Copolymer for cosmetics

Details Copolymer for cosmetics Copolymer for cosmetics

1999-12-03

2002-12-31

Hartley, Michael G. (Department: 1617)

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Cosmetic, antiperspirant, dentifrice

C424S070100

Reexamination Certificate

active

06500439

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a copolymer for cosmetics, which copolymer can be easily incorporated in cosmetics and is excellent in water resistance, water- and oil-repellency, feeling when used, and safety, and also to a cosmetic containing said copolymer. The copolymer for cosmetics acts as a film forming agent for cosmetics, a compatibilizer or an emulsifier between a fluorine-containing raw material and a fluorine-free raw material, and a surface treatment agent for fluorine-containing compound-treated powder and silicone-treated powder.
DESCRIPTION OF RELATED ART
Heretofore, a hydrocarbon-based emulsion resin has been generally used as a film forming agent for cosmetics. The purpose of incorporating the film forming agent is to form a film after the application of a cosmetic so that the pigment and other effective ingredients are held on the skin for a long period of time. However, the water resistance and water- and oil-repellency of the conventional film forming agents are so insufficient that the film is destroyed by water coming into contact the film or by sweat or skin fat secreted from the skin. Recently, an acryl-silicone copolymer is used as a copolymer which overcame the drawback, i.e., insufficient water resistance and water-repellency, of the hydrocarbon-based emulsion resin (Japanese Patent Kokai Publication (JP-A) No. 247,110/1990). The acryl-silicone copolymer is a copolymer comprising a hydrocarbon-based acrylate and a silicone macromonomer and the film thereof has excellent water resistance and water-repellency.
However, since the acryl-silicone copolymer also has almost no water-repellency, a messy makeup caused by skin fat cannot be prevented. There has been known a technology in which a copolymer between an alkyl (meth)acrylate having a long-chain alkyl group of 8 or more carbon atoms and a polyfluoroalkyl (meth)acrylate having an polyfluoroalkyl group of 4 or more carbon atoms is contained as a film forming agent so as to impart oil repellency (Japanese Patent Kokoku Publication (JP-B) No. 46,444/1991). This copolymer is associated with a drawback that no film is formed from an emulsion containing the copolymer dispersed in water because the softening point of the copolymer is higher than skin temperature. On the other hand, if the molecular weight of the copolymer is lowered to a point which makes the copolymer soluble in a solvent so that a film can be formed from the solution, the copolymer does not exhibit oil repellency.
Meanwhile, as a recent trend, a fluorine-containing raw material, such as fluorine-containing compound-treated powder and perfluoropolyether, is incorporated into cosmetics. Since the affinity of these fluorine-containing raw materials for a conventionally employed fluorine-free raw material such as a hydrocarbon-based raw material or a silicone-based raw material is so poor that it is very difficult to incorporate the above-described fluorine-containing raw material in a cosmetic in a stable manner. Therefore, there is a need for the development of a compatibilizer capable of enhancing the affinity between the fluorine-containing raw material and the fluorine-free raw material.
SUMMARY OF THE INVENTION
After extensive studies to overcome the foregoing problems, the present inventors have found that a copolymer, which is a fluorine-containing (meth)acrylate copolymer having specific ingredients and soluble or dispersible in water or a solvent, has excellent characteristics as a copolymer for cosmetics. More specifically, the copolymer for cosmetics can be easily incorporated in conventional cosmetics and, when applied to a skin, the cosmetic incorporated with the copolymer forms a film excellent in water resistance, water- and oil-repellency, feeling when used, and safety.
Further, the copolymer for cosmetics acts as a compatibilizer between a fluorine-containing raw material and a fluorine-free raw material. In this way, the copolymer is effective in stabilizing the cosmetics.
The present invention provides a copolymer for cosmetics, said copolymer comprising
(A) 5 to 95% by weight of the repeating units derived from a fluorine-containing (meth)acrylate, and
(B) 95 to 5% by weight of the repeating units derived from at least one fluorine-free monomer selected from the group consisting of a silicone macromonomer, a polyalkylene glycol (meth)acrylate, an alkyl (meth)acrylate macromonomer, and an alkyl (meth)acrylate,
wherein the copolymer comprises:
(i) a fluorine-containing (meth)acrylate and a silicone macromonomer,
(ii) a fluorine-containing (meth)acrylate and a polyalkylene glycol (meth)acrylate,
(iii) a fluorine-containing (meth)acrylate and an alkyl (meth)acrylate macromonomer,
(iv) a fluorine-containing (meth)acrylate and a C
1-4
alkyl-containing alkyl (meth)acrylate,
(v) a fluorine-containing (meth)acrylate, a silicone macromonomer, and a C
1-22
alkyl-containing alkyl (meth)acrylate, or
(vi) a fluorine-containing (meth)acrylate, a silicone macromonomer, and an alkyl (meth)acrylate macromonomer.
The fluorine-containing (meth)acrylate to be used in the copolymer for cosmetics may have the following structural formula:
wherein Rf is a polyfluoroalkyl group having 6 to 16 carbon atoms or a perfluoropolyether group; and A is an alkylene group having 1 to 4 carbon atoms,
(wherein R
1
is an alkyl group having 1 to 4 carbon atoms and R
2
is an alkylene group having 1 to 4 carbon atoms), or
X is a hydrogen atom or a methyl group.
Further, the fluorine-containing (meth)acrylate may be, for example, a fluorine-containing (meth)acrylate macromonomer having the following structural formula:
wherein Rf is a polyfluoroalkyl group having 6 to 16 carbon atoms or a perfluoropolyether group; A
1
is an alkylene group having 1 to 4 carbon atoms,
(wherein R
1
is an alkyl group having 1 to 4 carbon atoms and R
2
is an alkylene group having 1 to 4 carbon atoms), or
X
11
is a hydrogen atom or a methyl group; Y
11
is a hydrogen atom or a methyl group; and m is 5 to 100.
Specific examples of the perfluoropolyether group include the following.
F(CF(CF
3
)CF
2
O)
n
CF
2
CF
2
— (wherein n is an integer of 3 to 30),
CF
3
O(CF(CF
3
)CF
2
O)
n
(CF
2
O)
m
CF
2
— (wherein n is an integer of 2 to 30 and m is an integer of 3 to 70),
CF
3
O(CF
2
CF
2
O)
n
(CF
2
O)
m
CF
2
— (wherein n is an integer of 2 to 40 and m is an integer of 4 to 70), and
F(CF
2
CF
2
CF
2
O)
n
CF
2
CF
2
— (wherein n is an integer of 3 to 30).
It is preferable that the number average molecular weight (as measured by
19
F-NMR) of the perfluoropolyether group is in the range of from 500 to 5,000.
Specific examples of the fluorine-containing (meth)acrylate include the following.
CF
3
(CF
2
)
7
(CH
2
)OCOCH═CH
2
,
CF
3
(CF
2
)
6
(CH
2
)OCOC(CH
3
)═CH
2
,
(CF
3
)
2
CF(CF
2
)
6
(CH
2
)
2
OCOCH═CH
2
,
CF
3
(CF
2
)
7
(CH
2
)
2
OCOC(CH
3
)═CH
2
,
CF
3
(CF
2
)
7
(CH
2
)
2
OCOCH═CH
2
,
HCF
2
(CF
2
)
7
(CH
2
)
2
OCOCH═CH
2
,
CF
3
(CF
2
)
5
(CH
2
)
2
OCOCH═CH
2
,
CF
3
(CF
2
)
7
SO
2
N(CH
3
)(CH)
2
OCOCH═CH
2
,
CF
3
(CF
2
)
7
SO
2
N(C
2
H
5
)(CH
2
)
2
OCOC(CH
3
)═CH
2
,
(CF
3
)
2
CF(CF
2
)
6
CH
2
CH(OCOCH
3
)CH
2
OCOC(CH
3
)═CH
2
,
(CF
3
)
2
CF(CF
2
)
6
CH
2
CH(OH)CH
2
OCOCH═CH
2
,
F(CF(CF
3
)CF
2
O)
10
CF
2
CF
2
—COOCH
2
CH
2
CH═CH
2
,
These fluorine-containing (meth)acrylates may be used in a combination of two or more of them.
In the present invention, the fluorine-free monomer which is used in the radical polymerization with the fluorine-containing (meth)acrylate is classified into four types, namely, a silicone macromonomer, a polyalkylene glycol (meth)acrylate, an alkyl (meth)acrylate macromonomer, and an alkyl (meth)acrylate.
The silicone macromonomer has a structural formula such as the following formula:
wherein Me is a methyl group and R
1
is a methyl group or a hydrogen atom; R
2
is a divalent saturated hydrocarbon group having 1 to 10 carbon atoms which has a straight or branched carbon chain and which may be disjoined by one or two ether linkages in some cases; R
3
is an alkyl group

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