, G. Bwembya, K. J. Webb, Inorg. Synth. 1997, 31, 19-24.
77. M. Westerhausen, Inorg. Chem. 1991, 30, 96-101.
78. Y. Sarazin, R. H. Howard, D. L. Hughes, S. M. Humphrey, M. Bochmann, Dalton Trans. 2006, 340-350.
79. The probability of a meso enchainment for two consecutive chiral centers was determined by examination of the methine region in the 1H homonuclear decoupled NMR spectrum of PLA samples according to Ref. [5] and M. H. Chisholm, S. S. Iyer, M. E. Matison, Chem. Commun. 1997, 1999-2000.
80. The largest discrepancy between calculated and experimental Mn was that obtained with [5]/[TEMPO-OH]=1:1 (Table 3, entry 9), which can tentatively be explained by the fact that the Mark-Houwink factor of 0.58 commonly used for the determination of molecular weights of PLLA samples by size exclusion chromatography (SEby using polystyrene standards is erroneous for materials of such length. See: M. Save, M. Schappacher, A. Soum, Macromol. Chem. Phys. 2002, 203, 889-899.
81. The short induction periods, better observed at 80°C and 100°C, can be accounted for by the time necessary so that a significant fraction of the monomer had dissolved in styrene, due to the experimental procedure we used. Under these experimental conditions, that is, [l-LA]0= 2.0m and [l-LA]/[5]/[TEMPO-OH]=1000:1:10, complete dissolution of the monomer was typically ensured after 1-2 min at temperatures of 80-100 °C. The polymers remained fully soluble at these temperatures, even at full conversion of the monomer.
82. We have shown that the thermally self-initiated homopolymerization of styrene only takes place to a noticeable extent at 105°C (or morafter several hours of reaction time and yields amorphous atactic PS: S. Bogaert, J.-F. Carpentier, T. Chenal, A. Mortreux, G. Ricart, Macromol. Chem. Phys. 2000, 201, 1813-1822.
83. The small discrepancies between observed and calculated molecular weights (notably for DP=24) are due to the automatic peak peaking, which is not able to detect systematically the main peak in a given isotopic distribution. This default of our software could unfortunately not be circumvented.
84. As the hydrodynamic volume of a PLLA-block-PS in solution most likely lies in between those of the corresponding PLLA and PS homopolymers, the Mark-Houwink factor of 0.58 normally used for the determination of the molecular weight of PLA samples (Ref. [37]), was not applied to the calculation of the molecular weight of the final diblock copolymer.
85. NMR spectroscopy and SEC characterization of these copolymers are given in the Supporting Information