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WO2003075864A1 - Produits cosmetiques huileux - Google Patents

Produits cosmetiques huileux Download PDF

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Publication number
WO2003075864A1
WO2003075864A1 PCT/JP2003/002876 JP0302876W WO03075864A1 WO 2003075864 A1 WO2003075864 A1 WO 2003075864A1 JP 0302876 W JP0302876 W JP 0302876W WO 03075864 A1 WO03075864 A1 WO 03075864A1
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WO
WIPO (PCT)
Prior art keywords
group
oil
acid
general formula
carbon atoms
Prior art date
Application number
PCT/JP2003/002876
Other languages
English (en)
Japanese (ja)
Inventor
Tetsuo Nakanishi
Kiyomi Tachibana
Original Assignee
Shin-Etsu Chemical Co., Ltd.
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Filing date
Publication date
Application filed by Shin-Etsu Chemical Co., Ltd. filed Critical Shin-Etsu Chemical Co., Ltd.
Priority to JP2003574140A priority Critical patent/JP3625471B2/ja
Publication of WO2003075864A1 publication Critical patent/WO2003075864A1/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
    • A61K8/891—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
    • A61K8/18—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
    • A61K8/892—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a hydroxy group, e.g. dimethiconol
    • 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
    • A61Q19/00—Preparations for care of the skin

Definitions

  • the present invention relates to an oil-based cosmetic, and particularly to a clear touch obtained by blending a long-chain alkyl group-containing polyglycerin-modified silicone compound having a long-chain alkyl group and a hydrophilic group, polydariserin, simultaneously.
  • the present invention relates to a lubricating oily cosmetic which has a light and smooth feel without being sticky, has excellent adhesion to the skin, and has a very long lasting makeup.
  • oily dangling cosmetics are excellent in adhesion to the skin and their persistence, but have a very strong oily feeling when used, and are uncomfortable in terms of stickiness, weight, film thickness, etc. Prone to. Therefore, studies have been made to reduce the oiliness by blending silicone oil or the like having excellent extensibility and refreshing feeling. However, when silicone oil is added, the oily feeling is reduced, but negative sensations such as poor fit to the skin and lack of moistness, which are peculiar to silicone oil, appear. Goodness is lost. In addition, gloss for improving the quality of cosmetics was not satisfactory.
  • a polyglycerin-modified silicone compound having an alkyl group having 1 to 10 carbon atoms is contained as an oil agent component in order to reduce the unfamiliarity of the silicone oil to the skin and the lack of moist feeling.
  • An oil-based cosmetic characterized by this is also being developed (Japanese Patent Application Laid-Open No. 9-71504).
  • many oils such as paste oil and solid oil are used for oily cosmetics such as lipstick and oily foundation in order to maintain their form. These oils are rich in hydrocarbon oils, ester oils, higher alcohols and higher fatty acids having a carbon chain of 20 or more. Therefore, an alkyl group having 1 to 10 carbon atoms does not have sufficient compatibility, and the oily cosmetic composition is sufficiently satisfactory with respect to the tight feeling and the gloss that enhances the quality of cosmetics, which are characteristic of oily cosmetics. Then won.
  • the present inventors have further studied oil-based cosmetics.
  • oil-based cosmetics when a long-chain alkyl group-containing polyglycerin-modified silicone compound is added to the oil-based cosmetics, the adhesive properties characteristic of oil-based cosmetics are obtained.
  • the inventors have found that the present invention can be obtained, and have completed the present invention.
  • the present invention provides a lubricating oily dandelion cosmetic which has a moist touch, is non-greasy, has a light, smooth spread and feel, is extremely excellent in adhesion to the skin, and is excellent in long-lasting makeup.
  • the purpose is to provide. Disclosure of the invention
  • an oily cosmetic composition comprising a long chain alkyl group-containing polydariserine-modified silicone compound represented by the following general formula.
  • Si-A af SiO (SiO) a (SiO) b (SiO).
  • R 1 in the formula is an alkyl group having 1 to 10 carbon atoms, an aryl group, an aralkyl group, an amino-substituted alkyl group, a carboxyl-substituted alkyl group (may be partially substituted with halogen), Or the following general formula
  • R 1 s may be the same or different.
  • R 2 may be the same or different, and is an alkyl group having 11 to 30 carbon atoms.
  • R 3 is the following formula OH OH
  • R 4 is a hydrocarbon group having 4 to 30 carbon atoms, a halogen-substituted hydrocarbon group, or a carbon atom having 2 to 2 carbon atoms.
  • A is an organic group selected from R 2 or R 3
  • Q represents a divalent hydrocarbon group having 3 to 20 carbon atoms, and these hydrocarbon groups may contain an ether bond and an ester bond. ,.
  • a, b, and c are integers that satisfy the relationship 0 ⁇ a ⁇ 1 ⁇ 0, 1 ⁇ b ⁇ 100, 1 ⁇ c ⁇ 100 ⁇ 2 ⁇ a + b + c ⁇ 300, respectively.
  • d and e are integers of 0 ⁇ d ⁇ 15, 0 ⁇ e ⁇ 50, g and h are integers of 1 ⁇ g ⁇ 20, 1 ⁇ h ⁇ 20 respectively, and f is 1, 2 or 3 It is.
  • the polyglycerin-modified silicone compound having a long chain alkyl group used in the present invention is a compound represented by the following general formula (1) in which polyglycerin is bonded to a silicone chain via a bonding group.
  • R 1 in the compound represented by the general formula (1) is an alkyl group having 1 to 10 carbon atoms, an aryl group, an aralkyl group, an amino-substituted alkyl group, a carboxyl-substituted alkyl group (partially substituted with halogen). And all R 1 are the same. Or different.
  • R 1 examples include an alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nor group, and a decyl group; Examples thereof include alkyl groups such as alkyl groups such as hexyl groups, aryl groups such as phenyl and tolyl groups, aralkyl groups such as benzyl group and phenethyl group, 3-aminopropyl group, 3- [(2 —Aminoethyl) amino amino-substituted alkyl group such as propyl group, and carboxy-substituted alkyl group such as 3-carboxypropyl group.
  • a compound in which a part of hydrogen is replaced by halogen such as a trifluoropropyl group and a nonafluor
  • Part of R 1 may be an organic group represented by the following general formula (2).
  • R 4 is a hydrocarbon group having 4 to 30 carbon atoms, a halogen-substituted hydrocarbon group, or an acyl group having 2 to 30 carbon atoms.
  • d and e are integers of 0 ⁇ d ⁇ 15 and 0 ⁇ e ⁇ 50, respectively. Accordingly, the groups represented by the above general formula (2) are alcohol residues and alkenyl ether adduct residues. .
  • e ⁇ l it is an alcohol residue of a higher alcohol propylene oxide adduct (terminal is a hydroxyl group).
  • e is not 0, an alkoxy group or an ester group is present via polyoxypropylene.
  • hydrolysis resistance may be poor, and when d is 15 or more, the oily odor is strong, so d is preferably 3 to 5. ,.
  • R 2 is an alkyl group having 11 to 30 carbon atoms (which may be partially substituted by halogen).
  • it is an decyl group, a dodecinole group, a tridecyl group, a tetradecyl group, a hexadecyl group, an octadecyl group, a behenyl group, and an alkyl group partially substituted with halogen.
  • a dodecyl group and a hexadecyl group are preferred.
  • the oily odor due to the raw material is weak, and sufficient compatibility with an oil agent can be obtained.
  • R 3 is an organic polyglycerin group represented by the following general formula (3), (4) or (5).
  • Q represents a divalent hydrocarbon group having 3 to 20 carbon atoms, which may contain an ether bond and a ester bond.
  • Specific examples one (CH 2) 2 _, _ (CH 2) 3 -, - CH 2 CH (CH 3) CH 2 -, one (CH 2) 4 -, - (CH 2) 5 -, - (CH 2) 6 -, one (CH 2) 7 -, one (CH 2) 8 -, - (CH 2) 2 _CH (CH 2 CH 2 CH 3) -, -CH 2 - CH (CH 2 CH 3 ) - one (CH 2) 3 - O_ ( CH 2) 2 -, _ (CH 2) 3 - 0- (CH 2) 2 _0- (CH 2) 2 -, one (CH 2) "0- CH 2 CH (CH 3 ) — and —CH 2 —CH (CH 3 ) —COO (CH 2 ) 2 — ⁇ .
  • g and h are integers of 1 to 20, and include polyglycerols such as diglycerin, triglycerin, tetraglycerin, octaglycerin, decaglycerin, hexadecane glycerin, and octadecaglycerin Glycerin, also represented by (5) b
  • Triglycerin may be bonded via Q, and a part of the hydroxyl group of polyglycerin may be substituted with an alkoxy group or an ester group. If the force g is large, the viscosity is low and the usability is poor. Therefore, g and h are preferably integers of 1 to 10.
  • A is an organic group selected from R 2 or R 3 , and f is 1, 2 or 3 Force.
  • f is preferably 2 or 3.
  • a, b, and c are 0 ⁇ a ⁇ 100, 1 ⁇ b ⁇ 100, 1 ⁇ c ⁇ 100, and are integers satisfying 2 a + b + c ⁇ 300.
  • the oily cosmetic can be imparted with a smooth feel peculiar to the silicone compound.
  • a is in the range of 20 ⁇ a ⁇ 60, it is preferable that 5 ⁇ b ⁇ 40, and c is 5 c ⁇ 20, because of compatibility with the oil agent. By doing so, it is possible to provide a lubricating oily cosmetic which is extremely excellent in adhesion to the skin and also has a long lasting makeup.
  • the polyglycerin-modified silicone compound containing a long-chain alkyl group of the above formula (1) used in the present invention is preferably an organohydrogenpolysiloxane and, for example, a triglycerin aryl ether compound represented by the following formula (ii), particularly preferably: Is the following equation (iii)
  • R 4 and e in the formula (i) and g in the formula (ii) are the same as those described above.
  • the above addition reaction is preferably carried out in the presence of a platinum catalyst or a rhodium catalyst.
  • a catalyst such as chloroplatinic acid, alcohol-modified chloroplatinic acid, or chloroplatinic acid-vinylsiloxane complex is used. It is preferred to use.
  • the amount of the catalyst used may be a catalytic amount, but is preferably 50 ppm or less, particularly preferably 20 ppm or less in terms of platinum or rhodium.
  • the above addition reaction may be performed in an organic solvent, if necessary.
  • the organic solvent include aliphatic alcohols such as methanol, ethanol, 2-propanol and butanol, aromatic hydrocarbons such as toluene and xylene, and aliphatic or fatty acids such as n-pentane, n-hexane and cyclohexane.
  • Examples include cyclic hydrocarbons, dichloromethane, chloroform, halogenated hydrocarbons such as carbon tetrachloride, and the like.
  • the conditions for the addition reaction are not particularly limited, but the reaction is preferably carried out under reflux for 1 to 10 hours.
  • the reaction is preferably carried out under reflux for 1 to 10 hours.
  • 0.1N HC1 water is added so that the concentration becomes 10 to 30% with respect to the reaction mixture, and the mixture is heated and stirred at 50 to 100 ° C for 5 to 10 hours. Do by doing.
  • the amount of the compound is 0.1 to 0.1% with respect to the cosmetic.
  • the content is preferably from 70 to 70% by weight, particularly preferably from 1 to 50% by weight.
  • the oily cosmetics of the present invention include not only make-up cosmetics such as lipsticks and oily foundations, skin cosmetics and hair cosmetics, but also all oily products used externally on the skin, such as external medicines. Is done.
  • the oil-based cosmetic of the present invention includes, in addition to the components described above, solids used in ordinary cosmetics.
  • Semi-solid, liquid oils and the like can be used.
  • natural animal and vegetable oils and fats and semi-synthetic oils include apogado oil, linseed oil, almond oil, ibotaro, eno oil, olive oil, cocoa butter, kapok wax, kaya oil, carnauba wax, oil, candelilla wax, tallow , Beef tallow, beef bone fat, hardened beef tallow, kiyoun oil, spermaceti, hardened oil, wheat germ oil, sesame oil, rice germ oil, rice oil, sugar cane wax, sazanka oil, safflower oil, shea butter, Cinnamon oil, cinnamon oil, jojoba wax, squalene, shellac wax, turtle oil, soybean oil, teaseed oil, camellia oil, evening primrose oil, corn oil, lard, rap
  • hydrocarbon oils examples include ozokerite, squalane, squalene, ceresin, paraffin, paraffin wax, polyethylene wax, polyethylene 'polypropylene wax, liquid paraffin, pristane, polyisobutylene, microcrystalline wax, petrolatum, etc .; Acid, myristic acid, norremitic acid, stearic acid, behenic acid, pendecilenic acid, oleic acid, linoleic acid, linolenic acid, arachidonic acid, eicosapentaenoic acid (EPA), docosahexanoic acid (DHA), isostearic acid , 12-hydroxystearic acid and the like.
  • Acid myristic acid, norremitic acid, stearic acid, behenic acid, pendecilenic acid, oleic acid, linoleic acid, linolenic acid, arachidonic acid, eicosapentaenoic acid (EPA),
  • Higher alcohols include lauryl alcohol, myristyl alcohol, palmityl alcohol, stearyl alcohol, behenyl alcohol, hexadecinole alcohol, saiylrail alcohol, isosteararyl alcohol, hexildodecanol, otatildodecanol, and setosteryl alcohol. , 2-decyltetra Desinore, cholesterol, phytosterole, POE cholesterol, monostearyl glycerin ether (Bacyl alcohol), monoleinol glyceryl ethereole (Seracyl alcohol) and the like.
  • Ester oils include diisobutyl adipate, 2-hexyldecyl adipate, di-2-butyltyl adipate, isononyl isononanoate, N-alkyldaricol monoisostearate, isocetyl isostearate, trimethylolpropane triisostearate, Ethylene glycol di-2-ethylhexanoate, cetyl 2-ethylhexanoate, trimethylolpropane tri-2-ethylhexanoate, pentaerythritol tetra-2-ethylhexanoate, cetyl octanoate, octyl dodecyl gum ester Oleyl oleate, otatyl dodecyl oleate, decyl oleate, neopentyl dicholic dicaprate, triethyl citrate, 2-ethy
  • silicone oil examples include low- to high-viscosity linear or branched organopolysiloxanes such as dimethinolepolysiloxane, methinorefenylpolysiloxane, methhydrodienepolysiloxane, and dimethinolesiloxane / methinolephenylsiloxane copolymer. 4 ⁇ cyclotetrasiloxane, decamethylcyclopentane ⁇ U
  • Cyclic siloxanes such as roxane, dodecamethylcyclohexasiloxane, tetramethyltetrahydrogencyclotetrasiloxane, tetramethyltetraphenylenocyclotetrasiloxane, gum dimethylpolysiloxane with a high degree of polymerization, gum dimethylsiloxane methyl Silicone rubber such as phenyl siloxane copolymer, and cyclic siloxane solution of silicone rubber, cyclic siloxane solution of trimethylsiloxykeic acid, trimethylsiloxykeic acid, higher alkoxy-modified silicone such as stearoxysilicone, higher fatty acid-modified silicone, alkyl Modified silicones, amino-modified silicones, fluorine-modified silicones, silicone resins, and melts of silicone resins, and the like are included.
  • the fluorinated oil examples include perfluoropolyether, perfluorodephosphorus, perfluorooctane, and the like.
  • the compounding amount of these oils is preferably in the range of 1 to 99% by weight of the whole cosmetic.
  • Powders can be further used in the cosmetic of the present invention according to the purpose.
  • the powder if it is used for ordinary cosmetics, its shape (spherical shape, needle shape, plate shape, etc.), particle size (fog shape, fine particles, pigment grade, etc.), particle structure (porosity) Irrespective of the quality, non-porous, etc.).
  • examples include inorganic powders, organic powders, surfactant metal salt powders, colored pigments, pearl pigments, metal powder pigments, and natural pigments.
  • the inorganic powder include titanium oxide, zirconium oxide, zinc oxide, cerium oxide, magnesium oxide, barium sulfate, calcium sulfate, magnesium sulfate, calcium carbonate, magnesium carbonate, talc, myriki, kaolin, and sericite.
  • Muscovite synthetic mica, phlogopite, phlogopite, biotite, lithic mica, caicic acid, silicate, aluminum silicate, magnesium silicate, aluminum silicate magnesium, calcium silicate, barium silicate, silicate Strontium acid, metal tandastate, hydroxyapatite, vermiculite, hygilite, bentonite, montmorillonite, hectrite, zeolite, ceramics powder, dibasic calcium phosphate, alumina, aluminum hydroxide, nitrided Examples include boron, boron nitride, and silica. .
  • organic powder examples include polyamide powder, polyester powder, and polyethylene powder.
  • Fine powder of crosslinked silicone with modified structure fine powder of polymethylsilsesquioxane, styrene / acrylic acid copolymer, dibutylbenzene 'styrene copolymer, butyl resin, urea resin, phenol resin, fluororesin Resin powder such as silicone resin, silicone resin, acrylic resin, melamine resin, epoxy resin, and polycarbonate resin, microcrystalline fiber powder, starch powder, and radiolysine powder.
  • Surfactant metal salt powders include zinc stearate, anolemme-stearate, calcium stearate, magnesium stearate, zinc myristate, magnesium myristate, zinc cetyl phosphate, calcium cetyl phosphate
  • specific examples of colored pigments include inorganic red pigments such as iron oxide, iron hydroxide, and iron titanate; inorganic brown pigments such as ⁇ -iron oxide; yellow iron oxide; Inorganic black pigments such as black iron oxide, carbon black, etc .; inorganic purple pigments such as manganese violet and cobalt violet; hydroxy hydric chrome, oxidized chromium, oxidized cobalt, and cobalt titanate.
  • inorganic green pigments navy blue, ultramarine blue, etc., and tar pigments And natural lakes, synthetic resin powders obtained by compounding these powders, and the like.
  • pearl pigments examples include titanium oxide-coated mica, titanium oxide-coated myric, oxychloride bismuth, oxidized titanium-coated oxychloride bismuth, titanium oxide-coated talc, fish scale foil, and titanium oxide-coated colored mica.
  • Pigments aluminum powder, kappa powder, stainless powder, etc .; tar pigments: Red No. 3, Red No. 104, Red No. 106, Red No. 201, Red No. 02, Red No. 2 04, red 205, red 220, red 222, red 227, red 228, red 230, red 410, red 501 No. 5, Yellow No. 4, Yellow No. 5, Yellow No. 02, Yellow No. 203, Yellow No. 204, Yellow No. 401, Blue No.
  • Natural pigments include carminic acid, laccaic acid, canolethamine, brasilin, closin, etc. And the like.
  • powders that absorb and scatter ultraviolet rays such as fine particle titanium oxide, fine particle iron-containing titanium oxide, fine particle oxidized zinc, fine particle acid hyserium, and composites thereof, may also be used.
  • these powders those obtained by compounding the powder or treating with a general oil agent, a silicone oil other than the present invention, a fluorine compound, a surfactant or the like within a range not to impair the effects of the present invention.
  • a general oil agent e.g., a silicone oil other than the present invention, a fluorine compound, a surfactant or the like within a range not to impair the effects of the present invention.
  • a fluorine compound e.g., a surfactant or the like
  • one or more kinds of crosslinked organopolysiloxanes may be used according to the purpose.
  • the crosslinked organopolysiloxane is 0. To 6 5 mm 2 / sec ⁇ 1 0 0. 0 mm 2 / s low viscosity silicone, it absorbs the low viscosity silicone or its own weight is to swell preferable.
  • the cross-linking agent of this cross-linked organopolysiloxane has a cross-linking structure by having two or more bulging reaction sites in the molecule and reacting with a hydrogen atom directly bonded to a silicon atom. Preferably, it is formed.
  • the crosslinked organopolysiloxane may contain at least one moiety selected from the group consisting of a polyoxyalkylene moiety, an alkyl moiety, an alkenyl moiety, an aryl moiety, and a fluoroalkyl moiety in the crosslinked molecule. good. These are not limited, but as commercial products, KSG_15, KSG-16, KSG-18, and KSG-21 gelled with silicone oil (all are Shin-Etsu Chemical Co., Ltd. ) Product name).
  • cross-linked organopolysilane port hexane the 0. 6 5 mm 2 / sec ⁇ 1 0 0. 0 mm 2 / oil agent other than the low came Uranaido silicone seconds, which swells to the amount absorbed than its own weight Is also used.
  • the cross-linking agent of this cross-linked organopolysiloxane has a cross-linking structure by reacting with a hydrogen atom directly bonded to a silicon atom and having two or more bi-el reactive sites in the molecule.
  • the crosslinked organopolysiloxane is selected from the group consisting of a polyoxyalkylene moiety, an alkyl moiety, an alkenyl moiety, an aryl moiety, and a fluoroalkyl moiety. At least one selected from them may be contained in the crosslinking molecule.
  • these are not particularly limited, but commercially available products include KSG-31, KSG_32, KSG-33, KSG-34, KSG-34, KSG-41, KSG-42, gelled with hydrocarbon oil and triglyceride oil.
  • KSG-43 and KSG-44 both are trade names manufactured by Shin-Etsu Chemical Co., Ltd.).
  • One or two or more silicone resins may be used in the cosmetic of the present invention depending on the purpose.
  • This silicone resin is preferably an acrylic silicone resin of an acrylic / silicone graft or block copolymer.
  • an acrylyl silicone containing at least one kind selected from a pyrrolidone moiety, a long-chain alkyl moiety, a polyoxyalkylene moiety, a fluoroalkyl moiety, and an aryon moiety such as carboxylic acid in the molecule. Can also be used.
  • this silicone resin is preferably a silicone network compound represented as MQ, MDQ, MT, MDT, MD TQ as a constituent.
  • M, D, T, and Q are R 3 S i 0, respectively. . 5 units, RS i O units, RS i 0 L5 unit, which represents the S i 0 2 Unit, are those commonly used in the silicone industry.
  • the silicone network resin is generally known as MQ resin, MT resin, or MDT resin, and may have a portion represented by MDQ or MDTQ.
  • silicone resins are commercially available as a solution such as octamethylcyclotetrasiloxane, and are selected from a pyrrolidone portion, a long-chain alkyl portion, a polyoxyalkylene portion, a fluoroalkyl portion, and an amino portion. At least one kind of moiety may be contained in the molecule.
  • one or more oil-soluble gelling agents or organically modified clay minerals can be used according to the purpose.
  • oil-soluble gelling agent examples include metal soaps such as arminium stearate, magnesium stearate, and zinc myristate; amino acid derivatives such as N-lauroyl-L-glutamic acid, ⁇ , page - ⁇ -butylylamine, and the like.
  • Dextrin fatty acid esters such as dextrin palmitic acid ester, dextrin stearate ester, dextrin 2-ethylhexanoate palmitate ester, sucrose palmite Sucrose fatty acid esters such as citrate esters and sucrose stearates, benzylidene derivatives of sorbitol such as monobenzylidene sorbitol and dibenzylidene sorbitol, dimethylbenzyldecylmonium montmorillonite cream, dimethyldiocta Gelling agents selected from organically modified clay minerals such as decyl ammonium montmorillonite clay are exemplified.
  • one or more organic ultraviolet absorbers may be used according to the purpose.
  • benzoic acid-based ultraviolet absorbers such as para-aminobenzoic acid
  • anthranilic acid-based ultraviolet absorbers such as methyl anthranilate
  • salicylic acid-based ultraviolet absorbers such as methyl salicylate
  • octyl paramethoxy citrate Ca-cinnamic acid UV absorber benzophenone UV absorber such as 2,4-dihydroxybenzophenone, etc.
  • Perocanic acid UV absorber such as ethyl perocyanate, 4-t-butyl-4'-methoxydibenzo And dibenzoylmethane-based ultraviolet absorbers such as ethylmethane.
  • antibacterial agents such as alkyl paraoxybenzoate, benzoic acid, sodium benzoate, sorbic acid, potassium sorbate, phenoxyethanol, etc.
  • antibacterial agents include benzoic acid, salicylic acid, phenolic acid, sorbic acid, alkyl parabenzoyl ester, Antibacterial and preservatives such as parachloromethcresol, hexaclofen, benzalcohemium chloride, chlorhexidine chloride, trichlorocarbanilide, photosensitizer, phenoxetanol, tocopherol, butylhydroxyanisole, An antioxidant such as dibutylhydroxytoluene and phytic acid can also be added.
  • the oily cosmetic of the present invention includes water; lower alcohols such as ethanol and isopropanol; sugar alcohols such as sorbitol and maltose; cholesterol, sitosterol, phytosterol and lanosterol as long as the effects of the present invention are not impaired.
  • Polyhydric alcohols such as butylene glycol, propylene dalicol, and dibutylene glycol; water-soluble or water-swellable polymers; anionic, cationic, nonionic and amphoteric surfactants; It can also be used.
  • aluminum chlorohydrate, aluminum chloride, aluminum sesquichlorohydrate, zirconinoleoxycyclolide, aluminum zirconium hydroxychloride, aluminum aluminum are used as long as the effects of the present invention are not impaired.
  • PH control of antiperspirants selected from muzirconium glycine complexes, lactic acid, citric acid, glycolic acid, conodic acid, tartaric acid, d1-malic acid, carbonated lime, sodium bicarbonate, ammonium bicarbonate, etc.
  • Agents such as alanine, sodium edetate, sodium polyphosphate, sodium metaphosphate, and phosphoric acid; cooling agents such as L-menthol, camphor; allantoin; glycyrrhizic acid and its salts; glycyrrhetinic acid and glycyrrhetinic acid
  • Anti-inflammatory agents such as stearyl, tranexamic acid, and azulene can be added.
  • a beautiful skin component can be blended.
  • the above-mentioned components for skin beautifulness include whitening agents such as placenta extract, arbutin, daltathione, and extract of saxifraga, royal jelly, photosensitizer, cholesterol derivatives, cell activators such as calf blood extract, skin roughening agents, Nonylate perenylamide, nicotinic acid benzyl ester, nicotinic acid 3-butoxystil ester, capsaicin, zingerone, cantharistine tincture, dictamol, caffeine, tangeric acid, monobonoleneol, tocopherol nicotinate, inositol hexanicotinate, cycla Blood circulation promoters such as dernate, cinnarizine, tolazoline, acetylcholine, verapamil, cepharanthin, and V-oryzanol; skin
  • vitamins and diamino acids can be blended as long as the effects of the present invention are not hindered.
  • vitamin A such as vitamin A oil, retinol, retinol acetate, retinol palmitate
  • vitamin B2 such as riboflavin, riboflavin butyrate, flavin adenine nucleotide, pyridoxine hydrochloride, pyridoxindione Vitamin B6 such as kutanoate and pyridoxine tripalmitate
  • vitamin B12 and its derivatives vitamin B15 such as vitamin B15 and its derivatives
  • vitamins D such as ergocalciferol and cholecalciferol
  • ⁇ tocopheron
  • amino acid amino acids include glycine, valine, leucine, isoleucine, serine, threonine, pheninolealanine, arginine, lysine, aspartic acid, glutamic acid, cystine, cystine, methionine, tryptophan, etc.
  • Examples include estradiol, ethurestradiol and the like.
  • % described below means “% by weight”.
  • a raw material of the triglycerin derivative an aryl ether derivative represented by the following (iii) and a polyglycerin aryl ether represented by the following ( ⁇ ) were used.
  • Siloxane compound 1 Alkyl / triglycerin co-modified silicone
  • methylhydrogenpolysiloxane represented by the following average composition formula (6), 700 g of an aryl ether derivative, 90 g of 1-hexadecene, 340 g of isopropyl alcohol (IPA) and 340 g of chloroplatinic acid 0.5 weight 0/0 of I PA soluble ⁇ I
  • reaction solution was transferred to an autoclave, 75 g of Raney nickel was added, hydrogen was introduced, and the reaction was carried out at 120 ° C for 3 hours. During the reaction, the hydrogen pressure was kept at 0.5 MPa.
  • reaction mixture from which the catalyst was filtered was charged into the reactor again, and 140 g of a 0.1N aqueous HC1 solution was added thereto, and the mixture was hydrolyzed at 70 ° C. for 3 hours to distill acetone.
  • Siloxane compound 2 Alkyl (PO) ⁇ triglycerin co-modified silicone
  • methyl hydrogen polysiloxane 300 g represented by the following average composition formula (8), aryl ether derivative 130 g, oleyl polyoxypropylene (3 ) Arirueteru ⁇ Nippon emulsifier Co., Ltd. RG- 1252 ⁇ 60 g, isopropyl alcohol (I PA) 0.99 g, a I PA solution 0. 2 g of Oyopi Shioi ⁇ aurate 0.5 wt 0/0
  • the reaction was carried out under the reflux of the solvent for 8 hours.
  • reaction solution was transferred to an autoclave, and after adding 32 g of Raney nickel, hydrogen was introduced and reacted at 120 ° C. for 3 hours. During the reaction, the hydrogen pressure was kept at 0.5 MPa.
  • Siloxane compound 3 Alkyl / triglycerin co-modified silicone
  • methyl hydrogen polysiloxane represented by the following average composition formula (10), 130 g of an aryl ether derivative, 120 g of 1-hexadecene, 180 g of isopropyl alcohol (IPA), and chloroplatinic acid g of IPA solution 0. 3 g of 0.5 wt 0/0, and allowed to react for 8 hours under reflux of the solvent.
  • IPA isopropyl alcohol
  • reaction solution was transferred to an autoclave, 40 g of Raneykel was added, hydrogen was introduced, and the mixture was reacted at 120 ° C. for 3 hours. During the reaction, the hydrogen pressure was maintained at 0.5 MPa.
  • reaction mixture from which the catalyst was filtered was charged into the reactor again, and 26 g of a 0.1N aqueous solution of HC1 was added thereto, and the mixture was hydrolyzed with 70 for 3 hours to distill acetone.
  • This product was a pale yellow transparent liquid, having a viscosity of 11.0 Pa ⁇ s (25 ° C) and a refractive index of 1.413 (25 ° C).
  • Siloxane compound 4 alkyl-polyglycerin-modified silicone
  • a reactor is charged with 200 g of methylhydrogenpolysiloxane of the average composition formula (12), 240 g of polyglycerinyl ether having an unsaturation degree of 3.44 meq / g, 500 g of isopropyl alcohol (IPA), and sodium chloride.
  • IPA isopropyl alcohol
  • 0.3 g of 0.5% 1% solution of platinic acid was charged and reacted under reflux of the solvent for 8 hours. Further, 120 g of dexadecene was added dropwise under reflux of the solvent to complete the reaction.
  • This product was a pale yellow transparent liquid, having a viscosity of 70 Pa ⁇ s (25 ° C) and a refractive index of 1.450 (25 ° C).
  • Siloxane compound 5 alkyl'polyglycerin-modified silicone
  • m is 3 on average.
  • This product was a pale yellow, transparent liquid, having a viscosity of 21 Pa ⁇ s (25 ° C) and a refractive index of 1.426 (25 ° C).
  • Siloxane compound 5 Triglycerin co-modified silicone without long chain (Reference Example 1 of JP-A-9-71504)
  • methyl hydrogen polysiloxane represented by the following average composition formula (16)
  • 100 g of an aryldiglycerin ether derivative 200 g of isopropyl alcohol (IPA), and 0.5 g of Shiraidani platinum acid were added.
  • IPA solution 0. 5 g of weight 0/0, the reaction was conducted for 3 hours under reflux of the solvent.
  • A Components 1 to 10 were dissolved by heating.
  • B was uniformly dispersed with three rollers.
  • the oily foundation of Example 13 in which the polyglycerin-modified silicone corn compound containing a long-chain alkyl group of the present invention was blended showed a higher product surface compared to Comparative Example 12. It is an oily foundation that has excellent gloss, closeness to skin, tightness, and softness, has no stickiness, is moist, and has a beautiful finish. It turned out to be. Also, compared to Comparative Example 3, the product surface is excellent in luster and tightness, and it also has a good sense of adhesion, firmness, beautiful finish and good makeup, and is full of luxury. I understood.
  • Pentaerythrin rosin acid 5.0 5.0 5.0 5.0 5.0 5.0
  • component 14 was added, filled and molded.
  • the lipsticks of Examples 4 to 5 in which the long-chain alkyl group-containing polyglycerin-modified silicone compound of the present invention was blended had much more gloss on the product surface than Comparative Examples 3 and 4. And no stickiness after application.
  • a part of components 1 to 8 and 9 were mixed by heating and dissolved.
  • the lipstick obtained as described above had a glossy surface, was light in color, had no oiliness or powderiness, and gave a refreshing feel. In addition, it had good water resistance and water repellency, good durability, and excellent stability.
  • A Components 1 to 7 were mixed.
  • component 8 After packing A in an aerosol can, component 8 was filled to obtain a brushing agent.
  • the brushing agent spray obtained as described above was glossy, very smooth, and excellent in sustainability.
  • the powder was excellent in dispersibility of the powder during use, had good combability, and was very good with luster.
  • dimethylpolysiloxane (6 mm 2 / sec (25 ° C)) 1 0. 0
  • A Components 1 to 6 were mixed.
  • the roll-on type antiperspirant obtained in the manner described above was lightly spreadable, had a refreshing sensation, was refreshing, and was not sticky or oily. Also, depending on temperature and aging There was no change and the usability and stability were very good. Industrial applicability
  • the oil-based cosmetic of the present invention containing the long-chain alkyl group-containing polyglycerin-modified silicone compound has excellent luster on the product surface, has a moist touch, and is non-greasy. It has a light touch, excellent adhesion to the skin, and a very high-quality oil-based cosmetic with a very long lasting makeup.

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Abstract

L'invention concerne des produits cosmétiques huileux, qui comprennent des silicones modifiés par polyglycérol présentant des groupes alkyle à chaîne longue représentés par la formule (1). Dans ladite formule, R1 est alkyle C1-10, aryle, aralkyle, aminoalkyle, carboxyalkyle (qui peut être partiellement remplacé par halogène), ou -CdH2d-O- (C3H6O) eR4; R2 est un alkyle comportant 11 à 30 atomes de carbone; R3 est un groupe polyglycérol spécifique; R4 est un groupe hydrocarboné comportant 4 à 30 atomes de carbone, un groupe hydrocarboné halogéné, ou un acyle comportant 2 à 30 atomes de carbone; A est R2 ou R3; et Q est un groupe hydrocarboné C3-30 divalent pouvant comporter une liaison éther ou ester.
PCT/JP2003/002876 2002-03-11 2003-03-11 Produits cosmetiques huileux WO2003075864A1 (fr)

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Cited By (14)

* Cited by examiner, † Cited by third party
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EP1579845A2 (fr) * 2004-03-22 2005-09-28 L'oreal Composition cosmétique contenant un élastomère de silicone polyglycérolé
JP2006069934A (ja) * 2004-08-31 2006-03-16 Kose Corp 化粧料
JP2008500349A (ja) * 2004-05-24 2008-01-10 ザ プロクター アンド ギャンブル カンパニー ファンデーション
JP2008500350A (ja) * 2004-05-24 2008-01-10 ザ プロクター アンド ギャンブル カンパニー 化粧用ファンデーション
WO2011049247A1 (fr) 2009-10-23 2011-04-28 東レ・ダウコーニング株式会社 Agent épaississant ou gélifiant pour des matières premières huileuses
WO2011049248A1 (fr) 2009-10-23 2011-04-28 東レ・ダウコーニング株式会社 Nouvel organopolysiloxane co-modifié
US8597619B2 (en) 2009-12-21 2013-12-03 Dow Corning Toray., Ltd. Thickener or gellant for oil materials, gel composition comprising same, and method of producing cosmetic material or topical agent
WO2014200111A1 (fr) * 2013-06-13 2014-12-18 東レ・ダウコーニング株式会社 Silicone modifiée par un dérivé diglycérine contenant des groupes hydrocarbonés à longue chaine, et son utilisation
JP2015003891A (ja) * 2013-06-24 2015-01-08 ライオン株式会社 デオドラントスティック組成物
US9133309B2 (en) 2009-10-23 2015-09-15 Dow Corning Toray Co., Ltd. Organopolysiloxane copolymer
WO2017148827A1 (fr) 2016-02-29 2017-09-08 Wacker Chemie Ag Utilisation de polysiloxanes modifiés par alkylglycosides dans des produits de soins personnels à base d'huile pure
US10406092B2 (en) 2012-12-28 2019-09-10 Dow Silicones Corporation Method for producing transparent or semi-transparent liquid glycerin-derivative-modified silicone composition
EP3854303A1 (fr) 2020-01-22 2021-07-28 Shin-Etsu Chemical Co., Ltd. Composition de bio-électrode, bio-électrode et procédé de fabrication de bio-électrode
WO2022172816A1 (fr) * 2021-02-10 2022-08-18 信越化学工業株式会社 Organopolysiloxane et produit cosmétique le contenant

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JP2002104934A (ja) * 2000-07-28 2002-04-10 Kao Corp 毛髪化粧料
JP2002348214A (ja) * 2001-05-25 2002-12-04 Kose Corp 毛穴隠し用水中油型乳化化粧料
JP2003081770A (ja) * 2001-09-06 2003-03-19 Shin Etsu Chem Co Ltd シリカ含有複合酸化物球状微粒子を含有する化粧料

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JP2002104934A (ja) * 2000-07-28 2002-04-10 Kao Corp 毛髪化粧料
JP2002348214A (ja) * 2001-05-25 2002-12-04 Kose Corp 毛穴隠し用水中油型乳化化粧料
JP2003081770A (ja) * 2001-09-06 2003-03-19 Shin Etsu Chem Co Ltd シリカ含有複合酸化物球状微粒子を含有する化粧料

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7378103B2 (en) 2004-03-22 2008-05-27 L'oreal Cosmetic composition comprising a polyglycerolated silicone elastomer
EP1579845A3 (fr) * 2004-03-22 2006-03-08 L'oreal Composition cosmétique contenant un élastomère de silicone polyglycérolé
EP1579845A2 (fr) * 2004-03-22 2005-09-28 L'oreal Composition cosmétique contenant un élastomère de silicone polyglycérolé
CN1781476B (zh) * 2004-03-22 2013-10-16 莱雅公司 包含聚甘油化硅氧烷弹性体的化妆品组合物
US7867505B2 (en) 2004-05-24 2011-01-11 The Procter & Gamble Company Foundation
JP2008500350A (ja) * 2004-05-24 2008-01-10 ザ プロクター アンド ギャンブル カンパニー 化粧用ファンデーション
US7892570B2 (en) 2004-05-24 2011-02-22 The Procter & Gamble Company Cosmetic foundation
JP2008500349A (ja) * 2004-05-24 2008-01-10 ザ プロクター アンド ギャンブル カンパニー ファンデーション
JP4629389B2 (ja) * 2004-08-31 2011-02-09 株式会社コーセー 化粧料
JP2006069934A (ja) * 2004-08-31 2006-03-16 Kose Corp 化粧料
US9133309B2 (en) 2009-10-23 2015-09-15 Dow Corning Toray Co., Ltd. Organopolysiloxane copolymer
WO2011049247A1 (fr) 2009-10-23 2011-04-28 東レ・ダウコーニング株式会社 Agent épaississant ou gélifiant pour des matières premières huileuses
WO2011049248A1 (fr) 2009-10-23 2011-04-28 東レ・ダウコーニング株式会社 Nouvel organopolysiloxane co-modifié
US9580600B2 (en) 2009-10-23 2017-02-28 Dow Conring Toray Co., Ltd. Thickening or gelling agent for oily raw materials
US8597619B2 (en) 2009-12-21 2013-12-03 Dow Corning Toray., Ltd. Thickener or gellant for oil materials, gel composition comprising same, and method of producing cosmetic material or topical agent
US10406092B2 (en) 2012-12-28 2019-09-10 Dow Silicones Corporation Method for producing transparent or semi-transparent liquid glycerin-derivative-modified silicone composition
WO2014200111A1 (fr) * 2013-06-13 2014-12-18 東レ・ダウコーニング株式会社 Silicone modifiée par un dérivé diglycérine contenant des groupes hydrocarbonés à longue chaine, et son utilisation
US9783643B2 (en) 2013-06-13 2017-10-10 Dow Corning Toray Co., Ltd. Silicone modified by long-chain hydrocarbon group-containing diglycerin derivative, and use thereof
JP2015003891A (ja) * 2013-06-24 2015-01-08 ライオン株式会社 デオドラントスティック組成物
WO2017148827A1 (fr) 2016-02-29 2017-09-08 Wacker Chemie Ag Utilisation de polysiloxanes modifiés par alkylglycosides dans des produits de soins personnels à base d'huile pure
EP3854303A1 (fr) 2020-01-22 2021-07-28 Shin-Etsu Chemical Co., Ltd. Composition de bio-électrode, bio-électrode et procédé de fabrication de bio-électrode
KR20210095044A (ko) 2020-01-22 2021-07-30 신에쓰 가가꾸 고교 가부시끼가이샤 생체 전극 조성물, 생체 전극 및 생체 전극의 제조 방법
US11998339B2 (en) 2020-01-22 2024-06-04 Shin-Etsu Chemical Co., Ltd. Bio-electrode composition, bio-electrode, and method for manufacturing bio-electrode
WO2022172816A1 (fr) * 2021-02-10 2022-08-18 信越化学工業株式会社 Organopolysiloxane et produit cosmétique le contenant
JP7509248B2 (ja) 2021-02-10 2024-07-02 信越化学工業株式会社 オルガノポリシロキサン及びこれを含有する化粧料

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