Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
  • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
  • C08F290/06—Polymers provided for in subclass C08G
  • C08F290/067—Polyurethanes; Polyureas
• • 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
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/37—Esters of carboxylic acids
  • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
• • 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
  • A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; 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
  • 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
  • A61Q3/00—Manicure or pedicure preparations
  • A61Q3/02—Nail coatings
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
  • C09D151/08—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• • 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 coating nails, a cured product, and a method for coating nails or artificial nails.
• a photocurable resin composition (UV nail gel) containing a photopolymerizable monomer and / or an oligomer is known.
• UV nail gels are applied to the nails using a brush or the like, and then irradiated with light to cure the nails to decorate and make up the nails. They have a beautiful luster and high adhesion to the nails.
• a nail makeup film can be obtained.
• a nail decorative film is generally formed by a plurality of layers of a base coat layer, a color layer, and a top coat layer.
• the top coat layer is most important for its glossy and colorless and transparent appearance in order to make the underlying decoration look beautiful, and the hardness (hardness) for coating the nail or artificial nail while protecting the decoration. ) Is also needed.
• JP-A-2010-37330 corresponding to US Patent Application Publication No. 2010/0008876
• radically polymerizable unsaturated as an artificial nail composition having less yellowing and excellent internal curability A compound having a double bond (component (a)); (i) an acylphosphine oxide type photopolymerization initiator, and (ii) a mixture of an acylphosphine oxide type photopolymerization initiator and an ⁇ -hydroxyalkylphenone type photopolymerization initiator.
• An artificial nail composition containing a component selected from the group consisting of (component (b)); in which the weight ratio of the above components (a) and (b) is within a specific range has been proposed.
• the amount of the photopolymerization initiator added is increased in order to enhance the photocurability, yellowing occurs when the composition is cured and the transparency is lost. On the contrary, the amount of the photopolymerization initiator added. If the amount is reduced, there is a problem that the curability of the composition is lowered and the glossiness is lowered, and it is difficult to achieve good transparency and glossiness at the same time.
• the present invention has been made in view of the above circumstances, and is capable of forming a cured product having excellent transparency and luster while having the hardness (hardness) required for coating nails or artificial nails. It is an object of the present invention to provide a photocurable resin composition for nails or artificial nails that can be produced. Another object of the present invention is to provide a cured product obtained by curing the photocurable resin composition for nails or artificial nails. Furthermore, another object of the present invention is to provide a method for covering a nail or an artificial nail using the above-mentioned photocurable resin composition for a nail or an artificial nail.
• the present inventors have obtained the hardness (hardness) required for coating nails or artificial nails in the photocurable resin composition for nails or artificial nails described in detail below.
• the present invention has been completed.
• the gist of the present invention will be described below.
• a photocurable resin composition for nails or artificial nails containing the following components (A) to (D): Component (A): Urethane (meth) Acrylate oligomer (B) Component: Compound having 3 or more (meth) acryloyl groups (excluding component (A)) Component (C): A compound having a molecular weight of 200 or less and having a hydroxyl group and a methacryloyl group (excluding components (A) and (B)).
• Component (D) Ingredient: Photoinitiator.
• a cured product of the photocurable resin composition for nails or artificial nails according to any one of [1] to [9].
• the photocurable resin composition for nails or artificial nails according to any one of [1] to [9] is applied onto the nails or artificial nails to form a coating film, and then irradiated with active energy rays.
• X to Y means the range including the numerical values (X and Y) described before and after it as the lower limit value and the upper limit value.
• concentration and% shall represent the mass concentration and the mass%, respectively, unless otherwise specified, and the ratio shall be the mass ratio unless otherwise specified.
• 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.
• a and / or B includes each and a combination of A and B, specifically, means at least one of A and B, and means A, B and a combination of A and B.
• the photocurable resin composition for nails or artificial nails (hereinafter, also referred to as "photocurable resin composition” or simply “composition”) according to one embodiment of the present invention is the following components (A) to (D). including: Component (A): Urethane (meth) acrylate oligomer (B) Component: Compound having 3 or more (meth) acryloyl groups (excluding component (A)) Component (C): A compound having a molecular weight of 200 or less and having a hydroxyl group and a methacryloyl group (excluding components (A) and (B)). (D) Ingredient: Photoinitiator.
• a cured product having excellent transparency and gloss can be formed. Further, according to the photocurable resin composition according to one embodiment of the present invention, it is possible to obtain a cured product having a hardness (hardness) necessary for coating a nail or an artificial nail.
• the compound contained as the component (C) particularly contributes to the suppression of yellowing (improvement of transparency) and the improvement of glossiness in a well-balanced manner. Specifically, when the molecular weight of the compound contained as the component (C) exceeds 200, the transparency and glossiness (particularly, transparency) are lowered (Comparative Examples 2 to 4 described later). Further, when the compound does not have a methacryloyl group (for example, it has an acryloyl group instead), the glossiness is particularly liable to decrease (Comparative Examples 1 and 6 described later). Further, when the compound does not have a hydroxyl group, it is difficult to suppress yellowing, and the transparency is particularly liable to decrease (Comparative Examples 5 to 7 described later).
• the compound contained as the component (B) contributes to the improvement of the hardness of the cured product.
• the photocurable resin composition does not contain the compound corresponding to the component (B)
• the hardness of the cured product decreases (Comparative Examples 8 to 10 described later).
• the component (A) contained in the photocurable resin composition according to the present invention is a urethane (meth) acrylate oligomer.
• the urethane (meth) acrylate oligomer refers to an oligomer having one or more urethane bonds and one or more (meth) acryloyl groups.
• a (meth) acryloyl group may have a (meth) acryloyl group in the form of a (meth) acryloyloxy group.
• the term “(meth) acrylate” includes both acrylate and methacrylate
• the term “(meth) acrylic” includes both acrylic and methacrylic.
• the "oligomer” means a polymer in which a monomer unit (including a monomer unit other than a (meth) acrylate monomer) is repeated about 2 to several tens.
• the component (A) is not particularly limited as long as it is an oligomer having one or more urethane bonds and one or more (meth) acryloyl groups. Further, in addition to three or more (meth) acryloyl groups, a compound having a urethane bond (however, an oligomer) shall be contained in the component (A) and not in the component (B).
• the number of (meth) acryloyl groups contained in the oligomer of the component (A) is not particularly limited as long as it is 1 or more, but contains 2 to 6 (meth) acryloyl groups (2 to 6 functional (meth) acrylate oligomers). ) Is preferable, and it is more preferable to have two (meth) acryloyl groups (bifunctional (meth) acrylate oligomer). Further, 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 carboxy group, a phosphoric acid group, an epoxy group and a hydroxyl group.
• the weight average molecular weight of the oligomer of the component (A) is preferably 1,000 to 100,000, more preferably 2,000 to 30,000, and particularly preferably 3,000 to 20,000. Within such a range, the curability of the cured product can be improved while maintaining a good viscosity for workability.
• a value measured by gel permeation chromatography (GPC) using polystyrene as a standard substance is adopted as a weight average molecular weight.
• the urethane (meth) acrylate oligomer as the component (A) either a synthetic product or a commercially available product may be used.
• the urethane (meth) acrylate oligomer of the component (A) can be produced by a conventionally known method or by appropriately modifying these methods.
• a method for synthesizing a urethane (meth) acrylate oligomer for example, a compound having a urethane bond formed by a reaction between a polyol and a polyisocyanate and having a hydroxyl group and a (meth) acryloyl group in the molecule with respect to an unreacted isocyanate group.
• it can be synthesized by adding (meth) acrylic acid, but the method for synthesizing the urethane (meth) acrylate oligomer is not limited to this method.
• the component (A) preferably contains a urethane (meth) acrylate oligomer having a polyether skeleton.
• a polyether skeleton urethane using an aliphatic polyether polyol or an aromatic polyether polyol having a bisphenol skeleton or the like is used. It is preferable to use a (meth) acrylate oligomer.
• urethane (meth) acrylate oligomers for example, polyester skeleton-containing urethane (meth) acrylate oligomer, polycaprolactone skeleton-containing urethane (meth) acrylate oligomer, polycarbonate skeleton-containing urethane (meth) acrylate oligomer, etc. Can also be used in combination.
• oligomer of the component (A) examples include AH-600, UA-510H (manufactured by Kyoeisha Chemical Co., Ltd.), SUA-008, SUA-023 (manufactured by Asia Industries Co., Ltd.), UN-6060S, and the like.
• UN-6060PTM, UN-6200, UN-6207, UN-6303, UN-6304, UN-6305, UN-6306 (manufactured by Negami Kogyo Co., Ltd.) and the like can be mentioned, but the present invention is not limited thereto.
• the urethane (meth) acrylate oligomer as the component (A) may be used alone or in combination of two or more.
• the content of the component (A) refers to the total amount.
• the component (B) contained in the photocurable resin composition according to the present invention is a compound having three or more (meth) acryloyl groups (trifunctional group or more) (however, excluding the component (A)).
• a cured product having the hardness (hardness) required for coating nails or artificial nails can be obtained.
• the number of (meth) acryloyl groups contained in one molecule is not particularly limited as long as it is 3 or more. Further, a compound having a molecular weight of 200 or less and having one or more hydroxyl groups and three or more methacryloyl groups shall be included in the component (B) and not included in the component (C). And.
• the number of (meth) acryloyl groups contained in the compound of the component (B) is not particularly limited as long as it is 3 or more, but 3 to 8 (3) for the purpose of obtaining a cured product having good hardness (hardness). It is preferably 8 to 8 functional, more preferably 3 to 6 (3 to 6 functional), even more preferably 4 to 6 (4 to 6 functional), and even more preferably 5 or 6 (5 or 6). (Sensual) is particularly preferable. From the viewpoint of effectively suppressing the yellowing of the cured product, the number of (meth) acryloyl groups contained in one molecule is preferably 3 or 4 (3 or 4 functional), and 3 (trifunctional). ) Is more preferable.
• the (meth) acryloyl group contained in the compound of the component (B) is preferably an acryloyl group.
• the (meth) acryloyl group contained in the compound of the component (B) is preferably a methacryloyl group.
• the component (B) preferably contains an ester monomer having three or more (meth) acryloyl groups (that is, a (meth) acrylate monomer). ..
• the preferred number of (meth) acryloyl groups contained in the (meth) acrylate monomer is the same as described above.
• the molecular weight of the compound of the component (B) is not particularly limited, but is preferably less than 1000, more preferably 600 or less, from the viewpoint of improving the curability of the photocurable resin composition. Further, from the viewpoint of excellent compatibility with the component (A), the molecular weight of the compound of the component (B) is preferably more than 200, more preferably 300 or more.
• the molecular weight of the compound (low molecular weight compound) can be measured by a known method such as gas chromatography-mass spectrometry (GC-MS). Further, the structure of the compound can be specified by a method such as NMR, and the molecular weight can be specified by performing a calculation based on the structure.
• component (B) contained in the photocurable resin composition according to the present invention include trimethylolpropane tri (meth) acrylate, trimethylolethanetri (meth) acrylate, and ethoxylated trimethylolpropane tri (meth).
• the component (B) preferably contains at least one selected from the group consisting of dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate and trimethylolpropane trimethacrylate.
• the component (B) one type alone or two or more types may be used in combination. When two or more kinds are used in combination, the content of the component (B) refers to the total amount.
• the content of the component (B) is preferably 20 to 80 parts by mass, more preferably 30 to 70 parts by mass with respect to 100 parts by mass of the component (A).
• the content of the component (B) is even more preferably 40 to 60 parts by mass with respect to 100 parts by mass of the component (A). ..
• the component (B) is 20 parts by mass or more with respect to 100 parts by mass of the component (A)
• the hardness of the cured product can be maintained satisfactorily.
• (B) is 80 parts by mass or less, the transparency of the cured product can be well maintained.
• the component (C) contained in the photocurable resin composition according to the present invention is a compound having a molecular weight of 200 or less and having a hydroxyl group and a methacryloyl group (however, the component (A) and the component (B) are excluded).
• both the transparency and glossiness of the cured product can be improved in a well-balanced manner.
• the molecular weight of the compound used as the component (C) is not particularly limited as long as it is 200 or less, but from the viewpoint of transparency, it is preferably 100 or more and 200 or less, more preferably 100 or more and 180 or less, and 100. More than 150 or less is particularly preferable.
• the compound of the component (C) may have two or more hydroxyl groups and / or two or more methacryloyl groups. However, from the viewpoint of transparency, it is preferable that the number of hydroxyl groups and methacryloyl groups contained in the compound of the component (C) is 2 or less, respectively. From the same viewpoint as above, the number of hydroxyl groups and methacryloyl groups contained in the compound of the component (C) is more preferably one.
• the component (C) may have a carboxy group, a phosphoric acid group, an epoxy group, and other functional groups in addition to the hydroxyl group and the methacryloyl group.
• the "hydroxyl group” contained in the component (C) does not include "-OH" contained in an oxo acid group such as a carboxy group or a phosphoric acid group.
• the component (C) preferably has a molecular weight of 200 or less and contains an ester monomer having a hydroxyl group and a methacryloyl group (that is, a methacrylate monomer).
• the preferred molecular weight of the methacrylate monomer and the preferred number of methacryloyl groups contained therein are the same as described above.
• the hydroxyl group contained in the compound of the component (C) is preferably contained as an alcohol skeleton or a phenol skeleton. Further, the substitution position of the hydroxyl group is not particularly limited and may be present at the end of the compound or may be present as a side chain (on the side chain). From the viewpoint of transparency, it is preferable that the hydroxyl group contained in the compound of the component (C) is contained (in the side chain) as a side chain of the compound.
• the hydroxyl group contained in the compound of the component (C) may be any of a primary hydroxyl group, a secondary hydroxyl group, and a tertiary hydroxyl group. Among them, from the viewpoint of transparency, a secondary hydroxyl group or a tertiary hydroxyl group is preferable, and a secondary hydroxyl group is more preferable. That is, the compound of the component (C) is preferably a secondary alcohol or a tertiary alcohol, and more preferably a secondary alcohol, from the viewpoint of transparency.
• the component (C) contained in the photocurable resin composition according to the present invention include 2-hydroxyethyl methacrylate (primary alcohol), 2-hydroxypropyl methacrylate (secondary alcohol), and 2-hydroxy.
• the component (C) one type alone or two or more types may be used in combination. When two or more kinds are used in combination, the content of the component (C) refers to the total amount.
• the content of the component (C) is preferably 1 to 50 parts by mass, more preferably 5 to 45 parts by mass with respect to 100 parts by mass of the component (A).
• the content of the component (C) is even more preferably 10 to 40 parts by mass with respect to 100 parts by mass of the component (A). Yes, particularly preferably 15 to 30 parts by mass.
• the component (C) is 1 part by mass or more with respect to 100 parts by mass of the component (A)
• the glossiness of the cured product can be maintained satisfactorily.
• the component (C) is 50 parts by mass or less, the transparency of the cured product can be well maintained.
• the component (D) contained in the photocurable resin composition according to the present invention is a photoinitiator (photopolymerization initiator).
• a radical photoinitiator that generates a radical species by irradiation with active energy rays such as visible light, ultraviolet rays, X-rays, and electron beams
• a cationic photoinitiator that generates a cation species, and an anion species
• anionic light generators that are generated, and among them, radical photoinitiators are preferable.
• radical photoinitiator examples include an alkylphenone-based compound, an acylphosphine oxide-based compound, a titanosen-based compound, an oxime ester-based compound, a benzoin-based compound, an acetophenone-based compound, a benzophenone-based compound, a thioxanthone-based compound, and an ⁇ -acyloxime ester.
• examples thereof include system compounds, phenylglioxylate compounds, benzyl compounds, azo compounds, diphenyl sulfide compounds, organic dye compounds, iron-phthalocyanine compounds, benzoin ether compounds, anthraquinone compounds and the like.
• alkylphenone-based compounds and acylphosphine oxide-based compounds are preferable from the viewpoint of reactivity and the like. That is, the component (D) is preferably an acylphosphine oxide-based photoinitiator and / or an alkylphenone-based photoinitiator.
• alkylphenone-based compound examples include 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-phenyl-propane-1-one, ⁇ -aminoalkylphenone and the like, and examples thereof include acylphosphine oxide-based compounds. Examples include 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide and bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide.
• the component (D) one type alone or two or more types may be used in combination. When two or more kinds are used in combination, the content of the component (D) refers to the total amount.
• the component (D) preferably contains an acylphosphine oxide-based photoinitiator and an alkylphenone-based photoinitiator.
• the content of the component (D) is preferably 0.1 to 15 parts by mass, more preferably 1 to 12 parts by mass with respect to 100 parts by mass of the component (A). It is by mass, and even more preferably 3 to 9 parts by mass.
• the component (D) is 0.1 part by mass or more with respect to 100 parts by mass of the component (A)
• the glossiness of the cured product can be maintained satisfactorily.
• the component (D) is 15 parts by mass or less, the transparency of the cured product can be well maintained.
• the photocurable resin composition according to the present invention is a compound having a (meth) acryloyl group in addition to the above components (A) to (D), as long as the object of the present invention is not impaired (however, (A) to (A) to (Excluding component (C)), fillers, conductive fillers, silane coupling agents, plasticizers, adhesives, defoamers, pigments, rust preventives, leveling agents, dispersants, rheology adjusters, flame retardants, etc. Additional additives may be included.
• examples of the compound having a (meth) acryloyl group that can be contained in addition to the component (A), the component (B), and the component (C) include the following monofunctional compounds. Examples thereof include (meth) acrylate compounds and bifunctional (meth) acrylate compounds.
• the (monofunctional) (meth) acrylate compound having one (meth) acryloyl group other than the component (A), the component (B), and the component (C) include lauryl (meth) acrylate and stearyl (meth).
• the (bifunctional) (meth) acrylate compound having two (meth) acryloyl groups other than the component (A), the component (B), and the component (C) include 1,3-butylene glycol di (meth). Acrylate, 1,4-butylene glycol di (meth) acrylate, tricyclodecanedimethanol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1,6-hexane glycol di (meth) acrylate, ethylene glycol diacrylate Late, 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
• Examples thereof include (meth) acrylate, neopentyl glycol-modified trimethylolpropandi (meth) acrylate, dicyclopentenyldi (meth) acrylate, ethylene oxide-modified dicyclopentenyldi (meth) acrylate, and diacryloyl isocyanurate. Not limited to.
• the photocurable resin composition according to the present invention is added to the above components (A) to (D) in addition to the above components (A) to (D) for the purpose of improving the elastic modulus, fluidity, etc. of the cured product, as long as the object of the present invention is not impaired.
• It may further contain a filler.
• the filler include inorganic powder, organic powder and the like.
• the filler for the inorganic powder examples 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. However, it is not limited to these. These may be used alone or in combination of two or more.
• the blending amount of the inorganic powder (when two or more kinds are contained, the total amount thereof) is preferably about 0.1 to 200 parts by mass with respect to 100 parts by mass of the component (A).
• Fused silica can be blended for the purpose of adjusting the viscosity of the photocurable resin composition or improving the mechanical strength of the cured product.
• fumed silica surface-treated with dimethylsilane, trimethylsilane, alkylsilane, methacryloyloxysilane, organochlorosilane, polydimethylsiloxane, hexamethyldisilazane and the like is used.
• fumed silica products include, for example, Aerosil® R972, R972V, R972CF, R974, R976, R976S, R9200, RX50, NAX50, NX90, RX200, RX300, R812, R812S, R8200, RY50, NY50.
• examples thereof include, but are not limited to, RY200S, RY200, RY300, R104, R106, R202, R805, R816, T805, R711, R7200, etc. (manufactured by Nippon Aerosil Co., Ltd.). These may be used alone or in combination of two or more.
• the filler for the organic powder examples 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 blending amount of the organic powder (when two or more kinds are contained, the total amount thereof) is preferably about 0.1 to 200 parts by mass with respect to 100 parts by mass of the component (A).
• the photocurable resin composition according to the present invention may further contain a conductive filler in addition to the above components (A) to (D) as long as the object of the present invention is not impaired.
• a conductive filler include, but are not limited to, gold, silver, platinum, nickel, palladium, and plated particles obtained by coating organic polymer particles with a metal thin film. These may be used alone or in combination of two or more.
• the photocurable resin composition according to the present invention may further contain a silane coupling agent in addition to the above components (A) to (D) as long as the object of the present invention is not impaired.
• a silane coupling agent include ⁇ -chloropropyltrimethoxysilane, octenyltrimethoxysilane, glycidoxyoctyltrimethoxysilane, ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxysilane, and ⁇ -glycidoxy.
• the content of the silane coupling agent (when two or more kinds are contained, the total amount thereof) is preferably 0.05 to 30 parts by mass, more preferably 0.2 to 10 parts by mass with respect to 100 parts by mass of the component (A). It is a mass part.
• the method for producing the photocurable resin composition according to the present invention is not particularly limited, and can be produced by a conventionally known method.
• the components (A) to (D) and the components (arbitrary components) to be added arbitrarily are weighed in predetermined amounts, added to the mixing pot sequentially or simultaneously in any order, and then added to a planetary mixer or the like.
• the production conditions are not particularly limited, but for the purpose of suppressing the increase in viscosity, it is preferable to carry out under light-shielding conditions, the mixing temperature is preferably 10 to 50 ° C., and the mixing time is set. , 0.1 to 5 hours is preferable.
• Another embodiment of the present invention is a cured product obtained by curing the photocurable resin composition (cured product of the photocurable resin composition).
• cured product a top coat used for nail color art can be mentioned.
• the cured product according to the present invention has excellent transparency and luster while having the hardness (hardness) required for coating nails or artificial nails.
• the hardness of the cured product obtained by curing the photocurable resin composition according to the present invention is preferably 70 or more (D70 or more) as measured by the method described in Examples. Further, it is preferable that the yellowness of the cured product measured by the method described in Examples is 1.25 or less. Further, it is preferable that the glossiness of the cured product measured by the method described in Examples is 80 or more when it is 60 ° and 70 or more when it is 20 °.
• the method for producing a cured product (for example, top coat, etc.) of the photocurable resin composition is not particularly limited, and a known method can be used. Of these, a method of curing the photocurable resin composition using active energy rays is preferable. That is, the present invention also provides a method for producing a cured product, which comprises irradiating the photocurable resin composition with active energy rays to cure it.
• the method for producing the cured product is not particularly limited, and a known method can be used.
• a method may be used in which the photocurable resin composition according to the present invention is molded into a desired shape and then irradiated with active energy rays (light or the like) to be cured.
• the irradiation light used for irradiating the active energy rays is not particularly limited, but usually, irradiation light in the wavelength range of 200 to 750 nm is preferable.
• the irradiation device is not particularly limited, and a known device can be used according to a desired wavelength.
• a low-pressure mercury lamp, a medium-pressure mercury lamp, a high-pressure mercury lamp, a xenon lamp, a metal halide lamp, an LED lamp, or the like can be used.
• a high-pressure mercury lamp or an LED lamp is preferable from the viewpoint of curability, curing efficiency, and the like.
• the irradiation time of the active energy ray is not particularly limited, but for example, when an LED lamp is used, it is preferably 15 to 120 seconds, and more preferably 20 to 70 seconds. Further, as the integrated light quantity is preferably 200 ⁇ 5000mJ / cm 2, more preferably 300 ⁇ 1500mJ / cm 2, particularly preferably 500 ⁇ 1000mJ / cm 2. In addition, at the time of curing, the active energy ray irradiation may be performed a plurality of times as needed.
• Another embodiment of the present invention comprises applying the photocurable resin composition onto a nail or an artificial nail to form a coating film, and then irradiating the nail with active energy rays to cure the coating film.
• This is a method of covering artificial nails.
• "applying on a nail or an artificial nail” means a form of applying directly to the surface of a human nail (ground nail) or an artificial nail (nail tip), or a human nail or an artificial nail. Includes a form of application to the outermost surface of a single or multiple other layers formed on the surface of the.
• a photocurable resin composition for nails or artificial nails containing the following components (A) to (D) is applied onto a nail (nail) or artificial nail to form a coating film.
• a method for coating a nail or an artificial nail which comprises irradiating the coating with active energy rays to cure the coating film.
• Component Compound having 3 or more (meth) acryloyl groups (excluding component (A))
• the 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 artificial nail also includes a resin base material (nail 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 may be formed so as to cover the nail, or may be formed larger than the nail for the purpose of extending the nail.
• an item (decorative tool) such as a stone for improving the aesthetic appearance may be formed for the purpose of adhering to the nail.
• the composition of the artificial nail is generally a base coat layer (a layer for the purpose of imparting adhesion to the nail, prevention of color transfer, etc.), a color layer (a layer for the purpose of decoration including a coloring material, etc.), It has a structure in which top coat layers (layers for the purpose of coating, imparting gloss, and improving aesthetics) are laminated in this order. Further, as the forming method, first, a base coat layer formed by curing a photocurable resin composition for a base coat is formed on the surface of a nail, and then a color layer formed by curing a photocurable resin composition for a color is formed on the base coat layer.
• a top coat layer formed by curing a photocurable resin composition for a top coat is formed on the top coat layer.
• the photocurable resin composition according to the present invention is not particularly limited as long as it is used for the purpose of forming a layer on a nail or an artificial nail, but it has good glossiness and transparency in a well-balanced manner. , It is preferable to use it as a photocurable resin composition for a top coat. That is, the photocurable resin composition according to the present invention is preferably for a top coat.
• the method of applying the photocurable resin composition and the method of curing the coating film (applied photocurable resin composition) are not particularly limited, and can be performed by a method known to those skilled in the art.
• the description regarding the method for producing a cured product described in the above [Cured product] section is incorporated.
• a preferable example of the method for covering (decorating) a nail or an artificial nail according to the present invention is shown below, but the method according to the present invention is not limited to this method.
• the photocurable resin composition according to the present invention When the photocurable resin composition according to the present invention is directly applied to nails, it is preferable to perform the following operations as necessary in order to improve the adhesion of the coating film. That is, it is preferable to sand the surface of the nail with a file (file) or the like before applying the photocurable resin composition. After that, it is preferable to remove dust, oil, water and the like with a nail solvent containing ethanol as a main component. Next, the photocurable resin composition according to the present invention is applied onto the nail so as to form a coating film having a thickness of 50 to 300 ⁇ m in a state before curing with a brush or a brush (formation of the coating film).
• a coating film is formed by applying the photocurable resin composition according to the present invention on another previously formed layer (cured film of resin for base coat, cured film of resin for color). May be good.
• a primer may be used in advance at the time of application.
• the coating film is irradiated with active energy rays to cure the coating film (coated photocurable resin composition).
• the device for irradiating the active energy rays at the time of curing is not particularly limited, but a commercially available UV lamp for nails, an LED lamp for nails, or the like can be used.
• the irradiation time of the active energy ray is preferably 15 to 120 seconds, and more preferably 20 to 70 seconds in consideration of the influence on the finger.
• the integrated light quantity is preferably 200 ⁇ 5000mJ / cm 2, more preferably 300 ⁇ 1500mJ / cm 2, particularly preferably 500 ⁇ 1000mJ / cm 2.
• the active energy ray irradiation may be performed a plurality of times as needed.
• Spacers are set at both ends of a 0.7 x 50 x 50 mm non-alkali glass plate (Corning Eagle XG (registered trademark)) so that the film thickness is about 0.1 mm, and a photocurable resin composition is placed on the glass plate. About 1.5 to 2 g of the substance was applied. Next, another non-alkali glass plate was put together to prevent air bubbles from entering the measurement site, and the four corners were pinched. The photocurable resin composition was left to stand for about 1 minute until the thickness of the applied photocurable resin composition became stable, and the squeezed resin was wiped off.
• the photocurable resin composition was cured using an LED lamp for nails (Lexia EX 30W wavelength 395 to 405 nm) to prepare two cured products for measurement (curing conditions: irradiation time 30 seconds, integrated light amount 750 mJ / cm 2 ).
• the absorbance of the two cured products for measurement was measured using an ultraviolet-visible spectrophotometer (UV-VIS) under the following measurement conditions. ..
• the yellowness was calculated using an Excel macro file for calculating the yellowness (YI value), and the average value of the two cured products was taken as the yellowness.
• the standard light was calculated using D65.
• the yellowness measured by the above procedure is preferably 1.25 or less, more preferably 1.20 or less, and particularly preferably 1.00 or less.
• the lower limit thereof is not particularly limited, but is substantially 0.01 or more.
• UV-VIS Ultraviolet-visible spectrophotometer
• Values at 60 ° and 20 ° were measured using a glossy checker (manufactured by HORIBA).
• the glossiness measured by the above procedure is preferably 80 or more at 60 ° and 70 or more at 20 °. Further, the glossiness is more preferably 85 or more at 60 ° and 75 or more at 20 °.
• the upper limit thereof is not particularly limited, but is substantially 90 or less at 60 ° and 88 or less at 20 °. In Table 1 below, it is described as "value at 60 ° / value at 20 °".
• a spacer having a thickness of 1 mm was placed on a blue plate glass having a thickness of 3.0 ⁇ 150 ⁇ 150 mm, and a photocurable resin composition was applied.
• a PET film is layered on top of it, another blue plate glass is layered on top of each other, a photocurable resin composition is sandwiched between them, and the surface of the two blue plate glasses is surfaced using a high-pressure mercury lamp (curing condition: integrated light amount 30 kJ / m 2).
• a cured product having a thickness of 1 mm was prepared by irradiating from the back surface and the back surface once, for a total of two times (curing was performed by adjusting the UV light transmitted through the PET film and the blue plate glass to the above curing conditions). ..
• Three cured products were prepared in the same manner as above, and left for 2 hours. Then, the blue plate glass and the PET film were peeled off, and three 1 mm-thick sheet-like cured products were stacked so that the side to which the PET film was attached faced up. The hardness of the sheet-like cured products stacked on the smooth surface was measured. At this time, the hardness was measured based on JIS K7215: 1986 using a type D durometer tester under the following measurement conditions.
• the measurement was performed 5 times, and the average value of 3 times excluding the maximum value and the minimum value was obtained.
• the hardness measured by the above procedure is preferably 70 or more, more preferably 75 or more, and particularly preferably 80 or more.
• the upper limit thereof is not particularly limited, but is substantially 100 or less.
• the photocurable resin composition according to the embodiment of the present invention is a photocurable resin composition having a low yellowness and excellent transparency and gloss when cured. Recognize.
• the component (C) is different between Examples 1 and 2, the yellowness at the time of curing is obtained by using a compound having a molecular weight of 200 or less and having a hydroxyl group and a methacryloyl group as the component (C). And, a photocurable resin composition satisfying the required values in terms of glossiness can be obtained.
• Example 1 a cured product having a low yellowness and a high glossiness can be obtained, and the hardness of the cured product is sufficiently high, so that the top coat can be obtained. It can be seen that the layer meets the required hardness.
• Comparative Example 1 in Comparative Example 1, as c'1, the molecular weight is 200 or less and the hydroxyl group is present, but the methacryloyl group is not present and the acryloyl group is present. It can be seen that the glossiness of the cured product is low when the compound is used. It can be seen that when Comparative Examples 2 to 4 use compounds having a molecular weight of 200 or less as c'2 to c'4, the cured product has a high yellowness and low transparency. Further, it can be seen that when the compounds having no hydroxyl group are used as c'5 to c'7 in Comparative Examples 5 to 7, the cured product has high yellowness and low transparency.
• Comparative Example 5 when a compound having a methacryloyl group as c'5 but not satisfying a molecular weight of 200 or less and having no hydroxyl group is used, the yellowness of the cured product is high and transparent. It turns out that the sex is low. Further, in Comparative Example 6, when a compound having a molecular weight of 200 or less, no hydroxyl group and no methacryloyl group, and an acryloyl group was used as c'6, the yellowness of the cured product was high and transparent. It can be seen that not only the property is low, but also the glossiness is insufficient.
• Comparative Example 7 when a compound having a molecular weight of 200 or less and having a methacryloyl group but not having a hydroxyl group is used as c'7, the yellowness of the cured product is high and the transparency is low. You can see that.
• Comparative Examples 8 to 10 when the composition does not contain the component (B), the hardness of the cured product is low and the hardness required for coating nails and artificial nails is not obtained.
• the photocurable resin composition according to one embodiment of the present invention has the hardness (hardness) necessary for coating nails and artificial nails, and can form a cured product having excellent transparency and luster. It can be widely used in the decorative field.

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• 2021
  • 2021-07-05 KR KR1020227043025A patent/KR20230041963A/ko active Pending
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