WO2011071029A1 - Composition de résine durcissable pour recouvrir un ongle ou un ongle artificiel - Google Patents

Composition de résine durcissable pour recouvrir un ongle ou un ongle artificiel Download PDF

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Publication number
WO2011071029A1
WO2011071029A1 PCT/JP2010/071862 JP2010071862W WO2011071029A1 WO 2011071029 A1 WO2011071029 A1 WO 2011071029A1 JP 2010071862 W JP2010071862 W JP 2010071862W WO 2011071029 A1 WO2011071029 A1 WO 2011071029A1
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WIPO (PCT)
Prior art keywords
nail
resin composition
curable resin
irradiation
mass
Prior art date
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PCT/JP2010/071862
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English (en)
Japanese (ja)
Inventor
一宏 小島
ハ，ホイ－グェン
ルロワ アントニー
Original Assignee
株式会社スリーボンド
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Filing date
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Application filed by 株式会社スリーボンド filed Critical 株式会社スリーボンド
Priority to US13/514,818 priority Critical patent/US8846011B2/en
Priority to CN201080055682.6A priority patent/CN102770119B/zh
Priority to EP10835949.8A priority patent/EP2510920A4/fr
Publication of WO2011071029A1 publication Critical patent/WO2011071029A1/fr

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Classifications

    • 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
    • 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
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/55—Phosphorus compounds
    • 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
    • A61K8/86—Polyethers
    • 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
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/81—Preparation or application process involves irradiation

Definitions

  • the present invention relates to a curable resin composition for covering a nail or an artificial nail, and more specifically, a curable resin composition for covering a nail or an artificial nail that covers and decorates and / or protects the nail or an artificial nail. It is about things.
  • keratin coating materials are applied to keratin such as nails, and then the organic solvent is volatilized to give a film having excellent gloss in a short time.
  • the film formed on the nail can be easily wiped off using an organic solvent such as acetone.
  • this type of keratin coating material essentially contains an organic solvent. Accordingly, there is a problem that the user directly sucks the organic solvent that volatilizes during use. Further, the formed film cannot be easily removed with water, and it is necessary to wipe it off by immersing it in a large amount of an organic solvent, and the organic solvent has a strong odor and is harmful to the health of the user. Further, the organic solvent may cause a decrease in the physiological functions of the nails and skin. In addition, many organic solvents are flammable and are very dangerous for use in ordinary households.
  • a composition containing a non-reactive polymer material and a composition containing a reactive curable resin are known.
  • a composition containing a non-reactive polymer material forms a polymer film by volatilization of a solvent or a diluent contained in the composition. Since the formation of the film does not involve a chemical reaction, the composition has excellent properties such as good stability during storage and low physiological irritation. However, since the formed film is not cross-linked by a chemical reaction, it cannot be a tough film, and the film formed on the stratum corneum easily peels off by stimulation such as abrasion. It was.
  • a composition containing a reactive curable resin produces a crosslinked polymer film by a chemical reaction, so that a tough film can be formed.
  • the reaction in order to cause a chemical reaction within a range that has little influence on the human body, the reaction must be caused under relatively mild conditions. Therefore, the prepared composition has a problem in storability because the reaction may gradually proceed in a storage environment.
  • the physiological stimulus is greater than that of the non-reactive composition.
  • Patent Document 1 discloses a photocrosslinkable nail polish composition containing a polymer containing an ethylene-based double bond and a predetermined amount of a free radical photoinitiator in a physiologically acceptable medium.
  • a polymer containing an ethylenic double bond an ethylenically unsaturated polyester, a polyester containing a (meth) acrylate side group and / or a terminal group, a polyurethane and / or a polyurea containing a (meth) acrylate group
  • Poly (C 1-50 alkyl (meth) acrylate) containing at least two functional groups containing an ethylene-based double bond with a polyether-based, epoxy acrylate, hydrocarbon-based side and / or end having a meth) acrylate group
  • the photocrosslinkable nail polish composition includes auxiliary agents and additives commonly used in nail polish, such as pigments and colorants, plasticizers, coalescent agents, preservatives, waxes, thickening agents. It is described that further agents, fragrances, UV screening agents, nail care cosmetic actives, diffusing agents, antifoaming agents and dispersing agents can be added.
  • the invention does not use low molecular weight molecules with high reactivity, but by using reactive components with sufficiently large molecular weight to prevent diffusion to adjacent biological substrates, It is intended to solve the toxicity problem of cosmetic compositions. However, the solution to the toxicity problem is still not sufficient, and the appearance after curing cannot be said to be good.
  • Patent Document 2 discloses a photocurable solventless nail polish containing a polymerizable unsaturated group-containing compound and a photopolymerization initiator.
  • the polymerizable unsaturated group-containing compound is a monomer or oligomer having a polymerizable unsaturated group, for example, polyethylene glycol diacrylate, ethoxydiethylene glycol acrylate, phenoxyethyl acrylate, phenoxy polyethylene glycol acrylate, or the like. Substances are listed.
  • the photocurable solventless nail polish includes a photopolymerization initiation aid, a colorant, a pearl brightener, a matting agent, a fragrance, an ultraviolet absorber, a wetting agent, an antifoaming agent, and a coupling. It is described that agents, thixotropic agents and the like can be added.
  • the object of the present invention is to provide a solventless nail polish.
  • the polymerizable unsaturated group-containing compound, the photopolymerization initiator and other additives are directly applied to the human body without diluting, so that there are not a few adverse effects on the human body.
  • the viscosity of the nail polish itself is high, and there is also a problem that it is not easy to uniformly apply to the nails.
  • Patent Document 3 discloses a nail nail polish obtained by mixing a photocurable resin and a coating film release agent in an organic solvent system for nail polish.
  • ⁇ -hydroxycyclohexyl phenyl ketone is used as the photocurable resin
  • polyester urethane acrylate is used as the coating film release agent.
  • triethylene glycol dimethacrylate, polyether-modified silicone oil, epoxy methacrylate, and epoxy acrylate are further used.
  • the invention has an effect that it is quick-drying and can be peeled off without damaging the surface of the nail. However, since it is a non-aqueous system, the safety to the human body is still insufficient, and sufficient caution was required for handling.
  • Patent Document 4 discloses an aqueous resin emulsion in which an aqueous pigment dispersion containing, as a dispersant, an addition polymer of an ethylenically unsaturated molecule containing a surfactant and / or an ⁇ , ⁇ -monoethylenically unsaturated acid.
  • a nail polish and a method for producing the same are disclosed.
  • the aqueous resin emulsion for example, a monomer selected from the group consisting of ⁇ , ⁇ -ethylenically unsaturated carboxylic acid, methacrylic acid ester, acrylic acid ester and styrene is polymerized with a reactive surfactant.
  • Patent Document 5 is obtained by polymerizing a monomer selected from the group consisting of ⁇ , ⁇ -ethylenically unsaturated carboxylic acid, methacrylic acid ester, acrylic acid ester and styrene and a reactive surfactant.
  • An aqueous nail polish containing a resin is disclosed. These nail polishes include pH adjusters, pigments, dyes, dispersion aids, drugs, UV absorbers, bactericides, preservatives, fragrances, plasticizers such as glycol-based film forming agents, film smoothing agents and thickeners. It is described that it can contain a sticky agent and the like.
  • these nail polishes are aqueous, there are no problems such as health problems and nail deterioration. In addition, it not only gives a coating film excellent in adhesion to the nails, and gloss and color tone, but also the obtained coating film is excellent in water resistance.
  • the aqueous nail polish agent contains a non-reactive polymer material as described above, the adhesion of the film to the nail is not sufficient, and the problem is that it easily peels off by stimulation such as friction. was there.
  • Patent Document 6 discloses a water-based beauty nail material containing two or more acrylic polymer emulsions having a glass transition temperature difference of 10 ° C. or more.
  • the water-based beauty nail material may contain a film forming aid, a plasticizer, a pigment, a dye, a preservative, a fragrance, a thickener, and the like.
  • film forming aids and plasticizers include numerous substances such as ethylene glycol, propylene glycol, pentaerythritol, glycerin, liquid paraffin, chlorinated paraffin, and machine oil.
  • the water-based nail polish uses two or more types of acrylic polymer emulsion as compared with an aqueous nail polish using a simple acrylic polymer emulsion, with respect to gloss, adhesion and coating strength, Some improvement has been made. However, the durability such as adhesion, scratch resistance, and toughness of the film has not yet been sufficient.
  • Patent Document 7 discloses an aqueous nail polish characterized by containing an aqueous emulsion containing a self-emulsifiable vinyl polymer and a cellulose derivative.
  • the aqueous nail polish can contain plasticizers, film forming aids, pigments, thickeners, dyes, preservatives, and fragrances.
  • the aqueous nail polish is excellent in adhesion, friction resistance, water resistance and the like, and has good gloss and durability. However, its water resistance is not sufficient, and there is a drawback that it easily peels off during use in daily life, and it cannot be said that it can withstand practical use.
  • the present invention is not only excellent in appearance after application, but also excellent in water resistance and scratch resistance, and has little odor, damage to nails, skin irritation, etc., and therefore has high safety to the human body.
  • the present invention provides a curable resin composition for covering a nail or an artificial nail having excellent storage stability.
  • non-reactive polymers it has been found that there is a limit to improving the adhesion.
  • a water system use of an organic solvent can be avoided, the influence on the human body of inclusions, such as a polymer to be used, can be eased, and a safer composition can be manufactured.
  • the material used is a reactive material, that is, a material that hardens on the nail, sufficient adhesion of the obtained coating film to the nail can be ensured.
  • a material that cures on the nails even a water-based composition cannot ensure sufficient safety for the human body.
  • Patent Document 1 the use of a low-molecular-weight reactive monomer is excluded in order to ensure safety to the human body.
  • this alone could not ensure sufficient safety for the human body. Therefore, the present inventors have further studied how the safety to the human body can be further improved while ensuring sufficient adhesion to the nail of the obtained film. .
  • the component (B) polyethylene glycol is added to the following predetermined components (A) and (C), not only viscosity adjustment but also penetration into the resin network based on the component (A) during the formation of the cured film. Then, it is found that the unreacted functional group of the component (A) remaining slightly after curing is included to prevent the unreacted functional group from reacting with the nail, and in addition, as the component (C), the molecule It has been found that if a material containing no nitrogen atom is used, there is almost no odor and no coloring when applied to nails or artificial nails, and further no discoloration or the like with the passage of time occurs.
  • the present inventors have found that the physiological stimulation of the curable resin composition for covering a nail or an artificial nail can be reduced and that all the above problems can be solved, and the present invention has been completed. Further, it is described in the prior art that various additives can be included as described above.
  • the curable resin composition for covering an aqueous nail or artificial nail when a material that causes a curing reaction on the human body, such as a nail, is used, and if polyethylene glycol is further included, the human body that is a feature of the aqueous composition While maintaining the safety to the body and maintaining the excellent adhesion to the nail, etc., which is a feature of the reactive material, it relaxes the strong physiological irritation, which is a defect of the reactive material, and is safe for the human body It is not known at all in the prior art that not only the property can be ensured but also the appearance after coating can be improved to a very good one.
  • the present invention (1) (A) An aqueous emulsion of a polymer containing a functional group capable of undergoing a polymerization reaction upon irradiation with active energy rays, (B) polyethylene glycol, and (C) a photoradical initiator (however, those containing a nitrogen atom in the molecule) A curable resin composition for covering nails or artificial nails.
  • (2) The nail or artificial nail coating curable resin composition according to the above (1), wherein the functional group capable of undergoing a polymerization reaction upon irradiation with active energy rays is a (meth) acryloyl group
  • (3) The nail or artificial nail coating according to (1) or (2) above, wherein the polymer containing a functional group capable of undergoing a polymerization reaction upon irradiation with active energy rays has a polyacrylic skeleton or a polyurethane skeleton as the main chain structure Curable resin composition
  • (4) The nail or the curable resin for covering an artificial nail according to the above (1) or (2), wherein the polymer containing a functional group capable of undergoing a polymerization reaction upon irradiation with active energy rays has a polyacrylic skeleton as a main chain structure Composition
  • (5) Any one of (1) to (4) above, wherein the aqueous emulsion (A) contains a polymer containing a functional group capable of
  • a curable resin composition for covering a nail or an artificial nail as described in (6) The number average molecular weight of the polymer containing a functional group capable of undergoing a polymerization reaction upon irradiation with active energy rays is 10,000 to 500,000, according to any one of (1) to (5) above Curable resin composition for covering nail or artificial nail, (7) The nail according to any one of (1) to (6) above, wherein the polymer containing a functional group capable of undergoing a polymerization reaction by irradiation with active energy rays contains at least two of the functional groups in the molecule.
  • Curable resin composition for artificial nail coating (8) 0.1 to 30 parts by mass of (B) polyethylene glycol with respect to 100 parts by mass of the polymer containing a functional group capable of undergoing a polymerization reaction by irradiation with active energy rays, contained in the aqueous emulsion (A).
  • a nail or artificial nail coating curable resin composition according to any one of the above (1) to (7), (9) (B) 2 to 20 parts by mass of polyethylene glycol is contained in 100 parts by mass of the polymer containing a functional group capable of undergoing a polymerization reaction by irradiation with active energy rays, contained in the aqueous emulsion (A).
  • the curable resin composition for covering a nail or an artificial nail according to any one of the above (1) to (7), (10) (B) 3 to 15 parts by mass of polyethylene glycol is contained in 100 parts by mass of the polymer containing a functional group capable of undergoing a polymerization reaction by irradiation with active energy rays, contained in the aqueous emulsion (A).
  • the curable resin composition for covering a nail or an artificial nail according to any one of the above (1) to (7), (11) The nail or artificial nail coating curable resin composition according to any one of the above (1) to (10), wherein the weight average molecular weight of polyethylene glycol (B) is 1,000 to 2,000.
  • (C) 1 to 10 parts by mass of (C) the photo radical initiator is contained in the aqueous emulsion (A) and contains 100 parts by mass of a polymer containing a functional group capable of undergoing a polymerization reaction by irradiation with active energy rays.
  • a nail or artificial nail coating curable resin composition according to any one of the above (1) to (11), (13) Any of (1) to (12) above, wherein the (C) photoradical initiator is ethyl 2,4,6-trimethylbenzoylphenylphosphinate, 1-benzoyl-1-cyclohexanol, or a mixture thereof.
  • a curable resin composition for covering a nail or an artificial nail according to any one of the above, (14)
  • (D) A wax derived from a natural product is contained in the aqueous emulsion (A) in an amount of 0.1 to 100 parts by mass with respect to 100 parts by mass of a polymer containing a functional group capable of undergoing a polymerization reaction by active energy ray irradiation.
  • the natural product-derived wax is one or more selected from the group consisting of carnauba wax, beeswax, palm wax, lacquer wax and ibota wax.
  • claw description of description can be mentioned.
  • the curable resin composition for covering a nail or artificial nail of the present invention is excellent in appearance after coating, and is excellent in water resistance and scratch resistance, so that the coating may peel off for a long time after coating. Absent. Therefore, the coating applied to the nail or the like is always beautiful and useful for protecting and reinforcing the nail. In addition, there is little odor, damage to nails, skin irritation, etc., and safety to the human body is high. Accordingly, it is not necessary to describe danger labels and risk phrases based on GHS ("Globally Harmonized System of Classification and Labeling of Chemicals"). In addition, it has excellent storage stability.
  • GHS Globally Harmonized System of Classification and Labeling of Chemicals
  • the functional group capable of undergoing a polymerization reaction by irradiation with active energy rays in the polymer contained in the aqueous emulsion of component (A) is not particularly limited as long as it can be polymerized by a photoradical reaction.
  • the functional group containing various ethylene type double bonds as described in said patent document 1 can be mentioned.
  • a (meth) acryloyl group is mentioned. Two or more of these groups are preferably contained in one molecule of the polymer.
  • the upper limit of the number of the groups is not particularly limited, but is preferably 5 or less. Thereby, the polymer fully bridge
  • polymer itself containing the functional group as a skeleton.
  • various polymers as described in Patent Document 1 such as polyester, polyurethane, polyurea, polyether, polyorganosiloxane, perfluoropolyether and the like can be mentioned.
  • (meth) acrylic resin is mentioned.
  • a polymer having a polyacrylic skeleton or a polyurethane skeleton as the main chain structure is preferable.
  • a polymer having a polyacrylic skeleton as the main chain structure is particularly preferred because damage due to permeability to nails is small and a cured product having a uniform hardness can be obtained.
  • the polymer containing a functional group capable of undergoing a polymerization reaction upon irradiation with active energy rays contained in the aqueous emulsion of component (A) is one in which the above various functional groups are bonded to the various polymers as the skeleton. Is included.
  • polyesters containing (meth) acrylate side groups and / or end groups polyurethanes and / or polyureas containing (meth) acrylate groups, hydroxyls of C 1-4 alkylene glycol homopolymers or copolymers
  • Poly (C 1-50 alkyl (meth) acrylate) containing functional group, polyorganosiloxane containing (meth) acrylate or (meth) acrylamide group, perfluoropolyether containing acrylate group, and (meth) acrylate or (meth) Has acrylamide May be mentioned that dendrimers and hyperbranched polymers.
  • a polymer having a polymethacrylic skeleton as the main chain structure is particularly preferred as the polymer having a (meth) acryloyl group as a functional group capable of undergoing a polymerization reaction upon irradiation with active energy rays.
  • the upper limit of the number average molecular weight of the polymer containing a functional group capable of undergoing a polymerization reaction by irradiation with active energy rays is preferably 500,000, more preferably 300,000, and the lower limit is preferably 10,000. More preferably, it is 50,000. If the above upper limit is exceeded, the viscosity becomes too high, so that the stability as an emulsion is lowered, and there is also a problem in workability during coating. On the other hand, if it is less than the above lower limit, the coating film after cross-linking and curing cannot be sufficiently grown, and since it does not become a flexible coating film, followability with respect to nails and artificial nails cannot be obtained sufficiently, so that the coating film is difficult to peel off. Further, the toxicity due to the polymer is increased, and even when component (B) polyethylene glycol is added, sufficient safety to the human body may not be ensured.
  • a preferred embodiment of the present invention is a polymer having a (meth) acryloyl group as a functional group capable of undergoing a polymerization reaction upon irradiation with active energy rays and having a polyacrylic skeleton as a main chain structure. It can manufacture by the well-known method of, for example, the following method.
  • a polymer having a polyacrylic skeleton as the main chain structure can be obtained, for example, by copolymerizing a (meth) acrylic monomer or oligomer and, if necessary, a small amount of other monomers.
  • the polymer having a polyacrylic skeleton as the main chain structure thus obtained preferably has a reactive group such as a hydroxyl group, an isocyanate group, an amino group, or a carboxyl group at the terminal or side chain of the polymer.
  • a (meth) acryloyl group is introduced into the polymer.
  • the polymer has a hydroxyl group
  • (meth) acryloyl bonded by a urethane bond by reacting an acrylic group-containing compound having an isocyanate group such as 2- (methacryloyloxy) ethyl isocyanate.
  • Groups can be introduced.
  • the polymer has an amino group, for example, by reacting an acryl group-containing compound having a carboxy group, and when the polymer has an isocyanate group, for example, a hydroxyl group or an amide group is added.
  • a (meth) acryloyl group can be introduced by reacting the acrylic group-containing compound.
  • a (meth) acryloyl group can also be directly introduced into the terminal or side chain of a polymer having a polyacrylic skeleton as the main chain structure by living radical polymerization or the like.
  • (meth) acrylic monomer for example, ethyl acrylate, ethyl methacrylate, methyl acrylate, methyl methacrylate, acrylic acid, methacrylic acid, n-butyl acrylate, n-butyl methacrylate, isopropyl acrylate
  • (Meth) acrylic acid alkyl esters such as isopropyl methacrylate, isobutyl acrylate, isobutyl methacrylate, 2-ethylhexyl methacrylate; hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, acrylic acid Hydroxyl group-containing acrylates such as hydroxybutyl and hydroxybutyl methacrylate; 2- (1-hydroxyethyl) acrylonitrile, (meth) acrylamide, N-methyl (meth) ) (Meth) acrylamide derivatives such as
  • ethyl acrylate methyl methacrylate, acrylic acid, methacrylic acid, n-butyl acrylate, 2-ethylhexyl methacrylate, n-butyl methacrylate, hydroxyethyl acrylate and hydroxyethyl methacrylate are preferred.
  • Examples of other copolymerizable monomers include styrene, ⁇ -methylstyrene, vinyl acetate, vinyl propionate, vinyl chloride, vinylidene chloride, (meth) acrylonitrile, vinyl fluoride, vinylidene fluoride, and the like.
  • the polymer containing a functional group capable of undergoing a polymerization reaction by irradiation with active energy rays obtained as described above is preferably subjected to an alkali treatment for emulsification.
  • the alkali treatment is carried out so that the pH of the aqueous emulsion of component (A) is preferably 6.5 to 9.5, more preferably 7.0 to 8.0. If the pH is less than the above lower limit, the dispersibility of the aqueous emulsion becomes insufficient. On the other hand, if the pH exceeds the upper limit, a hydrolysis reaction may occur over time, and the polymer molecules may be cleaved. .
  • the alkali treatment can further improve the safety and storage stability for the human body.
  • a substance capable of reacting with a carboxyl group or an ester thereof is preferably used.
  • ammonia, ethylamine, trimethylamine, triethylamine, triisopropylamine, tributylamine, triethanolamine, N-methyldiethanolamine, N-phenyldiethanolamine, monoethanolamine, dimethylethanolamine, diethylethanolamine, morpholine, N-methylmorpholine examples thereof include organic amines such as 2-amino-2-ethyl-1-propanol, alkali metals such as lithium, potassium and sodium, and inorganic alkalis such as sodium hydroxide and potassium hydroxide.
  • alkali metals and inorganic alkalis are preferable from the viewpoint of safety to the human body.
  • these substances can be used individually or in mixture of 2 or more types.
  • a crosslinkable group-containing monomer can be further copolymerized with the polymer in the aqueous emulsion of component (A).
  • the crosslinkable group-containing monomer can not only self-crosslink when the composition of the present invention is applied to the nail or artificial nail, but also the nail or artificial nail and the surface of the decorated or painted nail or artificial nail It can be cross-linked with the hydroxyl group present in As a result, even when a decorative component that is hard to be cured and a pigment or dye that is difficult to transmit light is used, the internal crosslinking can be surely progressed, and an accident during use, in particular, the penetration of the composition into the skin is minimized. Can be suppressed. Therefore, the safety for the human body can be further enhanced.
  • the lowest temperature [MFFT (min. Film forming temp.)] At which the crosslinkable group-containing monomer can self-crosslink is preferably 25 ° C. or less, and more preferably 10 ° C. or less.
  • the crosslinkable group-containing monomer used include N-methylol (meth) acrylamide, N-methoxymethyl acrylamide, N-butoxymethyl acrylamide, acrylamide, and glycidyl (meth) acrylate.
  • a polymer containing a functional group capable of undergoing a polymerization reaction upon irradiation with active energy rays can be produced by a conventionally known method such as emulsion polymerization, bulk polymerization, solution polymerization, suspension polymerization, precipitation polymerization or the like. From the viewpoint of the particle size and stability of the aqueous emulsion (A) obtained, it is preferable to produce the emulsion using an emulsion polymerization method. There is no restriction
  • a surfactant can also be used to further increase the stability of the aqueous emulsion.
  • the emulsion particle diameter in the obtained aqueous emulsion is preferably 5 to 5,000 nm, more preferably 10 to 1000 nm. If it is less than the above lower limit, the water resistance of the coating film to be formed and the storage stability of the composition are not preferable, and if it exceeds the above upper limit, the emulsion particles cause sedimentation over time, thereby impairing the transparency of the coating film and becoming cloudy. There is a tendency.
  • the aqueous emulsion (A) of the present invention may be preferably produced by bulk polymerization. At this time, those produced by catalyst-free bulk polymerization are particularly preferred.
  • the polymer is contained in the aqueous emulsion (A) in an amount of 10 to 70% by mass, more preferably 20 to 60% by mass, still more preferably 30 to 50% by mass, and particularly preferably 35 to 45% by mass. If it is less than the above lower limit, it takes time to dry after applying the composition of the present invention to the nail, etc., and if it exceeds the above upper limit, the polymer cannot settle well as an emulsion and settles over time. May end up.
  • component (B) polyethyleneglycol used by this invention There is no restriction
  • the well-known polyethyleneglycol manufactured by arbitrary manufacturing methods can be used.
  • the upper limit of the weight average molecular weight of polyethylene glycol is preferably 3,000, more preferably 2,000, and the lower limit is preferably 500, more preferably 1,000. If the above upper limit is exceeded, dissolution and dispersion in the composition will be difficult, and the physical properties of the cured film will be adversely affected. Specifically, the cured film will be too soft and the scratch resistance will be reduced.
  • the upper limit of the content of component (B) polyethylene glycol is preferably 30 parts by weight, more preferably 20 parts by weight, with respect to 100 parts by weight of the polymer containing a functional group capable of undergoing a polymerization reaction upon irradiation with active energy rays.
  • the amount is preferably 15 parts by mass, and the lower limit is preferably 0.1 parts by mass, more preferably 2 parts by mass, and even more preferably 3 parts by mass. If it is less than the above lower limit, safety to the human body cannot be sufficiently ensured, and if it exceeds the above upper limit, the stability of the aqueous emulsion may be impaired.
  • a known substance can be used as the photoradical initiator not containing a nitrogen atom in the component (C) molecule used in the present invention.
  • a known substance can be used.
  • ethyl 2,4,6-trimethylbenzoylphenylphosphinate 1-benzoyl-1-cyclohexanol or a mixture thereof is preferably used.
  • a commercial item can be used as this photoradical initiator.
  • Commercially available products include Irugacure 127, 184, 500, 651, 819, 819 DW, 907, 1700, 1800, 1870, 2959 (Darocur 1173, all manufactured by Ciba Specialty Chemicals), Lucirine TPO, TPO- manufactured by BASF L, TPO-XO (both are trademarks) and the like.
  • photo radical initiators that do not fall under any of the environmental hazards, hazards, and irritation based on the safety management classification by GHS (World Harmonized System for Classification and Labeling of Chemicals), such as Irgacure 184 (1- Benzoyl-1-cyclohexanol), Irgacure 2959 (1- [4- (2-hydroxyethoxy) -phenyl] -2-hydroxy-2-methyl-1-propan-1-one), Lucirin TPO-L (2, More preferred is ethyl 4,6-trimethylbenzoylphenylphosphinate). Moreover, in order to apply to a human body, the thing of low odor is more preferable.
  • Irgacure 184 and TPO-L are preferred because of their particularly low odor. Especially, since Irgacure 184 has higher safety, it is not necessary to describe a risk phrase on the GHS classification. Moreover, since the coloring property at the time of apply
  • a component (C) photoinitiator does not contain a nitrogen atom in a molecule
  • the upper limit of the content of the component (C) photoradical initiator is preferably 10 parts by mass, more preferably 6 parts by mass with respect to 100 parts by mass of the polymer containing a functional group capable of undergoing a polymerization reaction by irradiation with active energy rays.
  • the lower limit is preferably 1 part by mass, more preferably 3 parts by mass.
  • the curable resin composition for covering nail or artificial nail of the present invention is for the purpose of adding good gloss, moisture resistance and heat resistance to the cured film in addition to the above components (A), (B) and (C).
  • the wax derived from a component (D) natural product can be included.
  • the wax derived from a natural product include carnauba wax, beeswax, palm wax, lacquer wax, and ibota wax.
  • the upper limit of the content of the component (D) natural product-derived wax is preferably 15 parts by mass, more preferably 10 parts by mass with respect to 100 parts by mass of the polymer containing a functional group capable of undergoing a polymerization reaction by irradiation with active energy rays.
  • the lower limit is preferably 0.1 parts by mass, more preferably 0.5 parts by mass. If it is less than the above lower limit, good gloss, moisture resistance and heat resistance cannot be imparted to the cured film, and if it exceeds the above upper limit, the adhesiveness of the cured film is lowered and the scratch resistance is remarkably reduced.
  • a viscosity adjusting agent such as polyurethane, nonionic polyurethane, xanthan gum, hydroxy can be used as long as the effect of the present invention is not impaired.
  • ⁇ Comparison component (A)> Acrylate monomer: Ditrimethylolpropane tetraacrylate, Ebecryl 40 (trademark) manufactured by UCB Polyether acrylate: amine-modified polyether acrylate, Ebecryl 83 (trademark) manufactured by UCB Urethane acrylate: urethane acrylate oligomer, Craynor 435 (trademark) manufactured by Cray Valley
  • Component (D) Wax derived from natural products> Carnauba wax: Carnaubawax (trademark) manufactured by Toa Kasei Co., Ltd.
  • Leveling and antifoaming agent Mixture of foam-breaking polysiloxane, BYK028 (trademark) manufactured by Byk Chemie, foam-breaking polysiloxane, hydrophobic particles and polyglycol
  • Test method The test methods used in Examples and Comparative Examples are as follows.
  • ⁇ Risk phrase> For each of the compositions obtained in the examples and comparative examples, it was determined which of the classification numbers representing the contents of the risk of hazardous chemical substances established in the European Union. The contents of the determination result and the classification number are as follows. ⁇ : Risk phrase unnecessary R10: Flammable R36: Irritating to eyes R50: Strongly toxic to aquatic organisms R52: Harmful to aquatic organisms R53: May cause long-term adverse effects in the aquatic environment R66: Repeated exposure may cause skin dryness or cracking R67: Gases may cause drowsiness and dizziness
  • Examples 1 to 12 and Comparative Examples 1 to 12 A preparation container having a light-shielding area was prepared. Subsequently, the components (parts by mass) shown in Tables 1 and 2 were each taken in the preparation container, and then sufficiently stirred and mixed at room temperature to obtain a uniform composition. The compositions were then evaluated by performing each of the above tests. The evaluation results are shown in Tables 1 and 2.
  • Examples 1 to 9 and 12 are aqueous emulsion (1) as component (A), that is, the functional group capable of undergoing a polymerization reaction upon irradiation with active energy rays is an acryloyl group, and has a polyacrylic skeleton as the main chain structure. A polymer is used. In both cases, good evaluation results were obtained. Also in Example 2 using Irgacure 184 and Lucirin TPO-L as component (C), Example 8 using Irgacure 500, Example 9 using Irgacure 500 and Lucirin TPO-L, and Example 12 using benzophenone As with Example 1, using Irgacure 184, good evaluation results were shown.
  • Example 3 and 6 the blending amount of component (B) polyethylene glycol was changed. Although Examples 3 and 6 were somewhat inferior to Examples 1 in terms of appearance after curing, water resistance, scratch resistance, and odor before curing, the effects of the present invention were sufficiently exhibited.
  • an aqueous emulsion (2) is used as the component (A), that is, a polymer having a acryloyl group as a functional group capable of undergoing a polymerization reaction by irradiation with active energy rays and having a polyurethane-based skeleton as a main chain structure. It is what was used.
  • the aqueous emulsion (1) that is, Examples 1 and 2 in which the functional group capable of undergoing a polymerization reaction by active energy ray irradiation is an acryloyl group and a polymer having a polyacrylic skeleton as a main chain structure, Similarly, good evaluation results were shown.
  • Comparative Examples 1 to 3 use acrylate monomers, polyether acrylates, and urethane acrylates that were conventionally used in curable resin compositions for covering nails or artificial nails, and use component (B) polyethylene glycol. I didn't. In either case, the damage to the nails and skin irritation were large, and the odor before curing was strong.
  • the component (C) Irgacure 500 in Comparative Example 1 is replaced with Irgacure 184. As in Comparative Example 1, the damage to the nails and skin irritation were large, and the odor before curing was strong.
  • water is added to polyether acrylate and urethane acrylate, respectively.
  • Examples 13 to 17 and Comparative Examples 10 to 14 A basic composition was produced in the same manner as described above using the components (parts by mass) shown in Table 3. Subsequently, the basic composition of the quantity (part by mass) shown in Table 4 and the component (B) or the comparative component (B) were used to obtain a uniform composition. Next, the appearance of the composition before and after curing was evaluated. The evaluation results are shown in Table 4.
  • Example 13 the blending amount of component (B) polyethylene glycol was changed. Although there was no significant change in the appearance after curing, in Example 17 in which the amount of component (B) was increased, the appearance before curing was somewhat deteriorated. However, the function as a curable resin composition for nail or artificial nail coating was not impaired.
  • Comparative Examples 10 to 14 instead of the component (B) polyethylene glycol in Example 13, hydroxyethyl cellulose, propylene glycol alginate, sodium carboxymethyl cellulose, sodium polyacrylate and silica were used, respectively. In all cases, the appearance before curing was remarkably deteriorated. Therefore, when these compositions were applied to the nails, it was not possible to form a smooth coating film with no irregularities on the surface. In Comparative Examples 11 and 12, the appearance after curing was also inferior, and in Comparative Examples 13 and 14, the appearance after curing was remarkably deteriorated.
  • the curable resin composition for covering a nail or artificial nail of the present invention is excellent in appearance after coating, and is excellent in water resistance and scratch resistance, so that the coating may peel off for a long time after coating. No odor, damage to nails, skin irritation, etc., and high safety to human body. Therefore, it is useful not only for decoration but also for protection and reinforcement for preventing cracking of nails and the like, and can be used as nail care products such as manicure, pedicure and sculpture.

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Abstract

La présente invention concerne une composition de résine durcissable pour recouvrir un ongle ou un ongle artificiel. En premier lieu, ladite composition de résine présente un aspect excellent après application, mais elle est également très résistante à l'eau et à l'abrasion, non odorante, n'endommage pas l'ongle, et est hypoallergénique. La composition de résine produite est, par conséquent, à la fois très sûre en ce qui concerne le corps humain et a une excellente stabilité à la conservation. La composition de résine contient (A) une émulsion à base aqueuse d'un polymère qui contient un groupe fonctionnel qui peut subir une réaction de polymérisation après irradiation avec des rayonnements d'énergie active, (B) du polyéthylèneglycol, et (C) un initiateur de polymérisation photoradicalaire (dont les molécules ne contiennent pas d'atomes d'azote).
PCT/JP2010/071862 2009-12-08 2010-12-07 Composition de résine durcissable pour recouvrir un ongle ou un ongle artificiel WO2011071029A1 (fr)

Priority Applications (3)

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US13/514,818 US8846011B2 (en) 2009-12-08 2010-12-07 Curable resin composition for covering a fingernail or artificial fingernail
CN201080055682.6A CN102770119B (zh) 2009-12-08 2010-12-07 指甲或人工指甲被覆用硬化性树脂组合物
EP10835949.8A EP2510920A4 (fr) 2009-12-08 2010-12-07 Composition de résine durcissable pour recouvrir un ongle ou un ongle artificiel

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JP2009278268A JP5544533B2 (ja) 2009-12-08 2009-12-08 爪又は人工爪被覆用硬化性樹脂組成物

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US9701857B2 (en) * 2013-05-27 2017-07-11 DIC Corporation (Tokyo) Active energy ray-curable composition, and ink composition for inkjet recording use which is prepared using said composition
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US9820931B2 (en) 2014-10-13 2017-11-21 L'oreal Latex nail compositions having low amounts of photo-initiator
US9636293B2 (en) * 2014-10-13 2017-05-02 L'oréal Latex nail compositions having low amounts of photo-initiator
US9649272B2 (en) 2014-10-13 2017-05-16 L'oréal Latex nail compositions having low amounts of photo-initiator
US20170312201A1 (en) * 2014-11-05 2017-11-02 Three Bond Co., Ltd. Photocurable composition for topcoat of nails or artificial nails
WO2016152546A1 (fr) * 2015-03-25 2016-09-29 富士フイルム株式会社 Composition pour ongles artificiels, ongle artificiel, procédé de retrait d'ongles artificiels et kit de décoration d'ongles
CN108348445A (zh) * 2015-11-09 2018-07-31 三键有限公司 指甲或人工指甲用光固化性组合物、包含其的底涂剂、它们的固化物、它们的固化物的制造方法及它们的固化物的剥离方法、使用了它们的涂覆方法、以及它们的使用方法
TWI595890B (zh) * 2016-05-09 2017-08-21 穗曄實業股份有限公司 光固化甲油膠組成物
CN106074219B (zh) * 2016-06-07 2018-09-28 杭州淳浠化妆品有限公司 一种耐水水性指甲油及其制备方法
TW201829537A (zh) * 2016-07-29 2018-08-16 日商東亞合成股份有限公司 硬化型組成物
CN110072514B (zh) 2016-12-19 2022-07-15 三键有限公司 指甲或人工指甲用光固化性树脂组合物
US10362850B2 (en) 2017-01-10 2019-07-30 L'oréal Dye-free nail varnish compositions and methods thereof
CN109008156A (zh) * 2018-07-02 2018-12-18 李东洪 一种无痕甲片
JP7217106B2 (ja) * 2018-08-09 2023-02-02 花王株式会社 インクジェット記録用水性組成物
JP7178206B2 (ja) 2018-08-09 2022-11-25 花王株式会社 インクジェット記録用水性組成物
JPWO2022163248A1 (fr) * 2021-01-28 2022-08-04
JPWO2022259947A1 (fr) * 2021-06-08 2022-12-15
KR102384577B1 (ko) * 2021-09-23 2022-04-08 이미숙 내향성 손발톱 교정용 조성물
CN115444371A (zh) * 2022-09-27 2022-12-09 中山大学附属第三医院 一种嗅觉测试装置

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JP2011121867A (ja) 2011-06-23
JP5544533B2 (ja) 2014-07-09
CN102770119B (zh) 2015-04-08
EP2510920A4 (fr) 2015-07-22
CN102770119A (zh) 2012-11-07
KR20120103682A (ko) 2012-09-19
TW201132362A (en) 2011-10-01
EP2510920A1 (fr) 2012-10-17
US8846011B2 (en) 2014-09-30

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