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WO2019188623A1 - Produit cosmétique de nettoyage - Google Patents

Produit cosmétique de nettoyage Download PDF

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Publication number
WO2019188623A1
WO2019188623A1 PCT/JP2019/011607 JP2019011607W WO2019188623A1 WO 2019188623 A1 WO2019188623 A1 WO 2019188623A1 JP 2019011607 W JP2019011607 W JP 2019011607W WO 2019188623 A1 WO2019188623 A1 WO 2019188623A1
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WO
WIPO (PCT)
Prior art keywords
oil
cleansing cosmetic
weight
carbon atoms
thickener
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/JP2019/011607
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English (en)
Japanese (ja)
Inventor
鈴木陽二
坂西裕一
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Daicel Corp
Original Assignee
Daicel Corp
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 Daicel Corp filed Critical Daicel Corp
Priority to JP2020510759A priority Critical patent/JPWO2019188623A1/ja
Publication of WO2019188623A1 publication Critical patent/WO2019188623A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • A61K8/30—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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • 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
    • 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
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/14—Preparations for removing make-up

Definitions

  • the present invention relates to a cleansing cosmetic suitable for an application for removing oily dirt.
  • This application claims the priority of Japanese Patent Application No. 2018-069675 for which it applied to Japan on March 30, 2018, and uses the content here.
  • the thing which can be washed away is calculated
  • liquid cleansing cosmetics especially when filled in a pump-type container, scatter when discharging, dripping from between fingers when picked up, or dripping from the discharge port of the container. It was a problem to contaminate the container.
  • a method of adding a thickener to moderately thicken the oil can be considered.
  • conventional thickeners for example, the polystyrene-hydrogenated polyisoprene block copolymer described in JP-A-8-59765
  • JP-A-8-59765 have a viscosity that is too high, so that it can be discharged from a pump-type container or applied to the skin. It was found that the spreadability during application deteriorates.
  • JP-A-2009-155592 discloses 1,2,3-propanetricarboxylic acid tris (2-methylcyclohexylamide) as a gelling agent (thickening agent) for hydrophilic or lipophilic compounds.
  • this compound is difficult to dissolve in an oil and it is difficult to use it as a thickener for the oil. That is, it turned out that it is difficult to use it for cleansing cosmetics with an oil agent with the conventionally well-known thickener (gelling agent).
  • an object of the present invention is a cleansing cosmetic that is excellent in detergency of oily stains and can be washed away with water by using a thickener added to the oil agent.
  • An object of the present invention is to provide a cleansing cosmetic that is difficult to fall off, has excellent spreadability, and is particularly excellent in dischargeability when filled in a pump-type container.
  • a compound having a specific structure can increase the viscosity of an oil agent to an arbitrary viscosity and maintain the viscosity stably.
  • Cleansing cosmetics that contain moderately thickened oils and surfactants have excellent cleaning performance for oily stains, can be washed away with water, and have excellent discharge properties when filled in pump-type containers. It has been found that when applied to the skin, it is difficult to sag when it is taken, and it is difficult to spill liquid from the outlet of the container. The present invention has been completed based on these findings.
  • the present invention is a cleansing cosmetic comprising a thickener (A), an oil agent (B) and a surfactant (C), wherein the thickener (A) is represented by the following formula (1):
  • R 1 is a monovalent linear aliphatic hydrocarbon group having 10 to 25 carbon atoms
  • R 2 and R 3 are the same or different and are divalent having 2, 4, 6, or 8 carbon atoms
  • R 4 represents an aliphatic hydrocarbon group, a bivalent alicyclic hydrocarbon group having 6 carbon atoms, or a divalent aromatic hydrocarbon group
  • R 4 represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms.
  • R 5 and R 6 are the same or different and represent a monovalent aliphatic hydrocarbon group having 1 to 3 carbon atoms or a hydroxyalkyl ether group, L 1 to L 3 represent an amide bond, and L 1 and When L 3 is —CONH—, L 2 is —NHCO—, and when L 1 and L 3 are —NHCO—, L 2 is —CONH—.) And 0.5 to 30.0% by weight of the thickener (A) and the oil agent (B), and the oil agent (B) is added to the thickener (A). And cleansing cosmetics containing 70.0 to 99.5% by weight based on the sum of the contents of oil and oil (B).
  • the oil agent (B) is preferably a polar oil or a nonpolar oil.
  • the sum of the contents of the thickener (A) and the oil (B) is preferably 10.0% by weight or more based on the total amount of the cleansing cosmetic.
  • the cleansing cosmetic of the present invention preferably has a viscosity of 300 to 3000 mPa ⁇ s at a temperature of 25 ° C. and a shear rate of 10 s ⁇ 1 .
  • the cleansing cosmetic composition of the present invention contains an oil agent and a surfactant that are thickened by the compound represented by the above formula (1) and have an appropriate viscosity and the viscosity is stably maintained over time. It has excellent detergency for oily stains, can be easily blended with skin stains, makeup stains, etc., and can be washed away by rinsing with water. Furthermore, since the cleansing cosmetic composition of the present invention has an appropriate viscosity, it is difficult to fall off between fingers when it is picked up by hand, and is excellent in spreadability. In addition, the cleansing cosmetic of the present invention is particularly excellent in dischargeability when filled in a pump-type container, and hardly leaks from the discharge port of the container. Therefore, the cleansing cosmetic composition of the present invention is most suitable for cleansing applications for oily dirt on the skin used by filling a pump-type container.
  • the cleansing cosmetic composition of the present invention contains a thickener (A), an oil agent (B), and a surfactant (C).
  • the cleansing cosmetic composition of the present invention may have other components described later in addition to the thickener (A), the oil agent (B), and the surfactant (C).
  • a mixture of the thickener (A) and the oil agent (B) may be referred to as an “oil composition”.
  • This oil composition is a mixture of a thickener (A) and an oil agent (B), and particularly means a form in which the oil agent is thickened and stabilized (gelled) by the thickener.
  • the combination of the oil composition may be a combination in which the thickener (A) and the oil agent (B) are compatible, and the combination is not particularly limited.
  • the thickener (A) in the cleansing cosmetic composition of the present invention contains a compound represented by the following formula (1) (hereinafter sometimes referred to as “compound (1)”).
  • compound (1) is added in an amount of 0.5 to 30.0 relative to the sum of the contents of the thickener (A) and the oil (B) (for example, the total amount of the oil composition). Includes weight percent.
  • the “thickener” in the cleansing cosmetic composition of the present invention includes not only a thickener that imparts viscosity, but also a gelling agent that gels and a stabilizer that uniformly stabilizes the components of the composition. It is a concept.
  • R 1 is a monovalent linear aliphatic hydrocarbon group having 10 to 25 carbon atoms
  • R 2 and R 3 are the same or different and are divalent having 2, 4, 6, or 8 carbon atoms
  • R 4 represents an aliphatic hydrocarbon group, a bivalent alicyclic hydrocarbon group having 6 carbon atoms, or a divalent aromatic hydrocarbon group
  • R 4 represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms.
  • R 5 and R 6 are the same or different and represent a monovalent aliphatic hydrocarbon group having 1 to 3 carbon atoms or a hydroxyalkyl ether group, L 1 to L 3 represent an amide bond, and L 1 and When L 3 is —CONH—, L 2 is —NHCO—, and when L 1 and L 3 are —NHCO—, L 2 is —CONH—.)
  • Examples of the monovalent linear aliphatic hydrocarbon group having 10 to 25 carbon atoms of R 1 include decyl group, lauryl group, myristyl group, pentadecyl group, stearyl group, palmityl group, nonadecyl group, eicosyl group, and behenyl.
  • a linear alkyl group such as a group; a linear alkynyl group such as a decenyl group, a pentadecenyl group, an oleyl group, and an eicocenyl group; and a linear alkynyl group such as a pentadecynyl group, an octadecynyl group, and a nonadecynyl group.
  • R 1 is a monovalent linear aliphatic hydrocarbon group having 14 to 25 carbon atoms (in terms of excellent thickening effect of a fluid organic substance (for example, the oil agent (B) in the present invention)). Particularly preferred is an alkyl group having 14 to 25 carbon atoms, and particularly preferred is a monovalent linear aliphatic hydrocarbon group having 18 to 21 carbon atoms (particularly preferred is an alkyl group having 18 to 21 carbon atoms). It is.
  • Examples of the divalent aliphatic hydrocarbon group having 2, 4, 6, or 8 carbon atoms in R 2 and R 3 include an ethylene group, an n-butylene group, an n-hexylene group, and an n-octylene group. .
  • Examples of the divalent alicyclic hydrocarbon group having 6 carbon atoms in R 2 and R 3 include a 1,4-cyclohexylene group, a 1,3-cyclohexylene group, and a 1,2-cyclohexylene group. .
  • Examples of the divalent aromatic hydrocarbon group in R 2 and R 3 include arylene groups having 6 to 10 carbon atoms such as 1,4-phenylene group, 1,3-phenylene group, and 1,2-phenylene group. Can be mentioned.
  • R 2 and R 3 are, among them, a divalent aliphatic hydrocarbon group having 2, 4, 6 carbon atoms (particularly preferably a straight-chain alkylene group) from the viewpoint of excellent thickening effect of the fluid organic substance. ), Particularly preferably a divalent aliphatic hydrocarbon group having 2 or 4 carbon atoms (particularly preferably a linear alkylene group), most preferably a divalent aliphatic hydrocarbon group having 2 carbon atoms (particularly, Preferably, it is a linear alkylene group.
  • R 4 represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms, and among them, a linear or branched alkylene group is preferable and particularly preferable because it is excellent in the thickening effect of a fluid organic substance. Is a linear alkylene group.
  • R 4 represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms.
  • a divalent aliphatic hydrocarbon group having 1 to 7 carbon atoms is more preferable because it is excellent in the thickening effect of the fluid organic substance.
  • Aliphatic hydrocarbon group particularly preferably a divalent aliphatic hydrocarbon group having 3 to 7 carbon atoms, most preferably a divalent aliphatic hydrocarbon group having 3 to 6 carbon atoms, particularly preferably 3 to 5 carbon atoms
  • These are divalent aliphatic hydrocarbon groups.
  • R 4 is preferably a linear or branched alkylene group having 1 to 8 carbon atoms, more preferably a linear alkylene group having 1 to 7 carbon atoms, particularly preferably a straight chain having 3 to 7 carbon atoms.
  • a linear alkylene group most preferably a linear alkylene group having 3 to 6 carbon atoms, particularly preferably a linear alkylene group having 3 to 5 carbon atoms.
  • Examples of the monovalent aliphatic hydrocarbon group having 1 to 3 carbon atoms in R 5 and R 6 include a straight or branched chain having 1 to 3 carbon atoms such as a methyl group, an ethyl group, a propyl group, and an isopropyl group.
  • hydroxyalkyl ether group in R 5 and R 6 examples include mono- or dihydroxy C 1-3 alkyl ether groups such as 2-hydroxyethoxy group, 2-hydroxypropoxy group, and 2,3-dihydroxypropoxy group. .
  • R 5 and R 6 are the same or different and are preferably monovalent aliphatic hydrocarbon groups having 1 to 3 carbon atoms, more preferably linear or branched alkyl groups having 1 to 3 carbon atoms. Group, particularly preferably a linear alkyl group having 1 to 3 carbon atoms, and particularly preferably a methyl group.
  • the compound (1) among them, compounds represented by the following formulas (1-1) to (1-9) are preferable from the viewpoint of excellent solubility of the fluid organic substance.
  • the compound (1) is also preferable in that it can be thickened and stabilized in a fluid organic substance. Further, when the fluid organic substance is transparent, the transparency can be maintained.
  • a compound represented by the following formula (2) (hereinafter sometimes referred to as “compound (2)”) is useful as a precursor of the compound represented by the above formula (1).
  • Compound (1) can be produced, for example, by oxidizing compound (2).
  • R 1 to R 6 and L 1 to L 3 in the above formula (2) are the same as those in the compound represented by the above formula (1).
  • the compound (2) includes a compound represented by the following formula (3) (hereinafter sometimes referred to as “compound (3)”) and a compound represented by the following formula (4) (hereinafter referred to as “compound (3)”). 4) ”or a compound represented by the following formula (3 ′) (hereinafter sometimes referred to as“ compound (3 ′) ”) and the following formula (4 ′): (Hereinafter, sometimes referred to as “compound (4 ′)”).
  • R 1 to R 6 and L 1 to L 3 are the same as those in the compound represented by the above formula (1).
  • R 7 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
  • OR 7 may form a ring by dehydration condensation or dealcohol condensation with a hydrogen atom constituting L 2 .
  • Examples of the alkyl group having 1 to 3 carbon atoms for R 7 in the above formulas (3) and (4 ′) include a methyl group, an ethyl group, a propyl group, and an isopropyl group.
  • Examples of the ring formed by OR 7 dehydration condensation or dealcohol condensation with the hydrogen atom constituting L 2 include a pyrrolidine-2,5-dione ring and a piperidine-2,6-dione ring.
  • the amount of the compound (4) used may be 1 mol or more with respect to 1 mol of the compound (3), and an excessive amount may be used.
  • the amount of the compound (4 ′) used may be 1 mol or more with respect to 1 mol of the compound (3 ′), and an excess amount may be used.
  • reaction of the compound (3) and the compound (4), or the compound (3 ') and the compound (4') can be carried out, for example, by stirring at a temperature of 100 to 120 ° C for 10 to 20 hours.
  • the reaction atmosphere is not particularly limited as long as the reaction is not inhibited, and may be any of an air atmosphere, a nitrogen atmosphere, an argon atmosphere, and the like.
  • the reaction can be carried out by any method such as batch, semi-batch and continuous methods.
  • the obtained reaction product can be separated and purified by separation means such as filtration, concentration, distillation, extraction, crystallization, adsorption, recrystallization, column chromatography, etc., or a combination means combining these.
  • Compound (1) can be produced by obtaining compound (2) by the above method and oxidizing the obtained compound (2).
  • hydrogen peroxide As the oxidizing agent used when oxidizing the compound (2) to obtain the compound (1), for example, hydrogen peroxide can be used.
  • hydrogen peroxide pure hydrogen peroxide may be used. However, from the viewpoint of handling, it is usually diluted with an appropriate solvent (for example, water) (for example, 5 to 70% by weight of hydrogen peroxide solution). ).
  • the amount of hydrogen peroxide to be used is, for example, about 0.1 to 10 mol with respect to 1 mol of compound (2).
  • the oxidation reaction can be performed, for example, by stirring at a temperature of 30 to 70 ° C. for 10 to 20 hours.
  • the above oxidation reaction is carried out in the presence or absence of a solvent.
  • a solvent examples of the solvent include alcohol solvents such as methanol, ethanol, 2-propanol, butanol; diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, dioxolane, 1,2- Ether solvents such as dimethoxyethane and cyclopentyl methyl ether; ester solvents such as butyl acetate and ethyl acetate; hydrocarbon solvents such as pentane, hexane, heptane and octane; nitrile solvents such as acetonitrile and benzonitrile .
  • alcohol solvents such as methanol, ethanol, 2-propanol, butanol
  • the obtained reaction product can be separated and purified by separation means such as filtration, concentration, distillation, extraction, crystallization, adsorption, recrystallization, column chromatography, etc., or a combination means combining these.
  • the compound represented, for example by following formula (3-1) can be manufactured by the following method, for example.
  • R 1 , R 2 , R 3 and R 7 are the same as those in the compounds represented by the above formulas (1), (3) and (4 ′).
  • R 7 in R 7 and wherein in formula (3a) (3d) may be the same or may be different.
  • two COORs 7 in the formula may be dehydrated and condensed to form an acid anhydride.
  • the compound (3 ') used as the raw material of the said reaction can be manufactured by the following method, for example.
  • R 1 , R 2 , R 3 and R 7 are the same as those in the compound represented by the above formula (1).
  • two COORs 7 in the formula may be subjected to dehydration condensation to form an acid anhydride.
  • the step [1] is a step of obtaining a compound represented by the formula (3c) by reacting the compound represented by the formula (3a) with the compound represented by the formula (3b).
  • the usage-amount of the compound represented by Formula (3b) should just be 1 mol or more with respect to 1 mol of compounds represented by Formula (3a), and can also use excess amount.
  • the reaction temperature of this reaction is, for example, 80 to 150 ° C., and the reaction time is, for example, about 1 to 24 hours.
  • the step [2] is a step of obtaining a compound represented by the formula (3-1) by reacting the compound represented by the formula (3c) with the compound represented by the formula (3d).
  • the amount of the compound represented by the formula (3d) may be 1 mol or more with respect to 1 mol of the compound represented by the formula (3c), for example, 1 to 3 mol.
  • the reaction temperature of this reaction is, for example, 80 to 150 ° C., and the reaction time is, for example, about 0.5 to 10 hours. As this reaction proceeds, water is produced. Therefore, it is preferable to perform the reaction while removing water using a dehydrating agent (for example, acetic anhydride) in order to promote the progress of the reaction.
  • a dehydrating agent for example, acetic anhydride
  • the reaction [2] is preferably performed in the presence of a solvent.
  • a solvent examples include pentafluorophenol, N, N-dimethylformamide, dimethylacetamide, o-dichlorobenzene and the like. These solvents can be used alone or in combination of two or more.
  • reaction [2] can be carried out in the presence of a base such as triethylamine, pyridine, 4-dimethylaminopyridine, if necessary.
  • a base such as triethylamine, pyridine, 4-dimethylaminopyridine, if necessary.
  • the step [3] is a step of obtaining the compound represented by the formula (3c ′) by reacting the compound represented by the formula (3a ′) with the compound represented by the formula (3b ′).
  • the reaction [3] can be carried out under conditions similar to those of the above reaction [2].
  • the step [4] is a step of obtaining a compound represented by the formula (3′-1) by reacting a compound represented by the formula (3c ′) with a compound represented by the formula (3d ′). .
  • the reaction [4] can be carried out under the same conditions as in the above reaction [1].
  • the obtained reaction product is separated by a separation means such as filtration, concentration, distillation, extraction, crystallization, adsorption, recrystallization, column chromatography, or a combination means combining these. It can be purified.
  • a separation means such as filtration, concentration, distillation, extraction, crystallization, adsorption, recrystallization, column chromatography, or a combination means combining these. It can be purified.
  • Oil agent (B) As the oil agent (B) in the cleansing cosmetic composition of the present invention, it is preferable to use liquid or paste-like oil at room temperature (23 ° C.), but even if it is a solid oil, a liquid cleansing cosmetic composition is used. If it is in the range which can prepare, it can be used. In the cleansing cosmetic of the present invention, the oil agent (B) is 70.0 to 99.5% by weight with respect to the sum of the contents of the thickener (A) and the oil agent (B) (for example, the total amount of the oil composition). % Is included. As the oil agent (B), for example, oils (compounds) listed below can be used according to the use and purpose of the cleansing cosmetic. As an oil agent (B), 1 type can be used individually or in combination of 2 or more types. The oil agent (B) does not include the thickener (A).
  • oil agent (B) examples include polar oils and nonpolar oils.
  • the polar oil is an oil agent that is insoluble in water, and refers to an oil agent having a polar bond such as an ether bond, an ester bond, or an amide bond in its molecule, and a nonpolar oil is , Hydrocarbon oils, and silicone oils that do not have polar substituents.
  • the oil agent (B) may be polar oil or nonpolar oil, and may be one or more selected from the group consisting of polar oil and nonpolar oil.
  • polar oil examples include natural oils such as sunflower oil, macadamia nut oil, avocado oil, almond oil, wheat germ oil, rice germ oil, olive oil, jojoba oil, evening primrose oil, coconut oil, mountain tea flower oil, and rosehip oil; 2-ethylhexyl isononanoate, hexyl laurate, isononyl isononanoate, isopropyl palmitate, isopropyl myristate, decyl oleate, cetyl octanoate, isodecyl isononanoate, octyl palmitate, octyl isopalmitate, isocetyl octanoate, isostearin Esters (esters) such as isopropyl acid, ethyl isostearate, stearyl 2-ethylhexanoate, isostearyl 2-ethylhexanoate, tri (capryl / capric acid
  • nonpolar oil examples include hydrocarbons such as (liquid) paraffin and squalane; silicone oils such as methylpolysiloxane, methylphenylpolysiloxane and decamethylcyclopentasiloxane.
  • the component (B) preferably contains a polar oil, and more preferably contains the esters.
  • the esters cetyl octoate is preferably used from the viewpoint of excellent compatibility with the component (A) and ease of washing with water.
  • the content of esters (particularly cetyl octanoate) in the oil (B) is, for example, 30% by weight or more (preferably 50% by weight or more, particularly preferably 70% by weight or more).
  • the surfactant (C) in the cleansing cosmetic of the present invention is not particularly limited as long as it is a component that can exhibit cleansing performance.
  • the surfactant (C) include a cationic surfactant, an anionic surfactant, an amphoteric surfactant, and a nonionic surfactant.
  • a nonionic surfactant from the viewpoint of safety.
  • 1 type can be used individually or in combination of 2 or more types.
  • Examples of the cationic surfactant include a quaternary ammonium salt, an alkylamine salt, and a compound having a pyridine ring.
  • Examples of the quaternary ammonium salt include tetramethylammonium chloride, tetramethylammonium hydroxide, tetrabutylammonium chloride, dodecyldimethylbenzylammonium chloride, alkyltrimethylammonium chloride, octyltrimethylammonium chloride, decyltrimethylammonium chloride, dodecyltrimethyl chloride.
  • Examples include ammonium, tetradecyltrimethylammonium chloride, cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, alkyltrimethylammonium bromide, hexadecyltrimethylammonium bromide, benzyltrimethylammonium chloride, and benzyltriethylammonium chloride.
  • Examples of the alkylamine salt include monomethylamine hydrochloride, dimethylamine hydrochloride, and trimethylamine hydrochloride.
  • Examples of the compound having a pyridine ring include butylpyridinium chloride, dodecylpyridinium chloride, and cetylpyridinium chloride.
  • anionic surfactant examples include carboxylate, sulfonate, sulfate ester salt, and phosphate ester salt.
  • carboxylate examples include sodium octanoate, sodium decanoate, sodium laurate, sodium myristate, sodium palmitate, and sodium stearate.
  • sulfonate examples include sodium 1-hexanesulfonate, sodium 1-octanesulfonate, sodium 1-decanesulfonate, sodium 1-dodecanesulfonate, perfluorobutanesulfonic acid, sodium linear alkylbenzenesulfonate, toluenesulfone.
  • Examples include sodium acid, sodium cumene sulfonate, sodium octylbenzene sulfonate, sodium naphthalene sulfonate, disodium naphthalene disulfonate, trisodium naphthalene trisulfonate, and sodium butyl naphthalene sulfonate.
  • sulfate salts include sodium lauryl sulfate, sodium myristyl sulfate, sodium laureth sulfate, sodium polyoxyethylene alkylphenol sulfonate, and ammonium lauryl sulfate.
  • Examples of phosphate ester salts include sodium lauryl phosphate and potassium lauryl phosphate.
  • amphoteric surfactants include alkyl betaine salts, fatty acid amidopropyl betaine salts, alkyl imidazole salts, amino acid salts, and amine oxide salts.
  • alkylbetaine salts include lauryldimethylaminoacetic acid betaine, stearyldimethylaminoacetic acid betaine, dodecylaminomethyldimethylsulfopropylbetaine, and octadecylaminomethyldimethylsulfopropylbetaine.
  • the fatty acid amidopropyl betaine salt include cocamidopropyl betaine and cocamidopropyl hydroxysultain.
  • alkyl imidazole salt examples include 2-alkyl-N-carboxymethyl-N-hydroxyethyl imidazolinium betaine.
  • amino acid salts include sodium lauroyl glutamate, potassium lauroyl glutamate, and lauroylmethyl- ⁇ -alanine.
  • amine oxide salt examples include lauryldimethylamine-N-oxide and oleyldimethylamine-N-oxide.
  • nonionic surfactants include ester type compounds, ether type compounds, and ether / ester type compounds.
  • ester compounds include glycerin fatty acid esters such as diglycerin monostearate; polyoxyethylene (5) hydrogenated castor oil, polyoxyethylene (7) hydrogenated castor oil, polyoxyethylene (10) hydrogenated castor oil, poly Oxyethylene (20) hydrogenated castor oil, polyoxyethylene (30) hydrogenated castor oil, polyoxyethylene (40) hydrogenated castor oil, polyoxyethylene (50) hydrogenated castor oil, polyoxyethylene (60) hydrogenated castor oil, poly Polyoxyethylene hydrogenated castor oil such as oxyethylene (100) hydrogenated castor oil; polyoxyethylene (3) glyceryl monoisostearate, polyoxyethylene (6) glyceryl monoisostearate, polyoxyethylene (8) glyceryl monoiso Stearate, polyoxye Len (10) glyceryl monoisostearate, polyoxyethylene (15) glyceryl monoisostearate, polyoxyethylene (20) glyceryl monoisostearate, polyoxyethylene (30) glyceryl monoisostearate,
  • ether type compounds include polyoxyethylene alkyl phenyl ethers such as polyoxyethylene octyl phenyl ether and polyoxyethylene nonyl phenyl ether, and polyoxyethylene alkyl ethers.
  • ether-ester type compound examples include polyoxyethylene (5) cetyl ether stearate and polyoxyethylene (10) cetyl ether stearate.
  • an ester type compound is preferable from the viewpoint of safety, and a polyoxyethylene glycerin fatty acid ester is more preferable.
  • polyoxyethylene glycerin having a fatty acid ester having 10 to 20 carbon atoms such as polyoxyethylene glyceryl monostearate, polyoxyethylene glyceryl monoisostearate, glyceryl polyoxyethylene oleate, polyoxyethylene glyceryl triisostearate is preferable.
  • the content (total) of these ester compounds in the surfactant (C) is, for example, 30% by weight or more (preferably 50% by weight or more, particularly preferably 70% by weight or more).
  • the cleansing cosmetic composition of the present invention is one of the components used in normal cleansing cosmetic compositions (hereinafter sometimes referred to as “other components”) as long as the effects of the present invention are not impaired. Or you may contain 2 or more types. Examples of the other components include preservatives, antibacterial agents, flame retardants, astringents, moisturizers, antioxidants, lower alcohols, water, colorants, and fragrances.
  • the content of the compound (1) [compound represented by the formula (1)] (the total amount when two or more compounds are contained) is the cleansing cosmetic composition.
  • the lower limit is preferably 1.0% by weight.
  • the upper limit is preferably 7.0% by weight, particularly preferably 5.0% by weight.
  • the cleansing cosmetic composition of the present invention may contain a thickener other than the compound (1) as the thickener (A), but the compound (1) in all the thickeners contained in the cleansing cosmetic composition. ) Is, for example, 30.0% by weight or more, preferably 50.0% by weight or more, particularly preferably 70.0% by weight or more, and most preferably 85.0% by weight or more. If the content of the other thickener is excessive, the effect of the present invention tends to be difficult to obtain.
  • the content of the thickener (A) in the cleansing cosmetic composition of the present invention can be appropriately adjusted according to the use, but the oil agent (B ) 100 parts by weight, for example, about 0.5 to 50.0 parts by weight (preferably 1.0 to 30.0 parts by weight, more preferably 1.5 to 20.0 parts by weight).
  • the thickener (A) is, for example, 0.5 to 30.0% by weight, preferably 1.% by weight based on the sum of the contents of the thickener (A) and the oil (B). 0 to 25.0% by weight, more preferably 2.0 to 20.0% by weight, still more preferably 2.5 to 15.0% by weight.
  • the oil agent (B) is added in an amount of 70.0 to 99.5% by weight, preferably 75.0 to 99.0% by weight, based on the sum of the contents of the thickener (A) and the oil agent (B).
  • the content is preferably 80.0 to 98.0% by weight, more preferably 85.0 to 95.0% by weight.
  • the compound (1) is added in an amount of 0.5 to 30.0% by weight, preferably 1.0 to 25%, based on the sum of the contents of the thickener (A) and the oil (B). 0.0 wt%, more preferably 2.0 to 20.0 wt%, still more preferably 5.0 to 15.0 wt%.
  • the thickener can appropriately thicken and stabilize the oil.
  • the content of the oil agent (B) in the cleansing cosmetic of the present invention is, for example, about 40.0 to 99.0% by weight with respect to the total amount of the cleansing cosmetic, and the lower limit is Preferably it is 50.0% by weight, particularly preferably 60.0% by weight, and most preferably 60.0% by weight.
  • the upper limit is preferably 90.0% by weight, particularly preferably 85.0% by weight, and most preferably 80.0% by weight.
  • the cleansing cosmetic containing the oil agent (B) in the above range is excellent in cleaning performance of oily dirt, and excellent in usability and dischargeability.
  • the sum of the contents of the thickener (A) and the oil (B) is, for example, 10.0% by weight or more, preferably 20.0 to 95. It is 0% by weight, particularly preferably 30.0 to 90.0% by weight.
  • the cleansing cosmetic containing the thickener (A) and the oil agent (B) in the above range is excellent in the detergency of oily dirt, and excellent in usability and dischargeability.
  • the cleansing cosmetic composition of the present invention contains about 5.0 to 50.0 parts by weight of the surfactant (C) with respect to 100 parts by weight of the sum of the contents of the thickener (A) and the oil (B). Is preferred.
  • the lower limit of the sum of the contents is preferably 10.0 parts by weight, particularly preferably 15.0 parts by weight, and most preferably 20.0 parts by weight.
  • the upper limit of the sum of the contents is preferably 40.0 parts by weight, particularly preferably 35.0 parts by weight, and most preferably 30.0 parts by weight.
  • the cleansing cosmetic containing the surfactant (C) in the above range is particularly excellent in the detergency of oily dirt.
  • the content of the surfactant (C) in the cleansing cosmetic of the present invention is, for example, about 3.0 to 50.0% by weight with respect to the total amount of the cleansing cosmetic.
  • the lower limit is preferably 5.0% by weight, particularly preferably 10.0% by weight, and most preferably 15.0% by weight.
  • the upper limit is preferably 40.0% by weight, particularly preferably 30.0% by weight, and most preferably 25.0% by weight.
  • the cleansing cosmetic containing the surfactant (C) in the above range is particularly excellent in the detergency of oily dirt.
  • the total content of the thickener (A), the oil agent (B), and the surfactant (C) is, for example, 60.0% by weight or more, preferably 70.0% by weight, based on the total amount of the cleansing cosmetic. Above, particularly preferably 80.0% by weight or more, most preferably 90.0% by weight or more.
  • the content of the other components in the cleansing cosmetic of the present invention is, for example, about 10.0% by weight or less, preferably 7.0% by weight or less, particularly preferably 5.0% by weight or less, based on the total amount of the cleansing cosmetic. It is.
  • the viscosity [at 25 ° C., shear rate of 10 s ⁇ 1 ] of the cleansing cosmetic of the present invention is, for example, about 300 to 3000 mPa ⁇ s, preferably 500 to 3000 mPa ⁇ s, particularly preferably 1000 to 3000 mPa ⁇ s, most preferably 2000. ⁇ 3000 mPa ⁇ s.
  • the viscosity [at 25 ° C., shear rate of 10 s ⁇ 1 ] of the cleansing cosmetic of the present invention is, for example, about 300 to 3000 mPa ⁇ s, preferably 500 to 3000 mPa ⁇ s, particularly preferably 1000 to 3000 mPa ⁇ s, most preferably 2000. ⁇ 3000 mPa ⁇ s.
  • the viscosity exceeds the above range, the dischargeability and usability tend to be reduced. If the viscosity is below the above range, it may scatter during discharge, or may fall from between fingers when picked up. In some cases, the liquid may leak from the discharge port and contaminate the container.
  • the cleansing cosmetic of the present invention may be aqueous (including oil-in-water type) or oily.
  • the cleansing cosmetic composition of the present invention may be in any form such as oil (cleansing oil), gel (cleansing gel), cream (cleansing cream), milk (cleansing milk) and the like.
  • seat etc. may be sufficient.
  • the cleansing cosmetic composition of the present invention is oily or milky.
  • the cleansing cosmetic composition of the present invention has the above-mentioned characteristics, it can be used for oily stains such as skin stains and makeup stains caused by oily cosmetics (for example, foundation, sunscreen cosmetics, lipstick, mascara) by lightly massaging with fingers. It can be blended and then washed off with water to remove it cleanly. Further, when filling a pump-type container, it can be discharged without being scattered, and dripping from the discharge port can be suppressed. Therefore, the cleansing cosmetic composition of the present invention is particularly suitable as a cleansing cosmetic composition for oily soil that is used by filling a pump-type container.
  • oily cosmetics for example, foundation, sunscreen cosmetics, lipstick, mascara
  • the cleansing cosmetic composition of the present invention can be produced, for example, through a step of making the thickener (A) and the oil agent (B) compatible. More specifically, the total amount of the thickener (A) and the oil agent (B) is mixed and heated, and after being dissolved, cooled, further cooled, and then added with the surfactant (C). Can be manufactured. Further, the thickener (A) may be mixed with a part of the oil agent (B), heated and compatible, then cooled, and then mixed with the remaining oil agent (B). it can.
  • the temperature at the time of compatibility is appropriately selected depending on the types of the thickener (A) and the oil agent (B), and is not particularly limited, but preferably does not exceed 100 ° C., and the boiling point of the oil agent (B) is In the case of 100 ° C. or lower, the boiling point is preferable. Cooling after the compatibilization may be performed as long as it can be cooled to room temperature (for example, 25 ° C. or less), and may be gradually cooled at room temperature, or may be rapidly cooled by ice cooling or the like.
  • N-dimethylformamide (40 ml) solution N-docosanoylethylenediamine (12.0 g, 31.4 mmol) obtained above, triethylamine (6.35 g, 62.8 mmol) and succinic anhydride (3.45 g) were added. 34.5 mmol) was added over 10 minutes, followed by stirring at 100 ° C. for 15 minutes to allow the reaction while dissolving succinic anhydride. After the reaction, acetic anhydride (4.81 g, 47.1 mmol) was further added dropwise to the reaction crude liquid over 10 minutes, followed by stirring at 100 ° C. for 1 hour for reaction.
  • N-docosanoylaminoethylsuccinimide (4.00 g, 8.60 mmol) and N, N-dimethyl-1,3-propanediamine (2.63 g, 25.8 mmol) were stirred at 120 ° C. for 18 hours. And reacted.
  • the reaction mixture was poured into methanol and the precipitate was filtered and washed with methanol. After washing, the obtained solid was purified by recrystallization using acetone and methanol.
  • N- (docosanoylaminoethylaminosuccinamoylaminopropyl) -N, N-dimethylamine (4.58 g, 8.08 mmol) represented by the following formula (2-3) as a white crystalline powder: Yield 94%).
  • N- (docosanoylaminoethylaminosuccinamoylaminopropyl) -N, N-dimethylamine oxide (2.84 g, 4.87 mmol, represented by the following formula (1-3) as a white solid Yield 69%).
  • N-docosanoylaminoethylsuccinimide (8.00 g, 17.2 mmol) and hexamethylenediamine (10.0 g, 86.1 mmol) were stirred and reacted at 120 ° C. for 18 hours.
  • the reaction mixture was poured into methanol and the precipitate was filtered and washed with methanol. After washing, the obtained solid was recrystallized using acetonitrile and methanol as a solvent and purified. After purification, N- (docosanoylaminoethyl) aminosuccinamoylaminohexylamine (6.91 g, 11.9 mmol, 69% yield) was obtained as a white crystalline powder.
  • N- (docosanoylaminoethyl) aminosuccinamoylaminohexylamine (3.25 g, 5.59 mmol), 37% aqueous formaldehyde solution (2.73 ml) and formic acid (1.55 g, 33.7 mmol) obtained above was dissolved in 2-propanol (15 ml) and reacted by stirring at 100 ° C. for 4 hours.
  • the reaction mixture was poured into 1M aqueous sodium hydroxide solution (20 ml), and crystals precipitated from the reaction mixture were filtered.
  • N-eicosanoylaminoethylsuccinimide (4.00 g, 9.16 mmol) and N, N-dimethyl-1,3-propanediamine (2.81 g, 27.5 mmol) obtained above were added at 120 ° C. for 18 hours. Stir to react. The reaction mixture was poured into methanol and the precipitate was filtered and washed with methanol. The obtained solid was purified by recrystallization using acetone and methanol. After purification, N- (eicosanoylaminoethylaminosuccinamoylaminopropyl) -N, N-dimethylamine represented by the following formula (2-1) as a white crystalline powder (4.49 g, 8. 34 mmol, yield 91%).
  • N- (eicosanoylaminoethylaminosuccinamoylaminopropyl) -N, N-dimethylamine (4.00 g, 7.42 mmol), 35% aqueous hydrogen peroxide (2.16 ml) and 2 -Propanol (10 ml) was reacted at 60 ° C. with stirring for 5 hours. Furthermore, palladium carbon (about 10 mg) was added to the reaction solution, and the mixture was stirred at room temperature for 18 hours to be reacted. The reaction solution was filtered and the solvent was distilled off, followed by purification by column chromatography (filler: silica gel, developing solvent: mixed solvent of 2-propanol and methanol).
  • N- (eicosanoylaminoethylaminosuccinamoylaminopropyl) -N, N-dimethylamine oxide (2.39 g, 4.30 mmol, represented by the following formula (1-1) as a white solid: Yield 58%).
  • Synthesis Example 4 ⁇ Production of Compound (1-5)> A compound represented by the following formula (2-5) was obtained in the same manner as in Synthesis Example 2 except that methyl octadecanoate was used instead of methyl docosanoate, and then represented by the following formula (1-5). A compound was obtained.
  • Synthesis Example 5 ⁇ Production of Compound (1-6)> A compound represented by the following formula (2-6) was obtained in the same manner as in Synthesis Example 1 except that methyl octadecanoate was used instead of methyl docosanoate, and then represented by the following formula (1-6). A compound was obtained.
  • Synthesis Example 6 ⁇ Production of Compound (1-7)> A compound represented by the following formula (2-7) was obtained in the same manner as in Synthesis Example 2 except that methyl palmitate was used instead of methyl docosinate, and then represented by the following formula (1-7). A compound was obtained.
  • Synthesis Example 7 ⁇ Production of Compound (1-8)> A compound represented by the following formula (2-8) was obtained in the same manner as in Synthesis Example 1 except that methyl palmitate was used instead of methyl docosanoate, and then represented by the following formula (1-8). A compound was obtained.
  • Synthesis Example 8 ⁇ Production of compound (1-9)> A compound represented by the following formula (2-9) was obtained in the same manner as in Synthesis Example 2 except that methyl myristate was used in place of methyl docosinate, and then represented by the following formula (1-9). A compound was obtained.
  • Example 1 Preparation of cleansing cosmetics 2 parts by weight of the compound (1-1) obtained in Synthesis Example 3 as a thickener (A) and cetyl octanoate (trade name “CEH”, manufactured by Higher Alcohol Industry Co., Ltd.) as an oil agent (B) ) 78 parts by weight, mixed by heating and stirring at 80 ° C., and then cooled to 25 ° C. to obtain an oil composition.
  • the obtained oil composition was mixed with a surfactant (C).
  • the cleansing cosmetic obtained above is filled in a pump-type container with a nozzle discharge port of 2.5 mm in diameter and 1.5 mL in discharge volume, and used by 20 female panelists for 2 weeks. Usability (can we prevent dripping at the discharge port and splashing at the time of discharge), feeling of cleansing cosmetics (does not fall off between fingers when picked up by hand, or spreadability is good), and Ease of washing is evaluated on a scale of 5 (+2: very good, +1: good, 0: normal, -1: bad, -2: very bad).
  • the cleansing cosmetics were comprehensively evaluated according to [Evaluation criteria] ⁇ : 1.0 point or more ⁇ : 0 point or more, less than 1.0 point ⁇ : Less than 0 point
  • cetyl octanoate trade name “CEH”, polyoxyethylene (10) glyceryl monoisostearate manufactured by Higher Alcohol Industry Co., Ltd .: trade name “EMALEX GWIS-110”, polyoxyethylene (8) manufactured by Nippon Emulsion Co., Ltd.
  • Glyceryl monoisostearate trade name “EMALEX GWIS-108”, manufactured by Nippon Emulsion Co., Ltd.
  • the cleansing cosmetics of the present invention of Examples 1 to 8 were evaluated to be excellent in usability and usability when used in a pump-type container and easily washed away with water.
  • Comparative Example 1 that is, when the thickener (A) was not used, the cleansing cosmetic was likely to splatter at the time of discharge, and the liquid was easily drained from the discharge port. Also, it was difficult to use because it fell from between fingers. For this reason, it was inferior to the usability by a pump type container, and it was evaluated that a usability
  • a cleansing cosmetic comprising a thickener (A), an oil agent (B), and a surfactant (C), wherein a compound represented by the following formula (1) is used as the thickener (A): 0.5 to 30.0% by weight based on the sum of the contents of the thickener (A) and the oil agent (B), and the oil agent (B)
  • a cleansing cosmetic comprising 70.0 to 99.5% by weight based on the sum of the contents.
  • R 1 is a monovalent linear aliphatic hydrocarbon group having 10 to 25 carbon atoms
  • R 2 and R 3 are the same or different and are divalent having 2, 4, 6, or 8 carbon atoms.
  • R 4 represents an aliphatic hydrocarbon group, a bivalent alicyclic hydrocarbon group having 6 carbon atoms, or a divalent aromatic hydrocarbon group, and R 4 represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms.
  • R 5 and R 6 are the same or different and represent a monovalent aliphatic hydrocarbon group having 1 to 3 carbon atoms or a hydroxyalkyl ether group, L 1 to L 3 represent an amide bond, and L 1 and When L 3 is —CONH—, L 2 is —NHCO—, and when L 1 and L 3 are —NHCO—, L 2 is —CONH—.)
  • R 1 is a monovalent linear aliphatic hydrocarbon group having 14 to 25 carbon atoms (preferably 18 to 21 carbon atoms) (preferably an alkyl group having 14 to 25 carbon atoms). Cleansing cosmetics according to].
  • R 2 and R 3 are a divalent linear alkylene group having 2, 4, 6, or 8 carbon atoms.
  • R 4 is a divalent linear or branched alkylene group having 1 to 8 carbon atoms (preferably 3 to 6 carbon atoms).
  • R 5 and R 6 are a linear or branched alkyl group having 1 to 3 carbon atoms, a linear or branched alkenyl group having 2 to 3 carbon atoms, or a straight chain having 2 to 3 carbon atoms.
  • the cleansing cosmetic according to any one of [1] to [9], wherein the surfactant (C) comprises a nonionic surfactant.
  • the sum of the contents of the thickener (A) and the oil (B) is 10.0% by weight or more based on the total amount of the cleansing cosmetic.
  • the content of the compound represented by the formula (1) is 0.1 to 10.0% by weight with respect to the total amount of the cleansing cosmetic, [1] to [11] Cleansing cosmetics.
  • the content of the thickener (A) is 0.5 to 50.0 parts by weight with respect to 100 parts by weight of the oil (B), according to any one of [1] to [12] Cleansing cosmetics.
  • the content of the compound represented by the formula (1) is 0.5 to 30.0% by weight based on the sum of the contents of the thickener (A) and the oil (B).
  • the cleansing cosmetic according to any one of to [13].
  • the content of the surfactant (C) is 5.0 to 50.0 parts by weight based on 100 parts by weight of the sum of the contents of the thickener (A) and the oil (B).
  • the cleansing cosmetic according to any one of [15] to [15].
  • the cleansing cosmetic of the present invention can be used for the purpose of removing oily dirt on the skin such as dirt due to sebum and makeup cosmetics.
  • oily dirt on the skin such as dirt due to sebum and makeup cosmetics.
  • it is difficult to sag when it is picked up by the hand, has excellent spreadability, and is particularly excellent in dischargeability when filled in a pump-type container.

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Abstract

L'invention concerne un produit cosmétique de nettoyage qui présente un excellent pouvoir détergent contre les taches huileuses et peut être rincé à l'eau, et qui est peu susceptible de s'égoutter lorsqu'il est distribué dans la main, présente une excellente extensibilité, et en particulier, peut être éjecté facilement lorsqu'il est rempli dans un récipient de type pompe. La présente invention concerne un produit cosmétique de nettoyage comprenant un agent épaississant (A), une solution huileuse (B) et un tensioactif (C), un composé représenté par la formule (1) étant inclus en tant qu'agent épaississant (A) en une quantité de 0,5 à 30,0 % en poids par rapport à la teneur totale de l'agent épaississant (A) et de la solution huileuse (B), et le contenu de la solution huileuse (B) représente 70,0 à 99,5 % en poids de la teneur totale de l'agent épaississant (A) et de la solution huileuse (B).
PCT/JP2019/011607 2018-03-30 2019-03-19 Produit cosmétique de nettoyage Ceased WO2019188623A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021149502A1 (fr) * 2020-01-22 2021-07-29 株式会社ダイセル Composition et son procédé de production

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005082839A1 (fr) * 2004-03-01 2005-09-09 Kao Corporation Compose amide
JP2011102256A (ja) * 2009-11-10 2011-05-26 Adeka Corp オイル用増粘剤およびこれを含むオイル組成物
WO2015190433A1 (fr) * 2014-06-09 2015-12-17 株式会社ダイセル Démaquillant
JP2016030765A (ja) * 2014-07-25 2016-03-07 シーシーアイ株式会社 ヒドロゲル化剤

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005082839A1 (fr) * 2004-03-01 2005-09-09 Kao Corporation Compose amide
JP2011102256A (ja) * 2009-11-10 2011-05-26 Adeka Corp オイル用増粘剤およびこれを含むオイル組成物
WO2015190433A1 (fr) * 2014-06-09 2015-12-17 株式会社ダイセル Démaquillant
JP2016030765A (ja) * 2014-07-25 2016-03-07 シーシーアイ株式会社 ヒドロゲル化剤

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
KAKEHASHI, RIE ET AL.: "Effects of the spacer length on the aggregate formation and the gelation of alkylamide amine oxides", COLLOID AND POLYMER SCIENCE, vol. 293, 5 June 2015 (2015-06-05), pages 3157 - 3165, XP035878329, doi:10.1007/s00396-015-3634-4 *
KAKEHASHI, RIE ET AL.: "Solution Behavior of Long-alkyl-chain Amide Amine Oxide Surfactants Having Multiple Hydrogen-bonding Sites", CHEM. LETT., vol. 41, 15 September 2012 (2012-09-15), pages 1050 - 1051, XP055638925 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021149502A1 (fr) * 2020-01-22 2021-07-29 株式会社ダイセル Composition et son procédé de production
CN115038689A (zh) * 2020-01-22 2022-09-09 株式会社大赛璐 组合物及其制造方法

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