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WO2025206167A1 - Particules de protection contre les uv traitées en surface, dispersion, produit cosmétique et procédé de production de particules de protection contre les uv traitées en surface - Google Patents

Particules de protection contre les uv traitées en surface, dispersion, produit cosmétique et procédé de production de particules de protection contre les uv traitées en surface

Info

Publication number
WO2025206167A1
WO2025206167A1 PCT/JP2025/012443 JP2025012443W WO2025206167A1 WO 2025206167 A1 WO2025206167 A1 WO 2025206167A1 JP 2025012443 W JP2025012443 W JP 2025012443W WO 2025206167 A1 WO2025206167 A1 WO 2025206167A1
Authority
WO
WIPO (PCT)
Prior art keywords
treated
ultraviolet
particles
shielding particles
shielding
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/JP2025/012443
Other languages
English (en)
Japanese (ja)
Inventor
浩和 松下
智海 伊藤
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Osaka Cement Co Ltd
Original Assignee
Sumitomo Osaka Cement Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sumitomo Osaka Cement Co Ltd filed Critical Sumitomo Osaka Cement Co Ltd
Publication of WO2025206167A1 publication Critical patent/WO2025206167A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • 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
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
    • C01G9/00—Compounds of zinc
    • C01G9/02—Oxides; Hydroxides

Definitions

  • the present invention relates to surface-treated ultraviolet-shielding particles, a dispersion, a composition, a cosmetic, and a method for producing the surface-treated ultraviolet-shielding particles.
  • Ultraviolet-shielding particles such as zinc oxide and titanium oxide, which have ultraviolet-shielding properties, are used in cosmetics such as sunscreens and foundations.
  • the surface of the ultraviolet-shielding particles is treated with a surface treatment agent in order to adapt the surface condition of the ultraviolet-shielding particles to the properties of the cosmetic and to suppress the catalytic activity of the ultraviolet-shielding particles.
  • UV-blocking particles include, for example, metal soaps such as magnesium stearate, silicone oils such as dimethicone and hydrogen dimethicone, and silane coupling agents with alkoxy groups such as octyltriethoxysilane (see, for example, Patent Documents 1 and 2).
  • Patent Document 3 proposes cosmetics with improved UV protection effects by incorporating powders of metal oxide powder and extender pigments that have both been surface-treated with metal soap.
  • UV-blocking particles surface-treated with metal soap had the problem of low alcohol resistance.
  • the present invention was made in consideration of the above circumstances, and aims to provide surface-treated UV-shielding particles that have excellent alcohol resistance and are surface-treated with a metal soap. It also aims to provide a dispersion and a cosmetic that contain these surface-treated UV-shielding particles that have been surface-treated with a metal soap. It also aims to provide a method for producing such surface-treated UV-shielding particles that have been surface-treated with a metal soap.
  • the present invention has the following aspects.
  • Ultraviolet-shielding particles surface-treated with a metal soap the metal soap is at least one selected from the group consisting of magnesium stearate, aluminum stearate, aluminum dimyristate, and aluminum myristate; Surface-treated ultraviolet-shielding particles, wherein the hydrophobicity of the ultraviolet-shielding particles after mixing with ethanol at 50°C is 25% or more.
  • the surface-treated ultraviolet-shielding particles according to [1], wherein the ultraviolet-shielding particles are at least one selected from the group consisting of zinc oxide particles, titanium oxide particles, cerium oxide particles, and iron oxide particles.
  • [3] The surface-treated ultraviolet shielding particles according to [1] or [2], which have a BET specific surface area of 1.5 m 2 /g or more and 65 m 2 /g or less.
  • [4] The surface-treated ultraviolet shielding particles according to any one of [1] to [3], wherein the hydroxyl group treatment rate after mixing with ethanol at 50°C is 90% or more.
  • [5] A dispersion liquid containing the surface-treated ultraviolet-shielding particles according to any one of [1] to [4] and a dispersion medium.
  • a cosmetic comprising at least one of the surface-treated ultraviolet shielding particles according to any one of [1] to [4] and the dispersion according to [5].
  • a cosmetic comprising the surface-treated ultraviolet-shielding particles according to any one of [1] to [4].
  • a cosmetic comprising the dispersion liquid according to [5].
  • the present invention can provide surface-treated ultraviolet-shielding particles with excellent alcohol resistance.
  • the present invention can also provide a dispersion containing such surface-treated ultraviolet-shielding particles, and a cosmetic preparation.
  • the present invention can also provide a method for producing such surface-treated ultraviolet-shielding particles.
  • the inventors After extensive investigation, the inventors have discovered that by melting a metal soap with excellent alcohol resistance and mixing the molten metal soap with UV-blocking particles at a predetermined energy level or higher without using a solvent, the UV-blocking particles can be surface-treated with the metal soap with excellent alcohol resistance.
  • This manufacturing method makes it possible to surface-treat UV-blocking particles using only the metal soap with excellent alcohol resistance, and has therefore discovered that UV-blocking particles surface-treated with the metal soap with excellent alcohol resistance can be obtained.
  • the hydrophobicity of the ultraviolet-shielding particles after mixing with ethanol at 50°C being 25% or more means that the surfaces of the ultraviolet-shielding particles surface-treated with the metal soap remain hydrophobic even after mixing with high-temperature alcohol.
  • the hydrophobicity of the ultraviolet-shielding particles after mixing with ethanol at 50°C being 25% or more means that the metal soap remains attached to the surface of the ultraviolet-shielding particles even after mixing with alcohol, resulting in excellent alcohol resistance. Since it is very difficult to confirm the degree of surface treatment of particles, this confirmation was made as a result of various investigations.
  • “hydrophobicity” is measured by the limit ethanol method.
  • the limit ethanol method involves adding a sample to a mixed solution of water and ethanol, and observing whether the sample precipitates.
  • the limit ethanol method involves increasing the ethanol ratio if the sample does not precipitate, and increasing the water ratio if the sample precipitates.
  • This method evaluates the degree of hydrophobicity of the surface of UV-blocking particles based on the ethanol ratio required for the sample to precipitate. This can also be considered the ethanol ratio at the point when the sample begins to precipitate. Specifically, the ethanol ratio (%) contained in the mixed solution when 10 or more surface-treated UV-blocking particles have precipitated is taken as the hydrophobicity of the surface-treated UV-blocking particles. A higher ethanol ratio indicates a more hydrophobic surface of the UV-blocking particles.
  • the hydrophobicity of the surface-treated ultraviolet shielding particles of this embodiment before mixing with 50°C ethanol may be 25% or more, 30% or more, 35% or more, or 40% or more.
  • the upper limit of the hydrophobicity may be 70% or less, 60% or less, or 50% or less.
  • the hydrophobicity may be adjusted depending on the degree of hydrophobicity of the substance into which the surface-treated ultraviolet-shielding particles are to be mixed, for example, a cosmetic product. If the hydrophobicity is 25% or more, the surface-treated ultraviolet shielding particles have excellent alcohol resistance.
  • the change in hydrophobicity of the surface-treated ultraviolet-shielding particles of this embodiment between before and after mixing with ethanol at 50° C. is preferably 20% or less, more preferably 10% or less, even more preferably 8% or less, and particularly preferably 5% or less.
  • the change in hydrophobicity is within the above range, the change in the surface state of the surface-treated ultraviolet shielding particles is suppressed even when the surface-treated ultraviolet shielding particles are exposed to high-temperature ethanol, and therefore the surface-treated ultraviolet shielding particles can be said to have excellent alcohol resistance.
  • the surface-treated ultraviolet shielding particles of this embodiment preferably have a hydroxyl group treatment rate of 95% or more, as measured by the following method.
  • the hydroxyl group treatment rate may be 96% or more, 97% or more, or 98% or more.
  • the upper limit of the hydroxyl group treatment rate is 100%.
  • a high hydroxyl group treatment rate means that the degree to which the hydroxyl groups on the surface of the ultraviolet-shielding particles have been treated is high. In other words, the higher the hydroxyl group treatment rate on the surface of the ultraviolet-shielding particles, the more the hydroxyl groups present on the surface of the ultraviolet-shielding particles have been treated and made hydrophobic. In other words, a high treatment rate can be considered to mean that the hydroxyl groups present on the surface of the ultraviolet-shielding particles have been treated more extensively with the metal soap.
  • hydroxyl group treatment rate refers to a value measured using a red dye that absorbs light at a wavelength of about 545 nm and is represented by the following general formula (1).
  • the red dye represented by the above general formula (1) can be produced, for example, by the following production method.
  • a mixed solution is prepared by mixing 1 mmol of 2,2'-dihydroxyazobenzene, 1 mmol of diphenyltin (IV) oxide as a metal source, and 30 mL of acetone. Next, this mixture is stirred at 70° C. for 3 hours to carry out a dehydration reaction, and diphenyltin oxide is coordinated with 2,2′-dihydroxyazobenzene.
  • the mixture after the dehydration reaction is filtered, the filtrate is recovered, and the solvent is distilled off from the filtrate to obtain the red pigment.
  • the red dye selectively adsorbs to hydroxyl groups present on the surface of ultraviolet-shielding particles and does not react with hydroxyl groups of water, alcohol, etc.
  • the red dye also does not react with dimethylpolysiloxane. Therefore, the red dye can qualitatively and quantitatively evaluate the amount of metal hydroxyl groups present on the surface of ultraviolet-shielding particles or the surface of surface-treated ultraviolet-shielding particles without being affected by moisture.
  • hydroxyl groups are present on the surface of the ultraviolet-shielding particles. Therefore, the red dye is adsorbed onto the ultraviolet-shielding particles before they are coated with the metal soap.
  • the degree of coverage of the ultraviolet-shielding particles with the metal soap can be determined by examining the amount of red dye adsorbed onto the ultraviolet-shielding particles before coating and the amount of red dye adsorbed onto the ultraviolet-shielding particles after coating (surface-treated ultraviolet-shielding particles).
  • a larger amount of red dye adsorbed indicates a larger number of hydroxyl groups present on the surface.
  • a larger hydroxyl group treatment rate indicates that the surface of the ultraviolet-shielding particles is more coated with the metal soap and thus more hydrophobic.
  • the hydroxyl group treatment rate in this embodiment is calculated from the adsorption amount of the red dye before and after coating. That is, the hydroxyl group treatment rate of the surface-treated ultraviolet-shielding particles of this embodiment is calculated by the formula 100-(B/A ⁇ 100)(%), where A is the adsorption amount before coating with the red dye and B is the adsorption amount after coating with the red dye. Note that the greater the degree of coating, the smaller the adsorption amount.
  • the hydroxyl group treatment rate with the red dye can be measured, for example, by the following method. 250 nmol (0.12 mg) of the red dye is dissolved in toluene to make 5 mL, thereby obtaining a 5 ⁇ 10 ⁇ 5 mol/L evaluation solution C1.
  • the absorbance C2 of solution C1 at a wavelength of 545 nm is measured.
  • the absorbance C2 is greater than the absorbance A2 and absorbance B2 described below.
  • the absorbance can be measured using, for example, a spectrophotometer (model number: V-770, manufactured by JASCO Corporation).
  • the unit of absorbance may be Abs.
  • Uncoated ultraviolet-shielding particles and surface-treated ultraviolet-shielding particles coated with a metal soap are prepared.
  • x g of uncoated ultraviolet-blocking particles is added to the evaluation solution C1, and the mixture is stirred and mixed at 60° C. for 4 hours to prepare a mixed solution.
  • the ultraviolet-blocking particles are removed from this mixed solution by centrifugation, filtration, or the like to obtain evaluation mixed solution A1 (mixed solution A1).
  • the absorbance A2 of this mixed solution A1 at a wavelength of 545 nm is measured.
  • y g of the surface-treated UV-blocking particles to be measured are added, and the mixture is stirred and mixed at 60°C for 4 hours to prepare a mixed solution.
  • the surface-treated UV-blocking particles are removed from this mixture by centrifugation, filtration, or the like to obtain the evaluation mixed solution B1 (solution B1 after mixing).
  • the absorbance B2 of this mixed solution B1 at a wavelength of 545 nm is measured.
  • the absorbance B2 is greater than the absorbance A2.
  • x and y may be adjusted depending on the BET specific surface area of the ultraviolet-shielding particles. For example, x and y are 1 mg to 50 mg. When the BET specific surface area is 40 m 2 /g, x and y are preferably about 4 ⁇ 10 -3 g. When the BET specific surface area is 5 m 2 /g, x and y are preferably about 32 ⁇ 10 -3 g. It is preferable that x and y have the same value.
  • the amount (mol/g) of the red dye adsorbed to the ultraviolet-shielding particles before coating is calculated using the following formula (2).
  • Adsorption amount A3 ((C2-A2)/C2) ⁇ 250 ⁇ 10-9 (mol)/x(g)...(2)
  • the amount (mol/g) of the red dye adsorbed to the surface-treated ultraviolet-shielding particles is calculated using the following formula (3).
  • Adsorption amount B3 ((C2-B2)/C2) ⁇ 250 ⁇ 10-9 (mol)/y(g)...(3)
  • a decrease in absorbance means that the dye is adsorbed, and therefore the adsorption amount of the red dye is calculated based on the idea that the rate of decrease in absorbance can be converted to the rate of dye adsorption.
  • the surface-treated ultraviolet-shielding particles of this embodiment preferably have a hydroxyl group treatment rate of 90% or more after mixing with ethanol at 50° C.
  • the surface-treated ultraviolet-shielding particles of this embodiment may have a hydroxyl group treatment rate of 92% or more, 95% or more, or 96% or more after mixing with ethanol at 50° C.
  • the upper limit of the hydroxyl group treatment rate after mixing with ethanol at 50° C. is 100%.
  • a hydroxyl group treatment rate of 90% or more means that the surfaces of the ultraviolet-shielding particles surface-treated with the metal soap remain hydrophobic even after mixing with high-temperature alcohol.
  • a hydroxyl group treatment rate of 90% or more of the ultraviolet-shielding particles after mixing with ethanol at 50° C. means that the metal soap remains attached to the surfaces of the ultraviolet-shielding particles even after mixing with alcohol, resulting in excellent alcohol resistance.
  • the change in the hydroxyl group treatment rate obtained by the above calculation formula i.e., the difference in the hydroxyl group treatment rate, between before and after mixing of the surface-treated ultraviolet-shielding particles with 50°C ethanol, is preferably 6% or less, more preferably 4% or less, and even more preferably 2% or less.
  • the change in the hydroxyl group treatment rate is within the above range, the change in the surface state of the surface-treated ultraviolet-shielding particles is suppressed even when the surface-treated ultraviolet-shielding particles are exposed to high-temperature ethanol, and therefore the surface-treated ultraviolet-shielding particles can be said to have excellent alcohol resistance.
  • the BET specific surface area of the surface-treated ultraviolet-shielding particles of this embodiment is not particularly limited and may be adjusted depending on the intended use.
  • the BET specific surface area is preferably 1.5 m 2 /g or more and 65 m 2 /g or less, and more preferably 1.5 m 2 /g or more and 8 m 2 /g or less.
  • BET specific surface area refers to the value measured by the BET method using a fully automatic specific surface area measuring device (trade name: Macsorb HM Model-1201, manufactured by Mountec Co., Ltd.).
  • BET specific surface area of surface-treated ultraviolet-shielding particles A preferred BET specific surface area of the surface-treated ultraviolet shielding particles for use in cosmetics will now be described.
  • the BET specific surface area of the surface-treated ultraviolet-shielding particles can be selected arbitrarily, but is preferably 1.5 m 2 /g or more, more preferably 2.5 m 2 /g or more, and even more preferably 3.5 m 2 /g or more.
  • the BET specific surface area of the surface-treated ultraviolet-shielding particles is preferably 65 m 2 /g or less, and more preferably 60 m 2 /g or less.
  • the BET specific surface area of the surface-treated ultraviolet-shielding particles may be 8 m 2 /g or less, or 6.0 m 2 /g or less.
  • the upper and lower limits of the BET specific surface area of the surface-treated ultraviolet-shielding particles can be combined arbitrarily. When the BET specific surface area of the surface-treated ultraviolet-shielding particles is 1.5 m 2 /g or more and 65 m 2 /g or less, the particles exhibit excellent transparency and ultraviolet-shielding properties when blended in cosmetics.
  • the hydrophobicity is more excellent.
  • the BET specific surface area of the ultraviolet-shielding particles before being coated with the metal soap does not change significantly from the BET specific surface area of the ultraviolet-shielding particles after being coated with the metal soap (surface-treated ultraviolet-shielding particles).
  • the average primary particle diameter of the surface-treated ultraviolet shielding particles of this embodiment is preferably 15 nm or more, more preferably 20 nm or more. It may be 50 nm or more, 80 nm or more, or 100 nm or more. From the viewpoint of increasing the hydrophobicity of the surface-treated ultraviolet shielding particles, the average primary particle diameter is preferably 130 nm or more, more preferably 150 nm or more, and even more preferably 200 nm or more. Furthermore, the average primary particle diameter of the surface-treated ultraviolet shielding particles of this embodiment is preferably 300 nm or less, more preferably 270 nm or less, and even more preferably 250 nm or less. When the average primary particle size of the surface-treated ultraviolet-shielding particles is 15 nm or more and 300 nm or less, the transparency and ultraviolet-shielding properties are excellent when blended in a cosmetic.
  • the average primary particle size of the surface-treated ultraviolet-shielding particles can be calculated by the following formula (5) using the BET specific surface area of the surface-treated ultraviolet-shielding particles.
  • Average primary particle diameter (nm) 6000/(BET specific surface area (m 2 /g) x ⁇ (g/cm 3 ))...(5) (In the formula, ⁇ is the density of the ultraviolet-shielding particles.
  • the average primary particle diameter of the surface-treated ultraviolet-shielding particles may be determined by the following method: Specifically, when the surface-treated ultraviolet-shielding particles are observed using a transmission electron microscope (TEM) or the like, a predetermined number of surface-treated ultraviolet-shielding particles, for example, 200 or 100 particles, are selected, and the longest linear portion (maximum major axis) of each of these surface-treated ultraviolet-shielding particles is measured, and the measured values are arithmetically averaged.
  • TEM transmission electron microscope
  • the aggregate particle size of the aggregate is not measured, but a predetermined number of surface-treated ultraviolet-shielding particles (primary particles) constituting the aggregate are measured and the average primary particle size is determined.
  • the particle diameter D50 of the surface-treated ultraviolet-shielding particles in this embodiment when the cumulative volume percentage of the dry particle size distribution is 50%, may be 40 ⁇ m or less, 30 ⁇ m or less, or 20 ⁇ m or less, and may be 100 nm or more, 500 nm or more, or 1 ⁇ m or more.
  • the particle size D90 when the cumulative volume percentage of the dry particle size distribution of the surface-treated ultraviolet shielding particles is 90% may be 150 ⁇ m or less, 130 ⁇ m or less, or 100 ⁇ m or less.
  • the maximum value D max of the dry particle size distribution of the surface-treated ultraviolet shielding particles in this embodiment may be 300 ⁇ m or less, 250 ⁇ m or less, or 200 ⁇ m or less.
  • the oil absorption of cyclopentasiloxane of the surface-treated ultraviolet shielding particles in this embodiment may be 30 ml/100 g or less, 20 ml/100 g or less, or 18 ml/100 g or less.
  • the ultraviolet-shielding particles in this embodiment are not particularly limited as long as they are metal oxide particles that can shield ultraviolet rays.
  • the ultraviolet-shielding particles in this embodiment are preferably at least one selected from the group consisting of zinc oxide particles, titanium oxide particles, iron oxide particles, and cerium oxide particles.
  • zinc oxide particles are preferred as the ultraviolet-shielding particles because they can block a wide range of ultraviolet wavelengths.
  • the BET specific surface area of the zinc oxide particles in this embodiment is preferably 1.5 m 2 /g or more and 65 m 2 /g or less.
  • the BET specific surface area is more preferably 2.5 m 2 /g or more, and even more preferably 4 m 2 /g or more.
  • the BET specific surface area of the zinc oxide particles may be, for example, 60 m 2 /g or less, 55 m 2 /g or less, 50 m 2 /g or less, or 45 m 2 /g or less. If necessary, the BET specific surface area of the zinc oxide particles may be 40 m 2 /g or less, 30 m 2 /g or less, or 10 m 2 /g or less.
  • the upper and lower limit values of the BET specific surface area of the zinc oxide particles can be arbitrarily combined. If the BET specific surface area of the zinc oxide particles is less than the lower limit value, transparency will decrease when the zinc oxide particles are incorporated into a cosmetic, which is not preferred. If the BET specific surface area of the zinc oxide particles exceeds the upper limit, when the zinc oxide particles surface-treated with the metal soap (hereinafter referred to as "metal soap-coated zinc oxide particles") are contained in a cosmetic at a high concentration, the particles may be prone to aggregation, which is undesirable.
  • the BET specific surface area of the zinc oxide particles is preferably 10.0 m 2 /g or less, more preferably 8.2 m 2 /g or less, even more preferably 7.1 m 2 /g or less, and particularly preferably 6.0 m 2 /g or less.
  • the BET specific surface area of zinc oxide particles decreases, the aggregation of particles is suppressed more and the amount of untreated surface area decreases, resulting in better alcohol resistance.
  • the BET specific surface area of zinc oxide particles refers to a value measured by the BET method using a fully automatic specific surface area measuring device (product name: Macsorb HM Model-1201, manufactured by Mountec Co., Ltd.).
  • the method for producing surface-treated ultraviolet-shielding particles of this embodiment is a method for producing surface-treated ultraviolet-shielding particles of this embodiment, and includes a step of heating and mixing ultraviolet-shielding particles with a metal soap that is at least one selected from the group consisting of magnesium stearate, aluminum stearate, aluminum dimyristate, and aluminum myristate, and surface-treating the ultraviolet-shielding particles with the molten metal soap (hereinafter referred to as the "surface treatment step").
  • the heating and mixing is performed without using a solvent.
  • the dispersion medium When used in cosmetics, the dispersion medium is not particularly limited as long as it can be formulated into the cosmetics and can disperse the surface-treated ultraviolet-shielding particles.
  • Suitable dispersion media include, for example, water, alcohols, esters, ethers, natural oils, ester oils, and silicone oils.
  • alcohols include methanol, ethanol, n-propanol, isopropanol, n-butanol, 2-butanol, octanol, and glycerin.
  • the above dispersion media may be used alone or in combination of two or more.
  • Suitable additives include, for example, preservatives, dispersants, dispersing aids, stabilizers, water-soluble binders, thickeners, oil-soluble chemicals, oil-soluble dyes, oil-soluble proteins, UV absorbers, etc.
  • the particle size (D50) of the surface-treated UV-blocking particles when the cumulative volume percentage of the particle size distribution in the dispersion of this embodiment is 50% can be selected at will, but is preferably 50 ⁇ m or less, more preferably 30 ⁇ m or less, and even more preferably 10 ⁇ m or less.
  • the lower limit of D50 in the dispersion of this embodiment is not particularly limited, and may be, for example, 130 nm or more, 140 nm or more, or 150 nm or more.
  • the upper and lower limits of D50 can be combined in any manner.
  • the particle size (D90) of the surface-treated UV-shielding particles when the cumulative volume percentage of the particle size distribution in the dispersion of this embodiment is 90% can be selected as desired, but is preferably 60 ⁇ m or less, more preferably 40 ⁇ m or less, and even more preferably 20 ⁇ m or less.
  • the lower limit of D90 in the dispersion of this embodiment is not particularly limited, and may be, for example, 150 nm or more, 200 nm or more, or 250 nm or more.
  • the upper and lower limits of D90 can be combined in any manner.
  • the D50 of the dispersion of this embodiment is 50 ⁇ m or less, when a cosmetic product prepared using this dispersion is applied to the skin, the surface-treated UV-blocking particles are more likely to be uniformly distributed, improving the UV-blocking effect, which is preferable. If the D90 of the dispersion of this embodiment is 60 ⁇ m or less, the transparency of the dispersion is high, and the transparency of the cosmetic product prepared using this dispersion is also high, which is preferable.
  • the cumulative volume percentage of the particle size distribution in a dispersion can be measured using the wet dispersion unit of a laser diffraction particle size distribution measuring device.
  • the content of the surface-treated UV-blocking particles relative to the total mass of the dispersion can be selected as desired, but is preferably 10% by mass or more, more preferably 20% by mass or more, and even more preferably 30% by mass or more. Furthermore, the content of the surface-treated UV-blocking particles relative to the total mass of the dispersion is preferably 90% by mass or less, more preferably 85% by mass or less, and even more preferably 80% by mass or less.
  • the upper and lower limit values for the content of the surface-treated UV-blocking particles relative to the total mass of the dispersion can be combined as desired.
  • the method for producing the dispersion liquid of the present embodiment is not particularly limited.
  • the method for producing the dispersion liquid of the present embodiment includes a method of mechanically dispersing the surface-treated ultraviolet-shielding particles of the present embodiment and a dispersion medium using a known dispersing device.
  • the dispersing device can be selected as necessary, and examples of the dispersing device include a stirrer, a planetary mixer, a homomixer, an ultrasonic homogenizer, a sand mill, a ball mill, and a roll mill.
  • the dispersion of this embodiment can be used in paints and other products that have UV blocking properties, gas permeation inhibition properties, etc.
  • the dispersion of this embodiment contains the surface-treated UV-blocking particles of this embodiment, so when blended into cosmetics, for example, the feeling of roughness is suppressed and the transparency and UV-blocking properties are excellent.
  • composition of the present embodiment contains the dispersion of the present embodiment and a resin.
  • the content of the surface-treated UV-blocking particles relative to the total mass of the composition of this embodiment may be adjusted appropriately to suit the desired properties.
  • the content is preferably 10% by mass or more and 40% by mass or less, and more preferably 20% by mass or more and 30% by mass or less.
  • the dispersion of this embodiment and the resin are mixed so that the content of the surface-treated UV-blocking particles relative to the total mass of the composition of this embodiment falls within the above range.
  • the solid content (surface-treated UV-blocking particles) is contained at a high concentration, allowing the properties of the surface-treated UV-blocking particles to be fully obtained and a composition in which the surface-treated UV-blocking particles are uniformly dispersed can be obtained.
  • the resin is not particularly limited as long as it is one that is commonly used for industrial purposes, but examples include acrylic resin, epoxy resin, urethane resin, polyester resin, silicone resin, etc.
  • the resin content relative to the total mass of the composition of this embodiment is not particularly limited and may be adjusted appropriately depending on the desired properties of the composition.
  • composition of the present embodiment may contain commonly used additives to the extent that the properties of the composition are not impaired.
  • additives include a polymerization initiator, a dispersant, and a preservative.
  • the method for producing the composition of this embodiment is not particularly limited, but examples include a method in which the surface-treated UV-blocking particles of this embodiment, a resin, and a dispersion medium are mechanically mixed using a known mixing device.
  • mixing devices include agitators, planetary mixers, homomixers, and ultrasonic homogenizers.
  • a cosmetic preparation in another embodiment contains a cosmetic base raw material and at least one selected from the group consisting of the surface-treated ultraviolet-shielding particles of the present embodiment and the dispersion of the present embodiment.
  • a cosmetic preparation in another embodiment contains a cosmetic base raw material and at least one selected from the group consisting of the surface-treated ultraviolet-shielding particles of the present embodiment, the dispersion of the present embodiment, and the composition of the present embodiment.
  • Cosmetic base raw materials are the raw materials that form the base material of cosmetics.
  • Examples of cosmetic base raw materials include oil-based raw materials, water-based raw materials, surfactants, and powder raw materials.
  • the oily raw material can be selected arbitrarily, and examples thereof include fats and oils, higher fatty acids, higher alcohols, and ester oils.
  • Powdered raw materials can be selected arbitrarily, and examples include colored pigments, white pigments, pearlescent agents, extender pigments, etc.
  • the content of the surface-treated UV-shielding particles relative to the total mass of the cosmetic of this embodiment may be adjusted appropriately depending on the desired properties.
  • the lower limit of the content of the surface-treated UV-shielding particles may be 0.01% by mass or more, 0.1% by mass or more, or 1% by mass or more.
  • the upper limit of the content of the surface-treated UV-shielding particles may be 50% by mass or less, 40% by mass or less, or 30% by mass or less.
  • the upper and lower limits of the content of the surface-treated UV-shielding particles in the cosmetic can be combined in any manner.
  • the sunscreen cosmetics will be specifically described below.
  • UVA long-wavelength ultraviolet rays
  • the lower limit of the content of the surface-treated ultraviolet-shielding particles relative to the total mass of the sunscreen cosmetic is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, and even more preferably 1% by mass or more.
  • the upper limit of the content of the surface-treated ultraviolet-shielding particles relative to the total mass of the sunscreen cosmetic may be 50% by mass or less, 40% by mass or less, or 30% by mass or less.
  • the upper and lower limits of the content of the surface-treated ultraviolet-shielding particles relative to the total mass of the sunscreen cosmetic can be combined in any desired manner.
  • a preferred range can be selected as desired, such as 5% to 15% by mass or 10% to 20% by mass.
  • Sunscreen cosmetics may contain, as necessary, hydrophobic dispersion media, inorganic fine particles or inorganic pigments other than surface-treated UV-blocking particles, hydrophilic dispersion media, oils and fats, surfactants, moisturizers, thickeners, pH adjusters, nutrients, antioxidants, fragrances, preservatives, dispersants, antifoaming agents, colorants, cosmetic ingredients, polymeric substances, biologically derived ingredients, plant-derived ingredients, antibacterial agents, disinfectants, antifungal agents, aqueous ingredients, oily ingredients, vitamins, emulsifiers, stabilizers, solubilizers, pearlescent agents, refatting substances, etc.
  • hydrophobic dispersion media examples include hydrocarbon oils, ester oils, silicone oils, higher fatty acids, and higher alcohols.
  • hydrocarbon oils include liquid paraffin, squalane, isoparaffin, branched chain light paraffin, petrolatum, and ceresin.
  • ester oils include isopropyl myristate, cetyl isooctanoate, and glyceryl trioctanoate.
  • silicone oils include decamethylcyclopentasiloxane, dimethylpolysiloxane, and methylphenylpolysiloxane.
  • higher fatty acids include lauric acid, myristic acid, palmitic acid, and stearic acid.
  • higher alcohols include lauryl alcohol, cetyl alcohol, stearyl alcohol, hexyldodecanol, and isostearyl alcohol.
  • inorganic fine particles and inorganic pigments other than surface-treated UV-blocking particles contained in cosmetics include calcium carbonate, calcium phosphate (apatite), magnesium carbonate, calcium silicate, magnesium silicate, aluminum silicate, kaolin, talc, titanium oxide, aluminum oxide, yellow iron oxide, gamma-iron oxide, cobalt titanate, cobalt violet, and silicon oxide.
  • the sunscreen cosmetic may further contain at least one organic UV absorber.
  • Cosmetics containing both surface-treated UV-blocking particles and an organic UV absorber are preferred because the booster effect broadens the UV-blocking range and increases UV-blocking properties.
  • organic UV absorbers examples include benzotriazole-based UV absorbers, benzoylmethane-based UV absorbers, benzoic acid-based UV absorbers, anthranilic acid-based UV absorbers, salicylic acid-based UV absorbers, cinnamic acid-based UV absorbers, silicone-based cinnamic acid UV absorbers, and triazine-based UV absorbers.
  • benzoylmethane-based ultraviolet absorbers examples include dibenzalazine, dianisoylmethane, 4-tert-butyl-4'-methoxydibenzoylmethane, 1-(4'-isopropylphenyl)-3-phenylpropane-1,3-dione, and 5-(3,3'-dimethyl-2-norbornylidene)-3-pentan-2-one.
  • benzoic acid-based UV absorbers examples include para-aminobenzoic acid (PABA), PABA monoglycerin ester, N,N-dipropoxy PABA ethyl ester, N,N-diethoxy PABA ethyl ester, N,N-dimethyl PABA ethyl ester, N,N-dimethyl PABA butyl ester, and N,N-dimethyl PABA methyl ester.
  • PABA para-aminobenzoic acid
  • PABA para-aminobenzoic acid
  • Cinnamic acid-based UV absorbers include, for example, octyl methoxycinnamate (ethylhexyl methoxycinnamate), glyceryl di-para-methoxycinnamate-mono-2-ethylhexanoate, octyl cinnamate, ethyl 4-isopropyl cinnamate, methyl 2,5-diisopropyl cinnamate, ethyl 2,4-diisopropyl cinnamate, methyl 2,4-diisopropyl cinnamate, propyl p-methoxycinnamate, isopropyl p- Examples include methoxycinnamate, isoamyl-p-methoxycinnamate, octyl-p-methoxycinnamate (2-ethylhexyl-p-methoxycinnamate), 2-ethoxyethy
  • silicone-based cinnamic acid ultraviolet absorbers include [3-bis(trimethylsiloxy)methylsilyl-1-methylpropyl]-3,4,5-trimethoxycinnamate, [3-bis(trimethylsiloxy)methylsilyl-3-methylpropyl]-3,4,5-trimethoxycinnamate, [3-bis(trimethylsiloxy)methylsilylpropyl]-3,4,5-trimethoxycinnamate, [3-bis(trimethylsiloxy)methylsilylbutyl]-3,4,5-trimethoxycinnamate, [3-tris(trimethylsiloxy)silylbutyl]-3,4,5-trimethoxycinnamate, and [3-tris(trimethylsiloxy)silyl-1-methylpropyl]-3,4-dimethoxycinnamate.
  • triazine-based ultraviolet absorbers examples include bisethylhexyloxyphenol methoxyphenyl triazine, ethylhexyl triazone, methylene bisbenzotriazolyl tetramethylbutylphenol, trisbiphenyl triazine, and diethylhexyl butamido triazone.
  • the critical wavelength of the cosmetic of this embodiment is preferably 370 nm or longer.
  • the cosmetic can block a wide range of ultraviolet rays, including long-wavelength ultraviolet (UVA) and short-wavelength ultraviolet (UVB).
  • UVA long-wavelength ultraviolet
  • UVB short-wavelength ultraviolet
  • the cosmetic of this embodiment contains at least one selected from the group consisting of the surface-treated UV-shielding particles of this embodiment, the dispersion of this embodiment, and the composition of this embodiment, making it possible to obtain a cosmetic with excellent quality stability.
  • Example 1 "Preparation of surface-treated zinc oxide particles” 97 parts by mass of zinc oxide particles A1 (BET specific surface area: 5 m2 /g, manufactured by Sumitomo Osaka Cement Co., Ltd.) and 3 parts by mass of magnesium stearate were mixed in a Henschel mixer heated to 130°C at a peripheral speed of 15 m/s for 4 hours to obtain surface-treated zinc oxide particles B1 of Example 1.
  • a mixed solution was prepared by adding 4.0 mg of zinc oxide particles A1 to solution C1 and stirring and mixing for 4 hours at 60° C. This mixed solution was filtered through a syringe filter (0.2 ⁇ m), and the absorbance A2 of the filtrate at 545 nm was measured. To the solution C1, 4.0 mg of the surface-treated zinc oxide particles B1 of Example 1 was added, and the mixture was stirred and mixed for 4 hours at 60° C. to prepare a mixed solution. This mixed solution was filtered through a syringe filter (0.2 ⁇ m), and the absorbance B2 of the filtrate at 545 nm was measured.
  • the amount of red dye adsorbed to the zinc oxide particles A1 and the amount of red dye adsorbed to the surface-treated zinc oxide particles B1 were calculated using the above formulas (2) and (3).
  • Amount of dye adsorbed on surface-treated zinc oxide particles B1 B3 ((C2 ⁇ B2)/C2) ⁇ 250 ⁇ 10 ⁇ 9 (mol)/4 ⁇ 10 ⁇ 3 (g)
  • Amount of dye adsorbed on zinc oxide particles A1 A3 ((C2 ⁇ A2)/C2) ⁇ 250 ⁇ 10 ⁇ 9 (mol)/4 ⁇ 10 ⁇ 3 (g) (2)
  • Example 2 Surface-treated zinc oxide particles of Example 2 were obtained in the same manner as in Example 1, except that 98 parts by mass of zinc oxide particles A1 and 2 parts by mass of magnesium stearate were used. The results of evaluation in the same manner as in Example 1 are shown in Table 1.
  • Example 3 Surface-treated zinc oxide particles of Example 3 were obtained in the same manner as in Example 1, except that 98.5 parts by mass of zinc oxide particles A1 and 1.5 parts by mass of magnesium stearate were used. The results of evaluation in the same manner as in Example 1 are shown in Table 1.
  • Example 4 Surface-treated zinc oxide particles of Example 4 were obtained in the same manner as in Example 1, except that 90 parts by mass of zinc oxide particles having a BET specific surface area of 40 m 2 /g and 10 parts by mass of magnesium stearate were used. The results of evaluation in the same manner as in Example 1 are shown in Table 1.
  • Comparative Example 1 Surface-treated zinc oxide particles of Comparative Example 1 were obtained in the same manner as in Example 1, except that 99 parts by mass of zinc oxide particles A1 and 1 part by mass of magnesium stearate were used. The results of evaluation in the same manner as in Example 1 are shown in Table 1.
  • zinc oxide particles surface-treated with a metal soap that has a hydrophobicity of 25% or more after mixing with ethanol at 50°C can prevent the metal soap from being released from the surface of the zinc oxide particles, even when mixed with ethanol at 50°C.
  • the surface-treated ultraviolet-shielding particles of this embodiment can be obtained by mixing molten metal soap and ultraviolet-shielding particles with a certain amount of energy or more without using a solvent.
  • the surface-treated zinc oxide particles of this embodiment have excellent alcohol resistance, which makes them easy to incorporate into oil-based cosmetics and ensures excellent quality stability after incorporation into cosmetics.

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Abstract

L'invention concerne des particules de protection contre les UV traitées en surface avec un savon métallique, le savon métallique étant au moins un savon choisi dans le groupe constitué par le stéarate de magnésium, le stéarate d'aluminium, le dimyristate d'aluminium et le myristate d'aluminium, et l'hydrophobicité des particules de protection contre les UV après mélange avec de l'éthanol à 50°C étant de 25% ou plus.
PCT/JP2025/012443 2024-03-29 2025-03-27 Particules de protection contre les uv traitées en surface, dispersion, produit cosmétique et procédé de production de particules de protection contre les uv traitées en surface Pending WO2025206167A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10182397A (ja) * 1996-12-27 1998-07-07 Kose Corp 紫外線防御化粧料
JP2011051913A (ja) * 2009-08-31 2011-03-17 Miyoshi Kasei Inc 紫外線遮蔽効果と皮脂固化能を有する化粧料用組成物及び化粧料
WO2020017346A1 (fr) * 2018-07-18 2020-01-23 信越化学工業株式会社 Dispersion, procédé pour sa production et produit cosmétique
JP2023108917A (ja) * 2022-01-26 2023-08-07 堺化学工業株式会社 硫酸バリウムとシリカとの球状複合粒子およびそれを含む化粧料

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10182397A (ja) * 1996-12-27 1998-07-07 Kose Corp 紫外線防御化粧料
JP2011051913A (ja) * 2009-08-31 2011-03-17 Miyoshi Kasei Inc 紫外線遮蔽効果と皮脂固化能を有する化粧料用組成物及び化粧料
WO2020017346A1 (fr) * 2018-07-18 2020-01-23 信越化学工業株式会社 Dispersion, procédé pour sa production et produit cosmétique
JP2023108917A (ja) * 2022-01-26 2023-08-07 堺化学工業株式会社 硫酸バリウムとシリカとの球状複合粒子およびそれを含む化粧料

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