JP7357940B2 - Active energy ray curable composition and method for producing cold stamped products - Google Patents

Description

The present invention relates to an active energy ray-curable composition and a method for producing a cold stamped product.

Currently, in order to improve the design and appeal of recorded objects on which characters and the like are recorded, a layer having special optical properties such as a metal foil or a hologram is sometimes provided on the surface of the recorded object. As a method for providing a layer having such special optical properties, a cold stamping process is known in which a layer having special optical properties is transferred onto the surface of a recorded material. In the cold stamping process, an adhesive layer is placed on the surface of the recorded material, and a transfer base material is further placed on the adhesive layer. The transfer base material has a base sheet and a transfer layer laminated on the base sheet. By transferring this transfer layer to the adhesive layer, a recorded matter having the transfer layer can be obtained. Active energy ray-curable compositions are known as compositions for obtaining such stamped adhesive layers, as disclosed in Patent Documents 1 and 2.

Special Publication No. 2020-525620 JP2009-226880A

In the cold stamping process as described above, it is required that the transfer layer of the transfer base material be transferred with higher precision to the cured film obtained from the active energy ray-curable composition.

In order to solve the above problems, one aspect of the present invention provides an active energy ray-curable composition that is used for cold stamping processing and is cured by irradiation with active energy rays, the composition comprising (A) a radically polymerizable compound. , and (B) a photopolymerization initiator, the photopolymerization initiator (B) containing (B1) an acylphosphine oxide compound, and (B1) the acylphosphine oxide in the active energy ray-curable composition. The content of the system compound is within the range of 2.0% by mass or more and 11.0% by mass or less.

According to the present invention, it is possible to improve the transfer accuracy in cold stamping processing.

FIG. 3 is a diagram illustrating a method for evaluating transferability in cold stamping processing, in which (a) is a plan view showing a base material with a coating layer, and (b) is a plan view showing a base material with a low fluidity film. be. (a) is a plan view showing the first laminate, and (b) is a plan view showing the second laminate. (a) is a plan view showing an evaluation sample, and (b) is a schematic plan view showing an enlarged image of the evaluation sample.

An embodiment of an active energy ray-curable composition and a method for producing a cold stamped product will be described below.
The active energy ray-curable composition of this embodiment is used for cold stamping. The active energy ray-curable composition is cured by irradiation with active energy rays. The active energy ray-curable composition contains (A) a radically polymerizable compound and (B) a photopolymerization initiator.

<(A) Radical polymerizable compound>
A radically polymerizable compound is a compound that hardens through a polymerization reaction when irradiated with active energy rays. Examples of active energy rays include ultraviolet rays (UV) and electron beams (EB).

The radically polymerizable compound is a radically polymerizable compound having a monofunctional group or a polyfunctional group, and may be a monomer or an oligomer.
Examples of the radically polymerizable compound having a monofunctional group include (meth)acrylate. Examples of monofunctional (meth)acrylates include butylcyclohexanol acrylate, isobornyl acrylate, 2-methyl-2-ethyl-1,3-dioxolan-4-ylmethyl acrylate, tetrahydrofurfuryl acrylate, cyclohexyl acrylate, -t-Butylcyclohexyl acrylate, caprolactone-modified tetrahydrofurfuryl acrylate, acryloylmorpholine, 1,4-cyclohexanedimethanol monoacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, isobutyl acrylate, t- Butyl acrylate, isooctyl acrylate, isodecyl acrylate, tridecyl acrylate, 2-methoxyethyl acrylate, methoxytriethylene glycol acrylate, 2-ethoxyethyl acrylate, 3-methoxybutyl acrylate, ethoxyethoxyethyl acrylate, butoxyethyl acrylate, ethoxydiethylene glycol Acrylate, methoxydipropylene glycol acrylate, dipropylene glycol acrylate, β-carboxylethyl acrylate, ethyl diglycol acrylate, trimethylolpropane formal monoacrylate, imide acrylate, isoamyl acrylate, ethoxylated succinic acrylate, trifluoroethyl acrylate, and ω - Carboxypolycaprolactone monoacrylate.

Examples of the radically polymerizable compound having a polyfunctional group include di(meth)acrylate. Examples of the di(meth)acrylate include dipropylene glycol diacrylate, tridipropylene glycol diacrylate, butanediol diacrylate, dimethylol-tricyclodecane diacrylate, propoxylated bisphenol A di(meth)acrylate, and ethoxylated bisphenol A diacrylate. (meth)acrylate, cyclohexanedimethanol di(meth)acrylate, dimethyloldicyclopentane diacrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, 1,6-hexane Diol di(meth)acrylate, ethoxylated 1,6-hexanediol diacrylate, neopentyl glycol di(meth)acrylate, polypropylene glycol diacrylate, 1,4-butanediol di(meth)acrylate, 1,9-nonanediol Diacrylate, tetraethylene glycol diacrylate, 2-n-butyl-2-ethyl-1,3-propanediol diacrylate, hydroxypivalic acid neopentyl glycol diacrylate, 1,3-butylene glycol di(meth)acrylate, ethoxy ethoxylated tripropylene glycol diacrylate, neopentyl glycol modified trimethylolpropane diacrylate, stearic acid modified pentaerythritol diacrylate, ethoxylated neopentyl glycol di(meth)acrylate, propoxylated neopentyl glycol di(meth)acrylate, and tripropylene Examples include glycol di(meth)acrylate.

Further examples of the radically polymerizable compound having a polyfunctional group include triacrylate, tetraacrylate, hexaacrylate, and oligoacrylate. Examples of the triacrylate include trimethylolpropane triacrylate, hydroxypivalic acid trimethylolpropane triacrylate, ethoxylated phosphoric acid triacrylate, ethoxylated isocyanuric acid triacrylate, tri(2-hydroxyethyl isocyanurate) triacrylate, penta Examples include erythritol triacrylate, tetramethylolpropane triacrylate, tetramethylolmethane triacrylate, caprolactone-modified trimethylolpropane triacrylate, propoxylate glyceryl triacrylate, ethoxylated trimethylolpropane triacrylate, and propoxylated trimethylolpropane triacrylate. Examples of the tetraacrylate include pentaerythritol tetraacrylate, tetramethylolmethane tetraacrylate, pentaerythritol tetraacrylate, ditrimethylolpropane tetraacrylate, and ethoxylated pentaerythritol tetraacrylate. Examples of pentaacrylate include dipentaerythritol hydroxypentaacrylate. Examples of the hexaacrylate include dipentaerythritol hexaacrylate and caprolactone-modified dipentaerythritol hexaacrylate. Examples of oligoacrylates include neopentyl glycol oligoacrylate, 1,4-butanediol oligoacrylate, 1,6-hexanediol oligoacrylate, trimethylolpropane oligoacrylate, and pentaerythritol oligoacrylate.

Furthermore, examples of radically polymerizable compounds include oligomers formed from the above-mentioned monomers, epoxy (meth)acrylates, oxetane (meth)acrylates, cyclic or linear aliphatic urethane (meth)acrylates, aromatic urethanes ( Examples include meth)acrylate, polyether (meth)acrylate, and polyester (meth)acrylate.

One type or two or more types of radically polymerizable compounds can be used. Note that (meth)acrylate refers to methacrylate or acrylate.
The number of functional groups in the radically polymerizable compound is preferably 1 to 3 from the viewpoint of lowering the viscosity of the active energy ray-curable composition.

The radically polymerizable compound preferably contains at least one polymerizable compound selected from the following (A1) first polymerizable compound, (A2) second polymerizable compound, and (A3) third polymerizable compound. In this case, it becomes easy to obtain a cured film that exhibits excellent reactivity upon irradiation with active energy rays and has appropriate flexibility during stamping.

(A1) The first polymerizable compound is a compound having an ether group, which is at least one of a vinyl ether group and an allyl ether group, and a (meth)acryloyl group. (A2) The second polymerizable compound is a (meth)acrylate compound having an aromatic skeleton. (A3) The third polymerizable compound is at least one compound selected from alkanediol (meth)acrylate compounds, alkylene glycol di(meth)acrylate compounds, and alkoxylated alkanediol (meth)acrylate compounds.

(A1) As the first polymerizable compound, for example, 2-(2-vinyloxyethoxy)ethyl acrylate (manufactured by Nippon Shokubai Co., Ltd., trade name: VEEA), 2-(2-vinyloxyethoxy)ethyl methacrylate ( Examples include Nippon Shokubai Co., Ltd., trade name: VEEM), and methyl 2-(allyloxymethyl)acrylate (Nippon Shokubai Co., Ltd., trade name: AOMA (FX-AO-MA)).

(A2) Examples of the second polymerizable compound include benzyl (meth)acrylate, methylphenoxyethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, phenoxypolyethylene glycol (meth)acrylate, and phenoxypolypropylene glycol (meth)acrylate. acrylate, phenoxypolyethylene polypropylene glycol (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, and 2-hydroxy-3-phenoxypropyl (meth)acrylate.

(A3) Examples of the third polymerizable compound include 1,3-butylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, dodecane di(meth)acrylate , dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, and alkoxylated hexanediol di(meth)acrylate.

The content of the radically polymerizable compound in the active energy ray-curable composition is preferably 60% by mass or more, more preferably 70% by mass or more, and still more preferably 75% by mass or more. The content of the polymerizable compound in the active energy ray-curable composition is preferably 98% by mass or less, more preferably 95% by mass or less, and still more preferably 89% by mass or less.

<(B) Photopolymerization initiator>
A photopolymerization initiator initiates a polymerization reaction of a radically polymerizable compound by irradiation with active energy rays. As the photopolymerization initiator, a photoradical polymerization type photopolymerization initiator can be used. Examples of photo-radical polymerization type photopolymerization initiators include intramolecular cleavage type photopolymerization initiators and hydrogen abstraction type photopolymerization initiators. One type or two or more types of photopolymerization initiators can be used.

(B) The photopolymerization initiator includes (B1) an acylphosphine oxide compound. (B1) Examples of the acylphosphine oxide compounds include 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, and phenyl(2,4, Examples include ethyl 6-trimethylbenzoyl)phosphinate and ethyl (3-benzoyl-2,4,6-trimethylbenzoyl)(phenyl)phosphine oxide. (B1) One type or two or more types of acylphosphine oxide compounds can be used.

The content of the acylphosphine oxide compound (B1) in the active energy ray-curable composition is in the range of 2.0% by mass or more and 11.0% by mass or less, preferably 2.3% by mass or more, It is within the range of 8.5% by mass or less, and more preferably within the range of 2.6% by mass or more and 7.0% by mass or less. When the content of the acylphosphine oxide compound (B1) in the active energy ray-curable composition is 2.0% by mass or more, the fluidity of the coated layer is likely to be reduced by irradiating the coated layer with active energy rays. Become. A low-fluidity film obtained by reducing the fluidity of the coating layer in this manner tends to maintain its shape when a transfer base material is placed on the coating layer. On the other hand, when the content of the acylphosphine oxide compound (B1) in the active energy ray-curable composition is 11.0% by mass or less, when the coating layer is irradiated with active energy rays, the coating layer is rapidly cured. Progress can be prevented. This makes it easier to maintain the flexibility and adhesiveness of the low-fluidity film, thereby improving transferability.

(B) The photopolymerization initiator preferably further contains (B2) a sulfur-based compound. (B2) The sulfur-based compound is at least one of a sulfone-based compound and a thiobenzoyl-based compound. Examples of sulfone compounds include 1-[4-(4-benzoylphenylsulfanyl)phenyl]-2-methyl-2-(4-methylphenylsulfonyl)propan-1-one and tribromomethylphenylsulfone. It will be done. Examples of thiobenzoyl compounds include 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 4-benzoyl 4'-methyldiphenyl sulfide, and 1-[4- (Phenylthio)phenyl]-octane-1,2-dione-2-(O-benzoyloxime) is mentioned.

The content of the sulfur-based compound (B2) in the active energy ray-curable composition is preferably 0.4% by mass or more. In this case, the fluidity of the coating layer can be easily reduced by irradiating the coating layer with active energy rays.

(B) The photopolymerization initiator preferably further includes (B3) a thioxanthone compound. (B3) Thioxanthone compounds include, for example, thioxanthone, 2-chlorothioxanthone, 2,4-dichlorothioxanthone, 2-methylthioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, isopropylthioxanthone, and 2- Isopropylthioxanthone is mentioned. The content of the thioxanthone compound (B3) in the active energy ray-curable composition is preferably 0.8% by mass or less, more preferably 0.5% by mass or less, and even more preferably 0.3% by mass. % by mass or less.

The photopolymerization initiator may contain compounds other than those listed above, if necessary. Examples of compounds other than those mentioned above in the photopolymerization initiator include alkylphenone compounds, imidazole compounds, and triazine compounds. However, as the photopolymerization initiator, it is preferable to select and use one that does not easily affect the color tone of the cured film obtained by curing the active energy ray-curable composition. In particular, in the case of an active energy ray-curable composition that forms a transparent cured film that does not contain a colorant, it is preferable to select and use a photopolymerization initiator that does not cause coloration such as yellowing of the cured film.

Examples of alkylphenone compounds include 2,2-dimethoxy-1,2-diphenylethan-1-one, 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one, 2-hydroxy-1-{4-[4-{2-hydroxy-2- Methylpropionyl}-benzyl]-phenyl}-2-methylpropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, and 2-dimethylamino-2 -(4-methylbenzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one.

Examples of imidazole compounds include 2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis(2-chlorophenyl) -4,4',5,5'-tetraphenyl-1,2'-biimidazole, and 2,2',4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4' , 5'-diphenyl-1,1'-biimidazole.

Examples of triazine compounds include 2-[2-(4-methoxyphenyl)ethenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine and 2-[4'-ethyl(1 , 1'-biphenyl)-4-yl]-4,6-bis(trichloromethyl)-1,3,5-triazine.

The content of the photopolymerization initiator in the active energy ray-curable composition is preferably 2.0% by mass or more, more preferably 2.3% by mass or more, and even more preferably 2.6% by mass. That's all. The content of the photopolymerization initiator in the active energy ray-curable composition is preferably 20% by mass or less, more preferably 18% by mass or less, and still more preferably 15% by mass or less.

<Ingredients other than the above>
The active energy ray-curable composition preferably contains (C) an amine compound.
Examples of the (C) amine compound include (C1) an amino-modified compound, (C2) an aromatic amine compound, and (C3) an aliphatic amine compound.

(C1) The amino-modified compound is at least one of an amino-modified acrylate oligomer and an amino-modified acrylate polymer. (C1) Amino-modified compounds include, for example, commercial products manufactured by Daicel Allnex Corporation (product names: EBECRYL80, EBECRYL7100), commercial products manufactured by Toagosei Co., Ltd. (product name: Aron DA), and commercial products manufactured by KJ Chemicals. (Product name: DMAPAA), commercial products manufactured by RAHN (Product names: GENOMER5142, GENOMER5161, GENOMER5271, GENOMER5275, GENOMER5695), and commercial products manufactured by Sartomer (Product names: CN383, CN371NS, CN386, CN5) 49NS, CN550, CN551NS , CN373).

(C2) Aromatic amine compounds include, for example, p-diethylaminoacetophenone, ethyl p-dimethylaminobenzoate, isoamyl p-dimethylaminobenzoate, {α-4-(dimethylamino)benzoylpoly(oxyethylene)- Poly[oxy(1-methylethylene)]-poly(oxyethylene)}4-(dimethylamino)-benzoate, poly(ethylene glycol) bis(p-dimethylaminobenzoate), N,N-dimethylbenzylamine, (methyl Examples include amino) diethane-2,1-diylbis[4-(dimethylamino)-benzoate] and 4,4'-bis(diethylamino)benzophenone.

(C3) Aliphatic amine compounds include, for example, trimethylamine, methyldimethanolamine, triethanolamine, and N-methyldiethanolamine.
(C) The amine compound preferably contains at least one of (C1) an amino-modified compound and (C2) an aromatic amine compound.

The content of the amine compound (C) in the active energy ray-curable composition is preferably 0.1% by mass or more. The content of the amine compound (C) in the active energy ray-curable composition is preferably 20% by mass or less. The content of the amine compound (C) in the active energy ray-curable composition is more preferably in the range of 0.5% by mass or more and 15% by mass or less, and even more preferably 1.0% by mass. The content is within the range of 10% by mass or less.

The active energy ray-curable composition can also contain a polymer. Examples of the polymer include (meth)acrylic resin, epoxy resin, ketone resin, diallyl phthalate resin, chlorinated polyolefin resin, vinyl chloride resin, polyvinyl acetal resin, and polyester resin. One type or two or more types of polymers can be used.

Examples of (meth)acrylic resins include copolymers of methyl methacrylate and n-butyl methacrylate, methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, and isobutyl (meth)acrylate. , t-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, and cyclohexyl (meth)acrylate.

Examples of the (meth)acrylic resin include commercially available products manufactured by Mitsubishi Rayon Co., Ltd. (product names: Dianal BR, Dianal HR, Dianal HW, Dianal LP, Dianal LR, Dianal LW, Dianal LX, Diamond Naal SE), commercial products manufactured by Hitachi Chemical Co., Ltd. (product names: Hitaloid 7975, Hitaloid 7988, Hitaloid 7975D), commercial products manufactured by Negami Kogyo Co., Ltd. (product names: Hypal M-4006, Hyperal M-4501, Hyperal M-) 5000, Hyperal M-5001), and commercial products manufactured by Arakawa Chemical Co., Ltd. (product names: Beam Set 243NS, Beam Set 255, Beam Set 261, Beam Set 271).

Examples of the epoxy resin include bisphenol A type and bisphenol F type.
Examples of the ketone resin include a ketone/aldehyde condensation resin, a ketone resin obtained by reacting an aldehyde compound such as formaldehyde, and a urethane-modified ketone resin. Examples of the ketone resin include commercial products manufactured by Arakawa Chemical Co., Ltd. (trade name: K-90) and commercial products manufactured by EVONIK Industries AG (trade names: VariPlus AP, VariPlus SK, VariPlus 1201TF, VariPlus CA). It will be done.

Examples of the diallyl phthalate resin include commercial products manufactured by Osaka Soda Co., Ltd. (trade names: Daiso Dapp, Daiso Isodap, Daiso Dapp Monomer, Daiso Dapp 100 Monomer).

Examples of the chlorinated polyolefin resin include commercial products manufactured by Nippon Paper Industries (Superchron 814HS, Superchron 390S), and commercial products manufactured by Toyobo (trade names: Hardren 13-LLP, Hardren 15-LLP). . Examples of vinyl chloride resins include commercial products manufactured by Nissin Chemical Industries, Ltd. (product names: Solvine CL, Solvine CNL, Solvine C5R, Solvine TA5R), and commercial products manufactured by Kaneka Corporation (product name: Kanevinyl M series). , Kanevinyl HM series, Kanevinyl T5 series).

Examples of the polyvinyl acetal resin include commercial products manufactured by Sekisui Chemical Co., Ltd. (trade names: S-LEC B, S-LEC KX, S-LEC KW). Examples of polyester resins include commercial products manufactured by Takamatsu Yushi Co., Ltd. (product names: Pesresin A series, Pesresin S series) and commercial products manufactured by Toyobo Co., Ltd. (product names: Byron 103, Byron 200, Byron 220). .

The content of the polymer in the active energy ray-curable composition is preferably 0.1 parts by mass or more, more preferably 1 part by mass or more, and even more preferably is 3 parts by mass or more. The content of the polymer in the active energy ray-curable composition is preferably 20 parts by mass or less, more preferably 15 parts by mass or less, and even more preferably 10 parts by mass, based on 100 parts by mass of the radically polymerizable compound. Parts by mass or less.

The active energy ray-curable composition can also contain a surface tension regulator. The surface tension adjuster is a compound that can adjust the surface tension of the active energy ray-curable composition to a predetermined range. Examples of surface tension modifiers include ionic surfactants, nonionic surfactants, modified silicone oils, and organic solvents.

Examples of the anionic surfactant of the ionic surfactant include fatty acid salts, alkyl sulfate ester salts, benzene sulfonates, naphthalene sulfonates, sulfosuccinate ester salts, polyoxyethylene sulfate ester salts, and phosphate esters. Examples include salts.

Examples of fatty acid salts include sodium stearate, potassium oleate, and sodium semi-hardened beef tallow fatty acid.
Examples of the alkyl sulfate ester salts include sodium dodecyl sulfate, tri(2-hydroxyethyl) ammonium dodecyl sulfate, and sodium octadecyl sulfate.

Examples of the benzenesulfonic acid salts include sodium nonylbenzenesulfonate, sodium dodecylbenzenesulfonate, sodium octadecylbenzenesulfonate, and sodium dodecyl diphenyl ether disulfonate.

Examples of naphthalene sulfonate salts include sodium dodecylnaphthalene sulfonate and naphthalene sulfonic acid formalin condensate.
Examples of the sulfosuccinic acid ester salts include didodecyl sodium sulfosuccinate and dioctadecyl sodium sulfosuccinate.

Examples of polyoxyethylene sulfate salts include sodium polyoxyethylene dodecyl ether sulfate, tri(2-hydroxyethyl) ammonium polyoxyethylene dodecyl ether sulfate, sodium polyoxyethylene octadecyl ether sulfate, and polyoxyethylene dodecyl ether sulfate. Examples include sodium.

Examples of phosphate ester salts include potassium dodecyl phosphate and sodium octadecyl phosphate.
Examples of the cationic surfactant of the ionic surfactant include quaternary ammonium salts. Examples of quaternary ammonium salts include octadecyl ammonium acetate, alkyl amine salts such as coconut oil amine acetate, dodecyltrimethylammonium chloride, octadecyltrimethylammonium chloride, diotadecyldimethylammonium chloride, and dodecylbenzyldimethylammonium chloride. .

Examples of the zwitterionic surfactant of the ionic surfactant include alkyl betaines and amine oxides. Examples of alkyl betaines include dodecyl betaine and octadecyl betaine. Examples of amine oxides include dodecyldimethylamine oxide.

Examples of the nonionic surfactant include polyoxyethylene alkyl ethers, polyoxyethylene phenyl ethers, oxirane polymers, sorbitan fatty acid esters, sorbitol fatty acid esters, and glycerin fatty acid esters.

Examples of polyoxyethylene alkyl ethers include polyoxyethylene dodecyl ether, polyoxyethylene hexadecyl ether, polyoxyethylene octadecyl ether, and polyoxyethylene (9-octadecenyl) ether.

Examples of polyoxyethylene phenyl ethers include polyoxyethylene octylphenyl ether and polyoxyethylene nonylphenyl ether.
Oxirane polymers include, for example, polyethylene oxide and co-polyethylene oxide propylene oxide.

Examples of sorbitan fatty acid esters include sorbitan dodecanoate, sorbitan hexadecanoate, sorbitan octadecanoate, sorbitan (9-octadecenoate) ester, sorbitan (9-octadecenoate) triester, and polyoxyethylene sorbitan dodecanoate. , polyoxyethylene sorbitan hexadecanoate ester, polyoxyethylene sorbitan octadecanoate ester, polyoxyethylene sorbitan octadecanoate triester, polyoxyethylene sorbitan (9-octadecenoic acid) ester, and polyoxyethylene sorbitan (9-octadecenoic acid) triester Examples include esters.

Examples of sorbitol fatty acid esters include polyoxyethylene sorbitol (9-octadecenoic acid) tetraester.
Examples of glycerin fatty acid esters include glycerin octadecanoic acid ester and glycerin (9-octadecenoic acid) ester.

Examples of the modified silicone oil include polyether-modified silicone oil, methylstyrene-modified silicone oil, olefin-modified silicone oil, alcohol-modified silicone oil, and alkyl-modified silicone oil. Among the modified silicone oils, it is preferable to use modified silicone oils into which various organic groups have been introduced since they exhibit good solubility in active energy ray-curable compositions. Examples of the modified silicone oil into which various organic groups are introduced include terminal (meth)acrylic modified silicone oil and terminal epoxy modified silicone oil.

The modified silicone oil does not excessively bleed onto the surface of the cured film formed on the base material. Therefore, stickiness on the surface of the cured film and migration of oil through the surface of the cured film can be suppressed. Among the modified silicone oils, compounds that are cured by active energy ray-curable irradiation are preferred, such as silicone polyether acrylate, polyether-modified siloxane copolymers, and epoxy-modified silicone oils.

Examples of the organic solvent include esters, ketones, cyclic ethers, amides, aromatic hydrocarbons, glycol ethers, diethylene glycol esters, aliphatic hydrocarbons, and alcohols.

Examples of esters include ethyl acetate, butyl acetate, isopropyl acetate, isobutyl acetate, cellosolve acetate, and propylene glycol methyl ether acetate.

Ketones include acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone. Examples of the cyclic ethers include tetrahydrofuran and dioxane. Examples of amides include N,N-dimethylformamide and N,N-dimethylacetamide.

Examples of aromatic hydrocarbons include xylene, toluene, and solvent naphtha.
Examples of glycol ethers include propylene glycol methyl ether and ethyl cellosolve.

Examples of diethylene glycol esters include carbitol acetate.
Aliphatic hydrocarbons include n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, n-undecane, n-dodecane, and mineral spirits.

Examples of alcohols include methyl alcohol, ethyl alcohol, and propyl alcohol.
The content of the surface tension modifier in the active energy ray-curable composition is preferably 0.001% by mass or more, more preferably 0.01% by mass or more. The content of the surface tension regulator in the active energy ray-curable composition is preferably 5% by mass or less, more preferably 3% by mass or less.

The active energy ray-curable composition can also contain a polymerization inhibitor. Examples of the polymerization inhibitor include hindered phenol compounds, hindered amine compounds, nitrosamine compounds, hydroquinone compounds, benzoquinone compounds, phosphorus compounds, and sulfur compounds.

The active energy ray-curable composition can also contain a filler. By containing a filler, the surface slipperiness and abrasion resistance of the cured film can be improved. Moreover, by containing a filler, a matte cured film can be obtained. Examples of fillers include extender pigments and resin beads. Examples of extender pigments include calcium carbonate, spherical silica, and hollow silica.

The active energy ray-curable composition can also contain a coloring component. Examples of coloring components include pigments and dyes. The pigment may be an organic pigment or an inorganic pigment. Examples of inorganic pigments include carbon black, iron oxide, titanium oxide, and calcium carbonate. Examples of organic pigments include azo pigments, lake pigments, phthalocyanine pigments, quinacridone pigments, dioxazine pigments, perylene red pigments, isoindolinone pigments, pyranthrone pigments, thioindigo pigments, benzimidazolone pigments, and quinophthalone pigments. Examples include organic pigments and isoindoline pigments. Examples of dyes include direct dyes, reactive dyes, acid dyes, cationic dyes, naphthol dyes, and disperse dyes.

When the active energy ray-curable composition contains a filler or a coloring component, a dispersant can be used as necessary. Examples of the dispersant include a polymer type dispersant and a low molecular type dispersant.

It is preferable that the active energy ray-curable composition does not contain a pigment from the viewpoint of further improving transfer accuracy in cold stamping processing.
<Substrate to which active energy ray curable composition is applied>
The substrate to which the active energy ray-curable composition is applied is not particularly limited. Examples of the base material include a paper base material, a resin base material, a metal base material, a glass base material, a rubber base material, and a ceramic base material. Paper substrates include, for example, coated paper, art paper, lightly coated paper, high quality paper, and synthetic paper. Examples of the resin of the resin base material include polyethylene resin, polyester resin, polypropylene resin, acrylic resin, polyamide resin, polycarbonate resin, polystyrene resin, and vinyl chloride resin. Examples of the shape of the resin base material include films, sheets, plates, and other molded products. Examples of the metal of the metal base material include stainless steel, aluminum, iron, and copper. Examples of the shape of the metal base material include plates and other molded products.

The substrate to which the active energy ray-curable composition is applied may be a recorded material on which information such as characters, photographs, illustrations, figures, or symbols is recorded. The method of recording information is not particularly limited. Examples of information recording methods include inkjet printing, offset printing, toner printing, flexographic printing, sublimation printing, gravure printing, silk screen printing, pad printing, spray coating, and brush and brush coating.

The base material may be a base material made of a composite of different materials. An example of a base material made of a composite of different materials is a vapor-deposited film in which metals or ceramics are vapor-deposited on a resin film.
<Method for manufacturing cold stamped products>
Next, a method for manufacturing a cold stamped product will be explained. In the method for producing a cold stamped product, the active energy ray-curable composition described above is used. The method for manufacturing a cold stamped product includes a coating layer forming step, a first irradiation step, a laminate forming step, and a second irradiation step.

In the coating layer forming step, a coating layer is formed on the substrate by coating the active energy ray-curable composition on the substrate. Examples of methods for forming the coating layer on the substrate include inkjet printing, offset printing, roll coater printing, flexographic printing, gravure printing, silk screen printing, pad printing, spray coating, and brush coating. The active energy ray-curable composition of this embodiment can be suitably used for inkjet printing.

The thickness of the coating layer obtained by applying the active energy ray-curable composition of the present embodiment to a base material can be appropriately selected depending on the shape to be drawn, the application, etc., and for example, the thickness may be 100 μm or less, or 85 μm or less. There may be. A coating layer having such a thickness can be easily formed by applying it to a base material by inkjet printing.

In the first irradiation step, the coating layer is irradiated with active energy rays to obtain a low-fluidity film with reduced fluidity. In the laminate forming step, the transfer base material is laminated on the low fluidity film to form a laminate in which the transfer layer of the transfer base material and the low fluidity film are in contact with each other.

In the second irradiation step, the low fluidity film of the laminate is irradiated with active energy rays to form a cured film in which the low fluidity film is cured. The active energy rays pass through the transfer base material and are irradiated onto the low fluidity membrane.

The wavelength of the active energy ray used in the first irradiation step and the wavelength of the active energy ray used in the second irradiation step may be the same wavelength or different wavelengths. It is preferable that the active energy rays used in the first irradiation step and the second irradiation step both have a wavelength within the range of 280 nm or more and 420 nm or less. The active energy ray used in the first irradiation step and the second irradiation step may be within the range of 350 nm or more and 420 nm or less, from the viewpoint of allowing the (B1) acylphosphine oxide compound to react more selectively. good.

In the method for producing a cold stamped product, a cold stamped pink product can be obtained by adhering the transfer layer of the transfer base material to the cured film of the laminate. This method for producing a cold stamped product uses a transfer base material that includes a base sheet and a transfer layer that can be peeled off from the base sheet. Examples of the transfer layer of the transfer base material include a metal vapor deposition layer and a hologram layer. The material and shape of the transfer base material are not particularly limited. The method for producing a cold stamped product using this transfer base material includes a step of peeling the base sheet from the laminate after the second irradiation step. As a result, a cold stamped product having a base material, a cured film, and a transfer layer is obtained. Furthermore, in the method for producing a cold stamped product, a cold stamped product can also be obtained by transferring the surface shape of the transfer layer of the transfer base material to the cured film of the laminate. This method of manufacturing a cold stamped product uses a transfer base material that includes a base sheet and a transfer layer that serves as a mold for transferring the uneven shape to the cured film. The material of the transfer base material, the overall shape, and the uneven shape of the transfer layer are not particularly limited. The method for manufacturing a cold stamped product using this transfer base material includes a step of peeling the transfer sheet from the laminate after the second irradiation step. As a result, a cold stamped product having a base material and a cured film having an uneven shape transferred to its surface is obtained.

<Actions and effects of this embodiment>
Next, the functions and effects of this embodiment will be explained.
(1) The active energy ray curable composition is used for cold stamping processing, and is cured by irradiation with active energy rays. The active energy ray-curable composition contains (A) a radically polymerizable compound and (B) a photopolymerization initiator. (B) The photopolymerization initiator includes (B1) an acylphosphine oxide compound. The content of the acylphosphine oxide compound (B1) in the active energy ray-curable composition is within the range of 2.0% by mass or more and 11.0% by mass or less.

According to this configuration, it is possible to improve the transfer accuracy in cold stamping processing. Specifically, as described above, when the content of the acylphosphine oxide compound (B1) is 2.0% by mass or more, the fluidity of the coating layer is likely to be reduced by irradiating the coating layer with active energy rays. Become. A low-fluidity film obtained by reducing the fluidity of the coating layer in this manner tends to maintain its shape when a transfer base material is placed on the coating layer. On the other hand, as described above, when the content of the acylphosphine oxide compound (B1) is 11.0% by mass or less, when the coating layer is irradiated with active energy rays, the hardening of the coating layer is suppressed from progressing rapidly. be able to. This makes it easier to maintain the flexibility and adhesiveness of the low-fluidity film, thereby improving transferability. As a result, even when performing cold stamping on delicate shapes, even in the case of cold stamping, every detail will adhere to the transfer base material, resulting in poor adhesion of the transfer layer on the transfer base material and transfer abnormalities due to uneven shapes on the transfer layer. It becomes difficult to do. That is, it is possible to realize highly accurate transfer along the outer shape of the coating layer.

Moreover, the radically polymerizable compound (A) contained in the active energy ray-curable composition is cheaper and more versatile than the cationic polymerizable compound. Therefore, in the active energy ray-curable composition of the present embodiment, it is possible to reduce the amount of a relatively expensive cationically polymerizable compound or a photoacid generator used for polymerizing the cationically polymerizable compound. This makes it possible to reduce the cost of cold stamped products.

(2) (A) The radical polymerizable compound is at least one polymerizable compound selected from the above-mentioned (A1) first polymerizable compound, (A2) second polymerizable compound, and (A3) third polymerizable compound. It is preferable to include. In this case, the reactivity upon irradiation with active energy rays is excellent, and the flexibility of the low-fluidity membrane obtained by irradiation with active energy rays can be increased. Therefore, it is possible to further improve the transfer accuracy in cold stamping processing.

(3) It is preferable that the photopolymerization initiator (B) further contains the above-mentioned (B2) sulfur-based compound. In this case, even if the thickness of the coating layer of the active energy ray-curable composition is relatively thin, it is possible to obtain good curability. Therefore, it can be suitably used, for example, in inkjet printing applications in which a coating layer is formed by inkjet printing.

(4) It is preferable that the photopolymerization initiator (B) further contains (B3) a thioxanthone compound. In this case, for example, it becomes possible to improve the adhesion between the low-fluidity film obtained by irradiating the coating layer with active energy rays and the transfer base material. Therefore, it is possible to further improve the transfer accuracy in cold stamping processing. Here, when the content of the (B3) thioxanthone compound in the active energy ray-curable composition is 0.8% by mass or less, for example, a low fluidity film obtained by irradiating the coating layer with active energy rays is used. It is possible to suppress a decrease in flexibility or adhesiveness of the material. This makes it possible to further improve the transfer accuracy in cold stamping.

(5) The active energy ray-curable composition preferably further contains (C) an amine compound. In this case, it becomes possible to improve the curability of the active energy ray-curable composition. To explain in detail, the radical polymerization of the radically polymerizable compound (A) is likely to be inhibited by oxygen dissolved in the active energy ray-curable composition or oxygen in the atmosphere. In this respect, the amine compound (C) is presumed to reduce inhibition of radical polymerization due to oxygen. That is, the amine compound (C) is presumed to improve the curability of the active energy ray-curable composition by promoting the reaction by the photopolymerization initiator (B).

For example, when the active energy ray-curable composition contains the above-mentioned (B2) sulfur-based compound, the sulfone-based compound of the sulfur-based compound (B2) has a sulfur atom that serves as a radical generation point, and thus has a reactive property. It is assumed that a high amount of sulfonic acid radicals are generated. (B2) It is presumed that the sulfur-based compound thiobenzoyl-based compound generates highly reactive thio radicals by having a sulfur atom in the conjugated system connected to the ketone group of the thiobenzoyl group, which serves as a radical generation point. For example, when the active energy ray-curable composition contains (B3) a thioxanthone-based compound, the thioxanthone-based compound (B3) has a sulfur atom in a conjugated system connected to a ketone group that serves as a radical generation point. It is assumed that highly reactive thio radicals are generated.

The actions of (B2) the sulfur-based compound and (B3) the thioxanthone-based compound are promoted by the (C) amine-based compound. Specifically, the amine compound (C) promotes a hydrogen abstraction type radical generation reaction. Furthermore, it is presumed that thiols and sulfonated products are generated by the hydrogen of the amine compound (C), and these thiols and sulfonated products further promote radical reactions as chain transfer agents.

(6) The amine compound (C) preferably contains at least one of the above-mentioned (C1) amino-modified compound and (C2) aromatic amine compound. In this case, it becomes possible to further improve the curability of the active energy ray-curable composition.

(7) The number of functional groups in the radically polymerizable compound (A) is preferably 1 to 3. In this case, it becomes possible to reduce the viscosity of the active energy ray-curable composition. Therefore, for example, when the active energy ray-curable composition is used for application to a substrate by inkjet printing, the ejection properties from the inkjet head can be improved.

(8) The active energy ray-curable composition preferably does not contain a pigment. In this case, it becomes possible to further improve the transfer accuracy in the cold stamping process. Furthermore, since the reactivity due to irradiation with active energy rays can be increased, energy consumption can be suppressed.

(9) The active energy ray-curable composition is preferably used for inkjet printing. In this case, cold stamping can be efficiently performed by efficiently obtaining a thinner cured film.

(10) By incorporating a polymer into the active energy ray curable composition, for example, the curability of the active energy ray curable composition, the glossiness of the cured film, the flexibility of the cured film, and the relationship between the base material and the cured film can be improved. It becomes possible to improve performance such as adhesion.

(11) A method for producing a cold stamped product uses the active energy ray-curable composition described above. As described above, the method for manufacturing a cold stamped product includes a coating layer forming step, a first irradiation step, a laminate forming step, and a second irradiation step. According to this method, it is possible to obtain a cold stamped product with higher transfer accuracy.

(12) In the method for manufacturing a cold stamped product, it is preferable that the active energy rays used in the first irradiation step and the second irradiation step both have a wavelength within a range of 280 nm or more and 420 nm or less. In this case, in the first irradiation step and the second irradiation step, the active energy rays can be irradiated using, for example, the same light source. Therefore, it is possible to reduce the cost of manufacturing equipment for cold stamped products.

Next, examples and comparative examples will be described.
(Examples 1 to 23)
In Examples 1 to 23, each raw material was placed in a container so as to have the composition shown in Tables 1 to 3, and stirred in a water bath at 40 to 50°C until no solid matter was left. An active energy ray-curable composition was prepared by filtration using GS-25 (trade name: GS-25, manufactured by Co., Ltd.).

In Tables 1 to 3, the unit of numerical values indicating the composition is mass %. Furthermore, the abbreviations in Tables 1 to 3 are as follows.
“Polymerizable compound A1” is the first polymerizable compound (A1), and is 2-(2-vinyloxyethoxy)ethyl acrylate (manufactured by Nippon Shokubai Co., Ltd., trade name: VEEA).

"Polymerizable compound A2" is the second polymerizable compound (A2), and is phenoxypolyethylene glycol acrylate (manufactured by Sartomer, trade name: SR9087).
“Polymerizable compound A3” is 1,6-hexanediol diacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd., trade name: NK Ester A-HD-N).

"Polymerizable compound A4" is isooctyl acrylate (manufactured by Sartomer, trade name: SR440).
“Photopolymerization initiator B11” is (B1) an acylphosphine oxide compound, which is bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide (manufactured by IGM Resins, trade name: OMNIRAD 819). .

“Photopolymerization initiator B12” is (B1) an acylphosphine oxide compound, and is 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide (manufactured by IGM Resins, trade name: OMNIRAD TPO).

“Photopolymerization initiator B13” is (B1) an acylphosphine oxide compound, and is ethyl (3-benzoyl-2,4,6-trimethylbenzoyl)(phenyl)phosphine oxide (manufactured by Lambson, trade name: Speedcure TPO) -L).

“Photopolymerization initiator B21” is a sulfone-based compound of (B2) a sulfur-based compound, and is 1-[4-(4-benzoylphenylsulfanyl)phenyl]-2-methyl-2-(4-methylphenylsulfonyl). Propan-1-one (manufactured by IGM Resins, trade name: ESACURE1001M).

“Photopolymerization initiator B22” is (B2) a thiobenzoyl-based sulfur-based compound, and is 4-benzoyl 4′-methyldiphenyl sulfide (manufactured by IGM Resins, trade name: OMNIRAD BMS).

“Photopolymerization initiator B23” is (B2) a thiobenzoyl-based sulfur-based compound, and is 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one (RAHN Co., Ltd. (product name: GENOCURE PMP).

“Photopolymerization initiator B3” is (B3) a thioxanthone-based compound, and is 2-isopropylthioxanthone (manufactured by DKSH Japan, trade name: Lunacure 2-ITX).

“Photopolymerization initiator B4” is 1-hydroxycyclohexylphenyl ketone (manufactured by DKSH Japan, trade name: Lunacure 200).
"Amine-based compound C1" is an amine-based compound (C), and is an aminoacrylate oligomer (manufactured by Daicel Allnex, trade name: EBECRYL80).

“Amine compound C2” is an amine compound (C), and is an aromatic amine compound (manufactured by RAHN, trade name: GENOPOL AB-2).
The "polymer" is a ketone resin (manufactured by EVONIK Industries AG, trade name: TEGO VARIPLUS SK).

The "surface tension modifier" is a polyether-modified siloxane copolymer (manufactured by EVONIK Industries AG, trade name: TEGO GLIDE 440).
The “polymerization inhibitor” is pentaerythritol tetrakis (3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate) (manufactured by BASF, trade name: Irganox 1010).

(Comparative Examples 1 and 2)
In Comparative Examples 1 and 2, active energy ray-curable compositions were prepared in the same manner as in Examples 1 to 23, except that the composition was changed as shown in Table 3. In Table 3, the unit of numerical values indicating the composition is mass %.

(Evaluation of transferability)
Using a bar coater, the active energy ray-curable composition of Example 1 was applied to a portion of the substrate. Thereby, as shown in FIG. 1(a), a base material 31 with a coating layer formed by laminating the coating layer 21 on a part of the base material 11 was obtained. The boundary between the coating layer 21 and the exposed portion 11a where the base material 11 is exposed is linear. As the base material 11, coated paper (manufactured by Oji Materia Co., Ltd., trade name: OK Super Post) was used.

Next, the coating layer 21 of the coating layer-coated base material 31 was irradiated with ultraviolet rays using an LED lamp having a wavelength of 385 nm. As a result, as shown in FIG. 1(b), a base material 32 with a low-fluidity membrane, in which the low-fluidity membrane 22 was laminated on the base material 11, was obtained. The average thickness of the low fluidity membrane 22 was 15 μm.

Subsequently, as shown in FIG. 2(a), a transfer base material 41 for cold stamping was placed on the low-fluidity film-attached base material 32 to obtain a first laminate 33. The transfer base material 41 has a base sheet 41a and a transfer layer 41b laminated on the base sheet 41a. As the transfer base material 41, a metal vapor deposited film (manufactured by Murata Kinpaku Co., Ltd., trade name: GNC-F, No. 3 gold) having a metal vapor deposited layer as the transfer layer 41b was used. The transfer base material 41 is arranged so as to straddle the boundary between the low-fluidity film 22 and the exposed portion 11a.

Next, the transfer base material 41 of the first laminate 33 was irradiated with ultraviolet light using an LED lamp with a wavelength of 385 nm. As a result, the low-fluidity film 22 is irradiated with ultraviolet light that has passed through the transfer base material 41 . The low fluidity film 22 was cured by irradiation with ultraviolet rays, thereby obtaining a second laminate 34 having a cured film 23, as shown in FIG. 2(b).

Subsequently, the base sheet 41a was peeled off from the second laminate 34 to obtain an evaluation sample 35 in which the transfer layer 41b was transferred onto the cured film 23, as shown in FIG. 3(a).
In the evaluation sample 35, the boundary between the transfer layer 41b and the exposed portion 11a was imaged using a microscope (manufactured by Sato Shoji Co., Ltd., trade name: Dino-Lite Pro) at a magnification of 60 times. An image 36 for evaluation was obtained as shown in FIG. 3(b). This image was analyzed using image analysis software, and a reference line BL serving as a boundary between the cured film 23 and the exposed portion 11a of the base material 11 was determined.

Next, using image analysis software, calculate the length L1 [mm] of the reference line and the area A1 [mm ² ] of the excessively transferred portion 36a where the metal vapor deposition layer protrudes and is transferred on the exposed portion side of the reference line. was calculated. Furthermore, using image analysis software, the area A2 [mm ² ] of the defective portion 36b to which the metal vapor deposition layer was not transferred was calculated on the second cured film side with respect to the reference line. Subsequently, the transfer accuracy [mm] was calculated according to the following formula.

Transfer accuracy [mm] = (A1-A2)/L1
Based on the above transfer accuracy, transferability was evaluated using the following evaluation criteria.
When the transfer accuracy is within the range of ±0.050 mm: Very good transferability (◎).

When the transfer accuracy is within the range of +0.051 mm or more and +0.100 mm or less, or within the range of -0.100 mm or more and -0.051 mm or less: Excellent transferability (○).
When the transfer accuracy is within the range of +0.101 mm or more or -0.101 mm or less: poor transferability (×).

The active energy ray curable compositions of Examples 2 to 23 and Comparative Examples 1 and 2 were also evaluated for transferability in the same manner as the active energy ray curable composition of Example 1. The evaluation results of transferability are shown in Tables 1 to 3.

It can be seen that the active energy ray curable compositions of Examples 1 to 23 have better transferability than the active energy ray curable compositions of Comparative Examples 1 and 2.

11... Base material 21... Coating layer 22... Low fluidity film 23... Cured film 41... Transfer base material 41b... Transfer layer

Claims (11)

An active energy ray-curable composition that is used for cold stamping processing and is cured by irradiation with active energy rays,
The cold stamping process includes a coating layer forming step of forming a coating layer on the substrate by coating the active energy ray-curable composition on the substrate;
A first irradiation step of obtaining a low fluidity film with reduced fluidity by irradiating the coating layer with active energy rays;
a laminate forming step of laminating a transfer base material on the low fluidity film to form a laminate in which the transfer layer of the transfer base material and the low fluidity film are in contact;
a second irradiation step of forming a cured film in which the low fluidity film is cured by irradiating the low fluidity film of the laminate with active energy rays;
The active energy ray-curable composition includes:
(A) a radically polymerizable compound, and (B) a photopolymerization initiator;
The radically polymerizable compound (A) includes at least one of (A1) a first polymerizable compound and (A2) a second polymerizable compound,
The first polymerizable compound (A1) is a compound having at least one ether group of a vinyl ether group and an allyl ether group and a (meth)acryloyl group,
The second polymerizable compound (A2) is a (meth)acrylate compound having an aromatic skeleton,
The photopolymerization initiator (B) includes (B1) an acylphosphine oxide compound,
The active energy ray curable composition wherein the content of the acylphosphine oxide compound (B1) in the active energy ray curable composition is in the range of 2.0% by mass or more and 11.0% by mass or less. The radically polymerizable compound (A) includes ( A3) a third polymerizable compound ,
The third polymerizable compound (A3) is at least one compound selected from an alkanediol (meth)acrylate compound, an alkylene glycol di(meth)acrylate compound, and an alkoxylated alkanediol (meth)acrylate compound. Item 1. The active energy ray-curable composition according to item 1. The photopolymerization initiator (B) further includes (B2) a sulfur-based compound,
The active energy ray-curable composition according to claim 1 or 2, wherein the sulfur-based compound (B2) is at least one of a sulfone-based compound and a thiobenzoyl-based compound. The photopolymerization initiator (B) further includes (B3) a thioxanthone compound,
The active energy ray curable composition according to any one of claims 1 to 3, wherein the content of the thioxanthone compound (B3) in the active energy ray curable composition is 0.8% by mass or less. Composition. (C) The active energy ray-curable composition according to any one of claims 1 to 4, further comprising an amine compound. The (C) amine compound includes at least one of (C1) an amino-modified compound and (C2) an aromatic amine compound, and the (C1) amino-modified compound includes at least one of an amino-modified acrylate oligomer and an amino-modified acrylate polymer. The active energy ray-curable composition according to claim 5, which is one of the above. The active energy ray-curable composition according to any one of claims 1 to 6, wherein the radically polymerizable compound (A) has 1 to 3 functional groups. The active energy ray curable composition according to any one of claims 1 to 7, wherein the active energy ray curable composition does not contain a pigment. The active energy ray curable composition according to any one of claims 1 to 8, wherein the active energy ray curable composition is used for inkjet printing. A method for producing a cold stamped product using an active energy ray-curable composition, the method comprising:
a coating layer forming step of forming a coating layer on the substrate by applying the active energy ray-curable composition to the substrate;
A first irradiation step of obtaining a low fluidity film with reduced fluidity by irradiating the coating layer with active energy rays;
a laminate forming step of laminating a transfer base material on the low fluidity film to form a laminate in which the transfer layer of the transfer base material and the low fluidity film are in contact;
a second irradiation step of forming a cured film in which the low fluidity film is cured by irradiating the low fluidity film of the laminate with active energy rays ;
The active energy ray-curable composition includes:
(A) a radically polymerizable compound, and (B) a photopolymerization initiator;
The radically polymerizable compound (A) includes at least one of (A1) a first polymerizable compound and (A2) a second polymerizable compound,
The first polymerizable compound (A1) is a compound having at least one ether group of a vinyl ether group and an allyl ether group and a (meth)acryloyl group,
The second polymerizable compound (A2) is a (meth)acrylate compound having an aromatic skeleton,
The photopolymerization initiator (B) includes (B1) an acylphosphine oxide compound,
A method for producing a cold stamped product, wherein the content of the acylphosphine oxide compound (B1) in the active energy ray-curable composition is within a range of 2.0% by mass or more and 11.0% by mass or less. The method for manufacturing a cold stamped product according to claim 10, wherein the active energy rays used in the first irradiation step and the second irradiation step each have a wavelength within a range of 280 nm or more and 420 nm or less.