Functionalized polystyrene as a versatile support for olefin polymerization catalysts

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 38, Issue 16, 2000, Pages 2979-2992

  Roscoe, Stephen B ^a   Gong, Caiguo ^a   Fréchet, Jean M J ^a   Walzer, John F ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b EXXONMOBIL UPSTREAM RESEARCH COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; BINDING ENERGY; CATALYSTS; CROSSLINKING; ETHYLENE; EXTRACTION; MORPHOLOGY; POLYMERIZATION; POLYPROPYLENES; POLYSTYRENES; SURFACE STRUCTURE; SYNTHESIS (CHEMICAL);

FUNCTIONALIZED POLYSTYRENE; METALLOCENIUM SALTS; OLEFIN POLYMERIZATION CATALYSTS; PARTICLE MORPHOLOGY; POLYMER SUPPORTED CATALYST; PREMATURE CATALYST FRAGMENTATION; VERSATILE SUPPORT;

POLYOLEFINS;

EID: 0034251234     PISSN: 0887624X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0518(20000815)38:16<2979::AID-POLA160>3.0.CO;2-Q     Document Type: Article

References (82)

1. (a) Gladysz, J. A. Chem Rev 2000, 100, 1167-1168 (editorial) and subsequent articles in this thematic issue, "Frontiers in Metal-Catalyzed Polymerization."
2. For other relevant reviews, see (b) Bochmann, M. J Chem Soc Dalton Trans 1996, 255-270;
3. (c) Kaminsky, W. Macromol Chem Phys 1996, 197, 3907-3945;
4. (d) Brintzinger, H. H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew Chem Int Ed Engl 1995, 34, 1143-1170;
5. (e) Mohring, P. C.; Coville, N. J. J Organomet Chem 1994, 479, 1.
6. (a) Recent reviews include Hlatky, G. G. Chem Rev 2000, 100, 1347-1376;
7. (b) Fink, G.; Steinmetz, B.; Zechlin, J.; Przybyla, C.; Tesche, B. Chem Rev 2000, 100, 1377-90.
8. (a) Roos, P.; Meier, G. B.; Samson, J. J. C.; Wieckert, G.; Westerterp, K. R. Macromol Rapid Commun 1997, 18, 319-324;
9. (b) Uozumi, T.; Toneri, T.; Soga, K. Macromol Rapid Commun 1997, 18, 9-15;
10. (c) Chen, Y.; Rausch, M. D.; Chien, J. C. W. J Polym Sci Part A: Polym Chem 1995, 33, 2093-2108;
11. (d) Soga, K.; Kim, H. J.; Shiono, J. Macromol Chem Phys 1994, 195, 3347-3360;
12. (e) Altomare, A.; Solaro, R.; Ciardelli, F.; Barrazoni, L.; Menconi, F.; Malquori, S.; Masi, F. Polymer 1992, 33, 1768-1770;
13. (f) Collins, S.; Kelley, W. M.; Holden, D. A. Macromolecules 1992, 25, 1780-1785;
14. (g) Kaminaka, M.; Soga, K. Polymer 1992, 33, 1105-1107;
15. (h) Marks, T. J. Acc Chem Res 1992, 25, 57-65;
16. (i) Tullock, C. W.; Tebbe, F. N.; Mulhaupt, R.; Ovenall, D. W.; Setterquist, R. A.; Ittel, S. D. J Polym Sci Part A: Polym Chem 1989, 27, 3063-3081;
17. (j) Slotfeldt-Ellingsen, D.; Dahl, I. M.; Ellestaad, O. H. J Mol Catal 1980, 9, 423-434.
18. (a) Soga, K.; Kim, H. J.; Shiono, T. Macromol Rapid Commun 1994, 15, 139-143;
19. (b) Kaminsky, W.; Renner, F. Macromol Rapid Commun 1993, 14, 239-243;
20. (c) Chien, J. C. W.; He, D. J Polym Sci Part A: Polym Chem 1991, 29, 1603-1607;
21. (d) Lee, D.; Yoon, K.; Noh, S. Macromol Rapid Commun 1997, 18, 427-431;
22. (e) Soga, K.; Kaminaka, M. Macromol Chem Phys 1994, 195, 1369-1379;
23. (f) Kaminaka, M.; Soga, K. Macromol Rapid Commun 1991, 12, 367-372.
24. (a) Metza, S. B.; Hsu, C. C.; Bacon, D. W. J Polym Sci Part A: Polym Chem 1996, 34, 1693;
25. (b) Yu, G.; Chen, H.; Zhang, X.; Jiang, Z.; Huang, B. J Polym Sci Part A: Polym Chem 1996, 34, 2237;
26. (c) Mori, H.; Ohnishi, K.; Terano, M. Macromol Rapid Commun 1996, 17, 25-29;
27. (d) Sun, L.; Shariati, A.; Hsu, J. C.; Bacon, D. W. Stud Surf Sci Catal 1994, 89, 81;
28. (e) Sun, L.; Hsu, C. C.; Bacon, D. W. J Polym Sci Part A: Polym Chem 1994, 32, 2127;
29. (f) Bochkin, A. M.; Pomogailo, A. D.; Dyachkovskii, F. S. React Polym 1988, 9, 99-107;
30. (g) Mkrtchyan, S. A.; Uvarov, B. A.; Tsvetkova, V. I.; Yu. Tovmasyan, M.; Chistyakov, S. O.; Rachinskii, G. F.; D'yachkovskii, F. B. Polym Sci USSR 1986, 28, 2343-2350.
31. (a) Galli, P.; Collina, G.; Sgarzi, P. Baruzzi, G.; Marchetti, E. J Appl Polym Sci 1997, 66, 1831-1837;
32. (b) Hungenberg, K. D.; Kerth, J.; Langhauser, F.; Marczinke, B.; Schlund, R. In Ziegler Catalysts; Fink, G.; Mülhaupt, R.; Brintzinger, H. H., Eds.; Springer-Verlag: Berlin, 1995; pp 363-386.
33. (a) Arai, T.; Hoang, B. T.; Uozumi, T.; Soga, K. Macromol Chem Phys 1997, 198, 229-237;
34. (b) Kitagawa, T.; Uozumi, T.; Soga, K.; Takata, T. Polymer 1997, 38, 615-620;
35. (c) Soga, K.; Arai, T.; Hoang, B. T.; Uozumi, T. Macromol Rapid Commun 1995, 16, 905-911;
36. (d) Nishisda, H.; Uozumi, T.; Arai, T.; Soga, K. Macromol Rapid Commun 1995, 16, 821-830.
37. Lee, D.; Yoon, K. Macromol Rapid Commun 1994, 15, 841.
38. For some patents on polymer-supported olefin polymerization catalysts, see (a) Soga, K.; Kim, H.; Lee, S.; Jung, M.; Son, B.; Thosiya, W.; Thaksahi, I.; Nishida, H. U.S. Patent 5,610,115, 1997;
39. (b) Dimaio, A. J.; Meverden, C. C. U.S. Patent 4,246,134, 1996;
40. (c) Furtek, A. B.; Krause, M. J. U.S. Patent 5,455,214, 1996;
41. (d) Turner, H. W. U.S. Patent 5,427,991, 1995;
42. (e) Cann, K. J.; Brady, R. C.; Gau, Y. U.S. Patent 5,102,841, 1992;
43. (f) Maly, N. A. U.S. Patent 4,463,135, 1984.
44. (a) Scollard, J. D.; McConville, D. H.; Payne, N. C.; Vittal, J. J. Macromolecules 1996, 29, 5241-5243;
45. (b) Johnson, L. K.; Mecking, S.; Brookhart, M. J Am Chem Soc 1996, 118, 267;
46. (c) Johnson, L. K.; Killian, C. M.; Brookhart, M. J Am Chem Soc 1995, 117, 6414;
47. (d) Coates, G. W.; Waymouth, R. M. Science 1995, 267, 217-219;
48. (e) Shapiro, P. J.; Bunel, E.; Schaefer, W. P.; Bercaw, J. E. Organometallics 1990, 9, 867.
49. (a) Canich, J. A. (Exxon). Eur. Pat. Appl. EP-420-436-A1, 1991;
50. (b) Stevens, J. C.; Timmers, F. J.; Wilson, D. R.; Schmidt, G. F.; Nickias, P. N.; Rosen, R. K.; Knight, G. W.; Lai, S. Y. (Dow). Eur. Pat. Appl. EP-416-815-A2, 1991.
51. (a) Hodge, P.; Sherrington, D. C. Polymer-Supported Reactions in Organic Synthesis; Wiley: New York, 1980; pp 44-52;
52. (b) Grubbs, R. H. CHEMTECH 1977, 7, 512-518;
53. (c) Fréchet, J. M. J.; Farrall, M. J. In Chemistry and Properties of Crosslinked Polymers; Labana, S. S., Ed.; Academic: New York, 1977; pp 59-83;
54. (d) Fréchet, J. M. J.; de Smet, M.; Farrall, M. J. J Org Chem 1979, 44, 1774-1779;
55. (e) Farrall, M. J.; Fréchet, J. M. J. J Org Chem 1976, 41, 3877-3882.
56. (a) Chen, E. Y.-X.; Marks, T. J. Chem Rev 2000, 100, 1391-1434;
57. (b) Yang, X.; Stern, C.; Marks, T. J. Organometallics 1991, 10, 840;
58. (c) Hlatky, G. G.; Upton, D. T.; Turner, H. W. U.S. Pat. Appl. 459,921, 1990.
59. Chien, J. C. W.; Tsai, W.-M.; Rausch, M. D. J Am Chem Soc 1991, 113, 8570-8571.
60. Xiang, X. D.; Sun, X.; Briceño, G.; Lou, Y.; Wang, K.-A.; Chang, H.; Wallace-Freedman, W. G.; Chen, S.-W.; Schultz, P. G. Science 1995, 268, 1738-1740.
61. Roscoe, S. B.; Fréchet, J. M. J.; Walzer, J. F.; Dias, A. J. Science 1998, 280, 270-273.
62. Farrall, M. J.; Fréchet, J. M. J. J Org Chem 1976, 41, 3877-3882.
63. (a) Merrifield, R. B. J Am Chem Soc 2149-2154, 85, 1963;
64. (b) Fréchet, J. M. J.; Schuerch, C. J Am Chem Soc 1971, 93, 492-496;
65. (c) Sparrow, J. T. Tetrahedron Lett 1975, 52, 4637-4638.
66. Pepper, K. W.; Paisley, H. M.; Young, M. A. J Chem Soc 1953, 4097-4105.
67. (a) Xie, T.; McAuley, K. B.; Hsu, J. C. C.; Bacon, D. W. Ind Eng Chem Res 1994, 33, 449-479 and references therein;
68. (b) Kakugo, M.; Sadatoshi, H.; Yokoyama, M.; Kojima, K. In Transition Metals and Organometallics as Catalysts for Olefin Polymerization; Kaminsky, W.; Sinn, H., Eds.; Springer-Verlag: Berlin, 1988; p 433;
69. (c) Baker, R. T. K.; Harris, P. S.; Waite, R. J.; Roper, A. N. J Polym Sci Part B: Polym Lett 1972, 11, 45-53;
70. (d) Mackie, P.; Berger, M. N.; Grieveson, B. M.; Lawson, D. Polym Lett 1967, 5, 493-494.
71. Hutchinson, R. A.; Chen, C. M.; Ray, W. H. J Appl Polym Sci 1992, 44, 1389-1414.
72. The observation that samples of lower catalyst loading display markedly higher specific activities (Table II) suggests that the polymerization rate is limited by the diffusion rate of the monomers, at least for the higher loadings tested.
73. 2 were run to constant ethylene consumption. The amount of polymer formed during the polymerization is assessed in real time on the basis of the ethylene consumption, and, with experience, the time required for a certain amount of product can be estimated with reasonable accuracy.
74. The term comonomer effect is used here to describe a situation in which the addition of a comonomer that homopolymerizes more slowly than ethylene, such as hexene or octene, leads to higher overall productivity by plasticizing the polymer particle produced. Because these particles effectively encapsulate the active sites, this plasticization allows higher diffusion rates for both monomers and thus a greater overall polymerization rate.
75. (a) Spalek, W.; Küber, F.; Winter, W.; Rohrmann, J.; Bachmann, B.; Antberg, M.; Dolle, V.; Paulus, E. F. Organometallics 1994, 13, 954-963;
76. (b) Spalek, W.; Antberg, M.; Rohrmann, J.; Winter, W.; Bachmann, B.; Kiprof, P.; Behm, J.; Herrmann, W. A. Angew Chem Int Ed Engl 1992, 31, 1347-1350.
77. 3).
78. (a) Suhm, J.; Schneider, M. J.; Mülhaupt, R. J Polym Sci Part A: Polym Chem 1997, 35, 735-740;
79. (b) Mühlenbrock, P. H.; Fink, G. Z Naturforsch B: Chem Sci 1995, 50, 423-429;
80. (c) Kaminsky, W.; Schlobohm, M. Macromol Chem Macromol Symp 1986, 4, 103-118.
81. Lange's Handbook of Chemistry, 13th ed.; Dean, T. A., Ed.; McGraw-Hill: New York, 1985; pp 5-18-5-60.
82. a Predictions for Organic Acids and Bases; Chapman & Hall: London, 1981; pp 21-26.