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WO2002009658A1 - Composition de resine cosmetique - Google Patents

Composition de resine cosmetique Download PDF

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Publication number
WO2002009658A1
WO2002009658A1 PCT/US2000/009957 US0009957W WO0209658A1 WO 2002009658 A1 WO2002009658 A1 WO 2002009658A1 US 0009957 W US0009957 W US 0009957W WO 0209658 A1 WO0209658 A1 WO 0209658A1
Authority
WO
WIPO (PCT)
Prior art keywords
urethane resin
cosmetic
compound
resin composition
amphoteric urethane
Prior art date
Application number
PCT/US2000/009957
Other languages
English (en)
Inventor
Seiji Asaoka
Takahiro Sakurai
Katsuya Koyama
Toshitaka Tsuzuki
Tomohiro Hashimoto
Original Assignee
National Starch And Chemical Investiment Holding Corporation
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 National Starch And Chemical Investiment Holding Corporation filed Critical National Starch And Chemical Investiment Holding Corporation
Priority to DE60022194T priority Critical patent/DE60022194T2/de
Priority to CN00811598.2A priority patent/CN1222268C/zh
Priority to EP00923327A priority patent/EP1191921B1/fr
Priority to PCT/US2000/009957 priority patent/WO2002009658A1/fr
Priority to AU2000243473A priority patent/AU2000243473A1/en
Priority to BR0011621-1A priority patent/BR0011621A/pt
Priority to MXPA01012886A priority patent/MXPA01012886A/es
Priority to US10/009,960 priority patent/US6884853B1/en
Publication of WO2002009658A1 publication Critical patent/WO2002009658A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/896—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
    • A61K8/72—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
    • A61K8/87—Polyurethanes
    • 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
    • A61Q3/00—Manicure or pedicure preparations
    • A61Q3/02—Nail coatings
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
    • C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
    • C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
    • C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/61—Polysiloxanes
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6633—Compounds of group C08G18/42
    • C08G18/6659—Compounds of group C08G18/42 with compounds of group C08G18/34
    • 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
    • C08G77/458—Block-or graft-polymers containing polysiloxane sequences containing polyurethane sequences
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/10—Preparations containing skin colorants, e.g. pigments for eyes, e.g. eyeliner, mascara
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q9/00—Preparations for removing hair or for aiding hair removal
    • A61Q9/02—Shaving preparations

Definitions

  • the present invention relates to a cosmetic resin composition consisting essentially of amphoteric urethane resin and a cosmetic using such a resin composition, and particularly, to a cosmetic resin composition used for a skin care product, a hair care product and the like as a hair fixative, a film forming agent, a conditioning agent, a viscosity controlling agent and the like, and a cosmetic using the same.
  • a cationic acrylic resin, an anionic acrylic resin, an amphoteric or anionic/cationic acrylic resin, a nonionic polyvinyl pyrrolidone resin and the like are used as a base resin of a hair fixative.
  • a resin is used as a base resin, hair is set stiff, resulting in a good setting property (stiffness), but feel and combability are inferior and also flaking may occur.
  • feel and combability come first, not only setting property becomes insufficient, but also problems such as stickiness and the like may occur.
  • an application of an anionic urethane resin as a base resin for a hair fixative is proposed as seen in Japanese Provisional Publication TOKKAIHEI 6-321741.
  • a hair fixative having good stiffness, feel, shampoo removability and anti-flaking property, which are inconsistent to each other can be prepared, in this viewpoint, a hair fixative using such an anionic urethane resin is superior to a hair fixative using the above mentioned acrylic resin.
  • problems such as a rough feel, inferiority in gloss and combability may be caused.
  • a cosmetic resin composition consisting essentially of an amphoteric urethane resin having a carboxyl group and a tertiary amino group in one molecule thereof, the amphoteric urethane resin having polysiloxane linkage in its structure, in accordance with a second aspect of the present invention, there is provided cosmetics using the cosmetic resin composition.
  • a hair fixative having stiffness, feel, combability, anti-flaking property and the like can be obtained by using an amphoteric urethane resin having a carboxyl group and a tertiary amino group in one molecule thereof as a base resin and filed a patent application about a resin composition consisting essentially of the amphoteric urethane resin (Japanese Patent Application No. TOKUGANHEl 10-27595). Improvement in each property when using the amphoteric resin is due to the following reason.
  • urethane resin as a main skeleton of a base resin makes It possible that stiffness is compatible with feel, combability and anti-flaking property, which are originally contrary to each other, due to elasticity and toughness of the urethane resin.
  • amphoteric urethane resin having a carboxyl group and a tertiary amino group, it becomes possible to prepare a hair fixative superior in waterproof against neutral water because the carboxyl group and the tertiary amino group are ion-bonded, and also superior in shampoo removability because the ion-bond is cut by shampoo, in addition, since the amphoteric urethane resin has a cationic tertiary amino group, which interacts with a negatively charged hair surface, in its molecular chains, better adhesion can be obtained compared with a conventional anionic urethane resin.
  • the inventors further made researches about the resin composition consisting essentially of the amphoteric urethane resin.
  • the cosmetic resin composition of the present invention consists essentially of an amphoteric resin having a carboxyl group and a tertiary amino group in one molecule thereof.
  • the most characteristic point of the present invention is that the amphoteric urethane resin has polysiloxane linkage in its structure.
  • the phrase "consisting essentially of an amphoteric urethane resin” means generally preparation of the cosmetic resin composition of interest by adding other components into the amphoteric urethane resin, however, includes the case where the cosmetic resin composition consists only of the amphoteric urethane resin.
  • amphoteric urethane resin having polysiloxane linkage may be obtained, for example, by reacting a polyol compound [component (A)], a polyisocyanate compound [component (B)i, a polysiloxane compound [component (C)l having an active hydrogen and a compound [component (D)l having an active hydrogen and a carboxyl group with each other in excess of isocyanate groups so as to produce a prepolymer containing an isocyanate group and reacting the prepolymer with a compound [component (E)] having an active hydrogen and a tertiary amino group.
  • the amphoteric urethane resin having polysiloxane linkage may be obtained by changing the reaction order of the component (D) for the component (E), i.e., by reacting component (A), the component (B), the component (C) and the component (E), i.e., by reacting the component (A), the component (B), the component (C) and the component (E) in excess of isocyanate groups so as to produce a prepolymer containing an isocyanate group and reacting the prepolymer with the component (D).
  • the amphoteric urethane resin of interest can be produced more easily and more safely by such methods than the conventional methods, in addition, if both the component (D) and the component (E) are simultaneously reacted together with the components (A) to (C) in the above methods, a carboxyl group of the component (E) initially form a salt which becomes insoluble to the reaction system and a reaction with the isocyanate compound may not occur even in the presence of an OH group. As a result, the amphoteric urethane resin of interest cannot be produced.
  • amphoteric urethane resin having polysiloxane linkage can be produced by firstly reacting one of the component (D) and the component (E) together with the components (A) to (C) and then reacting the other component (D) or (E).
  • the polyol compound of the component (A) is not specifically limited, but any of the polyol compounds generally used for producing polyurethane.
  • the polyol compound include polyester polyol, polyether polyol, polycarbonate polyol, polybutadiene polyol, polyisoprene polyol, polyolefin polyol, polyacrylic ester polyol. These may be used either alone or in combination thereof. Among all, polyester polyol and polyether polyol are especially preferred.
  • polyester polyol inlcude products obtained by condensation polymerizing at least one of dicarboxylic acids such as succinic acid, glutaric acid, adipic acid, sebacic acid, azelaic acid, maleic acid, fumaric acid, phthalic acid, terephthalic acid and the like with at least one of polyhydric alcohols such as ethylene glycol, propylene glycol, 1,4-butanediol, ,3-butanediol, 1,6-hexanediol, neopentyl glycol, 1,8-octanediol, ,10-decanediol, diethylene glycol, spiroglycol, trimethylolpropane and thelike, and products obtained by ring-opening addition polymerizing cyclic ethers such as ethylene oxide, propylene oxide oxetane and tetrahydrofuran into water, polyol, phenols such as bisphenol
  • Examples of such products include polyoxyethylene polyol, polyoxypropylene polyol, polyoxytetramethylene polyol and products (either a blocked copolymer or a random copolymer in case of a copolymer) obtained by ring-opening addition polymerizing at least one of propylene oxide and ethylene oxide into bisphenol A.
  • the polyisocyanate compound of the component (B) is not specifically limited. Examples thereof include organic diisocyanate compounds such as aliphatic diisocyanate compounds, alicyclic diisocyanate compounds and aromatic diisocyanate compounds. These may be used either alone or in combination thereof. Examples of the aliphatic diisocyanate compounds include ethylene diisocyanate, 2,2,4-trimethyl hexamethylene diisocyanate, 1,6-hexamethylene diisocyanate.
  • Examples of the alicyclic diisocyanate compounds include hydrogenated diphenyl methane-4,4'-diisocyanate, 1,4- cyclohexane diisocyanate methylcyclohexylene diisocyanate, isophorone diisocyanate, norbornane diisocyanate.
  • Examples of the aromatic diisocyanate compounds include diphenyl methane- 4,4'-diisoc ⁇ anate, xylylene diisocyanate, toluene diisocyanate, toluene diisocyanate and naphthalene diisocyanate.
  • 1,6-hexamethylene diisocyanate, isophorone diisocyanate, norbornane diisocyanate and the like are preferred in viewpoints of the performance cost.
  • the specific polysiloxane compound of the component (C) is not specifically limited, but any of compound wherein polysiloxane linkage, a chain of siloxane bonds (Si-O), can be introduced into the structure of the amphoteric urethane resin, may be used.
  • the polysiloxane linkage introduced into the structure of the amphoteric urethane resin preferably has a repetitive number n of a range between 5 and 300, more preferably a range between 20 and 150.
  • the repetitive number n is less than 5
  • the proportion of the polysiloxane linkage of thus obtained amphoteric urethane resin becomes too low and sufficient effect on feel, combability and the like, which may be originally obtained by introduction of the polysiloxane bond, may not be obtained.
  • the repetitive number n is more than 300, a high hydrophobic property deteriorates compatibility with other materials and becomes difficult to react therewith. Further, since the thus obtained polymer becomes too hydrophobic, there may be caused the fear that adhesion after combing is prohibited.
  • the specific polysiloxane compound of the component (C) is not specifically limited, but any of compound which have an active hydrogen and polysiloxane linkage in its molecule.
  • Examples include a compound having OH groups at both terminals, a compound having NH 2 groups at both terminals, a compound having an OH group at one terminal and a compound having an NH 2 at one terminal.
  • the amphoteric urethane resin having polysiloxane linkage as a main chain can be obtained.
  • the amphoteric urethane resin having polysiloxane linkage as a side chain or at a terminal can be obtained.
  • polysiloxane compound [component (C)l may comprise combinations, each which has a different number in carbons of the alkyl groups to be combined with Si of each siloxane bond
  • examples of the polydialkyl siloxane diol include polydimethyl siloxane diol and polymethylethyl siloxane diol.
  • examples of the polydialkyl siloxane monool include polydimethyl siloxane monool and polymethylethyl siloxane monool.
  • polydialkyl siloxane diamine and polymethylethyl siloxane diamine examples of the polydialkyl siloxane monoam ⁇ ne polymethylethyl siloxane monoamine.
  • the compound [component (D)l having an active hydrogen and a carboxyl group is not specifically limited, but any of compound which may have at least one active hydrogen and at least one carboxyl group in its molecule.
  • Examples include dimethylol propionic acid (DMPA), dimethylol butanoic acid and polycaprolactone diol having a carboxyl group. These may be used either alone or in combination thereof.
  • the compound [component (EH having an active hydrogen and a tertiary amino group is not specifically limited, but any of compound which may have at least one active hydrogen and at least one tertiary amino group in its molecule. Examples include N-alkvldialkanolamine compound such as N- methyldiethanolamine, and dimethylaminoethanol.
  • chain extender in preparation of the prepolymer containing an isocyanate group by using each of the above components, it is preferred to use a chain extender.
  • the use of the chain extender makes it possible to adjust various properties of the obtained amphoteric urethane resin as a final product.
  • the chain extender is not specifically limited. Examples include low molecular weight polyols include glycols such as ethylene glycol, propylene glycol, 1,4-butanediol, diethylene glycol, 1,6-hexanediol, spiroglycol, bis(- hydroxyethoxy) benzene and xylene glycol and triols such as trimethylolpropane and glycerin.
  • amines examples include methylene (bis-o-chloroaniline).
  • solvents may be used, as required.
  • solvents which may solve both a raw material and the obtained polyurethane.
  • examples include amides such as N- methyl pyrrolidone, dimethylformamide and dimethylacetamide, ketones such as acetone and methyl ethyl ketone and esters such as ethyl acetate as well as cellosolve acetate and cellosolve ether, in addition, in preparation of the amphoteric urethane resin, a polymerization catalyst coventionally known in the field of polyurethane may be used.
  • Examples include tertiary amine catalyst and organometallic catalyst.
  • tertiary amine catalyst 12,2,21 diazabicyclo octane (DABCO), tetramethylene diamine, N-methylmorpholine, diazbicyclo undecene (DBU) may be used.
  • DBU diazabicyclo octane
  • examples include dibutyltindilaurate.
  • any other ingredients generally used in cosmetics other than the specific amphoteric urethane resin such as pigment, coloring matter, colorant, fragrance, surfactant, moisturizer, preservative, antiseptic, disinfectant and antioxidant may be added to the cosmetic resin composition.
  • the cosmetic resin composition of the present invention is used for, for example, hair fixatives such as a mousse hair fixative, a gel hair fixative, a spray hair fixative and a pump spray hair fixative, a conditioning shaving cream agent, a film forming agent such as skin care lotion, foundation, eye liner and manicure, and viscosity adjuster.
  • hair fixatives such as a mousse hair fixative, a gel hair fixative, a spray hair fixative and a pump spray hair fixative
  • a conditioning shaving cream agent such as skin care lotion, foundation, eye liner and manicure
  • a film forming agent such as skin care lotion, foundation, eye liner and manicure
  • viscosity adjuster Especially, the cosmetic resin composition is useful for a hair fixative.
  • the specific amphoteric urethane resin is applied for the above usage after being dispersed as a dispersion by dispersing thereof into water or being solubilized as an aqueous solution by solubilizing thereof into water, respectively, in this case, it is preferred that the amphoteric urethane resin is dispersed into water containing aliphatic polyamine. That is, when the polymer is reacted with the aliphatic polyamine as the polymer is dispersed into water by controlling polymerization in excess of isocyanate groups, NH groups and NH 2 groups of the aliphatic polyamide rapidly react with the isocyanate groups to generate urea bonds in water, resulting in acceleration of polymerization.
  • the aliphatic polyamine is not specifically limited. Examples include triethylamine, ethylene diamine, propylene diamine, piperazine and diethylene triamine. Further, it is possible that silane coupling agent may be added into the dispersion of the amphoteric urethane resin for improvement of adhesive property with other base materials, still further, various antibacterial agent and an antifungal agent may be added to give preservation stability. Examples will next be described along with Comparative
  • IPDD isophorone diisocyanate
  • DEGA diethylene glycol adipate
  • DEGA diethylene glycol adipate
  • Newpol BP3P an adduct of bisphenol A with ethylene oxide
  • DMPA dimethylol propionic acid
  • ethyl acetate as a solvent and 0.02 g of dibutyltindilaurate (DBTDU as a catalyst were added thereto, warmed to 80 by an oil bath to be allowed to react for 4 hours. Thereafter, 5.6 g of N-methyldiethanolamine (NMDEtA) and 60 g of ethyl acetate were added thereto and allowed to react at 80 for 2 hours, for obtaining polyurethane prepolymer solution wherein NCO groups remain.
  • DBTDU dibutyltindilaurate
  • Example 2 70 g of isophorone diisocyanate (IPDI), 56 g of polytetraoxy methylene glycol (PTiVlG, molecular weight 2,000), 20 g of an adduct of bisphenol A with ethylene oxide (ADK polyether BPX21 available from Asahi Denka Kogyo KK, molecular weight 400), 26 g of polyethylene glycol (PEG, molecular weight 2,000), 26 g of polydimethyl siloxane diol (a type having OH groups at both terminals, molecular weight 2,000) and 16.9 g of dimethylol propionic acid (DMPA) were put into a four-neck flask provided with a stirrer, a thermometer, an inlet tube for nitrogen and a reflux condenser.
  • IPDI isophorone diisocyanate
  • PEG polyethylene glycol
  • polydimethyl siloxane diol a type having OH groups at both terminals, mole
  • ethyl acetate as a solvent and 0.02 g of dibutyltindilaurate (DBTDU as a catalyst were added thereto, warmed to 80 by an oil bath to be allowed to react for 4 hours. Thereafter, 5.6 g of N-methyldiethanolamine (NMDEtA) and 60 g of ethyl acetate were added thereto and allowed to react at 80 for 2 hours, for obtaining polyurethane prepolymer solution wherein NCO groups remain.
  • DBTDU dibutyltindilaurate
  • IPDI isophorone diisocyanate
  • DEGA diethylene glycdol adipate
  • DMPA dimethylol propionic acid
  • ethyl acetate as a solvent and 0.02 g of dibutyltindilaurate (DBTDU as a catalyst were added thereto, warmed to 80 by an oil bath to be allowed to react for 4 hours. Thereafter, 5.6 g of N-methyldiethanolamine (NMDEtA) and 60 g of ethyl acetate were added thereto and allowed to react at 80 for 2 hours, for obtaining polyurethane prepolymer solution where NCO groups remain.
  • DBTDU dibutyltindilaurate
  • IPDI isophorone diisocyanate
  • DEGA diethylene glycol adipate
  • DEGA diethylene glycol adipate
  • Newpol BP3P available from Sanyo Chemical industries, Ltd., molecular weight 400
  • 10 g of polydimethyl siloxane diol a type having OH groups at both terminals, molecular weight 800
  • 16.9 g of dimethylol propionic acid (DMPA) were put into a four-neck flask provided with a stirrer, a thermometer, an inlet tube for nitrogen and a reflux condenser.
  • DMPA dimethylol propionic acid
  • ethyl acetate as a solvent and 0.02 g of dibutyltindilaurate (DBTD ⁇ as a catalyst were added thereto, warmed to 80 by an oil bath to be allowed to react for 4 hours. Thereafter, 5.6 g of N-methyldiethanolamine (NMDEtA) and 60 g of ethyl acetate were added thereto and allowed to react at 80 for 2 hours, for obtaining polyurethane prepolymer solution wherein NCO groups remain.
  • NMDEtA N-methyldiethanolamine
  • Example 5 70 g of isophorone diisocyanate (IPDI), 80 g of diethylene glycol adipate (DEGA, molecular weight 2,000), 20 g of an adduct of bisphenol A with ethylene oxide (Newpol BP3P available from Sanyo Chemical industries, Ltd., molecular weight 400), 26 g of polydimethyl siloxane diol (a type having OH groups at both terminals, molecular weight 5,000) and 16.9 g of dimethylol propionic acid (DMPA) were put into a four-neck flask provided with a stirrer, a thermometer, an inlet tube for nitrogen and a reflux condenser.
  • IPDI isophorone diisocyanate
  • DEGA diethylene glycol adipate
  • DEGA diethylene glycol adipate
  • Newpol BP3P available from Sanyo Chemical industries, Ltd., molecular weight 400
  • 26 g of polydimethyl siloxane diol
  • ethyl acetate as a solvent and 0.02 g of dibutuyltindilaurate (DBTDU as a catalyst were added thereto, warmed to 80 by an oil bath to be allowed to react for 4 hours. Thereafter, 5.6 g of N-methyldiethanolamine (NMDEtA) and 60 g of ethyl acetate were added thereto and allowed to react at 80 for 2 hours, for obtaining polyurethane prepolymer solution wherein NCO groups remain.
  • DBTDU dibutuyltindilaurate
  • IPDI isophorone diisocyanate
  • DEGA diethylene glycol adipate
  • DEGA diethylene glycol adipate
  • Newpol BP3P available from Sanyo Chemical industries Ltd., molecular weight 400
  • 16.9 g of dimethylol propionic acid (DMPA) were put into a four-neck flask provided with a stirrer, a thermometer, an inlet tube for nitrogen and a reflux condenser.
  • DMPA dimethylol propionic acid
  • ethyl acetate as a solvent and 0.02 g of dibutyltindilaurate (DBTDU as a catalyst were added thereto, warmed to 80 by an oil bath to be allowed to react for 4 hours. Thereafter, 5.6 g of N- methyldiethanolamine (NMDEtA) and 60 g of ethyl acetate were added thereto and allowed to react at 80 for 2 hours, for obtaining polyurethane prepolymer solution wherein NCO groups remain.
  • DBTDU dibutyltindilaurate
  • Comparative Example 1 70 g of isophorone diisocyanate (IPDD.106 g of diethylene glycol adipate (DEGA, molecular weight 2,000), 20 g of an adduct of bisphenol A with ethylene oxide (Newpol BP3P available from Sanyo chemical Industries, Ltd., molecular weight 400) and 16..9 g of dimethylol propionic acid (DMPA) were put into a four-neck flask provided with a stirrer, a thermometer, an inlet tube for nitrogen and a reflux condenser.
  • IPDD.106 g of diethylene glycol adipate (DEGA, molecular weight 2,000) 20 g of an adduct of bisphenol A with ethylene oxide (Newpol BP3P available from Sanyo chemical Industries, Ltd., molecular weight 400) and 16..9 g of dimethylol propionic acid (DMPA) were put into a four-neck flask provided with a stirrer, a thermometer
  • ethyl acetate as a solvent and 0.02 g of dibutyltindilaurate (DBTDU as a catalyst were added thereto, warmed to 80 by an oil bath to be allowed to react for 4 hours. Thereafter, 5.6 g of N-methyldiethanolamine (NMDEtA) and 60 g of ethyl acetate were added thereto and allowed to react at 80 for 2 hours, for obtaining polyurethane prepolymer solution wherein NCO groups remain.
  • DBTDU dibutyltindilaurate
  • IPDI isophorone diisocyanate
  • DEGA diethylene glycol adipate
  • DMPA dimethylol propionic acid
  • Mousse hair fixatives a to i were prepared by using thus obtained dispersions of Examples and Comparative Examples at mixing ratios as follows.
  • a mousse hair fixative a ingredients shown in the following Table 1 were blended at proportions shown in the same table, and mixed until thus obtained mixture became homogenous, for obtaining X component. Then, Y component shown in the same table was added into the X component, for obtaining a mousse hair fixative a.
  • mousse hair fixatives b, c, d, e and f were prepared in the same way as the mousse hair fixative a.
  • Example 1 instead of the dispersion obtained by Example 1 shown in the Table 1, each dispersion of Comparative Examples 1, 2 and 3 was used. Except for that, mousse hair fixatives g, h and l were prepared in the same way as the mousse hair fixative a.
  • each 0.6 g of the thus obtained mousse hair fixatives was applied on a separate hair swatch of black virgin black (15 cm in length, 3 g in weight), respectively, and the hair swatch was dried at room temperature, for obtaining each hair-dressed swatch. After each swatch was slightly loosened in warm water of 40 for 30 seconds, 0.4 g of 10% shampoo solution was applied thereon and washed for 30 seconds. Thereafter, each swatch was rinsed in warm water of 40 so as to be washed out, and then dried sufficiently at 50.
  • FEEL indicates that no hair dishevelment was caused on a swatch after being dried and elasticity was excellent, indicates that elasticity was good and indicates that feel was slightly inferior.
  • STIFFNESS indicates that no hair dishevelment was caused on a swatch after being dried and stiffness was excellent, indicates that stiffness was good and indicates that stiffness was slightly inferior.
  • TACTILE PROPERTY Indicates that a swatch after being dried had smooth tactile property or a swatch had an excellent touch, indicates a good touch and indicates a slightly rough touch.
  • COMBABILITY indicates that combability of a swatch after being dried was excellent, indicates that combability is good, indicates that combability is slightly inferior and x indicates that combability is inferior.
  • ANTI-FLAKING PROPERTY indicates that no flake was caused on a swatch after being dried with 10-time combing, indicates that almost no flake caused and indicates that slightly flake caused.
  • mousse hair fixatives a to f are superior in all properties of curl retention, shampoo removability, feel, stiffness, gloss, tactile property, combability and anti-flaking property. Also, it is found that mousse hair fixatives a to f are further superior to a mousse hair fixative g, which uses an amphoteric urethane resin not having a dimethyl siloxane chain in its structure, in gloss, tactile property, combability and anti-flaking property because the mousse hair fixatives a to f use amphoteric urethane resin having a dimethyl siloxane chain in its structure, in addition, it is found that a mousse hair fixative b is excellent in shampoo removability, feel and stiffness due to the presence of an ethylene oxide chain as a nonionic hydrophilic component in the structure of the amphoteric urethane resin.
  • a mousse hair fixative g is good in curl retention, shampoo removability, feel and stiffness due to the glosss, tactile property, combability and anti-flaking property because the amphoteric urethane resin used therein does not have a dimethyl siloxane chain in its structure
  • a mousse hair fixative h is remarkably inferior in combability because anionic urethane resin is used, and is also inferior in other properties except for stiffness.
  • a mousse hair fixative i is improved in gloss, tactile property, combability and anti-flaking property compared with the mousse hair fixatives g and h because the mousse hair fixative i uses a dispersion containing an amphoteric urethane resin and dimethyl siloxane, but is inferior to the mousse hair fixatives a to f in the same properties because the above mentioned dimethyl siloxane is not bonded to the amphoteric urethane resin.
  • gel hair fixatives a to i were prepared using each dispersion of Examples and comparative Examples in accordance with the following proportions.
  • Gel Hair Fixatives a ingredients shown in the following Table 3 were blended in proportions shown in the same table and mixed until a viscous gel was formed, for obtaining X component.
  • ingredients shown in Table 3 were blended in proportions shown in the same table, for obtaining Y component.
  • Y component was added into thus obtained X component and mixed until it became homogeneous, for obtaining a gel hair fixative a.
  • Gel Hair Fixatives b, c, d, e and f instead of the dispersion of Example 1 for Y component shown in the above Table 3, each dispersion of Examples 2, 3, 4, 5 and 6 was used. Except for that, gel hair fixatives b, c, d, e and f were prepared in the same way as the gel hair fixative a.
  • Examples 1, 2 and 3 was used. Except for that, gel hair fixatives g, h and i. were prepared in the same way as the gel hair fixative a.
  • Spray Hair Fixatives b, c, d, e and f instead of the dispersion of Example 1 for X component shown in the above Table 4, each dispersion of Examples 2, 3, 4, 5 and 6 was used. Except for that, spray hair fixatives b, c, d, e and f were prepared in the same way as the spray hair fixative a.
  • Spray Hair Fixatives g, h and I instead of the dispersion of Example 1 for X component shown in the above Table 4, each dispersion of comparative
  • pump spray Hair Fixatives b, c, d, e and f instead of the dispersion of Example 1 shown in the above Table 5, each dispersion of Examples 2, 3, 4, 5 and 6 was used. Except for that, pump spray hair fixatives b, c, d, e and f were prepared in the same way as the pump spray hair fixative a.
  • Pump Spray Hair Fixatives g, h and I instead of the dispersion of Example 1 shown in the above Table 5, each dispersion of Comparative Examples 1, 2 and 3 was used. Except for that, pump spray hair fixatives g, h and I were prepared in the same way as the pump spray hair fixative a.
  • the cosmetic resin composition of the present invention may be used for a conditioning shaving cream agent, a film forming agent such as skin care lotion, emulsified foundation, cream foundation, eye liner and manicure, as mentioned below.
  • Conditioning Shaving Cream Agent ingredients sown in the following Table 6 were mixed in the proportions as shown in the same table and was warmed up to 80, for obtaining X component. Next, ingredients shown in the same table were mixed in the proportions shown in the same table and was warmed up to 80, for obtaining Y component. Then, the X component and the Y component were mixed at 80, the resulting mixture was cooled down to 40 and antiseptic and fragrance were added at each suitable amount, for obtaining the conditioning shaving cream agent of interest.
  • Skin care Lotion ingredients shown in the following Table 7 were mixed in the proportions shown in the same table and was warmed up to 80, for obtaining X component.
  • ingredients shown in the same table were mixed in the proportions shown in the same table and was warmed up to 80, for obtaining Y component.
  • the X component and the Y component were mixed and agitated at 80 for 30 minutes.
  • 20.00 weight % of 2% Carbopol 940 aqueous solution was added into the resulting mixture and agitated until it became homogenous. Thereafter, it was cooled down to 40, for obtaining the skin care lotion of interest.
  • the oil phase was added to the pigment dispersion with agitation. Then, the resulting mixture was cooled down, and fragrance was added thereto when temperature thereof was 50. The resulting mixture was further cooled with agitation down to room temperature, for obtaining the cream foundation of interest.
  • Example 1 After pigment was dispersed in ion-exchanged water, the dispersion of Example 1 and other ingredients shown in the following Table 11 were added thereto in proportions shown in the same table. The resulting mixture was mixed with agitation until it became homogenous and was deaerated finally for obtaining the manicure of interest.
  • the cosmetic resin composition of the present invention consists essentially of amphoteric urethane resin having a carboxyl group and a tertiary amino group in one molecule thereof.
  • urethane resin as a main skeleton of a base resin makes it possible due to elasticity and toughness of the urethane resin that stiffness is compatible with feel, combability and anti-flaking property, which are originally contrary to each other.
  • amphoteric urethane resin having a carboxyl group and a tertiary amino group it becomes possible to prepare a hair fixative superior in waterproof against neutral water because the carboxyl group and the tertiary amino group are ion-bonded, and also superior in shampoo removability because the amphoteric urethane resin has a cationic tertiary amino group, which interacts with a negatively charged hair surface, in its molecular chain, better adhesion can be obtained compared with conventional anionic urethane resin, in addition, further improvement in gloss, tactile property, combability and anti-flaking property can be obtained by introducing polysiloxane linkage in the structure of the amphoteric urethane resin.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
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  • Manufacturing & Machinery (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne une composition à base de résine à usage cosmétique permettant de préparer un fixateur pour les cheveux, qui présente à la fois des propriétés relatives à la raideur, à la capacité d'enlèvement du shampooing, à la sensation, au brillant, à l'aptitude au peignage et une propriété d'anti-desquamation. La composition à base de résine à usage cosmétique comprend essentiellement une résine d'uréthanne amphotère possédant un groupe carboxyle et un groupe amino tertiaire dans une molécule de celui-ci, la résine d'uréthanne amphotère possédant une liaison polysiloxane dans sa structure.
PCT/US2000/009957 1998-12-22 2000-04-13 Composition de resine cosmetique WO2002009658A1 (fr)

Priority Applications (8)

Application Number Priority Date Filing Date Title
DE60022194T DE60022194T2 (de) 1998-12-22 2000-04-13 Kosmetische harzzusammensetzung
CN00811598.2A CN1222268C (zh) 2000-04-13 2000-04-13 化妆树脂组合物和使用它们的化妆品
EP00923327A EP1191921B1 (fr) 1998-12-22 2000-04-13 Composition de resine cosmetique
PCT/US2000/009957 WO2002009658A1 (fr) 2000-04-13 2000-04-13 Composition de resine cosmetique
AU2000243473A AU2000243473A1 (en) 2000-04-13 2000-04-13 Cosmetic resin composition
BR0011621-1A BR0011621A (pt) 2000-04-13 2000-04-13 Composição de resina cosmética, e cosmético
MXPA01012886A MXPA01012886A (es) 2000-04-13 2000-04-13 Composicion de resina cosmetica y cosmetico que lo usa.
US10/009,960 US6884853B1 (en) 2000-04-13 2000-04-13 Cosmetic resin composition

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2000/009957 WO2002009658A1 (fr) 2000-04-13 2000-04-13 Composition de resine cosmetique

Publications (1)

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WO2002009658A1 true WO2002009658A1 (fr) 2002-02-07

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AU (1) AU2000243473A1 (fr)
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US6646092B2 (en) 2001-06-27 2003-11-11 National Starch And Chemical Investment Holding Corporation Method for manufacturing amphoteric urethane resin and amphoteric urethane resin and resin composition obtained therewith
EP1410782A1 (fr) * 2001-06-27 2004-04-21 Shiseido Company, Ltd. Produit cosmetique
EP2105126A1 (fr) * 2008-03-26 2009-09-30 Bayer MaterialScience AG Compositions cosmétiques décoratives
EP2105120A1 (fr) * 2008-03-26 2009-09-30 Bayer MaterialScience AG Préparations cosmétiques destinées à être appliquées sur la peau
EP2105125A1 (fr) * 2008-03-26 2009-09-30 Bayer MaterialScience AG Compositions de soins de la peau
EP2105127A1 (fr) * 2008-03-26 2009-09-30 Bayer MaterialScience AG Composition de fixation des cheveux
EP2105124A1 (fr) * 2008-03-26 2009-09-30 Bayer MaterialScience AG Compositions de protection solaire
EP2356981A1 (fr) * 2009-12-18 2011-08-17 L'Oréal SA Mascara comprenant une dispersion aqueuse de polyuréthane et une cire dure

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WO2017155906A1 (fr) 2016-03-08 2017-09-14 Living Proof, Inc. Compositions cosmétiques longue durée
AU2017239039A1 (en) * 2016-03-21 2018-08-23 Commonwealth Scientific And Industrial Research Organisation Hydrophobic-hydrophilic switchable polymers for use in agriculture
US11672768B2 (en) * 2016-09-19 2023-06-13 Dow Silicones Corporation Skin contact adhesive and methods for its preparation and use
JP7244494B2 (ja) 2017-09-13 2023-03-22 リビング プルーフ インコーポレイテッド 色保護剤組成物
AU2018370210B2 (en) 2017-11-20 2024-09-26 Living Proof, Inc. Properties for achieving long-lasting cosmetic performance
AU2019257739A1 (en) * 2018-04-27 2020-11-12 Living Proof, Inc. Long lasting cosmetic compositions
CN109970940B (zh) * 2019-03-19 2021-10-22 上海工程技术大学 有机硅改性水性聚氨酯分散体和由其制备的水性指甲油

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DE19821731A1 (de) * 1998-05-14 1999-11-18 Basf Ag Kosmetisches Mittel
WO2000012588A1 (fr) * 1998-08-26 2000-03-09 Basf Aktiengesellschaft Urethan(meth)acrylates radicalement polymerisables et contenant des groupes siloxanes ainsi que polymere a base de ces acrylates

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EP0751162A1 (fr) * 1995-06-27 1997-01-02 L'oreal Utilisation dans et pour la fabrication de compositions cosmétiques ou dermatologiques de polycondensats séquencés polyuréthanes et/ou polyurées à greffons siliconés
DE19821731A1 (de) * 1998-05-14 1999-11-18 Basf Ag Kosmetisches Mittel
WO2000012588A1 (fr) * 1998-08-26 2000-03-09 Basf Aktiengesellschaft Urethan(meth)acrylates radicalement polymerisables et contenant des groupes siloxanes ainsi que polymere a base de ces acrylates

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6646092B2 (en) 2001-06-27 2003-11-11 National Starch And Chemical Investment Holding Corporation Method for manufacturing amphoteric urethane resin and amphoteric urethane resin and resin composition obtained therewith
EP1410782A1 (fr) * 2001-06-27 2004-04-21 Shiseido Company, Ltd. Produit cosmetique
EP1410782A4 (fr) * 2001-06-27 2005-11-02 Shiseido Co Ltd Produit cosmetique
WO2009118103A1 (fr) * 2008-03-26 2009-10-01 Bayer Materialscience Ag Compositions de protection solaire
KR20100127795A (ko) * 2008-03-26 2010-12-06 바이엘 머티리얼사이언스 아게 자외선 차단 조성물
EP2105125A1 (fr) * 2008-03-26 2009-09-30 Bayer MaterialScience AG Compositions de soins de la peau
EP2105127A1 (fr) * 2008-03-26 2009-09-30 Bayer MaterialScience AG Composition de fixation des cheveux
EP2105124A1 (fr) * 2008-03-26 2009-09-30 Bayer MaterialScience AG Compositions de protection solaire
WO2009118104A1 (fr) * 2008-03-26 2009-10-01 Bayer Materialscience Ag Compositions cosmétiques à appliquer sur la peau
WO2009118106A1 (fr) * 2008-03-26 2009-10-01 Bayer Materialscience Ag Compositions cosmétiques de maquillage
WO2009118107A2 (fr) * 2008-03-26 2009-10-01 Bayer Materialscience Ag Composition d'un produit de soins cutanés
WO2009118105A1 (fr) * 2008-03-26 2009-10-01 Bayer Materialscience Ag Composition pour fixateurs capillaires
EP2105126A1 (fr) * 2008-03-26 2009-09-30 Bayer MaterialScience AG Compositions cosmétiques décoratives
WO2009118107A3 (fr) * 2008-03-26 2009-12-03 Bayer Materialscience Ag Composition d'un produit de soins cutanés
EP2105120A1 (fr) * 2008-03-26 2009-09-30 Bayer MaterialScience AG Préparations cosmétiques destinées à être appliquées sur la peau
KR20100127794A (ko) * 2008-03-26 2010-12-06 바이엘 머티리얼사이언스 아게 미용 화장 조성물
KR20100135241A (ko) * 2008-03-26 2010-12-24 바이엘 머티리얼사이언스 아게 피부 관리 조성물
US10045930B2 (en) 2008-03-26 2018-08-14 Covestro Deutschland Ag Decorative cosmetic compositions
RU2491053C2 (ru) * 2008-03-26 2013-08-27 Байер Матириальсайенс Аг Декоративные косметические композиции
RU2491053C9 (ru) * 2008-03-26 2014-01-20 Байер Матириальсайенс Аг Декоративные косметические композиции
KR101685212B1 (ko) 2008-03-26 2016-12-09 코베스트로 도이칠란드 아게 자외선 차단 조성물
KR101634407B1 (ko) 2008-03-26 2016-06-28 코베스트로 도이칠란드 아게 피부 관리 조성물
KR101685211B1 (ko) 2008-03-26 2016-12-09 코베스트로 도이칠란드 아게 미용 화장 조성물
US9072686B2 (en) 2009-12-18 2015-07-07 L'oreal Mascara containing aqueous dispersion of polyurethane and a hard wax
EP2356981A1 (fr) * 2009-12-18 2011-08-17 L'Oréal SA Mascara comprenant une dispersion aqueuse de polyuréthane et une cire dure

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CN1370063A (zh) 2002-09-18
CN1222268C (zh) 2005-10-12
AU2000243473A1 (en) 2002-02-13
MXPA01012886A (es) 2002-07-31

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