WO2010122694A1 - Oil gel comprising reverse thread-like micelle - Google Patents
Oil gel comprising reverse thread-like micelle Download PDFInfo
- Publication number
- WO2010122694A1 WO2010122694A1 PCT/JP2010/000350 JP2010000350W WO2010122694A1 WO 2010122694 A1 WO2010122694 A1 WO 2010122694A1 JP 2010000350 W JP2010000350 W JP 2010000350W WO 2010122694 A1 WO2010122694 A1 WO 2010122694A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oil
- component
- gelling agent
- composition
- lecithin
- Prior art date
Links
- 239000000693 micelle Substances 0.000 title claims abstract description 51
- 230000002441 reversible effect Effects 0.000 title claims abstract description 46
- 239000003921 oil Substances 0.000 claims abstract description 132
- 239000000203 mixture Substances 0.000 claims abstract description 110
- 239000003349 gelling agent Substances 0.000 claims abstract description 73
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims abstract description 52
- 239000000787 lecithin Substances 0.000 claims abstract description 51
- 235000010445 lecithin Nutrition 0.000 claims abstract description 51
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- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 claims description 9
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Images
Classifications
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- A—HUMAN NECESSITIES
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
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- A61K8/60—Sugars; Derivatives thereof
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- A—HUMAN NECESSITIES
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- 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
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- 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
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- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
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- 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
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- 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
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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
- C10M161/00—Lubricating compositions characterised by the additive being a mixture of a macromolecular compound and a non-macromolecular compound, each of these compounds being essential
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- 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
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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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/12—Polysaccharides, e.g. cellulose, biopolymers
- C10M2209/126—Polysaccharides, e.g. cellulose, biopolymers used as thickening agents
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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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/10—Amides of carbonic or haloformic acids
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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
- 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
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).
- it requires heating and dissolution, and has high safety against living bodies and the environment.
- 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). Moreover, ethylene glycol, formamide, and bile salts (Non-patent Document 3) have only been reported as substitutes for water. Normally, 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.
- the present inventors have used lecithin / saccharide as an oil gelling agent for various oils, and also used a three-component mixed system of these lecithin / saccharide / various oils.
- lecithin / saccharide as an oil gelling agent for various oils
- a three-component mixed system of these lecithin / saccharide / various oils thus, it is possible to obtain a thickened gel-like composition having a reverse cord-like micelle structure, and the thickened gel-like composition is extremely safe for the human body and the environment, has a good gelling performance, and has a long-term It has been found that the above problems can be solved.
- the present inventors include an oil gelling agent containing lecithin and saccharides to form reverse string micelles, and a thickened gel-like composition containing the oil gelling agent and various oil components to form reverse string micelles. It came to invent.
- an oil gelling agent which contains (a) lecithin and (b) saccharides to form reverse string micelles.
- the (b) saccharide comprises at least one of a monosaccharide, an oligosaccharide, a polysaccharide, and a deoxy form thereof. .
- the oil gelling agent that forms the reverse string micelle of the present invention has not only the advantage and effect of being environmentally friendly with high safety to living bodies and the environment, but also gels the target oil with a small amount of addition. It can be widely used as an oil gelling agent for various cosmetics, pharmaceuticals, foods, paints, inks, lubricating oils and the like.
- the resulting thickened gel-like composition has thixotropic properties, is difficult to drip, 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. In addition, 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) saccharide, and thickened or gelled when various (c) oil components are added and mixed to form a reverse string-like micelle structure. Become a 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 that it has two or more functional groups capable of hydrogen bonding with the phosphate group of lecithin, and the second is that it has a slight hydrophobicity. It has been found that reverse string-like micelles can be formed with sugars and various oils.
- the present inventors observed the structure of the obtained thickened or gel-like preparation, specifically, the thickened gel-like preparation formed by mixing lecithin, D-ribose and n-decane. .
- 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, 0.2% by mass of D-ribose and 97.8% by mass of n-decane, 10% by mass of lecithin, D- Thickening gel composition 2 (sample 2) mixed with 1% by weight ribose and 89% by weight n-decane, thickened by mixing 20% by weight lecithin, 2% by weight D-ribose and 78% by weight n-decane
- the scattering curve (relationship of scattering intensity I (q) and scattering vector q) of the small-angle X-ray scattering measurement with the gel-like composition 3 (sample 3) is shown.
- 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.
- the amount of reverse string micelle per unit volume in the sample is increased. That is, it can be considered that the contribution of the structure factor is increased due to the proximity of the reverse string micelles, and the scattering intensity on the low q side is reduced.
- 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.
- Saccharides as oil gelling agents of the present invention are synonymous with saccharides, are widely distributed in nature, and are the most important among human nutrients, and extremely safe for living bodies and the environment.
- monosaccharides include glyceraldehyde, erythrose, xylitol, D-xylose, D-ribose, D-galactose, D-glucose, D-sorbitol, fructose and the like.
- Examples of oligosaccharides include maltose, cellobiose, lactose, and sucrose.
- polysaccharides examples include amylose, amylopectin, glycogen, and dextran.
- deoxy sugar by which the alcoholic hydroxyl group of these saccharides of monosaccharide, oligosaccharide, and polysaccharide was substituted by hydrogen can be illustrated.
- constituent sugars of ribonucleic acid, food additives, D-ribose as a sweetener, D-glucose and galactose as glucose, and deoxy sugars thereof can be exemplified as preferable examples. Since these are widely distributed in nature and are also human nutrients or biological components, they are not toxic to the human body, are highly safe, are industrially inexpensive and easy to obtain.
- the mixing ratio with the (a) lecithin (b) saccharide constituting the oil gelling agent of the present invention may be any range as long as it is a mixing ratio capable of forming reverse string micelles.
- the mass can be set to mass%, more preferably 0.2 to 5.2 mass%.
- the mass ratio of (b) saccharides to the total amount of the oil gelling agent varies depending on (c) oil component, but when expressed in 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 3% by mass or more, and the upper limit is experimentally 50% by mass or less, preferably 40% by mass or less, more preferably 30% by mass or less. It is.
- 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 the oil component (c) is gelled with the oil gelling agent containing (a) lecithin (b) saccharide of the present invention, the oil gelling agent is thickened or gelled with respect to the oil component, and the reverse string-like micelle is formed. Any amount can be mixed as long as it can be formed.
- the mixing ratio of the oil component is (a) 1 to 70% by mass of lecithin, preferably 1.5 to 45% by mass, more preferably 2 to 25% by mass, and (b) 0.1 to 30% by mass of saccharides.
- the oil component When the content is 0.15 to 15% by mass, more preferably 0.2 to 5.2% by mass, (c) the oil component is 30 to 99% by mass, preferably 50 to 98% by mass, more preferably It can be 70 to 97% by 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 1.5% by mass or more, more preferably 2% 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. % Or less.
- the thickening gel-like composition of the present invention contains (a) lecithin (b) saccharide, various (c) oil components are added, and other additive components are added as necessary to dissolve uniformly. By this, it can be gelled to form an inverted string micelle structure.
- component an organic solvent solution of lecithin and
- component saccharides are each enclosed in a required amount container, stirred, and completely
- component saccharides. After the organic solvent is dissolved, 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 placed in a room temperature constant temperature bath for stabilization as needed.
- It can be obtained by standing for days. It can also be prepared by dissolving a mixture of (a) lecithin, (b) saccharide and various (c) oil components by heating and cooling to room temperature. The heating at this time may be any temperature as long as the mixture dissolves, but is preferably in the range of 50 ° C to 80 ° C. At this time, in order to prevent lecithin from being oxidized, it is preferably carried out in a nitrogen atmosphere or by adding an antioxidant.
- 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. These reverse string micelles are nanometer-scale extremely fine molecular aggregates, and these reverse string micelles have a lecithin-saccharide molecule polar group facing inward and a hydrophobic group facing outward. Since many are gathered, a hydrophilic environment, that is, a small water pool (water phase) is formed inside. Examples of 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 saccharide that are highly safe and biodegradable for living bodies and the environment, and is an environmentally harmonious type.
- 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.
- Viscosity measurement was performed at a constant temperature of 25 ° C. using a cone plate (diameter 60, 35 mm, cone angle 1 ° and 4 °) and a rotational rheometer (RheoStress 600, manufactured by HAAKE) equipped with a Peltier temperature controller.
- a rotational rheometer Renishaw 600, manufactured by HAAKE
- Examples 1 to 8 (Formulation of thickening gel composition) As a component lecithin (a), soybean lecithin (trade name “L- ⁇ -Phosphatidylcholine (Soy-95%)” manufactured by Avanti Polar Lipids, Inc.), as a saccharide of component (b), D-ribose (Kanto Chemical ( Co., Ltd.), and (c) component, n-decane (manufactured by Kanto Chemical Co., Ltd. 0.774 mPa ⁇ s (25 ° C.)) was used as a blending composition shown in Table 1, and a thickened gel composition was prepared. . Examples 1 to 8 were made according to each composition.
- Preparation of thickened gel composition Preparation of the thickened gel-like composition was carried out by enclosing the required amount of (a) component: methanol solution of lecithin and (b) component: D-ribose in a bottle and stirring with a magnetic stirrer. After completely dissolving the component (b): D-ribose, the methanol is completely evaporated by drying under reduced pressure. (C) The required amount of oil component was added, and the mixture was further stirred overnight, and prepared by allowing the bottle to stand for several days in a thermostatic bath at 25 ° C. for stabilization. In the following Examples 9 to 27 and Comparative Examples 1 to 5, the thickening gel composition was prepared by the same preparation means.
- Examples 1 to 8 are prepared by preparing thickening gel-like compositions with (a) component: 2 to 25% by mass of lecithin.
- the ratio of D-ribose in these oil gelling agents, that is, (b) component / ((a) component + (b) component) is 9% by mass to 17% by mass, and the oil gelation in the thickened gel-like composition
- the ratio of the agent, that is, ((a) component + (b) component) / ((a) component + (b) component + (c) component) is 2% by mass to 30% by mass.
- the state of the thickening gel was transparent, both were gelled to ⁇ , and the storage stability was also ⁇ good.
- the state of the gel of Example 1 was a thickening ⁇ , but there was no problem in use.
- the evaluation results are shown in Table 1.
- Example 9 to 12 (Formulation of thickening gel composition)
- soybean lecithin (trade name “L- ⁇ -Phosphatidylcholine (Soy-95%)” manufactured by Avanti Polar Lipids, Inc.)
- component (b) D-ribose (manufactured by Kanto Chemical Co., Inc.)
- Example 11 was further mixed with liquid paraffin (Kanto Chemical ( 146 mPa ⁇ s (25 ° C.)), a thickened gel composition was prepared and used as Example 12.
- the composition is shown in Table 1.
- the ratio of D-ribose in the oil gelling agents of Examples 9 to 12, that is, (b) component / ((a) component + (b) component) is 3% to 29% by mass, in the thickened gel composition
- the ratio of the oil gelling agent ((a) component + (b) component) / ((a) component + (b) component + (c) component) is 10 mass% to 14 mass%.
- the state of the thickening gel was transparent, both were gelled ⁇ , and the storage stability was ⁇ good or ⁇ . In Example 12, the storage stability was ⁇ , but it was translucent and stable in the usual standard of 3 months, and it was in a state where there was no problem in use. The evaluation results are shown in Table 1.
- Example 13 to 22 (Formulation of thickening gel composition)
- soybean lecithin (trade name “L- ⁇ -hosphatidylcholine (Soy-95%)” manufactured by Avanti Polar Lipids, Inc.)
- component (b) was 2-deoxy-D-ribose (Kanto Chemical)
- a thickened gel-like composition was prepared with n-decane (manufactured by Kanto Chemical Co., Ltd.) as the component (c) and the formulation shown in Table 1. According to each compounding composition, it was set as Examples 13-17.
- component (b) was changed to 2-deoxy-D-glucose (manufactured by Kanto Chemical Co., Inc.), and a thickened gel-like composition was prepared as the composition shown in Table 2. According to each compounding composition, it was set as Examples 18-22.
- Example 13 to 17 the viscosity was increased by using (a) component: lecithin in an amount of 5 to 25% by mass, (b) component: 2-deoxy-D-ribose, and (c) component: n-decane.
- a gel composition was prepared.
- the ratio of 2-deoxy-D-ribose in these oil gelling agents, that is, (b) component / ((a) component + (b) component) is 11% by mass to 16% by mass, in the thickened gel-like composition
- the ratio of the oil gelling agent ((a) component + (b) component) / ((a) component + (b) component + (c) component) is 6 mass% to 30 mass%.
- the state of the thickening gel was transparent, both of which were gelled to ⁇ , and the storage stability was ⁇ .
- the state of the gel of Example 13 was a thickening ⁇ , but there was no problem in use.
- the evaluation results are shown in Table 1.
- Example 23 to 27 (Formulation of thickening gel composition)
- A Component: As lecithin, soybean lecithin (trade name “L- ⁇ -Phosphatidylcholine (Soy-95%)” manufactured by Avanti Polar Lipids, Inc.), (b) component as D-glucose (Wako Pure Chemical Industries, Ltd.) ) And n-decane (manufactured by Kanto Chemical Co., Inc.) as a component (c), and a thickened gel composition was prepared as Example 23.
- 2-deoxy-D-galactose manufactured by Tokyo Chemical Industry Co., Ltd.
- Examples 24 and 25 were used depending on the respective compositions.
- component (b) was 6-deoxy-D-galactose (manufactured by Tokyo Chemical Industry Co., Ltd.), and Examples 26 and 27 were used depending on the respective composition compositions. Table 2 shows the composition.
- Example 23 a thickened gel-like composition was prepared using the required amounts of (b) component: D-glucose and (c) component: n-decane.
- Examples 24 and 25 were prepared as component (b).
- Examples 26 and 27 are (b) component: thickened gel using 6-deoxy-D-galactose respectively in the required amount A composition is prepared.
- the mixing ratio is 7% to 12% by mass of the ratio of saccharide in the oil gelling agent (b) component / ((a) component + (b) component).
- the ratio of the oil gelling agent ((a) component + (b) component) / ((a) component + (b) component + (c) component) is from 6% by mass to 11% by mass.
- the gel state was transparent, and both gelation was excellent and the storage stability was good.
- the state of the gel of Examples 24 and 26 is thickening (circle), it was a state which does not pose any problem on use.
- the evaluation results are shown in Table 2.
- Example 28 to 32 (Preparation of thickened gel composition) Preparation of the thickened gel-like composition was carried out in Examples 4, 9, 10, 11, and 12, with (a) component: lecithin, (b) component: D-ribose, and (c) oil component in the required amount bottles. The mixture was sealed, dissolved by heating at about 60 ° C., and cooled to room temperature. At that time, it was performed in a nitrogen atmosphere to prevent oxidation of lecithin. As a blending composition shown in Table 3, a thickened gel composition was prepared. Examples 28 to 32 were used depending on the composition.
- Example 28 (a) component: 10% by mass of lecithin, (b) component: D-ribose, (c) component: n-decane, cyclohexane, isopropyl myristate, isopropyl palmitate, fluid
- component 10% by mass of lecithin
- component D-ribose
- component component: n-decane, cyclohexane, isopropyl myristate, isopropyl palmitate
- fluid A thickened gel-like composition was prepared using the required amount of paraffin, and the thickened gels were all in gelation ⁇ and ⁇ , and the storage stability was also good.
- the state of the thickening gel of Example 29 was thickening ⁇ , but there was no problem in use.
- the transparency of the gel is determined by enclosing the thickened gel-like composition in a sample bottle with a diameter of 27.5 mm and a height of 70 mm and storing it in a thermostatic bath set at 25 ° C. for 6 months, and then UV-visible.
- 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 3.
- the transparency is either transparent or cloudy, and can provide transparency according to the application used as the thickening gel composition.
- Component (a) As lecithin, soybean lecithin (trade name “L- ⁇ -Phosphatidylcholine (Soy-95%)” Avanti Polar Lipids, Inc.) 10% by mass, as component (c) n-decane (Kanto Chemical)
- a thickened gel-like composition was prepared using 90% by mass as a blending composition, and it was designated as Comparative Example 1.
- a thickened gel-like composition was prepared as Comparative Example 2 in the same manner as in Comparative Example 1 except that the component (c) was changed to cyclohexane (manufactured by Kanto Chemical Co., Ltd.).
- a thickened gel composition was prepared as Comparative Example 3 in the same manner as in Comparative Example 1 except that the component (c) was changed to isopropyl myristate (manufactured by Wako Pure Chemical Industries, Ltd.).
- a thickened gel composition was prepared as Comparative Example 4 in the same manner as in Comparative Example 1 except that the component (c) was changed to isopropyl palmitate (manufactured by Wako Pure Chemical Industries, Ltd.).
- a thickened gel composition was prepared as Comparative Example 5 in the same manner as Comparative Example 1 except that component (c) was changed to liquid paraffin (manufactured by Kanto Chemical Co., Inc.).
- Comparative Examples 1 to 5 did not use the saccharide of component (b), so that no thickening gel could be formed.
- Table 2 shows the composition and the evaluation results.
- the oil component (c) n-decane has a viscosity increase of 2.5 million times at 0.774 mPa ⁇ s at 25 ° C.
- the cyclohexane has a viscosity of 25 ° C.
- the oil gelling agent which can form a reverse string-like micelle with the 3 component mixed system of a lecithin / sugar / various oil
- the thickened gel-like composition formed with reverse string micelles has a hydrophilic environment inside the reverse string micelles, and can contain water-soluble ingredients, drugs, enzymes, etc. It can be widely used as an oil gelling agent for pharmaceuticals and foods.
- 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
Description
[1] (a)レシチン、(b)糖類を含有し逆紐状ミセルを形成するオイルゲル化剤。
[2] 前記(a)レシチンが、大豆レシチンまたは卵黄レシチンのいずれかであることを特徴とする上記[1]に記載のオイルゲル化剤。
[3] 前記(b)糖類が、単糖類、オリゴ糖、多糖類、及びこれらのデオキシ体のうち少なくとも一つからなることを特徴とする上記[1]または[2]に記載のオイルゲル化剤。
[4] 前記(a)レシチンと(b)糖類との混合割合として、(a)レシチンと(b)糖類の合計質量に対して、(b)糖類を0.1質量%から50質量%含有することを特徴とする上記[1]~[3]のいづれかに記載のオイルゲル化剤。
[5] 上記[1]~[4]のいずれかに記載のオイルゲル化剤と(c)オイル成分とを少なくとも含み逆紐状ミセルを形成した増粘ゲル状組成物。
[6] 前記増粘ゲル状組成物が、化粧料、医薬品、食品、塗料、インク、潤滑油の少なくともいずれか一つであることを特徴とする上記[5]に記載の増粘ゲル状組成物。
[7] 前記オイルゲル化剤と(c)オイル成分との混合割合として、オイルゲル化剤を増粘ゲル状組成物に対して1質量%から70質量%含有することを特徴とする上記[5]または[6]に記載の増粘ゲル状組成物。 That is, the present invention
[1] An oil gelling agent which contains (a) lecithin and (b) saccharides to form reverse string micelles.
[2] The oil gelling agent according to [1] above, wherein the (a) lecithin is either soybean lecithin or egg yolk lecithin.
[3] The oil gelling agent according to the above [1] or [2], wherein the (b) saccharide comprises at least one of a monosaccharide, an oligosaccharide, a polysaccharide, and a deoxy form thereof. .
[4] As a mixing ratio of (a) lecithin and (b) saccharide, 0.1 to 50% by mass of (b) saccharide is contained with respect to the total mass of (a) lecithin and (b) saccharide. The oil gelling agent according to any one of [1] to [3] above, wherein
[5] A thickened gel-like composition comprising at least an oil gelling agent according to any one of [1] to [4] above and (c) an oil component to form reverse string micelles.
[6] The thickened gel-like composition as described in [5] above, wherein the thickened gel-like composition is at least one of cosmetics, pharmaceuticals, foods, paints, inks, and lubricating oils object.
[7] The above-mentioned [5], wherein the oil gelling agent is contained in an amount of 1% by mass to 70% by mass with respect to the thickened gel-like composition as a mixing ratio of the oil gelling agent and (c) the oil component. Or the thickening gel-like composition as described in [6].
また、本発明の増粘ゲル状組成物は、逆紐状ミセルを形成しているゆえに、増粘又はゲル化されるオイルにもよるが、オイル自体が透明であるならば透明なものである。 The present inventors observed the structure of the obtained thickened or gel-like preparation, specifically, the thickened gel-like preparation formed by mixing lecithin, D-ribose and n-decane. . 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.
In addition, 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. .
この3つのサンプルの中で最もオイルゲル化剤濃度の低いサンプル1の散乱曲線では、両対数プロットの低q側の勾配が-1になっている。これは長い棒状の粒子、すなわち逆紐状ミセルの存在を示唆する。また(1)式および(2)式に基づくCross-sectionプロットにより、逆紐状ミセルの断面半径(r)は1.9nmと求められた。
ここで、Rcは断面の回転半径である。また、測定範囲の制約のために逆紐状ミセルの正確な長さは算出できなかったが、(3)式を用いたシミュレーションから逆紐状ミセルの長さ(t)は約500Å以上であることが示された。
ここで、J1は一次のベッセル関数である。また、サンプル2およびサンプル3では低q側の散乱強度が減少し、傾きも緩やかになる傾向が認められた。この結果は、サンプル2およびサンプル3では、試料内の単位体積当たりの逆紐状ミセル量が増加していることを示している。すなわち、逆紐状ミセル同士が近接することで構造因子の寄与が強くなり、低q側の散乱強度が減少したと考えられる。
更に、本発明のオイルゲル化剤を用いてオイル成分を増粘又はゲル化させた増粘ゲル状組成物は、そのゲル化の状態、物性からすると、同様に逆紐状ミセルが形成されているといえる。 FIG. 2 shows a thickened gel composition 1 (sample 1) in which 2% by mass of lecithin, 0.2% by mass of D-ribose and 97.8% by mass of n-decane, 10% by mass of lecithin, D- Thickening gel composition 2 (sample 2) mixed with 1% by weight ribose and 89% by weight n-decane, thickened by mixing 20% by weight lecithin, 2% by weight D-ribose and 78% by weight n-decane The scattering curve (relationship of scattering intensity I (q) and scattering vector q) of the small-angle X-ray scattering measurement with the gel-like composition 3 (sample 3) is shown. Here, q = (4π / λ) sin θ, θ is the scattering angle, and λ is the wavelength of the X-ray. According to this, since no scattering curve showed a clear diffraction peak, it can be seen that no regular structure was formed.
In the scattering curve of Sample 1 having the lowest oil gelling agent concentration among these three samples, the slope on the low q side of the log-log plot is -1. This suggests the presence of long rod-like particles, ie reverse string micelles. Further, the cross-section radius (r) of the reverse cord-like micelle was determined to be 1.9 nm by the Cross-section plot based on the equations (1) and (2).
Here, Rc is the radius of rotation of the cross section. In addition, 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.
Here, J 1 is a first-order Bessel function. In Samples 2 and 3, the low q-side scattering intensity decreased and the inclination tended to be gentle. This result shows that in Sample 2 and Sample 3, the amount of reverse string micelle per unit volume in the sample is increased. That is, it can be considered that the contribution of the structure factor is increased due to the proximity of the reverse string micelles, and the scattering intensity on the low q side is reduced.
Further, 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.
本発明のオイルゲル化剤は、さらに、上記以外の医薬部外品、インキ、塗料、潤滑油や、プラスチック、ゴム、金属等の加工分野のほか、農業、水産業、廃油処理等の分野でも用いることができる。 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”. Moreover, the oil gelling agent of the present invention is made of material components such as lecithin and saccharide that are highly safe and biodegradable for living bodies and the environment, and is an environmentally harmonious type.
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.
粘度測定は、コーンプレート(直径が60、35mmでコーン角が1度と4度)とペルチェ温度コントローラを備えた回転レオメーター(RheoStress600、HAAKE社製)を用いて25℃恒温下で行った。なお、溶媒の蒸発を防止するためにソルベントトラップを用いて測定した。具体的には、コーンプレートと試料台の間に試料を挟みこみ、コーンプレートを一定方向に回転させて試料に段階的にずり速度を加えた。それぞれのずり速度ごとにずり応力を求めて、粘度=ずり応力/ずり速度の関係から粘度を算出した。
また、これに基づき、増粘ゲル化の状態を以下のように評価した。
◎ゲル化(100Pa・s以上のもの):○増粘(10Pa・s以上100Pa・s未満のもの):×増粘ゲル化が不十分(10Pa・s未満のもの) [Evaluation of thickening gel composition]
Viscosity measurement was performed at a constant temperature of 25 ° C. using a cone plate (diameter 60, 35 mm, cone angle 1 ° and 4 °) and a rotational rheometer (RheoStress 600, manufactured by HAAKE) equipped with a Peltier temperature controller. In addition, in order to prevent evaporation of a solvent, it measured using the solvent trap. Specifically, the sample was sandwiched between the cone plate and the sample stage, and the cone plate was rotated in a fixed direction to apply a shear rate stepwise to the sample. The shear stress was calculated for each shear rate, and the viscosity was calculated from the relationship of viscosity = shear stress / shear rate.
Moreover, based on this, the state of thickening gelation was evaluated as follows.
◎ Gelation (100 Pa · s or more): ○ Thickening (10 Pa · s or more and less than 100 Pa · s): x Insufficient thickening gelation (less than 10 Pa · s)
保存安定性の確認は、実施例、比較例で調製した増粘ゲル状組成物を直径27.5mm、高さ70mmのサンプル瓶に封入し、25℃に設定した恒温槽中に6か月保存した後、増粘ゲル状組成物の分離状態を目視観察し、下記の基準により保存安定性を評価した。
◎良好である : ○少量分離している : ×悪い [Storage stability of thickened gel composition]
Storage stability was confirmed by enclosing the thickened gel composition prepared in Examples and Comparative Examples in a sample bottle with a diameter of 27.5 mm and a height of 70 mm and storing it in a thermostatic bath set at 25 ° C. for 6 months. Then, the separated state of the thickened gel composition was visually observed, and the storage stability was evaluated according to the following criteria.
◎ Good: ○ Slightly separated: × Poor
(増粘ゲル状組成物の配合)
(a)成分のレシチンとして、大豆レシチン(商品名「L-α-Phosphatidylcholine (Soy-95%)」Avanti Polar Lipids, Inc.製)、(b)成分の糖類として、D-リボース(関東化学(株)製)、(c)成分として、n-デカン(関東化学(株)製 0.774mPa・s(25℃))を、表1に示す配合組成として、増粘ゲル状組成物を調製した。各配合組成に応じて、実施例1~8とした。 [Examples 1 to 8]
(Formulation of thickening gel composition)
As a component lecithin (a), soybean lecithin (trade name “L-α-Phosphatidylcholine (Soy-95%)” manufactured by Avanti Polar Lipids, Inc.), as a saccharide of component (b), D-ribose (Kanto Chemical ( Co., Ltd.), and (c) component, n-decane (manufactured by Kanto Chemical Co., Ltd. 0.774 mPa · s (25 ° C.)) was used as a blending composition shown in Table 1, and a thickened gel composition was prepared. . Examples 1 to 8 were made according to each composition.
増粘ゲル状組成物の調製は、(a)成分:レシチンのメタノール溶液と、(b)成分:D-リボースをそれぞれ必要量ボトルに封入し、マグネチックスターラーを用いて攪拌した。完全に(b)成分:D-リボースを溶解させた後、減圧乾燥によりメタノールを完全に蒸発させる。(c)オイル成分を必要量加えてさらに一晩撹拌し、安定化のためにボトルを25℃の恒温槽で数日間静置することによって調製した。なお、以下の実施例9~27、比較例1~5においても、増粘ゲル状組成物の調製は、これと同じ調製手段によった。 (Preparation of thickened gel composition)
Preparation of the thickened gel-like composition was carried out by enclosing the required amount of (a) component: methanol solution of lecithin and (b) component: D-ribose in a bottle and stirring with a magnetic stirrer. After completely dissolving the component (b): D-ribose, the methanol is completely evaporated by drying under reduced pressure. (C) The required amount of oil component was added, and the mixture was further stirred overnight, and prepared by allowing the bottle to stand for several days in a thermostatic bath at 25 ° C. for stabilization. In the following Examples 9 to 27 and Comparative Examples 1 to 5, the thickening gel composition was prepared by the same preparation means.
(増粘ゲル状組成物の配合)
(a)成分のレシチンとして、大豆レシチン(商品名「L-α-Phosphatidylcholine (Soy-95%)」Avanti Polar Lipids, Inc.製)、(b)成分のD-リボース(関東化学(株)製)、(c)成分として、シクロヘキサン(関東化学(株)製 0.828mPa・s(25℃))を、増粘ゲル状組成物を調製し実施例9とした。
次に(c)成分をミリスチン酸イソプロピル(和光純薬工業(株)製 4.74mPa・s(25℃))に変え、増粘ゲル状組成物を調製し実施例10、(c)成分をパルミチン酸イソプロピル(和光純薬工業(株)製 6.09mPa・s(25℃))に変え、増粘ゲル状組成物を調製し実施例11、更に(c)成分を流動パラフィン(関東化学(株)製 146mPa・s(25℃))に変え、増粘ゲル状組成物を調製し実施例12とした。配合組成を表1に示す。 [Examples 9 to 12]
(Formulation of thickening gel composition)
As the component lecithin (a), soybean lecithin (trade name “L-α-Phosphatidylcholine (Soy-95%)” manufactured by Avanti Polar Lipids, Inc.), component (b) D-ribose (manufactured by Kanto Chemical Co., Inc.) ), (C) As a component, cyclohexane (0.828 mPa · s (25 ° C.) manufactured by Kanto Chemical Co., Inc.) was used to prepare a thickened gel composition, which was used in Example 9.
Next, the component (c) was changed to isopropyl myristate (4.74 mPa · s (25 ° C.) manufactured by Wako Pure Chemical Industries, Ltd.) to prepare a thickened gel-like composition. By changing to isopropyl palmitate (6.09 mPa · s (25 ° C.) manufactured by Wako Pure Chemical Industries, Ltd.), a thickened gel-like composition was prepared, and Example 11 was further mixed with liquid paraffin (Kanto Chemical ( 146 mPa · s (25 ° C.)), a thickened gel composition was prepared and used as Example 12. The composition is shown in Table 1.
(増粘ゲル状組成物の配合)
(a)成分のレシチンとして、大豆レシチン(商品名「L-α-hosphatidylcholine (Soy-95%)」Avanti Polar Lipids, Inc.製)、(b)成分を2-デオキシ-D-リボース(関東化学(株)製)とし、(c)成分として、n-デカン(関東化学(株)製)を、表1に示す配合組成として、増粘ゲル状組成物を調製した。各配合組成に応じて、実施例13~17とした。
次に(b)成分を2-デオキシ-D-グルコース(関東化学(株)製)に変え表2に示す配合組成として、増粘ゲル状組成物を調製した。各配合組成に応じて、実施例18~22とした。 [Examples 13 to 22]
(Formulation of thickening gel composition)
As the component lecithin (a), soybean lecithin (trade name “L-α-hosphatidylcholine (Soy-95%)” manufactured by Avanti Polar Lipids, Inc.), component (b) was 2-deoxy-D-ribose (Kanto Chemical) A thickened gel-like composition was prepared with n-decane (manufactured by Kanto Chemical Co., Ltd.) as the component (c) and the formulation shown in Table 1. According to each compounding composition, it was set as Examples 13-17.
Next, component (b) was changed to 2-deoxy-D-glucose (manufactured by Kanto Chemical Co., Inc.), and a thickened gel-like composition was prepared as the composition shown in Table 2. According to each compounding composition, it was set as Examples 18-22.
これらのオイルゲル化剤中の2-デオキシ-D-グルコースの割合、(b)成分/((a)成分+(b)成分)は11質量%から14質量%、増粘ゲル状組成物中のオイルゲル化剤の割合((a)成分+(b)成分)/((a)成分+(b)成分+(c)成分)は6質量%から29質量%としたものである。増粘ゲルの状態は、いずれもゲル化 ◎であり、保存安定性もすべて◎良好であり、いずれも透明であった。評価結果を表2に示す。 In Examples 18 to 22, the amount of (a) component: lecithin was 5 to 25% by mass, (b) component: 2-deoxy-D-glucose, and (c) component: n-decane were used in the required amounts. A thickened gel composition was prepared as shown in FIG.
The ratio of 2-deoxy-D-glucose in these oil gelling agents, (b) component / ((a) component + (b) component) is 11% by mass to 14% by mass, in the thickened gel-like composition The ratio of the oil gelling agent (component (a) + component (b)) / (component (a) + component (b) + component (c)) is 6 mass% to 29 mass%. The states of the thickening gel were all gelled ◎, all the storage stability was ◎ good, and all were transparent. The evaluation results are shown in Table 2.
(増粘ゲル状組成物の配合)
(a)成分:レシチンとして、大豆レシチン(商品名「L-α-Phosphatidylcholine (Soy-95%)」Avanti Polar Lipids, Inc.製)、(b)成分をD-グルコース(和光純薬工業(株)製)、(c)成分として、n-デカン(関東化学(株)製)を、増粘ゲル状組成物を調製し実施例23とした。
次に、(b)成分を2-デオキシ-D-ガラクトース(東京化成工業(株)製)とし、各配合組成に応じて、実施例24、25とした。
更に、(b)成分を6-デオキシ-D-ガラクトース(東京化成工業(株)製)とし、各配合組成に応じて、実施例26、27とした。表2に配合組成を示す。 [Examples 23 to 27]
(Formulation of thickening gel composition)
(A) Component: As lecithin, soybean lecithin (trade name “L-α-Phosphatidylcholine (Soy-95%)” manufactured by Avanti Polar Lipids, Inc.), (b) component as D-glucose (Wako Pure Chemical Industries, Ltd.) ) And n-decane (manufactured by Kanto Chemical Co., Inc.) as a component (c), and a thickened gel composition was prepared as Example 23.
Next, 2-deoxy-D-galactose (manufactured by Tokyo Chemical Industry Co., Ltd.) was used as the component (b), and Examples 24 and 25 were used depending on the respective compositions.
Furthermore, component (b) was 6-deoxy-D-galactose (manufactured by Tokyo Chemical Industry Co., Ltd.), and Examples 26 and 27 were used depending on the respective composition compositions. Table 2 shows the composition.
(増粘ゲル状組成物の調製)
増粘ゲル状組成物の調製は、実施例4、9、10、11、12において、(a)成分:レシチン、(b)成分:D-リボース、(c)オイル成分をそれぞれ必要量ボトルに封入し、60℃程度で加熱溶解し、室温まで冷却することによって調製した。その際、レシチンの酸化防止のために窒素雰囲気下で行った。
表3に示す配合組成として、増粘ゲル状組成物を調製した。各配合組成に応じて、実施例28~32とした。 [Examples 28 to 32]
(Preparation of thickened gel composition)
Preparation of the thickened gel-like composition was carried out in Examples 4, 9, 10, 11, and 12, with (a) component: lecithin, (b) component: D-ribose, and (c) oil component in the required amount bottles. The mixture was sealed, dissolved by heating at about 60 ° C., and cooled to room temperature. At that time, it was performed in a nitrogen atmosphere to prevent oxidation of lecithin.
As a blending composition shown in Table 3, a thickened gel composition was prepared. Examples 28 to 32 were used depending on the composition.
透明性は、いずれも透明又は白濁であり、増粘ゲル状組成物として用いる用途に応じた透明性を提供できる。 According to Examples 28 to 32, (a) component: 10% by mass of lecithin, (b) component: D-ribose, (c) component: n-decane, cyclohexane, isopropyl myristate, isopropyl palmitate, fluid A thickened gel-like composition was prepared using the required amount of paraffin, and the thickened gels were all in gelation ◎ and ◯, and the storage stability was also good. The state of the thickening gel of Example 29 was thickening ◯, but there was no problem in use. The transparency of the gel is determined by enclosing the thickened gel-like composition in a sample bottle with a diameter of 27.5 mm and a height of 70 mm and storing it in a thermostatic bath set at 25 ° C. for 6 months, and then UV-visible. 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 3.
The transparency is either transparent or cloudy, and can provide transparency according to the application used as the thickening gel composition.
(増粘ゲル状組成物の配合)
(a)成分:レシチンとして、大豆レシチン(商品名「L-α-Phosphatidylcholine (Soy-95%)」Avanti Polar Lipids, Inc.製)10質量%、(c)成分として、n-デカン(関東化学(株)製)90質量%を配合組成として、増粘ゲル状組成物を調製し比較例1とした。(c)成分をシクロヘキサン(関東化学(株)製)に変えた以外は比較例1と同じにして、増粘ゲル状組成物を調製し比較例2とした。(c)成分をミリスチン酸イソプロピル(和光純薬工業(株)製)に変えた以外は比較例1と同じにして、増粘ゲル状組成物を調製し比較例3とした。(c)成分をパルミチン酸イソプロピル(和光純薬工業(株)製)に変えた以外は比較例1と同じにして、増粘ゲル状組成物を調製し比較例4とした。又(c)成分を流動パラフィン(関東化学(株)製)に変えた以外は比較例1と同じにして、増粘ゲル状組成物を調製し比較例5とした。 [Comparative Examples 1 to 5]
(Formulation of thickening gel composition)
Component (a): As lecithin, soybean lecithin (trade name “L-α-Phosphatidylcholine (Soy-95%)” Avanti Polar Lipids, Inc.) 10% by mass, as component (c) n-decane (Kanto Chemical) A thickened gel-like composition was prepared using 90% by mass as a blending composition, and it was designated as Comparative Example 1. A thickened gel-like composition was prepared as Comparative Example 2 in the same manner as in Comparative Example 1 except that the component (c) was changed to cyclohexane (manufactured by Kanto Chemical Co., Ltd.). A thickened gel composition was prepared as Comparative Example 3 in the same manner as in Comparative Example 1 except that the component (c) was changed to isopropyl myristate (manufactured by Wako Pure Chemical Industries, Ltd.). A thickened gel composition was prepared as Comparative Example 4 in the same manner as in Comparative Example 1 except that the component (c) was changed to isopropyl palmitate (manufactured by Wako Pure Chemical Industries, Ltd.). A thickened gel composition was prepared as Comparative Example 5 in the same manner as Comparative Example 1 except that component (c) was changed to liquid paraffin (manufactured by Kanto Chemical Co., Inc.).
ADVANTAGE OF THE INVENTION According to this invention, the oil gelling agent which can form a reverse string-like micelle with the 3 component mixed system of a lecithin / sugar / various oil can be provided. The thickened gel-like composition formed with reverse string micelles has a hydrophilic environment inside the reverse string micelles, and can contain water-soluble ingredients, drugs, enzymes, etc. It can be widely used as an oil gelling agent for pharmaceuticals and foods. Further, the thickened gel composition formed by using the oil gelling agent has thixotropic properties, good handling properties, and good long-term stability.
Claims (7)
- (a)レシチン、(b)糖類を含有し逆紐状ミセルを形成するオイルゲル化剤。 (A) An oil gelling agent containing lecithin and (b) saccharides to form reverse string micelles.
- 前記(a)レシチンが、大豆レシチンまたは卵黄レシチンのいずれかであることを特徴とする請求項1に記載のオイルゲル化剤。 The oil gelling agent according to claim 1, wherein the (a) lecithin is either soybean lecithin or egg yolk lecithin.
- 前記(b)糖類が、単糖類、オリゴ糖、多糖類、及びこれらのデオキシ体のうち少なくとも一つからなることを特徴とする請求項1または2に記載のオイルゲル化剤。 The oil gelling agent according to claim 1 or 2, wherein the (b) saccharide comprises at least one of a monosaccharide, an oligosaccharide, a polysaccharide, and a deoxy form thereof.
- 前記(a)レシチンと(b)糖類との混合割合として、(a)レシチンと(b)糖類の合計質量に対して、(b)糖類を0.1質量%から50質量%含有することを特徴とする請求項1~3のいずれかに記載のオイルゲル化剤。 As a mixing ratio of the (a) lecithin and (b) saccharide, 0.1 to 50% by mass of (b) saccharide is contained with respect to the total mass of (a) lecithin and (b) saccharide. The oil gelling agent according to any one of claims 1 to 3, wherein
- 請求項1~4のいずれかに記載のオイルゲル化剤と(c)オイル成分とを少なくとも含み逆紐状ミセルを形成した増粘ゲル状組成物。 A thickened gel-like composition comprising at least the oil gelling agent according to any one of claims 1 to 4 and (c) an oil component to form reverse string micelles.
- 前記増粘ゲル状組成物が、化粧料、医薬品、食品、塗料、インク、潤滑油の少なくともいずれか一つであることを特徴とする請求項5に記載の増粘ゲル状組成物。 The thickening gel-like composition according to claim 5, wherein the thickening gel-like composition is at least one of cosmetics, pharmaceuticals, foods, paints, inks, and lubricating oils.
- 前記オイルゲル化剤と(c)オイル成分との混合割合として、オイルゲル化剤を増粘ゲル状組成物に対して1質量%から70質量%含有することを特徴とする請求項5または6に記載の増粘ゲル状組成物。 The oil gelling agent is contained in an amount of 1% by mass to 70% by mass with respect to the thickened gel-like composition as a mixing ratio of the oil gelling agent and (c) the oil component. Thickening gel composition.
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WO2013081120A1 (en) | 2011-11-30 | 2013-06-06 | 学校法人日本大学 | Lecithin-organogel-forming agent |
WO2013176243A1 (en) * | 2012-05-25 | 2013-11-28 | 学校法人日本大学 | Lecithin organogel formation agent |
JP2015531005A (en) * | 2012-07-12 | 2015-10-29 | プレジデント アンド フェローズ オブ ハーバード カレッジ | Slippery self-lubricating polymer surface |
WO2020203808A1 (en) * | 2019-03-29 | 2020-10-08 | 日産化学株式会社 | Novel method for producing lecithin organogel |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013081120A1 (en) | 2011-11-30 | 2013-06-06 | 学校法人日本大学 | Lecithin-organogel-forming agent |
WO2013176243A1 (en) * | 2012-05-25 | 2013-11-28 | 学校法人日本大学 | Lecithin organogel formation agent |
JPWO2013176243A1 (en) * | 2012-05-25 | 2016-01-14 | 学校法人日本大学 | Lecithin organogel former |
JP2015531005A (en) * | 2012-07-12 | 2015-10-29 | プレジデント アンド フェローズ オブ ハーバード カレッジ | Slippery self-lubricating polymer surface |
WO2020203808A1 (en) * | 2019-03-29 | 2020-10-08 | 日産化学株式会社 | Novel method for producing lecithin organogel |
Also Published As
Publication number | Publication date |
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JP5679215B2 (en) | 2015-03-04 |
JPWO2010122694A1 (en) | 2012-10-25 |
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