Study of the high temperature reactions of a hindered aryl phosphite (Hostanox PAR 24) used as a processing stabiliser in polyolefins

Polymer Degradation and Stability

Volumn 95, Issue 9, 2010, Pages 1883-1893

  Kriston, Ildikó ^a,b   Pénzes, Gábor ^a,b   Szijjártó, Gábor ^a,b   Szabó, Pál ^a   Staniek, Peter ^c   Földes, Enikod́ ^a,b   Pukánszky, Béla ^a,b  

^a CHEMICAL RESEARCH CENTER   (Hungary)

^b BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^c SÜD CHEMIE AG   (Germany)

Author keywords

Heat stability; Hindered aryl phosphite; Oxidation; Processing stabilisation of polyolefins; Reactions with radicals

Indexed keywords

AZOBISISOBUTYRONITRILE; CHEMICAL COMPOSITIONS; CUMENE HYDROPEROXIDE; DICUMYL PEROXIDE; HEAT-STABILITY; HIGH-TEMPERATURE REACTION; HINDERED ARYL PHOSPHITE; OXYGEN ATMOSPHERE; PEROXY RADICALS; PHOSPHOROUS ANTIOXIDANTS; POLYETHYLENE PROCESSING; REACTIONS WITH RADICALS; RECOMBINATION REACTIONS; STABILISATION; STABILISER; THERMAL DECOMPOSITIONS; THERMO-OXIDATIVE STABILITY; THERMOGRAVIMETRIC METHOD;

ARGON; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION; PHOSPHORUS; POLYETHYLENES; PYROLYSIS; STABILITY;

MOLECULAR OXYGEN;

EID: 77955514602     PISSN: 01413910     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.polymdegradstab.2010.04.017     Document Type: Article

References (43)

1. H. Zweifel Stabilization of polymeric materials 1998 Springer Berlin
2. I. Kriston, Á Orbán-Mester, G. Nagy, P. Staniek, E. Földes, and B. Pukánszky Melt stabilisation of Phillips type polyethylene, part I: the role of phenolic and phosphorous antioxidants Polym Degrad Stab 94 2009 719 729
3. T. Haruna Aspects of stabilization with phosphorous antioxidants in polymers Angew Makromol Chem 232 1995 119 131
4. I. Kriston, Á Orbán-Mester, G. Nagy, P. Staniek, E. Földes, and B. Pukánszky Melt stabilisation of Phillips type polyethylene, part II: correlation between additive consumption and polymer properties Polym Degrad Stab 94 2009 1448 1456
5. J. Tocháek, and J. Sedlá Hydrolysis and stabilization performance of bis(2,4-di- t-butylphenyl)pentaerythrityl diphosphite in polypropylene Polym Degrad Stab 50 1995 345 352
6. M.S. Dopico-García, J.M. López-Vilarino, and M.V. González-Rodríguez Determination of antioxidants by solid-phase extraction method in aqueous food simulants Talanta 66 2005 1103 1107
7. K. Schwetlick, and W.D. Habicher Organophosphorus antioxidants action mechanisms and new trends Angew Makromol Chem 232 1995 239 246
8. Ch Walling, and R. Rabinowitz The reaction of trialkyl phosphites with thiyl and alkoxy radicals J Am Chem Soc 81 1959 1243 1249
9. C. Neri, S. Costanzi, R.M. Riva, R. Farris, and R. Colombo Mechanism of action of phosphites in polyolefin stabilisation Polym Degrad Stab 49 1995 65 69
10. N.S. Allen, E. Hoang, C.M. Liauw, M. Edge, and E. Fontan Influence of processing aids on the thermal and photostabilisation of HDPE with antioxidant blends Polym Degrad Stab 72 2001 367 376
11. A. Parrondo, N.S. Allen, M. Edge, C.M. Liauw, E. Fontan, and T. Corrales Additive interactions in the stabilization of film grade high-density polyethylene. Part I: stabilization and influence of zinc stearate during melt processing J Vinyl Additive Technol 8 2002 75 89 (Pubitemid 135691294)
12. W. Voight, and R. Todesco New approaches to the melt stabilization of polyolefins Polym Degrad Stab 77 2002 397 402
13. N. Ortuoste, N.S. Allen, M. Papanastasiou, A. McMahon, M. Edge, B. Johanson, and K. Keck-Antoine Hydrolytic stability and hydrolysis reaction mechanism of bis(2,4-di-tert-butyl)pentaerythritol diphosphite (Alkanox P-24) Polym Degrad Stab 91 2006 195 211
14. J.K. Kochi, and P.J. Krusic Displacement of alkyl groups from organophosphorus compounds studied by electron spin resonance J Am Chem Soc 91 1969 3944 3946
15. W.G. Bentrude, E.R. Hansen, W.A. Khan, T.B. Min, and P.E. Rogers Free-radical chemistry of organophosphorus compounds. III. α vs. β scission reactions of alkoxy and thiyl radicals with trivalent oraganophosphorus derivatives J Am Chem Soc 95 1973 2286 2293
16. C. Walling, and M.S. Pearson Some radical reactions of trivalent phosphorus derivatives with mercaptans, peroxides, and olefins. A new radical cyclization J Am Chem Soc 86 1964 2262 2266
17. 4P J Am Chem Soc 94 1972 1025 1026
18. C. Walling, O.H. Basedow, and E.S. Savas Some extensions of the reaction of trivalent phosphorus derivatives with alkoxy and thiyl radicals; a new synthesis of thioesters J Am Chem Soc 82 1960 2181 2184
19. K. Schwetlick, T. König, C. Rüger, J. Pionteck, and W.D. Habicher Chain-breaking antioxidant activity of phosphite esters Polym Degrad Stab 15 1986 97 108
20. K. Schwetlick, J. Pionteck, T. König, and W.D. Habicher Organophosphorus antioxidants - VIII. Kinetics and mechanism of the reaction of organic phosphites with peroxyl radicals Eur Polym J 23 1987 383 388
21. W.-S. Hwang, and J.T. Yoke Autoxidation of ethyl phosphinite, phosphonite, and phosphite esters J Org Chem 45 1980 2088 2091
22. S.A. Buckler Autoxidation of trialkylphosphines J Am Chem Soc 84 1962 3093 3097
23. I. Bauer, W.D. Habicher, C. Rautengberg, and S. Al-Malaika Antioxidant interaction between organic phosphites and hindered amine light stabilisers during processing and thermoxidation of polypropylene Polym Degrad Stab 48 1995 427 440
24. I. Bauer, W.D. Habicher, S. Korner, and S. Al-Malaika Antioxidant interaction between organic phosphites and hindered amine light stabilizers: effects during photoxidation of polypropylene - II Polym Degrad Stab 55 1997 217 224
25. K. Schwetlick, T. König, J. Pionteck, D. Sasse, and W.D. Habicher Organophosphorus antioxidants part IX - inhibition of the oxidation of hydrocarbons by hindered aryl phosphites Polym Degrad Stab 22 1988 357 373
26. K. Schwetlick, J. Pionteck, A. Winkler, U. Hähner, H. Korschwitz, and W.D. Habicher Organophosphorus antioxidants part X - mechanism of antioxidant action of aryl phosphites and phosphonites at high temperatures Polym Degrad Stab 31 1991 219 228
27. B. Jacques, J. Devaux, and R. Legras Reactions induced by triphenyl phosphite addition during melt mixing of PET/PBT blends: chromatographic evidence of a molecular weight increase due to the creation of bonds of two different natures Polymer 38 1997 5367 5377
28. I. Bauer, S. Körner, B. Pawelke, S. Al-Malaika, and W.D. Habicher Hydroperoxide decomposing ability and hydrolytic stability of organic phosphites containing hindered amine moieties (HALS-phosphites) Polym Degrad Stab 62 1998 175 186
29. M. Papanastasiou, A.W. McMahon, N.S. Allen, A.M. Doyle, B.J. Johnson, and K. Keck-Antoine The hydrolysis mechanism of bis(2,4-di-tert-butyl) pentaerythritol diphosphite (Alkanox P24): an atmospheric pressure photoionisation mass spectrometric study Polym Degrad Stab 91 2006 2675 2682
30. J.A. Cicero, J.R. Dorgan, S.F. Dec, and D.M. Knauss Phosphite stabilization effects on two-step melt-spun fibers of polylactide Polym Degrad Stab 78 2009 95 105
31. D.J. Carlsson, M.E. Krzymien, L. Deschenes, M. Mercier, and C. Vachon Phosphite additives and their transformation products in polyethylene packing for γ-irradiation Food Addit Contam 18 2001 581 591 (Pubitemid 32519680)
32. N.S. Allen, R.A. Ortiz, and G.J. Anderson Comparison of the thermal and light stabilising action of novel aromatic phosphites substituted with 2-hydroxybenzophenone and hindered piperidine moieties in polyolefins Polym Degrad Stab 46 1994 75 84
33. E. Maloschik, E. Földes, Nagy G. Janecska Á, and B. Pukánszky Comparison of the efficiency of phosphorous stabilizers in metallocene polyethylene Prague 42nd Microsymposium of P.M.M. Degradation, stabilization and recycling of polymers July 2003 14 17
34. E. Földes, E. Maloschik, I. Kriston, P. Staniek, and B. Pukánszky Efficiency and mechanism of phosphorous antioxidants in Phillips type PE Polym Degrad Stab 91 2006 479 487
35. S. Al-Malaika, and X. Peng Stabilisation of metallocene ethylene-1-octene copolymers during multiple extrusions Polym Degrad Stab 93 2008 1619 1631
36. J.B. Knight, P.D. Calvert, and N.C. Billingham Localization of oxidation in polypropylene Polymer 26 1985 1713 1718
37. M. Celina, G.A. George, and N.C. Billingham Physical spreading of oxidation in solid polypropylene as studied by chemiluminescence Polym Degrad Stab 42 1993 335 344
38. N.C. Billingham Basel Heterogeneity in polymer oxidation. Abstract book 5th European polymer federation symposium on polymeric materials 1994 p. 1.195
39. F. Gugumus Physico-chemical aspects of polyethylene processing in an open mixer. Part 8: various reactions of polyethylene hydroperoxide in the melt Polym Degrad Stab 75 2002 131 142 (Pubitemid 33142204)
40. F. Gugumus Physico-chemical aspects of polyethylene processing in an open mixer. Part 11: heterogeneous kinetics of hydroxyl group formation Polym Degrad Stab 94 2005 449 463 (Pubitemid 40146227)
41. G. Socrates Infrared characteristic group frequencies 1980 John Wiley & Sons Chichester-New York-Brisbane-Toronto
42. J.-J.L. Fu, W.G. Bentrude, and C.E. Griffin Free-radical chemistry of organophosphorus compounds. II. Reactivity of phenyl radical toward trimethyl phosphite and the mechanism of the corresponding photo-Arbuzov reaction with phenyl iodide J Am Chem Soc 94 1972 7717 7722
43. Y.-S. Duh, C.-S. Kao, H.-H. Hwang, and W.W.-L. Lee Thermal decomposition kinetics of cumene hydroperoxide Trans I Chem E 76B 1998 271 276