WO2014103742A1 - Composition vésiculaire réversible et son procédé de fabrication - Google Patents

Composition vésiculaire réversible et son procédé de fabrication Download PDF

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Publication number
WO2014103742A1
WO2014103742A1 PCT/JP2013/083382 JP2013083382W WO2014103742A1 WO 2014103742 A1 WO2014103742 A1 WO 2014103742A1 JP 2013083382 W JP2013083382 W JP 2013083382W WO 2014103742 A1 WO2014103742 A1 WO 2014103742A1
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Prior art keywords
reverse
oil
reverse vesicle
vesicle composition
composition according
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PCT/JP2013/083382
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English (en)
Japanese (ja)
Inventor
亘 堀江
ウルフ オルソン
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ポーラ化成工業株式会社
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Priority claimed from JP2012285269A external-priority patent/JP6239822B2/ja
Priority claimed from JP2013076166A external-priority patent/JP6242582B2/ja
Priority claimed from JP2013076159A external-priority patent/JP6242581B2/ja
Application filed by ポーラ化成工業株式会社 filed Critical ポーラ化成工業株式会社
Publication of WO2014103742A1 publication Critical patent/WO2014103742A1/fr

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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
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/55—Phosphorus compounds
    • A61K8/553—Phospholipids, e.g. lecithin
    • 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
    • A61K8/14—Liposomes; Vesicles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/894—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use
    • 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
    • A61Q1/12—Face or body powders for grooming, adorning or absorbing
    • 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

Definitions

  • the present invention relates to an inverse vesicle, an inverse vesicle composition, an external preparation for skin using the same, and a method for producing them.
  • microencapsulating active ingredients and applying them inside and outside the living body is expected to be applied in the pharmaceutical and food fields as well as in the cosmetics field because of the advantages such as the effectiveness of the active ingredients in the capsules.
  • a vesicle having a phospholipid such as lecithin as a bilayer component is conventionally known.
  • Lecithin is a natural lipid and is widely used as an emulsifier and stabilizer in the cosmetics and food fields.
  • vesicles using lecithin were mainly water-dispersed vesicles in which the hydrophilic groups of phospholipids were oriented outward and dispersed in an aqueous phase.
  • silicone surfactants are those obtained by introducing hydrophilic organic groups into silicone having water repellency, and are applied to various applications because of the ease of molecular design.
  • low HLB silicone surfactants are used as emulsifiers in preparing W / O emulsions.
  • High HLB silicone surfactants are used in hair care products such as O / W emulsions because they can impart slipperiness and antistatic effects to hair.
  • Patent Document 1 describes a reverse vesicle using a sucrose fatty acid ester. It also describes forming a water-in-oil emulsion by the three-phase emulsification method using the reverse vesicle as an emulsifier.
  • Patent Document 2 describes a reverse vesicle composition using sphingosines.
  • Non-Patent Document 1 describes the formation of reverse vesicles containing lecithin, and it is reported that specific lecithins form reverse vesicles in cyclohexane.
  • Non-Patent Document 2 shows that a lecithin having a carbon chain different from the above does not form a coexisting phase of an oil and a lamellar layer necessary for forming a reverse vesicle in the same oil agent.
  • Non-Patent Document 3 describes a reverse vesicle composition using tetraethylene glycol dodecyl ether.
  • Non-Patent Document 4 describes a reverse vesicle composition using a diglycerin fatty acid ester.
  • Non-Patent Document 5 describes a reverse vesicle composition using polyoxyethylene oleyl ether (C18: 1EO50.8).
  • the conventional reverse vesicle described above has been manufactured by mixing the lamellar phase and the oil agent, which are constituents of the reverse vesicle, by applying physical stirring force by hand stirring or ultrasonic irradiation (the above-mentioned patent documents, (See non-patent literature.)
  • the dispersion of the lamella phase into the oil can be performed with a weaker stirring force as the flexibility of the lamella phase increases. It is reported that it is important to swell with an oil component (Non-patent Document 6).
  • Non-Patent Document 1 when lecithin and C4-lecithin are combined in cyclohexane, a reverse vesicle composition can be formed. When using lecithin, it was difficult to form reverse vesicles. In addition, as shown in Non-Patent Document 1, it is necessary to add a salt such as NaCl in order to stably form an inverted vesicle in cyclohexane.
  • a salt such as NaCl
  • the present invention is intended to solve the above-described problems, and an object thereof is to provide a reverse vesicle composition using lecithin.
  • Non-Patent Document 5 in order to form a reverse vesicle using a surfactant having a long hydrophilic group, it is necessary to add an oil solvent having a small molecular weight in order to make the curvature negative. is there.
  • an oil agent having an extremely small molecular weight is difficult to apply to an external preparation for skin due to safety issues. For the above reasons, when examining an external preparation for skin containing reverse vesicles, there are great restrictions on the surfactants that can be selected.
  • the present invention is intended to solve the above-described problems, and an object thereof is to provide a novel reverse vesicle composition.
  • an object thereof is to provide a novel reverse vesicle composition.
  • a surfactant having a large hydrophilic group it is possible to easily obtain a balanced state for forming a bilayer film, and to provide a technique for stably producing a reverse vesicle.
  • the present invention is intended to solve the above-described problems, and an object thereof is to provide a novel method for producing a reverse vesicle composition.
  • an object of the present invention is to provide a production method that facilitates the formation of a reverse vesicle composition as compared with the conventional method when an oil agent having a large molecular weight is used.
  • the first aspect of the present invention for solving the above problems is a reverse vesicle composition containing lecithin and a reverse vesicle composition containing a liquid oil at 25 ° C. having a molecular weight of greater than 114 g / mol.
  • the reverse vesicle of lecithin is stably formed in an oil agent.
  • the stable formation of the reverse vesicle means that the composition containing the reverse vesicle is retained in the composition without phase separation into an oil and a lamellar phase. .
  • the oil agent is selected from silicone oil, hydrocarbon oil, ester oil, natural animal and vegetable oil, and fluorine oil.
  • the said reverse vesicle composition contains the said oil agent 40 mass% or more.
  • a reverse vesicle composition containing 40% by mass of the oil agent has high reverse vesicle formation.
  • the said reverse vesicle contains water.
  • the formation property of the reverse vesicle is improved, and the reverse vesicle composition having higher stability is obtained.
  • a water-soluble component that is an active ingredient such as cosmetics can be held in the reverse vesicle.
  • the inside of a reverse vesicle can also be used as a reaction field.
  • the content of the water in the inverse vesicle composition is not more than 1 mass times the content of the bilayer constituent components including lecithin.
  • the said reverse vesicle contains a water-soluble active ingredient.
  • An inverse vesicle composition containing such an inverse vesicle composition can function as a composition having various activities on biological tissues such as skin.
  • the inverse vesicle composition of the invention is non-emulsifying.
  • the inverse vesicle composition in such a form has high stability.
  • Another aspect of the present invention is an external preparation for skin comprising the reverse vesicle composition of the present invention described above.
  • the external preparation for skin containing such a reverse vesicle composition can hold a water-soluble active ingredient in the reverse vesicle, and thus can stably hold the active ingredient in the preparation.
  • Another aspect of the present invention is a reverse vesicle comprising preparing a mixture by mixing lecithin and a liquid oil component having a molecular weight of greater than 114 g / mol at 25 ° C., and then shaking or stirring the mixture. It is a manufacturing method of a composition. According to the production method of the present invention, a stable composition containing an inverted vesicle containing lecithin can be produced efficiently.
  • Another aspect of the present invention is a method for producing a reverse vesicle, which comprises recovering the reverse vesicle from the reverse vesicle composition described above.
  • Another aspect of the present invention is an external preparation for skin containing the reverse vesicle collected above.
  • this invention which solves the subject regarding the magnitude
  • the reverse vesicle composition of the present invention is such that a reverse vesicle containing a silicone surfactant and water is stably formed in an oil.
  • the stable formation of the reverse vesicle means that the composition containing the reverse vesicle is retained in the composition without phase separation into an oil and a lamellar phase. .
  • the silicone surfactant is selected from polyoxyethylene-modified silicone, polyoxypropylene-modified silicone, polyoxyethylene / polyoxypropylene-modified silicone, and polyglycerin-modified silicone.
  • the silicone surfactant has an HLB of 3 to 13.
  • the oil agent is selected from silicone oil, hydrocarbon oil, ester oil, natural animal and vegetable oil, and fluorine oil.
  • a reverse vesicle composition contains the said oil agent 40 mass% or more.
  • a reverse vesicle composition containing 40% by mass of the oil agent has high reverse vesicle formation.
  • the content mass of the water is not more than 1 times the content mass of the bilayer membrane component containing the silicone surfactant.
  • the said reverse vesicle contains a water-soluble active ingredient.
  • An inverse vesicle composition containing such an inverse vesicle can function as a composition having various activities on biological tissues such as skin.
  • the inverse vesicle composition is non-emulsifying.
  • the inverse vesicle composition in such a form has high stability.
  • Another aspect of the present invention is an external preparation for skin comprising the reverse vesicle composition of the present invention described above.
  • the external preparation for skin containing such a reverse vesicle composition can hold a water-soluble active ingredient in the reverse vesicle, and thus can stably hold the active ingredient in the preparation.
  • Another aspect of the present invention is a reverse vesicle composition
  • a reverse vesicle composition comprising mixing a silicone surfactant, water, and an oil component that is liquid at 25 ° C. to prepare a mixture, and then shaking or stirring the mixture. It is a manufacturing method. According to the production method of the present invention, a stable composition containing an inverted vesicle containing a silicone surfactant can be produced efficiently.
  • Another aspect of the present invention is a method for producing a reverse vesicle, which comprises recovering the reverse vesicle from the reverse vesicle composition described above.
  • Another aspect of the present invention is an external preparation for skin containing the reverse vesicle collected above.
  • the manufacturing method 1 of a reverse vesicle composition for solving the problems related to the method for producing the reverse vesicle composition described above, Dissolving a bilayer component in a volatile solvent to obtain a first isotropic solution; Mixing the first isotropic solution with an oil to obtain a second isotropic solution; Volatilizing the volatile solvent in the second isotropic solution; A volatilization step of forming a reverse vesicle of the bilayer component by volatilization of a volatile solvent; Is a method for producing a reverse vesicle composition.
  • the bilayer component is dissolved in a volatile solvent to form an isotropic solution, then mixed with an oil agent, and then the volatile solvent is volatilized, so that the lamellar is removed from the isotropic solution.
  • a reverse vesicle composition can be obtained by causing a phase transition to.
  • an inverse vesicle composition is produced even in a system in which the bilayer component is difficult to disperse in an oil agent by physical stirring, for example, a system using an oil agent having a large molecular weight. It becomes possible to do.
  • an inverse vesicle composition containing fine inverse vesicles can be easily produced.
  • the volatile solvent is selected from alcohols, hydrocarbons, aromatics, ketones, ethers, esters, volatile silicone oils, and isoparaffins.
  • the oil agent is selected from silicone oil, hydrocarbon oil, ester oil, natural animal and vegetable oil, and fluorine oil.
  • the bilayer component is not particularly limited.
  • lecithin and / or a nonionic surfactant are preferably mentioned.
  • the first isotropic solution may contain water that is not more than 1 times the content of the bilayer component.
  • the second isotropic solution is a two-phase solution in which particles of the first isotropic solution are dispersed in the oil.
  • the volatile solvent and the oil may form one phase or two phases. In the latter case, the particles of the first isotropic solution are dispersed in the oil.
  • the volatile solvent is volatilized under reduced pressure.
  • the present invention relates to a method for producing a reverse vesicle composition
  • a reverse vesicle composition comprising a reverse vesicle containing lecithin and an oil agent which has a molecular weight greater than 114 g / mol and is liquid at 25 ° C.
  • this invention relates to the manufacturing method of the reverse vesicle composition containing a silicone surfactant and water, and the reverse vesicle composition containing an oil agent liquid at 25 degreeC.
  • the present invention also relates to a method for producing an external preparation for skin, comprising mixing the reverse vesicle composition produced by the production method described above with other components.
  • the present invention for solving the problems related to the production method of the reverse vesicle composition described above, Mixing the bilayer component and the oil and heating to obtain an isotropic solution; A cooling step for cooling the isotropic solution; Forming a reverse vesicle of the bilayer component by the cooling; and Is a method for producing a reverse vesicle composition.
  • an isotropic solution is prepared by mixing and heating a bilayer component and an oil agent, and cooling this to cause a phase transition from the isotropic solution to the lamella, thereby causing a reverse vesicle.
  • a composition can be obtained.
  • an inverse vesicle composition is produced even in a system in which the bilayer component is difficult to disperse in an oil agent by physical stirring, for example, a system using an oil agent having a large molecular weight. It becomes possible to do.
  • an inverse vesicle composition containing fine inverse vesicles can be easily produced.
  • the oil agent is selected from silicone oil, hydrocarbon oil, ester oil, natural animal and vegetable oil, and fluorine oil.
  • the bilayer component is not particularly limited.
  • lecithin and / or a nonionic surfactant are preferably mentioned.
  • the isotropic solution may contain water that is not more than 1 times the content of the bilayer component.
  • the heating is performed to a temperature at which the bilayer membrane component and the oil agent form a one-phase isotropic solution.
  • the heating is performed at a temperature at which the bilayer component forms a one-phase isotropic solution with at least one oil agent. It may be done.
  • the cooling is performed by diluting the isotropic solution with a cooling solvent having a temperature lower than that of the isotropic solution.
  • the cooling solvent preferably contains the oil agent.
  • the present invention relates to a method for producing a reverse vesicle composition
  • a reverse vesicle composition comprising a reverse vesicle containing lecithin and an oil agent which has a molecular weight greater than 114 g / mol and is liquid at 25 ° C.
  • this invention relates to the manufacturing method of the reverse vesicle composition containing a silicone surfactant and water, and the reverse vesicle composition containing an oil agent liquid at 25 degreeC.
  • the present invention also relates to a method for producing an external preparation for skin, comprising mixing the reverse vesicle composition produced by the production method described above with other components.
  • the inverse vesicle composition of the present invention has high stability.
  • the reverse vesicle composition of the present invention can contain a water-soluble active ingredient in the reverse vesicle of the reverse vesicle composition, and also uses the water pool in the reverse vesicle as a reaction field. It is also possible.
  • the reverse vesicle composition of the present invention can achieve high safety even when it is assumed to be used for external preparations for skin, foods and the like.
  • the manufacturing method of the reverse vesicle composition of this invention makes it possible to manufacture the said reverse vesicle composition efficiently.
  • a reverse vesicle composition of the present invention it is possible to easily produce a reverse vesicle as compared with a conventional method for producing a reverse vesicle.
  • a reverse vesicle composition is produced using an oil agent having a large molecular weight, it is not necessary to use a physical stirring force as compared with the case of using a conventional method, and productivity is improved in industrial production. It becomes possible.
  • a reverse vesicle composition containing fine reverse vesicles can be produced relatively easily.
  • the vertical axis represents the scattering intensity
  • the horizontal axis represents the size of the scattering vector. It is a figure showing the small angle X-ray-scattering spectrum of a lecithin / dipotassium glycyrrhizinate aqueous solution.
  • the vertical axis represents the scattering intensity
  • the horizontal axis represents the size of the scattering vector.
  • the inverse vesicle composition of the present invention comprises an inverse vesicle containing lecithin and an oil that is liquid at 25 ° C. with a molecular weight of greater than 114 g / mol.
  • each component which comprises this composition is demonstrated.
  • the reverse vesicle in the reverse vesicle composition of the present invention contains lecithin.
  • the lecithin forming the inverted vesicle of the present invention may be extracted from living organisms of plants, animals and microorganisms and purified as desired, or may be synthesized.
  • plant-derived lecithin such as soybean, corn, peanut, rapeseed, and wheat, or animal-derived lecithin such as egg yolk can be used.
  • the lecithin in the present invention includes phosphatidylcholine, phosphatidic acid, phosphatidylglycerol, phosphatidylinositol, phosphatidylethanolamine, phosphatidylmethylethanolamine, phosphatidylserine, bisphosphatidic acid, diphosphatidylglycerol (cardiolipin) and the like.
  • lecithin also includes hydrogenated lecithin, enzymatically decomposed lecithin, enzymatically decomposed hydrogenated lecithin, lysolecithin and the like.
  • the number of carbon atoms of the fatty acid constituting the hydrophobic group portion of lecithin is not particularly limited, and for example, those having 8 to 20 carbon atoms, preferably 16 to 18 carbon atoms can be mainly used.
  • the fatty acid may be saturated or unsaturated.
  • the fatty acid may be linear or branched.
  • the inverse vesicle composition of the present invention is advantageous in that lecithin having an unsaturated fatty acid can be used as a main component. As shown in Examples described later, in a conventionally known reverse vesicle composition using cyclohexane as a solvent, it was difficult to use lecithin having an unsaturated fatty acid as a main component.
  • lecithin can be used in the form of a single kind of the above-mentioned compound or in the form of a mixture of the above-mentioned plural kinds of phospholipids.
  • the composition of lecithin is preferably composed mainly of phosphatidylcholine, for example, 20% by mass or more, and preferably 50% by mass or more is phosphatidylcholine.
  • a commercially available lecithin can be used.
  • the following commercially available products can be used.
  • Resinol S-10 Nikko Chemicals (hydrogenated: ⁇ , PC (phosphatidylcholine) content: 25-30%)
  • Resinol S-10E Nikko Chemicals (hydrogenated: ⁇ , PC content: 75-85%)
  • Resinol S-10EX Nikko Chemicals (hydrogenated: ⁇ , PC content:> 95%)
  • Basis LP-20H Nisshin Oilio Co., Ltd.
  • the reverse vesicle containing lecithin in the present invention is a vesicle of a bilayer membrane in which the fatty acid chain of lecithin described above is oriented outward.
  • the reverse vesicle in the present invention may contain an auxiliary surfactant (nonionic surfactant, ionic surfactant) other than lecithin as a bilayer constituent.
  • lecithin accounts for 60% by mass or more, more preferably 80% by mass or more, of the bilayer constituent components forming the reverse vesicle.
  • the reverse vesicle in the present invention preferably contains water. Water is retained in the bilayer membrane of the reverse vesicle.
  • the stability in the composition of a reverse vesicle improves. It is also possible to retain a water-soluble active ingredient in the bilayer membrane.
  • the active ingredient include ingredients effective for improving skin tissue and promoting health.
  • the reverse vesicle contains water, the content of water is preferably 1 mass times or less of the content of the bilayer constituent component containing lecithin. In addition, the content of water is preferably 0.1 to 0.7 times the content of the bilayer membrane component including lecithin. As a result, the reverse vesicle can be stably held without overflowing excessive water from the bilayer membrane of the reverse vesicle.
  • the liquid oil at 25 ° C. with a molecular weight greater than 114 g / mol used in the present invention constitutes the external and internal phases of the aforementioned reverse vesicle.
  • the oil agent is not particularly limited as long as it has a molecular weight of greater than 114 g / mol and is liquid at 25 ° C.
  • an oil agent having a molecular weight of 114 g / mol or less is used, a coexisting phase of a lamellar phase and an oil agent necessary for forming a reverse vesicle cannot be formed.
  • the solubility of lecithin in the oil agent can be lowered, and a coexisting phase of the lamellar phase and the oil agent can be formed.
  • the molecular weight of the oil agent is preferably 282 g / mol or more.
  • the oil agent has a molecular weight or less capable of realizing fluidity at room temperature.
  • oils used in the present invention include silicone oil, hydrocarbon oil, ester oil, natural animal and vegetable oil, and fluorine oil.
  • silicone oil examples include organopolysiloxanes such as dimethylpolysiloxane, methylphenylpolysiloxane, dimethylsiloxane / methylphenylsiloxane copolymer, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, etc.
  • organopolysiloxanes such as dimethylpolysiloxane, methylphenylpolysiloxane, dimethylsiloxane / methylphenylsiloxane copolymer, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, etc.
  • examples thereof include cyclic siloxane. Among these, the cyclic siloxane described above is preferably used.
  • Hydrocarbon oils include chain and cyclic hydrocarbons such as ⁇ -olefin oligomers, light isoparaffins, light liquid isoparaffins, squalane, liquid paraffin, liquid isoparaffins, hydrogenated isobutene, isooctane, decane, isododecane, isohexadecane, Polybutene, decyltetradecanol and the like can be mentioned.
  • chain and cyclic hydrocarbons such as ⁇ -olefin oligomers, light isoparaffins, light liquid isoparaffins, squalane, liquid paraffin, liquid isoparaffins, hydrogenated isobutene, isooctane, decane, isododecane, isohexadecane, Polybutene, decyltetradecanol and the like can be mentioned.
  • Ester oils include dioctyl succinate, diisobutyl adipate, dioctyl adipate, di (2-heptylundecyl) adipate, diisopropyl sebacate, dioctyl sebacate, dibutyl octyl sebacate, diisostearyl malate, triethyl citrate , Ethylene glycol dioctanoate, neopentyl glycol dioctanoate, propylene glycol dicaprate, neopentyl glycol dicaprate, trimethylolpropane trioctanoate, trimethylolpropane triisostearate, pentaerythritol tetraoleate, ethyl acetate, butyl acetate, amyl acetate Octyldodecyl neopentanoate, cetyl octanoate, is
  • Natural animal and vegetable oils include avocado oil, almond oil, olive oil, wheat germ oil, safflower oil, jojoba oil, macadamia nut oil, cottonseed oil, coconut oil, and the like.
  • Fluorine oil includes perfluoro oils.
  • the reverse vesicle composition of the present invention is obtained by forming the above-described reverse vesicle in the above-described oil agent.
  • the upper limit of the content of lecithin in the reverse vesicle composition of the present invention is not particularly limited as long as the reverse vesicle composition can be formed, but is usually 10% by mass, preferably 5% by mass, more preferably 2% by mass. More preferably, it is 1% by mass.
  • the lower limit of the content of lecithin in the reverse vesicle composition of the present invention is preferably 0.001% by mass, more preferably 0.01% by mass, and more preferably 0.1% by mass.
  • the lower limit of the content of the oil agent in the reverse vesicle composition of the present invention is not particularly limited as long as the reverse vesicle composition can be formed, but is preferably 60% by mass, more preferably 80% by mass, and still more preferably 90%. It is 95 mass%, More preferably, it is 95 mass%.
  • the upper limit of the content of the oil agent in the reverse vesicle composition of the present invention is not particularly limited, but is preferably 99.99% by mass, more preferably 99.90% by mass, and more preferably 99.00% by mass.
  • the reverse vesicle composition of the present invention may contain water.
  • the water is preferably held in the reverse vesicle.
  • a part of the water in the composition may form an emulsion together with the oil.
  • the reverse vesicle composition of the present invention is more preferably not an emulsion type. From such a viewpoint, the mass of water in the reverse vesicle composition is preferably equal to or less than that of lecithin. By doing in this way, separation of water from the lamellar phase can be suppressed, and most of the water can be held in the reverse vesicle.
  • the particle size of the reverse vesicle in the reverse vesicle composition of the present invention is preferably 200 ⁇ m or less, more preferably 20 ⁇ m, and even more preferably 2 ⁇ m or less, immediately after preparation. There is an advantage that the smaller the particle diameter is, the more difficult it is to settle in the dispersion. However, the particle size of the inverse vesicle does not particularly affect the stability of the inverse vesicle itself.
  • the particle size of the inverse vesicle can be measured by a dynamic light scattering method or a laser diffraction method.
  • the reverse vesicle composition of the present invention may contain other optional components such as preservatives, thickeners, and fragrances as long as they do not interfere with the formation of the reverse vesicles.
  • the reverse vesicle composition mentioned above can be performed by the method similar to manufacture of the conventional vesicle. That is, it can be produced by mixing the above-mentioned lecithin, an oil agent, and optionally water to prepare a mixture, and then shaking or stirring the mixture. Shaking can be performed using a shaker or the like. Stirring can be performed using an ultrasonic disperser or the like. Moreover, it is more preferable to manufacture the reverse vesicle composition mentioned above by the manufacturing method of the reverse vesicle composition of this invention mentioned later. Confirmation that the reverse vesicle is formed can be confirmed, for example, by performing microscopic observation under polarized light.
  • recovery here contains the concept of concentration.
  • the method in the reverse vesicle composition, after the reverse vesicle is precipitated, the supernatant is removed.
  • the reverse vesicle composition of the present invention contains a reverse vesicle containing a silicone surfactant and water, and an oil agent that is liquid at 25 ° C.
  • each component which comprises this composition is demonstrated.
  • the reverse vesicle in the reverse vesicle composition of the present invention contains a silicone surfactant.
  • the silicone surfactant is a surfactant having a polyorganosiloxane (silicone chain) in a hydrophobic group.
  • the hydrophilic group is preferably selected from polyether or polyglycerin.
  • Preferred examples of the polyether include polyoxyethylene, polyoxypropylene, and oxyethylene / oxypropylene copolymers.
  • the average degree of polymerization of polyoxyethylene or polyoxypropylene, oxyethylene / oxypropylene copolymer, and polyglycerin is, for example, about 8 to 15.
  • the polyorganosiloxane may be linear or branched. A plurality of polyorganosiloxane chains may be cross-linked.
  • the silicone chain may be modified with an alkyl group.
  • the HLB of the silicone surfactant is preferably 3 to 13, more preferably 6 to 10.
  • the silicone surfactant is soluble or dispersible in the oil agent. Moreover, it is preferable that it is a liquid at room temperature.
  • the silicone surfactant can be used in the form of a single kind of the above compound, or in the form of a mixture of plural kinds.
  • silicone surfactants are known as cosmetic raw materials, and any of them can be used.
  • Commercially available silicone surfactants can be used.
  • the following commercially available products can be used.
  • ⁇ SH3772M PEG-12 dimethicone (polyoxyethylene type), HLB: 6, Toray Dow Corning)
  • SH3773M PEG-12 dimethicone (polyoxyethylene type), HLB: 8, Toray Dow Corning)
  • FZ2222 polysilicone-13 (oxyethylene / oxypropylene type), HLB: 6, Toray Dow Corning
  • KF6013 PEG-9 dimethicone ((polyoxyethylene type)
  • HLB 10, Shin-Etsu Silicone
  • KF6100 polyglyceryl 3 disiloxane dimethicone (polyglycerin), Shin-Etsu Silicone
  • the reverse vesicle in the present invention is a bilayer vesicle in which the siloxane chain of the above-described silicone surfactant is oriented outward.
  • the reverse vesicle in the present invention may contain a co-surfactant (nonionic surfactant, ionic surfactant) other than the silicone surfactant as a bilayer constituent.
  • the silicone surfactant preferably accounts for 50% by mass or more, and more preferably 80% by mass or more.
  • the reverse vesicle in the present invention contains water. Water is retained in the bilayer membrane of the reverse vesicle. It is also possible to retain a water-soluble active ingredient in the bilayer membrane. Examples of the active ingredient include ingredients effective for improving skin tissue and promoting health.
  • the content of water is preferably 1 mass times or less of the content of the bilayer constituent component including the silicone surfactant.
  • the water content is preferably 0.05 to 0.7 mass times the content of the bilayer constituent component including the silicone surfactant.
  • Oil agent that is liquid at 25 ° C. The oil agent that is liquid at 25 ° C. used in the present invention constitutes the external and internal phases of the above-described reverse vesicle.
  • the oil agent preferably has a molecular weight or less that can realize fluidity at room temperature.
  • the same oil as described in ⁇ Reverse vesicle composition containing lecithin> can be used.
  • the reverse vesicle composition of the present invention is obtained by forming the above-described reverse vesicle in the above-described oil agent.
  • the upper limit of the content of the silicone surfactant in the reverse vesicle composition of the present invention is not particularly limited as long as the reverse vesicle composition can be formed, but is usually 10% by mass, preferably 5% by mass, and more preferably 2% by mass, more preferably 1% by mass.
  • the lower limit of the content of the silicone surfactant in the reverse vesicle composition of the present invention is preferably 0.01% by mass, and more preferably 0.1% by mass.
  • the water is included.
  • the water is preferably held in the reverse vesicle.
  • a part of the water in the composition may form an emulsion together with the oil.
  • the reverse vesicle composition of the present invention is more preferably not an emulsion type.
  • the mass of water in the reverse vesicle composition is preferably equal to or less than that of the silicone surfactant.
  • the lower limit of the content of the oil agent in the reverse vesicle composition of the present invention is not particularly limited as long as the reverse vesicle composition can be formed, but is preferably 60% by mass, more preferably 80% by mass, and still more preferably 90%. It is 95 mass%, More preferably, it is 95 mass%.
  • the upper limit of the content of the oil agent in the reverse vesicle composition of the present invention is not particularly limited, but is preferably 99.99% by mass, more preferably 99.90% by mass, and more preferably 99.00% by mass.
  • the particle size of the reverse vesicle in the reverse vesicle composition of the present invention is preferably 200 ⁇ m or less, more preferably 20 ⁇ m, and even more preferably 2 ⁇ m or less, immediately after preparation. There is an advantage that the smaller the particle diameter is, the more difficult it is to settle in the dispersion. However, the particle size of the inverse vesicle does not particularly affect the stability of the inverse vesicle itself.
  • the particle size of the inverse vesicle can be measured by a dynamic light scattering method or a laser diffraction method.
  • the reverse vesicle composition of the present invention may contain other optional components such as preservatives, thickeners, and fragrances as long as they do not interfere with the formation of the reverse vesicles.
  • the reverse vesicle composition containing the silicone surfactant described above can be produced in the same manner as the production of conventional vesicles, as is the case with the reverse vesicle composition containing lecithin. it can. Moreover, it is more preferable to manufacture the reverse vesicle composition mentioned above by the manufacturing method of the reverse vesicle composition of this invention mentioned later. Confirmation that the reverse vesicle is formed can be confirmed by, for example, microscopic observation.
  • recovery here contains the concept of concentration.
  • the method in the reverse vesicle composition, after the reverse vesicle is precipitated, the supernatant is removed.
  • the reverse vesicle composition containing the lecithin or silicone surfactant of the present invention can be used as a raw material for the skin external preparation.
  • the reverse vesicle composition containing the lecithin or silicone surfactant of the present invention can be used as it is as a skin external preparation.
  • the external preparation for skin containing such a reverse vesicle composition can hold a water-soluble active ingredient in the reverse vesicle, and thus can stably hold the active ingredient in the preparation.
  • water-soluble active ingredients include tranexamic acid, glycyrrhizic acid and salts thereof, ascorbic acid, ascorbic acid phosphate ester, 3-O-ethylascorbic acid, ascorbic acid glucoside, and ascorbic acids such as salts thereof.
  • Ursolates such as arbutin, potassium ursolate phosphate, vitamin B such as pyridoxine, riboflavin or salts thereof, hyaluronic acid or salts thereof, fucoidan, sulfated trehalose or salts thereof, trehalose, amino acids and amino acid derivatives,
  • Preferred examples include esculetin glycosides, plant extracts (including liquid and solid forms) and the like.
  • the reverse vesicle composition of the present invention is particularly preferably used as a raw material for cosmetics.
  • the reverse vesicle composition of the present invention can be used as a skin external preparation in the form of lotion or oil as it is.
  • the reverse vesicle composition of the present invention can be used as a skin external preparation in the form of a lotion or cream by mixing with other components and emulsifying as necessary.
  • it can also be set as powder type cosmetics by mixing the reverse vesicle composition of this invention with the raw material powder of cosmetics.
  • Step of obtaining first isotropic solution In the production method of the present invention, first, the bilayer membrane component 1 is dissolved in the volatile solvent 2 to obtain the first isotropic solution 3.
  • the bilayer component indicates a component of the bilayer that constitutes the reverse vesicle.
  • any amphiphilic substance is not particularly limited, and any of an ionic surfactant and a nonionic surfactant can be used.
  • lecithin which is an amphoteric surfactant is used.
  • Nonionic surfactants can also be preferably used.
  • silicone surfactants, polyoxyethylene alkyl ethers, sucrose fatty acid esters, sphingosines, fatty acids and the like can be preferably used.
  • the production method of the present invention is effective when lecithin is used which has a rigid bimolecular film and is difficult to form reverse vesicles by conventional physical agitation.
  • nonionic surfactants such as lecithin and silicone surfactant are preferably used from the viewpoint of safety.
  • the lecithin or silicone surfactant comprises ⁇ an inverse vesicle composition comprising lecithin> or ⁇ a silicone surfactant.
  • Various lecithins or silicone surfactants described in the column “Reverse Vesicle Composition> can be used without limitation.
  • lecithin When lecithin is mainly used, it can be combined with other auxiliary surfactants (nonionic surfactants, ionic surfactants). In this case, it is preferable that lecithin accounts for 60% by mass or more, more preferably 80% by mass or more, among the bilayer components forming the reverse vesicle.
  • Examples of the volatile solvent for dissolving the above-described bilayer component include alcohols such as methanol, ethanol, propanol, and isopropanol, hydrocarbons such as pentane, hexane, and cyclopentane, aromatics such as benzene, acetone, and the like. And volatile silicone oils such as ketones, ethers, esters and decamethylpentasiloxane, fluorocarbons, isoparaffins and the like. Of these, ethanol, propanol, acetone and the like are preferably used.
  • the content of the bilayer component in the first isotropic solution may be in a range where the bilayer component is sufficiently dissolved.
  • the content of the bilayer component can be 10 to 90% by mass. This is because when the amount is less than 10% by mass, the volatilization time of the volatile solvent may become long, and when it exceeds 90% by mass, the solution becomes viscous and may be difficult to dissolve.
  • the first isotropic solution may contain water. Since the production method of the present invention is intended to form an inverted vesicle without relying on conventional physical agitation, the presence of water is not necessary for the purpose of assisting dispersion by physical agitation, but rather there is little water. It can be said that it is useful in the system. However, in the formation of inverted vesicles by volatilization of the volatile solvent, the presence of water may assist the formation of a bilayer. From these viewpoints, the present invention may contain water having a mass of 1 or less that of the bilayer membrane component. In this case, the bilayer component can be mixed with water and mixed with a volatile solvent (FIG. 1 (a)). Of course, a bilayer component, water, and a volatile solvent may be mixed.
  • the bilayer membrane component 1 is dissolved in the volatile solvent 2 to prepare a first isotropic solution 3.
  • This preparation can be performed by ordinary mixing and stirring.
  • the first isotropic solution 3 obtained by dissolving the bilayer membrane component 1 in the volatile solvent 2 is in a state where the bilayer membrane component 1 is monodispersed in the volatile solvent 2 or in the volatile solvent 2. In this state, aggregates such as reverse micelles of the bilayer membrane component 1 are formed (FIG. 1B).
  • Such an isotropic solution has a high fluidity and is easy to mix with a subsequent oil agent.
  • Step of obtaining a second isotropic solution In the production method of the present invention, subsequently, the first isotropic solution 3 obtained above is mixed with an oil agent 4 to obtain a second isotropic solution. Get 5.
  • the same oil as described in ⁇ Reverse vesicle composition containing lecithin> can be used.
  • the oil agent is not particularly limited as long as it can be mixed with the first isotropic solution, but a liquid oil agent at 25 ° C. can be preferably used.
  • the mixing ratio of the first isotropic solution and the oil agent can be set such that the content of the bilayer component in the manufactured reverse vesicle composition is 0.1 to 10% by mass. .
  • an isotropic solution (second isotropic solution) 5 in which the bilayer membrane component 1 is dispersed in the oil agent 4 can be obtained.
  • the form of dispersion of the bilayer membrane component in the oil agent varies depending on the solubility of the volatile solvent used in the oil agent.
  • the first isotropic solution 3 is compatible with the oil agent to form a one-phase solution. That is, the bilayer component 1 contained in the first isotropic solution 3 is present in a monodispersed state or a state in which aggregates such as reverse micelles are formed in the one-phase solutions 2 and 4. (FIG. 1 (c)).
  • the first isotropic solution 3 is not compatible with the oil agent 4 and forms a two-phase solution. That is, the particles 31 of the first isotropic solution 3 are dispersed in the continuous phase of the oil agent 4 (FIG. 1D). As shown in FIG. 1 (d2), the particles 31 are in a state where the bilayer component 1 is monodispersed in the volatile solvent 2, or an aggregate such as a reverse micelle of the bilayer component 1 in the volatile solvent 2. It is in the state which formed. This state can be easily formed by a normal shaking or stirring operation in the mixing step.
  • the component that is insoluble in the oil agent is dissolved in a volatile solvent, and the component that is soluble in the oil agent It is also possible to dissolve these in an oil and mix them.
  • Step of volatilizing volatile solvent In the production method of the present invention, subsequently, the volatile solvent 2 is volatilized from the second isotropic solution 5 obtained by the above operation.
  • Volatilization of the volatile solvent can be performed by vaporizing the volatile solvent by reducing the pressure by a conventional method. Moreover, it is possible to carry out by heating a liquid mixture to the temperature which a volatile solvent vaporizes. Volatilization is preferably performed under reduced pressure. Moreover, when heating, it heats below the temperature which can maintain a lamellar phase (reverse vesicle), ie, below the temperature which does not phase-transform.
  • the first isotropic solution is sufficiently dispersed in the oil by shaking or stirring, and then this step is entered. Is preferred. It is also preferable to apply a stirring force during volatilization from the viewpoint of forming fine reverse vesicles.
  • the second isotropic solution 5 is phase-transduced, and the inverse vesicle composition 8 in which the inverse vesicle 7 is dispersed in the oil agent 4 can be obtained (FIG. 1). (E)).
  • the state of the formed reverse vesicle may be a single layer or a multilayer. Confirmation that the reverse vesicle is formed can be confirmed, for example, by performing microscopic observation under polarized light.
  • the particle size of the reverse vesicle in the reverse vesicle composition produced in this manner is, for example, 200 ⁇ m or less, 20 ⁇ m in a more preferable form, and 2 ⁇ m or less in a more preferable form immediately after the production.
  • the particle size of the inverse vesicle does not particularly affect the stability of the inverse vesicle itself.
  • the particle size of the inverse vesicle can be measured by a dynamic light scattering method or a laser diffraction method.
  • the reverse vesicle composition of the present invention may contain other optional components such as preservatives, thickeners, and fragrances as long as they do not interfere with the formation of the reverse vesicles.
  • recovery here contains the concept of concentration.
  • the method in the reverse vesicle composition, after the reverse vesicle is precipitated, the supernatant is removed.
  • the inverse vesicle composition can be produced by the following method.
  • Step of obtaining an isotropic solution first, a mixture obtained by mixing the bilayer membrane component 1 and the oil agent 2 is heated to obtain the isotropic solution 3.
  • the lamella (L ⁇ ) of the bilayer membrane component 1 is dissolved in the oil agent 2 (L1) at this time, thereby forming a one-phase isotropic solution 3 (L1).
  • the bilayer component indicates a component of the bilayer that constitutes the reverse vesicle.
  • any amphiphilic substance is not particularly limited, and any of an ionic surfactant and a nonionic surfactant can be used.
  • lecithin which is an amphoteric surfactant is used.
  • Nonionic surfactants can also be preferably used.
  • silicone surfactants, polyoxyethylene alkyl ethers, sucrose fatty acid esters, sphingosines, fatty acids and the like can be preferably used.
  • the production method of the present invention is extremely effective in the case of using lecithin in which the bilayer membrane is rigid and it is difficult to form reverse vesicles by conventional physical stirring.
  • nonionic surfactants such as lecithin and silicone surfactant are preferably used from the viewpoint of safety.
  • the lecithin or silicone surfactant comprises ⁇ an inverse vesicle composition comprising lecithin> or ⁇ a silicone surfactant.
  • Various lecithins or silicone surfactants described in the column “Reverse Vesicle Composition> can be used without limitation.
  • the mixture obtained by mixing the bilayer component with the oil is heated.
  • the said bilayer membrane component and oil agent can also be mixed, heating.
  • an oil agent which is liquid at 25 ° C. can be preferably used.
  • the same oil as described in ⁇ Reverse vesicle composition containing lecithin> can be used. Only 1 type may be used for an oil agent, and 2 or more types may be mixed and used for it. Moreover, when mixing 2 or more types, you may combine the oil agent which mutually melt
  • the mixing ratio of the bilayer membrane component and the oil agent can be set such that the content of the bilayer membrane component in the manufactured reverse vesicle composition is 0.1 to 10% by mass.
  • Heating may be performed until the lamella (FIG. 2A) of the bilayer component 1 undergoes phase transition and the mixture becomes an isotropic solution. Whether or not it is an isotropic solution can be determined by observing the solution through a polarizing plate. Further, the isotropic solution obtained by heating may be one-phase or two-phase, but it is more preferable to heat it until it becomes one-phase (see FIG. 2B, L1). In addition, when the said oil agent contains 2 or more types of oil agents, it is preferable that the said bilayer membrane component is performed to the temperature which forms a one-phase isotropic solution with at least 1 type of the said oil agent.
  • the isotropic solution is one-phase or two-phase can be distinguished by observing the presence or absence of separation by leaving it at a constant temperature, or by measuring the light transmittance of the solution.
  • the phase transition temperature of the mixture varies depending on the combination of the bilayer component and the oil used. Therefore, the heating temperature may be adjusted in consideration of the phase transition temperature according to these combinations. For example, when lecithin is used as a bilayer component and squalane is used as an oil agent, a phase transition from a lamellar phase to a two-phase isotropic solution is observed at around 65 ° C., and a two-phase is observed at around 90 ° C. A phase transition from an isotropic solution to a one-phase isotropic solution is seen.
  • the heating temperature in this case is preferably 65 ° C. or higher, more preferably 90 ° C. or higher.
  • the isotropic solution 3 obtained by heating the mixture of the bilayer membrane component 1 and the oil agent 2 is in a state where reverse micelles of the bilayer membrane component 1 are formed in the oil agent 2 (FIG. 2 (b)).
  • the heating is performed until a one-phase isotropic solution is obtained.
  • the heating is performed until the two-phase isotropic solution (L1 + L2) as shown in FIG. 2C is obtained. Form may be sufficient.
  • the highly viscous isotropic solution (L2) containing the reverse-like micelles of the bilayer membrane component 1 in the oil agent 2 is phase-separated from the oil agent (L1).
  • L1 the highly viscous isotropic solution
  • the mixture of the bilayer membrane component and the oil agent may further contain water. Since the production method of the present invention is intended to form an inverted vesicle without relying on conventional physical agitation, the presence of water is not necessary for the purpose of assisting dispersion by physical agitation, but rather there is little water. It can be said that it is useful in the system. However, in the formation of inverted vesicles by cooling, which will be described later, the presence of water may assist the formation of a bilayer. From these viewpoints, the present invention may contain water having a mass of 1 or less that of the bilayer membrane component. The smaller the water content, the lower the transition temperature to the isotropic solution. Therefore, when the production efficiency in the present invention is taken into consideration, it is advantageous that the water content is small.
  • the cooling method is not particularly limited, and examples thereof include a method of placing the isotropic solution at a temperature below room temperature and a method of cooling with a refrigerant. Moreover, it can cool by mixing the dilution solvent of temperature lower than the isotropic solution mixed. For example, you may mix the cooled oil agent as a dilution solvent.
  • the cooling temperature may be equal to or lower than the temperature at which the isotropic solution undergoes phase transition and the coexisting phase of the lamellar liquid crystal and the oil agent is formed. As a guide, cooling to about room temperature can be mentioned.
  • the isotropic solution forms an isotropic solution containing reverse micelles (FIG. 2B).
  • a highly viscous isotropic solution containing reverse string micelles is phase-separated (FIG. 2 (c)), and finally the inverted vesicle 4 is formed. (FIG. 2 (d)). Confirmation that the reverse vesicle is formed can be confirmed, for example, by performing microscopic observation under polarized light.
  • the particle size of the reverse vesicle in the reverse vesicle composition produced in this manner is, for example, 200 ⁇ m or less, 20 ⁇ m in a more preferable form, and 2 ⁇ m or less in a more preferable form in a state immediately after preparation.
  • the particle size of the inverse vesicle does not particularly affect the stability of the inverse vesicle itself.
  • the particle size of the inverse vesicle can be measured by a dynamic light scattering method or a laser diffraction method.
  • the reverse vesicle composition of the present invention may contain other optional components such as preservatives, thickeners, and fragrances as long as they do not interfere with the formation of the reverse vesicles.
  • recovery here contains the concept of concentration.
  • the method in the reverse vesicle composition, after the reverse vesicle is precipitated, the supernatant is removed.
  • the reverse vesicle composition manufactured by the above-described reverse vesicle composition manufacturing methods 1 and 2 of the present invention can be used as a raw material for an external preparation for skin.
  • the reverse vesicle composition produced by such a method can be used as a skin external preparation as it is.
  • the external preparation for skin include pharmaceuticals and cosmetics, and it is particularly preferable to use cosmetics.
  • the reverse vesicle composition can be used as a skin external preparation in the form of lotion or oil as it is or with optional components added.
  • the reverse vesicle composition can be used as a skin external preparation in the form of a lotion or cream by mixing with other components and emulsifying as necessary.
  • it can also be set as a powder type cosmetic by mixing the said reverse vesicle composition with the raw material powder of cosmetics.
  • Test example 1 Each component was mixed with the composition shown in Table 1, and the lamellar phase was dispersed in the oil with a chip-type ultrasonic disperser (product name: VCX130 (manufactured by Sonics & Materials)). Thereafter, formation of reverse vesicles was confirmed using a polarizing microscope. For those in which the formation of reverse vesicles was confirmed, ⁇ was entered, and for those in which the formation of reverse vesicles was not confirmed, x was entered.
  • Resinol S-10 manufactured by Nikko Chemicals Co., Ltd.
  • Epikron 200 manufactured by Cargill * Mainly composed of fatty acids having 16 or more carbon atoms, and the molecular weight exceeds 114.
  • Test example 2 It was confirmed that a reverse vesicle was formed with a combination of lecithin and oil different from those in Test Example 1.
  • Table 2 shows the lecithin and oil used. A mixture containing lecithin 0.8% by mass, water 0.2% by mass, and oil agent 99% by mass was prepared, and the lamellar phase was dispersed in the oil agent using a chip-type ultrasonic disperser. Thereafter, the formation of reverse vesicles was confirmed using a polarizing microscope. For those in which the formation of reverse vesicles was confirmed, ⁇ was entered, and for those in which the formation of reverse vesicles was not confirmed, x was entered. The combinations of lecithin and oil that were not tested are blank in Table 2.
  • Test example 3 We investigated whether crystalline water-soluble active ingredients could inhibit the formation of lamellar phase necessary for the formation of reverse vesicles.
  • three types of crystalline water-soluble active ingredients ascorbic acid 2-glucoside, tranexamic acid, and dipotassium glycyrrhizinate were examined.
  • the solubility of the above three components in water was examined.
  • the results are shown in Table 3.
  • 40% ascorbic acid 2-glucoside aqueous solution, 10% tranexamic acid aqueous solution, and 10% glycylic salicylic acid aqueous solution are the highest concentration aqueous solutions in which each component dissolves. Went.
  • Lecithin (Epicuron 200) and each aqueous solution were mixed at 8: 2, and the presence of a lamellar phase was observed for this mixture using small-angle X-ray scattering.
  • a lamellar phase is formed, a scattering spectrum peculiar to the lamellar phase having a peak ratio of 1: 2 is observed.
  • the measurement results of small angle X-ray scattering of each mixture are shown in FIGS.
  • FIGS. 3 to 5 a scattering spectrum peculiar to the lamellar phase having a peak ratio of 1: 2 was obtained in all the mixtures. That is, it was confirmed that any water-soluble active ingredient was not contained in the lamellar phase without inhibiting the formation of the lamellar phase.
  • a reverse vesicle is formed using the lamellar phase formed as in this test example, a reverse vesicle composition containing a water-soluble active ingredient can be obtained.
  • Example 1 Treatment oil (A) Lecithin 0.4 (A) Water 0.1 (B) Squalane 69.4 (B) Olive oil 20 (B) Jojoba oil 10 (B) Fragrance 0.1
  • Example 2 Cream (A) Dimethicone 31.5 (A) Cyclopentasiloxane (A) (Dimethicone / Vinyl Dimethicone) Crosspolymer 5 (A) Polyether-modified silicone 2 (A) Sorbitan sesquiisostearate 1 (A) Phenoxyethanol 0.5 (B) Water 30 (B) 1,3-butanediol 10 (C) Reverse vesicle solution 10 (C-1) Lecithin 2 (C-2) Squalane 98
  • a reverse vesicle solution (C) was prepared by previously mixing (C-1 and 2) and dispersing with an ultrasonic disperser.
  • the components of group (A) were mixed uniformly, the components of group (B) were mixed, and an emulsion was formed using a homogenizer. Thereafter, the emulsion and (C) prepared in advance were mixed by hand stirring. As a result, a cream containing reverse vesicles was produced.
  • Example 3 Sunscreen cosmetics
  • Cyclopentasiloxane 26.7 A) Polyether-modified silicone 3
  • A) 40% hydrophobized fine particle titanium oxide slurry * 15 A) 40% hydrophobized fine particle zinc slurry * 10 * Dispersion medium: cyclopentasiloxane (B) water 30 (B) 1,3-BG 5 (B) Methylparaben 0.3
  • a reverse vesicle solution (C) was prepared in the same manner as in Example 1 using (C-1 to 3) in advance.
  • the components of group (A) were uniformly mixed by hand stirring and heated to 80 ° C. What was heated and stirred at 80 degreeC of the component of (B) group was added there, and it emulsified with the homogenizer. When the emulsion was cooled and reached 35 ° C., the emulsion and the previously prepared (C) were mixed by hand stirring. As a result, a sunscreen cosmetic containing reverse vesicles was produced.
  • Example 4 Emulsion type foundation
  • Cyclopentasiloxane 24.2 (A) Diphenylsiloxyphenyl trimethicone 10 (A) Polyether-modified silicone 4 (A) Ethylhexyl methoxycinnamate 5 (A) Diethylaminohydroxybenzoyl hexyl benzoate 0.5 (B) Pigment dye (titanium oxide, iron oxide) 10 (C) Organically modified bentonite 1 (D) Water 30 (D) Glycerin 10 (D) Methylparaben 0.3 (E) Reverse vesicle solution 5 (E-1) Lecithin 1.4 (E-2) Water 0.6 (E-3) Cyclopentasiloxane 98
  • a reverse vesicle solution (E) was prepared in the same manner as in Example 1 using (E-1 to 3) in advance.
  • the components of group (A) were uniformly mixed by hand stirring and heated to 80 ° C.
  • the component of (B) group is disperse
  • the obtained oil phase and (D) group uniformly mixed at 80 ° C. are mixed and emulsified.
  • the emulsion was cooled and reached 35 ° C. the emulsion and (E) prepared in advance were mixed by hand stirring. As a result, an emulsified foundation containing a reverse vesicle was produced.
  • FIG. Powder foundation (A) Silicone-treated pigment dye (titanium oxide, iron oxide) 15 (A) Talc 29.7 (A) Mica 10 (A) Fluorine-treated sericite 10 (A) Silica 10 (A) Methyl methacrylate cross polymer 10 (A) Mica titanium 5 (A) Methylparaben 0.3 (B) Reverse vesicle solution 10 (B-1) Lecithin 3 (B-2) Water 0.3 (B-3) Polyoxyethylene alkyl ether 0.3 (B-4) Dimethicone 40 (B-5) Jojoba oil 56.4
  • a reverse vesicle solution (B) was prepared in the same manner as in Example 1 using (B-1 to 5) in advance. After mixing the components of (A) group and coarsely pulverizing with a pulverizer, (B) was added and mixed with a Henschel mixer. Then, it grind
  • Example 6 Treatment oil (A) Polyoxyethylene-modified silicone (HLB8) * 0.4 (A) Water 0.1 (B) Squalane 69.4 (B) Olive oil 20 (B) Jojoba oil 10 (B) Fragrance 0.1 * SH3773M, HLB: 8, Toray Dow Corning
  • Example 7 Cream (A) Dimethicone 31.5 (A) Cyclopentasiloxane (A) (Dimethicone / Vinyl Dimethicone) Crosspolymer 5 (A) Polyether-modified silicone 2 (A) Sorbitan sesquiisostearate 1 (A) Phenoxyethanol 0.5 (B) Water 30 (B) 1,3-butanediol 10 (C) Reverse vesicle solution 10 (C-1) Polyether-modified silicone (HLB8) * 1.5 (C-2) Water 0.5 (C-3) (Dimethicone / Vinyl Dimethicone) Crosspolymer 10 (C-4) Dimethicone 30 (C-5) Cyclopentasiloxane 58 * SH3773M, HLB: 8, Toray Dow Corning
  • a reverse vesicle solution (C) was prepared in the same manner as in Example 6 using (C-1 to 5) in advance.
  • the components of group (A) were mixed uniformly, the components of group (B) were mixed, and an emulsion was formed using a homogenizer. Thereafter, the emulsion and (C) prepared in advance were mixed by hand stirring. As a result, a cream containing reverse vesicles was produced.
  • FIG. Sunscreen cosmetics (A) Cyclopentasiloxane 26.7 (A) Polyether-modified silicone 3 (A) 40% hydrophobized fine particle titanium oxide slurry * 15 (A) 40% hydrophobized fine particle zinc slurry * 10 * Dispersion medium: cyclopentasiloxane (B) water 30 (B) 1,3-BG 5 (B) Methylparaben 0.3 (C) Reverse vesicle solution 10 (C-1) Block copolymer polyether-modified silicone * 0.9 (C-2) Water 0.1 (C-3) Diphenylsiloxyphenyl trimethicone 99 * FZ2222, POE / POP block copolymer type, HLB: 6, Toray Dow Corning
  • a reverse vesicle solution (C) was prepared in the same manner as in Example 6 using (C-1 to 3) in advance.
  • the components of group (A) were uniformly mixed by hand stirring and heated to 80 ° C. What was heated and stirred at 80 degreeC of the component of (B) group was added there, and it emulsified with the homogenizer. When the emulsion was cooled and reached 35 ° C., the emulsion and the previously prepared (C) were mixed by hand stirring. As a result, a sunscreen cosmetic containing reverse vesicles was produced.
  • Example 9 Emulsification foundation Example 9 Emulsion type foundation (A) cyclopentasiloxane 24.2 (A) Diphenylsiloxyphenyl trimethicone 10 (A) Polyether-modified silicone 4 (A) Ethylhexyl methoxycinnamate 5 (A) Diethylaminohydroxybenzoyl hexyl benzoate 0.5 (B) Pigment dye (titanium oxide, iron oxide) 10 (C) Organically modified bentonite 1 (D) Water 30 (D) Glycerin 10 (D) Methylparaben 0.3 (E) Reverse vesicle solution 5 (E-1) Block copolymer polyether-modified silicone (HLB6) * 1.6 (E-2) Block copolymer polyether-modified silicone (HLB3) * 0.1 (E-3) Water 0.3 (E-4) (Dimethicone / Vinyl Dimethicone) Crosspolymer 10 (E-5) Dimethicone 30 (E-
  • a reverse vesicle solution (E) was prepared in the same manner as in Example 6 using (E-1 to 6) in advance.
  • the components of group (A) were uniformly mixed by hand stirring and heated to 80 ° C.
  • the component of (B) group is disperse
  • the obtained oil phase and (D) group uniformly mixed at 80 ° C. are mixed and emulsified.
  • the emulsion was cooled and reached 35 ° C. the emulsion and (E) prepared in advance were mixed by hand stirring. As a result, an emulsified foundation containing a reverse vesicle was produced.
  • Example 10 Powder foundation (A) Silicone-treated pigment dye (titanium oxide, iron oxide) 15 (A) Talc 29.7 (A) Mica 10 (A) Fluorine-treated sericite 10 (A) Silica 10 (A) Methyl methacrylate cross polymer 10 (A) Mica titanium 5 (A) Methylparaben 0.3 (B) Reverse vesicle solution 10 (B-1) Polyglycerin-modified silicone * 1.4 (B-2) Water 0.6 (B-3) Dimethicone 98 * KF6100, Shin-Etsu Silicone
  • a reverse vesicle solution (B) was prepared in the same manner as in Example 6 using (B-1 to 3) in advance. After mixing the components of (A) group and coarsely pulverizing with a pulverizer, (B) was added and mixed with a Henschel mixer. Then, it grind
  • an inverse vesicle composition was produced by the following method. That is, for samples A to D, a mixture of bilayer components and water (lamellar mixture) was dissolved in a volatile solvent to prepare an intermediate solution (first isotropic solution). Subsequently, this intermediate solution was mixed with an oil agent to obtain a mixed solution. This solution formed two phases. Subsequently, this mixed solution was stirred with a vortex mixer for 1 minute to obtain a dispersion (second isotropic solution) in which the intermediate solution was dispersed in the oil, and then heated to 35 ° C. in a reduced pressure oven. Dry until volatile solvent is gone.
  • sample E a mixture of the bilayer component and water was mixed with an oil agent, and the mixed solution was stirred with a vortex mixer under the same conditions as described above.
  • formation of the reverse vesicle was confirmed using the polarization microscope.
  • ⁇ was entered, and for those in which the formation of reverse vesicles was not confirmed, x was entered.
  • an inverted vesicle composition can be produced by applying a stronger stirring force using an ultrasonic disperser or the like.
  • the production method of the present invention can produce a reverse vesicle composition without requiring a strong stirring force by such an ultrasonic disperser, and is useful in this respect when assuming industrial production. It can be said that there is.
  • the oil agent with a larger molecular weight than the oil agent used in the present Example it is thought that the manufacturing method of this invention becomes very useful.
  • Example 11 Treatment oil (A) Lecithin 0.4 (A) Water 0.1 (A) Ethanol 0.2 (B) Squalane 69.4 (B) Olive oil 20 (B) Jojoba oil 10 (B) Fragrance 0.1
  • Example 12 Cream (A) Dimethicone 31.5 (A) Cyclopentasiloxane (A) (Dimethicone / Vinyl Dimethicone) Crosspolymer 5 (A) Polyether-modified silicone 2 (A) Sorbitan sesquiisostearate 1 (A) Phenoxyethanol 0.5 (B) Water 30 (B) 1,3-butanediol 10 (C) Reverse vesicle solution 10 (C-1) Lecithin 2 (C-2) Propanol 2 (C-3) Squalane 98
  • a reverse vesicle solution (C) was prepared in the same manner as in Example 11.
  • the components of group (A) were mixed uniformly, the components of group (B) were mixed, and an emulsion was formed using a homogenizer. Thereafter, the emulsion and (C) prepared in advance were mixed by hand stirring. As a result, a cream containing reverse vesicles was produced.
  • Example 13 Sunscreen cosmetics
  • Cyclopentasiloxane 26.7 A) Polyether-modified silicone 3
  • A) 40% hydrophobized fine particle titanium oxide slurry * 15 A) 40% hydrophobized fine particle zinc slurry * 10 * Dispersion medium: cyclopentasiloxane (B) water 30 (B) 1,3-BG 5 (B) Methylparaben 0.3
  • a reverse vesicle solution (C) was prepared in the same manner as in Example 11 using (C-1 to 4) in advance.
  • the components of group (A) were uniformly mixed by hand stirring and heated to 80 ° C. What was heated and stirred at 80 degreeC of the component of (B) group was added there, and it emulsified with the homogenizer. When the emulsion was cooled and reached 35 ° C., the emulsion and the previously prepared (C) were mixed by hand stirring. As a result, a sunscreen cosmetic containing reverse vesicles was produced.
  • Example 14 Emulsion type foundation
  • Cyclopentasiloxane 24.2 (A) Diphenylsiloxyphenyl trimethicone 10 (A) Polyether-modified silicone 4 (A) Ethylhexyl methoxycinnamate 5 (A) Diethylaminohydroxybenzoyl hexyl benzoate 0.5 (B) Pigment dye (titanium oxide, iron oxide) 10 (C) Organically modified bentonite 1 (D) Water 30 (D) Glycerin 10 (D) Methylparaben 0.3 (E) Reverse vesicle solution 5 (E-1) Lecithin 1.4 (E-2) Water 0.6 (E-3) Ethanol 3 (E-4) Cyclopentasiloxane 98
  • a reverse vesicle solution (E) was prepared in the same manner as in Example 11 using (E-1 to 4) in advance.
  • the components of group (A) were uniformly mixed by hand stirring and heated to 80 ° C.
  • the component of (B) group is disperse
  • the obtained oil phase and (D) group uniformly mixed at 80 ° C. are mixed and emulsified.
  • the emulsion was cooled and reached 35 ° C. the emulsion and (E) prepared in advance were mixed by hand stirring. As a result, an emulsified foundation containing a reverse vesicle was produced.
  • Example 15 Powder Foundation (A) Silicone-treated pigment dye (titanium oxide, iron oxide) 15 (A) Talc 29.7 (A) Mica 10 (A) Fluorine-treated sericite 10 (A) Silica 10 (A) Methyl methacrylate cross polymer 10 (A) Mica titanium 5 (A) Methylparaben 0.3 (B) Reverse vesicle solution 10 (B-1) Lecithin 3 (B-2) Water 0.3 (B-3) Acetone 1 (B-4) Polyoxyethylene alkyl ether 0.3 (B-5) Dimethicone 40 (B-6) Jojoba oil 56.4
  • a reverse vesicle solution (B) was prepared in the same manner as in Example 1 using (B-1 to 6) in advance. After mixing the components of (A) group and coarsely pulverizing with a pulverizer, (B) was added and mixed with a Henschel mixer. Then, it grind
  • the manufacturing method 2 of a reverse vesicle composition was manufactured with the composition shown in Table 6 by the following method. That is, for Samples A to D, the bilayer component, water, and squalane were mixed at the ratio shown in Table 4 and heated to the heating temperature shown in Table 4. It was confirmed through the polarizing plate that all of the obtained solutions were isotropic solutions. The number of phases was determined by allowing the sample to stand for a long time while maintaining a constant temperature to obtain an equilibrium state or observing whether the sample had turbidity. Subsequently, the heated solution was allowed to stand in a cooling chamber having a cooling temperature shown in Table 4 and cooled.
  • each sample was cooled to a temperature at which it transitioned from the isotropic solution to the lamellar phase.
  • sample E after preparing an isotropic solution in which the concentration of the mixture of lecithin and water was twice that of samples A to D, 0 ° C. squalane was finally mixed to the ratio shown in Table 4 did.
  • sample F the mixture of a bilayer membrane component and water was mixed with the oil agent, and this mixed solution was stirred with the vortex mixer.
  • formation of the reverse vesicle was confirmed using the polarization microscope. For those in which the formation of reverse vesicles was confirmed, ⁇ was entered, and for those in which the formation of reverse vesicles was not confirmed, x was entered.
  • an inverted vesicle composition can be produced by applying a stronger stirring force using an ultrasonic disperser or the like.
  • the production method of the present invention can produce a reverse vesicle composition without requiring a strong stirring force by such an ultrasonic disperser, and is useful in this respect when assuming industrial production. It can be said that there is.
  • the oil agent with a larger molecular weight than the oil agent used in the present Example it is thought that the manufacturing method of this invention becomes very useful.
  • Example 16 Treatment oil lecithin 0.4 Water 0.1 Squalane 69.4 Olive oil 20 Jojoba oil 10 Fragrance 0.1
  • Each component was mixed and heated to 90 ° C., and then cooled to about room temperature in a 0 ° C. cooling chamber. As a result, a treatment oil containing a reverse vesicle (reverse vesicle solution) was produced.
  • Example 17 Cream (A) Dimethicone 31.5 (A) Cyclopentasiloxane (A) (Dimethicone / Vinyl Dimethicone) Crosspolymer 5 (A) Polyether-modified silicone 2 (A) Sorbitan sesquiisostearate 1 (A) Phenoxyethanol 0.5 (B) Water 30 (B) 1,3-butanediol 10 (C) Reverse vesicle solution 10 (C-1) Lecithin 2 (C-2) Squalane 98
  • a reverse vesicle solution (C) was prepared in the same manner as in Example 16 using (C-1, 2).
  • the components of group (A) were mixed uniformly, the components of group (B) were mixed, and an emulsion was formed using a homogenizer. Thereafter, the emulsion and (C) prepared in advance were mixed by hand stirring. As a result, a cream containing reverse vesicles was produced.
  • Example 18 Sunscreen cosmetics
  • Cyclopentasiloxane 26.7 A) Polyether-modified silicone 3
  • A) 40% hydrophobized fine particle titanium oxide slurry * 15 A) 40% hydrophobized fine particle zinc slurry * 10 * Dispersion medium: cyclopentasiloxane (B) water 30 (B) 1,3-BG 5 (B) Methylparaben 0.3
  • a reverse vesicle solution (C) was prepared in the same manner as in Example 16 using (C-1 to 4) in advance.
  • the components of group (A) were uniformly mixed by hand stirring and heated to 80 ° C. What was heated and stirred at 80 degreeC of the component of (B) group was added there, and it emulsified with the homogenizer. When the emulsion was cooled and reached 35 ° C., the emulsion and the previously prepared (C) were mixed by hand stirring. As a result, a sunscreen cosmetic containing reverse vesicles was produced.
  • Example 19 Emulsion type foundation (A) Cyclopentasiloxane 24.2 (A) Diphenylsiloxyphenyl trimethicone 10 (A) Polyether-modified silicone 4 (A) Ethylhexyl methoxycinnamate 5 (A) Diethylaminohydroxybenzoyl hexyl benzoate 0.5 (B) Pigment dye (titanium oxide, iron oxide) 10 (C) Organically modified bentonite 1 (D) Water 30 (D) Glycerin 10 (D) Methylparaben 0.3 (E) Reverse vesicle solution 5 (E-1) Lecithin 1.4 (E-2) Water 0.6 (E-3) Cyclopentasiloxane 18 (E-4) Diphenylsiloxyphenyl trimethicone 80 (A) Cyclopentasiloxane 24.2 (A) Diphenylsiloxyphenyl trimethicone 10 (A) Polyether-modified silicone
  • a reverse vesicle solution (E) was prepared in the same manner as in Example 16 using (E-1 to 4) in advance.
  • the components of group (A) were uniformly mixed by hand stirring and heated to 80 ° C.
  • the component of (B) group is disperse
  • the obtained oil phase and (D) group uniformly mixed at 80 ° C. are mixed and emulsified.
  • the emulsion was cooled and reached 35 ° C. the emulsion and (E) prepared in advance were mixed by hand stirring. As a result, an emulsified foundation containing a reverse vesicle was produced.
  • Example 20 Powder Foundation (A) Silicone-treated pigment dye (titanium oxide, iron oxide) 15 (A) Talc 29.7 (A) Mica 10 (A) Fluorine-treated sericite 10 (A) Silica 10 (A) Methyl methacrylate cross polymer 10 (A) Mica titanium 5 (A) Methylparaben 0.3 (B) Reverse vesicle solution 10 (B-1) Lecithin 3 (B-2) Water 0.3 (B-3) Polyoxyethylene alkyl ether 0.3 (B-4) Cyclopentasiloxane 40 (B-5) Jojoba oil 56.4
  • a reverse vesicle solution (B) was prepared in the same manner as in Example 16 using (B-1 to 5) in advance. After mixing the components of (A) group and coarsely pulverizing with a pulverizer, (B) was added and mixed with a Henschel mixer. Then, it grind
  • the present invention can be applied to the production of cosmetics and foods.

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Abstract

La présente invention concerne une composition vésiculaire réversible stable utilisant de la lécithine. La composition vésiculaire réversible selon l'invention comprend une vésicule réversible contenant de la lécithine et une solution huileuse dont le poids moléculaire dépasse 114 g/mol et qui est liquide à 25 °C.
PCT/JP2013/083382 2012-12-25 2013-12-12 Composition vésiculaire réversible et son procédé de fabrication WO2014103742A1 (fr)

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JP2012-280723 2012-12-25
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JP2012-285269 2012-12-27
JP2012285269A JP6239822B2 (ja) 2012-12-27 2012-12-27 逆ベシクル組成物
JP2013-076166 2013-04-01
JP2013076166A JP6242582B2 (ja) 2013-04-01 2013-04-01 逆ベシクル組成物の製造方法
JP2013076159A JP6242581B2 (ja) 2013-04-01 2013-04-01 逆ベシクル組成物の製造方法
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014141461A (ja) * 2012-12-25 2014-08-07 Pola Chem Ind Inc 逆ベシクル組成物
WO2015093324A1 (fr) * 2013-12-18 2015-06-25 ポーラ化成工業株式会社 Composition pulverulente contenant une poudre formant un composite avec une phase lamellaire, et procede de fabrication de cette composition

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JPH09508415A (ja) * 1994-02-04 1997-08-26 スコーツイア・リピツドテクニク・アクチエボラーグ 親油性担体製剤
JP2000510474A (ja) * 1996-05-10 2000-08-15 ヤマノウチ ユーロープ ベスローテン フェンノートシャップ インスタントベシクル製品
JP2001522795A (ja) * 1997-11-05 2001-11-20 バイヤースドルフ・アクチエンゲゼルシヤフト リポソームの調製法
JP2002531412A (ja) * 1998-12-03 2002-09-24 リポコーア・ホールディング・アクチエボラーグ 脂質キャリヤー中にサイクロスポリンを含む医薬組成物
WO2005073355A1 (fr) * 2004-02-02 2005-08-11 Taiyo Kagaku Co., Ltd. Composition ferrique
WO2009019891A1 (fr) * 2007-08-09 2009-02-12 Kao Corporation Vesicule inversée

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JPH09508415A (ja) * 1994-02-04 1997-08-26 スコーツイア・リピツドテクニク・アクチエボラーグ 親油性担体製剤
JP2000510474A (ja) * 1996-05-10 2000-08-15 ヤマノウチ ユーロープ ベスローテン フェンノートシャップ インスタントベシクル製品
JP2001522795A (ja) * 1997-11-05 2001-11-20 バイヤースドルフ・アクチエンゲゼルシヤフト リポソームの調製法
JP2002531412A (ja) * 1998-12-03 2002-09-24 リポコーア・ホールディング・アクチエボラーグ 脂質キャリヤー中にサイクロスポリンを含む医薬組成物
WO2005073355A1 (fr) * 2004-02-02 2005-08-11 Taiyo Kagaku Co., Ltd. Composition ferrique
WO2009019891A1 (fr) * 2007-08-09 2009-02-12 Kao Corporation Vesicule inversée

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014141461A (ja) * 2012-12-25 2014-08-07 Pola Chem Ind Inc 逆ベシクル組成物
WO2015093324A1 (fr) * 2013-12-18 2015-06-25 ポーラ化成工業株式会社 Composition pulverulente contenant une poudre formant un composite avec une phase lamellaire, et procede de fabrication de cette composition
JP2015134748A (ja) * 2013-12-18 2015-07-27 ポーラ化成工業株式会社 ラメラ相が複合化した粉体を含む粉体組成物とその製造方法

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