Tetramethylammonium tetraorganylborates as coinitiators with 5,7-diiodo-3-butoxy-6-fluorone in visible light polymerization of acrylates

Macromolecules

Volumn 29, Issue 25, 1996, Pages 8274-8276

  Polykarpov, Alexander Y ^a   Hassoon, Salah ^a   Neckers, Douglas C ^a  

^a BOWLING GREEN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORON COMPOUNDS; DISSOLUTION; INITIATORS (CHEMICAL); PHOTOCHEMICAL REACTIONS; POLYACRYLATES; POLYMERIZATION; SOLUBILITY; STABILITY;

COINITIATORS; DIIODO BUTOXY FLUORONE; TETRAMETHYLAMMONIUM TETRAORGANYLBORATES; VISIBLE LIGHT POLYMERIZATION;

SALTS;

EID: 0030566522     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma960597w     Document Type: Article

References (25)

1. Contribution No. 273 from the Center for Photochemical Sciences.
2. For a summary, see: Schuster, G. B. Pure Appl. Chem. 1990, 62, 1565.
3. Chatterjee, S.; Gottschalk, P.; Davis, P. D.; Schuster, G. B. J. Am. Chem. Soc. 1988, 110, 2326. Chatterjee, S.; Gottschalk, P.; Davis, P. D.; Kurz, M. E.; Saurwein, B.; Yang, X.; Schuster, G. B. J. Am. Chem. Soc. 1990, 112, 6329. Schuster, G. B.; Yang, X.; Zou, C.; Saurwein, B. J. Photochem. Photobiol. A: Chem. 1992, 65, 191. Murphy, S.; Yang, X.; Schuster, G. B. J. Org. Chem. 1995, 60, 2411.
4. Chatterjee, S.; Gottschalk, P.; Davis, P. D.; Schuster, G. B. J. Am. Chem. Soc. 1988, 110, 2326. Chatterjee, S.; Gottschalk, P.; Davis, P. D.; Kurz, M. E.; Saurwein, B.; Yang, X.; Schuster, G. B. J. Am. Chem. Soc. 1990, 112, 6329. Schuster, G. B.; Yang, X.; Zou, C.; Saurwein, B. J. Photochem. Photobiol. A: Chem. 1992, 65, 191. Murphy, S.; Yang, X.; Schuster, G. B. J. Org. Chem. 1995, 60, 2411.
5. Chatterjee, S.; Gottschalk, P.; Davis, P. D.; Schuster, G. B. J. Am. Chem. Soc. 1988, 110, 2326. Chatterjee, S.; Gottschalk, P.; Davis, P. D.; Kurz, M. E.; Saurwein, B.; Yang, X.; Schuster, G. B. J. Am. Chem. Soc. 1990, 112, 6329. Schuster, G. B.; Yang, X.; Zou, C.; Saurwein, B. J. Photochem. Photobiol. A: Chem. 1992, 65, 191. Murphy, S.; Yang, X.; Schuster, G. B. J. Org. Chem. 1995, 60, 2411.
6. Chatterjee, S.; Gottschalk, P.; Davis, P. D.; Schuster, G. B. J. Am. Chem. Soc. 1988, 110, 2326. Chatterjee, S.; Gottschalk, P.; Davis, P. D.; Kurz, M. E.; Saurwein, B.; Yang, X.; Schuster, G. B. J. Am. Chem. Soc. 1990, 112, 6329. Schuster, G. B.; Yang, X.; Zou, C.; Saurwein, B. J. Photochem. Photobiol. A: Chem. 1992, 65, 191. Murphy, S.; Yang, X.; Schuster, G. B. J. Org. Chem. 1995, 60, 2411.
7. For examples of cyanine dyes, see (a) Gottschalk, P.; Neckers, D. C.; Schuster, G. B. U.S. Patent 4772530, Sept 20, 1988; U.S. Patent 4842980, June 27, 1989.
8. (b) Gottschalk, P. U.S. Patent 4874450, Oct 17, 1989.
9. (c) Weed, G. C.; Monroe, B. M. U.S. Patent 5143818, Sept 1, 1992.
10. (d) Matsuoka, M.; Hikida, T.; Murobushi, K.; Hosoda, Y. J. Chem. Soc., Chem. Commun. 1993, 299. For pyrylium and thiopyrylium dyes, see:
11. (e) Kawamura, K.; Okamoto, Y. U.S. Patent 4971891, Nov 20, 1990. For coumarin dyes with borates as photoinitiators, see:
12. (f) Koike, M.; Kita, N. U.S. Patent 4950581, Aug 21, 1990. Xanthene dyes and borates are patented in:
13. (g) Gottschalk, P.; Neckers, D. C.; Schuster, G. B. U.S. Patent 5151520, Sept 29, 1992.
14. For the estimation of oxidation potentials of tetraarylborates, see: Murphy, S. T.; Zou, C.; Miers, J. B.; Ballew, R.; Dlott, D.; Schuster, G. B. J. Phys. Chem. 1993, 97, 13152.
15. Sarker, A. M.; Polykarpov, A. Y.; Neckers, D. C.; deRaaff, A. M.; Marino, T. J. Polym. Sci., Part A: Polym. Chem. 1996, 34, 2817.
16. Tanabe, T.; Torres-Filho, A.; Neckers, D. C. J. Polym. Sci., Part A: Polym. Chem. 1995, 33, 1691.
17. For the synthesis of organoborates by the addition of organolithiums to boranes, see: Negishi, E.; Idacavage, M. J.; Chiu, K. W.; Yoshida, T.; Abramovitch, A.; Goettel, M. E.; Silveira, A.; Bretherick, H. D. J. Chem. Soc., Perkin Trans. 2 1978, 1225. Damico, R. J. Org. Chem. 1964, 29, 1971.
18. For the synthesis of organoborates by the addition of organolithiums to boranes, see: Negishi, E.; Idacavage, M. J.; Chiu, K. W.; Yoshida, T.; Abramovitch, A.; Goettel, M. E.; Silveira, A.; Bretherick, H. D. J. Chem. Soc., Perkin Trans. 2 1978, 1225. Damico, R. J. Org. Chem. 1964, 29, 1971.
19. Torres-Filho, A.; Neckers, D. C. J. Appl. Polym. Sci. 1994, 51, 931.
20. Osteryoung, J.; O'Dea, J. J. In Electroanalytical Chemistry; Bard, A. J., Ed.; Marcel Dekker: New York, 1986; Vol. 14, pp 209-308.
21. Mann, C. K.; Barnes, K. K. Electrochemical Reactions in Non-Aqueous Systems; Marcel Dekker: New York, 1970.
22. Hassoon, S.; Neckers, D. C. J. Phys. Chem. 1995, 99, 9416.
23. Rehm, D.; Weller, A. Isr. J. Chem. 1970, 8, 259.
24. For the kinetic method of determination of redox potentials, see: Murphy, S.; Schuster, G. B. J. Phys. Chem. 1995, 99, 511. Also, see refs 3 and 5.
25. Tetraorganylborates become more soluble with the increase of the number of alkyl groups per boron and with more methylenes in the alkyl ligands. The solubility in the monomer can also be improved by altering the ammonium counterion, as in ref 6.