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WO2022009738A1 - Agent de base pour compositions cosmétiques en émulsion eau dans huile, et composition cosmétique en émulsion eau dans huile contenant ledit agent de base - Google Patents

Agent de base pour compositions cosmétiques en émulsion eau dans huile, et composition cosmétique en émulsion eau dans huile contenant ledit agent de base Download PDF

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WO2022009738A1
WO2022009738A1 PCT/JP2021/024587 JP2021024587W WO2022009738A1 WO 2022009738 A1 WO2022009738 A1 WO 2022009738A1 JP 2021024587 W JP2021024587 W JP 2021024587W WO 2022009738 A1 WO2022009738 A1 WO 2022009738A1
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oil
water
meth
mass
monomer
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Japanese (ja)
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友香 佐藤
悠治 園山
允人 宇山
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Shiseido Co Ltd
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Shiseido Co Ltd
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Priority to CN202180041880.5A priority Critical patent/CN115768401A/zh
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • 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
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • 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
    • 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

Definitions

  • This disclosure relates to water-in-oil emulsified cosmetics.
  • water-in-oil emulsified cosmetics that can impart not only oil and oil-soluble components but also water and water-soluble components to the skin are used. Then, in order to improve the usability of the cosmetic, an attempt to thicken or gel the water-in-oil emulsified cosmetic has been studied.
  • Patent Document 1 describes (A) 6 to 40% by mass of an ultraviolet absorber, (B) an organically modified clay mineral such as Benton, and (C) 0.1 to 15% by mass of an oil phase increase other than the above (B). It contains a viscous agent, (D) a silicone-based surfactant having an HLB of less than 8 by weight of 0.1 to 8% by mass, (E) a spherical resin powder, and (F) a volatile silicone oil.
  • Water-in-oil emulsified sunscreen cosmetics having a ratio of (C) total amount with ingredients] / [(G) total amount of non-volatile liquid oil other than silicone oil] 0.04 or more and less than 0.68 It has been disclosed.
  • Patent Document 2 describes a water-in-oil emulsified cosmetic containing an oily gelling agent composed of a copolymer composed of a specific hydrophobic monomer and a specific hydrophilic monomer, and an oil component such as a hydrocarbon oil. It has been disclosed.
  • Patent Document 3 describes cosmetic oil thickeners, hydrocarbon oils, and the like, which are composed of a copolymer composed of an easily crystalline hydrophobic monomer, a poorly crystalline hydrophobic monomer, and a hydrophilic monomer. Water-in-oil emulsified cosmetics containing the above oils are disclosed.
  • the copolymer composed of the specific monomers described in Patent Documents 2 and 3 can be used as an oil gelling agent or an oil thickener, and such a copolymer is a silicone oil. Due to its low compatibility with, it is typically not used as a thickener or gelling agent for water-in-oil emulsified cosmetics containing silicone oil.
  • the subject of the present disclosure is a novel base capable of thickening a water-in-oil emulsified cosmetic containing silicone oil, and water in oil containing a silicone oil thickened using the base. It is to provide emulsified cosmetics.
  • R 1 is hydrogen atom, glyceryl group, a linear or branched hydroxyalkyl group having 1-4 carbon atoms, or - indicated by (C 3 H 6 O) n H, integer n is 2 to 10 a polypropylene glycol group is, and R 2 is a hydrogen atom or a methyl group
  • R 3 is a hydrogen atom or a methyl group
  • R 4 is a linear or branched alkyl group or hydroxyalkyl group having 1 to 4 carbon atoms, or a substituent of the following formula 3.
  • R 5 is a linear or branched alkyl group having 16 to 22 carbon atoms
  • R 6 is a hydrogen atom or a methyl group.
  • the monomer of the formula 1 is 2-hydroxyethyl (meth) acrylate, glyceryl (meth) acrylate, PPG-6 (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate. At least one selected from hydroxy-2-methylpropyl and (meth) acrylic acid, and the monomer of the formula 2 is N- (2-hydroxyethyl) (meth) acrylamide, N-isopropyl (meth).
  • the monomer unit of the hydrophilic monomer is contained in the range of 30 to 50 mol%
  • the monomer unit of the hydrophobic monomer is contained in the range of 50 to 70 mol%.
  • the silicone oil is at least one selected from dimethyl silicone, methylphenyl polysiloxane, and cyclic polysiloxane.
  • the polar oil is a polar oil having an IOB value of 0.10 or more.
  • ⁇ Aspect 13> The cosmetic according to aspect 11 or 12, wherein the content of the silicone oil is 10% by mass or more.
  • a novel base capable of thickening water-in-oil emulsified cosmetics containing silicone oil, and water-in-oil emulsification containing silicone oil thickened using the base.
  • Cosmetics can be provided.
  • (A) is a schematic diagram of a base in which the oil-soluble copolymer of the present disclosure is blended in a continuous phase composed of silicone oil
  • (b) is a schematic diagram of a base obtained by adding water to the base of (a).
  • (A) is a schematic diagram of a base in which the oil-soluble copolymer of the present disclosure is blended in a continuous phase composed of silicone oil and polar oil
  • (b) is a schematic diagram of water as the base of (a). It is a schematic diagram of a water-in-oil emulsified cosmetic prepared by adding.
  • the water-in-oil emulsified cosmetic base of the present disclosure (sometimes referred to simply as "base”) is a silicone oil, a polar oil, and at least one hydrophilic selected from the above formulas 1 and 2. It contains an oil-soluble copolymer having a monomer unit composed of a sex monomer and a monomer unit composed of a hydrophobic monomer of the above formula 4.
  • the oil-soluble copolymer of the present disclosure is gelled, which is a kind of thickening, with respect to hydrocarbon oils such as liquid paraffin and ester oils such as cetyl 2-ethylhexanoate. It is known that it can cause.
  • this oil-soluble copolymer has low compatibility with silicone oil. Therefore, for example, when this oil-soluble copolymer is blended with silicone oil such as dimethylpolysiloxane, the oil-soluble copolymer is blended. As shown in FIG. 1 (a), a precipitate of only the polymer of the oil-soluble copolymer 11 was likely to be formed.
  • the precipitated state can be eliminated and an emulsion can be obtained, but the obtained water in oil can be obtained.
  • the type emulsified cosmetic was not thickened and exhibited a silky state, and was in an unstable emulsified state in which it separated immediately after being allowed to stand. This is because the oil-soluble copolymer has a site composed of a specific hydrophilic monomer, and therefore, as shown in FIG. 1 (b), the interface between the aqueous phase (water droplet 13) and the oil phase. It is considered that the oil-soluble copolymer 11 is arranged in the vicinity.
  • the site composed of a specific hydrophobic monomer is difficult to spread in the silicone oil which is difficult to be compatible with each other, and it is difficult to form a network structure for taking in the oil due to the site. It is considered that the polymer is difficult to thicken the water-in-oil emulsified cosmetic containing silicone oil.
  • the base of the present disclosure contains polar oil in addition to silicone oil.
  • This polar oil is easily compatible with a portion of the oil-soluble copolymer composed of a specific hydrophobic monomer.
  • the oil-soluble copolymer and the polar oil are mixed in an oil containing a high amount of silicone oil.
  • the thickening effect of the base was poor, and in some cases, a gel or a swollen layer containing a part of the oil was formed.
  • the present inventor prepares a water-in-oil emulsified cosmetic by adding water to such a base, surprisingly, in the case of such a cosmetic, thickening can be exhibited. I found.
  • the moiety of the oil-soluble copolymer composed of a specific hydrophobic monomer is more likely to spread in the oil phase than in the case of a base containing only silicone oil as the oil phase. Therefore, as shown in FIG. 2A, oil content is taken in to some extent even in a place where the oil-soluble copolymer 21 is precipitated, and a gel or a swollen layer is formed to locally thicken the viscosity. However, it is considered that such thickening action does not contribute to the thickening of the entire base.
  • the emulsified water droplets are dispersed throughout the system, and accordingly, the oil-soluble copolymer arranged near the interface between the aqueous phase and the oil phase is also dispersed throughout the system. It is thought that it will be. Further, the portion of the oil-soluble copolymer composed of a specific hydrophobic monomer is more likely to spread in the oil phase when the oil phase contains silicone oil and polar oil than when the oil phase contains only silicone oil. As a result, as shown in FIG. 2B, the site composed of a specific hydrophobic monomer spread around the water droplet 23 forms a network structure in the entire system with the water droplet 23 as a cross-linking point to release oil. In order to retain it, we believe that water-in-oil emulsified cosmetics containing silicone oil can be thickened.
  • the hydrophobic monomer unit existing so as to spread in the oil phase becomes a steric obstacle and is adjacent. It is considered that the emulsification stability of cosmetics is improved because the coalescence of water droplets is suppressed.
  • the "hydrophilic monomer” is intended to be a monomer that dissolves in water at an arbitrary ratio
  • the “hydrophobic monomer” is intended to be another monomer, that is, a monomer that is basically immiscible with water. ..
  • (meth) acrylic means acrylic or methacrylic.
  • the water-in-oil emulsified cosmetic base of the present disclosure comprises a monomer unit composed of a silicone oil, a polar oil, and at least one hydrophilic monomer selected from the above-mentioned formulas 1 and 2, and the above-mentioned. It contains an oil-soluble copolymer having a monomer unit composed of the hydrophobic monomer of the formula 4, and has a performance of thickening when water is added.
  • the blending amount of the silicone oil in the base of the present disclosure is not particularly limited, and may be, for example, 50% by mass or more, 55% by mass or more, or 60% by mass or more with respect to the total amount of the base. It can be 80% by mass or less, 75% by mass or less, or 70% by mass or less.
  • the blending amount of the silicone oil can be, for example, larger than the blending amount of the polar oil to be blended at the same time. As mentioned above, it can be 70% by mass or more, or 75% by mass or more, and can be 95% by mass or less, 90% by mass or less, or 85% by mass or less.
  • the silicone oil is not particularly limited, and is, for example, dimethyl silicone (sometimes referred to as "dimethylpolysiloxane” or “dimethicone”); trimethylpentaphenyltrisiloxane, diphenyldimethicone, diphenylsiloxyphenyltrimethicone, phenyltrimethicone, Methylphenylpolysiloxane such as phenyldimethicone (sometimes referred to as "methylphenylsilicone”); cyclic polysiloxane (“cyclic silicone”) such as octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane.
  • dimethyl silicone sometimes referred to as "dimethylpolysiloxane” or “dimethicone”
  • trimethylpentaphenyltrisiloxane diphenyldimethicone, diphen
  • Methylhydrogenpolysiloxane methylphenyl polysiloxane, and cyclic polysiloxane is preferable from the viewpoint of thickening viscosity, emulsion stability, etc., and further, cosmetics can be used as a liquid foundation.
  • Dimethylsilicone is more preferable from the viewpoint of separation resistance (crack resistance) and the like when prepared.
  • the base contains only silicone oil as an oil, it cannot be significantly thickened even if water is added in combination with the oil-soluble copolymer of the present disclosure. That is, the polar oil blended in the base of the present disclosure can, so to speak, function as a binder component for thickening the silicone oil and the oil-soluble copolymer.
  • the blending amount of the polar oil is not particularly limited, and may be, for example, 5.0% by mass or more, 10% by mass or more, or 15% by mass or more, and 30% by mass or less, based on the total amount of the base. , 25% by mass or less, or 20% by mass or less.
  • the blending amount of the polar oil can be, for example, 5.0% by mass or more, 10% by mass or more, or 15% by mass or more, and 45% by mass or less, 40% by mass, based on the total amount of the oil content.
  • it can be 35% by mass or less, 30% by mass or less, or 25% by mass or less.
  • the mixing ratio of the silicone oil and the polar oil is not particularly limited, but the silicone oil and the polar oil are polar from the viewpoint of emulsion stability, for example, separation resistance (crack resistance) when the cosmetic is prepared as a liquid foundation.
  • the mass ratio with oil is preferably in the range of 9: 1 to 4: 1 (8: 2), more preferably in the range of 9: 1 to 8.5: 1.5.
  • the polar oil blended in the base of the present disclosure is not particularly limited as long as it can function as a binder component for thickening, and for example, a polar oil having an IOB value of 0.10 or more may be adopted. can.
  • the IOB value of the polar oil can be, for example, 0.11 or more, 0.12 or more, 0.13 or more, 0.14 or more, or 0.15 or more, and 0.65 or less and 0.60 or less. , 0.55 or less, 0.50 or less, 0.45 or less, or 0.40 or less. Among them, the IOB value of the polar oil is preferably 0.15 or more and 0.55 or less, and more preferably 0.20 or more and 0.55 or less from the viewpoint of long-term viscosity increasing performance or emulsion stabilizing performance. , 0.20 or more and 0.50 or less are particularly preferable.
  • Inorganic value and “organic value” are set according to the atom or functional group, and the “inorganic value” and “organic value” of all the atoms and functional groups in the organic compound are integrated. Can be used to calculate the IOB value of the organic compound (see, for example, Yoshio Koda, “Organic Conceptual Diagram-Basics and Applications-", pp. 11-17, Sankyo Publishing, 1984).
  • octylmethoxycinnamate can be used alone or in combination of two or more.
  • at least one selected from octylmethoxycinnamate, tripropylene glycol dipivalate, cetyl ethylhexanate, diisostearyl malate, and octyl salicylate is preferable from the viewpoint of thickening viscosity, emulsion stability, and the like, and octylmethoxy is preferable.
  • At least one selected from cinnamate, tripropylene glycol dipivalate, and diisostearyl malate is more preferable, and further, for example, from the viewpoint of separation resistance (crack resistance) when cosmetics are prepared as a liquid foundation. Therefore, octylmethoxycinnamate is particularly preferable.
  • the oil content in the base of the present disclosure may be only silicone oil and polar oil, but an oil component other than silicone oil and polar oil may be optionally blended as long as it does not affect the effect of the present invention. May be good.
  • oils include hydrocarbon oils, higher alcohols, and oil-soluble polyhydric alcohols. These can be used alone or in combination of two or more.
  • hydrocarbon oil examples include liquid paraffin, tetraisobutane, hydrogenated polydecene, olefin oligomer, isododecane, isohexadecane, squalane, hydrogenated polyisobutane and the like.
  • higher alcohols examples include isostearyl alcohol and oleyl alcohol.
  • oil-soluble polyhydric alcohol examples include polybutylene glycol and the like.
  • the oil content can be blended in the range of 15% by mass or less, 10% by mass or less, or 5.0% by mass or less with respect to the total amount of the base. Alternatively, it can be blended in the range of 10% by mass or less, 5.0% by mass or less, or 1.0% by mass or less with respect to the total amount of oil.
  • the lower limit of the blending amount of any oil is not particularly limited, but may be more than 0% by mass or 0.1% by mass or more with respect to the total amount of the base or the oil.
  • the base of the present disclosure contains an oil-soluble copolymer that can function as a thickener in a water-in-oil emulsified cosmetic.
  • Such an oil-soluble copolymer contains at least a monomer unit composed of at least one hydrophilic monomer selected from the above formulas 1 and 2 and a monomer unit composed of the hydrophobic monomer of the above formula 4.
  • Each of these monomer units may be composed of a single monomer unit, or may be composed of two or more kinds of monomer units.
  • the hydrophilic monomer unit may be composed of one kind of monomer unit
  • the hydrophobic monomer unit may be composed of two kinds of monomer units.
  • the polymerization form of the oil-soluble copolymer is not particularly limited, and for example, a random type, a block type, or the like can be adopted, but the random type is preferable from the viewpoint of easiness of synthesis.
  • the ratio of the monomer unit composed of the hydrophilic monomer to the monomer unit composed of the hydrophobic monomer in the oil-soluble copolymer is not particularly limited, but is, for example, from the viewpoint of viscosity thickening, emulsion stability and the like.
  • the monomer unit of the hydrophilic monomer may be contained in an amount of 30 mol% or more, 32 mol% or more, 35 mol% or more, or 40 mol% or more, and 50 mol% or less, 48 mol% or less, or 45. It may be contained in an amount of mol% or less.
  • the monomer unit of the hydrophobic monomer may be contained in an amount of 50 mol% or more, 52 mol% or more, or 55 mol% or more, and 70. It may be contained in an amount of mol% or less, 68 mol% or less, 65 mol% or less, or 60 mol% or less.
  • the content of the oil-soluble copolymer can be 0.1% by mass or more, 0.5% by mass or more, or 1.0% by mass or more, and 10% by mass or less, based on the total amount of the base. , 5.0% by mass or less, or 3.0% by mass or less.
  • the ratio of the oil-soluble copolymer to the total amount of oil shall be 0.5% by mass or more, 0.7% by mass or more, 1.0% by mass or more, 1.2% by mass or more, or 1.5% by mass or more. In addition, it should be 8.0% by mass or less, 7.0% by mass or less, 6.0% by mass or less, 5.0% by mass or less, 4.5% by mass or less, or 4.0% by mass or less. Can be done.
  • hydrophilic monomer As the hydrophilic monomer, at least one monomer selected from the following formulas 1 and 2 can be used.
  • R 1 is represented by a hydrogen atom, a glyceryl group, a linear or branched hydroxyalkyl group having 1 to 4 carbon atoms, or-(C 3 H 6 O) n H, where n is 2. It is a polypropylene glycol group which is an integer of about 10, and R 2 is a hydrogen atom or a methyl group.
  • examples of the hydroxyalkyl group include 2-hydroxyethyl group, 2-hydroxypropyl group, 2-hydroxyethyl-2-methylpropyl group, 2-hydroxybutyl group, 3-hydroxybutyl group and 4-hydroxybutyl group. The group can be mentioned.
  • hydrophilic monomer represented by the formula 1 examples include 2-hydroxyethyl (meth) acrylate, glyceryl (meth) acrylate, PPG-6 (meth) acrylate, and 2 (meth) acrylate.
  • -Hydroxypropyl, (meth) acrylic acid 2-hydroxy-2-methylpropyl, (meth) acrylic acid can be mentioned.
  • These can be used alone or in combination of two or more.
  • glyceryl (meth) acrylate is preferable, and glyceryl methacrylate is more preferable, from the viewpoint of viscosity thickening, emulsion stability and the like.
  • R 3 is a hydrogen atom or a methyl group
  • R 4 is a linear or branched alkyl group or hydroxyalkyl group having 1 to 4 carbon atoms, or a substitution of the following formula 3. It is a group.
  • the alkyl group in R 4 for example, an ethyl group, a propyl group, an isopropyl group, and a butyl group, a hydroxyalkyl group, e.g., 2-hydroxyethyl group, 2-hydroxypropyl group, Examples thereof include 2-hydroxyethyl-2-methylpropyl group, 2-hydroxybutyl group, 3-hydroxybutyl group and 4-hydroxybutyl group.
  • hydrophilic monomer represented by the formula 2 examples include N- (2-hydroxyethyl) (meth) acrylamide, N-isopropyl (meth) acrylamide, and 2- (meth) acrylamide-2-methylpropane. Sulfonic acid can be mentioned. These can be used alone or in combination of two or more. Of these, N- (2-hydroxyethyl) (meth) acrylamide is preferable, and N- (2-hydroxyethyl) acrylamide is more preferable, from the viewpoints of viscosity thickening, emulsion stability and the like.
  • R 5 is a linear or branched alkyl group having 16 to 22 carbon atoms
  • R 6 is a hydrogen atom or a methyl group.
  • examples of the linear or branched alkyl group having 16 to 22 carbon atoms include a cetyl group, a stearyl group, an isostearyl group, and a behenyl group.
  • a linear alkyl group having 16 to 22 carbon atoms is preferable, and a cetyl group, a stearyl group, and a behenyl group are more preferable, from the viewpoints of thickening viscosity, emulsion stability, compatibility with polar oil, and the like.
  • the hydrophobic monomer is a (meth) acrylic acid alkyl ester, that is, an ester composed of (meth) acrylic acid and an alcohol having a linear or branched alkyl group having 16 to 22 carbon atoms.
  • Specific examples thereof include cetyl (meth) acrylate, stearyl (meth) acrylate, isostearyl (meth) acrylate, and behenyl (meth) acrylate. These can be used alone or in combination of two or more.
  • cetyl (meth) acrylate, stearyl (meth) acrylate, and behenyl (meth) acrylate are preferable, and stearyl (meth) acrylate is preferable from the viewpoint of viscosity increase, emulsion stability, compatibility with polar oil, and the like. Is more preferable.
  • the oil-soluble copolymer of the present disclosure preferably does not contain a monomer unit composed of monomers other than the above formulas 1, 2, and 4, but the present invention. Other monomer units may be further contained as long as the effect is not impaired.
  • the proportion of such monomer units can be 30 mol% or less, 20 mol% or less, 15 mol% or less, 10 mol% or less, or 5 mol% or less, and 0 mol% or less, based on the total amount of the constituent monomer units. It can be super 1 mol% or more, or 3 mol% or more.
  • Examples of the monomers other than the above formulas 1, 2, and 4 include one or more monomers selected from the group consisting of various anionic monomers, cationic monomers, nonionic monomers, and monomers other than these. ..
  • examples of the hydrophilic monomer other than the hydrophilic monomer represented by the formula 1 or the formula 2 include vinylpyrrolidone, vinylimidazole, methoxypolyethylene glycol (meth) acrylate, and N, N-dimethyl (meth) acrylamide. , N, N-diethyl (meth) acrylamide, acryloylmorpholin, metaacryloylmorpholin, N- (2-methacryloyloxyethyl) ethyleneurea, 2-methacryloyloxyethylphosphorylcholine.
  • hydrophobic monomer other than the hydrophobic monomer represented by the formula 4 examples include methylstyrene, styrene, benzyl (meth) acrylate, phenyl (meth) acrylate, tris (trimethylsiloxy) silylpropyl (meth) acrylate, and the like.
  • (Meta) Acrylic acid-2-perfluorohexyl-2-ethyl can be mentioned.
  • hydrophobic monomer represented by the following formula 5 can be used:
  • R 7 is a branched alkyl group having 18 or less carbon atoms or a linear alkyl group having 12 or less carbon atoms
  • R 8 is a hydrogen atom or a methyl group.
  • the linear or branched alkyl group in R 7 an alkyl group having 3 or more carbon atoms, 4 or more, 5 or more, 6 or more, 7 or more, or 8 or more can be used.
  • R 8 a hydrogen atom is preferable.
  • the monomer unit composed of the hydrophobic monomer represented by the above formula 4 crystallizes by the hydrophobic monomer unit between the copolymers as the oil-soluble copolymers approach each other, so that the oil component is taken in. It is thought that the network structure is formed in the form.
  • the monomer unit composed of the hydrophobic monomer represented by the formula 5 inhibits the crystallization by the monomer unit composed of the hydrophobic monomer represented by the formula 4, and suppresses the expression of the network structure based on the crystallization. Therefore, the thickening can be controlled by introducing a monomer unit composed of the hydrophobic monomer represented by the formula 5.
  • hydrophobic monomer represented by the formula 5 examples include hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, and (meth).
  • Decyl acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, isostearyl (meth) acrylate and the like can be mentioned. These can be used alone or in combination of two or more.
  • 2-ethylhexyl (meth) acrylate, octyl (meth) acrylate, lauryl (meth) acrylate, and isostearyl (meth) acrylate are preferable, and octyl (meth) acrylate, lauryl (meth) acrylate, Isostearyl (meth) acrylate is more preferred, and octyl (meth) acrylate and isostearyl (meth) acrylate are even more preferred.
  • the oil-soluble copolymer of the present disclosure can be obtained by a known polymerization method.
  • the method is not limited to the following method, but for example, a mixture of a hydrophilic monomer and a hydrophobic monomer, a polymerization solvent, and a polymerization initiator are charged in a reaction vessel and maintained for several hours while being heated to maintain a constant temperature for polymerization. Proceed with the reaction. Then, the oil-soluble copolymer can be obtained by distilling off the polymerization solvent from the solution in the reaction vessel.
  • a copolymer can also be obtained by the living radical polymerization method.
  • the molecular weight of the copolymer can be easily adjusted, and a copolymer having a narrow molecular weight distribution can be produced.
  • polymerization solvent a solvent that does not show reactivity with the functional group of the monomer is appropriately selected.
  • Hydrocarbon solvents such as, but not limited to, n-hexane, n-octane, n-decane, isodecane, cyclohexane, methylcyclohexane, toluene, xylene, ethylbenzene, cumene; methanol, ethanol, n-propanol.
  • polymerization initiator As the polymerization initiator, conventionally known ones can be used, and the polymerization initiator is not particularly limited, and for example, an organic peroxide or an azo compound can be used. Specifically, benzoyl peroxide, dicumyl peroxide, diisopropyl peroxide, di-t-butylperoxide, t-butylperoxybenzoate, t-hexylperoxybenzoate, t-butylperoxy-2-ethylhexanoate.
  • the time for maintaining the reflux state is preferably continued until the monomer is exhausted, and is not particularly limited, but may be, for example, 1 hour or more, 2 hours or more, or 3 hours or more. Further, it can be 144 hours or less, 72 hours or less, or 48 hours or less.
  • the polymerization atmosphere is not particularly limited, and may be polymerized as it is in an atmospheric atmosphere, that is, oxygen may be present in the polymerization system within a normal range, and oxygen may be removed if necessary. Therefore, it may be carried out in an atmosphere of an inert gas such as nitrogen or argon. As the various materials to be used, impurities may be removed by distillation, activated carbon, alumina or the like, or commercially available products may be used as they are. Further, the polymerization may be carried out under light shielding, or may be carried out in a transparent container such as glass.
  • ком ⁇ онент that contribute to the polymerization reaction
  • other components such as a chain transfer agent may be added to the reaction vessel as needed.
  • the chain transfer agent is not particularly limited, and examples thereof include compounds having a mercapto group such as lauryl mercaptan and thioglycerol; inorganic salts such as sodium hypophosphite and sodium hydrogen sulfite; ⁇ -methylstyrene dimer and the like. ..
  • the amount of the chain transfer agent to be used is appropriately determined so that the molecular weight of the copolymer is within the desired range, but is usually preferably in the range of 0.01 to 10% by mass with respect to the monomer.
  • the water-in-oil emulsified cosmetic of the present disclosure contains the above-mentioned base and water droplets dispersed in the base and containing water.
  • the water-in-oil emulsified cosmetic of the present disclosure contains polar oil in addition to silicone oil as the oil component of the continuous phase, and contains water droplets of the dispersed phase and the oil-soluble copolymer described above, resulting in excellent thickening. The effect can be exhibited.
  • a B-type viscometer (TVB type viscometer TVB-10, manufactured by Toki Sangyo Co., Ltd.) was used, and the rotor No. It can be evaluated by any of 2 to 4 and the viscosity measured under the measurement condition of the rotation speed of 12 rpm.
  • the unshaken viscosity or the post-shaking viscosity of the cosmetics of the present disclosure having a composition containing no powder such as a pigment is 500 mPa ⁇ s or more, 600 mPa ⁇ s or more, and the like. It is possible to achieve 700 mPa ⁇ s or more, 800 mPa ⁇ s or more, or 900 mPa ⁇ s or more.
  • the upper limit of the viscosity is not particularly limited, but is, for example, 30,000 mPa ⁇ s or less, 15,000 mPa ⁇ s or less, 10,000 mPa ⁇ s or less, 5,000 mPa ⁇ s or less, or 3,000 mPa ⁇ s or less. Can be.
  • the unshaken viscosity or the post-shaking viscosity of the cosmetics of the present disclosure comprising powders such as pigments is 4,000 mPa ⁇ s or more, 5,000 mPa ⁇ . It is possible to achieve s or more, 6,000 mPa ⁇ s or more, 7,000 mPa ⁇ s or more, 8,000 mPa ⁇ s or more, or 9,000 mPa ⁇ s or more.
  • the upper limit of the viscosity is not particularly limited, but may be, for example, 60,000 mPa ⁇ s or less, 55,000 mPa ⁇ s or less, 50,000 mPa ⁇ s or less, or 45,000 mPa ⁇ s or less.
  • the viscosity of the cosmetic is at least one of 1 day, 4 days, 2 weeks, and 4 weeks after the preparation of the cosmetic.
  • the viscosity at the time point is intended, it is preferable to intend the viscosity 2 weeks or 4 weeks after the cosmetic is prepared from the viewpoint of the index of the thickening effect over a long period of time.
  • the viscosity of the cosmetic after shaking is intended to be the viscosity when measured after shaking by hand several to several tens of times (for example, 3 to 20 times) so that the entire cosmetic is substantially uniform. ..
  • water-in-oil emulsified cosmetics containing silicone oil prepared using organically modified clay minerals such as Benton
  • organically modified clay minerals such as Benton
  • the water-in-oil emulsified cosmetics of the present disclosure have a novel feeling of use, for example, creamy use, which is different from the case of using an organically modified clay mineral such as Benton. It is possible to express a feeling and a mellow feeling of use.
  • the water-in-oil emulsified cosmetic of the present disclosure contains the above-mentioned silicone oil, polar oil, and oil-soluble copolymer contained in the base.
  • the blending ratios of the silicone oil, the polar oil, and the oil-soluble copolymer to the total amount of oil in the cosmetics and the mass ratio of the silicone oil and the polar oil
  • the blending ratios of the above-mentioned bases and the blending ratios The mass ratio can be adopted as well.
  • the content of the silicone oil in the cosmetic may be 10% by mass or more, 15% by mass or more, 20% by mass or more, or 25% by mass or more, and 40% by mass or more, based on the total amount of the cosmetic. It can be mass% or less, 35 mass% or less, or 30 mass% or less.
  • the content of polar oil in the cosmetic may be 1.0% by mass or more, 3.0% by mass or more, or 5.0% by mass or more, and 20% by mass, based on the total amount of the cosmetic. % Or less, 15% by mass or less, or 10% by mass or less.
  • the content of the oil-soluble copolymer in the cosmetics is 0.1% by mass or more, 0.3% by mass or more, 0.5% by mass or more, 0.7% by mass or more, based on the total amount of the cosmetics. Alternatively, it can be 1.0% by mass or more, and can be 5.0% by mass or less, 4.0% by mass or less, 3.0% by mass or less, or 2.0% by mass or less. Since the water-in-oil emulsified cosmetic of the present disclosure may also exhibit a thickening effect based on the packing action of a plurality of water droplets contained in the cosmetic, the oil-soluble copolymer as a thickener is thus used. It is considered that the cosmetics of the present disclosure can exhibit excellent thickening even in a relatively low amount.
  • the water-in-oil emulsified cosmetics of the present disclosure are prepared by adding water to the above-mentioned base, and as a result, such cosmetics contain water droplets as an aqueous phase or a dispersed phase.
  • water The water that can be used in the water-in-oil emulsified cosmetics of the present disclosure is not particularly limited, but water used for cosmetics, quasi-drugs, and the like can be used.
  • purified water, ion-exchanged water, tap water and the like can be used.
  • the content of water can be 30% by mass or more, 35% by mass or more, 40% by mass or more, 45% by mass or more, 50% by mass or more, or 55% by mass or more with respect to the total amount of cosmetics. , 70% by mass or less, 65% by mass or less, or 60% by mass or less.
  • the number of water droplets can be increased, resulting in an increase in the cross-linking points of the network structure as shown in FIG. 2 (b) and the thickening effect based on the packing action of the water droplets. be able to. That is, an increase in the water content can contribute to an increase in the viscosity of the cosmetic.
  • a surfactant In the water-in-oil emulsified cosmetics of the present disclosure, a surfactant is typically used at the time of preparation thereof.
  • the surfactant is generally present mainly near the interface between the aqueous phase and the oil phase, that is, near the outer periphery of the water droplet, and a part of the surfactant is dispersed in the oil. Further, the surfactant may be blended in the above-mentioned base, or may be blended in an aqueous phase part containing water or the like.
  • the surfactant that can be used in the water-in-oil emulsified cosmetics of the present disclosure is not particularly limited, and known surfactants can be used alone or in combination of two or more.
  • silicone surfactants in particular silicone surfactants modified with a polyether group or a polyglycerin group, can be used.
  • silicone surfactant modified by the polyether group examples include PEG-11 methyl ether dimethicone, PEG-10 dimethicone, PEG-9 polydimethylsiloxyethyl dimethicone, lauryl PEG-9 polydimethylsiloxyethyl dimethicone, and cetyl PEG. / PPG-10 / 1 dimethicone and the like can be mentioned.
  • silicone surfactant modified by the polyglycerin group examples include polyglyceryl-3 disiloxane dimethicone, polyglyceryl-3 polydimethylsiloxyethyl dimethicone, and lauryl polyglyceryl-3 polydimethylsiloxyethyl dimethicone.
  • the blending amount of the surfactant may be 0.1% by mass or more, 0.5% by mass or more, or 1.0% by mass or more with respect to the total amount of the cosmetics from the viewpoint of emulsion stability and the like. Further, it can be 8.0% by mass or less, 6.0% by mass or less, or 5.0% by mass or less.
  • the water-in-oil emulsified cosmetic of the present disclosure can appropriately contain various components as long as it does not affect the effects of the present invention.
  • various ingredients include additive ingredients that can be usually blended in cosmetics.
  • moisturizers such as dynamite glycerin, water-soluble polymers, film-forming agents such as siliconeized polysaccharides, metal ion blockers, lower alcohols, polyhydric alcohols (eg, 1,3-butylene glycol, PEG1500, dipropylene glycol).
  • Etc. higher fatty acids such as isostearic acid, various extracts, sugars, amino acids, organic amines, polymer emulsions, chelating agents, UV absorbers, pH regulators, skin nutrients, vitamins, pharmaceuticals, non-pharmaceutical products, cosmetics
  • Alkaline components and the like can be mentioned.
  • These optional components can be used alone or in combination of two or more, and can be appropriately blended in the oil phase or the aqueous phase. Further, these optional components, particularly oil-soluble components or powder components such as pigments, may be previously blended in the above-mentioned base.
  • the cosmetics of the present disclosure may contain organically modified clay minerals such as Benton, but from the viewpoint of obtaining the above-mentioned novel feeling of use, such clay minerals are 1. It is preferably used in the range of 0% by mass or less, 0.5% by mass or less, less than 0.1% by mass, or 0.05% by mass or less, and more preferably no organically modified clay mineral is used.
  • the product form of the water-in-oil emulsified cosmetic of the present disclosure is not particularly limited, but for example, skin care cosmetics such as milky lotion, cream, face oil, body oil, and beauty liquid; foundation, makeup base, etc.
  • Makeup cosmetics such as lipstick, cheek red, eye shadow, mascara, and mascara base; skin cleaning agents such as makeup remover; hair cleaning agents; hair treatments, hair cosmetics such as hair oil; sunscreen cosmetics; hair dyes, etc. ..
  • the water-in-oil emulsified cosmetics of the present disclosure can improve the longevity of makeup by blending silicone oil, and can be blended with a specific oil-soluble copolymer and polar oil in oil containing silicone oil.
  • water-based emulsified cosmetics it is possible to develop a new feeling of use that has never been seen before, for example, a creamy feeling of use, a mellow feeling of use, and the like.
  • the water-in-oil emulsified cosmetic of the present disclosure can reduce or prevent problems such as separation (cracking) when a pigment is blended, for example.
  • the water-in-oil emulsified cosmetic of the present disclosure can be produced by a conventional method.
  • an oil-soluble copolymer and a surfactant can be added to an oil component and stirred to prepare a base, and water can be added to the base and stirred to obtain a water-in-oil emulsified cosmetic.
  • the above-mentioned optional components may be appropriately added to water or oil, or heating means may be applied.
  • a water-in-oil emulsified cosmetic containing a powder component such as a foundation
  • a powder component such as a foundation
  • an oil containing silicone oil and a polar oil is heated, and an oil-soluble copolymer and a surface activity thereof are heated therein.
  • the powder parts containing pigments and the like are mixed with the heated oil phase parts to prepare a base, and then the aqueous phase parts containing heated water and the like are mixed with the base and slowly cooled.
  • a water-in-oil emulsified cosmetic containing a powder component such as a pigment can be prepared.
  • the heating temperature condition can be, for example, 70 ° C. or higher, 75 ° C. or higher, or 80 ° C. or higher, and can be 95 ° C. or lower, 90 ° C. or lower, or 85 ° C. or lower. ..
  • the temperature condition for slow cooling can be, for example, 50 ° C. or lower, 45 ° C. or lower, or 40 ° C. or lower, and 25 ° C. or higher, 30 ° C. or higher, or 35 ° C. or higher.
  • ⁇ Evaluation method 1> evaluation of viscosity
  • the viscosity of the cosmetic was determined by using a B-type viscometer (TVB type viscometer TVB-10, manufactured by Toki Sangyo Co., Ltd.) under an atmosphere of 25 ° C. It was evaluated under the measurement conditions of any of 2 to 4 and the rotation speed of 12 rpm.
  • the viscosity of the cosmetic after shaking was evaluated by the above viscometer and measurement conditions after shaking by hand about 10 times so that the entire cosmetic was substantially uniform.
  • the rotor was No. No. 4 was adopted, and in the cosmetics of Examples 3 to 4 and Comparative Examples 1 and 2, the rotor was No. No. 2 was adopted, and in the cosmetics of Examples 5 to 8, the rotor was No. 3 was adopted.
  • Example 1 to 4 Comparative Examples 1 to 2> In Examples 1 to 4 and Comparative Examples 1 to 2, the presence or absence of an oil-soluble copolymer or polar oil and the influence of the type of silicone oil were evaluated. The results are shown in Table 1.
  • Example 1 An oil containing octylmethoxycinnamate and dimethylsilicone was heated to 80 to 90 ° C., PEG-10 dimethicone, an oil-soluble copolymer, and isostearic acid were added to the oil, and the mixture was stirred to prepare a base. .. While heating the base, water was added to the base and stirred, and then slowly cooled to 40 ° C. to prepare a water-in-oil emulsified cosmetic.
  • Example 1 The base prepared in Example 1 was cloudy when heated, and when left at room temperature, a transparent gel-like substance was formed on the bottom. On the other hand, no gel-like substance was formed in the obtained water-in-oil emulsified cosmetic.
  • Examples 2 to 4 Comparative Examples 1 to 2
  • Cosmetics of Examples 2 to 4 and Comparative Examples 1 and 2 were prepared in the same manner as in Example 1 except that the blending ratios in Table 1 were changed.
  • the bases prepared in Examples 2 to 4 are all in a transparent state when heated, and when left at room temperature, the bases of Examples 3 and 4 are transparent at the bottom. A gel-like substance was formed. On the other hand, no gel-like substance was produced in any of the obtained water-in-oil emulsified cosmetics.
  • Examples 5 to 8 In Examples 5 to 8, the influence of the type of polar oil was evaluated. The results are shown in Table 2. Table 2 also shows the results of Example 4 and Comparative Examples 1 and 2.
  • Examples 5 to 8 The cosmetics of Examples 5 to 8 were prepared in the same manner as in Example 1 except that the blending ratios in Table 2 were changed.
  • the bases of Examples 5 and 7 became cloudy at the time of heating, and the bases of Examples 6 and 8 were clouded at the time of heating. It was in a transparent state. Moreover, when these were left at room temperature, a transparent gel-like substance was formed on the bottom. On the other hand, no gel-like substance was produced in any of the obtained water-in-oil emulsified cosmetics.
  • the polar oil contributes to an increase in the viscosity of the water-in-oil emulsified cosmetic containing the silicone oil and the oil-soluble copolymer at the time of preparation, and when the viscosity of the cosmetic decreases over time, the polar oil contributes to the increase in viscosity. It was found that it has a function of recovering its viscosity by shaking.
  • Examples 9 to 13 are formulations that can be used for foundations and the like containing pigments, and the influence of the blending ratio of the oil-soluble copolymer on the cosmetics of such formulations was evaluated. The results are shown in Table 3.
  • ⁇ Evaluation method 2> evaluation of viscosity
  • the viscosity of the cosmetic was determined by using a B-type viscometer (TVB type viscometer TVB-10, manufactured by Toki Sangyo Co., Ltd.) under an atmosphere of 25 ° C. It was evaluated under the measurement conditions of 2 to 4 and the rotation speed of 12 rpm.
  • Example 9 An oil containing octylmethoxycinnamate and dimethylsilicone is heated to 80 to 90 ° C., PEG-10 dimethicone, an oil-soluble copolymer, and isostearic acid are added to the oil, and the mixture is stirred to prepare an oil phase part. did. While heating the oil phase parts, each component of the powder parts shown in Table 3 was added and stirred to prepare a base. While heating the base, water was added to the base and stirred, and then slowly cooled to 40 ° C. to prepare a water-in-oil emulsified cosmetic containing a pigment.
  • Example 10 to 13 The cosmetics of Examples 10 to 13 were prepared in the same manner as in Example 9 except that the blending ratios in Table 3 were changed.
  • the viscosity of the cosmetics of Examples 9 to 13 is significantly higher than the viscosity of the cosmetics of Examples 1 to 8, which is considered to be influenced by the blending of the pigment.
  • Example 14 to 16 The formulations of Examples 14 to 16 are also formulations that can be used for foundations and the like containing pigments, and the effects of silicone oil and polar oil on cosmetics of such formulations were evaluated. The results are shown in Table 4. Table 4 also shows the results of Example 11.
  • ⁇ Evaluation method 3> evaluation of viscosity
  • the viscosity of the cosmetic was determined by using a B-type viscometer (TVB type viscometer TVB-10, manufactured by Toki Sangyo Co., Ltd.) under an atmosphere of 25 ° C. It was evaluated under the measurement conditions of 2 to 4 and the rotation speed of 12 rpm.
  • Example 14 to 16 The cosmetics of Examples 14 to 16 were prepared in the same manner as in Example 9 except that the blending ratios in Table 4 were changed.

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Abstract

La présente invention concerne : un nouvel agent de base qui est capable d'épaissir une composition cosmétique en émulsion eau dans huile qui contient une huile de silicone ; et une composition cosmétique en émulsion eau dans huile contenant une huile de silicone, ladite composition cosmétique en émulsion eau dans huile étant épaissie à l'aide de l'agent de base.　Un agent de base pour des compositions cosmétiques en émulsion eau dans huile selon la présente invention contient une huile de silicone, une huile polaire et un copolymère soluble dans l'huile qui a une unité monomère qui est composée d'un monomère hydrophile spécifique et une unité monomère qui est composée d'un monomère hydrophobe spécifique.
PCT/JP2021/024587 2020-07-10 2021-06-29 Agent de base pour compositions cosmétiques en émulsion eau dans huile, et composition cosmétique en émulsion eau dans huile contenant ledit agent de base Ceased WO2022009738A1 (fr)

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JP2003212744A (ja) * 2002-01-24 2003-07-30 L'oreal Sa 半結晶性ポリマーを含む、皮膚または毛髪の抗日光保護用組成物
JP2003238348A (ja) * 2002-01-24 2003-08-27 L'oreal Sa 半結晶性ポリマーでゲル化された化粧品組成物
WO2016098456A1 (fr) * 2014-12-19 2016-06-23 株式会社 資生堂 Copolymère et agent gélifiant huileux

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JPH1053625A (ja) * 1996-06-05 1998-02-24 Shiseido Co Ltd アクリル酸系ポリマー及びこれを配合した乳化組成物
JP2015113296A (ja) 2013-12-10 2015-06-22 花王株式会社 乳化化粧料組成物
US20190053999A1 (en) * 2015-10-09 2019-02-21 Dow Corning Toray Co., Ltd. Film forming agent, and cosmetic composition and cosmetic using same
JP7316604B2 (ja) * 2018-05-23 2023-07-28 株式会社 資生堂 化粧料用オイル増粘剤及び油溶性共重合体

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JP2003212744A (ja) * 2002-01-24 2003-07-30 L'oreal Sa 半結晶性ポリマーを含む、皮膚または毛髪の抗日光保護用組成物
JP2003238348A (ja) * 2002-01-24 2003-08-27 L'oreal Sa 半結晶性ポリマーでゲル化された化粧品組成物
WO2016098456A1 (fr) * 2014-12-19 2016-06-23 株式会社 資生堂 Copolymère et agent gélifiant huileux

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