WO2002051939A1 - Composition sous forme de gel - Google Patents

Composition sous forme de gel Download PDF

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Publication number
WO2002051939A1
WO2002051939A1 PCT/JP2001/011238 JP0111238W WO02051939A1 WO 2002051939 A1 WO2002051939 A1 WO 2002051939A1 JP 0111238 W JP0111238 W JP 0111238W WO 02051939 A1 WO02051939 A1 WO 02051939A1
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WO
WIPO (PCT)
Prior art keywords
polymer
associative
production example
composition according
acid
Prior art date
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PCT/JP2001/011238
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English (en)
Japanese (ja)
Inventor
Katsunori Yoshida
Isamu Kaneda
Toshio Yanaki
Original Assignee
Shiseido Co., Ltd.
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
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Application filed by Shiseido Co., Ltd. filed Critical Shiseido Co., Ltd.
Priority to JP2002553422A priority Critical patent/JPWO2002051939A1/ja
Publication of WO2002051939A1 publication Critical patent/WO2002051939A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • 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
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/894—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/042—Gels
    • 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
    • A61K8/89—Polysiloxanes
    • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
    • 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
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
    • C08L83/12—Block- or graft-copolymers containing polysiloxane sequences containing polyether sequences

Definitions

  • the present invention relates to an improvement in a gel composition, particularly an associative polymer having a silicone group. [Background technology]
  • Japanese Patent No. 2682966 describes a cosmetic composition containing a polysiloxane-polyoxyalkylene linear block copolymer.
  • the above-mentioned block copolymer is used as a fine dispersant of a non-volatile insoluble silicone or a conditioning agent selected from fluorinated oils or waxes. Due to the large proportion of polysiloxane (hydrophobic chain portion) occupying, it was insoluble in water and did not show a thickening effect in water.
  • the present invention has been made in view of the problems of the related art, and has as its object to provide a gel composition containing an associative polymer, which has viscosity and has a non-greasy and refreshing feel.
  • R i to R 4 are the same or different hydrocarbon groups, and Y is selected from the group consisting of a hydroxyl group, an alkylene oxide, or a residue of urethane, ether, ester, or urea.
  • A is one or more selected from the group consisting of urethane, ether, ester, and urea residues
  • Z is one or more selected from the group consisting of urethane, ether, ester, and urea residues.
  • One or more selected from the group consisting of hydrocarbon groups or urethane, ether, ester, and urine residues a is an average of 2 or more, b is an average of 10 to 300, and c is an average 1 to 500.
  • the molecular weight of the associative polymer is preferably 600 or more. is there.
  • the mass fraction of the silicone chain in the associative polymer is 0.1 or less.
  • a of the associative polymer represented by the formula (I) is polyethylene oxide.
  • the associative polymer is preferably a multi-block polymer.
  • the associative polymer is a triplock polymer.
  • the multi-block polymer is a double-ended silicone type block polymer.
  • a of the associative polymer represented by the formula (I) is 2, b is 65 or more, and c is 3 to 105.
  • the content of the associative polymer is 0.1 to 5% by mass.
  • composition it is good suitable oil which is a 0.1 to 2 5 mass 0/0 containing emulsion.
  • the associative polymer according to the present invention is a silicone-modified alkylene oxide sequential polymer, and generally has an alkylene oxide, preferably ethylene oxide, and a hydrophilic polymer such as Z or a copolymer thereof in the chain. It is a non-ionic sequencial copolymer that contains both the hydrophobic sequences and the hydrophobic chains of the silicone chain.
  • theta-encyanole copolymer has the meaning of a block copolymer.
  • the polymer can be sequential in the form of a triblock (tri_block) as in the general formula (II) or a multi-block as in the general formula (III). BCACB... (II)
  • a hydrophobic linking moiety can be present at each end of the chain (eg, a triblock copolymer with a central hydrophilic linking moiety) or can be located in the chain or at both ends of the chain.
  • Yes eg, multi-sequential copolymer.
  • the polymer may be a graft copolymer.
  • the HLB value of the associative polymer according to the present invention is suitably from 16.0 to 19.5, and most preferably from 17.0 to 19.4. If it is less than 16.0 or more than 19.5, it may not show a thickening effect. .
  • the molecular weight of the associative polymer according to the present invention is preferably 6000 or more, and most preferably 8000 or more. If it is less than 6000, the network of the meeting may not be developed.
  • the mass fraction of the silicone chain is preferably 0.1 or less, more preferably 0.05 or less. If it exceeds 0.1, the solubility in water may be reduced, and there may be no viscous effect.
  • a of the associative polymer represented by the formula (I) is 2, b is 65 or more, and c is 3 to 105.
  • a force S2 is 65 or more and c is 3 to 105, and it is particularly preferable that a is 2, 2 is 75 or more, and c is 5 to 70.
  • the content of the associative polymer is preferably from 0.1 to 5% by mass, and most preferably from 0.5 to 2% by mass. 0.1 mass. If it is less than / 0 , the effect of the present invention may not be sufficient, and if it exceeds 5% by mass, the viscosity may be too high and the usability may be unfavorable.
  • the composition of the present invention further has an oil content of 0.1 to 25 mass. / 0 can be included.
  • vegetable oils such as olive oil and castor oil, boxes such as carnauba wax and candelilla wax, liquid paraffin, squalane, petrolatum, hydrocarbon oils such as polyethylene oxide propylene oxide alkyl ether, lauric acid, stearic acid , Higher fatty acids such as sostearic acid and 12-hydroxystearic acid, cetyl alcohol Higher alcohols such as glue, stearyl alcohol, behenyl alcohol, etc., esters such as isopropyl myristate, cetyl 2-ethylhexanoate, jetoxestenole succinate, methyl polysiloxane, methyl phenyl polysiloxane, long chain alkyl Silicone oil such as siloxane may be included.
  • composition can be in any pharmaceutical formulation suitable for topical application, in particular water-in-oil (W / O) or oil-in-water (O / W) or triple (W / O) / O / W or OZW / O) can be provided in the form of a dispersion or emulsion.
  • W / O water-in-oil
  • O / W oil-in-water
  • OZW / O triple
  • the composition of the present invention preferably has a viscosity range of 0.1 to 10 OPa ⁇ s, more preferably 1 to 5 OPa ⁇ s, wherein the viscosity at 25 ° C is Brookfield type. It is measured using a viscometer. This is true whether it is an aqueous gel, an emulsion or a dispersion.
  • the gel-like composition may further comprise any additional components conventionally used in the cosmetic and / or dermatological field.
  • anionic surfactants such as fatty acid soaps, alkyl sulfates, polyoxyethylene alkyl ether sulfates, acyl-N-methyltadulinates, alkyl ether phosphates, N-acylaminates, and organic acid monoglycerides
  • cationic surfactants such as salted alkytrimethylammonium, dialkyldimethylammonium chloride, benzalcodium chloride, alkylpyridinium chloride, betaine alkyldimethylaminoacetate, and alkylamidedimethylaminoacetate Tyne, 2-alkyl-1-N-carboxy-1-N-hydroxyimidazolinidum betaine
  • amphoteric surfactants such as lecithin, enzymatically degraded lecithin, alkyl polyoxyethylene type, polyhydric alcohol esterative, acy
  • UV absorbers such as molecules, high molecular weight silicones, benzophenone derivatives, paraaminobenzoic acid derivatives, and methoxycinnamic acid derivatives; antioxidants such as tocopherol and BHT; EDTA, cunic acid, hexamethalic acid, and pyrosulfite Metal sequestering agents, fine emulsions such as silicone mic mouth emulsions, high pressure emulsified mic mouth emulsions, alcohols, and the like.
  • Further effective ingredients include, for example, whitening agents such as alptin, ascorbic acid and its derivatives, anti-aging agents such as retinol and its derivatives, ⁇ - hydroxy acids such as lactic acid and glycolic acid, hair restorers, vitamins, anti-inflammatory agents, It can contain fungicides, various salts, etc.
  • the form of use is also optional.
  • lotion, cream, milky lotion, lotion, pack, ointment, mousse, and soap foundation, eye shadow, stain, kuma cover, lip balm, mascara, lipstick, body
  • Make-up cosmetics such as make-up products, hair rinses, shampoos, sunscreen or tanning creams for the skin, as well as dermatological ointments and bath preparations, etc., which are used in conventional cosmetics and / or dermatological areas Any configuration can be used.
  • a container equipped with a thermometer, a nitrogen inlet tube and a stirrer l In a four-neck OO OmL flask, add 40 parts of polyethylene glycol (PEG) (molecular weight: about 20,000) and 300 parts of toluene and melt at 70 ° C did. After azeotropically removing water, at 80 ° C, 0.7 parts of hexamethylene diisocyanate, 0.03 parts of dibutyltin lauric acid, dimethyl silicone having a hydroxyl group terminal (FM0411, manufactured by Nisso, molecular weight 4 parts were added, and the mixture was reacted overnight at 70 ° C under a nitrogen stream, and the reaction was stopped by adding water. Remove the solvent and select the desired polymer:? Pita.
  • PEG polyethylene glycol
  • a container equipped with a thermometer, a nitrogen inlet tube and a stirrer l In a four-neck flask of OO OmL, add 40 parts of poly (ethylene glycol) (PEG) (molecular weight: about 20,000) and 300 parts of toluene, and place at 70 ° C. And dissolved. After azeotropically removing water, 3 parts of epoxy-terminated methylsilicone (FM0511, manufactured by Chisso, molecular weight: about 1,000) and 0.3 parts of potassium laurate are added, and the mixture is heated at 70 ° C under a nitrogen stream. The reaction was allowed to proceed overnight, and the reaction was stopped by adding ethanol. The solvent was removed to obtain the desired polymer.
  • PEG poly (ethylene glycol)
  • FM0511 epoxy-terminated methylsilicone
  • a container equipped with a thermometer, a nitrogen inlet tube and a stirrer l In a four-neck OO OmL flask, add 40 parts of polyethylene glycol (PEG) (molecular weight: about 20,000) and 300 parts of toluene and melt at 70 ° C did. After azeotropically removing water, 4 parts of dimethyl silicone having a hydroxyl group terminal (FM0411, manufactured by Nisso, molecular weight: about 1,000), polyethylene glycol diglycidyl ether (Denacol EX 810, manufactured by Nagase Kasei Kogyo) 0.7 And 0.07 part of potassium hydroxide were added thereto, and the mixture was reacted overnight at 70 ° C. under a nitrogen stream, and the reaction was stopped by adding ethanol. The solvent was removed to obtain the desired polymer.
  • PEG polyethylene glycol
  • FM0411 dimethyl silicone having a hydroxyl group terminal
  • Denacol EX 810 manufactured by Nagase
  • a container equipped with a thermometer, a nitrogen inlet tube and a stirrer l In a four-neck OO OmL flask, add 20 parts of polyethylene glycol (PEG) (molecular weight: about 35,000) and 300 parts of toluene and melt at 70 ° C did. After azeotropically removing water, add 4 parts of dimethyl silicone having epoxy groups at both ends (FM0511, manufactured by Chisso, molecular weight: about 1,000) and 0.3 part of potassium laurate, and add 70 ° C under a nitrogen stream. The reaction was allowed to proceed overnight at C, and the reaction was stopped by adding ethanol. The solvent was removed to obtain the desired polymer.
  • PEG polyethylene glycol
  • PEG poly (ethylene glycol)
  • toluene 300 parts
  • hydroxyl-terminated dimethyl silicone (FM0411, manufactured by Nisso, molecular weight approx. 1,000) 25 parts ethylene oxide 25 mol adduct 6 parts, adipic acid 0.6 part, sodium hydroxide 0.1 part was added and reacted overnight at 70 ° C under a nitrogen stream. The solvent was removed to obtain the desired polymer.
  • a container equipped with a thermometer, a nitrogen inlet tube and a stirrer l In a four-neck OO OmL flask, add 40 parts of polyethylene glycol (PEG) (molecular weight: about 20,000) and 300 parts of toluene and melt at 70 ° C did. After azeotropically removing water, dimethyl ⁇ / silicone having hydroxyl groups at both ends (FM441J manufactured by Chisso, molecular weight approx. 1,000) 9 parts of 25 mol ethylene oxide adduct, 1.2 parts of didipic acid Then, 1 part of sodium hydroxide was added, and the mixture was reacted overnight at 70 ° C under a nitrogen stream. The solvent was removed to obtain the desired polymer.
  • PEG polyethylene glycol
  • a container equipped with a thermometer, a nitrogen inlet tube and a stirrer l In a four-necked OOO mL flask, 70 parts of poly (ethylene glycol) (PEG) (molecular weight: about 35,000) and 300 parts of toluene were added and dissolved at 70 ° C. . After azeotropically removing water, at 80 ° C 0.7 parts of hexamethylene diisocyanate, 0.03 parts of dibutyltin lauric acid, dimethyl silicone having an amino group end (molecular weight: about 1,000) 4 The reaction was continued overnight at 70 ° C under a nitrogen stream, and water was added to stop the reaction. The solvent was removed to obtain the desired polymer.
  • PEG poly (ethylene glycol)
  • a container equipped with a thermometer, a nitrogen inlet tube and a stirrer l In a OO OmL four-necked flask, put 70 parts of polyethylene glycol (PEG) (molecular weight: about 35,000) and 300 parts of tomerene at 70 ° C. Dissolved. After azeotropically removing water, at 80 ° C 1.1 parts of hexamethylene diisocyanate, 0.03 part of dibutinoresuzulauric acid, dimethyl silicone having both terminal amino groups (FM4421, nitrogen And a molecular weight of about 5,000), and the mixture was allowed to react overnight at 70 ° C. under a nitrogen stream, and the reaction was stopped by adding water. The solvent was removed to obtain the desired polymer.
  • PEG polyethylene glycol
  • the polymer obtained in Production Example 10 has 1 ⁇ to 4 and Z
  • CH 3 , A, and Y are —CH 2 CH 20 —
  • X is a residue of an ether bond
  • a small amount of pyridine was added to 1.6 parts of chloride and 300 parts of toluene.
  • Forty parts of polyethylene glycol (PEG) (molecular weight: about 20,000), which had been methanolized with diphenylmethane methane beforehand, were added and reacted at 70 ° C under a nitrogen stream. The solvent was removed to obtain the desired polymer.
  • PEG polyethylene glycol
  • a container equipped with a thermometer, a nitrogen inlet tube and a stirrer l In a four-neck OO OmL flask, add 40 parts of poly (ethylene glycol) (PEG) (molecular weight: about 20,000) and 300 parts of Tonolen at 70 ° C. Dissolved. After azeotropically removing water, at 80 ° C, 0.7 parts of hexamethylenedidisocyanate, 0.03 parts of dibutyltin lauric acid, lauryl alcohol (C12, molecular weight of about 186.34) ) was added, and the reaction was allowed to proceed overnight at 70 ° C under a nitrogen stream, and the reaction was stopped by adding water. The solvent was removed to obtain the desired polymer.
  • PEG poly (ethylene glycol)
  • the reaction was stopped by adding ethanol. The solvent was removed to obtain the desired polymer.
  • the polymer obtained in Comparative Production Example 1 is a polymer represented by the following formula (XV).
  • a vessel equipped with a thermometer, a nitrogen inlet tube and a stirrer l In a four-neck OO OmL flask, add 40 parts of polyethylene glycol (PEG) (molecular weight: about 20,000) and 300 parts of Tonolen, and dissolve at 70 ° C did. After azeotropically removing water, add 0.7 parts of hexamethylenedidisocyanate, 0.03 parts of dibutyltin diaperic acid, and myristyl alcohol (C14, molecular weight of about 214.38) at 80 ° C. The reaction was allowed to proceed overnight at 70 ° C. under a nitrogen stream, and the reaction was stopped by adding water. The solvent was removed to obtain the desired polymer.
  • PEG polyethylene glycol
  • the reaction was stopped by adding ethanol. The solvent was removed to obtain the desired polymer.
  • the polymer obtained in Comparative Production Example 2 is a polymer represented by the following formula (XIV). -(-(- ⁇ 2 ⁇ 2 ⁇ -1 ⁇ 25- CNH (CH 2 ) 6 NHCO-C "H 2 2 ⁇ (XVI)
  • the reaction was stopped by adding ethanol. The solvent was removed to obtain the desired polymer.
  • the polymer obtained in Comparative Production Example 3 is a polymer represented by the following formula (XVII).
  • the reaction was stopped by adding ethanol. The solvent was removed to obtain the desired polymer.
  • the polymer obtained by Comparative Production Example 4 is a polymer represented by the following formula (XVIII).
  • a preferable value of c depends on a value of b. That is, from the balance of hydrophilicity / hydrophobicity of the molecule, it is considered that a suitable value of c is larger for larger b and smaller for smaller b. These are called HLB (Hydrophi lie Lipophilic Balance).
  • the reaction was allowed to proceed overnight at 70 ° C., and the reaction was stopped by adding water. The solvent was removed to obtain a polymer.
  • the obtained polymer is represented by the formula (I) wherein A and Y are each —CH 2 CH 2
  • HLB b X 20 X a Z Total molecular weight (Griff in equation)... (XX)
  • Test example 1-1 0 19.6 ⁇ X
  • Test example 1-2 1 19.6 ⁇ X
  • Test example 1-3 3 19.5 ⁇ ⁇
  • Test example 1-6 50 17.7 ⁇ ⁇
  • Test example 1-7 70 17.0 ⁇ ⁇ Test example 1-8 105 16.0 ⁇ ⁇
  • the obtained polymer is represented by the above formula (I), wherein A and Y are one CH 2 CH 2 ,
  • Test example 2-1 35 0 16.6 3800 ⁇ X
  • Test Example 2-2 45 1 16.9 4800 ⁇ X
  • Test example 2-3 60 5 16. 7 6 800 ⁇ ⁇
  • Test example 2-4 75 8 16.8 8600 ⁇ ⁇
  • Test example 2-5 125 18 16.9 15000 ⁇ ⁇
  • dimethylsiloxane maintains a liquid state even when its molecular weight is increased. While the feeling of use is not sticky, the properties of higher alcohols change from liquid to solid as the number of alkyl chains increases, and Comparative Example 11 :!
  • the alkylated associative polymers of (1) to (14) do not have a thickening property when the alkyl group is in a liquid state, but have a thickening feeling when the alkyl group is in a solid state, but have a sticky feeling. Therefore, it was confirmed that the polymer of the present invention was superior in terms of viscosity increase and feeling of use as compared with the conventional alkylidene associative polymer.
  • a portion of the purified water was taken to dissolve the chelating agent, and a thickener was mixed and stirred to prepare a viscous liquid.
  • a humectant and a buffer were added to the remaining portion of the purified water and dissolved at room temperature, and the above-mentioned viscous liquid was added thereto to obtain a uniform aqueous solution.
  • Preservatives, surfactants, and fragrances were added to ethanol to form an alcohol solution, which was added to the above-mentioned aqueous solution and mixed for solubilization.
  • a humectant, an alkali, and a thickener were added to the purified water and heated to 70 ° C. After heating and dissolving the oil, a surfactant, a preservative, an antioxidant, and a fragrance were added, and the mixture was heated to 70 ° C. This was added to the previous aqueous phase and pre-emulsified. After homogenizing the emulsified particles using a homomixer, deaeration, filtration and cooling were performed.
  • Associative viscosity agent Polymer of Production Example 1 1
  • Water-soluble polymer xanthan gum 0.4 methinoresenololose 0.2
  • Emulsifier Noreboxyl vinyl polymer 0 1 5
  • Example 7 The humectant, buffer, thickener, whitening agent, and emulsifier were dissolved in purified water at room temperature. Ethanor After dissolving the oil, emollient, fragrance, and P-type preservative in the oil, it was solubilized in the aqueous phase described above.
  • Example 7 pack The humectant, buffer, thickener, whitening agent, and emulsifier were dissolved in purified water at room temperature. Ethanor After dissolving the oil, emollient, fragrance, and P-type preservative in the oil, it was solubilized in the aqueous phase described above. Example 7 pack
  • Coating agent Polyvinylinolenocore 15
  • the buffer and humectant were heated to 70 ° C in purified water.
  • a thickener and a film agent were added and dissolved with stirring.
  • Flavors, preservatives, and surfactants were added to ethanol, dissolved, and then added to the aqueous phase to solubilize.
  • Titanium dioxide, Red 201 and Red 202 are added to a part of castor oil and treated with a roller (pigment part).
  • the Red No. 2 23 dissolved in castor oil (dye portion).
  • the other components are mixed and heated and melted, and then the pigment and dye parts are added and dispersed uniformly with a homomixer. After that, the aqueous phase was added, emulsified and dispersed by a homomixer, poured into a mold, quenched, and formed into a stick.
  • Example 10 0—Nenole Enamel
  • the associative thickener was heated and dissolved in ion-exchanged water and added to the polymer emulsion.
  • diisobutyl adipate and carbitol were gradually added, and other components were added and uniformly dispersed, followed by degassing.
  • Associative thickener Polymer of Production Example 1 0 5
  • Flavors, pigments, preservatives are Flavors, pigments, preservatives:
  • Oil phase Fatty acid-treated titanium oxide 2
  • fragrances Preservatives, fragrances
  • the oil phase and the aqueous phase were each heated to 70 ° C. and dissolved.
  • the oil phase was added to the water phase, emulsified using a homogenizer, and cooled using a heat exchanger.
  • compositions prepared in Examples 1 to 14 and the compositions of Comparative Examples 1 to 14 using the alkylated associative polymer of Comparative Production Example 1 in place of the polymer of Production Example 1 were used. A sensory test of feeling was performed.
  • the composition of the comparative example using the alkylated associative polymer while the product a of the example using the silicone-associated associative polymer has a good feeling in use. Things are inferior to use. Therefore, it was confirmed that the composition of the present invention had a superior feeling in use as compared with a composition using a conventional alkyl-lighng associative polymer.
  • compositions of Examples 1 to 26 all had a non-greasy and refreshing feeling. Also, when the polymers of Production Examples 2 to 11 were used in place of the polymer of Production Example 1, a composition having a sticky and refreshing feeling was similarly obtained.
  • a non-sticky and refreshing feeling can be obtained.
  • a gel composition having characteristics such as sebum and sweat resistance can be obtained.

Abstract

L'invention concerne une composition sous forme de gel, constituée d'eau et d'un polymère pouvant être associé (I) contenant deux chaînes de silicium ou plus, séparées par une chaîne hydrophile, et ayant un HLB de 16.0 à 19.5. (I), où R1à R4 sont tous des groupes hydrocarbure ; Y est hydroxy, un oxyde d'alkylène ou un résidu d'uréthanne, d'éther, d'ester ou d'urée ; A signifie une chaîne hydrophile formée par un oxyde d'alkylène ; X représente un résidu d'uréthanne, d'éther, d'ester ou d'urée ; Z est un hydrocarbure ou un résidu d'uréthanne, d'éther, d'ester ou d'urée ; a est égal ou supérieur à 2 en moyenne ; b est un nombre entre 10 et 3000 en moyenne ; c est un nombre entre 1 et 500 en moyenne.
PCT/JP2001/011238 2000-12-22 2001-12-21 Composition sous forme de gel WO2002051939A1 (fr)

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JP2000-390898 2000-12-22
JP2000390898 2000-12-22

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KR (1) KR20030016223A (fr)
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Cited By (11)

* Cited by examiner, † Cited by third party
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JP2005225771A (ja) * 2004-02-10 2005-08-25 Shiseido Co Ltd 水中油型乳化組成物
WO2006075679A1 (fr) * 2005-01-17 2006-07-20 Shiseido Company, Ltd. Produit cosmétique
JP2007008915A (ja) * 2005-01-17 2007-01-18 Shiseido Co Ltd 化粧料
JP2007023277A (ja) * 2005-07-12 2007-02-01 Johnson & Johnson Consumer France Sas レチノイドを含有している水中シリコーン形エマルジョン組成物
JP2007533831A (ja) * 2004-04-20 2007-11-22 ダウ・コーニング・コーポレイション シリコーンポリエーテルブロック共重合体の水性分散液
US8080239B2 (en) 2005-01-17 2011-12-20 Shiseido Co., Ltd. Cosmetic
JP2018070794A (ja) * 2016-10-31 2018-05-10 信越化学工業株式会社 ポリエーテル変性シロキサン及び増粘剤
JP2018070790A (ja) * 2016-10-31 2018-05-10 信越化学工業株式会社 ヒドロキシル基含有シロキサン又はカルボキシ基含有シロキサンのエステル化方法
WO2020162248A1 (fr) * 2019-02-07 2020-08-13 株式会社Adeka Silicone modifiée par uréthane, et composition huileuse et composition cosmétique la contenant
CN112566616A (zh) * 2018-08-10 2021-03-26 株式会社资生堂 乳化化妆品
US11104766B2 (en) 2017-05-31 2021-08-31 Toray Industries, Inc. Block copolymer and method of producing same, epoxy resin composition and cured product thereof, and semiconductor encapsulating material

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5481197B2 (ja) * 2006-12-26 2014-04-23 ボミ・パテル・フラムローゼ 高色素沈着した皮膚のための皮膚美白組成物
JP5164179B2 (ja) * 2009-12-28 2013-03-13 株式会社 資生堂 液状化粧料
JP2012031125A (ja) * 2010-08-03 2012-02-16 Nikko Chemical Co Ltd 紫外線吸収剤を含有する微細エマルション組成物並びに化粧料
US11395795B2 (en) * 2010-09-20 2022-07-26 L'oreal Aqueous cosmetic composition comprising alkylcellulose
WO2012038374A2 (fr) * 2010-09-20 2012-03-29 L'oreal Composition cosmétique aqueuse comprenant de l'alkylcellulose
JP5551550B2 (ja) * 2010-09-28 2014-07-16 ライオン株式会社 粘土鉱物分散液の製造方法
FR3052357B1 (fr) * 2016-06-14 2019-08-30 Chanel Parfums Beaute Composition cosmetique comprenant au moins un polymere silicone-polyurethane et une resine de silicone
JP2018043980A (ja) * 2016-09-13 2018-03-22 日油株式会社 透明系シャンプー組成物
US11771630B2 (en) 2018-08-10 2023-10-03 Shiseido Company, Ltd. Oil-based cosmetic
JP7427592B2 (ja) * 2018-08-10 2024-02-05 株式会社 資生堂 化粧料
WO2020032243A1 (fr) * 2018-08-10 2020-02-13 株式会社 資生堂 Produit cosmétique en émulsion
JP7231213B2 (ja) * 2019-03-28 2023-03-01 株式会社ダリヤ 水中油型化粧料組成物

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05311076A (ja) * 1992-05-01 1993-11-22 Toray Dow Corning Silicone Co Ltd ゲル状シリコーン組成物
JPH07126392A (ja) * 1993-11-02 1995-05-16 Shin Etsu Chem Co Ltd ポリエーテル−シロキサンブロック共重合体及びその製造方法
US5919441A (en) * 1996-04-01 1999-07-06 Colgate-Palmolive Company Cosmetic composition containing thickening agent of siloxane polymer with hydrogen-bonding groups
JP2000178359A (ja) * 1998-12-16 2000-06-27 Chisso Corp ポリオキシアルキレン−ｂｌｏｃｋ−アルキレン−ｂｌｏｃｋ−ポリオルガノシロキサン及びゲル組成物
JP2001288233A (ja) * 2000-04-06 2001-10-16 Shiseido Co Ltd 新規高分子およびこれを用いた化粧料

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2720274B1 (fr) * 1994-05-26 1997-01-24 Oreal Compositions cosmétiques contenant un copolymère bloc linéaire polysiloxane-polyoxyalkylène, un agent de conditionnement insoluble non volatile et un alcool hydrosoluble, et leurs utilisations.
JPH09143499A (ja) * 1995-11-22 1997-06-03 Nippon Oil & Fats Co Ltd 洗浄剤組成物
JPH09175951A (ja) * 1995-12-25 1997-07-08 Nippon Oil & Fats Co Ltd 毛髪化粧料
JP3947668B2 (ja) * 2000-12-22 2007-07-25 株式会社資生堂 水系溶媒用会合性増粘剤、それを含むゲル状組成物及びエマルション組成物
WO2015122547A1 (fr) * 2015-02-27 2015-08-20 株式会社小松製作所 Pelle hydraulique

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05311076A (ja) * 1992-05-01 1993-11-22 Toray Dow Corning Silicone Co Ltd ゲル状シリコーン組成物
JPH07126392A (ja) * 1993-11-02 1995-05-16 Shin Etsu Chem Co Ltd ポリエーテル−シロキサンブロック共重合体及びその製造方法
US5919441A (en) * 1996-04-01 1999-07-06 Colgate-Palmolive Company Cosmetic composition containing thickening agent of siloxane polymer with hydrogen-bonding groups
JP2000178359A (ja) * 1998-12-16 2000-06-27 Chisso Corp ポリオキシアルキレン−ｂｌｏｃｋ−アルキレン−ｂｌｏｃｋ−ポリオルガノシロキサン及びゲル組成物
JP2001288233A (ja) * 2000-04-06 2001-10-16 Shiseido Co Ltd 新規高分子およびこれを用いた化粧料

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005225771A (ja) * 2004-02-10 2005-08-25 Shiseido Co Ltd 水中油型乳化組成物
JP4908400B2 (ja) * 2004-04-20 2012-04-04 ダウ・コーニング・コーポレイション シリコーンポリエーテルブロック共重合体の水性分散液
JP2007533831A (ja) * 2004-04-20 2007-11-22 ダウ・コーニング・コーポレイション シリコーンポリエーテルブロック共重合体の水性分散液
WO2006075679A1 (fr) * 2005-01-17 2006-07-20 Shiseido Company, Ltd. Produit cosmétique
JP2007008915A (ja) * 2005-01-17 2007-01-18 Shiseido Co Ltd 化粧料
JP4567585B2 (ja) * 2005-01-17 2010-10-20 株式会社資生堂 化粧料
CN101106970B (zh) * 2005-01-17 2011-06-08 株式会社资生堂 化妆品
US8080239B2 (en) 2005-01-17 2011-12-20 Shiseido Co., Ltd. Cosmetic
JP2007023277A (ja) * 2005-07-12 2007-02-01 Johnson & Johnson Consumer France Sas レチノイドを含有している水中シリコーン形エマルジョン組成物
JP2018070794A (ja) * 2016-10-31 2018-05-10 信越化学工業株式会社 ポリエーテル変性シロキサン及び増粘剤
JP2018070790A (ja) * 2016-10-31 2018-05-10 信越化学工業株式会社 ヒドロキシル基含有シロキサン又はカルボキシ基含有シロキサンのエステル化方法
US11104766B2 (en) 2017-05-31 2021-08-31 Toray Industries, Inc. Block copolymer and method of producing same, epoxy resin composition and cured product thereof, and semiconductor encapsulating material
CN112566616A (zh) * 2018-08-10 2021-03-26 株式会社资生堂 乳化化妆品
EP3834807A4 (fr) * 2018-08-10 2022-05-04 Shiseido Company, Ltd. Produit cosmétique émulsifié
WO2020162248A1 (fr) * 2019-02-07 2020-08-13 株式会社Adeka Silicone modifiée par uréthane, et composition huileuse et composition cosmétique la contenant

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