WO2010114110A1 - Polymère de siloxane alcoxylé à modification fluor, poudre traitée en surface et produit cosmétique comprenant celle-ci - Google Patents

Polymère de siloxane alcoxylé à modification fluor, poudre traitée en surface et produit cosmétique comprenant celle-ci Download PDF

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Publication number
WO2010114110A1
WO2010114110A1 PCT/JP2010/056046 JP2010056046W WO2010114110A1 WO 2010114110 A1 WO2010114110 A1 WO 2010114110A1 JP 2010056046 W JP2010056046 W JP 2010056046W WO 2010114110 A1 WO2010114110 A1 WO 2010114110A1
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WIPO (PCT)
Prior art keywords
group
fluorine
sio
alkoxylated
siloxane polymer
Prior art date
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PCT/JP2010/056046
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English (en)
Inventor
Hisashi Mitsuhashi
Kenichi Saitou
Yasuo Itami
Tetsuya Masutani
Don Lee Kleyer
Janet M. Smith
Original Assignee
Daikin Industries, Ltd.
Dow Corning Corporation
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Application filed by Daikin Industries, Ltd., Dow Corning Corporation filed Critical Daikin Industries, Ltd.
Publication of WO2010114110A1 publication Critical patent/WO2010114110A1/fr

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Classifications

    • 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
    • C08L83/04—Polysiloxanes
    • C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • 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
    • A61K8/11—Encapsulated compositions
    • 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
    • A61K8/897—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing halogen, e.g. fluorosilicones
    • 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
    • A61Q1/12—Face or body powders for grooming, adorning or absorbing
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on 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; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns

Definitions

  • the present invention relates to a powder for cosmetics having surface treated with a surface treatment agent for cosmetics which comprises silane compound containing a short chain fluoroalkyl (Rf) group having at most 6 carbon atoms, and the cosmetics comprising the powder.
  • a surface treatment agent for cosmetics which comprises silane compound containing a short chain fluoroalkyl (Rf) group having at most 6 carbon atoms
  • the cosmetics comprising the powder. Since the surface treatment agent of the present invention does not include perfluorooctanoic acid (PFOA) analogue structure, the surface treatment agent is excellent in safety. In addition, the surface treatment agent has excellent water resistance, water- and oil-repellency, feeling of use, and dispersibility with other materials.
  • PFOA perfluorooctanoic acid
  • An object of the present invention is to provide a cosmetic powder surface-treated with a compound which does not have a perfluorooctanoic acid (PFOA) analogue structure and imparts excellent water resistance and water- and oil-repellency, and to provide a cosmetic characterized by containing said cosmetic powder.
  • PFOA perfluorooctanoic acid
  • a specific fluorine-modified siloxane polymer has excellent characteristics of a surface treatment agent for cosmetics.
  • the surface-treated powder and the cosmetic of the present invention are characterized by using a surface treatment agent which comprises an alkoxylated fluorine-modified siloxane polymer.
  • the present invention provides an alkoxylated fluorine-modified siloxane polymer consisting of
  • R 1 each is an unsubstituted or substituted monovalent organic group
  • Rf is a fluoroalkyl group having 1 to 6 carbon atoms wherein at least one fluorine atom is optionally substituted by hydrogen or halogen atom(s),
  • X is a bivalent organic group
  • R 2 each is a hydrogen atom or an unsubstituted or substituted monovalent organic group, and the alkoxylated fluorine-modified siloxane polymer has at least one R 2 -O- group.
  • the alkoxylated fluorine-modified siloxane polymer can be produced by a method comprising the steps of;
  • Rf is a fiuoroalkyl group having 1 to 6 carbon atoms wherein at least one fluorine atom is optionally substituted by hydrogen or halogen atom(s), X is a bivalent organic group, and
  • R 2 each is a hydrogen atom or an unsubstituted or substituted monovalent organic group, in the presence of
  • the present invention further provides a surface treated powder treated with the alkoxylated fluorine-modified siloxane polymer.
  • the present invention also provides cosmetics comprising the surface treated powder.
  • R 1 each is, the same or different, an unsubstituted or substituted monovalent organic group.
  • the monovalent organic group include, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group and an alkenyl group.
  • the alkyl group and the alkenyl group may have 1 to 20 carbon atoms
  • the cycloalkyl group may have 4 to 10 carbon atoms
  • the aryl group may have 6 to 20 carbon atoms
  • the aralkyl group may have 7 to 21 carbon atoms.
  • Examples of the monovalent organic group include alkyl groups such as a methyl group, an ethyl group, a propyl group and a butyl group; cycloalkyl groups such as a cyclopentyl group and a cyclohexyl group; aryl groups such as a phenyl group; aralkyl groups such as a benzyl group; alkenyl groups such as a vinyl group and an allyl group; fluoroalkyl groups such as 3,3,3-trifluoropropyl group.
  • the monovalent organic group is preferably the alkyl group or fluoroalkyl group.
  • the unit (2) may be SiO 2 , (R 2 -O-)SiO 3/2 , (R 2 -O-) 2 SiO and/or (R 2 -O-) 3 SiOi/ 2 .
  • a ratio by number of the unit (2) having the R 2 -O- group to whole unit (2) may be at least 10% by mol, for example, 20 to 100%, based on the whole unit (2).
  • the unit (3) may be (Rf-X-)(R 2 -O-) 2 SiO 172 , (Rf-X-)(R 2 -O-)SiO and/or (Rf-X-)SiO 3/2 .
  • a ratio by number of the unit (3) having the R 2 -O- group to whole unit (3) may be at least 10% by mol, for example, 20 to 100%, based on the whole unit (3).
  • the alkoxylated fluorine-modified siloxane polymer has at least one R 2 -O- group.
  • the Rf group is preferably a perfluoroalkyl group.
  • the Rf group has 1 to 6 carbon atoms.
  • Examples of the Rf group include -CF 3 , -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CF(CF 3 ) 2 , -CF 2 CF 2 CF 2 CF 3 , -CF 2 CF(CF 3 ) 2 , -C(CF 3 ) 3 , -(CF 2 ) 4 CF 3 , -(CF 2 ) 2 CF(CF 3 ) 2 , -CF 2 C(CFa) 3 , -CF(CF 3 )CF 2 CF 2 CF 3 , -(CF 2 ) 5 CF 3 , -(CF 2 ) 2 H, -CF 2 CFHCF 3 , -(CFz) 4 H and -(CF 2 ) ⁇ H.
  • the carbon atom number of the Rf group is from 1 to 6, particularly from 4 to 6, especially 6, from the viewpoint of the above-mentioned PFOA and function.
  • the Rf group may be linear or branched, and is preferably a linear fluoroalkyl group.
  • the X group may be an alkylene group having 1 to 10 carbon atoms which may be interrupted by at least one (for example, 1 to 5, particularly 1) oxygen atom.
  • Examples of X include -(CH 2 ) a -, -CH 2 OCH 2 CH 2 CH 2 -,
  • R 2 each is, the same or different, a hydrogen atom or an unsubstituted or substituted monovalent organic group.
  • the monovalent organic group include, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group and an alkenyl group.
  • the alkyl group and the alkenyl group may have 1 to 20 carbon atoms
  • the cycloalkyl group may have 4 to 10 carbon atoms
  • the aryl group may have 6 to 20 carbon atoms
  • the aralkyl group may have 7 to 21 carbon atoms.
  • Examples of the monovalent organic group include alkyl groups such as a methyl group, an ethyl group, a propyl group and a butyl group; polyether such as -(OCH 2 CH 2 )a-OR 2 ; cycloalkyl groups such as a cyclopentyl group and a cyclohexyl group; aryl groups such as a phenyl group; aralkyl groups such as a benzyl group; alkenyl groups such as a vinyl group and an allyl group; fluoroalkyl groups such as 3,3,3-trifiuoropropyl group.
  • the monovalent organic group is preferably the alkyl group or fluoroalkyl group.
  • An amount of the unit (1) is preferably from 1 to 50 % by mol, more preferably from 5 to 35 % by mol, an amount of the unit (2) is preferably from 1 to 70 % by mol, more preferably from 5 to 50 % by mol, and an amount of the unit (3) is preferably from 10 to 90 % by mol, more preferably from
  • (1), (2) and (3) is 100 % by mol.
  • the number of unit (1) may be from 1 to 1000, for example, from 2 to 500.
  • the number of unit (2) may be from 1 to 1000, for example, from 2 to 500.
  • the number of unit (3) may be from 2 to 2000, for example, 5 to 1000.
  • the alkoxylated fluorine-modified siloxane polymer may be used with or without, usually with the solvent to apply said polymer to the powder.
  • a fluorine-containing silane compound may be mixed with the alkoxylated fluorine-modified siloxane polymer, before the alkoxylated fluorine-modified siloxane polymer is used for the surface treatment of the powder.
  • the fluorine-containing silane compound is of the formula:
  • Rf is a fluoroalkyl group having 1 to 6 carbon atoms
  • Y is an (unsubstituted or substituted) bivalent organic group, and each A is, the same or different, a monovalent organic group or a hydrolyzable group such as alkoxy, halide or amino group, wherein at least one A is the hydrolyzable group.
  • the Rf group is preferably a perfluoroalkyl group.
  • the Rf group has 1 to 6 carbon atoms.
  • Examples of the Rf group include -CF 3 , -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CF(CF 3 ) 2 , -CF 2 CF 2 CF 2 CF 3 , -CF 2 CF(CF 3 ) 2 , -C(CF 3 ) 3 , -(CF 2 ) 4 CF 3 , -(CF 2 ) 2 CF(CF 3 ) 2 , -CF 2 C(CF 3 ),, -CF(CF 3 )CF 2 CF 2 CF 3 , -(CF 2 ) 5 CF 3 , -(CF 2 ) 2 H, -CF 2 CFHCF 3 , -(CFj) 4 H and -(CFz) 6 H.
  • the carbon atom number of the Rf group is from 1 to 6, particularly from 4 to 6, especially 6, from the viewpoint of the above-mentioned PFOA and function.
  • the Rf group may be linear or branched, and is preferably a linear fluoroalkyl group.
  • the Y group may be an alkylene group having 1 to 10 carbon atoms which may be interrupted by at least one (for example, 1 to 5, particularly 1) oxygen atom.
  • Examples of Y include -(CH 2 ) a -, -CH 2 OCH 2 CH 2 CH 2 -, -CH 2 CH 2 OCH 2 CH 2 CH 2 -, -, -CH 2 CH(OH)CH 2 NHCH 2 CH 2 CH 2 -, (-CH 2 CH(OH)CH 2 ) 2 NCH 2 CH 2 CH 2 -,
  • Y (-CH 2 CH(OH)CH 2 ) 2 NCH 2 CH 2 (-CH 2 CH(OH)CH 2 )NCH 2 CH 2 CH 2 -, -CH 2 CH(OH)CH 2 NCH 2 CH 2 HNCH 2 CH 2 CH 2 -, (wherein a is 1 to 10, particularly 1 to 6).
  • Y are -(CH 2 ) 2 -, -(CH 2 ) 3 -, -(CH 2 ) 4 - and -(CH 2 ) 6 -.
  • the A group each is, the same or different, an unsubstituted or substituted monovalent organic group.
  • the monovalent organic group include an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group and an alkenyl group.
  • the alkyl group and the alkenyl group may have 1 to 20 carbon atoms
  • the cycloalkyl group may have 4 to 10 carbon atoms
  • the aryl group may have 6 to 20 carbon atoms
  • the aralkyl group may have 7 to 21 carbon atoms.
  • Examples of the monovalent organic group include alkyl groups such as a methyl group, an ethyl group, a propyl group and a butyl group; polyether such as -(OCH 2 CH 2 ) a -OR 2 ; cycloalkyl groups such as a cyclopentyl group and a cyclohexyl group; aryl groups such as a phenyl group; aralkyl groups such as a benzyl group; alkenyl groups such as a vinyl group and an allyl group; fluoroalkyl groups such as 3,3,3-trifluoropropyl group.
  • At least one A is the hydrolyzable group. All of the A groups may be the hydrolyzable group.
  • Examples of the hydro lyzable group include an alkoxy group (having 1 to 10 carbon atoms), a halogen atom (such as chlorine, bromine and iodine) and an amino group.
  • the fluorine-containing silane compound is preferably of the formula:
  • Rf is a fluoroalkyl group having 1 to 6 carbon atoms
  • Y is an alkylene group having 1 to 10 carbon atoms
  • R 3 each is, the same or different, an alkyl having 1 to 10 carbon atoms or a phenyl group.
  • the alkoxylated fluorine-modified siloxane polymer is produced by reacting the component (A) with the component (B).
  • the component (A) is an MQ organosilicone resin of the empirical formula:
  • R 1 each is, the same or different, an unsubstituted or substituted monovalent organic group.
  • the monovalent organic group include, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group and an alkenyl group.
  • the alkyl group and the alkenyl group may have 1 to 20 carbon atoms
  • the cycloalkyl group may have 4 to 10 carbon atoms
  • the aryl group may have 6 to 20 carbon atoms
  • the aralkyl group may have 7 to 21 carbon atoms.
  • Examples of the monovalent organic group include alkyl groups such as a methyl group, an ethyl group, a propyl group and a butyl group; cycloalkyl groups such as a cyclopentyl group and a cyclohexyl group; aryl groups such as a phenyl group; aralkyl groups such as a benzyl group; alkenyl groups such as a vinyl group and an allyl group; fluoroalkyl groups such as 3,3,3-trifluoropropyl group.
  • the monovalent organic group is preferably the alkyl group or fluoroalkyl group.
  • MQ resins may contain a limited number of D and T units.
  • the value of parameters a, b, c and d are limited as set forth above such that the number of D and T units does not exceed 20 mole percent of the number of siloxy units.
  • the above limitations dictate that the number of M units must be greater than at least 0.3 of the sum of the number of D, T and Q units.
  • the ratio of M units to the sum of D, T and Q units is inversely proportional to the molecular weight of the resin.
  • Mn of the resin when that the ratio is in excess of 1.0, Mn of the resin is generally less than about 2,200.
  • Mn when that ratio is less than about 0.3, Mn generally exceeds about 7,700 and the resin looses its solubility in the preferred solvents.
  • the number average molecular weight of the MQ organosilicone resin is preferably about 2,200 to about 7,700, more preferably 2500 to about 7,000.
  • the component (B) is at least one fluorine-containing silane compound selected from the group of silanes having the empirical formula:
  • Rf is a fluoroalkyl group having 1 to 6 carbon atoms wherein at least one fluorine atom is optionally substituted by hydrogen or halogen atom(s),
  • X is a bivalent organic group
  • R 2 each is a hydrogen atom or an unsubstituted or substituted monovalent organic group.
  • Rf group is preferably a perfluoroalkyl group.
  • the Rf group has 1 to 6 carbon atoms.
  • examples of the Rf group include -CF 3 , -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CF(CF 3 ) 2 , -CF 2 CF 2 CF 3 , -CF 2 CF(CF 3 ),, -C(CF 3 ) 3 , -(CF 2 ) 4 CF 3 , -(CF 2 ) 2 CF(CF 3 ) 2 , -CF 2 C(CF 3 ),, -CF(CF 3 )CF 2 CF 2 CF 3 , -(CF 2 ) 5 CF 3 , -(CF 2 ) 2 H, -CF 2 CFHCF 3 , -(CFz) 4 H and -(CF 2 ) 6 H.
  • the carbon atom number of the Rf group is from 1 to 6, particularly from 4 to 6, especially 6, from the viewpoint of the above-mentioned PFOA and function.
  • the Rf group may be linear or branched, and is preferably a linear fluoroalkyl group.
  • X group may be an alkylene group having 1 to 10 carbon atoms which may be interrupted by at least one (for example, 1 to 5, particularly 1) oxygen atom.
  • Examples of X include -(CH 2 ) a -, -CH 2 OCH 2 CH 2 CH 2 -, -CH 2 CH 2 OCH 2 CH 2 CH 2 -, -CH 2 CH(OH)CH 2 NHCH 2 CH 2 CH 2 -, (-CH 2 CH(OH)CH 2 ) 2 NCH 2 CH 2 CH 2 -,
  • R 2 each is, the same or different, a hydrogen atom or an unsubstituted or substituted monovalent organic group.
  • the monovalent organic group include, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group and an alkenyl group.
  • the alkyl group and the alkenyl group may have 1 to 20 carbon atoms
  • the cycloalkyl group may have 4 to 10 carbon atoms
  • the aryl group may have 6 to 20 carbon atoms
  • the aralkyl group may have 7 to 21 carbon atoms.
  • Examples of the monovalent organic group include alkyl groups such as a methyl group, an ethyl group, a propyl group and a butyl group; polyether such as -(OCH 2 CH 2 ) a -OR 2 ; cycloalkyl groups such as a cyclopentyl group and a cyclohexyl group; aryl groups such as a phenyl group; aralkyl groups such as a benzyl group; alkenyl groups such as a vinyl group and an allyl group; fluoroalkyl groups such as 3,3,3-trifluoropropyl group.
  • the monovalent organic group is preferably the alkyl group or fluoroalkyl group.
  • the component (C) comprises a catalytic amount of a basic catalyst or an acidic catalyst.
  • Suitable basic catalysts include but are not limited to NaOH, KOH, NaOCH 3 , LiOH, potassium tertiary butoxide, LiOCH 3 , KOCH 3 , sodium silanolate and amines, such as ethanolamine and quaternary ammonium salts, such as tetrabutylammonium fluoride.
  • Suitable acidic catalysts include but are not limited to H 2 SO 4 , CF 3 SO 3 H and acid clays.
  • catalytic amount is such an amount of catalyst that causes the reaction of the invention to proceed at a predetermined desired rate.
  • the catalytic amount of catalyst will, of course, depend upon the type of basic catalyst, as some are more effective than others and the temperature at which the reaction is carried out.
  • the amount of catalyst is generally from 0.1 to 5 parts by weight, based on 100 parts by weight of the fluorine-containing silane compound.
  • the reacting step (I) is carried out under conditions of reflux.
  • the reaction of the invention will proceed at room temperature conditions, but it is well-known in the art that reaction rates are accelerated at elevated temperatures.
  • the MQ resin, as dissolved in an organic solvent, may be directly reacted.
  • a volatiles trap is employed which then substantially separates alcohols and volatile reaction products from the alkoxylated resin.
  • An amount of the fluorine-containing silane compound is from 0 to 500 parts by weight, preferably from 1 to 200 parts by weight, more preferably from 10 to 100 parts by weight, based on 100 parts by weight of the alkoxylated fluorine-modified siloxane polymer.
  • the present invention provides a mixture of the alkoxylated fluorine-modified siloxane polymer with the component (B) (that is, the fluorine-containing silane compound).
  • the surface treatment agent may comprise the mixture.
  • a weight ratio of the alkoxylated fluorine-modified siloxane polymer to the fluorine-containing silane compound may be 99:1 to 1:99, for example, 95:5 to 10:90.
  • An amount of the alkoxylated fluorine- modified siloxane polymer applied to the powder changes depending on a kind, a particle diameter, an oil absorption amount, a water absorption amount and a specific surface area of the powder.
  • the amount of the alkoxylated fluorine-modified siloxane polymer to be applied is from 0.05 to 40 parts by weight, preferably from 0.1 to 30 parts by weight, particularly 1 to 25 parts by weight, based on 100 parts by weight of the powder.
  • the powder used in the present invention is not restricted so for as the powder is one which is usually used for cosmetics as powder.
  • An average particle size of the powder may be usually 0.01 micrometers to 1 mm.
  • Examples of the powder include an inorganic powder and an organic powder.
  • the inorganic powder examples include boron nitride, sericite, natural mica, calcined mica, synthetic mica, synthetic sericite, alumina, mica, talc, kaolin, bentonite, smectite, calcium carbonate, magnesium carbonate, magnesium silicate, aluminum silicate, calcium phosphate, silicic acid anhydride, magnesium oxide, barium sulfate, magnesium aluminometasilicate, iron oxide, chrome oxide, titanium oxide, zinc oxide, cerium oxide, aluminum oxide, magnesium oxide, chromium hydroxide, iron blue, lapis lazuli, calcium carbonate, magnesium carbonate, calcium phosphate, aluminum hydroxide, barium sulfate, magnesium sulfate, silicic acid, magnesium aluminum silicate, calcium silicate, barium silicate, strontium silicate, silicon carbide, tungstate metal salt, magnesium aluminate, magnesium aluminometasilicate, chlorohydroxy aluminum, clay, zeolite
  • a method of applying the alkoxylated fluorine-modified siloxane polymer to the powder used for the cosmetics is not limited and may be a well-known method.
  • the surface treatment method When the surface treatment method is classified roughly, it has a dry process and a wet process.
  • the dry process can be performed by mixing the surface treatment agent (that is, the surface treatment agent) and the powder for a given time in agitators, such as a Henschel mixer, a ball mill, a jet mill, or a grinder.
  • agitators such as a Henschel mixer, a ball mill, a jet mill, or a grinder.
  • the powder is dispersed in water or a solvent, the surface treatment agent is added with stirring, and then the solvent is evaporated.
  • the powder to be treated with the surface treatment in the present invention may be treated with at least one of, for example, oxides or oxide hydrate of aluminum, calcium, magnesium, cerium, silicon, zirconium, titanium, zinc, iron, cobalt, manganese, nickel and/or tin in order to improve affinity and adherence with the surface treatment agent.
  • oxides or oxide hydrate of aluminum, calcium, magnesium, cerium, silicon, zirconium, titanium, zinc, iron, cobalt, manganese, nickel and/or tin in order to improve affinity and adherence with the surface treatment agent.
  • the surface-treated powder obtained by the present invention does not include perfluorooctanoic acid (PFOA) analogue structure and has the excellent water resistance and water- and oil-repellency.
  • PFOA perfluorooctanoic acid
  • One or more of the surface-treated powders can be blended into the cosmetic.
  • a cosmetic excellent in feeling of use, makeup result, and makeup durability is provided by blending the above-mentioned surface-treated powder.
  • the amount of the surface-treated powder changes depending on the kinds and agent forms of a cosmetic.
  • the powder surface-treated with the alkoxylated fluorine-modified siloxane polymer of the present invention can be blended with the cosmetic, in the amount of 0.1 to 99% by weight for example, 1 to 50% by weight, based on the whole cosmetic.
  • Examples of the cosmetic blended with the surface-treated powder obtained by the present invention include; makeup cosmetics, such as a makeup base, a powder foundation, a facial liquid foundation, an oily foundation, a stick foundation, a presto powder, a face powder, a white powder, a lipstick, a lipstick overcoat, a lip gloss, a concealer, a rouge, an eye shadow, an eyebrow, an eyeliner, a mascara, a water nail enamel, an oily nail enamel, an emulsified type nail enamel, an enamel topcoat and an enamel base coat; skin care cosmetics, such as an emollient cream, a cold cream, a whitening cream, a milky lotion, a liquid cosmetic, a beauty essence, a pack, a carmine lotion, a liquid face wash, a cleansing foam, a facial cleansing cream, a facial washing powder, a makeup cleansing cream, a body gross, a sunscreen, a suntan cream or a lotion; hair cosmetics, such as a hair growth, hair cream, a
  • a milky lotion, a soap, a bath additive, a perfume, etc. can be also mentioned.
  • other component to be incorporated into the cosmetic blended with the surface-treated powder of the present invention include an oily ingredient, an aqueous ingredient, and a surface active agent. If usually used for the cosmetic, there will be no limitation in particular to other components.
  • oils and fats such as a safflower oil, a soybean oil, an evening primrose oil, a grape-seeds oil, a rose hip oil, a kukui nuts oil, an almond oil, a sesame oil, a wheat germ oil, a corn oil, a cotton seed oil, an avocado oil, an olive oil, a camellia oil, a persic oil, a castor oil, peanut oil, hazelnut oil, a macadamia nuts oil, a meadowfoam oil, cacao butter, Shea butter, a tree low, a coconut oil, a palm oil, a palm kernel oil, a beef tallow, a horse fat, a mink oil, a milk fat, an egg yolk oil, a turtle oil and a jojoba oil; waxes, such as a bee wax, a whale wax, lanolin, a carnauba wax, a candelilla wax, and a microcrystalline wax
  • aqueous ingredient examples include; lower alcohols, such as ethanol and isopropanol; sugar alcohols, such as sorbitol, and maltose; water-soluble vegetable polymers, such as gum arabic, gum tragacanth, galactan, carob gum, guar gum, karaya gum, a carrageenan, pectin, agar, quince seed (quince), a starch
  • lower alcohols such as ethanol and isopropanol
  • sugar alcohols such as sorbitol, and maltose
  • water-soluble vegetable polymers such as gum arabic, gum tragacanth, galactan, carob gum, guar gum, karaya gum, a carrageenan, pectin, agar, quince seed (quince), a starch
  • water-soluble microorganism polymers such as xanthan gum, dextran, a succinoglucan, and pullulan
  • water-soluble animal polymers such as collagen, casein, albumin, and gelatin
  • water-soluble starch polymers such as carboxymethyl starch and methylhydroxypropyl starch
  • water-soluble cellulose polymer such as methyl cellulose, ethyl cellulose, methyl hydroxypropyl cellulose, carboxymethyl cellulose, hydroxymethyl cellulose, hydroxypropyl cellulose, cellulose nitrate, cellulose sodium sulfate, carboxymethyl cellulose sodium, crystalline cellulose, and cellulose powder
  • water-soluble alginic acid polymers such as sodium alginate, and propyleneglycol alginate ester
  • water-soluble vinyl polymers such as polyvinyl methyl ether and carboxyvinyl polymer
  • these water soluble polymers include also coat formation agents, such as polyvinyl alcohol and polyvinyl pyrrolidone.
  • the surface active agent examples include; anionic surface active agents, for example, fatty acid soap, such as sodium stearate and triethanolamine palmitate, alkyl ether carboxylic acid and its salt, a condensate salt of an amino acid and fatty acid, an alkane sulfonic acid salt, an alkene sulfonate salt, a sulfonate salt of fatty acid ester, a sulfonate salt of fatty acid amide, a formalin condensate sulfonate salt, an alkyl sulfate ester salt, a secondary higher alcohol sulfuric ester salt, alkyl and allyl ethereal sulfate ester salt, a sulfate ester salt of fatty acid ester, a sulfate ester salt of fatty acid alkylol amide, a sulfate ester salt of turkey red oil and the like, an alkyl phosphate salt, an ether phosphate salt,
  • N-acylamino acid-based activator cationic surface active agents, for example, amine salt, such as an alkylamine salt, polyamine, and amino alcohol fatty acid derivatives; an alkyl quarternary ammonium salt, an aromatic quarternary ammonium salt, a pyridium salt, and imidazolium salt; nonionic surface active agents, for example, sorbitan fatty acid ester, glycerine fatty acid ester, poly glycerine fatty acid ester, propylene glycol fatty acid ester, polyethylene glycol fatty acid ester, cane sugar fatty acid ester, polyoxyethylene alkyl ether, polyoxypropylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbitol fatty acid ester, polyoxyethylene glycerine fatty acid ester, polyoxyethylene propylene glycol fatty acid ester,
  • additives such as a pigment dispersion agent, an oil, a surface active agent, an ultraviolet absorber, an antiseptic, an antioxidant, a coating formation agent, a moisturizer, a thickener, a dye, a pigment, various drugs, and perfume which are used for the usual cosmetic can be suitably blended, if these do not spoil the effect of the present invention.
  • the surface treatment agent contains the alkoxylated fluorine-modified siloxane polymer as an active component.
  • the "treatment” means that the active component is adhered to the powder. Usually, the powder is partially or fully coated with the active component. The treatment gives the result that the powder exhibits the water resistance and water- and oil-repellency.
  • the starting MQ resin was dissolved in xylene at a concentration of 74% by weight.
  • the general formula comprised 51% (CH 3 ) 3 Si0 1/2 , 17% (HO)SiO 3 / 2 and 32% SiO 2 .
  • a 250 mL round bottom 3 neck flask was equipped with a motor driven stirrer, a Dean-Stark trap and water cooled condenser attached to CaSO 4 filled drying tube, thermometer and temperature controller was used for the synthesis.
  • the general formula of the resultant Compound 1 comprised 19% (CHs) 3 SiOy 2 , 5% F(CF 2 ) 6 (CH 2 ) 2 Si(OEt) 3 , 26% F(CFz) 6 (CHz) 2 Si(OEt) 2 Oi Z2 , 27% F(CF 2 ) 6 (CH 2 ) 2 Si(OEt)O, 5% F(CF 2 ) 6 (CH 2 ) 2 Si0 3 /z, 4% (EtO) 3 SiO 1/2 , 8% (EtO) 2 SiO, 4% (EtO)SiO 3/2 , and 0% SiO 2 .
  • the general formula of the resultant Compound 2 comprised 29% 2% F(CF 2 ) 6 (CH 2 ) 2 Si(OEt) 3 , 14% F(CF 2 ) 6 (CH 2 ) 2 Si(OEt) 2 O 1/2 , 20% F(CF 2 ) 6 (CH 2 ) 2 Si(OEt)O, 7% F(CF 2 ) 6 (CH 2 ) 2 SiO 3/2 , 2% (EtO) 3 SiOy 2 , 7% (EtO) 2 SiO, 8% (EtO)SiO 372 , and 11% SiO 2 .
  • the general formula of the resultant Compound 4 comprised 41% (CH 3 ) 3 SiOi/ 2 , 0% F(CF 2 MCHz) 2 Si(OMe) 3 , 5% F(CF 2 ) 6 (CH 2 ) 2 Si(OMe) 2 O 1/2 , 14% F(CF 2 ) 6 (CH 2 ) 2 Si(OMe)O, 12% F(CF 2 ) 6 (CH 2 ) 2 SiO 3/2 , 0% (MeO) 3 SiO 1 Z 2 , 4% (MeO) 2 SiO, 8% (MeO)SiO 3/2 , and 15% SiO 2 .
  • the general formula of the resultant Compound 5 comprised 18% (CH 3 ) 3 Si0iz 2 , 21% F(CF 2 ) 6 (CH 2 ) 2 Si(OEt) 3 , 29% F(CF 2 ) 6 (CH 2 ) 2 Si(OEt) 2 O 1/2 , 3% F(CF 2 ) 6 (CH 2 ) 2 Si(OEt)O, 0% F(CF 2 ) 6 (CH 2 ) 2 SiO 3/2 , 0% (EtO) 3 SiO 1 Z 2 , 1% (EtO) 2 SiO, 4% (EtO)SiO 3 Z 2 , and 24% SiO 2 .
  • the general formula of the resultant Compound 6 comprised 27% (CH 3 ) 3 Si0 1/2 , 7% F(CF 2 ) 6 (CH 2 ) 2 Si(OEt) 3 , 19% F(CF 2 ) 6 (CH 2 ) 2 Si(OEt) 2 O 1/2 , 4% F(CF 2 ) 6 (CH 2 ) 2 Si(OEt)O, 0% F(CF 2 ) 6 (CH 2 ) 2 SiO 3/2 , 0% (EtO) 3 SiOiZ 2 , 2% (EtO) 2 SiO, 6% (EtO)SiO 3 Z 2 , and 35% SiO 2 .
  • Example 1 to 6 and Comparative Example 1 The water and oil repellency of the samples of surface-treated powder obtained in Example 1 to 6 and Comparative Example 1 was evaluated. Measurement was conducted in the following manner. A pressed pellet was prepared from the sample powder. Water and squalane contact angles were measured at more than four points on the pellet. Average values for each sample were shown in Table 1.
  • This surface-treated powder and other components according to Table 3 were mixed well with a Henschel mixer, and then press-formed into a cake to give a powdery foundation.
  • the surface-treated powder of this invention treated with the alkoxylated fluorine-modified siloxane polymer or its mixture with the fluorine-modified silane compound has excellent water and oil repellency. Therefore, cosmetic preparations in which the surface-treated powder of this invention is used have good to excellent aesthetic stability and feeling in use.

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Abstract

L'invention concerne un polymère de siloxane alcoxylé à modification fluor, qui est constitué (1) d'une unité R1 3SiO1/2, (2) d'une unité SiO2, (R2-O-)SiO3/2, (R2-O-)2SiO et/ou (R2-O-)3SiO1/2 et (3) d'une unité (Rf-X)(R2-O-)2SiO1/2, (Rf-X-)(R2-O-)SiO et/ou (Rf-X-)SiO3/2, R1 représentant chacun un groupe organique monovalent non substitué ou substitué, Rf représentant un fluoroalkyle comportant de 1 à 6 atomes de carbone, au moins un atome de fluor étant éventuellement substitué par un ou plusieurs atome(s) d'hydrogène ou d'halogène, X représentant un groupe organique bivalent, R2 représentant chacun un atome d'hydrogène ou un groupe organique monovalent non substitué ou substitué, ledit polymère de siloxane alcoxylé à modification fluor comportant au moins un groupe R2-O.
PCT/JP2010/056046 2009-03-30 2010-03-26 Polymère de siloxane alcoxylé à modification fluor, poudre traitée en surface et produit cosmétique comprenant celle-ci WO2010114110A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107254054A (zh) * 2017-07-03 2017-10-17 陕西科技大学 一种溶剂型疏水疏油性纳米杂化氟硅树脂的制备方法及其应用
US10584186B2 (en) 2015-07-22 2020-03-10 Bridgestone Corporation Silane-functionalized polymer and process for making and using same

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JPH02218603A (ja) 1989-02-21 1990-08-31 Shiseido Co Ltd 化粧料
JPH03246210A (ja) 1990-02-23 1991-11-01 Daito Kasei Kogyo Kk 化粧料
JPH04330007A (ja) 1991-02-01 1992-11-18 Daito Kasei Kogyo Kk 化粧料
JPH0586984A (ja) 1991-09-30 1993-04-06 Suzuki Motor Corp 燃料制御装置
JPH06192594A (ja) 1992-01-29 1994-07-12 Teika Corp 撥水撥油性顔料およびそれを含有した粉体化粧料
JP2001002524A (ja) 1999-06-24 2001-01-09 Nonogawa Shoji Kk 化粧料
WO2001045643A1 (fr) * 1999-12-20 2001-06-28 Avon Products, Inc. Composition cosmetique renfermant des particules enrobees de fluorosilane
US20060229424A1 (en) * 2005-04-12 2006-10-12 General Electric Company Fluoroalkylsilylated MQ resin and solvent-resistant pressure sensitive adhesive composition containing same
JP2007238690A (ja) 2006-03-07 2007-09-20 Daito Kasei Kogyo Kk 撥水撥油性顔料およびそれを含有する化粧料
JP2008037813A (ja) 2006-08-08 2008-02-21 Daito Kasei Kogyo Kk 撥水撥油性化粧料用粉体顔料およびそれを含有する化粧料
JP2008110924A (ja) 2006-10-30 2008-05-15 Daito Kasei Kogyo Kk 撥水撥油性顔料およびそれを含有する化粧料

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62250074A (ja) 1986-04-21 1987-10-30 Daito Kasei Kogyo Kk 撥水撥油性顔料とその製造法
JPH02218603A (ja) 1989-02-21 1990-08-31 Shiseido Co Ltd 化粧料
JPH03246210A (ja) 1990-02-23 1991-11-01 Daito Kasei Kogyo Kk 化粧料
JPH04330007A (ja) 1991-02-01 1992-11-18 Daito Kasei Kogyo Kk 化粧料
JPH0586984A (ja) 1991-09-30 1993-04-06 Suzuki Motor Corp 燃料制御装置
JPH06192594A (ja) 1992-01-29 1994-07-12 Teika Corp 撥水撥油性顔料およびそれを含有した粉体化粧料
JP2001002524A (ja) 1999-06-24 2001-01-09 Nonogawa Shoji Kk 化粧料
WO2001045643A1 (fr) * 1999-12-20 2001-06-28 Avon Products, Inc. Composition cosmetique renfermant des particules enrobees de fluorosilane
US20060229424A1 (en) * 2005-04-12 2006-10-12 General Electric Company Fluoroalkylsilylated MQ resin and solvent-resistant pressure sensitive adhesive composition containing same
JP2007238690A (ja) 2006-03-07 2007-09-20 Daito Kasei Kogyo Kk 撥水撥油性顔料およびそれを含有する化粧料
JP2008037813A (ja) 2006-08-08 2008-02-21 Daito Kasei Kogyo Kk 撥水撥油性化粧料用粉体顔料およびそれを含有する化粧料
JP2008110924A (ja) 2006-10-30 2008-05-15 Daito Kasei Kogyo Kk 撥水撥油性顔料およびそれを含有する化粧料

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10584186B2 (en) 2015-07-22 2020-03-10 Bridgestone Corporation Silane-functionalized polymer and process for making and using same
CN107254054A (zh) * 2017-07-03 2017-10-17 陕西科技大学 一种溶剂型疏水疏油性纳米杂化氟硅树脂的制备方法及其应用
CN107254054B (zh) * 2017-07-03 2020-10-13 陕西科技大学 一种溶剂型疏水疏油性纳米杂化氟硅树脂的制备方法及其应用

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