Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Cosmetic – antiperspirant – dentifrice
Reexamination Certificate
2000-04-13
2003-01-21
Dees, Jose'G. (Department: 1616)
Drug, bio-affecting and body treating compositions
Preparations characterized by special physical form
Cosmetic, antiperspirant, dentifrice
Reexamination Certificate
active
06509023
ABSTRACT:
The present invention relates to a cosmetic composition comprising at least one functionalized polyorganosiloxane, as well as to the use of the said polyorganosiloxane as an emollient and/or vehicle and/or a transfer-resistance agent in cosmetic compositions for the skin and/or the hair.
A first subject of the invention consists of a cosmetic composition comprising at least one linear functionalized polyorganosiloxane 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 functionalized polyorganosiloxane of formula (I′)
in which:
in formula (I)
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
in formula (I′)
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
in formulae (I) and (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 linear or branched, saturated or unsaturated, C
6
-C
20
haloaliphatic radical, in particular a chloro- or fluoroaliphatic radical
a radical —X—Y, in which X represents a saturated or unsaturated, linear or branched aliphatic multivalent group containing from 2 to 10 carbon atoms, and Y represents
an aryl radical, preferably a C
6
aryl radical, optionally substituted with at least one C
1
-C
8
alkyl or C
6
aryl group or a halogen atom (in particular chlorine or fluorine),
an ethylenically unsaturated C
5
-C
6
cycloaliphatic radical optionally substituted with at least one C
1
-C
8
alkyl group or a halogen atom (in particular chlorine or fluorine),
a saturated C
5
-C
6
cycloaliphatic radical substituted with at least one halogen atom (in particular chlorine or fluorine),
C
4
-C
9
hydrocarbon-based heterocyclic radical containing at least one nitrogen and/or oxygen and/or sulphur hetero atom, the radical optionally being substituted with at least one C
1
-C
8
alkyl or C
6
aryl group or a halogen atom (in particular chlorine or fluorine),
the said symbol Z also possibly representing a phenyl radical (directly linked to the silicon) when n+m is equal to 0.
The said functionalized polyorganosiloxanes of formula (I) or (I′) have the following Hansen solubility space parameters
&dgr;
D
of London interactions ranging from 8 to 21 (J/cm
3
)
{fraction (1/2 )}
&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.
The said multivalent group X connecting the radical Y to the silicon can preferably be a divalent alkanediyl or alkenediyl group containing two carbon atoms, ethylene, methylmethylene or ethenylene, or three carbon atoms, methylethylene or methylethenylene.
As examples of radicals Z, mention may be made more particularly of the radicals obtained by opening the vinylic double bond of styrene, of &agr;-methylstyrene, of &agr;-methylstyrene dimer, of limonene, of vinylpyrrolidone, 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 cosmetic 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 diorganosiloxane MM of formula (I) in which n and m are equal to 0 and Z is 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.
Most particularly, the invention is directed towards a cosmetic composition comprising at least one organotrisiloxane containing a phenylalkyl or phenylalkenyl function, of formula (III)
(R
1
)(R
2
)(R
3
)Si—O—Si(R
4
)(Z)—O—Si(R
7
)(R
8
)(R
9
) (III)
in which formula
the symbols R
1
, R
2
, R
3
, R
4
, R
7
, R
8
and R
9
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 phenyl radical linked to the silicone via a linear or branched divalent alkanediyl or alkenediyl group containing 2 or 3 carbon atoms, preferably 2 carbon atoms.
Examples of functionalized polyorganosiloxanes that are most particularly advantageous according to the invention are organotrisiloxanes containing a phenylalkyl or phenylalkenyl function, of formulae (a) to (e) below
Me
3
SiO—(Me)Si(CH
2
—CH
2
—Ph)O—SiMe
3
(a)
Me
3
SiO—(Me)Si[CH(Me)—Ph]O—SiMe
3
(b)
Me
3
SiO—(Me)Si(CH═CH—Ph)O—SiMe
3
(c)
Me
3
SiO—(Me)Si(CH
2
—CH(Me)—Ph)O—SiMe
3
(d)
Me
3
SiO—(Me)Si[CH═C(Me)—Ph]O—SiMe
3
(e)
and diphenyltetramethyldisiloxane of formula PhSi(Me)
2
Ph
The said polyorganosiloxanes of formula (I) or (I′) in which the radical (Z) is other than phenyl can be obtained in a known manner by hydrosilylation between at least one hydrogeno polyorganosiloxane 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 R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
, R
8
, R
9
, n and m have the same meaning as those 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 from about 50° C. to 100° C., preferably from about 50° C. to 80° C., in the presence of 5 to 50 parts by mass of platinum (for example Karstedt catalyst) per million parts by mass of monomers used.
The hydrogenopolyorganosiloxanes preferably used are hydrogenoheptaorganotrisiloxanes MD′M, particularly hydrogenoheptamethyltrisiloxane.
Among the compounds containing vinylic or terminal acetylenic unsaturation which can be used, mention may be made of styrene, &agr;-methylstyrene, &agr;-methylstyrene dimer, limonene, vinylpyrrolidone and acetylene. The said compound is preferably styrene.
One specific embodiment of the first subject of the invention consists of a cosmetic composition comprising phenylmethy
Branlard Paul
Mignani Gerard
Olier Philippe
Willemin Claudie
Chimie Rhodia
Dees Jose'G.
George Konata M.
LandOfFree
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