Summary
A review on the transformation of triplet oxygen to singlet oxygen via sensitising agents commonly found in fatty oils is presented. The Wigner spin conservation rule restricts the direct reaction of triplet oxygen with organic molecules possessing singlet multiplicities. Sensitisers present in fatty oils are energetically and mechanistically capable of changing oxygen from its triplet state to its singlet state. Lowering the oxygen multiplicity overcomes the spin restriction, thus allowing for the oxidative curing of fatty acids commonly used in alkyd resins.
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References
Faulkner R N, ‘The autoxidation of methyl elaeostearate’,J Appl Chem,8, 448, July 1958
Muizebelt W J, F G H Van Wijk and J Van Velde, Proceedings from the 15th Int Conf Org Coat Sci Tech, 299, Athens, Greece, 1989
Muizebelt W J, J C Hubert and R A M Venderbosch, ‘Mechanistic study of drying of alkyd resins using ethyl linoleate as a model substance’,Prog Org Coat,24, 263, 1994
Johnston A E, K T Zilch, E Selke and H J Dutton, ‘Analysis of fat acid oxidation products by counter-current distribution methods. V: Low-temperature decomposition of methyl linoleate hydroperoxide’,J Am Oil Chem Soc,38, 367, 1961
Hartshorn J H, ‘Time-lapse spectroscopic investigation of alkyd and linseed oil cure’,J Coat Tech,54, (687), 53, 1982
Falla N A R, ‘Linoleic-based coatings: A study of the dry film structure’,J Coat Tech,64, (815), 55, 1992
Wexler H, ‘Polymerisation of drying oils’,Chemical Reviews,64, (6), 591, 1964
Fritsch C W and F E Deatherage, ‘A study of the volatile compounds produced by the autoxidation of methyl oleate, oleic acid and cis-9-octadecene’,J Am Oil Chem Soc,33, 109, 1956
Heslop R B and K Jones,Inorganic Chemistry, A Guide to Advanced Study, Elsevier Scientific Publish, New York, USA, 1976, ISBN 0 444 41426 6
Cotton F A and G Wilkinson,Advanced Inorganic Chemistry, Interscience Pub, J Wiley and Sons, New York, USA, 1972, ISBN 0 471 17560 9
Waters W A, ‘A possible role for singlet oxygen in the initiation of fatty acid autoxidation’,Trans Faraday Soc,42, 281, 1946
Wigner E P,Group Theory, Academic Press, New York, USA, 1959
Rawls H R and P J Van Santen, ‘Singlet oxygen and the initiation of fatty acid autoxidation’,J Am Oil Chem Soc,47, 121, 1970
Coe R M, US Patent 2,165,130, 1939
Hubert J C, R A M Venderbosch, W J Muizebelt, R P Klaasen and K H Zabel, ‘Singlet oxygen drying of alkyd resins and model compounds’,J Coat Tech,69, (869), 59, 1997
Swern D, J E Coleman, H B Knight, C Ricciuti, C O Willits and C R Eddy, ‘Reaction of fatty materials with oxygen. XIV: Polarographic and infrared spectrophotometric investigation of peroxides from autoxidised methyl oleate’,J Am Chem Soc,75, 3135, 1953
Hasenhuettl G L, Kirk-OthmerEncyclopedia of Chemical Technology, J Wiley and Sons, ISBN 0 471 52678 9, 1993
Wigner E and E E Witmer, ‘Molecular spectra of diatomic molecules in modern quantum mechanics’,Z Phys,51, 859, 1928
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Martyak, N.M. On the curing of fatty acids with singlet oxygen. Surface Coatings International Part B: Coatings Transactions 89, 177–181 (2006). https://doi.org/10.1007/BF02699648
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DOI: https://doi.org/10.1007/BF02699648