JP2011195571A - Surface-coated/treated powder using silicone phosphoric acid triester, and cosmetic containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To develop a novel silicone phosphoric acid triester and to apply the triester as a surface-treating agent of a powder or the like for cosmetics.SOLUTION: The silicone phosphoric acid triester is a compound represented by formula (I) (wherein, R's independently represent 1-4C alkyl; R represents a bivalent 2-7C hydrocarbon which may have at least one group selected from -O- and -CO-; and n represents an integer of 5 to 40). When the compound is used as the surface-treating agent of the powder, it provides water repellency and dispersibility by the treatment with a small amount, and exhibits good attachability. Especially, the compound is suitable for the surface covering treatment of a metal oxide such as titanium oxide, zinc oxide and iron oxide. A silicone phosphoric acid diester and/or a silicone phosphoric acid monoester may be contained in the cosmetics.

Description

  The present invention relates to a powder surface-treated with a novel silicone phosphate triester and a cosmetic containing the same.

  In cosmetics, powders such as inorganic powders, organic powders, and pigment powders are blended for the purpose of making up effects and adjusting touch. These powders are composed of inorganic and organic compounds, and are amphiphilic in nature, so that they are easily compatible with water and oil. For this reason, cosmetics containing such powders tend to get wet with secretions such as water, sweat, and sebum, and the original color tone of the cosmetics is impaired, sweating, facial movement, etc. A phenomenon of so-called “decoration of makeup” occurs in which uniformity is impaired.

Therefore, conventionally, techniques for coating the powder surface with various surface treatment agents have been developed as techniques for preventing makeup collapse due to sweat and sebum.
For example, silicones such as dimethicone, hydrogenmethylpolysiloxane, silane coupling agents such as perfluoroalkyldimethylmethoxysilane, fluorine compounds such as perfluoroalkyl phosphate diethanolamine salts, phosphate esters containing perfluoroalkyl groups, stearin Examples include fatty acid metal soaps such as zinc acid, acylated amino acid derivatives such as acyl glutamate aluminum, lecithin or metal salts thereof, and phosphate ester-modified organo (poly) siloxanes (for example, Patent Documents 1 to 10).

Among these, the phosphate ester-modified organo (poly) siloxane described in Patent Document 10 has the following structure.
At least one silicon atom of the organo (poly) siloxane has the formula

[R ¹ and R ² represent a C2-20 alkylene group, R ³ represents an optionally substituted C1-20 alkylene group, R ⁴ represents a C1-22 alkyl group, M Represents H or a monovalent cation, p and q represent numbers from 0 to 200, a, b and c represent the number of groups in parentheses bonded to a phosphorus atom, a + b + c = 3, a and c Is 1 or 2, and b is 0 or 1. ] The phosphate ester modified organo (poly) siloxane modified with the phosphate ester group represented by this.

Further, as a phosphate triester-modified organo (poly) siloxane that can be used in cosmetics, Patent Document 11 discloses that at least one silicon atom of organo (poly) siloxane is represented by the following formula [{—CH ₂ CH _{2 ^{-R 2 - (OR 1) p}} -O} 3 P = O] 1/3
[In the formula, in the trivalent group in the square brackets, 3p R ^{1 s} are the same or different and represent a linear or branched alkylene group having 2 to 20 carbon atoms, and three R ² are the same or different. And a hydroxyl group may be a linear or branched alkylene group having 7 to 20 carbon atoms which may be substituted, and three ps are the same or different and represent a number of 0 to 20. All three terminal carbon atoms are bonded to silicon atoms of the same or two or three different organo (poly) siloxane molecules. A phosphoric ester triester-modified organo (poly) siloxane modified with a group represented by the formula:

However, it is described that the phosphate triester-modified organo (poly) siloxane described in Patent Document 11 is used as a base material to be blended in cosmetics, and that it can be used as a surface treatment agent for cosmetic powders. Not listed. Moreover, although the said phosphoric acid triester modified organo (poly) siloxane has described the triester body which three organo (poly) siloxane couple | bonded with phosphoric acid, organo (poly) siloxane and phosphoric acid are- They are bonded via a CH ₂ CH ₂ —R ² — (OR ¹ ) _p — group, and the group has a long chain of 9 or more carbon atoms.
Further, in Patent Document 11, a phosphate triester-modified organo (poly) siloxane is an organopolysiloxane having at least one hydrogen atom bonded to a silicon atom.
^{_{{CH 2 = CH-R 2}} - (OR 1) p -O} 3 P = O
[Wherein, 3p R ^{1 s} are the same or different and represent a linear or branched alkylene group having 2 to 20 carbon atoms, and three R ² are the same or different and may be substituted with a hydroxyl group] A linear or branched alkylene group having a number of 7 to 20 is shown, and three p's are the same or different and represent a number of 0 to 20. In the method, the —CH ₂ CH ₂ —R ² — (OR ¹ ) _p — group is short as in the present invention. In some cases, synthesis was difficult.

^{_{Therefore, -CH 2 CH 2 -R 2 -}} (OR 1) p - for (also referred to as silicone phosphate triester) group is short phosphoric acid triester modified organo (poly) siloxanes, which have utility as substrates for cosmetics Of course, it has not been known at all that it is useful as a surface treatment agent for powders.

JP-A-5-339518 JP 2003-55142 A JP 2009-263213 A JP-A-62-250074 JP-A-10-167931 Japanese Patent Laid-Open No. 10-203926 JP 11-335227 A Patent Republication 2006-106728 JP 2008-247834 A JP 09-136815 A Japanese Patent Laid-Open No. 09-157397

An object of the present invention is to develop a silicone phosphate triester having a short —CH ₂ CH ₂ —R ² — (OR ¹ ) _p — group, which is different from the silicone phosphate triester described in Patent Document 11. Is applied as a surface treatment agent for powders such as cosmetic powders.

When the silicone phosphate triester compound having a short —CH ₂ CH ₂ —R ² — (OR ¹ ) _p — group is used as a surface treatment agent for powder, the present inventors have high water repellency with a small amount of treatment, The present invention has been completed by finding that it exhibits dispersibility and is excellent in powder processing efficiency.

That is, the present invention
(1) Formula (I)

(In the formula, each R ₁ independently represents an alkyl group having 1 to 4 carbon atoms, and R may have at least one selected from —O— and —CO—.) A powder coated with a surface coating with one or more of the silicone phosphate triesters represented by -7, wherein n represents an integer of 5 to 40),
(2) Formula (I)

(In the formula, each R ₁ independently represents an alkyl group having 1 to 4 carbon atoms, and R may have at least one selected from —O— and —CO—.) 1 to 2 or more of silicone phosphoric acid triester represented by n represents a divalent hydrocarbon group of ˜7, and n represents an integer of 5 to 40,
Formula (II)

(Wherein R ₁ , R and n are the same as defined in the above formula (I)), one or more silicone phosphate diesters represented by 0 to 35% by mass, and
Formula (III)

(Wherein R ₁ , R and n are the same as defined in the above formula (I)), the surface of the silicone phosphate monoester represented by 1 or 2 or more and 0 to 5% by mass of the silicone phosphate monoester The powder according to the above (1), which has been coated,
(3) The surface-coated powder according to (1) or (2) above, which further contains an organic titanate as a surface treating agent in addition to the silicone phosphate ester,
(4) The powder according to (3) above, wherein the mass ratio of the silicone phosphate ester and the organic titanate is 1: 9 to 9: 1,
(5) The powder according to (3) or (4) above, wherein the organic titanate is isopropyl triisostearyl titanate,
(6) The surface coating treatment according to any one of (1) to (5) above, wherein the powder is at least one selected from the group consisting of titanium oxide, zinc oxide and iron oxide The coating amount of the powder and (7) the silicone phosphate ester is 0.01 to 5% by mass of the surface coating treated powder, as described in any one of (1) to (6) above The present invention relates to a surface-coated powder.

Furthermore, the present invention provides
(8) A cosmetic comprising the surface-coated powder according to any one of (1) to (7).

  Since the silicone phosphate triester used in the present invention has many silicone chains, it exhibits water repellency and dispersibility with a small amount of treatment and has a phosphate group. Excellent adhesion due to strong bond. Moreover, the powder surface-treated with the silicone phosphate triester and organic titanate of the present invention is excellent in dispersibility in various oils. Furthermore, in the cosmetic containing the powder coated with the silicone phosphate triester of the present invention, the uniformity of the cosmetic film and the makeup lasting effect are excellent.

Details of the present invention will be described below.
(Silicone phosphate triester)
The silicone phosphate triester used in the present invention has the formula (I)

It is represented by
In the formula, each R ₁ independently represents an alkyl group having 1 to 4 carbon atoms, and R 2 may have at least one selected from —O— and —CO—. 7 represents a divalent hydrocarbon group, and n represents an integer of 5 to 40.

Examples of the “alkyl group having 1 to 4 carbon atoms” in R ₁ include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, and t-butyl. Groups. Of these, methyl is preferred as R ₁ .
“Divalent hydrocarbon group having 2 to 7 carbon atoms” of “Divalent hydrocarbon group having 2 to 7 carbon atoms which may have at least one selected from —O— and —CO—” in R Examples of "" include ethylene chain, propylene chain, methylethylene chain, butylene chain, 1,2-dimethylethylene chain, pentylene chain, 1-methylbutylene chain, 2-methylbutylene chain, hexylene chain, heptylene chain and the like.

The “C2-C7 divalent hydrocarbon group having at least one selected from —O— and —CO—” has one or more of —O— or —CO—. For example, —CH ₂ —O— (CH ₂ ) ₂ —, — (CH ₂ ) ₂ —O— (CH ₂ ) ₂ —, — (CH ₂ ) ₃ —O— (CH ₂ ) ₂ —, _{- (CH 2) 4 -O- (} CH 2) 2 -, - (CH 2) 2 -O (CH 2) 2 -O- (CH 2) 2 -, - (CH 2) 2 -O- (CH _{2) 4 -, - (CH} 2) 2 -O- (CH 2) 5 -, - (CH 2) 3 -O-CH 2 -, - CH 2 -CO- (CH 2) 2 -, - (CH ₂ ) _2- CO— (CH ₂ ) ₂ —, — (CH ₂ ) ₃ —CO— (CH ₂ ) ₂ —, — (CH ₂ ) ₄ —CO— (CH ₂ ) ₂ —, — (CH ₂ ) ₂ —CO— (CH ₂ ) ₄ —, — (CH ₂ ) ₂ —CO— (CH ₂ ) ₅ —, — (CH ₂ ) ₃ —CO—CH ₂ — and the like.
“C2-C7 divalent hydrocarbon group optionally having at least one selected from —O— and —CO—” includes — (CH ₂ ) ₃ O (CH ₂ ) _2- is preferred.

  Specific examples of silicone phosphate triesters include the following. However, n is an integer in any one of 5-40.

  These can be used singly or in a mixture of two or more.

(Method for producing silicone phosphate triester)
The silicone phosphate triester of the present invention can be produced, for example, by the method shown in the following reaction formula.

(Wherein R ₁ , R and n are the same as defined in formula (I))
One-terminal carbinol-modified silicone represented by the formula (IV) is reacted with phosphorus oxychloride represented by the formula (V) in the presence of a base in a solvent.

  As a solvent used in carrying out the above reaction, polar solvents such as tetrahydrofuran, dimethyl sulfoxide, N, N-dimethylformamide, acetone, diethyl ether and acetonitrile can be used.

Examples of the base include alkylamines such as diethylamine and triethylamine, heterocyclic amines such as piperazine and imidazole, quaternary ammonium salts such as benzyltriethylammonium chloride and methyltrioctylammonium chloride, n-butyllithium, lithium diisopropylamide and the like. Organic metals can be used.
The reaction temperature is usually about 25 ° C. to 50 ° C., and the reaction time is usually about 2 hours to 20 hours, although it varies depending on the silicone chain length.

Although the silicone phosphoric acid triester represented by the formula (I) is obtained by the above reaction, as a by-product, the silicone phosphoric acid diester represented by the formula (II), the silicone phosphoric acid represented by the formula (III) Monoesters are produced.
Although these by-products can be used as a mixture of silicone phosphate esters, the product is purified by a conventional method to obtain substantially only the silicone phosphate triester represented by the formula (I). May be used.

(Surface coated powder)
The surface-treating agent used for the surface-coated powder of the present invention is one or more of the silicone phosphate triesters represented by the above formula (I) and, if necessary, the formula (II )

(Wherein R ₁ , R and n are the same as defined in the above formula (I)) and / or two or more types of silicone phosphate diesters represented by formula (III)

(Wherein R ₁ , R, and n are the same as defined in the above formula (I)) are silicone phosphates containing one or more of the silicone phosphate monoesters.

  The compounding ratio of the silicone phosphate triester represented by the formula (I), the silicone phosphate diester represented by the formula (II) and the silicone phosphate monoester represented by the formula (III) is represented by the formula (I): The silicone phosphate triester represented is not particularly limited as long as the silicone phosphate triester has an effect as a powder surface treatment agent. Preferably, the silicone phosphate triester represented by the formula (I) is 60 to 100% by mass. The silicone phosphate diester represented by (II) is 0 to 35% by mass, and the silicone phosphate monoester represented by the formula (III) is 0 to 5% by mass.

As the powder subjected to surface coating treatment with the silicone phosphate triester represented by the above formula (I) alone or the silicone phosphate ester mixture containing the silicone phosphate triester represented by the formula (I), Usually, if it is a powder used in cosmetics, depending on the shape such as spherical shape, plate shape, needle shape, particle size such as fumes, fine particles, pigment grade, particle structure such as porous, nonporous, etc. There is no particular limitation, and inorganic powders, glitter powders, organic powders, pigment powders, composite powders and the like can be used.
Specifically, the following are mentioned, for example, These can be used 1 type or 2 types or more.

Inorganic powders:
Titanium oxide, black titanium oxide, conger, ultramarine, bengara, yellow iron oxide, black iron oxide, zinc oxide, aluminum oxide, silica, magnesium oxide, zirconium oxide, magnesium carbonate, calcium carbonate, chromium oxide, chromium hydroxide, carbon black Aluminum silicate, magnesium silicate, magnesium aluminum silicate, mica, synthetic mica, sericite, talc, kaolin, silicon carbide, barium sulfate, bentonite, smectite, boron nitride and the like.
Bright powders:
Bismuth oxychloride, titanium oxide coated mica, iron oxide coated mica, iron oxide coated mica titanium, organic pigment coated mica titanium, aluminum powder, etc.
Organic powders:
Nylon powder, polymethyl methacrylate powder, acrylonitrile-methacrylic acid copolymer powder, vinylidene chloride-methacrylic acid copolymer powder, polyethylene powder, polystyrene powder, organopolysiloxane elastomer powder, polymethylsilsesquioxane powder, polyurethane powder, Wool powder, silk powder, crystalline cellulose powder, N-acyl lysine powder, etc.
Dye powders:
Organic tar pigments, organic pigment lake pigments, etc.
Composite powders:
Fine titanium oxide coated mica titanium, fine zinc oxide coated mica titanium, barium sulfate coated mica titanium, titanium oxide-containing silica, zinc oxide-containing silica and the like.
Of these, titanium oxide, zinc oxide, iron oxide and the like are particularly suitable as the treated powder of the present invention.

  In the present invention, the method for surface-coating the silicone phosphate ester containing the silicone phosphate triester represented by the above formula (I) on these powders is not particularly limited, and is generally known. A processing method is used. Specifically, a method of directly mixing with powder (dry treatment method), a method using a solvent such as ethanol, isopropyl alcohol, n-hexane, benzene, toluene (wet method), a gas phase method, a mechanochemical method, etc. Can be mentioned.

  For example, a solvent such as hexane and a silicone phosphate ester containing a silicone phosphate triester represented by the above formula (I) are added and dissolved in a mixer such as a Henschel mixer, and then the powder is added and dispersed uniformly. Next, while stirring this solution, the solution is heated to about 100 ° C., the solvent is distilled off under reduced pressure, cooled to room temperature, and then pulverized with a pulverizer such as a pulverizer to obtain a powder coated with the surface. A method is mentioned. Then, you may bake at the temperature of 125 degreeC or more.

Further, in the present invention, a silicone compound, a fluorine compound, an oil agent, an oil and fat, a higher alcohol, a wax, a polymer, together with a silicone phosphate ester containing a silicone phosphate triester represented by the above formula (I) in the powder. A commonly known surface treating agent such as a resin can be coated at the same time.
Among these other surface treatment agents, one or more types can be selected, but it is particularly preferable to coat the organic titanate surface treatment agent at the same time because the dispersibility of the surface coating powder in the oil agent is improved. .

  The organic titanate has an alkoxy group, and examples thereof include long-chain carboxylic acid type, pyrophosphoric acid type, phosphorous acid type, amino acid type alkyl titanate and the like. As the alkoxy group of the organic titanate, those having an alkyl group having 1 to 4 carbon atoms are preferable from the viewpoint of reactivity with the powder, and these may be linear or branched, for example, methoxy group, ethoxy Group, propoxy group, butoxy group and the like.

Among these organic titanates, when a long-chain carboxylic acid type alkyl titanate having an alkyl group having 8 to 22 carbon atoms is selected, it is preferable from the viewpoint of dispersibility.
_{(R 2 O) -Ti- (OCOR} 3) 3 (VI)
(In the formula, R ₂ represents an alkyl group having 1 to 4 carbon atoms, R ₃ represents an alkyl group having 8 to 22 carbon atoms, and these alkyl groups may be linear or branched). A compound can be illustrated.
Specifically, isopropyl triisostearyl titanate, isopropyl triisomyristyroyl titanate, isopropyl trioctanoyl titanate, methyl triisostearoyl titanate, methyl triisomyristyroyl titanate, ethyl triisostearoyl titanate, ethyl triisomyristyro Il titanate etc. are mentioned, These can be used 1 type or 2 or more types. Among these, isopropyl triisostearyl titanate is particularly preferable because the dispersibility of the surface-coated powder in the oil becomes good.

  In the case where a plurality of surface treatment agents are coated simultaneously, if a solvent capable of uniformly dissolving the plurality of surface treatment agents is selected and a wet process is performed, the powder surface can be uniformly coated. This is preferable because it is possible.

The surface-treated powder of the present invention is obtained by coating the powder surface with a silicone phosphate ester containing a silicone phosphate triester represented by the above formula (I), and the coating amount is not particularly limited. However, 0.01-5 mass% is preferable with respect to powder. Within this range, a surface-coated powder having particularly excellent water resistance and adhesion to the skin can be obtained.
Moreover, when carrying out a coating process simultaneously with several surface treatment agents, such as organic titanate, the total amount of a surface treatment agent is preferable 0.01-10 mass%. In that case, the mass ratio of the silicone phosphate ester containing the silicone phosphate triester represented by the above formula (I) and the other surface treatment agent is preferably in the range of 1: 9 to 9: 1. Furthermore, a surface-coated powder having particularly excellent dispersibility in an oil agent can be obtained when the ratio is in the range of 1: 3 to 3: 1.

(Cosmetics)
The cosmetic of the present invention is produced by blending one or more of the above surface-coated powders in combination with known cosmetic ingredients according to a conventional method. The amount of the surface-coated powder in the cosmetic of the present invention is not particularly limited and varies depending on the cosmetic dosage form and item, but is 1 to 90% by mass, preferably 5 to 40% by mass. %is there.
Components that can be blended according to the type can be blended appropriately in the cosmetic.
For example, oils, surfactants, alcohols, water, moisturizers, gelling agents and thickeners, powders other than those subjected to the above surface coating treatment, UV absorbers, antiseptics, antibacterial agents, antioxidants, skin beautifying agents Ingredients (whitening agents, cell activators, anti-inflammatory agents, blood circulation promoters, skin astringents, antiseborrheic agents, etc.), vitamins, amino acids, nucleic acids, hormones and the like can be blended.

Examples of oils include solid oils, semi-solid oils, liquid oils, and examples include natural animal and vegetable oils and semi-synthetic oils, hydrocarbon oils, ester oils, glyceride oils, silicone oils, higher alcohols, higher fatty acids, and organic solvents. Is done.
Solid oils include carnauba wax, candelilla wax, cotton wax, shellac wax, natural waxes such as hardened oil, mineral waxes such as ozokerite, ceresin, paraffin wax, microcrystalline wax, polyethylene wax, Fischer-Tropsch wax, ethylene propylene copolymer And the like, synthetic alcohols such as behenyl alcohol, cetyl alcohol, stearyl alcohol, cholesterol and phytosterols, higher fatty acids such as stearic acid and behenic acid, and the like.
Liquid oils, including natural animal and vegetable oils and semi-synthetic oils, specifically avocado oil, linseed oil, almond oil, ibotarou, eno oil, olive oil, kaya oil, liver oil, kyounin oil, wheat germ oil, sesame oil, rice germ oil , Rice bran oil, sasanqua oil, safflower oil, cinnamon oil, cinnamon oil, turtle oil, soybean oil, tea seed oil, camellia oil, evening primrose oil, corn oil, rapeseed oil, Japanese kiri oil, nukarou, germ oil, permanent oil , Palm oil, palm kernel oil, castor oil, sunflower oil, grape oil, jojoba oil, macadamia nut oil, cottonseed oil, palm oil, tricoconut oil fatty acid glyceride, peanut oil, lanolin, liquid lanolin, reduced lanolin, lanolin alcohol, lanolin acetate, Lanolin fatty acid isopropyl, POE lanolin alcohol ether, POE lanolin alcohol acetate , Lanolin fatty acid polyethylene glycol, POE hydrogenated lanolin alcohol ether, yolk oil, and the like.
Examples of the hydrocarbon oil include squalane, squalene, liquid paraffin, pristane, polyisobutylene and the like.
Examples of ester oils include diisobutyl adipate, 2-hexyldecyl adipate, di-2-heptylundecyl adipate, N-alkyl glycol monoisostearate, isocetyl isostearate, trimethylolpropane triisostearate, 2-ethylhexanoic acid Cetyl, ethylene glycol di-2-ethylhexanoate, neopentyl glycol di-2-ethylhexanoate, trimethylolpropane tri-2-ethylhexanoate, pentaerythritol tetra-2-ethylhexanoate, cetyl octoate, octyldodecyl Gum ester, oleyl oleate, octyldodecyl oleate, decyl oleate, neopentyl glycol dicaprate, triethyl citrate, 2-ethylhexyl succinate, amyl acetate, ethyl acetate Butyl acetate, isocetyl stearate, butyl stearate, diisopropyl sebacate, di-2-ethylhexyl sebacate, cetyl lactate, myristyl lactate, isopropyl palmitate, 2-ethylhexyl palmitate, 2-hexyldecyl palmitate, palmitic acid 2 -Heptyl undecyl, cholesteryl 12-hydroxystearylate, dipentaerythritol fatty acid ester, isopropyl myristate, 2-octyldodecyl myristate, 2-hexyldecyl myristate, myristyl myristate, hexyldecyl dimethyloctanoate, ethyl laurate, Examples include hexyl laurate, N-lauroyl-L-glutamic acid-2-octyldodecyl ester, and diisostearyl malate.
Examples of glyceride oil include acetoglyceride, triisooctanoic acid glyceride, triisostearic acid glyceride, triisopalmitic acid glyceride, tri-2-ethylhexanoic acid glyceride, monostearic acid glyceride, di-2-heptylundecanoic acid glyceride, and trimyristic acid. A glyceride etc. are mentioned.
Silicone oils include dimethylpolysiloxane, methylphenylpolysiloxane, methylhydrogenpolysiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, tetramethyltetrahydrogencyclotetrasiloxane, alkyl-modified silicone. Etc.
Examples of the higher alcohol include oleyl alcohol, lauryl alcohol, stearyl alcohol, isostearyl alcohol, and 2-octyldodecanol.
Examples of higher fatty acids include oleic acid, palmitic acid, myristic acid, stearic acid, and isostearic acid.
Organic solvents: hydrocarbons such as n-hexane and cyclohexane, aromatic compounds such as benzene, toluene and xylene, non-aromatic compounds such as ethyl acetate and butyl acetate, chlorine compounds such as chloroform, dichloromethane and dichloroethane, dioxane, Ether compounds such as tetrahydrofuran, 2-propanol, benzyl alcohol, phenoxyethanol, carbitols, cellosolves, spindle oil and the like.

The surfactant is not particularly limited as long as it is usually used in cosmetics, and any surfactant can be used. Examples of the surfactant include an anionic surfactant, a cationic surfactant, a nonionic surfactant, and an amphoteric surfactant. These may be used alone or in combination of two or more as required. be able to.
Specific examples of anionic surfactants include fatty acid soaps such as sodium stearate and triethanolamine palmitate, alkyl ether carboxylic acids and salts thereof, carboxylates such as condensation of amino acids and fatty acids, alkyl sulfonic acids, and alkene sulfones. Acid salts, sulfonates of fatty acid esters, sulfonates of fatty acid amides, sulfonates of alkyl sulfonates and their formalin condensates, alkyl sulfate esters, secondary higher alcohol sulfates, alkyl and allyl ether sulfates Ester salts, fatty acid ester sulfates, fatty acid alkylolamide sulfates, polyoxyethylene alkyl sulfates, sulfate salts such as funnel oil, alkyl phosphates, ether phosphates, alkyl allyl ether phosphates A Dorin salts, such as N- acylamino acid-based active agents.
Cationic surfactants include long chain alkyltrimethylammonium salts, dilong chain alkyldimethylammonium salts, long chain alkyldimethylbenzylammonium salts, dipolyoxyethylene alkylmethylammonium salts, dipolyoxyethylene alkyl ether dimethylammonium salts, poly Alkyl quaternary ammonium salts such as oxypropylene methyl diethyl ammonium salt and aromatic quaternary ammonium salts, pyridinium salts such as alkyl pyridinium salts, imidazoline salts such as alkyl dihydroxyethyl imidazoline salts, N-acyl basic amino acid lower alkyl esters And amine salts such as alkylamine salts, polyamines, amino alcohol fatty acid derivatives and the like.
Nonionic surfactants include sorbitan fatty acid ester, glycerin fatty acid ester, polyglycerin fatty acid ester, propylene glycol fatty acid ester, polyethylene glycol fatty acid ester, sucrose fatty acid ester, polyoxyethylene alkyl ether, polyoxypropylene alkyl ether, polyoxy Ethylene alkyl phenyl ether, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbitol fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene propylene glycol fatty acid ester, polyoxyethylene castor oil, polyoxyethylene cured Castor oil, polyoxyethylene hydrogenated castor oil fatty acid ester, polyoxyethylene N-phytostanol ether, polyoxyethylene phytosterol ether, polyoxyethylene cholestanol ether, polyoxyethylene cholesteryl ether, polyoxyalkylene-modified organopolysiloxane, polyoxyalkylene / alkyl co-modified organopolysiloxane, alkanolamide, sugar ether, sugar Examples include amides.
Examples of amphoteric surfactants include carbobetaine-type amphoteric surfactants such as alkyldimethylaminoacetic acid betaine, fatty acid amidopropyldimethylaminoacetic acid betaine, alkyldihydroxyethylaminoacetic acid betaine, and sulfobetaine-type amphoteric surfactants such as alkylsulfobetaine, N -Amidoamine type (imidazoline type) amphoteric surfactants such as fatty acid acyl-N-carboxymethyl-N-hydroxyethylethylenediamine salt, N-fatty acid acyl-N-carboxymethoxyethyl-N-carboxymethylethylenediamine di-salt, N- [ Amino acid type amphoteric surfactants such as 3-alkyloxy-2-hydroxypropyl] arginine salt, and alkyliminodicarboxylate type amphoteric surfactants.

Specific examples of alcohols include lower alcohols such as ethanol and isopropanol, glycerin, diglycerin, polyglycerin, diethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, 1,3-butylene glycol, and erythritol. Examples include monohydric alcohols, sugar alcohols such as sorbitol, maltose, xylitol, maltitol, benzyl alcohol, and the like.
Examples of the humectant include urea, hyaluronic acid, chondroitin sulfate, pyrrolidone carboxylate and the like.

  Water-based thickeners and gelling agents include gum arabic, gum tragacanth, galactan, carob gum, guar gum, caraya gum, carrageenan, pectin, agar, quince seed (malmello), starch (rice, corn, potato, wheat), alge colloid, tolanto gum Plant polymers such as locust bean gum, microbial polymers such as xanthan gum, dextran, succinoglucan, pullulan, animal polymers such as collagen, casein, albumin, gelatin, carboxymethyl starch, methylhydroxypropyl starch, etc. Starch-based polymers, methylcellulose, ethylcellulose, hydroxypropylmethylcellulose, carboxymethylcellulose, hydroxymethylcellulose, hydroxypropylcellulose, nito Cellulose, cellulose sulfate sodium, sodium carboxymethyl cellulose, crystalline cellulose, cellulose-based cellulose polymer, alginic acid-based polymers such as sodium alginate, propylene glycol alginate, polyvinyl methyl ether, carboxyvinyl polymer, alkyl-modified carboxyvinyl polymer, etc. Vinyl polymer, polyoxyethylene polymer, polyoxyethylene polyoxypropylene copolymer polymer, acrylic polymer such as sodium polyacrylate, polyethyl acrylate, polyacrylamide, bentonite, magnesium aluminum silicate, laponite Inorganic thickeners such as hectorite and silicic anhydride, polyethyleneimine, and cationic polymers. Also included are film forming agents such as polyvinyl alcohol and polyvinyl pyrrolidone.

  Examples of oil gelling agents include metal soaps such as aluminum stearate, magnesium stearate, zinc myristate, amino acid derivatives such as N-lauroyl-L-glutamic acid, α, γ-di-n-butylamine, dextrin palmitate, Dextrin fatty acid esters such as dextrin stearic acid ester, dextrin 2-ethylhexanoic acid palmitic acid ester, sucrose fatty acid esters such as sucrose palmitic acid ester, sucrose stearic acid ester, benzylidene of sorbitol such as monobenzylidene sorbitol, dibenzylidene sorbitol Examples thereof include organically modified clay minerals such as derivatives, dimethylbenzyl dodecyl ammonium montmorillonite clay, and dimethyl dioctadecyl ammonium montmorillonite clay.

Examples of powders include inorganic powders, organic powders, metal soap powders, colored pigments, pearl pigments, metal powders, tar dyes, natural dyes, etc., and their particle shapes (spherical, needle, plate, etc.) and particles Any one can be used regardless of the diameter (smoke, fine particles, pigment grade, etc.) and the particle structure (porous, non-porous, etc.).
Specific inorganic powders include titanium oxide, zirconium oxide, zinc oxide, cerium oxide, magnesium oxide, barium sulfate, calcium sulfate, magnesium sulfate, calcium carbonate, magnesium carbonate, talc, mica, kaolin, sericite, muscovite , Synthetic mica, phlogopite, saucite, biotite, lithia mica, silicic acid, anhydrous silicic acid, aluminum silicate, magnesium silicate, magnesium aluminum silicate, calcium silicate, barium silicate, strontium silicate, tungstic acid Examples thereof include metal salts, hydroxyapatite, vermiculite, hydrite, bentonite, montmorillonite, hectorite, zeolite, ceramic powder, dicalcium phosphate, alumina, aluminum hydroxide, boron nitride and the like.
Organic powders include polyamide powder, polyester powder, polyethylene powder, polypropylene powder, polystyrene powder, polyurethane, benzoguanamine powder, polymethylbenzoguanamine powder, tetrafluoroethylene powder, polymethylmethacrylate powder, cellulose powder, silk powder, nylon powder ( 12 nylon, 6 nylon), styrene / acrylic acid copolymer powder, divinylbenzene / styrene copolymer powder, vinyl resin powder, urea resin powder, phenol resin powder, fluororesin powder, silicon resin powder, acrylic resin powder, melamine Resin powder, epoxy resin powder, polycarbonate resin powder, microcrystalline fiber powder powder, comedemp And lauroyl lysine.
Examples of metal soap powder (surfactant metal salt powder) include zinc stearate, aluminum stearate, calcium stearate, magnesium stearate, zinc myristate, magnesium myristate, zinc cetyl phosphate, calcium cetyl phosphate, and sodium zinc cetyl phosphate. Each powder is mentioned.
As colored pigments, inorganic red pigments such as iron oxide, iron hydroxide and iron titanate, inorganic brown pigments such as γ-iron oxide, inorganic yellow pigments such as yellow iron oxide and loess, black iron oxide, carbon black, etc. Lake inorganic black pigments, inorganic purple pigments such as manganese violet and cobalt violet, inorganic green pigments such as chromium hydroxide, chromium oxide, cobalt oxide and cobalt titanate, inorganic blue pigments such as bitumen and ultramarine blue, and tar dyes And those obtained by lacquering natural pigments and composite powders obtained by combining these powders.
Examples of the pearl pigment include titanium oxide-coated mica, titanium oxide-coated mica, bismuth oxychloride, titanium oxide-coated bismuth oxychloride, titanium oxide-coated talc, fish scale foil, titanium oxide-coated glass powder, and titanium oxide-coated colored mica. Examples of the metal powder include aluminum powder, copper powder, and stainless steel powder.
The tar pigments are red No. 3, red No. 104, red No. 106, red No. 201, red No. 202, red No. 204, red No. 205, red No. 220, red No. 226, red No. 227, red No. 228 and red 230. No., red 401, red 505, yellow 4, yellow 5, yellow 202, yellow 203, yellow 204, yellow 401, blue 1, blue 2, blue 201, blue 404, Green No. 3, Green No. 201, Green No. 204, Green No. 205, Orange No. 201, Orange No. 203, Orange No. 204, Orange No. 206, Orange No. 207 and the like, and natural pigments include carminic acid, lacaic acid, Examples include calsamine, bradylin, and crocin.
These powders may be used as they are, but these powders may be combined, or may be used after surface treatment with an oil agent, silicone, fluorine compound or the like.
The said powder can be used 1 type or in combination of 2 or more type as needed.

  As UV absorbers, benzoic acid UV absorbers such as paraaminobenzoic acid, anthranilic acid UV absorbers such as methyl anthranilate, salicylic acid UV absorbers such as methyl salicylate, and cinnamic acids such as octyl paramethoxycinnamate And benzophenone ultraviolet absorbers such as 2,4-dihydroxybenzophenone, and urocanic acid ultraviolet absorbers such as ethyl urocanate.

  As preservatives and antibacterial agents, paraoxybenzoic acid esters, benzoic acid, sodium benzoate, sorbic acid, potassium sorbate, phenoxyethanol, salicylic acid, coalic acid, sorbic acid, parachlorometacresol, hexachlorophene, benzalkonium chloride, chlorhexidine chloride , Trichlorocarbanilide, photosensitizer, isopropylmethylphenol and the like.

  Tocopherol, butylhydroxyanisole, dibutylhydroxytoluene and the like as antioxidants, and lactic acid, lactate, citric acid, citrate, glycolic acid, succinic acid, tartaric acid, malic acid, potassium carbonate, sodium bicarbonate as pH adjusters , Ammonium bicarbonate, etc., as a chelating agent alanine, sodium edetate, sodium polyphosphate, sodium metaphosphate, phosphate, hydroxyethane diphosphone, etc., as a refreshing agent, L-menthol, camphor, light cargo oil, peppermint oil Examples of anti-inflammatory agents such as eucalyptus oil include allantoin, glycyrrhetinate, glycyrrhetin derivatives, tranexamic acid, azulene and the like.

  As skin beautifying ingredients, whitening agents such as arbutin, glutathione, and yukinoshita extract, royal jelly, photosensitizer, cholesterol derivatives, cell activators such as calf blood extract, skin roughening agent, nonyl acid wallenyl amide, nicotinic acid benzyl ester, Nicotinic acid β-butoxyethyl ester, capsaicin, gingerone, cantalis tincture, ictamol, caffeine, tannic acid, α-borneol, tocopherol nicotinate, inositol hexanicotinate, cyclandrate, cinnarizine, trazoline, acetylcholine, verapamil, cephalanthin , Blood circulation promoters such as γ-oryzanol, skin astringents such as zinc oxide and tannic acid, and antiseborrheic agents such as sulfur and thianthol.

  Vitamins such as vitamin A oil, retinol, retinol acetate, retinol palmitate, vitamin B2 such as riboflavin, riboflavin butyrate, flavin adenine nucleotide, vitamin B6 such as pyridoxine hydrochloride, pyridoxine dioctanoate Vitamin C such as L-ascorbic acid, L-ascorbic acid dipalmitate, L-ascorbic acid-2-sodium sulfate, dl-α-tocopherol-L-ascorbic acid diester dipotassium, calcium pantothenate, D -Pantothenic alcohols, pantothenyl ethyl ether, pantothenic acids such as acetyl pantothenyl ethyl ether, vitamin Ds such as ergocalciferol, cholecalciferol, nicotinic acid, benzyl nicotinate, Nicotinic acids such as succinic acid amide, dl-α-tocopherol, dl-α-tocopherol acetate, dl-α-tocopherol nicotinate, vitamin E such as dl-α-tocopherol succinate, vitamin P, biotin, etc. .

  Amino acids include arginine, aspartic acid, cystine, cysteine, methionine, serine, leucine, isoleucine, tryptophan, alanine, glycine, proline and the like, nucleic acids such as deoxyribonucleic acid, and hormones such as estradiol and ethinylestradiol.

  Examples of the dosage form of the cosmetic of the present invention include a powder dosage form, an oil-in-water emulsifier type, a water-in-oil emulsifier type, an oily agent type, and a solvent type. Examples of cosmetic forms include powder, powder solid, oily solid, cream, gel, liquid, mousse, and spray. Further, the cosmetic of the present invention only needs to contain the surface-coated powder of the present invention, in particular, foundation, concealer, white powder, eye shadow, blusher, makeup base, eye color, lipstick, eyebrow, mascara, It can be suitably used for makeup cosmetics such as eyeliner and nail polish, and sunscreen cosmetics.

EXAMPLES Next, although an Example is given and this invention is demonstrated still in detail, this invention is not limited at all by these. In the following examples,% means mass%.
1 Production of silicone phosphate triester [Production Example 1]
265 g of carbinol-modified silicone (formula 2) and 136 g of tetrahydrofuran were mixed and cooled to -40 ° C. After adding 200 ml of lithium diisopropylamide (LDA) (1 mol / THF solution) dropwise and reacting for 90 minutes, 7.8 g of phosphorus oxychloride (formula 1) was added and allowed to react for 1 hour. After raising the temperature to 25 ° C. and further aging for 2 hours, 42 g of concentrated hydrochloric acid was added to terminate the reaction. The mixture containing silicone phosphate triester was obtained by washing with methanol and distilling off the solvent. According to ³¹ P-NMR measurement, the composition ratio of the obtained mixture was 92% for the formula (I) as a triester, 1% for the formula (II) as a diester, and other by-products containing polyphosphoric acid. 7%.

[Production Example 2]
302 g of carbinol-modified silicone (formula 3) and 150 g of tetrahydrofuran were mixed and cooled to −40 ° C. After 74 ml of n-butyllithium (1.6 mol / hexane solution) was added dropwise and reacted for 90 minutes, 5.4 g of phosphorus oxychloride (Formula 1) was added and reacted for 1 hour. After raising the temperature to 25 ° C. and aging for another 2 hours, 10 g of water was added to terminate the reaction. The mixture containing silicone phosphate triester was obtained by washing with methanol and distilling off the solvent. According to ³¹ P-NMR measurement, the composition ratio of the obtained mixture was 83% for the formula (I) as a triester and 17% for the formula (II) as a diester.

[Production Example 3]
291 g of carbinol-modified silicone (formula 2), 87 g of tetrahydrofuran and 19 g of triethylamine were mixed and cooled to −40 ° C. A mixed solution of 8.6 g of phosphorus oxychloride (Formula 1) and 18 g of tetrahydrofuran was added dropwise in about 30 minutes. After aging at −40 ° C. for 5 hours and at 25 ° C. for 12 hours, the mixture was washed with methanol and the solvent was distilled off to obtain a mixture containing silicone phosphate triester. According to ³¹ P-NMR measurement, the composition ratio of the obtained mixture was 64% for formula (I) as a triester, 18% for formula (II) as a diester, and other by-products containing polyphosphoric acid. 18%.

[Production Example 4]
6.1 g of phosphorus oxychloride (formula 1) was dissolved in 93 g of tetrahydrofuran at 25 ° C. To this solution, a mixed solution of 300 g of carbinol-modified silicone (formula 4) and 8.1 g of triethylamine was dropped in about 2 hours. After aging for 15 hours, 0.7 g of water and 4.1 g of triethylamine were added to complete the reaction. After washing with methanol, the solvent was distilled off to obtain a mixture containing silicone phosphate triester. According to ³¹ P-NMR measurement, the composition ratio of the obtained mixture was 11% for the formula (I) as a triester, 66% for the formula (II) as a diester, and the formula (III) as a monoester. Was 3%, and other by-products containing polyphosphoric acid were 20%.

2 Manufacture of surface-coated powder The surface-coated powder was prepared by the following method using the product containing the silicone phosphate triester manufactured by the above method. Other powders were similarly prepared.

[Production Example 5]
Example of Titanium Oxide A solution of 1.0 g of the product of Production Example 1 as a surface treatment agent and 70 g of n-hexane dissolved in 49.0 g of titanium oxide was added, and this was highly dispersed for 30 minutes with a paint shaker. I let you. Thereafter, the obtained slurry was air-dried, fired at 125 ° C. for 1 hour, pulverized with a pulverizer, and surface-treated with 2.0% of the product of Production Example 1 with respect to the powder. Got.

[Production Example 6]
Example of Bengala or iron oxide In the same manner as above, 47.5 g of Bengala or iron oxide was added with a mixture of 2.5 g of the product of Production Example 2 as a surface treatment agent and 70 g of n-hexane. Was highly dispersed in a paint shaker for 30 minutes. Thereafter, the obtained slurry was air-dried, fired at 125 ° C. for 1 hour, pulverized by a pulverizer, and surface-treated with 5.0% of the product of Production Example 2 with respect to the powder. Got.

[Production Example 7]
Example of talc, mica or sericite As above, a mixed solution in which 0.5 g of the product of Production Example 1 as a surface treatment agent and 70 g of n-hexane were dissolved in 49.5 g of talc, mica or sericite. This was added and highly dispersed in a paint shaker for 30 minutes. Thereafter, the obtained slurry was air-dried, fired at 125 ° C. for 1 hour, pulverized with a pulverizer, and surface-treated with 1.0% of the product of Production Example 1 based on the powder. Got.

[Production Example 8]
Example of Composite Treatment 45 g of the product of Production Example 2 as a surface treatment agent and 15 g of isopropyl triisostearyl titanate were dissolved in 750 g of isopropyl alcohol, and then charged into a 20 L Henschel mixer. 2940 g of titanium oxide (TIPAQUE CR-50 manufactured by Ishihara Sangyo) was added thereto and uniformly dispersed at 70 ° C. Next, it heated at 120 degreeC and stirred for about 2 hours, distilling a solvent off under reduced pressure. After the powder was dried, it was cooled to room temperature, removed from the mixer, and pulverized with an atomizer. Titanium oxide surface-treated with 1.5% of the product of Production Example 2 and 0.5% of isopropyltriisostearyl titanate after firing for 6 hours in a thermostat at 130 ° C. Got.

[Production Example 9]
Example of Composite Treatment 50 g of the product of Production Example 2 as a surface treatment agent and 50 g of isopropyl triisostearyl titanate were added to 1250 g of isopropyl alcohol and dissolved, and then charged into a 20 L Henschel mixer. 4900 g of titanium oxide (TIPAQUE CR-50 manufactured by Ishihara Sangyo) was added thereto and uniformly dispersed at 70 ° C. Next, it heated at 120 degreeC and stirred for about 2 hours, distilling a solvent off under reduced pressure. After the powder was dried, it was cooled to room temperature, removed from the mixer, and pulverized with an atomizer. Titanium oxide surface-treated with 1.0% of the product of Production Example 2 and 1.0% of isopropyltriisostearyl titanate after firing for 6 hours in a thermostatic bath at 130 ° C. Got.

[Production Example 10]
Example of Composite Treatment 15 g of the product of Production Example 2 as a surface treatment agent and 45 g of isopropyl triisostearyl titanate were added to 750 g of isopropyl alcohol and dissolved, and then charged into a 20 L Henschel mixer. 2940 g of titanium oxide (TIPAQUE CR-50 manufactured by Ishihara Sangyo) was added thereto and uniformly dispersed at 70 ° C. Next, it heated at 120 degreeC and stirred for about 2 hours, distilling a solvent off under reduced pressure. After the powder was dried, it was cooled to room temperature, removed from the mixer, and pulverized with an atomizer. Titanium oxide surface-treated with 0.5% of the product of Production Example 2 and 1.5% of isopropyltriisostearyl titanate after firing for 6 hours in a thermostat at 130 ° C. Got.

[Production Comparative Example 1]
A solution prepared by dissolving 1.0 g of isopropyl triisostearyl titanate and 50 g of isopropyl alcohol as a surface treatment agent was added to 49.0 g of titanium oxide, and this was highly dispersed for 30 minutes with a paint shaker. Thereafter, the obtained slurry was air-dried, fired at 125 ° C. for 1 hour, pulverized by a pulverizer, and titanium oxide surface-treated with 2.0% isopropyl triisostearyl titanate was obtained. It was.

3 Evaluation of Dispersibility of Surface-Coated Powder (Composite Treatment) The dispersibility of the surface-coated titanium oxide of Production Examples 8 to 10 and Production Comparative Example 1 was evaluated. Examples of the dispersion solvent include (1) decamethylcyclopentasiloxane, (2) glyceryl tri-2-ethylhexanoate, (3) decamethylcyclopentasiloxane, 2-methoxyhexyl paramethoxycinnamate, and isononane, which are widely used in cosmetics. A mixture of isotridecyl acid at a mass ratio of 22: 6: 2 (hereinafter referred to as a mixed solvent) was used. 1 g of the surface-coated powder was placed in a standard bottle, 30 ml of the above dispersion solvent was added thereto, the cap was capped, and the mixture was dispersed with an ultrasonic machine (BRANSONIC 1510J-DTH 42 kHz) for 30 minutes. Then, it was transferred to a settling tube having a bottom area of 1 cm ² and a height of 30 cm, left at room temperature, and the volume of the dispersed layer was visually evaluated after 6 days. At that time, the reading of the sedimentation tube scale (the height of the dispersion layer) was used as a criterion. The results are shown in Table 1.
(Criteria)
A: The height of the dispersed layer is 25 cm or more. O: The height of the dispersed layer is 20 cm or more and less than 25 cm. Δ: The height of the dispersed layer is 10 cm or more and less than 20 cm. X: The height of the dispersed layer is less than 10 cm.

4. Example of cosmetic preparation The surface-coated powder prepared by the above method was used in the following formulation.
In the following examples, for example, “Production Example 1 (2.0%) treated titanium oxide” means the product (silicone) obtained in Production Example 1 in an amount of 2.0% by mass relative to titanium oxide. It means a surface-treated powder coated with a mixture containing a phosphate triester.

[Examples 1 to 9 and Comparative Examples 1 to 3]
W / O type foundation

(Production method)
(1) The components 1-17 are processed with a roller.
(2) The components 18-21 are processed with a roller.
(3) (1), (2) and components 22 and 23 are uniformly mixed with a desper.
(4) Components 24 to 28 are gradually added to (3) and emulsified.
(5) (4) was defoamed and filled into a container to obtain a W / O-type foundation.

(Evaluation)
For the W / O-type foundations of Examples 1 to 9 and Comparative Examples 1 to 3, the 20 panelists specializing in cosmetics evaluation gave “uniformity of makeup film”, “makeup lasting effect”, and “smooth feeling of use”. Each of these items was evaluated according to the following criteria, using a 7-point rating according to the following criteria, and using the average score of all panels.
[Evaluation criteria]
(Evaluation result): (Grade)
Very good: 6 points Good: 5 points Somewhat good: 4 points Normal: 3 points Somewhat bad: 2 points Bad: 1 point Very bad: 0 points
[Criteria]
(Average score): (Judgment)
5.0 or more: ◎ Very good 3.5 or more to less than 5.0: ○ Good 1.5 or more to less than 3.5: △ Defect Less than 1.5: × Very poor

(result)
The W / O type foundations of Examples 1 to 9 were W / O type foundations excellent in the uniformity of the cosmetic film, the makeup lasting effect, and the smooth feeling of use. Since the W / O type foundation of Comparative Example 1 has a small amount of methyl hydrogen polysiloxane treatment to titanium oxide, it is inferior in the uniformity of the cosmetic film, makeup lasting effect, and smooth feeling of use, and the treatment to titanium oxide Even in Comparative Example 2 having a large amount, it was inferior in the uniformity of the cosmetic film, the makeup lasting effect, and the smooth feeling of use. Furthermore, the W / O type foundation of Comparative Example 3 was also inferior in the uniformity of the cosmetic film, the makeup sustaining effect, and the smooth feeling of use.

[Example 10]
O / W type liquid foundation (component) (%)
1. Monooleic acid polyoxyethylene sorbitan (20EO) 0.5
2. Sorbitan sesquioleate 0.5
3. 1,3-butylene glycol 10.0
4). Production Example 4 (3.0%) treated titanium oxide 10.0
5. Production Example 4 (3.0%) treated bengara 0.4
6). Production Example 4 (3.0%) treated yellow iron oxide 2.0
7). Production Example 4 (3.0%) treated black iron oxide 0.1
8). Production Example 4 (3.0%) treated talc 5.0
9. Carboxyvinyl polymer 0.3
10. Triethanolamine 1.0
11. Purified water remaining amount 12. Ethanol 2.0
13. Stearic acid 1.0
14 Behenyl alcohol 0.5
15. Liquid paraffin 2.0
16. Glyceryl tri-2-ethylhexanoate 2.0
17. 2-Ethylhexyl paramethoxycinnamate 2.0
18. Vaseline 0.5
19. Preservative appropriate amount20. Perfume

(Production method)
(1) Components 1 to 8 are uniformly dispersed with a roller.
(2) Mix components 9-12 uniformly.
(3) Add (1) to (2) and mix uniformly.
(4) Components 13 to 19 are mixed and dissolved at 80 ° C.
(5) Add (4) to (3) at 80 ° C. and emulsify.
(6) (5) was cooled, component 20 was added, and an O / W type foundation was obtained.

(result)
The O / W type foundation of Example 10 was an O / W type foundation excellent in the uniformity of the cosmetic film, the makeup lasting effect, and the smooth feeling of use.

[Example 11]
Oily solid foundation (component) (%)
1. Talc 15.0
2. Mica 10.0
3. Production Example 2 (5.0%) treated titanium oxide 15.0
4). Production Example 2 (5.0%) treated bengara 1.0
5. Production Example 2 (5.0%) treated yellow iron oxide 3.0
6). Production Example 2 (5.0%) treated black iron oxide 0.2
7). Polyethylene wax 7.0
8). Microcrystalline wax 6.0
9. 10. Glyceryl tri-2-ethylhexanoate remaining 10 Dimethylpolysiloxane 10.0
11. Liquid paraffin 20.0
12 Polyoxyethylene methylsiloxane / polyoxypropylene oleyl methylsiloxane / dimethylsiloxane copolymer (Note 3) 2.0
13. Preservative appropriate amount14. Perfume

(Production method)
(1) Components 7 to 13 are dissolved by heating at 90 ° C.
(2) Add components 1 to 6 to (1) and uniformly disperse with a roller.
(3) Component 14 was added to (2), dissolved at 80 ° C., and then filled into a metal pan to obtain an oily solid foundation.

(result)
The oily solid foundation of Example 11 was an oily solid foundation excellent in the uniformity of the cosmetic film, the makeup sustaining effect, and the smooth feeling of use.

[Example 12]
Sticky oily solid concealer (component) (%)
1. Paraffin wax 5.0
2. Polyethylene wax 5.0
3. Candelilla Row 2.0
4). Glyceryl tri-2-ethylhexanoate 15.0
5. Methylphenylpolysiloxane 25.0
6). Acetic acid liquid lanolin 10.0
7). 2-Ethylhexyl paramethoxycinnamate 5.0
8). Production Example 3 (7.0%) treated titanium oxide 20.0
9. Production Example 3 (7.0%) treated yellow iron oxide 2.0
10. Production Example 3 (7.0%) treated bengara 0.5
11. Production Example 3 (7.0%) treated black iron oxide 0.2
12 Mica 7.0
13. Preservative appropriate amount

(Production method)
(1) Components 1 to 7 are mixed and dissolved at 100 ° C.
(2) Ingredients 8 to 13 are uniformly mixed in (1) at 90 ° C.
(3) Process (2) with three rollers.
(4) (3) was defoamed, dissolved and filled in a capsule at 85 ° C., and then cooled at 4 ° C. to obtain a stick concealer.

(result)
The stick-like oily solid concealer of Example 12 was a stick-like oily solid concealer excellent in the uniformity of the cosmetic film, the makeup lasting effect, and the smooth feeling of use.

[Example 13]
Solid powder foundation (component) (%)
1. Production Example 1 (1.0%) treated talc 30.0
2. Production Example 1 (1.0%) treated mica 15.0
3. Production Example 1 (1.0%) treated mica titanium oxide 15.0
4). Production Example 1 (1.0%) treated sericite Production Example 1 (1.0%) yellow iron oxide 2.0
6). Production Example 1 (1.0%) Bengala 0.5
7). Production Example 1 (1.0%) black iron oxide 0.2
8). Synthetic phlogopite 5.0
9. Cross-linked silicone / reticulated silicone block copolymer 1.0
10. Preservative appropriate amount11. Liquid paraffin 3.0
12 Dimethylpolysiloxane 3.0
13. Glyceryl 2-ethylhexanoate 3.0
14 Perfume

(Production method)
(1) Components 1 to 10 are uniformly dispersed at 75 ° C. in a Henschel mixer (Mitsui Miike).
(2) The components 11 to 13 are mixed and dissolved uniformly.
(3) While stirring (1) with a Henschel mixer, add (2) and 14 and uniformly disperse.
(4) Grind (3) with a pulverizer.
(5) (4) was filled into a metal pan and compression molded to obtain a solid powdery foundation.

(result)
The solid powder foundation of Example 13 was a solid powder foundation excellent in the uniformity of the cosmetic film, the makeup lasting effect, and the smooth feeling of use.

[Example 14]
Solid powder eye shadow (component) (%)
1. Production Example 2 (1.0%) treated synthetic gold mica 10.0
2. Production Example 2 (1.0%) treated talc Titanium oxide coated mica 30.0
4). Boron nitride 5.0
5. Polyethylene terephthalate / aluminum / epoxy laminated powder 5.0
6). Ultramarine 2.0
7). Red 202 0.5
8). Polyalkyl acrylate 1.0
9. Preservative appropriate amount10. Liquid paraffin 3.0
11. Dimethylpolysiloxane 5.0
12.2-Glyceryl ethylhexanoate 3.0
13. Perfume

(Production method)
(1) Components 1 to 9 are uniformly dispersed at 75 ° C. in a Henschel mixer (Mitsui Miike).
(2) The components 10 to 12 are mixed and dissolved uniformly.
(3) While stirring (1) with a Henschel mixer, add (2) and 13 and uniformly disperse.
(4) Grind (3) with a pulverizer.
(5) A metal pan was filled with (4) and compression molded to obtain a solid powder eye shadow.

(result)
The solid powder eye shadow of Example 14 was a solid powder eye shadow excellent in the uniformity of the cosmetic film, the makeup lasting effect, and the smooth feeling of use.

[Example 15]
Solid powder face color (component) (%)
1. Production Example 3 (1.0%) treated mica 20.0
2. Production Example 3 (1.0%) treated talc Titanium oxide coated mica 10.0
4). Ultramarine 0.5
5. Red 226 0.2
6). Polyalkyl acrylate 1.0
7). Preservative appropriate amount 8. Liquid paraffin 2.0
9. Dimethylpolysiloxane 3.0
10.2-Glyceryl ethylhexanoate 3.0
11. Perfume

(Production method)
(1) Components 1 to 7 are uniformly dispersed at 75 ° C. in a Henschel mixer (Mitsui Miike).
(2) Heat components 8 to 10 to 65 ° C. and mix and dissolve uniformly.
(3) While stirring (1) with a Henschel mixer, add (2) and 11 and uniformly disperse.
(4) Grind (3) with a pulverizer.
(5) A metal pan was filled with (4) and compression molded to obtain a solid powder face color.

(result)
The solid powder face color of Example 15 was a solid powder face color excellent in the uniformity of the cosmetic film, the makeup lasting effect, and the smooth feeling of use.

[Example 16]
Powdered white powder (component) (%)
1. Production Example 1 (0.5%) treated mica 20.0
2. Production Example 1 (0.5%) treated talc Mica titanium 10.0
4). Red 226 0.5
5. Liquid paraffin 0.5
6). Glyceryl tri-2-ethylhexanoate 1.0
7). Preservative appropriate amount 8. Perfume

(Production method)
(1) Components 1 to 4 are mixed uniformly.
(2) While stirring (1) with a Henschel mixer, ingredients 5 to 8 are added and mixed uniformly.
(3) (2) was pulverized with a pulverizer to obtain white powder.

(result)
The powdery white powder of Example 16 was a powdery white powder excellent in the uniformity of the decorative film, the makeup lasting effect, and the smooth feeling of use.

[Example 17]
Stick-shaped lipstick (ingredient) (%)
1. Polyethylene wax 10.0
2. Carnauba wax 5.0
3. Paraffin wax 2.0
4. Cetyl 2-ethylhexanoate 5 Liquid paraffin 10.0
6). Isotridecyl isononanoate 10.0
7). Dimethylpolysiloxane 5.0
8). Red 202 0.5
9. Yellow 4 2.0
10. Production Example 2 (2.0%) treated mica titanium 3.0
11. Production Example 2 (2.0%) treated titanium oxide 0.5
12 Production Example 2 (2.0%) treated black iron oxide 0.1
13. α-Tocopherol 0.5
14 Perfume

(Production method)
(1) Components 1 to 7 are uniformly dissolved and mixed at 100 ° C.
(2) Add components 8 to 14 to (1) and mix uniformly.
(3) (2) was poured into a container and cooled to obtain a stick-shaped lipstick.

(result)
The stick-shaped lipstick of Example 17 was a stick-shaped lipstick excellent in the uniformity of the cosmetic film, the makeup lasting effect, and the smooth feeling of use.

[Example 18]
O / W type mascara (component) (%)
1. Stearic acid 2.0
2. Beeswax 10.0
3. Cetostearyl alcohol 1.0
4). Monooleic acid polyoxyethylene sorbitan (20EO) 1.5
5. Sorbitan sesquioleate 0.5
6). Dimethylpolysiloxane 5.0
7). Production Example 3 (5.0%) treated black iron oxide 5.0
8). Silicic anhydride 3.0
9. Purified water remaining amount 10.1,3-butylene glycol 10.0
11. Triethanolamine 1.5
12 Alkyl acrylate copolymer emulsion (Note 5) 30.0
13. Preservative appropriate amount14. Perfume appropriate amount (Note 5) Iodosol 32A707 (45% solids) (NSC Japan)

(Production method)
(1) Components 1 to 3 are uniformly mixed at 80 ° C.
(2) Components 4 to 8 are processed with a roller.
(3) Components 9 to 14 are mixed uniformly at 80 ° C.
(4) After mixing (1) and (2), (3) is added and emulsified.
(5) (4) was cooled to obtain an O / W type mascara.

(result)
The O / W type mascara of Example 18 was an O / W type mascara excellent in the uniformity of the cosmetic film, the makeup lasting effect, and the smooth feeling of use.

[Example 19]
Non-aqueous mascara (component) (%)
1. Rosin acid pentaerythritol 10.0
2. Candelilla resin 3.0
3. Beeswax 2.0
4). Ceresin wax 2.0
5. Dextrin palmitate 2.0
6). Trimethylsiloxysilicic acid 3.0
7). Dimethyl distearyl ammonium hectorite 5.0
8). Propion carbonate 1.0
9. Light liquid isoparaffin (Note 6) Dimethylpolysiloxane 3.0
11. Production Example 1 (10%) treated black iron oxide 5.0
12 Silica 3.0
13. Talc 5.0
(Note 6) IP solvent 1620 (made by Idemitsu Kosan Co., Ltd.)

(Production method)
(1) Ingredients 1-5 are heated to 110 ° C.
(2) Add components 6 to 10 to (1) and mix.
(3) Components 11 to 13 are added to and mixed with (2).
(4) (3) was processed with three rollers to obtain a non-aqueous mascara.

(result)
The non-aqueous mascara of Example 19 was a non-aqueous mascara excellent in the uniformity of the cosmetic film, the makeup lasting effect, and the smooth feeling of use.

[Example 20]
Oily eyeliner (component) (%)
1. Ceresin wax 11.0
2. Polyisobutylene 16.0
3. Polyethylene wax 8.0
4). Light liquid isoparaffin (Note 6) Dimethylpolysiloxane 3.0
6). Production Example 2 (0.5%) treated black iron oxide 15.0
7). Production Example 2 (0.5%) treated talc 5.0
8). Preservative appropriate amount 9. Perfume

(Production method)
(1) Ingredients 1-5 are heated to 100 ° C. and mixed uniformly.
(2) Ingredients 6-9 are heated to 80 ° C. and mixed uniformly.
(3) Add (2) to (1) and mix uniformly.
(4) (3) was processed with a roller to obtain an oily eyeliner.

(result)
The oily eyeliner of Example 20 was an oily eyeliner excellent in cosmetic film uniformity, makeup lasting effect, and smooth use feeling.

[Example 21]
W / O type sunscreen (component) (%)
1. Production Example 1 (5.0%) treated zinc oxide 2.0
2. Production Example 1 (5.0%) treated fine particle titanium oxide 5.0
3. Tri (capryl / capric acid) glyceryl 5.0
4). Dimethylpolysiloxane 3.0
5. Octyl palmitate 3.0
6). 2-Ethylhexyl paramethoxycinnamate 10.0
7). Decamethylcyclopentasiloxane 10.0
8). Methyl polysiloxane, cetyl methyl polysiloxane, poly (oxyethylene oxypropylene)
Methylpolysiloxane copolymer (Note 7) 1.8
9. Glyceryl tri-2-ethylhexanoate 3.0
10. Preservative appropriate amount11. Sodium chloride 0.3
12 Purified water remaining amount 13. Dipropylene glycol 3.0
14 Ethanol 3.0
15. Perfume proper amount (Note 7) ABIL EM-90 (Evonic Goldschmidt GMBH)

(Production method)
(1) After components 3 and 4 are heated and dissolved, components 1 and 2 are added and dispersed uniformly with three rollers.
(2) After components 5 to 10 are dissolved at 70 ° C., (1) is added at 60 ° C. and uniformly mixed and dissolved.
(3) Components 11 to 13 are mixed and dissolved, and then added to (2) at 60 ° C. to emulsify.
(4) Components 14 and 15 were added to (3) and mixed uniformly to obtain a W / O type sunscreen.

(result)
The W / O type sunscreen of Example 21 was a W / O type sunscreen excellent in the uniformity of the cosmetic film, the makeup lasting effect, and the smooth feeling of use.

Claims (8)

Formula (I)

(In the formula, each R ₁ independently represents an alkyl group having 1 to 4 carbon atoms, and R may have at least one selected from —O— and —CO—.) (7 represents a divalent hydrocarbon group of 7 to 7 and n represents an integer of 5 to 40). Formula (I)

(In the formula, each R ₁ independently represents an alkyl group having 1 to 4 carbon atoms, and R may have at least one selected from —O— and —CO—.) 1 to 2 or more of silicone phosphoric acid triester represented by n represents a divalent hydrocarbon group of ˜7, and n represents an integer of 5 to 40,
Formula (II)

(Wherein R ₁ , R and n are the same as defined in the above formula (I)), one or more silicone phosphate diesters represented by 0 to 35% by mass, and
Formula (III)

(Wherein R ₁ , R and n are the same as defined in the above formula (I)), the surface of the silicone phosphate monoester represented by 1 or 2 or more and 0 to 5% by mass of the silicone phosphate monoester The powder according to claim 1, wherein the powder is coated. 3. The surface-coated powder according to claim 1, further comprising an organic titanate as a surface treatment agent in addition to the silicone phosphate ester. The surface-coated powder according to claim 3, wherein the mass ratio of the silicone phosphate ester and the organic titanate is 1: 9 to 9: 1. 5. The surface-coated powder according to claim 3, wherein the organic titanate is isopropyl triisostearyl titanate. 6. The surface-coated powder according to claim 1, wherein the powder is at least one selected from the group consisting of titanium oxide, zinc oxide and iron oxide. The surface-coated powder according to any one of claims 1 to 6, wherein the coating amount of the silicone phosphate ester is 0.01 to 5% by mass of the surface-coated powder. A cosmetic comprising the surface-coated powder according to any one of claims 1 to 7.