WO2002005621A1 - Composition de resine cosmetique et produit cosmetique comprenant cette composition - Google Patents

Composition de resine cosmetique et produit cosmetique comprenant cette composition Download PDF

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Publication number
WO2002005621A1
WO2002005621A1 PCT/US2000/009956 US0009956W WO0205621A1 WO 2002005621 A1 WO2002005621 A1 WO 2002005621A1 US 0009956 W US0009956 W US 0009956W WO 0205621 A1 WO0205621 A1 WO 0205621A1
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WO
WIPO (PCT)
Prior art keywords
cosmetic
urethane resin
resin composition
amphoteric urethane
hair fixative
Prior art date
Application number
PCT/US2000/009956
Other languages
English (en)
Other versions
WO2002005621A8 (fr
Inventor
Seiji Asaoka
Takahiro Sakurai
Katsuya Koyama
Toshitaka Tsuzuki
Tomohiro Hashimoto
Original Assignee
National Starch And Chemical Investment 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 Investment Holding Corporation filed Critical National Starch And Chemical Investment Holding Corporation
Priority to US10/009,958 priority Critical patent/US6692729B1/en
Priority to AU2000243472A priority patent/AU2000243472A1/en
Priority to PCT/US2000/009956 priority patent/WO2002005621A1/fr
Priority to EP00923326A priority patent/EP1189573A1/fr
Priority to CNB008117675A priority patent/CN1183177C/zh
Priority to BR0011620-3A priority patent/BR0011620A/pt
Priority to MXPA01012885A priority patent/MXPA01012885A/es
Publication of WO2002005621A1 publication Critical patent/WO2002005621A1/fr
Publication of WO2002005621A8 publication Critical patent/WO2002005621A8/fr

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Classifications

    • 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
    • C08G18/6625—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/34
    • 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
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • 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
    • C08G18/0833—Manufacture of polymers containing ionic or ionogenic groups containing cationic or cationogenic groups together with anionic or anionogenic groups
    • 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
    • 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
    • A61Q3/00—Manicure or pedicure preparations
    • 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
    • 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, on the other hand, when 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 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.
  • the anionic urethane resin is used, a problem of inferior shampoo removability may be caused.
  • a cosmetic resin composition for preparation of a hair fixative having all the properties of stiffness, shampoo removability, feel, gloss, combability and anti-flaking property and to provide a cosmetic using such a cosmetic resin composition.
  • 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
  • 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
  • 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.
  • amphoteric urethane resin is used as a base resin
  • shampoo removability can be improved compared with the case where the conventional anionic urethane resin is used.
  • compositional restrictions to some degree, such as adjustment of molecular weight of the amphoteric urethane resin, choice of urethane skeleton or the like, which may be a defect of low degree of freedom in designing physical properties, such as hardness, flexibility or the like, important for polymer to be used for a hair fixative.
  • 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 a structural unit derived from an ethylene oxide in its structure, in addition, 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 a structural unit derived from an ethylene oxide may be obtained, for example, by reacting a polyol compound [component (A)l, a polyisocyanate compound icomponent (B)l, a polyethylene oxide derivative [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.
  • a polyol compound [component (A)l, a polyisocyanate compound icomponent (B)l, a polyethylene oxide derivative [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 prep
  • amphoteric urethane resin having a structural unit derived from an ethylene oxide may be obtained by changing the reaction order of the component (D) for 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 method, 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 (D) and a tertiary amino 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 a structural unit derived from an ethylene oxide 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, 1,3-butanediol, 1,6-hexanediol, neopentyl glycol, ,8-octanediol, 1,10-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 A
  • 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 polymerizing lactones.
  • examples of polyether polyol may be obtained by ring-opening addition polymerizing cyclic ethers such as ethylene oxide, propylene oxide oxetane and tetrahydrofuran into water, polyhydric alcohols for synthesizing the polyester polyol, phenols such as bisphenol A, hydrogenated phenols, primary amines and secondary amines.
  • 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.
  • aromatic diisocyanate compounds examples include diphenyl methane- 4,4'-diisocyanate, xylylene 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 polyethylene oxide derivative of the component (C) is not specifically limited, but any of compound wherein a structural unit derived from an ethylene oxide (abbreviated to "EO”, hereinafter) can be introduced into the structure of the amphoteric urethane resin, may be used.
  • the structural unit derived from the EO introduced into the structure of the amphoteric urethane resin includes an EO unit represented by the following general formula (1) and a propylene oxide (abbreviated to "PO”, hereinafter) unit represented by the following general formula (2), among which the EO unit is preferred.
  • the amphoteric urethane resin may have both of the EO unit and the PO unit.
  • the number 'n' is less than 3, the amount of the EO unit introduced into the amphoteric urethane resin is too small, so that sufficient hydrophilic property cannot be imparted, thereby sufficient shampoo removability may not be obtained, on the other hand, when the number 'n' exceeds 300, the hydrophilic property of the amphoteric urethane resin itself becomes too strong so as to have bad effects on moisture resistance and the like.
  • the polyethylene oxide derivative [component (Ol include polyoxyethylene glycol (PEG) and polyoxyethylene polyoxypropylene glycol (EOPO blocked copolymer), among which polyoxyethylene glycol is preferred.
  • the above polyethylene oxide derivative [component may be either of a type having OH groups at both terminals, a type having NH 2 groups at both terminals, a type having an OH group at one terminal and a type having an NH 2 at one terminal.
  • the amphoteric urethane resin having the EO unit as a main chain can be obtained.
  • the amphoteric urethane resin having the EO unit as a side chain or at a terminal can be obtained.
  • component o has preferaby a molecular weight of 200 to 20,000, more preferably 2,000 to 10, ooo.
  • the compound [component (D)i 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 (E)i 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-alkyldialkanolamine compound such as N-methyldiethanol- amine, and dimethylaminoethanol.
  • a 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 and amines.
  • solvents may be used, as required. For example, it is especially preferred to use 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.
  • amides such as N- methyl pyrrolidone, dimethylformamide and dimethylacetamide
  • ketones such as acetone and methyl ethyl ketone
  • esters such as ethyl acetate as well as cellosolve acetate and cellosolve ether
  • Examples include tertiary amine catalyst and organometallic catalyst, AS the tertiary amine catalyst, 12,2,21 diazabicyclo octane (DABCO), tetramethylene diamine, N-methylmorpholine, d ⁇ azbicyclo undecene (DBU) may be used.
  • 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, eve 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, eve liner and manicure
  • a film forming agent such as skin care lotion, foundation, eve 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 I ⁇ IH 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 additives such as a protective colloid agent, an antibacterial agent and an antifungal agent may be added to give preservation stability.
  • IPDI isophorone diisocyanate
  • DEGA diethylene glycol adipate
  • DEGA diethylene glycol adipate
  • Newpol BP3P an adduct of bisphenol A with ethylene oxide
  • 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
  • PEG polyoxyethylene glycol
  • n 50
  • DMPA dimethylol propionic acid
  • DBTDL dibutyltindilaurate
  • N-methyldiethanolamine N-methyldiethanolamine
  • ethyl acetate 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 was cooled down to 50, 600 g of water containing 12.7 g of triethylamine and 3.3 g of diethanolamine was added thereto under high-speed agitation to be dispersed, and then polymerized by chain-lengthening reaction at 50 for 3 hours. The ethyl acetate was withdrawn from thus obtained dispersion and an amphoteric urethane resin dispersion substantially not including solvent and having an ethylene oxide chain in its structure was obtained.
  • NMDEtA N-methyldiethanolamine
  • ethyl acetate 60 g of ethyl acetate was added thereto and allowed to react at 80 for 2 hours, for obtaining polyurethane prepolymer solution wherein NCO groups remain
  • IPDI isophorone diisocyanate
  • DEGA diethylene glycol adipate
  • DMPA dimethylol propionic acid
  • ethyl acetate as a solvent and 0.02 g of dibutyltindilaurate (DBTDL) 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 l ⁇ l- 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.
  • DBTDL dibutyltindilaurate
  • IPDI isophorone diisocyanate
  • DEGA diethylene glycol adipate
  • DEGA diethylene glycol adipate
  • DEGA diethylene glycol adipate
  • PEG polyoxyethylene glycol
  • ethyl acetate as a solvent and 0.02 g of dibutyltindilaurate (DBTDL) 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.
  • DBTDL dibutyltindilaurate
  • IPDI isophorone diisocyanate
  • DEGA diethylene glycol adipate
  • DEGA diethylene glycol adipate
  • DMPA dimethylol propionic acid
  • ethyl acetate as a solvent and 0.02 g of dibutuyltindilaurate (DBTDL) 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.
  • DBTDL dibutuyltindilaurate
  • IPDI isophorone diisocyanate
  • DEGA diethylene glycol adipate
  • DEGA diethylene glycol adipate
  • DMPA dimethylol propionic acid
  • ethyl acetate as a solvent and 0.02 g of dibutyltindilaurate (DBTDL) 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.
  • DBTDL dibutyltindilaurate
  • IPDI isophorone diisocyanate
  • DEGA diethylene glycol adipate
  • DEGA diethylene glycol adipate
  • DMPA dimethylol propionic acid
  • ethyl acetate as a solvent and 0.02 g of dibutyltindilaurate (DBTDL) 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.
  • DBTDL dibutyltindilaurate
  • IPDI isophorone diisocyanate
  • DEGA diethylene glycol adipate
  • DEGA diethylene glycol adipate
  • DMPA dimethylol propionic acid
  • IPDI isophorone diisocyanate
  • DEGA diethylene glycol adipate
  • 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.
  • Curl retention (%) ⁇ (L - b) / (L - a) ⁇ x 100
  • 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.
  • 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, combability and anti-flaking property. Also, it is found that mousse hair fixatives a to f are especially excellent in shampoo removability and feel because they use an amphoteric urethane resin having the EO unit in its structure. On the other hand, it is found that a mousse hair fixative g is superior to a mousse hair fixative h, which uses an anionic urethane resin, in shampoo removability, stiffness and combability, because the mousse hair fixative g uses the amphoteric urethane resin.
  • the hair fixative g is inferior to hair fixatives a to f, having the EO unit in the structure of the amphoteric urethane resin
  • a mousse hair fixative h is remarkably inferior in combability because the mousse hair fixative h uses an anionic urethane resin, and is also inferior in other properties except for feel.
  • a mousse hair fixative I contains the urethane resin which, though having the EO unit in the structure thereof, is not amphoteric but anionic. Therefore, it is found that the mousse hair fixative I is inferior in shampoo removability, feel, combability and anti-flaking property to mousse hair fixatives a to f containing the amphoteric urethane resin having the EO unit in the structure thereof.
  • 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.
  • gel hair fixatives a to i were determined in accordance with the above mentioned standards therefor. The generally same results were obtained as in the case where the mousse hair fixatives a to i were used. in addition, spray hair fixatives a to i were prepared using the dispersions of Examples and comparative Examples at mixing ratios as follows.
  • Spray Hair Fixative a ingredients shown in the following Table 4 were blended in proportions shown in the same table and mixed until it became homogeneous, for obtaining X component. Next, ingredients shown in the Table 4 were blended in proportions shown in the same table, for obtaining Y component. Thus obtained Y component was added into the X component, for obtaining a spray 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 ion-bond is cut by shampoo.
  • amphoteric urethane resin since 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, the amphoteric urethane resin, even though having a high molecular weight or a low glass transition temperature, further improves shampoo removability because it has a structural unit derived from an ethylene oxide therein as a nonionic hydrophilic component, and makes it possible to widely control hardness and elasticity of the base resin which contribute to feel or stiffness required for a hair fixative.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Polymers & Plastics (AREA)
  • Public Health (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne un procédé permettant d'obtenir une composition de résine cosmétique pour la préparation d'un produit fixant pour les cheveux, présentant toutes les propriétés de raideur, de facilité d'enlèvement, de facilité à peigner et des propriétés anti-desquamation. L'invention concerne une composition de résine cosmétique consistant essentiellement en une résine uréthanne amphotère présentant un groupe carboxylique et un groupe amino tertiaire dans une molécule de celle-ci. La résine uréthanne amphotère comprend une unité structurale provenant d'un oxyde d'éthylène dans sa structure.
PCT/US2000/009956 2000-04-13 2000-04-13 Composition de resine cosmetique et produit cosmetique comprenant cette composition WO2002005621A1 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
US10/009,958 US6692729B1 (en) 2000-04-13 2000-04-13 Cosmetic resin composition and cosmetic using the same
AU2000243472A AU2000243472A1 (en) 2000-04-13 2000-04-13 Cosmetic resin composition and cosmetic using the same
PCT/US2000/009956 WO2002005621A1 (fr) 2000-04-13 2000-04-13 Composition de resine cosmetique et produit cosmetique comprenant cette composition
EP00923326A EP1189573A1 (fr) 2000-04-13 2000-04-13 Composition de resine cosmetique et produit cosmetique comprenant cette composition
CNB008117675A CN1183177C (zh) 2000-04-13 2000-04-13 化妆树脂组合物和使用它们的化妆品
BR0011620-3A BR0011620A (pt) 2000-04-13 2000-04-13 Composição de resina cosmética para a preparação de um cosmético
MXPA01012885A MXPA01012885A (es) 2000-04-13 2000-04-13 Composicion de resina cosmetica y cosmetico que la usa.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2000/009956 WO2002005621A1 (fr) 2000-04-13 2000-04-13 Composition de resine cosmetique et produit cosmetique comprenant cette composition

Publications (2)

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WO2002005621A1 true WO2002005621A1 (fr) 2002-01-24
WO2002005621A8 WO2002005621A8 (fr) 2002-02-14

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CN (1) CN1183177C (fr)
AU (1) AU2000243472A1 (fr)
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WO (1) WO2002005621A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4450427B2 (ja) * 2007-11-13 2010-04-14 株式会社資生堂 皮膚化粧料
AU2017229125B2 (en) * 2016-03-08 2021-07-29 Living Proof, Inc. Long lasting cosmetic compositions
BR112020004215A2 (pt) 2017-09-13 2020-09-01 Living Proof, Inc. composições cosméticas de longa duração
US10842729B2 (en) 2017-09-13 2020-11-24 Living Proof, Inc. Color protectant compositions

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0268806A2 (fr) * 1986-11-28 1988-06-01 Akzo N.V. Polyuréthanes anioniques
JPH06321741A (ja) * 1993-04-06 1994-11-22 Natl Starch & Chem Investment Holding Corp 水性毛髪固定剤
US5626840A (en) * 1993-04-06 1997-05-06 National Starch And Chemical Investment Holding Corporation Use of polyurethanes with carboxylate functionality for hair fixative applications
US5759666A (en) * 1995-12-21 1998-06-02 Minnesota Mining And Manufacturing Company Carboxylic acid functional polyurethane polymers and blends thereof used in magnetic recording media

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4165669B2 (ja) * 1998-02-09 2008-10-15 日本エヌエスシー株式会社 化粧品用樹脂組成物およびその製法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0268806A2 (fr) * 1986-11-28 1988-06-01 Akzo N.V. Polyuréthanes anioniques
JPH06321741A (ja) * 1993-04-06 1994-11-22 Natl Starch & Chem Investment Holding Corp 水性毛髪固定剤
US5626840A (en) * 1993-04-06 1997-05-06 National Starch And Chemical Investment Holding Corporation Use of polyurethanes with carboxylate functionality for hair fixative applications
US5759666A (en) * 1995-12-21 1998-06-02 Minnesota Mining And Manufacturing Company Carboxylic acid functional polyurethane polymers and blends thereof used in magnetic recording media

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP1189573A1 *

Also Published As

Publication number Publication date
WO2002005621A8 (fr) 2002-02-14
EP1189573A1 (fr) 2002-03-27
AU2000243472A1 (en) 2002-01-30
MXPA01012885A (es) 2002-07-31
CN1370185A (zh) 2002-09-18
CN1183177C (zh) 2005-01-05

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