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WO2010114112A1 - Poudre traitée en surface par un aminosilane à modification fluor et produit cosmétique comprenant celle-ci - Google Patents

Poudre traitée en surface par un aminosilane à modification fluor et produit cosmétique comprenant celle-ci Download PDF

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Publication number
WO2010114112A1
WO2010114112A1 PCT/JP2010/056048 JP2010056048W WO2010114112A1 WO 2010114112 A1 WO2010114112 A1 WO 2010114112A1 JP 2010056048 W JP2010056048 W JP 2010056048W WO 2010114112 A1 WO2010114112 A1 WO 2010114112A1
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WO
WIPO (PCT)
Prior art keywords
group
carbon atoms
formula
powder
modified
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2010/056048
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English (en)
Inventor
Hisashi Mitsuhashi
Kenichi Saitou
Yasuo Itami
Tetsuya Masutani
Peter Cheshire Hupfield
Don Lee Kleyer
Janet M. Smith
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Daikin Industries Ltd
Dow Silicones Corp
Original Assignee
Daikin Industries Ltd
Dow Corning Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Daikin Industries Ltd, Dow Corning Corp filed Critical Daikin Industries Ltd
Publication of WO2010114112A1 publication Critical patent/WO2010114112A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0241—Containing particulates characterized by their shape and/or structure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/69—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing fluorine
    • A61K8/70—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing fluorine containing perfluoro groups, e.g. perfluoroethers
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • 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
    • A61K2800/60—Particulates further characterized by their structure or composition
    • A61K2800/61—Surface treated
    • A61K2800/62—Coated
    • A61K2800/622—Coated by organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/11—Compounds covalently bound to a solid support

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 specified fluorine-modified amino silane has excellent characteristics of a surface treatment agent (particularly a coating formation agent) for cosmetics.
  • the surface-treated powder and the cosmetic of the present invention are characterized by using a surface treatment agent which comprises a product compound obtained by reacting the following the compounds (a) and (b).
  • the present invention provides a surface treated powder treated with a fluorine-modified aminosilane prepared by reacting (a) an epoxy-modified fluorocompound of the formula:
  • Rf is a fluoroalkyl group having 1 to 6 carbon atoms whose fluorine atom(s) can be optionally substituted by hydrogen or halogen atom(s), and
  • R 1 is a bivalent organic group, with (b) an amino group-containing silane compound of the formula:
  • R 2 is a hydrogen atom or a monovalent organic group
  • X each is, the same or different, a bivalent organic group
  • Y each is, the same or different, a monovalent organic group or a hydrolyzable group, wherein at least one Y is a hydrolyzable group, and a is from 0 to 10.
  • the present invention also provides cosmetics comprising the surface treated powder.
  • 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 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.
  • R 1 is preferably a bivalent organic group containing at least one linkage selected from the group consisting Of -CH 2 -, -O-, -NR 11 -, -S-, -CO 2 -, -CONR 11 - and -SO 2 NR 11 -, where R 11 is a hydrogen atom or an alkyl group.
  • the alkyl group for R 11 may have 1 to 10, for example, 1 to 4 carbon atoms.
  • R 1 examples include -(CH 2 ) n -, -(CHO n OCH 2 -, -(CH 2 ) H -CONR 11 - and -(CHz) n -SO 2 NR 11 - (wherein n is 1 to 10, particularly 1 to 6).
  • R 1 is preferably 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.
  • Preferable examples of R 1 include -CH 2 -, -CH 2 OCH 2 - and -CH 2 CH 2 OCH 2 -, particularly -CH 2 -.
  • examples of R 2 include a hydrogen atom, 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 10 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.
  • X is preferably a linear or branched alkylene group having 1 to 10 carbon atoms.
  • X are -(CH 2 ) 2 -, -(CH 2 )3-, -(CH 2 ) 4 - and -(CH 2 )6-.
  • Y include a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group and an alkenyl group, a halogen atom (such as fluorine, chlorine, bromine and iodine) and -OR 21 (R 21 is an alkyl group having 1 to 6, for example, 1 to 4 carbon atoms or an aryl group having 6 to 20 carbon atoms).
  • the alkyl group and the alkenyl group may have 1 to 10 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.
  • At least one of the Y groups is the hydrolyzable group. All of the Y groups may be the hydrolyzable group.
  • hydrolyzable group examples include the halogen atom (such as chlorine, bromine and iodine), organoacylamido groups such as N-methylacetamido, diorganoketoxime groups such as methylethylketoxime, organoamino groups such as N-butylamino, N,N-diorganohydroxylamino groups such as N,N-diethylhydroxyamino and preferably alkoxy groups, -OR 21 , such as ethoxy.
  • halogen atom such as chlorine, bromine and iodine
  • organoacylamido groups such as N-methylacetamido
  • diorganoketoxime groups such as methylethylketoxime
  • organoamino groups such as N-butylamino
  • N,N-diorganohydroxylamino groups such as N,N-diethylhydroxyamino and preferably alkoxy groups
  • -OR 21 such as ethoxy.
  • the amino group-containing silane compound (b) is preferably of the formula:
  • R 2 is a hydrogen atom, an alkyl having 1 to 20 carbon atoms or a phenyl group, each of Z is, the same or different, an alkyl having 1 to 10 carbon atoms or a phenyl group, a is from 0 to 5, and p and q are, the same or different, from 1 to 10.
  • the epoxy-modified fluorocompound (a) is of the formula (I) wherein
  • Rf is a linear fluoroalkyl group having 1 to 6 carbon atoms
  • R 1 is -CH 2 -; and the amino group-containing silane compound (b) is of the formula (Ha) wherein
  • R 2 is a hydrogen atom
  • each of Z is, the same or different, an alkyl group having 1 to 4 carbon atoms
  • a is 0 or 1
  • p and q are, the same or different, from 1 to 10.
  • a molar ratio of the epoxy-modified fluorocompound (a) to the amino group-containing silane compound (b) subjected to the reaction may be 0.2: 1 to 5: 1, preferably 0.5:1 to 2:1, particularly 1: 1.
  • a catalyst may be used for the reaction, but the reaction can be conducted without the catalyst.
  • the reaction may be conducted in the presence of a solvent, but the reaction is conducted preferably in the absence of the solvent.
  • the solvent which can preferably dissolve the reactants such as the MQ resins [M: (R 3 Si(V2) and Q: (Si ⁇ 4 /2)], may be nonaromatic and aromatic organic solvents, including xylene and toluene.
  • the reaction temperature is not considered to be critical since progress can be easily monitored by many different spectroscopic means.
  • the reaction can be conducted at a temperature of from ambient (20 0 C) to 200 0 C for a time of 10 seconds to 100 hours, preferably 4 hours to 16 hours (preferably at 90°C without catalyst).
  • the resultant fluorine-modified aminosilane has a C-N linkage which is formed by the reaction between an epoxy ring in the epoxy-modified fluorocompound and an amine group in the amino group-containing siloxane group and in which the C atom is derived from the epoxy ring and the N atom is derived from the amine group.
  • An amount of the fluorine-modified aminosilane 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 fluorine- modified aminosilane 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 amount is as above-mentioned, the sufficient effects of the fluorine compound can achieved, and performances of the surface-treated powder and effects in the cosmetics caused by surface-treated powder are sufficiently high.
  • 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 fluorine-modified aminosilane to the powder used for the cosmetics is not limited and may be a well-known method.
  • the method may include the use of elevated temperature or catalyst to facilitate the application.
  • Suitable catalysts include acid, base or Lewis acids.
  • 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 fluorine-modified aminosilane 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
  • Examples of 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
  • water-soluble polyoxyethylene 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,
  • 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 fluorine-modified aminosilane 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.
  • a fluorine-modified silane compound C 6 Fi 3 (CH 2 ) 2 Si(OC 2 Hs) 3 was dissolved in 13 ml of isopropyl alcohol (IPA) at room temperature. 10 g of sericite powder was dispersed into this solution and surface-treated according to the same method described in Example 1.
  • 1O g of the mixed powder shown in Table 2 was surface-treated according to the same method described in Example 1 at room temperature (treated by the reaction product of the fluorine-modified epoxide compound represented by formula (A) and the amine-functionalized silane compound H 2 N(CH 2 ) 3 Si(OC 2 Hs) 3 in 1:1 molar ratio).
  • 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.
  • Example 2 Utilizing the surface-treating agent described in Example 2 (the reaction product of the fluorine-modified epoxide compound represented by formula (A) and the amine-functionalized silane compound H 2 N(CH2) 2 NH(CH 2 )3 Si(OC 2 Hs) 3 in 1:1 molar ratio), a powdery foundation was prepared according to the same method described in Example 3.
  • the surface-treated powder of this invention treated with the reaction product of the fluorine-modified epoxide compound and the amine-fimctionalized silane compound has excellent water- and oil-repellency. Therefore, cosmetic preparations containing the surface-treated powder of this invention have good or excellent aesthetic stability and feeling in use.

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Abstract

L'invention concerne une poudre traitée en surface à l'aide d'un aminosilane à modification fluor, qui est élaborée par la mise en réaction de: (a) un composé fluoré à modification époxyde représenté par la formule (I), dans laquelle Rf représente un groupe alkyle fluoré doté de 1 à 6 atomes de carbone, au moins un atome de fluor étant éventuellement substitué par un atome d'hydrogène ou un atome d'halogène, et R1 représentant un groupe organique bivalent, avec (b) un composé de silane contenant un groupe amino et qui est représenté par la formule: NHR2-X-[NH-X]a-Si(Y)3 (II), dans laquelle R2 représente un atome d'hydrogène ou un groupe organique monovalent, chaque X est identique ou différent et représente un groupe organique bivalent, chaque Y est identique ou différent et représente un groupe organique monovalent ou un groupe hydrolysable, au moins un Y représentant un groupe hydrolysable et a est compris entre 0 et 10.
PCT/JP2010/056048 2009-03-30 2010-03-26 Poudre traitée en surface par un aminosilane à modification fluor et produit cosmétique comprenant celle-ci Ceased WO2010114112A1 (fr)

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US16461209P 2009-03-30 2009-03-30
US61/164,612 2009-03-30

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014001152A (ja) * 2012-06-15 2014-01-09 Shin Etsu Chem Co Ltd アミノ基と保護された水酸基を有する有機ケイ素化合物及びその製造方法
CN116903654A (zh) * 2023-07-03 2023-10-20 南开大学 疏水改性剂及其制备方法、制备改性无机填料的方法

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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
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JPH0586984A (ja) 1991-09-30 1993-04-06 Suzuki Motor Corp 燃料制御装置
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JPH05285370A (ja) * 1992-04-14 1993-11-02 Kao Corp 撥水・撥油性粉体及びこれを含有する化粧料
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WO2001045643A1 (fr) * 1999-12-20 2001-06-28 Avon Products, Inc. Composition cosmetique renfermant des particules enrobees de fluorosilane
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
JP2014001152A (ja) * 2012-06-15 2014-01-09 Shin Etsu Chem Co Ltd アミノ基と保護された水酸基を有する有機ケイ素化合物及びその製造方法
CN116903654A (zh) * 2023-07-03 2023-10-20 南开大学 疏水改性剂及其制备方法、制备改性无机填料的方法
CN116903654B (zh) * 2023-07-03 2025-07-22 南开大学 疏水改性剂及其制备方法、制备改性无机填料的方法

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