Perfume composition using organopolysiloxanes

Details Perfume composition using organopolysiloxanes Perfume composition using organopolysiloxanes

2000-04-21

2002-05-28

Dees, Jose′ G. (Department: 1616)

Perfume compositions

Perfume compositions

C424S401000, C512S002000

Reexamination Certificate

active

06395704

ABSTRACT:

The present invention relates to a fragrance composition comprising a fragrance base and a lipophilic solubilizing agent based on at least one polyorganosiloxane containing a polar or polarizable function; the invention also relates to the use of polyorganosiloxanes containing a polar or polarizable function as agents for dissolving fragrance bases and emollients in fragrance compositions.
A first subject of the invention consists of a fragrance composition comprising a fragrance base and a lipophilic agent for dissolving the said fragrance base, the said solubilizing agent being based on at least one linear polyorganosiloxane containing a polar or polarizable function of formula (I)
(R
1
)(R
2
)(R
3
)Si—O—[Si(R
4
)(Z)—O]
n
—[Si(R
5
)(R
6
)—O]
m
—Si(R
7
)(R
8
)(R
9
)  (I)
or a cyclic polyorganosiloxane of formula (I′)
in which formula (I)
the symbols R
1
and R
9
are identical or different and represent the symbol Z or an alkyl radical containing from 1 to 8 carbon atoms, preferably 1 or 2 carbon atoms, most particularly 1 carbon atom
the symbols R
2
, R
3
, R
4
, R
5
, R
6
, R
7
and R
8
are identical or different and represent an alkyl radical containing from 1 to 8 carbon atoms, preferably 1 or 2 carbon atoms, most particularly 1 carbon atom
the symbol Z represents a polar or polarizable organic radical
n is an integer or decimal number which can range from 0 to 5, preferably equal to 0 or 1,
at least one of the radicals R
1
and R
9
representing the symbol Z when n is equal to 0
m is an integer or decimal number which can range from 0 to 5, preferably equal to 0
formula (I′) in which
the symbols R
4
, R
5
, R
6
and Z have the same definition as that given above
n is an integer or decimal number which can range from 1 to 5, preferably equal to 1
m is an integer or decimal number which can range from 1 to 5, with n+m at least equal to 3,
the said polyorganosiloxane having the following Hansen solubility parameters
&dgr;
D
of London interactions ranging from 8 to 21 (J/cm
3
)
½
&dgr;
P
of Keesom interactions of greater than 0 and possibly ranging up to 25 (J/cm
3
)
½
&dgr;
H
of hydrogen bonding ranging from 0 to 23 (J/cm
3
)
½
.
The three-dimensional solubility space, in which the solvents and all the organic molecules exist, is defined by C M Hansen in “The three dimensional solubility parameters” J. Paint Technol. 39, 105 (1967); &dgr;
D
, &dgr;
P
and &dgr;
H
represent the partial solubility parameters associated, respectively, with the London dispersion forces, the Keesom polarity forces and the hydrogen bonding forces, given that these partial parameters are the components of the overall solubility parameter &dgr;, referred to as the Hildebrand solubility parameter, associated with the voluminal cohesion of the molecule.
Examples of polar organic radicals Z which may be mentioned are
ester groups of formulae —R′OOC—R″ and —R′—COOR″′ directly linked to silicon, in which formulae
R′ represents a saturated or unsaturated, linear or branched aliphatic multivalent group containing from 2 to 10 carbon atoms
R″ represents a C
1
-C
8
, preferably C
1
-C
3
, alkyl group
R″′ represents a C
1
-C
5
, preferably C
1
-C
3
, alkyl group
the hydroxyl or alcohol groups of formula —R′—O—(RO)
x
H directly linked to silicon, in which formula
R′ represents a saturated or unsaturated, linear or branched aliphatic multivalent group containing from 2 to 10 carbon atoms
R represents a linear or branched alkylene group, which may be identical or different, containing 2 or 3 carbon atoms
x can range from 0 to 20
primary or secondary amido groups —R′—CO—NH(R), directly linked-to silicon, in which R′ represents a saturated or unsaturated, linear or branched aliphatic multivalent group containing from 2 to 10 carbon atoms
carboxyl groups —R′—COOH, directly linked to silicon, in which R′ represents a saturated or unsaturated, linear or branched aliphatic multivalent group containing from 2 to 10 carbon atoms
linear or branched, saturated or unsaturated, C
6
-C
20
haloaliphatic radicals, in particular chloro- or fluoroaliphatic radicals
saturated or unsaturated, C
5
-C
6
halocycloaliphatic radicals, in particular chloro- or fluorocycloaliphatic radicals, directly linked to silicon via a saturated or unsaturated, linear or branched aliphatic multivalent group containing from 2 to 10 carbon atoms
aryl radicals, preferably C
6
aryl radicals, substituted with at least one halogen atom (in particular chlorine or fluorine), directly linked to silicon via a saturated or unsaturated, linear or branched aliphatic multivalent group containing from 2 to 10 carbon atoms.
Mention may be made more particularly of 3-propylol, 2-propyloxyethanol, diethyl 3-propyl malonate and ethylpyrrolidone radicals, which radicals can be obtained by opening the vinylic double bond of, respectively, allyl alcohol, allyloxyethanol, diethyl allyl malonate or vinylpyrrolidone, as well as 3-propylacetate.
Examples of polarizable organic radicals Z which may be mentioned are
linear or branched C
6
-C
20
aliphatic radicals containing at least one internal ethylenic unsaturation, preferably two conjugated double bonds
ethylenically unsaturated C
5
-C
6
cycloaliphatic radicals, optionally substituted with at least one C
1
-C
8
alkyl group, linked directly to silicon via a saturated or unsaturated, linear or branched aliphatic multivalent group containing from 2 to 10 carbon atoms
a phenyl radical
aryl radicals, preferably C
6
aryl radicals, optionally substituted with at least one C
1
-C
8
alkyl or C
6
aryl group, linked directly to silicon via a saturated or unsaturated, linear or branched aliphatic multivalent group containing from 2 to 10 carbon atoms.
Mention may be made more particularly of a phenyl radical and the radicals obtained by opening the vinylic double bond of styrene, of &agr;-methylstyrene, of &agr;-methylstyrene dimer, of dihydromyrcene, of limonene, etc., or the terminal triple bond of phenylacetylene, etc.
The said radical Z is preferably a phenyl radical, a phenylalkyl radical in which the alkyl residue contains from 2 to 10 carbon atoms, or a phenylalkenyl radical in which the alkenyl residue contains from 2 to 10 carbon atoms, in particular phenyl(methyl)methyl, phenylethenyl and, most particularly, phenylethyl. Most preferably, the fragrance composition comprises a mixture of polyorganosiloxanes predominantly containing a polyorganosiloxane containing a phenylethyl radical, a smaller amount of a polyorganosiloxane containing a phenyl(methyl)methyl radical and a small amount of a polyorganosiloxane containing a phenylethenyl radical.
Preferably, the said polyorganosiloxane is a organodisiloxane MM of formula (I) in which n and m are equal to 0 and R
1
and R
9
represent a phenyl radical, in particular diphenyltetramethyldisiloxane, or a linear organotrisiloxane MDM of formula (I) in which n is equal to 1 and m is equal to 0, the symbols R
1
, R
2
, R
3
, R
4
, R
7
, R
8
and R
9
preferably being methyl radicals.
The said polyorganosiloxanes of formula (I) or (I′) in which the polar or polarizable function (Z) is other than phenyl can be obtained in a known manner by hydrosilylation between at least one hydrogenopolyorganosiloxane of formula (II) or (II′)
(R
1
)(R
2
)(R
3
)Si—O—[Si(R
4
)(H)—O]
n
—[Si(R
5
)(R
6
)—O]
m
—Si(R
7
)(R
8
)(R
9
)  (II)
in which formulae the symbols R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
, R
8
, R
9
, n and m have the same definition as that given above,
and the compound containing vinylic or terminal acetylenic unsaturation from which the radical Z is derived, in the presence of a hydrosilylation catalyst, in particular such as platinum.
This operation can be carried out with a slight excess of one or other of the reagents, generally up to 10 mol % relative to the stoichiometry, at a temperature of about 50° C. to 100° C., preferably from about 50° C. to 80° C., in the presen

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