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WO2024232177A1 - Composition photodurcissable, article durci associé, et élément - Google Patents

Composition photodurcissable, article durci associé, et élément Download PDF

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Publication number
WO2024232177A1
WO2024232177A1 PCT/JP2024/011870 JP2024011870W WO2024232177A1 WO 2024232177 A1 WO2024232177 A1 WO 2024232177A1 JP 2024011870 W JP2024011870 W JP 2024011870W WO 2024232177 A1 WO2024232177 A1 WO 2024232177A1
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WO
WIPO (PCT)
Prior art keywords
meth
component
photocurable composition
acrylate
modified
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PCT/JP2024/011870
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English (en)
Japanese (ja)
Inventor
喜一 平田
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Daicel Allnex Ltd
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Daicel Allnex Ltd
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Publication of WO2024232177A1 publication Critical patent/WO2024232177A1/fr
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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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/38—Esters containing sulfur

Definitions

  • This embodiment relates to a photocurable composition and its cured product and component.
  • the objective of this disclosure is to provide a photocurable composition that can be used in interior components, water-related components, and the like, and that can further improve poor appearance of the cured coating film, as well as a cured product thereof, and a component comprising the cured product.
  • Component (A) a difunctional or higher functional (meth)acrylate monomer
  • Component (B) an acid-modified (meth)acrylate monomer and/or a hydroxyl group-containing (meth)acrylamide
  • Component (C) a (meth)acrylic-modified sulfonate.
  • this photocurable composition can impart hydrophilicity to a cured coating film without using fluorine or silicone, which are known to deteriorate anti-slip properties, or surfactants, which are known to deteriorate chemical resistance, and can therefore impart stain resistance, chemical resistance, anti-slip properties, and easy cleaning properties to the surface of the cured coating film, making it suitable for use in interior components, wet area components, and the like. Furthermore, since this photocurable composition is capable of suppressing haze in the cured coating film (i.e., has high transparency), it can be widely used for decorative substrates used in interior components and water-related components.
  • a composition comprising a curable component and a photopolymerization initiator,
  • the curable component is Component (A): a difunctional or higher functional (meth)acrylate monomer, Component (B): an acid-modified (meth)acrylate monomer and/or a hydroxyl group-containing (meth)acrylamide; and Component (C): a (meth)acrylic-modified sulfonate.
  • a photocurable composition comprising: [2] The photocurable composition according to [1], wherein the component (A) contains a di- or higher functional hydroxyl group-containing (meth)acrylate monomer (a1).
  • the first embodiment of this embodiment is as follows: Contains a curable component and a photopolymerization initiator,
  • the curable component is Component (A): a difunctional or higher functional (meth)acrylate monomer, Component (B): an acid-modified (meth)acrylate monomer and/or a hydroxyl group-containing (meth)acrylamide; and Component (C): a (meth)acrylic-modified sulfonate.
  • A a difunctional or higher functional (meth)acrylate monomer
  • Component (C): a (meth)acrylic-modified sulfonate According to the first embodiment, it is possible to provide a photocurable composition which can improve poor appearance of a cured coating film more than ever before.
  • the photocurable composition according to the first embodiment is Component (A): a difunctional or higher functional (meth)acrylate monomer, Component (B): an acid-modified (meth)acrylate monomer and/or a hydroxyl group-containing (meth)acrylamide; and Component (C): a (meth)acrylic-modified sulfonate.
  • the curable component comprises:
  • the curable component contains component (A): a di- or higher functional (meth)acrylate monomer.
  • the (meth)acrylate monomer as the component (A) may include both an acrylate and a methacrylate.
  • the (meth)acrylate monomer as the component (A) may be used alone or in combination of two or more kinds.
  • the term "bifunctional or higher” refers to the average number of functional groups (average number of functional groups) contained in component (A) being 2 or more.
  • the term "functional group” refers to a photopolymerizable functional group.
  • the average number of functional groups of the component (A) may be 2 to 6, 2 to 5, 2 to 4, or 3 to 4. When the average number of functional groups is within the above range, the appearance finish of the cured coating film is more likely to be improved.
  • the molecular weight (g/mol) of the difunctional or higher functional (meth)acrylate monomer (A) component is preferably 100 to 600, more preferably 150 to 600, even more preferably 150 to 500, and particularly preferably 150 to 400.
  • bifunctional or higher (meth)acrylate monomers include diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 4,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, pentaerythritol di(meth)acrylate, neopentyl glycol dimethacrylate, 3-methyl-1,5-pentanediol diacrylate, 2-hydroxy-3-acryloyloxypropyl methacrylate, dimethylol tricyclodecane diacrylate, and dicyclopentanyl diacrylate
  • trifunctional (meth)acrylate monomers include trimethylolpropane tri(meth)acrylate, ethylene oxide modified trimethylolpropane tri(meth)acrylate, ethoxylated glycerin tri(meth)acrylate, ethoxylated trimethylolpropane tri(meth)acrylate, propylene oxide modified trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol tri(meth)acrylate, alkyl modified dipentaerythritol tri(meth)acrylate, tris(2-acryloxyethyl)isocyanurate, ⁇ -caprolactone modified tris(2-acryloxyethyl)isocyanurate, etc.
  • non-limiting examples of tetrafunctional (meth)acrylate monomers include trimethylolpropane tetra(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol tetra(meth)acrylate, ethoxylated pentaerythritol tetra(meth)acrylate, and alkyl-modified dipentaerythritol tetra(meth)acrylate.
  • (meth)acrylate monomers having two or more functionalities non-limiting examples of pentafunctional (meth)acrylate monomers include dipentaerythritol penta(meth)acrylate, alkyl-modified dipentaerythritol penta(meth)acrylate, etc.
  • (meth)acrylate monomers having two or more functionalities non-limiting examples of hexafunctional (meth)acrylate monomers include dipentaerythritol hexa(meth)acrylate, caprolactone-modified dipentaerythritol hexa(meth)acrylate, etc.
  • component (A) is one or more bifunctional or higher (meth)acrylate monomers selected from the group consisting of pentaerythritol tetraacrylate, pentaerythritol triacrylate, trimethylolpropane triacrylate, ethoxylated pentaerythritol tetraacrylate, ethoxylated trimethylolpropane triacrylate, and ethoxylated glycerin triacrylate.
  • component (A) is one or more bifunctional or higher (meth)acrylate monomers selected from the group consisting of pentaerythritol tetraacrylate, pentaerythritol triacrylate, trimethylolpropane triacrylate, ethoxylated pentaerythritol tetraacrylate, ethoxylated trimethylolpropane triacrylate, and ethoxylated glycerin triacrylate.
  • the amount of component (A) in the photocurable composition according to the first embodiment may be 40 to 99.9% by mass, 50 to 99.9% by mass, 60 to 99.9% by mass, 70 to 99.9% by mass, 80 to 99.9% by mass, or 90 to 99.9% by mass, where the total amount of the curable components is 100% by mass.
  • the component (A) preferably contains a di- or higher functional hydroxyl-containing (meth)acrylate monomer (a1).
  • the number of hydroxyl groups in the hydroxyl-containing (meth)acrylate monomer (a1) is not particularly limited and may be 1 to 10 or 1 to 5.
  • the difunctional or higher hydroxyl group-containing (meth)acrylate monomer (a1) contained in the component (A) may use one type alone, or two or more types in combination.
  • the difunctional or higher hydroxyl group-containing (meth)acrylate monomer (a1) is preferably one or more difunctional or higher hydroxyl group-containing (meth)acrylate monomers selected from the group consisting of hydroxyl group-containing bifunctional (meth)acrylate compounds such as isocyanuric acid ethylene oxide modified diacrylate and glycerol epichlorohydrin modified 1,6-hexanediol diacrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, caprolactone modified dipentaerythritol penta(meth)acrylate, caprolactone modified pentaerythritol tri(meth)acrylate, ethylene oxide modified dipentaerythritol penta(meth)acrylate, ethylene oxide modified pentaerythritol tri(meth)acrylate, and other polyfunctional hydroxyl group-containing (meth)
  • the difunctional or higher hydroxyl group-containing (meth)acrylate monomer (a1) is preferably pentaerythritol tetraacrylate, pentaerythritol triacrylate, or a mixture thereof, and more preferably a mixture of pentaerythritol tetraacrylate and pentaerythritol triacrylate.
  • the total amount of the (A) component is taken as 100 mass%, and the difunctional or higher hydroxyl group-containing (meth)acrylate monomer (a1) may be 40 to 99.9 mass%, 50 to 99.9 mass%, 60 to 99.9 mass%, 70 to 99.9 mass%, 80 to 99.9 mass%, 90 to 99.9 mass%, or 100 mass%.
  • the curable component contains component (B): an acid-modified (meth)acrylate monomer and/or a hydroxyl group-containing (meth)acrylamide.
  • component (B) an acid-modified (meth)acrylate monomer and/or a hydroxyl group-containing (meth)acrylamide.
  • the hydroxyl group-containing (meth)acrylate monomer as the component (B) may include both an acrylate and a methacrylate.
  • the acid-modified (meth)acrylate monomer and the hydroxyl group-containing (meth)acrylamide as the component (B) may each be used alone or in combination of two or more kinds.
  • the component (B): the acid-modified (meth)acrylate monomer does not include one in which the acid-modified portion is in the form of a salt.
  • the acid value (mgKOH/g) of the component (B): the acid-modified (meth)acrylate monomer is preferably 80 to 800, more preferably 200 to 500, and particularly preferably 250 to 400.
  • non-limiting examples of the component (B): acid-modified (meth)acrylate monomer are preferably one or more acid-modified (meth)acrylate monomers selected from the group consisting of carboxylic acid-modified (meth)acrylates, phosphoric acid-modified (meth)acrylates, polybasic acid (succinic acid, phthalic acid, etc.)-modified (meth)acrylates, and sulfonic acid-modified (meth)acrylates.
  • non-limiting examples of the hydroxyl group-containing (meth)acrylamide as component (B) are preferably one or more hydroxyl group-containing (meth)acrylamides selected from the group consisting of hydroxyalkyl(meth)acrylamide having an alkyl group with 1 to 10 carbon atoms, N-hydroxyethyl(meth)acrylamide, N-hydroxymethyl(meth)acrylamide, N-hydroxy(meth)acrylamide, 2-hydroxyethyl(meth)acrylate, 4-hydroxybutyl(meth)acrylate, 6-hydroxyhexyl(meth)acrylate, and 8-hydroxyoctyl(meth)acrylate.
  • the component (B) is preferably one or more acid-modified (meth)acrylate monomers.
  • the component (B) is preferably an acid-modified (meth)acrylate monomer in which the acid component is one or more selected from carboxylic acid, phosphoric acid, and succinic acid, and/or a hydroxyalkyl (meth)acrylamide in which the alkyl group has 1 to 5 carbon atoms, more preferably one or more acid-modified (meth)acrylate monomers and/or hydroxyl group-containing (meth)acrylamides selected from the group consisting of ⁇ -carboxyethyl acrylate, phosphoric acid-modified methacrylate, phosphoric acid-modified acrylate, 2-acryloyloxyethyl succinic acid, and hydroxyethyl acrylamide, and particularly preferably one or more acid-modified (meth)acrylate monomers selected from the group consisting of ⁇ -carboxyethyl acrylate
  • the amount of component (B) in the photocurable composition according to the first embodiment may be 0.01 to 40 mass%, 0.01 to 35 mass%, 0.01 to 30 mass%, 0.01 to 25 mass%, 0.01 to 20 mass%, 0.01 to 15 mass%, or 0.01 to 10 mass%, relative to 100 mass% of the total amount of the curable components.
  • the (B) component is preferably blended in an amount of 0.1 to 20 parts by mass, more preferably 0.1 to 15 parts by mass, even more preferably 1 to 15 parts by mass, and particularly preferably 1 to 10 parts by mass, per 100 parts by mass of the (A) component.
  • the curable component includes component (C): a (meth)acrylic-modified sulfonate.
  • component (C): a (meth)acrylic-modified sulfonate may be used alone or in combination of two or more kinds.
  • the component (C): the (meth)acrylic-modified sulfonate, the acid-modified portion is in the form of a salt.
  • non-limiting examples of the component (C): (meth)acrylic-modified sulfonate are preferably one or more (meth)acrylic-modified sulfonates selected from the group consisting of potassium 3-sulfopropyl acrylate, potassium 3-sulfopropyl methacrylate, 2-((meth)acryloyloxy)ethanesulfonic acid, 3-((meth)acryloyloxy)propane-1-sulfonic acid, and sodium or potassium salts of acrylamido-tert-butylsulfonic acid.
  • the component (C) is more preferably one or more (meth)acrylic-modified sulfonates selected from the group consisting of potassium 3-sulfopropyl acrylate, potassium 3-sulfopropyl methacrylate, and mixtures thereof.
  • the amount of the component (C) in the photocurable composition according to the first embodiment may be 0.01 to 5 mass%, 0.01 to 4 mass%, 0.01 to 3 mass%, 0.01 to 2.5 mass%, 0.01 to 2 mass%, 0.01 to 1.5 mass%, or 0.01 to 1 mass%, relative to 100 mass% of the total amount of the curable components.
  • the (C) component is preferably blended in an amount of 0.1 to 5 parts by mass, more preferably 0.1 to 3 parts by mass, even more preferably 0.5 to 2 parts by mass, and particularly preferably 0.5 to 1.5 parts by mass, per 100 parts by mass of the (A) component.
  • the curable component may contain, in addition to the components (A) to (C), a component (D): a monofunctional hydroxyl group-containing (meth)acrylate monomer.
  • the number of hydroxyl groups in the component (D) is not particularly limited and may be 1 to 10 or 1 to 5.
  • the monofunctional hydroxyl group-containing (meth)acrylate monomer as the component (D) may be used alone or in combination of two or more.
  • non-limiting examples of the component (D): monofunctional hydroxyl group-containing (meth)acrylate monomer are preferably one or more monofunctional hydroxyl group-containing (meth)acrylate monomers selected from the group consisting of hydroxyl group-containing monofunctional (meth)acrylates such as 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 2-hydroxy-3-methoxypropyl (meth)acrylate, 1,4-cyclohexanedimethanol mono(meth)acrylate, caprolactone-modified 2-hydroxyethyl (meth)acrylate, polyethylene glycol mono(meth)acrylate, polypropylene glycol mono(meth)acrylate, bisphenol A diglycidyl mono(meth)acrylate, and other epoxy acrylates, and hydrogenated versions of these.
  • hydroxyl group-containing monofunctional (meth)acrylates such as 2-hydroxyethyl (meth)acrylate, 2-
  • the component (D) is more preferably one or more monofunctional hydroxyl group-containing (meth)acrylate monomers selected from the group consisting of hydroxyethyl methacrylate, hydroxypropyl methacrylate, hydroxybutyl acrylate, and mixtures thereof.
  • the (D) component when the photocurable composition includes the (D) component, the (D) component may be 0.01 to 50 mass%, 0.01 to 30 mass%, 0.01 to 25 mass%, 0.01 to 20 mass%, 0.01 to 15 mass%, or 0.01 to 1 mass%, relative to 100 mass% of the total amount of the curable components. In one embodiment, when the photocurable composition contains the component (D), the component (D) is preferably blended in an amount of 5 to 30 parts by mass, more preferably 5 to 25 parts by mass, even more preferably 5 to 20 parts by mass, and particularly preferably 10 to 20 parts by mass, per 100 parts by mass of the component (A).
  • the photocurable composition according to the first embodiment further contains a photopolymerization initiator.
  • the photopolymerization initiator include benzophenone, acetophenone benzyl, benzyl dimethyl ketone, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, dimethoxyacetophenone, dimethoxyphenylacetophenone, diethoxyacetophenone, diphenyl disulfite, methyl orthobenzoylbenzoate, ethyl 4-dimethylaminobenzoate (e.g., Nippon Kayaku Co., Ltd., trade name "KAYACURE (registered trademark) EPA” and the like), 2,4-diethylthioxanthone (e.g., Nippon Kayaku Co., Ltd., trade name "KAYACURE DETX” and the like), 2-methyl-1-[4-(2-aphthalaku) EPA)
  • the content of the photopolymerization initiator in the photocurable composition is preferably 1 to 5 mass % relative to the total mass of the curable composition, more preferably 2.5 to 5 mass %, and even more preferably 4 to 5 mass %.
  • the curable composition according to this embodiment can be appropriately cured by ultraviolet light, which will be described later.
  • the photocurable composition according to the present embodiment may contain any component (other additives) other than the curable component and the photopolymerization initiator.
  • the other additives are not particularly limited, and any additive that can be blended in the photocurable composition and/or the thermo-curable composition may be blended.
  • a radical polymerization initiator other than the photopolymerization initiator, an ultraviolet absorber, a reaction accelerator, a light stabilizer, a surface conditioner, etc. may be blended.
  • UV absorbers Any known or commonly used ultraviolet absorbers can be used, and are not particularly limited. Examples of the ultraviolet absorbers include cyanoacrylate-based, dihydroxybenzophenone-based, benzotriazole-based, triazine-based, and benzophenone-based ultraviolet absorbers.
  • Examples of cyanoacrylate ultraviolet absorbers include 2-ethylhexyl-2-cyano-3,3-diphenylacrylate, and ethyl-2-cyano-3,3-diphenylacrylate.
  • Examples of dihydroxybenzophenone-based ultraviolet absorbers include 2-hydroxy-4-methoxybenzophenone, (2,4-dihydroxyphenyl)-phenylmethanone, hydroxymethoxybenzophenonesulfonic acid, 2-(2H-benzotriazol-2-yl)-4-methyl, 2-(2H-benzotriazol-2-yl)-4,6-bis(1-methyl-1-phenylethyl), and 2-(5-chloro-2H-benzotriazol-2-yl)-6-(1,1-dimethylethyl)-4-methyl.
  • benzotriazole-based ultraviolet absorbers examples include 2-(2H-benzotriazol-2-yl)-p-cresol, 2-(5-chloro-2H-benzotriazol-2-yl)-6-tertiarybutyl-4-methylphenol, and 2,2'-methylenebis[6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol].
  • triazine-based ultraviolet absorbers examples include 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-[2-(2-ethylhexanoloxy)ethoxy]phenol, 2-(4-((2-hydroxy-3-dodecyloxypropyl)oxy)-2-hydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, and 2-(4-((2-hydroxy-3-tridecyloxypropyl)oxy)-2-hydroxyphenyl)-4,6-bis (2,4-dimethylphenyl)-1,3,5-triazine, 2-(4-((2-hydroxy-3-(2'ethyl)hexyl)oxy)-2-hydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2,4-bis(2-hydroxy-4-butyloxyphenyl)-6-(2,4-bisbutyloxy
  • Light stabilizer As the light stabilizer, known or conventional ones can be used, and there is no particular limitation.
  • the light stabilizer include 2,2,6,6-tetraalkyl-4-piperidyl esters (e.g., 2,2,6,6-tetramethyl-4-piperidyl esters), 4-alkoxy-2,2,6,6-tetraalkylpiperidines (e.g., 4-(C1-10 alkoxy)-2,2,6,6-piperidines such as 4-methoxy-2,2,6,6-tetramethylpiperidine; 4-(C6-10 aryloxy)-2,2,6,6-piperidines such as 4-phenoxy-2,2,6,6-tetramethylpiperidine; 4-(C6-10 aryl)-(C1-4 alkyl)-2,2,6,6-tetramethylpiperidines such as 4-benzyloxy-2,2,6,6-tetramethylpiperidine), bis( 2,2,6,6-tetraalkyl-4-piperidyloxy)alkanes [for example
  • reaction accelerators Any known or conventional reaction accelerators can be used, and are not particularly limited.
  • reaction accelerators include 1,8-diazabicyclo[5.4.0]undecene-7 (DBU) or a salt thereof (e.g., phenol salt, octylate salt, p-toluenesulfonate, formate salt, tetraphenylborate salt, etc.); 1,5-diazabicyclo[4.3.0]nonene-5 (DBN) or a salt thereof (e.g., phenol salt, octylate salt, p-toluenesulfonate, formate salt, tetraphenylborate salt, etc.); benzyldimethylamine, 2,4,6-tris(dimethylamine),
  • the reaction accelerator include tertiary amines such as 2-ethyl-4-methylimidazole and 1-cyanoethyl-2-ethyl-4-methylimidazole, phospho
  • compositions combining sulfonates modified with (meth)acryloyl groups and (meth)acryloyl monomers have been known, but as mentioned above, they often result in poor appearance of the cured coating film.
  • the inventors of the present application have discovered that poor compatibility between the resin composition and the sulfonate causes poor appearance of the cured coating film.
  • the photocurable composition according to this embodiment can improve poor appearance of the cured coating film compared to conventional compositions by combining the (A) and (C) components with the (B) component.
  • the curable component contains a relatively low molecular weight compound, the viscosity is low and the flowability is likely to be good.
  • the viscosity of the photocurable composition at 25°C may be 1 to 1000 mPa.s, or may be 1 to 500 mPa.s. If the viscosity of the photocurable composition is within the above range, it is possible to form a film with good adhesion, to form a film by spraying or curtain coating, and the finish of the coating film is likely to be good.
  • the photocurable composition according to the first embodiment can be produced by mixing the above-mentioned curable component, the photopolymerization initiator, and, if necessary, the above-mentioned other additives and solvent.
  • the photocurable composition according to the first embodiment has a higher compatibility between the resin components (components (A) and (B)) and the component (C), so it is possible to reduce the amount of solvent used to dissolve the component (C) or to prepare a composition without using a solvent.
  • a solvent it is preferable to use a hydrophilic solvent such as a lower alcohol or 2-methoxyethanol.
  • a means for mixing known or conventional means, for example, various mixers such as a dissolver or homogenizer, a kneader, a roll, a bead mill, a self-revolving stirring device, etc. can be used. Conditions such as temperature and rotation speed during mixing are not particularly limited and can be set appropriately.
  • the photocurable composition according to the first embodiment is capable of improving the poor appearance of the cured coating film by photocuring it, more than ever before.
  • a photocurable composition can be suitably used, for example, as various components, particularly interior components or wet-area components. It should be noted that the uses of the photocurable composition are not limited to interior components and wet-area components.
  • the second embodiment of this embodiment is a cured product of the photocurable composition according to the first embodiment.
  • the photocurable composition according to the first embodiment can be made into a cured product by light irradiation.
  • the cured product according to the second embodiment includes not only the above-mentioned photocurable composition irradiated with light such as ultraviolet light or active energy rays to be described later to promote the curing reaction, but also a completely cured product.
  • a "semi-cured product" in which the photocurable composition is irradiated with light and cured to the extent that it loses fluidity is also included in the cured product of this embodiment.
  • the cured product according to this embodiment can be obtained as a cured coating film, for example, by applying the photocurable composition according to the first embodiment to an object such as a substrate and then photocuring the composition.
  • the photocurable composition of the present invention can be applied to the surface of a substrate as a coating liquid using a dilution solvent as necessary.
  • a dilution solvent as necessary.
  • any known method can be used, such as gravure coating, roll coating, reverse coating, knife coating, die coating, lip coating, doctor coating, extrusion coating, slide coating, wire bar coating, curtain coating, extrusion coating, spin coating, etc.
  • the photocuring is preferably carried out by irradiation with active energy rays such as ultraviolet rays or electron beams.
  • active energy rays such as ultraviolet rays or electron beams.
  • light sources used for ultraviolet irradiation include high-pressure mercury lamps, ultra-high-pressure mercury lamps, carbon arc lamps, xenon lamps, metal halide lamps, etc.
  • the ultraviolet irradiation time can be adjusted as desired between several seconds and several tens of seconds depending on the type of light source, the distance between the light source and the coated surface, and other conditions.
  • electron beam irradiation it is preferable to use an electron beam having an energy in the range of, for example, 50 to 1000 KeV, and to set the irradiation dose at 2 to 5 Mrad.
  • an irradiation source with a lamp output of about 80 to 300 W/cm is used.
  • the thickness of the cured coating film is not particularly limited and can be adjusted as desired depending on the application. For example, it may be adjusted to a range of 10 to 1000 ⁇ m, preferably 300 to 500 ⁇ m.
  • the object (subject) to which the photocurable composition is applied is not particularly limited in shape, material, etc., and examples of the material include resin, metal, glass, wood, paper, etc.
  • resins include polyvinyl chloride, polypropylene, polyethylene, polyethylene terephthalate (PET), polycarbonate, acrylonitrile butadiene styrene (ABS), polypropylene sulfide, nylon-6, etc.
  • resins include polyvinyl chloride, polypropylene, polyethylene, polyethylene terephthalate (PET), polycarbonate, acrylonitrile butadiene styrene (ABS), polypropylene sulfide, nylon-6, etc.
  • metals include aluminum, SUS, iron, copper, etc.
  • the substrate may be one whose surface has been subjected to metal deposition, such as resin, glass, wood, paper, etc., or the coated surface of the substrate may have been subjected to a release treatment or the like.
  • the haze of a 20 ⁇ m-thick cured coating film measured under the following conditions is preferably 1.2% or less, and more preferably 1% or less.
  • a Haze measurement conditions The photocurable composition is applied to a PET film substrate (e.g., Cosmoshine (registered trademark) A4160 (100 ⁇ m), manufactured by Toyobo Co., Ltd.) to a thickness of 20 ⁇ m, and then irradiated with a UV lamp to form a cured coating film.
  • the haze of the resulting cured coating film is measured using a haze meter (e.g., NDH 4000, manufactured by Nippon Denshoku Industries Co., Ltd.).
  • the third embodiment of this embodiment is a member having the cured product according to the second embodiment.
  • the member is an interior member or a water-related member.
  • the details of the interior member and the water-related member will be described as one aspect of the member.
  • interior components refers to all components that can be used in manufacturing walls, floors, ceilings, etc., regardless of whether they are finishing materials that cover the surface parts of the interior or base materials that serve as a base for installing finishing materials.
  • Non-limiting examples include flooring, tatami mats, wallpaper, tiles, painted walls, structural plywood, etc.
  • water-related components refers to all components that can be used in places where water or hot water is used, such as a bathroom, a toilet, a washroom, a swimming pool, etc.
  • Non-limiting examples include ceilings, walls, sinks, hoses, pipes, valves, etc. in a bathroom, a toilet, a washroom, a swimming pool, etc.
  • Examples 1 to 17 and Comparative Examples 1 to 8 Using the above materials, each component was weighed into an brown screw cap bottle in the ratio shown in Tables 1 to 3 and heated at 70° C. for 1 hour. Stirring and degassing were performed using a stirring and degassing device ("Mazerustar (registered trademark), Kurabo Industries Ltd.) and dissolution was confirmed visually to obtain each photocurable composition according to the examples and comparative examples. Each of the photocurable compositions according to the examples and comparative examples was photocured by the following steps to obtain a cured coating film. (1) Coating Step Using a wire bar coater No. 14-18, each photocurable composition was applied onto a glass plate (70 mm ⁇ 150 mm ⁇ 1.0 mm).
  • a contact angle meter (Drop Master DM700, manufactured by Kyowa Interface Science Co., Ltd.) was used to measure the contact angle 1 second after detection of a drop (a drop of ion-exchanged water (2 ⁇ l)) on the surface of the cured coating film.
  • ⁇ Chemical resistance evaluation> (1) Hair dye and mouthwash Approximately 0.2 g of hair dye (Bigen Creamtone (registered trademark) 7G, manufactured by Hoyu Corporation) and mouthwash (Isodine (registered trademark), manufactured by Mundipharma K.K.) were placed on each cured coating film, and then the films were left to stand for 24 hours at 23° C. and a relative humidity of 50% RH, after which any traces of contamination were visually checked.
  • the numbers in Tables 1 to 3 have the following meanings.
  • the photocurable composition according to the first embodiment can impart hydrophilicity without using fluorine or silicone, which are known to deteriorate anti-slip properties, or surfactants, which are known to deteriorate chemical resistance, and can impart antifouling properties, chemical resistance, anti-slip properties, and easy cleaning properties to the cured coating film surface.
  • the photocurable composition which can give such a cured coating film can be suitably used for interior components, water-related components, and the like.
  • the photocurable composition according to this embodiment can improve the appearance defects of cured coating films more than ever before, and therefore has industrial applicability as interior building materials, water-related components, etc.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention fournit une composition photodurcissable qui permet une application à un matériau de construction intérieur, un élément de plomberie, ou similaire, et qui peut améliorer les défauts d'apparence d'un film de revêtement durci en comparaison avec l'art antérieur. L'invention fournit également un article durci associé, et un élément équipé de cet article durci. Plus précisément, l'invention concerne une composition photodurcissable qui contient un composant durcissable, et un initiateur de photopolymérisation. Ledit composant durcissable contient : un monomère de (méth)acrylate bifonctionnel ou plus en tant que composant (A) ; un monomère de (méth)acrylate modifié par un acide et/ou (méth)acrylamide à teneur en groupe hydroxyle en tant que composant (B) ; et un sel d'acide sulfonique modifié par un (méth)acrylique en tant que composant (C).
PCT/JP2024/011870 2023-05-11 2024-03-26 Composition photodurcissable, article durci associé, et élément Pending WO2024232177A1 (fr)

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JP2023078799A JP7674414B2 (ja) 2023-05-11 2023-05-11 光硬化性組成物及びその硬化物、部材
JP2023-078799 2023-05-11

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5590516A (en) * 1978-12-28 1980-07-09 Mitsubishi Rayon Co Ltd Coating composition with excellent functionality
WO2013014733A1 (fr) * 2011-07-25 2013-01-31 三井化学株式会社 Film monocouche et matériau hydrophile le contenant

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5590516A (en) * 1978-12-28 1980-07-09 Mitsubishi Rayon Co Ltd Coating composition with excellent functionality
WO2013014733A1 (fr) * 2011-07-25 2013-01-31 三井化学株式会社 Film monocouche et matériau hydrophile le contenant

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