Skip to main content
SpringerLink
Log in

Mechanisms of oxidative photodegradation and of UV stabilization of polyolefins

  • Conference paper
  • First Online:
Fortschritte der Hochpolymeren-Forschung

Part of the book series: Advances in Polymer Science ((POLYMER,volume 7/1))

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

V. References

  1. Hirt, R. H.: Ultraviolet spectral energy distributions of natural sunlight and accelerated light sources. National Meeting of the Optical Society of America, Detroit, Mich. (Oct. 9, 1958).

    Google Scholar 

  2. Achhammer, B. G., M. Tryon, and G. M. Kline: Chemical structure and stability relations in polymers. Mod. Plastics 37, 131 (1959).

    CAS  Google Scholar 

  3. Scott, G.: Antioxidants. Chem. Ind. (London) 1963, 271.

    Google Scholar 

  4. Norrish, R. G. W., and M. H. Searby: The photochemical decomposition of dicumenyl peroxide and cumene hydroperoxide in solution. Proc. Roy. Soc. A 237, 464 (1956).

    Google Scholar 

  5. Pitts, J. N., Jr., R. L. Letsinger, R. P. Taylor, J. M. Patterson, G. Recktenwald, and R. B. Martin: Photochemical reactions of benzophenone in alcohols. J. Am. Chem. Soc. 81, 1068 (1959).

    Article  CAS  Google Scholar 

  6. Calvert, J. G., and J. N. Pitts, Jr.: Photochemistry, Chap. 4 and Chap 5. New York: John Wiley and Sons Inc. 1966.

    Google Scholar 

  7. Neiman, M. B.: Aging and stabilization of polymers, Chap. 4. New York: Consultants Bureau 1965.

    Google Scholar 

  8. Hawkins, W. L.: Oxidative degradation of high polymers. Oxidn Combust. Rev. 1, 169 (1965).

    CAS  Google Scholar 

  9. Scott, G.: Atmospheric oxidation and antioxidants, Chap. 3 and Chap. 5. New York: Elsevier Publ. Co. 1965.

    Google Scholar 

  10. Burgess, A. R.: Polymer degradation mechanisms. Natl. Bur. St. Circular 525, 149 (1953).

    CAS  Google Scholar 

  11. Winslow, F. H., and W. L. Hawkins: Some weathering characteristics of plastics. Appl. Polymer Symp. 4, 29 (1967).

    Google Scholar 

  12. Allara, D. L., T. Mill, and F. R. Mayo: Original Manuscripts Submitted to International Oxidation Symposium. Stanford Research Institute, 1967, p. 1–373.

    Google Scholar 

  13. Mayo, F. R.: Free-radical autoxidations of hydrocarbons. Account Chem. Res. 1, 193 (1968).

    Article  CAS  Google Scholar 

  14. Howard, J. A., and K. U. Ingold: Absolute rate constants for hydrocarbon autoxidation. I. Styrene. Can. J. Chem. 43, 2729 (1965).

    Article  CAS  Google Scholar 

  15. Factor, A., C. A. Russel, and T. G. Traylor: Bimolecular combination reaction of oxyradicals. J. Am. Chem. Soc. 87, 3692 (1965).

    Article  CAS  Google Scholar 

  16. Hiatt, R. R., and T. G. Traylor: Cage recombination of t-butoxy radicals. J. Am. Chem. Soc. 87, 3766 (1965).

    Article  CAS  Google Scholar 

  17. Hiatt, R. R., T. Mill, F. R. Mayo, K. C. Irvin, J. K. Castleman, and C. W. Gould: Homoyltic decompositions of hydroperoxides. J. Org. Chem. 33, 1416, 1421, 1428, 1430, 1436 (1968).

    Article  CAS  Google Scholar 

  18. Wibaut, J. P., and A. Strang: Autoxidation of saturated hydrocarbons in the liquid phase. Koninkl. Ned. Akad. Wetenschap. Proc. Ser. B 54, 102 (1951).

    Google Scholar 

  19. Rust, F. F., and D. O. Collamer: The high temperature oxidations of 2,2,4-trimethylpentane and 2,2-dimethylbutane. J. Am. Chem. Soc. 76, 1055 (1954)

    Article  CAS  Google Scholar 

  20. Rust, F. F.: Intramolecular oxidation. The autoxidation of some dimethylalkanes. J. Am. Chem. Soc. 79, 4000 (1957).

    Article  CAS  Google Scholar 

  21. Criegee, R., and P. Ludwig: Mechanismen of autoxidation of hydrocarbons to dihydroperoxides. Erdöl Kohle 15, 523 (1962).

    Google Scholar 

  22. Dulog, L., E. Radlmann, and W. Kern: Über die Autoxydation gesättigter makromolekularer Kohlenwasserstoffe. Makromol. Chem. 60, 1 (1963).

    Article  CAS  Google Scholar 

  23. Chien, J. C. W., and C. R. Boss: Polymer reactions. V. Kinetics of autoxidation of polypropylene. J. Polymer Sci. Part A-1, 5, 3091 (1967).

    Article  CAS  Google Scholar 

  24. Bawn, C. E. H., and S. A. Chaudri: Autoxidation of atactic polypropylene in solution. I. 2,2′-azobisisobutyronitrile initiated autoxidation. Polymer 9, 113 (1968).

    Article  CAS  Google Scholar 

  25. Nayes, R. M.: Kinetics of competitive processes when reactive fragments are produced in pairs. J. Am. Chem. Soc. 77, 2042 (1955).

    Article  Google Scholar 

  26. Allen, P. E. M., and C. R. Patrick: Generation of radicals in pairs and the kinetics of radical chain reactions in solution. Nature 191, 1194 (1961).

    CAS  Google Scholar 

  27. Mayo, F. R.: The oxidation of polymers. Preprints of papers. Div. Polymer Chem. 8 (1), 11, (1967).

    CAS  Google Scholar 

  28. For clarifications of the symbols of the electronic states used in this review see: Calvert, J. C., and J. N. Pitts, Jr.: Photochemistry, p. 205, 245. New York: John Wiley and Sons Inc 1966.

    Google Scholar 

  29. Evans, D. F.: Magnetic perturbation of singlet-triplet transitions. Part IV. Unsaturated compounds. J. Chem. Soc. 1960, 1735.

    Google Scholar 

  30. Munck, A. V., and R. Scott: Ultraviolett absorption of oxygen in organic solvents. Nature 177, 587 (1956).

    CAS  Google Scholar 

  31. Evans, D. F.: Molecular association of oxygen and aromatic solvents. J. Chem. Soc. 1953, 345.

    Google Scholar 

  32. Tsubomura, H., and R. S. Mulliken: Molecular Complexes and their spectra. XII. Ultraviolett absorption spectra caused by the interaction of oxygen with organic molecules. J. Am. Chem. Soc. 82, 5966 (1960).

    Article  CAS  Google Scholar 

  33. Carlsonn, D. J., and J. C. Robb: Liquid-phase oxidation of hydrocarbons. Trans. Faraday Soc. 62, 3403 (1966).

    Article  Google Scholar 

  34. Chien, J. C. W.: On the possible initiation of photoxidation by charge-transfer excitation. J. Phys. Chem. 69, 4317 (1965).

    CAS  Google Scholar 

  35. Allen, A. O., and A. Hummel: Determination of the number of separated ion pairs produced in the irradiations of a liquid. Discussions Faraday Soc. 36, 95 (1964).

    Article  Google Scholar 

  36. Noyes, W. A., Jr., G. S. Hammond, and J. N. Pitts, Jr.: Advances in photochemistry, Vol. 1, p. 23. New York: Interscience Publ. Inc. 1963.

    Google Scholar 

  37. Longi, P., G. Mazzanti, A. Roggero, and A. M. Lachi: High temperature anionic stereospecific polymerization of propylene. Makromol. Chem. 61, 63 (1963).

    Article  CAS  Google Scholar 

  38. Ziegler, K., K. Nagel, and W. Pfohl: Organometallic compounds. XXXVIII. Pyrolysis of aluminum trialkyls. Liebigs Ann. Chem. 629, 210 (1960).

    CAS  Google Scholar 

  39. Rugg, F. M., J. J. Smith, and R. C. Bacon: Infrared spectrophotometric studies on polyethylene. II. Oxidation. J. Polymer Sci. 13, 535 (1954).

    Article  CAS  Google Scholar 

  40. Milinchuk, V. K.: Free radical formation by oxygen in polymers. Vysokomolekul. Soyedin. 7, 1293 (1965).

    CAS  Google Scholar 

  41. Kujirai, C., S. Hashiya, K. Shibuya, and K. Nishio: Photochemistry of polypropylene. I. A fundamental research. Chem. High Polymer (Tokyo) 25, 193 (1968).

    CAS  Google Scholar 

  42. Calvert, J. G., and J. N. Pitts, Jr.: Photochemistry, p. 270. New York: John Wiley and Sons Inc. 1966.

    Google Scholar 

  43. Uri, N.: Inorganic free radicals in solution. Chem. Rev. 50, 375 (9152).

    Article  Google Scholar 

  44. Cicchetti, O.: Unpublished results.

    Google Scholar 

  45. Betts, A. T., and N. Uri: Inhibition of iron-photosensitized autoxidation of amides. Chem. Ind. 1967, 512.

    Google Scholar 

  46. Evans, M. G., M. Santappa, and N. Uri: Photoinitiated free-radical polymerization of vinyl compounds in aqueous solution. J. Polymer Sci. 7, 243 (1951).

    Article  CAS  Google Scholar 

  47. Scott, G.: Atmospheric oxidation and antioxidants, Chap. 7. New York: Elsevier Publ. Co. 1965.

    Google Scholar 

  48. Briggs, P. J., and J. F. McKellar: Mechanism of photostabilization of polypropylene by nickel oxime chelates. J. Appl. Polymer Sci. 12, 1825 (1968) and references reported here.

    Article  CAS  Google Scholar 

  49. Charlesby, A., and R. H. Partridge: The identification of luminescence centers in polyethylene and other polymers. Proc. Roy. Soc. (London) A 288, 312 (1965)

    Google Scholar 

  50. Thermoluminescence and phosphorescence in polyethylene under ultraviolet irradiation. Proc. Roy. Soc. (London), A 283, 329 (1965).

    Google Scholar 

  51. Pinner, S. A.: Weathering and degradation of plastics. London: Columbia Press 1966.

    Google Scholar 

  52. Cicchetti, O., S. Fontani e G. Gratani: Influenza di composti del TiIV sull'ossidazione di modelli del polipropilene; unpublished results.

    Google Scholar 

  53. Calvert, J. G., and J. N. Pitts, Jr.: Photochemistry, p. 441. New York: John Wiley and Sons Inc. 1966.

    Google Scholar 

  54. Ershov, Yu. A., A. F. Lukovnikov, and A. A. Baturina: Photochemical decomposition of poylpropylene hydroperoxide. Kinetica i Analiz, 7, 597 (1966).

    CAS  Google Scholar 

  55. Karjakin, A. V., V. A. Nikitin, and A. N. Sidorov: Photochemical decomposition of hydroperoxides. Zh. Ziz Khim. 29, 1624 (1955).

    Google Scholar 

  56. Tupikov, V. I. and S. Ya. Pshezhetskij: Migration of the open valence in stabilized olefin radicals under the action of light. Dokl. Akad. Nauk SSSR 156 144 (1964).

    Google Scholar 

  57. For reviews of this nomenclature, see Noyes, W. A., Jr., G. S. Hammond, and J. N. Pitts, Jr.: Advances in photochemistry, Vol. 1, Chap. 1. New York: Interscience Publ. Inc. 1963.

    Google Scholar 

  58. Hartley, G. H., and J. E. Guillet: Photochemistry of ketone polymers. I. Studies of ethylene-carbon monoxide copolymers. Macromolecules 1, 165 (1968).

    Article  CAS  Google Scholar 

  59. — —Photochemistry of ketone polymers. Studies of model compounds. Macromolecules 1, 413 (1968).

    Article  CAS  Google Scholar 

  60. Yang, N. C.: Reactivity of the photoexcited organic molecule. Proceedings of the Thirteenth Conference on Chemistry at the University of Brussels, October 1965, p. 148.

    Google Scholar 

  61. Turro, N. J.: Molecular photochemistry. New York: W. A. Benjamin Inc. 1965.

    Google Scholar 

  62. Kan, R. O.: Organic photochemistry. New York: McGraw-Hill Book Co. Inc. 1966.

    Google Scholar 

  63. Necker, D. C.: Mechanistic organic photochemistry. New York: Reinhold Publ. Corp. 1967.

    Google Scholar 

  64. Dekker, M.: Organic photochemistry, Vol. 1. New York: O. L. Chapman 1967.

    Google Scholar 

  65. Wagner, P. J., and G. S. Hammond: Mechanism of type II photoelimination. J. Am. Chem. Soc. 87, 4009 (1965); — Mechanisms of photochemical reactions in solution. XXXVIII. Quenching of the type II photoelimination reaction. J. Am. Chem. Coc. 88, 1245 (1966).

    Article  CAS  Google Scholar 

  66. Nicol, C. H., and J. G. Calvert: Relations between photodecomposition modes and molecular structure in the series of carbonyl compounds. J. Am. Chem. Soc. 89, 1790 (1967).

    Article  CAS  Google Scholar 

  67. Yang, N. C., and Eu. D. Feit: Photochemistry of t-butyl alkyl ketones in solution. J. Am. Chem. Soc. 90, 504 (1968).

    Article  CAS  Google Scholar 

  68. Bamford, C. H., and R. G. W. Norrish: Primary photochemical reactions. Part III. Photochemical decomposition of iso-valeraldehyde and di-n-propyl ketone. J. Chem. Soc. 1935, 1504.

    Google Scholar 

  69. Srinivasan, R.: The photochemical type II process in 2-hexanone-5,5-d2 and 2-hexanone. J. Am. Chem. Soc. 81, 5061 (1959).

    Article  CAS  Google Scholar 

  70. McMillan, G. R., J. G. Calvert, and J. N. Pitts, Jr.: Detection and lifetime of enol-acetone in the photolysis of 2-pentanone vapor. J. Am. Chem. Soc. 86, 3602 (1964).

    Article  CAS  Google Scholar 

  71. Rice, F. O., and E. Teller: The role of free radicals in elementary organic reactions. J. Chem. Phys. 6, 489 (1938).

    Article  CAS  Google Scholar 

  72. Davis, W., Jr., and W. A. Noyes, Jr.: Photochemical studies. XXXVIII. A further study of the photochemistry of methyl n-butyl ketone. J. Am. Chem. Soc. 60, 2153 (1947).

    Article  Google Scholar 

  73. Manning, P. P.: The photolysis of saturated aldehydes and ketones. J. Am. Chem. Soc. 79, 5151 (1957).

    Article  CAS  Google Scholar 

  74. Yang, N. C., and D. D. H. Yang: Photochemical reactions of ketones in solution. J. Am. Chem. Soc. 80, 2913 (1958).

    Article  CAS  Google Scholar 

  75. Baum, E. J., J. K. S. Wan, and J. N. Pitts, Jr.: Symposium on structure and reactivity of excited molecules, Abstracts 149th National Meeting, American Chemical Society, Detroit, April, 1965; Abstracts, Div. Phys. Chem., Detroit, April, 1965, 30 S.; from reference (6); — Baum, E. J.: Doctoral Dissertation, University of California, Riverside, 1965; from reference (6).

    Google Scholar 

  76. Guillet, J. E., and R. G. W. Norrish: The photolysis of polymethyl vinyl ketone. Proc. Roy. Soc. (London), A 233, 153 (1955).

    Google Scholar 

  77. Wissbrun, K. F.: The photolysis of polymethyl vinyl ketone and polymethyl isopropenyl ketone. J. Am. Chem. Soc. 81, 58 (1959).

    Article  CAS  Google Scholar 

  78. Osborn, K. R.: Quantum yield of polymer chain cleavage. Am. Chem. Soc., Div. Org. Coatings Plastics Chem., Preprints, 21, 411 (1961).

    CAS  Google Scholar 

  79. Manahan, A. R.: Photolysis of poly (tert-butyl acrylate) in the region of the glass transition temperature. J. Polymer Sci. Part A-1, 4, 2381 (1966). — Photochemistry of poly (tert-butyl acrylate). Effect of ester spatial conformation on the cycloelimination process. J. Polymer Sci. Part A-1, 5, 2333 (1967).

    Article  Google Scholar 

  80. Boyer, R. F.: Relation of transition temperatures to chemical structure in high polymers. Rubber Chem. Technol. 36, 1303 (1963).

    CAS  Google Scholar 

  81. Frank, J., and E. Rabinowitch: Free radicals and the photochemistry of solution. Trans. Faraday Soc. 30, 120 (1934).

    Article  Google Scholar 

  82. Noyes, R. M.: Effects of diffusion rates on chemical kinetics. Progr. Reaction Kinetics 2, 129 (1961).

    Google Scholar 

  83. Herzberg, G., and D. A. Ramsay: The 7500–4500 Å absorption system of the free HCO radical. Proc. Roy. Soc. (London) A 233, 34 (1955).

    Google Scholar 

  84. McKellar, T. F., and R. G. W. Norrish: Combustion of gaseous aldehydes studied by flash photolysis and kinetic spectroscopy. Proc. Roy. Soc. (London) A 254, 147 (1960).

    Google Scholar 

  85. Trozzolo, A. M., and F. H. Winslow: A mechanism for the oxidative photodegradation of polyethylene. Macromolecules 1, 98 (1968).

    Article  CAS  Google Scholar 

  86. Dougherty, T. J.: Type II photolysis of 2-octanone. J. Am. Chem. Soc. 87, 4011 (1965); and references reported here.

    Article  CAS  Google Scholar 

  87. Guillet, J. E., J. Dhanray, F. J. Golemba, and G. H. Hartley: 153rd National Meeting of the American Chemical Society, Miami Beach, Flo., April 1967; from reference (80).

    Google Scholar 

  88. Pross, A. W., and R. M. Black: Photocatalyzed oxidation of polyethylene. J. Soc. Chem. Ind. 69, 113 (1950).

    CAS  Google Scholar 

  89. Winslow, F. H., W. Matreyeck, A. M. Trozzolo, and R. H. Hansen: Oxidative photodegradation of poylethylene. ACS Div. Polymer Chem. Polymer, preprints, 9, 377 (1968).

    CAS  Google Scholar 

  90. Yang, N. C., A. Morduchowitz, and D. H. Yang: On the mechanism of photochemical formation of cyclobutanols. J. Am. Chem. Soc. 85, 1017 (1963).

    Article  CAS  Google Scholar 

  91. Ausloos, P., and R. E. Rebbert: Photoelimination of ethylene from 2-pentanone. J. Am. Chem. Soc. 86, 4512 (1964).

    Article  CAS  Google Scholar 

  92. Coulson, D. R., and N. C. Yang: Deuterium isotope effects in the photochemistry of 2-hexanone. J. Am. Chem. Soc. 88, 4511 (1966).

    Article  CAS  Google Scholar 

  93. Baum, E. J., J. K. S. Wan, and J. N. Pitts, Jr.: Reactivity of excited states. Intramolecular hydrogen atom abstraction in substituted butyrophenones. J. Am. Chem. Soc. 88, 2652 (1966).

    Article  CAS  Google Scholar 

  94. Yang, N. C., and S. P. Elliott: Reactivity of the n,Ï€* singlet-state of 2-hexanone. J. Am. Chem. Soc. 90, 4194 (1968).

    Article  CAS  Google Scholar 

  95. Heskins, M., and T. E. Guillet: Mechanism of ultraviolet stabilization of polymers. Macromolecules 1, 97 (1968).

    Article  CAS  Google Scholar 

  96. Kautsky, H.: Quenching of luminiscence by oxygen. Trans. Faraday Soc. 35, 216 (1939).

    Article  CAS  Google Scholar 

  97. Sharp, D. B.: Stereospecific photo-oxidation of olefins. Quantum yield and olefin structure. Abstracts, 138th Meeting of the American Chemical Society, New York, Sept. 1960, p. 79 P.

    Google Scholar 

  98. Foote, C. S., S. Wexler, and W. Ando: Chemistry of singlet oxygen. III. Product selectivity. Tetrahedron Letters 1965, 4111.

    Google Scholar 

  99. Carey, E. J., and W. C. Taylor: A study of the peroxidation of the organic compounds by externally generated singlet oxygen molecules. J. Am. Chem. Soc. 86, 3881 (1964).

    Article  Google Scholar 

  100. Kawaoka, K., A. U. Khan, and D. R. Kearns: Role of singlet excited states of molecular oxygen in the quenching of organic triplet states. J. Chem. Phys. 46, 1842 (1967).

    Article  CAS  Google Scholar 

  101. Foote, C. S., and S. Wexler: Singlet oxygen. A probable intermediate in photosensitized autoxidations. J. Am. Chem. Soc. 86, 3880 (1964); — Wilson, T.: Excited singlet molecular oxygen in photooxidation. J. Am. Chem. Soc. 88, 2898 (1966).

    Article  CAS  Google Scholar 

  102. Trozzolo, A. M., and S. R. Fahrenholtz: Unpublished results; from reference (80).

    Google Scholar 

  103. Valentine, D., N. J. Turro, Jr., and G. S. Hammond: Thermal and photosensitized dimerizations of cyclohexadiene. J. Am. Chem. Soc. 86, 5202 (1964).

    Article  CAS  Google Scholar 

  104. Kearns, D. R., R. A. Hollins, A. U. Khan, R. W. Chambers, and P. Radlick: Evidence for the participation of 1Σ +g and 1Δ g oxygen in dyesensitized photooxygenation reactions. I. J. Am. Chem. Soc. 89, 5456 (1967); — Kearns, D. R., R. A. Hollins, A. U. Khan, and P. Radlick: Evidence for the participation of 1Σ +g and 1Δ g oxygen in dye-sensitized photooxygenation reactions. II. J. Am. Chem. Soc. 89, 5456 (1967).

    Article  CAS  Google Scholar 

  105. Foote, C. S.: Photosensitized oxygenations and the role of singlet oxygen. Accounts Chem. Res. 1968, 104, and references reported here.

    Google Scholar 

  106. Gollnick, K., and G. O. Schenck: Mechanism and stereoselectivity of photosensitized oxygen transfer reactions. Pure Appl. Chem. 9, 507 (1964); — Kopecky, K. R., and H. J. Reich: Reactivities in photosensitized olefin oxidations. Can. J. Chem. 43, 2265 (1965).

    Article  CAS  Google Scholar 

  107. Mill, T., K. C. Irwin, and F. R. Mayo: Accelerated oxidations of polyisoprene. III. Photosensitized oxidations in solution. Rubber Chem. Technol. 41, 296 (1968).

    CAS  Google Scholar 

  108. Chien, J. C. W., and H. Jablomer: Polymer reactions. IV. Thermal decompositions of polypropylene hidroperoxides. J. Polymer Sci. Part A-1, 6, 393 (1968).

    Article  CAS  Google Scholar 

  109. Carlsson, D. J., Yosh. Kato, and D. M. Wiles: The effect of oxidation products on the photostability of polypropylene films. Macromolecules 1, 459 (1968).

    Article  CAS  Google Scholar 

  110. Bacha, J. D., and J. K. Kochi: Polar and solvent effects in the cleavage of t-alcoxy radicals. J. Org. Chem. 30, 3272 (1965).

    CAS  Google Scholar 

  111. Oswald, H. J., and E. Turi: Deterioration of polypropylene by oxidative degradation. Polymer Eng. Sci. 5, 152 (1965).

    Article  CAS  Google Scholar 

  112. O'Leary, R. K., W. L. Guess, and J. Autian: Effects of heat and ultraviolet radiation on the stability of a polypropylene-polyisobutylene alloy. J. Pharm. Sci. 57, 1552 (1968).

    Google Scholar 

  113. Ouannes, C., and T. Wilson: Quenching of singlet oxygen by tertiary aliphatic amines. J. Am. Chem. Soc. 90, 6527 (1968).

    Article  CAS  Google Scholar 

  114. Pirovarov, A. P., and A. F. Lukovnikov: On the mechanism of the action of light stabilizers in polystyrene. Vysokomolekul. Soyedin. A 9, 2727 (1967) [Translated in Polymer Sci. USSR., 9, 3087 (1967)] and references reported here.

    Google Scholar 

  115. Schmitt, R. G., and R. G. Hirt: Investigation of the protective ultraviolet absorbers in a space environment. III. Protective effectiveness. J. Appl. Polymer Sci. 7, 1565 (1963).

    Article  CAS  Google Scholar 

  116. Goldenberg, V. N., V. Ya. Shlyapintokh, and L. M. Postnikov: On the action mechanism of photostabilizers of polymers in the photosensitized oxidation reaction of hydrocarbons. Note I. The action mechanism of photostabilizers. Izv. Akad. Nauk. SSSR, No. 7, 1483 (1968).

    Google Scholar 

  117. Drogin, I.: The use of carbon black in plastics. SPE Journal, 1965, 248.

    Google Scholar 

  118. McTigue, F. H., and M. Blumberg: Factors affecting light resistence of polypropylene. Appl. Polymer Symp. No. 4, 175 (1967).

    Google Scholar 

  119. Haward, R. N.: Additives in plastics. Chem. Ind. 1964, 1442.

    Google Scholar 

  120. Calvert, J. G., and J. N. Pitts, Jr.: Photochemistry, p. 170. New York: John Wiley and Sons Inc. 1966.

    Google Scholar 

  121. Coleman, R. A., and J. A. Weicksel: Ultraviolet absorbers for plastics. Modern Plastics 1959, 117.

    Google Scholar 

  122. Cicchetti, O., M. Dubini, P. Parrini, G. P. Vicario, and E. Bua: Diffusion of organic compounds in saturated polyolefins. European Polymer J. 4, 419 (1968).

    Article  CAS  Google Scholar 

  123. Dubini, M., O. Cicchetti, G. P. Vicario, and E. Bua: Diffusion of thiodipropionic esters and hydroxybenzophenones in isotactic polypropylene. European Polymer J. 3, 473 (1967).

    Article  CAS  Google Scholar 

  124. Oster, G.: Dye-sensitized photopolymerization. Nature 173, 300 (1954).

    CAS  Google Scholar 

  125. Pitts, J. N., Jr., and R. M. Martin: Abstract 27 B, Report to the American Chemical Society, Petroleum Research Fund, 1959; from reference (6).

    Google Scholar 

  126. Chaudet, J. H., G. C. Newland, H. W. Patton, and J. W. Tamblyn: Mechanisms of ultraviolet stabilization of plastics. S.P.E. Transaction 1, 26 (1961).

    CAS  Google Scholar 

  127. Ermolaev, V. L.: Sensitized phosphorescence of organic compounds: triplet-triplet transfer of energy. In: Elementary photoprocesses in molecules. Ed. Bertol'd S. Neporent, translated from Russian. New York: Consultants Bureau 1968.

    Google Scholar 

  128. Liu, R. S. H.: Photosensitized isomerization of 1,3-cyclo-octadienes and conversion to bicyclo-[4.2.0.]-oct.-7-ene. J. Am. Chem. Soc. 89, 112 (1967).

    Article  CAS  Google Scholar 

  129. Turro, N. J.: Molecular photochemistry, p. 132. New York: W. A. Benjamin Inc. 1965.

    Google Scholar 

  130. Dougherty, T. J.: Type II photolysis of 2-octanone. J. Am. Chem. Soc. 87, 4011 (1965).

    Article  CAS  Google Scholar 

  131. Brit. Patent, 858, 889 (1961), Stabilized polypropylene (Ferro Corp.); — Brit. Patent, 945,050 (1963), Improvements in or relating to complex salts of nickel as light stabilizers for polypropylene (Hercules Powder Comp.).

    Google Scholar 

  132. U.S. Patent, 3,296,191 (1967), Stabilizers for polypropylene (FMC Corp.); U.S. Patent, 3,296,192 (1967), Light stabilizers for polymers (Hercules Inc.).

    Google Scholar 

  133. U.S. Patent, 2,971,941 (1961), Stabilized polyethylene (Ferro Corp.).

    Google Scholar 

  134. Brit. Patent, 943,061 (1962), (American Cyanamid).

    Google Scholar 

  135. U.S. Patent, 3,310,575 (1967), Metal derivates of hindered phenol substituted phosphonic acids (Geigy Chem. Comp.).

    Google Scholar 

  136. Brit. Patent, Application 44 655/65 (ICI); from reference (121).

    Google Scholar 

  137. Fry, A. J., R. S. H. Liu, and G. S. Hammond: Mechanics of photochemical reactions in solution. XLI. Comparison of rates of fast triplet quenching reactions. J. Am. Chem. Soc. 88, 4781 (1966).

    Article  CAS  Google Scholar 

  138. Foss, R. P., D. O. Cowan, and G. S. Hammond: Mechanism of photoreactions in solution. XXI. Quenching of excited singlet states of benzophenone. J. Phys. Chem. 68, 3747 (1964).

    CAS  Google Scholar 

  139. Bell, J. A., and H. J. Linschitz: Decay kinetics of the 1-naphthaldehyde and benzophenone triplet states in benzene. J. Am. Chem. Soc. 85, 528 (1963); — Hammond, G. S., and R. P. Foss: Mechanisms of photoreactions in solution. XX. Quenching of excited states of benzophenone by metal chelates. J. Phys. Chem. 68, 3739 (1964).

    Article  CAS  Google Scholar 

  140. Briggs, P. J., and J. F. McKellar: Effect of some nickel chelate ultraviolet stabilizers on triplet anthracene. Chem. Ind. (London) 1967, 622.

    Google Scholar 

  141. Porter, G., and M. R. Wright: Energy transfer from the triplet state in solution. J. Chem. Phys. 55, 705 (1958).

    CAS  Google Scholar 

  142. Linschitz, H. J., and L. Pekkarinen: Quenching of triplet states of anthracene and porphyrins. J. Am. Chem. Soc. 82, 2411 (1960).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Centro Ricerche di Milano, Montecatini Edison S.p.A., Milan, Italy

    O. Cicchetti

Authors
  1. O. Cicchetti
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

Copyright information

© 1970 Springer-Verlag

About this paper

Cite this paper

Cicchetti, O. (1970). Mechanisms of oxidative photodegradation and of UV stabilization of polyolefins. In: Fortschritte der Hochpolymeren-Forschung. Advances in Polymer Science, vol 7/1. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0051109

Download citation

  • DOI: https://doi.org/10.1007/BFb0051109

  • Received:

  • Published:

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-04762-9

  • Online ISBN: 978-3-540-36176-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation