Original crosslinking of poly(vinylidene fluoride) via trialkoxysilane- containing cure-site monomers

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 44, Issue 12, 2006, Pages 3896-3910

  Cuiot, J ^a   Ameduri, B ^a   Boutevin, B ^a   Lannuzel, T ^b  

^a INSTITUT CHARLES GERHARDT   (France)

^b SOLVAY S A   (Belgium)

Author keywords

Copolymerization; Crosslinking; Curing of polymers; Fluoropolymers; Functionalization of polymers; High performance polymers

Indexed keywords

COPOLYMERIZATION; CROSSLINKING; CURING; FLUORINE CONTAINING POLYMERS; MOISTURE CONTROL; NUCLEAR MAGNETIC RESONANCE; SILANES; SILICON; SOLVENTS;

CURING OF POLYMERS; FLUOROMONOMERS; FUNCTIONALIZATION OF POLYMERS; HIGH PERFORMANCE POLYMERS; POLYVINYLIDENE FLUORIDE (VDF); RADICAL COPOLYMERIZATION; TRIALKOXYSILANE;

MONOMERS;

EID: 33745654771     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.21489     Document Type: Article

References (83)

1. Dohany, R. E. Encycl Polym Sci Technol 1989, 17, 532-547.
2. Seiler, D. A. In Modern Fluoropolymers; Scheirs, J., Ed.; Wiley: New York, 1997; Chapter 25, pp 487-506.
3. Hedli, L.; Wood, K. A.; Cypcar, C. J Fluorine Chem 2000, 104, 63-70.
4. Ameduri, B.; Boutevin, B.Well-Architectured Fluoropolymers: Synthesis, Properties and Applications; Elsevier: Amsterdam, 2004.
5. (a) Schmiegel, W. W. Angew Makromol Chem 1979, 76, 39-53;
6. (b) Logothetis, A. L. Prog Polym Sci 1989, 14, 251-286;
7. (c) Arcella, V.; Ferro, R. In Modern Fluoropolymers; Scheirs, J., Ed.; Wiley: New York, 1997; Chapter 2, pp 71-90;
8. (d) Van Cleeff, A. In Modern Fluoropolymers; Scheirs, J., Ed.; Wiley: New York, 1997; Chapter 32, pp 597-614;
9. (e) Ameduri, B.; Boutevin, B.; Rostov, G. Prog Polym Sci 2001, 26, 105-187;
10. (f) Taguet, A.; Ameduri, B.; Boutevin, B. Adv Polym Sci 2005, 184, 127-211.
11. (a) Tournut, C. Macromol Symp 1994, 82, 99-106;
12. (b) Tournut, C. In Modern Fluoropolymers; Scheirs, J., Ed.; Wiley: New York, 1997; Chapter 31, pp 577-596.
13. (a) Ohmori, A.; Tomihashi, N.; Inukai, H.; Shimizu, Y. (Daikin Kogyo Co., Ltd.). Eur. Pat. Appl. 0,138,091, 1984;
14. (b) Nguyen, T.; Wakselman, C. J Fluorine Chem 1995, 74, 273-280;
15. (c) Dolbier, W. R., Jr.; Kong, X. X.; Barberger, M. D.; Koroniak, H.; Smart, B. E.; Yang, Z. Y. J Chem Soc Perkin Trans 1998, 2, 219-230;
16. (d) Ameduri, B.; Boutevin, B.; Kostov, G.; Petrova, P. J Fluorine Chem 1999, 92, 69-76;
17. (e) Guiot, J.; Ameduri, B.; Boutevin, B. J Polym Sci Part A: Polym Chem 2002, 40, 3634-3643.
18. Ameduri, B.; Boutevin, B.; Rostov, G.; Petrova, P. J Fluorine Chem 1999, 92, 77-84.
19. Ameduri, B.; Bauduin, G.; Boutevin, B.; Rostov, G.; Petrova, P. Macromolecules 1999, 32, 4544-4550.
20. Ameduri, B.; Boutevin, B.; Fruchier, A.; Rostov, G. R.; Petrova, P. J Fluorine Chem 1998, 89, 167-172.
21. (a) Ameduri, B.; Boutevin, B.; Rostov, G.; Petrova, P. Des Monomers Polym 1999, 2, 267-285;
22. (b) Petrova, P.; Ameduri, B.; Boutevin, B.; Rostov, G. (Solvay). U.S. Patent 6,753,392 B1, 2004.
23. (a) Tatemoto, M.; Nakamira, T. (Daikin). Eur. Pat. Sp. 0,398,250 B1, 1990;
24. (b) Rotov, S.; Pedersen, S. D.; Qiu, W.; Qiu, Z. M.; Burton, D. J. J Fluorine Chem 1997, 82, 13-20;
25. (c) Hu, L.-Q.; Mah, C.; Steck, A. E.; Stone, C. J New Mater Electrochem Syst 2000, 3, 43-54;
26. (d) Yamabe, M.; Akiyama, R.; Akatsuda, Y.; Kato, M. Eur Polym J 2000, 36, 1035-1042.
27. (a) Connolly, D. J.; Gresham, W. F. (DuPont). U.S. Patent 3,282,875, 1966;
28. (b) Feiring, A. E.; Doyle, C. M.; Roelofs, M. G.; Farnham, W. B.; Bekiaram, P. G.; Blair, H. A. R. (DuPont). PCT Patent WO 997 45048, 1999;
29. (c) Farnham, W. B.; Feiring, A. E.; Morken, P. (DuPont). PCT Patent WO 99/41292A, 1999;
30. (d) Farnham, W. B.; Bekarian, P. G. (DuPont). PCT Patent WO 00/52060A, 2000;
31. (e) Ameduri, B.; Armand, M.; Boucher, M.; Manseri, A. (Hydro-Que bec). European Patent EP 1, 252, 205, 2005;
32. (f) Bekiarian, P. G.; Doyle, C. M.; Farnham, W. B.; Feiring, A. E.; Morken, P.; Roelofs, M. G.; Marshall, W. J. J Fluorine Chem 2004, 125, 1187-1204.
33. Guiot, J.; Ameduri, B.; Boutevin, B.; Lannuzel, T. Eur Polym J 2003, 39, 887-896.
34. (a) Albin, J. R.; Gallagher, G. A. (DuPont). U.S. Patent 3,136,745, 1964;
35. (b) Schuman, P. D. Sci Technol Aerospace Rep 1968, 6, 957-985
36. (NASA Contract Report NASA-CR-93172, 1966);
37. (c) Tatemoto, M.; Amano, T. (Daikin). Eur. Pat. Sp. 0,077,998, 1982;
38. (d) Yamabe, M.; Rojima, G.; Wachi, H.; Rodama, S. (Asahi Glass Co, Ltd.). U.S. Patent 4,418,186, 1983;
39. (e) Albano, M.; Arcella, V.; Chiodini, G.; Minutillo, A. (Ausimont). European Patent EP 0,618,241 B1, 1994;
40. (f) Rruger, R.; Piejko, R. E.; Negele, M.; Eisele, U.; Marhold, A. (Bayer). U.S. Patent 5,426,165, 1995.
41. (a) Worm, A. (Dyneon). PCT Patent WO 00/12574, 2001;
42. (b) Ameduri, B.; Boucher, M.; Manseri, A. (Hydro-Quebec). International Demand Patent WO 01/96268, 2001.
43. (a) Apotheker, D.; Krusic, P. J. (DuPont). U.S. Patent 4,214,060, 1976;
44. (b) Moggi, G.; Bonardelli, P.; Monti, C.; Bart, J. C. J. Polym Bull 1984, 11, 35;
45. (c) Chiodino, G.; Lagostina, A.; Merenda, M.; Minutillo, A.; Montessoro, E. (Ausimont). Eur. Pat. Appl. 0,410,351 B1, 1992;
46. (d) Arcella, V.; Albano, M.; Barchiesi, E.; Brinati, G.; Chiodini, G. Rubber World 1993, 207, 18-26;
47. (e) Ameduri, B.; Boucher, M.; Manseri, A. (Hydro-Quebec). PCT Patent WO 01/96268, 2001.
48. (a) Kabeta, K.; Zenbayashi, M.; Shinohara, K. (Toshiba Silicone, K.K.). Japanese Patent 3-17087-A, 1989;
49. (b) Kabeta, K.; Zenbayashi, M.; Shinohara, K. (Toshiba Silicone, K.K.). Japanese Patent 3-17088-A, 1989.
50. Gorbunova, T. L.; Khonina, T. G.; Kodess, M. I.; Podol'skii, A. V.; Saloutin, V. I. Metallurg Khim 1992, 5, 1001-1004;
51. Chem Abstr 1992, 118, 124623.
52. Ameduri, B.; Boutevin, B.; Rostov, G. K.; Petrova, P. J Fluorine Chem 1995, 74, 261-267.
53. Guiot, J.; Neouze, M. A.; Sauguet, L.; Ameduri, B.; Boutevin, B. J Polym Sci Part A: Polym Chem 2005, 43, 917-935.
54. Organic Peroxides, Half-Life Times; Internox Technical Brochure; Akzo-Nobel: Amsterdam, 1991.
55. Kotora, M.; Hajek, M.; Kvicala, J.; Ameduri, B.; Boutevin, B. J Fluorine Chem 1993, 64, 259-267.
56. Gorbunova, T. I.; Kodess, M. I.; Podol'skii, A. V.; Saloutin, V. I. Zh Obshch Khim 1991, 61, 2364-2370.
57. (a) Lukevics, E. Russ Chem Rev 1977, 46, 264-281;
58. (b) Speier, J. L. Adv Organomet Chem 1979, 17, 407-419;
59. (c) Boutevin, B.; Pietrasanta, Y. Prog Org Coat 1985, 13, 297-305;
60. (d) Marciniec, B.Comprehensive Handbook on Hydrosilylation;Pergamon: Oxford, 1992;
61. (e) Boutevin, B.; Guida-Pietrasanta, F.; Ratsmihety, A.; Caporiccio, G.; Gornowicz, G. J Fluorine Chem 1993, 60, 211-218;
62. (f) Lukevics, E.; Belyakova, Z. V.; Pomerantseva, M. G.; Voronkov, M. G. J Organomet Chem Libr (Organomet Chem Rev) 1997, 5, 1-179.
63. (a) Hazeldine, R. N.; Newlands, M. J.; Plumb, J. B. J Chem Soc 1965, 2101-2105;
64. (b) Hazeldine, R. N.; Newlands, M. J.; Iles, B. R. British Patent 1075101, 1967.
65. (a) Kim, Y. K.; Pierce, O. R. J Org Chem 1969, 34, 602-613;
66. (b) Riley, M. O.; Kim, Y. K.; Pierce, O. R. J Fluorine Chem 1971, 10, 85-99.
67. Ameduri, B.; Boutevin, B.; Caporiccio, G.; Guida Pietrasanta, F.; Manseri, A.; Ratsemihety, A. In Fluoropolymers; Hougham, G.; Cassidy, P.; Johns, K.; Davidson, T., Eds.; Kluvert: New York, 1999; Vol. 1, Chapter 5, pp 67-80.
68. (a) Kim, Y. K.; Pierce, O. R.; Bajzer, W. J.; Smith, A. G. J Fluorine Chem 1971, 10, 203-212;
69. (b) Kim, Y. K.; Smith, A. G.; Pierce, O. R. J Org Chem 1973, 38, 1615-1620;
70. (c) Boutevin, B.; Pietrasanta, Y.; Youssef, B. J Fluorine Chem 1986, 31, 57-65;
71. (d) Boutevin, B.; Pietrasanta, Y.; Youssef, B. J Fluorine Chem 1986, 34, 167-173;
72. (e) Ameduri, B.; Won Chi Man, M.; Boutevin, B.; Moreau, J. J Fluorine Chem 2000, 104, 185-194.
73. Tarrant, P.; Oliver, W. H. J Org Chem 1966, 31, 1143-1150.
74. Eleuterio, H. S.; Pensak, D. Proceedings of the 13th European Conference in Fluorine Chemistry, Bordeaux, France, July 2001; Oral Communication C-2.
75. (a) Russo, S.; Behari, K.; Chengji, S.; Pianca, M.; Barchiesi, E.; Moggi, G. Polymer 1993, 34, 4777-4788;
76. (b) Balague, J.; Ameduri, B.; Boutevin, B.; Caporiccio, G. J Fluorine Chem 1995, 70, 215-223;
77. (c) Duc, M.; Ameduri, B.; Boutevin, B.; Kharroubi, M.; Sage, J. M. Macromol Chem Phys 1998, 199, 1271-1289;
78. (d) Pianca, M.; Barchiesi, E.; Esposto, G.; Radice, S. J Fluorine Chem 1999, 95, 71-89.
79. Rostov, G.; Ameduri, B.; Bauduin, G.; Boutevin, B.; Stankova, M. J Polym Sci Part A: Polym Chem 2004, 42, 1693-1706.
80. Duc, M.; Ameduri, B.; Boutevin, B. J Fluorine Chem 2001, 112, 3-12.
81. Rosen, J. J. J Coat Technol 1978, 50, 70-82.
82. Guiot, J.; Ameduri, B.; Boutevin, B.; Lannuzel, T. (Solvay). French Patent 2852316, 2004.
83. Bes, L.; Boutevin, B.; Rousseau, A.; Mercier, R.; Bellini, B.; Decoster, D.; Larchanche, J. F.; Vilcot, J. P. Synth Met 2000, 115, 251-258.