Photochemical behavior of a new long-chain UV absorber derived from 4-tert-butyl-4'-methoxydibenzoylmethane.
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 alpha-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 (beta-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.
Wetz
Fabienne
F
IMRCP-UMR CNRS 5623, Université Paul Sabatier, 31062 Toulouse, France.
Routaboul
Corinne
C
Lavabre
Dominique
D
Garrigues
Jean-Christophe
JC
Rico-Lattes
Isabelle
I
Pernet
Ingrid
I
Denis
Alain
A