Perfume compositions – Perfume compositions – Oxygen containing active ingredient
Reexamination Certificate
2001-02-27
2002-12-10
Warden, Jill (Department: 1743)
Perfume compositions
Perfume compositions
Oxygen containing active ingredient
C512S002000, C512S025000, C512S026000, C560S129000
Reexamination Certificate
active
06492323
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.
DETAILED DESCRIPTION OF THE INVENTION
We have now developed a fragrance delivery system which is capable of releasing fragrant aldehydes or ketones and/or fragrant compounds containing an olefin function upon exposure to light, and in particular daylight.
The object of the present invention is a fragrance delivery system comprising &agr;-keto esters of formula
in which
R′* is hydrogen or a linear or branched, unsubstituted or substituted alkyl group or alkylene group from C
1
to C
35
, an unsubstituted or substituted cycloalkyl group from C
3
to C
8
, an unsubstituted or substituted phenyl group, wherein said alkyl, alkylene, cycloalkyl and phenyl groups may comprise one or several hetero atoms not directly linked to the &agr;-keto group and selected from the group consisting of oxygen, nitrogen, phosphorous and sulfur, or
R′* is a substituted or unsubstituted, linear or branched alkyl group carrying an abstractable hydrogen in &ggr;-position relative to the &agr;-keto function and comprising a moiety from which is derived a fragrant compound containing an olefin function, such that said fragrant compound containing an olefin function is eliminated after abstraction of said &ggr;-hydrogen atom;
R″* is hydrogen or a methyl, ethyl or tert-butyl group or is the organic part of a primary or secondary alcohol from which is derived a fragrant aldehyde or ketone, and at least one of the groups R′* and R″* being a group which is derived from a fragrant compound.
Many of the &agr;-keto ester compounds of the above formula are new. Certain compounds are not, however, such as those of the above formula when R′* is a methyl group, or when R″* is a menthyl or a benzyl group. Specifically, (−)-(1S,1R)-1,7,7- trimethylbicyclo[2.2.1]heptan-2-yl (4-methylphenyl)oxoacetate and hexyl(cyclohexyl)oxoacetate are excluded.
In the above definition, when reference is made to a fragrant compound, aldehyde or ketone, it is always meant a compound which not only has an odor, but which is also known to a person skilled in the art as being useful as a perfuming ingredient for the formulation of perfumes or perfumed articles. The criteria a useful perfuming ingredient has to fulfil are known to a person skilled in the art and include, amongst others, a certain originality of the odoriferous note, stability and a certain price/performance ratio. Non-limiting examples for fragrant compounds which can be used with the &agr;-keto esters of the invention will be mentioned below.
The &agr;-keto esters of the above formula (I) release fragrant compounds upon exposure to light, in particular daylight. The &agr;-keto esters of formula (I), however, are also capable of releasing a fragrant compound containing an olefin function from the group R′* in 1-position relative to the keto function, or a fragrant aldehyde or ketone which is derived from the alcohol R″*OH from which the organic part R″* is present in the ester function of the keto esters of the present invention, or even both.
From the above, it is clear that when reference is made to the organic part R″* of a fragrant alcohol R″*OH, R″* is the hydrocarbyl rest of said alcohol, e.g. a menthyl radical in case R″*OH is menthol.
The release of the fragrant compound from the keto esters occurs in an elimination reaction after an intramolecular transfer of an abstractable hydrogen radical, in &ggr;-position to the &agr;-keto function, to said keto function. The respective part of the molecule from which the hydrogen radical has been abstracted is subsequently released from the reduced keto ester, with concomitant formation of a double bond. The above is illustrated in the scheme below in which possible substituents in the respective parts of the molecules have been omitted for reasons of clarity. The double bonds which will be formed after elimination are indicated by dotted lines.
It is to be understood that the &agr;-keto esters of the present invention can release only one or both molecules of fragrant compound per molecule of &agr;-keto ester. When the hydrogen transfer to the &agr;-keto function is able to occur from the one or the other side of said function, as illustrated above, a certain part of the molecules will release a ketone or aldehyde and a certain part will release the olefin compound. The proportions of the two products released depend on the relative rate of each hydrogen transfer reaction. According to the effect desired, the &agr;-keto esters of the invention can be tailored to release exclusively a fragrant ketone or aldehyde, or exclusively a fragrant compound containing an olefin group, or both. When only one of the two classes of fragrant compounds is to be released from the &agr;-keto esters of the invention, the part of the molecule from which no release shall occur does not contain an abstractable hydrogen atom in &ggr;-position to the keto function, i.e. either no hydrogen atom at all is present in the said position, or it is one which is not abstracted.
It is also clear that the &agr;-keto esters according to the invention can, in a first step, release the olefin compound under formation of a molecule which does not any longer contain an abstractable hydrogen atom in &ggr;-position to the keto function (left side of the molecule as designed above) ; in a second step, this molecule can then release the ketone or aldehyde from the ester function.
A fragrance delivery system which contains the &agr;-keto esters of the above formula (I) has the advantages that the release of the fragrant compound occurs in a more or less constant amount. No initial burst of very
Cole Monique T.
Firmenich SA
Warden Jill
Winston & Strawn
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