JPH09249518A - Modified siloxane compound, production of the same and cosmetics containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new modified siloxane compound capable of stably compounding fluorine compound, manifesting a high affinity to skin useful for obtaining cosmetics excellent in stability and high adhesion to skin. SOLUTION: This compound is a modified siloxane compound having degree of polymerization of 2-4000, especially 4-500 of the siloxane unit expressed in formula I and II (R<1> , R<2> are each a 1-18C hydrocarbon; Q is a divalent connecting group containing a heteroatom; Rf is a 1-20C perfluoroalkyl; m and p are each 2-16; n is 1-6), for example, the compound of formula III. The compound having siloxane unit of formula I is obtained by reacting the compound of formula V to hydrogenpolysiloxane having the siloxane unit of formula IV. The compound having the siloxane unit of formula II is obtained in the same manner. The preferred compounding amount of this modified siloxane compound to cosmetics is 0.01-80wt.%, especially 0.1-50wt.%.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a modified siloxane compound, a method for producing the same, and a cosmetic containing the same, more specifically, a fluorine compound can be stably blended,
The present invention also relates to a novel modified siloxane compound having high skin affinity, a method for producing the same, and a cosmetic containing the same, which has good stability and high adhesion to the skin.

[0002]

2. Description of the Related Art In recent years, a fluorine-based liquid oil agent having water and oil repellency (Japanese Patent Application Laid-Open No. 2-295912, Japanese Patent Application Laid-Open No. 5-2472) for the purpose of preventing makeup breakdown due to sweat or sebum.
No. 14, JP-A-6-184312, JP-A-6-184312
No. 234858) is used. on the other hand,
Although silicones are used in a wide range of fields, the only nonionic activator that has both water and oil repellency that is used in the cosmetics field is a polyether-modified silicone consisting of a silicone having a polyoxyalkylene group as a side chain. is there.

[0003]

However, such a fluorine-based liquid oil agent is difficult to be compatible with other commonly used additives, and a polyether-modified silicone generally used in the cosmetic field is used as an emulsifier. Even when used, it was difficult to obtain stable cosmetics.

Therefore, an object of the present invention is to provide a modified siloxane compound which can be stably blended with a fluorine-based compound and has a high skin affinity, and which contains the modified siloxane compound and which has good stability and high adhesion to the skin. To provide cosmetics.

[0005]

Means for Solving the Problems As a result of intensive studies in view of such circumstances, the present inventors have found that a specific modified siloxane compound having a perfluoroalkyl group and a glyceryl group can be stably blended with a fluorine compound. Moreover, they have found that they have high skin affinity, and have completed the present invention.

That is, the general formula (1) and the general formula (2)

[0007]

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[In the formula, R ¹ and R ² represent a hydrocarbon group having 1 to 18 carbon atoms, Q represents a divalent linking group containing a hetero atom, and Rf represents a perfluoroalkyl group having 1 to 20 carbon atoms. Represents a group, m and p represent an integer of 2 to 16, and n is 1 to
Indicates an integer of 6. ] A modified siloxane compound having a siloxane unit represented by the following formula and having a degree of polymerization of 2 to 4000, a method for producing the same, and a cosmetic containing the same are provided.

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION Modified siloxane compound of the present invention
Is at least two of the usual organopolysiloxanes
The siloxane unit has the structure of (1) or (2) above.
It is. In the above formula, R¹And R^TwoHas 1 to 18 carbon atoms
Indicates a hydrocarbon group, such as methyl, ethyl, propyl, buty
Le, pentyl, hexyl, octyl, decyl, dodeci
Direct addition of ruble, tetradecyl, hexadecyl, octadecyl, etc.
Chain alkyl group; isopropyl, sec-butyl, ter
t-butyl, neopentyl, 1-ethylpropyl, 2-
Branched chain alkyl groups such as ethylhexyl; cyclopentyl
And cyclic alkyl groups such as cyclohexyl.
You. Of these, alkyl groups having 1 to 6 carbon atoms, especially methyl
Groups are preferred. Q represents a divalent linking group containing a hetero atom
However, examples of the hetero atom include an oxygen atom and a sulfur atom.
It is. Examples of Q include an ether group (-O-) and polio.
Xyalkylene group, thioether group (-S-), ester
Group (-OCO-) and the like, but the stability of the compound
From the viewpoint of properties, ether group, polyoxyalkylene group (-
(OC_2-4Alkylene)_2-6-) Is preferred. R is the carbon number
It shows a divalent hydrocarbon group of 2 to 16 but has 2 to 5 carbon atoms.
A straight chain or branched chain alkylene group is preferred, and especially
Group and propylene group are preferred. Rf has 1 to 1 carbon atoms
20 shows a perfluoroalkyl group, CF_Three-, C_TwoF
_Five-, C_FourF₉-, C₆F₁₃-, C₈F ₁₇-, C_TenF_{twenty one}-, C₁₂F
_{twenty five}-, C₁₄F₂₉-, C₁₆F₃₃-, C₁₈F₃₇, C₂₀F₄₁-N
Examples include perfluoroalkanes having 6 to 20 carbon atoms.
Kill group is more preferred, especially C₆F₁₃-, C₈F₁₇-, C_Ten
F_{twenty one}-, C₁₂F_{twenty five}-And mixtures of these (mixtures of different chain lengths)
Is preferred. m and p represent an integer of 2 to 16, but in particular
3-11 is preferable. -(CH_Two)_m-And- (CH_Two)_p
Specific examples of − include trimethylene, tetramethylene, and
Ntamethylene, hexamethylene, heptamethylene, octane
Tamethylene, nonamethylene, decamethylene, undecame
Tylene, dodecamethylene, tetradecamethylene, hexa
Examples include decamethylene. n represents an integer of 1 to 6
However, 2 (specifically, ethylene) is particularly preferable.

The degree of polymerization (number of siloxane units) of the modified siloxane compound of the present invention is 2 to 4000, but 4 to 20.
00, especially 4 to 500 is preferable. The proportion (modification rate) of the modified siloxane units of the formulas (1) and (2) in all the siloxane units is 0.1 to 90%, particularly 1 to 5%.
0% is preferred.

A more preferred structure of the modified siloxane compound of the present invention is as follows.

[0012]

[Chemical 6]

[A is an integer of 2 to 200, b and c are 1 to
It represents an integer of 200, and R ¹ , R ² , Rf, m and p have the same meanings as described above. The modified siloxane compound of the present invention has, for example, the following general formulas (4) and (5):

[0014]

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[In the formula, R ¹ and R ² have the same meanings as described above. ] To the hydrogen polysiloxane having a siloxane unit represented by the general formula (6) and the general formula (7)
A compound represented by

[0016]

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[In the formula, Q, Rf, m, n and p have the same meanings as described above. ] It is manufactured by making it react.

Preferred examples of the raw material hydrogen polysiloxane include those having the following structures.

[0019]

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[D is an integer of 2 to 1000, e is 2 to 10
Indicates an integer of 00. This reaction is carried out in the presence of a catalyst, and the catalyst generally used for hydrosilylation, for example, a free radical initiator; a photoinitiator; a metal compound such as ruthenium, rhodium, palladium, osmium, iridium or platinum; Complex compounds of these metals; those obtained by supporting these on silica gel, activated carbon, alumina or the like can be mentioned. Among these, chloroplatinic acid, an alcohol solution of chloroplatinic acid, a Karstedt catalyst, platinum carbon and the like are particularly preferable. Although the amount of the catalyst used is not particularly limited, it is preferably in the range of 10 ⁻⁶ to 10 ⁻¹ mol with respect to ¹ mol of the olefin used.

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, and examples thereof include hydrocarbon solvents such as pentane, hexane and cyclohexane; benzene solvents such as benzene, toluene and xylene; diethyl ether, diisopropyl ether, THF ( Ethereal solvents such as tetrahydrofuran); alcoholic solvents such as methanol, ethanol, isopropyl alcohol, butanol and the like. If an alcohol solvent is used, Si
In order to prevent or suppress the dehydrogenation reaction between -H and -OH, a pH adjusting agent such as potassium acetate (JP-A-57 / 1982).
No. 149290) is preferably used. This hydrosilylation proceeds at 0 ° C to 200 ° C, but it is preferably performed at 20 ° C to 130 ° C in consideration of the reaction rate and the coloring of the product. The reaction time is preferably about 0.5 to 24 hours.

When the modified siloxane compound thus obtained is blended with cosmetics, the blending amount is not particularly limited, but is usually 0.01 to 80% by weight (hereinafter, simply indicated by "%"). , Preferably 0.1 to 50%.

In addition to the above-mentioned modified siloxane compound, the cosmetics of the present invention may optionally contain components which are usually added to cosmetics as long as the effects of the present invention are not impaired. Examples of such components include solid and semi-solid oil components such as petrolatum, lanolin, ceresin, microcrystalline wax, carnauba wax, higher fatty acids, and higher alcohols; olive oil, jojoba oil, castor oil,
Hydrocarbon-based liquid oils such as squalane, liquid paraffin, ester oils, diglycerides, triglycerides; silicone oils such as octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dimethylpolysiloxane, methylphenylpolysiloxane; perfluoropolyether, per Fluorine-based liquid oils such as fluorodecalin, perfluoroadamantane, perfluorobutyltetrahydrofuran, perfluoropentane, perfluorooctane, perfluorononane, perfluorodecane, perfluorododecane, and fluorine-modified silicone; inorganic and organic pigments, silicon or fluorine Colorants such as inorganic and organic pigments and organic dyes treated with compounds; water-soluble and oil-soluble polymers; nonionic surfactants, anionic surfactants, cationic interfaces Sex agent, dimethyl polysiloxane
Surfactants such as polyoxyalkylene copolymers; water, preservatives, antioxidants, pigments, thickeners, pH adjusters, fragrances, ultraviolet absorbers, moisturizers, blood circulation promoters, cooling sensation agents, antiperspirants Agents, bactericides, skin activating agents and the like.

The cosmetic composition of the present invention is not particularly limited in its dosage form, kind and the like, and can be produced by a conventional method. For example, oily cosmetics, emulsified cosmetics, aqueous cosmetics, lipsticks, blushers, It is applied as a foundation, skin cleanser, hair cleanser, etc.

[0025]

EFFECTS OF THE INVENTION The modified siloxane compound of the present invention can be stably blended with a fluorine-based compound and has high skin affinity.
It has good adhesiveness, does not easily lose the makeup component, and has good stability.

[0026]

The present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.

Example 1 Formula (A),

[0028]

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Methyl hydrogen polysiloxane represented by
100 g (19.6 mmol) of xane, C ₈F₁₇-(CH_Two)
_Two-O-CH_TwoCH = CH_Two 47.5g (94.3mmo
l), H_TwoC = CHCH_Two-O-CH_TwoCH (OH) CH_Two
OH 10.4 g (78.5 mmol), 2% H_TwoPtCl₆
50mg of the isopropanol solution from above is mixed and kept at 70 ° C for 3 hours.
For a while. Remaining Si-H amount is hydrogen generation amount by KOH
The reaction rate was approximately 100% when titrated from.
Excess C₈F₁₇(CH)_Two-O-CH_TwoCH = CH_TwoDecompress
Evaporation gave 135 g of the desired product (A ').

[0030]

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¹ H-NMR (ppm, CHCl ₃ standard (7.28 ppm) in CDCl ₃ ): 0.01-0.1 (s, 402 H ) Si—CH ₃ 0.34-0.50 (t , 16H, integral value _{criterion) Si-C H 2 - 1.45-1.65} (m, 16H) Si-CH 2 -C H 2 - 2.18-2.47 (m, 8H) -C H 2 _{-C 8 F 17 3.28-3.83 (m,} 44H) -C H 2 -O-, -O-C H -

Example 2 Formula (B),

[0033]

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70 g (3.9 mmol) of methyl hydrogen polysiloxane represented by: C ₆ F _{1 3-} (CH ₂ ) _{2-
O-CH 2 CH = CH 2} 47.2g (116.7mmo
_{l), H 2 C = CHCH} 2 -O-CH 2 CH (OH) CH 2
OH 12.8 g (97.2 mmol), 2% H ₂ PtCl ₆
50 mg of the isopropanol solution of was mixed and heated at 70 ° C. for 3 hours. When the amount of residual Si—H was titrated from the amount of hydrogen generated by KOH, the reaction rate was almost 100%.
Excess _{C 6 F 13 - (CH 2} ) 2 -O-CH 2 CH = CH 2 The desired product was evaporated under reduced pressure (B ') to obtain 112 g.

[0035]

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¹ H-NMR (ppm, CHCl ₃ standard (7.28 ppm) in CDCl ₃ ): 0.01-0.1 (s, 1368 H) Si—CH ₃ 0.34-0.50 (t, 100H, integral value _{criterion) Si-CH 2 - 1.45-1.65 (} m, 100H) Si-CH 2 -CH 2 - 2.18-2.47 (m, 50H) -CH 2 -C 8 F _{17 3.28-3.83 (m, 275H) -CH} 2 -O-, -O-CH-

Example 3 Formula (C),

[0038]

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[0039] Methyl represented by hydrogen polysiloxane _{50g (11.2mmol), C 9 F} 19 - (CH 2) 2
_{-O-CH 2 CH = CH 2} 179.0g (322.9mm
ol; fluorinated alkyl group is a mixture of different chain lengths), H ₂ C = CH
_{(CH 2) 4 -O-CH} 2 CH (OH) CH 2 OH 15.
6 g (89.7 mmol), 50 mg of 2% H ₂ PtCl ₆ in isopropanol were mixed and heated at 70 ° C. for 3 hours.
When the amount of residual Si—H was titrated from the amount of hydrogen generated by KOH, the reaction rate was almost 100%. Excess C ₉ F
_{19 - (CH 2) 2 -O} -CH 2 CH = CH 2 The desired product was evaporated under reduced pressure (C ') to obtain 193 g.

[0040]

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¹ H-NMR (ppm, CHCl ₃ standard in CDCl ₃ (7.28 ppm)): 0.01-0.1 (s, 306 H) Si—CH ₃ 0.34-0.50 (t, 64H, the integral value _{reference) Si-CH 2 - 1.15-1.30 (} m, 48H) -CH 2 - (O, not adjacent to Si) 1.45-1.65 (m, 64H) Si-CH _{2 -CH 2 - 2.18-2.47 (m,} 48H) -CH 2 -C 8 F 17 3.28-3.83 (m, 152H) -CH 2 -O-, -O-CH-

Example 4 Formula (C),

[0043]

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[0044] Methyl represented by hydrogen polysiloxane _{50g (11.2mmol), C 8 F} 17 - (CH 2) 2
_{-O-CH 2 CH = CH 2} 189.9g (376.7mm
ol), formula (8),

[0045]

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11.0 g (44.8 mm) of the compound represented by
ol) 50 mg of 2% H ₂ PtCl ₆ in isopropanol
Were mixed and heated at 70 ° C. for 3 hours. When the amount of residual Si—H was titrated from the amount of hydrogen generated by KOH, the reaction rate was almost 100%. Excess _{C 8 F 17 - (CH 2} ) 2 -
The desired product O-CH ₂ CH = CH ₂ was evaporated under reduced pressure and (C1) to give 90 g.

[0047]

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¹ H-NMR (ppm, CHCl ₃ standard (7.28 ppm) in CDCl ₃ ): 0.01-0.1 (s, 306 H) Si—CH ₃ 0.34-0.50 (t, 64H, the integral value _{reference) Si-CH 2 - 1.15-1.30 (} m, 64H) -CH 2 - (O, not adjacent to Si) 1.45-1.65 (m, 64H) Si-CH _{2 -CH 2 - 2.18-2.47 (m,} 56H) -CH 2 -C 8 F 17 3.28-3.83 (m, 140H) -CH 2 -O-, -O-CH-

Example 5 Formula (D),

[0050]

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Methyl hydrogen polysiloxane represented by
120 g (22.5 mmol) of xane, C ₈F₁₇-(CH_Two)
_Two-O-CH_TwoCH = CH_Two 108.9g (216.0m
mol), 22.0 g (90.0 mmo) of the above compound (8)
l) 2% H_TwoPtCl₆50mg of isopropanol solution
Were mixed and heated at 70 ° C. for 3 hours. The amount of residual Si-H
When titrated from the amount of hydrogen generated by KOH, the reaction rate is
It was almost 100%. Excess C₈F₁₇-(CH_Two)_Two−
O-CH_TwoCH = CH_TwoIs distilled off under reduced pressure to obtain the target product (D ').
214 g were obtained.

[0052]

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¹ H-NMR (ppm, CHCl ₃ standard (7.28 ppm) in CDCl ₃ ): 0.01-0.1 (s, 414 H) Si—CH ₃ 0.34-0.50 (t, 24H, the integral value _{reference) Si-CH 2 - 1.15-1.30 (} m, 64H) -CH 2 - (O, not adjacent to Si) 1.45-1.65 (m, 24H) Si-CH _{2 -CH 2 - 2.18-2.47 (m,} 16H) -CH 2 -C 8 F 17 3.28-3.83 (m, 60H) -CH 2 -O-, -O-CH-

Example 6 and Comparative Examples 1 and 2 (emulsified cosmetics) The aqueous phase components shown in Table 1 were mixed by heating and maintained at 70 ° C, and the oil phase components were similarly dissolved by heating at 70 ° C. The aqueous phase component was added to the phase component, emulsified with an emulsifier, and the emulsion was cooled to a final temperature of 25 ° C. with a heat exchanger to obtain an emulsified cosmetic. The obtained emulsified cosmetic composition was stored at 40 ° C. for 7 days, and then its appearance was visually evaluated to evaluate the stability. In addition, the test items in Table 1 were evaluated by 10 professional panelists according to the following evaluation criteria. Table 1 shows the results.

Evaluation Criteria ⊚: 8 or more out of 10 evaluated as good. ：: 6 or more out of 10 evaluated as good. B: 4 or more out of 10 evaluated as good. ×: Three or less out of ten evaluated as good.

[0056]

[Table 1]

As is clear from the results shown in Table 1, the cosmetics of the present invention have good stability and excellent usability.

Examples 7 to 9 and Comparative Examples 3 to 4 (lipstick) Each component shown in Table 2 was heated to 80 ° C. and uniformly mixed,
It was poured into a mold-eluting mold, cooled and solidified to produce a lipstick. The lipsticks thus obtained were evaluated by 10 professional panelists on the evaluation items shown in Table 3 according to the following evaluation criteria. The results are shown in Table 3.

Evaluation Criteria ⊚: Eight or more out of 10 evaluated as good. ：: 6 or more out of 10 evaluated as good. B: 4 or more out of 10 evaluated as good. ×: Three or less out of ten evaluated as good.

[0060]

[Table 2]

[0061]

[Table 3]

As is clear from Table 3, the lipstick containing the modified siloxane compound of the present invention is excellent in the spreadability, the familiarity, the non-stickiness, the finishing taste, the longevity of makeup and the moist feeling. Is.

Example 10 (two-layer liquid foundation) In the following composition, components (2) to (7) were dissolved at room temperature, and then component (1) was dispersed with a disper, and then components (8) to (8) were dispersed. What melt | dissolved (10) at room temperature was added with stirring, and it emulsified, and the target two-layer type liquid foundation was obtained.

[0064]

[Table 4] (Components) (%) (1) Silicone-treated pigment (commercially available product treated with polymethylhydrogensiloxane) Titanium oxide 6.0 Sericite 8.0 Iron oxide (red, yellow, black) 1.2 (2) Octamethylcyclotetrasiloxane 20.0 (3) Modified siloxane compound of Example 1 1.0 (4) Perfluoropolyether (FOMBLIN HC / 04, manufactured by Ausimont) 10.0 (5) Dimethylpolysiloxane (KF-96A, 6cs, manufactured by Shin-Etsu Chemical Co., Ltd.) 2.0 (6) Octyl methoxycinnamate 2.0 (7) Perfume 0.1 (8) Ethanol 10.0 (9) Glycerin 2.0 (10) Purified water balance

Example 11 (Emulsion foundation) The following components (1) to (5) were heated and mixed and kept at 70 ° C. Similarly, the components (8) to (11) were also dissolved by heating at 70 ° C., and then the component (12) was added and dispersed. To this, a mixture obtained by heating and mixing the components (1) to (5) was added and emulsified by an emulsifying machine. The emulsion was cooled to a final temperature of 25 ° C. with a heat exchanger, and components (6) and (7) were further added with stirring to obtain a milky liquid foundation.

[0066]

[Table 5] (Components) (%) (1) α-monoisostearyl glyceryl ether 1.0 (2) Modified siloxane compound of Example 2 2.0 (3) Dimethyl polysiloxane (KF-96L, 2cs, Shin-Etsu Chemical Industry Co., Ltd.) 10.0 (4) Perfluoropolyether (FOMBLIN HC / 03, manufactured by Ausimont Co., Ltd.) 10.0 (5) Octyl methoxycinnamate 2.0 (6) Octamethylcyclotetrasiloxane 15.0 ( 7) Fragrance 0.1 (8) Magnesium sulfate 1.0 (9) Methyl paraoxybenzoate 0.1 (10) Glycerin 7.0 (11) Purified water balance (12) Fluorine compound treated powder (according to production method 1 The treated one is mixed later) Titanium oxide 7.0 Sericite 6.1 Red iron oxide 0.5 Yellow iron oxide 1.3 Black iron oxide 0.1

Production Method 1 150 g of sericite was placed in a round-bottomed flask (or kneader), and C ₈ F ₁₇ CH ₂ CH ₂ OP (O) (OH) ₂ and (C ₈ F ₁₇ CH ₂ CH ₂ O) were added thereto. ₂ P (O) OH of about 1: 1 mixture (7.5 g) was dissolved in 1500 g of isopropyl alcohol by heating (50 ° C.), and the mixture was added at 60 ° C.
Mix for hours. Then, isopropyl alcohol was distilled off under reduced pressure at 40 to 50 ° C. and dried to obtain 155 g of the target powder.
I got

Example 12 (Hand cream) The following components (1) to (4) were mixed and heated to 75 ° C, and the mixture of components (5) to (7) heated to 75 ° C was stirred therein. Gradually added and emulsified, cooled to room temperature to obtain a hand cream.

[0069]

[Table 6] (Component) (%) (1) Modified siloxane compound of Example 4 2.0 (2) Aluminum chloride 0.8 (3) Isopropyl myristate 4.0 (4) Dimethyl polysiloxane (KF-96A) , 6cs, manufactured by Shin-Etsu Chemical Co., Ltd.) 10.0 (5) Methyl paraoxybenzoate 0.2 (6) Sorbitol 10.0 (7) Purified water balance

Example 13 (two-layer type sunscreen emulsion) A two-layer type sunscreen emulsion having the following composition was obtained in the same manner as in Example 10.

[0071]

[Table 7] (Component) (%) (1) Octamethylcyclotetrasiloxane 25.0 (2) Modified siloxane compound of Example 5 1.0 (3) Dimethylpolysiloxane (KF-96A, 6cs, Shin-Etsu Chemical Co., Ltd. 10.0) (4) Octyl methoxycinnamate 2.0 (5) Glycerin 2.0 (6) Ethanol 12.0 (7) Purified water balance (8) Silicone treated pigment (treated with methyl hydrogen polysiloxane Commercial products) Zinc oxide 5.5 Titanium oxide 2.0 Talc 5.0 (9) Fragrance

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification number Internal reference number FI Technical display location C08G 77/46 NUL C08G 77/46 NUL 81/00 NUU 81/00 NUU (72) Inventor Akira Yamamuro 2606 Kao stock company research institute, Kaigacho, Haga-gun, Tochigi prefecture (72) Inventor Koichi Nakamura 2606 Akabane shellfish, Kai-cho, Haga-gun, Tochigi prefecture Kao stock company research institute

Claims (4)

[Claims] 1. A general formula (1) and a general formula (2): [In the formula, R ¹ and R ² represent a hydrocarbon group having 1 to 18 carbon atoms, Q represents a divalent linking group containing a hetero atom, and Rf
Represents a perfluoroalkyl group having 1 to 20 carbon atoms, m
And p represent the integer of 2-16, n shows the integer of 1-6. ] Having a siloxane unit represented by
4000 modified siloxane compounds. 2. Q is represented by the general formula (3): [In the formula, R represents a divalent hydrocarbon group having 2 to 16 carbon atoms, and q represents an integer of 0 to 50. ] The modified siloxane compound according to claim 1, which is a group represented by: 3. General formulas (4) and (5): Wherein, R ¹ and R ² is a hydrocarbon group having 1 to 18 carbon atoms. ] To the hydrogen polysiloxane having a siloxane unit represented by the general formula (6) and the general formula (7)
A compound represented by: [In the formula, Q, Rf, m, n and p have the same meanings as described above. ] The method for producing a modified siloxane compound according to claim 1, wherein 4. A cosmetic containing the modified siloxane compound according to claim 1.