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1 September 2004 Photochemical Behavior of a New Long-chain UV Absorber Derived from 4-tert-Butyl-4′-Methoxydibenzoylmethane
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Abstract

A new UV filter, the 1-(4-tert-butylphenyl)-2-decanyl-3-(4′-methoxyphenyl)-propane-1,3-dione, called C10-DBM, was prepared by grafting a 10-carbon aliphatic chain to the α-carbonyl position of 4-tert-butyl-4′-methoxydibenzoylmethane (BM-DBM), a well-known and often used UV filter. The UV-A absorption efficiency of organic solutions containing the new filter was tested and compared with identical solutions containing BM-DBM with or without irradiation (xenon lamp). The originality of this new filter is that its UV-A absorbance appeared during irradiation of the molecule. Although the molar absorption coefficient of C10-DBM in the UV-A domain was lower than that of BM-DBM, the solutions absorption exhibited a much more photostable behavior under irradiation. In this study, we first demonstrated that C10-DBM was a precursor of BM-DBM (enol isomer) by means of high-performance liquid chromatography followed by mass spectrometry. Indeed, we showed that the UV-A absorption of C10-DBM solutions appearing during the irradiation of the molecule was due to a Norrish-II reaction (β-cleavage), which induced the release of the BM-DBM enol form and 1-decene. Then, we established a kinetic model for the photochemistry of C10-DBM and fitted the variation of UV absorption spectra to confirm the proposed mechanism.

Fabienne Wetz, Corinne Routaboul, Dominique Lavabre, Jean-Christophe Garrigues, Isabelle Rico-Lattes, Ingrid Pernet, and Alain Denis "Photochemical Behavior of a New Long-chain UV Absorber Derived from 4-tert-Butyl-4′-Methoxydibenzoylmethane," Photochemistry and Photobiology 80(2), 316-321, (1 September 2004). https://doi.org/10.1562/2004-03-09-RA-106.1
Received: 9 March 2004; Accepted: 1 May 2004; Published: 1 September 2004
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