Atmospheric oxidation of poly(oxyethylene) alcohols. Identification of ethoxylated formates as oxidation products and study of their contact allergenic activity

Journal of Pharmaceutical Sciences

Volumn 88, Issue 4, 1999, Pages 483-488

  Bergh, Margareta ^a   Shao, Li Ping ^a   Magnusson, Kerstin ^a   Gäfvert, Elisabeth ^a   Nilsson, J Lars G ^a   Karlberg, Ann Therese ^a  

^a NATIONAL INSTITUTE FOR WORKING LIFE   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALLERGEN; FORMALDEHYDE; INDUSTRIAL CHEMICAL; POLYOXYETHYLENE; SURFACTANT;

ALLERGENICITY; ARTICLE; CONTACT ALLERGY; GAS CHROMATOGRAPHY; HUMAN; OCCUPATIONAL ALLERGY; OCCUPATIONAL EXPOSURE; OCCUPATIONAL SKIN DISEASE; OXIDATION; PATCH TEST; SKIN ALLERGY;

EID: 0345471456     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1021/js980210y     Document Type: Article

References (27)

1. Modler, F.; Willhalm, R.; Yoshida, Y. Surfactants, household detergents and their raw material. In CEH (Chemical Economics Handbook); Stanford Research Institute: Palo Alto, CA, 1994; pp 583.8001A-583.0003J.
2. Bergh, M.; Magnusson, M.; Nilsson, J. L. G.; Karlberg, A.-T. Contact allergenic activity of Tween 80 before and after air exposure. Contact Dermatitis 1997, 37, 9-18.
3. Bergh, M.; Shao, L. P.; Gäfvert, E.; Nilsson, J. L. G.; Karlberg, A.-T. Contact allergens from surfactants. Atmospheric oxidation of polyoxyethylene alcohols, formation of ethoxylated aldehydes and their allergenic activity. J. Pharm. Sci. 1998, 87, 276-282.
4. Bergh, M.; Magnussson, K.; Nilsson J. L. G.; Karlberg, A.-T. Formation of formaldehyde and peroxides by air oxidation of high purity polyoxyethylene surfactants. Contact Dermatitis 1998, 39, 14-20.
5. Evetts, S.; Kovalski, C.; Levin, M.; Stafford, M. High-temperature stability of alcohol ethoxylates. JOACS 1995, 72, 811-816.
6. Donbrow, M. Stability of the polyoxyethylene chain. In Surfactant Science Series volume 23, Nonionic surfactants: Physical chemistry; Schick, M. J., Ed.; Marcel Dekker, Inc.: New York, 1987; pp 1011-1067.
7. Decker, C.; Manchal, J. Polyoxyéthylène: produits d'oxidation et schéma cinétique. Makromol. Chem. 1973, 66, 155-178.
8. Hypersensitivity induced by chemicals: Report on a WHO consultation. In Allergic hypersensitivities induced by chemicals: recommendations for prevention. Vos, J. G., Younes, M., Smith, E., Eds.; CRC Press: Boca Raton, FL, 1996; pp 3-18.
9. Rycroft, R. J. G. Occupational contact dermatitis. In Textbook of Contact Dermatitis, 2nd ed.; Rycroft, R. J. G., Menné, T., Frosch, P. J., Eds.; Springer-Verlag: Berlin, 1995; pp 343-357.
10. Effendy, I.; Maibach, H. I. Surfactants and experimental irritant contact dermatitis. Contact Dermatitis 1995, 33, 217-225.
11. Dooms-Goossens, A.; Blockeel, I. Allergic contact dermatitis and photoallergic contact dermatitis due to soaps and detergents. Clin. Dermatol. 1996, 14, 67-76.
12. Pasche-Koo, F.; Piletta, P.-A.; Hunziker, N.; Hauser, C. High sensitization rate'to emulsifiers in patients with chronic leg ulcers. Contact Dermatitis 1994, 31, 226-228.
13. Cronin; E. Formaldehyde is a significant allergen in women with hand eczema. Contact Dermatitis 1991, 25, 276-282.
14. Dymicky, M. A general method for the preparation of formates. Org. Prep. Proc. Int. 1982, 14, 177-181.
15. Martinez, J.; Laur, J. Active esters of formic acid as useful formylating agents: Improvements in the synthesis of formyl-amino acid esters, N-α-Formyl-Met-Leu-Phe-OH, and Formyl-Met-Lys-Pro-Arg, a phagocytosis stimulating peptide. Synthesis 1982, 11, 979-981.
16. Bhart, I.; William, R.; Gelbaum L. T. Methanol-formic acid esterification equilibrium in sulfuric acid solution: Influence of Sodium Salts. Ind. Eng. Chem. Res. 1993, 32, 981-985.
17. Tsuchyia, S.; Kondo, M.; Okamoto, K.; Takase, Y. The cumulative contact enhancement test. In Contact Allergy Test in Guinea Pigs; Andersen, K. E., Maibach, H. I., Eds.; Karger: Basel, 1985; pp 208-219.
18. Boman, A.; Karlberg A-T.; Wahlberg, J. E. Experiences with Freund's complete adjuvant test (FCAT) when screening for contact allergens in colophony. Contact Dermatitis 1988, 18, 25-29.
19. Karlberg, A.-T.; Gäfvert, E.; Hagelthorn, G.; Nilsson, J. L. G. Maleopimaric acid - a potent sensitizer in modified rosin. Contact Dermatitis 1990, 22, 193-201.
20. Ribeiro, A. A.; Dennis, E. A. Motion in nonionic micelles and mixed micelles with phospholipids-C-13 spin-lattice relaxation study on p-tert-octylphenylpolyoxyethylene ethers. J. Phys. Chem. 1976, 80, 1746-1753.
21. Ribeiro, A. A. ; Dennis, E. A. A carbon - 13 and proton nuclear magnetic resonance study on the structure and mobility of nonionic alkyl polyoxyethylene ether micelles. J. Phys. Chem. 1977, 81, 957-963.
22. McLafferty, F. W.; Turecek, F. Detailed mechanisms of ion fragmentation. Interpretation of mass spectra; University Science Books: Mill Valley: CA, 1993; pp 261-264.
23. European Pharmacopoeia III; Council of Europe: 67075 Strasbourg Cedex, ISBN 9287129916; p 2.5.5.
24. Foglia, A.; Sibert, L. S.; Vail, P. D. Gas-liquid and high-performance liguid chromatographic analysis of aliphatic hydroperoxides and dialkyl hydroperoxides. J. Chromatogr. 1993, 637, 157-165.
25. Blute, I.; Svensson, M.; Holmberg, K.; Bergh, M.; Karlberg, A.-T. Solution behavior of a surfactant aldehyde - the oxidation product of an alcohol ethoxylate. Colloids Surf., A, in press.
26. Herbert, W. J. Handbook of Experimental Immunology. In Application of Immunological Methods; Weir, D. M., Ed.; Blackwell Scientific Publications: Cambridge, MA, 1979; Vol. 3, pp A 3.1-A 3.12.
27. Roberts, D. W.; Lepoittevin, J.-P. Hapten-protein interactions. In Allergic contact dermatitis. The molecular basis; Lepoittevin, J.-P., Basketter, D. A., Goossens, A., Karlberg A-T., Eds.; Springer-Verlag: Berlin, 1998; pp 81-111.