Fragrance precursor compounds

Details Fragrance precursor compounds Fragrance precursor compounds

1998-05-12

2001-07-17

Geist, Gary (Department: 1623)

Organic compounds -- part of the class 532-570 series

Organic compounds

Silicon containing

C556S415000, C556S416000, C556S417000, C528S041000, C528S043000, C424S047000, C424S060000, C424S070120

Reexamination Certificate

active

06262287

ABSTRACT:

FIELD OF THE INVENTION
The present invention provides fragrance precursor compounds. In particular, the invention provides a method for the use of several classes of compounds which can act as fragrance precursors in cosmetic products, such as deodorants and antiperspirants. These compounds can also act as fragrance precursors in laundry products such as detergents and fabric softeners. The compounds are normally odorless or nearly so, 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. in laundry products.
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. For example, the fragrance material can 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 of fragrance during storage.
In some cases, fragrances are microencapsulated 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 can be too expensive.
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 associated with the use of cyclodextrins as stated above.
The Japanese Patent Application No. 07/179 328 discloses sustained release of aromatic compounds which are perfume derivatives for control of perspiration. The compositions perfume when they are gradually decomposed by bacteria usually residing on the body surface, resulting in a long, stable perfuming effect. A preferred derivative is said to contain one or a mixture of phosphoric ester, amino acid and carboxylic derivatives of perfumes. The active fragrancing substance, i.e. an alcohol, an aldehyde or a ketone, is released slowly after laundering a fabric to prolong the fragrancing of the fabric after laundering.
The PCT Application WO 95/04809 discloses the use of esters for scenting fabrics being washed in the presence of a lipase-containing detergent.
The PCT application WO 96/1999119 describes the addition of silicone polymers to perfumes to improve surface residuality of a fragrance. The fragrance is not bound to the polymer.
U.S. Pat. No. 3,215,719 describes silicate esters of essential alcohols where the oxy group RO— of an alcohol is directly bonded to silicone as Si—OR which can be applied to textiles to impart thereto a lasting fragrance.
SUMMARY OF THE INVENTION
The present invention provides compounds which have a low level of odor, or are even 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 as they react with microorrganisms present on the skin, i.e. Axilla bacteria. The compounds of the present invention also release odorant molecules when used in the presence of lipase-containing products.
The compounds of the present invention are organosiloxane compounds having at least one unit of the formula
or a mixture thereof. In addition, if any other unit(s) in the siloxanes is/are present this/these unit(s) have the following formula
wherein R represents a substituted or unsubstituted C
1-8
alkyl group or a substituted or unsubstituted aryl group; R″ represents a hydrogen atom, a monovalent C
1-8
hydrocarbon group or a monovalent C
1-8
halogenated hydrocarbon group; R
1
represents a hydrogen atom, a substituted or unsubstituted C
1-8
alkyl group or a substituted or unsubstituted aryl group or a bond connecting CR
1
and CR
3
; R
3
represents a hydrogen atom or a substituted or unsubstituted C
1-8
alkyl group, or a substituted or unsubstituted aryl group; A represents (CR
4
2
)
n
whereby R
4
represents a substituted or unsubstituted C
1-8
alkyl group, a substituted or unsubstituted aryl group, or a hydrogen atom, n is from 0-20, preferably 1 to 10, and each R
4
is the same or different; OR
2
represents the residue of an olfactive alcohol or of the enol form of an olfactive aldehyde or olfactive ketone;
is 0, 1 or 2; and
is 0, 1, 2 or 3.
DETAILED DESCRIPTION OF THE INVENTION
In the general formula of the organosiloxane compounds of the invention, R may be for example methyl, ethyl, butyl or phenyl. R″ may be for example alkyl, alkenyl, aryl, alkaryl, aralkyl and halogen substituted alkyl, alkenyl, aryl, alkaryl and aralkyl. Specific examples are methyl, ethyl, vinyl, phenyl and 3,3,3-trifluoropropyl. R
4
preferably is a hydrogen atom or methyl. It is preferred that at least 80% of all R and R″ groups are methyl groups.
In addition,
is preferably 1, while
is preferably 2, making either a substantially linear organosiloxane compound or a cyclic diorganosiloxane polymer. However, if the diorganosiloxane is a substantially linear polymer, at least two endblocking units must be present, thus requiring the presence of two units when
is 2, two units when the value of
is 3, one unit when
is 2 and one unit when
is 3. Therefore, suitable preferred polymers have either the general formula
wherein R and R″ are as defined above; X denotes a group Y or a group R″; and Y denotes a group of the formula Ia or Ib,
is from 0 to 1000;
is from 0 to 1000, whereby at least one X denotes Y in the case that
=0;
has the value of from 0 to 10; and
has the value of from 1 to 10. Preferably
is from 3 to 6. Further embodiments occur when
is greater than 3, or
has a value of at least 3.
The organosiloxane compounds of the present invention have at least one unit falling within the general formula Ia or Ib. Suitable organosiloxane compounds include polymeric materials, which may be homopolymers consisting only of such units Ia or Ib or copolymers containing in addition units having the general formula II.
The compounds of formula Ia or Ib are not limited to any particular stereoisomers, all possible stereoisomers as well as racemates are thus included within the scope of formula Ia or Ib.
The units of formula Ia or Ib may be distributed randomly in an organosiloxane copolymer. Units of formula Ia or Ib may be end-blocking units of these polymers or they may be located at both the end of the copolymer and in the chain of the copolymer.
The organosiloxane compounds may vary from freely flowing liquids to highly viscous gum-like materials to resinous solids. Preferred, at least for cosmetic applications, are monomers or liquid, substantially linear, organosiloxane homopolymers and copolymers, most preferably those having a viscosity of from 25 to 500 mm
2
/s since these are more easily mixed with other ingredients to make cosmetic compositions and they will spread more easily onto the skin.
Suitable examples of alcohols R
2
OH are primary or secondary alcohols or phenols such as listed in Table 1.
Table 1
amyl alcohol
hexyl alcohol*
2-hexyl alcohol*
heptyl alcohol*
octyl alcohol*
nonyl alcohol*
decyl alcohol*
undecyl alcohol*
lauryl alcohol*
myristic alcohol
3-methyl-but-2-en-1-ol*
3-methyl-1-pentanol
cis-3-hexenol**
cis-4-hexenol*
3,5,5-trimethyl hexanol
3,4,5,6,6-pentamethylheptan-2-ol
citronellol**
geraniol**
oct-1-en-3-ol
2,5,7-trimethyl octan-3-ol
2-cis-3,7-dimethyl-2,6-octadien-1-ol
6-ethyl-3-methyl-5-octen-1-ol*
3,7-dimethyl-oct-3,6-dienol*
3,7-dimethyloctanol*
7-methoxy-3,7-dimethyl-octan-2-ol*
cis-6-nonenol*
5-ethyl-2-nonanol
6,8-dimethyl-2-nonanol*
2,2,8-trimethyl-7 (8)-nonene-3-ol
nona-2,6-dien-1-ol
4-methyl-3-decen-5-ol**
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-

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