Mn2 (CO)10-Visible Light Photomediated, Controlled Radical Polymerization of Main Chain Fluorinated Monomers and Synthesis of Block Copolymers Thereof

Handbook of Fluoropolymer Science and Technology

Volumn , Issue , 2014, Pages 21-42

  Asandei, Alexandru D ^a   Adebolu, Olumide I ^a   Simpson, Christopher P ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

Block copolymers; Chain transfer agent (CTA); Main chain fluorinated monomers; Mn2(CO)10; Radical polymerization; Vinylidene fluoride (VDF)

Indexed keywords

ATOM TRANSFER RADICAL POLYMERIZATION; CHAINS; DIELECTRIC MATERIALS; FLUORINE CONTAINING POLYMERS; FREE RADICAL POLYMERIZATION; LIGHT; MANGANESE COMPOUNDS; METAL HALIDES; MONOMERS; REFRACTIVE INDEX;

CHAIN TRANSFER AGENTS; CONTROLLED RADICAL POLYMERIZATION; FLUORINATED MONOMERS; MN2(CO)10; MOISTURE ABSORPTION; SPECIALTY MATERIALS; VINYLIDENE FLUORIDE; WEATHER RESISTANCE;

BLOCK COPOLYMERS;

EID: 84940835474     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9781118850220.ch2     Document Type: Chapter

References (152)

1. Ameduri, B. Macromolecules 2010, 43, 10163-10184.
2. Lena, F.; Matyjaszewski, K. Prog. Polym. Sci. 2010, 35, 959-1021.
3. Matyjaszewski, K.; Davis, T. P. Handbook of Radical Polymerization; John Wiley & Sons: New York, 2002.
4. Braunecker, W. A.; Matyjaszewski, K. Prog. Polym. Sci. 2007, 32, 93-146.
5. Goto, A.; Fukuda, T. Progr. Polym. Sci. 2004, 29, 329.
6. Fukuda, T. J. Polym. Sci.: Part A: Polym. Chem. 2004, 42, 4743-4755.
7. Ameduri, B. Chem. Rev. 2009, 109, 6632-6686.
8. Hansen, N. M. L.; Jankova, K.; Hvilsted, S. Eur. Polym. J. 2007, 43, 255-293.
9. Fukuda, T.; Goto, A.; Tsujii, Y. Kinetics of Living Radical Polymerization. In Handbook of Radical Polymerization; Matyjaszewski, K., Davis, T. P., Eds.; John Wiley & Sons:New York, 2002; pp. 407-462.
10. Oka, M.; Tatemoto, M. Vinylidene Fluoride-Hexafluoropropylene Copolymer Having Terminal Iodines. In Contemporary Topics in Polymer Science; Bailey, W. J., Tsuruta, T., Eds.; Plenun Press: New York, 1984; Vol. 4, pp 763-781.
11. Tatemoto, M. Int. Poly. Sc. Tech. 1985, 12, 85-98.
12. Tatemoto, M. In Polymeric Materials Encyclopedia; Salamone, J. C., Ed.; CRC: Boca Raton, FL, 1996; Vol. 5, pp 3847-3862.
13. Tatemoto, M.; Shimizu, T. Thermoplastic Elastomers. In Modern Fluoropolymers; Scheirs, J., Ed., John Wiley & Sons: New York, 1997; pp. 565-576.
14. Tatemoto, M.; Nakagawa, T. US Patent 4,158,678, 1979.
15. Gaynor, S. G.; Wang, J. S.; Matyjaszewski, K. Macromolecules 1995, 28, 8051-8056.
16. David, G.; Boyer, C.; Tonnar, J.; Ameduri, B.; Lacroix-Desmazes, P.; Boutevin, B. Chem. Rev. 2006, 106, 3936-3962.
17. Boutevin, B. J. Polym. Sci.: Part A: Polym. Chem. 2000, 38, 3235-3243.
18. Ameduri, B.; Boutevin, B. Top. Curr. Chem. 1997, 192, 165-233.
19. Ameduri, B.; Boutevin, B. Well Architectured Fluoropolymers: Synthesis, Properties and Applications; Elsevier: Amsterdam, 2004; pp. 1-99.
20. Ameduri, B.; Ladavière, C.; Delolme, F.; Boutevin, B. Macromolecules 2004, 37, 7602-7612.
21. Montefusco, F.; Bongiovanni, R.; Priola, A.; Ameduri, B. Macromolecules 2004, 37, 9804-9813.
22. Cape, J. N.; Greig, A. C.; Tedder, J. M.; Walton, J. C. J. Chem. Soc., Faraday Trans. 1:Phys. Chem. Condens. Phases 1975, 71, 592.
23. Hauptschein, M.; Braid, M.; Lawlor, F. E. J. Am. Chem. Soc. 1958, 80, 846-851.
24. Soueni, A. E.; Tedder, J. M.; Walton, J. C. J. Fluor. Chem. 1978, 11, 407-417.
25. Combes, J. R.; Guan, Z.; DeSimone, J. M. Macromolecules 1994, 27, 865-886.
26. Balague, J.; Ameduri, B.; Boutevin, B.; Caporiccio, G. J. Fluorine Chem. 1995, 70, 215-223.
27. Boyer, C.; Valade, D.; Sauguet, L.; Ameduri, B.; Boutevin, B. Macromolecules 2005, 38, 10353-10362.
28. Boyer, C.; David, V.; Lacroix-Desmazes, P.; Ameduri, B.; Boutevin, B. J. Polym. Sci.:Part A: Polym. Chem. 2006, 44, 5763-5777.
29. Imran-ul-haq, M.; Förster, N.; Vukicevic, R.; Herrmann, K.; Siegmann, R.; Beuermann, S. ACS Symp. Ser. 2009, 1024, 233-243.
30. Apostolo, M.; Arcella, V.; Storti, G.; Morbidelli, M. Macromolecules 2002, 35, 6154-6166.
31. Valade, D.; Boyer, C.; Ameduri, B.; Boutevin, B. Macromolecules 2006, 39, 8639-8651.
32. MacMurray, N.; Tedder, J. M.; Vertommen, L. L. T.; Walton, J. C. J. Chem. Soc., Perkin Trans. 1976, 2, 63-69.
33. Hung, M. H. US Patent 5,231,154, 1993.
34. Low, H. C.; Tedder, J. M.; Walton, J. C. J. Chem. Soc., Faraday Trans. 1: Phys. Chem. Condens. Phases 1976, 72, 1707.
35. Apostolo, M.; Arcella, V.; Storti, G.; Morbidelli, M. Macromolecules 1999, 32, 989.
36. Ameduri, B.; Boutevin, B. J. Fluorine. Chem. 1999, 100, 97-116.
37. Zhang, Z. C.; Chung, T. C. Macromolecules 2006, 39, 5187-5189.
38. Balague, J.; Ameduri, B.; Boutevin, B.; Caporiccio, G. J. Fluorine Chem. 2000, 102, 253-268.
39. Nguyen, B. V.; Yang, Z. Y.; Burton, D. J. J. Org. Chem. 1998, 63, 2887-2891.
40. Li, A. R.; Chen, Q. Y. J. Fluorine Chem. 1997, 81(2), 99-101.
41. Chen, M. Y.; Yang, Z. Y.; Zhao, C. X.; Qiu, Z. M. J. Chem. Soc. Perkin Trans. I. 1988, 3, 563.
42. Metzerg, J. O.; Linker, U. Liebigs Ann. Chem. 1992, 3, 209-216.
43. Hu, C. M.; Qiu, Y. L. J. Chem. Soc. Perkin Trans. 1. 1992, 13, 1569-1572.
44. Huang, W. Y.; Zhang, H. Z.; Lu, L. J. Fluorine Chem. 1990, 50(1), 133-140
45. Leung, L.; Linclau, B. J. Fluorine Chem. 2008, 129, 986-990.
46. Fang, X.; Yang, X.; Yang, X.; Mao, S.; Wang, Z.; Chena, G.; Wua, F. Tetrahedron. 2007, 63, 10684-10692.
47. Hu, C. M.; Qing, F. L. J. Org. Chem. 1991, 56, 6348-6351.
48. Yang, Z. Y.; Burton, D. J. J. Org. Chem. 1991, 56, 1037-1041.
49. Tsunoi, S.; Ryu, I.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Noburu, S. Synlett. 1999, 5, 1249-1252.
50. Benefice-Malouet, S.; Blancou, H.; Commeyras, A. J. Fluorine Chem. 1993, 63(3), 217-226.
51. Asandei, A. D.; Adebolu, O. I.; Simpson, C. P. J. Am. Chem. Soc. 2012, 134, 6080-6083.
52. Asandei, A. D.; Adebolu, O. I.; Simpson, C. P.; Kim, J. S. Angew. Chem. Int. Ed. 2013, 52, 10027-10030.
53. Asandei, A. D.; Simpson, C. P.; Adebolu, O.; Chen, Y. Polym. Prepr. 2011, 52(2), 728-729.
54. Asandei, A. D.; Adebolu, O. I.; Simpson, C. P. Acs. Symp. Ser. 2012, 1106, 47-63.
55. Asandei, A. D.; Simpson, C. P.; Adebolu, O.; Chen, Y. Polym. Prepr. 2011, 52(2), 554-555.
56. Sauguet, L.; Boyer, C.; Ameduri, B.; Boutevin, B. Macromolecules 2006, 39, 9087-9101.
57. Messina, M. T.; Metrangolo, P.; Resnati, G. ACS Symp. Ser. 1999, 746, 239-254.
58. Rowlands, G. J. Tetrahedron 2009, 65, 8603-8655.
59. Gilbert, B. C.; Parsons, A. F. J. Chem. Soc., Perkin Trans. 2. 2002, 3, 367-387.
60. Haszeldine, R. N.; Steele, B. R. J. Chem. Soc. 1954, 923.
61. Saint-Loup, R.; Ameduri, B. J. Fluorine Chem. 2002, 116, 27-34.
62. Asandei, A. D.; Chen, Y. Polym. Mater: Sci. Eng. 2008, 98, 346-347.
63. Asandei, A. D.; Chen, Y. Polym. Prepr. 2007, 48(2), 452-453.
64. Asandei, A. D.; Chen, Y. Polym. Mater: Sci. Eng. 2007, 97, 270-271.
65. Asandei, A. D.; Chen, Y. Polym. Prepr. 2005, 46(2), 633.
66. Asandei, A. D.; Moran, I. W. J. Am. Chem. Soc. 2004, 126, 15932-15933.
67. Asandei, A. D.; Simpson, C. P.; Yu, H. S.; Adebolu, O. I.; Saha, G.; Chen, Y. ACS Symp. Ser. 2009, 1024, 149-166.
68. Abrahamson, H. B.; Wrighton, M. S. J. Am. Chem. Soc. 1977, 99, 5510-5512.
69. Meckstroth, W. K.; Walters, R. T.; Waltz, W. L.; Wojcicki, A.; Dorfman, L. M. J. Am. Chem. Soc. 1982, 104, 1842-1846.
70. Fawcett, J. P.; Poe, A.; Sharma, K. R. J. Chem. Soc., Dalton Trans.: Inorg. Chem. 1979, 12, 1886-1890.
71. Brimm, E. O.; Lynch, M. A., Jr.; Sesny, W. J. J. Am. Chem. Soc., 1954, 76(14), 3831-3835.
72. Treichel, P. M. Manganese carbonyls and manganese carbonyl halides. In Comprehensive Organometallic Chemistry II Vol. 6, Manganese Group; Abel, E. W., Stone, F. G. A., Wilkinson, G., Casey, C. P., Eds.; Pergamon, 1995; pp. 1-19.
73. Tenhaeff, S. C.; Covert, K. J.; Castellani, M. P.; Grunkemeier, J.; Kunz, C.; Weakley, T. J. R.; Koenig, T.; Tyler, D. R. Organometallics 1993, 12, 5000-5004.
74. Martinho Simoes, J. A.; Beauchamp, J. A. Chem. Rev. 1990, 90, 629-688.
75. Friestad, G. K.; Qin, J. J. Am. Chem. Soc. 2001, 123, 9922-9923.
76. Jackson, R. A.; Poe, A. Inorg. Chem. 1978, 17, 997-1003.
77. Fawcett, J. P.; Poe, A.; Sharma, K. R. J. Am. Chem. Soc. 1976, 98, 1401.
78. Rothberg, L. J.; Cooper, J. N.; Peters, K. S.; Vaida, V. J. Am. Chem. Soc. 1982, 104, 3536-3537.
79. Robert, H. C.; Michael, P., Eds. Comprehensive Organometallic Chemistry III, Volume 5; Elsevier: Providence, RI, 2007; pp. 440-746.
80. Zhang, J. Z.; Harris, C. B. J. Chem. Phys. 1991, 95(6), 4024-4032.
81. Sarakha, M. Ferraudi, G. Inorg. Chem. 1999, 38, 4605-4607.
82. Sullivan, R. J.; Brown, T. L. J. Am. Chem. Soc. 1991, 113, 9155-9161.
83. Gilbert, B. C.; Kalz, W.; Lindsay, C. I.; McGrail, P. T.; Parsons, A. F.; Whittaker, D. T. E. J. Chem. Soc., Perkin Trans. 1. 2000, 1187-1194.
84. Gilbert, B. C.; Lindsay, C. I.; McGrail, P. T.; Parsons, A. F.; Whittaker, D. T. E. Synth. Commun. 1999, 29(15), 2711-2718.
85. Hallock, S. A.; Wojcicki, A. J. Organomet. Chem. 1979, 182(4), 521-535.
86. Herrick, R. S.; Herrinton, T. R.; Walker, H. W.; Brown, T. L. Organometallics 1985, 4, 42-45.
87. Bamford, C. H.; Mahmud, M. U. J. Chem. Soc., Chem. Commun. 1972, 13, 762-763.
88. Bamford, C. H.; Mullik, S. U. Polymer 1973, 14(1), 38-39.
89. Bamford, C. H.; Mullik, S. U. Polymer. 1976, 17(3), 225-230.
90. Aliwi, S. M.; Bamford, C. H.; Mullik, S. U. J. Polym. Sci., Polym. Symp. 1975, 50, 33-50.
91. Bamford, C. H.; Mullik, S. U. J. Chem. Soc., Faraday Trans. 1. 1975, 71(3), 625-636.
92. Bamford, C. H.; Mullik, S. U. Polymer 1976, 17, 94-95.
93. Bamford, C. H.; Mullik, S. U. J. Chem. Soc., Faraday Trans. 1. 1976, 72(2), 368-375.
94. Bamford, C. H.; Denyer, R. Nature 1968, 217, 59-60.
95. Bamford, C. H.; Duncan, F. J.; Reynolds, R. J. W.; Seddon, J. D. J. Polym. Sci., Part C:Polym. Symp. 1968, 23, 419-432.
96. Bamford, C. H.; Dyson, R. W.; Eastmond, G. C. J. Polym. Sci., Part C. 1967, 16, 2425.
97. Jiang, M.; Wang, S.; Jin X. J. Mater. Sci. Lett. 1990, 9, 1239-1240.
98. Jenkins, D. W.; Hudson, S. M. Macromolecules 2002, 35, 3413.
99. Eastmond, G. C.; Parr, K. J.; Woot, J. Polymer 1988, 29(5), 950-957.
100. Eastmond, G. C.; Richardson, J. E. Macromolecules 1991, 24, 3189-3200.
101. Iskin, B.; Yilmaz, G.; Yagci, Y. Macromol. Chem. Phys. 2013, 214, 94-98.
102. Koumura, K.; Satoh, K.; Kamigaito, M. Macromolecules 2008, 41(20), 7359-7367.
103. Koumura, K.; Satoh, K.; Kamigaito, M. J. Polym. Sci: Part A: Polym. Chem. 2009, 47, 1343-1353.
104. Koumura, K.; Satoh, K.; Kamigaito, M. Macromolecules 2009, 42, 2497-2504.
105. Kimura, K.; Satoh, K, Kamigaito, M. Polym. J. 2009, 41, 595-603.
106. Doll, W. W.; Lando, J. B. J. Appl. Polym. Sci. 1970, 14(7), 1767-1773.
107. Russo, S.; Behari, K.; Chengji, S.; Pianca, M.; Barchiesi, E.; Moggi, G. Polymer 1993, 34(22), 4777-4781.
108. Duc, M.; Ameduri, B.; Boutevin, B.; Kharroubi, M.; Sage, J.-M. Macromol. Chem. Phys. 1998, 199, 1271-1289.
109. Galin, M.; Maslinkot, L. Macromolecules 1985, 18, 2192-2196.
110. Galin, J. C.; Lutringer, G.; Galin, M. J. Appl. Polym. Sci. 1989, 37, 487-498.
111. Lutringer, G.; Meurer, B.; Weill, G. Polymer 1991, 32, 884-891.
112. Kutringer, G.; Weill, G. Polymer 1991, 32, 877-883.
113. Bottino, A.; Campanelli, G.; Munari, S.; Turturro, A. J. Polym. Sci.: Part B: Polym. Phys. 1988, 26, 785-794.
114. Lee, W. H. Cyclic Carbonates. In Chemistry of Nonaqueous Solvents Vol. 4; Lagowski, J. J., Ed.; Academic Press: New York, 1976; p 167.
115. Odian G. Principles of Polymerization, 4th ed.; John Wiley & Sons, 2004; pp 292-298.
116. Ahmeda, T. S.; DeSimone, J. M.; Roberts, G. W. Chem. Eng. Sci. 2010, 65, 651-659.
117. DiNoia, T. P.; Conway, S. E.; Lim, J. S.; Mchugh, M. A. J. Polym. Sci., Part B: Polym. Phys. 2000, 38, 2832-2840.
118. Tundo, P.; Selva, M. Acc. Chem. Res. 2002, 35, 706-716.
119. Gordon, A. S.; Norris, W. P. J. Phys. Chem. 1965, 69(9), 3013-3017.
120. Thynne, J. C. J.; Gray, P. Trans. Faraday Soc. 1962, 58, 2403-2409.
121. Wijnen, M. H. J. J. Chem. Phys. 1961, 34, 1465-1466.
122. Yee Quee, M. J.; Thynne, J. C. J. Trans. Faraday Soc. 1966, 62, 3154-3161.
123. Zeldes, H.; Livingston, R. J. Magn. Reson. 1976, 21(1), 109-113.
124. Bilde, M.; Møgelberg, T. E.; Sehested, J.; Nielsen, O. J.; Wallington, T. J.; Hurley, M. D.; Japar, S. M.; Dill M., Orkin, V. L.; Buckley, T. J.; Huie, R. E.; Kurylo, M. J. J. Phys. Chem. A. 1997, 101, 3514-3525.
125. Griller D.; Roberts, B. P. J. Chem. Soc. Perkin Trans. II. 1972, 6, 747-751.
126. McRae, J. A.; Symons, M. C. R. J. Chem. Soc. (B), Phys. Org. 1968, 428-430.
127. Hudson, R. L.; Williams, F. J. Phys. Chem. 1981, 85(5), 510-511.
128. Freunberger, S. A.; Chen, Y.; Peng, Z.; Griffin, J. M.; Hardwick, L. J.; Barde, F.; Novak, P.; Bruce, P. G. J. Am. Chem. Soc. 2011, 133, 8040-8047.
129. Burchill, M. T. Diffusion Effects of Carbonate Solvents in PVDF and PVDF Copolymers. In Progress in Batteries and Battery Materials; 1998, Vol. 17, pp 144-156, ITE-JEC Press.
130. Saunier, J.; Alloin, F.; Sanchez, J. Y.; Barriere, B. J. Polym. Sci.: Part B: Polym. Phys. 2004, 42, 532-543.
131. Saunier, J.; Alloin, F.; Sanchez, J. Y.; Barriere, B. J. Polym. Sci.: Part B: Polym. Phys. 2004, 42, 544-552.
132. Saunier, J.; Alloin, F.; Sanchez, J. Y.; Maniguet, L. J. Polym. Sci.: Part B: Polym. Phys. 2004, 42, 2308-2317.
133. Drago, R. S.; Wong, N. M.; Ferris, D. C. J. Am. Chem. Soc. 1992, 114, 91-98.
134. Friestad, G. K; Marie, J. C.; Suh, Y. S.; Qin, J. J. Org. Chem. 2006, 71, 7016.
135. Duc, M.; Ameduri, B.; Ghislain, D.; Boutevin, B. J. Fluorine Chem. 2007, 128, 144-149.
136. Hallock, S. A.; Wojcicki, A. J. Organomet. Chem. 1979, 182, 521-535.
137. Dolbier, W. R., Jr. Top. Curr. Chem. 1997, 192, 97-163.
138. Pan, X.; Philbin, C. E.; Castellani, M. P.; Tyler, D. R. Inorg. Chem. 1988, 27, 671-676.
139. Martinho Simoes, J. A.; Beauchamp, J. L. Chem. Rev. 1990, 90, 629-688.
140. Okafo, E. N.; Whittle, E. Int. J. Chem. Kinet. 1975, 7, 287-300.
141. Sarakha, M.; Ferraudi, G. Inorg. Chem. 1999, 38, 4605.
142. Koumura, K.; Satoh, K.; Kamigaito, M. Macromolecules 2006, 39, 4054-4061.
143. Gelin, M.; Ameduri, B. J. Polym. Sci.: Part A. Polym. Chem. 2003, 41, 160-171.
144. Laruelle, G.; Nicol, E.; Ameduri, B.; Tassin, J. F, Ajellal, N. J. Polym. Sci. Part A: Polym. Chem. 2011, 49, 3960-3969.
145. Ming, E.; Tsang, W.; Shi, Z.; Holdcroft, S. Macromolecules 2011, 44, 8845-8857.
146. Yang, Y.; Shi, Z.; Holdcroft, S. Macromolecules 2004, 37, 1678-1681.
147. Jol, S. M.; Lee, W. S.; Ahn, B.S.; Park, K Y.; Kim, K. A.; Paeng, I. R. Polym. Bull. 2000, 44, 1-8.
148. Sauguet, L.; Boyer, C.; Ameduri, B.; Boutevin, B. Macromolecules 2006, 39, 9087-9101.
149. Manseri, A.; Ameduri, B.; Boutevin, B.; Kotora, M.; Caporiccio, G. J. Fluorine Chem. 1997, 81, 103-113.
150. Balague, J.; Ameduri, B.; Boutevin, B.; Caporiccio, G. J. Fluorine Chem. 2000, 102, 253-268.
151. Vukicevic, R.; Beuermann, S. Macromolecules 2011, 44, 2597-2603.
152. Wormald, P.; Ameduri, B.; Harris, R. K.; Hazendonk, P. Polymer 2008, 49, 3629-3638.