Method of using an aralkylsiloxane

Details Method of using an aralkylsiloxane Method of using an aralkylsiloxane

1998-11-06

2002-04-02

Page, Thurman K. (Department: 1615)

Drug, bio-affecting and body treating compositions

Live hair or scalp treating compositions

Polymer containing

C424S070100

Reexamination Certificate

active

06365141

ABSTRACT:

FIELD OF THE INVENTION
The invention relates to the use of certain siloxane compounds, more particularly to the use of certain aralkylsiloxane compounds.
BRIEF DESCRIPTION OF THE RELATED ART
The use of phenyltrimethicone in personal care compositions, for example, skin lotions, antiperspirants, hair care products to enhance shine, lubricity and/or visual masking of inorganic components, is known. Typical methods for making phenyltrimethicone, such as for example, by cohydrolysis of phenyltrichlorosilane and chlorotrimethylsilane may introduce impurities, such as for example, side products and catalyst residues, into the phenyltrimethicone product which are undesirable in the context of using the phenyltrimethicone product as a component in a personal care composition.
SUMMARY OF THE INVENTION
In a first aspect, the present invention is directed to a method of using of an aralkylsiloxane, comprising adding the aralkylsiloxane as a component in a personal care composition, in an amount effective to enhance one or more properties of the personal care composition. For example, the aralkylsiloxane enhances the shine, emolliency and lubricity of personal care compositions and aids in visually masking inorganic components of such compositions.
In a second aspect, the present invention is directed to a method for making an aralkyl siloxane, comprising contacting a silylhydride-functional polysiloxane with a terminally unsaturated arylalkene under hydrosilylation conditions. Aralkylsiloxanes made by the preferred process exhibit a low, preferably an undetectably low, level of impurities and thus allow the amount of impurities introduced into the personal care composition by addition of such aralkylsiloxanes to be minimized.
In a third aspect, the present invention is directed to a method for making an improved personal care composition, said personal care composition being an analog of a first personal care composition that contains phenyltrimethicone as a component thereof, comprising making a personal care composition analogous to the first personal care composition wherein an aralkylsiloxane is substituted for the phenyltrimethicone of the first personal care composition.
DETAILED DESCRIPTION OF THE INVENTION
In a preferred embodiment, the personal care composition comprises, based on 100 parts by weight (“pbw”) of the personal care composition, from about 0.5 pbw to about 50 pbw, more preferably from about 1 pbw to about 30 pbw, still more preferably from about 2 pbw to about 20 pbw, of the aralkylalkylsiloxane.
Aralkylsiloxanes that are suitable as the aralkylsiloxane component of the present invention are those comprising one or more compounds according to formula (I):
wherein:
R
1
, R
2
, R
3
, R
4
, R
5
, R
8
and R
9
and R
10
are each independently H, alkyl, more preferably (C
1
-C
6
)alkyl, haloalkyl, more preferably halo(C
1
-C
6
)alkyl, aryl or aralkyl,
R
6
, R
7
are each independently H, alkyl, more preferably (C
1
-C
6
)alkyl, haloalkyl, more preferably halo(C
1
-C
6
)alkyl, or aryl; n and m are each independently integers from 0 to 6, provided that (n+m)≧1, preferably 1≧(n+m)≦8, still more preferably 1≦(n+m)≦4 and provided that at least one substituent group of the compound of formula (I) is aralkyl; or of formula (II):
wherein:
R
11
and R
12
are each independently H, alkyl, more preferably (C
1
-C
6
)alkyl, haloalkyl, more preferably halo(C
1
-C
6
)alkyl, aryl or aralkyl; R
13
and R
14
are each independently H, alkyl, more preferably (C
1
-C
6
)alkyl, haloalkyl, more preferably halo(C
1
-C
6
)alkyl, or aryl; x and y are each independently integers from 0 to 6, provided that 3≦(x+y)≦10, preferably 4≦(x+y)≦6, and provided that at least one substituent group of the compound of formula (II) is aralkyl.
As used herein, the term “(C
1
-C
6
)alkyl” means a linear or branched alkyl group containing from 1 to 6 carbons per group, such as, for example, methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, pentyl, hexyl, preferably methyl.
As used herein, the term “halo(C
1
-C
6
)alkyl” means a linear or branched alkyl group containing from 1 to 6 carbons per group that is substituted with one or more halo substituents, such as, for example, chloromethyl, trifluoromethyl.
As used herein, the term “aryl” means a monovalent unsaturated hydrocarbon ring system containing one or more aromatic rings per group, which may optionally be substituted on the one or more aromatic rings, preferably with one or more groups selected from amino, nitro, (C
1
-C
6
)alkyl, and which, in the case of two or more rings, may be fused rings, including, for example, phenyl, 2,4,6-trimethylphenyl, 2-isopropylmethylphenyl, 1-pentalenyl, naphthyl, anthryl, preferably phenyl.
As used herein, the term “aralkyl” means an aryl derivative of an alkyl group, preferably a (C
2
-C
6
)alkyl group, wherein the alkyl portion of the aryl derivative may, optionally, be interrupted by an oxygen atom, such as, for example, phenylethyl, phenylpropyl, 2-(1-naphthyl)ethyl, preferably phenylpropyl, phenyoxypropyl, biphenyloxypropyl.
In a highly preferred embodiment, the aralkylsiloxane comprises a compound according to formula (I), wherein R
1
and R
10
are each aralkyl, more preferably phenylpropyl, R
2
, R
3
, R
6
, R
7
, R
8
and R
9
are each (C
1
-C
6
) alkyl, more preferably methyl, n is 0 and 2≦m≦5,, more preferably n is 0 and m is 3. In a very highly preferred embodiment, the aralkylsiloxane comprises &agr;,&ohgr;-bis(2-phenylpropyl)siloxane.
In a preferred embodiment, the aralkylsiloxane comprises a compound according to formula (I), wherein R
1
, R
2
, R
3
, R
4
, R
6
, R
7
, R
8
, R
9
and R
10
are each (C
1
-C
6
) alkyl, preferably methyl, R
5
is aralkyl, more preferably phenylpropyl, , n is 1 or 2 and 1≦m≦8, more preferably, n is 1 and m is 2.
In a preferred embodiment, the aralkyl siloxane comprises a compound according to the structural formula (II), wherein R
11
, R
13
and R
14
are each (C
1
-C
6
) alkyl, preferably methyl, R
12
is aralkyl, more preferably phenylpropyl, 1≦×≦4 and 2≦y≦10, more preferably x is 1 and y is 4.
In a highly preferred embodiment, the aralkyl content of the aralklysiloxane is selected to provide a refractive index of from 1.40 to 1.50, more preferably from about 1.44 to 1.48, at 25° C. In a highly preferred embodiment, the aralkylsiloxane comprises, based on the molecular weight of the aralkylsiloxane, from about 25 to about 65 percent by weight (“wt %”), more preferably from about 30 to about 50 wt % and still more preferably from about 33 to about 45 wt %, of one or more aralkyl substituent groups.
Suitable aralkylsiloxane can be made by known methods, see, for example, U.S. Pat. Nos. 3,088,964 and 5,300,669 and 5,384,383, the disclosures of which are each incorporated herein by reference.
In a preferred embodiment, the aralkylsiloxane is made by contacting a silylhydride-functional polysiloxane with an terminally unsaturated arylalkene, such as for example, styrene or 2-phenylpropene, under hydrosilylation conditions, preferably in the presence of a solid hydrosilylation catalyst. In a preferred embodiment, the solid hydrosiliylation catalyst comprises a catalytically active metal, such as for example, platinum, supported on an inert support, such as for example, alumina. Preferably, the aralkylsiloxane product exhibits a hydride content of less than 100 parts per million (“ppm”), based on the weight of aralkylsiloxane. The catalyst and excess arylalkene may be easily removed form the product mixture to yield an aralkylsiloxane having a low to undetectably low content of impurities. In a preferred embodiment, the solid catalyst is removed from the aralkylsiloxane product by filtration. Excess arylalkene may be removed by heating the product mixture by vacuum stripping the aralkylsiloxane.
The personal care applications in which an aralkylalkylsiloxane may be employed include, but are not limited to, deodorants, antiperspirants, skin lotions, moisturizers, hair car

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