Synthesis of polystyrenes-poly(alkyl methacrylates) block copolymers via anionic polymerization using an integrated flow microreactor system

Macromolecules

Volumn 43, Issue 20, 2010, Pages 8424-8429

  Nagaki, Aiichiro ^a   Miyazaki, Atsuo ^a   Yoshida, Jun Ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BUTYLLITHIUM; DIBLOCK COPOLYMER; LIVING POLYMERS; MACROINITIATORS; MICROREACTOR SYSTEM; ORGANOLITHIUM SPECIES; POLY(ALKYL METHACRYLATES); RESIDENCE TIME; TRIBLOCK COPOLYMERS;

ALKYLATION; BLOCK COPOLYMERS; CHEMICALS; COPOLYMERIZATION; LIVING POLYMERIZATION; POLYMER BLENDS; POLYMERS; POLYSTYRENES; STYRENE;

ANIONIC POLYMERIZATION;

EID: 77958191632     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma101663x     Document Type: Article

References (114)

1. Chem. Rev. 2001, 101, issue 12.
2. Szwarc, M. Nature 1956, 178, 1168-1169
3. Living cationic polymerization: Matyjaszewski, K.; Sawamoto, M. in Cationic Polymerizations, Matyjaszewski, K., Ed. Marcel Dekker, New York, 1996.
4. Living anionic polymerization: Hsieh, H. L.; Quirk, R. P. Anionic polymerization: principles and practical applications; Marcel Dekker: New York, 1996.
5. Hong, K.; Uhrig, D.; Mays, J. W. Current Opinion in Solid State and Material Science 1999, 4, 531-538
6. Jagur-grodzinski, J. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 2116-2133
7. Smid, J. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 2101-2107
8. Hirao, A.; Loykulnant, S.; Ishizone, T. Prog. Polym. Sci. 2002, 27, 1399-1471
9. Hadjichristidis, N.; Pitsikalis, M.; Pispas, S.; Iatrou, H. Chem. Rev. 2001, 101, 3747-3792 and references therein
10. Living radical polymerization: Matyjaszewski, K.; Davis, T. P. Handbook of Radical Polymerization, 1 st ed.; Wiley: New York, 2002.
11. Moad, G.; Solomon, D. H. The Chemistry of Radical Polymerization, 2 nd ed.; Elsevier: Amsterdam, 2006.
12. Flash chemistry: Yoshida, J. Flash Chemistry Fast Organic Synthesis in Microsystems; Wiley: Chichester, 2008.
13. Yoshida, J. Chem. Commun. 2005, 4509-4516
14. Yoshida, J.; Nagaki, A.; Yamada, T. Chem.-Eur. J. 2008, 14, 7450-7459
15. Hessel, V.; Hardt, S.; Löwe, H. Chemical Micro Process Engineering; Wiely-VCH Verlag: Weinheim, 2004.
16. Wirth, T. Microreactors in Organic Synthesis and Catalysis; Wiley-VCH Verlag: Weinheim, 2008.
17. Hessel, V.; Renken, A.; Schouten, J. C.; Yoshida, J. Micro Process Engineering; Wiley-VCH Verlag: Weinheim, 2009.
18. Reviews for microreactor: Fletcher, P. D. I.; Haswell, S. J.; Pombo-Villar, E.; Warrington, B. H.; Watts, P.; Wong, S. Y. F.; Zhang, X. Tetrahedron 2002, 58, 4735-4757
19. Jähnisch, K.; Hessel, V.; Löwe, H.; Baerns, M. Angew. Chem., Int. Ed. 2004, 43, 406-446
20. Doku, G. N.; Verboom, W.; Reinhoudt, D. N.; van den Berg, A. Tetrahedron 2005, 61, 2733-2742
21. Watts, P.; Haswell, S. J. Chem. Soc. Rev. 2005, 34, 235-246
22. Geyer, K.; Codee, J. D. C.; Seeberger, P. H. Chem.-Eur. J. 2006, 12, 8434-8442
23. deMello, A. J. Nature 2006, 442, 394-402
24. Song, H.; Chen, D. L.; Ismagilov, R. F. Angew. Chem., Int. Ed. 2006, 45, 7336-7356
25. Kobayashi, J.; Mori, Y.; Kobayashi, S. Chem. Asian J. 2006, 1, 22-35
26. Mason, B. P.; Price, K. E.; Steinbacher, J. L.; Bogdan, A. R.; McQuade, D. T. Chem. Rev. 2007, 107, 2300-2318
27. Ahmed-Omer, B.; Brandtand, J. C.; Wirth, T. Org. Biomol. Chem. 2007, 5, 733-740
28. Fukuyama, T.; Rahman, M. T.; Sato, M.; Ryu, I. Synlett 2008, 151-163
29. McMullen, J. P.; Jensen, K. F. Annu. Rev. Anal. Chem. 2010, 3, 19-42
30. Recent examples: de Bellefon, C.; Tanchoux, N.; Caravieilhes, S.; Grenouillet, P.; Hessel, V. Angew. Chem., Int. Ed. 2000, 39, 3442-3445
31. Watts, P.; Wiles, C.; Haswell, S. J.; Pombo-Villar, E.; Styring, P. Chem. Commun. 2001, 990-991
32. Hisamoto, H.; Saito, T.; Tokeshi, M.; Hibara, A.; Kitamori, T. Chem. Commun. 2001, 2662-2663
33. Suga, S.; Okajima, M.; Fujiwara, K.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 7941-7942
34. Wiles, C.; Watts, P.; Haswell, S. J.; Pombo-Villar, E. Chem. Commun. 2002, 1034-1035
35. Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691-1694
36. Ueno, M.; Hisamoto, H.; Kitamori, T.; Kobayashi, S. Chem. Commun. 2003, 936-937
37. Garcia-Egido, E.; Spikmans, V.; Wong, S. Y. F.; Warrington, B. H. Lab Chip 2003, 3, 73-76
38. Lai, S. M.; Martin-Aranda, R.; Yeung, K. L. Chem. Commun. 2003, 218-219
39. Mikami, K.; Yamanaka, M.; Islam, M. N.; Kudo, K.; Seino, N.; Shinoda, M. Tetrahedron Lett. 2003, 44, 7545-7548
40. Suga, S.; Nagaki, A.; Tsutsui, Y.; Yoshida, J. Org. Lett. 2003, 5, 945-947
41. Kobayashi, J.; Mori, Y.; Okamoto, K.; Akiyama, R.; Ueno, M.; Kitamori, T.; Kobayashi, S. Science 2004, 304, 1305-1308
42. Horcajada, R.; Okajima, M.; Suga, S.; Yoshida, J. Chem. Commun. 2005, 1303-1305
43. Ducry, L.; Roberge, D. M. Angew. Chem., Int. Ed. 2005, 44, 7972-7975
44. He, P.; Watts, P.; Marken, F.; Haswell, S. J. Angew. Chem., Int. Ed. 2006, 45, 4146-4149
45. Uozumi, Y.; Yamada, Y.; Beppu, T.; Fukuyama, N.; Ueno, M.; Kitamori, T. J. Am. Chem. Soc. 2006, 128, 15994-15995
46. Tanaka, K.; Motomatsu, S.; Koyama, K.; Tanaka, S.; Fukase, K. Org. Lett. 2007, 9, 299-302
47. Ushiogi, Y.; Hase, T.; Iinuma, Y.; Takata, A.; Yoshida, J. Chem. Commun. 2007, 2947-2949
48. Sahoo, H. R.; Kralj, J. G.; Jensen, K. F. Angew. Chem., Int. Ed. 2007, 46, 5704-5708
49. Hornung, C. H.; Mackley, M. R.; Baxendale, I. R.; Ley, S. V. Org. Process Res. Dev. 2007, 11, 399-405
50. Fukuyama, T.; Kobayashi, M.; Rahman, M. T.; Kamata, N.; Ryu, I. Org. Lett. 2008, 10, 533-536
51. Reviews on polymerizations using microreactors: Hessel, V.; Serra, C.; Löwe, H.; Hadziioannou, G. Chemie Ingenieur Technik 2005, 77, 1693-1714
52. Steinbacher, J. L.; Mcquade, D. T. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 6505-6533 and references therein
53. Cationic polymerization using microreactors: Nagaki, A.; Kawamura, K.; Suga, S.; Ando, T.; Sawamoto, M.; Yoshida, J. J. Am. Chem. Soc. 2004, 126, 14702-14703
54. Iwasaki, T.; Nagaki, A.; Yoshida, J. Chem. Commun. 2007, 1263-1265
55. Nagaki, A.; Iwasaki, T.; Kawamura, K.; Yamada, D.; Suga, S.; Ando, T.; Sawamoto, M.; Yoshida, J. Chem. Asian J. 2008, 3, 1558-1567
56. Suga, S.; Nagaki, A.; Yoshida, J. Chem. Commun. 2003, 354-355
57. Nagaki, A.; Togai, M.; Suga, S.; Aoki, N.; Mae, K.; Yoshida, J. J. Am. Chem. Soc. 2005, 127, 11666-11675
58. Yoshida, J.; Nagaki, A.; Iwasaki, T.; Suga, S. Chem. Eng. Technol. 2005, 28, 259-266
59. Nagaki, A.; Takabayashi, N.; Tomida, Y.; Yoshida, J. Org. Lett. 2008, 18, 3937-3940
60. Nagaki, A.; Takabayashi, N.; Tomida, Y.; Yoshida, J. Beilstein J. Org. Chem. 2009, 5, No16
61. Kawaguchi, T.; Miyata, H.; Ataka, K.; Mae, K.; Yoshida, J. Angew. Chem., Int. Ed. 2005, 44, 2413-2416
62. Usutani, H.; Tomida, Y.; Nagaki, A.; Okamoto, H.; Nokami, T.; Yoshida, J. J. Am. Chem. Soc. 2007, 129, 3046-3047
63. Nagaki, A.; Tomida, Y.; Usutani, H.; Kim, H.; Takabayashi, N.; Nokami, T.; Okamoto, H.; Yoshida, J. Chem. Asian J. 2007, 2, 1513-1523
64. Nagaki, A.; Kim, H.; Yoshida, J. Angew. Chem., Int. Ed. 2008, 47, 7833-7836
65. Nagaki, A.; Takizawa, E.; Yoshida, J. J. Am. Chem. Soc. 2009, 131, 1654-1655
66. Nagaki, A.; Takizawa, E.; Yoshida, J. Chem. Lett. 2009, 38, 486-487
67. Tomida, Y.; Nagaki, A.; Yoshida, J. Org. Lett. 2009, 11, 3614-3617
68. Nagaki, A.; Takizawa, E.; Yoshida, J. Chem. Lett. 2009, 38, 1060-1061
69. Nagaki, A.; Kim, H.; Yoshida, J. Angew. Chem., Int. Ed. 2009, 48, 8063-8065
70. Nagaki, A.; Kim, H.; Matsuo, C.; Yoshida, J. Org. Biomol. Chem. 2010, 8, 1212-1217
71. Living radical polymerization using microreactors: Wu, T.; Mei, Y.; Cabral, J. T.; Xu, C.; Beers, K. L. J. Am. Chem. Soc. 2004, 126, 9880-9881
72. Serra, C.; Sary, N.; Schlatter, G.; Hadziioannou, G.; Hessel, V. Lab Chip 2005, 5, 966-973
73. Enright, T. E.; Cunningham, M. F.; Keoshkerian, B. Macromol. Rapid Commun. 2005, 26, 221-225
74. Russum, J. P.; Jones, C. W.; Schork, F. J. Ind. Eng. Chem. Res. 2005, 44, 2484-2493
75. Xu, C.; Wu, T.; Drain, C. M.; Batteas, J. D.; Beers, K. L. Macromolecules 2005, 38, 6-8
76. Rosenfeld, C.; Serra, C.; Brochon, C.; Hadziioannou, G. Chem. Eng. Sci. 2007, 62, 5245-5250
77. Rosenfeld, C.; Serra, C.; Brochon, C.; Hadziioannou, G. Lab Chip 2008, 8, 1682-1687
78. Enright, T. M.; Cunningham, M. F.; Keoshkerian, B. Macromol. React. Eng. 2010, 4, 186-196
79. Control of molecular weights of polymers in radical polymerization by modulating the residence time in the microreactor: Russum, J. P.; Jones, C. W.; Schork, F. J. Macromol. Rapid Commun. 2004, 25, 1064-1068
80. Wu, T.; Mei, Y.; Xu, C.; Byrd, H. C. M.; Beers, K. L. Macromol. Rapid Commun. 2005, 26, 1037-1042
81. Radical polymerization using microreactors: Iwasaki, T.; Yoshida, J. Macromolecules 2005, 38, 1159-1165
82. Iwasaki, T.; Kawano, N.; Yoshida, J. Org. Process Res. Dev. 2006, 10, 1126-1131
83. Synthesis of polymers of well-defined end-structures by anionic polymerization: Morton, M.; Fetters, L. J. J. Polym. Sci., Macromol. Rev. 1967, 2, 71-113
84. French, D. M. Rubber Chem. Technol. 1969, 42, 71-109
85. Bi, L.-K.; Fetters, L. J. Macromolecules 1976, 9, 732-742
86. Hirao, A.; Hattori, I.; Sasagawa, T.; Yamaguchi, K.; Nakahama, S. Makromol. Chem. 1982, RC3, 59-63
87. Young, R. N.; Quirk, R. P.; Fetters, L. J. Adv. Polym. Sci. 1984, 56, 1-90
88. Quirk, R. P.; Yin, J.; Guo, S.-H.; Hu, X.-W.; Summers, G.; Kim, J.; Zhu, L.-F.; Schock, L. E. Makromol. Chem., Macromol. Symp. 1990, 32, 47-59
89. Hirao, A.; Nagahama, H.; Ishizone, T.; Nakahama, S. Macromolecules 1993, 26, 2145-2150
90. Allgaier, J.; Young, R. N.; Efstratiadis, V.; Hadjichristidis, N. Macromolecules 1996, 29, 1794-1797
91. Floudas, G.; Pispas, S.; Hadjichristidis, N.; Pakula, T.; Erukhimovich, I. Macromolecules 1996, 29, 4142-4154
92. Avgeropoulos, A.; Hadjichristidis, N. J. Polym. Sci., Part A: Polym. Chem. 1997, 35, 813-816
93. Beyer, F. L.; Gido, S. P.; Poulos, Y.; Avgeropoulos, A.; Hadjichristidis, N. Macromolecules 1997, 30, 2373-2376
94. Uhrig, D.; Mays, J. W. Macromolecules 2002, 35, 7182-7190
95. Zhao, Y.; Higashihara, T.; Sugiyama, K.; Hirao, A. J. Am. Chem. Soc. 2005, 127, 14158-14159
96. Schappacher, M.; Deffieux, A. Macromolecules 2005, 38, 7209-7213
97. Ji, H.; Sakellariou, G.; Mays, J. W. Macromolecules 2007, 40, 3461-3467
98. Anionic polymerization using microreactors: Wurm, F.; Wilms, D.; Klos, J.; Löwe, H.; Frey, H. Macromol. Chem. Phys. 2008, 209, 1106-1114
99. Nagaki, A.; Tomida, Y.; Yoshida, J. Macromolecules 2008, 41, 6322-6330
100. Nagaki, A.; Tomida, Y.; Miyazaki, A.; Yoshida, J. Macromolecules 2009, 42, 4384-4387
101. Iida, K.; Chastek, T. Q.; Beers, K. L.; Cavicchi, K. A.; Chunc, J.; Fasolka, M. J. Lab Chip 2009, 9, 339-345
102. Suga, S.; Yamada, D.; Yoshida, J. Chem. Lett. 2010, 39, 404-406
103. Freyss, D.; Rempp, P.; Benoit, H. Polym. Lett. 1964, 2, 217-222
104. Ramireddy, C.; Tuzar, Z.; Procházka, K.; Webber, S. E.; Munk, P. Macromolecules 1992, 25, 2541-2545
105. Kiserow, D.; Chan, J.; Ramireddy, C.; Munk, P.; Webber, S. E. Macromolecules 1992, 25, 5338-5344
106. Chan, J.; Fox, S.; Kiserow, D.; Ramireddy, C.; Munk, P.; Webber, S. E. Macromolecules 1993, 26, 7016-7023
107. Pitsikalis, M.; Siakali-Kioulafa, E.; Hadjichristidis, N. Macromolecules 2000, 33, 5460-5469
108. Weidisch, R.; Michler, G. H.; Arnold, M. Polymer 2000, 41, 2231-2240
109. Kim, W.; Han, J.; Ryu, C. Y.; Yang, H. J. Polym. Sci., Part B: Polym. Phys. 2006, 44, 3612-3620
110. Auschra, C.; Stadler, R. Polym. Bull. 1993, 30, 257-264
111. Feldthusen, J.; Ivan, B.; Müller, A. H. E. Macromolecules 1998, 31, 578-585
112. Matsumoto, K.; Wahnes, C.; Mouri, E.; Matsuoka, H.; Yamaoka, H. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 86-92
113. Cho, J. C.; Cheng, G.; Feng, D.; Faust, R.; Richard, R.; Schwarz, M.; Chan, K.; Boden, M. Biomacromolecules 2006, 7, 2997-3007
114. Feng, D.; Higashihara, T.; Faust, R. Polymer 2008, 49, 386-393