Perfume compositions – Perfume compositions – Ring containing active ingredient
Reexamination Certificate
2000-08-10
2002-04-09
Warden, Jill (Department: 1743)
Perfume compositions
Perfume compositions
Ring containing active ingredient
C512S027000, C560S037000, C560S052000, C560S053000, C560S054000
Reexamination Certificate
active
06369026
ABSTRACT:
TECHNICAL FIELD AND PRIOR ART
The present invention relates to the field of perfumery. It relates, more particularly, to perfuming compositions or perfumed products containing a class of aliphatic or aromatic keto esters of fragrant alcohols, as defined below, which are capable of releasing said fragrant alcohol upon exposure to light, more particularly daylight. The present invention also relates 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 to have good substantivity, i.e. they will cling to 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 after one or two days or even after several hours.
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.
DESCRIPTION OF THE INVENTION
We have now developed a fragrance delivery system which is capable of releasing fragrant alcohols upon exposure to light, and in particular daylight. One object of the present invention is a delivery system which comprises 2-benzoyl benzoates and 2-alkanoyl benzoates of formulae
in which
R
1
represents hydrogen or a group of formula
in which X and Y can be identical or different and represent, independently from each other, hydrogen, a linear or branched alkyl or alkoxy group from C
1
to C
12
, a phenyl group which is optionally substituted, an olefinic group from C
2
to C
12
, an alcohol group, a CO
2
M group, a —NR
6
R
7
group or a group of formula
R
2
can be identical to R
1
or different from it and represents hydrogen, a linear or branched alkyl or alkoxy group from C
1
to C
12
, a phenyl group which is optionally substituted, an olefinic group from C
2
to C
12
, an alcohol group, a CO
2
M group, a —NR
6
R
7
group, a group of formula
or a polyalcohol or polyether group;
R
3
represents hydrogen, an alkyl or alkoxy group from C
1
to C
4
, linear or branched, a OH group or a NH
2
group;
R
4
and R
5
, taken separately, have the meaning given above for R
1
and can be identical to or different from R
1
or from each other; or
R
4
and R
5
, taken together, form a bridging group between the two aromatic rings, which bridging group can be a methylene or a keto group;
m is an integer from 0 to 3 and n is an integer from 0 to 2; R
6
and R
7
, taken separately, each represents hydrogen, an alkyl group from C
1
to C
4
, an alcohol group having an alkyl chain from C
1
to C
12
, or a phenyl group, or, R
6
and R
7
, taken together with the nitrogen atom form a 5-membered or six-membered ring possibly containing another hetero atom;
R
8
represents hydrogen, an alkyl group from C
1
to C
4
, an alcohol group having an alkyl chain from C
1
to C
12
or a phenyl group;
M represents hydrogen or an alkali metal; and
R* is the organic part derived from a primary or secondary fragrant alcohol R* OH.
In the above definition, when reference is made to a fragrant alcohol, there is always meant an alcohol which not only has an odor, but which is also known to a person skilled in the art as being useful as 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 alcohols which can be used with the benzoates of the invention will be mentioned below.
The advantage of the fragrance delivery system of the present invention lies in its capacity to slowly release the fragrant alcohols R*OH from which the benzoyl benzoate esters of formula (I) or the alkanoyl benzoate esters of formula (II) are derived. The release occurs when said esters are exposed to daylight in particular. Upon absorption of energy from said light, the ester undergoes a photoreaction in the course of which the fragrant alcohol is released from the molecule into the surroundings. Said release occurs in a controlled manner, i.e. a more or less constant amount of alcohol R*OH is formed over a period of time, without an initial burst of very intense odor which becomes rapidly imperceptible as is the case with volatile alcohols. Because the release of the alcohol R*OH can occur over several days or weeks, the use of the system of the present invention obviates the drawbacks of many fragrant alcohols R*OH which are of pleasant smell but also very volatile. Good examples are citronellol and geraniol which can only be perceived over a short period of, say, one or two hours, when applied to the surface of, for example, tiles and windows in the course of a cleaning procedure using liquid cleaners; even in solution, the typical smell of said alcohols disappears within several hours. It goes without saying that the concentration of the alcohols in the application plays an important role in the time during which the fragrant molecules can be perceived.
With the system of the present invention, the typical odor of the alcohol R*OH is perceived over a much more prolonged period of time, as the 2-benzoyl benzoate or the 2-alkanoyl benzoate of the fragrance delivery system, which are not volatile, remain on the surface to which they are applied or in the solution into which they are incorporated. Upon exposure to light, the fragrant alcohol R*OH is released, and it is clear that this reaction can provide perceptible amounts of the alcohol over days or weeks, depending, amongst others, on the amount or the concentration of the fragrance delivery system, the time of exposure to light, its intensity and its wavelength.
2-Benzoyl benzoate esters of the above formula (I) which can carry various substituents in positions R
1
, R
2
, R
3
, R
4
and R
5
are known to be photolabile compounds. It was suggested to use these esters as protective groups for alcohols in organic synthesis and subsequently release the alcohol present in the ester function by photolysis (see Porter et al., J. Org. Chem 1996, 61, 9455-9461). The authors conducted experiments with different alcohols, and they described the elimination of geraniol from the geranyl 2-benzoyl benzoate (R
1
═R
2
═R
3
═R
4
═R
5
═H). However, it has not been described or suggested to use the said esters in perfumery, as a fragrance delivery system which is capable of releasing the fragrant alcohol over a prolonged period of time and thus provide a slow release fragrance effect.
As fragrant alcohol R*OH derived radical R* in the above formula (I), in principle a group derived from any fragrant alcohol which is known in the art can be used. Primary and secondary alcohols are shown to be useful in the present invention as they are liberated when exposed to daylight.
As non-limiting examples of alcohols which can be used in the present invention in the form of the 2-benzoyl benzoate esters, one can cite anisic alcohol,
Herrmann Andreas
Pika Jana
Vial Christian
Cole Monique T.
Firmenich SA
Warden Jill
Winston & Strawn
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