CN116406391A - Active energy ray-curable hard coating agent, hard coating layer, and laminate - Google Patents
Active energy ray-curable hard coating agent, hard coating layer, and laminate Download PDFInfo
- Publication number
- CN116406391A CN116406391A CN202180074368.0A CN202180074368A CN116406391A CN 116406391 A CN116406391 A CN 116406391A CN 202180074368 A CN202180074368 A CN 202180074368A CN 116406391 A CN116406391 A CN 116406391A
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- China
- Prior art keywords
- hard coat
- active energy
- energy ray
- meth
- compound
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- ZEDSKTISNTXEQI-UHFFFAOYSA-N [(2,6-dichlorobenzoyl)-(4-propylphenyl)phosphoryl]-(2,6-dichlorophenyl)methanone Chemical compound C1=CC(CCC)=CC=C1P(=O)(C(=O)C=1C(=CC=CC=1Cl)Cl)C(=O)C1=C(Cl)C=CC=C1Cl ZEDSKTISNTXEQI-UHFFFAOYSA-N 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 1
- VEBCLRKUSAGCDF-UHFFFAOYSA-N ac1mi23b Chemical compound C1C2C3C(COC(=O)C=C)CCC3C1C(COC(=O)C=C)C2 VEBCLRKUSAGCDF-UHFFFAOYSA-N 0.000 description 1
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- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- PJIFJEUHCQYNHO-UHFFFAOYSA-N diethoxy-(3-isocyanatopropyl)-methylsilane Chemical compound CCO[Si](C)(OCC)CCCN=C=O PJIFJEUHCQYNHO-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
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- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
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- 239000004715 ethylene vinyl alcohol Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RZXDTJIXPSCHCI-UHFFFAOYSA-N hexa-1,5-diene-2,5-diol Chemical compound OC(=C)CCC(O)=C RZXDTJIXPSCHCI-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229920000587 hyperbranched polymer Polymers 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
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- 239000000314 lubricant Substances 0.000 description 1
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- ADFPJHOAARPYLP-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;styrene Chemical compound COC(=O)C(C)=C.C=CC1=CC=CC=C1 ADFPJHOAARPYLP-UHFFFAOYSA-N 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
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- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- 239000011368 organic material Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
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- 229920003023 plastic Polymers 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920005575 poly(amic acid) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 1
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- 229920005668 polycarbonate resin Polymers 0.000 description 1
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- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
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- 229920000306 polymethylpentene Polymers 0.000 description 1
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- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
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- MVQLEZWPIWKLBY-UHFFFAOYSA-N tert-butyl 2-benzoylbenzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 MVQLEZWPIWKLBY-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
- B32B15/082—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin comprising vinyl resins; comprising acrylic resins
-
- 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
- C08F122/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
- C08F122/10—Esters
- C08F122/1006—Esters of polyhydric alcohols or polyhydric phenols, e.g. ethylene glycol dimethacrylate
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- 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
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
-
- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/105—Esters of polyhydric alcohols or polyhydric phenols of pentaalcohols
-
- 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/06—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/71—Monoisocyanates or monoisothiocyanates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/544—Silicon-containing compounds containing nitrogen
- C08K5/5465—Silicon-containing compounds containing nitrogen containing at least one C=N bond
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Paints Or Removers (AREA)
- Laminated Bodies (AREA)
- Polyurethanes Or Polyureas (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
One embodiment relates to an active energy ray-curable hard coat agent for forming a hard coat layer having a metal thin film on the hard coat layer, the active energy ray-curable hard coat agent comprising: the compound (A) having three or more (meth) acryloyl groups, the silane coupling agent (B) having isocyanate groups, and the photopolymerization initiator (C) are contained in an amount of 70 parts by mass or more based on 100 parts by mass of the nonvolatile component of the active energy ray-curable hard coat agent.
Description
Technical Field
Embodiments of the present invention relate to an active energy ray hardening hard coat agent, a hard coat layer, and a laminate for forming a hard coat layer having a metal thin film on the hard coat layer.
Background
Transparent conductive films formed by laminating a transparent conductive material on a transparent plastic film base material are widely used in applications in the fields of flat panel displays such as liquid crystal displays and electroluminescent (hereinafter abbreviated as EL (electroluminescence)) displays, touch panels, lighting, solar cells, electric and electronic devices, and the like.
As the transparent conductive material, a material containing Indium Oxide, that is, indium Tin Oxide (hereinafter, abbreviated as ITO) as a main component is widely used because of its high visible light transmittance, low surface resistance value, and excellent environmental characteristics. However, the lower limit of the surface resistance value of ITO is 50 Ω/γ, and when used as an electrode for a large-sized display, the responsiveness is insufficient and unsuitable. The ITO film is brittle and has poor bending resistance, and has a high surface resistance value when bent, so that it is difficult to cope with flexibility of the display.
Therefore, development of a material or technology for replacing ITO, such as a metal mesh, in which an electrode pattern is not visible when a thin film of a metal material such as silver, copper, or aluminum alloy is formed on a substrate by a physical vapor deposition method (PDV/Physical Vapor Deposition) such as a vacuum vapor deposition method or a sputtering method, or a chemical vapor deposition method (CVD/Chemical Vapor Deposition), or a conductive ink, in which a metal is nano-dispersed, is performed by performing fine patterning.
Patent document 1 discloses a photosensitive resin composition, a porous resin, a circuit board, and a suspension board with a circuit, each of which contains a solvent and one selected from a polyamic acid resin, a photosensitive material, an isocyanurate compound, a carbonate compound, a dendrimer or hyperbranched polymer having a molecular weight of 100 to 10,000.
Patent document 2 discloses an active energy ray-curable resin composition comprising a urethane (meth) acrylate resin obtained by reacting a trimer of a diisocyanate with a hydroxyl group-containing (meth) acrylate, and at least one selected from the group consisting of a Michael adduct of (meth) acrylic acid and a 2- (meth) acryloxyalkyl carboxylic acid monoester.
Patent document 3 discloses an ultraviolet curable resin composition and a film, and a conductive film, each comprising a (meth) acrylate monomer and/or acrylate oligomer having a (meth) acryloyl group, a thiourea type silane coupling agent, and nano silica particles having an average particle diameter of 100nm to 500 nm.
Patent document 4 discloses a resin material and a method for producing the same, the resin material comprising: a coating layer comprising a metal oxide, and a primer layer comprising a reaction product of a tri (meth) acrylate compound having an isocyanurate ring, a di (meth) acrylate having an aromatic ring, and a tetrahydrophthalimide type silane coupling agent with colloidal silica.
Patent document 5 discloses an active energy ray-curable resin composition, a coating agent, and a coating agent for precoating metals, which contain: urethane (meth) acrylate compounds obtained by reacting a polyvalent isocyanate compound with a hydroxyl group-containing (meth) acrylate compound containing a structural moiety derived from epsilon-caprolactone, and nitrogen-containing (meth) acrylate compounds other than urethane (meth) acrylates.
In order to form a metal material on a film base material, a primer treatment is generally required, but a conventional treatment with a tackifier paint improves good adhesion to a metal material, and reduces surface hardness, so that a countermeasure against damage in a manufacturing process, a processing process, or the like of a conductive film is a problem.
In order to solve the above problems, ultraviolet (UV) curable adhesion promoters containing organic and/or inorganic materials having excellent affinity for metal materials have been studied as follows, but these curable films tend to be as follows: when the crosslinking density is increased to increase the surface hardness, the performance as a tie coat tends to be low, and the adhesion to a metal material tends to be low.
Patent document 6 discloses a primer for a base material with a copper thin film, which contains: an acrylic copolymer (A) having a hydroxyl group, an alkyl ester group and a nitrile group, and optionally having a primary amide group, a polyisocyanate (B) having at least three isocyanate groups, an active energy ray-polymerizable compound (C) having at least three groups containing carbon-carbon double bonds, and a reactive alkoxysilane group compound (D) having a reactive group selected from reactive groups containing isocyanate groups.
Patent document 7 proposes a primer for a base material with a copper thin film, which contains: a polyester polyol (A) having dicarboxylic acids and diols as reaction components and having a glass transition temperature of 80 ℃ or lower, a polyisocyanate (B) having at least three isocyanate groups, a reactive alkoxysilane-based compound (C) having a reactive group selected from the group consisting of reactive groups containing isocyanate groups, and an active energy ray-polymerizable compound (E) having at least three groups containing carbon-carbon double bonds.
As described above, when a thermally crosslinkable inert resin and an active energy ray polymerizable compound are used in combination, the problem of scratch resistance in the production process, the processing process, and the like of a conductive film using a reactive alkoxy compound is not solved. In addition, in order to suppress an increase in dielectric constant or dielectric loss tangent, it is necessary to suppress the use of a highly polar material for the undercoat layer as much as possible in response to the development of high-speed data communication.
However, in the materials disclosed in the above documents, a hard coat layer having high transparency, hardness, scratch resistance, alkali resistance, and adhesion to a metal thin film cannot be formed at the time of forming the hard coat layer.
Prior art literature
Patent literature
Patent document 1: japanese patent laid-open No. 2001-214058
Patent document 2: japanese patent laid-open No. 2002-285043
Patent document 3: japanese patent laid-open publication 2016-008241
Patent document 4: japanese patent laid-open publication 2016-112702
Patent document 5: japanese patent laid-open publication No. 2019-112637
Patent document 6: japanese patent laid-open publication 2016-069653
Patent document 7: japanese patent laid-open No. 2015-199946
Disclosure of Invention
Problems to be solved by the invention
The object to be solved by the embodiments of the present invention is to provide an active energy ray-curable hard coating agent for forming a hard coating layer having high transparency and hardness and excellent scratch resistance, alkali resistance, and adhesion to a metal thin film when forming the hard coating layer. Another object of another embodiment of the present invention is to provide a hard coat layer formed using the active energy ray-curable hard coat agent, and a laminate including the hard coat layer.
Technical means for solving the problems
The present inventors have made diligent studies to solve the above problems, and as a result, have completed the following invention.
That is, the first embodiment relates to an active energy ray-curable hard coat agent for forming a hard coat layer having a metal thin film on the hard coat layer, the active energy ray-curable hard coat agent comprising: the compound (A) having three or more (meth) acryloyl groups, the silane coupling agent (B) having isocyanate groups, and the photopolymerization initiator (C) are contained in an amount of 70 parts by mass or more based on 100 parts by mass of the nonvolatile component of the active energy ray-curable hard coat agent.
In addition, the second embodiment relates to the active energy ray-curable hard coat agent, wherein the compound (a) contains a compound (a 1) having three or more (meth) acryloyl groups and having a nitrogen atom.
The third embodiment relates to the active energy ray-curable hard coat agent, wherein the compound (a 1) contains a compound (a 2) having three or more (meth) acryloyl groups and having a urethane ring skeleton.
In addition, a fourth embodiment relates to the active energy ray-curable hard coat agent, wherein the silane coupling agent (B) is contained in an amount of 5 to 30 parts by mass based on 100 parts by mass of a nonvolatile component of the active energy ray-curable hard coat agent.
In addition, a fifth embodiment relates to a hard coat layer formed from the active energy ray-curable hard coat agent.
In addition, a sixth embodiment relates to the hard coat layer, wherein the relative dielectric constant at a frequency of 1GHz and 23 ℃ is 3.2 or less, and the dielectric loss tangent is 0.02 or less.
In addition, a seventh embodiment relates to a laminate in which the hard coat layer is laminated on a base material.
Further, an eighth embodiment relates to the laminate, wherein a metal thin film is laminated on a hard coat layer.
ADVANTAGEOUS EFFECTS OF INVENTION
According to an embodiment of the present invention, an active energy ray-curable hard coat agent for forming a hard coat layer having high transparency and hardness and excellent scratch resistance, alkali resistance, and adhesion to a metal thin film when forming a hard coat layer can be provided. In addition, according to another embodiment of the present invention, there can be provided a hard coat layer formed using the active energy ray-curable hard coat agent, and a laminate including the hard coat layer.
Detailed Description
Hereinafter, embodiments of the present invention will be described, and first, terms used in the present specification will be described. In the present specification, unless otherwise specified, the expressions "(meth) acrylic group", "(meth) acrylic acid", "(meth) acrylic ester", and "(meth) acryloyloxy group" are used to denote "acrylic group or methacrylic group", "acryl group or methacryloyl group", "acrylic acid or methacrylic acid", "acrylate or methacrylate" and "acryloyloxy group or methacryloyloxy group", respectively. Unless otherwise specified, "parts" means "parts by mass" and "%" means "% by mass". In addition, the "active energy ray-curable hard coat agent" according to the embodiment of the present invention may be simply referred to as a "hard coat agent", the "compound (a) having three or more (meth) acryloyl groups" may be simply referred to as a "compound (a)", the "silane coupling agent (B) having isocyanate groups" may be simply referred to as a "silane coupling agent (B)", the "compound (a 1) having three or more (meth) acryloyl groups and having a nitrogen atom" may be simply referred to as a "compound (a 1)", the "compound (a 2) having three or more (meth) acryloyl groups and having a urethane ring skeleton" may be simply referred to as a "compound (a)", the "compound (a) other than the" compound (a 2) "may be simply referred to as a" compound (a) ", and the" compound (a 0) having one or two (meth) acryloyl groups "may be simply referred to as a" compound (a 0) ".
The hard coat agent according to an embodiment of the present invention is characterized by comprising the compound (a), the silane coupling agent (B), and the photopolymerization initiator (C), wherein the compound (a) is contained in an amount of 70 parts by mass or more based on 100 parts by mass of the nonvolatile component of the active energy ray-curable hard coat agent.
< Compound (A) having three or more (meth) acryloyl groups >
Examples of the compound (a) include:
polyol poly (meth) acrylate compounds such as trimethylolpropane tri (meth) acrylate, glycerol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, pentaerythritol tri (meth) acrylate, and pentaerythritol tetra (meth) acrylate;
trimers (isocyanurates) of (meth) acrylic acid esters having isocyanato groups, such as tris (2-acryloxyethyl) isocyanurate, ethylene Oxide (EO) modified tris (2-acryloxyethyl) isocyanurate, propylene Oxide (PO) modified tris (2-acryloxyethyl) isocyanurate, and epsilon-caprolactone modified tris (2-acryloxyethyl) isocyanurate; and
the (meth) acryl group is a polyacrylate of a polymer polyol such as three or more polyacrylic poly (meth) acrylates, polyurethane poly (meth) acrylates, and polyester (meth) acrylates;
and polyepoxy (meth) acrylates, etc., but are not limited thereto.
Further, from the viewpoint of adhesion to a metal thin film, the compound (a) is preferably a compound (a 1) having three or more (meth) acryloyl groups and having a nitrogen atom, and more preferably a compound (a 2) having three or more (meth) acryloyl groups and having a urethane ring structure. By containing the compound (a 1), a hard coat layer excellent in hardness, scratch resistance, and adhesion to a metal thin film can be obtained. Since the urethane ring structure is a trimer of an isocyanate compound having a nitrogen atom and is a six-membered ring, polymerization of a (meth) acryloyl group proceeds around the rigid six-membered ring and reacts, and excellent hardness, scratch resistance, and adhesion of a metal thin film are exhibited by a synergistic effect of affinity with both the silane coupling agent (B) and the metal thin film.
Examples of the compound (a 1) include, but are not limited to, urethane acrylates having three or more (meth) acryloyl groups, such as Fan Keli (FANCRYL) FA-731A manufactured by Hitachi chemical Co., ltd.), new front Takava (NEW FRONTIER TEICA) (GX-8430) manufactured by the first Industrial pharmaceutical Co., ltd.), EO-modified tris (2-ethoxyethyl) isocyanurate (Aronix) M-313 and M-315 manufactured by Tokyo chemical Co., ltd., NK esters (NK Ester) A-9300 manufactured by New Sanremo chemical Co., ltd., arkema (SARTOMER) SR-368 and the like), PO-modified tris (2-ethoxyethyl) isocyanurate, and epsilon-caprolactone-modified tris (2-ethoxyethyl) isocyanurate (NK Ester (Ester) A-9300-1 and the like manufactured by New Sanremo chemical Co., ltd.).
In the embodiment of the present invention, when the compound (a) is contained in at least 70 parts by weight in 100 parts by weight of the nonvolatile component of the active energy ray-curable hard coat agent, a hard coat layer capable of forming a metal thin film excellent in hardness and scratch resistance can be obtained. The upper limit of the content of the compound (a) in 100 parts by weight of the nonvolatile component of the active energy ray-curable hard coat agent is less than 100 parts. The content of the compound (a) is, for example, 80 parts or more, or 90 parts or more.
Silane coupling agent (B) having isocyanato group
The silane coupling agent (B) is preferably of the general formula (1): X1-Si (R1) a (OR2) 3-a (in the formula (1), X1 represents an isocyanate group, R1 represents a hydrocarbon group having 1 to 8 carbon atoms, R2 represents a hydrocarbon group having 1 to 8 carbon atoms, and a represents a reactive alkoxysilane group represented by 0, 1 or 2). The silane coupling agent (B) may contain an isocyanato group, and X1 may be an isocyanatoalkyl group.
The silane coupling agent (B) may be: 3-isocyanatopropyl trimethoxysilane, 3-isocyanatopropyl triethoxysilane, 3-isocyanatopropyl methyl dimethoxysilane, 3-isocyanatopropyl methyl diethoxysilane, and trimers (isocyanurates) of these compounds.
Examples of the commercially available silane coupling agent (B) include: KBE-9007N (3-isocyanatopropyl triethoxysilane, manufactured by Xin Yue chemical Co., ltd.), X-12-1159 (chemical structure is unknown, manufactured by Xin Yue chemical Co., ltd.), KBM-9659 (tris (trimethoxysilylpropyl) isocyanurate, manufactured by Xin Yue chemical Co., ltd.), xieluest Silane (SILQUEST Silane) A-1310 (3-isocyanatopropyl triethoxysilane, manufactured by Michime (MOMENTIVE) Co., ltd.), and Xieluest Silane (SILQUEST Silane) Y-5187 (3-isocyanatopropyl trimethoxysilane, manufactured by Michime (MOMENTIVE)) and the like.
The silane coupling agent (B) is preferably contained in an amount of 5 to 30 parts, more preferably 7 to 25 parts, and even more preferably 8 to 15 parts, in 100 parts of the nonvolatile component of the active energy ray-curable hard coat agent, in terms of both hardness and scratch resistance, and adhesion to the metal thin film.
In the embodiment of the present invention, the hard coat agent may contain, in addition to the above, the compound (a 0), a silane coupling agent or silane compound having no isocyanate group, a condensate thereof, and other additives described later.
Examples of the compound (a 0) include:
di (meth) acrylates such as 1, 3-butanediol di (meth) acrylate, 1, 4-butanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, diethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, and ethylene oxide modified di (meth) acrylate of bisphenol a;
di (meth) acrylate oligomers such as polyurethane poly (meth) acrylate and polyester poly (meth) acrylate; and
mono (meth) acrylates such as 2-ethylhexyl (meth) acrylate, isodecyl (meth) acrylate, isooctyl (meth) acrylate, benzyl (meth) acrylate, cyclopentylalkyl (meth) acrylate, cyclohexyl (meth) acrylate, dicyclopentenyl (meth) acrylate, and isobornyl (meth) acrylate are not limited thereto.
Photopolymerization initiator (C) >)
Examples of the photopolymerization initiator (C) include a monocarbonyl-based photopolymerization initiator, a dicarbonyl-based photopolymerization initiator, an acetophenone-based photopolymerization initiator, a benzoin ether-based photopolymerization initiator, an acylphosphine oxide-based photopolymerization initiator, and an aminocarbonyl-based photopolymerization initiator.
Examples of the photopolymerization initiator (C) include:
monocarbonyl-based photopolymerization initiators such as benzophenone, 4-methylbenzophenone, 2,4, 6-trimethylbenzophenone, methylparaben, 4-phenylbenzophenone, 3', 4' -tetrakis (t-butylperoxycarbonyl) benzophenone, 2-/4-isopropylthioxanthone, 2, 4-diethylthioxanthone, 2, 4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone;
dicarbonyl photopolymerization initiators such as 2-ethylanthraquinone, 9, 10-phenanthrenequinone, and methyl- α -oxo-phenylacetate;
acetophenone photopolymerization initiators such as 2-hydroxy-2-methyl-1-phenylpropane-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methyl-1-phenylpropane-1-one, 1-hydroxy-cyclohexylphenyl ketone, diethoxyacetophenone, dibutoxyacetophenone, 2-dimethoxy-1, 2-diphenylethan-1-one, 2-diethoxy-1, 2-diphenylethan-1-one, 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholinopropane-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one, and 1-phenyl-1, 2-propanedione-2- (o-ethoxycarbonyl) oxime;
benzoin ether photopolymerization initiators such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzoin n-butyl ether;
an acylphosphine oxide-based photopolymerization initiator such as 2,4, 6-trimethylbenzoyl diphenyl phosphine oxide and 4-n-propylphenyl-bis (2, 6-dichlorobenzoyl) phosphine oxide; and
aminocarbonyl-based photopolymerization initiators such as ethyl-4- (dimethylamino) benzoate, 2-n-butoxyethyl-4- (dimethylamino) benzoate, isopentyl-4- (dimethylamino) benzoate, 2- (dimethylamino) ethylbenzoate, 4' -bis-4-dimethylaminobenzophenone, 4' -bis-4-diethylaminobenzophenone, and 2,5' -bis (4-diethylaminobenzylidene) cyclopentanone.
Examples of the commercial products of the photopolymerization initiator (C) include, for example, acibenzolar (Lucirin) TPO manufactured by IGM resin (IGM-Resins b.v.) company, namely, omnirad (Omnirad) 184, 651, 500, 907, 127, 369, 784, 2959, ai Sagu ten thousand (Esacure one), BASF (BASF) (strand), and the like. In particular, from the viewpoint of yellowing resistance after active energy ray hardening, ohmic nilrad (Omnirad) 184 or Ai Sagu ten thousand (Esacure one) is preferable.
The photopolymerization initiator (C) may be used in combination of two or more kinds. In addition, a sensitizer may be used in combination.
The content of the photopolymerization initiator (C) is preferably 1 to 15 parts, more preferably 3 to 10 parts, in terms of the curing speed, the hardness and the scratch resistance, of 100 parts of the nonvolatile component of the active energy ray-curable hard coat agent. Further preferably 3 to 8 parts.
In embodiments of the present invention, the hard coating agent may include an organic solvent (D). As the organic solvent used, there may be used: aromatic organic solvents such as toluene and xylene; ketone-based organic solvents such as methyl ethyl ketone and methyl isobutyl ketone; ester-based organic solvents such as ethyl acetate, n-propyl acetate, isopropyl acetate, isobutyl acetate, and the like; alcohol-based organic solvents such as methanol, ethanol, n-propanol, isopropanol, and n-butanol; known organic solvents such as glycol ether-based organic solvents, e.g., propylene glycol monomethyl ether. Particularly preferred is an organic solvent containing a glycol ether system.
In the embodiment of the present invention, the content of the organic solvent (D) when the organic solvent (D) is contained is preferably in the range of 1% to 60% of the nonvolatile concentration of the hard coat agent from the viewpoints of coatability and film-forming property.
In the embodiment of the present invention, various additives may be further contained in the hard coat agent. As the additive, there may be mentioned: thermosetting resins, polymerization inhibitors, leveling agents, lubricants, defoamers, surfactants, antibacterial agents, antiblocking agents, plasticizers, ultraviolet absorbers, infrared absorbers, antioxidants, silane coupling agents, conductive agents, inorganic fillers, pigments, dyes, and the like. The hard coat agent may contain an acrylic resin such as a (meth) acrylic copolymer having a hydroxyl group.
< laminate >
The laminate according to the embodiment of the present invention is a laminate in which a hard coat layer formed from the hard coat agent according to the embodiment is laminated on the surface of a base material. In addition, as the laminate according to the embodiment of the present invention, a metal thin film may be further laminated on the hard coat layer.
Further, the laminated body according to the embodiment of the present invention includes, for example: a hard coat layer formed using the hard coat agent of the embodiment, and a metal thin film formed on the hard coat layer. The method for producing the laminate includes, for example: the hard coat layer is formed using the hard coat agent of the embodiment, and a metal thin film is formed on the hard coat layer. Further, according to an embodiment of the present invention, a laminated body includes, for example: the hard coat layer is formed by using the hard coat agent of the embodiment on the substrate, and a metal thin film formed on the hard coat layer. The method for producing the laminate includes, for example: the hard coat agent of the embodiment is used to form a hard coat layer on a substrate, and a metal thin film is formed on the hard coat layer.
The substrate (also referred to as a support) is not particularly limited, and examples thereof include: glass, synthetic resin molded articles, films, and the like. The synthetic resin molded article may be: and molded articles of synthetic resins such as polymethyl methacrylate resins, copolymer resins containing methyl methacrylate as a main component, polystyrene resins, styrene-methyl methacrylate copolymer resins, styrene-acrylonitrile copolymer resins, polycarbonate resins, cellulose acetate butyrate resins, polyallyldiethylene glycol carbonate resins, polyvinyl chloride resins, and polyester resins.
Examples of the film include: polyester film, polyethylene film, polypropylene film, cellophane film, diacetyl cellulose film, triacetyl cellulose (triacetyl cellulose, TAC) film, acetyl cellulose butyrate film, polyvinyl chloride film, polyvinylidene chloride film, polyvinyl alcohol film, ethylene vinyl alcohol film, polyolefin film, polystyrene film, polycarbonate film, polymethylpentene film, polysulfone film, polyetheretherketone film, polyethersulfone film, polyetherimide film, polyimide film, fluororesin film, nylon film, acrylic film, and the like.
The thickness of the hard coat layer is not particularly limited, but is usually about 0.1 μm to 5 μm.
Examples of the metal thin film include: a metal vapor deposited film, a metal sputtered film, and a metal CVD film. In the embodiment of the present invention, when the laminate is to be provided to an electrode film, a metal deposited film or a metal sputtered film is particularly preferable as the metal thin film. The thickness of the metal thin film is not particularly limited, but is usually about 0.1 μm to 2 μm. The metal constituting the metal thin film includes: copper, aluminum, silver, etc., but are not limited thereto.
The method for producing the laminate according to the embodiment of the present invention is not particularly limited. For example, the method can be carried out by the following steps: the hard coat agent of the embodiment is (1) applied to the surface of a substrate (one side or both sides in the case of a film-shaped substrate, for example), (2) heated, and then (3) hardened by further irradiation with an active energy ray to form a hard coat layer. Further, as necessary, a form manufactured by the step of forming a metal thin film on the hard coat layer by (4) can be mentioned.
In the step (1), the conditions for applying the hard coating agent to the surface of the substrate (one side or both sides in the case where the substrate is a film-like substrate, for example) are not particularly limited, and examples of the application method include: spray, roll coater, reverse roll coater, gravure coater, knife coater, bar coater, spot coater, and the like. The coating amount is not particularly limited, and is usually 0.01g/m as a dry nonvolatile component 2 ～10g/m 2 Left and right.
The conditions for heating the substrate in the step (2) are not particularly limited, and the temperature is usually about 80 to 150℃and the time is about 10 seconds to 2 minutes.
The conditions for irradiation with the active energy ray in the step (3) are not particularly limited. Examples of the active energy ray include ultraviolet rays and electron beams. As a source of ultraviolet rays, for example, a high-pressure mercury lamp, a metal halide lamp, or the like, the irradiation energy of which is usually 100mJ/cm, can be mentioned 2 ～2,000mJ/cm 2 Left and right. Examples of the electron beam supply system include a scanning electron beam irradiation method and a curtain electron beam irradiation method, and the irradiation energy is usually about 10kGy to 200 kGy.
The method for forming the metal thin film in the hard coat layer in the step (4) is not particularly limited, but a dry coating method is preferable. Specifically, examples thereof include physical methods such as vacuum vapor deposition and sputtering, and chemical methods (chemical vapor phase reaction, etc.) such as CVD.
The method for producing the conductive film is not particularly limited, but when it is used as an electrode film, the following method can be mentioned: various resists are coated on the metal vapor-deposited plastic film or the metal sputtering film, and after the electrode pattern is drawn, the film is immersed in an etching solution (alkali solution) to remove the resists. The shape of the electrode pattern may be any form such as a thin line, a dot, a net, or a plane.
The hard coat layer according to the embodiment of the present invention preferably has a relative dielectric constant of 3.2 or less, more preferably 3 or less at a frequency of 1GHz and 23 ℃ in terms of suppressing transmission loss due to refraction or reflection of an electric wave and reducing signal loss due to high-speed transmission. The dielectric loss tangent is preferably 0.02 or less, more preferably 0.01 or less.
Examples
The present invention will be described more specifically with reference to examples and comparative examples, but the following examples do not limit the technical scope of the present invention at all.
Production of acrylic copolymer (comparative example) >
Comparative production example 1
A reaction vessel including a stirrer, a thermometer, a reflux condenser, a dropping funnel and a nitrogen inlet tube was charged with 40.8 parts (13.6 mol%) of hydroxyethyl acrylate (hydroxy ethyl acrylate, HEA), 72.0 parts (27.7 mol%) of methyl methacrylate (methyl methacrylate, MMA), 79.2 parts (23.8 mol%) of Butyl Acrylate (BA), 48.0 parts (about 34.9 mol%) of Acrylonitrile (AN), 445.7 parts of ethyl acetate, and the reaction system was set to 70 ℃. Subsequently, 1.2 parts of 2,2'-azobis (2, 4-dimethylvaleronitrile) (2, 2' -azobis (2, 4-dimethyl valeronitrile), ABN-V) was charged, and the mixture was kept at a temperature of about 70℃for 6 hours. Subsequently, 2.4 parts of ABN-V was charged, and the reaction system was further incubated at around the above temperature for 6 hours. Then, the reaction system was cooled to room temperature to obtain a solution of an acrylic copolymer having a glass transition temperature of 13℃and a hydroxyl value of 80mgKOH/g and a nonvolatile content of 35.0%.
< preparation of hard coating agent >)
Example 1
90 parts of Aronix M-403 (manufactured by east Asia Synthesis Co., ltd.), 10 parts of KBE-9007N (3-isocyanatopropyl triethoxysilane manufactured by Xinyue chemical industry Co., ltd.), and 5 parts of Ai Sagu kilo (Esacure one) (manufactured by Japanese DKSH Co., ltd.) were thoroughly mixed, and propylene glycol monomethyl ether as an organic solvent was adjusted so that the nonvolatile content became 40%, to obtain a hard coat agent.
Examples 2 to 11 and comparative examples 1 to 5
A hard coat agent having a nonvolatile content of 40% was obtained in the same manner as in example 1, except that the components were blended in the compositions (nonvolatile content conversion) shown in table 1. Unless otherwise specified, the numerical values in table 1 represent "parts" and the blank indicates that they are not prepared.
Details of the respective materials shown in table 1 are as follows.
< Compound (A) >)
Aronix M-403 (mixture of dipentaerythritol hexaacrylate (number of functional groups: six): 40% to 50% and dipentaerythritol pentaacrylate (number of functional groups: five): 50% to 60%; manufactured by east Asia Synthesis Co., ltd.)
< Compound (a 1) >)
Mi Lamo (Miramer) PU610 (urethane acrylate, weight-average molecular weight: 1800, number of functional groups: six, manufactured by MiWON Co., ltd.)
Mi Lamo (Miramer) MU9800 (urethane acrylate, weight average molecular weight: 3500, functional groups: nine, manufactured by MiWON Co., ltd.)
< Compound (a 2) >)
Aronix (Aronix) M-315 (isocyanuric acid ethylene oxide modified triacrylate, functional group: three, manufactured by east Asia Synthesis Co., ltd.)
Silane coupling agent (B) having isocyanato group
KBE-9007N (3-isocyanatopropyl triethoxysilane, manufactured by Xinyue chemical industry Co., ltd.)
KBM-9659 (tris (trimethoxysilylpropyl) isocyanurate, manufactured by Xinyue chemical industry Co., ltd.)
Cellulose nyquist Silane (SILQUEST Silane) Y-5187 (3-isocyanatopropyl trimethoxysilane, manufactured by Michaelk (MOMENTIVE) Co., ltd.)
Photopolymerization initiator (C) >)
Esacure one (Ai Sagu Wan, acetophenone photopolymerization initiator, manufactured by Japanese DKSH (stock))
< others >
< Compound (a 0) having two (meth) acryloyl groups >
NK esters (NK Ester) A-DCP (tricyclodecane dimethanol diacrylate, molecular weight: 304, number of acryl groups: two, manufactured by Xinzhongcun chemical industries, ltd.)
Silane coupling agent (b 0) having acryl group
KBM-5103 (3-acryloxypropyl trimethoxysilane, manufactured by Xinyue chemical industry Co., ltd.)
Acrylic polyol (comparative production example 1) >
Acrylic polyol (solution of acrylic copolymer having a glass transition temperature of 13℃and a hydroxyl value of 80mgKOH/g and a nonvolatile content of 35.0% synthesized in production example 1)
< alumina particle Dispersion >)
Nanopick (nano-propylene acetate dispersion, non-volatile matter concentration: 37% manufactured by the company BYK-Chemie Japan) 3610
Hard coating and laminate production
The hard coating agents obtained in examples and comparative examples were applied to 50 μm thick polyethylene terephthalate (polyethylene terephthalate, PET) films ("Lu Mila (Lumiror) U403", manufactured by Toli (Co.)) respectively, using a bar coater so that the film thickness after drying became 1.0. Mu.m, and then irradiated with a high-pressure mercury lamp at 500mJ/cm 2 To form a hard coat layer, thereby producing a laminate.
Pencil hardness
For the laminate thus produced, pencils of various hardness were made to touch the surface of the hard coat layer of the laminate at an angle of 45 ° in accordance with japanese industrial standard (Japanese Industrial Standards, JIS) K5600-5-4, and a scratch test was performed by applying a load, and the hardness of the hardest pencil that was not damaged was regarded as pencil hardness.
Determination of haze value
The haze value (HZ) of the hard coat layer surface was measured on the laminate thus produced by using a "haze meter SH7000" manufactured by japan electric color industry company.
Most preferred: less than 1.0%
Good: more than 1.0% and less than 2.0%
Poor: 2.0% or more
Scratch resistance
The laminate thus produced was evaluated for scratch resistance by using a "vibration type rubbing fastness Tester" manufactured by the detector industry (Tester Sangyo). On the friction member (surface area 1 cm) 2 ) Steel wool #0000 was mounted on the surface of the hard coat layer (1 cm. Times.15 cm) to make 10 round trips. Thereafter, the number of scratches on the surface of the hard coat layer was counted and evaluated according to the following criteria.
3: scratch-free (0 root)
2: scratches are more than 1 and less than 10
1: scoring more than 11
Copper adhesion
On the hard coat layer of the laminate thus produced, copper was sputtered to a thickness of 300nm, 500nm, and 1 μm by "magnetron sputtering MSP-30T" manufactured by Vacuum apparatus, inc., to form a copper thin film. Regarding the adhesion between the copper film and the primer hard coat layer, scratches were attached to the copper film in a checkered pattern using a cutter at 1mm intervals, and after forming a 100-mesh lattice pattern, a cellophane tape was attached so as to cover the entire checkered pattern, and the peeled state of the copper film was visually observed and evaluated according to the following criteria.
5: the perimeter of the scored line was completely smooth and any lattice did not flake off.
4: small flaking of the copper film was observed around the intersection of the scratches, but the total of the flaked areas was less than 5% of the checkerboard.
3: the copper film is peeled off along the edge direction of the scribe line, or the copper film is peeled off at the crossing point of the scribe line, or the total of peeled areas is 5% or more and less than 15% of the checkerboard.
2: the total of the peeled areas is 15% or more and less than 35% of the checkerboard.
1: the total of the peeled areas is 35% or more and less than 80% of the checkerboard.
0: the total of the peeled areas was 80% or more of the checkered scratches, and peeling was also observed outside the checkered scratches.
Alkali resistance
The laminate having the copper thin film (thickness 300 nm) not subjected to copper adhesion evaluation was immersed in a 5% aqueous sodium hydroxide solution heated to 40 ℃ for 5 minutes, then washed with water, dried in an oven heated to 100 ℃ for 15 minutes, and then dehydrated, and then copper adhesion was evaluated in the same manner as described above.
Determination of relative permittivity and dielectric loss tangent
The hard coating agents of examples and comparative examples were applied to a commercially available polyester film (trade name "Lu Mila (Lumirror) U48", manufactured by Toli (stock) and 100 μm thick) by a bar coater so that the dry film thickness became about 80 μm, and dried at 120℃for 1 minute. Then, at 300mJ/cm 2 UV hardening was performed to obtain a coating film (laminate) for measurement. The obtained measurement coating film was cut into a size of 3mm wide by 100mm long to obtain a measurement test piece. According to "flexible printed wiring board and material for flexible printed wiring board" of the Japanese society for electronic circuit, its two general standards- (JCA-DG 03) ", the relative dielectric constant and dielectric loss tangent of the obtained test piece for measurement were measured by the following procedure. Three test pieces were set on an "ADMS01Oc" of a relative dielectric constant measuring apparatus manufactured by AET company, and the relative dielectric constant and dielectric loss tangent at a measuring temperature of 23℃and a measuring frequency of 1GHz were obtained by a cavity resonator method. The results are shown in Table 1.
As shown in table 1, it was clear that when the hard coating agent according to the embodiment of the present invention was used, a hard coating layer having high transparency and hardness and excellent scratch resistance, alkali resistance, and adhesion to a metal thin film was formed.
TABLE 1
The disclosure of the present invention relates to the subject matter described in japanese patent application No. 2020-211044, filed on 12 months 21 in 2020, the disclosure of which is incorporated herein by reference.
Claims (8)
1. An active energy ray-curable hard coat agent for forming a hard coat layer having a metal thin film on the hard coat layer, comprising: the compound (A) having three or more (meth) acryloyl groups, the silane coupling agent (B) having isocyanate groups, and the photopolymerization initiator (C) are contained in an amount of 70 parts by mass or more based on 100 parts by mass of the nonvolatile component of the active energy ray-curable hard coat agent.
2. The active energy ray-curable hard coat agent according to claim 1, wherein the compound (a) contains a compound (a 1) having three or more (meth) acryloyl groups and having a nitrogen atom.
3. The active energy ray-curable hard coat agent according to claim 2, wherein the compound (a 1) contains a compound (a 2) having three or more (meth) acryloyl groups and having a urethane ring skeleton.
4. The active energy ray-curable hard coat agent according to any one of claims 1 to 3, wherein the silane coupling agent (B) is contained in an amount of 5 to 30 parts by mass based on 100 parts by mass of a nonvolatile component of the active energy ray-curable hard coat agent.
5. A hard coat layer formed from the active energy ray-curable hard coat agent according to any one of claims 1 to 4.
6. The hard coat layer according to claim 5, wherein the relative dielectric constant at a frequency of 1GHz at 23 ℃ is 3.2 or less and the dielectric loss tangent is 0.02 or less.
7. A laminate comprising a substrate and the hard coat layer according to claim 5 or 6 laminated on the substrate.
8. The laminate according to claim 7, further comprising a metal thin film laminated on the hard coat layer.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2020211044A JP6979559B1 (en) | 2020-12-21 | 2020-12-21 | Active energy ray-curable hard coat agent, hard coat layer and laminate |
| JP2020-211044 | 2020-12-21 | ||
| PCT/JP2021/044546 WO2022138082A1 (en) | 2020-12-21 | 2021-12-03 | Active-energy-curable hard coat agent, hard coat layer, and laminate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116406391A true CN116406391A (en) | 2023-07-07 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202180074368.0A Pending CN116406391A (en) | 2020-12-21 | 2021-12-03 | Active energy ray-curable hard coating agent, hard coating layer, and laminate |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP6979559B1 (en) |
| KR (1) | KR20230060537A (en) |
| CN (1) | CN116406391A (en) |
| TW (1) | TW202227562A (en) |
| WO (1) | WO2022138082A1 (en) |
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Also Published As
| Publication number | Publication date |
|---|---|
| KR20230060537A (en) | 2023-05-04 |
| JP2022097848A (en) | 2022-07-01 |
| TW202227562A (en) | 2022-07-16 |
| JP6979559B1 (en) | 2021-12-15 |
| WO2022138082A1 (en) | 2022-06-30 |
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