WO2014112280A1 - Composition huileuse et agent épaississant ou de formation de gel - Google Patents

Composition huileuse et agent épaississant ou de formation de gel Download PDF

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Publication number
WO2014112280A1
WO2014112280A1 PCT/JP2013/084077 JP2013084077W WO2014112280A1 WO 2014112280 A1 WO2014112280 A1 WO 2014112280A1 JP 2013084077 W JP2013084077 W JP 2013084077W WO 2014112280 A1 WO2014112280 A1 WO 2014112280A1
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formula
alkyl group
compound
compound represented
linear
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PCT/JP2013/084077
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English (en)
Japanese (ja)
Inventor
橋崎要
齋藤好廣
田口博之
鈴木崇将
高瀬一郎
坂西裕一
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学校法人日本大学
株式会社ダイセル
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Priority to JP2014557369A priority Critical patent/JPWO2014112280A1/ja
Publication of WO2014112280A1 publication Critical patent/WO2014112280A1/fr

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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
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/20—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/10—Phosphatides, e.g. lecithin
    • C07F9/106—Adducts, complexes, salts of phosphatides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/48—Thickener, Thickening system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids

Definitions

  • the present invention relates to an oily composition and a thickening or gel forming agent. More specifically, a thickening or gel-forming agent that is easy to prepare, yet has high safety against living bodies and the environment, good thickening and gel-forming ability, excellent usability, and has all the good handling characteristics. And an oily composition containing the thickening or gel-forming agent.
  • the present application includes Japanese Patent Application Nos. 2013-006484 and 2013-006485 filed in Japan on January 17, 2013, Japanese Patent Application No. 2013-017068 filed in Japan on January 31, 2013, and Japanese Patent Application No. 2013. Insist on priority of -017069, the contents of which are incorporated herein.
  • Gel formers that thicken or solidify various oil phase components such as animal and vegetable oils, mineral oils, hydrocarbons, fatty acid esters, etc. are cosmetics, pharmaceuticals, foods, paints, inks, lubricants It is widely used in various fields.
  • the performance generally required for a gel-forming agent and the like includes that the desired oil phase component can be thickened or gel-formed with a small amount of addition, and that the obtained gel and the like are 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 produce a gel having thixotropic properties, and to have a good tactile sensation such as the obtained gel.
  • a thickening or gel forming agent a low molecular thickening or gel forming agent (1,2,3,4-dibenzylidene-D-sorbitol, 12-hydroxystearic acid, amino acid derivatives, etc.), a high molecular weight Thickening or gel forming agents (polyacrylic acid derivatives, dextrin derivatives, etc.) are known.
  • a low molecular thickening or gel forming agent self-assembles in the oil phase component and forms a huge network structure, which makes the oil phase component non-fluidized and thickens or gels.
  • the thickening or gel-forming agents are those that cause the thickening or gel formation of the oil phase components by complex entanglement and formation of a network structure.
  • Non-patent Documents 1-6 a small number of thickening and gel formation of oil phase components by reverse string micelles have 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.
  • the reverse string micelle has a hydrophilic environment inside, so it can contain water-soluble drugs and enzymes, etc. Yes.
  • a typical system for forming the reverse string micelle a three-component mixed system of lecithin / water / various oil phase components has been reported (Non-Patent Document 1).
  • water substitutes include ethylene glycol, formamide, glycerin, bile salts (Non-Patent Document 3), urea (Non-Patent Document 4), sucrose fatty acid ester (Non-Patent Document 5), D-ribose and D -Deoxyribose (Non-Patent Document 6) has been reported. Recently, it has been reported that similar oil thickening occurs in the combination of lecithin and polyglycerin (Patent Document 1).
  • lecithin forms reverse spherical micelles or reverse elliptical micelles in the oil phase component, 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. Therefore, it is believed that reverse string micelles grow.
  • Patent Document 2 it is a gel emulsion obtained by combining one or more surfactants such as lecithin and sucrose fatty acid ester and adding higher alcohol, glycerin and oil phase components thereto.
  • JP 2012-20979 A Japanese Patent Laid-Open No. 5-4911
  • 1,2,3,4-Dibenzylidene-D-sorbitol a low molecular thickening or gel forming agent
  • 12-hydroxystearic acid is commercially available as a thickening or gel-forming agent for waste tempura oil, but lacks thixotropic properties.
  • the thickener or gel former of the amino acid derivative is poorly soluble in the oil phase component, complicated operations such as heating at a high temperature and stirring for a long time are required to dissolve it.
  • dextrin derivatives of polymer thickeners or gel formers need to be added at a high concentration for gel formation or the like, and also have a “stickiness” peculiar to polymers and are not good in use.
  • Polyacrylic acid derivatives show good thickening and 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.
  • the hydrophilic substance is a liquid, but a further problem is that lecithin is expensive.
  • Patent Document 2 discloses a gel emulsion in which one or more surfactants such as lecithin and sucrose fatty acid ester are combined and a higher alcohol, glycerin and an oil phase component are added thereto.
  • This gel has low elasticity compared to the above-described thickening or gels composed of gel formers and reverse string micelles, so that it is easy to spill and poor handling, and either higher alcohol or glycerin is not available. If it lacks, there is a problem that the effect cannot be obtained.
  • the object of the present invention is simple preparation, high safety to the living body and environment, good thickening and gel-forming ability, excellent usability, all good handling, etc.
  • the object is to provide a cost-effective oily composition and a thickening or gel-forming agent.
  • the present invention relates to a compound (racemate) represented by the following formula (I):
  • R 1 and R 2 are the same or different and each represents an alkenyl group, a branched alkyl group, or a linear alkyl group (provided that R 1 and R 2 are linear at the same time) (It cannot be an alkyl group), Me represents a methyl group)
  • a compound represented by the following formula (II): (In the above formula (II), R 3 and R 4 are the same or different and each represents an alkenyl group, a branched alkyl group, or a linear alkyl group (provided that R 3 and R 4 are linear at the same time) (It cannot be an alkyl group), Me represents a methyl group)
  • An oily composition comprising at least one compound (A) selected from the group consisting of: and an oil phase component (B), wherein the compound (A) is represented by the formulas (I) to (IV).
  • an oily composition characterized by further containing a polyol and / or hydroxypolycarboxylic acid as the hydrophilic additive (C) is provided.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 9 , R 12 , R 13 , R 14 , and R 15 in formulas (I) to (VI) of the oily composition are: It is preferably the same or different and each represents an alkenyl group or a branched alkyl group.
  • the polyol of the oily composition is preferably at least one selected from the group consisting of polyglycerin and D-ribose.
  • the hydroxypolycarboxylic acid of the oily composition is preferably citric acid.
  • the compound (A) of the oily composition is a compound (racemate) represented by the formula (I) and a compound represented by the formula (II), or a compound represented by the formula (III).
  • the blending ratio (former / latter (molar ratio)) of the compound represented by formula (I) (racemate) and the compound represented by formula (II) of the oily composition is greater than 0/100 and 50 / Preferably it is less than 50.
  • a thickening or gel-forming agent comprising at least one compound (A) selected from the group consisting of: wherein the compound (A) is a compound represented by the above formulas (I) to (IV)
  • the present invention also provides a thickening or gel-forming agent characterized by containing a polyol and / or hydroxypolycarboxylic acid as the hydrophilic additive (C).
  • the compound (A) in the thickening or gel forming agent is a compound represented by the formula (I) (racemate) and a compound represented by the formula (II), represented by the formula (III).
  • a compound is preferred.
  • the compounding ratio (former / latter (molar ratio)) of the compound represented by the formula (I) (racemate) and the compound represented by the formula (II) in the thickening or gel forming agent is from 0/100 Preferably greater than 50/50
  • the present invention provides a compound represented by the following formula (IV).
  • R 9 represents an alkenyl group or a branched alkyl group
  • R 10 and R 11 are the same or different, each represents an alkyl group having 1 to 4 carbon atoms, and n is 0 to 14) Indicates an integer
  • a composition comprising a compound represented by the following formula (I) (racemate) and a compound represented by the following formula (II), the compound represented by the formula (I) (racemate) ) And the compound represented by formula (II) (former / latter (molar ratio)) is also provided in the composition of more than 0/100 and less than 50/50.
  • R 1 and R 2 are the same or different and each represents an alkenyl group, a branched alkyl group, or a linear alkyl group (provided that R 1 and R 2 are linear at the same time) (It cannot be an alkyl group), Me represents a methyl group)
  • R 3 and R 4 are the same or different and each represents an alkenyl group, a branched alkyl group, or a linear alkyl group (provided that R 3 and R 4 are linear at the same time) (It cannot be an alkyl group), Me represents a methyl group)
  • the present invention relates to the following.
  • Compound (racemate) represented by formula (I), compound represented by formula (II), compound represented by formula (III), compound represented by formula (IV) At least one compound (A) selected from the group consisting of the compound represented by formula (V) (optically active form or racemic form), and the compound represented by formula (VI), and an oil phase
  • the oily composition contains the component (B) and the compound (A) is a compound represented by the formula (I) to the formula (IV), a polyol and / or a hydrophilic additive (C)
  • An oily composition comprising a hydroxypolycarboxylic acid.
  • the compound (A) is a compound represented by the formula (I) (racemate) and a compound represented by the formula (II) (1) to (7) The oily composition as described.
  • the compound (A) is a compound represented by the formula (V) (an optically active substance or a racemate) and a compound represented by the formula (VI)
  • the compounding ratio (the former / the latter (molar ratio)) of the compound represented by the above formula (I) (racemate) and the compound represented by the above formula (II) is greater than 0/100 and 50/50
  • the oil-based composition as described in (8) which is less than.
  • the compounding ratio (former / latter (molar ratio)) of the compound represented by the formula (V) (optical isomer or racemate) and the compound represented by the formula (VI) is 0/100.
  • the total amount of the compound (A) and the hydrophilic additive (C) is 1 to 40% by weight with respect to the total amount (100% by weight) of the oily composition.
  • the content of the oil phase component (B) is 70 to 99% by weight with respect to the total amount (100% by weight) of the oily composition, as described in any one of (1) to (15) Oily composition.
  • the content of the hydroxypolycarboxylic acid is any one of (1) to (20), which is 0.1 to 10% by weight with respect to the total amount (100% by weight) of the oily composition.
  • the total amount of the optional components other than the compound (A), the oil phase component (B), and the hydrophilic additive (C) is based on the total amount (100% by weight) of the oil composition.
  • a cosmetic comprising the oily composition according to any one of (1) to (22).
  • R 15 are the same or different and each is an alkenyl group or a branched alkyl group, (23) The thickening or gel-forming agent.
  • the compound (A) in the thickening or gel forming agent is a compound represented by the formula (I) (racemate) and a compound represented by the formula (II) (23) to (28) ) Or thickener or gel former.
  • the compound (A) in the thickening or gel forming agent is a compound represented by the formula (V) (an optically active substance or a racemate) and a compound represented by the formula (VI) (23 ) To (28) The thickening or gel forming agent according to any one of the above.
  • the compounding ratio (former / latter (molar ratio)) of the compound represented by the formula (I) (racemate) and the compound represented by the formula (II) is greater than 0/100 and 50/50
  • the compounding ratio (former / latter (molar ratio)) of the compound represented by the formula (V) (optical isomer or racemate) and the compound represented by the formula (VI) is 0/100.
  • a composition comprising a compound represented by the formula (I) (racemate) and a compound represented by the following formula (II), wherein the compound (racemate) represented by the formula (I):
  • oily composition and the thickening or gel-forming agent of the present invention have the above-described configuration, they can be produced at a lower cost than using natural lecithin (L- ⁇ -phosphatidylcholine). Therefore, it is easy to prepare, yet has high safety for living organisms and the environment, good thickening and gel-forming ability, excellent usability, good handling, etc. It is possible to obtain the effect that the process can be realized.
  • natural lecithin L- ⁇ -phosphatidylcholine
  • the compound (A) used in the present invention may be at least one compound selected from the group consisting of the compounds represented by the formulas (I) to (VI), either alone or in combination of two or more. Can be used.
  • the compound represented by the formula (I) is a racemate, and the compound represented by the formula (V) is an optically active substance or a racemate.
  • 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”.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 9 , R 12 , R 13 , R 14 , and R 15 are the same or different.
  • Each represents an alkenyl group, a branched alkyl group, or a linear alkyl group (provided that R 1 and R 2 ; R 3 and R 4 ; R 5 and R 6 ; R 12 and R 13 ; R 14 and R 15 Do not simultaneously become a linear alkyl group), preferably an alkenyl group or a branched alkyl group.
  • the carbon number of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 9 , R 12 , R 13 , R 14 , and R 15 is not particularly limited. In view of the above, it is preferably 7 to 23, more preferably 7 to 20, and still more preferably 7 to 17.
  • fatty acids corresponding to R 1 and R 2 in formula (I) (R 1 COOH, R 2 COOH), fatty acids corresponding to R 3 and R 4 in formula (II) (R 3 COOH, R 4 COOH), fatty acids corresponding to R 5 and R 6 in formula (III) (R 5 COOH, R 6 COOH), fatty acids corresponding to R 9 in formula (IV) (R 9 COOH), formula Fatty acids corresponding to R 12 and R 13 in (V) (R 12 COOH, R 13 COOH), fatty acids corresponding to R 14 and R 15 in formula (VI) (R 14 COOH, R 15 COOH) are thickened.
  • R 7 , R 8 , R 10 , and R 11 are the same or different and may be any alkyl group having 1 to 4 carbon atoms, and are not particularly limited. From the viewpoint of gelation ability, for example, methyl, ethyl, propyl, isopropyl, butyl, s-butyl, t-butyl group and the like can be mentioned, and methyl group is more preferable.
  • n is not particularly limited, but is preferably an integer of 0 to 14, more preferably an integer of 0 to 10, and further preferably 0 to 8 from the viewpoint of raw material availability and gelling ability. It is preferable that it is an integer.
  • a compound (racemate) represented by formula (I) and a compound represented by formula (II) can be used in combination as compound (A).
  • the compound (optical isomer or racemate) represented by the formula (V) and the formula (VI) can be used in combination as the compound (A).
  • these may be called a composition.
  • thickening or gel formation agent, or oil-based composition can be used for the compounding ratio of a composition.
  • Oil phase component (B) The oil phase component used in the present invention is mainly composed of polar oil alone, a mixture of polar oil and nonpolar oil, or nonpolar oil.
  • Nonpolar oils include hydrocarbons such as squalane, petrolatum, liquid paraffin, n-decane, cyclohexane, chain or cyclic silicone oils, etc.
  • polar oils include fats and oils such as olive oil, Waxes such as lanolin, esters such as isopropyl myristate, decyl oleate, glycerin tri-2-ethylhexanoate [esters of fatty acids and alcohols having 8 or more carbon atoms (preferably 8 to 25 carbon atoms)] Higher fatty acids such as oleic acid and lauric acid [fatty acids having 12 or more carbon atoms (preferably, 12 to 25 carbon atoms)], higher alcohols solid at room temperature such as cetanol [12 or more carbon atoms (preferably, And alcohols having 12 to 25 carbon atoms].
  • Waxes such as lanolin
  • esters such as isopropyl myristate, decyl oleate, glycerin tri-2-ethylhexanoate
  • Higher fatty acids such as oleic acid and lauric acid [fatty acids having 12 or more carbon atoms (preferably, 12 to 25 carbon
  • the hydrocarbons are not particularly limited, but are preferably liquid hydrocarbon oils having an average molecular weight of 100 to 4000, more preferably the average molecular weight is 100 to 2000, and the average molecular weight. Is more preferably 100 to 1,000.
  • the oil phase components can be used alone or in combination.
  • hydrophilic additive (C) examples include polyol and hydroxypolycarboxylic acid, and these can be used alone or in admixture of two or more.
  • the polyol is not particularly limited, but from the viewpoint of safety, for example, a polyhydric alcohol polymer, a monosaccharide, a lower alcohol, a polyhydric alcohol, a dihydric alcohol alkyl ether, a dihydric alcohol alkyl ether, 2
  • a polyhydric alcohol polymer a monosaccharide, a lower alcohol
  • a polyhydric alcohol a dihydric alcohol alkyl ether
  • a dihydric alcohol alkyl ether a dihydric alcohol alkyl ether
  • 2 One or more selected from monohydric alcohol ether esters, glycerin monoalkyl ethers, sugar alcohols, oligosaccharides, polysaccharides, and derivatives thereof, selected from polyhydric alcohol polymers, monosaccharides, and derivatives thereof It is preferable that it is 1 type or 2 types or more.
  • the weight average molecular weight of the polyol is not particularly limited, but is, for example, about 70 to 4
  • the polyhydric alcohol polymer is not particularly limited, but from the viewpoint of safety, for example, polyglycerin, polyglycerin fatty acid ester, diethylene glycol, dipropylene glycol-triethylene glycol, polypropylene glycol, tetraethylene glycol, diglycerin-triglycerin. Tetraglycerin and the like, polyglycerin, polyglycerin fatty acid ester, polyethylene glycol and the like are preferable, and polyglycerin, polyglycerin fatty acid ester and the like are more preferable.
  • the weight average molecular weight of the polyhydric alcohol polymer is not particularly limited, but is, for example, about 500 to 4000, preferably 600 to 2000.
  • Polyglycerin is manufactured using various methods. For example, (1) a method of addition polymerization of glycidol to glycerin, (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 glycerin with a hydroxyl group protected is added to glycerin, followed by depolymerization and then deprotection, and this is repeated until an arbitrary degree of polymerization is obtained. (4) A method in which glycerin is thermally condensed in the presence of an alkali.
  • the most preferable production method is the method (1), which can be suitably used for the thickening or gel forming agent of the oily composition.
  • the polymerization degree of the glycerin unit of the polyglycerol is preferably 3 to 20, and more preferably 3 to 10. When the degree of polymerization is less than 3, it becomes difficult to obtain a stable gel, and when it is greater than 20, it becomes an emulsified composition, making it difficult to obtain a transparent gel, and also making it difficult to obtain the gel itself.
  • 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.
  • the IOB calculated from the organic conceptual diagram is a value obtained by the following formula (A).
  • HLB ⁇ inorganic / ⁇ organic ⁇ 10 (B) (Reference: Nippon Emulsion Co., Ltd. “Emulsion formulation design based on organic concept”)
  • the monosaccharide is not particularly limited, but from the viewpoint of safety, for example, a tricarbon sugar (for example, D-glyceryl aldehyde, dihydroxyacetone, etc.); a tetracarbon sugar (for example, D-erythrose, D-erythritol) Pentose (eg, L-arabinose, D-xylos, L-lyxose, D-arabinose, D-ribose, D-ribulo) Hexose (eg, D-glucose, D-talose, D-bucikose, D-galactose, D-fruct) -Carbon, L-galactose, L-mannose, D-tagatose, etc.); heptose sugar (for example, aldoheptose, heproose, etc.); octose sugar (for example, octulose, etc.)
  • a tricarbon sugar
  • pentose sugars (among others, D-ribose, arabinose) D-ribose and the like are more preferable among xylose, lyxose, xylulose, ribulose and the like.
  • D-ribose is a kind of aldopentose and is a constituent sugar such as ribonucleic acid (RNA) and many nucleotides. It is also recognized as a food additive and is used as a sweetener. Furthermore, since it is also a biological component, its toxicity to the human body is very low, safety is high, and it is industrially inexpensive and easy to obtain.
  • RNA ribonucleic acid
  • the hydroxypolycarboxylic acid is not particularly limited, but from the viewpoint of safety, for example, one or more selected from the group consisting of citric acid, malic acid, tartaric acid, and hydroxymalonic acid may be mentioned, It is preferably one or more selected from the group consisting of citric acid, malic acid and tartaric acid, more preferably one or more selected from the group consisting of citric acid and malic acid. .
  • ingredients such as vitamin B, vitamin E and various fragrances can be added as optional components to the oily composition of the present invention.
  • 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, etc.
  • fungi and bacteria present in the keratin when a plant anti-inflammatory / moisturizing component such as glycyrrhizic acid is added, 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.
  • 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 same applies to the thickening or gel forming agent of the present invention.
  • the thickening or gel forming agent of the present invention is a compound represented by the formula (I) to the formula (VI) (provided that the compound represented by the formula (I) is a racemate,
  • the compound represented by () may contain at least one compound (A) selected from the group consisting of an optically active form or a racemic form.
  • it is sufficient that it further contains a polyol and / or hydroxypolycarboxylic acid as a hydrophilic additive, and is not particularly limited in other respects.
  • the content of the hydrophilic additive (C) is particularly Although not limited, it is preferably 0 to 100 parts by weight, more preferably 1 to 80 parts by weight, still more preferably 10 to 60 parts by weight with respect to 100 parts by weight of the compound (A) from the viewpoint of increasing transparency and improving the appearance. Part.
  • the compound represented by the formula (I) in the thickening or gel forming agent of the present invention contains a compound represented by the formula (I) (racemate) and a compound represented by the formula (II), the compound represented by the formula (I)
  • the compounding ratio (former / latter (molar ratio)) of the compound represented by formula (II) and the compound represented by formula (II) is not particularly limited, but may be greater than 0/100 and less than 99/1. More preferably, it is more than 5/95 and less than 95/5, more preferably more than 10/90 and less than 90/10.
  • the compound represented by the formula (II) is more than the compound represented by the formula (I) (racemate), and when the hydrophilic additive (C) is a polyol, the compound is greater than 0/100 and 50 Less than 50/50, more preferably greater than 20/80 and less than 40/60.
  • the hydrophilic additive (C) is a hydroxypolycarboxylic acid, it is preferably greater than 0/100 and less than 50/50, more preferably. Is greater than 20/80 and less than 40/60.
  • the compounding ratio (former / latter (molar ratio)) of the compound represented by V) (optical isomer or racemate) and the compound represented by formula (VI) is not particularly limited, but is greater than 0/100 It is preferably less than 99/1, more preferably greater than 5/95 and less than 95/5, and even more preferably greater than 10/90 and less than 90/10.
  • the compound represented by formula (VI) is preferably more than the compound represented by formula (V) (racemate).
  • the blending ratio is greater than 0/100 and less than 50/50. More preferably, it is greater than 5/95 and less than 45/55, more preferably greater than 10/90 and less than 40/60.
  • content of the said arbitrary components other than a compound (A) and a hydrophilic additive (C) in the thickening or gel formation agent of this invention is not specifically limited, From a viewpoint of thickening and a gelling ability, it is thickened. Alternatively, it is preferably 20% by weight or less (for example, 0 to 20% by weight), more preferably 10% by weight or less (for example, 0 to 10% by weight), further preferably, based on the total amount of the gel forming agent (100% by weight). Is 5% by weight or less (for example, 0 to 5% by weight).
  • the oily composition of the present invention comprises a compound represented by the formula (I) to the formula (VI) (provided that the compound represented by the formula (I) is a racemate and represented by the formula (V).
  • the compound to be obtained may contain at least one compound (A) selected from the group consisting of an optically active substance or a racemate) and an oil phase component (B).
  • the compound represented by (IV) it is sufficient that it further contains a polyol and / or hydroxypolycarboxylic acid as a hydrophilic additive, and is not particularly limited in other respects.
  • the total amount of the compound (A) and the hydrophilic additive (C) is not particularly limited, but is the total amount (100% by weight) of the oily composition.
  • the content is preferably 1 to 40% by weight, more preferably 2 to 30% by weight, still more preferably 3 to 25% by weight. If the total amount (thickening or gel forming agent content) of the compound (A) and the hydrophilic additive (C) with respect to the whole oily composition is small, thickening and gel formation will be poor, and a stable oily composition will be obtained. It becomes difficult.
  • the content of the thickening or gel forming agent in the whole oily composition is large, there is no merit of using a large amount because the thickening and gel forming ability and the moisturizing / moisturizing effect reach a peak, which is advantageous from the economical viewpoint. Not. Therefore, it is preferable to contain in the said range.
  • the content of the compound (A) in the oily composition of the present invention is not particularly limited, but is based on the total amount (100% by weight) of the oily composition It is preferably 1 to 30% by weight, more preferably 5 to 20% by weight. The above range is determined from the viewpoint of thickening and the balance between gelling ability and economy.
  • the compound represented by formula (I) contains a compound (racemate) represented by formula (I) and a compound represented by formula (II), the compound represented by formula (I)
  • the compounding ratio (the former / the latter (molar ratio)) between the (racemate) and the compound represented by formula (II) is not particularly limited, but is preferably greater than 0/100 and less than 99/1. Preferably it is greater than 5/95 and less than 95/5, more preferably greater than 10/90 and less than 90/10.
  • the compound represented by the formula (II) is more than the compound represented by the formula (I) (racemate), and when the hydrophilic additive (C) is a polyol, the compound is greater than 0/100 and 50 Less than 50/50, more preferably greater than 20/80 and less than 40/60.
  • the hydrophilic additive (C) is a hydroxypolycarboxylic acid, it is preferably greater than 0/100 and less than 50/50, more preferably. Is greater than 20/80 and less than 40/60. Since the mixture in the above range can be produced at low cost, it is advantageous from the viewpoint of economy.
  • the compounding ratio (the former / the latter (molar ratio)) of the compound represented by the formula (VI) and the compound represented by the formula (VI) is not particularly limited, but greater than 0/100 and 99/1. It is preferably less than, more preferably more than 5/95 and less than 95/5, still more preferably more than 10/90 and less than 90/10.
  • the compound represented by formula (VI) is preferably more than the compound represented by formula (V) (racemate).
  • the blending ratio is greater than 0/100 and less than 50/50. More preferably, it is greater than 5/95 and less than 45/55, more preferably greater than 10/90 and less than 40/60.
  • the content of the oil phase component (B) in the oily composition of the present invention is not particularly limited, but is the total amount (100% by weight) of the oily composition. On the other hand, it is preferably 70 to 99% by weight, more preferably 75 to 97% by weight, still more preferably 80 to 95% by weight.
  • the content of the oil phase component is lower than 70% by weight, the amount of the gel forming agent is excessively large, and when it exceeds 99% by weight, the stability of the gel is deteriorated. .
  • the content of the oil phase component (B) in the oil-based composition of the present invention is not particularly limited, but with respect to 100 parts by weight of the compound (A),
  • the amount is preferably 500 to 1500 parts by weight, more preferably 600 to 1400 parts by weight, and still more preferably 700 to 1300 parts by weight.
  • the above range is determined from the viewpoint of thickening and the balance between gelling ability and economy.
  • the content of the hydrophilic additive (C) (mixing amount; if two or more types are included, the total amount thereof) is not particularly limited.
  • the content is preferably 0.1 to 15% by weight, more preferably 0.3 to 10% by weight, based on the total amount (100% by weight) of the oily composition.
  • the hydrophilic additive (C) is a polyol
  • the content of the polyol is not particularly limited, but is preferably 0.1 to 15% by weight, more preferably based on the total amount (100% by weight) of the oily composition. Is 0.3 to 10% by weight.
  • the hydrophilic additive (C) is a polyhydric alcohol polymer such as polyglycerin
  • the content of the polyhydric alcohol polymer is not particularly limited, but is based on the total amount (100% by weight) of the oily composition.
  • the content is preferably 0.1 to 10% by weight, more preferably 0.5 to 8% by weight.
  • the hydrophilic additive (C) is a monosaccharide such as D-ribose
  • the content of the monosaccharide is not particularly limited, but is 0.1 to 0.1% with respect to the total amount (100% by weight) of the oily composition. It is preferably 5% by weight, more preferably 0.3-2% by weight.
  • the hydrophilic additive (C) is a hydroxypolycarboxylic acid
  • the content of the hydroxypolycarboxylic acid is not particularly limited, but is 0.1 to 10% by weight with respect to the total amount (100% by weight) of the oily composition. % Is preferable, and more preferably 0.5 to 5% by weight. As described above, the above range is determined from the viewpoint of the balance between thickening and gelling ability and economy. If the amount of the hydrophilic additive (C) is too small, the gelling ability is lowered. On the other hand, if the amount of the hydrophilic additive (C) is too large, problems such as white turbidity may occur.
  • the total amount of the optional components other than the compound (A), the oil phase component (B), and the hydrophilic additive (C) is based on the total amount (100% by weight) of the oily composition.
  • it is 29% by weight or less (for example, 0 to 29% by weight), preferably 20% by weight or less (for example, 0 to 20% by weight), and more preferably 10% by weight or less (for example, 0 to 10% by weight).
  • the oily composition of the present invention is stable over a long period of, for example, 3 months or longer. 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 the rheological measurement of the oily composition of the present invention is defined as follows. That is, in the 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, and the viscosity in that region does not vary and shows a certain value.
  • 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.
  • the present invention will be described in more detail based on examples, but the present invention is not limited to these examples.
  • the ratio of the compound indicates a weight ratio.
  • “-” means that the component was not blended.
  • Phosphorus oxychloride (1.69 g, 11.0 mmol) was dissolved in chloroform (20 mL), and pyridine (5.06 g, 64.0 mmol) was added and stirred at 0 ° C. After 15 minutes, a solution of compound 4 (6.22 g, 10.0 mmol) in chloroform (60 mL) was added dropwise over 1 hour and stirred at room temperature. After 1 hour, a solution of choline chloride (2.79 g, 20.0 mmol) in pyridine (100 mL) was added, and the mixture was warmed to room temperature and stirred overnight. Ion exchange water (100 mL) was added to the resulting reaction mixture to stop the reaction, and the two phases were separated.
  • N, N′-carbonyldiimidazole (4.7 g, 29.0 mmol) was added and stirred at 25 ° C. After 5 hours, the reaction mixture was concentrated under reduced pressure, and the resulting residue was washed with 5% aqueous sodium dihydrogen phosphate solution (100 mL) and dried over anhydrous sodium sulfate. The residue obtained by filtering the solid and then concentrating under reduced pressure was dissolved in N, N′-dimethylformamide (150 mL). N, N′-dimethylethylenediamine (4.3 g, 48.4 mmol) was added at room temperature and stirred overnight.
  • N, N′-dicarbonyldiimidazole (4.28 g, 26.4 mmol) was added to a pyridine (11 mL) solution of compound 11 (7.53 g, 22.1 mmol) at 0 ° C., and the mixture was stirred at room temperature. Two hours later, toluene was added to the reaction mixture, and the mixture was concentrated under reduced pressure to remove pyridine. The obtained residue was dissolved in dichloromethane (100 mL), washed with 5% aqueous sodium dihydrogen phosphate (100 mL), and dried over anhydrous sodium sulfate. The solid was filtered and concentrated under reduced pressure to obtain a yellow liquid.
  • 1,4-Butanediol (15.1 g, 168 mmol) and triethylamine (16 ml) were placed in a 500 ml four-necked flask, and dichloromethane (250 ml) was added to obtain a homogeneous solution.
  • Ion exchange water 200 ml was added to the reaction mixture to stop the reaction, and the dichloromethane was distilled off by concentration under reduced pressure.
  • the following compound 14 was obtained by changing 1,3 propanediol of Production Example 6 to 1,2 ethylene glycol and treating in the same manner as Production Example 6.
  • the following compound 15 was obtained by changing 1,3 propanediol of Production Example 6 to 1,6 hexanediol and treating in the same manner as Production Example 6.
  • the following compound 16 was obtained by changing 1,3 propanediol of Production Example 6 to 1,8 octanediol and treating in the same manner as Production Example 6.
  • the following compound 17 was obtained by treating 1,3 propanediol of Production Example 6 with 1,10 decanediol and treating in the same manner as in Production Example 6.
  • Examples 1 to 7 Compound 6 obtained in Production Example 1, D-ribose (manufactured by Wako Pure Chemical Industries, Ltd.) or polyglycerin (manufactured by Daicel Corporation), and n-decane (manufactured by Wako Pure Chemical Industries, Ltd.) as an oil component are listed in Table 6 and An oily composition was prepared by mixing at a ratio shown in Table 7. While evaluating the gelatinization ability of the obtained oil-based composition, the transparency (appearance) of each composition was evaluated. The results are shown in Tables 6 and 7. The numerical values in the table represent the blending ratio (% by weight) of each component. Preparation methods and evaluation methods are shown below.
  • Example 8 to 13 Compound 8 or 9 obtained in Production Example 4, D-ribose or citric acid (manufactured by Wako Pure Chemical Industries, Ltd.), and n-decane as an oil component are mixed at a ratio shown in Table 8 and Table 9 to obtain an oily property.
  • a composition was prepared. The gelation ability of the obtained oily composition was evaluated. The results are shown in Tables 8 and 9. The numerical values in the table represent the blending ratio (% by weight) of each component. Preparation methods and evaluation methods are shown below.
  • Example 14 to 16 An oily composition was prepared by mixing the compound 10 obtained in Production Example 5, citric acid, and n-decane as an oily component at a ratio shown in Table 10. While evaluating the gelatinization ability of the obtained oil-based composition, the transparency (appearance) of each composition was evaluated. The results are shown in Table 10. The numerical values in the table represent the blending ratio (% by weight) of each component. Preparation methods and evaluation methods are shown below.
  • ⁇ Preparation method (Examples 14 to 16)> The required amount of compound 10 and citric acid were dissolved in methanol to obtain a uniform solution. Next, drying under reduced pressure was performed to completely remove methanol, and then n-decane was added thereto, followed by stirring 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.
  • Examples 17 to 25 Compounds 12 to 17 obtained in Production Examples 6 to 11, citric acid, and n-decane as an oil phase component were mixed at a ratio shown in Tables 11 and 12 to prepare an oily composition. The gelation ability of the obtained oily composition was evaluated. The results are shown in Tables 11 and 12. The numerical values in the table represent the blending ratio (% by weight) of each component. Preparation methods and evaluation methods are shown below.
  • ⁇ Preparation method Necessary amounts of compounds 12 to 17 and citric acid were dissolved in methanol to obtain a uniform solution. Next, drying under reduced pressure was performed to completely remove methanol, and then n-decane was added thereto, followed by stirring 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.
  • Example 26 to 35 The ratio shown in Table 13 and Table 14 for compound 18 (manufactured by H holstein, LIPOID S PE, purified phosphatidylethanolamine), polyglycerin, and n-decane or cyclohexane (manufactured by Wako Pure Chemical Industries, Ltd.) as the oil phase component
  • To prepare an oily composition The gelation ability of the obtained oily composition was evaluated.
  • the results are shown in Tables 13 and 14.
  • the numerical values in the table represent the blending ratio (% by weight) of each component.
  • 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). ⁇ : 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 oily composition and the thickening or gel-forming agent of the present invention are easy to prepare, yet have high safety to living bodies and the environment, good thickening and gel-forming ability, excellent use feeling, good handling properties, etc. Since these are all low-cost, they can be used as cosmetics, pharmaceuticals, foods, detergents, deodorants, bathing agents, fragrances, deodorants, etc., as various products that exhibit a gel state at room temperature. Especially suitable for cosmetics and pharmaceutical applications. Examples of 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. Moreover, since it shows characteristic viscoelastic behavior, it can be used for industrial oils such as thickeners and viscosity modifiers.

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Abstract

L'invention concerne : une composition huileuse à bas coût qui est facilement préparée, et en outre qui a la combinaison de tous parmi une sécurité élevée par rapport aux organismes vivants et l'environnement, une performance favorable d'épaississement et de formation de gel, une sensation supérieure lors de l'utilisation, des caractéristiques de manipulation favorables, et similaires ; et un agent épaississant ou de formation de gel. La composition huileuse est caractérisée en ce qu'elle contient un composant de phase huileuse et un composé (A) (dans la formule (I), R1 et R2 sont identiques ou différents, et chacun représente un groupe alcényle, un groupe alkyle à chaîne ramifiée ou un groupe alkyle à chaîne droite (où R1 et R2 ne représentent pas simultanément un groupe alkyle à chaîne droite) et Me représente un groupe méthyle) ou similaire.
PCT/JP2013/084077 2013-01-17 2013-12-19 Composition huileuse et agent épaississant ou de formation de gel WO2014112280A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2647395A1 (de) * 1976-10-20 1978-04-27 Nattermann A & Cie Verfahren zur herstellung von estern des glycerophosphocholins
JPS63139188A (ja) * 1986-11-13 1988-06-10 ハフスルント・ニコメド・フアルマ・アクチエンゲゼルシヤフト 混合置換された１、２‐ジーアシルーｓｎ−グリセロ‐３‐ホスホコリンの一段階製造法
JPH06234726A (ja) * 1992-11-24 1994-08-23 Takeda Chem Ind Ltd 防菌・防かび性化合物、その製造法および剤
WO1994019314A1 (fr) * 1993-02-19 1994-09-01 Nippon Shinyaku Co., Ltd. Derive de glycerol, dispositif et composition pharmaceutique
JP2003321319A (ja) * 2002-05-07 2003-11-11 Q P Corp 化粧料
JP2012020979A (ja) * 2010-07-16 2012-02-02 Daicel Corp 油性ゲル状組成物

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2647395A1 (de) * 1976-10-20 1978-04-27 Nattermann A & Cie Verfahren zur herstellung von estern des glycerophosphocholins
JPS63139188A (ja) * 1986-11-13 1988-06-10 ハフスルント・ニコメド・フアルマ・アクチエンゲゼルシヤフト 混合置換された１、２‐ジーアシルーｓｎ−グリセロ‐３‐ホスホコリンの一段階製造法
JPH06234726A (ja) * 1992-11-24 1994-08-23 Takeda Chem Ind Ltd 防菌・防かび性化合物、その製造法および剤
WO1994019314A1 (fr) * 1993-02-19 1994-09-01 Nippon Shinyaku Co., Ltd. Derive de glycerol, dispositif et composition pharmaceutique
JP2003321319A (ja) * 2002-05-07 2003-11-11 Q P Corp 化粧料
JP2012020979A (ja) * 2010-07-16 2012-02-02 Daicel Corp 油性ゲル状組成物

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
MIKO IMAI ET AL.: "A new reverse worm-like micellar system from a lecithin, multivalent carboxylic acid and oil mixture", JOURNAL OF COLLOID AND INTERFACE SCIENCE, vol. 403, 1 August 2013 (2013-08-01), pages 77 - 83 *

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