WO2013081120A1 - レシチンオルガノゲル形成剤 - Google Patents
レシチンオルガノゲル形成剤 Download PDFInfo
- Publication number
- WO2013081120A1 WO2013081120A1 PCT/JP2012/081125 JP2012081125W WO2013081120A1 WO 2013081120 A1 WO2013081120 A1 WO 2013081120A1 JP 2012081125 W JP2012081125 W JP 2012081125W WO 2013081120 A1 WO2013081120 A1 WO 2013081120A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ascorbic acid
- organogel
- lecithin
- forming agent
- composition
- Prior art date
Links
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims abstract description 115
- 239000000203 mixture Substances 0.000 claims abstract description 82
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1535—Five-membered rings
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
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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
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/16—Ethers
- C10M129/20—Cyclic ethers having 4 or more ring atoms, e.g. furans, dioxolanes
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- 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
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
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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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/02—Well-defined aliphatic compounds
- C10M2203/0206—Well-defined aliphatic compounds used as base material
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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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/106—Carboxylix acids; Neutral salts thereof used as thickening agents
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- 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
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
- C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
- C10M2207/1236—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic used as thickening agent
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- 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
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
- C10M2207/124—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms containing hydroxy groups; Ethers thereof
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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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
- C10M2207/2815—Esters of (cyclo)aliphatic monocarboxylic acids used as base material
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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
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- 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 a lecithin organogel forming agent that thickens or gels oils such as animal and vegetable oils, mineral oils, hydrocarbons, and fatty acid esters.
- Organogel forming agents that thicken or gelate oils such as animal and vegetable oils, mineral oils, hydrocarbons, fatty acid esters, etc. are used in various fields such as cosmetics, pharmaceuticals, foods, paints, inks, and lubricating oils. Widely used in The performance generally required for the organogel forming 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.
- oils such as animal and vegetable oils, mineral oils, hydrocarbons, fatty acid esters, etc.
- organogel forming agents low molecular 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.
- An organogel forming agent that is excellent in handling properties and has 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 cord-like micelle, it can contain water-soluble drugs, enzymes and the like, and has characteristics not found in the above-mentioned organogel forming agent.
- 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 Non-Patent Document 2
- formamide Non-Patent Document 2
- bile salts Non-Patent Document 3
- 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.
- Patent Document 2 As an organogelator that forms lecithin / sucrose fatty acid ester (Patent Document 2), lecithin / saccharide (Patent Document 3), and lecithin / urea (Patent Document 4) reverse string micelles, We have proposed organogel formers that have high environmental safety, good gelation ability, excellent usability, and good handling properties, but those using sucrose fatty acid esters or saccharides have a unique odor There was a problem that those using urea were not suitable for the food field.
- the present invention as an organogel-forming agent and thickening gel-like composition that forms reverse string micelles, is required to have high safety to the living body and the environment, excellent usability, and good gelling ability. It is an object of the present invention to provide an organogel-forming agent that has both, and a thickened gel-like composition using the organogel-forming agent.
- lecithin / ascorbic acid or an ascorbic acid derivative acts as an organogel-forming agent that forms reverse string micelles of various oils, and these lecithins It is possible to obtain a thickened gel-like composition having an inverted string-like micelle structure by using a three-component mixed system of / ascorbic acid or ascorbic acid derivatives / various oils, and the thickened gel-like composition is human body and environment It was found that the above-mentioned problems can be solved by being extremely safe, having good gelling performance and having long-term stability.
- an organogel-forming agent containing (a) lecithin, (b) ascorbic acid or an ascorbic acid derivative and forming reverse string micelles.
- [2] As a mixing ratio of (a) lecithin and (b) ascorbic acid or ascorbic acid derivative, (b) ascorbic acid with respect to the total mass of (a) lecithin and (b) ascorbic acid or ascorbic acid derivative Or the ascorbic acid derivative is contained in an amount of 0.1 to 35% by mass, the organogel forming agent as described in [1] above.
- a thickened gel-like composition comprising at least the organogel-forming agent according to the above [1] or [2] and (c) an oil component to form reverse string micelles.
- the organogel-forming agent is contained in an amount of 1 to 70% by mass with respect to the thickened gel-like composition as a mixing ratio of the organogel-forming agent and (c) the oil component.
- the thickening gel-like composition as described in [4].
- a method for producing an organogel forming agent for forming reverse string micelles wherein (a) lecithin and (b) ascorbic acid or an ascorbic acid derivative are dissolved in an organic solvent, and then the organic solvent is evaporated.
- a method for producing an organogel forming agent [7] A method for producing a thickened gel-like composition in which reverse string micelles are formed, wherein (a) lecithin and (b) ascorbic acid or an ascorbic acid derivative are dissolved in an organic solvent, and then the organic solvent is evaporated.
- a method for producing a thickened gel-like composition in which reverse-like micelles are formed characterized in that an organogel-forming agent is added and (c) an oil component is added to and mixed with the organogel-forming agent.
- the organogel forming agent for forming reverse string micelles of the present invention not only has 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. And can be widely used as various cosmetics, pharmaceuticals, foods, paints, inks, lubricants, 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 also be adjusted according to the organogel former used, the preparation conditions for 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 organogel forming agent of the present invention is a material that can thicken or gel various oil components to form reverse string micelles.
- the organogel-forming agent of the present invention contains (a) lecithin, (b) ascorbic acid or an ascorbic acid derivative, and when various (c) oil components are added and mixed, it thickens or gels to form an inverted string-like micelle structure. The resulting thickened gel 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 viscoelastic 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 with the phosphate group of lecithin, and the second is to have a slight hydrophobicity, and ascorbic acid or ascorbic acid derivatives have to satisfy these two. We noticed that it was possible to form reverse-like micelles with lecithin and ascorbic acid or ascorbic acid derivatives and various oils.
- the inventors observed the structure of the thickened or gel-like preparation obtained, specifically, the thickened gel-like preparation formed by mixing lecithin, ascorbic acid 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. The SAXS measurement was performed at 25 ° C.
- FIG. 2 shows a scattering curve (scattering intensity I (q) of a small-angle X-ray scattering measurement of a thickened gel composition in which 2% by mass of lecithin, 0.26% by mass of ascorbic acid and 97.74% by mass of n-decane are mixed. ) And the scattering vector q).
- q (4 ⁇ / ⁇ ) sin ⁇
- ⁇ is the scattering angle
- ⁇ is the wavelength of the X-ray.
- the cross-section radius (r) of the reverse cord-like micelle was determined to be 1.8 nm by the Cross-section plot based on the equations (1) and (2).
- Rc is the radius of rotation of the cross section.
- the exact length of the reverse-like micelles could not be calculated due to the limitation of the measurement range, but the simulation using the theoretical scattering function assuming rod-like particles using equation (3) (Calculated curve in the figure) ) Shows that the length (t) of the reverse string micelle is longer than 50 nm.
- J 1 is a linear Bessel function.
- the thickened gel-like composition obtained by thickening or gelling the oil component using the organogel-forming agent of the present invention can be said to have reverse cord-like micelles formed from the gelation state and physical properties. .
- Lecithin as the organogel-forming agent of the present invention is a lipid product mainly composed of phosphatidylcholine and widely distributed in living organisms such as natural animals, plants, and microorganisms, and is used in liver, egg yolk, soybean, yeast, etc. Many are known to be included.
- Representative lecithin includes egg yolk lecithin, soybean lecithin and the like, and it is preferable to use them.
- Lecithin can be used alone or in admixture of two or more, and the lecithin preferably has a phosphatidylcholine content of about 55 to 99% by weight.
- Natural lecithin is only in the L- ⁇ -form, but others can be used. Since natural lecithin is easily oxidized and unstable, it may be hydrogenated by a known method before use. In the present invention, such hydrogenated lecithin is also included in “lecithin”.
- Phosphatidylcholine means an ester obtained by reacting glycerol (glycerin) with at least one unsaturated fatty acid and phosphoric acid, the proton of which is substituted with choline as the amine function.
- phosphatidylcholine in which an unsaturated bond is hydrogenated is also included in “phosphatidylcholine”.
- phosphatidylcholine is particularly defined according to the following general formula (I).
- R 1 and R 2 independently of each other, are (corresponding) aliphatic hydrocarbon groups derived from saturated or unsaturated fatty acids having 4 to 24 carbon atoms (that is, saturated or saturated carbon atoms having 3 to 23 carbon atoms).
- Unsaturated aliphatic hydrocarbon groups which may be either linear or branched and may be substituted with one or more hydroxyl and / or amine functional groups.
- X represents a choline residue.
- the phosphatidylcholine may be one of the compounds represented by the formula (I) or a mixture of two or more.
- fatty acids corresponding to R 1 and R 2 are, for example, butyric acid, caproic acid, caprylic acid, capric acid, caproleic acid, lauric acid, laurolein. Acid, myristic acid, tyristoleic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, arachidic acid, isostearic acid, dihydroxtearic acid, and ricinoleic acid.
- PC phosphatidylcholine
- Natural PC can be obtained by extraction from animal or plant sources such as soybeans, sunflowers, or eggs.
- Unhydrogenated phosphatidylcholine obtained from natural products, such as soybeans, is commonly used as fatty acids esterifying glycerol, palmitic acid, stearic acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid, and possibly C20- Contains C22 fatty acids.
- ascorbic acid or an ascorbic acid derivative is used as the component (b) as the organogel forming agent of the present invention.
- L-ascorbic acid vitamin C, hereinafter referred to as “alcorbic acid”
- alcorbic acid is a kind of water-soluble vitamin that acts as an important antioxidant in the body as well as producing collagen and is widely used in medical products, foods, supplements, cosmetics, etc. It is used, has no toxicity to the human body, is highly safe, and is industrially inexpensive and easy to obtain.
- Ascorbic acid or ascorbic acid derivatives can be used as long as they are soluble in an organic solvent used in preparing the thickened gel composition.
- Ascorbic acid derivatives include ascorbic acid alkyl ethers, ascorbic acid alkyl esters, ascorbic acid glucosides, isomers of ascorbic acid such as erythorbic acid, and derivatives thereof.
- 3-O-alkylascorbic acid as ascorbic acid alkyl ether is preferably used.
- 3-O-alkyl ascorbic acid 3-O-alkyl ascorbic acid having an alkyl group having 1 to 22 carbon atoms is used.
- the alkyl group having 1 to 22 carbon atoms may be linear, branched or cyclic, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group and an isobutyl group.
- the mixing ratio of (a) lecithin (b) ascorbic acid or ascorbic acid derivative constituting the organogel-forming agent of the present invention may be any range as long as the reverse string-like micelle can be formed.
- the mass ratio of (b) ascorbic acid or ascorbic acid derivative to the total amount of the organogel forming agent is expressed by mass% of (b) component / ((a) component + (b) component), although it varies depending on (c) oil 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 35% by mass or less, preferably 30% by mass or less, more preferably. Is 25% by mass or less.
- the organogel forming agent of the present invention In order to produce the organogel forming agent of the present invention, (a) lecithin and (b) ascorbic acid or an ascorbic acid derivative are both dissolved in an organic solvent, and then the organic solvent is evaporated to produce the organogel forming agent. be able to. A thickened gel-like composition in which reverse cord-like micelles are formed by adding and mixing the oil component (c) to the produced organogel-forming agent can be obtained.
- 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, n-decane, isooctane, n-octane, n-heptane, n-hexane, cyclohexane; lauric acid, palmitic acid, stearic acid, oleic acid, behenic acid, etc.
- fatty acids such as isopropyl myristate, 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 gelation.
- 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 organogel-forming agent containing (a) lecithin (b) ascorbic acid or ascorbic acid derivative of the present invention
- the organogel-forming agent is thickened or gelled with respect to the oil component. Any amount can be mixed as long as reverse string micelles can be formed.
- the mixing ratio of the oil component (a) lecithin is 1 to 70% by mass, preferably 1.5 to 45% by mass, more preferably 2 to 25% by mass, and (b) ascorbic acid or an ascorbic acid derivative is 0.
- 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 organogel forming 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 gel strength can be adjusted by the concentration of the organogel forming agent and the mixing ratio of (a) lecithin and (b) ascorbic acid or an ascorbic acid derivative.
- the thickening gel composition of the present invention contains (a) lecithin (b) ascorbic acid or an ascorbic acid derivative, various (c) oil components are added, and other additive components are added as necessary. By dissolving uniformly, it can be gelled to form a reverse string-like micelle structure.
- lecithin and ascorbic acid or an ascorbic acid derivative are respectively sealed in a container, and an organic solvent is added and stirred.
- the organic solvent is completely evaporated by drying under reduced pressure, and then (c) the required amount of the oil component is added and stirred overnight, and the container is required in a room temperature bath 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.
- the thickened gel composition of the present invention As a method for producing the thickened gel composition of the present invention, (a) lecithin and (b) ascorbic acid or an ascorbic acid derivative were dissolved in an organic solvent, and then the organic solvent was evaporated to form an organogel-forming agent. It is preferable to produce a thickened gel-like composition in which reverse cord-like micelles are formed by adding and mixing the oil component (c) with the organogel-forming agent.
- organic solvent used in preparing the organogel forming agent and the thickened gel composition examples include lower alcohols such as methanol, ethanol, propanol and butyl alcohol; polyhydric alcohols such as ethylene glycol and propylene glycol; acetone, 2- Ketones such as butanone and cyclohequinone; ethers such as tetrahydrofuran and 1,4-dioxane; esters such as ethyl acetate and butyl acetate; amides such as N, N-dimethylformamide and N, N-dimethylacetamide; chloroform Halogenated hydrocarbons such as carbon tetrachloride, dichloromethane, dichloroethane, isopropyl bromide, ethyl bromide, dichlorobenzene, tetrachloroethane, trichloroethane, trichloroethylene, and ethylene tetrachloride; Preferably used
- 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. Particularly suitable for use in detergents, cosmetics, pharmaceuticals, and foods.
- 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 organogel-forming agent of the present invention forms a reverse string-like micelle structure, so that it has a hydrophilic environment inside and is a water-soluble component ⁇ It is possible to enclose drugs and enzymes.
- These reverse-like micelles are nanometer-scale extremely fine molecular aggregates.
- the polar groups of lecithin and ascorbic acid or ascorbic acid derivative molecules face inward, and the hydrophobic groups face outward. Since a large number of cords are gathered facing each other, a hydrophilic environment, that is, a small water pool (water phase) is formed inside.
- water-soluble substances that can be encapsulated include whitening agents, anti-inflammatory agents, antibacterial agents, hormone agents, vitamins, various amino acids and their derivatives, enzymes, antioxidants, hair restorers, and other pharmaceutical ingredients. It is done.
- 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 thickened gel-like composition formed can be adjusted according to the organogel-forming 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 organogel forming agent of the present invention is excellent in gelation ability with respect to various oils, can form a stable gel over a long period of 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" in touch.
- the organogel forming agent of the present invention is made of a material component such as lecithin, ascorbic acid or an ascorbic acid derivative that is highly safe and biodegradable for living bodies and the environment, and is environmentally conscious.
- the organogel-forming agent of the present invention is further used in fields other than the above, such as quasi-drugs, inks, paints, lubricants, 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
- 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.
- Example 1 to 11 (Formulation of thickening gel composition) As the component lecithin (a), soybean lecithin (trade name “L- ⁇ -Phosphatidylcholine (Soy-95%)” manufactured by Avanti Polar Lipids, Inc.), component (b) ascorbic acid (trade name “L-(+ ) -Ascorbic acid "manufactured by Wako Pure Chemical Industries, Ltd.), as component (c), n-decane (manufactured by Kanto Chemical Co., Ltd., 0.774 mPa ⁇ s (25 ° C.)) is shown in Table 1. A thickened gel composition was prepared. Examples 1 to 11 were made according to the respective composition compositions.
- Preparation of thickened gel composition Preparation of the thickened gel-like composition was carried out by enclosing the necessary amount of (a) component: lecithin and (b) component: ascorbic acid in a bottle, adding methanol, and stirring using a magnetic stirrer. After completely dissolving lecithin and ascorbic acid, methanol is completely evaporated by drying under reduced pressure. (C) A necessary amount of the oil component was added and further stirred overnight, and the bottle was prepared by allowing it to stand for several days in a thermostatic bath at 25 ° C. for stabilization. In the following examples and comparative examples, the thickening gel composition was prepared by the same preparation means.
- Examples 1 to 11 are prepared by preparing thickening gel compositions with component (a): lecithin in an amount of 5.0 to 20.0% by mass.
- the proportion of ascorbic acid in these organogel forming agents, that is, (b) component / ((a) component + (b) component) is 7 to 16% by mass
- the proportion of the organogelator in the thickened gel composition That is, ((a) component + (b) component) / ((a) component + (b) component + (c) component) is 5.7 mass% to 24 mass%.
- the state of the thickening gel was transparent or translucent, and all were gelled or ⁇ .
- the gels of Examples 2 and 6 were thickened ⁇ , but there was no problem in use. The evaluation results are shown in Table 1.
- Example 12 to 21 (Formulation of thickening gel composition)
- soybean lecithin (trade name “L- ⁇ -Phosphatidylcholine (Soy-95%)” manufactured by Avanti Polar Lipids, Inc.)
- component (b) ascorbic acid (trade name “L-(+ ) -Ascorbic acid ”manufactured by Wako Pure Chemical Industries, Ltd.)
- component, isopropyl myristate (Wako Pure Chemical Industries, Ltd. 4.74 mPa ⁇ s (25 ° C.)) is shown in Table 2.
- thickened gel compositions were prepared as Examples 12 to 21.
- the proportion of ascorbic acid in the organogel formers of Examples 12 to 21, that is, (b) component / ((a) component + (b) component) was from 16% by mass to 24% by mass.
- the ratio ((a) component + (b) component) / ((a) component + (b) component + (c) component) of the organogel forming agent is set to 6.2 mass% to 26 mass%.
- the state of the thickening gel was transparent or translucent, and all were gelled or ⁇ . Even if the gel was thickened ⁇ , there was no problem in use.
- the evaluation results are shown in Table 2.
- Example 22 to 24 Preparation of thickened gel composition
- Preparation of the thickened gel composition was carried out in Examples 2 and 4 using 3-O-ethylascorbic acid (manufactured by Junsei Chemical Co., Ltd.) instead of the component (b) L-ascorbic acid.
- Examples 23 and 24 were prepared, and in Example 2, Example 23 was prepared with 1.25% by mass of 3-O-ethylascorbic acid instead of L-ascorbic acid as component (b).
- a thickened gel composition was prepared.
- component: lecithin was 10% by mass
- component: n-decane were used to increase the viscosity.
- a gel composition was prepared, and the thickened gels were all thickened ⁇ and the transparency was ⁇ transparent. The evaluation results are shown in Table 3.
- the organogel formation agent which can form a reverse cord-like micelle by the 3 component mixed system of a lecithin / ascorbic acid or ascorbic acid derivative / various oil can be provided, and the thickening by which the reverse cord-like micelle was formed.
- the gel-like composition has a hydrophilic environment inside the reverse string micelle and can contain water-soluble components, drugs, enzymes, and the like. It can be widely used as an organogel forming agent for various cosmetics, pharmaceuticals, foods and the like.
- the thickening gel composition formed by using the organogel forming 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)アスコルビン酸またはアスコルビン酸誘導体を含有し逆紐状ミセルを形成するオルガノゲル形成剤。
[2] 前記(a)レシチンと(b)アスコルビン酸またはアスコルビン酸誘導体との混合割合として、(a)レシチンと(b)アスコルビン酸またはアスコルビン酸誘導体の合計質量に対して、(b)アスコルビン酸またはアスコルビン酸誘導体を0.1質量%から35質量%含有することを特徴とする上記[1]に記載のオルガノゲル形成剤。
[3] 上記[1]または[2]に記載のオルガノゲル形成剤と(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。
[4] 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[3]に記載の増粘ゲル状組成物。
[5] 前記オルガノゲル形成剤と(c)オイル成分との混合割合として、オルガノゲル形成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[3]または[4]に記載の増粘ゲル状組成物。
[6] 逆紐状ミセルを形成するオルガノゲル形成剤の製造方法であって、(a)レシチンと(b)アスコルビン酸またはアスコルビン酸誘導体を有機溶媒に溶解後、有機溶媒を蒸発させることを特徴とするオルガノゲル形成剤の製造方法。
[7] 逆紐状ミセルを形成した増粘ゲル状組成物の製造方法であって、(a)レシチンと(b)アスコルビン酸またはアスコルビン酸誘導体を有機溶媒に溶解後、有機溶媒を蒸発させることによりオルガノゲル形成剤とし、該オルガノゲル形成剤に(c)オイル成分を添加混合させることを特徴とする逆紐状ミセルを形成した増粘ゲル状組成物の製造方法。
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。
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)式を用いた棒状粒子を仮定した理論散乱関数を用いたシミュレーション(図中のCalculated curve)から逆紐状ミセルの長さ(t)は50nmよりも長いことが示された。
ここで、J1は一次のベッセル関数である。また、本発明のオルガノゲル形成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、逆紐状ミセルが形成されているといえる。
本発明のオルガノゲル形成剤は、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。
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ゼロシアー粘度を算出した。
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(ゼロシアー粘度100Pa・s以上のもの):○増粘(ゼロシアー粘度10Pa・s以上100Pa・s未満のもの):×増粘ゲル化が不十分(ゼロシアー粘度10Pa・s未満のもの)
ゲルの透明性は、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1か月保存した後、目視により観察したもので、◎:透明である、○:半透明である、△:白濁してる、×:二相分離しているとして評価したものである。
(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)成分のアスコルビン酸(商品名「L-(+)-アスコルビン酸」和光純薬工業(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1~11とした。
増粘ゲル状組成物の調製は、(a)成分:レシチンと(b)成分:アスコルビン酸をそれぞれ必要量ボトルに封入し、メタノールを加えマグネチックスターラーを用いて攪拌した。完全にレシチンとアスコルビン酸を溶解させた後、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、ボトルを安定化のために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、比較例においても、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。
(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)成分のアスコルビン酸(商品名「L-(+)-アスコルビン酸」和光純薬工業(株)製)、(c)成分として、ミリスチン酸イソプロピル(和光純薬工業(株)製 4.74mPa・s(25℃))を、表2に示す配合組成として、増粘ゲル状組成物を調製し実施例12~21とした。
(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2、4において、(b)成分のL-アスコルビン酸に換えて3-O-エチルアスコルビン酸(純正化学(株)製)を用いたものを実施例22,24とし、また、実施例2において、(b)成分のL-アスコルビン酸に換えて3-O-エチルアスコルビン酸を1.25質量%として実施例23を調製した。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。
(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2とした。
Claims (7)
- (a)レシチン、(b)アスコルビン酸またはアスコルビン酸誘導体を含有し逆紐状ミセルを形成するオルガノゲル形成剤。
- 前記(a)レシチンと(b)アスコルビン酸またはアスコルビン酸誘導体との混合割合として、(a)レシチンと(b)アスコルビン酸またはアスコルビン酸誘導体の合計質量に対して、(b)アスコルビン酸またはアスコルビン酸誘導体を0.1質量%から35質量%含有することを特徴とする請求項1に記載のオルガノゲル形成剤。
- 上記請求項1または2に記載のオルガノゲル形成剤と(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。
- 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3に記載の増粘ゲル状組成物。
- 前記オルガノゲル形成剤と(c)オイル成分との混合割合として、オルガノゲル形成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3または4に記載の増粘ゲル状組成物。
- 逆紐状ミセルを形成するオルガノゲル形成剤の製造方法であって、(a)レシチンと(b)アスコルビン酸またはアスコルビン酸誘導体を有機溶媒に溶解後、有機溶媒を蒸発させることを特徴とするオルガノゲル形成剤の製造方法。
- 逆紐状ミセルを形成した増粘ゲル状組成物の製造方法であって、(a)レシチンと(b)アスコルビン酸またはアスコルビン酸誘導体を有機溶媒に溶解後、有機溶媒を蒸発させることによりオルガノゲル形成剤とし、該オルガノゲル形成剤に(c)オイル成分を添加混合させることを特徴とする逆紐状ミセルを形成した増粘ゲル状組成物の製造方法。
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US14/361,491 US20140371333A1 (en) | 2011-11-30 | 2012-11-30 | Lecithin-organogelling agent |
EP12852762.9A EP2787050A4 (en) | 2011-11-30 | 2012-11-30 | LECITHIN-Organogel formers |
JP2013547239A JP6192047B2 (ja) | 2011-11-30 | 2012-11-30 | レシチンオルガノゲル形成剤 |
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WO2013176243A1 (ja) * | 2012-05-25 | 2013-11-28 | 学校法人日本大学 | レシチンオルガノゲル形成剤 |
WO2020203808A1 (ja) * | 2019-03-29 | 2020-10-08 | 日産化学株式会社 | レシチンオルガノゲルの新規製造方法 |
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WO2013176243A1 (ja) * | 2012-05-25 | 2013-11-28 | 学校法人日本大学 | レシチンオルガノゲル形成剤 |
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 |
WO2020203808A1 (ja) * | 2019-03-29 | 2020-10-08 | 日産化学株式会社 | レシチンオルガノゲルの新規製造方法 |
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US20140371333A1 (en) | 2014-12-18 |
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EP2787050A1 (en) | 2014-10-08 |
JP6192047B2 (ja) | 2017-09-06 |
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