WO2024142926A1 - 水中油型乳化組成物 - Google Patents

水中油型乳化組成物 Download PDF

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Publication number
WO2024142926A1
WO2024142926A1 PCT/JP2023/044555 JP2023044555W WO2024142926A1 WO 2024142926 A1 WO2024142926 A1 WO 2024142926A1 JP 2023044555 W JP2023044555 W JP 2023044555W WO 2024142926 A1 WO2024142926 A1 WO 2024142926A1
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Prior art keywords
oil
water emulsion
component
emulsion composition
meth
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English (en)
French (fr)
Japanese (ja)
Inventor
巧 渡邉
紘平 大谷
慶一 羽山
祐斗 井尾
恵悟 渡辺
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Kose Corp
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Kose Corp
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Priority to JP2024567445A priority Critical patent/JPWO2024142926A1/ja
Priority to KR1020257021516A priority patent/KR20250125369A/ko
Priority to CN202380089662.8A priority patent/CN120435280A/zh
Publication of WO2024142926A1 publication Critical patent/WO2024142926A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04Dispersions; Emulsions
    • A61K8/06Emulsions
    • A61K8/062Oil-in-water emulsions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04Dispersions; Emulsions
    • A61K8/06Emulsions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/27Zinc; Compounds thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • A61K8/375Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/445Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof aromatic, i.e. the carboxylic acid directly linked to the aromatic ring
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4966Triazines or their condensed derivatives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/58Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585Organosilicon compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8158Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86Polyethers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89Polysiloxanes
    • A61K8/891Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02Preparations containing skin colorants, e.g. pigments
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00Barrier 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
    • A61Q17/04Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30Characterized by the absence of a particular group of ingredients
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30Characterized by the absence of a particular group of ingredients
    • A61K2800/33Free of surfactant
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/60Particulates further characterized by their structure or composition
    • A61K2800/61Surface treated
    • A61K2800/62Coated
    • A61K2800/624Coated by macromolecular compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/60Particulates further characterized by their structure or composition
    • A61K2800/65Characterized by the composition of the particulate/core
    • A61K2800/651The particulate/core comprising inorganic material

Definitions

  • the present invention relates to an oil-in-water emulsion composition.
  • compositions with various functions have been developed.
  • oil-in-water emulsion compositions have been proposed that have a high UV protection effect that protects the skin from UVA (long-wavelength UV rays with wavelengths of 320-400 nm) and UVB (medium-wavelength UV rays with wavelengths of 290-320 nm).
  • UVA long-wavelength UV rays with wavelengths of 320-400 nm
  • UVB medium-wavelength UV rays with wavelengths of 290-320 nm
  • oil-in-water emulsion compositions have been developed that have UV protection effects while also being highly durable, so that the makeup film will not run off due to water or sweat, etc., in anticipation of various usage scenarios, and are widely used in foundations, sunscreens, etc.
  • an oil-in-water emulsion cosmetic e.g., Patent Document 1
  • Patent Document 1 contains a water-insoluble organic UV absorber that is solid at 25°C, a liquid oil, an acrylamide polymer, and a hydrophobized metal oxide particle, and the total content of 2-ethylhexyl paramethoxycinnamate and octocrylene is 2 mass% or less of the total amount of the oil-in-water emulsion cosmetic.
  • Patent Document 1 has excellent UV protection effects, it is sometimes lacking in terms of the fresh feel when applied, the absence of precipitation of the solid UV absorber, and durability.
  • Oil-in-water emulsion compositions having ultraviolet protection effects are often used in cosmetics for sunscreen applications, such as sunscreens and foundations. Since these cosmetics are used not only on the body but also on the face, many customers desire a light finish. In this context, a good feeling of use that does not burden the skin and makes the customer want to use it repeatedly is preferred, and a fresh feeling of use when applied is strongly desired. Oil-in-water emulsion compositions having high ultraviolet protection effects are particularly desired to have a fresh feeling of use, since they are significantly burdensome to the skin due to the incorporation of ultraviolet absorbers and metal oxides. Accordingly, an object of the present invention is to provide an oil-in-water emulsion composition which provides a fresh feel when applied, has excellent emulsion stability, is free of precipitation of a solid ultraviolet absorber, and has excellent durability and ultraviolet protection effect.
  • a water-soluble polymer with high salt resistance is blended to improve stability, but in the present invention, it is extremely difficult to realize a satisfactory fresh feeling of use at the time of application with a general-purpose salt-resistant water-soluble polymer such as (sodium acrylate/sodium acroyldimethyltaurate) copolymer, and the emulsion stability and durability were also insufficient.
  • a general-purpose salt-resistant water-soluble polymer such as (sodium acrylate/sodium acroyldimethyltaurate) copolymer
  • an oil-in-water emulsion composition containing an ultraviolet absorber that is solid at 25°C, a specific amount of a hydrophobized metal oxide, and a specific amount of an ester oil that is liquid at 25°C, and containing an ester copolymer of (meth)acrylic acid, (meth)acrylic acid alkyl ester, and (meth)acrylic acid (polyoxyethylene monoalkyl ether), and a (hydroxyethyl acrylate/sodium acryloyldimethyl taurate) copolymer in a specific range in total content and ratio, exhibits excellent emulsion stability without undergoing phase inversion during production, is free of precipitation of the solid ultraviolet absorber over time, and also provides a fresh feel when applied, durability, and ultraviolet protection effect, leading to the completion of the present invention.
  • the present invention provides the following.
  • the oil-in-water emulsion composition has a mass ratio (B)/(A) of the component (B) to the component (A) of 1 to 50.
  • the oil-in-water emulsion composition according to [1] or [2] further contains a component (F) ethanol.
  • the oil-in-water emulsion composition of the present invention has excellent emulsion stability and no precipitation of solid UV absorbers at 25°C, while providing a fresh feel when applied, excellent durability, and excellent UV protection effect.
  • an oil-in-water emulsion composition that exhibits sufficient UV protection effect while being substantially free of ethylhexyl methoxycinnamate (2-ethylhexyl paramethoxycinnamate), and that has excellent emulsion stability, a refreshing feel when applied, no precipitation of solid UV absorbers, and durability.
  • an oil-in-water emulsion composition that exhibits sufficient emulsion stability without substantially containing a surfactant, has a refreshing feel when applied, is free of precipitation of the solid UV absorber, and has excellent durability and UV protection effect.
  • the ester copolymer of component (A) used in the present invention is a copolymer comprising one or more monomers selected from the group consisting of an ester of (meth)acrylic acid and a polyoxyethylene alkyl ether, and (meth)acrylic acid or a simple ester thereof.
  • the component (A) is obtained by copolymerizing a monomer (a) selected from the group consisting of (meth)acrylic acid and (meth)acrylic acid alkyl esters, and a monomer (b) consisting of a polyoxyalkylene alkyl ether (meth)acrylate.
  • the bonding mode is not particularly limited, and may be any of block bonding, random bonding, etc. In addition, it may contain other monomers and may have a crosslinked structure.
  • the other monomers are preferably less than 10 mol% (lower limit 0 mol%), more preferably 5 mol% or less (lower limit 0 mol%), and even more preferably 1 mol% or less (lower limit 0 mol%) based on the total monomers.
  • the contents of the structural units (a) and (b) correspond to the amounts of the monomers (a) and (b) added in the production stage.
  • the content ratio of the structural unit (a) and the structural unit (b) is not particularly limited, and for example, the molar ratio of the structural unit (a):structural unit (b) is 1:100 to 100:1.
  • (meth)acrylic acid includes both acrylic acid and methacrylic acid.
  • the alkyl group of the alkyl ester preferably has 1 to 22 carbon atoms, more preferably 1 to 18 carbon atoms, and even more preferably 1 to 8 carbon atoms.
  • Examples of the (meth)acrylic acid alkyl ester include methyl (meth)acrylate, ethyl (meth)acrylate, and propyl (meth)acrylate.
  • the number of moles of polyoxyethylene added in the polyoxyethylene monoalkyl ether (meth)acrylate is preferably 10 to 30, more preferably 12 to 25, and even more preferably 20 to 25.
  • the alkyl group of the alkyl ether preferably has 12 to 24 carbon atoms, and more preferably has 16 to 22 carbon atoms.
  • Specific examples of polyoxyethylene monoalkyl ether (meth)acrylate include esters of acrylic acid and polyoxyethylene (20) stearyl ether, esters of methacrylic acid and polyoxyethylene (20) stearyl ether, esters of acrylic acid and polyoxyethylene (25) behenyl ether, and esters of methacrylic acid and polyoxyethylene (25) behenyl ether, with esters of methacrylic acid and polyoxyethylene (25) behenyl ether being even more preferred, and still more preferred being esters of methacrylic acid and polyoxyethylene (25) behenyl ether.
  • the numbers in parentheses indicate the number of moles of ethylene oxide added.
  • ester copolymer of component (A) include (meth)acrylic acid/(meth)acrylic acid alkyl ester/(meth)acrylic acid polyoxyethylene alkyl ether copolymers such as acrylates/polyoxyethylene methacrylate (20) cetyl ether copolymer, acrylates/polyoxyethylene methacrylate (20) stearyl ether copolymer, and acrylates/polyoxyethylene methacrylate (25) behenyl ether copolymer.
  • the numbers in parentheses indicate the number of moles of ethylene oxide added.
  • component (A) is preferably an (acrylates/stearate methacrylate) copolymer or an (acrylates/beheneth methacrylate) copolymer, more preferably an (acrylates/beheneth methacrylate) copolymer, and even more preferably an (acrylates/beheneth-25 methacrylate) copolymer.
  • Examples of commercially available products include acrylates/polyoxyethylene (20) methacrylate stearyl ether copolymer (acrylates/steareth-20 methacrylate copolymer), such as trade name: Accurin (registered trademark) 22 (manufactured by Rohm and Haas Co.), and acrylates/polyoxyethylene (25) methacrylate behenyl ether copolymer (acrylates/beheneth-25 methacrylate copolymer), such as trade name: Accurin 28 (manufactured by Rohm and Haas Co.), and trade name: NOVETHIX (registered trademark) L-10 (manufactured by Lubrizol Co., Ltd.).
  • the content of component (A) of the present invention is not particularly limited, but the lower limit is preferably 0.01% by mass (hereinafter simply abbreviated as %) or more, more preferably 0.02% or more, even more preferably 0.04% or more, and even more preferably 0.05% or more.
  • the upper limit is preferably 0.5% or less, more preferably 0.3% or less, even more preferably 0.25% or less, and even more preferably 0.2% or less. This range is more preferable because it provides a fresh feel when applied, emulsion stability, durability, and the like.
  • the content of component (A) of the present invention is not particularly limited, but is preferably 0.01 to 0.5%, more preferably 0.02 to 0.3%, even more preferably 0.04 to 0.25%, and even more preferably 0.05 to 0.2%. This range is more preferable because it provides a fresh feel when applied, emulsion stability, durability, etc.
  • the component (B) used in the present invention is a copolymer of hydroxyethyl acrylate and sodium acryloyldimethyltaurate.
  • Commercially available (hydroxyethyl acrylate/Na acryloyldimethyltaurate) copolymers include SIMULGEL FL (manufactured by SEPPIC).
  • the content of component (B) of the present invention is not particularly limited, but the lower limit is preferably 0.2% or more, more preferably 0.24% or more, even more preferably 0.25% or more, and even more preferably 0.3% or more.
  • the upper limit is preferably less than 0.9%, more preferably 0.8% or less, even more preferably 0.7% or less, and even more preferably 0.6% or less. This range is more preferable because it provides a fresh feel when applied, emulsion stability, durability, and the like.
  • component (B) of the present invention is not particularly limited, but is preferably 0.2% or more and less than 0.9%, more preferably 0.24 to 0.8%, even more preferably 0.25 to 0.7%, and even more preferably 0.3 to 0.6%. This range is more preferable because it provides a fresh feel when applied, emulsion stability, durability, etc.
  • the total content (A) + (B) of components (A) and (B) is 0.2% or more as a lower limit, preferably 0.25% or more, more preferably 0.3% or more, even more preferably 0.35% or more, and even more preferably 0.4% or more, from the viewpoint of emulsion stability, etc.
  • the upper limit is 0.9% or less, preferably 0.85% or less, more preferably 0.8% or less, even more preferably 0.7% or less, and even more preferably 0.6% or less.
  • the total content (A) + (B) of components (A) and (B) is 0.2 to 0.9%, preferably 0.25 to 0.85%, more preferably 0.3 to 0.8%, even more preferably 0.35 to 0.7%, and even more preferably 0.4 to 0.6%. This range is more preferable because it provides a fresh feel when applied, emulsion stability, durability, etc.
  • the mass ratio (B)/(A) of component (B) to component (A) is, from the viewpoints of a fresh feel when applied, emulsion stability, and durability, a lower limit of 1 or more, preferably 2 or more, more preferably 2.5 or more, and even more preferably 3 or more.
  • the upper limit is 50 or less, preferably 40 or less, more preferably 30 or less, even more preferably 20 or less, and even more preferably 10 or less.
  • the mass ratio (B)/(A) of component (B) to component (A) is 1 to 50, preferably 2 to 40, more preferably 2.5 to 30, even more preferably 3 to 20, and even more preferably 3 to 10. This range is more preferable because it provides a fresh feel when applied, emulsion stability, durability, and the like.
  • ⁇ Component (C) Ester oil that is liquid at 25°C>
  • the component (C) used in the present invention is an ester of a linear or branched fatty acid and a linear or branched monohydric or polyhydric alcohol.
  • liquid at 25°C refers to one having a viscosity of 7000 mPa ⁇ s or less when measured at 25°C and 1 atmospheric pressure using a B-type viscometer (rotor No. 2).
  • Component (C) of the present invention is not particularly limited as long as it is an ester oil that is liquid at 25°C, but examples thereof include jojoba oil, alkyl benzoate (C12-C15), cetyl 2-ethylhexanoate, isononyl isononanoate, isotridecyl isononanoate, isopropyl myristate, isopropyl palmitate, octyldodecyl myristate, isotridecyl isononanoate, ethyl oleate, glyceryl tri-2-ethylhexanoate, propylene glycol dicaprate, neopentyl glycol dicaprate, polyglyceryl-2 triisostearate, glyceryl tribehenate, diisostearyl malate, regardless of origin, such as animal oil, vegetable oil, or synthetic oil.
  • jojoba oil alkyl benzoate (C12
  • Examples include ethylhexyl dimethyl p-aminobenzoate, ethylhexyl salicylate, diethylhexyl succinate, tri(caprylic/capric acid)glyceryl, 2-ethylhexyl hydroxystearate, ethylhexyl palmitate, polyglyceryl-2 diisostearate, polyglyceryl-2 tetraisostearate, neopentyl glycol diethylhexanoate, pentaerythrityl tetraethylhexanoate, diisopropyl sebacate, dibutyl adipate, dicaprylyl carbonate, tocopherol acetate, olive oil, castor oil, mink oil, macadamia nut oil, meadowfoam oil, rosehip oil, rice bran oil, avocado oil, etc.
  • the molecular weight of component (C) of the present invention is preferably 200 to 1000, more preferably 200 to 800, and even more preferably 200 to 500.
  • examples include alkyl benzoate (C12-C15), propylene glycol dicaprate, neopentyl glycol dicaprate, isononyl isononanoate, isotridecyl isononanoate, cetyl 2-ethylhexanoate, glyceryl tri-2-ethylhexanoate, polyglyceryl-2 triisostearate, caprylic/capric triglyceride, 2-ethylhexyl hydroxystearate, diisostearyl malate, diisopropyl sebacate, dicaprylyl carbonate, dibutyl adipate, and ethylhexyl salicylate.
  • alkyl benzoate (C12-C15) and propylene glycol dicaprylate are more preferred because they provide a fresh feel when applied, have excellent solubility of the solid UV absorber, and are particularly effective in preventing precipitation of the solid UV absorber.
  • component (C) for example, commercially available products such as FINSOLV TN (manufactured by Innospec Performance Chemicals Europe Limited) and Nikkol PDD (manufactured by Nippon Surfactant Kogyo Co., Ltd.) can be used. These can be used alone or in combination of two or more types, as necessary.
  • component (C) is not particularly limited as long as it is an ester oil that is liquid at 25°C, but from the viewpoint of providing a fresh feel when applied and increasing the solubility of the solid UV absorber, the IOB value is preferably 0.1 to 0.5, more preferably 0.1 to 0.4, and even more preferably 0.1 to 0.3.
  • the hydrophobic treatment agent of component (D) is not particularly limited as long as it is one that is commonly used in cosmetics, quasi-drugs, pharmaceuticals, etc., but examples include silicone treatment agents, fluorine treatment agents, organic titanate treatment agents, fatty acid treatment agents, lecithin treatment agents, amino acid treatment agents, acylated amino acid treatment agents, etc.
  • one or more selected from silicone treatment agents, organic titanate treatment agents, fatty acid treatment agents, and acylated amino acid treatments are preferred, and one or more selected from silicone treatment agents, organic titanate treatment agents, and acylated amino acid treatments are particularly preferred.
  • the silane coupling agent is preferably a trialkoxyalkylsilane.
  • a trialkoxyalkylsilane is a compound in which three alkoxy groups and one alkyl group are bonded to a silicon atom, and the alkoxy group reacts with hydroxyl groups and the like on the powder surface to chemically modify the powder surface.
  • the alkoxy group is preferably an alkoxy group having 1 to 3 carbon atoms, such as methoxy, ethoxy, or propoxy.
  • Fatty acid treating agents include fatty acids and their metal salts, and among these, fatty acids with 12 to 18 carbon atoms are preferred from the standpoint of redispersibility of component (D), and examples of their salts include calcium, magnesium, zinc, and aluminum, with aluminum salts being preferred. Among these, stearic acid and its metal salts are particularly preferred.
  • the method of hydrophobization treatment in component (D) is not particularly limited, and can be produced by a commonly known method.
  • the hydrophobization treatment agent and powder particles to be treated are added to a solvent, stirred in a ball mill or the like, dried as necessary, washed with water, filtered repeatedly to remove impurities, and then dried and pulverized to obtain the desired hydrophobized powder.
  • several types of compounds that are surface treatment agents can be surface-treated simultaneously, or one compound can be used for surface treatment beforehand, and then another compound can be used for surface treatment.
  • the amount of hydrophobization treatment agent used for the metal oxide is not particularly limited, but from the viewpoints of emulsion stability, fresh feeling when applied, durability, and ultraviolet protection effect, 5 to 40% is preferable, and 10 to 35% is more preferable.
  • the content of component (D) of the present invention is at least 9% as a lower limit, preferably at least 10%, and more preferably at least 12%. Also, from the viewpoints of a fresh feeling when applied and emulsion stability, the content is at most 20%, preferably at most 19%, and more preferably at most 18%.
  • component (E) examples include 2-ethylhexyl dimethoxybenzylidene dioxoimidazolidinepropionate, diethylaminohydroxybenzoylhexyl benzoate, 2,4-bis ⁇ [4-(2-ethylhexyloxy)-2-hydroxy]-phenyl ⁇ -6-(4-methoxyphenyl)-1,3,5-triazine, 2,4,6-tris[4-(2-ethylhexyloxycarbonyl)anilino]-1,3,5-triazine, drometrizole trisiloxane, 4-tert-butyl-4'-methoxydibenzoylmethane, and 2-hydroxy-4-methoxybenzophenone.
  • the compound is two or more selected from the group consisting of diethylamino hydroxybenzoyl hexyl benzoate, 2,4-bis ⁇ [4-(2-ethylhexyloxy)-2-hydroxy]-phenyl ⁇ -6-(4-methoxyphenyl)-1,3,5-triazine, 2,4,6-tris[4-(2-ethylhexyloxycarbonyl)anilino]-1,3,5-triazine, and drometrizole trisiloxane, and it is even more preferable that the compound is three or more selected from the group consisting of diethylamino hydroxybenzoyl hexyl benzoate, 2,4-bis ⁇ [4-(2-ethylhexyloxy)-2-hydroxy]-phenyl ⁇ -6-(4-methoxyphenyl)-1,3,5-triazine, and drometrizole trisiloxane.
  • the content of component (E) of the present invention is not particularly limited, but from the viewpoint of ultraviolet protection effect, etc., the lower limit is preferably 1% or more, more preferably 2% or more, and even more preferably 4% or more. Also, from the viewpoint of no precipitation of the solid ultraviolet absorber, emulsion stability, and a fresh feeling when applied, the upper limit is preferably 20% or less, more preferably 10% or less, and even more preferably 8% or less.
  • component (F) of the present invention is not particularly limited, but is preferably 1 to 15%, more preferably 3 to 12%, and even more preferably 5 to 9%. This range is preferable because it provides a fresh feel when applied, prevents precipitation of the solid ultraviolet absorber, and provides excellent durability.
  • an oil-in-water emulsion composition that has excellent UV protection effect can be obtained even if it does not substantially contain ethylhexyl methoxycinnamate (2-ethylhexyl paramethoxycinnamate).
  • substantially not containing ethylhexyl methoxycinnamate means that the oil-in-water emulsion composition contains 1% or less, preferably 0.5% or less, more preferably 0.1% or less, and even more preferably 0% (no ethylhexyl).
  • the content of the oil-in-water emulsion composition of the present invention contained in the cosmetic is not particularly limited, but is preferably 20 to 100%.
  • the oil-in-water emulsion composition has a mass ratio (B)/(A) of the component (B) to the component (A) of 1 to 50.
  • ⁇ 5> The oil-in-water emulsion composition according to any one of ⁇ 1> to ⁇ 4>, further comprising a component (F) ethanol.
  • ⁇ 6> The oil-in-water emulsion composition according to any one of ⁇ 1> to ⁇ 5>, wherein the oil-in-water emulsion composition is substantially free of a surfactant.
  • ⁇ 7> The oil-in-water emulsion composition according to any one of ⁇ 1> to ⁇ 6>, wherein the viscosity at 30° C. is 5,000 to 10,000 mPa ⁇ s.
  • ⁇ 8> The oil-in-water emulsion composition according to any one of ⁇ 1> to ⁇ 7>, wherein the oil-in-water emulsion composition is a cosmetic used for sunscreen purposes.
  • the sunscreens of Examples 1 to 16 had a refreshing feel when applied, no precipitation of the solid ultraviolet absorber, and were excellent in emulsion stability, durability, and ultraviolet protection effect.
  • Comparative Example 1 in which the total content of components (A) and (B), (A) + (B), exceeded 0.9%, the fresh feel upon application and durability were sometimes inferior.
  • Comparative Example 2 in which the total content of components (A) and (B), (A) + (B), was less than 0.2%, phase inversion occurred during the production process, the emulsion stability was poor, and other effects could not be evaluated in some cases.
  • Comparative Example 3 in which the mass ratio (B)/(A) of component (B) to component (A) exceeded 50, phase inversion occurred during the production process, the emulsion stability was poor, and other effects could not be evaluated in some cases.
  • Comparative Example 4 in which the mass ratio (B)/(A) of component (B) to component (A) was less than 1, phase inversion occurred during the production process, the emulsion stability was poor, and other effects could not be evaluated in some cases.
  • Comparative Example 5 in which a salt-resistant water-soluble polymer, (sodium acrylate/sodium acryloyldimethyltaurate) copolymer, was used instead of components (A) and (B), the moist feel upon application and durability were sometimes inferior.
  • Comparative Example 6 in which a (sodium acrylate/sodium acryloyldimethyltaurate) copolymer was used as a substitute for component (A), phase inversion occurred during the production process, emulsion stability was poor, and other effects could not be evaluated in some cases.
  • Comparative Example 7 which did not contain component (B), phase inversion occurred during the production process, the emulsion stability was poor, and it was sometimes impossible to evaluate other effects.
  • Comparative Example 8 in which a (sodium acrylate/sodium acryloyldimethyltaurate) copolymer was used as a substitute for component (B), the fresh feeling upon application and durability were sometimes inferior.
  • Comparative Example 9 in which the amount of component (C) was less than 15%, the solid ultraviolet absorber precipitated, and the fresh feeling upon application, durability, and ultraviolet protection effect were sometimes inferior.
  • Comparative Example 10 in which the amount of component (C) was more than 35%, phase inversion occurred during the production process, the emulsion stability was poor, and it was sometimes impossible to evaluate other effects.
  • Comparative Example 11 in which the component (D) was less than 9%, durability and ultraviolet protection effect were sometimes inferior.
  • Comparative Example 12 in which the amount of component (D) was more than 20%, phase inversion occurred during the production process, the emulsion stability was poor, and it was sometimes impossible to evaluate other effects.
  • Comparative Example 13 in which a metal oxide that had not been subjected to a hydrophobic treatment was used as a substitute for component (D), the moist feeling upon application and durability were sometimes inferior.
  • Example 17 Cream (oil-in-water type) (Components) (% by mass) 1. (Acrylates/Beheneth-25 Methacrylate) Copolymer (Component (A)) Note 1 0.08 2. (Hydroxyethyl acrylate/Sodium acryloyldimethyltaurate) Copolymer (Component (B)) Note 2 0.4 3. OTS-treated zinc oxide (ingredient (D)) Note 10 10 4. Polyhydroxystearic acid Note 11 0.2 5. Trilaureth-4 Phosphate Note 12 0.1 6. Sodium N-stearoyl-N-methyl taurate Note 13 0.1 7. Triethanolamine 0.1 8.
  • A Mix ingredients 3 and 4 and disperse using a three-roll mill.
  • B Disperse A uniformly into components 8 to 13 at 70°C.
  • C Components 1, 2, 5, 6, 14 and components 17 to 19 are dispersed uniformly at 70°C.
  • D Add ingredient 7 to C and neutralize.
  • E Add B to D and disperse evenly.
  • F E was cooled to room temperature, and ingredients 15 and 16 were added and dispersed uniformly to obtain a cream (oil-in-water type).
  • Example 19 Base (oil-in-water type) (Components) (% by mass) 1. 1,3-butylene glycol 10 2. Glycerin 5 3. Tricetearyl phosphate 0.1 4. Polysorbate-80 0.1 5. Silica-treated titanium dioxide Note 18 1 6. Silica-treated red iron oxide Note 15 0.1 7. Silica-treated yellow iron oxide Note 16 0.1 8. Silica-treated black iron oxide Note 17 0.1 9. OTS-treated zinc oxide Note 10 (Component (D)) 15 10. Cetostearyl alcohol 0.3 11. Sorbitan sesquioleate 0.3 12. Dimethicone (dynamic viscosity at 25°C 10 mm2/s) 2 13. Drometrizole trisiloxane (ingredient (E)) Note 9 3 14.

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Publication number Priority date Publication date Assignee Title
JP7755112B1 (ja) * 2023-12-05 2025-10-15 株式会社コーセー 水中油型乳化化粧料
WO2026042767A1 (ja) * 2024-08-20 2026-02-26 花王株式会社 水中油型乳化組成物

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Publication number Priority date Publication date Assignee Title
WO2018062469A1 (ja) * 2016-09-29 2018-04-05 ロート製薬株式会社 皮膚外用組成物
JP2021011463A (ja) * 2019-07-09 2021-02-04 株式会社マンダム 水中油型皮膚洗浄料
WO2021193854A1 (ja) * 2020-03-26 2021-09-30 花王株式会社 水中油型乳化化粧料
JP2021161048A (ja) * 2020-03-31 2021-10-11 株式会社コーセー 水中油型組成物
WO2021241559A1 (ja) * 2020-05-25 2021-12-02 ロート製薬株式会社 水中油型化粧料

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Publication number Priority date Publication date Assignee Title
WO2018062469A1 (ja) * 2016-09-29 2018-04-05 ロート製薬株式会社 皮膚外用組成物
JP2021011463A (ja) * 2019-07-09 2021-02-04 株式会社マンダム 水中油型皮膚洗浄料
WO2021193854A1 (ja) * 2020-03-26 2021-09-30 花王株式会社 水中油型乳化化粧料
JP2021161048A (ja) * 2020-03-31 2021-10-11 株式会社コーセー 水中油型組成物
WO2021241559A1 (ja) * 2020-05-25 2021-12-02 ロート製薬株式会社 水中油型化粧料

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7755112B1 (ja) * 2023-12-05 2025-10-15 株式会社コーセー 水中油型乳化化粧料
WO2026042767A1 (ja) * 2024-08-20 2026-02-26 花王株式会社 水中油型乳化組成物

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