Mechanism and selectivity of 2,3-dimethyl-2,3-diphenylbutane mediated addition of vinyltriethoxysilane to polyethylene

European Polymer Journal

Volumn 42, Issue 5, 2006, Pages 971-980

  Scott Parent, J ^a   Wu, Wei ^a   Sengupta, Saurav S ^a   Jackson, Peter ^b  

^a QUEEN S UNIVERSITY   (Canada)

^b ShawCor Ltd   (Canada)

Author keywords

Bicumene; Free radical grafting; Model compounds; Polymer modification; Vinylsilane

Indexed keywords

ADDITION REACTIONS; HYDROCARBONS; HYDROGEN; LOW DENSITY POLYETHYLENES; REACTION KINETICS;

BICUMENE; FREE RADICAL GRAFTING; MODEL COMPOUNDS; POLYMER MODIFICATION; VINYLSILANE;

HIGH DENSITY POLYETHYLENES;

EID: 33645963487     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.eurpolymj.2005.11.007     Document Type: Article

References (31)

1. Munteanu D. In: Al-Malaika S. (Ed). Reactive modifiers for polymers (1997), Blackie Academic and Professional, London 196-265
2. Moad G. The synthesis of polyolefin graft copolymers by reactive extrusion. Prog Polym Sci 24 (1999) 81-142
3. Parent J.S., Cirtwill S., Penciu A., Whitney R.A., and Jackson P. 2,3-Dimethyl-2,3-diphenylbutane mediated grafting of vinyltriethoxysilane to polyethylene: a novel radical initiation system. Polymer 44 (2003) 953-961
4. Russell K.E. Free radical graft polymerization and copolymerization at higher temperatures. Prog Polym Sci 27 (2002) 1007-1038
5. In: Brandrup J., Immergut E.H., and Grulke E.A. (Eds). Polymer handbook. 4th ed. (1999), Wiley, New York II-68
6. The C-H bond dissociation energy of cumene is 353.1 kJ/mol, compared to 399.6 kJ/mol for cyclohexane.
7. Parent J.S., Tripp M., and Dupont J. Selectivity of peroxide-initiated graft modification of ethylene copolymers. Polym Eng Sci 43 (2003) 234-242
8. Spencer M., Parent J.S., and Whitney R.A. Composition distribution in poly(ethylene-graft-vinyltrimethoxysilane). Polymer 44 (2003) 2015-2023
9. Hamielec A.E., Gloor P.E., and Zhu S. Kinetics of free radical modification of polyolefins in extruders - chain scission, crosslinking and grafting. Can J Chem Eng 69 (1991) 611-618 And references therein
10. Alfassi Z.B., and Feldman L. The kinetics of radiation induced hydrogen abstraction by trichloromethyl radicals in the liquid phase: cyclanes. Int J Chem Kinet 13 (1981) 517-526
11. Fujisaki N., Ruf A., and Gaumann T. Kinetic isotope effects for hydrogen abstractions from n-alkanes by hydrogen atoms in the gas phase. J Chem Phys 80 (1984) 2570-2577
12. Nelsen S.F., and Bartlett P.D. Azocumene. I. Preparation and decomposition of azocumene. Unsymmetrical coupling products of the cumyl radical. J Am Chem Soc 88 (1966) 137-143
13. Fujisaki N., Ruf A., and Gaumann T. Kinetic isotope effects for hydrogen abstraction from a series of cycloalkanes and branched alkanes by hydrogen atoms in the gaseous phase. J Am Chem Soc 107 (1985) 1605-1610
14. Wampler F.B., and Kuntz R.R. Hydrogen abstraction reactions of the trichloromethyl radical. Int J Chem Kinet 3 (1971) 283-289
15. Cook G.K., and Mayer J.M. C-H bond activation by metal oxo species: chromyl chloride oxidations of cyclooctane, isobutane, and toluene. J Am Chem Soc 117 (1995) 7139-7156
16. Rauer K, Demel P. Degradation of polyethylene by radical formers. Eur Patent 0273274, 1987.
17. Rosales C., Perra R., Ichazo M., Gonzalez J., Rojas H., Sanchez A., et al. Grafting of polyethylenes by reactive extrusion. I. Influence on the molecular structure. J Appl Polym Sci 70 (1998) 161-176
18. Wong W.K., and Varrall D.C. Role of molecular structure on the silane crosslinking of polyethylene: the importance of resin molecular structure change during vinyltrimethoxysilane grafting. Polymer 35 (1994) 5447-5452
19. Forsyth J.C., Baker W.E., Russell K.E., and Whitney R.A. Peroxide-initiated vinylsilane grafting: structural studies on a hydrocarbon substrate. J Polym Sci Part A: Polym Chem 35 (1998) 3517-3525
20. Gibian M.J., and Corely R.C. Organic radical-radical reactions. Disproportionation vs. combination. Chem Rev 73 (1973) 441-464
21. Muenger K., and Fisher H. Separation of polar and steric effects on absolute rate constants and Arrhenius parameters for the reaction of tert-butyl radicals with alkenes. Int J Chem Kinet 17 (1985) 809-829
22. Ingold K.U. In: Kochi J.K. (Ed). Free radicals vol. I (1973), J Wiley & Sons, New York 37-112
23. Howard J.A., Bennett J.E., and Brunton G. Absolute rate constants for hydrocarbon autoxidation. 30. On the self-reaction of the α-cumylperoxy radical in solution. Can J Chem 59 (1981) 2253-2260
24. Bell E.R., Raley J.H., Rust F.F., Seubold F.H., and Vaughan W.E. Reactions of free radicals associated with low-temperature oxidation of paraffins. Discuss Faraday Soc 10 (1951) 242-249
25. Benson S.W. Effects of resonance and structure on the thermochemistry of organic peroxy radicals and the kinetics of combustion reactions. J Am Chem Soc 87 (1965) 972-979
26. Walling C. Limiting rates of hydrocarbon autoxidations. J Am Chem Soc 91 (1969) 7590-7594
27. Kharasch M.S., Fono A., and Nudenberg W. Hydroperoxides. VI. The thermal decomposition of α-cumyl hydroperoxide. J Org Chem 16 (1951) 113-127
28. Tolman C.A., Druliner J.D., Nappa M.J., and Herron N. Activation and functionalization of alkanes. In: Hill C.L. (Ed) (1989), John Wiley & Sons 303-360
29. Brown N., Hartig M.J., Roedel M.J., Anderson A., and Schweitzer C.E. Cycloalkanone peroxides. I. Preparation of "cyclohexanone peroxide" by oxidation of cyclohexanol. J Am Chem Soc 77 (1955) 1756-1759
30. Michaels A., and Bixler H.J. Solubility of gases in polyethylene [and rubbery polymers]. J Polym Sci 50 (1961) 393-412
31. Wilcock R.J., Battino R., and Wilhelm E.J. The solubility of gases in liquids. 10. The solubility of helium, neon, argon, krypton, nitrogen, oxygen, carbon monoxide, carbon dioxide, methane, tetrafluoromethane and sulfur hexafluoride in cyclooctane at 289-313 K. Chem Thermodyn 9 (1977) 111-115