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WO2013058080A1 - Composition de gel huileuse - Google Patents

Composition de gel huileuse Download PDF

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Publication number
WO2013058080A1
WO2013058080A1 PCT/JP2012/075091 JP2012075091W WO2013058080A1 WO 2013058080 A1 WO2013058080 A1 WO 2013058080A1 JP 2012075091 W JP2012075091 W JP 2012075091W WO 2013058080 A1 WO2013058080 A1 WO 2013058080A1
Authority
WO
WIPO (PCT)
Prior art keywords
gel
weight
forming agent
lecithin
oily
Prior art date
Application number
PCT/JP2012/075091
Other languages
English (en)
Japanese (ja)
Inventor
坂西裕一
橋崎要
齋藤好廣
田口博之
Original Assignee
株式会社ダイセル
学校法人日本大学
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 株式会社ダイセル, 学校法人日本大学 filed Critical 株式会社ダイセル
Publication of WO2013058080A1 publication Critical patent/WO2013058080A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86—Polyethers
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/31—Hydrocarbons
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/55—Phosphorus compounds
    • A61K8/553—Phospholipids, e.g. lecithin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use

Definitions

  • the present invention relates to a gel-forming agent and an oily gel-like composition containing the gel-forming agent and an oil phase component.
  • Gel-forming agents that thicken or gel-form various oil phase components such as animal and vegetable oils, mineral oils and hydrocarbons are used in various fields such as cosmetics, pharmaceuticals, foods, paints, inks, and lubricating oils.
  • the performance generally required for a gel-forming agent includes that a desired oil phase component can be gel-formed with a small amount of addition, and the obtained gel is stable over a long period of time. Furthermore, depending on the application, it is required to have high safety to the human body and the environment, to generate a gel having thixotropy, and to have a good tactile sensation of the obtained gel.
  • Conventional gel formers include low-molecular gel formers (1,2,3,4-dibenzylidene-D-sorbitol, 12-hydroxystearic acid, amino acid derivatives, etc.), polymer gel formers (polyacrylic acid derivatives) , Dextrin derivatives, etc.) are known.
  • Low-molecular gel formers self-assemble in the oil phase components and form a huge network structure to make the oil phase components non-fluidized to form gels, while polymer gel formers make them complex. By forming an entangled network structure, gel formation of the oil phase component is caused.
  • Non-patent Documents 1-6 gel formation of oil phase components by reverse string micelles has also been reported (Non-patent Documents 1-6).
  • the reverse string micelle is a kind of self-assembly formed by a surfactant and is known to cause gel formation in order to form a network structure in the oil phase component. Since the reverse string micelle has a hydrophilic environment inside, it can contain a water-soluble drug, enzyme, etc., and has a feature not found in the above-mentioned gel forming agent.
  • Non-patent Document 1 A three-component mixed system of lecithin / water / various oil phase components has been reported as a typical system for forming the reverse string micelle (Non-patent Document 1).
  • water substitutes include ethylene glycol, formamide, glycerin, bile salts (Non-patent Document 3), urea (Non-patent Document 4), sucrose (Non-patent Document 5), D-ribose and D-deoxy. Ribose (Non-patent Document 6) has been reported.
  • lecithin forms reverse spherical micelles or reverse elliptical micelles in the oil phase component, but when a small amount of water or the like is added thereto, this hydrogen bonds to the phosphate group of lecithin, and the interface curvature of the molecular assembly is reduced. It is believed that reverse string micelle growth occurs to decrease.
  • Patent Document 1 gel formation of an oil phase component by an emulsion has been reported as a method for forming an oil phase component in a gel other than the above (Patent Document 1). That is, it is a gel emulsion in which one or more surfactants such as lecithin and sucrose are combined and a higher alcohol, glycerin and an oil phase component are added thereto.
  • one or more surfactants such as lecithin and sucrose are combined and a higher alcohol, glycerin and an oil phase component are added thereto.
  • 1,2,3,4-Dibenzylidene-D-sorbitol which is a low molecular gel forming agent, is an excellent compound capable of gel-forming various types of oil phase components, but it decomposes to produce benzaldehyde.
  • 12-hydroxystearic acid is commercially available as a gel-forming agent for waste tempura oil, but lacks thixotropic properties.
  • the gel forming agent of an amino acid derivative is hardly soluble in the oil phase component, complicated operations such as heating at a high temperature and long-time stirring are required to dissolve it.
  • a dextrin derivative of a polymer gel-forming agent needs to be added at a high concentration for gel formation, and also causes a “stickiness” peculiar to a polymer and is not good in use.
  • Polyacrylic acid derivatives show good thickening gel formation 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 is a gel emulsion in which one or more surfactants such as lecithin and sucrose are combined and a higher alcohol, glycerin and oil phase components are added thereto.
  • This gel has low elasticity compared to the gels composed of the gel formers and reverse string micelles described above, so it is easy to spill and poor handling, and it is effective if either higher alcohol or glycerin is missing. There is a problem that it cannot be obtained.
  • an object of the present invention is to provide a gel-forming agent that is easy to prepare and has all of high safety against living bodies and the environment, good gel-forming ability, excellent usability, and good handling properties.
  • Another object of the present invention is to provide an oily gel-like composition having excellent gel stability, which comprises the gel-forming agent having the above-mentioned excellent properties and an oil phase component.
  • the desired oil phase component is added with a small amount. It is required that a gel can be formed and that the obtained gel is stable over a long period of time. Furthermore, depending on the application, it is required that the gel is extremely safe for the human body, generate a gel having thixotropy, and have a good tactile sensation. However, in the prior art, it was not possible to obtain a sufficient gel forming agent having all of them.
  • the present inventors have used a three-component mixed system of lecithin / polyglycerin / oil phase component, and formed a gel-forming agent composed of reverse string micelles and a thickened gel. Succeeded in obtaining the composition.
  • the lecithin used in the present invention is an amphoteric phospholipid having two alkyl chains, and is widely used as a food emulsifier for emulsification of dairy products, viscosity reduction of chocolate, and pharmaceutical preparations.
  • polyglycerin is used as a moisturizer for cosmetics and as an emulsifier for food because of its strong hydrogen bonding ability and high safety.
  • a three-component mixed system of lecithin / polyglycerin / oil phase component was used for the preparation of a gel-forming agent capable of forming reverse cord-like micelles. It has been found that there is a blending range.
  • an oily gel composition comprising 1 to 30% by weight of a gel forming agent and 70 to 99% by weight of an oil phase component
  • the gel forming agent is a gel forming agent in which 1 to Y parts by weight of polyglycerin having a polymerization degree X is blended with 100 parts by weight of lecithin.
  • the nonpolar oil is preferably liquid paraffin, and the liquid paraffin preferably has an average molecular weight of 250 to 500.
  • oily gel-like composition referred to in the present invention refers to a gel-like composition that does not contain water or contains a very small amount (for example, 1% by weight or less, preferably 0.2% by weight or less).
  • the gel forming agent of the present invention Since the gel forming agent of the present invention has the above-described configuration, it is easy to prepare, has high safety to living bodies and the environment, and has all of good gel forming ability, excellent usability, and good handling properties. Moreover, it is excellent also in transparency. Since the oily gel-like composition of the present invention has the above-described configuration, it has high safety with respect to a living body and the environment, and has excellent usability and gel stability. Moreover, it is excellent also in transparency.
  • Lecithin is a lipid product mainly composed of phosphatidylcholine, widely distributed in living organisms such as natural animals, plants, and microorganisms, and is known to be contained in a large amount in liver, egg yolk, soybean, yeast and the like.
  • Representative lecithin includes egg yolk lecithin, soybean lecithin and the like.
  • Lecithin can be used alone or in admixture of two or more.
  • a phosphatidylcholine content of about 55 to 99% by weight is preferable. Those in this range tend to be creamy, have a moderate consistency, do not flow down when applied to the skin, and have a good feeling of use.
  • 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, and the proton of the phosphoric acid is substituted with choline as an amine functional group.
  • 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.
  • Non-hydrogenated phosphatidylcholines (PC) that are suitable for the practice of the compositions of the present invention may be of “natural” or “synthetic” origin.
  • 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 generally used as fatty acids esterifying glycerol as palmitic acid, stearic acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid, and possibly C 20. Contains ⁇ 22 fatty acids.
  • the polyglycerin used in the present invention is produced using various methods. For example, (1) a method of addition polymerization of glycidol to glycerol, (2) an operation of addition polymerization of epichlorohydrin to glycerol, dehydrochlorination under alkaline conditions, and then ring-opening with dilute sulfuric acid to the desired degree of polymerization (3) A method in which glycidol protected with a hydroxyl group is added to glycerin, followed by deprotection, and this is repeated until the desired degree of polymerization.
  • the most preferable production method is the method (1), which can be suitably used as a gel forming agent for the oily gel composition.
  • the degree of polymerization of the glycerin unit of the polyglycerin used is 3 to 20, particularly preferably 3 to 10. If the degree of polymerization is less than 3, a stable gel cannot be obtained, and if it is greater than 20, an emulsified composition is obtained, and a transparent gel cannot be obtained, and the gel itself cannot be obtained.
  • Polyglycerin can be used alone or in combination of a plurality of polymerization degrees.
  • the IOB calculated from the organic conceptual diagram is not particularly limited, but is preferably 2 or more, more preferably 2 to 3.
  • the gel composition can be obtained more easily.
  • the IOB calculated in the organic conceptual diagram is 2 to 3, it can be more reliably prevented from becoming an emulsified composition, and it becomes easier to obtain a gel composition.
  • Y 5-20
  • X is not particularly limited as long as 3 ⁇ X ⁇ 20 is satisfied, more preferably 4 ⁇ X ⁇ 20, further preferably 5 ⁇ X ⁇ 20, and 10 ⁇ X ⁇ 20. Is particularly preferred.
  • the gel forming agent can be contained in an amount of 1 to 30% by weight, preferably 5 to 20% by weight, particularly preferably 10 to 15% by weight, based on the entire oily gel composition. If the content of the gel forming agent (the total amount of lecithin and the polyglycerin) relative to the entire oily gel-like composition is small, gel formation is poor and a stable oily gel-like composition cannot be obtained. Moreover, when there is much content of the gel formation agent with respect to the whole oil-based gel-like composition, since gel formation power and a moisturizing and water retention effect will reach a peak, there is no merit to use in large quantities, and it is not economical. Therefore, it is preferable to contain in the said range.
  • the lecithin content in the entire oily gel composition can be calculated from the above, but it is preferably in the range of 1 to 30% by weight, particularly preferably in the range of 5 to 20% by weight.
  • the content of lecithin is low, poor gel formation tends to occur and a stable oily gel composition cannot be obtained.
  • the content is too large, the gel forming ability and the moisturizing / water retaining effect reach a peak, so there is no merit of using a large amount and it is not economical. Therefore, it is preferable to contain in the said range.
  • the content of phosphatidylcholine in the entire oily gel composition is, for example, 0.75 to 19% by weight, preferably 4 to 14% by weight.
  • the content of the polyglycerin in the entire oily gel composition can also be calculated from the above, but is preferably in the range of 0.1 to 5% by weight, particularly in the range of 3 to 5% by weight. preferable. If the polyglycerin content is low, a stable oily gel-like composition cannot be obtained, and if the content is too high, the gel forming ability and the moisturizing / water-retaining effect will reach a peak, so the advantage of using a large amount Not economical. Therefore, it is preferable to contain in the said range.
  • the oil phase component used in the present invention is mainly composed of nonpolar oil.
  • the non-polar oil is not particularly limited and may include hydrocarbons such as liquid paraffin, squalane and petrolatum, but liquid paraffin is preferable.
  • the hydrocarbons are not particularly limited but are preferably liquid hydrocarbon oils having an average molecular weight of 250 to 500.
  • the content of these oil phase components is in the range of 70 to 99% by weight based on the total amount of the oily gel composition, and is blended alone or in combination.
  • the content of the oil phase component is preferably 80 to 95% by weight, more preferably 85 to 90% by weight, based on the total amount of the oily gel composition.
  • Lecithin itself is effective as a cosmetic that softens aged keratin by reaching all the corners of the skin, but in order to further enhance the effect as a cosmetic for skin, vitamin B, vitamin Components such as E and various fragrances can be added.
  • vitamin B vitamin Components such as E and various fragrances
  • ascorbic acid is particularly effective.
  • the pH value of ascorbic acid is about 2, and when this is added, the pH value of the cosmetic is lowered, the keratolytic action is exhibited, and the old keratin is removed.
  • an ascorbic acid derivative such as ascorbyl palmitate can be used.
  • a component having antibacterial action such as hinokitiol, fucoidan, salicylic acid
  • fungi and bacteria present in the keratin.
  • a plant anti-inflammatory / moisturizing component such as glutyrrhizic acid
  • a sedative / moisturizing effect can be expected in a state where the cured keratin is lacerated and inflamed.
  • powders such as a silica, a silicon powder, an alkyl acrylate copolymer, can also be added.
  • oily gel composition of the present invention in addition to the above-described components, components used in ordinary general cosmetics can be blended.
  • components 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. Vitamins, amino acids, placenta extract, and the like, which can be used alone or in combination.
  • the content of the components other than the gel forming agent and the oil phase component in the oily gel composition of the present invention is usually 29% by weight or less (for example, 0.1 to 29% by weight), preferably 20% by weight or less ( For example, 0.1 to 20% by weight), more preferably 10% by weight or less (for example, 0.1 to 10% by weight).
  • the oily gel composition obtained in the present invention is stable for a long period of, for example, 3 months or more. Further, since it was confirmed that the rheology measurement has an appropriate elasticity, it is judged that the liquid is difficult to drip and the handling property is good. Furthermore, since it has thixotropic properties, it has good elongation when applied to, for example, skin.
  • the zero shear viscosity obtained from the viscosity curve obtained by rheological measurement of the oily gel composition of the present invention is defined as follows. That is, in a region where the shear rate is as close to zero as possible, there is a region that can be approximated to a Newtonian fluid even if it is a non-Newtonian fluid.
  • the viscosity ⁇ at this time is defined as a zero shear viscosity obtained from a viscosity curve obtained by rheology measurement.
  • the zero shear viscosity is not particularly limited, but is preferably 50 Pa ⁇ s or more, particularly preferably 100 Pa ⁇ s or more, from the viewpoint of gel stability, feel of the gel, feeling of use, handleability, and the like.
  • the upper limit of the zero shear viscosity is not particularly limited and varies depending on the application, but is, for example, 2000 Pa ⁇ s, preferably 1000 Pa ⁇ s.
  • Examples 1 to 9 Comparative Examples 1 to 22 Lecithin, polyglycerin and liquid paraffin (Molesco White P-100: manufactured by Moresco) were mixed at a ratio shown in Tables 1 to 4 to prepare an oily gel composition.
  • the rheology of the obtained oily gel composition was measured to evaluate the formation of a thickening gel and the transparency of each composition was evaluated.
  • the results are shown in Tables 1 to 4.
  • the numerical values in the table represent the blending ratio (% by weight) of each component.
  • the reagents, preparation methods, and evaluation methods used are shown below.
  • Soy lecithin was used as lecithin. Soy lecithin was from Avanti Polar Lipids, Inc. (phosphatidylcholine concentration 95%). As the liquid paraffin, Moresco White P-100 (manufactured by Moresco) was used as it was. Various polyglycerins used Daicel products as they were.
  • ⁇ Preparation method> Necessary amounts of lecithin, polyglycerin and liquid paraffin were sealed in a bottle and stirred using a magnetic stirrer. Thereafter, the sample was allowed to stand for several days in a constant temperature bath at 25 ° C. to reach equilibrium, thereby preparing a sample.
  • the viscosity becomes a constant value when the shear rate is 0.1 (s ⁇ 1 ) or less, and the value is defined as zero shear viscosity ⁇ 0 .
  • Evaluation of thickening gel formation was determined as follows based on this zero shear viscosity ⁇ 0 (Pa ⁇ s). The results are shown in Tables 1 to 4. ⁇ : Zero shear viscosity ⁇ 0 is 100 Pa ⁇ s or more ⁇ : Zero shear viscosity ⁇ 0 is 50 Pa ⁇ s or more and less than 100 Pa ⁇ s ⁇ : Zero shear viscosity ⁇ 0 is less than 50 Pa ⁇ s
  • the gel-forming agent and thickening gel-like composition characterized by the reverse string micelle obtained in the present invention are extremely safe for the human body and the environment, cosmetics, pharmaceuticals, foods, detergents, It can be used as various products exhibiting a gel form at room temperature as odorants, bathing agents, fragrances, deodorants and the like. Especially suitable for cosmetics and pharmaceutical applications.
  • cosmetics include creams, emulsions, lotions, cleansing agents, bath cosmetics, moisturizing cosmetics, blood circulation promoting / massaging agents, pack cosmetics, hair cosmetics, and the like.
  • Examples of pharmaceuticals include ointments, molded cataplasms, sustained-release preparation bases, transdermal absorption preparations, drug delivery system carriers, electrophoresis gels, and the like.
  • ointments molded cataplasms, sustained-release preparation bases, transdermal absorption preparations, drug delivery system carriers, electrophoresis gels, and the like.
  • it since it exhibits a characteristic viscoelastic behavior, it can be used for industrial oils such as thickeners and viscosity adjusters.

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  • Jellies, Jams, And Syrups (AREA)
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Abstract

L'invention concerne un agent de formation de gel qui est facilement préparé et qui combine une sûreté biologique et environnementale élevée, une aptitude favorable à la formation de gel, une excellente facilité d'utilisation et une facilité favorable de manipulation. L'invention concerne un agent de formation de gel caractérisé en ce qu'1 à Y parties en poids de polyglycérol d'un degré de polymérisation X sont mélangées pour 100 parties en poids de lécithine. (X et Y sont des nombres satisfaisants 3 ≤ X ≤ 20 et Y = 8,2Ln(X)-3,5). L'invention concerne également une composition de gel huileuse comprenant 1-30 % en poids de l'agent de formation de gel et 70-99 % en poids d'un composant à phase huileuse, la composition de gel huileuse étant caractérisée en ce que le composant huileux est principalement composé d'une huile non polaire.
PCT/JP2012/075091 2011-10-21 2012-09-28 Composition de gel huileuse WO2013058080A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2011-231747 2011-10-21
JP2011231747A JP2013087113A (ja) 2011-10-21 2011-10-21 油性ゲル状組成物

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WO2013058080A1 true WO2013058080A1 (fr) 2013-04-25

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020203808A1 (fr) * 2019-03-29 2020-10-08 日産化学株式会社 Nouveau procédé de production d'organogel de lécithine

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08257388A (ja) * 1995-03-23 1996-10-08 Nisshin Oil Mills Ltd:The 水分保持剤組成物およびこれを含有してなる基剤
JPH09220464A (ja) * 1996-02-14 1997-08-26 Nisshin Oil Mills Ltd:The 油中多価アルコールゲル型乳化組成物及びその製造方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08257388A (ja) * 1995-03-23 1996-10-08 Nisshin Oil Mills Ltd:The 水分保持剤組成物およびこれを含有してなる基剤
JPH09220464A (ja) * 1996-02-14 1997-08-26 Nisshin Oil Mills Ltd:The 油中多価アルコールゲル型乳化組成物及びその製造方法

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020203808A1 (fr) * 2019-03-29 2020-10-08 日産化学株式会社 Nouveau procédé de production d'organogel de lécithine

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