Clarifying the mechanism of the denisov cycle: How do hindered amine light stabilizers protect polymer coatings from photo-oxidative degradation?

Macromolecules

Volumn 43, Issue 10, 2010, Pages 4573-4583

  Hodgson, Jennifer L ^a   Coote, Michelle L ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ALKOXYAMINES; ALKOXYL; ALKOXYL RADICALS; AMINYL RADICAL; COMPUTATIONAL TECHNIQUE; CONCERTED MECHANISM; DIOXYGENS; DIRECT DECOMPOSITION; HINDERED AMINE LIGHT STABILIZER; HYDROGEN TRANSFER; HYDROPEROXIDES; HYDROXYL RADICALS; INTERMEDIATE SPECIE; INTRAMOLECULAR HYDROGEN TRANSFER; NITROXIDE RADICALS; NITROXIDES; PEROXYL RADICAL; PHOTO-OXIDATIVE DEGRADATION; PHOTOOXIDATIVE DAMAGE; POLYMER COATING; POLYMER SYSTEMS; POLYMERIC RADICALS; RADICAL SPECIES; REACTION PATHWAYS; SECONDARY ALCOHOLS; SIDE REACTIONS; SIX-MEMBERED RINGS; SURFACE COATINGS;

AMINES; HYDROCARBONS; HYDROGEN; KETONES; POLYMERS; REACTION KINETICS;

PLASTIC COATINGS;

EID: 77952520909     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma100453d     Document Type: Article

References (53)

1. Yebra, D. M.; Kill, S.; Dam-Johansen, K. Prog. Org. Coat. 2004, 50, 75
2. Allen, N. S. Chem. Soc. Rev. 1986, 15, 373
3. Denisov, E. T. Dev. Poly. Degrad. 1982, 5, 23
4. Bolland, J. L. Proc. R. Soc. London, A 1946, 186, 218
5. Bolland, J. L.; Gee, G. Trans. Faraday Soc. 1946, 42, 236
6. Bolland, J. L.; Gee, G. Trans. Faraday Soc. 1946, 42, 244
7. Step, E. N.; Turro, N. J.; Klemchuk, P. P.; Gande, M. E. Angew. Makromol. Chem. 1995, 232, 65
8. Bortolus, P.; Camaioni, N.; Flamigni, L.; Minto, F.; Monti, S. J. Photochem. Photobiol. A: Chem. 1992, 68, 239
9. Pospísil, J. Adv. Polym. Sci. 1995, 124, 87
10. Gugumus, F. Polym. Degrad. Stab. 1993, 40, 167
11. Pospísil, J.; Pilar, J.; Nespurek, S. J. Vinyl Add. Tech. 2007, 13, 119
12. Pan, J.-Q.; Yan, S. Polym. Degrad. Stab. 1991, 32, 79
13. Carlsson, D. J.; Wiles, D. M. Polym. Degrad. Stab. 1984, 6, 1
14. Wiles, D. M.; Tovborg-Jesen, J. P.; Carlsson, D. J. Pure Appl. Chem. 1983, 55, 1651
15. Klemchuk, P. P.; Gande, M. E.; Cordola, E. Polym. Degrad. Stab. 1990, 27, 65
16. Stipa, P. J. Chem. Soc., Perkin Trans. 2 2001, 1793
17. Kysel, O.; Mach, P.; Micov, M. Polym. Degrad. Stab. 1993, 40, 31
18. Rossi, I.; Venturini, A.; Zedda, A. J. Am. Chem. Soc. 1999, 121, 7914
19. Barton, D. H. R.; Le Gloahec, V. N.; Smith, J. Tetrahedron Lett. 1998, 39, 7483
20. Ma, Z.; Bobbitt, J. M. J. Org. Chem. 1991, 56, 6110
21. Schwetlick, K.; Habicher, W. D. Polym. Degrad. Stab. 2002, 78, 35
22. Goldstein, S.; Samuni, A. J. Phys. Chem. A 2007, 111, 1066
23. Golubev, V. A.; Zhdanov, R. I.; Gida, V. M.; Rozantsev, E. G. Bull. Acad. Sci. U.S.S.R., Chem. Ser. 1971, 20, 768
24. Ganem, B. J. Org. Chem. 1975, 40, 1998
25. Semmelhack, M. F.; Schmid, C. R.; Cortés, D. A. Tetrahedron Lett. 1986, 27, 1119
26. Izgorodina, E. I.; Brittain, D. B. R.; Hodgson, J. L.; Krenske, E. H.; Lin, C. Y.; Namazian, M.; Coote, M. L. J. Phys. Chem. A 2007, 111, 10754
27. Hodgson, J. L.; Namazian, M.; Bottle, S. E.; Coote, M. L. J. Phys. Chem. A 2007, 111, 13595
28. Blinco, J. P.; Hodgson, J. L.; Morrow, B. J.; Walker, J. R.; Will, G. D.; Coote, M. L.; Bottle, S. E. J. Org. Chem. 2008, 73, 6763
29. Hodgson, J. L.; Lin, C. Y.; Coote, M. L.; Marque, S. R. A.; Matyjaszewski, K. Macromolecules 2010, 43, 3728 - 3743.
30. Hehre, W. J.; Radom, L.; Schleyer, P. V. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
31. Koch, W.; Holthausen, M. C. A Chemist's Guide to Density Functional Theory; Wiley-VCH: Weinheim, Germany, 2000.
32. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision B.03; Gaussian, Inc.: Pittsburgh PA, 2003.
33. Werner, H.-J.; Knowles, P. J.; Amos, R. D.; Bernhardsson, A.; Berning, A.; Celani, P.; Cooper, D. L.; Deegan, M. J. O.; Dobbyn, A. J.; Eckert, F.; Hampel, C.; Hetzer, G.; Korona, T.; Lindh, R.; Lloyd, A. W.; McNicholas, S. J.; Manby, F. R.; Meyer, W.; Mura, M. E.; Nicklass, A.; Palmieri, P.; Pitzer, R.; Rauhut, G.; Schütz, M.; Stoll, H.; Stone, A. J.; Tarroni, R.; Thorsteinsson, T. MOLPRO 2000.6; University of Birmingham: Birmingham, U.K., 1999.
34. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502
35. Henry, D. J.; Sullivan, M. B.; Radom, L. J. Chem. Phys. 2003, 118, 4849
36. Curtiss, L. A.; Raghavachari, K. Theor. Chem. Acc. 2002, 108, 61
37. Lin, C. Y.; Hodgson, J. L.; Namazian, M.; Coote, M. L. J. Phys. Chem. A 2009, 113, 3690
38. Humbel, S.; Sieber, S.; Morokuma, K. J. Chem. Phys. 1996, 105, 1959
39. See for example Steinfeld, J. I.; Francisco, J. S.; Hase, W. L. Chemical Kinetics and Dynamics; Prentice Hall: Englewood Cliffs, NJ, 1989.
40. These formulas are outlined in full in the Supporting Information of an earlier publication in this journal: Coote, M. L.; Radom, L. Macromolecules 2004, 37, 590
41. Eckart, C. Phys. Rev. 1930, 35, 1303
42. For a description of this method, see, for example: Coote, M. L.; Collins, M. A.; Radom, L. Mol. Phys. 2003, 101, 1329
43. Goldstein, S.; Samuni, A.; Russo, A. J. Am. Chem. Soc. 2003, 125, 8364
44. Lindsay Smith, J. R.; Nagatomi, E.; Stead, A.; Waddington, D. J.; Bévi're, S. D. J. Chem. Soc., Perkin Trans. 2 2000, 1193
45. Lindsay Smith, J. R.; Nagatomi, E.; Waddington, D. J. J. Chem. Soc., Perkin Trans. 2 2000, 2248
46. Lindsay Smith, J. R.; Nagatomi, E.; Stead, A.; Waddington, D. J. J. Chem. Soc., Perkin Trans. 2 2001, 1527
47. Sobek, J.; Martschke, R.; Fischer, H. J. Am. Chem. Soc. 2001, 123, 2849
48. Beckwith, A. L. J.; Bowry, V. W.; O'Leary, M.; Moad, G.; Rizzardo, E.; Solomon, D. H. J. Chem. Soc., Chem. Comm. 1986, 1003
49. Gaudel-Siri, A.; Siri, D.; Tordo, P. ChemPhysChem 2006, 7, 430
50. Miura, Y.; Utsumi, H.; Hamada, A. Arch. Biochem. Biophys. 1993, 300, 148
51. Russell, G. A. J. Am. Chem. Soc. 1957, 79, 3871
52. Howard, J. A.; Ingold, K. U. J. Am. Chem. Soc. 1968, 90, 1056
53. Foster, J. P.; Weinhold, F. J. Am. Chem. Soc. 1980, 102, 7211