Perfume compositions – Perfume compositions – Oxygen containing active ingredient
Reexamination Certificate
1999-05-21
2001-04-17
Kelly, Cynthia Harris (Department: 1743)
Perfume compositions
Perfume compositions
Oxygen containing active ingredient
C512S002000, C512S025000, C512S026000, C424S076400, C510S101000, C560S129000
Reexamination Certificate
active
06218355
ABSTRACT:
BRIEF SUMMARY OF THE INVENTION
The present invention describes a fragrance delivery system which releases fragrant aldehydes or ketones and/or fragrant compounds containing an olefin function upon exposure to light. This system comprises &agr;-keto esters of formula
in which R′
*
and R″
*
have the meaning as defined in the application and which are generally, in case of R′
*
, an alkyl group carrying an abstractable hydrogen in &ggr;-position relative to the &agr;-keto function and carrying a moiety from which is derived a fragrant compound containing an olefin function, and, in case of R″
*
, the organic part of a primary or secondary alcohol from R″
*
OH which is derived a fragrant aldehyde or ketone.
BACKGROUND OF THE INVENTION
The present invention relates to the field of perfumery. It relates, more particularly, to &agr;-keto esters, as defined below, of alcohols which are precursors of fragrant aldehydes and ketones and which are capable of releasing said fragrant ketone or aldehyde upon exposure to light, more particularly daylight. Said &agr;-keto esters may furthermore contain, in &agr;-position to the keto group, an alkyl group which may contain various substituents and which alkyl group is derived from a fragrant molecule possessing an olefinic unsaturation. The unsaturated molecule and/or the aldehyde or ketone are released upon exposure to light, in particular daylight, of the &agr;-keto ester.
There exists, in perfumery, a particular interest in compounds which are capable of “fixing” fragrant molecules, for example by chemical bonding or intramolecular forces like absorption, and releasing said fragrant molecules over a prolonged period of time, for example by the action of heat, enzymes, or even sunlight. Fragrant molecules have to be volatile in order to be perceived. Although many fragrant compounds are known which show a good substantivity, i.e. they will remain on a surface to which they have been applied for several days and can hence be perceived over such a period of time, a great number of fragrant compounds are very volatile, and their characteristic smell can no longer be perceived several hours after their application.
It is thus desirable to dispose of fragrance delivery systems which are capable of releasing the fragrant compound or compounds in a controlled manner, maintaining a desired smell over a prolonged period of time.
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patent: 5032382 (1991-07-01), Grollier et al.
patent: 06 121 822 (1994-05-01), None
Hu, Shengkui et al., “Photochemical Reactions of Alkenyl Phenylglyoxylates,” Journal of Organic Chemistry, 62(20): 6820-6826, 1997.*
Krause, George A., et al., “1,5 and 1,9-Hydrogen Atom Abstractions, Photochemical Strategies for Radical Cyclizations,” Journal of the American Chemical Society, 114(22):8705-8707, 1992.*
Klimova, E. I. et al., in Chemical Abstracts, 112 473d, vol. 71, No. 23, 1969.*
Jones, Paul B. et al., “2-Benzoylbenzoic Acid: A Photolabile Mask for Alcohols and Thiols,” Journal of Organic Chemistry, 61(26):9455-9461, 1996.
Cole Monique T.
Firmenich SA
Harris Kelly Cynthia
Pennie & Edmonds LLP
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