Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
  • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
  • C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
  • A61K8/27—Zinc; Compounds thereof
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
  • A61K8/29—Titanium; Compounds thereof
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
  • A61K8/89—Polysiloxanes
  • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
  • A61K8/89—Polysiloxanes
  • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
  • A61K8/894—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
  • A61Q1/02—Preparations containing skin colorants, e.g. pigments
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
  • A61Q1/02—Preparations containing skin colorants, e.g. pigments
  • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
  • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
  • C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
  • C08G77/50—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms by carbon linkages
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
  • C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
  • C08L83/12—Block- or graft-copolymers containing polysiloxane sequences containing polyether sequences
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
  • C08L83/14—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
  • C09K23/54—Silicon compounds

Definitions

• the present invention relates to organopolysiloxanes, dispersions containing the same, and cosmetics containing these. Note that in the present invention, compositions for cosmetics may be referred to as cosmetics.
• silicone-based surfactants have been widely used as emulsifiers to emulsify silicone.
• polyglycerin-modified silicone combines the adhesiveness of polyglycerin to the skin with the light feel characteristic of silicone, and is widely used in emulsified cosmetics, etc., but is known to have a tendency to cause sensory stickiness (Patent Document 1).
• metal oxide powders such as titanium oxide and zinc oxide are generally used in the form of so-called fine particle metal oxide powders with an average particle size of 100 nm or less in order to improve transparency and enhance the UV shielding effect.
• the surface area of fine particle metal oxide powders is large, which strengthens the bonding force between the particles, and as a result, they tend to aggregate easily. For this reason, when using these fine particle metal oxide powders in sunscreen cosmetics, it is important that they can be contained stably without agglomeration.
• Patent Document 2 proposes a silicone-branched polyglycerin-modified silicone that has high dispersibility in powders. However, this structure results in high viscosity. Patent Documents 3 and 4 propose it as an ABA copolymer as a dispersion stabilizer for powders. However, there has been insufficient research into silicone chain length and dispersibility due to its bias.
• JP 2002-3334 A International Publication No. WO 2016/178380 JP 2006-218472 A JP 2012-207078 A
• the present invention has been made in consideration of the above circumstances, and aims to provide an organopolysiloxane with excellent powder dispersibility. In addition, it aims to provide a dispersion with good stability, and a cosmetic with excellent usability and spreadability.
• an organopolysiloxane in which each end of polyglycerin is modified with an organopolysiloxane chain of a specific chain length has excellent powder dispersibility. Furthermore, because the organopolysiloxane has high powder dispersion stability, they discovered a dispersion containing the organopolysiloxane and having excellent stability, and a cosmetic composition containing the organopolysiloxane or the dispersion and having excellent usability and spreadability, which led to the present invention.
• a cosmetic preparation comprising the organopolysiloxane according to any one of 1 to 6. 8.
• a dispersion comprising the organopolysiloxane according to any one of 1 to 6, a powder, and an oil.
• the organopolysiloxane is represented by formula (1), where q is 0 ⁇ q ⁇ 9 and r is 0 ⁇ r ⁇ 9, and the powder has an average primary particle size of less than 15 nm.
• a cosmetic comprising the dispersion according to any one of 8 to 10.
• the present invention provides an organopolysiloxane with excellent powder dispersion stability.
• this organopolysiloxane is processed into a powder, a dispersion with good stability can be provided.
• this organopolysiloxane or a dispersion using this organopolysiloxane is used in a cosmetic, a cosmetic with a good feel and excellent spreadability can be provided.
• the present invention is described in detail below, but is not limited thereto.
• the use in cosmetics is described in detail below, but the use is not particularly limited.
• the ingredient name may be written as the cosmetic display name or the International Nomenclature of Cosmetic Ingredient (INCI).
• the cosmetic display name and INCI correspond, the cosmetic display name or English description may be omitted.
• the organopolysiloxane of the present invention is an organopolysiloxane represented by the following formula (1), and may be used alone or in combination of two or more.
• R 1 is independently a group selected from an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and an aralkyl group having 7 to 20 carbon atoms.
• R 2 is independently a divalent organic group having 3 to 15 carbon atoms which may be connected via an oxygen atom.
• p is 0 ⁇ p ⁇ 9
• q is 0 ⁇ q ⁇ 200
• r is 0 ⁇ r ⁇ 200
• m is 0 ⁇ m ⁇ 10
• n2 is an integer of 0 ⁇ n2 ⁇ 5.
• the bonds of each glycerin unit bracketed by m and n1 may be in blocks or random.
• R 1 is independently a group selected from an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and an aralkyl group having 7 to 20 carbon atoms.
• R 1 is preferably an alkyl group having 1 to 15 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an alkyl group in which a portion of the hydrogen atoms of the alkyl group is substituted with a fluorine atom.
• examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, an octyl group, a decyl group, a dodecyl 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 preferred.
• R 2 is independently a divalent organic group having 3 to 15 carbon atoms which may have an oxygen atom in between.
• R 2 is independently a divalent organic group having 3 to 15 carbon atoms which may have an oxygen atom in between. Examples include -(CH 2 ) 3 -, -(CH 2 ) 4 -, -CH 2 CH(CH 3 )CH 2 -, -(CH 2 ) 8 -, -(CH 2 ) 11 -, -(CH 2 ) 3 -O-(CH 2 ) 2 -, and -(CH 2 ) 2 -O-(CH 2 ) 3 -. Among them, -(CH 2 ) 3 - and -CH 2 CH(CH 3 )CH 2 - are preferred.
• p is 0 ⁇ p ⁇ 9, preferably 1 ⁇ p ⁇ 9, and more preferably 3 ⁇ p ⁇ 9. If p is greater than the upper limit, when used as a dispersant, the adsorption to the powder is poor and the dispersibility is deteriorated.
• q is 0 ⁇ q ⁇ 200.
• the average primary particle size of the powder is less than 15 nm, 0 ⁇ q ⁇ 9 is preferable. If q is 9 or less, the adsorption to the powder is good and the dispersibility is also good. Also, if the average primary particle size of the powder is 15 nm or more, 10 ⁇ q ⁇ 200 is preferable.
• q 10 or more, the hydrophobic group is of sufficient length and the particles are less likely to aggregate, so the dispersibility is good.
• r is 0 ⁇ r ⁇ 200, and if the average primary particle size of the powder is less than 15 nm, 0 ⁇ r ⁇ 9 is preferable. If r is 9 or less, the adsorption to the powder is good and the dispersibility is also good.
• the average primary particle size of the powder was measured by averaging 100 randomly selected particles using a transmission electron microscope (hereinafter the same).
• n1 is 5 or less, the polarity of the dispersant is reduced, and the compatibility of the oil and the dispersant is increased.
• n2 is 0 ⁇ n2 ⁇ 5, preferably 1 ⁇ n2 ⁇ 3, and more preferably 1 ⁇ n2 ⁇ 2. If n2 is greater than 5, the polarity of the dispersant becomes high, which may lead to a deterioration in the compatibility of the oil agent and the dispersant, particularly when silicone oil is used as the oil agent.
• the bonds of each glycerin unit bounded by m and n1 may be block or random. The order of bonds of each siloxane unit is not limited.
• organopolysiloxanes in which q is 0 ⁇ q ⁇ 9 and r is 0 ⁇ r ⁇ 9 have short siloxane units, good adsorption to powders with an average primary particle size of less than 15 nm, and high dispersion stability, making them suitable for use as dispersants for powders with small average primary particle sizes.
• organopolysiloxanes in which q is 10 ⁇ q ⁇ 200 have long siloxane units, good adsorption to powders with an average primary particle size of 15 nm or more, and high dispersion stability, and are therefore suitable for use as dispersants for powders with a large average primary particle size.
• the organopolysiloxane of the present invention can be used as a dispersant that can well disperse powders of any particle size by optimizing its structure.
• the method for synthesizing the organopolysiloxane of the present invention is not particularly limited, but the organopolysiloxane can be obtained by an addition reaction of a polyglycerol compound having two or more alkenyl groups as a raw material with one or more organohydrogenpolysiloxanes having a hydrosilyl group at one end.
• the compound can be obtained by subjecting a polyglycerol compound having two or more alkenyl groups represented by the following formula (2) to a hydrosilylation reaction with one or more organohydrogenpolysiloxanes having a hydrosilyl group at one end represented by the following formula (3).
• the hydrosilylation reaction may also be carried out in the presence of a platinum catalyst or a rhodium catalyst.
• Polyglycerol compounds having two or more alkenyl groups can be obtained by subjecting epoxy compounds such as monoallyl glycidyl ether, monooctenyl glycidyl ether, glycidol, and glycidyl methyl ether to a ring-opening reaction of the epoxy groups in the presence of an alkali catalyst with compounds having hydroxyl groups such as glycerin, diglycerin, glycerin monoallyl ether, and glycidol.
• epoxy compounds such as monoallyl glycidyl ether, monooctenyl glycidyl ether, glycidol, and glycidyl methyl ether
• the ring-opening reaction of hydroxyl groups and epoxy groups is known, and there is no particular restriction on the type of alkali catalyst, but examples that can be used include alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate, alkali metal carbonates such as sodium carbonate and potassium carbonate, and sodium methoxide.
• the amount of alkali catalyst added is 0.2 to 2 mol %, preferably 0.2 to 1 mol %, based on 100 mol % of the compound having a hydroxyl group.
• the ring-opening reaction product of the hydroxyl group and epoxy group contains various isomers depending on the composition of the raw materials, and is usually a mixture of these.
• the above-mentioned production method using the hydrosilylation reaction is described in more detail below.
• the molar ratio of hydrosilyl groups/alkenyl groups is preferably 0.5 to 2.0, and more preferably 0.8 to 1.2.
• This hydrosilylation reaction is preferably carried out in the presence of a platinum or rhodium catalyst.
• a platinum or rhodium catalyst for example, chloroplatinic acid, alcohol-modified chloroplatinic acid, chloroplatinic acid-vinylsiloxane complex, etc. are preferred.
• the reaction product will become colored, so the amount of platinum or rhodium used is preferably 50 ppm (by mass) or less, and more preferably 20 ppm or less.
• the above addition reaction may be carried out in the presence of an organic solvent, if necessary.
• the organic solvent include cyclic organopolysiloxanes such as octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and dodecamethylcyclohexasiloxane; 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, and cyclohexane; monohydric 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-methyl
• the amount of solvent used is preferably 1 to 80% by mass of the entire reaction liquid (system), and more preferably 5 to 50% by mass. Within the above range, the reaction system is kept uniform and the reaction proceeds efficiently.
• 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.
• a step of removing the rhodium catalyst or platinum catalyst used with activated carbon may be included.
• the amount of activated carbon used is preferably 0.001 to 5.0% by mass, and more preferably 0.01 to 1.0% by mass, of the entire system. If it is within the above range, coloration of the reaction product can be further suppressed.
• Unreacted hydrosilyl groups may be present in the organopolysiloxane after the addition reaction. Furthermore, if the organic solvent used in the addition reaction is an aliphatic alcohol, alcohol exchange reactions and dehydrogenation reactions will occur as side reactions, and alkoxy groups may remain.
• a step of substituting remaining hydrosilyl groups with hydroxysilyl groups may be included.
• the hydrosilyl groups may be inactivated over time by a dehydrogenation reaction, which may result in the generation of hydrogen gas, which is problematic from the standpoint of safety, so it is preferable to include a step of substituting hydrosilyl groups with hydroxysilyl groups.
• the process of replacing hydrosilyl groups with hydroxysilyl groups involves hydrolyzing unreacted hydrosilyl groups in the presence of a basic catalyst such as an alkali metal carbonate, an alkali metal hydrogen carbonate, or an alkali metal hydroxide, and then adding an acid catalyst in an amount equal to the molar equivalent of the basic catalyst to neutralize.
• a basic catalyst such as an alkali metal carbonate, an alkali metal hydrogen carbonate, or an alkali metal hydroxide
• an acid catalyst in an amount equal to the molar equivalent of the basic catalyst to neutralize.
• Specific examples of basic catalysts include strong basic catalysts such as lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, and barium hydroxide, and weak basic catalysts such as sodium carbonate, calcium carbonate, and sodium hydrogen carbonate. In terms of promoting the dehydrogenation reaction, it is particularly preferable to use a strong basic catalyst, and sodium hydroxide is particularly preferred.
• acid catalysts include inorganic acids such as hydrochloric acid, sulfuric acid, sulfurous acid, fuming sulfuric acid, and phosphoric acid, sulfonic acids such as p-toluenesulfonic acid, methanesulfonic acid, and trifluoromethanesulfonic acid, and carboxylic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, benzoic acid, citric acid, and oxalic acid.
• inorganic acids such as hydrochloric acid, sulfuric acid, sulfurous acid, fuming sulfuric acid, and phosphoric acid
• sulfonic acids such as p-toluenesulfonic acid, methanesulfonic acid, and trifluoromethanesulfonic acid
• carboxylic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, benzoic acid, citric acid, and oxalic acid.
• a deodorizing process to reduce odor can be included as necessary.
• a deodorizing process since odors develop over time.
• the odor-developing mechanism of general polyether-modified silicones can be explained as follows. When an addition reaction is carried out between allyl-etherified polyether and hydrogen polyorganosiloxane in the presence of a platinum catalyst, the allyl group undergoes internal transfer as a side reaction to produce propenyl-etherified polyether. This propenyl-etherified polyether has no addition reactivity with hydrogen polyorganosiloxane, so it remains in the system as an impurity.
• the first method involves adding an acid catalyst to the solution after the addition reaction to hydrolyze all of the propenyl ether remaining in the system, and then distilling off the resulting propionaldehyde.
• acid catalysts used in the first formulation 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 formic acid, acetic acid, propionic acid, trifluoroacetic acid, benzoic acid, oxalic acid, and citric acid.
• 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
• carboxylic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, benzoic acid, oxalic acid, and citric acid.
• acids are used in combination with water, but when it is necessary to remove the acid used, it is preferable to use an acid with a low boiling point such as hydrochloric acid, formic acid, acetic acid, or trifluoroacetic acid.
• an acid with a low boiling point such as hydrochloric acid, formic acid, acetic acid, or trifluoroacetic acid.
• strong acids such as hydrochloric acid and trifluoroacetic acid
• weak acids such as citric acid and acetic acid.
• the treatment temperature is preferably 80°C or less to prevent oxidation of the hydrophilic groups.
• the amount of acidic aqueous solution added is preferably 0.1 to 100% by mass relative to the organic group-modified organosilicon resin, and more preferably 5 to 30% by mass.
• an aqueous solution to the solution after the reaction so that the pH becomes 7 or less, and then heat and stir the solution before strip purification.
• the above strip purification can be carried out at room temperature or under reduced pressure, but the temperature condition is preferably 120°C or less, and in order to efficiently strip purification under this temperature condition, it is preferable to carry out the purification under reduced pressure, or in the case of normal pressure, to carry out the purification under aeration of an inert gas such as nitrogen or argon.
• the second method is to add hydrogen to the solution after the addition reaction to alkylate the unsaturated double bonds (a so-called hydrogenation reaction), thereby stably controlling the generation of aldehyde compounds over time.
• Hydrogenation reactions can be carried out using hydrogen or metal hydrides, and can also be homogeneous or heterogeneous. These can be carried out alone or in combination. However, heterogeneous catalytic hydrogenation reactions using solid catalysts are preferred, as they have the advantage that the catalyst used does not remain in the product.
• Solid catalysts include, for example, nickel, palladium, platinum, rhodium, cobalt, chromium, copper, iron, and other elements or compounds.
• a catalyst carrier is not necessary, but if one is used, activated carbon, silica, silica alumina, alumina, zeolite, etc. are used. These catalysts can be used alone or in combination.
• the most preferred catalyst is Raney nickel, which is economically advantageous. Raney nickel is usually used by developing it with an alkali, so it is particularly important to carefully measure the pH of the reaction solution. In addition, the reaction system becomes weakly alkaline, so hydrolysis reactions using an acidic aqueous solution are particularly effective for deodorization.
• Hydrogenation reactions are generally preferably carried out at a pressure of 1 to 100 MPa and a temperature of 50 to 200°C.
• the hydrogenation reaction may be either palindromic or continuous. In the case of a palindromic reaction, the reaction time depends on the amount of catalyst and temperature, but is generally 3 to 12 hours.
• the hydrogen pressure can be adjusted to a constant pressure as appropriate, but the end point of the hydrogenation reaction is the point at which the hydrogen pressure no longer changes, and can be determined by carefully observing the pressure change.
• the amount of aldehyde contained in the crosslinked organosilicon resin purified by such acid treatment or hydrogenation reaction treatment can be preferably 70 ppm or less, more preferably 20 ppm or less, and even more preferably 10 ppm or less.
• the acid treatment method can decompose and remove aldehyde compounds, but there is a limit to completely removing unsaturated double bonds, so it is not possible to completely suppress the generation of aldehydes, which are the cause of odors.
• the hydrogenation reaction method can reduce the amount of aldehyde compounds generated by eliminating unsaturated double bonds, but aldehyde condensates generated by condensation of some of the aldehydes remain in the system even after the above treatment, and are difficult to remove by strip purification. Therefore, if a hydrogenation reaction is performed on the solution after the addition reaction to alkylate the remaining unsaturated double bonds, and then an acid catalyst is added to decompose the aldehyde condensates in the system, complete deodorization is possible.
• the weight average molecular weight of the organopolysiloxane of the present invention is preferably from 1,000 to 20,000, more preferably from 1,000 to 10,000, and even more preferably from 1,000 to 7,000.
• the weight-average molecular weight of the organopolysiloxane is 1,000 or more, it will be more effective in suppressing the aggregation of powder particles when used as a dispersant. If the weight-average molecular weight is 20,000 or less, the adsorptivity to powder will be more sufficient. This range is also preferable in terms of performance and workability such as filtration. For these reasons, the molecular weight of the organopolysiloxane of the present invention is preferably 1,000 to 20,000.
• the weight average molecular weight in the present invention is determined as a polystyrene-equivalent weight average molecular weight by gel permeation chromatography (GPC) analysis under the following conditions.
• GPC gel permeation chromatography
• the organopolysiloxane of the present invention has excellent dispersion stability of the powder, and therefore can provide a dispersion having excellent stability, for example, dispersion, viscosity and hardness stability of the powder.
• the dispersion include a dispersion containing the organopolysiloxane of the present invention, an oil and a powder.
• the blending amount is appropriately determined, and is preferably 0.1 to 30 mass% in the dispersion containing the organopolysiloxane of the present invention, an oil and a powder, and more preferably 0.5 to 15 mass%, and even more preferably 1 to 10 mass%.
• the viscosity of the liquid dispersion at 25°C is not particularly limited, but when produced by a medium stirring mill such as a bead mill, it is preferably less than 1,000 mPa ⁇ s from the viewpoint of ease of filtering the beads and ease of blending into cosmetics. Furthermore, it is more preferably less than 750 mPa ⁇ s, and even more preferably less than 500 mPa ⁇ s from the viewpoint of usability.
• the lower limit is not particularly limited, but by making it 100 mPa ⁇ s or more, the separation of light and dark in the dispersion is easily suppressed.
• the viscosity measurement conditions are a B-type viscometer, for example, a spindle LV-2, and the viscosity after 60 seconds at 30 revolutions.
• the hardness of the paste-like dispersion is also not particularly limited, but in the case of production with a three-roll machine, the hardness is preferably 100 or less from the viewpoint of ease of processing. Furthermore, from the viewpoint of ease of blending in cosmetics, it is more preferable that the hardness is less than 80, and even more preferable that the hardness is less than 50.
• the lower limit is not particularly limited, but by making it 5 or more, the separation of light and dark in the dispersion is easily suppressed.
• the hardness is a value measured with a rheometer, for example, a rheometer RT-2002D ⁇ D (manufactured by Rheotec Co., Ltd., measuring terminal: 10 mm ⁇ , needle penetration depth: 10 mm, sample stage rising speed: 5 cm/min, temperature: 25°C, range: 200).
• the powder to be dispersed is not particularly limited as long as it is a raw material that can be normally incorporated into cosmetics, and examples of such powder include fine metal oxide powders, hydrophobically treated color pigments, inorganic powders, metal powders, organic powders, inorganic-organic composite powders, etc. Specific examples are as follows.
• Fine particle metal oxide powder The fine particle metal oxide used in the present invention is one or more selected from fine particles of titanium oxide (display name (INCI: Titanium Dioxide)), iron-containing titanium oxide, zinc oxide (display name (INCI: Zinc Oxide)), cerium oxide (display name (INCI: Cerium Oxide)) and composites thereof. These metal oxides may be composite powders with other powders.
• the average primary particle size is preferably 200 nm or less, more preferably 120 nm or less. If the particle size is larger than this, the ultraviolet protection function decreases and white residue occurs.
• inorganic treatments include silica (display name (INCI: Silica)), alumina (display name (INCI: Alumina)), and aluminum hydroxide (display name (INCI: Aluminum Hydroxide)), while organic treatments include silanes or silylating agents such as triethoxycaprylylsilane (display name (INCI: Triethoxycaprylylsilane)), dimethicone (display name (INCI: Dimethicone)), hydrogen dimethicone (display name (INCI: Hydrogen Dimethicone)), and triethoxysilane (display name (INCI: Hydrogen Dimethicone)).
• inorganic treatments include silica (display name (INCI: Silica)), alumina (display name (INCI: Alumina)), and aluminum hydroxide (display name (INCI: Aluminum Hydroxide)
• organic treatments include silanes or silylating agents such as triethoxycaprylylsilane (display
• suitable organic fluorine compounds include silicone oils such as triethyl polydimethylsiloxyethylhexyl dimethicone (display name (INCI: Triethoxysilylethyl Polydimethylsiloxyethyl Hexyl Dimethicone)), waxes, paraffins, organic fluorine compounds such as perfluoroalkyl phosphates, surfactants, amino acids such as N-acyl glutamic acid, and metal soaps such as aluminum stearate (display name (INCI: Aluminum Stearate)) and magnesium myristate (display name (INCI: Magnesium Myristate)).
• silicone oils such as triethyl polydimethylsiloxyethylhexyl dimethicone (display name (INCI: Triethoxysilylethyl Polydimethylsiloxyethyl Hexyl Dimethicone)
• waxes such as triethoxysilyleth
• triethoxysilylethyl polydimethylsiloxyethylhexyl dimethicone (display name (INCI: Triethoxysilylethyl Polydimethylsiloxyethyl Hexyl Dimethicone)) is used in sunscreens and foundations because it has high dispersibility in both silicones and oils, and triethoxycaprylylsilane (display name (INCI: Triethoxycaprylylsilane)) and metal soap treatments are preferred in terms of compatibility with component (B) and component (D) described below. These surface treatments may be used alone or in combination of two or more depending on the purpose.
• fine titanium oxide particles are commercially available under the trade names STR-100C-LP, STR-100A-LP, STR-100W, STR-100W-LP, STR-100C-LF, STR-40-LP (manufactured by Sakai Chemical Industry Co., Ltd.), MT-N1, MT-01, MT-05, MT-100Z, MT-100TV, MT-100AQ, MT-100WP, MTY-100SAS, MT-150EX, MT-500B, MT-505SAS, MT-700B, MT-700Z, MT-014Z, SMT-500SAS (manufactured by Teika Co., Ltd.), ST-455, ST-455WS, ST-457ECS, ST-495M (manufactured by Titanium Industries Co., Ltd.), and the like.
• STR-100C-LP trade names STR-100C-LP, STR-100A-LP, STR-100W, STR-100
• the blending amount of the fine particle metal oxide is not particularly limited, but is preferably 0.1 to 70% by mass, more preferably 5 to 65% by mass, and even more preferably 45 to 65% by mass, based on the total amount of the dispersion. If it is less than 0.1% by mass, a sufficient ultraviolet shielding effect cannot be obtained, and if it is blended in excess of 70% by mass, the spread during use may be poor, or the cosmetic film may become white or powdery.
• the hydrophobically treated color pigments are not particularly limited as long as they are pigments that are normally used for the purpose of coloring cosmetics, and examples of such pigments include red iron oxide (display name (INCI: Iron Oxides)), yellow iron oxide (display name (INCI: Iron Oxides)), white titanium oxide (display name (INCI: Titanium Dioxide)), black iron oxide (display name (INCI: Iron Oxides)), ultramarines (display name (INCI: Ultramarines)), ferric iron oxide (display name (INCI: Ferric Ferrocyanide, Ferric Ammonium Ferrocyanide)), manganese violet (display name (INCI: Manganese (InCI: Titanium Violet)), cobalt titanate (InCI: Cobalt Titanium Oxide)), chromium hydroxide (InCI: Chromium Hydroxide Green)), chromium oxide (InCI: Chromium Oxide Greens)), aluminum/cobalt oxide (InCI: Cobalt Titanium Oxide)), chro
• the shape of the hydrophobically treated color pigment may be any shape, such as spherical, approximately spherical, rod-shaped, spindle-shaped, petal-shaped, rectangular, or irregular, and there is no particular limitation on its geometric form, so long as it is capable of imparting color to the cosmetic.
• the particle size i.e., the volume average particle size
• the volume average particle size can be measured by TEM, etc. If it is less than 150 nm, the hiding power is low, and the coloring efficiency of the cosmetic may be reduced, and if it is more than 600 nm, the feeling in use may be deteriorated.
• the pigment according to the present invention may be partially or completely surface-treated with an inorganic compound such as alumina (display name (INCI: Alumina)), aluminum hydroxide (display name (INCI: Aluminum Hydroxide)), silica (display name (INCI: Silica)), or hydrated silica (display name (INCI: Hydrated Silica)).
• an inorganic compound such as alumina (display name (INCI: Alumina)), aluminum hydroxide (display name (INCI: Aluminum Hydroxide)), silica (display name (INCI: Silica)), or hydrated silica (display name (INCI: Hydrated Silica)).
• the hydrophobization of the hydrophobized color pigment refers to subjecting the color pigment to a surface treatment with a hydrophobizing agent.
• the surface hydrophobizing agent for the color pigment of the present invention is not particularly limited as long as it can impart hydrophobicity, and examples of such agents include silicone treatment agents, waxes, paraffins, organic fluorine compounds such as perfluoroalkyl and phosphates, surfactants, amino acids such as N-acyl glutamic acid, and metal soaps such as aluminum stearate (display name (INCI: Aluminum Stearate)) and magnesium myristate (display name (INCI: Magnesium Myristate)).
• silicone treatment agents are preferably used, and examples of such agents include silanes or silylating agents such as triethoxycaprylylsilane (display name (INCI: Triethoxycaprylylsilane)) or trimethoxysilyl dimethicone (display name (INCI: Trimethoxysilyl Dimethicone)), dimethicone (display name (INCI: Dimethicone)), hydrogen dimethicone (display name (INCI: Hydrogen Dimethicone)), triethoxysilylethyl polydimethylsiloxyethylhexyl dimethicone (display name (INCI: Triethoxysilylethyl Polydimethylsiloxyethylhexyl Dimethicone)).
• silanes or silylating agents such as triethoxycaprylylsilane (display name (INCI: Triethoxycaprylylsilane)) or trimeth
• silicone oil examples include silicone oils such as (Acrylates/Tridecyl Acrylate/Triethoxysilylpropyl Methacrylate/Dimethicone Methacrylate) Copolymer (Display name (INCI: Acrylates/Tridecyl Acrylate/Triethoxysilylpropyl Methacrylate/Dimethicone Methacrylate Copolymer)) and silicone compounds such as (Acrylates/Dimethicone) Copolymer (Display name (INCI: Acrylates/Dimethicone Copolymer)).
• silicone treatment agent the silicone powder treatment agent described in Patent No.
• 3912961 is preferably used, and in particular, triethoxysilylethyl polydimethylsiloxyethylhexyl dimethicone (display name (INCI: Triethoxysilylethyl Polydimethylsiloxyethyl Hexyl Dimethicone)), which is a dimethylpolysiloxane having a triethoxysilyl group, a polydimethylsiloxyethyl group, and a hexyl group on the side chain, is effectively used because it exhibits high affinity even when the dispersion medium for dispersing the highly hydrophobic treated color pigment is a mixture composition of silicone and hydrocarbon.
• the above surface hydrophobic treatment agents can be used alone or in combination of two or more.
• the manufacturing method for surface-treating the color pigment using a hydrophobic treatment agent is not particularly limited, and can be carried out by a known method.
• Surface treatment methods can be broadly divided into dry methods and wet methods.
• any stirrer, grinder, mixer, disperser, etc. such as a Henschel mixer, ball mill, jet mill, kneader, planetary mixer, sand mill, attritor, ribbon blender, disperser mixer, homomixer, etc., can be used to mix/contact the color pigment used in the present invention with the hydrophobic treatment agent.
• the treatment may be performed while applying energy such as heating, mechanochemical mechanical force, superheated steam, etc.
• the treatment may be performed by applying energy such as heating, mechanochemical mechanical force, superheated steam, etc.
• energy such as heating, mechanochemical mechanical force, superheated steam, etc.
• the hydrophobic treatment agent may be dissolved or dispersed in advance in an arbitrary amount of water, solvent, or supercritical fluid, and then sprayed onto the colored pigment.
• the colored pigment and the hydrophobic treatment agent are dispersed in water, solvent, or supercritical fluid, mixed/contacted, and then the solvent is evaporated, and further, energy such as heating, mechanochemical mechanical force, or superheated steam is separately applied to perform the treatment.
• color pigments that have been subjected to hydrophobic surface treatment include the KTP-09 series, in particular KTP-09W, KTP-09R, KTP-09Y, and KTP-09B (manufactured by Shin-Etsu Chemical Co., Ltd.).
• Inorganic powders include zirconium oxide (indication name (INCI: Zirconium Dioxide)), zinc oxide (indication name (INCI: Zinc Oxide)), cerium oxide (indication name (INCI: Cerium Oxide)), Mg (display name (INCI: Magnesium Oxide)), Ba sulfate (display name (INCI: Barium Sulfate)), calcium sulfate (display name (INCI: Calcium Sulfate)), Mg sulfate (display name (INCI: Magnesium Sulfate)) , Ca carbonate (indication name (INCI: Calcium Carbonate)), Mg carbonate (indication name (INCI: Magnesium) Carbonate), talc (indication name (INCI: Talc)), cleaved talc (indication name (INCI: Talc)), mica (indication name (INCI: Mica)), kaolin (indication name (INCI: Kaolin)), Ser
• Bismuth oxychloride coated with titanium oxide (INCI:Titanium Dioxide) (Indication name (INCI:Bismuth Oxychloride)
• talc coated with titanium oxide Indication name (INCI:Titanium Dioxide)
• Examples of the surface treatment include pearl pigments such as titanium dioxide (indicated by INCI: Talc), fish scale foil, and titanium dioxide (indicated by INCI: Titanium Dioxide)-coated colored mica. These are known surface treatments that are generally used in cosmetics even when untreated. But there is no particular limitation.
• Metal Powders examples include fine metal particles made of aluminum (display name (INCI: Aluminum Powder)), copper (display name (INCI: Copper Powder)), silver (display name (INCI: Silver Powder)), etc.
• organic powders examples include powders made of silicone, polyamide, polyacrylic acid/acrylic acid ester, polyester, polyethylene, polypropylene, polystyrene, styrene/acrylic acid copolymer, divinylbenzene/styrene copolymer, polyurethane, vinyl resin, urea resin, melamine resin, benzoguanamine, polymethylbenzoguanamine, tetrafluoroethylene, polymethyl methacrylate (e.g., polymethyl methacrylate), cellulose, silk, nylon, phenolic resin, epoxy resin, polycarbonate, and the like.
• silicone silicone
• polyamide polyacrylic acid/acrylic acid ester
• polyester polyethylene
• polypropylene polystyrene
• polystyrene/acrylic acid copolymer divinylbenzene/styrene copolymer
• polyurethane vinyl resin
• urea resin melamine resin
• benzoguanamine polymethylbenzogu
• silicone examples include silicone resin particles (specific examples include polymethylsilsesquioxane (display name (INCI: Polymethylsilsesquioxane)) and the like) and silicone resin-coated silicone rubber powder (specific examples include (vinyl dimethicone/methicone silsesquioxane) crosspolymer (display name (INCI: Vinyl Dimethicone/Methicone Silsesquioxane Crosspolymer)), (diphenyl dimethicone/vinyl diphenyl dimethicone/silsesquioxane) crosspolymer (display name (INCI: Diphenyl Dimethicone/Vinyl Diphenyl Dimethicone/Silsesquioxane)
• Examples of the polysilicone-1 crosspolymer include polysilicone-1 crosspolymer (labeled name (INCI: Polysilicone-1 Crosspolymer)), polysilicone-22 (labeled name (INCI: Polymethyl
• Metal soaps are also included, and specific examples thereof include zinc stearate (labeled name (INCI: Zinc Stearate)), aluminum stearate (labeled name (INCI: Aluminum Stearate)), calcium stearate (labeled name (INCI: Calcium Stearate)), magnesium stearate (labeled name (INCI: Magnesium Stearate)), zinc myristate (labeled name (INCI: Zinc Myristate)), magnesium myristate (labeled name (INCI: Magnesium Stearate)), and the like.
• Examples of the pigment include powders of zinc/sodium cetyl phosphate (display name (INCI: Sodium Zinc Cetyl Phosphate)), potassium cetyl phosphate (display name (INCI: Potassium Cetyl Phosphate)), and the like.
• examples of the pigment include organic pigments, and specific examples thereof include Red 3, Red 104(1) (display name (INCI: Red 28, Red 28 Lake)), Red 106, Red 201 (display name (INCI: Red 6)), Red 202 (display name (INCI: Red 7)), Red 204, Red 205, Red 220 (display name (INCI: Red 34)), Red 226 (display name (INCI: Red 30)), Red 227 (Display name (INCI: Red 33,, RED 33 Lake)), Red 228 (Display name (INCI: Red 36)), Red 230 (1) (Display name (INCI: Red 22, Red 22 Lake)), Red 230 (2), Red 401, Red 505, Yellow 4 (Display Name (INCI: Yellow 5)), Yellow 5 (Display name (INCI: Yellow 6, Yellow 6 Lake)), Yellow 202 (1) (Display name (INCI: Yellow 8)), Yellow 203 (Display name (INCI: Yellow 10, Yellow 10 Lake)) 4 (Display name (INCI: Yellow 11)), Yellow 3,
• inorganic-Organic Composite Powders examples include composite powders in which the surface of an inorganic powder is coated with an organic powder by a publicly known method.
• the amount of powder in the dispersion containing the organopolysiloxane of the present invention, oil, and powder is preferably 30 to 90 mass%, more preferably 40 to 85 mass%, and even more preferably 50 to 85 mass%.
• the oil that is the dispersion medium in which the powder is dispersed by the organopolysiloxane of the present invention is not particularly limited, but preferably has a kinetic viscosity of 1 to 100 mm 2 /s, more preferably 1 to 30 mm 2 /s, at 25°C as measured with a Cannon-Fenske viscometer according to the method described in JIS Z 8803: 2011, and even more preferably has a kinetic viscosity of 1 to 20 mm 2 /s from the viewpoint of compatibility with the organopolysiloxane of the present invention.
• Specific examples of the oil include silicone oil, hydrocarbon oil, ester oil, higher fatty acid, natural oil, and fluorine-based oil. The uses of these oils are not limited to dispersing media for powders, but they can be incorporated into cosmetics for a variety of purposes.
• silicone oils examples include trisiloxane (display name (INCI: Trisiloxane)), volatile dimethicone (display name (INCI: Dimethicone)), low viscosity dimethicone (display name (INCI: Dimethicone)), cyclotetrasiloxane (display name (INCI: Cyclotetrasiloxane)), cyclopentasiloxane (display name (INCI: Cyclopentasiloxane)), cyclohexasiloxane (display name (INCI: Cyclohexasiloxane)), methyl trimethicone (display name (INCI: Methyl Trimethicone)), and caprylyl methicone (display name (INCI: Caprylyl Methicone), Phenyl Trimethicone (Display name (INCI: Phenyl Trimethicone)), Methylphenylpoly
• examples of commercially available silicone oils include KF-96L-1cs, KF-96L-1.5cs, KF-96L-2cs, KF-96A-6cs, KF-4422, KF-4418, KF-56A, and KF-995, all manufactured by Shin-Etsu Chemical Co., Ltd.
• silicone rubbers such as highly polymerized gummy dimethicone (display name (INCI: Dimethicone)), gummy amodimethicone (display name (INCI: Amodimethicone)), gummy dimethylsiloxane-methylphenylsiloxane copolymer, as well as cyclic organopolysiloxane solutions of silicone gums and rubbers, amino acid-modified silicones, fluorine-modified silicones, silicone resins and silicone resin solutions.
• examples of commercially available silicone oils include KF-54 and KF-54HV.
• hydrocarbon oil examples include linear or branched hydrocarbon oils, and may be either volatile or non-volatile hydrocarbon oils.
• olefin oligomers ICI
• isododecane display name (INCI: Isododecane)
• dodecane display name (INCI: Dodecane)
• isohexadecane display name (INCI: Isohexadecane)
• undecane decane
• squalane display name (INCI: Squalane)
• squalene dislay name (INCI: Squalene)
• mineral oil mineral Oil
• mineral Oil mineral Oil
• Ester oils are liquid oils formed by condensing fatty acids having 1 to 20 carbon atoms with alcohols having 1 to 20 carbon atoms, and like the natural oils, they include compositions derived from animals and plants, and examples of such oils include monoesters, diesters, and triesters.
• alkyl glycol monoisostearates such as diisobutyl adipate (display name: INCI: Diisobutyl Adipate), dihexyldecyl adipate (display name: INCI: Diheptylundecyl Adipate), and isostearyl isostearate (display name: INCI: Isostearyl Isostearate), isocetyl isostearate (display name: INCI: Isocetyl Isostearate), trimethylolpropane triisostearate (display name: INCI: Trimethylolpropane Triisostearate), and glycol diethylhexanoate (display name: INCI: Glycol Diethylhexanoate), Cetyl ethylhexanoate (Display name (INCI: Cetyl Ethylhexanoate)), Triethylhexanoin (Display name (INCI)
• Higher fatty acids examples include oleic acid (display name (INCI: Oleic Acid)), linoleic acid (display name (INCI: Linoleic Acid)), linolenic acid (display name (INCI: Linolenic Acid)), arachidonic acid (display name (INCI: Arachidonic Acid)), eicosapentaenoic acid (EPA) (display name (INCI: Eicosapentaenoic Acid)), docosahexaenoic acid (DHA) (display name (INCI: Docosahexaenoic Acid)), isostearic acid (display name (INCI: Isostearic Acid)), and hydroxystearic acid (display name (INCI: Hydroxystearic Acid)).
• oleic acid display name (INCI: Oleic Acid)
• linoleic acid display name (INCI: Linoleic Acid)
• Natural oils include natural animal and vegetable oils and semi-synthetic oils and fats. Specific examples of the natural oils include avocado oil (labeled name (INCI: Persea Gratissima (Avocado) Oil)), linseed oil (labeled name (INCI: Linum Usitatissimum (Linseed) Seed Oil)), almond oil (labeled name (INCI: Prunus Amygdalus Dulcis (Sweet Almond) Oil)), olive oil (labeled name (INCI: Olea Europaea (Olive) Fruit Oil)), and American grass oil (labeled name (INCI: Torreya California (California) Oil)).
• avocado oil label (INCI: Persea Gratissima (Avocado) Oil)
• linseed oil label (INCI: Linum Usitatissimum (Linseed) Seed Oil)
• almond oil label (labeled name (INCI: Prunus
• fluorine-based oils include perfluoropolyethers such as polyperfluoromethylisopropyl ether (display name (INCI: Polyperfluoromethylisopropyl Ether)), and perfluorocarbons such as perfluorodecalin (display name (INCI: Perfluorodecalin)) and perfluorohexane (display name (INCI: Perfluorohexane)).
• perfluoropolyethers such as polyperfluoromethylisopropyl ether (display name (INCI: Polyperfluoromethylisopropyl Ether)
• perfluorocarbons such as perfluorodecalin (display name (INCI: Perfluorodecalin)) and perfluorohexane (display name (INCI: Perfluorohexane)).
• the amount of oil in the dispersion containing the organopolysiloxane of the present invention, oil, and powder is preferably 9 to 69 mass%, more preferably 14 to 50 mass%, and even more preferably 14 to 45 mass%.
• the method for preparing the dispersion is preferably a dispersion in which the powder is premixed with the organopolysiloxane of the present invention and oil.
• a suitable dispersing machine such as a three-roll mill, homomixer, disperser, media stirring mill such as a bead mill, a wet high pressure dispersing machine, or an ultrasonic dispersing machine is appropriately selected and used.
• the cosmetic is not particularly limited as long as it contains the organopolysiloxane of the present invention.
• the powder can be blended into the cosmetic in the same manner as other components without any prior treatment, but when higher dispersibility in the cosmetic is desired, it is preferable to prepare a dispersion in which the powder is previously mixed with other components and then blend this.
• the organopolysiloxane of the present invention When used in a cosmetic, it may be used alone or in combination of two or more. As described above, the organopolysiloxane of the present invention has excellent powder dispersibility, but its use in cosmetics is not limited to dispersants. For example, it may be used as an emulsifier when making a water-in-oil emulsion, or as a stabilizer for an oil-in-water emulsion, or as a feel adjuster or compatibilizer for non-aqueous preparations.
• the amount of the organopolysiloxane is preferably in the range of 0.1 to 40% by mass of the entire cosmetic, and as an emulsifier, it is more preferably in the range of 0.1 to 5% by mass of the entire cosmetic. Even when it is used as a dispersion, the amount of the organopolysiloxane can be appropriately adjusted so that it falls within the above range.
• the cosmetic of the present invention has excellent usability, spreadability, and preferably stability.
• the cosmetic of the present invention may contain, in addition to the oil and powder, various ingredients used in ordinary cosmetics to the extent that the effect of the present invention is not impaired.
• it may contain (1) an oil, (2) an aqueous component, (3) a surfactant, (4) a powder, (5) a composition consisting of a cross-linked organopolysiloxane and an oil that is liquid at room temperature, (6) a film-forming agent, and (7) other additives. These may be used alone or in appropriate combinations of two or more, each in an appropriate amount. It may also contain the powder and oil exemplified in the above dispersion.
• Oil Agent may be volatile or non-volatile and may be solid, semi-solid, or liquid at room temperature (25° C.).
• examples of the oil agent include the oils described above, as well as the oils used in the above dispersions, components that are solid or semi-solid at room temperature (25° C.), and ultraviolet absorbers.
• the oily component that is solid at 25°C preferably has a melting point of 40°C or higher, more preferably 60 to 110°C, and examples of such components include waxes, hydrocarbons, esters, higher alcohols, and higher fatty acids.
• a melting point 40°C or higher, more preferably 60 to 110°C
• examples of such components include waxes, hydrocarbons, esters, higher alcohols, and higher fatty acids.
• the waxes include vegetable waxes such as carnauba wax, sugarcane wax, candelilla wax, refined candelilla wax, rice wax, wood wax, jojoba wax, kapok wax, rice bran wax, white bayberry fruit wax, shea butter, cacao butter, Rhus succedanea fruit wax (INCI: Rhus succedanea fruit wax), Montan wax (INCI: Montan wax), and hydrogenated castor oil isostearate; animal waxes such as beeswax, beef tallow, beef bone fat, lard (INCI: Lard), horse fat (INCI: Horse Fat), sheep tallow, lanolin (INCI: Lanolin), Chinese laurel, shellac wax, and whale wax; semi-synthetic waxes such as lanolin esters, lanolin fatty acid esters, and beeswax acid esters; hydrogenated oils such as hydrogenated castor oil and hydrogenated coconut oil; solid palm oils; Examples of the wax include hydrocarbon waxes
• Ultraviolet absorbing agents include oxybenzone-1 (label name: INCI: Benzophenone-1), oxybenzone-2 (label name: INCI: Benzophenone-2), oxybenzone-3 (label name: INCI: Benzophenone-3), oxybenzone-4 (label name: INCI: Benzophenone-4), oxybenzone-5 (label name: INCI: Benzophenone-5), oxybenzone-6 (label name: INCI: Benzophenone-6), oxybenzone-9 (label name: INCI: Benzophenone-9), homosalate (INCI), octocrylene (INCI), t-butyl methoxydibenzoylmethane (label name: INCI: Butyl Methoxydibenzoylmethane), lmethane), Ethylhexyl Salicylate (Display name (INCI: Ethylhexyl Salicylate)), Diethylamino Hydr
• UVA absorber e.g., diethylaminohydroxybenzoyl hexyl benzoate, etc.
• UVB absorber e.g., ethylhexyl methoxycinnamate, etc.
• the amount of oil in the cosmetic is preferably 1 to 85% by mass, more preferably 3 to 30% by mass, and even more preferably 5 to 20% by mass.
• the aqueous component is not particularly limited as long as it is an aqueous component that can be normally incorporated into cosmetics.
• Specific examples include water, lower alcohols preferably having 2 to 5 carbon atoms, such as ethanol (display name (INCI: Alcohol)) and isopropanol (display name (INCI: Isopropyl Alcohol)), and sugar alcohols, such as sorbitol (INCI), maltose (INCI), and xylitol (INCI).
• polyhydric alcohols such as BG (display name (INCI: Butylene Glycol)), PG (display name (INCI: Propylene Glycol)), DPG (display name (INCI: Dipropylene Glycol)), pentylene glycol (INCI), 1,10-decanediol (INCI), octanediol (INCI), 1,2-hexanediol (INCI), erythritol (INCI), glycerin (INCI), diglycerin (INCI), and polyethylene glycol; glucose (INCI), glyceryl glucoside (INCI), betaine (INCI), sodium chondroitin sulfate (display name (INCI: Sodium Chondroitin Sulfate)), and sodium PCA (display name (INCI: Sodium Chondroitin Sulfate)).
• moisturizing agents include PCA), methyl gluceth-10 (INCI), methyl gluceth-20 (INCI), hyaluronic acid, egg yolk lecithin, soybean lecithin, phosphatidylcholine, phosphatidylethanolamine, phosphatidylserine, phosphatidylglycerol, phosphatidylinositol, sphingophospholipid, etc.
• the blended amount of water, etc. may be the remainder.
• the surfactant may be nonionic, anionic, cationic or amphoteric, but is not particularly limited, and any surfactant used in ordinary cosmetics may be used.
• these surfactants one or more selected from non-crosslinked silicone surfactants and crosslinked silicone surfactants are preferred from the viewpoint of obtaining a stable cosmetic.
• the amount of the surfactant is preferably 0.1 to 20% by mass of the entire cosmetic. If it is 0.1% or more, the function of dispersion and emulsification can be sufficiently performed, and if it is 20% by mass or less, there is no risk of the cosmetic having a sticky feel.
• the HLB of the surfactant is not limited, but is preferably 2 to 14.5 from the viewpoint of maintaining the water resistance of the cosmetic.
• Non-crosslinked silicone surfactants are those in which some of the methyl groups in a linear or branched silicone main chain have been replaced with hydrophilic groups such as polyethylene glycol or polyglycerin, and specifically, preferred are linear or branched polyoxyethylene-modified organopolysiloxanes, linear or branched polyoxyethylene-polyoxypropylene-modified organopolysiloxanes, linear or branched polyoxyethylene-alkyl-co-modified organopolysiloxanes, linear or branched polyoxyethylene-polyoxypropylene-alkyl-co-modified organopolysiloxanes, linear or branched polyglycerin-modified organopolysiloxanes, linear or branched polyglycerin-alkyl-co-modified organopolysiloxanes, and linear or branched pyrrolidone-modified organopolysiloxanes.
• Examples include PEG-11 methyl ether dimethicone (INCI), PEG/PPG-20/22 butyl ether dimethicone (INCI), PEG-3 dimethicone (INCI), PEG-10 dimethicone (INCI), PEG-9 polydimethylsiloxyethyl dimethicone (INCI), lauryl PEG-9 polydimethylsiloxyethyl dimethicone (INCI), cetyl PEG/PPG-10/1 dimethicone (INCI), polyglyceryl-3 disiloxane dimethicone (INCI), polyglyceryl-3 polydimethylsiloxyethyl dimethicone (INCI), lauryl polyglyceryl-3 polydimethylsiloxyethyl dimethicone (INCI), bis-butyl dimethicone polyglyceryl-3 (INCI), etc.
• cross-linked silicone surfactants include cross-linked polyether-modified silicones such as (dimethicone/(PEG-10/15)) crosspolymer (INCI), (PEG-15/lauryl dimethicone) crosspolymer (INCI), (PEG-10/lauryl dimethicone) crosspolymer (INCI), and (PEG-15/lauryl polydimethylsiloxyethyl dimethicone) crosspolymer (INCI), as well as cross-linked polyglycerin-modified silicones such as (dimethicone/polyglycerin-3) crosspolymer (INCI), (lauryl dimethicone/polyglycerin-3) crosspolymer (INCI), and (polyglycerin-3/lauryl polydimethylsiloxyethyl dimethicone) crosspolymer (INCI).
• cross-linked polyether-modified silicones such as (dimethicone/(PEG-10/15)) cross
• cross-linked silicone surfactant when used, in a composition consisting of the cross-linked silicone surfactant and an oily agent that is liquid at room temperature, it is preferable that the cross-linked silicone surfactant swells with the liquid oil by absorbing an amount of the liquid oily agent that is equal to or greater than its own weight.
• liquid silicone oil liquid silicone oil, hydrocarbon oil, ester oil, natural animal and vegetable oil, semi-synthetic oil, etc., as listed above, and fluorine-based oil
• examples include cyclopentasiloxane (INCI), dimethicone (INCI), mineral oil (INCI), isododecane (INCI), isohexadecane (INCI), triethylhexanoin (INCI), isotridecyl isononanoate (display name: INCI: Isotridecyl Isononanoate), squalane (INCI), etc.
• Examples of commercially available cross-linked silicone surfactants that swell when they contain a liquid oil include those manufactured by Shin-Etsu Chemical Co., Ltd.: KSG-210, KSG-240, KSG-270, KSG-310, KSG-320, KSG-330, KSG-340, KSG-320Z, KSG-350Z, KSG-710, KSG-810, KSG-820, KSG-830, KSG-840, KSG-820Z, KSG-850Z, etc.
• the powder can be used separately or in combination with the organopolysiloxane as a dispersion. Alternatively, the powder can be incorporated into the cosmetic as another dispersion.
• Specific examples of dispersions in which particles that absorb and scatter ultraviolet light are dispersed in an oil agent include the SPD series (product name) manufactured by Shin-Etsu Chemical Co., Ltd., in particular SPD-T5, T5L, Z5, Z5L, T6, Z6, T7, and Z7L.
• the amount of powder in the cosmetic is preferably 0.5 to 90% by mass, more preferably 1 to 30% by mass, and even more preferably 5 to 20% by mass.
• composition consisting of crosslinked organopolysiloxane and oil agent liquid at room temperature In a composition consisting of crosslinked organopolysiloxane and oil agent liquid at room temperature, it is preferable that the crosslinked organopolysiloxane swells with the liquid oil by absorbing more than its own weight of the liquid oil.
• the liquid oil agent may be a liquid silicone oil, a hydrocarbon oil, an ester oil, a natural animal or vegetable oil, a semi-synthetic oil, or a fluorine-based oil, as listed above, and examples of the liquid oil include cyclopentasiloxane (INCI), dimethicone (INCI), mineral oil (INCI), isododecane (INCI), isohexadecane (INCI), triethylhexanoin (INCI), isotridecyl isononanoate (display name (INCI: Isotridecyl Isononanoate)), squalane (INCI), etc.
• component (5) is a compound that does not have a polyether or polyglycerin structure in its molecular structure, and specific examples include dimethicone/vinyl dimethicone crosspolymer (INCI), dimethicone/phenylvinyl dimethicone crosspolymer (INCI), vinyl dimethicone/lauryl dimethicone crosspolymer (INCI), lauryl polydimethylsiloxyethyl dimethicone/bisvinyl dimethicone crosspolymer (INCI), and the like.
• Film-forming agents are mainly blended for the purpose of further maintaining the durability of the cosmetic effect.
• the composition is a silicone-based composition from the viewpoint of imparting water repellency.
• trimethylsiloxysilicate, crosslinked trimethylsiloxysilicate, modified trimethylsiloxysilicate, acrylic-silicone film-forming agent, silicone-modified norbornene, silicone-modified pullulan, silicone-modified polyvinyl alcohol, etc. can be used.
• film-forming agents for silicone-based compositions include trimethylsiloxysilicate (labeled as (INCI): Trimethylsiloxysilicate), (acrylates/dimethicone) copolymer (INCI), (norbornene/tris(trimethylsiloxy)silylnorbornene) copolymer (INCI), tri(trimethylsiloxy)silylpropylcarbamate pullulan (labeled as (INCI): Trimethylsiloxysilylcarbamoyl Pullulan) and the like.
• the film-forming agent may be dissolved in a liquid oil at room temperature beforehand and then blended into the cosmetic.
• the liquid oil may be liquid silicone oil, hydrocarbon oil, ester oil, natural animal and vegetable oil, semi-synthetic oil, or fluorine-based oil, which are included in the optional component (1) oil.
• Specific examples of commercially available silicone film-forming agents include KF-7312J, KP-545, KP-549, KP-543, NBN-30-ID, TSPL-30-ID, TSPL-30-D5, and the like, all manufactured by Shin-Etsu Chemical Co., Ltd.
• additives examples include oil-soluble gelling agents, preservatives/bactericides, antiperspirants, fragrances, salts, antioxidants, pH adjusters, chelating agents, cooling agents, anti-inflammatory agents, skin beautifying ingredients (skin whitening agents, cell activators, skin roughness improving agents, blood circulation promoters, skin astringents, antiseborrheic agents, etc.), vitamins, amino acids, nucleic acids, hormones, inclusion compounds, etc.
• Oil-soluble gelling agents examples include metal soaps such as aluminum stearate, magnesium stearate, and zinc myristate; amino acid derivatives such as lauroyl glutamic acid (display name (INCI: Lauroyl Glutamic Acid)) and ⁇ , ⁇ -di-n-butylamine; dextrin palmitate (display name (INCI: Dextrin Palmitate)), dextrin isostearate (display name (INCI: Dextrin Isostearate)), dextrin myristate (display name (INCI: Dextrin Myristate)), inulin stearate (display name (INCI: Stearoyl Inulin)), and dextrin (palmitic acid/ethylhexanoate) (display name (INCI: Dextrin dextrin fatty acid esters such as sucrose palmitate, sucrose stearate, etc.; fructooligosaccharide fatty acid
• preservatives and disinfectants examples include paraoxybenzoic acid alkyl esters, benzoic acid, sodium benzoate, sorbic acid, potassium sorbate, phenoxyethanol, imidazolidinyl urea, salicylic acid, isopropyl methylphenol, carbolic acid, parachlormetacresol, hexachlorophene, benzalkonium chloride, chlorhexidine chloride, trichlorocarbanilide, iodide propynyl butylcarbamate, polylysine, photosensitizers, silver, plant extracts, etc.
• preservatives and disinfectants include paraoxybenzoic acid alkyl esters, benzoic acid, sodium benzoate, sorbic acid, potassium sorbate, phenoxyethanol, imidazolidinyl urea, salicylic acid, isopropyl methylphenol, carbolic acid, parachlormetacresol, hexachlorophene, benzalkonium chloride
• Antiperspirants include hydroxyaluminum halides such as chlorohydroxy AL, aluminum halides such as AL chloride, aluminum allantoin salt, tannic acid, persimmon tannin, sulfuric acid (AL/K), zinc oxide, zinc paraphenolsulfonate, burnt alum, tetrachloro(Al/zirconium) hydrate, trichlorohydrex glycine (Al/zirconium), etc.
• hydroxyaluminum halides such as chlorohydroxy AL
• aluminum halides such as AL chloride, aluminum allantoin salt, tannic acid, persimmon tannin, sulfuric acid (AL/K), zinc oxide, zinc paraphenolsulfonate, burnt alum, tetrachloro(Al/zirconium) hydrate, trichlorohydrex glycine (Al/zirconium), etc.
• hydroxyaluminum halides, aluminum halides, and complexes or mixtures thereof with zirconyl oxyhalides and zirconyl hydroxyhalides are preferred.
• zirconyl oxyhalides and zirconyl hydroxyhalides e.g., tetrachloro(Al/zirconium) hydrate, trichlorohydrex glycine (Al/zirconium)
• Fragrances Fragrances include natural fragrances and synthetic fragrances. Natural fragrances include plant-based fragrances isolated from flowers, leaves, wood, peels, etc.; and animal-based fragrances such as musk and civet. Synthetic fragrances include hydrocarbons such as monoterpenes, alcohols such as aliphatic alcohols and aromatic alcohols, aldehydes such as terpene aldehydes and aromatic aldehydes, ketones such as alicyclic ketones, esters such as terpene esters, lactones, phenols, oxides, nitrogen-containing compounds, and acetals.
• Natural fragrances include plant-based fragrances isolated from flowers, leaves, wood, peels, etc.; and animal-based fragrances such as musk and civet.
• Synthetic fragrances include hydrocarbons such as monoterpenes, alcohols such as aliphatic alcohols and aromatic alcohols, aldehydes such as terpene aldehydes and aromatic aldehydes, keto
• salts include inorganic salts, organic acid salts, amine salts, and amino acid salts.
• inorganic salts include sodium salts, potassium salts, magnesium salts, calcium salts, aluminum salts, zirconium salts, zinc salts, and the like of inorganic acids such as hydrochloric acid, sulfuric acid, carbonic acid, and nitric acid;
• organic acid salts include salts of organic acids such as acetic acid, dehydroacetic acid, citric acid, malic acid, succinic acid, ascorbic acid, and stearic acid;
• examples of amine salts and amino acid salts include salts of amines such as triethanolamine, and salts of amino acids such as glutamic acid.
• salts of hyaluronic acid, chondroitin sulfate, and the like, aluminum zirconium glycine complexes, and further neutral salts of acids and alkalis used in cosmetic formulations can also be used.
• Antioxidants are not particularly limited, but examples thereof include carotenoids, ascorbic acid and its salts, ascorbyl stearate, tocopherol, tocopherol acetate, tocopherol, p-t-butylphenol, butylhydroxyanisole, dibutylhydroxytoluene, phytic acid, ferulic acid, thiotaurine, hypotaurine, sulfites, erythorbic acid and its salts, chlorogenic acid, epicatechin, epigallocatechin, epigallocatechin gallate, apigenin, campherol, myricetin, quercetin, etc. Only one type of antioxidant may be used, or two or more types may be used in combination.
• pH Adjusting Agent examples include lactic acid, citric acid, glycolic acid, succinic acid, tartaric acid, dl-malic acid, potassium carbonate, sodium hydrogen carbonate, and ammonium hydrogen carbonate.
• Chelating Agents examples include alanine, edetic acid sodium salt, sodium polyphosphate, sodium metaphosphate, phosphoric acid, and the like.
• Cooling agents include L-menthol, camphor, menthyl lactate, and the like.
• Anti-inflammatory Agents examples include allantoin, glycyrrhizinic acid and its salts, glycyrrhetinic acid and stearyl glycyrrhetinate, tranexamic acid, azulene, and the like.
• Skin-beautifying ingredients include whitening agents such as placenta extract, arbutin, glutathione, and saxifrage extract; cell activators such as royal jelly, photosensitizers, cholesterol derivatives, and calf blood extract; rough skin improving agents; blood circulation promoters such as nonylic acid wasteamide, nicotinic acid benzyl ester, nicotinic acid ⁇ -butoxyethyl ester, capsaicin, zingerone, cantharides tincture, ichthammol, caffeine, tannic acid, ⁇ -borneol, tocopherol nicotinate, inositol hexanicotinate, cyclandelate, cinnarizine, tolazoline, acetylcholine, verapamil, cepharanthine, and ⁇ -oryzanol; skin astringents such as zinc oxide and tannic acid; and antiseborr
• Vitamins include vitamin A oil, vitamin A derivatives such as retinol, retinol acetate, and retinol palmitate, vitamin B2 derivatives such as riboflavin, riboflavin butyrate, and flavin adenine nucleotide, vitamin B6 derivatives such as pyridoxine hydrochloride, pyridoxine dioctanoate, and pyridoxine tripalmitate, vitamin B derivatives such as vitamin B12 and its derivatives, and vitamin B15 and its derivatives, L-ascorbic acid, L-ascorbic acid dipalmitate, sodium L-ascorbic acid 2-sulfate, and dipotassium L-ascorbic acid phosphate diester.
• vitamin A derivatives such as retinol, retinol acetate, and retinol palmitate
• vitamin B2 derivatives such as riboflavin, riboflavin butyrate, and flavin adenine nucleot
• vitamin C such as ergocalciferol and cholecalciferol
• vitamin D such as ⁇ -tocopherol, ⁇ -tocopherol, ⁇ -tocopherol, dl- ⁇ -tocopherol acetate, dl- ⁇ -tocopherol nicotinate, and dl- ⁇ -tocopherol succinate
• nicotinic acids such as nicotinic acid, benzyl nicotinate, and nicotinamide
• vitamin H vitamin P
• pantothenic acids such as calcium pantothenate, D-pantothenyl alcohol, pantothenyl ethyl ether, and acetyl pantothenyl ethyl ether
• biotin such as calcium pantothenate, D-pantothenyl alcohol, pantothenyl ethyl ether, and acetyl pantothenyl ethyl ether
• Amino acids include glycine, valine, leucine, isoleucine, serine, threonine, phenylalanine, arginine, lysine, aspartic acid, glutamic acid, cystine, cysteine, methionine, tryptophan, and the like.
• nucleic acids examples include deoxyribonucleic acid.
• Hormones include estradiol, ethenyl estradiol, etc.
• inclusion compounds examples include cyclodextrin.
• the present invention is applicable to various types of cosmetics, but is particularly preferred for skin care cosmetics, makeup cosmetics, antiperspirant cosmetics, UV protection cosmetics, and other cosmetics applied to the skin, hair cosmetics, and other cosmetics applied to the hair, and nail cosmetics.
• skin care cosmetics include lotions, milky lotions, creams, cleansing products, packs, oil liquids, massage products, beauty serums, beauty oils, cleaning agents, deodorants, hand creams, lip balms, wrinkle concealers, and the like.
• makeup cosmetics include makeup bases, foundations, concealers, face powders, cheek colors, eye colors, eye shadows, mascaras, eyeliners, eyebrow products, lipsticks, and the like.
• antiperspirant cosmetics include antiperspirant cosmetics of the roll-on type, cream type, solution type, stick type, and the like.
• UV protection cosmetics include sunscreen oils, sunscreen milky lotions, sunscreen creams, and the like.
• hair cosmetics include shampoos, rinses, treatments, setting agents, and the like.
• the cosmetic of the present invention may be in any form, for example, a powder, an oily liquid, a water-in-oil emulsion, an oil-in-water emulsion, a non-aqueous emulsion, or a multi-emulsion such as a W/O/W type or an O/W/O type.
• the cosmetic of the present invention may be in any form, such as a liquid, milky lotion, cream, solid, paste, gel, powder, pressed, multi-layered, mousse, spray, stick, or pencil.
• the present invention will be explained in more detail below with examples and comparative examples, but the present invention is not limited to the following examples.
• the "%" of the composition is mass % and the blend amount is the blend amount of the blended product described.
• E-1 triglycerin diallyl ether represented by the following formula (E-2)
• 102.2 g of 0.01 N hydrochloric acid was added and heated at 80° C. for 3 hours to carry out hydrolysis, and then neutralized with 1.5 g of 5% aqueous sodium bicarbonate solution.
• the reaction solution was heated under reduced pressure to distill off the solvent, and filtered to obtain the target product (organopolysiloxane) which was a fluid viscous liquid represented by the following formula (E-7).
• E-8 diglycerin diallyl ether represented by the following formula (E-8)
• E-12 pentaglycerin triallyl ether represented by the following formula (E-12)
• isopropyl alcohol 0.13 g of a 3% ethanol solution of platinum-1,3-divinyl-1,1,3,3-tetramethyl
• 37.0 g of isopropyl alcohol 37.0 g
• 0.01 g of a 3% ethanol solution of platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex were charged into a reactor and reacted by heating at 80° C. for 3 hours.
• 75.4 g of 0.01N hydrochloric acid was added and heated at 80° C. for 3 hours to carry out hydrolysis, followed by neutralization with 1.1 g of 5% sodium bicarbonate water.
• the reaction solution was heated under reduced pressure to distill off the solvent, and filtered to obtain the target product (organopolysiloxane) which is a fluid, viscous liquid represented by the following formula (E-19).
• E-20 tetraglycerin triallyl ether represented by the following formula (E-20)
• 13.2 g of isopropyl alcohol 14.2 g
• 0.01 g of a 3% ethanol solution of platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex were charged into a reactor and reacted by heating at 80° C. for 3 hours.
• 215.0 g of 0.01N hydrochloric acid was added and heated at 80° C. for 3 hours to carry out hydrolysis, followed by neutralization with 3.2 g of 5% sodium bicarbonate water.
• the reaction solution was heated under reduced pressure to distill off the solvent, and filtered to obtain the target product (organopolysiloxane) which is a fluid, viscous liquid represented by the following formula (E-27).
• 93.8 g of 0.01 N hydrochloric acid was added and heated at 80° C. for 3 hours to carry out hydrolysis, and then neutralized with 1.4 g of 5% aqueous sodium bicarbonate solution.
• the reaction solution was heated under reduced pressure to distill off the solvent, and filtered to obtain the target product (organopolysiloxane) which was a fluid viscous liquid represented by the following formula (E-31).
• E-12 pentaglycerin triallyl ether represented by the following formula (E-12)
• isopropyl alcohol 0.22 g of a 3% ethanol solution of platinum-1,3-divinyl-1,1,3,3-tetramethyl
• 22.7 g of isopropyl alcohol, 0.02 g of a 3% ethanol solution of platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex was charged into a reactor and reacted by heating for 3 hours at 80 ° C.
• 79.2 g of 0.01 N hydrochloric acid was added and heated at 80° C. for 3 hours to carry out hydrolysis, and then neutralized with 1.2 g of 5% aqueous sodium bicarbonate solution.
• the reaction solution was heated under reduced pressure to distill off the solvent, and filtered to obtain the target product (organopolysiloxane) which was a viscous liquid with flowability represented by the following formula (E-34).
• E-36 organohydrogenpolysiloxane represented by the following formula (E-36) (hydrosily
• the average particle size in the table is the "average primary particle size.”
• the results in Table 1 above show that the organopolysiloxane of the present invention has excellent dispersibility and can be used to prepare a paste with a lower viscosity.
• the paste has improved dispersibility, allowing for greater freedom in formulation, and also has excellent dispersion stability.
• Dispersions having the formulations shown in Table 2 were prepared.
• Viscosity stability When comparing the viscosity of the obtained dispersion on the day and after one week at 25°C, a change rate of less than 150% was marked as " ⁇ ”, a change rate of less than 200% was marked as “ ⁇ ”, and a change rate of 200% or more due to poor stability was marked as " ⁇ ”. Viscosity values exceeding the upper limit of the viscosity measurement were not evaluated.
• KF-96L-2cs (Dimethicone): Shin-Etsu Chemical Co., Ltd. (hereinafter the same)
• Dispersions having the formulations shown in Table 3 were prepared.
• Viscosity stability When the viscosity of the obtained dispersion was compared on the day and after one week at 25°C, a change rate of less than 150% was marked as "A”, a change rate of less than 200% was marked as “O”, and a change rate of 200% or more due to poor stability was marked as "X”. Viscosity values exceeding the upper limit of the measurement were not evaluated.
• Dispersions having the formulations shown in Table 4 were prepared.
• Viscosity stability When the viscosity of the obtained dispersion was compared on the day and after one week at 25°C, a change rate of less than 150% was marked as "A”, a change rate of less than 200% was marked as “O”, and a change rate of 200% or more due to poor stability was marked as "X”. Viscosity values exceeding the upper limit of the measurement were not evaluated.
• Example 21 O/W Sunscreen Cream Composition % 1. 0.5% of the organopolysiloxane of Example 3 2. Silicone-treated zinc oxide microparticles 5 3. Decamethylcyclopentasiloxane 5 4. Ethylhexyl methoxycinnamate 5 5. KF-56A (Note 1) 3 6. Cetanol 0.5 7. Polyoxyethylene sorbitan monooleate 2.5 8. Glyceryl stearate (SE) 0.5 9. KF-6011P (Note 2) 1 10. Dipropylene glycol 6 11. 1,3-Butylene glycol 6 12. Carboxyvinyl polymer 0.3 13. Acrylic polymer compound 0.3 14. Methylparaben 0.2 15. Phenoxyethanol 0.3 16.
• Disodium edetate (appropriate amount) 17. Water (remaining amount) 18. 10% sodium hydroxide solution (appropriate amount) Total 100.0 (Note 1) Shin-Etsu Chemical Co., Ltd.: Diphenylsiloxyphenyl trimethicone (Note 2) Shin-Etsu Chemical Co., Ltd.: PEG-11 methyl ether dimethicone
• the obtained O/W sunscreen had high transparency, was less sticky, and had a good feel when used.
• Example 22 W/O cream composition % 1. KSG-710 (Note 1) 4 2. KSG-15 (Note 2) 1 3. Organopolysiloxane of Example 5 3 4. Dimethylpolysiloxane (6cs) 13 5. 1,3-Butylene glycol 8 6. Sorbitol 5 7. Phenoxyethanol 0.3 8. Sodium citrate (as needed) 9. Sodium chloride (as needed) 10.
• the obtained W/O shaking sunscreen contains a high content of fine powder, but has low viscosity, high transparency, no stickiness, and a good feel when used. In addition, the increase in viscosity at high temperatures is suppressed, and the sunscreen has excellent stability.
• the obtained W/O liquid foundation was highly powder-containing, but had low viscosity, good spreadability, and a good feel when used. In addition, the increase in viscosity at high temperatures was suppressed, and the stability was excellent.
• the obtained W/O cream foundation contained a high powder content, but had good spreadability and a good feel when used.
• Non-aqueous concealer composition % 1.
• KSP-101 (Note 1) 23 2.
• KSP-300 (Note 2) 5 3.
• KSG-19 (Note 3) 6 4.
• Dimethylpolysiloxane (6cs) 40 5.
• KF-56A (Note 4) 7
• TMF-1.5 (Note 5) Remaining amount 7.
• Triethylhexanoin 0.2
• 0.5% of the organopolysiloxane of Example 9 9.
• AES-3083 treated titanium oxide (Note 6) 0.3 10.
• AES-3083 treated iron oxide (Note 6) Appropriate amount Total 100.0 (Note 1) Shin-Etsu Chemical Co., Ltd.: (vinyl dimethicone / methicone silsesquioxane) crosspolymer (Note 2) Shin-Etsu Chemical Co., Ltd.: (diphenyl dimethicone / vinyl diphenyl dimethicone / silsesquioxane) crosspolymer (Note 3) Shin-Etsu Chemical Co., Ltd.: Mixture of 80-90% dimethicone + 10-20% (dimethicone / vinyl dimethicone) crosspolymer (Note 4) Shin-Etsu Chemical Co., Ltd.: Diphenylsiloxyphenyl trimethicone (Note 5) Shin-Etsu Chemical Co., Ltd.: Methyl trimethicone (Note 6) Shin-Etsu Chemical Co., Ltd.: Triethoxycap
• Example 27 Lipstick composition % 1. Candelilla wax 3 2. Polyethylene 2 3. Microcrystalline wax 2.5 4. Ceresin 6 5. KP-561P (Note 1) 13 6. Macadamia nut oil 23 7. Diisostearyl malate 8.5 8. Hydrogenated polyisobutene 8.5 9. Isotridecyl isononanoate 15 10. Polyglyceryl-2 triisostearate 4.5 11. Organopolysiloxane of Example 10 2.5 12. Red No. 201 0.4 13. Red No. 202 0.4 14. Yellow No. 4 1.6 15. KTP-09W (Note 2) 3 16. KTP-09R (Note 2) 0.7 17. KTP-09B (Note 2) 0.2 18.
• A Components 10 to 18 were dispersed using a roll mill.
• B Components 1 to 9 were mixed uniformly at 90°C.
• C To the mixture obtained in B, the mixture obtained in A and component 19 were added, mixed uniformly at 80°C, poured into a mold, and then slowly cooled to obtain a lipstick.
• the obtained lipstick had excellent adhesion and a good feel when used. This shows that the lipstick can be applied to other non-aqueous oil-based cosmetics such as gloss, stick concealer, and pour-on foundation.
• the obtained W/O solid foundation had a good feel in use, good application properties, and excellent storage stability.
• Example 29 Lipstick composition % 1. Synthetic wax 6 2. Paraffin 6 3. Microcrystalline wax 2 4. Organopolysiloxane of Example 9 2.5 5. KF-56A (Note 1) 5 6. Dipentaerythrityl tripolyhydroxystearate balance 7. Jojoba seed oil 1.5 8. Hydrogenated polyisobutene 12 9. Di(phytosteryl/octyldodecyl) lauroyl glutamate 1.5 10. Organopolysiloxane 3 of Example 10 11. Triethylhexanoin 15 12. Caprylic/capric triglyceride 7 13. Red No. 202 0.6 14. Yellow No. 4 2.2 15. KTP-09W (Note 2) 5 16.
• A Components 13 to 19 were dispersed using a roll mill.
• B Components 1 to 12 were mixed uniformly at 90°C.
• C To the mixture obtained in B, the mixture obtained in A and component 19 were added, mixed uniformly at 80°C, poured into a mold, and then slowly cooled to obtain a lipstick.
• the resulting lipstick had excellent adhesion, transfer resistance, and gloss, and also felt good when used.
• the obtained W/O sunscreen contains a high content of fine powder, but has low viscosity, high transparency, is not sticky, and has a good feel when used. In addition, the increase in viscosity at high temperatures is suppressed, and the sunscreen has excellent stability.
• Pentylene glycol 1 17. Caprylyl glycol, appropriate amount 18. Sodium citrate, appropriate amount 19. Sodium chloride, 0.5 20. Purified water 41.4 Total 100.0 (Note 1) Shin-Etsu Chemical Co., Ltd.: Mixture of 70-80% dimethicone (6cs) + 20-30% (dimethicone/polyglycerin-3) crosspolymer (Note 2) Shin-Etsu Chemical Co., Ltd.: Mixture of 65-75% triethylhexanoin + 25-35% (vinyl dimethicone/lauryl dimethicone) crosspolymer (Note 3) Shin-Etsu Chemical Co., Ltd.: Lauryl polyglyceryl-3 polydimethylsiloxyethyl Dimethicone (Note 4) Shin-Etsu Chemical Co., Ltd.: Methyl trimethicone (Note 5) Shin-Etsu Chemical Co., Ltd.: Trimethylsiloxysilicate 50%

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