WO2010082487A1 - Gélifiant d'huile comprenant des micelles inverses en forme de ver et composition de type gel épaissie - Google Patents

Gélifiant d'huile comprenant des micelles inverses en forme de ver et composition de type gel épaissie Download PDF

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WO2010082487A1
WO2010082487A1 PCT/JP2010/000159 JP2010000159W WO2010082487A1 WO 2010082487 A1 WO2010082487 A1 WO 2010082487A1 JP 2010000159 W JP2010000159 W JP 2010000159W WO 2010082487 A1 WO2010082487 A1 WO 2010082487A1
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oil
gelling agent
composition
component
acid ester
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PCT/JP2010/000159
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Japanese (ja)
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橋崎要
齋藤好廣
田口博之
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学校法人日本大学
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Priority to JP2010546593A priority Critical patent/JP5586026B2/ja
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M123/00—Lubricating compositions characterised by the thickener being a mixture of two or more compounds covered by more than one of the main groups C10M113/00 - C10M121/00, each of these compounds being essential
    • C10M123/02—Lubricating compositions characterised by the thickener being a mixture of two or more compounds covered by more than one of the main groups C10M113/00 - C10M121/00, each of these compounds being essential at least one of them being a non-macromolecular compound
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/10—Foods or foodstuffs containing additives; Preparation or treatment thereof containing emulsifiers
    • 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
    • A61K8/0291—Micelles
    • 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
    • A61K8/042—Gels
    • 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
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/43—Thickening agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/70—Additives characterised by shape, e.g. fibres, flakes or microspheres
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • 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
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/48—Thickener, Thickening system
    • 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
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/006—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions used as thickening agents
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/10—Phosphatides, e.g. lecithin, cephalin
    • C10M2223/106—Phosphatides, e.g. lecithin, cephalin used as thickening agents
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/64—Environmental friendly compositions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy

Definitions

  • the present invention relates to an oil gelling agent for thickening or gelling oil such as animal and vegetable oils, mineral oils, hydrocarbons, fatty acid esters, and the like, and a thickening gel-like composition containing the oil and oil gelling agent Related to things.
  • Oil gelling agents that thicken or gelate oils such as animal and vegetable oils, mineral oils, hydrocarbons, and fatty acid esters are used in various fields such as cosmetics, pharmaceuticals, foods, paints, inks, and lubricating oils.
  • the performance generally required for the oil gelling agent includes that the target oil can be gelled with a small amount of addition, and that the obtained gel is stable over a long period of time. Furthermore, depending on the application, it is required to have high safety for the human body, to produce a gel having thixotropy, and to have a good tactile feel of the obtained gel.
  • oil gelling agents low molecular weight gelling agents (1,2,3,4-dibenzylidene-D-sorbitol, 12-hydroxystearic acid, amino acid derivatives, etc.), polymer gelling agents (polyacrylic acid derivatives) , Dextrin derivatives, etc.) are known.
  • Low-molecular gelling agents self-assemble in oil and form a huge network structure, and the oil becomes non-fluidized to form a gel.
  • high-molecular gelling agents are intertwined in a complex network structure. Forming oil causes gelation of the oil.
  • 1,2,3,4-Dibenzylidene-D-sorbitol a low-molecular gelling agent
  • 12-hydroxystearic acid is commercially available as a gelling agent for waste tempura oil, but lacks thixotropic properties.
  • the gelling agent of an amino acid derivative is hardly soluble in oil, complicated operations such as heating at a high temperature and stirring for a long time are required to dissolve it.
  • such an operation has a problem in that it may cause a change in the quality of other components blended in the gel.
  • a dextrin derivative of a polymer gelling agent needs to be added at a high concentration for gelation, and also causes a “sticky feeling” peculiar to polymers and is not good in use.
  • Polyacrylic acid derivatives show good thickening gelation when added in a small amount, but when used on the skin, a “stickiness” peculiar to polymers is produced, and the feeling of use is not good.
  • Patent Document 1 a gel emulsion (Patent Document 1) containing 1 or 2 kinds of natural surfactants such as lecithin and sucrose fatty acid ester, higher alcohol, glycerin and oil has been proposed. Therefore, there is a problem that dripping or the like is liable to occur and handling property is poor, and if either higher alcohol or glycerin is missing, the effect cannot be obtained.
  • an oil gelling agent that is safe for the human body
  • an agent containing an ⁇ -aminolactam derivative as an active ingredient has been proposed (Patent Document 2).
  • Heating and dissolution are required, and high safety to living bodies and the environment is proposed.
  • an oil gelling agent having excellent gelling ability, excellent usability, and good handling properties has not been obtained.
  • Non-Patent Documents 1-3 There are a few reports of gelation of oil by reverse string micelles (Non-Patent Documents 1-3).
  • the reverse string micelle is a kind of self-assembly formed by a surfactant, and is known to cause gelation in order to form a network structure in oil. Since it has a hydrophilic environment inside the reverse string micelle, it is possible to encapsulate water-soluble drugs, enzymes, etc., and it has a feature not found in the oil gelling agent described above.
  • Non-patent Document 1 A three-component mixed system of lecithin / water / various oils has been reported as a typical system for forming this reverse string micelle (Non-patent Document 1).
  • ethylene glycol, formamide, glycerin, and bile salts (Non-patent Document 3) have only been reported as substitutes for water.
  • lecithin forms reverse spherical micelles or reverse elliptical micelles in oil, but when a small amount of water is added to this, hydrogen bonds to the phosphate groups of lecithin and the interface curvature of the molecular assembly decreases. It is believed that reverse string micelle growth occurs.
  • reverse-like micelles consisting of typical lecithin / water / various oils
  • drugs that are susceptible to hydrolysis are blended. I can't.
  • ethylene glycol and formamide which are substitutes for water, cannot be applied to the human body because they have strong irritation to the skin, eyes, mucous membranes and the like.
  • bile salts are surfactants derived from living organisms, but they may cause inflammation when attached to the skin, eyes, etc., and are highly safe for the living body and the environment, good gelation ability, excellent use feeling, No oil gelling agent that has all the good handling properties has been obtained.
  • the present invention requires an oil gelling agent and a thickened gel-like composition for forming reverse string micelles, which are required to have high safety against living bodies and the environment, excellent usability, and good gelling ability. It is an object of the present invention to provide an oil gelling agent and a thickened gel-like composition using the oil gelling agent.
  • lecithin / sucrose fatty acid ester acts as an oil gelling agent for various oils, and these lecithin / sucrose fatty acid ester / various oils. It is possible to obtain a thickened gel-like composition having a reverse cord-like micelle structure by using a three-component mixed system, and the thickened gel-like composition is extremely safe for the human body and the environment, and has good gelation It has been found that it has performance and long-term stability and can solve the above problems.
  • the present inventors include an oil gelling agent containing lecithin and a sucrose fatty acid ester to form a reverse string-like micelle, and a thickening gel containing the oil gelling agent and various oil components to form a reverse string-like micelle.
  • an oil gelling agent which contains (a) lecithin and (b) sucrose fatty acid ester to form reverse string micelles.
  • sucrose fatty acid ester comprises at least one of sucrose capric acid ester, sucrose lauric acid ester, sucrose myristic acid ester, and sucrose palmitic acid ester
  • sucrose fatty acid ester comprises at least one of sucrose capric acid ester, sucrose lauric acid ester, sucrose myristic acid ester, and sucrose palmitic acid ester
  • the oil gelling agent according to any one of [3].
  • sucrose fatty acid ester is 0 with respect to the total mass of (a) lecithin and (b) sucrose fatty acid ester.
  • a thickened gel-like composition comprising at least the oil gelling agent according to any one of [1] to [5] above and (c) an oil component to form reverse string micelles.
  • the oil gelling agent is contained in an amount of 1% by mass to 70% by mass with respect to the thickened gel composition as a mixing ratio of the oil gelling agent and (c) the oil component.
  • the thickening gel-like composition as described in [7].
  • the oil gelling agent that forms the reverse corded micelle of the present invention changes the type of fatty acid of the sucrose fatty acid ester to be used, as well as the advantages and effects of being environmentally friendly with high safety for living bodies and the environment.
  • HLB hydrophilic / lipophilic balance
  • the resulting thickened gel-like composition has thixotropic properties, is difficult to spill, has good handling properties, and has long-term stability over one year.
  • the transparency of the thickened gel-like composition can be adjusted depending on the oil gelling agent used, the preparation conditions of the thickened gel-like composition, and the like, from transparent to translucent, white turbid, and the application used.
  • it has a hydrophilic environment inside the reverse cord-like micelle structure, and has characteristics not found in conventional thickening gel-like compositions that can contain water-soluble components, drugs, enzymes, and the like.
  • the oil gelling agent of the present invention is a material that can thicken or gel various oil components to form reverse string micelles.
  • the oil gelling agent of the present invention contains (a) lecithin, (b) sucrose fatty acid ester, and when various (c) oil components are added and mixed, it is thickened or gelled to form an inverted cord-like micelle structure. It becomes a viscous gel-like composition.
  • Reverse string-like micelles are a kind of self-assembly formed by a surfactant.
  • the surfactant is an amphiphilic substance having a hydrophilic group and a hydrophobic group in the molecule, and forms a self-assembly in water or oil according to the balance of the groups.
  • the reverse string-like micelle in which the micelle has grown into a cylindrical shape forms a temporary network structure and forms a highly elastic gel.
  • it since it has a hydrophilic environment inside, it is possible to enclose water-soluble components, drugs, enzymes, and the like.
  • the inventors of the present invention have conducted extensive research on reverse string micelles, and as a result, have found that a substance that causes reverse string micelle growth requires two conditions. One is to have two or more functional groups capable of hydrogen bonding to the phosphate group of lecithin, and the second is to have a slight hydrophobicity.
  • the present inventors have found that reverse string-like micelles can be formed from lecithin, sucrose fatty acid ester and various oils.
  • the present inventors have described the structure of the obtained thickened or gel-like preparation, specifically the thickened gel-like preparation formed by mixing lecithin, sucrose myristate and n-decane. Observed.
  • the thickened gel-like preparation is transparent, has no crystal structure, is optically isotropic, and does not show a characteristic pattern as a polarized image. From the scattering curve measured by small angle X-ray scattering (SAXS), since a clear diffraction peak was not obtained, no regular structure was formed, and the thickened gel-like composition of the present invention was an inverted string micelle. It can be said that it forms.
  • the thickened gel composition of the present invention forms a reverse string-like micelle, and thus depends on the oil to be thickened or gelled, but is transparent if the oil itself is transparent. .
  • SAXS measurement was performed using a Nano-STAR manufactured by Bruker AXS, with an X-ray source of CuK ⁇ rays and an output of 45 kV / 120 mA. All SAXS measurements were performed at 25 ° C.
  • FIG. 2 shows a thickened gel composition 1 (sample 1) in which 2% by mass of lecithin, 0.4% by mass of sucrose myristic acid ester, 97.6% by mass of n-decane, 10% by mass of lecithin, Thickened gel composition 2 (sample 2) in which 2% by mass of sucrose myristic acid ester and 88% by mass of n-decane are mixed, 25% by mass of lecithin, 5% by mass of sucrose myristic acid ester, 70% by mass of n-decane 2 shows a scattering curve (relationship between scattering intensity I (q) and scattering vector q) of small-angle X-ray scattering measurement with a thickened gel-like composition 3 (sample 3) mixed with%.
  • Example 1 shows a thickened gel composition 1 in which 2% by mass of lecithin, 0.4% by mass of sucrose myristic acid ester, 97.6% by mass of n-decane, 10% by mass of lec
  • the exact length of the reverse string micelle could not be calculated due to the limitation of the measurement range, but the length (t) of the reverse string micelle is about 500 mm or more from the simulation using the equation (3). It was shown that.
  • J 1 is a first-order Bessel function.
  • the low q-side scattering intensity decreased and the inclination tended to be gentle.
  • a slight peak due to the interparticle interaction is observed at a position where q is about 0.07 ⁇ - 1 . This result shows that in Sample 2 and Sample 3, the amount of reverse string micelle per unit volume in the sample is increased.
  • the thickened gel-like composition obtained by thickening or gelling the oil component using the oil gelling agent of the present invention is similarly formed with reverse string-like micelles in view of the gelation state and physical properties. It can be said.
  • Lecithin as the oil gelling agent of the present invention is a mixture of naturally occurring phospholipids, such as soybean-derived soybean lecithin, egg yolk-derived egg yolk lecithin, purified lecithin with increased purity, enzyme-treated lysolecithin, etc. Modified lecithin can be used.
  • Lecithin is an amphoteric phospholipid having two alkyl chains, and is widely used as a food emulsifier in emulsification of dairy products, reduction in viscosity of chocolate, and in pharmaceutical preparations. Moreover, it is a hydrophobic amphoteric surfactant and has high safety to living bodies and the environment. In the present invention, it is preferable to use soybean lecithin and egg yolk lecithin among lecithins.
  • the (b) sucrose fatty acid ester as the oil gelling agent of the present invention is a nonionic surfactant obtained by esterifying a fatty acid derived from edible fats and oils to the hydroxyl group of sucrose, and is approved as a food additive and is a human body. Safety is also high.
  • the lower limit of the carbon number as the fatty acid is 6 or more, preferably 10 or more, and the upper limit of the carbon number is 24 or less, preferably 18 or less, and more preferably 16 or less. If the number of carbon atoms in the fatty acid is too small, the ability to form micelles may decrease, and thickening or gelation may not occur. If the number of carbon atoms in the fatty acid is too large, the melting point may increase and stability at low temperatures may decrease. .
  • These fatty acids may be used alone or in combination of two or more.
  • sucrose fatty acid ester In the sucrose fatty acid ester, a wide range of HLB (hydrophilic lipophilic balance) types can be obtained by changing the carbon number of the fatty acid.
  • the sucrose fatty acid ester used in the present invention has an HLB of 5 or more and 18 or less, preferably 9 or more and 17 or less, more preferably 11 or more and 16 or less. If the HLB is too low, the hydrogen bonding ability will be reduced, and if the HLB is too high, it will be difficult to solubilize inside the micelle, and thickening or gelation may not occur.
  • fatty acids that form esters include caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, partoleic acid, stearic acid, isostearic acid, oleic acid, Linoleic acid, behenic acid, erucic acid, ricinoleic acid, hydroxystearic acid and the like can be mentioned.
  • capric acid having 10 carbon atoms lauric acid having 12 carbon atoms
  • myristic acid having 14 carbon atoms and palmitic acid having 16 carbon atoms are preferably used.
  • Sucrose fatty acid esters include monoesters to octaesters as the degree of esterification of fatty acids to sucrose.
  • sucrose fatty acid esters of any degree of esterification can be used, and commercially available sucrose fatty acid esters can also be used as they are.
  • the monoester content of commercially available sucrose fatty acid esters is usually 0 to 100% and includes those having a plurality of esterification degrees. In the present invention, the monoester content is preferably 40 to 100%, more preferably 80 to 100%. When the monoester content is reduced, thickening gelation may not occur, or even when thickening gelation occurs, a preferred thickening property may not be obtained.
  • the mixing ratio with (a) lecithin (b) sucrose fatty acid ester constituting the oil gelling agent of the present invention may be in any range as long as it is a mixing ratio capable of forming reverse string micelles.
  • the mass ratio of (b) sucrose fatty acid ester to the total amount of the oil gelling agent varies depending on (c) oil component, but it is expressed as mass% of (b) component / ((a) component + (b) component).
  • the lower limit is 0.1% by mass or more, preferably 1% by mass or more, more preferably 7% by mass or more, and the upper limit is experimentally 70% by mass or less, preferably 60% by mass or less, more preferably 50% by mass. % Or
  • Oil components that can be gelled in the present invention are not particularly limited, and are oils such as animal and vegetable oils, mineral oils, hydrocarbons, and fatty acid esters. Only polar oil, nonpolar oil, or a mixture of polar oil and nonpolar oil may be used.
  • fish oil such as fish oil, liver oil, whale oil, head oil, lard, horse oil, sheep oil, animal oil, vegetable oil such as animal oil, palm oil, palm oil, cacao butter, olive oil, rapeseed oil, linseed oil, etc .
  • Hydrocarbons such as liquid paraffin, isoparaffin, kerosene, heavy oil, isooctane, n-heptane, n-decane and cyclohexane; higher fatty acids such as lauric acid, palmitic acid, stearic acid, oleic acid and behenic acid, isopropyl myristate And fatty acid esters such as 2-octyldodecyl myristate and isopropyl palmitate.
  • These oils can be used singly or as a mixture of two or more.
  • the additive component may be dissolved, dispersed, emulsified, suspended or mixed at a concentration that does not hinder thickening or gelling.
  • additive components include surfactants, ultraviolet absorbers, moisturizers, preservatives, preservatives, bactericides, depending on the application such as cosmetics, pharmaceuticals, foods, paints, inks, and lubricating oils.
  • antioxidants fluidity improvers, fragrances, pigments, enzymes, physiologically active substances, and the like, and examples include organic compounds or inorganic compounds such as titanium oxide, talc, mica, and water.
  • the oil gelling agent When (c) the oil component is gelled with the oil gelling agent containing (a) lecithin (b) sucrose fatty acid ester of the present invention, the oil gelling agent is thickened or gelled with respect to the oil component, and the reverse string Any amount can be mixed as long as it is within the range in which the micelles can be formed.
  • the mixing ratio of the oil component is (a) 1 to 70% by mass of lecithin, preferably 3 to 45% by mass, more preferably 5 to 25% by mass, and (b) 0.1 to 40% by mass of sucrose fatty acid ester. %, Preferably 0.4 to 25% by mass, more preferably 0.8 to 15% by mass, and (c) the oil component is 30 to 99% by mass, preferably 50 to 96% by mass, more preferably 70%. It can be set to -94 mass%.
  • the mixing ratio of the oil gelling agent to the thickened gel-like composition is expressed by mass% of ((a) component + (b) component) / ((a) component + (b) component + (c) component).
  • the lower limit is 1% by mass or more, preferably 4% by mass or more, more preferably 6% by mass or more, and the upper limit is 70% by mass or less, preferably 50% by mass or less, and more preferably 30% by mass.
  • the gel strength can be adjusted by the concentration of the oil gelling agent and the mixing ratio of (a) lecithin and (b) sucrose fatty acid ester.
  • the thickened gel-like composition of the present invention contains (a) lecithin (b) sucrose fatty acid ester, various (c) oil components are added, and other additive components are added as necessary, uniformly. By dissolving, it can be gelled to form an inverted string micelle structure.
  • component an organic solvent solution of lecithin
  • component sucrose fatty acid ester
  • Ingredient After dissolving the sucrose fatty acid ester, the organic solvent is completely evaporated by drying under reduced pressure, and then (c) the required amount of the oil component is added and further stirred overnight, and the container is kept at room temperature for stabilization.
  • the thickening gel-like composition is produced immediately by adding, mixing, and stirring each component, and long-time stirring and standing for stabilizing the gel-like material is appropriately performed as necessary. It only has to be set, and in some cases it is not necessary.
  • Examples of the organic solvent used in preparing the thickened gel composition include lower alcohols such as methanol, ethanol, propanol, and butyl alcohol; polyhydric alcohols such as ethylene glycol and propylene glycol; acetone, 2-butanone, and cyclohequinone.
  • lower alcohols such as methanol, ethanol, propanol, and butyl alcohol
  • polyhydric alcohols such as ethylene glycol and propylene glycol
  • acetone, 2-butanone, and cyclohequinone examples of the organic solvent used in preparing the thickened gel composition.
  • Ketones such as tetrahydrofuran, ethers such as 1,4-dioxane; esters such as ethyl acetate and butyl acetate; amides such as N, N-dimethylformamide and N, N-dimethylacetamide; chloroform and carbon tetrachloride
  • Halogenated hydrocarbons such as dichloromethane, dichloroethane, isopropyl bromide, ethyl bromide, dichlorobenzene, tetrachloroethane, trichloroethane, trichloroethylene, ethylene tetrachloride; water, etc., but it is preferable to use lower alcohols. There. These organic solvents may be used alone or in combination.
  • the thickened gel-like composition of the present invention can be used as various products that exhibit gel-like properties at room temperature as detergents, cosmetics, medicines, foods, deodorants, bath agents, fragrances, deodorizers, and the like.
  • detergents include food detergents, dish detergents, kitchen detergents, facial cleansers, body soaps, shampoos, rinses and the like.
  • Cosmetics include creams, emulsions, lotions, cleansing agents, bath cosmetics, moisturizing cosmetics, blood circulation promoting / massaging agents, pack cosmetics, hair cosmetics, and the like.
  • pharmaceuticals include ointments, molded cataplasms, sustained-release preparation bases, transdermal absorption preparations, drug delivery system carriers, electrophoresis gels, and the like.
  • ingredients used in ordinary general cosmetics can be blended.
  • examples include fragrances, pigments, preservatives, antioxidants, anti-inflammatory agents, ultraviolet absorbers, ultraviolet reflectors, pH adjusters, and various other medicinal ingredients such as hyaluronic acid, allantoin, and the like.
  • the thickened gel-like composition formed by adding and mixing various oils to the oil gelling agent of the present invention has a reverse string-like micelle structure, so it has a hydrophilic environment inside and is a water-soluble component ⁇ It is possible to enclose drugs and enzymes.
  • This reverse-like micelle is a nanometer-scale extremely fine molecular assembly.
  • the polar groups of lecithin and sucrose fatty acid ester molecules face inward, and the hydrophobic groups face outward. Since many strings are gathered together, a hydrophilic environment, that is, a small water pool (water phase) is formed inside.
  • water-soluble substances that can be encapsulated include moisturizers, whitening agents, anti-inflammatory agents, antibacterial agents, hormone agents, vitamins, various amino acids and their derivatives, enzymes, antioxidants, hair restorers, etc. Ingredients.
  • the thickened gel composition formed by adding and mixing various oils to the oil gelling agent of the present invention a water-soluble substance, a water-soluble drug, and an enzyme that are hardly soluble or insoluble in the oil are directly or When the aqueous solution is contacted, mixed and stirred, the water-soluble substance is taken into the reverse string micelle and can be dissolved in the thickening gel.
  • the transparency of the formed thickened gel-like composition can be adjusted according to the oil gelling agent used, the preparation conditions of the thickened gel-like composition, and the like, from transparent to translucent, white turbid, and the application used.
  • the oil gelling agent of the present invention is excellent in gelation ability for various oils, can form a stable gel for a long time even when added at a low concentration, and particularly a gel of higher hydrocarbons has excellent thixotropic properties, and There is no shortcoming such as “stickiness”.
  • the oil gelling agent of the present invention is made of material components such as lecithin and sucrose fatty acid ester that are highly safe and biodegradable for living bodies and the environment, and is environmentally friendly.
  • the oil gelling agent of the present invention is further used in fields other than the above, such as quasi-drugs, inks, paints, lubricating oils, plastics, rubbers, metals, etc., as well as agriculture, fisheries, waste oil treatment, etc. be able to.
  • Examples 1 to 8 (Formulation of thickening gel composition)
  • a component lecithin soybean lecithin product name “L- ⁇ -Phosphatidylcholine (Soy-95%)” manufactured by Avanti Polar Lipids, Inc.
  • component sucrose capric acid ester “Plate” (manufactured by Dojindo Laboratories Co., Ltd.), n-decane (0.774 mPa ⁇ s (25 ° C.) manufactured by Kanto Chemical Co., Ltd.) as component (c) was increased as the composition shown in Table 1.
  • a viscous gel composition was prepared. Examples 1 to 8 were made according to each composition.
  • Preparation of thickened gel composition Preparation of the thickened gel composition was carried out by encapsulating (a) component: lecithin ethanol solution and (b) component: sucrose fatty acid ester in required bottles, respectively, and stirring using a magnetic stirrer. (B) component: After dissolving sucrose fatty acid ester, ethanol is completely evaporated by drying under reduced pressure. (C) The required amount of oil component was added and further stirred overnight, and the bottle was prepared by allowing it to stand in a thermostatic bath at 25 ° C. for several days for equilibration. In the following Examples 9 to 42 and Comparative Examples 1 to 4, the thickening gel composition was prepared by the same preparation means.
  • a thickened gel composition is prepared.
  • the ratio of sucrose capric acid ester in these oil gelling agents, that is, (b) component / ((a) component + (b) component) is 11% by mass to 23% by mass in the thickened gel-like composition.
  • the ratio of the oil gelling agent, that is, ((a) component + (b) component) / ((a) component + (b) component + (c) component) is 12% by mass to 30% by mass.
  • the state of the thickening gel was transparent, both gelled and ⁇ , and the storage stability was also ⁇ .
  • the evaluation results are shown in Table 1.
  • Example 9 to 20 (Formulation of thickening gel composition)
  • b) the component as sucrose laurate, the product name “Ryoto sugar ester L-1695 "(manufactured by Mitsubishi Chemical Foods), n-decane (manufactured by Kanto Chemical Co., Ltd.) as component (c), and a thickened gel-like composition having the composition shown in Table 1 were prepared. . According to each compounding composition, it was set as Examples 9-16.
  • (c) component was changed to cyclohexane (0.828 mPa * s (25 degreeC) by Kanto Chemical Co., Inc.), and the thickening gel-like composition was prepared as a compounding composition shown in Table 2. It was set as Examples 17 and 18 according to each compounding composition.
  • Example 19 And (c) component was changed to liquid paraffin (manufactured by Kanto Chemical Co., Ltd., 146 mPa ⁇ s (25 ° C.)), and a thickening gel-like composition was prepared as a formulation shown in Table 2 to obtain Example 20.
  • component (a): lecithin was 5, 10, 15, 20, 25% by mass
  • component (c): n-decane in required amounts It is used to prepare a thickened gel composition.
  • the ratio of sucrose laurate in these oil gelling agents that is, (b) component / ((a) component + (b) component) is 11% to 25% by mass
  • the oil gel in the thickened gel composition The ratio of the agent ((a) component + (b) component) / ((a) component + (b) component + (c) component) is 6 mass% to 28 mass%.
  • the state of the thickening gel was transparent, both gelled and ⁇ , and the storage stability was also ⁇ .
  • the evaluation results are shown in Table 1.
  • Example 17 to 20 (a) component: lecithin was 10% by mass, (b) component: sucrose laurate, (c) component: cyclohexane, isopropyl palmitate, and liquid paraffin were used.
  • a viscous gel composition is prepared. The ratio of sucrose laurate in these oil gelling agents, (b) component / ((a) component + (b) component) is 7% to 58% by mass, oil gelation in the thickened gel composition The ratio of the agent ((a) component + (b) component) / ((a) component + (b) component + (c) component) is from 11% by mass to 24% by mass. The states of the thickening gel were all gelled, and the storage stability was all excellent except for Example 20, and all were transparent. In component (c) of Example 20, liquid paraffin was separated in a small amount, but it was sufficiently transparent and stable in the usual standard of 3 months, and there was no problem in use. . The evaluation results are shown in Table 2.
  • Example 21 to 33 (Formulation of thickening gel composition)
  • (b) as sucrose myristic ester, trade name “Ryoto Sugar Ester M-1695 "(Mitsubishi Chemical Foods Co., Ltd.), n-decane (manufactured by Kanto Chemical Co., Ltd.) as component (c), and a thickened gel-like composition having the composition shown in Table 2 were prepared.
  • Examples 21 to 29 were made according to the respective composition compositions.
  • Example 30 The component was changed to cyclohexane (made by Kanto Chemical Co., Inc.), and the thickening gel-like composition was prepared as a compounding composition shown in Table 2. It was set as Example 30 and Example 31 according to each compounding composition.
  • (c) component was changed to isopropyl palmitate (manufactured by Wako Pure Chemical Industries, Ltd.), and a thickening gel-like composition was prepared as a blending composition shown in Table 2 to give Example 32, and component (c) was liquid paraffin.
  • a blending composition shown in Table 3 in place of (manufactured by Kanto Chemical Co., Inc.), a thickened gel composition was prepared as Example 33.
  • Example 21 In Examples 21 to 29, (a) component: lecithin was 5, 10, 15, 20, and 25% by mass, (b) component: sucrose myristic acid ester, and (c) component: n-decane, respectively, as required.
  • Examples 30 and 31 were prepared by using a thickened gel composition, and (a) component: lecithin was 10% by mass, (b) component: sucrose myristic acid ester, and (c) component: cyclohexane.
  • Example 32 a thickened gel-like composition was prepared by using (a) component: lecithin at 10% by mass, (b) component: sucrose myristic acid ester, and (c) component: isopropyl palmitate.
  • Example 33 a thickened gel-like composition was prepared by using 10% by mass of lecithin as the component (a), (b) component: sucrose myristic acid ester, and (c) component: liquid paraffin.
  • the mixing ratio is 7% to 58% by mass of the ratio (b) component / ((a) component + (b) component) of the sucrose myristic acid ester in the oil gelling agent.
  • the ratio of the oil gelling agent in the gel composition is 7% to 30% by mass.
  • the thickening gel was transparent, and both gelled and storage stability was good.
  • the gel of Example 32 is thickened ⁇ , but it does not cause any problems in use, and the storage stability of Example 33 is ⁇ small amount separated, but it is a normal guideline. In 3 months, it was sufficiently transparent and stable, and there was no problem in use. The evaluation results are shown in Tables 2 and 3.
  • Example 34 to 42 (Formulation of thickening gel composition)
  • the ratio (b) component / ((a) component + (b) component) of sucrose palmitate in the oil gelling agent was changed from 11% by mass to 33% by mass to increase the viscosity of the gel.
  • the ratio of the oil gelling agent in the composition ((a) component + (b) component) / ((a) component + (b) component + (c) component) was changed from 6 mass% to 30 mass%. is there.
  • Example 34 (a) component: lecithin was 5, 10, 15, 20, and 25% by mass, (b) component: sucrose palmitate ester, and (c) component: n-decane, respectively. Even when the thickened gel-like composition was prepared using the required amount, the state of the thickened gel was transparent, and in both cases, the gelation was excellent and the storage stability was excellent. In Example 34, the gel was in a thickened state, but it was not a problem in use. The evaluation results are shown in Table 3.
  • Example 43 to 46 Preparation of thickened gel composition
  • Preparation of the thickened gel-like composition was carried out in Examples 23, 31, 32, and 33, in which (a) component: lecithin, (b) component: sucrose fatty acid ester, and (c) oil component were enclosed in the required amount bottles, respectively. It was prepared by heating and dissolving at about 60 ° C. and cooling to room temperature. At that time, it was performed in a nitrogen atmosphere to prevent oxidation of lecithin.
  • a thickened gel composition shown in Table 4 a thickened gel composition was prepared. According to each compounding composition, it was set as Examples 43-46.
  • the transmittance was measured at a wavelength of 550 nm using a spectrophotometer (V-530, manufactured by JASCO Corporation). Based on the transmittances of 100 to 90%, 89 to 50%, and 49% or less, they were evaluated as transparent: 1, translucent: 2, white turbidity: 3. The evaluation results are shown in Table 4.
  • the transparency is transparent or translucent, and can provide transparency according to the application used as the thickening gel composition.
  • a thickened gel composition was prepared in the same manner as Comparative Example 1 except that the component (c) was changed to isopropyl palmitate (manufactured by Wako Pure Chemical Industries, Ltd.). Further, a thickened gel composition was prepared as Comparative Example 4 in the same manner as Comparative Example 1 except that the component (c) was changed to liquid paraffin (manufactured by Kanto Chemical Co., Inc.).
  • Comparative Examples 1 to 4 did not use the sucrose fatty acid ester as the component (b), so that the thickening gel was insufficiently formed or could not be formed.
  • Table 3 shows the composition and evaluation results.
  • the oil component (c) n-decane has a viscosity increase of 3 million times at 25 ° C. and 0.774 mPa ⁇ s
  • cyclohexane has a temperature of 25 ° C.
  • the viscosity increased by 2.5 million times
  • isopropyl palmitate the viscosity increased by 6.09 mPa ⁇ s at 25 ° C. by 600,000 times.
  • a tenfold increase in viscosity was easily obtained.
  • the sucrose fatty acid ester of component (b) and the oil component (c) were insufficiently formed or could not be formed. *
  • the oil gelling agent which can form a reverse string-like micelle by the 3 component mixed system of a lecithin / sucrose fatty acid ester / various oil can be provided, and the thickening gel form in which the reverse string-like micelle was formed
  • the composition has a hydrophilic environment inside reverse string micelles and can contain water-soluble components, drugs, enzymes, and the like. Further, by changing the type of fatty acid of the sucrose fatty acid ester to be used, a wide range of HLB (hydrophilic lipophilic balance) types can be obtained, and it can be widely used as oil gelling agents for various cosmetics, pharmaceuticals, foods and the like. Further, the thickened gel composition formed by using the oil gelling agent has thixotropic properties, good handling properties, and good long-term stability.

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Abstract

L'invention concerne un gélifiant d'huile extrêmement sûr vis-à-vis des organismes vivants et de l'environnement, présentant une texture préférée lors de son utilisation ainsi qu'un bon pouvoir gélifiant. L'invention concerne également une composition de type gel épaissie contenant ledit gélifiant d'huile pouvant former des micelles inverses en forme de ver et une composition de type gel épaissie. Une combinaison de lécithine/ester d'acides gras et de saccharose sert de gélifiant d'huile pouvant former des micelles inverses, en forme de ver, de différentes huiles. L'utilisation d'un système mélangeant trois composants, constitué de lécithine/ester d'acides gras et de saccharose/différentes huiles, permet d'obtenir une composition de type gel épaissie présentant une structure de micelles inverses en forme de ver. On peut ainsi obtenir facilement un bon gélifiant d'huile, qui est extrêmement sûr vis-à-vis des êtres humains et de l'environnement, présente une stabilité élevée sur une longue période et présente les propriétés requises pour un gélifiant d'huile, ainsi qu'une composition de type gel épaissie comprenant ledit gélifiant d'huile et un composant huileux, dans laquelle des micelles inverses de type de ver ont été formées.
PCT/JP2010/000159 2009-01-16 2010-01-14 Gélifiant d'huile comprenant des micelles inverses en forme de ver et composition de type gel épaissie WO2010082487A1 (fr)

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WO2013081120A1 (fr) 2011-11-30 2013-06-06 学校法人日本大学 Agent de formation d'organogel lécithine
WO2013176243A1 (fr) * 2012-05-25 2013-11-28 学校法人日本大学 Agent de formation d'organogel de lécithine
US11337906B2 (en) 2018-12-31 2022-05-24 L'oreal Hair care and conditioning compositions

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JPH04100535A (ja) * 1990-08-15 1992-04-02 Seven Kagaku:Kk 多価アルコール中油型乳化組成物
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013081120A1 (fr) 2011-11-30 2013-06-06 学校法人日本大学 Agent de formation d'organogel lécithine
WO2013176243A1 (fr) * 2012-05-25 2013-11-28 学校法人日本大学 Agent de formation d'organogel de lécithine
JPWO2013176243A1 (ja) * 2012-05-25 2016-01-14 学校法人日本大学 レシチンオルガノゲル形成剤
US11337906B2 (en) 2018-12-31 2022-05-24 L'oreal Hair care and conditioning compositions

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