Study on the hydrogen donating abilities of benzofuranones as chain-breaking antioxidants using laser flash photolysis technique

Polymer Degradation and Stability

Volumn 92, Issue 1, 2007, Pages 184-188

  Meng, Xin ^a   Xin, Zhong ^a   Li, Yongrong ^a   Cai, Zhi ^b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b CHINA PETROLEUM AND CHEMICAL CORPORATION   (China)

Author keywords

3 Aryl benzofuranone; Antioxidant; Hydrogen donation; Laser flash photolysis

Indexed keywords

ANTIOXIDANTS; BENZENE; HYDROGEN; LASER APPLICATIONS; PHOTOLYSIS;

3-ARYL-BENZOFURANONE; HYDROGEN DONATION; LASER FLASH PHOTOLYSIS (LFP);

KETONES;

EID: 33845617170     PISSN: 01413910     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.polymdegradstab.2006.07.024     Document Type: Article

References (26)

1. Font-Sanchis, Aliaga C., and Scaiano J.C. Greatly attenuated reactivity of nitrile-derived carbon-centered radicals toward oxygen. Chemical Communications 15 (2002) 1576-1577
2. Lundgren C.V., Koner A.L., Tinkl M., Pischel U., and Nau W.M. Reaction of singlet-excited 2,3-diazabicyclo[2.2.2]oct-2-ene and tert-butoxyl radicals with aryl-substituted benzofuranones. Journal of Organic Chemistry 71 (2006) 1977-1983
3. Bejan E.V., Font-Sanchis E., and Scaiano J.C. Lactone-derived carbon-centered radicals: formation and reactivity with oxygen. Organic Letters 3 25 (2001) 4059-4062
4. Perez-Prieto J., Galian R.E., Miranda M.A., and Lopez-Ortiz F. Benzo[d]-1,2-oxaphospholes as precursors of stabilized C-centered radicals. Organic Letters 6 4 (2004) 561-564
5. Solera P. New trends in polymer stabilization. Journal of Vinyl and Additive Technology 4 3 (1998) 197-210
6. Pospisil J., and Nespurek S. Chain-breaking stabilizers in polymers: the current status. Polymer Degradation and Stability 49 (1995) 99-110
7. Rex I., Graham B.A., and Thompson M.R. Studying single-pass degradation of a high-density polyethylene in an injection molding process. Polymer Degradation and Stability 90 (2005) 136-146
8. King R.E., and Stadler U. Impact of stabilization additive on the controlled degradation of polypropylene. Die Angewandte Makromolekulare Chemie 261/262 (1998) 189-204
9. Mar'in A., Greci L., and Dubs P. Antioxidant activity of 3-aryl-benzofuran-2-one stabilizers (Irganox HP-136) in polypropylene. Polymer Degradation and Stability 76 (2002) 489-494
10. Mar'in A., Greci L., and Dubs P. Physical behavior of 3-aryl-benzofuran-2-one (Irganox HP-136) in polypropylene. Polymer Degradation and Stability 78 (2002) 263-267
11. Pauquet J.R. Breakthrough chemistry for processing stabilization of polypropylene. Journal of Macromolecular Science Part A Pure and Applied Chemistry 36 11 (1999) 1717-1730
12. Das P.K., Encinas M.V., Steenken S., and Scaiano J.C. Reaction of tert-butoxyl radical with phenol: comparison with the reaction of carbonyl triplets. Journal of the American Chemical Society 103 (1981) 4162-4166
13. Valgimigli L., Ingold K.U., and Lusztyk J. Antioxidant activity of vitamin E analogues in water and Kamlet-Taft β-value for water. Journal of the American Chemical Society 118 (1996) 3545-3549
14. Bisby R.H., and Parker A.W. Reaction of ascorbate with α-tocopheroxyl radical in micellar and bilayer membrane systems. Archives of Biochemistry and Biophysics 317 1 (1995) 170-178
15. Mortensen A., and Skibsted L.H. Reactivity of β-carotene towards peroxyl radicals studied by laser flash and steady-state photolysis. FEBS Letters 426 (1998) 392-396
16. Small R.D., and Scaiano J.C. Absolute rates of hydrogen abstraction by tert-butoxy radicals. Journal of the American Chemical Society 100 1 (1978) 296-298
17. Paul H., Small R.D., and Scaiano J.C. Hydrogen abstraction by tert-butoxyl radical. A laser photolysis and electron spin resonance study. Journal of the American Chemical Society 100 14 (1978) 4520-4527
18. Font-Sanchis, Aliaga C., Bejan E.V., Cornejo R., and Scaiano J.C. Generation and reactivity toward oxygen of carbon-centered radicals containing indane, indene, and fluorenyl moieties. Journal of Organic Chemistry 68 (2003) 3199-3204
19. Nesvadba P, Evans S. Process for the preparation of 3-aryl-benzofuranones. US Patent 5607624; 1997.
20. Nesvadba P, Evans S. 3-Aryl-benzofuranones. US Patent 5516920; 1996.
21. Ito O., Alam M.M., Koga Y., and Ouchi A. Laser flash photolysis of 1,8-bis(halomethyl)napthalenes. Journal of Photochemistry and Photobiology A Chemistry 97 (1996) 19-23
22. Font-Sanchis E., Aliaga C., Cornejo R., and Scaiano J.C. Reactivity toward oxygen of isobenzofuranyl radicals: effect of nitro group substitution. Organic Letters 5 9 (2003) 1515-1518
23. Thomas M.J. The role of free radicals and antioxidants. Nutrition 16 7/8 (2000) 716-718
24. Scaiano J.C., Martin A., Yap G.P.A., and Ingold K.U. A carbon-centered radical unreactive toward oxygen: unusual radical stabilization by a lactone ring. Organic Letters 2 7 (2000) 899-901
25. Pérez-Prieto J., Galian R.E., and López-Ortiz F. Influence of substitution at the benzylic position on the behavior of stereoisomeric phosphorus compounds as precursors of stabilized carbon-centered radicals. Organic Letters 7 18 (2005) 3869-3872
26. Aliaga C., Stuart R.S., Aspee A., and Scaiano J.C. Solvent effects on hydrogen abstraction reaction from lactones with antioxidant properties. Organic Letters 7 17 (2005) 3665-3668