Classifications

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  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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  • 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
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  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
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  • 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
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  • 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
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  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
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  • A61K8/89—Polysiloxanes
  • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
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  • 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
  • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
  • A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • 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
  • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • 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
  • A61Q15/00—Anti-perspirants or body deodorants
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/12—Preparations containing hair conditioners
• • 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
  • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
  • C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
• • C—CHEMISTRY; METALLURGY
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  • 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
  • C08G77/48—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
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  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/54—Silicon-containing compounds
  • C08K5/541—Silicon-containing compounds containing oxygen
  • C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
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  • 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
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  • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
  • C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
  • C08L83/12—Block- or graft-copolymers containing polysiloxane sequences containing polyether sequences
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  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
• • 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
  • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups

Definitions

• the present invention relates to organopolysiloxanes and cosmetics using the same.
• Silicone surfactants are widely used because they are refreshing, non-sticky, and provide an excellent feel when used.
• many emulsion compositions containing polyether-modified silicones or polyglycerin-modified silicones have been proposed (Patent Documents 1 and 2).
• Patent Documents 1 and 2 polar oils such as ester oils are used as the oil agent, emulsion stability is insufficient, and phase separation can occur over time.
• Patent Document 3 also proposes using carboxy-modified silicone in an oil-in-water emulsion composition.
• JP 2021-075488 A International Publication No. 2018/117172 JP 2020-172481 A
• the present invention has been made in consideration of the above circumstances, and aims to provide an organopolysiloxane with excellent emulsion stability, as well as a cosmetic preparation using said organopolysiloxane.
• the inventors discovered that the storage stability of the resulting emulsion composition is extremely excellent when an organopolysiloxane having both a (poly)glycerin group or a polyoxyalkylene group and a carboxy group is used as an emulsifier, and this led to the creation of the present invention.
• the present invention provides a carboxyl-modified organopolysiloxane having a (poly)glycerin group or a polyoxyalkylene group, as shown below, and this organopolysiloxane and a cosmetic composition using the same.
• R 1 is independently a monovalent hydrocarbon group selected from an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 15 carbon atoms, and an aralkyl group having 7 to 15 carbon atoms
• R 2 is independently a group represented by the following formula (2) or (3):
• R 5 represents the following formula (2-1) or a group in which a hydrogen atom or a monovalent hydrocarbon group having 1 to 30 carbon atoms is bonded independently to the oxygen atom terminal of a group represented by formula (2-1) or to the oxygen atom terminal of a group in which a plurality of groups represented by formula (2-1) are linked together
• g in formula (2) is an integer satisfying 0 ⁇ g ⁇ 20
• the number h of groups represented by formula (2-1) in R 5 is an integer satisfying 1 ⁇ h ⁇ 10.
• R6 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 30 carbon atoms
• i is an integer satisfying 0 ⁇ i ⁇ 20
• j1 and j2 are integers satisfying 2 ⁇ j1 ⁇ 100 and 0 ⁇ j2 ⁇ 100, respectively.
• R 3 is independently a group represented by the following formula (4): (In the formula, L1 and L2 are each a divalent linking group having 2 to 20 carbon atoms, R7 is a divalent alkylene group having 2 to 4 carbon atoms, k is an integer satisfying 0 ⁇ k ⁇ 100, and l is 0 or 1.)
• R 4 is independently a group represented by the following formula (5), (6), (7), or (8), (In the formula, R1 is defined as above, n and m are integers satisfying 0 ⁇ n ⁇ 5 and 0 ⁇ m ⁇ 100, and m1, m2, and m3 are integers satisfying 0 ⁇ m1 ⁇ 2, 0 ⁇ m2 ⁇ 2, and 0 ⁇ m3 ⁇ 2.) a, b, c, d, e, and f are respectively 0 ⁇ a ⁇ 100, 1 ⁇ b ⁇ 10, 1 ⁇ c ⁇ 10, 0 ⁇ d ⁇ 10, It is
• the order of the structural units grouped by a to f is arbitrary.
• the carboxyl group-modified organopolysiloxane is represented by the formula: [2]
• the organopolysiloxane is represented by the following formula (1-1): (In the formula, R 1 , R 2 , R 3 , R 4 , a, b, c, and d are the same as defined above.)
• the carboxyl group-modified organopolysiloxane according to [1] which is represented by the following formula: [3]
• A a carboxyl group-modified organopolysiloxane represented by formula (1) according to [1] or [2]
• a cosmetic preparation comprising (B) an oil and (C) water.
• the emulsion composition of the present invention containing the carboxyl-modified organopolysiloxane having a (poly)glycerin group or a polyoxyalkylene group exhibits little change in viscosity or particle size over time, and the cosmetic product obtained using the emulsion composition has excellent stability.
• the organopolysiloxane of the present invention is represented by the following formula (1):
• R 1 is independently a monovalent hydrocarbon group selected from an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 15 carbon atoms, and an aralkyl group having 7 to 15 carbon atoms
• R 2 is independently a group represented by the following formula (2) or (3):
• R 5 represents the following formula (2-1) or a group in which a hydrogen atom or a monovalent hydrocarbon group having 1 to 30 carbon atoms is bonded independently to the oxygen atom terminal of a group represented by formula (2-1) or to the oxygen atom terminal of a group in which a plurality of groups represented by formula (2-1) are linked together
• g in formula (2) is an integer satisfying 0 ⁇ g ⁇ 20
• the number h of groups represented by formula (2-1) in R 5 is an integer satisfying 1 ⁇
• R6 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 30 carbon atoms
• i is an integer satisfying 0 ⁇ i ⁇ 20
• j1 and j2 are integers satisfying 2 ⁇ j1 ⁇ 100 and 0 ⁇ j2 ⁇ 100, respectively.
• R 3 is independently a group represented by the following formula (4): (In the formula, L1 and L2 are each a divalent linking group having 2 to 20 carbon atoms, R7 is a divalent alkylene group having 2 to 4 carbon atoms, k is an integer satisfying 0 ⁇ k ⁇ 100, and z is 0 or 1.)
• R 4 is independently a group represented by the following formula (5), (6), (7), or (8), (In the formula, R1 is defined as above, n and m are integers satisfying 0 ⁇ n ⁇ 5 and 0 ⁇ m ⁇ 100, and m1, m2, and m3 are integers satisfying 0 ⁇ m1 ⁇ 2, 0 ⁇ m2 ⁇ 2, and 0 ⁇ m3 ⁇ 2.) a, b, c, d, e, and f are respectively 0 ⁇ a ⁇ 100, 1 ⁇ b ⁇ 10, 1 ⁇ c ⁇ 10, 0 ⁇ d ⁇ 10, It is
• the order of the structural units grouped by a to f is arbitrary.
• the organopolysiloxane is a carboxyl-modified organopolysiloxane having a (poly)glycerin group or a polyoxyalkylene group, represented by the following formula:
• the order of the structural units grouped by a to f is arbitrary.
• the structural unit group grouped by a, the structural unit group grouped by b, the structural unit group grouped by c, the structural unit group grouped by d, the structural unit group grouped by e, and the structural unit group grouped by f may be arranged in any order for each structural unit group, and each structural unit grouped by a, each structural unit grouped by b, each structural unit grouped by c, each structural unit grouped by d, each structural unit grouped by e, and each structural unit grouped by f may be arranged in any order for all of these structural units.
• R 1 is independently a monovalent hydrocarbon group selected from an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 15 carbon atoms, and an aralkyl group having 7 to 15 carbon atoms.
• the alkyl group may be linear or branched, or may be cyclic.
• R 1 examples include alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, and hexadecyl; cycloalkyl groups such as cyclopentyl; aryl groups such as phenyl and tolyl; and aralkyl groups such as benzyl and phenethyl.
• R 1 is preferably a methyl group.
• the organopolysiloxane of formula (1) has an alkyl group having 6 or more carbon atoms as R1 , the alkyl group having 6 or more carbon atoms preferably accounts for 5 to 40 mass %, and more preferably 10 to 30 mass %, of the total mass of the organopolysiloxane of formula (1).
• R 2 is independently a group represented by the following formula (2) or (3), and each molecule may contain different R 2 .
• R 5 is represented by the following formula (2-1): or a group in which a plurality of groups represented by formula (2-1) are linked together, each of which independently has a hydrogen atom or a monovalent hydrocarbon group having 1 to 30 carbon atoms bonded to the oxygen atom terminal of the group represented by formula (2-3).
• examples of the linking structure include a linear structure in which the 1st or 3rd positions of glycerin are linked together, and a branched structure in which the 2nd position of glycerin is linked to the 1st or 3rd position of glycerin.
• the number of branching points is not particularly limited, but is preferably 2 or less, and more preferably 1 or less.
• examples of the hydrocarbon group include alkyl groups having 1 to 30 carbon atoms, preferably 1 to 16 carbon atoms, aryl groups having 6 to 30 carbon atoms, preferably 6 to 15 carbon atoms, and aralkyl groups having 7 to 30 carbon atoms, preferably 7 to 15 carbon atoms.
• alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, cyclopentyl, hexyl, cyclohexyl, heptyl, octyl, neopentyl, decyl, lauryl, stearyl, and oleyl groups; aryl groups such as phenyl and naphthyl groups; and aralkyl groups such as benzyl and 2-phenylethyl groups.
• g is an integer satisfying 0 ⁇ g ⁇ 20, and g may be 2 or more, or may be 3 or more.
• Specific examples of -C g H 2g - include -(CH 2 ) 2 -, -(CH 2 ) 3 -, -CH 2 CH(CH 3 )CH 2 -, -(CH 2 ) 4 -, -(CH 2 ) 5 -, -(CH 2 ) 6 -, -(CH 2 ) 7 -, -(CH 2 ) 8 -, -(CH 2 ) 2 -CH(CH 2 CH 2 CH 3 )-, -CH 2 -CH(CH 2 CH 3 )-, and the like.
• the number h of groups represented by formula (2-1) in R5 is an integer satisfying 1 ⁇ h ⁇ 10, preferably 2 ⁇ h ⁇ 5, and more preferably 2 ⁇ h ⁇ 3. If h exceeds 10, the viscosity of the organopolysiloxane itself increases, resulting in a deterioration in the feel and usability.
• the (poly)glycerin group includes monoglycerin groups and polyglycerin groups, and also includes structural isomers.
• R 6 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 30 carbon atoms.
• the hydrocarbon group include an alkyl group having 1 to 30 carbon atoms, preferably 1 to 16 carbon atoms, an aryl group having 6 to 30 carbon atoms, preferably 6 to 15 carbon atoms, and an aralkyl group having 7 to 30 carbon atoms, preferably 7 to 15 carbon atoms.
• alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, cyclopentyl, hexyl, cyclohexyl, heptyl, octyl, neopentyl, decyl, lauryl, stearyl, and oleyl groups; aryl groups such as phenyl and naphthyl groups; and aralkyl groups such as benzyl and 2-phenylethyl groups.
• i is an integer satisfying 0 ⁇ i ⁇ 20, and may be 2 or more, or may be 3 or more.
• Specific examples of -CiH2i- include -( CH2 ) 2- , -( CH2 ) 3- , -CH2CH( CH3 ) CH2- , - (CH2 ) 4- , -( CH2 ) 5- , -( CH2 ) 6- , -( CH2 ) 7- , -( CH2 ) 8- , -( CH2 ) 2 - CH ( CH2CH2CH3 )-, -CH2 - CH ( CH2CH3 )-, and the like.
• j1 is an integer that satisfies 2 ⁇ j1 ⁇ 100, preferably 2 ⁇ j1 ⁇ 50, and more preferably 2 ⁇ j1 ⁇ 15.
• j2 is an integer that satisfies 0 ⁇ j2 ⁇ 100, preferably 0 ⁇ j2 ⁇ 50, and more preferably 0 ⁇ j2 ⁇ 5.
• the oxyalkylene units bounded by j1 and j2 in formula (3) may be arranged in any order, either in blocks or randomly.
• R2 preferably accounts for 5 to 70 mass %, and more preferably 10 to 60 mass %, of the total mass of the organopolysiloxane.
• R 3 is independently a group represented by the following formula (4), and different groups may be contained in one molecule.
• L1 and L2 are each a divalent linking group having 2 to 20 carbon atoms
• R7 is a divalent alkylene group having 2 to 4 carbon atoms
• k is an integer satisfying 0 ⁇ k ⁇ 100
• z is 0 or 1.
• L1 and L2 are each a divalent linking group having 2 to 20 carbon atoms.
• the divalent linking group include alkylene groups having 2 to 20 carbon atoms, preferably 2 to 10 carbon atoms. Specific examples include a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group, a heptamethylene group, an octamethylene group, a decamethylene group, a dodecamethylene group, and an octadecamethylene group.
• R7 is a divalent alkylene group having 2 to 4 carbon atoms.
• Examples of the divalent alkylene group include an ethylene group, a trimethylene group, and a tetramethylene group.
• k is an integer satisfying 0 ⁇ k ⁇ 100, preferably 0 ⁇ k ⁇ 50, and more preferably 0 ⁇ k ⁇ 5.
• R3 preferably accounts for 1 to 50 mass % and more preferably 1 to 25 mass % of the total mass of the organopolysiloxane.
• R3 include groups derived from carboxylic acids of the following general formulas (16) to (18).
• R 4 is independently a group represented by the following general formula (5), (6), (7), or (8), and each molecule may contain different R 4 .
• R1 is defined as above, n and m are integers satisfying 0 ⁇ n ⁇ 5 and 0 ⁇ m ⁇ 100, and m1, m2, and m3 are integers satisfying 0 ⁇ m1 ⁇ 2, 0 ⁇ m2 ⁇ 2, and 0 ⁇ m3 ⁇ 2.
• n is an integer that satisfies 0 ⁇ n ⁇ 5.
• n is 0.
• m is an integer that satisfies 0 ⁇ m ⁇ 100, and preferably 1 ⁇ m ⁇ 30.
• m1, m2, and m3 are integers that satisfy 0 ⁇ m1 ⁇ 2, 0 ⁇ m2 ⁇ 2, and 0 ⁇ m3 ⁇ 2.
• a, b, c, d, e, and f are integers satisfying 0 ⁇ a ⁇ 100, 1 ⁇ b ⁇ 10, 1 ⁇ c ⁇ 10, 0 ⁇ d ⁇ 10, e ⁇ 0, and f ⁇ 0.
• a is an integer satisfying 0 ⁇ a ⁇ 100, preferably 1 ⁇ a ⁇ 80, and more preferably 5 ⁇ a ⁇ 60.
• b is an integer satisfying 1 ⁇ b ⁇ 10, preferably 1 ⁇ b ⁇ 8, and more preferably 1 ⁇ b ⁇ 5.
• c is an integer satisfying 1 ⁇ c ⁇ 10, preferably 1 ⁇ c ⁇ 8, and more preferably 1 ⁇ c ⁇ 5.
• d is an integer satisfying 1 ⁇ d ⁇ 10, preferably 1 ⁇ d ⁇ 8, and more preferably 1 ⁇ d ⁇ 3.
• e is an integer satisfying e ⁇ 0, preferably 0 ⁇ e ⁇ 10, and more preferably 0 ⁇ e ⁇ 5.
• f is an integer satisfying f ⁇ 0, preferably 0 ⁇ f ⁇ 10, and more preferably 0 ⁇ f ⁇ 5.
• the organopolysiloxane of the present invention is represented by the following formula (1-1): (In the formula, R 1 , R 2 , R 3 , R 4 , a, b, c, and d are the same as defined above.) It is preferable that the formula is represented by the formula:
• the organopolysiloxane of the present invention represented by formula (1) can be synthesized by a hydrosilylation reaction between an organohydrogenpolysiloxane (H) having hydrosilyl groups, which are reactive sites, and a compound having an alkenyl group (carbon-carbon unsaturated bond) at its terminal, which serves as the raw materials for R2 and R3 in formula (1), and optionally a compound having an alkenyl group at its terminal, which serves as the raw materials for R1 and R4 .
• H organohydrogenpolysiloxane
• An example of an organohydrogenpolysiloxane (H) having hydrosilyl groups as reactive sites is a compound in which R 2 , R 3 , and R 4 in the above formula (1-1) are replaced with hydrogen atoms and, optionally, a portion of R 1 is replaced with a hydrogen atom.
• the carboxy group represented by formula (4) which is a feature of the present invention, can be introduced by subjecting a compound represented by formula (ii) below, which has an alkenyl group at its terminal and serves as the raw material for R3 , to a hydrosilylation reaction with organohydrogenpolysiloxane (H).
• R 3 ' is a group in which --CH 2 CH 2 R 3 ' becomes R 3. That is, R 3 ' has a carboxy group, but this carboxy group in R 3 ' is preferably substituted with a protecting group such as a trimethylsilyl group, a t-butyl group, a benzyl group, etc.
• a protecting group such as a trimethylsilyl group, a t-butyl group, a benzyl group, etc.
• the (poly)glycerin group or polyoxyalkylene group represented by the above formula (2) or (3) can be introduced by subjecting a compound represented by the following formula (iii), which has an alkenyl group at its terminal and serves as the raw material for R2 , to a hydrosilylation reaction with organohydrogenpolysiloxane (H).
• R 2 ' is a group such that --CH 2 CH 2 R 2 ' is R 2 .
• R1 in the above formula (1) can be introduced by subjecting a compound represented by the following formula (iv), which has an alkenyl group at its terminal and serves as a raw material for R1 , to a hydrosilylation reaction with organohydrogenpolysiloxane (H).
• R 1 ' is a group such that --CH 2 CH 2 R 1 ' is R 1 .
• the group represented by the above formula (5), (6), (7), or (8) can be introduced by subjecting any compound represented by the following formula (v), which has an alkenyl group at its terminal and serves as the raw material for R4 , to a hydrosilylation reaction with organohydrogenpolysiloxane (H).
• the hydrosilylation reaction can be carried out by a known method.
• the composition of formula (1) can be adjusted by the raw materials used and their amounts.
• organohydrogenpolysiloxane (H) compounds represented by formulas (ii) and (iii), and optionally compounds represented by formulas (iv) and (v) are added to a reactor in the desired molar ratio, and a platinum catalyst is further added to carry out the reaction.
• the order of addition of the compounds represented by formulae (ii), (iii), (iv), and (v) is not particularly limited, but for example, the compounds can be added in the order of formulae (iv), (ii), (v), and (iii).
• the platinum catalyst is not particularly limited, but examples thereof include PtCl, HPtCl.6HO , Pt - ether complexes, Pt-olefin complexes, PdCl ( PPh ) , PdCl (PhCN) , RhCl ( PPh ) (wherein Ph is a phenyl group), platinum chloride, complexes of chloroplatinic acid or chloroplatinate with vinyl group-containing siloxanes, and the like. These catalysts may be used alone or in combination of two or more.
• Karstedt's catalyst (a complex of 1,1,3,3-tetramethyl-1,3-divinyldisiloxane and chloroplatinic acid neutralized with sodium bicarbonate) is particularly preferred.
• the amount of the platinum catalyst is not particularly limited as long as it is a catalytic amount.
• the catalytic amount is an amount sufficient to cause the hydrosilylation reaction to proceed, and is, for example, preferably 0.02 parts by mass or less, more preferably 0.00001 to 0.02 parts by mass, still more preferably 0.0001 to 0.01 parts by mass, and particularly preferably 0.0003 to 0.005 parts by mass, in terms of the platinum metal atom amount of the platinum catalyst, relative to 100 parts by mass of the organohydrogenpolysiloxane (H).
• the reaction temperature is not particularly limited, but may be, for example, 50 to 90°C. It is preferable to use a solvent during the reaction, and examples of the solvent include, but are not limited to, isopropyl alcohol, tetrahydrofuran, and toluene.
• a solvent include, but are not limited to, isopropyl alcohol, tetrahydrofuran, and toluene.
• the cosmetic composition of the present invention comprises: (A) a carboxyl-modified organopolysiloxane represented by formula (1), Contains (B) an oil solution and (C) water.
• the cosmetic preparation is in the form of a composition.
• the component (A) is a carboxyl-modified organopolysiloxane having a (poly)glycerin group or a polyoxyalkylene group, represented by formula (1), and may use either a single compound or a combination of two or more compounds.
• the amount of component (A) is not particularly limited, but is preferably 0.1 to 30% by mass, and more preferably 0.1 to 15% by mass, of the total cosmetic composition.
• the component (B) of the present invention is an oil agent
• the oil agent (B) of the present invention may be any of liquid, solid, and semi-solid, and examples thereof include hydrocarbon oils, higher fatty acids, higher alcohols, natural animal and vegetable oils and semi-synthetic oils and fats, ester oils, silicone oils, and fluorine-based oil agents. These may be used alone or in combination of two or more.
• the hydrocarbon oil may be a linear or branched hydrocarbon oil, and may be a volatile or non-volatile hydrocarbon oil.
• examples include olefin oligomers, isododecane (display name (INCI: Isododecane)), dodecane (display name (INCI: Dodecane)), isohexadecane (display name (INCI: Isohexadecane)), undecane (display name (INCI: Undecane)), squalane (display name (INCI: Squalane)), squalene (display name (INCI: Squalene)), mineral oil (display name (INCI: Mineral Oil)), liquid isoparaffin, polyisobutylene (display name), hydrogenated polyisobutene (display name (INCI: Hydrogenated Polyisobutene)), (C13-15) alkane (display name (INCI: C13-15 Alkane)), etc.
• Higher fatty acids include oleic acid (labeled as "Oleic Acid” by INCI), linoleic acid (labeled as “Linoleic Acid” by INCI), linolenic acid (labeled as “Linolenic Acid” by INCI), arachidonic acid (labeled as “Arachidonic Acid” by INCI), eicosapentaenoic acid (EPA) (labeled as “Eicosapentaenoic Acid” by INCI), docosahexaenoic acid (DHA) (labeled as "Docosahexaenoic Acid” by INCI), isostearic acid (labeled as “Isostearic Acid” by INCI), and hydroxystearic acid (labeled as "Hydroxystearic Acid” by INCI).
• oleic acid labeleled as "Oleic Acid” by INCI
• linoleic Acid labeleled as "L
• higher alcohols include straight-chain saturated alcohols with 6 or more carbon atoms, such as lauryl alcohol (INCI), hexyldecanol (INCI), oleyl alcohol (INCI), isostearyl alcohol (INCI), octyldodecanol (INCI), decyltetradecanol (INCI), myristyl alcohol (INCI), cetyl alcohol (INCI), stearyl alcohol (INCI), and behenyl alcohol (INCI), as well as batyl alcohol (INCI).
• sterols such as cholesterol (INCI), sitosterol (display name (INCI: Beta-Sitosterol)), phytosterols (INCI), and lanosterol (INCI).
• Natural animal and vegetable oils and semi-synthetic oils include avocado oil (labeled name (INCI: Persea Gratissima (Avocado) Oil)), linseed oil (labeled name (INCI: Linum Usitatissimum (Linseed) Seed Oil)), almond oil (labeled name (INCI: Prunus Amygdalus Dulcis (Sweet Almond) Oil)), and olive oil (labeled name (INCI: Olea Europaea (Olive Fruit Oil)), Torreya California (California Nutmeg Oil)), Cymbopogon Nardus (Citronella) Oil (Indication name (INCI: Cymbopogon Nardus (Citronella) Oil)), Shark Liver Oil (Indication name (INCI: Shark Liver Oil)), Cod Liver Oil (Indication name (INCI: Cod Liver Oil) ver Oil)), fish liver oil (indication name (INCI: Fish Liver Oil)), kyonin
• Ester oils are liquid oils formed by condensing fatty acids having 1 to 20 carbon atoms with alcohols having 1 to 20 carbon atoms, and include polyesters such as monoesters, diesters, and triesters.
• n-alkyl glycol monoisostearates such as diisobutyl adipate (display name (INCI: Diisobutyl Adipate)), dihexyldecyl adipate (display name), diheptylundecyl adipate (display name (INCI: Diheptylundecyl Adipate)), isostearyl isostearate (display name (INCI: Isostearyl Isostearate)), isocetyl isostearate (display name (INCI: Isocetyl Isostearate)), trimethylolpropane triisostearate (display name (INCI: Trimethylol olpropane triisostearate), glycol die
• silicone oils include trisiloxane (display name (INCI: Trisiloxane)), volatile dimethicone (display name (INCI: Dimethicone)), low viscosity dimethicone (display name (INCI: Dimethicone)), cyclotetrasiloxane (display name (INCI: Cyclotetrasiloxane)), cyclopentasiloxane (display name (INCI: Cyclopentasiloxane)), and cyclohexasiloxane (display name (INCI: Cyclopentasiloxane)).
• Fluorine-based oils include perfluoropolyethers such as polyperfluoromethylisopropyl ether (labeled as Polyperfluoromethylisopropyl Ether by INCI), and perfluorocarbons such as perfluorodecalin (labeled as Perfluorodecalin by INCI) and perfluorohexane (labeled as Perfluorohexane by INCI).
• perfluoropolyethers such as polyperfluoromethylisopropyl ether (labeled as Polyperfluoromethylisopropyl Ether by INCI)
• perfluorocarbons such as perfluorodecalin (labeled as Perfluorodecalin by INCI) and perfluorohexane (labeled as Perfluorohexane by INCI).
• the (B) component is preferably one or more selected from silicone oil, hydrocarbon oil, and fatty acid ester.
• the amount of component (B) is not particularly limited, but is preferably 1 to 50% by mass, and more preferably 1 to 25% by mass, of the total cosmetic composition.
• the component (C) of the present invention is water, and examples of such water include purified water and distilled water from fruits or plants that are commonly used in cosmetics, as well as seawater (INCI: Sea Water), hot spring water (Onsen-Sui), peat water (INCI: Pea Water), and the like, which are defined by their display names.
• the amount of (C) water is not particularly limited, but is preferably 5 to 95% by mass, and more preferably 40 to 80% by mass, of the total cosmetic composition.
• the cosmetic preparation of the present invention may further contain one or more polyhydric alcohols, if necessary, in addition to the above components (A) to (C).
• polyhydric alcohols examples include ethylene glycol, propylene glycol, dipropylene glycol, 1,3-butylene glycol, pentylene glycol, glycerin, diglycerin, triglycerin, and polyglycerin.
• 1,3-butylene glycol, propylene glycol, diglycerin, glycerin, and combinations thereof are preferred.
• component (D) When component (D) is included, its amount is not particularly limited, but is preferably 1 to 50% by mass, and more preferably 1 to 25% by mass, of the total cosmetic composition.
• the cosmetic composition of the present invention may contain optional ingredients, as described below, to the extent that the effects of the present invention are not impaired.
• the form of the cosmetic of the present invention is not particularly limited, and examples of the form include liquid, cream, paste, solid, mousse, spray, gel, and emulsion.
• the use is also not particularly limited, and the cosmetic can be used, for example, as skin care cosmetics, makeup cosmetics, hair cosmetics, and sunscreen cosmetics.
• Specific examples of the cosmetic include makeup cosmetics such as skin care cosmetics, hair care cosmetics, cleansers, makeup bases, concealers, liquid foundations, cream foundations, solid foundations, blushers, eye shadows, mascara, eyeliners, eyebrows, and lipsticks that contain the above cosmetic ingredients, and UV protection cosmetics such as sunscreen emulsions and sunscreen creams.
• the cosmetic composition of the present invention may be in any form, including, for example, oil-based cosmetics, aqueous cosmetics, oil-in-water emulsion cosmetics, and water-in-oil emulsion cosmetics, but an oil-in-water emulsion cosmetic form is preferred.
• an oil-in-water emulsion cosmetic form the organopolysiloxane of component (A) stabilizes the emulsion interface, providing an emulsion composition with excellent stability over time. This improves the cosmetic's long-lasting effect and the feel when used.
• the cosmetic of the present invention may further contain other optional components that are commonly used in the field of cosmetics.
• the optional components include ultraviolet absorbers, surfactants other than component (A), film-forming agents, antiperspirants, antibacterial agents, preservatives, fragrances, salts, antioxidants, moisturizing agents, pH adjusters, chelating agents, cooling agents, anti-inflammatory agents, skin beautifying components (skin whitening agents, cell activators, skin roughness improving agents, blood circulation promoters, skin astringents, antiseborrheic agents, etc.), vitamins, amino acids, nucleic acids, hormones, inclusion compounds, powders, organic resins, thickeners, etc., which may be used alone or in combination of two or more in appropriate amounts.
• the ultraviolet absorbing agent is not particularly limited as long as it is a raw material that can be normally incorporated into cosmetics, and one type may be used alone or two or more types may be used in combination.
• oil-soluble ultraviolet absorbing agents include homosalate (display name (INCI: Homosalate)), octocrylene (display name (INCI: Octocrylene)), t-butyl methoxydibenzoylmethane (display name (INCI: Butyl Methoxydibenzoylmethane)), ethylhexyl salicylate (display name (INCI: Ethylhexyl Salicylate)), diethylamino hydroxybenzoyl benzoate, and the like.
• Hexyl zoate label name (INCI: Diethylamino Hydroxybenzoyl Hexyl Benzoate)), oxybenzone-6 (label name (INCI: Benzophenone-6)), oxybenzone-9 (label name (INCI: Ben) zophenone-9)), oxybenzone-1 (labeled name (INCI: Benzophenone-1)), polysilicone-15 (labeled name (INCI: Polysilicone-) 15)), Dimethoxybenzylidene dioxoimidazolidine propionate octyl (Display name (INCI: Ethylhexyl Dimethoxybenzylidene Dioxoimidazolidine Propionate)), Oxybenzone-2 (Display name (INCI: Benzophenone-2)), Terephthalylidene dicamphor sulfonic acid (Display name (INCI: Terephthalylidene Dicamphor Sulfonic Acid)
• UVA absorber e.g., diethylamino hydroxybenzoyl hexyl benzoate (display name (INCI: Diethylamino Hydroxybenzoyl Hexyl Benzoate)
• UVB absorber e.g., ethylhexyl methoxycinnamate (display name (INCI: Ethylhexyl Methoxycinnamate))
• ethylhexyl methoxycinnamate (display name (INCI: Ethylhexyl Methoxycinnamate)), diethylamino hydroxybenzoyl hexyl benzoate (display name (INCI: Diethylamino Hydroxybenzoyl Hexyl Benzoate)), octyl salicylate (display name (INCI: Ethylhexyl Salicylate)), polysilicone-15 (display name (INCI: Polysilicone-15)), t-butyl methoxydibenzoylmethane (display name (INCI: Butyl Methoxydibenzoylmethane)), and oxybenzone (display name ( One or more oil-soluble UV absorbers selected from the group consisting of methylene bis-benzotriazolyl tetramethylbutylphenol (indicated name: INCI: Methylene Bis-Benzotriazolyl Tetra
• the surfactant other than the component (A) may be a nonionic, anionic, cationic or amphoteric active agent, but is not particularly limited, and any surfactant used in ordinary cosmetics may be used.
• these surfactants partially crosslinked polyether-modified silicone, partially crosslinked polyglycerin-modified silicone, linear or branched polyoxyethylene-modified organopolysiloxane, linear or branched polyoxyethylene polyoxypropylene-modified organopolysiloxane, linear or branched polyoxyethylene-alkyl-co-modified organopolysiloxane, linear or branched polyoxyethylene polyoxypropylene-alkyl-co-modified organopolysiloxane, linear or branched polyglycerin-modified organopolysiloxane, linear or branched polyglycerin-modified organopolysiloxane, linear or branched polyglycerin-modified organopolysilox
• the amount of hydrophilic polyoxyethylene group, polyoxyethylene polyoxypropylene group or polyglycerin residue in the molecule preferably accounts for 10 to 70 mass %.
• a partially crosslinked polyether-modified silicone or a partially crosslinked polyglycerin-modified silicone it is preferable that in a composition consisting of the crosslinked organopolysiloxane and an oil agent that is liquid at 25°C, the crosslinked organopolysiloxane swells in the liquid oil by absorbing an amount of the liquid oil agent equal to or greater than its own weight.
• the liquid oil agent may be any of the liquid silicones, hydrocarbon oils, ester oils, natural animal and vegetable oils, semi-synthetic oils and fluorine-based oils contained in the optional oil agent, and examples thereof include low-viscosity silicones having a kinetic viscosity of 0.65 to 100 mm2 /s at 25°C, liquid paraffin, hydrocarbon oils such as squalane, isododecane and isohexadecane, glyceride oils such as trioctanoin, ester oils such as isotridecyl isononanoate, N-acyl glutamic acid esters and lauroyl sarcosinic acid esters, and natural animal and vegetable oils such as macadamia nut oil.
• Specific examples include KSG-210, KSG-240, KSG-310, KSG-320, KSG-330, KSG-340, KSG-320Z, KSG-350Z, KSG-710, KSG-810, KSG-820, KSG-830, KSG-840, KSG-820Z, and KSG-850Z manufactured by Shin-Etsu Chemical Co., Ltd.
• Specific examples of surfactants that are not crosslinked organopolysiloxanes include KF-6011, KF-6013, KF-6043, KF-6017, KF-6028, KF-6038, KF-6048, KF-6100, KF-6104, KF-6105, and KF-6106 manufactured by Shin-Etsu Chemical Co., Ltd.
• the amount of the surfactant is preferably 0.1 to 20% by mass in the entire cosmetic. If it is 0.1% by mass or more, the function of dispersion and emulsification can be sufficiently performed, and if it is 20% by mass or less, it is preferable because there is no risk of the cosmetic having a sticky feel when used.
• the HLB of the surfactant is not limited, but is preferably 2 to 14.5 for the purpose of maintaining the water resistance of the cosmetic.
• the film-forming agent is blended mainly for the purpose of further maintaining the durability of the cosmetic effect.
• the composition be a silicone-based composition from the viewpoint of imparting water repellency.
• trimethylsiloxysilicate display name: trimethylsiloxysilicate (INCI)
• acrylic-silicone film-forming agent silicone-modified norbornene, silicone-modified pullulan, etc.
• the film-forming agent may be dissolved in a liquid oil at room temperature before blending into the cosmetic.
• liquid oil liquid silicone, hydrocarbon oil, ester oil, natural animal and vegetable oil, semi-synthetic oil, and fluorine-based oil in the optional oil can be used.
• a liquid oil having a kinetic viscosity at 25°C of 0.65 to 100 mm2 examples include low-viscosity silicones of 100/s, liquid paraffin, squalane, isododecane, isohexadecane, and other hydrocarbon oils, glyceride oils such as trioctanoin, isotridecyl isononanoate, N-acyl glutamic acid esters, lauroyl sarcosinate, and other ester oils, and natural animal and vegetable oils such as macadamia nut oil.
• KF-7312J a silicone solution of trimethylsiloxysilicate
• KP-545 and KP-549 silicone solutions of acrylic-silicone coating agents
• NBN-30-ID a silicone-modified norbornene solution in isododecane
• TSPL-30-ID a silicone-modified pullulan solution in isododecane
• TSPL-30-D5 a silicone solution, all of which are manufactured by Shin-Etsu Chemical Co., Ltd.
• an antiperspirant can be optionally blended.
• the antiperspirant is not particularly limited as long as it is a component that suppresses sweat generation by astringing the skin, and a wide variety of general-purpose components can be used. Examples include aluminum chlorhydrate, aluminum chloride, aluminum chlorhydrate allantoin, aluminum salt of allantoin, tannic acid, aluminum potassium sulfate, zinc oxide, zinc paraphenolsulfonate, burnt alum, tetrachloro (Al/zirconium) hydrate, trichlorohydrex glycine (Al/zirconium), etc.
• components that exhibit high effects are preferably antiperspirant active ingredients selected from the group consisting of aluminum halides, aluminum hydroxyhalides, and complexes or mixtures of these with zirconyl oxyhalides and zirconyl hydroxyhalides.
• antiperspirants can be dissolved in water and blended, or the powder can be blended directly into the formulation.
• Commercially available products can also be used as antiperspirants.
• the commercially available products used may be in the form of a mixed raw material with other components.
• the amount of antiperspirant blended is not particularly limited and can be changed as appropriate depending on the amount of other ingredients blended.
• the blended amount is preferably 0.001 to 30% by mass, more preferably 0.01 to 20% by mass, of the total cosmetic.
• antibacterial agent there are no particular limitations on the antibacterial agent, so long as it is a component that can obtain a deodorizing effect by suppressing the growth of bacteria normally present on the skin that produce the substances that cause body odor.
• commonly used antibacterial agents include triclosan, benzalkonium chloride, benzothonium chloride, chlorhexidine hydrochloride, chlorhexidine gluconate, halocarban, and isomethylphenol.
• essential oils and extracts derived from herbal medicines, such as dry distillation extract of green tea, that have antibacterial properties may also be added.
• antibacterial agents with deodorizing effects such as essential oils and extracts derived from herbal medicines
• examples of antibacterial agents with deodorizing effects include green tea extract, lavender extract, Scutellaria root extract, Coptis japonica extract, Plantain extract, Artemisia capillaris extract, Aloe arborescens extract, Sophora arborescens root extract, Sasa kumamoto leaf extract, garlic extract, Hamamelis extract, black tea extract, sage leaf extract, Zanthoxylum pepper extract, ginger root extract, Calamus calamus root extract, Hedera helix extract, Houttuynia cordata extract, peach fruit extract, peach leaf extract, peppermint leaf extract, Cnidium officinalis extract, eucalyptus leaf extract, peanut seed coat extract, lychee extract, and Sanguisorba officinalis extract.
• Preservatives include alkyl paraoxybenzoates, benzoic acid, sodium benzoate, sorbic acid, potassium sorbate, phenoxyethanol, etc.
• antibacterial agents include benzoic acid, salicylic acid, carbolic acid, sorbic acid, alkyl paraoxybenzoates, parachlorometacresol, hexachlorophene, trichlorocarbanilide, photosensitizers, etc.
• Fragrances include natural fragrances and synthetic fragrances. Natural fragrances include plant-based fragrances isolated from flowers, leaves, wood, peels, etc.; and animal-based fragrances such as musk and civet. Synthetic fragrances include hydrocarbons such as monoterpenes, alcohols such as aliphatic alcohols and aromatic alcohols, aldehydes such as terpene aldehydes and aromatic aldehydes, ketones such as alicyclic ketones, esters such as terpene esters, lactones, phenols, oxides, nitrogen-containing compounds, and acetals.
• natural fragrances include plant-based fragrances isolated from flowers, leaves, wood, peels, etc.; and animal-based fragrances such as musk and civet.
• Synthetic fragrances include hydrocarbons such as monoterpenes, alcohols such as aliphatic alcohols and aromatic alcohols, aldehydes such as terpene aldehydes and aromatic aldehydes, ketones such as
• Salts include inorganic salts, organic acid salts, amine salts, and amino acid salts.
• Inorganic salts include, for example, sodium salts, potassium salts, magnesium salts, calcium salts, aluminum salts, zirconium salts, zinc salts, and the like of inorganic acids such as hydrochloric acid, sulfuric acid, carbonic acid, and nitric acid;
• organic acid salts include, for example, salts of organic acids such as acetic acid, dehydroacetic acid, citric acid, malic acid, succinic acid, ascorbic acid, and stearic acid;
• amine salts and amino acid salts include, for example, salts of amines such as triethanolamine, and salts of amino acids such as glutamic acid.
• salts of hyaluronic acid, chondroitin sulfate, and the like, aluminum zirconium glycine complexes, and even acid-alkali neutral salts used in cosmetic formulations can also be used
• Antioxidants include carotenoids, ascorbic acid and its salts, ascorbyl stearate, tocopherol acetate, tocopherol, p-t-butylphenol, butylhydroxyanisole, dibutylhydroxytoluene, phytic acid, ferulic acid, thiotaurine, hypotaurine, sulfites, erythorbic acid and its salts, chlorogenic acid, epicatechin, epigallocatechin, epigallocatechin gallate, apigenin, campherol, myricetin, and quercetin.
• Humectants include glucose, xylitol, maltitol, polyethylene glycol, hyaluronic acid, chondroitin sulfate, pyrrolidone carboxylate, polyoxyethylene methylglucoside, polyoxypropylene methylglucoside, egg yolk lecithin, soy lecithin, phosphatidylcholine, phosphatidylethanolamine, phosphatidylserine, phosphatidylglycerol, phosphatidylinositol, sphingophospholipids, etc.
• Examples of the pH adjuster include lactic acid, citric acid, glycolic acid, succinic acid, tartaric acid, dl-malic acid, potassium carbonate, sodium hydrogen carbonate, and ammonium hydrogen carbonate.
• Examples of the chelating agent include alanine, edetic acid sodium salt, sodium polyphosphate, sodium metaphosphate, phosphoric acid, aspartic acid diacetate, and ethylenediamine disuccinic acid.
• Examples of cooling agents include L-menthol and camphor.
• Anti-inflammatory agents include allantoin, glycyrrhizic acid and its salts, glycyrrhetinic acid and stearyl glycyrrhetinate, tranexamic acid, azulene, and the like.
• Skin-beautifying ingredients include whitening agents such as vitamin C derivatives, hydroquinone, tranexamic acid, arbutin, phenylethyl resorcinol, kojic acid, and plant extracts; cell activators such as royal jelly, photosensitizers, cholesterol derivatives, and calf blood extract; rough skin improving agents; blood circulation promoters such as nonylic acid valenylamide, nicotinic acid benzyl ester, nicotinic acid ⁇ -butoxyethyl ester, capsaicin, zingerone, cantharides tincture, ichthammol, caffeine, tannic acid, ⁇ -borneol, tocopherol nicotinate, inositol hexanicotinate, cyclandelate, cinnarizine, tolazoline, acetylcholine, verapamil, cepharanthine, and ⁇ -oryzanol; skin a
• Vitamins include vitamin A oil, retinol, retinol acetate, retinol palmitate and other vitamin A derivatives, riboflavin, riboflavin butyrate, flavin adenine nucleotide and other vitamin B2 derivatives, pyridoxine hydrochloride, pyridoxine dioctanoate, pyridoxine tripalmitate and other vitamin B6 derivatives, vitamin B12 and its derivatives, vitamin B Vitamin B such as vitamin 15 and derivatives thereof; vitamin C such as L-ascorbic acid, L-ascorbic acid dipalmitate, sodium L-ascorbic acid-2-sulfate, and dipotassium L-ascorbic acid phosphate diester; vitamin D such as ergocalciferol and cholecalciferol; vitamin E such as ⁇ -tocopherol, ⁇ -tocopherol, ⁇ -tocopherol, dl- ⁇ -tocopherol acetate, dl-
• amino acid examples include glycine, valine, leucine, isoleucine, serine, threonine, phenylalanine, arginine, lysine, aspartic acid, glutamic acid, cystine, cysteine, methionine, and tryptophan.
• the nucleic acid includes deoxyribonucleic acid and the like.
• Hormones include estradiol, ethenyl estradiol, and the like.
• inclusion compound examples include cyclodextrin.
• powders include fine metal oxide powders, color pigments, inorganic powders, metal powders, organic powders, and inorganic/organic composite powders.
• the fine metal oxide powder is one or more selected from fine particles of titanium oxide (display name (INCI: Titanium Dioxide)), iron-containing titanium oxide, zinc oxide (display name (INCI: Zinc Oxide)), cerium oxide (display name (INCI: Cerium Oxide)), and composites thereof. These metal oxides may be composite powders with other powders.
• coloring pigments there are no particular limitations on the coloring pigments, so long as they are pigments normally used for the purpose of coloring cosmetics, and examples of such pigments include red iron oxide (display name (INCI: Iron Oxides)), yellow iron oxide (display name (INCI: Iron Oxides)), white titanium oxide (display name (INCI: Titanium Dioxide)), black iron oxide (display name (INCI: Iron Oxides)), gunjo (display name (INCI: Ultramarines)), and konjo (display name (INCI: Ferric Ferrocyanide)).
• the coloring pigment has a particle size, i.e., a volume average particle size, in the range of 150 to 600 nm.
• the volume average particle size can be measured by TEM, etc. If it is less than 150 nm, the hiding power is low, and the coloring efficiency of the cosmetic may be low, and if it is more than 600 nm, the feeling of use may be deteriorated.
• the pigment according to the present invention may be partially or fully surface-treated with an inorganic compound such as alumina (display name (INCI: Alumina)), aluminum hydroxide (display name (INCI: Aluminum Hydroxide)), silica (display name (INCI: Silica)), hydrated silica (display name (INCI: Hydrated Silica)), etc.
• an inorganic compound such as alumina (display name (INCI: Alumina)), aluminum hydroxide (display name (INCI: Aluminum Hydroxide)), silica (display name (INCI: Silica)), hydrated silica (display name (INCI: Hydrated Silica)), etc.
• Inorganic powders include zirconium oxide (indication name (INCI: Zirconium Dioxide)), zinc oxide (indication name (INCI: Zinc Oxide)), cerium oxide (indication name (INCI: Cerium Oxide)), Mg oxide (indication name (INCI: Magnesium Oxide)), Ba sulfate (indication name (INCI: Barium Sulfate)), calcium sulfate (indication name (INCI: Calcium Carbonate)), Mg sulfate (indication name (INCI: Magnesium Sulfate)) )), Ca carbonate ( Display name (INCI: Calcium Carbonate)), Mg carbonate (Display name (INCI: Magnesium Carbonate)), Talc ( Display name (INCI: Talc)), cleaved talc (display name (INCI: Talc)), mica (display name (INCI: Mica)), kaolin (display name (INCI: Kaolin)), sericite (display name ( Syn
• Inorganic colored pearl pigments include pearl agents such as titanium oxide-coated mica, bismuth oxychloride (display name (INCI: Bismuth Oxychloride)), and bismuth oxychloride coated with titanium oxide (display name (INCI: Titanium Dioxide)). (Display name (INCI: Bismuth Oxychloride)), talc coated with titanium oxide (Display name (INCI: Titanium Dioxide)), fish scale foil, titanium oxide (Display name (INCI: Titanium Dioxide) ) Pearl pigments such as coated colored mica.
• metal powder examples include fine metal particles made of aluminum (display name (INCI: Aluminum Powder)), copper (display name (INCI: Copper Powder)), silver (display name (INCI: Silver Powder)), etc.
• organic powders examples include powders made of silicone, polyamide, polyacrylic acid/acrylic acid ester, polyester, polyethylene, polypropylene, polystyrene, styrene/acrylic acid copolymer, divinylbenzene/styrene copolymer, polyurethane, vinyl resin, urea resin, melamine resin, benzoguanamine, polymethylbenzoguanamine, tetrafluoroethylene, polymethyl methacrylate (e.g., polymethyl methacrylate, etc.), cellulose, silk, nylon, phenolic resin, epoxy resin, polycarbonate, etc.
• silicones include silicone resin particles (specific examples include polymethylsilsesquioxane (display name (INCI: Polymethylsilsesquioxane)) and the like), silicone resin-coated silicone rubber powder (specific examples include (vinyl dimethicone/methicone silsesquioxane) crosspolymer (display name (INCI: Vinyl Dimethicone/Methicone Silsesquioxane Crosspolymer)), (diphenyl dimethicone/vinyl diphenyl dimethicone) Examples of the crosspolymer include diphenyl dimethicone/vinyl diphenyl dimethicone/silsesquioxane crosspolymer (display name (INCI: diphenyl dimethicone/vinyl dimethicone/silsesquioxane crosspolymer)), polysilicone-1 crosspolymer (display name (INCI: polysilicone-1 crosspolymer)), polysilicon
• Metal soaps are also included, and a specific example is stearyl alcohol.
• Zinc stearate (display name (INCI: Zinc stearate)), Aluminum stearate (display name (INCI: Aluminum stearate)), Calcium stearate (display name (INCI: Calcium stearate)), Magnesium stearate (display name (INCI: Magnesium stearate)), Zinc myristate (display name (INCI: Zinc myristate)), Magnesium myristate (display name (INCI: Magnesium myristate)), Cetyl phosphate (zinc/N a) (display name (INCI: Sodium Zinc Cetyl Phosphate)), potassium cetyl phosphate (display name (INCI: Potassium Cetyl Phosphate)), etc.
• organic dyes and the like can also be mentioned, and specific examples thereof include Red 3, Red 104 (1) (display name (INCI: Red 28, Red 28 Lake)), Red 106, Red 201 (display name (INCI: Red 6)), Red 202 (display name (INCI: Red 7)), Red 204, Red 205, Red 220 (display name Red 226 (Display name (INCI: Red 30)), Red 227 (Display name (INCI: Red 33, RED 33 Lake))), Red 228 (Display name (INCI: Red 36)), Red 230 (1) (Display name (I NCI: Red 22, Red 22 Lake)), Red 230 (2), Red 401, Red 505, Yellow 4 (Display name (INCI: Yellow 5))), Yellow 5 (Display name (INCI: Yellow 6, Yellow 6 Lake)), Yellow 202 (1) ) (Display name (INC) Yellow 203 (Display name (INCI: Yellow 10, Yellow 10 Lake)), Yellow 204 (Display name (INCI: Yellow 11)
• the inorganic-organic composite powder may be, for example, a composite powder in which the surface of an inorganic powder is coated with an organic powder by a publicly known method.
• the powder may be hydrophobized.
• the hydrophobizing agent for surface-treating the raw material powder is not particularly limited as long as it can impart hydrophobicity, and specific examples of the hydrophobizing agent include silicone treatment agents, waxes, paraffins, organic fluorine compounds such as perfluoroalkyl and phosphates, surfactants, amino acids such as N-acyl glutamic acid, and metal soaps such as aluminum stearate (display name (INCI: Aluminum Stearate)) and magnesium myristate (display name (INCI: Magnesium Myristate)).
• silicone treatment agents are preferably used, and examples of such agents include silanes or silylating agents such as triethoxycaprylylsilane (display name (INCI: Triethoxycaprylylsilane)) or trimethoxysilyl dimethicone (display name (INCI: Trimethoxysilyl Dimethicone)), dimethicone (display name (INCI: Dimethicone)), hydrogen dimethicone (display name (INCI: Hydrogen Dimethicone)), triethoxysilylethyl polydimethylsiloxyethylhexyl dimethicone (display name (INCI: Triethoxysilylethyl Polydimethylsiloxyethylhexyl Dimethicone)).
• silanes or silylating agents such as triethoxycaprylylsilane (display name (INCI: Triethoxycaprylylsilane)) or trimeth
• silicone oil examples include silicone oils such as (Acrylates/Tridecyl Acrylate/Triethoxysilylpropyl Methacrylate/Dimethicone Methacrylate) Copolymer (Display name (INCI: Acrylates/Tridecyl Acrylate/Triethoxysilylpropyl Methacrylate/Dimethicone Methacrylate Copolymer)), and silicone compounds such as (Acrylates/Dimethicone) Copolymer (Display name (INCI: Acrylates/Dimethicone Copolymer)).
• the above surface hydrophobic treatment agents can be used alone or in combination of two or more.
• hydrophobic powder examples include synthetic and natural materials.
• hydrophobized fine metal oxide powder commercially available products can also be used.
• fine titanium oxide particles are commercially available under the trade names STR-100C-LP, STR-100A-LP, STR-100W, STR-100W-LP, STR-100W-OTS, STR-100C-LF, STR-40-LP (manufactured by Sakai Chemical Industry Co., Ltd.), MT-01, MT-05, MT-100Z, MT-100TV, MT-100AQ, MT-150EX, MT-500B, MT-505SAS, MT-700B, MT-014Z, SMT-500SAS (manufactured by Teika Co., Ltd.), ST-455, ST-455WS, ST-457ECS, ST-495M (manufactured by Titanium Industries Co., Ltd.), etc.
• FINEX-50S-LP2, FINEX-30S-LP2, FINEX-50W, FINEX-30W, FINEX-50W-LP2, FINEX-52W-LP2, FINEX-30W-LP2, FINEX-33W-LP2, FINEX-50-LPT, FINEX-25-LPT, FINEX-50S- These are commercially available under the trade names of FINEX-LPT, FINEX-30S-LPT, FINEX-30-OTS (manufactured by Sakai Chemical Industry Co., Ltd.), MZ-150, MZ-200, MZ-300, MZ-306X, MZ-500HP, MZ-505T, MZ-506X, MZY-203S, MZY-210M3S, TMZ-HA1, MZX-5080TS (manufactured by Teika Co., Ltd.), etc.
• color pigments that have been hydrophobized include the KTP-09 series, in particular KTP-09W, KTP-09R, KTP-09Y, and KTP-09B (manufactured by Shin-Etsu Chemical Co., Ltd.).
• R1 having 6 or more carbon atoms in (A-1) was 18 mass%.
• Examples 1 to 7, Comparative Examples 1 to 3 The components shown in Table 2 were mixed in the amounts shown in Table 2 by the following production method to obtain an oil-in-water emulsion composition.
• Step 1 Components (1) and (2) were mixed, and components (3) to (5) were added thereto and mixed uniformly.
• Step 2 Component (6) and a part of component (8) were mixed.
• Step 3 Under stirring, the mixture obtained in step 2 was added to the mixture obtained in step 1 and mixed.
• Step 4 With stirring, component (7) and the remainder of component (8) were further added to the mixture obtained in step 3 and mixed to obtain an oil-in-water emulsion composition.
• Examples 8 to 10, Comparative Examples 4 to 5 The components shown in Table 3 were mixed in the amounts shown in Table 3 by the following production method to obtain an oil-in-water emulsion composition.
• Step 1 A part of component (2) and components (9) to (11) were mixed and the mixture was dispersed in a part of component (14).
• Step 2 Component (7) and a part of component (14) other than that used in step 1 were mixed.
• Step 3 While stirring, component (1) and the remainder of component (2) were mixed, and components (3) to (6) were added thereto, and further component (8) and the remainder of component (14) were added thereto to obtain a mixture.
• Step 4 The mixture obtained in step 2 and the dispersion obtained in step 1 were added to the mixture obtained in step 3 under stirring, and then components (12) and (13) were further added and mixed to obtain an oil-in-water emulsion composition.
• Example 11 to 12 The components shown in Table 4 were mixed in the amounts shown in Table 4 by the following production method to obtain an oil-in-water emulsion composition.
• Step 1 Components (1) to (4) were mixed uniformly.
• Step 2 Components (5) to (8) were mixed uniformly.
• Step 3 The mixture obtained in step 2 was added to the mixture obtained in step 1 under stirring, and emulsified to obtain a water-in-oil emulsion composition.
• Example 13 An oil-in-water liquid foundation was obtained by mixing the components in the amounts shown in Table 5 according to the manufacturing method described below.
• Step 1 Component 13 and a part of component 2 were mixed, and then components 9 to 12 were added and mixed uniformly.
• Step 2 Components 4 and 5 were mixed uniformly.
• Step 3 Component 1 and the remainder of component 2 were mixed uniformly.
• Step 4 Component 3, component 6 and the mixture obtained in step 2 were mixed uniformly.
• Step 5 Component 7 and a portion of component 14 were mixed uniformly.
• Step 6 The mixture obtained in step 4 was added to the mixture obtained in step 3 and emulsified, and the mixture obtained in step 5 was further added thereto.
• Step 7 To the mixture obtained in step 6, the remainder of component 8 and component 14, and the mixture obtained in step 1 were added to obtain an oil-in-water (O/W) type liquid foundation.
• O/W oil-in-water
• the oil-in-water liquid foundation obtained in Example 13 had excellent stability over time, spread well on the skin, and gave a smooth feel when used.
• the cosmetic film obtained was uniform, had good water resistance, and lasted well.

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