WO2011013293A1 - Préparation cosmétique dans laquelle un copolymère contenant du fluor est incorporé par mélange - Google Patents

Préparation cosmétique dans laquelle un copolymère contenant du fluor est incorporé par mélange Download PDF

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Publication number
WO2011013293A1
WO2011013293A1 PCT/JP2010/004131 JP2010004131W WO2011013293A1 WO 2011013293 A1 WO2011013293 A1 WO 2011013293A1 JP 2010004131 W JP2010004131 W JP 2010004131W WO 2011013293 A1 WO2011013293 A1 WO 2011013293A1
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Prior art keywords
fluorine
group
cosmetic
components
carbon atoms
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PCT/JP2010/004131
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English (en)
Japanese (ja)
Inventor
長谷川幸夫
今関雅文
竹内康
齋藤三也
野口幸嗣
前田昌彦
福田晃之
丸山茂
Original Assignee
三好化成株式会社
ダイキン工業株式会社
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Publication of WO2011013293A1 publication Critical patent/WO2011013293A1/fr

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    • 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
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • 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
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • 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
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
    • A61Q1/06—Lipsticks
    • 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
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/10—Preparations containing skin colorants, e.g. pigments for eyes, e.g. eyeliner, mascara
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/22—Esters containing halogen
    • C08F220/24—Esters containing halogen containing perhaloalkyl radicals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen

Definitions

  • the present invention relates to a cosmetic containing a fluorine-containing copolymer that can impart oil resistance and friction resistance to skin and hair by application.
  • Cosmetics aimed at protecting the skin from oil are commercially available. In general, these are solid cream preparations, and a film composed of a surfactant and an oil film is formed on the skin to prevent the attached oil agent from directly attaching to the skin. However, depending on the type of oil agent, the protective effect may be significantly impaired due to dissolution of the protective agent.
  • a cosmetic containing a polymer fluorine compound such as a perfluoropolyether or a compound having a perfluoroalkyl group.
  • the polymer fluorine compound has water and oil repellency and is difficult to dissolve in an oil agent, so that a protective film can be formed on the skin more stably.
  • the water and oil repellency of the polymer fluorine compound is not compatible with other oily bases and aqueous bases that make up the formulation at the same time. It was difficult to maintain the formulation.
  • Non-patent document 1 of recent research results, etc. have revealed the concern of environmental burden to PFOA (perfluorooctanoic acid), a kind of long-chain fluoroalkyl compound, April 2003
  • EPA US Environmental Protection Agency
  • Non-Patent Document 2 discloses that telomers may generate PFOA by decomposition or metabolism (telomers are long-chain fluoroalkyl groups). means).
  • telomers are used in many products such as foam, water- and oil-repellent and antifouling foams, care products, cleaning products, carpets, textiles, paper and leather. Yes.
  • perfluoroalkylsilanes and fluorine-containing copolymers having a perfluoroalkyl group having 6 or less carbon atoms and excellent water and oil repellency have been disclosed and developed as surface treatment agents for cosmetic powders (patents) References 1 and 2).
  • fluorine having a perfluoroalkyl group having 6 or less carbon atoms which can be stably blended in cosmetics comprising an aqueous base or oil base, and the coating film can exhibit oil resistance and friction resistance.
  • the compound has not yet been developed.
  • the present invention has been made under such circumstances, and can be applied to impart oil resistance and friction resistance to the skin and hair, and can be easily removed by washing with water. It is an issue to provide high and stable cosmetics.
  • the present inventors can stably blend a specific fluorine-containing copolymer into a cosmetic preparation system and achieve this object.
  • the specific fluorine-containing copolymer is designed to be excellent in safety to the living body and safety to the environment.
  • Cosmetics containing this fluorine-containing copolymer are suitable for skin and hair. It was found that when applied, excellent oil resistance and friction resistance can be imparted, and it can be easily washed off from the skin and hair by washing with water, thereby completing the present invention.
  • the present invention is a copolymer of (a) a fluorine-containing monomer represented by the following general formula (I) and (b) an alkoxy group-containing monomer represented by the following general formula (II). It is related with the cosmetics which mix
  • X is a hydrogen atom, a methyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a CFX1X2 group (wherein X1 and X2 are each a hydrogen atom, a fluorine atom or a chlorine atom), cyano.
  • Y is —O— or —NH—;
  • Z is a direct bond, —S— or —SO 2 —;
  • Rf is a fluoroalkyl group having 1 to 6 carbon atoms;
  • m is 1 to 10, n is 0 to 10, and p is 0 or 1.
  • X3 represents a hydrogen atom or a methyl group
  • X4 is a hydrogen atom or an unsaturated or saturated hydrocarbon group having 1 to 22 carbon atoms
  • R is an alkylene group having 2 to 4 carbon atoms in which some or all of the hydrogen atoms may be substituted with hydroxyl groups
  • q is an integer of 1 to 50.
  • the ratio of the fluorine-containing monomer (a) to the alkoxy group-containing monomer (b) is alkoxy with respect to 100 parts by weight of the fluorine-containing monomer (a).
  • the cosmetic according to (1), wherein the group-containing monomer (b) is 10 to 400 parts by weight, preferably 25 to 150 parts by weight, more preferably 43 to 100 parts by weight.
  • the fluorine-containing copolymer has a weight average molecular weight in the range of 5,000 to 100,000, preferably a weight average molecular weight in the range of 5,000 to 50,000, more preferably a weight average molecular weight of 5,
  • the above-mentioned fluorine-containing copolymer is dispersed or dissolved in a lower alcohol having 2 or 3 carbon atoms, more preferably ethyl alcohol as a medium, and blended in a pharmaceutical formulation system as a dispersion.
  • a lower alcohol having 2 or 3 carbon atoms more preferably ethyl alcohol as a medium
  • a pharmaceutical formulation system as a dispersion.
  • the cosmetic according to any one of (1) to (6) above which is any one of skin care cosmetics, makeup cosmetics, sunscreen cosmetics, and hair care cosmetics.
  • a highly safe and stable cosmetic that can impart oil resistance and friction resistance to skin and hair by application and can be easily removed by washing with water. be able to. More specifically, smooth use feeling, improvement of makeup sustainability due to film formation effect, improvement of hygroscopicity and moisture retention, solubilization and emulsification improver from surface active ability, function as a single emulsifier, The effect of easy washing and easy cleansing of the decorative film is obtained.
  • the merit of cosmetics containing powders is improved powder dispersibility and dispersion stability. Furthermore, the decomposition
  • the fluorine-containing copolymer which is the component (A) in the present invention includes (a) a fluorine-containing monomer represented by the following general formula (I) and (b) an alkoxy represented by the general formula (II) described later. It is obtained by copolymerizing a monomer that essentially contains a group-containing monomer.
  • Fluorine-containing monomer (a) is represented by the general formula:
  • X is a hydrogen atom, a methyl group, a linear or branched alkyl group having 1 to 21 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a CFX1X2 group (where X1 and X2 are Each represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom or an iodine atom), a cyano group, a linear or branched fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted benzyl group, a substituted group Or an unsubstituted phenyl group; Y is —O— or —NH—; Z is a direct bond, —S— or —SO 2 —; Rf is a fluoroalkyl group having 1 to 6 carbon atoms; m is 1 to 10, n is
  • p is preferably 0.
  • a preferred example of X is a hydrogen atom.
  • the fluorine-containing monomer (a) generally has a perfluoroalkyl group and / or a partially fluorinated fluoroalkyl group.
  • a perfluoroalkyl group is preferred.
  • the Rf group has 1 to 6 carbon atoms. The number of carbon atoms in the Rf group is preferably 4, 5, or 6, particularly 6.
  • Rf groups are -CF3, -CF2CF3, -CF2CF2CF3, -CF (CF3) 2, -CF2CF2CF2CF3, -CF2CF (CF3) 2, -C (CF3) 3,-(CF2) 4CF3,-(CF2) 2CF (CF3) 2, -CF2C (CF3) 3, -CF (CF3) CF2CF2CF3,-(CF2) 5CF3, and the like.
  • Fluorine-containing monomer (a) may be used alone or in combination of two or more.
  • fluorine-containing monomer (a) examples include the following.
  • fluorine-containing monomer (a) include, but are not limited to, for example, the following.
  • the alkoxy group-containing monomer (b) is a non-fluorine monomer and is a compound (alkylene glycol (meth) acrylate) represented by the following general formula (II).
  • X3 represents a hydrogen atom or a methyl group
  • X4 is a hydrogen atom or an unsaturated or saturated hydrocarbon group having 1 to 22 carbon atoms
  • R is an alkylene group having 2 to 4 carbon atoms in which some or all of the hydrogen atoms may be substituted with hydroxyl groups
  • q is an integer of 1 to 50.
  • q is preferably 1 to 30, for example 2 to 10, particularly 2 to 5.
  • R is preferably ethylene or propylene, particularly ethylene.
  • R in the general formula (II) may be a combination of two or more types of alkylene. In that case, at least one of R is preferably ethylene. Examples of the combination of R include an ethylene group / propylene group combination and an ethylene group / butylene group combination.
  • the alkoxy group-containing monomer (b) may be a mixture of two or more types.
  • alkoxy group-containing monomer (b) include, for example, the following, but are not limited thereto.
  • the ratio of the fluorine-containing monomer (a) to the alkoxy group-containing monomer (b) is 100 parts by weight of the fluorine-containing monomer (a).
  • the alkoxy group-containing monomer (b) is 10 to 400 parts by weight, preferably 25 to 150 parts by weight, and more preferably 43 to 100 parts by weight.
  • the weight average molecular weight of the fluorinated copolymer (A) is in the range of about 5,000 to 100,000, preferably about 5,000 to 50,000, more preferably about 5,000 to 30,000. is there. When the weight average molecular weight is smaller than this, there is a tendency that the affinity for water is improved and the water resistance of the coating film is lowered. Further, when the weight average molecular weight is larger than this, dispersibility in the vehicle is lowered, viscosity is increased, and there is a tendency that the suitability for blending in cosmetics and the usability of cosmetics are lowered.
  • the weight average molecular weight is a value obtained by gel permeation chromatography in terms of polystyrene.
  • the fluorine-containing copolymer (A) used in the present invention can be synthesized by a method disclosed in, for example, Japanese Patent Application Laid-Open No. 2000-290640.
  • various polymerization methods such as bulk polymerization, solution polymerization, emulsion polymerization, and radiation polymerization can be selected for the synthesis of the fluorinated copolymer, but are not limited to these examples.
  • solution polymerization using an organic solvent or emulsion polymerization using water or an organic solvent and water in combination can be selected.
  • the amount of the fluorine-containing copolymer (A) varies depending on the properties of the cosmetic, but in order to obtain the component retention and the durability of the effect in the present invention, it is necessary to add 100 parts by weight of the cosmetic.
  • the amount is preferably 0.01 to 40 parts by weight, more preferably 0.1 to 10 parts by weight.
  • the method for formulating and blending the fluorine-containing copolymer (A) of the present invention into cosmetics is not particularly limited.
  • one or more of the fluorine-containing copolymers as the component (A) can be formulated alone, but water or lower alcohols such as ethanol and isopropyl alcohol are used as a medium.
  • water or lower alcohols such as ethanol and isopropyl alcohol are used as a medium.
  • the fluorine-containing copolymer (A) After the fluorine-containing copolymer (A) is dissolved or dispersed, it can be easily blended into a cosmetic formulation using this mixed solution or dispersion. By this operation, even when the fluorine-containing copolymer as the component (A) has a high weight average molecular weight and a high viscosity, blending into the formulation can be facilitated.
  • a dispersion / mixture of the fluorinated copolymer (A) and a lower alcohol a dispersion / mixture is obtained by diluting with water or a lower alcohol such as ethanol or isopropanol after polymerization. Can do. Also, it is possible to obtain an alcohol dispersion of a fluorinated copolymer by using a lower alcohol as a polymerization solvent.
  • the fluorine-containing copolymer as the component (A) is essential for the cosmetic of the present invention
  • an aqueous component, an oil agent, powders, an interface are used as long as the effects of the invention are not impaired at the same time during the production of the cosmetic.
  • Other components that can be blended such as activators, ultraviolet absorbers, fragrances, preservatives, bactericides, moisturizers, physiologically active ingredients, and propellants can be blended. As these other components that can be blended, those commonly used in cosmetics can be used as they are.
  • aqueous component examples include many lower alcohols such as ethanol and isopropanol, 1,3-butylene glycol, propylene glycol, polyethylene glycol, glycerin, diglycerin, polyglycerin, trehalose, erythritol, mannitol, xylitol, sorbitol, maltose, and the like.
  • lower alcohols such as ethanol and isopropanol, 1,3-butylene glycol, propylene glycol, polyethylene glycol, glycerin, diglycerin, polyglycerin, trehalose, erythritol, mannitol, xylitol, sorbitol, maltose, and the like.
  • Dihydric alcohol Dihydric alcohol, gum arabic, tragacanth, galactan, carob gum, guar gum, karaya gum, carrageenan, pectin, agar, quince seed (quince), starch (rice, corn, potato, wheat), dextrin, dextran, alge colloid, tran gum, locust Plant water-soluble polymers such as bean gum, microbial water-soluble such as xanthan gum, dextran, succinoglucan and pullulan Molecules, water-soluble polymers such as collagen, casein, albumin and gelatin, starch-based water-soluble polymers such as carboxymethyl starch and methylhydroxypropyl starch, methylcellulose, ethylcellulose, methylhydroxypropylcellulose, carboxymethylcellulose, hydroxymethylcellulose, Hydroxypropylcellulose, nitrocellulose, sodium cellulose sulfate, sodium carboxymethylcellulose, crystalline cellulose, cellulose water-soluble polymer of cellulose powder, water-soluble al
  • the stability of cosmetics tends to be improved and the oil resistance tends to be improved, which is preferable.
  • examples of the oil agent include safflower oil, soybean oil, evening primrose oil, grape seed oil, rosehip oil, cucumber nut oil, almond oil, sesame oil, wheat germ oil, corn oil, cottonseed oil, avocado oil , Olive oil, camellia oil, persic oil, castor oil, peanut oil, hazelnut oil, macadamia nut oil, medfoam oil, cocoa butter, shea fat, tree wax, palm oil, palm oil, palm kernel oil, beef tallow, horse fat, mink Oils, milk fat, egg yolk oil, turtle oil and other oils, beeswax, whale wax, lanolin, carnauba wax, candelilla wax, jojoba oil and other waxes, liquid paraffin, liquid isoparaffin, squalane, squalene, petrolatum, paraffin, ceresin, Hydrocarbons such as microcrystalline wax, lauric acid, myristic Acids, palmitic acid, stearic acid, be
  • powders include, for example, boron nitride, sericite, natural mica, calcined mica, synthetic mica, synthetic sericite, alumina, mica, talc, kaolin, bentonite, smectite, calcium carbonate, Magnesium carbonate, calcium phosphate, anhydrous silicic acid, magnesium oxide, tin oxide, iron oxide, yttrium oxide, chromium oxide, titanium oxide, zinc oxide, cerium oxide, aluminum oxide, magnesium oxide, chromium hydroxide, bitumen, ultramarine, calcium phosphate, water Aluminum oxide, barium sulfate, magnesium sulfate, silicic acid, magnesium aluminum silicate, calcium silicate, barium silicate, magnesium silicate, aluminum silicate, strontium silicate, silicon carbide, magnesium fluoride, gold tungstate Salt, magnesium aluminate, magnesium aluminate metasilicate, chlorohydroxyaluminum, clay, zeolite, hydroxyapati
  • organic powders include metal soaps, N-mono long chain acyl basic amino acids, polyamido amide sulfonates, salt powder, carbon black, tar pigments, and natural pigments , Polyamide powder, Polyester powder, Polyethylene powder, Polyurethane powder, Polypropylene powder, Polystyrene powder, Penzoguanamine powder, Polymethylpenzoguanamine powder, PTFE powder, Cellulose powder, Silk powder, Silicone powder, Divinylbenzene / styrene copolymer , Vinyl resin, urea resin, phenol resin, fluorine resin, silicon resin, acrylic resin, melamine resin, epoxy resin, polycarbonate resin and other synthetic resin powder, nylon fiber, polyester fiber Microcrystalline fiber powder, starch powder and the like, CI Pigment Yellow, CI Pigment Orange, and the like.
  • red No. 3 red No. 10, red No. 106, red No. 201, red No. 202, red No. 204, red No. 205, red No. 220, red No. 226, red No. 227, red No. 228, red 230 No., red 401, red 505, yellow 4, yellow 5, yellow 202, yellow 203, yellow 204, yellow 401, blue 1, blue 2, blue 201, blue 404, Green No. 3, Green No. 201, Green No. 204, Green No. 205, Orange No. 201, Orange No. 203, Orange No. 204, Orange No. 206, Orange No. 207, etc .; natural pigments include carmine, laccaic acid, calsamine, bradylin And powders of natural pigments such as crocin, chlorophyll, ⁇ -carotene and safflower powder.
  • the shape of the powder that can be blended in the cosmetic of the present invention is not particularly specified.
  • a spherical shape, a rod shape, a needle shape, a spindle shape, a plate shape, an irregular shape, a fiber shape, and the like may be used.
  • the particle diameter may be in the range of about 1 nm to 2000 ⁇ m as long as it can be incorporated into cosmetics.
  • these powders may be a powder obtained by mixing or combining two or more kinds.
  • These powders are conventionally known surface treatments such as fluorine compound treatment, silicone treatment, pendant treatment, silane coupling agent treatment, titanium coupling agent treatment, oil agent treatment, acylated amino acid treatment, polyacrylic acid treatment, metal It may or may not be pretreated by soap treatment, amino acid treatment, inorganic compound treatment, plasma treatment, mechanochemical treatment, or the like.
  • surfactants include fatty acid soaps such as sodium stearate and triethanolamine palmitate, alkyl ether carboxylic acids and salts thereof, condensates of amino acids and fatty acids, alkane sulfonates, alkene sulfonates, fatty acid esters Sulfonate, fatty acid amide sulfonate, formalin condensation sulfonate, alkyl sulfate, secondary higher alcohol sulfate, alkyl and allyl ether sulfate, fatty acid sulfate, fatty acid alkyl
  • Anionic surfactant composed of sulfate ester salt of roll amide, sulfate salt such as funnel oil, alkyl phosphate, ether phosphate, alkyl allyl ether phosphate, amide phosphate, N-acyl amino acid type activator Agent, alkylamine salt Cationic surfactants such as amine salts such as polyamines and amino alcohol fatty acid
  • UV absorbers such as ethylhexyl methoxycinnamate, octocrylene, and avobenzone, synthetic or natural fragrances, preservatives such as benzoate and dehydroacetic acid, fungicides such as hibitenes, moisturizers such as plant extracts,
  • Bioactive ingredient vitamins such as anti-inflammatory agents such as indomethacin include vitamin E, vitamin C, vitamin B1, and derivatives thereof, vitamin K, vitamin B2, vitamin 12, biotin, pantothenic acid, vitamin A, ⁇ -carotene, ⁇ -lipoic acid and salts thereof, or a mixture thereof, ubiquinone, ubiquinol, arbutin, placenta extract, sake lees extract, winter and summer grass extract and the like can be blended.
  • the cosmetic of the present invention can be applied to aerosol preparations by blending propellants such as propane and butane.
  • the cosmetic of the present invention is not particularly limited as long as the fluorine-containing copolymer of the present invention or a dispersion thereof can be blended.
  • the cosmetic dosage form for example, conventionally known dosage forms such as liquid, emulsion, cream, solid, paste, gel, powder, mousse, and spray can be selected. It is not limited to these. Further, in the production of the cosmetic of the present invention, a special device is not required, and it can be produced using a device conventionally used for cosmetic production.
  • PV perbutyl PV
  • IPA distilled off from the resulting solution under reduced pressure at about 70 ° C. to obtain a C6 fluorine acrylate / polyalkylene glycol acrylate copolymer residue.
  • ethanol was added to the obtained polymer, and the internal temperature was kept at about 80 ° C. for 1 hour or more, followed by cooling to prepare a fluorine-containing copolymer ethanol dispersion having a solid content concentration of about 40% by weight.
  • the weight average molecular weight of the fluorinated copolymer synthesized in Production Example 1 was measured by GPC (gel permeation chromatography).
  • the weight average molecular weight in terms of polyethylene glycol was about 12,500.
  • the polymerization reaction was carried out in the same manner as in Example 1, replacing with PE350 (b)) to prepare a fluorine-containing copolymer aqueous dispersion having a solid content concentration of about 50% by weight.
  • the synthesized fluorine-containing copolymer had a weight average molecular weight of about 9,500 as measured by GPC.
  • IPA IPA was added to the obtained polymer, the internal temperature was kept at about 80 ° C. for 1 hour or longer, and then cooled to prepare a fluorinated copolymer IPA dispersion having a solid content concentration of about 40% by weight.
  • the synthesized fluorine-containing copolymer had a weight average molecular weight of about 26,600 as measured by GPC.
  • Examples 1 to 3 A lotion having the composition shown in Table 1 was produced. The blending amount is expressed in parts by weight.
  • the obtained lotions all showed a uniform appearance and were highly stable. Moreover, the evaluation mentioned later was performed about each obtained lotion. The results are shown in Table 2.
  • Comparative Example 1 Fluorine-containing copolymer aqueous dispersion was changed to 2.0 parts by weight of polyperfluoromethylisopropyl ether (FOMBLIN HC / 04 manufactured by Solvay Solexis), which is a fluorinated oil used in conventional cosmetics, and purified water
  • the lotion of Comparative Example 1 was obtained in the same manner as Example 1 except that the total amount was adjusted to 100.0 parts. Polyperfluoromethyl isopropyl ether precipitated in the lotion.
  • Comparative Example 2 The fluorine-containing copolymer aqueous dispersion was changed to 5.0 parts by weight of acrylic-modified silicone (KP-575, solid content concentration 40% IPA solution manufactured by Shin-Etsu Silicone), which has been used as a film-forming agent in conventional cosmetics. Except for the above, a lotion of Comparative Example 2 was obtained in the same manner as Example 3. The lotion was thickened and the appearance was slightly turbid.
  • acrylic-modified silicone KP-575, solid content concentration 40% IPA solution manufactured by Shin-Etsu Silicone
  • Comparative Example 3 Without adding the fluorine-containing copolymer aqueous dispersion, the total amount was adjusted to 100.0 parts with purified water, and a lotion of Comparative Example 2 was obtained in the same manner as in Example 1.
  • Filter paper (Advantech, qualitative filter paper No. 2) was soaked in the skin lotions of Examples 1 to 3 and Comparative Examples 1 to 3, and dried at 37 ° C. to prepare cast filter paper.
  • the cast filter paper was rubbed 30 times with a nonwoven fabric, and then evaluated by the same method as the stain resistance evaluation method. Those that are not easily removed from the cast filter paper against the friction of the nonwoven fabric are considered to have high friction resistance. Similar to the antifouling property evaluation, the antifriction property was also expressed according to the following three-level evaluation criteria. Colored squalane does not soak and does not stain ⁇ Colored squalane partially soaks and causes color stains partially ⁇ All the colored squalane soaked and was completely soiled ⁇
  • the fluorine-containing copolymers of Production Examples 1 to 3 could be stably dispersed in Examples 1 to 3.
  • the coating films obtained in Examples 1 to 3 had high oil resistance and antifouling resistance, and good friction resistance. Furthermore, evaluation of a feeling of use was also high.
  • Example 4 and Comparative Example 4 Production of Protective Cream A protective cream having the composition shown in Table 3 was produced as Example 4 by the following method. Further, Comparative Example 4 was obtained by replacing the fluorinated copolymer of the present invention with an acrylic emulsion. Table 4 shows the evaluation results.
  • Example 4 The creams obtained in Example 4 and Comparative Example 4 were used by 10 panelists, and the usability was evaluated in the same manner as in Examples 1 to 3. In addition, after the cream was applied to the upper arm and dried for 30 minutes, one drop of methylene blue was dropped on the application part, and then the application part was washed out under running water, and the methylene blue dyeing property was evaluated. The results are shown in Table 4.
  • Example 4 which is the present invention was provided with good characteristics excellent in use feeling as compared with Comparative Example 4. Moreover, the methylene blue which is a contamination target was prevented from being dyed, and the antifouling property was high. Moreover, the protective cream of Example 4 was highly stable.
  • Example 5 The water fortification obtained in Example 5 was applied to the skin, and after drying, one drop of squalane colored with 0.1% of red No. 202 dye was dropped on the coated part to evaluate oil resistance. Next, this squalane was lightly wiped off using tissue paper, and then washed under running water to confirm the persistence of water. On the water-applied application part, squalane was in the form of oil droplets, and these oil droplets could be easily removed by tissue-off, and dyeing to the skin was not seen. In addition, by rinsing under running water, the water fountain could be easily removed from the skin.
  • Example 6 Aqueous gel lotion The aqueous gel lotion having the composition shown in Table 6 was produced by the following method.
  • Example 7 Production of aqueous eye shadow An aqueous eye shadow having the composition shown in Table 7 was produced by the following method.
  • Example 8 Manufacture of two-layer sunscreen A two-layer sunscreen having the composition shown in Table 8 was manufactured by the following method.
  • Example 10 Production of water-containing powder formulation A water-containing powder formulation having the composition shown in Table 10 was produced by the following method.
  • Example 6 to Example 10 it can be evaluated by the evaluation method in Example 4, and the same result can be obtained, and the cosmetic of the present invention provides oil resistance and friction resistance to the skin and hair by applying. It was a highly safe and stable cosmetic that can be applied and easily removed by washing with water.
  • Example 11 Lotion Toner lotion having the following composition was produced by the following method. In all of the following examples, “%” represents% by weight.
  • the lotion of Example 11 was a lotion with a smooth feeling of use and excellent makeup lasting effect.
  • Example 12 Two-layer lotion A two-layer lotion having the following composition was produced by the following method.
  • the two-layer lotion of Example 12 was a two-layer lotion having excellent powder dispersibility, a smooth feeling of use, and an excellent makeup sustaining effect.
  • the emulsion of Example 13 was an emulsion having excellent emulsification stability, a smooth feeling of use, and an excellent cosmetic lasting effect.
  • Cream A cream having the following composition was produced by the following method.
  • the cream of Example 14 was excellent in emulsification stability, smooth use feeling, and excellent makeup lasting effect.
  • Cosmetic liquid A cosmetic liquid having the following composition was produced by the following method.
  • Example 15 The essence of Example 15 was an essence having excellent emulsification stability, a smooth feeling of use, and an excellent makeup sustaining effect.
  • the pack of Example 16 was excellent in emulsification stability, smooth use feeling and excellent makeup lasting effect.
  • the face wash of Example 17 was a face wash having excellent water washability.
  • the cleansing gel of Example 18 was a cleansing gel excellent in water washability.
  • the cleansing cream of Example 19 was a cleansing cream with excellent emulsification stability and excellent water washability.
  • Example 20 Mousse hair styling A mousse hair styling having the composition shown below was produced by the following method.
  • the mousse hair styling agent of Example 20 was a mousse hair styling agent having excellent hair styling properties, a smooth feeling of use, and excellent water washing properties.
  • Example 21 Spray hair styling A spray hair styling composition having the following composition was produced by the following method.
  • the spray-type hair styling material of Example 21 was a spray-type hair styling that was excellent in hair styling properties, had a smooth feeling of use, and was excellent in water washability.
  • Hair wax A hair wax having the following composition was produced by the following method.
  • the hair wax of Example 22 was a hair wax having excellent hair styling properties, a smooth feeling of use, and excellent water washing properties.
  • Oily eyeliner having the following composition was produced by the following method.
  • the eyeliner of Example 23 was an eyeliner excellent in smooth use feeling and makeup lasting effect.
  • Example 24 Aqueous eyeliner having the following composition was produced by the following method.
  • the water-based eyeliner of Example 24 was a water-based eyeliner excellent in smooth use feeling and makeup sustaining effect.
  • the eyebrow of Example 25 was an eyebrow excellent in smooth use feeling and makeup lasting effect.
  • Example 26 O / W type mascara An O / W type mascara having the following composition was produced by the following method.
  • the O / W type mascara of Example 26 was an O / W type mascara excellent in powder dispersibility and emulsification stability, smooth in feeling of use, and excellent in makeup lasting effect.
  • Nonaqueous mascara A nonaqueous mascara having the following composition was produced by the following method.
  • the non-aqueous mascara of Example 27 was a non-aqueous mascara excellent in smooth use feeling and makeup lasting effect.
  • the stick-shaped lipstick of Example 28 was a lipstick with a smooth use feeling and excellent makeup lasting effect.
  • Example 29 O / W type foundation The O / W type foundation of the composition shown below was manufactured with the following method.
  • the O / W type foundation of Example 29 was an O / W type foundation excellent in powder dispersibility and emulsification stability, smooth in feeling of use, and excellent in makeup effect.
  • Example 30 W / O type foundation The W / O type foundation of the composition shown below was manufactured with the following method.
  • the W / O type foundation of Example 30 was a W / O type foundation excellent in powder dispersibility and emulsification stability, smooth in feeling of use, and excellent in makeup sustaining effect.
  • Example 31 O / W Eye Color A W / O eye color having the composition shown below was produced by the following method.
  • the O / W type eye color of Example 31 was excellent in powder dispersibility and emulsion stability, and was an O / W type eye color excellent in smooth use feeling and makeup sustaining effect.
  • Oily solid foundation An oily solid foundation having the following composition was produced by the following method.
  • the oil-based solid foundation of Example 32 was an oil-based solid foundation that was excellent in powder dispersibility, smooth in feeling of use, and excellent in makeup lasting effect.
  • the stick concealer of Example 33 was a stick concealer having excellent powder dispersibility, a smooth feeling of use, and an excellent makeup sustaining effect.
  • Body soap A body soap having the following composition was produced by the following method.
  • the body soap of Example 34 was a body soap excellent in smooth use feeling and water washability.
  • Example 35 Body Milk Body milk having the following composition was produced by the following method.
  • the body milk of Example 35 was excellent in emulsification stability, smooth use feeling, and excellent makeup lasting effect.
  • the shampoo of Example 36 was a shampoo with a smooth feeling of use and excellent water washing properties.
  • Conditioner A conditioner having the following composition was produced by the following method.
  • the conditioner of Example 37 was a conditioner with a smooth feeling of use and excellent water washing properties.
  • Hairpack A hairpack having the composition shown below was produced by the following method.
  • the hair pack of Example 38 had a smooth feeling and was excellent in water washability.
  • the W / O sunscreen of Example 39 was a sunscreen excellent in powder dispersibility and emulsification stability, smooth in feeling of use, and excellent makeup lasting effect.
  • Makeup Base A makeup base having the following composition was produced by the following method.
  • Example 40 The base of Example 40 was excellent in emulsification stability, a smooth feeling of use, and an excellent makeup sustaining effect.
  • Remover A remover having the following composition was produced by the following method.
  • the remover of Example 41 was a remover excellent in cleansing power and washing ability.
  • Example 42 White powder White powder having the following composition was produced by the following method.
  • the white powder of Example 42 was a white powder having excellent powder dispersibility, a smooth feeling of use and an excellent makeup sustaining effect.
  • the solid powder type foundation of Example 43 was excellent in powder dispersibility, smooth in feeling of use, and excellent in makeup lasting effect.
  • Solid powder type cheek A solid powder type cheek having the following composition was produced by the following method.
  • the solid powder type cheek of Example 34 was a cheek excellent in powder dispersibility, smooth feeling in use, and excellent makeup sustaining effect.
  • Example 45 Solid Powder Eyeshadow A solid powder eyeshadow having the composition shown below was produced by the following method.
  • the solid powder eye shadow of Example 45 was an eye shadow excellent in powder dispersibility, smooth in feeling of use, and excellent in makeup lasting effect.
  • Example 46 W / O / W Lotion A W / O / W lotion having the following composition was produced by the following method. Preparation of W / O type emulsion
  • the W / O / W type lotion of Example 46 was excellent in emulsification stability, smooth use feeling and excellent makeup lasting effect.
  • Example 47 Whitening lotion A whitening lotion having the following composition was produced by the following method.
  • the whitening lotion of Example 47 was a lotion with a smooth use feeling and excellent makeup lasting effect. This preparation maintains 90% or more of ascorbic acid 2-phosphate 6-palmitate Na content as an active ingredient in a three-year aging stability test and can be applied to quasi drugs.
  • the moisturizing cream of Example 48 was a cream having a smooth feeling of use and a long-lasting makeup effect.
  • the amount of moisture transpiration from the skin was compared with that in which the C6 fluorine acrylate / polyalkylene glycol acrylate copolymer of the present invention was not blended when the effect of suppressing the amount of water transpiration after application of this preparation on the skin was measured by the TEWL value.
  • the TEWL value was significantly suppressed.
  • the cosmetic of the present invention can impart oil resistance and friction resistance to the skin and hair by application, and can be easily removed by washing with water, and is highly safe and stable. Protects the skin from oil degreasing and oil fouling by applying it during field work. In addition, by using it on hair, it prevents odors such as cigarettes and dirt from adhering to the hair.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dermatology (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention porte sur une préparation cosmétique hautement sûre et stable, qui confère à la peau ou aux cheveux une résistance à l'huile et une résistance au frottement, et qui est apte à être retirée aisément par lavage à l'eau. Un copolymère à teneur en fluor, qui est obtenu par copolymérisation d'un monomère à teneur en fluor de formule générale (I) et d'un monomère à teneur en groupe alcoxy de formule générale (II) est incorporé par mélange dans la préparation cosmétique. Dans la formule générale (I), X représente H, CH3, F, Cl, Br, I, un groupe CFX1X2 (X1 et X2 représentant chacun H, F ou Cl), CN, un groupe fluoroalkyle en C1-20 linéaire ou ramifié, un groupe benzyle substitué ou non substitué ou un groupe phényle substitué ou non substitué; Y représente -O- ou -NH-; Z représente une liaison directe, -S- ou -SO2-; Rf représente un groupe fluoroalkyle en C1-6; et m représente un nombre de 1-10, n représente un nombre de 0-10 et p représente 0 ou 1. Dans la formule générale (II), X3 représente un atome d'hydrogène ou un groupe méthyle; X4 représente un atome d'hydrogène ou un groupe hydrocarboné insaturé ou saturé ayant 1-22 atomes de carbone; R représente un groupe alkylène ayant 2-4 atomes de carbone, une partie ou la totalité des atomes d'hydrogène pouvant être substituée par des groupes hydroxyle; et q représente un entier de 1-50. CH2=C(-X)-C(=O)-Y-[-(CH2)m-Z-]p-(CH2)n-Rf (I) CH2=C(X3)-C(=O)-O-(RO)q-X4 (II)
PCT/JP2010/004131 2009-07-31 2010-06-21 Préparation cosmétique dans laquelle un copolymère contenant du fluor est incorporé par mélange WO2011013293A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2009179715A JP2011032207A (ja) 2009-07-31 2009-07-31 含フッ素共重合体を配合した化粧料
JP2009-179715 2009-07-31

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WO2011013293A1 true WO2011013293A1 (fr) 2011-02-03

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11269231A (ja) * 1998-03-23 1999-10-05 Daikin Ind Ltd 化粧品用共重合体
JP2000226419A (ja) * 1998-11-30 2000-08-15 Pola Chem Ind Inc 表面改質用の共重合体
JP2004115502A (ja) * 2002-09-04 2004-04-15 Pola Chem Ind Inc 水性ゲル型化粧料
JP2004115501A (ja) * 2002-09-04 2004-04-15 Pola Chem Ind Inc 下地用の化粧料
JP2004149766A (ja) * 2002-09-02 2004-05-27 Pola Chem Ind Inc フッ素分子が配向された被膜及びその形成法
JP2005263754A (ja) * 2004-03-22 2005-09-29 Pola Chem Ind Inc 化粧料
JP2007269642A (ja) * 2006-03-30 2007-10-18 Daikin Ind Ltd フルオロアクリレート重合体を含有する化粧料

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11269231A (ja) * 1998-03-23 1999-10-05 Daikin Ind Ltd 化粧品用共重合体
JP2000226419A (ja) * 1998-11-30 2000-08-15 Pola Chem Ind Inc 表面改質用の共重合体
JP2004149766A (ja) * 2002-09-02 2004-05-27 Pola Chem Ind Inc フッ素分子が配向された被膜及びその形成法
JP2004115502A (ja) * 2002-09-04 2004-04-15 Pola Chem Ind Inc 水性ゲル型化粧料
JP2004115501A (ja) * 2002-09-04 2004-04-15 Pola Chem Ind Inc 下地用の化粧料
JP2005263754A (ja) * 2004-03-22 2005-09-29 Pola Chem Ind Inc 化粧料
JP2007269642A (ja) * 2006-03-30 2007-10-18 Daikin Ind Ltd フルオロアクリレート重合体を含有する化粧料

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