Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Silicon containing doai
Reexamination Certificate
2000-07-31
2003-06-10
Padmanabhan, Sreeni (Department: 1617)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Silicon containing doai
C424S401000, C424S078030, C556S443000
Reexamination Certificate
active
06576623
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to a silicone compound having high affinity for various unctuous agents, such as silicone oils, and excellent emulsifying capability, and further to cosmetic materials containing such a silicone compound.
FIELD OF THE INVENTION
In recent years, silicone oils have been used as an unctuous agent mixed in emulsified compositions of water-in-oil type to ensure no greasiness, less tackiness and good water repellency for the emulsified compositions. However, it is still difficult to impart good stability to water-in-oil emulsions containing silicone oils by the use of conventional emulsifiers, such as polyoxyalkylene fatty acid esters.
So the methods of using polyoxyalkylene-modified organopolysiloxanes (polyether-modified silicones) highly compatible with silicone oils as surfactants in water-in-oil emulsions have been proposed in, e.g., JP-A-61-293903, JP-A-61-293904, JP-A-62-187406, JP-A-62-215510 and JP-A-62-216635 (the term “JP-A” as used herein means an “unexamined published Japanese patent application). However, not only silicone oils alone but also mixtures with ester oils and hydrocarbon oils are used in many of emulsions for cosmetics use. In water-in-oil emulsions using those oil mixtures as an unctuous agent, the foregoing polyether-modified silicone surfactants have inferior power of emulsification, so they are difficult to impart satisfactory stability to the emulsions of the aforementioned type.
As a method for solving the foregoing problem, the method of using as an emulsifier an organopolysiloxane having both long-chain alkyl and polyoxyalkylene groups, which is represented by the following formula, is proposed in JP-A-61-90732.
Although the organopolysiloxane compounds represented by the foregoing formula have excellent emulsifying power in systems containing mixed oils rich in ester oil and hydrocarbon oil, they have a drawback of sometimes failing to ensure high stability and no change upon storage for the systems containing mixed oils rich in silicone oils. Therefore, it has been desired to develop emulsifiers suitable for cosmetic materials, namely compounds having excellent capability to emulsify conventional unctuous agents, such as silicone oils, ester oils and hydrocarbon oils, for general cosmetics use to ensure high storage stability of the cosmetic materials.
SUMMARY OF THE INVENTION
A first object of the present invention is to provide a silicone compound having a great capability to emulsify various unctuous agents, including silicone oils, for cosmetics use and ensuring high emulsion stability.
A second object of the invention is to provide a cosmetic material which has high stability in an emulsified state to ensure satisfactory storage stability.
As a result of our intensive studies to attain the aforementioned objects, it has been found that the silicone compounds produced by addition of polyoxyalkylene compounds and silicone compounds to organohydrogenpolysiloxanes have a very strong affinity for silicone oils to ensure a great capability to emulsify them, and so when they are used as emulsifier the resultant emulsions can have very good stability. Further, it has also been found that the silicone compounds produced by addition of long-chain alkyl group-containing organic compounds besides polyoxyalkylene compounds and silicone compounds to organohydrogenpolysiloxanes have a very strong affinity for unctuous agents used in general cosmetic materials, including silicone oils, ester oils and hydrocarbon oils, to ensure a great capability to emulsify them, and so when they are used as emulsifier the resultant emulsions can have very good stability and a high degree of effectiveness for cosmetics use, thereby achieving the present invention.
While such silicone compounds as to be produced by the addition reaction of silicone compounds to organohydrogenpolysiloxanes are disclosed in JP-A-7-197055 as actuation silicone oils having good low temperature characteristics, it is our finding that those silicone compounds are particularly effective as ingredients of cosmetic materials. Further, we have found that, when the aforementioned silicone compounds have relatively low molecular weight, they are instrumental in cleansing not only sebum stains but also makeup stains from cosmetics of the type which are hard to come off, and besides, the cleansing composition comprising them has a very good touch during and after cleansing treatment.
The present invention thus provides a silicone compound represented by the following formula (1), and cosmetic materials containing such a silicone compound:
R
1
a
R
2
b
R
3
c
SiO
(4−a−b−c)/2
(1)
wherein
R
1
groups, which are the same or different, are each an organic group selected from the class consisting of 1-30C alkyl groups, aryl groups, aralkyl groups, fluorinated alkyl groups and organic groups represented by the following formula (2),
—C
m
H
2m
—O—(C
2
H
4
O)
d
(C
3
H
6
O)
e
R
4
(2);
R
2
groups are polyoxyalkylene moiety-containing organic groups represented by the following formula (3),
—C
m
H
2m
—O—(C
2
H
4
O)
f
(C
3
H
6
O)
g
R
5
(3);
R
3
groups are organosiloxane compound residues represented by the following formula (4),
R
4
represents a 4-30C hydrocarbon group or an acyl group represented by R
6
—CO—; R
5
represents a hydrogen atom, a 1-30C hydrocarbon group or an acyl group represented by R
6
—CO—; R
6
represents a 1-30C hydrocarbon group; a, b and c are values in the ranges 1.0≦a≦2.5, 0.001≦b≦1.5 and 0.001≦c≦1.5; d and e are each an integer of from 0 to 50; f is an integer of from 2 to 200 and g is an integer of from 0 to 200, provided that the sum of f and g is an integer of from 3 to 200; m is an integer of from 0 to 15; h is an integer of from 0 to 500; and n is an integer of from 1 to 5.
DETAILED DESCRIPTION OF THE INVENTION
R
1
groups in formula (1) may be the same or different, and each of them represents a 1-30C alkyl group, an aryl group, an aralkyl group, a fluorinated alkyl group or an organic group represented by formula (2). Examples of an alkyl group represented by R
1
include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl octyl, nonyl, decyl, cyclopentyl and cyclohexyl groups; those of an aryl group include phenyl and tolyl groups; those of an aralkyl group include benzyl and phenetyl groups; and those of a fluorinated alkyl group include trifluoropropyl and heptadecafluorodecyl groups.
The organic group —C
m
H
2m
—O—(C
2
H
4
O)
d
(C
3
H
6
O)
e
R
4
(formula (2)), represented by R
1
includes an alkoxy group, an acyloxy group, an alkenyl ether residue and an alkenyl ester residue. Additionally, R
4
in formula (2) represents a monovalent 4-30C hydrocarbon group or an acyl group of formula R
6
CO— (wherein R
6
is a 1-30C hydrocarbon group), d and e in formula (2) are each an integer of from 0 to 50, and m in formula (2) is an integer of from 0 to 15.
More specifically, when m, d and e are all zero, the formula (2) represents a 4-30 C alkoxy group including from lower alkoxy groups, such as butoxy and pentoxy, to higher alkoxy groups such as oleyloxy and stearoxy, or an acyloxy group such as a residue of acetic, lactic, butyric, oleic, stearic or behenic acid.
When m is not zero but d and e are zero, m is preferably 3, 5 or 11. In such a case, R
1
represents a 1- or 2-propenyl ether residue, a pentenyl ether residue, or an undecenyl ether residue. When R
4
is a hydrdocarbon group, such an ether residue is, e.g., an allyl stearyl ether residue, a pentenyl behenyl ether residue or an undecenyl oleyl ether residue. When d or e is not zero, the formula (2) assumes such a form that polyoxyalkylene is cut in an ether or ester linkage.
When m is 0, irrespective of the values of d and e, R
1
of formula (2) tends to have inferior resistance to hydrolysis; while, when m is greater than 15, the resultant silicone compound has a strong oily smell. It is therefore advantageous for m to be from 3 to 11.
For the present silicone compound, it is desirable that at lea
Nakanishi Tetsuo
Ono Ichiro
Millen White Zelano & Branigan P.C.
Padmanabhan Sreeni
Shin-Etsu Chemical Co. , Ltd.
Wells Lauren Q.
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