Pro-fragrances

Details Pro-fragrances Pro-fragrances

2001-10-22

2003-04-22

Richter, Johann (Department: 1621)

Perfume compositions

Perfume compositions

With preservative, stabilizer, or fixative

C512S008000, C512S012000, C512S022000, C512S024000, C564S454000, C568S591000

Reexamination Certificate

active

06551987

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to &bgr;-amino ketone pro-fragrances which are capable of delivering fragrance raw material ketones, preferably &agr;,&bgr;-unsaturated ketones, inter alia, damascones, ionones, to a situs, especially to human.skin wherein said pro-fragrances release the fragrance raw material ketones providing the user with extended aesthetic benefits.
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. Aside from common “perfume vehicles” inter alia, fine perfumes, colognes, eau de toilettes, and after-shave lotions, a wide variety of personal care or personal hygiene items also deliver for aesthetic reasons fragrance notes, accords, or fragrance “characteristics”.
It is well known that mixtures of perfume or fragrance raw materials when deposited on the skin lose intensity and may change character with time, mainly due to factors such as differential evaporation and skin penetration. Many attempts have been made to minimize these drawbacks, but so far without notable success. Particularly, efforts have been made to prolong the diffusion, as well as to improve other characteristics of fragrance materials, by e.g. increasing the fragrance raw material concentration or by using additives such as silicones, glycerol, polyethylene glycols and so on. Such additions, however, have never been adequate to increase the longevity of the fragrance odor.
Recently the advent of pro-fragrance and pro-accords have afforded the fine fragrance and perfume formulator with the ability to deliver fragrance raw materials to human skin in a controllable manner thus enhancing the longevity of the fragrance. Most pro-accords inter alia orthoesters, are suitable for delivery fragrance raw material alcohols and esters. Aldehydes and ketones have been delivered via acetals and ketals respectively, however, both of these pro-fragrance materials depend upon the modification of the carbonyl moiety and the rate of ketone fragrance raw material release has been difficult to fine tune to the subtleties of fine fragrance and perfume accords.
Accordingly, there remains a need in the art for a ketone fragrance raw material releasing pro-fragrance which can be formulated into fine fragrances, perfumes, personal care and personal hygiene products wherein the ketone fragrance raw material components can be released in a highly controllable manner to provide enhanced fragrance longevity.
SUMMARY OF THE INVENTION
The present invention meets the aforementioned needs in that it has been surprisingly discovered that certain ketone fragrance raw materials inter alia derivatives of ionone and damascone can be controllably released from novel &bgr;-amino ketone pro-fragrances. The &bgr;-amino pro-fragrances, preferably &bgr;-amino ketone pro-fragrances, of the present invention are useful in fragrance delivery systems which deliver fine fragrances with an enhanced perfume longevity.
A first aspect of the present invention relates to compositions comprising:
A) from 0.01% by weight, of a pro-fragrance component comprising:
a) at least 0.01% by weight, of an &bgr;-amino ketone pro-fragrance component, said pro-fragrance having the formula:
 wherein G
1
is —CN, —C(O)Y
1
, —CO
2
Y
1
, and mixtures thereof; G
2
is G
1
, Y
2
, or mixtures thereof, Y
1
and Y
2
are each independently C
1
-C
18
alkyl, C
1
-C
18
alkenyl, C
1
-C
15
cycloalkyl, C
1
-C
15
cycloalkenyl, C
6
-C
15
aryl, C
6
-C
15
alkyl substituted aryl, and mixtures thereof; R and R
1
are each independently C
1
-C
22
substituted or unsubstituted, branched or unbranched alkyl, C
2
-C
22
substituted or unsubstituted, branched or unbranched alkenyl, C
2
-C
20
substituted or unsubstituted, branched or unbranched hydroxyalkyl, C
7
-C
20
substituted or unsubstituted alkylenearyl, C
3
-C
20
substituted or unsubstituted cycloalkyl, alkyleneoxy units having the formula:
—(R
4
O)
x
R
5
 wherein R
4
is C
2
-C
4
alkylene, R
5
is hydrogen, C
1
-C
4
alkyl, and mixtures thereof, x is from 1 to 6; C
6
-C
20
aryl, C
5
-C
20
heteroaryl comprising one or more heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, and mixtures thereof; two of the units Y
1
, Y
2
, R or R
1
when taken together form one or more aromatic or non-aromatic, heterocyclic or non-heterocyclic, single rings, fused rings, bicyclo rings, spiroannulated rings, or mixtures thereof, said rings comprising from 3 to 20 carbon atoms and one or more heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, and mixtures thereof; and R
2
and R
3
are hydrogen;
b) at least 0.01% by weight, of an aldehyde or ketone releasing pro-fragrance component, said pro-fragrance having the formula:
 wherein said pro-fragrance or pro-accord releases an aldehyde or a ketone fragrance raw material, wherein X is oxygen or sulfur; R
a
is:
i) C
6
-C
22
substituted or unsubstituted linear alkyl;
ii) C
6
-C
22
substituted or unsubstituted branched alkyl;
iii) C
6
-C
22
substituted or unsubstituted linear alkenyl;
iv) C
6
-C
22
substituted or unsubstituted branched alkenyl;
v) C
6
-C
22
substituted or unsubstituted cycloalkyl;
vi) C
6
-C
22
substituted or unsubstituted branched cycloalkyl;
vii) C
6
-C
22
substituted or unsubstituted cycloalkenyl;
viii) C
6
-C
22
substituted or unsubstituted branched cycloalkenyl;
ix) C
6
-C
22
substituted or unsubstituted aryl;
x) C
6
-C
22
substituted or unsubstituted heterocyclicalkyl;
xi) C
6
-C
22
substituted or unsubstituted heterocyclicalkenyl;
xii) and mixtures thereof;
 R
b
is:
i) hydrogen;
ii) C
1
-C
10
substituted or unsubstituted linear alkyl;
iii) C
3
-C
10
substituted or unsubstituted branched alkyl;
iv) C
2
-C
10
substituted or unsubstituted linear alkenyl;
v) C
3
-C
10
substituted or unsubstituted branched alkenyl;
vi) C
3
-C
15
substituted or unsubstituted cycloalkyl;
vii) C
4
-C
15
substituted or unsubstituted branched cycloalkyl;
viii) C
4
-C
15
substituted or unsubstituted cycloalkenyl;
ix) C
5
-C
15
substituted or unsubstituted branched cycloalkenyl;
x) C
6
-C
15
substituted or unsubstituted aryl;
xi) C
6
-C
22
substituted or unsubstituted heterocyclicalkyl;
xii) C
6
-C
22
substituted or unsubstituted heterocyclicalkenyl;
 R
a
and R
b
when taken together form a substituted or unsubstituted ring having in the ring from 3 to 10 carbon atoms; and
 each R
c
, R
d
, R
6
and each R
4
and R
5
pair are independently:
i) R
b
;
ii) hydroxyl;
iii) a carbonyl comprising unit having the formula:
—(CH
2
)
v
COR
7
 wherein R
7
is:
a) —OH;
b) —OR
8
wherein R
8
is hydrogen, C
1
-C
15
substituted or unsubstituted linear alkyl, C
1
-C
15
substituted or unsubstituted branched alkyl, C
2
-C
22
substituted or unsubstituted linear alkenyl, C
3
-C
22
substituted or unsubstituted branched alkenyl, or mixtures thereof;
c) —N(R
9
)
2
wherein R
9
is hydrogen, C
1
-C
6
substituted or unsubstituted linear alkyl, C
3
-C
6
substituted or unsubstituted branched alkyl, or mixtures thereof;
d) C
1
-C
22
substituted or unsubstituted linear alkyl;
e) C
1
-C
22
substituted or unsubstituted branched alkyl;
f) C
2
-C
22
substituted or unsubstituted linear alkenyl;
g) C
3
-C
22
substituted or unsubstituted branched alkenyl;
h) C
3
-C
22
substituted or unsubstituted cycloalkyl;
i) C
6
-C
22
substituted or unsubstituted aryl;
j) C
6
-C
22
substituted or unsubstituted heterocyclicalkyl;
k) C
6
-C
22
substituted or unsubstituted heterocyclicalkenyl;
 the index v is from 0 to 22;
iv) alkyleneoxy unit

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