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
  • A61K8/87—Polyurethanes
• • 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
  • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
• • 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
  • A61K8/35—Ketones, e.g. benzophenone
• • 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
  • A61K8/81—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
  • A61K8/72—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
  • 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
  • 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
• • 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
  • A61K2800/95—Involves in-situ formation or cross-linking of polymers

Definitions

• the present invention relates to a photocurable resin composition suitable for covering nails or artificial nails.
• UV gel nails photocurable resin compositions containing photopolymerizable monomers and/or oligomers have been known in the nail field. These UV gel nails are made by applying resin to the nail using a brush or the like, and then curing the nail by irradiating it with light to decorate and make up the nail. A cosmetic film is obtained. This UV gel nail is made up of multiple layers: a base coat layer, a color layer, and a top coat layer. Hardness to protect and coat is also needed.
• JP 2019-6689 discloses a urethane (meth) acrylate oligomer, a polyfunctional thiol compound having two or more thiol groups in one molecule and one or more radically polymerizable unsaturated bonds in one molecule.
• An artificial nail composition with excellent surface gloss is disclosed which contains a radically polymerizable compound.
• Japanese Unexamined Patent Publication No. 2017-210475 discloses a lustrous photocurable artificial nail composition containing a urethane (meth)acrylate oligomer, a (meth)acrylic monomer, a polyfunctional thiol and a photopolymerization initiator. .
• the present invention has been made in view of the above circumstances, and an object of the present invention is to provide a photocurable resin composition for nails or artificial nails that can form a cured product having excellent gloss.
• Photocurable resin composition for nails or artificial nails containing 0.01 parts by mass or more and 3 (3.0) parts by mass or less of component (C):
• the photocurable resin composition for nails or artificial nails is applied to a film thickness of 0.1 mm, cured with an integrated light amount of 7.5 kJ / m2 , and the uncured material on the surface of the cured product is removed with a solvent.
• the coating film is irradiated with energy rays.
• a method of covering a nail or artificial nail comprising curing a film.
• X to Y is used to mean that the numerical values (X and Y) before and after it are included as lower and upper limits.
• operations and measurements of physical properties are performed under the conditions of room temperature (20 to 25° C.)/relative humidity of 40 to 50% RH.
• One form of the present invention contains the following components (A) to (D), with respect to 100 parts by mass of a compound having a (meth)acryloyl group, 0.01 parts by mass or more and 3.0 parts by mass of the component (C)
• a photocurable resin composition for nails or artificial nails comprising: (A) component: urethane (meth)acrylate oligomer; (B) component: a compound having three or more (meth)acryloyl groups (excluding component (A)); (C) component: polyfunctional thiol compound; and (D) component: photoinitiator.
• a cured product having excellent glossiness can be formed.
• the (A) component contained in the photocurable resin composition according to the present invention is a urethane (meth)acrylate oligomer, and the (A) component has at least one urethane bond and at least one (meth)acryloyl group. Any oligomer can be used. Addition of a urethane (meth)acrylate oligomer can improve the adhesion to nails or artificial nails, and improve the curability and strength of the photocurable resin composition (coating film).
• oligomer refers to a polymer in which two to several tens of monomer units (including monomer units other than (meth)acrylate monomers) are repeated.
• the compound which has a (meth)acryloyl group points out the thing of (meth)acrylate.
• the (meth)acryloyl group may have a (meth)acryloyl group in the form of a (meth)acryloyloxy group.
• the term "(meth)acryloyl” includes both acryloyl and methacryloyl.
• the term “(meth)acrylate” includes both acrylate and methacrylate
• the term “(meth)acryl” includes both acrylic and methacrylic.
• Component (A) is not particularly limited as long as it is an oligomer having one or more urethane bonds and (meth)acryloyl groups, but preferably contains 2 to 6 (meth)acryloyl groups. It is more preferable to have 2 to 3, and most preferably to have 3 (meth)acryloyl groups. Most preferably, component (A) has two (meth)acryloyl groups. Also, the (meth)acryloyl group of the component (A) is preferably an acryloyl group. In addition to the urethane bond and the (meth)acryloyl group, it may have other functional groups such as a carboxyl group, a phosphoric acid group, and a hydroxyl group.
• the weight average molecular weight of the (A) component oligomer is preferably 1,000 to 100,000, more preferably 1,200 to 30,000, and particularly preferably 1,500 to 20,000. Within such a range, it is possible to improve the curability of the cured product while maintaining the viscosity with good workability.
• the weight average molecular weight adopts the value measured by gel filtration chromatography (Gel Permeation Chromatography; GPC) using polystyrene as a standard substance.
• Component (A) forms a urethane bond through the reaction of polyol and polyisocyanate, and adds a compound having a hydroxyl group and (meth)acryloyl group in the molecule or (meth)acrylic acid to the unreacted isocyanate group.
• the method for synthesizing the urethane (meth)acrylate oligomer is not limited to this method.
• polyether polyol or a polyether-skeletal urethane (meth)acrylate oligomer using polyether polyol having an aromatic group such as bisphenol as the polyol.
• Component (A) is preferably a polyether skeleton bifunctional urethane (meth)acrylate oligomer.
• other urethane (meth)acrylate oligomers such as polyester skeleton urethane (meth)acrylate oligomers, polycaprolactone skeleton urethane (meth)acrylate oligomers, polycarbonate skeleton urethane (meth)acrylate oligomers, etc. can also be used in combination.
• Component (A) may be used singly or in combination of two or more.
• Component (B) contained in the photocurable resin composition according to the present invention is a compound having three or more (meth)acryloyl groups (excluding component (A)).
• the number of (meth)acryloyl groups contained in one molecule is not particularly limited as long as it is 3 or more functional groups. It is more preferably 6 functional groups, and most preferably 3 functional groups.
• component (B) is a compound having three (meth)acryloyl groups as functional groups.
• component (B) contained in the photocurable resin composition according to the present invention include trimethylolpropane tri(meth)acrylate, trimethylolethane tri(meth)acrylate, and ethoxylated trimethylolpropane (meth)acrylate.
• ethoxylated trimethylolpropane tri(meth)acrylate isocyanuric acid EO-modified tri(meth)acrylate, pentaerythritol tri(meth)acrylate, EO-modified trimethylolpropane tri(meth)acrylate, PO-modified trimethylolpropane tri(meth)acrylate Acrylate, ECH-modified trimethylolpropane tri(meth)acrylate, ECH-modified glycerol tri(meth)acrylate, tris(acryloyloxyethyl)isocyanurate, pentaerythritol tetra(meth)acrylate, tetramethylolmethane tetra(meth)acrylate, dipenta Erythritol tetra(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, dipentaerythritol hexa(meth)
• Component (B) may be used singly or in combination of two or more.
• the content of component (B) is 3 to 50 parts by mass, more preferably 5 to 40 parts by mass, still more preferably 10 to 30 parts by mass, per 100 parts by mass of component (A). Department.
• component (B) is 3 parts by mass or more, the hardness of the cured product can be maintained.
• (B) is 50 parts by mass or less, the transparency of the cured product can be maintained.
• the (C) component contained in the photocurable resin composition according to the present invention is a polyfunctional thiol compound.
• the content of the component (C) is the compound having a (meth)acryloyl group contained in the photocurable resin composition or the compound having a (meth)acryloyl group containing the component (A) and the component (B) 100
• parts by mass for example, 0.01 to 4.0 parts by mass, 0.01 to 3 (3.0) parts by mass, more preferably 0.1 to 2.8 parts by mass, more preferably is 1 to 2.5 parts by mass.
• the polyfunctional thiol compound any compound having two or more thiol groups in one molecule can be used, but from the viewpoint of glossiness, the thiol group has 3 to 6 functional groups. is preferred, and trifunctional groups are most preferred.
• the ratio of (meth)acryloyl groups to thiol groups is preferably 9 or more, more preferably 11 or more (number of (meth)acryloyl groups/number of thiol groups). Although not particularly limited, the upper limit is 1,000 (number of (meth)acryloyl groups/number of thiol groups).
• the above-mentioned "100 parts by mass of a compound having a (meth)acryloyl group” means 100 parts by mass in consideration of the amount of component (E) in the case of a composition containing component (E), which will be described later.
• "Functional group ratio of (meth)acryloyl group and thiol group” means a ratio considering the (meth)acryloyl group of the component (E) in the case of a composition containing the component (E) described later.
• the content of component (C) is, for example, 0.01 to 4.0 parts by mass, preferably 0.1 to 3 parts by mass, with respect to a total of 100 parts by mass of component (A) and component (B). 0.9 parts by mass, more preferably 1 to 3.8 parts by mass.
• the functional group ratio of the (meth)acryloyl group and the thiol group can be calculated from the (meth)acryloyl group equivalent and the thiol group equivalent determined by the following method, for example.
• the following method can be used as a method for measuring the (meth)acryloyl group equivalent.
• S is the mass (g) of the compound having a (meth)acryloyl group
• f is the titer of a 0.5 mol/L hydrogen chloride methanol solution.
• the following method (iodine titration method) can be used.
• a sample solution is prepared by adding 20 mL of chloroform to 0.2 g of a polyfunctional thiol compound.
• a starch indicator 0.275 g of soluble starch is dissolved in 30 g of pure water.
• 20 mL of pure water, 10 mL of isopropyl alcohol and 1 mL of starch indicator are added to the sample solution and stirred with a stirrer.
• An iodine solution was added dropwise, and the point at which the chloroform layer turned green was taken as the end point.
• Thiol group equivalent (g/eq) mass (g) of polyfunctional thiol compound ⁇ 10000/titration amount of iodine solution (mL) ⁇ factor of iodine solution.
• component (C) contained in the photocurable resin composition according to the present invention include 1,2-ethanedithiol, 1,2-propanedithiol, 1,3-propanedithiol, 1,3-butanedithiol, 2,3-butanedithiol, 1,5-pentanedithiol, 1,6-hexanedithiol, 1,8-octanedithiol, 1,9-nonanedithiol, 1,10-decanedithiol, 1,2-benzenedithiol, 1 , 3-benzenedithiol, 1,4-benzenedithiol, 3,6-dichloro-1,2-benzenedithiol, toluene-3,4-dithiol, 1,5-naphthalenedithiol, ethylene glycol bis(thioglycolate), Ethylene glycol bis(3-mercaptopropionate), 1,4-butanediol bisthioglycolate,
• Preferred polyfunctional thiol compounds include polyfunctional thiol compounds having a trimethylolpropane skeleton, a pentaerythritol skeleton and a dipentaerythritol skeleton, particularly preferably trimethylolpropane tris (3-mercaptopropionate), tri methylolpropane tris(3-mercaptobutyrate), tris[(3-mercaptopropionyloxy)-ethyl]-isocyanurate, pentaerythritol tetrakis(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptobutyrate), Dipentaerythritol hexakis (3-mercaptopropionate), dipentaerythritol hexakis (3-mercaptobutyrate), more preferably polyfunctional thiol having a trimethylolpropane skeleton, most preferably trimethyl
• component (C) is a polyfunctional thiol compound having a trimethylolpropane skeleton.
• Component (C) may be used singly or in combination of two or more.
• the (D) component contained in the photocurable resin composition according to the present invention is a photoinitiator.
• Component (D) includes radical photoinitiators that generate radical species when exposed to energy rays such as visible light, ultraviolet rays, X-rays, and electron beams, cationic photoinitiators that generate cationic species, and anions that generate anionic species.
• radical photoinitiators are preferable from the viewpoint of reactivity and the like, and it is preferable to use a visible light radical photoinitiator and an ultraviolet radical photoinitiator in combination. From the viewpoint of long-term storage stability, it is preferable that the ultraviolet radical photoinitiator and the visible light radical photoinitiator are contained in a ratio (mass ratio) of 5:5 to 7:3.
• Radical photoinitiators include, for example, acetophenone radical initiators, benzoin radical initiators, benzophenone radical initiators, thioxanthone radical initiators, acylphosphine oxide radical initiators, titanocene radical initiators, and the like.
• acetophenone-based radical initiators and acylphosphine oxide-based radical initiators are preferred from the viewpoint of excellent photocurability.
• these may be used independently and 2 or more types may be used together.
• An acetophenone radical initiator corresponds to an ultraviolet radical photoinitiator
• an acylphosphine oxide radical initiator corresponds to a visible light radical photoinitiator.
• acetophenone-based radical initiators include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethylketal, 4-(2-hydroxyethoxy)phenyl-(2-hydroxy-2 -propyl)ketone, 1-hydroxy-cyclohexyl-phenyl-ketone, 2-methyl-2-morpholino(4-thiomethylphenyl)propan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl)butanone, 2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propanone oligomers and the like, and acylphosphine oxide radical initiators include 2,4,6-trimethyl benzoyl-diphenyl-phosphine oxide, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide and the like.
• Component (D) may be used singly or in combination of two or more. From the viewpoint of compatibility between glossiness and curability, it is preferable to use an acetophenone radical initiator and an acylphosphine oxide radical initiator together. Specifically, it is more preferable to use 1-hydroxy-cyclohexyl-phenyl-ketone and 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide together.
• the content of the component (D) is a compound having a (meth)acryloyl group contained in the photocurable resin composition or a (meth)acryloyl group containing the component (A) and the component (B) It is, for example, 0.1 to 15 parts by mass, more preferably 1 to 12 parts by mass, and even more preferably 3 to 9 parts by mass with respect to 100 parts by mass of the compound having When the component (D) is 0.1 part by mass or more, the glossiness of the cured product can be maintained. On the other hand, when the component (D) is 15 parts by mass or less, the transparency of the cured product can be maintained.
• 100 parts by mass of a compound having a (meth)acryloyl group means 100 parts by mass in consideration of the amount of component (E) when the composition contains component (E), which will be described later.
• the content of component (D) is preferably 3 to 10 parts by mass with respect to a total of 100 parts by mass of components (A) and (B).
• the photocurable resin composition according to the present invention preferably does not contain a solvent from the viewpoint of adhesion to nails.
• a compound having a (meth)acryloyl group other than the (A) component and the (B) component may be added as the (E) component to the photocurable resin composition according to the present invention.
• the photocurable resin composition according to the present invention further contains a compound having a (meth)acryloyl group other than the (A) component and the (B) component as the (E) component.
• the mass ratio of the sum of components (A) and (B) to component (E) ((A)+(B):(E)) is preferably 7:3 to 5:5.
• compounds having one functional group (meth)acryloyl group other than components (A) and (B) include lauryl (meth)acrylate, stearyl (meth)acrylate, ethylcarbitol (meth)acrylate, tetrahydrofuran Furyl (meth)acrylate, caprolactone-modified tetrahydrofurfuryl (meth)acrylate, cyclohexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, isobornyl (meth)acrylate, benzyl (meth)acrylate, phenyl (meth)acrylate, phenoxy Ethyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, phenoxytetraethylene glycol (meth) acrylate, nonylphenoxyethyl (meth) acrylate, nonylphenoxytetraethylene glycol (meth) acrylate, methoxyd
• compounds having two functional groups (meth)acryloyl groups other than components (A) and (B) include 1,3-butylene glycol di(meth)acrylate and 1,4-butylene glycol di(meth) Acrylates, tricyclodecanedimethanol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,6-hexane glycol di(meth)acrylate, ethylene glycol diacrylate, tetraethylene glycol di(meth)acrylate , polyethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, ethylene oxide-modified neopentyl glycol di(meth)acrylate, propylene oxide-modified neopentyl glycol di(meth)acrylate, Bisphenol A ethoxylate di(meth)acrylate, ethylene oxide-modified bisphenol A di(meth)acrylate,
• Component (E) may be used singly or in combination of two or more.
• a filler may be added to the photocurable resin composition according to the present invention for the purpose of improving the elastic modulus, fluidity, etc. of the cured product within a range that does not impair the purpose of the present invention.
• Specific examples include inorganic powders and organic powders.
• Inorganic powder fillers include glass, fumed silica, alumina, mica, ceramics, silicone rubber powder, calcium carbonate, aluminum nitride, carbon powder, kaolin clay, dried clay minerals, dried diatomaceous earth, kaolin, and the like. are not limited to these. These may be used alone or in combination of two or more.
• the amount of the inorganic powder compounded is preferably about 0.1 to 200 parts by mass per 100 parts by mass of component (A).
• Fumed silica is blended for the purpose of adjusting the viscosity of the photocurable resin composition or improving the mechanical strength of the cured product. Fumed silica or the like surface-treated with dimethylsilane, trimethylsilane, alkylsilane, methacryloxysilane, organochlorosilane, polydimethylsiloxane, hexamethyldisilazane or the like is preferably used.
• fumed silica Commercial products of fumed silica include, for example, Aerosil R972, R972V, R972CF, R974, R976, R976S, R9200, RX50, NAX50, NX90, RX200, RX300, R812, R812S, R8200, RY50, NY50, RY200S, RY200, Examples include RY300, R104, R106, R202, R805, R816, T805, R711, R7200 (manufactured by Nippon Aerosil Co., Ltd.), but are not limited thereto. These may be used alone or in combination of two or more.
• organic powder fillers include, but are not limited to, polyethylene, polypropylene, polystyrene, nylon, polyester, polyvinyl alcohol, polyvinyl butyral, polycarbonate, and polymethyl (meth)acrylate. These may be used alone or in combination of two or more.
• the amount of the organic powder compounded is preferably about 0.1 to 200 parts by mass per 100 parts by mass of component (A).
• a conductive filler may be added to the photocurable resin composition according to the present invention.
• conductive fillers include, but are not limited to, gold, silver, platinum, nickel, palladium, and plated particles obtained by coating metal thin films on organic polymer particles. These may be used alone or in combination of two or more.
• a silane coupling agent may be added to the photocurable resin composition according to the present invention.
• silane coupling agents include ⁇ -chloropropyltrimethoxysilane, octenyltrimethoxysilane, glycidoxyoctyltrimethoxysilane, ⁇ -(3,4-epoxycyclohexyl)ethyltrimethoxysilane, ⁇ -glycidoxysilane.
• a plasticizer as the component (F) to the photocurable resin composition according to the present invention.
• Component (F) is not particularly limited, but examples thereof include compounds having a polyether skeleton as polyether plasticizers.
• a polyether skeleton means a skeleton having an alkylene oxide such as polypropylene glycol, polyethylene glycol, and polybutylene glycol.
• the repeating number of the alkylene oxide is not particularly limited, but is, for example, 3-300, more preferably 5-100, particularly preferably 10-60.
• polycarboxylic acid ester plasticizers include aromatic polycarboxylic acid esters
• phthalic acid esters include dioctyl phthalate (DOP), dibutyl phthalate (DBP), diheptyl phthalate (DHP), diisononyl phthalate (DINP), and diisodecyl phthalate (DIDP).
• DOP dioctyl phthalate
• DBP dibutyl phthalate
• DHP diheptyl phthalate
• DINP diisononyl phthalate
• IDDP diisodecyl phthalate
• BBP butyl benzyl phthalate
• TOTM trioctyl trimellitate
• TITM triisodecyl trimellitate
• trimellitate esters tetraoctyl pyromellitate as pyromellitic esters
• aliphatic polycarboxylic acid esters as di-2-ethylhexyl adipate (DOA), isodecyl adipate (DIDA), di-2-ethylhexyl sebacate (DOS), dibutyl sebacate (DBS), di-2-ethylhexyl maleate (DOM), dibutyl fumarate (DBF ), di-2-ethylhexyl azelate (DOZ), di-2-ethylhexyl epoxyhexahydrophthalate, trioctyl citrate, glycerol triacetate, and the like, but are not limited thereto.
• DOA di-2-ethylhexyl adipate
• DIDA di-2-ethylhexyl sebacate
• DBS dibutyl sebacate
• DOM di-2
• phosphate plasticizers trimethyl phosphate, tributyl phosphate, tri-(2-ethylhexyl) phosphate, tributoxyethyl phosphate, triphenyl phosphate, tricresyl phosphate, alkylallyl phosphate, triethyl phosphate, tri(chloroethyl) Phosphate, trisdichloropropyl phosphate, tris( ⁇ -chloropropyl) phosphate, octyldiphenyl phosphate, tris(isopropylphenyl) phosphate, cresylphenyl phosphate, and the like, but are not limited to these.
• a combination of multiple plasticizers can also be used.
• the photocurable resin composition according to the present invention further contains a polyether plasticizer as component (F).
• the number average molecular weight of component (F) is not particularly limited, it is, for example, in the range of 200 to 30,000, preferably in the range of 350 to 10,000, and particularly preferably in the range of 500 to 5,000.
• the number average molecular weight is calculated by a standard polystyrene conversion method using size exclusion chromatography (SEC), unless otherwise specified.
• SEC size exclusion chromatography
• polyether-based plasticizers of component (F) are not particularly limited, but examples include PEG#300, PEG#400, PEG#600, PEG#1000, PEG#1500, PEG#15400, PEG# 2000, PEG#4000, PEG#6000, PEG#1100, PEG#2000, Uniol D-700, D-1000, D-1200, D-2000, D-4000, PB-500, PB-700, PB-1000 , PB-2000 (manufactured by NOF Corporation) and the like.
• the amount of component (F) is a compound having a (meth)acryloyl group contained in the photocurable resin composition or a compound having a (meth)acryloyl group containing the component (A) and the component (B).
• 1 to 20 parts by mass is preferable, 3 to 15 parts by mass is more preferable, and 5 to 13 parts by mass is particularly preferable with respect to 100 parts by mass.
• 100 parts by mass of a compound having a (meth)acryloyl group means 100 parts by mass in consideration of the blending amount of component (E) in the case of a composition containing component (E). Also, the content of component (F) is preferably 5 to 18 parts by mass with respect to a total of 100 parts by mass of components (A) and (B).
• a cured product having excellent glossiness can be formed.
• the photocurable resin composition for nail or artificial nail according to the present invention is applied so as to have a film thickness of 0.1 mm, cured at an integrated light amount of 7.5 kJ/m 2 , and then treated with a solvent.
• the glossiness of the surface of the cured product is 67 or more and 88 or less at 20°.
• One embodiment of the present invention is a cured product obtained by curing the photocurable resin composition for nails or artificial nails according to the present invention.
• An artificial nail in the present invention refers to a layer formed on a human or animal nail for the purpose of decoration and/or protection.
• the above other artificial nails include a resin base material (artificial nail) having an arbitrary shape for the purpose of decorating and/or protecting the nail.
• the shape of the artificial nail is not particularly limited, and it may be formed so as to cover the nail, or may be formed in a shape larger than the nail for the purpose of extending the nail. Also, it may be formed for the purpose of adhering an item such as a stone to the nail to improve the appearance.
• Artificial nails are generally constructed by forming a base coat layer (a layer for the purpose of imparting adhesion to the nail, preventing color transfer, etc.) formed by curing a base coat photocurable resin composition on the surface of the nail, On top of that, a color layer (a layer containing a coloring material and the like for the purpose of decoration) formed by curing a photocurable resin composition for color is formed, and a photocurable resin composition for a top coat is further cured thereon. Then, a top coat layer (a layer for coating, glossing, and improving aesthetics) is formed.
• the photocurable resin composition of the present invention is not particularly limited as long as it is used for the purpose of forming a layer on a nail or artificial nail. It is preferably used as a resin composition. In a preferred embodiment, the photocurable resin composition according to the present invention is for forming a topcoat layer.
• the photocurable resin composition according to the present invention Before applying the photocurable resin composition according to the present invention, when applying directly to the nail, sand the surface of the nail with a file (file) or the like in order to improve adhesion, and then use ethanol as the main component. Remove dust, oil, moisture, etc. with a special solvent for nails.
• a coating film having a thickness of 50 to 300 ⁇ m is formed before curing with a brush or the like.
• the photocurable resin composition according to the present invention may be applied directly onto a cured film of a base coat resin, a color resin, or the like. A primer may be used prior to application.
• the photocurable composition is cured by irradiating energy rays.
• the energy rays referred to here include radiation such as ⁇ rays and ⁇ rays, electromagnetic waves such as ⁇ rays and X rays, electron beams (EB), ultraviolet rays with a wavelength of about 100 to 380 nm, visible rays with a wavelength of about 381 to 800 nm, etc. It includes all light in a broad sense, preferably ultraviolet light and visible light.
• a commercially available nail UV lamp or nail LED lamp is used as an irradiation device for curing.
• the irradiation time is 15 to 120 seconds, preferably 20 to 70 seconds considering the effect on fingers.
• the integrated amount of light is preferably 3 to 15 kJ/m 2 , more preferably 5 to 10 kJ/m 2 .
• the nail wiping solvent include, but are not limited to, those containing ethanol, isopropyl alcohol, methyl ethyl ketone, acetone, and the like as main components.
• Another embodiment of the present invention comprises applying the photocurable resin composition according to the present invention to a nail or an artificial nail to form a coating film, and then irradiating energy rays to cure the coating film. Or a method of covering an artificial nail.
• the photocurable resin composition of the present invention can be produced by a conventionally known method.
• components (A) to (D) and, if necessary, other components are blended in predetermined amounts, and mixed using a mixing means such as a planetary mixer at a temperature of preferably 10 to 50°C under light-shielding conditions. preferably by mixing for 0.1 to 5 hours.
• the photocurable resin composition is simply referred to as a resin.
• ⁇ (A) Component> a1 polyether skeleton bifunctional urethane acrylate (ART RESIN UN-6303, manufactured by Negami Industries Co., Ltd., weight average molecular weight: 4000)
• b1 isocyanuric acid EO-modified triacrylate (Aronix M-313 (65% by mass), manufactured by Toagosei Co., Ltd.)
• b2 trimethylolpropane triacrylate (NK ester A-TMPT, manufactured by Shin-Nakamura Chemical Co., Ltd.)
• b3 trimethylolpropane trimethacrylate (NK ester TMPT, manufactured by Shin-Nakamura Chemical Co., Ltd.)
• b4 ethoxylated trimethylolpropane triacrylate (Sartomer SR502, manufactured by Sartomer)
• c1 trimethylolpropane tris(3-mercaptopropionate) (TMMP-20
• test methods used in the examples and comparative examples in Table 1 are as follows.
• ⁇ is preferable and ⁇ is more preferable in the following evaluation criteria.
• a 1 mm-thick spacer was placed on a soda plate glass of 1.0 ⁇ 150 ⁇ 150 mm, and the photocurable resin composition was applied thereon.
• a PET film is overlaid thereon, and another soda lime glass is overlaid to sandwich the photocurable resin composition, and a high pressure mercury lamp (curing condition: integrated light intensity 30 kJ / m 2 ) is used to illuminate the surface of the two soda lime glasses. and irradiated twice from the back surface to prepare a cured product having a thickness of 1 mm (curing was performed by adjusting the above curing conditions for UV transmitted through the PET film and soda lime glass). Three cured products were prepared in the same manner and allowed to stand for 2 hours.
• the soda lime glass and the PET film were peeled off, and three 1 mm-thick cured sheets were stacked with the PET film-adhered surface facing upward.
• the hardness of the laminated sheet-like cured product was measured using a type D durometer tester on a smooth surface. In addition, the measurement was performed 5 times, and the average value of 3 times excluding the maximum and minimum values was obtained. In order to be less likely to be scratched and peeled off in daily life, it is preferable to be evaluated as ⁇ in the following evaluation criteria.
• the photocurable resin composition is capable of forming a cured product with excellent glossiness.
• the component (C) is different between Example 1 and Examples 3 to 6, both cured products have excellent glossiness, and the component (B) is used in Example 1 and Examples 7 to 9. Although different, both cured products have excellent glossiness.
• Comparative Example 1 since Comparative Example 1 does not contain the (C) component, the glossiness of the cured product is inferior.
• the amount of component (C) added exceeded 3 parts by mass (3.0) with respect to 100 parts by mass of components (A), (B) and (E). I know it's inferior.
• Comparative Examples 3 and 4 although the (B) component was replaced with the (E) component, the glossiness of the cured product was not excellent.
• Comparative Example 5 since the component (B) is not included, it can be seen that the glossiness of the cured product is inferior.
• the photocurable resin composition of the present invention is a photocurable resin composition for nails or artificial nails that has hardness necessary for coating when cured and can form a glossy cured product. Can be widely used in the field.

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• 2022
  • 2022-06-02 KR KR1020237037939A patent/KR20240018424A/ko active Pending
  • 2022-06-02 CN CN202280034085.8A patent/CN117279616A/zh active Pending
  • 2022-06-02 EP EP22820129.9A patent/EP4353219A4/en active Pending
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