Physical and chemical probes of the bond strength between trialkylboranes and amines and their utility as stabilized free radical polymerization catalysts

Macromolecules

Volumn 39, Issue 7, 2006, Pages 2507-2513

  Sonnenschein, Mark F ^a   Webb, Steven P ^a   Redwine, O David ^a   Wendt, Benjamin L ^a   Rondan, Nelson G ^a  

^a DOW CHEMICAL COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BOND STRENGTH; CHEMICAL PROBES; TRIALKYLBORANES;

ADHESION; CATALYSTS; CHEMICAL BONDS; FREE RADICAL POLYMERIZATION; OXYGEN;

AMINES;

EID: 33645977200     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma060268w     Document Type: Article

References (44)

1. Brewis, D. M.; Briggs, D. Polymer 1981, 22, 7-16.
2. Rahut, H. W. Adhes. Age 1969, 12, 28-38.
3. Devine, A. T.; Bodnar, M. J. Adhes. Age 1969, 12, 35-37.
4. Clemens, R. J.; et al. Prog. Org. Coat. 1994, 24, 43-54.
5. Badey, J. P.; et al. Int. J. Adhes. Adhes. 1996, 16, 173-178.
6. Schonhorn, H.; Hansen, R. H. J. Appl. Polym. Sci. 1967, 11, 1461-1474.
7. Westerdahl, C. W.; Hall, J. R.; Schramm, E. C.; Levi, D. W. J. Colloid Interface Sci. 1974, 47, 610-620.
8. Biais, P.; Carlsson, D. J.; Csullog, G. W.; Wiles, D. M. J. Colloid Interface Sci. 1974, 47, 636-649.
9. Schmitz, P. J.; Holubka, J. W. J. Adhes. 1995, 48, 137-148.
10. Brewis, D. M. Mathiewson, I.; Wolfsenberger, M. Int. J. Adhes. Adhes. 1995, 15, 87-90.
11. Yang, J.; Garton, A. J. Appl. Polym. Sci. 1993, 48, 359-370.
12. (a) Sonnenschein, M. F.; Webb, S. P.; Rondan, N. U.S. Patent 6,-706,831, 2004.
13. (b) Sonnenschein, M. F.; Webb, S. P.; Rondan, N. U.S. Patent 6,713,578, 2004.
14. (c) Sonnenschein, M. F.; Webb, S. P.; Rondan, N. U.S. Patent 6,730,759, 2004.
15. (d) Webb, S. P.; Sonnenschein, M. F.; U.S. Patent 6,740,716, 2004.
16. (e) Sonnenschein, M. F.; Webb, S. P.; Wendt, B. L.; Harrington, D. R.; U.S. Patent 6,762,260, 2004.
17. (f) Sonnenschein, M. F.; Wendt, B. L. PCT WO 2005/082912 A1, 2005.
18. Skoultchi, M. M.; Merlo, N. V. U.S. Patent 5,106,928, 1992.
19. (a) Zharov, J. V.; Krasno, J. N. U.S. Patent 5,539,070, 1996.
20. (b) Deviny, E. J. U.S. Patent 5,990,036, 1999.
21. (c) Pocius, A. U.S. Patent 6,093,778, 2000.
22. Maandi, E. U.S. Patent 6,632,908, 2003.
23. Kendall, J. L. Righettini, R. F.; Abbey, K. J. U.S. Patent 6,646,076, 2004.
24. Diakoumakos, C. D. Kotzev, D. L. PCT. WO 2005/044867 A1, 2005.
25. Chung, T. C.; Jiang, G. J.; Rhubright, D. Macromolecules 1993, 26, 3467-3471.
26. Wang, Z. M.; Hong, H.; Chung, T. C. Macromolecules 2005, 38, 8966-8970.
27. Ingold, K. U. In Free Radicals; Kochi, J., Ed.; Wiley: New York, 1973; Vol. 1, p 80.
28. Sonnenschein, M. F.; Webb, S. P.; Kastl, P. K.; Arriola, D. J. Wendt, B. L.; Harrington, D. R.; Rondan, N. G. Macromolecules 2004, 37, 7974-7978.
29. Muetterties, E. J. The Chemistry of Boron and its Derivatives; Wiley: New York, 1967.
30. Hoberg, H.; Gotz, V. J. Organomet. Chem. 1976, 118, C3-C5.
31. Welch, F. J. J. Polym. Sci. 1962, 61, 243-252.
32. Johnson, R. M.; Siddiqi, I. W. The Determination of Organic Peroxides; Pergamon Press: Oxford, U.K., 1970.
33. Pocius, A. V. Adhesion and Adhesives Technology; Hanser, Munich, Germany, 1997 pp 42-45.
34. Spartan 2004 Wavefunction Inc.: Irvine, CA.
35. The reliability of these calculations is illustrated by comparing the calculated the dissociation energy of diethylperoxide 36.5 kcal/mol with the experimental value of 37.9 ± 1 kcal/mol. Cf.: Batt, L.; Christic, K.; Milne, R. T.; Summers, A. J. Int. J. Chem. Kinet. 1974, 6, 813.
36. Cox, S. R.; Williams, D. E. J. Comput. Chem. 1981, 2, 304-323.
37. Johnson, J. R.; Snyder, H. R.; Van Campen, M. G. J. Am. Chem. Soc. 1938, 60, 115-121.
38. Peerboom, R. A.; Ingmann, S.; Nibbering, N. M.; Liebman, J. F. J. Chem. Soc., Perkin Trans. 2 1990, 1825-1827.
39. Gonzalez, A. I.; et al. J. Phys. Chem. 1996, 100, 10490-10496.
40. Alder, R. W. Chem. Rev. 1989, 89, 1215-1223.
41. Spiegel, D. A.; Wiberg, K. B.; Schacherer, L. N.; Medeiros, M. R.; Wood, J. L. J. Am. Chem. Soc. 2005, 127, 12513-12515.
42. Nöth, H.; Wrackmeyer, B. Chem. Ber. 1974, 107, 3070-3088.
43. House, H. O. Modern Synthetic Reactions; Benjamin Cummings: Menlo Park, CA, 1972.
44. Herrington, R.; Nafziger, L.; Hock, K.; Moore, R.; Casati, F.; Lidy, W. In Flexible Polyurethane Foams; Herrington, R., Ed.; Dow Chemical: Midland, MI, 1997; pp 2-32.