Perfume compositions – Perfume compositions – Oxygen containing active ingredient
Reexamination Certificate
2000-08-23
2003-04-08
Warden, Jill (Department: 1743)
Perfume compositions
Perfume compositions
Oxygen containing active ingredient
C512S002000, C512S012000, C549S200000, C549S346000, C549S347000, C549S356000, C549S357000
Reexamination Certificate
active
06544945
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to cyclic pro-perfumes capable of releasing at least one fragrance raw material alcohol, preferably a tertiary fragrance raw material alcohol. The novel pro-perfumes of the present invention can be modified by the formulator to control the rate at which the fragrance raw material alcohol is released once the material is applied, for example, to human skin.
BACKGROUND OF THE INVENTION
Humans have applied scents and fragrances to their skin since antiquity. Originally these aesthetically pleasing materials were commonly isolated in raw form as resins, gums or essential oils from natural sources, inter alia, the bark, roots, leaves and fruit of indigenous plants. These resins, gums, and oils were directly applied to the body or diluted with water or other solvent, including in some cases, wine. With the advent of modern chemistry, individual components responsible for the odor properties of these resins, gums and oils were isolated and subsequently characterized. Modern perfumery involves the artful compounding of fragrance materials to achieve novel fragrance compositions having defined “characteristics”.
Many modem fragrances are no longer derived from natural sources but are synthesized by modern chemical methods as highly pure fragrance raw materials (FRM). These FRM's are currently formulated to produce fine perfumes, colognes, eau de toilettes, after-shave lotions, and other personal fragrance compositions. Those skilled in the art of preparing these fragrance-containing compositions have categorized fragrances into three types based on their relative volatility; top, middle, and base notes.
Top, middle, and base notes each serve a different purpose in the blending of fragrances and when properly formulated produce a “balanced fragrance” composition. Based on volatility, these notes are described by those skilled in the art as: the base notes having the most long lasting aroma; the middle notes, have a medium volatility; and the top notes are the most volatile. Key to successfully formulating a fragrance-containing composition is the precise balance between these three groups of materials producing a fragrance-containing composition that diffuses during its evaporation in a manner which has an aesthetic quality.
It has been the goal of those skilled in the art of perfumes and fragrances to provide aesthetically pleasant odor compositions wherein the initial top, middle, and base note balance is maintained for an extended period of time. Due to the uneven rate of evaporation of the components which comprise a fine perfume or fragrance, the initial fragrance may be quite different than the aroma perceived several hours later. This problem is solved in many different ways by the user. One method is to “load up” on the perfume initially and rely on the natural evaporation rate to diminish the fragrance to a suitable level several hours later when the desired effect is needed. Another method which is used is to continually renew the fragrance by reapplying small amounts of the perfume to the skin at short time intervals. Neither of these solutions is adequate to overcome the diminishing level of top and middle notes over time. In fact, base notes which are present over a protracted period by virtue of their low volatility, begin to accumulate with each “re-freshing” of perfume. After some time these base notes overwhelm the other fragrance notes and destroy the original fragrance balance.
However, despite these artful approaches and compensating for the physical properties of perfume ingredients, formulators have not been able to well control the rate at which fragrance raw materials, especially fragrance raw material alcohols, are released when applied, for example, on human skin, hair, etc. Therefore, there has been a long felt need for a means of releasing at least one fragrance raw material alcohol, preferably tertiary alcohols, at a controllable rate.
It has now been surprisingly discovered that the novel cyclic pro-perfumes, which are the subject matter of the present invention, can not only release fragrance raw material alcohols but can be modified to release said alcohols within a range of time desirable to the formulator. In addition, the cyclic pro-perfumes described herein are capable of delivering highly desirable tertiary alcohols.
SUMMARY OF THE INVENTION
The present invention meets the aforementioned needs in that it has been surprisingly discovered than certain cyclic pro-perfumes can be modified to release their fragrance raw material alcohols at variable rates after being exposed to an acid milieu inter alia human skin.
A first aspect of the present invention relates to cyclic pro-perfumes capable of releasing at least one fragrance raw material alcohol, said pro-perfumes having the formula:
wherein —OR is a unit derived from a fragrance raw material alcohol; R
1
is hydrogen, C
1
-C
22
alkyl, C
1
-C
22
alkenyl, C
6
-C
12
aryl, C
6
-C
22
alkylenearyl, C
3
-C
20
substituted or unsubstituted alkyleneoxyalkyl, and mixtures thereof; R
2
, R
3
, R
4
, and R
5
are each independently selected from hydrogen, C
1
-C
30
substituted or unsubstituted linear alkyl, C
3
-C
30
substituted or unsubstituted branched alkyl, C
3
-C
30
substituted or unsubstituted cyclic alky, C
2
-C
30
substituted or unsubstituted linear alkenyl, C
3
-C
30
substituted or unsubstituted branched alkenyl, C
3
-C
30
substituted or unsubstituted cyclic alkenyl, C
2
-C
30
substituted or unsubstituted linear alkynyl, C
3
-C
30
substituted or unsubstituted branched alkynyl, C
6
-C
30
substituted or unsubstituted alkylenearyl, C
6
-C
30
substituted or unsubstituted aryl, C
2
-C
20
substituted or unsubstituted alkyleneoxy, C
3
-C
20
substituted or unsubstituted alkyleneoxyalkyl, C
7
-C
20
substituted or unsubstituted alkylenearyl, C
6
-C
20
substituted or unsubstituted alkyleneoxyaryl, and mixtures thereof, or any two R
2
, R
3
, R
4
, or R
5
can be taken together to form a fused ring or spiroannulated ring having from 3 to 8 carbons and optionally one or more heteroatoms in said ring, said ring is optionally further substituted by one or more C
1
-C
22
alkyl, C
1
-C
22
alkenyl, C
6
-C
12
aryl, C
6
-C
22
alkylenearyl units, and mixtures thereof, Y is —CR
6
R
7
—, C═O, and mixtures thereof, wherein R
6
and R
7
are independently hydrogen, hydroxyl, nitro, nitrilo, C
1
-C
30
substituted or unsubstituted linear alkyl, C
3
-C
30
substituted or unsubstituted branched alkyl, C
3
-C
30
substituted or unsubstituted cyclic alkyl, C
2
-C
30
substituted or unsubstituted linear alkenyl, C
3
-C
30
substituted or unsubstituted branched alkenyl, C
3
-C
30
substituted or unsubstituted cyclic alkenyl, C
2
-C
30
substituted or unsubstituted linear alkynyl, C
3
-C
30
substituted or unsubstituted branched alkynyl, C
6
-C
30
substituted or unsubstituted alkylenearyl, C
6
-C
30
substituted or unsubstituted aryl, C
2
-C
20
substituted or unsubstituted alkyleneoxy, C
3
-C
20
substituted or unsubstituted alkyleneoxyalkyl, C
7
-C
20
substituted or unsubstituted alkylenearyl, C
6
-C
20
substituted or unsubstituted alkyleneoxyaryl, and mixtures thereof, or R
6
and R
7
can be taken together to form a spiroannulated ring or taken together with any R
2
, R
3
, R
4
, or R
5
to form a fused ring, said spiroannulated or fused ring having from 3 to 8 carbons and optionally one or more heteroatoms in said ring, said ring further optionally substituted by one or more C
1
-C
22
alkyl, C
1
-C
22
alkenyl, C
6
-C
12
aryl, C
6
-C
22
alkylenearyl units, and mixtures thereof; n is from 0 to 3.
The present invention also relates to fine fragrance compositions inter alia perfumes, colognes, after shaves, and eau de toilettes comprising said cyclic pro-perfumes. In addition, personal care and personal hygiene articles may comprise the cyclic pro-perfumes described herein. Non-limiting examples of these personal care items include deodorants, body lotions or creams, sun tan lotions, and shampoos.
The present invention also relates to a fragra
Gray Lon Montgomery
Miracle Gregory Scot
Price Kenneth Nathan
Cole Monique T.
Echler Sr. Richard S.
McBride James F.
The Procter & Gamble & Company
Warden Jill
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