Surface-coated powder and cosmetic containing surface-coated powder

A crosslinked organosilicon resin-coated powder addresses the issues of water repellency, spreadability, and adhesiveness in cosmetics by forming a uniform fine structure, enhancing cosmetic performance.

WO2025142746A1PCT designated stage expired Publication Date: 2025-07-03KOSE CORPORATION
View PDF 7 Cites 0 Cited by

Patent Information

Application Number
PCT/JP2024/045046
Authority / Receiving Office
WO · WO
Patent Type
Applications
Current Assignee / Owner
Priority Date
2023-12-28
Filing Date
2024-12-19
Publication Date
2025-07-03

AI Technical Summary

Technical Problem

Existing cosmetic powders face issues with water repellency, smooth spreadability, skin adhesiveness, and aggregation, as addressed by previous surface treatment agents such as alkyl polysiloxane, n-octyltrimethoxysilane, tridecafluorooctyltriethoxysilane, and silicone gel.

Method used

A surface-coated powder using a crosslinked organosilicon resin, formed by an addition reaction between an alkenyl-containing organosilicon resin and organohydrogenpolysiloxane, which prevents aggregation and enhances water repellency and skin adhesiveness through a uniform fine uneven structure.

Benefits of technology

The crosslinked organosilicon resin-coated powder achieves high water repellency, smooth spreadability, and strong skin adhesiveness, improving makeup persistence and pore covering effects in cosmetics.

✦ Generated by Eureka AI based on patent content.

Smart Images

  • Figure JP2024045046_03072025_PF_FP_ABST
    Figure JP2024045046_03072025_PF_FP_ABST
Patent Text Reader

Abstract

The present invention addresses the problem of providing a surface-coated powder which has high water repellency, smooth spreadability, and skin adhesion, and in which aggregation does not occur. The present invention also addresses the problem of providing a cosmetic containing a surface-coated powder and exhibiting excellent cosmetic persistence, smooth spreadability, skin adhesion, and pore-covering effect. A surface-coated powder that solves the problem of the present invention is characterized by involving surface-coating a powder with a specific crosslinked organic silicon resin. A cosmetic that solves the problem of the present invention is characterized by comprising a powder that is surface-coated with a specific crosslinked organic silicon resin.
Need to check novelty before this filing date? Find Prior Art

Description

Surface-coated powder and cosmetic containing the surface-coated powder

[0001] The present invention relates to a surface-coated powder coated with a crosslinked organosilicon resin and a cosmetic composition containing the same.

[0002] In the field of cosmetics, surface-coated powders using various surface treatment agents and cosmetics containing the same have been studied for the purpose of improving the dispersibility of powders, improving the cosmetic durability, and adjusting the feel of the powder. For example, there is a surface-treated powder using alkylpolysiloxane and methylhydrogenpolysiloxane as surface treatment agents, which has excellent adhesion to the skin, no aggregation, is particularly smooth and pleasant to the touch, has a highly saturated color tone when used in combination with a coloring pigment, and is excellent in hydrophobicity and water resistance (see, for example, Patent Document 1); a surface-treated powder which is coated with n-octyltrimethoxysilane or n-octyltriethoxysilane by a silane coupling reaction, has high water repellency, feels moist and not heavy to the touch, and has high adhesion to the skin (see, for example, Patent Document 2); Proposed technologies include a surface-treated pigment that uses octyltriethoxysilane as a surface treatment agent and has excellent water and oil repellency (see, for example, Patent Document 3), a surface-treated powder that uses a specific silicone gel as a surface treatment agent and can provide a smooth and light feel, has a moist feel when used, has excellent adhesion to the skin, and improves the moldability and impact resistance of solid powder cosmetics (see, for example, Patent Document 4), and a technology that includes a powder of titanium oxide coated with a silicone resin in a sunscreen cosmetic, which has a high UV protection effect, does not leave a white cast on the skin after application, and achieves a smooth finish (see, for example, Patent Document 5).

[0003] Japanese Patent Laid-Open No. 11-148028 Japanese Patent Laid-Open No. 2001-181136 Japanese Patent Laid-Open No. 2007-238690 International Publication No. 2014 / 102863 Pamphlet Japanese Patent Laid-Open No. 2014-91736

[0004] However, for example, in Patent Documents 1 and 2, although the oil treatment provides a pleasant feel and improves skin adhesion, the water repellency and smooth spreadability that contribute to cosmetic long-lasting properties are not satisfactory. Furthermore, in Patent Document 3, the high water and oil repellency and lack of aggregation that are characteristic of fluorinated oil agents are exhibited, but the skin adhesion is poor. In Patent Document 4, the soft feel characteristic of silicone gel is imparted, but the silicone gel induces aggregation, so the smooth spreadability and lack of aggregation are unsatisfactory. Furthermore, in Patent Document 5, a powder in which titanium oxide is coated with a silicone resin used in sunscreen cosmetics is improved in dispersibility, but the water repellency and skin adhesion are unsatisfactory.

[0005] Therefore, an object of the present invention is to develop a surface-coated powder that is not only water-repellent and non-aggregating, but also exhibits smooth spreading upon application and high skin adhesion.

[0006] In light of these circumstances, the present inventors conducted extensive research and found that by preparing a surface-coated powder coated with a specific crosslinked organosilicon resin, the crosslinked portions of the crosslinked organosilicon resin prevent the resin portions from agglomerating during the surface coating treatment of the powder, resulting in a uniform coating treatment on the powder surface and the formation of a fine, uniform uneven structure on the powder surface. Furthermore, the prepared surface-coated powder has a uniform powder surface, which allows smooth spreading when applied to the skin, and the fine uneven structure produces a lotus effect (the effect of increasing the contact angle of water), resulting in high water repellency. In addition, the inventors found that the increased contact points with the skin result in high skin adhesion, and further prevent aggregation of the powder particles themselves. Furthermore, the inventors found that cosmetics containing this surface-coated powder have excellent cosmetic durability, smooth spreading, skin adhesion, and pore-covering effect, leading to the completion of the present invention.

[0007] That is, the present invention includes the following aspects: [1] Powder that has been surface-coated with the following component (A): (A) a crosslinked organosilicon resin that is an addition reaction product of the following components (X) and (Y), wherein the amount of hydrogen gas generated per mass from this crosslinked organosilicon resin is 1.5 mL / g or less under standard conditions; (X) an alkenyl-containing organosilicon resin represented by the following formula (1) and having one or more alkenyl groups per molecule: [In the formula, R 1 are each independently an alkenyl group having 2 to 8 carbon atoms, and R 2 are each independently a group selected from an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, and an aralkyl group having 7 to 30 carbon atoms. 3 are each independently an organopolysiloxane-containing group, and the R 2 and each R 3 3 SiO 1/2 R in units 3 at least one of the above is an organopolysiloxane-containing group. a1, a2, a3, b, c, and d are numbers that satisfy 0<a1≦5, 0<a2≦400, 0≦a3≦400, 0≦b≦320, 0≦c≦320, and 0<d≦1,000, and 0.5≦(a1+a2+a3) / d≦1.5.] (Y) An organohydrogenpolysiloxane represented by the following formula (2) and having two or more hydrosilyl groups per molecule: an amount such that the amount of hydrosilyl groups is 0.5 to 1.2 moles per mole of alkenyl groups in the above component (X). [In the formula, R 2 is the same as above, and R 4 are each independently a hydrogen atom or the R 2 and all R 4Two or more of the elements are hydrogen atoms, and e, f, g, and h are 0 or positive numbers, with the proviso that 2≦e+f+g+h<32 is satisfied.] [2] The surface-coated powder according to [1], wherein the powder is a plate-like powder. [3] The surface-coated powder according to [1] or [2], wherein the amount of surface-coated component (A) is 0.5 to 10 mass% relative to the total amount of powder to be treated. [4] The surface-coated powder according to [1] or [2], obtained by surface-coating component (A) and the powder using a media mill. [5] A cosmetic preparation containing the surface-coated powder according to [1]. [6] The cosmetic preparation according to [5], further containing component (B) spherical powder. [7] The cosmetic preparation according to [5] or [6], wherein the content of the surface-coated powder is 0.01 to 99 mass%. [8] The cosmetic preparation according to [6], wherein the content of component (B) is 3 to 80 mass%. [9] The cosmetic preparation according to [6] or [8], wherein the content mass ratio of the surface-coated powder to the component (B) [surface-coated powder / component (B)] is 0.01 to 30.

[10] The cosmetic preparation according to [5], [6] or [8], which is a powder cosmetic preparation.

[0008] The present invention provides a surface-coated powder that has high water repellency, smooth spreadability, excellent skin adhesion, and low aggregation. Furthermore, cosmetics containing this surface-coated powder have even greater smooth spreadability, as well as long-lasting makeup, excellent skin adhesion, and excellent pore-covering properties.

[0009] 1 is a photograph showing the surface state of Production Example 1 and a graph showing the undulations at the white line portion of the photograph. 2 is a photograph showing the surface state of Comparative Production Example 1 and a graph showing the undulations at the white line portion of the photograph.

[0010] Preferred embodiments of the present invention are described in detail below. However, the present invention is not limited to the following preferred embodiments and can be freely modified within the scope of the present invention. In this specification, the symbol "to" means a range including the numerical values ​​before and after it. In this specification, percentages are expressed by mass unless otherwise specified. The "average particle size" of a powder in this specification refers to the median diameter D50 value evaluated using image analysis. However, the "average particle size" of a surface-coated powder in this specification refers to the median diameter D50 value determined by measurement using a particle size distribution analyzer (LA-960, manufactured by HORIBA). The average particle size of powders other than surface-coated powders is determined by observing the surface condition using a scanning electron microscope (JEOL, JSM-7800prime) and measuring the major axis using an image analyzer (Luzex AP, manufactured by Nireco Corporation) to obtain the value (D50). The average thickness is determined by the arithmetic mean of all particles whose thickness can be read within the same field of view of the scanning electron microscope.

[0011] <Surface-coated powder> Component (A) of the present invention will be described in detail below. Component (A) is a crosslinked organosilicon resin that is an addition reaction product of the following components (X) and (Y), and the amount of hydrogen gas generated per mass from this crosslinked organosilicon resin is 1.5 mL / g or less under standard conditions.

[0012] [Component (X)] Component (X) is an alkenyl group-containing organosilicon resin represented by the following formula (1) and containing one or more alkenyl groups per molecule, and can be used alone or in combination of two or more types. [In the formula, R 1 are each independently an alkenyl group having 2 to 8 carbon atoms, and R 2 are each independently a group selected from an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, and an aralkyl group having 7 to 30 carbon atoms. 3 are each independently an organopolysiloxane-containing group, and the R 2 and each R 3 3 SiO 1/2 R in units3 At least one of the groups is an organopolysiloxane-containing group. a1, a2, a3, b, c, and d are numbers that satisfy 0<a1≦5, 0<a2≦400, 0≦a3≦400, 0≦b≦320, 0≦c≦320, and 0<d≦1,000, and 0.5≦(a1+a2+a3) / d≦1.5.

[0013] In the above formula, R 1 are each independently an alkenyl group having 2 to 8 carbon atoms. More specific examples include a vinyl group, an allyl group, an isopropenyl group, a butenyl group, a pentenyl group, a hexenyl group, a cyclohexenyl group, and an octenyl group. A vinyl group and an allyl group are particularly preferred.

[0014] In the above formula, R 2 are each independently a group selected from an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, and an aralkyl group having 7 to 30 carbon atoms. Among these, an alkyl group, an aryl group, an aralkyl group, and a fluorine-substituted alkyl group having 1 to 10 carbon atoms are preferred. More specifically, examples include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a cyclopentyl group, a cyclohexyl group, a phenyl group, a tolyl group, and a trifluoropropyl group. An alkyl group having 1 to 5 carbon atoms, a phenyl group, or a trifluoropropyl group is particularly preferred. In addition, optionally, R 2 A part of the group may contain one or more groups selected from a hydroxyl group or an alkoxy group having 1 to 8 carbon atoms.

[0015] In the above formula, R 3 are each independently an organopolysiloxane-containing group, and the R 2 Examples of the organopolysiloxane-containing group include groups represented by the following formulas (3) to (6): 3 3 SiO 1/2 In each of the units, one or more R 3 is an organopolysiloxane-containing group. 3 A part of may be a hydroxyl group. [In the formula, R 2is the same as above, m is an integer that satisfies 0≦m≦5, i is an integer that satisfies 0≦i≦500, and j1 to j3 are each an integer that is 0 or more and 2 or less.]

[0016] m is an integer satisfying 0≦m≦5, preferably 0≦m≦2, and i is an integer satisfying 0≦i≦500, preferably 1≦i≦100, more preferably 1≦i≦50. If i is greater than 500, the melting point of the resin will be low, resulting in poor film-forming properties. j1 to j3 are each integers of 0 or more and 2 or less.

[0017] In the alkenyl group-containing organosilicon resin represented by the above formula (1), a1, a2, a3, b, c, and d are 0<a1≦5, preferably 0<a1≦4.5, more preferably 1≦a1≦4, and even more preferably 1≦a1≦3. If a1 is greater than 5, the possibility of gelation increases and film-forming properties are poor. 0<a2≦400, preferably 0<a2≦100, more preferably 0<a2≦50. 0≦a3≦400, preferably 0≦a3≦100, more preferably 0≦a3≦50. If a3 is greater than 400, the melting point of the resin is low, resulting in poor film-forming properties.

[0018] 0≦b≦320, 0≦c≦320, with b=0 and c=0 being preferred. When b and c are 0, the alkenyl group-containing organosilicon resin does not contain a flexible skeleton such as D units or T units, and is composed only of M units and Q units. By using an alkenyl group-containing organosilicon resin that does not contain D units or T units as a raw material, the crosslinked organosilicon resin, which is the addition reaction product, can form a strong coating.

[0019] It is a number that satisfies 0<d≦1,000, 0.5≦(a1+a2+a3) / d≦1.5, and preferably 0.7≦(a1+a2+a3) / d≦1.2. If the value of (a1+a2+a3) / d is less than the lower limit, the degree of crosslinking increases, the molecular weight increases, and the polymer becomes gel-like. If it exceeds the upper limit, the molecular weight decreases, resulting in poor film-forming properties.

[0020] The alkenyl group-containing organosilicon resin represented by the above formula (1) is a Q unit (SiO 4/2 ), M units (R 2 3 SiO 1/2 and R1 R 2 2 SiO 1/2 ) is an essential structure, and D unit (R 2 2 SiO 2/2 ), T unit (R 2 SiO 3/2 ) in any structure. It may be solid or liquid at 25°C, but solid is preferred from the viewpoint of film-forming properties. Examples include MQ resin, MTQ resin, MDQ resin, and MDTQ resin. Its weight-average molecular weight is preferably in the range of 1,000 to 30,000, and more preferably in the range of 3,000 to 15,000 from the viewpoint of performance and workability such as filtration. The weight-average molecular weight can be determined as the weight-average molecular weight converted into polystyrene by gel permeation chromatography (GPC) analysis.

[0021] [Component (Y)] Component (Y) is an organohydrogenpolysiloxane represented by the following formula (2) having two or more hydrosilyl groups per molecule, and can be used alone or in combination of two or more. The addition reaction amount is an amount that results in 0.5 to 1.2 moles of hydrosilyl groups per mole of alkenyl groups in component (X), preferably 0.5 to 1.2 moles, more preferably 0.8 to 1.2, and even more preferably 0.9 to 1.1. [In the formula, R 2 is the same as above, and R 4 are each independently a hydrogen atom or the above R 2 and all R 4 Two or more of them are hydrogen atoms, and e, f, g, and h are 0 or positive numbers, provided that 2≦e+f+g+h<32 is satisfied.

[0022] In the organohydrogenpolysiloxane having two or more hydrosilyl groups in one molecule represented by the above formula (2), R 4 are each independently a hydrogen atom or a monovalent hydrocarbon group having 1 to 30 carbon atoms and no aliphatic unsaturated bond, and all R 4 At least two of them are hydrogen atoms.

[0023] In the above formula (2), e, f, g, and h are 0 or positive numbers and may be selected to satisfy the relationship 2≦e+f+g+h<32. Preferably, g=0 and h=0 (i.e., 2≦e+f<32), more preferably, e=2, 0≦f<30, g=0, and h=0, and even more preferably, e=2, 10≦f≦30, g=0, and h=0. When the number of silicon atoms contained in component (Y) is 32 or more, the crosslinked organosilicon resin tends to embrace the solvent and become a gel. Therefore, a sticky film tends to form after the solvent evaporates. When the number of silicon atoms contained in component (Y) is less than 32, the crosslinked organosilicon resin tends to dissolve in the solvent and become a liquid. Therefore, a non-sticky film tends to be obtained after the solvent evaporates.

[0024] In the above formula (2), it is preferable that g = 0 and h = 0. When g and h are 0, the organohydrogenpolysiloxane does not contain branched components such as T units and Q units, and is a linear molecule composed only of M units and D units. By using a linear organohydrogenpolysiloxane as a raw material, the crosslinked organosilicon resin, which is the addition reaction product, can form a flexible coating.

[0025] The organohydrogenpolysiloxane of formula (2) may also contain two or more types. As the chain length of the organohydrogenpolysiloxane of formula (2) increases, it has the effect of imparting flexibility to the organosilicon resin. Therefore, for example, by including two types of organohydrogenpolysiloxane of formula (2) with different chain lengths, the physical properties of the coating can be controlled.

[0026] [Physical Properties of Crosslinked Organosilicon Resin] The weight-average molecular weight of the crosslinked organosilicon resin of component (A) is preferably 5,000 to 1,000,000, more preferably 8,000 to 500,000, and even more preferably 10,000 to 500,000. Having a molecular weight within this range is more preferable in terms of performance and ease of filtration and other operations. The weight-average molecular weight can be determined as a polystyrene-equivalent weight-average molecular weight by gel permeation chromatography (GPC) analysis (the same applies hereinafter).

[0027] The crosslinked organosilicon resin of component (A) may be solid, gel, or liquid at 25°C. For example, by dissolving it in a liquid oil and volatilizing it, a film can be easily formed. This film is brittle and strong before crosslinking, but after crosslinking, its brittleness improves, resulting in a non-sticky, flexible film. From the viewpoint of film-forming ability, a solid or gel state is preferred, with a solid state being more preferred. Film-forming ability can be determined by dropping 1.5 g of a solution diluted with 30% by weight (hereinafter simply abbreviated as "%)" with isododecane or decamethylcyclopentasiloxane onto PTFE (fluororesin), drying at 105°C for 3 hours, and determining whether a free-standing film is formed. If a film is not formed, oil seeps through cracks in the film, significantly reducing oil resistance and resulting in poor skin conformability, resulting in an unnatural finish.

[0028] The crosslinked organosilicon resin of component (A) can be more suitably used as a film-forming agent. While organosilicon resins before crosslinking form brittle, strong films, crosslinked organosilicon resins after crosslinking have improved brittleness and form flexible films without stickiness. This is because organosilicon resins before crosslinking form strong films, but crosslinking with flexible chains imparts flexibility to the film. Generally, hard films tend to have low flexibility, while highly flexible films tend to be soft, so film strength and flexibility have been considered to be in a trade-off relationship. However, this crosslinked organosilicon resin has the characteristic of having excellent followability due to its high flexibility despite forming a strong film.

[0029] Furthermore, the film formed by the crosslinked organosilicon resin of component (A) has significantly improved oil resistance to oil agents such as sebum, compared to the film formed by the organosilicon resin before crosslinking. Organosilicon resins tend to have improved oil resistance as their molecular weight increases, but since there is a limit to how much the molecular weight of organosilicon resin can be increased, there is also a limit to the oil resistance. Crosslinking organosilicon resins with crosslinking agents leads to a pseudo increase in the molecular weight of the organosilicon resin, which has the effect of raising this limit. Therefore, crosslinked organosilicon resins have oil resistance that cannot be achieved by conventional organosilicon resins.

[0030] A crosslinked organosilicon resin in which f in the above formula (2) is an integer that satisfies 0≦f<30 is solid at 25° C. and has particularly excellent film-forming properties.

[0031] In addition, f in the above formula (2) satisfies 0≦f<30, and R 4 A crosslinked organosilicon resin in which two of the groups are hydrogen atoms is solid at 25°C and has particularly excellent film-forming properties. 4 If three or more of these are hydrogen atoms, there is a high possibility that the composition will become gel-like when the diluting solvent is removed. In this case, the composition will have film-forming properties, but will have a gel-like feel.

[0032] In the above formula (1), a1 satisfies 0<a1≦3, and f in the above formula (2) satisfies 0≦f<30, and R 4 Crosslinked organosilicon resins in which two of the radicals are hydrogen atoms are solid at 25°C and can be obtained as crosslinked organosilicon resins with particularly excellent film-forming properties. The resulting films exhibit particularly excellent flex resistance and oil resistance.

[0033] The amount of hydrogen gas generated per mass of the crosslinked organosilicon resin is 1.5 mL or less under standard conditions. If the amount exceeds 1.5 mL / g, the resin may generate hydrogen gas over time or react with the remaining hydroxyl or alkoxy groups and hydrosilyl groups, increasing the likelihood of viscosity increase over time and reducing stability over time. The amount of hydrogen gas generated is preferably 0.01 to 1.2 mL / g, and more preferably 0.02 to 1.0 mL / g.

[0034] The amount of hydrogen gas per mass can be calculated from the volume of hydrogen gas generated by the reaction of the hydrosilyl group with the base. Examples of calculation methods include, but are not limited to, the following method. <Method for measuring the amount of hydrogen gas> 10 g of a 20% aqueous sodium hydroxide solution is added dropwise to a mixed solution of 50 g of a crosslinked organosilicon resin diluted to 50% with decamethylcyclopentasiloxane and 10 g of 1-butanol. The amount of hydrogen gas per mass can be determined by dividing the volume of the generated hydrogen gas by the pure content of the crosslinked organosilicon resin.

[0035] [Production Method] The crosslinked organosilicon resin of component (A) can be synthesized by various methods known in the art. For example, crosslinking can be achieved by reacting the surface silanol groups of an organosilicon resin with an organopolysiloxane having hydroxyl groups at both ends. However, since it is difficult to completely control the amount of silanol groups on the organosilicon resin surface, it is difficult to accurately control the amount of organopolysiloxane to be crosslinked. Alternatively, it can be synthesized by the addition reaction of an organosilicon resin having hydrosilyl groups with an organopolysiloxane having alkenyl groups at both ends. However, the hydrosilyl groups in the organosilicon resin have low reactivity, and the remaining hydrosilyl groups react over time, resulting in increased viscosity and the generation of hydrogen gas. Therefore, a preferred method for producing a silicone-crosslinked crosslinked organosilicon resin is the addition reaction of an organosilicon resin having alkenyl groups with an organopolysiloxane having hydrosilyl groups at both ends.

[0036] The method for producing a crosslinked organosilicon resin by the hydrosilylation reaction is described in more detail below. In the hydrosilylation reaction step between the alkenyl group-containing organosilicon resin represented by formula (1) and the organohydrogenpolysiloxane represented by formula (2), the molar ratio of terminal hydrosilyl groups to unsaturated groups can be selected from the range of 0.5 to 2.0, preferably 0.5 to 1.2, more preferably 0.8 to 1.2, and even more preferably 0.9 to 1.1. If this ratio is too high, the amount of residual hydrosilyl groups will increase, which may result in poor stability over time.

[0037] This hydrosilylation reaction is preferably carried out in the presence of a platinum or rhodium catalyst. Examples of suitable catalysts include chloroplatinic acid, alcohol-modified chloroplatinic acid, and chloroplatinic acid-vinylsiloxane complexes. Furthermore, since an excessive amount of catalyst will cause coloration of the sample, the amount of platinum or rhodium used is preferably 50 ppm or less, and more preferably 20 ppm or less.

[0038] Furthermore, the above addition reaction may be carried out in the presence of an organic solvent, if necessary. Examples of the organic solvent include cyclic organopolysiloxanes such as octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and dodecamethylcyclohexasiloxane; short-chain silicone oils such as methyl trimethicone and short-chain dimethicone; aromatic hydrocarbons such as toluene and xylene; ketone-based organic solvents such as acetone, methyl ethyl ketone, diethyl ketone, and methyl isobutyl ketone; aliphatic hydrocarbons such as hexane, heptane, octane, decane, isododecane, and cyclohexane; and aliphatic alcohols such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-methyl-1-propanol, 2-butanol, 2-methyl-2-propanol, 1-pentanol, 2-methylbutanol, 2-pentanol, 1-hexanol, 2-methylpentanol, 1-heptanol, 1-octanol, 1-nonanol, 1-decanol, phenol, benzyl alcohol, ethylene glycol, and 1,2-propylene glycol. In particular, ethanol, 1-propanol, and 2-propanol are preferred from the viewpoint of reactivity.

[0039] The amount of the solvent used is preferably 1 to 80%, more preferably 5 to 50%, of the total reaction solution (system). Within this range, the reaction system is maintained uniformly and the reaction proceeds efficiently.

[0040] The crosslinked organosilicon resin of component (A) used in the present invention can be dissolved in an organic solvent and used as a pre-dissolved product. The organic solvent used during the addition reaction can be used as is, or it can be replaced after the addition reaction, and the organic solvent to be replaced can be selected depending on the application. The replacement solvent is not particularly limited and can be selected from the organic solvents mentioned above.

[0041] The addition reaction conditions are not particularly limited, but it is preferable to heat under reflux at a temperature of 50 to 150°C, more preferably 80 to 120°C, for about 1 to 10 hours.

[0042] After the addition reaction, a step of removing the rhodium or platinum catalyst used with activated carbon may be included. The amount of activated carbon used is preferably 0.001 to 5.0% of the entire system, and more preferably 0.01 to 1.0%. By keeping the amount within this range, coloration of the sample can be further suppressed.

[0043] After the addition reaction, a step of removing the remaining hydrosilyl groups can be included as needed. In particular, when used in applications such as cosmetics, the hydrosilyl groups may be deactivated over time by dehydrogenation. Since hydrogen gas is generated, which is a safety issue, it is preferable to include a step of removing the hydrosilyl groups.

[0044] The hydrosilyl group removal process involves adding a basic catalyst to hydrolyze unreacted hydrosilyl groups, followed by neutralization by adding an acidic catalyst in an amount equal to the molar equivalent of the basic catalyst. Examples of basic catalysts include strongly basic catalysts and weakly basic catalysts. Examples of strongly basic catalysts include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, and barium hydroxide. Examples of weakly basic catalysts include alkali metal carbonates such as sodium carbonate and calcium carbonate, and alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate. In terms of promoting the dehydrogenation reaction, it is particularly preferable to use a strongly basic catalyst, and specifically, sodium hydroxide is preferred. Examples of acidic catalysts include inorganic acids such as hydrochloric acid, sulfuric acid, sulfurous acid, oleum, and phosphoric acid; sulfonic acids such as p-toluenesulfonic acid, methanesulfonic acid, and trifluoromethanesulfonic acid; and carboxylic acids such as oxalic acid, formic acid, acetic acid, propionic acid, benzoic acid, citric acid, and trifluoroacetic acid.

[0045] In general, rather than using an acid or base alone, it is preferable to use them in combination with water and heat them at a temperature below the boiling point of water. This process converts hydrosilyl groups (SiH groups) into hydroxysilyl groups (SiOH groups). However, when a crosslinked organosilicon resin is treated with a base catalyst, the silanol groups and alkoxy groups in the organosilicon resin react, causing changes in physical properties, so it is not preferable to remove hydrosilyl groups using this method.

[0046] <Powder to be surface-coated> The powder to be surface-coated can be used without any particular limitation in terms of shape (e.g., spherical, plate-like, acicular, etc.), particle size (e.g., mist-like, fine particles, pigment-grade, etc.), particle structure (e.g., porous, non-porous, etc.), etc. Examples include inorganic powders, glitter powders, organic powders, organic pigment powders, composite inorganic powders, etc.

[0047] Examples of the inorganic powder include metal soaps such as titanium oxide, black titanium oxide, ferruginous ferrous metal, ultramarine blue, red iron oxide, yellow iron oxide, black iron oxide, zinc oxide, aluminum oxide, magnesium oxide, zirconium oxide, zinc laurate, magnesium myristate, zinc myristate, magnesium stearate, aluminum stearate, and zinc stearate; magnesium carbonate, calcium carbonate, chromium oxide, chromium hydroxide, carbon black, silica, aluminum silicate, magnesium silicate, aluminum magnesium silicate, bismuth oxychloride, barium sulfate, boron nitride, mica, synthetic fluorphlogopite, sericite, talc, (fluoride / hydroxide / oxide) / (Mg / K / silicon), glass powder, kaolin, silicon carbide, barium sulfate, bentonite, and smectite, and these may be used alone or in combination.

[0048] Examples of the glittering powder include titanium mica, iron oxide-coated mica, iron oxide-coated titanium mica, organic pigment-coated titanium mica, titanium oxide-coated synthetic fluorophlogopite, titanium oxide-coated glass powder, iron oxide / titanium oxide-coated glass powder, and aluminum powder, and these can be used alone or in combination of two or more.

[0049] Examples of the organic powder include nylon powder, polymethyl methacrylate powder, acrylonitrile-methacrylic acid copolymer powder, vinylidene chloride-methacrylic acid copolymer powder, PET resin powder, polyethylene powder, polystyrene powder, organopolysiloxane elastomer powder, polymethylsilsesquioxane powder, polyurethane powder, wool powder, silk powder, polylactic acid powder, crystalline cellulose powder, and N-acyl lysine powder, and these can be used alone or in combination of two or more.

[0050] The organic colorant powder may be one or more selected from organic tar-based pigments, organic colorant lake pigments, etc. Examples include Red No. 201, Red No. 202, Red No. 205, Red No. 218, Red No. 223, Red No. 226, Red No. 228, Orange No. 203, Orange No. 204, Blue No. 404, Yellow No. 401, Red No. 3, Red No. 104, Red No. 106, Orange No. 205, Yellow No. 4, Yellow No. 5, Green No. 3, Blue No. 1, etc.

[0051] Examples of the composite inorganic powder include fine particle titanium oxide-coated mica, fine particle zinc oxide-coated mica titanium, barium sulfate-coated mica titanium, titanium oxide-containing silica, zinc oxide-containing silica, and the like, and these can be used alone or in combination of two or more.

[0052] Among these, one or more selected from the group consisting of inorganic powder, glittering powder, organic powder, and composite inorganic powder are preferred. Examples of inorganic powders include mica, synthetic fluorophlogopite, sericite, (fluoride / hydroxide / oxide) / (Mg / K / silicon), boron nitride, bismuth oxychloride, barium sulfate, glass powder, and metal soap. Furthermore, glittering powders and composite inorganic powders are more preferably those based on the inorganic powders described above, with titanium mica, iron oxide-coated titanium mica, titanium oxide-coated synthetic fluorophlogopite, titanium oxide-coated glass powder, and iron oxide-coated titanium oxide-coated glass powder being even more preferred. N-acyl lysine powder is more preferred as the organic powder.

[0053] Furthermore, plate-like powders with a large contact area with the skin are preferred. Plate-like powders have a smooth surface. The plate-like powder is not particularly limited in terms of aspect ratio, refractive index, etc., and any type can be used. In particular, from the viewpoint of smooth spreadability, an aspect ratio of 10 or more is preferred, and 30 or more is more preferred. The average particle diameter (major axis) is preferably 1 to 100 μm, and plate-like powders with a diameter of 3 to 50 μm are more preferred. This range is preferred in terms of less aggregation and a balance between adhesion and unevenness correction. The aspect ratio of a powder is a value calculated from (average particle diameter) / (average thickness).

[0054] The amount of surface coating treatment with component (A) in the surface-coated powder of the present invention is not particularly limited, but is preferably 0.5% or more, more preferably 1.5% or more, in terms of solids content. It is also preferably 10% or less, more preferably 4% or less. The range is preferably 0.5 to 10%, more preferably 1.5 to 4%. This range is preferred because it provides excellent water repellency, smooth spreadability, and lack of aggregation.

[0055] The treatment method for the surface-coated powder of the present invention is not particularly limited, and can be dry treatment or wet treatment. Dry treatment means that the layer containing component (A) does not become a clayey continuous layer when mixed with volatile oil. On the other hand, wet treatment is a method in which the layer containing component (A) is mixed with volatile oil to obtain a slurry, and the volatile oil is evaporated by drying under reduced pressure at a high temperature (e.g., 90°C). In the present invention, dry treatment is preferred in terms of cost, time, and load on the equipment during treatment.

[0056] The equipment used for the surface coating treatment is not particularly limited. For example, a dry media mill is preferred because it can apply shear to component (A) and the powder to be surface-coated, thereby improving the dispersibility of component (A). A dry media mill refers to an equipment that can grind a powdered surface coating treatment agent, the powder to be coated, and optionally a volatile oil by stirring them with a grinding medium selected from balls or beads such as aluminum oxide, hardened steel, stainless steel, tungsten carbide, agate, sintered aluminum oxide, silicon nitride, and zirconium oxide. Specific examples include ball mills (manufactured by Makino Corporation), planetary ball mills (manufactured by Fritsch), Attritor (manufactured by Nippon Coke & Engineering Co., Ltd.), Drystar (manufactured by Ashizawa Finetech Co., Ltd.), and Converge Mills (manufactured by Makabe Giken Co., Ltd.), and one or more of these can be used. In particular, grinding using a planetary ball mill is preferred because it results in less aggregation, uniform adhesion, and excellent unevenness-covering ability. The processing time, the force applied during processing, etc. are adjusted appropriately depending on the equipment.

[0057] When producing the surface-coated powder of the present invention, it is preferable to include a volatile oil during treatment, although there are no particular limitations on the type of oil. Volatile oil refers to an oil that is volatile at room temperature, and oils such as hydrocarbon oils such as isoparaffin and silicone oils with low boiling points (boiling points of 260°C or less at normal pressure) are preferably used, and one or a combination of two or more types can be used as needed. The volatile oil is not particularly limited, and is preferably one that uniformly dissolves component (A) in order to increase the dispersibility of component (A) during surface coating treatment and to increase the uniformity of the surface coating treatment.

[0058] Examples of hydrocarbon oils (light isoparaffins) such as low-boiling isoparaffins include isododecane, isohexadecane, etc. Commercially available products include Isopar A, Isopar C, Isopar E, Isopar G, Isopar H, Isopar K, Isopar L, and Isopar M (all manufactured by Exxon), Shellsol 71 (manufactured by Shell), Soltrol 100, Soltrol 130, and Soltrol 220 (all manufactured by Philips), and ISODODECANE (INEOS OLIGOMERS).

[0059] Examples of volatile silicone oils include cyclic silicone oils (cyclomethicones), such as hexamethylcyclotrisiloxane, octamethyltetracyclosiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, and tetradecamethylcycloheptasiloxane. Commercially available products include Execol D-4 (manufactured by Shin-Etsu Chemical Co., Ltd.), SH244, and SH344 (all manufactured by Dow Corning Toray Co., Ltd.) as octamethyltetracyclosiloxanes, Execol D-5 (manufactured by Shin-Etsu Chemical Co., Ltd.), SH245, and DC345 (all manufactured by Dow Corning Toray Co., Ltd.) as decamethylcyclopentasiloxanes, and DC246 (manufactured by Dow Corning Toray Co., Ltd.) as dodecamethylcyclohexasiloxanes. Examples of low-boiling dimethylpolysiloxanes include KF-96L-2CS and KF-96L-1.5CS (both manufactured by Shin-Etsu Chemical Co., Ltd.), and examples of branched siloxanes include TMF-1.5 (manufactured by Shin-Etsu Chemical Co., Ltd.).

[0060] The content of the volatile oil in the production process of the surface-coated powder is not particularly limited and can be adjusted appropriately depending on the specific surface area of ​​the powder to be coated. Specifically, it is preferably 0.5 to 83%, more preferably 0.5 to 50%, and even more preferably 1.5 to 10%. For example, if the content of the volatile oil does not reach the oil absorption capacity of the powder to be surface-coated and the layer containing component (A) does not become a continuous layer, dry processing becomes easier. In this case, reducing the content of the volatile oil is preferable because it ultimately leads to a shortening of the drying processing time.

[0061] The surface-coated powder of the present invention may be further subjected to a surface-coating treatment with a conventionally known surface-coating treatment agent, such as a silicone treatment, a pendant treatment, a silane coupling agent treatment, a titanium coupling agent treatment, an oil treatment, an N-acylated amino acid treatment, a metal soap treatment, an amino acid treatment, an inorganic compound treatment, a plasma treatment, a mechanochemical treatment, or an organic titanate treatment.

[0062] <Cosmetics> The surface-coated powder of the present invention can be used in cosmetics. The cosmetics are not particularly limited as long as they are applied to the body (for example, skin, hair, nails, etc.). In particular, cosmetics to be applied to the skin are preferred in terms of exerting the effect of skin adhesion.

[0063] The content of the surface-coated powder varies depending on the formulation of the cosmetic, but is preferably 0.01% or more, more preferably 0.5% or more, and even more preferably 5% or more, based on the total amount of the cosmetic. It is also preferably 99% or less, more preferably 90% or less, and even more preferably 80% or less. The range is preferably 0.01 to 99%, more preferably 0.5 to 90%, and even more preferably 5 to 80%. This range is preferred in terms of longer cosmetic wear, smooth spreadability, and excellent skin adhesion. A lower limit may also be set, for example, to 10%, 15%, or 20%. An upper limit may also be set, for example, to 70%, 60%, 50%, or 40%.

[0064] Cosmetics using the surface-coated powder of the present invention can further contain component (B), spherical powder. The term "spherical" does not necessarily mean a perfect sphere, but also includes ellipsoids, approximate spheres, and those with minute holes or irregularities on the surface. A spherical shape is preferably one in which the ratio of the minor axis to the major axis is 1:1 to 1:2.

[0065] The spherical powder is not particularly limited, and specific examples thereof include inorganic powders such as zinc oxide, aluminum oxide, silicon dioxide (silica, silicic anhydride), magnesium oxide, zirconium oxide, magnesium carbonate, calcium carbonate, calcium sulfate, chromium oxide, chromium hydroxide, carbon black, aluminum silicate, magnesium silicate, magnesium aluminum silicate, talc, kaolin, silicon carbide, barium sulfate, bentonite, smectite, and boron nitride; acrylic powders such as polymethyl methacrylate, methyl methacrylate crosspolymer, acrylonitrile-methacrylic acid copolymer, and vinylidene chloride-methacrylic acid copolymer; silicone-based resin powders such as dimethicone / vinyl dimethicone crosspolymers, (vinyl dimethicone / methicone silsesquioxane) crosspolymers, (diphenyl dimethicone / vinyl diphenyl dimethicone / silsesquioxane) crosspolymers and polymethyl silsesquioxane; organic powders such as nylon, cellulose acetate, cellulose, polylactic acid, polyurethane, polyethylene, polystyrene and (HDI / PPG / polycaprolactone) crosspolymers; and composite powders such as titanium oxide-containing silica and zinc oxide-containing silica, and these can be used alone or in combination of two or more.

[0066] From the viewpoints of powder dispersibility, smooth spreadability, pore-covering effect, etc., component (B) is preferably at least one powder selected from the group consisting of silicone resin powder, urethane, nylon, cellulose acetate, cellulose, starch, polylactic acid, acrylic resin powder, and silica, and more preferably at least one powder selected from the group consisting of cellulose acetate, cellulose, starch, polylactic acid, acrylic resin powder, and silica. Furthermore, an embodiment in which the component (B) is a plant-derived powder or an inorganic powder is even more preferable, and specifically at least one powder selected from the group consisting of cellulose, starch, and silica is preferable.

[0067] From the viewpoint of smooth spreading and pore-covering effect, the content of component (B) in the cosmetic is preferably 3% or more, more preferably 7% or more, even more preferably 15% or more, and most preferably 20% or more. Also, the content is preferably 80% or less, more preferably 75% or less, and even more preferably 70% or less. The range is preferably 3 to 80%, more preferably 15 to 75%, and even more preferably 20 to 70%.

[0068] Furthermore, the mass ratio of the surface-coated powder to component (B) in the cosmetic [surface-coated powder / component (B)] is not particularly limited, and is, for example, preferably 0.01 or more, more preferably 0.05 or more, and even more preferably 0.1 or more. It is also preferably 30 or less, more preferably 10 or less, more preferably 5 or less, and even more preferably 1 or less. The range is preferably 0.01 to 30, more preferably 0.05 to 10, even more preferably 0.1 to 5, and most preferably 0.1 to 1. This range is preferable because it makes it easier to balance the cosmetic's unevenness-covering power and adhesion.

[0069] In addition to the surface-coated powder and component (B), cosmetics using the surface-coated powder of the present invention can contain ingredients commonly used in cosmetics, such as oils, powders (pigments, colorants, and extender powders), fluorine compounds, resins, surfactants, thickeners, waxes, preservatives, fragrances, ultraviolet absorbers (including organic and inorganic ones, and may be resistant to either UV-A or UV-B), moisturizers, salts, solvents, antioxidants, chelating agents, neutralizing agents, pH adjusters, and cosmetic ingredients (skin whitening agents, cell activators, anti-inflammatory agents, blood circulation promoters, skin astringents, antiseborrheic agents, etc.), as long as the effects of the present invention are not impaired.

[0070] The method for producing the cosmetic of the present invention is not particularly limited, and it can be produced by a conventional method. For example, the surface-coated powder, component (B), and other components that may be contained as needed can be mixed and dispersed to form a cosmetic composition, which can then be added to various dosage forms to produce the cosmetic.

[0071] Furthermore, examples of dosage forms include aqueous dosage forms, solubilized dosage forms, oil-in-water dosage forms, water-in-oil dosage forms, oil-based dosage forms, and powder dosage forms. Among these, powder cosmetics are particularly preferred in terms of exerting water-repellent effects. Powder cosmetics include unmolded powder forms (loose forms) and solid powder forms. When preparing a solid form, examples include a method of filling and molding the cosmetic composition into a metal or resin dish-shaped container (dry filling molding), or a method of dispersing the cosmetic composition in a solvent before filling the container, removing the solvent, and then dry molding (wet filling molding). When preparing a powder form, the cosmetic composition obtained above can be pulverized and sized as necessary, and then filled into a container.

[0072] Examples of the items include makeup cosmetics such as sunscreen, foundation, concealer, face powder, eye shadow, eyebrow, and blush; skin care cosmetics such as lotion, emulsion, body powder, wrinkle powder, antiperspirant, and body lotion; and hair cosmetics such as hair coloring. Makeup cosmetics or sunscreen cosmetics are particularly preferred. The cosmetics may be used by applying them directly to the skin, using a cosmetic tool such as a puff, or as an aerosol filled in a pressure-resistant container together with a propellant.

[0073] The present invention can also take the following forms: [1] Powder surface-coated with the following component (A): (A) a crosslinked organosilicon resin that is an addition reaction product of the following components (X) and (Y), wherein the amount of hydrogen gas generated per mass from this crosslinked organosilicon resin is 1.5 mL / g or less under standard conditions; (X) an alkenyl-containing organosilicon resin represented by the following formula (1) and having one or more alkenyl groups per molecule: [In the formula, R 1 are each independently an alkenyl group having 2 to 8 carbon atoms, and R 2 are each independently a group selected from an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, and an aralkyl group having 7 to 30 carbon atoms. 3 are each independently an organopolysiloxane-containing group, and the R 2 and each R 3 3SiO 1/2 R in units 3 at least one of the above is an organopolysiloxane-containing group. a1, a2, a3, b, c, and d are numbers that satisfy 0<a1≦5, 0<a2≦400, 0≦a3≦400, 0≦b≦320, 0≦c≦320, and 0<d≦1,000, and 0.5≦(a1+a2+a3) / d≦1.5.] (Y) An organohydrogenpolysiloxane represented by the following formula (2) and having two or more hydrosilyl groups per molecule: an amount such that the amount of hydrosilyl groups is 0.5 to 1.2 moles per mole of alkenyl groups in the above component (X). [In the formula, R 2 is the same as above, and R 4 are each independently a hydrogen atom or the R 2 and all R 4 where two or more of them are hydrogen atoms, and e, f, g, and h are 0 or positive numbers, with the proviso that 2≦e+f+g+h<32 is satisfied.] [2] The surface-coated powder according to [1], wherein the powder is a plate-like powder. [3] The surface-coated powder according to [1] or [2], wherein the amount of surface-coated component (A) is 0.5 to 10% based on the total amount of powder to be treated. [4] The surface-coated powder according to any one of [1] to [3], obtained by surface-coating component (A) and the powder using a media mill. [5] A cosmetic preparation containing the surface-coated powder according to any one of [1] to [4]. [6] The cosmetic preparation according to [5], further containing component (B) spherical powder. [7] The cosmetic preparation according to [5] or [6], wherein the content of the surface-coated powder is 0.01 to 99%. [8] The cosmetic preparation according to [6] or [7], wherein the content of the component (B) is 3 to 80%. [9] The cosmetic preparation according to any one of [6] to [8], wherein the content mass ratio of the surface-coated powder to the component (B) [surface-coated powder / component (B)] is 0.01 to 30.

[10] The cosmetic preparation according to any one of [5] to [9], which is a powder cosmetic preparation.

[0074] The present invention will be described in more detail below with reference to examples and comparative examples, but the present invention is not limited to the following examples.

[0075] The alkenyl group-containing organosilicon resins used as raw materials in the following examples were synthesized according to known manufacturing methods. In the following manufacturing examples and comparative examples, the reaction rate of the alkenyl group is 1 The amount was calculated based on the amount of alkenyl groups remaining after the reaction by H-NMR spectrum analysis.

[0076] (Production Examples of Surface Coating Treatment Agents) [Production Example 1] Method for producing a 30% solution of crosslinked organosilicon resin / decamethylcyclopentasiloxane 1,000 g of a 50% decamethylcyclopentasiloxane solution of a powdered alkenyl group-containing organosilicon resin (weight average molecular weight 7,430, vinyl value: 0.229 mmol / g) represented by the following formula (E1), 700 g of decamethylcyclopentasiloxane, 126.9 g of an organopolysiloxane having hydrosilyl groups at both ends represented by the following formula (E2) (amount of hydrogen gas generated: 20.3 mL / g, hydrosilyl group / vinyl group = 1.0), and 0.6 g of a 0.5% 2-propanol solution of chloroplatinic acid were charged into a reactor and reacted by heating at 120°C for 8 hours. The solvent was then distilled off by heating under reduced pressure. Decamethylcyclopentasiloxane was added to adjust the concentration to 30%, followed by filtration to obtain a decamethylcyclopentasiloxane solution of a crosslinked organosilicon resin. The resulting decamethylcyclopentasiloxane solution of a crosslinked organosilicon resin was heated to 120-130°C under reduced pressure to remove the decamethylcyclopentasiloxane, yielding a solid powder (weight average molecular weight 221,000). The conversion of alkenyl groups was 92%, and the amount of hydrogen gas generated from the remaining hydrosilyl groups was 0.8 mL / g. Formula (E1): Formula (E2):

[0077] [Production Example 2] Method for producing a 30% crosslinked organosilicon resin / decamethylcyclopentasiloxane solution 1,000 g of a 50% decamethylcyclopentasiloxane solution of a powdered alkenyl group-containing organosilicon resin (weight average molecular weight 8,050, vinyl value: 0.224 mmol / g) represented by formula (E3) below, 700 g of decamethylcyclopentasiloxane, 53.8 g of an organopolysiloxane having hydrosilyl groups at both ends represented by formula (E4) below (hydrogen gas generation rate: 51.3 mL / g, hydrosilyl group / vinyl group ratio = 1.1), and 0.6 g of a 0.5% chloroplatinic acid 2-propanol solution were charged into a reactor and heated at 110°C for 5 hours to carry out a reaction. The solvent was then distilled off by heating under reduced pressure. Decamethylcyclopentasiloxane was added to adjust the concentration to 30%, and the mixture was then filtered to obtain a decamethylcyclopentasiloxane solution of a crosslinked organosilicon resin.

[0078] The resulting decamethylcyclopentasiloxane solution of the crosslinked organosilicon resin was heated to 120-130°C under reduced pressure to remove the decamethylcyclopentasiloxane. The resulting product was a solid powder (weight average molecular weight 154,000). The conversion of alkenyl groups was 93%, and the amount of hydrogen gas generated from the remaining hydrosilyl groups was 1.0 mL / g. Formula (E3): Formula (E4):

[0079] [Production Example 3] Method for producing a 30% crosslinked organosilicon resin / decamethylcyclopentasiloxane solution 1,000 g of a 50% decamethylcyclopentasiloxane solution of a powdered alkenyl group-containing organosilicon resin (weight average molecular weight 14,860, vinyl value: 0.323 mmol / g) represented by formula (E5) below, 700 g of decamethylcyclopentasiloxane, 160.0 g of an organopolysiloxane having hydrosilyl groups at both ends represented by formula (E6) below (hydrogen gas generation rate: 22.6 mL / g, hydrosilyl group / vinyl group ratio = 1.0), and 0.6 g of a 0.5% chloroplatinic acid 2-propanol solution were charged into a reactor and heated at 110°C for 3 hours to carry out a reaction. The solvent was then distilled off by heating under reduced pressure. Decamethylcyclopentasiloxane was added to adjust the concentration to 30%, and the mixture was then filtered to obtain a decamethylcyclopentasiloxane solution of a crosslinked organosilicon resin.

[0080] The resulting decamethylcyclopentasiloxane solution of the crosslinked organosilicon resin was heated to 120-130°C under reduced pressure to remove the decamethylcyclopentasiloxane. The resulting product was a solid powder (weight average molecular weight 168,500). The conversion of alkenyl groups was 92%, and the amount of hydrogen gas generated from the remaining hydrosilyl groups was 0.5 mL / g. Formula (E5): Formula (E6):

[0081] [Production Example 4] Method for producing a 30% crosslinked organosilicon resin / decamethylcyclopentasiloxane solution 1,000 g of a 50% decamethylcyclopentasiloxane solution of a powdered alkenyl group-containing organosilicon resin (weight average molecular weight 11,730, vinyl value: 0.307 mmol / g) represented by the following formula (E7), 700 g of decamethylcyclopentasiloxane, 78.5 g of an organopolysiloxane having hydrosilyl groups at both ends represented by the following formula (E8) (hydrogen gas generation rate: 43.8 mL / g, hydrosilyl group / vinyl group ratio = 1.0), and 0.6 g of a 0.5% chloroplatinic acid 2-propanol solution were charged into a reactor and heated at 120°C for 5 hours to carry out a reaction. The solvent was then distilled off by heating under reduced pressure. Decamethylcyclopentasiloxane was added to adjust the concentration to 30%, and the mixture was then filtered to obtain a decamethylcyclopentasiloxane solution of a crosslinked organosilicon resin.

[0082] The resulting decamethylcyclopentasiloxane solution of the crosslinked organosilicon resin was heated to 120-130°C under reduced pressure to remove the decamethylcyclopentasiloxane. The resulting product was a solid powder (weight average molecular weight 96,500). The conversion of alkenyl groups was 97%, and the amount of hydrogen gas generated from the remaining hydrosilyl groups was 0.9 mL / g. Formula (E7): Formula (E8):

[0083] (Production Examples and Comparative Production Examples of Surface-Coated Powders) Surface-coated powders of Production Examples 1 to 10 and Comparative Production Examples 1 to 3 were prepared based on the compositions in Table 1 and the production methods described below. The resulting surface-coated powders were evaluated for water repellency, smooth spreadability, skin adhesion, and lack of aggregation using the methods described below. The results are also shown in Table 1.

[0084] Treatment method A (dry): surface-coated powder Production Examples 1 to 8 Mica was placed in a sealable alumina grinding container (volume 500 ml), and 200 ml of alumina grinding balls (diameter 20 mm) were then added. Next, component (A) obtained in Production Examples 1 to 4 was dissolved in an equal amount of isododecane at 110°C and cooled to room temperature to obtain a solution (solid content 50%). This solution was added to the alumina grinding container and mixed uniformly using a tabletop disperser to prepare a dispersion. Thereafter, the mixture was ground for 10 hours at 100 rpm using a tabletop ball mill (V-1ML type / manufactured by Irie Shokai Co., Ltd.), and the isododecane was evaporated to obtain a surface-coated powder.

[0085] Treatment method A (dry): surface-coated powder Production Example 10 A surface-coated powder was obtained by the same production method as in Production Example 3, except that the powder to be surface-coated was changed from mica to (fluoride / hydroxide / oxide) / (Mg / K / silicon).

[0086] Treatment method B (wet): surface-coated powder Production Example 9 97 parts by mass of mica, 6 parts by mass of a solution (solid content 50%) prepared by dissolving the component (A) obtained in Production Example 1 in an equal amount of isododecane at 110°C and cooling to room temperature, and 80 parts by mass of isopropanol were charged into an automatic mortar. The mixture was then stirred at 80 rpm for 10 minutes to obtain a slurry. The obtained slurry was dried under reduced pressure at 90°C to obtain a surface-coated powder.

[0087] Treatment method B (wet): surface-coated powder Comparative Production Example 1 In Comparative Production Example 1, a surface-coated powder was obtained by the same method as in Production Example 9, except that trimethylsiloxysilicate was used instead of Production Example 1.

[0088] Treatment method B (wet): surface-coated powder Comparative Production Example 2 In Comparative Production Example 2, a surface-coated powder was obtained by the same production method as in Production Example 9, except that dimethicone (kinematic viscosity 100 cSt) was used instead of Production Example 1 and isododecane was not added.

[0089] Treatment method C (baking): surface-coated powder Comparative Production Example 3 97 parts by mass of mica, 3 parts by mass of methicone (KF-99-P: manufactured by Shin-Etsu Chemical Co., Ltd.), and 100 parts by mass of isopropanol were charged into an automatic mortar. The mixture was then stirred at 80 rpm for 10 minutes to obtain a slurry. The obtained slurry was dried under reduced pressure at 90°C and further baked at 120°C for 30 minutes to obtain a surface-coated powder.

[0090] *1: Mica powder Y-3000 (manufactured by Yamaguchi Mica Co., Ltd.) (average particle size 23 μm) *2: Micromica MK-200K (manufactured by Co-op Chemical Co., Ltd.) (average particle size 7.5 μm)

[0091] (Evaluation Method: A. Water Repellency) 10 g of each of Production Examples 1 to 10 and Comparative Production Examples 1 to 3 was filled into a metal dish (length 4 cm, width 4 cm, thickness 0.4 cm) and pressed under a pressure of 200 kg / cm. 2 The specimen was press-molded under a pressure of 0.015 to obtain a measurement sample. Measurements were carried out using a contact angle measuring device (Dropmaster DM500 manufactured by Kyowa Interface Science Co., Ltd.) and the sessile drop method (θ / 2 method). 1.0 μL of a mixture prepared from purified water and ethanol at a ratio of 2.5:1.5 was dropped onto the surface of the measurement sample, and the contact angle was measured after 1.0 seconds. Measurements were carried out five times (measurements were taken at five locations per sample), and the average value was used as the contact angle. [Contact angle]: [Evaluation] 70° or more: ◎ 65° or more and less than 70°: ◯ 50° or more and less than 65°: △ Less than 50°: ×

[0092] (Evaluation Method: B. Smooth Spreading) The "smooth spreading" of the surface-coated powders of the Production Examples and Comparative Production Examples listed in Table 1 was evaluated according to the following procedure. 10 mg of each sample was placed on an artificial cheek skin model (No. 10D, female model in her 50s: manufactured by Beaulux Co., Ltd.) and applied with a finger. Five cosmetic expert evaluators evaluated the "smooth spreading" on a four-point scale according to the following evaluation criteria, assigning a score to each sample. The average score of all expert evaluators was then judged according to the following judgment criteria. (Evaluation Criteria) [Evaluation Results]: [Score] Good: 4 points Fair: 3 points Fair: 2 points Poor: 1 point (Judgment Criteria) [Average Score]: [Judgment] 4.0 points: ◎ 3.5 points or more and less than 4.0 points: ◯ 2.0 points or more and less than 3.5 points: △ 1.0 point or more and less than 2.0 points: ×

[0093] (Evaluation method: c. Skin adhesion) The "skin adhesion" of the surface-coated powders of the Production Examples and Comparative Production Examples listed in Table 1 was evaluated according to the following procedure. Five cosmetic expert evaluators applied 0.5 g of each sample to their face with their fingers, and evaluated the "skin adhesion" during application. Each evaluator gave a score for each sample on a four-point scale according to the following evaluation criteria, and the average of all the evaluators' scores was then judged according to the following judgment criteria. (Evaluation criteria) [Evaluation results]: [Score] Good: 4 points Fair: 3 points Fair: 2 points Poor: 1 point (Judgment criteria) [Average score]: [Judgment] 4.0 points: ◎ 3.5 points or more and less than 4.0 points: ◯ 2.0 points or more and less than 3.5 points: △ 1.0 point or more and less than 2.0 points: ×

[0094] (Evaluation Method: D. Absence of Agglomeration) The "absence of agglomeration" of the surface-coated powders of the Production Examples and Comparative Production Examples listed in Table 1 was evaluated according to the following procedure. 10 g of isopropanol was added to 10 g of sample and mixed for 5 minutes with a paddle mixer to obtain a uniform dispersion. This dispersion was measured using a laser diffraction / scattering particle size distribution analyzer (LA-960: manufactured by HORIBA) to obtain the median diameter D50(1). The base material of the surface-coated powder was also measured using the same method to obtain the median diameter D50(2). The "absence of agglomeration" was evaluated according to the following criteria from the obtained particle size ratio D50(1) / D50(2) and the shape of the particle size distribution. The shape of the particle size distribution was evaluated with particle size (2) plotted on the horizontal axis and frequency on the vertical axis. A distribution with one maximum was evaluated as unimodal, and a distribution with two or more maximums was evaluated as multimodal.

[0095] (Evaluation criteria) [Average particle size and particle size distribution shape]: [Evaluation] D50(1) / D50(2) ≦2.5 and particle size distribution is unimodal: ◎ 2.5<D50(1) / D50(2) ≦3.5 and particle size distribution is unimodal: O 3.5<D50(1) / D50(2) ≦4.5 and particle size distribution is unimodal: △ 4.5<D50(1) / D50(2) or particle size distribution is multimodal: ×

[0096] The surface-coated powders of Production Examples 1 to 10 exhibited excellent water repellency, smooth spreadability, high skin adhesion, and excellent lack of cohesion. This is presumably due to the formation of a uniform layer of crosslinked organosilicon resin on the powder surface, resulting in a dense, uniform microstructure on the surface that could not be achieved with conventional surface-coating treatments. In particular, when the surface-coating amount ranged from 1.5% in Production Example 2 to 10% in Production Example 8, the powders exhibited particularly excellent water repellency, while Production Examples 1 to 8 and 10, which were treated using Treatment Method A (dry), exhibited particularly excellent lack of cohesion. On the other hand, Comparative Production Example 1, which used trimethylsiloxysilicate, exhibited poor smooth spreadability and skin adhesion. This is believed to be due to the formation of an uneven resin film on the powder surface. In Comparative Production Example 2, which used dimethicone (100 cSt), treatment was performed with an oil agent rather than a silicone resin, but its molecular weight is smaller than that of silicone resin, which is thought to be why the water repellency was reduced. In Comparative Example 3, in which the oil agent was baked onto the powder surface, the polymer bonded to the powder via its side chain, which slightly increased water repellency, but the molecular weight was still not large enough to achieve a sufficient effect.

[0097] (Cosmetic Examples and Comparative Examples) The surface-coated powders prepared by the above method were used in the following formulations. <Cosmetic Examples 1 to 9 and Cosmetic Comparative Examples 1 to 3: Loose Powders> Loose powders of cosmetic examples 1 to 9 and cosmetic comparative examples 1 to 3 were prepared using the compositions and production methods shown in Table 2. Each of the resulting loose powders was evaluated for makeup durability, smooth spreadability, skin adhesion, and pore-covering effect using the methods shown below. The results are also shown in Table 2.

[0098] * 3: CS-400 (manufactured by Toshiki Pigment Co., Ltd.) * 4: KSP-100 (manufactured by Shin-Etsu Chemical Co., Ltd.) * 5: Matsumoto Microsphere M-305QD7 (manufactured by Matsumoto Yushi Pharmaceutical Co., Ltd.) (average particle diameter 7 μm) * 6: Sunsphere NP-100 (manufactured by AGC Si-Tech Co., Ltd.) * 7: Cosme Silica CQ4 (manufactured by Fuji Silysia Co., Ltd.)

[0099] (Production method) A: Components 1 to 15 are mixed and dispersed. B: Component 16 is added to A and mixed uniformly. C: B is pulverized in a pulverizer. D: C is filled into a container to obtain a loose powder.

[0100] (Evaluation method: E. Makeup retention) The "makeup retention" of the loose powders of the Examples and Comparative Examples listed in Table 2 was evaluated according to the following procedure. The prepared powder cosmetic was applied to the entire face in appropriate amounts using a puff. Five cosmetic expert evaluators evaluated the "makeup retention" 8 hours after application on a four-point scale according to the following evaluation criteria, assigning a score to each sample, and then judging the average of all the evaluations according to the following judgment criteria. (Evaluation criteria) [Evaluation results]: [Score] Good: 4 points Fair: 3 points Fair: 2 points Poor: 1 point (Judgment criteria) [Average score]: [Judgment] 4.0 points: ◎ 3.5 points or more and less than 4.0 points: ◯ 2.0 points or more and less than 3.5 points: △ 1.0 point or more and less than 2.0 points: ×

[0101] (Evaluation method: F. Pore covering effect) The "pore covering effect" of the loose powders of the Examples and Comparative Examples listed in Table 2 was evaluated according to the following procedure. Five cosmetic product expert evaluators placed 0.5 g of each sample on the cheeks and spread it with their fingers, and the "pore covering effect" was evaluated on a four-point scale according to the following evaluation criteria, and a score was assigned to each sample. The average score of all the evaluators was then judged according to the following judgment criteria. (Evaluation criteria) [Evaluation results]: [Score] Good: 4 points Fair: 3 points Fair: 2 points Poor: 1 point (Judgment criteria) [Average score]: [Judgment] 4.0 points: ◎ 3.5 points or more and less than 4.0 points: ◯ 2.0 points or more and less than 3.5 points: △ 1.0 point or more and less than 2.0 points: ×

[0102] The loose powders of the Examples and Comparative Examples shown in Table 2 were evaluated and judged for "smooth spreadability" and "adhesion to skin" using the same evaluation method as for the surface-coated powders described above.

[0103] The loose powders of cosmetic Examples 1 to 9 were characterized by excellent makeup retention, smooth spread, skin adhesion, and pore-covering effect. Example 9, which did not contain component (B), had results in which smooth spread and pore-covering effect were somewhat good, but skin adhesion was particularly excellent. On the other hand, cosmetic Comparative Example 1, which used Comparative Production Example 1, was inferior in smooth spread, skin adhesion, and pore-covering effect due to aggregation with sericite, and cosmetic Comparative Example 2, which used Comparative Production Example 2, had poor makeup retention. Furthermore, cosmetic Comparative Example 3, which used Comparative Production Example 3, did not achieve satisfactory quality in terms of makeup retention.

[0104] <Cosmetic Example 10: Powdery solid foundation> (Ingredients) (%) 1. Surface-coated mica from Production Example 3 15.0 2. Hydrophobized zinc oxide *8 5.0 3. Dimethicone crosspolymer *9 5.0 4. 0.1% phospholipid-treated titanium dioxide (average particle size: 0.27 μm) 7.0 5. Water-repellent titanium oxide nylon composite powder *10 10.0 6. Lauroyl lysine 3.0 7. Hydrophobized talc *11 23.0 8. Red iron oxide 0.7 9. Yellow iron oxide 1.8 10. Black iron oxide 0.2 11. Chlorphenesin 0.2 12. Boron nitride (average particle size: 6.5 μm) 5.0 13. Nylon-12 *12 1.5 14. Urethane powder *13 3.0 15. (Vinyl dimethicone / methicone silsesquioxane) crosspolymer *4 5.0 16. Silica *14 5.0 17. Plate-shaped barium sulfate balance 18. Ethylhexyl methoxycinnamate 5.0 19. Tridecyl isononanoate 1.5 20. Sorbitan sesquistearate 0.7 * 8: XZ-300F-LP (manufactured by Sakai Chemical Industry Co., Ltd.) * 9: DOWSIL EP-9610 Cosmetic Powder (manufactured by Dow Toray Industries, Inc.) * 10: MTXO70-NL (manufactured by Hayate Material Co., Ltd.) * 11: SE-TA-13 (manufactured by Miyoshi Chemicals Co., Ltd.) * 12: Amihope LL (manufactured by Ajinomoto Co., Inc.) * 13: D-400 (manufactured by Toshoku Pigment Co., Ltd.) * 14: HCS 160M5 (manufactured by JGC Catalysts and Chemicals Co., Ltd.)

[0105] <Manufacturing Method> (1) Mix components 1 to 17 uniformly. (2) While stirring (1) in a Henschel mixer, add components 18 to 20, which have been heated and dissolved at 70°C, and mix uniformly. (3) Pulverize (2) in a pulverizer, fill a resin dish, and compression-molde to obtain a powdery solid foundation.

[0106] <Results> The powder solid foundation of Cosmetic Example 10 was a foundation that had excellent makeup longevity, smooth spreadability, skin adhesion, and pore-covering effect.

[0107] <Cosmetic Example 11: Stick-type lipstick> (Ingredients) (%) 1. Synthetic wax *15 25.0 2. (Ethylene / propylene) copolymer *16 2.0 3. Dimethicone 10.0 4. Glyceryl tri-2-ethylhexanoate balance 5. (Dimethicone / vinyl dimethicone) crosspolymer mixture *17 20.0 6. BHT 0.02 7. Dipropylene glycol 0.3 8. Red No. 202 1.5 9. Dimethyl silylated silica *18 1.0 10. Synthetic phlogopite 1.0 11. Surface-coated mica from Production Example 3 15.0 12. Fragrance 0.03 13. Olive oil 0.001 14. Jojoba oil 0.001 15. Squalane 0.01 * 15: CIREWAX 80 (manufactured by CIREBELLE Co., Ltd.) * 16: EPS wax (manufactured by Nippon Natural Products Co., Ltd.) * 17: KSG-016F (solid content 25%, manufactured by Shin-Etsu Chemical Co., Ltd.) * 18: AEROSIL R976S (manufactured by Nippon Aerosil Co., Ltd.)

[0108] <Manufacturing Method> (1) Components 1 to 5 are mixed uniformly at 100°C. (2) Components 6 to 15 are added to (1) and mixed uniformly. (3) After heating and mixing (2) at 100°C, the mixture is filled into a lipstick stick container and cooled to room temperature to obtain a lipstick.

[0109] <Results> The stick lipstick of Cosmetic Example 11 was a lipstick that had excellent makeup longevity, spread smoothly, and adhered to the skin.

[0110] <Cosmetic Example 12: Oil-in-Water Foundation> (Ingredients) (%) 1. Polysorbate 80 0.5 2. Glyceryl stearate 0.5 3. Sorbitan sesquioleate 0.5 4. Sorbitan palmitate 0.5 5. Stearic acid 1.5 6. Lecithin 0.1 7. Triceteareth-4 phosphate 0.3 8. Behenyl alcohol 0.5 9. Ethylhexyl methoxycinnamate 5.0 10. Bis-ethylhexyloxyphenol methoxyphenyl triazine 1.0 11. Glyceryl tri-2-ethylhexanoate 1.0 12. Polyglyceryl-2 triisostearate 3.0 13. Mineral oil*19 0.5 14. 15. Dipentaerythrityl Hexa(hydroxystearic acid / stearic acid / rosin acid) 0.5 15. Di(octyldodecyl / phytosteryl / behenyl) lauroyl glutamate 2.0 16. Paraffin *20 1.0 17. Dimethicone *21 3.0 18. Titanium dioxide (average particle size 250 nm) *22 5.0 19. Iron oxide *23 1.0 20. Purified water balance 21. 1,3-butylene glycol 10.0 22. Ethanol 5.0 23. Triethanolamine 1.0 24. Phenoxyethanol 0.2 25. Disodium phosphate 0.126. Sodium phosphate 0.1 27. EDTA-2Na 0.1 28. (Acrylic acid / alkyl acrylate (C10-C30)) copolymer 0.01 29. Carbomer 0.2 30. Microcrystalline cellulose *24 0.005 31. 40% aqueous dispersion of methylene bisbenzotriazolyl tetramethylbutylphenol *25 8.0 32. Acrylates copolymer *26 0.1 33. Talc 0.5 34. Synthetic phlogopite 1.0 35. Surface-coated mica from Production Example 3 13.0 36. Bentonite 0.001 37. (PEG-240 / decyltetradeceth-20 / HDI) copolymer 0.005 38. Sage extract 0.01 39. Sodium hyaluronate 0.005 40. Chamomile flower extract 0.005 * 19: CARNATION (manufactured by SONNEBORN. LLC) * 20: PARACERA 256 (manufactured by PARAMELT) * 21: Silicon KF-96A (20CS) (manufactured by Shin-Etsu Chemical Co., Ltd.) * 22: CR-50 treated with 2% lecithin (Ishihara Sangyo Kaisha) * 23: Mixture of red iron oxide treated with 2% isopropyl triisostearoyl titanate: yellow iron oxide treated with 2% isopropyl triisostearoyl titanate: black iron oxide treated with 2% isopropyl triisostearoyl titanate = 0.15: 0.8: 0.05 * 24: Rheocrysta C2-SP (manufactured by Croda Japan Co., Ltd.) * 25: K22-M40 (manufactured by Dai Nippon Kasei Co., Ltd.) * 26: Ultrasol V-280C (manufactured by Aica Kogyo Co., Ltd.)

[0111] <Production Method> (1) Components 1 to 19 are mixed uniformly at 75°C. (2) Components 20 to 40 are mixed uniformly at 75°C. (3) (1) is added to (2) at 75°C and emulsified, and then cooled to 30°C to obtain an oil-in-water foundation.

[0112] <Results> The oil-in-water foundation of Cosmetic Example 12 was a foundation that had excellent makeup longevity, smooth spreadability, skin adhesion, and pore-covering effect.

[0113] <Cosmetic Example 13: Water-in-oil Foundation> (Ingredients) (%) 1. Cyclopentasiloxane 15.0 2. Phenyl trimethicone *27 10.0 3. Ethylhexyl methoxycinnamate 6.0 4. Diethylamino hydroxybenzoyl hexyl benzoate 1.0 5. PEG-9 polydimethylsiloxyethyl dimethicone *28 4.0 6. Ethylhexyl hydroxystearate 1.0 7. Cetyl lactate 2.0 8. Squalane 3.0 9. Stearkonium hectorite 0.3 10. Distearyldimonium hectorite 0.3 11. Surface-coated mica from Production Example 3 5.0 12. Cellulose *29 1.0 13. Talc 1.0 14. Mica 1.0 15. Titanium dioxide (average particle size: 250 nm) *30 10.0 16. Iron oxide *31 2.0 17. Purified water remaining 18.13-Butylene glycol 15.0 19. Ethanol 5.0 20. Phenoxyethanol 0.2 21. Sodium chloride 0.2 22. 40% water dispersion of methylenebisbenzotriazolyltetramethylbutylphenol*25 8.0 23. Tremella fuciformis extract*32 0.05 24. Niacinamide 1 * 27: SH556FLUID (manufactured by Toray Dow Corning Co., Ltd.) * 28: KF-6028P (manufactured by Shin-Etsu Chemical Co., Ltd.) * 29: CELLULOBEADS D-5 (spherical cellulose with an average particle size of 5 μm, manufactured by Daito Kasei Kogyo Co., Ltd.) * 30: Lauroyl glutamic acid Na 2% treated * 31: Lecithin 2% treated red iron oxide: lecithin 2% treated yellow iron oxide: lecithin 2% treated black iron oxide = 0.15: 0.8: 0.05 mixed * 32: TREMOIST-TP (manufactured by Nippon Fine Chemical Co., Ltd.),

[0114] <Production Method> (1) Components 1 to 16 were mixed uniformly at 60°C. (2) Components 17 to 24 were mixed uniformly. (3) (1) was added to (2) and emulsified to obtain a water-in-oil foundation.

[0115] <Results> The water-in-oil type foundation of Cosmetic Example 13 was a foundation that had excellent makeup longevity, smooth spreadability, skin adhesion, and pore-covering effect.

[0116] <Cosmetic Example 14: Powdery solid blush> (Ingredients) (%) 1. Hexagonal plate-shaped zinc oxide *33 2.0 2. Amodimethicone-treated mica *34 10.0 3. Dimethicone-coated talc *35 10.0 4. Silica-treated mica *36 10.0 5. Iron oxide mixture *37 4.0 6. Titanium mica *38 1.0 7. Synthetic fluorphlogopite balance 8. Zinc myristate (average particle size 2 μm) 2.0 9. Surface-coated mica of Production Example 3 10.0 10. Boron nitride 5.0 11. 2-decyltetradecanol 5.0 12. Dextrin palmitate *39 0.3 13. Propylene glycol dicaprate 4.0 14. Vaseline *40 4.0 15. Diisostearyl malate 2.0 16. (PEG-15 / Lauryl Dimethicone) Crosspolymer Liquid Paraffin Mixture *41 10.0 17. Rose Extract 0.01 18. Water-soluble Collagen 0.01 19. Tocopherol 0.005 20. Ascorbic acid 0.005 *33: XZ-300F (manufactured by Sakai Chemical Industry Co., Ltd.) *34: Y-2300WA1 (manufactured by Yamaguchi Mica) *35: SA-Talc JA-46R (manufactured by Miyoshi Chemical Industry Co., Ltd.) *36: SXI-5 (manufactured by Miyoshi Chemical Industry Co., Ltd.) *37: Bengala: yellow iron oxide = 1:4 *38: FLAMENCO SPARKLE GOLD 220J (manufactured by BASF) *39: Leopard TL2 (Chiba Flour Milling Co., Ltd.) *40: SNOW WHITE SPECIAL (manufactured by SONNNEBORN RN. LLC) *41: KSG-310 (solid content 30%, manufactured by Shin-Etsu Chemical Co., Ltd.)

[0117] <Production Method> (1) Mix ingredients 1 to 10 uniformly. (2) Mix ingredients 11 to 20 uniformly at 60°C and dissolve. (3) Add (2) and isododecane to (1) and mix uniformly to form a slurry, which is then molded into a metal dish and dried overnight at 70°C to obtain a powdery solid blush.

[0118] <Results> The powdery solid blush of Cosmetic Example 14 was a blush that had excellent makeup longevity, smooth spreadability, skin adhesion, and pore-covering effect.

[0119] Cosmetic Example 15: Powdered Solid Eye Shadow (Ingredients) (%) 1. Talc remaining 2. Paraben 0.2 3. Black iron oxide 2.0 4. Red iron oxide coated titanium mica *42 3.0 5. Titanium oxide coated synthetic fluorophlogopite *43 15.0 6. Titanium oxide coated glass powder *44 10.0 7. Surface-coated mica from Production Example 3 10.0 8. Diisostearyl malate 20.0 9. Cetyl ethylhexanoate 3.0 10. Glyceryl tri-2-ethylhexanoate 5.0 11. Dipentaerythrityl hexa(hydroxystearic acid / stearic acid / rosin acid) *45 1.0 *42: BLONDIEE SUPER BRONZE N-2220S (manufactured by CQV) *43: HELIOS R100S (manufactured by Topy Industries) *44: Microglass Metashine MT1080RS (manufactured by Nippon Sheet Glass) *45: Cosmoll 168ARV (manufactured by Nisshin Oillio)

[0120] <Manufacturing Method> (1) Mix components 1 to 7 uniformly. (2) Mix components 8 to 11 uniformly. (3) Add (2) to (1) and mix to obtain a cosmetic base. (4) Add 25 parts by mass of isododecane as a filling solvent to 100 parts by mass of (3), and mix uniformly to form a slurry. (5) Fill a metal dish with (4), place cellulose paper on top, and perform compression molding while removing the solvent. (6) Dry (5) at 70°C overnight to completely remove the solvent, obtaining a powdery solid eye shadow.

[0121] <Results> The powder solid eye shadow of Cosmetic Example 15 was an eye shadow that had excellent makeup longevity, smooth spreadability, skin adhesion, and pore-covering effect.

[0122] <Cosmetic Example 16: Oil-based unevenness correcting cosmetic> (Ingredients) (%) 1. Dimethicone crosspolymer / cyclomethicone mixture *46 balance 2. (Dimethicone / polyglycerin-3) crosspolymer / dimethicone mixture *47 20.0 3. Surface-coated mica from Production Example 3 20.0 4. Dimethicone (kinematic viscosity 2 cSt) 5.0 5. Squalane 5.0 6. Trimethylsiloxysilicate 3.0 *46: DOWSIL 9040 SILICONE ELASTOMER BLEND (Dow-Toray Industries, Inc.) *47: KSG-710 (Shin-Etsu Chemical Co., Ltd.)

[0123] <Production Method> (1) Components 1 to 6 were mixed uniformly. (2) Components 1 was poured into a glass jar and the surface was compressed and smoothed to obtain a cosmetic composition for correcting unevenness.

[0124] <Results> The unevenness-correcting cosmetic of Cosmetic Example 16 was an unevenness-correcting cosmetic that had excellent makeup durability, smooth spreadability, skin adhesion, and pore-covering effect.

[0125] <Cosmetic Example 17: Powdery White Powder> (Ingredients) (%) 1. (HDI / PPG / Polycaprolactone) Crosspolymer *3 25.0 2. (Vinyl Dimethicone / Methicone Silsesquioxane) Crosspolymer *4 5.0 3. Methyl Methacrylate Crosspolymer *5 8.5 4. Boron Nitride (Average Particle Size: 10 μm) 5.0 5. Synthetic Fluorphlogopite *48 10.0 6. Chlorphenesin 0.1 7. Hydrophobized Mica *49 Remaining 8. Ultramarines 2.0 9. Surface-Coated Mica of Production Example 3 10.0 10. Ethylhexylglycerin 0.35 11. 2-Cetyl Ethylhexanoate 7.0 12. Fragrance 0.03 13. Ethanol 0.1 *48: PDM-40L (manufactured by Topy Industries, Ltd.) *49: SE-MA-23 (manufactured by Miyoshi Chemicals Co., Ltd.)

[0126] <Production Method> (1) Mix components 1 to 9 uniformly. (2) While stirring (1) in a Henschel mixer, add components 10 to 13 and mix uniformly. (3) Pulverize (2) in a pulverizer to obtain a white powder.

[0127] <Results> The powdery face powder of Cosmetic Example 17 was a face powder that had excellent makeup longevity, smooth spreadability, skin adhesion, and pore-covering effect.

[0128] Cosmetic Example 18: Solid Powder Eyebrow (Ingredients) (%) 1. Surface-coated powder of Production Example 3 25.0 2. Surface-coated powder of Production Example 10 20.0 3. Boron nitride 8.0 4. Spherical silica (average particle size 10 μm) 3.0 5. Spherical cellulose (average particle size 10 μm) 13.0 6. Amodimethicone 3% treated mica (average particle size 12 μm) 10.0 7. Mica (average particle size 15 μm) balance 8. Lauroyl lysine 5.0 9. Dextrin palmitate 1% treated black iron oxide 3.0 10. Red iron oxide 0.7 11. Stearoyl glutamate sodium 1% treated yellow iron oxide 1.3 12. 13. Dimethylpolysiloxane (25°C kinematic viscosity 10 CS) 4.0 14. Octyldodecyl stearate 0.5 15. Squalane 1.0 16. Octyldodecanol 1.5 17. Diisostearyl malate 2.0 18. Peppermint extract 0.01 19. Menthol 0.005 20. Fragrance 0.02

[0129] (Production Method) (1) Mix ingredients 1 to 11 uniformly. (2) Mix ingredients 12 to 20 uniformly. (3) Add (2) to (1) and mix uniformly. (4) Crush (3), fill a metal dish, and compression-molde to obtain a solid powder eyebrow.

[0130] <Results> The solid powder eyebrow product of Cosmetic Example 18 was an eyebrow product that had excellent makeup longevity, smooth spreadability, and skin adhesion.

Claims

1. Powder surface-coated with the following component (A): (A) a crosslinked organosilicon resin which is an addition reaction product of the following components (X) and (Y), and which generates 1.5 mL / g or less of hydrogen gas per mass under standard conditions; (X) an alkenyl-containing organosilicon resin represented by the following formula (1) and having one or more alkenyl groups in each molecule. [In the formula, R 1 are each independently an alkenyl group having 2 to 8 carbon atoms; R 2 are each independently a group selected from an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, and an aralkyl group having 7 to 30 carbon atoms. 3 are each independently an organopolysiloxane-containing group, and the R 2 Each R 3 3 SiO 1/2 R in units 3 at least one of the above is an organopolysiloxane-containing group. a1, a2, a3, b, c, and d are numbers that satisfy 0<a1≦5, 0<a2≦400, 0≦a3≦400, 0≦b≦320, 0≦c≦320, and 0<d≦1,000, and 0.5≦(a1+a2+a3) / d≦1.5.] (Y) An organohydrogenpolysiloxane represented by the following formula (2) and having two or more hydrosilyl groups in one molecule: an amount such that the amount of hydrosilyl groups is 0.5 to 1.2 moles per mole of alkenyl groups in the above component (X). [In the formula, R 2 is the same as above, R 4 are each independently a hydrogen atom or the R 2 and all R 4 Two or more of them are hydrogen atoms, and e, f, g, and h are 0 or positive numbers, with the proviso that 2≦e+f+g+h<32 is satisfied.

2. The surface-coated powder according to claim 1, wherein the powder is plate-shaped powder.

3. The surface-coated powder according to claim 1 or 2, wherein the amount of the surface coating treatment of the component (A) is 0.5 to 10% by mass based on the total amount of the powder to be treated.

4. The surface-coated powder according to claim 1 or 2, which is obtained by subjecting the component (A) and the powder to surface coating treatment with a media mill.

5. A cosmetic containing the surface-coated powder according to claim 1.

6. The cosmetic according to claim 5, further containing a component (B) spherical powder.

7. The cosmetic according to claim 5 or 6, wherein the content of the surface-coated powder is 0.01 to 99% by mass.

8. The cosmetic according to claim 6, wherein the content of the component (B) is 3 to 80% by mass.

9. The cosmetic according to claim 6 or 8, wherein the content mass ratio of the surface-coated powder to the component (B) [surface-coated powder / component (B)] is 0.01 to 30.

10. The cosmetic according to claim 5, 6 or 8, which is a powder cosmetic.

Citation Information

Patent Citations

  • Novel organopolysiloxane, surfactant, emulsion composition, powder treatment agent, thickening agent of oil-based raw material, gelling agent, gel composition and cosmetic raw material comprising the organopolysiloxane, as well as, preparations for external use and cosmetics comprising the same

    JP2011246706A

  • Surface treated powder and external preparation for skin containing surface treated powder

    JP2015048305A

  • Surface treated powder and cosmetic mixed with the same

    JP2016145213A

  • Novel silicone surfactants, water-in-oil emulsion compositions, powder compositions, and their cosmetic / medical uses

    JP2017518167A

  • Novel co-modified organopolysiloxane

    WO2011049248A1