Fragrance precursors

Details Fragrance precursors Fragrance precursors

1999-05-24

2001-10-23

Warden, Jill (Department: 1743)

Perfume compositions

Perfume compositions

With preservative, stabilizer, or fixative

C512S008000, C512S011000, C512S021000, C512S025000, C512S026000, C512S027000, C512S007000, C424S065000, C424S076400, C510S101000, C510S102000, C510S105000, C510S107000, C558S260000

Reexamination Certificate

active

06306818

ABSTRACT:

FIELD OF THE INVENTION
The invention relates to fragrance precursors. In particular, the invention relates to the use of several classes of compounds which may act as fragrance precursors e.g. in cosmetic products such as deodorants and antiperspirants and in laundry products such as detergents and fabric softeners. These compounds are odorless, but upon contacting the skin as for example, in skin care compositions or in personal care compositions, produce fragrances. The compounds also produce fragrances when used in the presence of lipases, e.g. as used in (laundry) detergents, thus providing a prolongation of the fabric scenting effect.
BACKGROUND OF THE INVENTION
A principal strategy currently employed in imparting odors to consumer products is the admixing of the fragrance directly into the product. There are, however, several drawbacks to this strategy. The fragrance material may be too volatile, resulting in fragrance loss during manufacturing, storage, and use. Many fragrance materials are also unstable over time. This again results in loss during storage.
In some cases, fragrances are micro-encapsulated or treated with cyclodextrins to form inclusion complexes to help decrease volatility and improve stability. However, these methods are for a number of reasons often not successful. In addition, cyclodextrins may be too expensive for commercial processes.
In many consumer products, it is desirable for the fragrance to be released slowly over time. Microencapsulation and cyclodextrins have been used to provide slow-release properties, however, they are subject to the same limitations as above.
The present invention provides a solution for these and other problems.
SUMMARY OF THE INVENTION
The present invention provides compounds which are odorless, prior to application to the skin, but which release odorant molecules after application to the skin (that is, they provide a delayed release of the fragrance), in particular to the skin in the axilla. The compounds of the present invention also release odorant molecules when used in the presence of lipase-containing products, and, in this way, provide a prolongation of, e.g., the fabric scenting effect in detergents, fabric softeners, fabric softener sheets, and the like.
DETAILED DESCRIPTION OF THE INVENTION
In one embodiment of the present invention, a fragrance precursor of the formula I is provided:
wherein
X is O or S;
m is 0, 1 or 2, and n is 1-20;
R
1
is the radical of an alcohol R
1
OH or a mercaptan R
1
SH having more than five carbon atoms;
R
2
is the radical of an alcohol R
2
OH or a mercaptan R
2
SH having more than five carbon atoms; or
R
2
is a substituted or unsubstituted C
1-40
-alkyl or C
2-40
-alkenyl radical, a carbocyclic radical or an aromatic radical, wherein this R
2
may in addition contain one or more hetero atoms, —COOR
5
, and groups
which groups may further be substituted by —COOR
5
, wherein R
5
is the radical of an alcohol R
5
OH or a mercaptan R
5
SH having more than five carbon atoms, or
R
2
is a polyalcohol radical or a sugar radical, of which one or more of the hydroxyl functions may be substituted as carbonates containing R
1
and/or R
2
;
wherein at least one of R
1
OH, R
1
SH, R
2
OH, R
2
SH, R
5
OH and R
5
SH has fragrance properties;
R
3
and R
4
are H or C
1-6
alkyl or
R
3
and R
4
form a carbocyclic or heterocyclic ring.
In another embodiment of the present invention there is provided a compound of formula
wherein
X is O or S;
m is 0, 1 or 2, and n is 1-20;
R
1
is the radical of an alcohol R
1
OH or a mercaptan R
1
SH having more than five carbon atoms;
R
2
is the radical of an alcohol R
2
OH or a mercaptan R
2
SH having more than five carbon atoms; or
R
2
is a substituted or unsubstituted C
1-40
-alkyl or C
2-40
-alkenyl radical, a carbocyclic radical or an aromatic radical, wherein this R
2
may in addition contain one or more hetero atoms, —COOR
5
, and groups
which groups may further be substituted by —COOR
5
, wherein R
5
is the radical of an alcohol R
5
OH or a mercaptan R
5
SH having more than five carbon atoms, or
R
2
is a polyalcohol radical or a sugar radical, of which one or more of the hydroxyl functions may be substituted as carbonates containing R
1
and/or R
2
;
wherein at least one of R
1
OH, R
1
SH, R
2
OH, R
2
SH, R
5
OH and R
5
SH has fragrance properties;
R
3
and R
4
are H or C
1-6
alkyl or
R
3
and R
4
form a carbocyclic or heterocyclic ring.
Another embodiment of the present invention is process for prolonging the effect of diffusion of the characteristic odor of an odoriferous alcohol or mercaptan as defined above which includes applying to the skin a fragrance precursor as defined above.
Another embodiment of the invention is a method of suppressing human body malodor by means of the fragrance precursors set forth above. This process includes applying to human skin a composition set forth above in a cosmetically acceptable carrier.
Examples of alcohols R
1
OH or R
2
OH are primary or secondary alcohols or phenols, such as for example:
hexyl alcohol*
2-hexyl alcohol*
heptyl alcohol*
octyl alcohol*
nonyl alcohol*
decyl alcohol*
undecyl alcohol*
lauryl alcohol*
myristic alcohol
3-methyl-1-pentanol
cis-3-hexenol*
cis-4-hexenol*
3,5,5-trimethyl hexanol
3,4,5,6,6-pentamethylheptan-2-ol (KOHINOOL, International Flavors & Fragrances)*
citronellol*
geraniol*
oct-1-en-3-ol
2,5,7-trimethyl octan-3-ol (CORPS ABRICOT, Givaudan-Roure)
2-cis-3,7-dimethyl-2,6-octadien-1-ol
6-ethyl-3-methyl-5-octen-1-ol (MEO PARF, Givaudan-Roure)*
3,7-dimethyl-oct-3,6-dienol*
3,7-dimethyloctanol (PELARGOL, Givaudan-Roure)*
7-methoxy-3,7-dimethyl-octan-2-ol (OSYROL, BBA)*
cis-6-nonenol*
5-ethyl-2-nonanol
6,8-dimethyl-2-nonanol (NONADYL, Givaudan-Roure)*
2,2,8-trimethyl-7 (8)-nonene-3-ol (CORPS LAVANDE, Givaudan-Roure)
nona-2,6-dien-1-ol
4-methyl-3-decen-5-ol (UNDECAVERTOL, Givaudan-Roure)*
dec-9-en-1-ol
benzylalcohol
2-methyl undecanol
10-undecen-1-ol
1-phenyl ethanol*
2-phenyl ethanol*
2-methyl-3-phenyl-3-propenol
2-phenyl propanol*
3-phenyl propanol*
4-phenyl-2-butanol
2-methyl-5-phenyl pentanol (ROSAPHEN, H+R)*
2-methyl-4-phenyl-pentanol (PAMPLEFLEUR, International Flavors & Fragrances)*
3-methyl-5-phenyl-pentanol (PHENOXANOL, International Flavors & Fragrances)*
2-(2-methylphenyl)-ethanol*
4-(1-methylethyl)benzene methanol
4-(4-hydroxyphenyl)butan-2-one*
2-phenoxy ethanol*
4-(1-methylethyl)-2-hydroxy-1-methyl benzene
2-methoxy-4-methyl phenol
4-methyl phenol
anisic alcohol*
p-tolyl alcohol*
cinnamic alcohol*
vanillin*
ethyl vanillin*
eugenol*
isoeugenol*
thymol
anethol*
decahydro 2-naphthalenol
borneol*
cedrenol (Givaudan-Roure)*
farnesol*
fenchyl alcohol*
menthol*
3,7,11-trimethyl-2,6,10-dodecatrien-1-ol
alpha ionol*
tetrahydro ionol*
2-(1,1-dimethylethyl)cyclohexanol*
3-(1,1-dimethylethyl)cyclohexanol*
4-(1,1-dimethylethyl)cyclohexanol*
4-isopropyl cyclohexanol (FOLROSIA® Givaudan-Roure)
6,6-dimethyl-bicyclo [3.3.1]hept-2-ene-2-ethanol (DIEPTOL, Dragoco)
6,6-dimethyl-bicyclo [3.1.1]hept-2-ene-methanol (MYRTENOL, BBA)*
p-menth-8-en-3-ol (ISOPULEGOL, Givaudan-Roure)*
3,3,5-trimethyl cyclohexanol
2,4,6-trimethyl-3-cyclohexenyl-methanol*
4-(1-methylethyl)cyclohexyl-methanol (MAYOL, Firmenich)*
4-(1,1-dimethylethyl)cyclohexanol
2-(1,1-dimethylethyl)-cyclohexanol (VERDOL, International Flavors & Fragrances)
2,2,6-trimethyl-alpha-propyl cyclohexane propanol (TIMBEROL, Dragoco)*
5-(2,2,3-trimethyl-3-cyclopentenyl)-3-methyl pentan-2-ol (SANDALORE® Givaudan-Roure)*
3-methyl-5-(2,2,3-trimethyl cyclopentyl-3-enyl)pent-4en-2-ol(EBANOL, Givaudan-Roure)*
2-ethyl-4(2,2,3-trimethyl cyclopentyl-3-enyl)but-2-en-1-ol (RADJANOL, Givaudan-Roure)*
4-(5,5,6-trimethylbicyclo[2.2.1]hept-2-yl)-cyclohexanol (SANDELA, Givaudan-Roure)*
2-(2-methylpropyl)-4-hydroxy-4-methyl-tetrahydropyran* (FLOROSA Q, Quest)*
2-cyclohexyl propanol*
2-(1,1-dimethylethyl)-4-methyl cyclohexanol (ROOTANOL, BASF)*
1-(2-tert-butyl-cyclohexyloxy)-2-butanol (AMBER CORE, Kao)*
1-(4-isoporpyl-cyclohexyl)-ethanol (MUGETANOL, H&R)*
Examples of thiols R
1
XH or R
2
XH are:
3-mercapto-1-hexanol
2

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