JP3474932B2 - Fluorine-modified silicone, method for producing the same, and cosmetic containing the same - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a fluorine-modified siloxa.
Emissions relates cosmetics containing methods and this manufacturing, more particularly excellent novel fluorine-modified siloxanes having a repellent, good cosmetics of makeup and feeling contains methods and this manufacturing About.

[0002]

2. Description of the Related Art Conventionally, various water-repellent cosmetics have been used for the purpose of protecting the skin from water and sweat and for preventing the makeup from being damaged by water and sweat. For example, skin protection cosmetics such as skin creams and skin lotions and makeup cosmetics contain a silicone oil or silicone resin as a water repellent component. However, these silicone oils and silicone resins have a certain effect on water repellency, but do not have a sufficient effect on oil repellency. Therefore, there is a problem that cosmetics containing these components cause makeup loss due to sebum.

[0003] For this reason, various attempts have been made to develop compounds having both water repellency and oil repellency.
For example, JP-A-2-295912 discloses that a cosmetic containing a fluorine-modified silicone compound such as trifluoropropyl silicone is excellent in water resistance and sebum resistance.

By the way, the water-repellent and oil-repellent base used in cosmetics has (a) sufficient water and oil repellency against sweat and sebum, (b) excellent emulsion stability, C) It is necessary to satisfy all the conditions such as being strong against mechanical contact (for example, when held down with a handkerchief, a tissue, etc.), making it difficult to remove makeup, and (d) having a low viscosity and a good feeling upon use.

[0005]

However, the above-mentioned fluorine-modified silicone compound still does not sufficiently satisfy these conditions, and has poor emulsification stability due to poor compatibility with general cosmetic bases. Poor skin affinity and poor contact with the skin (for example, when held down with a handkerchief, tissue, etc.), and the viscosity is high, causing problems such as poor spread during application.

Accordingly, while being excellent in water repellency and oil repellency,
It has been desired to develop a compound that is stable even when incorporated into a cosmetic and gives a good feeling of use without causing makeup collapse.

[0007]

Means for Solving the Problems The present inventors have made intensive studies in view of the above circumstances and found that a fluorine-modified siloxane having a specific branched perfluoroalkyl group described later has excellent water and oil repellency, The present inventors have found that they have good familiarity with the skin and show good compatibility with cosmetics, and have completed the present invention.

That is, the present invention provides at least one compound represented by the general formula (1)

[0009]

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Wherein R ¹ represents a linear or branched aliphatic hydrocarbon group having 1 to 20 carbon atoms or an alicyclic or aromatic hydrocarbon group having 5 to 10 carbon atoms; [An integer of 10 is shown.] The fluorine-modified siloxane (A) having a degree of polymerization of 1 to 400 and having a siloxane unit represented by the formula:

Further, the present invention provides a cosmetic containing the fluorine-modified siloxane (A).

The fluorine-modified siloxane (A) of the present invention comprises:
The degree of polymerization (number of siloxane units) is 1 to 400,
It is a compound containing at least one fluorine-modified siloxane unit of the above general formula (1), more preferably 1 to 200
Siloxane unit represented by the following general formula (2):
It has about 200 pieces.

[0013]

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[Wherein, R ² and R ³ may be the same or different and each is a linear or branched aliphatic hydrocarbon group having 1 to 20 carbon atoms or an alicyclic or aromatic group having 5 to 10 carbon atoms. Represents a group hydrocarbon group)

The hydrocarbon groups represented by R ¹ , R ² and R ³ in the fluorine-modified siloxane (A) of the present invention include, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl Linear alkyl groups such as isopropyl, sec-butyl, t
tert-butyl, neopentyl, 1-ethylpropyl,
Branched alkyl groups such as 2-ethylhexyl; cyclic alkyl groups such as cyclopentyl and cyclohexyl; phenyl;
And aromatic hydrocarbon groups such as naphthyl.

The number (p) of the fluorine-modified siloxane unit (1) of the fluorine-modified siloxane (A) of the present invention is 1 to
200, particularly preferably 1 to 50, and the number (q) of the siloxane unit (2) is 0 to 200, particularly 0 to 50,
Further, 2 to 50 is preferable. Further, the constitutional ratio p / q of these structural units is preferably in the range of 4/1 to 1/4. Furthermore, of the fluorine-modified siloxane (A), the side-chain type modified silo in which the fluorine-modified siloxane unit (1) is in the chain.
Xane is preferred.

The preferred fluorine-modified siloxane is represented by the following formula (A ').

[0018]

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Wherein p ′ is an integer of 0 to 200;
When p 'is an integer of 1 to 200, R ^{4 to} R ⁹ may be the same or different, and may be a linear or branched aliphatic hydrocarbon group having 1 to 20 carbon atoms or an aliphatic hydrocarbon group having 5 to 10 carbon atoms. A cyclic or aromatic hydrocarbon group, and when p ′ is 0, R ⁴
At least one of R ⁹ is a group-(CH ₂ ) _{m + 2} -C (CF ₃ ) ₂ (C ₃ F ₇ )
And the remainder is a linear or branched aliphatic hydrocarbon group having 1 to 20 carbon atoms or an alicyclic or aromatic hydrocarbon group having 5 to 10 carbon atoms. R ¹ , R ² , R ³ , m and q
Is the same as above)

Among them, the following formulas (A'-1) to
(A'-3) is preferred, and (A'-3) is particularly preferred.

[0021]

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[Wherein m, p and q are the same as above]

The fluorine-modified siloxane (A) of the present invention comprises
For example, at least one general formula (3)

[0024]

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[0025] [In the formula, R ¹ is as defined above] and the general formula siloxane polymerization degree 1 to 400 having a siloxane unit represented by (B) (4)

[0026]

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Wherein m represents an integer of 0 to 10; and a perfluoroalkyl compound represented by the following formula:

As long as the siloxane (B) contains at least one siloxane unit (3), the molecular structure is not particularly limited, and various known siloxane units can be used. Specific examples of the siloxane (B) include:
Single-ended methylhydrogenpolysiloxane such as pentamethyldisiloxane and tridecamethylhexasiloxane, double-ended methylhydrogenpolysiloxane such as tetramethyldisiloxane, hexamethyltrisiloxane, octamethyltetrasiloxane and dodecamethylhexasiloxane And commercially available methyl hydrogen polysiloxane, for example, “TSF48” manufactured by Toshiba Silicone Co., Ltd.
4, "TSF483", Shin-Etsu Chemical Co., Ltd. "K
F99 "and the like.

The compound represented by the general formula (4) is described, for example, in W.S. Dmowski and Wozniakki,
J. Fluorine Chem. , 36 (1987)
385 can be produced by the following method.

[0030]

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Wherein M is an alkali metal, X is Cl,
Represents a halogen atom such as Br or I, and m is the same as described above.

That is, hexafluoropropene (5)
The compound (4) can be obtained by reacting the dimer (6) with a halogenated alkene (7). The halogenated alkene (7) has m of 0 in terms of reactivity and economy.
And X is preferably Br or I. Specific examples thereof include vinyl halide, allyl halide, halogenated butene, halogenated hexene, halogenated octene,
Halogenated decene, halogenated dodecene and the like can be mentioned. In this reaction, the compound represented by the general formula (7) is used in an amount of 1 molar equivalent or more, preferably 1.0 to 1.5 molar equivalents, relative to the compound represented by the general formula (6).
This reaction is carried out by heating and stirring in a temperature range of 0 to 200 ° C, preferably 10 to 100 ° C, using a solvent as necessary.

The compound thus obtained with (4)
The reaction with loxane (B) is performed in the presence of a catalyst. Examples of the catalyst used include those generally used for hydrosilylation, for example, free radical initiators; complex compounds of metals such as ruthenium, rhodium, palladium, osmium, iridium, and platinum; and those supported on silica gel or alumina. Is mentioned. Among these, chloroplatinic acid, Speyer reagent (isopropyl alcohol solution of chloroplatinic acid) and the like are particularly preferable. The amount of catalyst used may be an amount sufficient to promote reaction of the compound with a siloxane (B) (4), is not particularly limited, Compound (4) 10 ^-6 to 10 per 1 mol ^- A range of ¹ mole is preferred.

In this reaction, the use of a reaction solvent is not essential, but the reaction may be carried out in a suitable solvent if necessary. The reaction solvent is not particularly limited as long as it does not inhibit the reaction. Examples thereof include hydrocarbon solvents such as pentane, hexane, and cyclohexane; benzene solvents such as benzene, toluene, and xylene; diethyl ether;
Preferred are ether solvents such as diisopropyl ether; alcohol solvents such as methanol, ethanol, isopropyl alcohol and butanol.

The hydrosilylation proceeds at 0 to 200 ° C., and takes into account the reaction speed and the coloration of the product.
It is preferably performed at 0 ° C. The reaction time is 0.5 to 2
It is preferably about 4 hours.

The fluorine-modified product obtained by the above reaction
In order to control various properties of the siloxane (A) such as viscosity, solubility, and emulsion stability, the combination of the types and amounts of the siloxane (B) and the compound (4) may be appropriately changed.

The thus obtained fluorine-modified siloxane (A) of the present invention is excellent in water repellency and oil repellency and can control various properties such as viscosity depending on the purpose. When used as, it can be made to have a long-lasting makeup and excellent feeling in use. In this case, the blending amount of the fluorine-modified siloxane (A) is not particularly limited, but is usually 0.001 to 90% by weight (hereinafter, simply shown as “%”), preferably 0.01 to 80%. It is particularly preferably 0.1 to 70%, more preferably 3 to 30%.

The cosmetics of the present invention containing the fluorine-modified siloxane (A) can further use oils commonly used in cosmetics. Examples of such oils include cyclic silicones such as octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and dodecamethylcyclohexasiloxane; non-volatile silicones such as methylpolysiloxane, dimethylpolysiloxane, and methylphenylpolysiloxane; squalane and palm oil Animal and plant fats and oils; and other hydrocarbons, higher fatty acid esters, liquid paraffin, iso-liquid paraffin and the like.

Further, the cosmetics of the present invention may contain, if necessary, components to be added to ordinary cosmetics, for example, petrolatum, lanolin, ceresin, microcrystalline wax, carnauba wax, candelilla wax, higher fatty acids, higher alcohols, etc. Water-soluble and oil-soluble polymers; coloring agents such as inorganic and organic pigments, inorganic and organic pigments and organic dyes treated with silicone or fluorine compounds; anionic activators, cationic activators, Ionic activators,
Surfactants such as dimethylpolysiloxane / polyoxyalkylene copolymer and polyether-modified silicone; other water, preservatives, antioxidants, dyes, thickeners, pH adjusters,
A fragrance, an ultraviolet absorber, a humectant, a blood circulation promoter, a cooling agent, an antiperspirant, a bactericide, a skin activator, and the like can be appropriately compounded as long as the effects of the present invention are not impaired. In particular, when a pigment surface-treated with a fluorine compound is used, it is preferable because makeup is not lost due to sebum.

The cosmetic of the present invention is not particularly limited in the form and type of the cosmetic, and can be produced according to a usual method. Examples of the type include oil-based cosmetics, emulsified cosmetics, aqueous cosmetics, lipsticks, blushers, foundations, skin cleansers, hair cleansers, hair tonics, hair styling, hair tonics, hair restorers, and the like.

[0041]

The fluorine-modified siloxane of the present invention (A)
Has (1) high water and oil repellency, (2) good compatibility with cosmetic bases, (3) high emulsification stability, and (4)
It has excellent characteristics such as low viscosity and non-stickiness, (5) high skin affinity and difficulty in removing, and (6) extremely low skin irritation. Cosmetics containing this siloxane (A) have long lasting It has an excellent effect of being good and having a good feeling of use.

[0042]

EXAMPLES The present invention will be specifically described below with reference to examples and test examples, but the present invention is not limited to these examples. In the following examples, some of the chemical formulas are abbreviated as follows.

[0043]

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Embodiment 1

[0045]

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100 with stirrer, reflux and thermometer
ml four-necked flask, under a nitrogen atmosphere, methylhydrogenpolysiloxane _{^{(H MD 4 M H) 12.0g}} (27.
8 mmol), H ₂ C = CHCH ₂ C (CF ₃ ) ₂ (C ₃ F ₇ ) (hereinafter, compound (4
24.1 g (66.8 mmol) were charged. Then, after the temperature in the flask was raised to 80 ° C., 11% of a 2% isopropyl alcohol solution of chloroplatinic acid was added.
l (3.3 × 10 ⁻³ mmol) was added and stirred for 5 hours. The reaction mixture was cooled to room temperature, 50 ml of hexane and 1.1 g of activated carbon were added, and the mixture was stirred at room temperature for 1 hour. The activated carbon was filtered off and the solvent was distilled off. The unreacted compound (4a) was distilled off under reduced pressure to obtain 30.3 g of the target compound (1a) as a colorless and transparent oil (yield: 95%).

The following ¹ H-NMR [δ ppm, in CDCl ₃ , CHCl
₃ standards (7.24 ppm)]. δ: 0.00 to 0.05 (m, 36H, -SiC H ₃ ), 0.48 to 0.56 (m, 4H, a),
1.53 to 1.61 (m, 4H, b), 2.08 to 2.19 (m, 4H, c) The above Ha to Hc indicate protons at the following positions.

[0048]

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Embodiment 2

[0050]

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In the apparatus used in Example 1, 25.0 g of methyl hydrogen polysiloxane (MD ₂ ^DH ₂ M) (5
8.0 mmol), 50.1 g of compound (4a) (139.2)
mmol). Then, the temperature in the flask was raised to 80 ° C., and 230.0 μl (7.0 × 10 ⁻³ mmol) of a 2% chloroplatinic acid solution in isopropyl alcohol was added, followed by stirring for 5 hours. By the same method as in Example 1, 58.3 g of the target compound (1b) was obtained as a colorless and transparent oil (yield: 87%).

The following ¹ H-NMR [δ ppm, in CDCl ₃ , CHCl
₃ standards (7.24 ppm)]. δ: -0.01~0.06 (m, 36H, -SiC H 3), 0.45~0.54 (m, 4H, a),
1.50 to 1.73 (m, 4H, b), 2.09 to 2.22 (m, 4H, c) The above Ha to Hc indicate protons at the following positions.

[0053]

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Embodiment 3

[0055]

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In the apparatus used in Example 1, 20.0 g of methyl hydrogen polysiloxane (MD ₈ ^DH ₄ M) (20.0 g) was added.
0.1 mmol), 34.7 g (96.6 mm) of compound (4a)
ol). Then, the temperature in the flask was raised to 80 ° C., and 470 μl (14.5 × 10 ⁻³ mmol) of a 2% chloroplatinic acid solution in isopropyl alcohol was added, followed by stirring for 5 hours. The target compound (1) was prepared in the same manner as in Example 1.
c) 45.7 g were obtained as a colorless and transparent oil (yield 9).
3%).

The following ¹ H-NMR [δppm, in CDCl ₃ , CHCl
₃ standards (7.24 ppm)]. δ: 0.00 to 0.03 (m, 78H, -SiC H ₃ ), 0.44 to 0.53 (m, 8H, a),
1.50 to 1.66 (m, 8H, b), 2.08 to 2.14 (m, 8H, c) The above Ha to Hc indicate protons at the following positions.

[0058]

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Embodiment 4

[0060]

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In the apparatus used in Example 1, 29.5 g of methyl hydrogen polysiloxane (MD ₁₂ ^DH ₄ M) (2
2.8 mmol), 39.4 g of compound (4a) (109.5)
mmol). Then, the temperature in the flask was raised to 80 ° C., and 181 μl (5.5 × 10 ⁻³ mmol) of a 2% chloroplatinic acid solution in isopropyl alcohol was added, followed by stirring for 5 hours. The target compound (1) was prepared in the same manner as in Example 1.
d) 56.0 g was obtained as a colorless and transparent oil (yield 9).
0%).

The following ¹ H-NMR [δ ppm, in CDCl ₃ , CHCl
₃ standards (7.24 ppm)]. δ: -0.01~0.02 (m, 102H, -SiC H 3), 0.44~0.54 (m, 8H,
a), 1.51 to 1.68 (m, 8H, b), 2.08 to 2.15 (m, 8H, c) The above Ha to Hc indicate protons at the following positions.

[0063]

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Test Example 1 The compounds of Examples 1 to 3 and Comparative Examples 1 to 3 shown below were measured for water resistance, oil resistance, silicone compatibility, and difficulty in peeling from the skin when used as a cosmetic. Table 1 shows the results. [Water resistance] The contact angle with water (the angle between the oil film of each oil agent and the water droplet) was 100 ° or more, and を was 70 to less than 100 °. [Oil resistance] The contact angle with squalane (the angle between the oil film of each oil agent and the squalane droplet) was rated as ◎ when the contact angle was 50 ° or more, ○ when the contact angle was less than 40 to 50 °, and × when the contact angle was less than 40 °. [Silicon compatibility] The solubility in octamethylcyclotetrasiloxane was examined. [Difficulty to remove from skin when used in cosmetics] Black iron oxide 1
g and 1 g of a sample were uniformly kneaded to prepare a paste, and the paste was uniformly and thinly applied to the center of the male forehead, and after 4 hours, the portion coated with tissue paper was 200 g weight / cm ² . Hold down with pressure. The difficulty in removing the cosmetic was evaluated by the degree to which the tissue paper was colored by the black iron oxide transferred to the tissue paper. The evaluation criteria were ◎ for little coloring, ○ for slightly colored, Δ for colored, and x for fairly colored.

[0065]

[Table 1]

As is clear from the results shown in Table 1, the fluorine-modified siloxane of the present invention is superior in water and oil repellency, generally has low viscosity, and has good compatibility with the cosmetic base as compared with the conventional product. It can be seen that when the composition is used as a cosmetic, it is excellent in difficulty in removing from the skin.

Production Example 1 Production of Fluorine Compound Treated Sericite Sericite 1 was placed in a 1-liter round bottom flask (or kneader).
After adding 500 g of ion-exchanged water, 500 ml of ion-exchanged water was added thereto, and a perfluoroalkyl phosphate dioxyethylamine salt [(C _m F _{2m + 1} C ₂ H ₄ O) _y PO (ONH ₂ (CH ₂ CH ₂ OH) ) ₂ ) _3-y ]
[M = 6 to 18 (average chain length; 9), about 1 of 1 <y <2]
33 g of a 7.5% aqueous solution was added, and the mixture was stirred at 40 ° C. Next, 40 ml of 1N hydrochloric acid was added to lower the pH of the aqueous solution to 3 or less, and perfluoroalkylphosphoric acid was precipitated on the powder surface. This was filtered, washed with water and dried to obtain 105 g of the target fluorine compound-treated sericite. I got

Examples 5 to 7 and Comparative Examples 4 to 6 Two-layer liquid foundations: Two-layer liquid foundations having the compositions shown in Table 2 were produced according to the following production methods, respectively. It was evaluated by the following evaluation method. Table 3 shows the results. (Preparation method) After the oil phase is dissolved at room temperature, the pigment is dispersed with a disper. The aqueous phase is added to this with stirring and emulsified to obtain the desired two-phase liquid foundation.

[0069]

[Table 2]

(Evaluation Method) Make-up, persistence of foundation and feeling of use: Sensory evaluation was conducted by 10 expert panelists, and evaluated according to the following criteria. Table 3 shows the results. ○: “Good” is 8 or more. Δ: “Good” is 4 to 7 people. ×: “Good” is less than 4 people.

[0071]

[Table 3]

As is evident from Table 3, the liquid foundation of the present invention was more durable and more comfortable to use than the conventional one containing silicone.

Example 8 Powder foundation: A powder foundation having the composition shown in Table 4 was produced by the following method. (Preparation method) The pigment is mixed and pulverized through a pulverizer. This is transferred to a high-speed blender, and a binder and the like are mixed by heating, and the resulting mixture is added to the pigment and further mixed to make the mixture uniform. This is treated with a crusher, passed through a sieve, and after adjusting the particle size,
After leaving it for several days, it is compression molded in a container such as a gold plate to obtain a powder foundation.

[0074]

(Composition) (% by weight) (1) Fluorine compound-treated pigment (the following pigment is treated in the same manner as in Production Example 1) Titanium oxide 10.0 Sericite 30.0 Mica Balance Kaolin 5.0 Bengala 8 Yellow iron oxide 2.5 Black iron oxide 0.1 (2) Fluorine-modified siloxane of Example 1 8.0 (3) Beeswax 2.0 (4) Preservative 0.2 (5) Fragrance trace amount

Example 9 Blush: Blush having the composition shown in Table 5 was obtained in the same manner as in Example 8.

[0076]

(Composition) (% by weight) (1) Silicone-treated pigment (commercially available pigment treated with methyl hydrogen polysiloxane) Kaolin Balance Mica 13.0 Titanium oxide 12.0 Red No. 202 2.5 Iron oxide (Red, (Yellow, black) 5.0 (2) Fluorine-modified siloxane of Example 2 7.0 (3) Dimethylpolysiloxane ("KF96A", 6cs, manufactured by Shin-Etsu Chemical Co., Ltd.) 5.0 (4) Preservative 1 (5) Fragrance trace

Example 10 Powder Eye Shadow: Table 6
Was obtained by the following production method. (Production method) A pigment other than mica titanium is first mixed and pulverized, and then the mica titanium is mixed. Otherwise, the procedure of Example 8 is repeated to obtain the desired powder eye shadow.

[0078]

(Table 6) (Composition) (% by weight) (1) Water- and oil-repellent powder (the powder treated in the same manner as in Production Example 1 is later mixed) Titanium mica 4.9 Sericite Balance Mica 25.0 Oxidation Iron (red, yellow, black) 2.0 Ultramarine 9.0 Navy blue 12.0 (2) Fluorine-modified siloxane of Example 3 8.0 (3) Squalane 2.0 (4) Vaseline 1.5 (5) Sorbitan Trioleate 1.0 (6) Preservative 0.1 (7) Fragrance trace

Example 11 Dual-Use Powder Foundation: A dual-use powder foundation having the composition shown in Table 7 was obtained by the same method as in Example 10.

[0080]

(Composition) (% by weight) (1) Silicone-treated pigment (commercially available pigment treated with methyl hydrogen polysiloxane) Mica Balance Talc 4.8 Titanium oxide 14.0 Titanium mica 3.5 Iron oxide (red, yellow) , Black) 8.2 Zinc oxide 4.5 Aluminum oxide 10.0 Barium sulfate 5.0 (2) Fluorine-modified siloxane 6.0 of Example 1 (3) Lanolin 3.0 (4) Vaseline 1.0 (5 ) Isopropyl myristate 1.0 (6) Preservative 1.5 (7) Fragrance trace

Example 12 Two-layer sunscreen emulsion:
Example 5 A two-layer sunscreen emulsion having the composition shown in Table 8 was prepared.
To 7 were obtained by the same production method.

[0082]

(Composition) (% by weight) (1) Octamethylcyclotetrasiloxane 25.0 (2) Fluorine-modified siloxane 15.0 of Example 2 (3) Dimethylpolysiloxane / polyoxyalkylene copolymer 0 (4) Glycerin 2.0 (5) Ethanol 12.0 (6) Purified water balance (7) Octyl methoxycinnamate 2.0 (8) Silicone-treated pigment (commercially available pigment treated with methyl hydrogen polysiloxane) Zinc oxide 5.5 Titanium oxide 2.0 Talc 5.0 (9) Fragrance trace

Example 13 Nutritional cream: A nutritional cream having the composition shown in Table 9 was obtained by the following method. (Production method) (1) to (5) were mixed and heated to 75 ° C.
(6), (7) and (10) are mixed into this mixture,
The mixture heated to 70 ° C. is added under stirring to emulsify. After the emulsification, the mixture is cooled to 60 ° C., (8) and (9) are added thereto, and further cooled to room temperature to obtain a nutritional cream.

[0084]

(Composition) (% by weight) (1) Polyoxyethylene (50) hydrogenated castor oil 2.0 (2) Potassium sulfate 0.5 (3) Fluorine-modified siloxane of Example 3 6.0 (4) Liquid paraffin 5.0 (5) hexadecyl-2-ethylhexanoate 2.0 (6) sodium benzoate 0.3 (7) propylene glycol 2.0 (8) acetic acid-d1-α-tocopherol 0.1 ( 9) Fragrance 0.1 (10) Purified water balance

Example 14 Hand cream A hand cream having the composition shown in Table 10 was obtained by the following method. (Preparation method) (1) to (5) are mixed and heated to 75 ° C.
The mixture of (6) to (8) heated to 75 ° C. is gradually added thereto under stirring to emulsify. Cool to room temperature to obtain a hand cream.

[0086]

(Table 10) (Composition) (% by weight) (1) Polyoxyethylene (20) Sorbitan palmitate 1.5 (2) Aluminum chloride 0.8 (3) Isopropyl myristate 4.5 (4) Dimethylpolysiloxane ( (KF-96A, 6cs, manufactured by Shin-Etsu Chemical Co., Ltd.) 4.0 (5) Fluorine-modified siloxane 6.0 of Example 1 (6) Methyl parahydroxybenzoate 0.2 (7) Sorbitol 10.0 (8) ) Purified water balance

Example 15 Cream foundation (water-in-oil type) A cream foundation having the composition shown in Table 11 was obtained by the following method. (Preparation method) (1) to (6) are mixed and heated to 75 ° C.
(7) is dispersed by a disper. The mixture of (9) to (14) is heated to 75 ° C. and gradually added under stirring to emulsify. Then cooled to 30 ° C (8)
And (15), and further cooled to room temperature to obtain the desired creamy foundation (W / O type).

[0088]

(Composition) (% by weight) (1) Dimethylpolysiloxane / polyoxyalkylene copolymer 2.0 (2) Fluorine-modified siloxane of Example 2 10.0 (3) Dimethylpolysiloxane (Shin-Etsu Chemical Co., Ltd.) ("KF-96A", 6 cs) 5.0 (4) Aluminum stearate 0.2 (5) 1-isostearoyl-3-myristoyl-glycerol 2.0 (6) Octyl methoxycinnamate 2.0 (7) Fluorine compound-treated pigment (the following pigment is treated in the same manner as in Production Example 1) Talc 5.0 Titanium oxide 9.0 Iron oxide (red, yellow, black) 1.2 (8) Decamethylcyclopentasiloxane 15 0.0 (9) Butyl paraoxybenzoate 0.1 (10) Sodium benzoate 0.2 (11) Magnesium sulfate 0.5 (12) Glycerin 5.5 (13) 1,3-butyric acid Len glycol 2.5 (14) Purified water Balance (15) Fragrance 0.1

Example 16 Disinfecting cream: A disinfecting cream having the composition shown in Table 12 was obtained by the following method. (Production method) (6) to (11) are mixed so as to be uniform. This is added to the aqueous components (1) to (5) under stirring and emulsified to obtain a desired antiseptic cream.

[0090]

(Composition) (% by weight) (1) Polyoxyethylene (50) hydrogenated castor oil 0.5 (2) Polyoxyethylene (20) sorbitan palmitate 1.0 (3) Glycerin 6.0 (4) ) 1,3-butylene glycol 6.0 (5) Purified water balance (6) Squalane 5.0 (7) Jojoba oil 5.0 (8) Octamethylcyclotetrasiloxane 18.0 (9) Octyl methoxycinnamate 2 0.0 (10) Fluorine-modified siloxane of Example 3 30.0 (11) Disinfectant ("Irgasan DP-300") 0.2

The various cosmetics obtained in the above Examples 5 to 16 all had good cosmetic durability and were excellent in usability.

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI C08G77 / 385 C08G77 / 385 C08L 83/08 C08L 83/08 (72) Inventor Makoto Torizuka 1-17- Higashi Ikuta, Kawasaki City, Kanagawa Prefecture 5-402 (72) Inventor Masahiko Asahi 4-34-2 Otsuka, Bunkyo-ku, Tokyo (56) References JP-A-2-178292 (JP, A) JP-A-7-17984 (JP, A) JP-A 5-1150 (JP, A) JP-A-5-78491 (JP, A) JP-A-64-83086 (JP, A) JP-A-2-295912 (JP, A) JP-A-3-95226 (JP, A) A) JP-A-6-199629 (JP, A) JP-A-3-290901 (JP, A) JP-A-2-287151 (JP, A) JP-A-7-330545 (JP, A) JP-A-7 -277914 (JP, A) JP-A-7-330544 (JP, A) Table 7-505399 (JP, A) German Patent Application No. 2062816 (DE, A1) West German Patent Application No. 2444073 (DE, A1) USSR Patent Invention 626569 (SU, A) USSR Patent Invention 626554 (SU, A) USSR Patent Invention 869294 (SU, A) A) Soviet Patent Invention 1032761 (SU, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) C08G 77/00-77/62 A61K ⁷ /00-7/50 CA (STN) REGISTRY ( STN)

Claims (1)

(57) [Claims] 1. A compound of the general formula (A ') [In the formula, p 'represents an integer of 0 to 200, and p' is 1 to 2
When the integer is 00, R ^{4 to} R ⁹ are the same or different.
May be a straight-chain or branched-chain aliphatic having 1 to 20 carbon atoms.
Hydrocarbon group or alicyclic or aromatic having 5 to 10 carbon atoms
A hydrocarbon group, when p 'is 0 less of R ⁴ to R ⁹
At least one represents a group-(CH ₂ ) _{m + 2} -C (CF ₃ ) ₂ (C ₃ F ₇ ),
Is a linear or branched aliphatic hydrocarbon having 1 to 20 carbon atoms
A basic group or an alicyclic or aromatic hydrocarbon having 5 to 10 carbon atoms
R ¹ , R ² and R ³ are the same or different
May be a straight-chain or branched-chain fat having 1 to 20 carbon atoms
Group hydrocarbon group or alicyclic or aromatic having 5 to 10 carbon atoms
Represents a group hydrocarbon group, m represents an integer of 0 to 10, and q represents
A fluorine-modified siloxae represented by the following formula:
Cosmetics characterized by containing (A ') .