CN109312012B - Active energy ray-curable composition and film using same - Google Patents
Active energy ray-curable composition and film using same Download PDFInfo
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- CN109312012B CN109312012B CN201780039287.0A CN201780039287A CN109312012B CN 109312012 B CN109312012 B CN 109312012B CN 201780039287 A CN201780039287 A CN 201780039287A CN 109312012 B CN109312012 B CN 109312012B
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- Prior art keywords
- meth
- acrylate
- active energy
- mass
- energy ray
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- 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
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920002454 poly(glycidyl methacrylate) polymer Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ZKDDJTYSFCWVGS-UHFFFAOYSA-M sodium;diethoxy-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Na+].CCOP([S-])(=S)OCC ZKDDJTYSFCWVGS-UHFFFAOYSA-M 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 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
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- FCGQIZKUTMUWDC-UHFFFAOYSA-M trimethyl(propyl)azanium;bromide Chemical compound [Br-].CCC[N+](C)(C)C FCGQIZKUTMUWDC-UHFFFAOYSA-M 0.000 description 1
- NRWCNEBHECBWRJ-UHFFFAOYSA-M trimethyl(propyl)azanium;chloride Chemical compound [Cl-].CCC[N+](C)(C)C NRWCNEBHECBWRJ-UHFFFAOYSA-M 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- RSJKGSCJYJTIGS-BJUDXGSMSA-N undecane Chemical group CCCCCCCCCC[11CH3] RSJKGSCJYJTIGS-BJUDXGSMSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/16—Layered products comprising a layer of synthetic resin specially treated, e.g. irradiated
-
- 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
-
- 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
- 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
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (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
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
- C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
- C08L101/025—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing nitrogen atoms
-
- 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
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
-
- 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
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
- C09D201/02—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
- C09D201/025—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing nitrogen atoms
-
- 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
Abstract
The invention provides an active energy ray-curable composition capable of forming a hard coat layer having both high refractive index and high antistatic property, and a film using the same. The present invention uses an active energy ray-curable composition containing a high-refractive-index polymerizable monomer (A) having a refractive index of 1.55 or more, a polyfunctional polymerizable monomer (B), a resin (C) having an alicyclic structure and a quaternary ammonium salt, and an organic solvent (D). Further, the active energy ray-curable composition is used, wherein the resin (C) is a polymer using 5 to 40 mass% of a polymerizable monomer having an alicyclic structure as a raw material. The organic solvent (D) has a dispersion term (delta D) of 15.5 to 16.1MPa in terms of Hansen solubility parameter0.5In the range of 6.3 to 10.4MPa in terms of polarity (delta P)0.5In the range of 5.1 to 11.6MPa in terms of hydrogen bond term (delta H)0.5An organic solvent in the range of (1).
Description
Technical Field
The present invention relates to an active energy ray-curable composition capable of forming a hard coat layer having a high refractive index and high antistatic properties on a film surface by applying the composition to the surface of the film and curing the composition, and a film using the active energy ray-curable composition.
Background
An antireflection (LR) film used for a surface of a Flat Panel Display (FPD) such as a Liquid Crystal Display (LCD), an organic EL display (OLED), or a Plasma Display (PDP) is realized by forming a multilayer structure (substrate/high refractive index layer/low refractive index layer) having 2 layers with a large refractive index difference on a film substrate. Each of the above layers is required to have high scratch resistance in order to prevent damage of the antireflection film during the production process, and also to have high antistatic properties in order to prevent contamination of the film and blocking. Further, since the antireflection film is an optical film, each layer is also required to have high transparency.
Among the above-described required properties, as a method for imparting antistatic properties, it has been proposed to use a material containing a resin having a quaternary ammonium salt (see, for example, patent documents 1 to 3). However, these materials are not high refractive index materials.
Therefore, an active energy ray-curable composition capable of forming a hard coat layer having a high refractive index and high antistatic properties is required.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open No. 2012 and 102166
Patent document 2: japanese laid-open patent publication No. 2008-013636
Patent document 3: japanese patent laid-open No. 2008-255184
Disclosure of Invention
Technical problem to be solved by the invention
The present invention addresses the problem of providing an active energy ray-curable composition capable of forming a hard coat layer having both a high refractive index and high antistatic properties, and a film using the active energy ray-curable composition.
Means for solving the problems
The present inventors have intensively studied to solve the above-mentioned problems, and as a result, they have found that a hard coat layer having both a high refractive index and a high antistatic property can be formed by blending a specific high refractive index polymerizable monomer, a resin having an alicyclic structure and a quaternary ammonium salt, and the like in an active energy ray-curable composition, and have completed the present invention.
That is, the present invention provides an active energy ray-curable composition containing a high refractive index polymerizable monomer (a) having a refractive index of 1.55 or more, a polyfunctional polymerizable monomer (B), a resin (C) having an alicyclic structure and a quaternary ammonium salt, and an organic solvent (D), and a film using the same.
ADVANTAGEOUS EFFECTS OF INVENTION
The active energy ray-curable composition of the present invention is applied to the surface of a film and cured, thereby forming a hard coat layer having a high refractive index and high antistatic properties on the surface of the film. Therefore, the cured coating film of the active energy ray-curable composition of the present invention is very useful as a material for an antireflection film.
In addition, a film having a hard coat layer comprising a cured coating film of the active energy ray-curable composition of the present invention can be suitably used as an optical film used in a Flat Panel Display (FPD) such as a Liquid Crystal Display (LCD), an organic EL display (OLED), and a Plasma Display (PDP). Further, when used for these applications, the antistatic properties are excellent, and adhesion of dust and the like can be suppressed. Further, when the film is used for a liquid crystal display or the like, it is possible to prevent malfunction of the display due to static electricity generated.
Detailed Description
The active energy ray-curable composition of the present invention contains a high-refractive-index polymerizable monomer (A) having a refractive index of 1.55 or more, a polyfunctional polymerizable monomer (B), a resin (C) having an alicyclic structure and a quaternary ammonium salt, and an organic solvent (D).
The polymerizable monomer (a) may be any polymerizable monomer having a high refractive index of 1.55 or more before curing, and examples thereof include: aromatic polymerizable monomers having 2 to 6 aromatic rings, fluorene polymerizable monomers, and the like. Specific examples of the polymerizable monomer (a) include: a compound represented by the following general formula (1); (meth) acrylate compounds having a phenylbenzyl group such as o-phenylbenzyl (meth) acrylate and p-phenylbenzyl (meth) acrylate; (meth) acrylate compounds having a phenylphenol group such as phenylphenol EO acrylate; bisphenol compounds having 2 to 4 (meth) acryloyl groups such as propoxylated bisphenol a di (meth) acrylate, ethoxylated bisphenol a di (meth) acrylate, bisphenol a di (meth) acrylate having a hydroxyethyl group, bisphenol a tri (meth) acrylate having a hydroxyethyl group, and the like. These polymerizable monomers (A) may be used in 1 kind, or two or more kinds may be used in combination. Among these, from the viewpoint of controlling the refractive index, 1 or more monomers selected from the group consisting of the compound represented by the following general formula (1), the (meth) acrylate compound having a phenylbenzyl group, and the bisphenol compound having 2 to 4 (meth) acryloyl groups are preferably used, and more preferably the compound represented by the following general formula (1) alone, the compound represented by the following general formula (1) and the (meth) acrylate compound having a phenylbenzyl group in combination, and the bisphenol compound having 2 to 4 (meth) acryloyl groups are preferably used alone. When the compound represented by the following general formula (1) is used in combination with a (meth) acrylate compound having a phenylbenzyl group, the mass ratio is preferably in the range of 30/70 to 70/30.
[ solution 1]
(in the formula (1), R1、R2Each represents a hydrogen group or a methyl group, and m and n each represents an integer of 0 to 5. )
In the present invention, "(meth) acrylate" means one or both of acrylate and methacrylate, and "(meth) acryloyl" means one or both of acryloyl and methacryloyl.
The polymerizable monomer (B) is a polyfunctional polymerizable monomer and has 2 or more polymerizable groups in 1 molecule. The polymerizable group may be a vinyl group or a (meth) acryloyl group as a carbon-carbon double bond, and a (meth) acryloyl group is preferable because it is excellent in curability.
Examples of the polymerizable monomer (B) having a (meth) acryloyl group include: 1, 4-butanediol di (meth) acrylate, 3-methyl-1, 5-pentanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 2-methyl-1, 8-octanediol di (meth) acrylate, 2-butyl-2-ethyl-1, 3-propanediol di (meth) acrylate, tricyclodecane dimethanol di (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate and other diol di (meth) acrylates, polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, and polypropylene glycol acrylate, and/or polypropylene glycol di (meth) acrylate, polypropylene glycol acrylate, and/or polypropylene glycol acrylate, polypropylene glycol di (meth) acrylate, and/or polypropylene glycol acrylate, Polypropylene glycol di (meth) acrylate, di (meth) acrylate of tris (2-hydroxyethyl) isocyanurate, di (meth) acrylate of diol obtained by adding 4 or more moles of ethylene oxide or propylene oxide to 1 mole of neopentyl glycol, di (meth) acrylate of diol obtained by adding 2 or more moles of ethylene oxide or propylene oxide to 1 moles of bisphenol a, trimethylolpropane tri (meth) acrylate, ethylene oxide-modified trimethylolpropane tri (meth) acrylate, propylene oxide-modified trimethylolpropane tri (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, tris (2- (meth) acryloyloxyethyl) isocyanurate, pentaerythritol tri (meth) acrylate, propylene oxide, and propylene oxide, and the like, Pentaerythritol tetra (meth) acrylate, dipentaerythritol tri (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and the like. These polyfunctional polymerizable monomers (B) may be used in 1 kind, or two or more kinds may be used in combination. Among these polyfunctional polymerizable monomers (B), dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate, pentaerythritol tetra (meth) acrylate, and pentaerythritol tri (meth) acrylate are preferable in terms of improving scratch resistance of a cured coating film of the active energy ray-curable composition of the present invention.
In the active energy ray-curable composition of the present invention, urethane (meth) acrylate may be further blended as a polymerizable component other than the polymerizable monomer (a) and the polymerizable monomer (B). The urethane (meth) acrylate (E) is obtained by reacting a polyisocyanate (E1) with a (meth) acrylate (E2) having a hydroxyl group.
Examples of the polyisocyanate (e1) include: the aliphatic polyisocyanate and the aromatic polyisocyanate are preferably aliphatic polyisocyanates from the viewpoint of reducing the coloring of the cured coating film of the active energy ray-curable composition of the present invention.
The aliphatic polyisocyanate is a compound in which the portion other than the isocyanate group is composed of an aliphatic hydrocarbon. Specific examples of the aliphatic polyisocyanate include: aliphatic polyisocyanates such as hexamethylene diisocyanate, lysine diisocyanate, and lysine triisocyanate; alicyclic polyisocyanates such as norbornane diisocyanate, isophorone diisocyanate, methylenebis (4-cyclohexyl isocyanate), 1, 3-bis (isocyanatomethyl) cyclohexane, 2-methyl-1, 3-diisocyanatocyclohexane, and 2-methyl-1, 5-diisocyanatocyclohexane. In addition, a trimer obtained by trimerizing the aliphatic polyisocyanate or the alicyclic polyisocyanate may be used as the aliphatic polyisocyanate. These aliphatic polyisocyanates may be used in 1 kind, or two or more kinds may be used in combination.
Among the above aliphatic polyisocyanates, hexamethylene diisocyanate, which is a diisocyanate of a straight chain aliphatic hydrocarbon, norbornane diisocyanate, which is an alicyclic diisocyanate, and isophorone diisocyanate are preferable in order to improve the scratch resistance of a coating film.
The (meth) acrylate (e2) is a compound having a hydroxyl group and a (meth) acryloyl group. Specific examples of the (meth) acrylic acid ester (e2) include: mono (meth) acrylates of glycols such as 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 1, 5-pentanediol mono (meth) acrylate, 1, 6-hexanediol mono (meth) acrylate, neopentyl glycol mono (meth) acrylate, hydroxypivalic acid neopentyl glycol mono (meth) acrylate, and the like; trimethylolpropane di (meth) acrylate, Ethylene Oxide (EO) -modified trimethylolpropane (meth) acrylate, Propylene Oxide (PO) -modified trimethylolpropane di (meth) acrylate, glycerol di (meth) acrylate, bis (2- (meth) acryloyloxyethyl) hydroxyethyl isocyanurate and the like trihydric alcohol mono or di (meth) acrylate, or hydroxyl group-containing mono and di (meth) acrylates obtained by modifying a part of these alcoholic hydroxyl groups with epsilon-caprolactone; a compound having a 1-functional hydroxyl group and a (meth) acryloyl group having 3 or more functional groups, such as pentaerythritol tri (meth) acrylate, ditrimethylol propane tri (meth) acrylate, and dipentaerythritol penta (meth) acrylate, or a polyfunctional (meth) acrylate having a hydroxyl group, which is obtained by modifying the compound with e-caprolactone; (meth) acrylates having an oxyalkylene chain such as dipropylene glycol mono (meth) acrylate, diethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, and polyethylene glycol mono (meth) acrylate; (meth) acrylates having an oxyalkylene chain with a block structure such as polyethylene glycol-polypropylene glycol mono (meth) acrylate and polyoxybutylene-polyoxypropylene mono (meth) acrylate; and (meth) acrylates having an oxyalkylene chain of a random structure such as poly (ethylene glycol-tetramethylene glycol) mono (meth) acrylate and poly (propylene glycol-tetramethylene glycol) mono (meth) acrylate. These (meth) acrylates (e2) may be used in 1 kind, or two or more kinds may be used in combination.
Among the urethane (meth) acrylates (e2), urethane (meth) acrylates having 4 or more (meth) acryloyl groups in 1 molecule are preferable in order to improve the scratch resistance of the cured coating film of the active energy ray-curable composition of the present invention. In order to make the urethane (meth) acrylate (E) a urethane (meth) acrylate having 4 or more (meth) acryloyl groups in 1 molecule, the (meth) acrylate (E2) is preferably a (meth) acrylate having 2 or more (meth) acryloyl groups. Examples of such (meth) acrylic acid esters (e2) include: trimethylolpropane di (meth) acrylate, ethylene oxide-modified trimethylolpropane di (meth) acrylate, propylene oxide-modified trimethylolpropane di (meth) acrylate, glycerol di (meth) acrylate, bis (2- (meth) acryloyloxyethyl) hydroxyethyl isocyanurate, pentaerythritol tri (meth) acrylate, ditrimethylolpropane tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, and the like. These (meth) acrylic acid esters (e2) may be used in 1 kind or in combination of two or more kinds with respect to 1 kind of the above aliphatic polyisocyanate. Among these (meth) acrylates (e2), pentaerythritol tri (meth) acrylate and dipentaerythritol penta (meth) acrylate are preferable because scratch resistance can be improved.
The reaction of the above polyisocyanate (e1) with the above (meth) acrylic acid ester (e2) can be carried out by a urethanization reaction in a conventional manner. In addition, in order to promote the progress of the urethanization reaction, it is preferable to carry out the urethanization reaction in the presence of a urethanization catalyst. Examples of the urethane-forming catalyst include: amine compounds such as pyridine, pyrrole, triethylamine, diethylamine and dibutylamine; phosphorus compounds such as triphenylphosphine and triethylphosphine; and organic tin compounds such as dibutyltin dilaurate, octyltin trilaurate, octyltin diacetate, dibutyltin diacetate, and tin octylate, and organic zinc compounds such as zinc octylate.
In the active energy ray-curable composition of the present invention, epoxy (meth) acrylate, polyester (meth) acrylate, polyether (meth) acrylate, or the like may be used as necessary as polymerizable components other than the polymerizable monomer (a), the polymerizable monomer (B), and the urethane (meth) acrylate (E). Examples of the epoxy (meth) acrylate include: an epoxy (meth) acrylate obtained by reacting (meth) acrylic acid with a bisphenol-type epoxy resin, a novolac-type epoxy resin, a polyglycidyl methacrylate, or the like, and esterifying the resulting product. Examples of the polyester (meth) acrylate include: a polyester (meth) acrylate obtained by esterification by reacting (meth) acrylic acid with a polyester having hydroxyl groups at both ends obtained by polycondensing a polycarboxylic acid and a polyhydric alcohol, or a polyester (meth) acrylate obtained by esterification by reacting (meth) acrylic acid with a substance obtained by adding an alkylene oxide to a polycarboxylic acid. Further, examples of the polyether (meth) acrylate include: polyether (meth) acrylates obtained by reacting (meth) acrylic acid with polyether polyols are esterified.
The resin (B) is a resin having an alicyclic structure and a quaternary ammonium salt.
Examples of the method for producing the resin (C) include the following methods: the polymerizable monomer (c1) and the polymerizable monomer (c2) are copolymerized with a copolymerizable polymerizable monomer (c3) using a polymerizable monomer (c1) having an alicyclic structure and a polymerizable monomer (c2) having a quaternary ammonium salt as essential components.
The polymerizable monomer (c1) is a polymerizable monomer having an alicyclic structure. Examples of the alicyclic structure include: a monocyclic alicyclic structure such as a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, a cyclooctane ring, a cyclononane ring, or a cyclodecane ring; bicyclic undecane ring, decahydronaphthalene (decalin) ring, tricyclic [5.2.1.0 ]2，6]Decane ring, bicyclo [4.3.0]Nonane ring, tricyclo [5.3.1.1]Dodecane ring, tricyclo [5.3.1.1]Dodecyl ring, spiro [3.4 ]]And polycyclic alicyclic structures such as octane rings. Specific examples of the polymerizable monomer (b1) include cyclohexyl (meth) acrylate, 1, 4-cyclohexanedimethanol mono (meth) acrylate, isobornyl (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, and dicyclopentanyl (meth) acrylate. These polymerizable monomers (c1) may be used in 1 kind, or two or more kinds may be used in combination.
Examples of the polymerizable monomer (c2) include: polymerizable monomers having chloride as a counter anion, such as 2- [ (meth) acryloyloxy ] ethyltrimethylammonium chloride and 3- [ (meth) acryloyloxy ] propyltrimethylammonium chloride; polymerizable monomers having bromide as a counter anion, such as 2- [ (meth) acryloyloxy ] ethyltrimethylammonium bromide and 3- [ (meth) acryloyloxy ] propyltrimethylammonium bromide; and polymerizable monomers having a non-halogen counter anion such as 2- [ (meth) acryloyloxy ] ethyltrimethylammonium methylphenylsulfonate, 2- [ (meth) acryloyloxy ] ethyltrimethylammonium methanesulfonate, 3- [ (meth) acryloyloxy ] propyltrimethylammonium methylphenylsulfonate, 3- [ (meth) acryloyloxy ] propyltrimethylammonium methanesulfonate, 2- [ (meth) acryloyloxy ] ethyltrimethylammonium methylsulfate, and 3- [ (meth) acryloyloxy ] propyltrimethylammonium methylsulfate. These polymerizable monomers (c2) may be used in 1 kind, or two or more kinds may be used in combination.
Examples of the polymerizable monomer (c3) include: alkyl (meth) acrylates such as methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, n-pentyl (meth) acrylate, n-hexyl (meth) acrylate, n-heptyl (meth) acrylate, n-octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, and dodecyl (meth) acrylate; polyalkylene glycol mono (meth) acrylates such as methoxy polyethylene glycol mono (meth) acrylate, octyloxy polyethylene glycol-polypropylene glycol mono (meth) acrylate, lauryloxy polyethylene glycol mono (meth) acrylate, stearyloxy polyethylene glycol mono (meth) acrylate, phenoxy polyethylene glycol-polypropylene glycol mono (meth) acrylate, nonylphenoxypolypropylene glycol mono (meth) acrylate, and nonylphenoxypoly (ethylene glycol-propylene glycol) mono (meth) acrylate; and (meth) acrylates having a fluoroalkyl group such as 2-perfluorohexylethyl (meth) acrylate. These polymerizable monomers (c3) may be used in 1 kind, or two or more kinds may be used in combination.
Among the polymerizable monomers (c3), polyalkylene glycol mono (meth) acrylates are preferable, and methoxypolyethylene glycol mono (meth) acrylates are more preferable, from the viewpoint of further improving the antistatic properties of the cured coating film of the active energy ray-curable composition of the present invention. The (meth) acrylate having a fluoroalkyl group is also preferable in that it has an effect of further improving the antistatic property of the cured coating film of the active energy ray-curable composition of the present invention.
In the above-mentioned mono (meth) acrylate of a polyalkylene glycol, the number average molecular weight of the polyalkylene glycol which is a raw material of the mono (meth) acrylate of a polyalkylene glycol is preferably in the range of 200 to 8,000, more preferably in the range of 300 to 6,000, further preferably in the range of 400 to 4,000, and particularly preferably in the range of 400 to 2,000, in view of further improving the antistatic property of the cured coating film of the active energy ray-curable composition of the present invention.
The proportion of the polymerizable monomer (C1) in the total amount of the raw materials of the resin (C) is preferably in the range of 5 to 55 mass%, more preferably in the range of 10 to 50 mass%, and still more preferably in the range of 12 to 45 mass%, from the viewpoint of further improving the antistatic property of the cured coating film of the active energy ray-curable composition of the present invention.
In addition, from the viewpoint of further improving the antistatic property of the cured coating film of the active energy ray-curable composition of the present invention, the ratio of the polymerizable monomer (C2) in the total amount of the raw materials of the resin (C) is preferably in the range of 30 to 90% by mass, more preferably in the range of 40 to 80% by mass, and more preferably in the range of 45 to 70% by mass.
Further, in the case where the above-mentioned polyalkylene glycol mono (meth) acrylate is used as the above-mentioned polymerizable monomer (C3), the proportion of the polyalkylene glycol mono (meth) acrylate in the total amount of the raw materials of the resin (C) is preferably in the range of 5 to 60 mass%, more preferably in the range of 10 to 50 mass%, and still more preferably in the range of 20 to 40 mass%, from the viewpoint of further improving the antistatic property of the cured coating film of the active energy ray-curable composition of the present invention.
In addition, in the case where the (meth) acrylate having the fluoroalkyl group is used as the polymerizable monomer (C3), the ratio of the (meth) acrylate having the fluoroalkyl group in the total amount of the raw materials of the resin (C) is preferably in the range of 0.1 to 20 mass%, more preferably in the range of 0.5 to 10 mass%, and still more preferably in the range of 1 to 5 mass%, in view of further improving the antistatic property of the cured coating film of the active energy ray-curable composition of the present invention.
The weight average molecular weight of the resin (C) is preferably in the range of 1,000 to 100,000, more preferably 2,000 to 50,000, and even more preferably 3,000 to 30,000, in view of further improving the antistatic property of the cured coating film of the active energy ray-curable composition of the present invention. The weight average molecular weight in the present invention is a value in terms of polystyrene measured by a Gel Permeation Chromatography (GPC) method.
The amount of the resin (C) blended is preferably in the range of 0.1 to 30 parts by mass, more preferably 0.5 to 20 parts by mass, even more preferably 1 to 10 parts by mass, and particularly preferably 1.5 to 7 parts by mass, based on 100 parts by mass of the total of the polymerizable monomer (a) and the polymerizable monomer (B), from the viewpoint of further improving the antistatic property of a cured coating film of the active energy ray-curable composition of the present invention.
The organic solvent (D) is not particularly limited as long as it can dissolve other components in the active energy ray-curable composition of the present invention. In addition, from the viewpoint of further improving the antistatic property of the cured coating film of the active energy ray-curable composition of the present invention, it is preferable that the dispersion term (δ D) in terms of hansen solubility parameter is 15.5 to 16.1MPa0.5In the range of 6.3 to 10.4MPa in terms of polarity (delta P)0.5In the range of 5.1 to 11.6MPa in terms of hydrogen bond term (delta H)0.5An organic solvent in the range of (1).
It should be noted that the definition and calculation of Hansen Solubility Parameters are described in Charles m.hansen, Hansen "Hansen Solubility Parameters; a Users Handbook (CRC Press, 2007) "is described. Further, by using computer software "Hansen Solubility Parameters In Practice (HSPiP)", Hansen Solubility Parameters can be deduced from the chemical structure of an organic solvent which is not described in the literature as a parameter value. In the present invention, the values are used for organic solvents having parameter values described in the literature, and the parameter values estimated by using HSPiP version 4.1.06 are used for organic solvents having no parameter values described in the literature.
The organic solvent (D) may be 1 type of organic solvent, or two or more types of organic solvents may be used in combination as a mixed solvent. When two or more kinds of organic solvents are used in combination, a value obtained by weighted averaging 3 hansen solubility parameters of the respective organic solvents may be used in combination within the above range.
When two or more organic solvents are used in combination as the organic solvent (D), examples of a method for adjusting the range of the hansen solubility parameter include: ethanol (δ D ═ 15.8 MPa)0.5、δP＝8.8MPa0.5、δH＝19.4MPa0.5) Isoalcohol solvent and methyl ethyl ketone (delta D ═ 16.0 MPa)0.5、δP＝9.0MPa0.5、δH＝5.1MPa0.5) Combinations of the ketone solvents include the ketone solvents mentioned above and methyl acetate (δ D15.5 MPa)0.5、δP＝7.2MPa0.5、δH＝7.6MPa0.5) And combinations of the like. In addition to the combination of the alcohol solvent and the ketone solvent, the organic solvent (D) may further contain 3 to 40 mass% of diacetone alcohol (delta D15.8 MPa)0.5、δP＝8.2MPa0.5、δH＝10.8MPa0.5) Acetylacetone (δ D ═ 16.1 MPa)0.5、δP＝10.0MPa0.5、δH＝6.2MPa0.5) Dimethyl carbitol (delta D15.7 MPa)0.5、δP＝6.1MPa0.5、δH＝6.5MPa0.5) Propylene glycol monomethyl ether acetate (. delta.D 15.6 MPa)0.5、δP＝5.6MPa0.5、δH＝9.8MPa0.5) A high boiling point solvent having a boiling point of 100 to 180 ℃ is preferably used, because the coating stability can be improved and the appearance of the coating film can be improved by preventing the occurrence of cracks in the cured coating film.
The amount of the organic solvent (D) to be blended in the active energy ray-curable composition of the present invention is preferably an amount to achieve a viscosity suitable for a coating method described later.
The active energy ray-curable composition of the present invention can be applied to a substrate and then irradiated with an active energy ray to form a cured coating film. The active energy ray is an ionizing radiation such as ultraviolet ray, electron ray, alpha ray, beta ray, or gamma ray. When a cured coating film is formed by irradiating ultraviolet rays as active energy rays, it is preferable to add a photopolymerization initiator (F) to the active energy ray-curable composition of the present invention to improve curability. If necessary, a photosensitizer (G) may be further added to improve curability. On the other hand, when ionizing radiation such as electron beam, α -ray, β -ray, or γ -ray is used, the curing proceeds rapidly without using the photopolymerization initiator (F) or the photosensitizer (G), and therefore, it is not necessary to add the photopolymerization initiator (F) or the photosensitizer (G) in particular.
Examples of the photopolymerization initiator (F) include: diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, oligo { 2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl ] propanone }, benzildimethylketal, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, acetophenone compounds such as 4- (2-hydroxyethoxy) phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-2-morpholino (4-thiomethylphenyl) propan-1-one, and 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone; benzoin-based compounds such as benzoin, benzoin methyl ether, and benzoin isopropyl ether; acylphosphine oxide-based compounds such as 2, 4, 6-trimethylbenzoin diphenylphosphine oxide and bis (2, 4, 6-trimethylbenzoyl) -phenylphosphine oxide; benzil-based compounds such as benzil (dibenzoyl), methylphenylglyoxylic acid ester, 2- (2-hydroxyethoxy) ethyl hydroxyphenylacetate, and 2- (2-oxo-2-phenylacetoxyethoxy) ethyl hydroxyphenylacetate; benzophenone-based compounds such as benzophenone, methyl o-benzoylbenzoate-4-phenylbenzophenone, 4, 4 ' -dichlorobenzophenone, hydroxybenzophenone, 4-benzoyl-4 ' -methyl-diphenylsulfide, acrylated benzophenone, 3 ', 4, 4 ' -tetrakis (t-butylperoxycarbonyl) benzophenone, 3 ' -dimethyl-4-methoxybenzophenone, 2, 4, 6-trimethylbenzophenone, and 4-methylbenzophenone; thioxanthone compounds such as 2-isopropylthioxanthone, 2, 4-dimethylthioxanthone, 2, 4-diethylthioxanthone and 2, 4-dichlorothioxanthone; aminobenzophenone-based compounds such as Michler's ketone and 4, 4' -diethylaminobenzophenone; 10-butyl-2-chloroacridone, 2-ethylanthraquinone, 9, 10-phenanthrenequinone, camphorquinone, 1- [4- (4-benzoylphenylthio) phenyl ] -2-methyl-2- (4-methylphenylsulfonyl) propan-1-one, and the like. These photopolymerization initiators (F) may be used in 1 kind, or two or more kinds may be used in combination.
Examples of the photosensitizer (G) include: tertiary amine compounds such as diethanolamine, N-methyldiethanolamine and tributylamine, urea compounds such as o-tolylthiourea, and sulfur compounds such as sodium diethyldithiophosphate and s-benzylisothiourea p-toluenesulfonate.
The amounts of the photopolymerization initiator (F) and the photosensitizer (G) used are preferably 0.05 to 20 parts by mass, more preferably 0.5 to 10 parts by mass, based on 100 parts by mass of the total of polymerizable components including the polymerizable monomer (a) and the polymerizable monomer (B) in the active energy ray-curable composition of the present invention.
In the active energy ray-curable composition of the present invention, as other compounds than the above-mentioned components (a) to (G), additives such as a polymerization inhibitor, a surface conditioner, an antistatic agent, an antifoaming agent, a viscosity modifier, a light-resistant stabilizer, a weather-resistant stabilizer, a heat-resistant stabilizer, an ultraviolet absorber, an antioxidant, a leveling agent, an organic pigment, an inorganic pigment, a pigment dispersant, silica beads, and organic beads may be blended according to the use and the required characteristics; inorganic fillers such as silica, alumina, titania, zirconia, and antimony pentoxide. These other complexes may be used in 1 kind, or two or more kinds may be used in combination.
The film of the present invention is obtained by applying the active energy ray-curable composition of the present invention to at least 1 surface of a film substrate, and then irradiating the film with active energy rays to form a cured coating film.
As a material of the film base used in the film of the present invention, a resin having high transparency is preferable, and examples thereof include: polyester resins such as polyethylene terephthalate, polybutylene terephthalate, and polyethylene naphthalate; polyolefin resins such as polypropylene, polyethylene and polymethylpentene-1; cellulose resins such as cellulose acetate (e.g., diacetylcellulose and triacetylcellulose), cellulose acetate propionate, cellulose acetate butyrate, cellulose acetate propionate butyrate, cellulose acetate phthalate, and cellulose nitrate; acrylic resins such as polymethyl methacrylate; vinyl chloride resins such as polyvinyl chloride and polyvinylidene chloride; polyvinyl alcohol; ethylene-vinyl acetate copolymers; polystyrene; a polyamide; a polycarbonate; polysulfones; polyether sulfone; polyether ether ketone; polyimide resins such as polyimide and polyetherimide; norbornene-based resins (for example, "ZEONOR" manufactured by Zeon Corporation), modified norbornene-based resins (for example, "ARTON" manufactured by JSR Corporation), cyclic olefin copolymers (for example, "APEL" manufactured by mitsui chemical Corporation), and the like. Further, a substrate obtained by laminating two or more substrates containing these resins may be used.
The film base may be in the form of a film or a sheet, and the thickness thereof is preferably in the range of 20 to 500 μm. When a film-like base film is used, the thickness is preferably in the range of 20 to 200. mu.m, more preferably in the range of 30 to 150. mu.m, and still more preferably in the range of 40 to 130. mu.m. By setting the thickness of the film base material in this range, even when a hard coat layer is provided on one surface of the film by the active energy ray-curable composition of the present invention, curling can be easily suppressed.
Examples of the method for applying the active energy ray-curable composition of the present invention to the film substrate include: die coating, microgravure coating, gravure coating, roll coating, comma coating, air knife coating, lick coating, spray coating, dip coating, spin coating, brush coating, full-size coating with a screen, wire bar coating, flow coating, and the like.
In the case where the active energy ray-curable composition of the present invention contains an organic solvent, it is preferable to perform heating or drying at room temperature in order to volatilize the organic solvent after the active energy ray-curable composition is applied to the substrate film and before the active energy ray irradiation, and to segregate the resin (B) on the surface of the coating film. The conditions for the heat drying are not particularly limited as long as the organic solvent is volatilized, and it is usually preferable to perform the heat drying at a temperature of 50 to 100 ℃ for a time of 0.5 to 10 minutes.
The active energy ray for curing the active energy ray-curable composition of the present invention is, as described above, an ionizing radiation such as an ultraviolet ray, an electron ray, an α ray, a β ray, or a γ ray. Here, when ultraviolet rays are used as the active energy rays, examples of the means for irradiating the ultraviolet rays include: low-pressure mercury lamps, high-pressure mercury lamps, ultra-high pressure mercury lamps, metal halide lamps, electrodeless lamps (fusion lamps), chemical lamps, black-light lamps, mercury-xenon lamps, short-arc lamps, helium-cadmium lasers, argon lasers, sunlight, LED lamps, and the like.
The thickness of the cured coating film when the cured coating film of the active energy ray-curable composition of the present invention is formed on the film base is preferably in the range of 1 to 30 μm, more preferably in the range of 3 to 15 μm, and further preferably in the range of 4 to 10 μm, from the viewpoint of making the hardness of the cured coating film sufficient and suppressing curling of the film due to curing shrinkage of the coating film.
Examples
The present invention will be described more specifically with reference to examples.
Production example 1 production of resin (C-1) having alicyclic Structure and Quaternary ammonium salt
Nitrogen gas was introduced into a flask equipped with a stirrer, a reflux condenser and a nitrogen gas inlet tube, and the air in the flask was replaced with nitrogen gas. Then, 53.7 parts by mass of 2- (methacryloyloxy) ethyltrimethyl ammonium chloride, 29.3 parts by mass of cyclohexyl methacrylate, 14.6 parts by mass of methoxypolyethylene glycol methacrylate ("BLEMMER PME-1000" manufactured by Nichigan Co., Ltd.; number of repeating units n. about.23, molecular weight 1,000), 1.9 parts by mass of 2-perfluorohexylethyl acrylate, 0.5 parts by mass of methacrylic acid, 50 parts by mass of methanol, and 10 parts by mass of propylene glycol monomethyl ether (hereinafter abbreviated as "PGME") were added to the flask. Then, a solution obtained by dissolving 0.1 part by mass of a polymerization initiator (azobisisobutyronitrile) with 2.4 parts by mass of PGME was added dropwise over 30 minutes, followed by reaction at 65 ℃ for 3 hours. Then, methanol was added thereto for dilution to obtain a 45 mass% solution of the resin (C-1) having an alicyclic structure and a quaternary ammonium salt. The weight-average molecular weight of the resulting resin (C-1) was 1 ten thousand.
Production example 2 production of resin (C-2) having alicyclic Structure and Quaternary ammonium salt
Nitrogen gas was introduced into a flask equipped with a stirrer, a reflux condenser and a nitrogen gas inlet tube, and the air in the flask was replaced with nitrogen gas. Then, 53.7 parts by mass of 2- (methacryloyloxy) ethyltrimethyl ammonium chloride, 14.6 parts by mass of cyclohexyl methacrylate, 29.3 parts by mass of methoxypolyethylene glycol methacrylate ("BLEMMER PME-1000" manufactured by Nichigan Co., Ltd.; number of repeating units n. about.23, molecular weight 1,000), 1.9 parts by mass of 2-perfluorohexylethyl methacrylate, 0.5 part by mass of methacrylic acid, 50 parts by mass of methanol, and 10 parts by mass of PGME were added to the flask. Then, a solution obtained by dissolving 0.1 part by mass of a polymerization initiator (azobisisobutyronitrile) with 2.4 parts by mass of PGME was added dropwise over 30 minutes, followed by reaction at 65 ℃ for 3 hours. Then, methanol was added thereto for dilution to obtain a 45 mass% solution of the resin (C-2) having an alicyclic structure and a quaternary ammonium salt. The weight-average molecular weight of the resulting resin (C-2) was 1 ten thousand.
Production example 3 production of resin (C-3) having alicyclic Structure and Quaternary ammonium salt
Nitrogen gas was introduced into a flask equipped with a stirrer, a reflux condenser and a nitrogen gas inlet tube, and the air in the flask was replaced with nitrogen gas. Then, 53.7 parts by mass of 2- (methacryloyloxy) ethyltrimethyl ammonium chloride, 14.6 parts by mass of cyclohexyl methacrylate, 29.3 parts by mass of methoxypolyethylene glycol methacrylate ("BLEMMER PME-1000" manufactured by Nichigan Co., Ltd.; number of repeating units n. about.23, molecular weight 1,000), 1.9 parts by mass of 2-perfluorohexylethyl acrylate, 0.5 part by mass of methacrylic acid, 50 parts by mass of methanol, and 10 parts by mass of PGME were added to the flask. Then, a solution obtained by dissolving 0.1 part by mass of a polymerization initiator (azobisisobutyronitrile) with 2.4 parts by mass of PGME was added dropwise over 30 minutes, followed by reaction at 65 ℃ for 3 hours. Then, methanol was added thereto for dilution to obtain a 45 mass% solution of the resin (C-3) having an alicyclic structure and a quaternary ammonium salt. The weight-average molecular weight of the resulting resin (C-3) was 1 ten thousand.
Production example 4 production of resin (C-4) having alicyclic Structure and Quaternary ammonium salt
Nitrogen gas was introduced into a flask equipped with a stirrer, a reflux condenser and a nitrogen gas inlet tube, and the air in the flask was replaced with nitrogen gas. Then, 53.7 parts by mass of 2- (methacryloyloxy) ethyltrimethyl ammonium chloride, 43.9 parts by mass of cyclohexyl methacrylate, 1.9 parts by mass of 2-perfluorohexylethyl acrylate, 0.5 part by mass of methacrylic acid, 50 parts by mass of methanol and 10 parts by mass of PGME were added to the flask. Then, a solution obtained by dissolving 0.1 part by mass of a polymerization initiator (azobisisobutyronitrile) with 2.4 parts by mass of PGME was added dropwise over 30 minutes, followed by reaction at 65 ℃ for 3 hours. Then, methanol was added thereto for dilution to obtain a 45 mass% solution of the resin (C-4) having an alicyclic structure and a quaternary ammonium salt. The weight-average molecular weight of the resulting resin (C-4) was 1 ten thousand.
Production example 5 production of resin (C-5) having alicyclic Structure and Quaternary ammonium salt
Nitrogen gas was introduced into a flask equipped with a stirrer, a reflux condenser and a nitrogen gas inlet tube, and the air in the flask was replaced with nitrogen gas. Then, 54.7 parts by mass of 2- (methacryloyloxy) ethyltrimethyl ammonium chloride, 19.9 parts by mass of cyclohexyl methacrylate, 24.9 parts by mass of methoxypolyethylene glycol methacrylate ("BLEMMER PME-1000" manufactured by Nichigan Co., Ltd.; number of repeating units n. about.23, molecular weight 1,000), 0.5 part by mass of methacrylic acid, 50 parts by mass of methanol, and 10 parts by mass of PGME were added to the flask. Then, a solution obtained by dissolving 0.1 part by mass of a polymerization initiator (azobisisobutyronitrile) with 2.4 parts by mass of PGME was added dropwise over 30 minutes, followed by reaction at 65 ℃ for 3 hours. Then, methanol was added thereto for dilution to obtain a 45 mass% solution of the resin (C-5) having an alicyclic structure and a quaternary ammonium salt. The weight-average molecular weight of the resulting resin (C-5) was 1 ten thousand.
Production example 6 production of resin (C' -1) having alicyclic Structure and Quaternary ammonium salt
Nitrogen gas was introduced into a flask equipped with a stirrer, a reflux condenser and a nitrogen gas inlet tube, and the air in the flask was replaced with nitrogen gas. Then, 54.0 parts by mass of 2- (methacryloyloxy) ethyltrimethyl ammonium chloride, 44.1 parts by mass of methoxypolyethylene glycol methacrylate ("BLEMMER PME-1000" manufactured by Nichigan Co., Ltd.; number of repeating units n. about.23, molecular weight 1,000), 1.9 parts by mass of 2-perfluorohexylethyl acrylate, 50 parts by mass of methanol, and 10 parts by mass of PGME were added to the flask. Then, a solution obtained by dissolving 0.1 part by mass of a polymerization initiator (azobisisobutyronitrile) with 2.4 parts by mass of PGME was added dropwise over 30 minutes, followed by reaction at 65 ℃ for 3 hours. Then, methanol was added to dilute the solution to obtain a 45 mass% solution of the resin (C' -1) having an alicyclic structure and a quaternary ammonium salt. The weight average molecular weight of the resulting resin (C' -1) was 1 ten thousand.
Production example 7 production of resin (C' -2) having alicyclic Structure and Quaternary ammonium salt
Nitrogen gas was introduced into a flask equipped with a stirrer, a reflux condenser and a nitrogen gas inlet tube, and the air in the flask was replaced with nitrogen gas. Then, 54.7 parts by mass of 2- (methacryloyloxy) ethyltrimethyl ammonium chloride, 44.8 parts by mass of methoxypolyethylene glycol methacrylate ("BLEMMER PME-1000" manufactured by Nichigan Co., Ltd.; number of repeating units n. apprxeq.23, molecular weight 1,000), 0.5 part by mass of methacrylic acid, 50 parts by mass of methanol, and 10 parts by mass of PGME were added to the flask. Then, a solution obtained by dissolving 0.1 part by mass of a polymerization initiator (azobisisobutyronitrile) with 2.4 parts by mass of PGME was added dropwise over 30 minutes, followed by reaction at 65 ℃ for 3 hours. Then, methanol was added to dilute the solution to obtain a 45 mass% solution of the resin (C' -2) having an alicyclic structure and a quaternary ammonium salt. The weight average molecular weight of the resulting resin (C' -2) was 1 ten thousand.
The weight average molecular weights of the resins (C-1) to (C-5), (C '-1) and (C' -2) obtained above were measured by a Gel Permeation Chromatography (GPC) method under the following conditions.
A measuring device: high-speed GPC apparatus (HLC-8220 GPC, manufactured by Tosoh corporation)
Column: the following columns manufactured by Tosoh corporation were connected in series for use.
"TSKgel G5000" (7.8 mmI.D.. times.30 cm). times.1 roots
"TSKgel G4000" (7.8mm I.D.. times.30 cm). times.1 roots
"TSKgel G3000" (7.8 mmI.D.. times.30 cm). times.1 roots
"TSKgel G2000" (7.8 mmI.D.. times.30 cm). times.1 roots
A detector: RI (differential refractometer)
Column temperature: 40 deg.C
Eluent: tetrahydrofuran (THF)
Flow rate: 1.0 mL/min
Injection amount: 100 μ L (tetrahydrofuran solution with a sample concentration of 0.4% by mass)
Standard sample: the standard curve was made using the standard polystyrene described below.
(Standard polystyrene)
TSKgel Standard polystyrene A-500 manufactured by Tosoh corporation "
TSKgel Standard polystyrene A-1000 manufactured by Tosoh corporation "
TSKgel Standard polystyrene A-2500 manufactured by Tosoh corporation "
TSKgel Standard polystyrene A-5000 manufactured by Tosoh corporation "
TSKgel Standard polystyrene F-1 manufactured by Tosoh corporation "
TSKgel Standard polystyrene F-2 manufactured by Tosoh corporation "
TSKgel Standard polystyrene F-4 manufactured by Tosoh corporation "
TSKgel Standard polystyrene F-10 manufactured by Tosoh corporation "
TSKgel Standard polystyrene F-20 manufactured by Tosoh corporation "
TSKgel Standard polystyrene F-40 manufactured by Tosoh corporation "
TSKgel Standard polystyrene F-80 manufactured by Tosoh corporation "
TSKgel Standard polystyrene F-128 manufactured by Tosoh corporation "
TSKgel Standard polystyrene F-288 manufactured by Tosoh corporation "
TSKgel Standard polystyrene F-550 manufactured by Tosoh corporation "
(example 1)
17 parts by mass of a high-refractive-index polymerizable monomer (9, 9-bis [4- (2-acryloyloxyethoxy) phenyl ] fluorene, a refractive index of 1.616) (hereinafter abbreviated as "monomer (A-1)"), 17 parts by mass of a high-refractive-index polymerizable monomer (an equivalent mixture of o-phenylbenzylacrylate and p-phenylbenzylacrylate, a refractive index of 1.591, and a phenyl) (hereinafter abbreviated as "monomer (A-2)"), 66 parts by mass of a polyfunctional acrylate mixture (a mixture of 64% by mass of dipentaerythritol hexaacrylate, 17% by mass of dipentaerythritol pentaacrylate, and 19% by mass of dipentaerythritol tetraacrylate) (hereinafter abbreviated as "monomer (B-1)"), 6.7 parts by mass of a 45% solution of the resin (C-1) obtained in production example 1 (3 parts by mass of the resin (C-1)), 6.7 parts by mass of a 45% solution of the resin (C-1), and 3 parts by mass of a, 5 parts by mass of a photopolymerization initiator (IRGACURE 184; 1-hydroxycyclohexyl phenyl ketone, BASF Japan K.K.), 40 parts by mass of methyl ethyl ketone (hereinafter abbreviated as "MEK"), and 60 parts by mass of PGME were uniformly mixed to obtain an active energy ray-curable composition (1) having a nonvolatile content of 50% by mass.
(examples 2 to 7)
Active energy ray-curable compositions (2) to (7) were obtained in the same manner as in example 1, except that the compositions shown in tables 1 to 3 were changed.
Comparative examples 1 to 2
Active energy ray-curable compositions (R1) and (R2) were obtained in the same manner as in example 1, except that the compositions shown in table 3 were changed.
The abbreviations shown in tables 1 to 3 represent the following.
Monomer (A-3): "UNIDIC EQS-1179" (bisphenol A type multifunctional acrylate, refractive index 1.555) manufactured by DIC corporation
DMC: carbonic acid dimethyl ester
The following tests and measurements were carried out using the active energy ray-curable compositions (1) to (7), (R1) and (R2) obtained in examples 1 to 7 and comparative examples 1 to 2.
[ preparation of sample for evaluation ]
The active energy ray-curable composition was applied to a triacetyl cellulose (TAC) film (manufactured by Fuji photo film Co., Ltd.) having a thickness of 60 μm by a bar coater so that the film thickness became 5 μm, dried at 60 ℃ for 1.5 minutes, and then irradiated with a light amount of 3kJ/m using an ultraviolet irradiation apparatus (Eye Graphics Co., Ltd., high-pressure mercury lamp) under an air atmosphere2Irradiation was performed to obtain a TAC film having a cured coating film as a sample for evaluation.
[ measurement of Pencil hardness ]
The surface of the cured coating film of the above-obtained evaluation sample was measured in accordance with JIS test method K5600-5-4: 1999, pencil hardness was measured.
[ measurement of haze (evaluation of transparency) ]
For the above-obtained evaluation sample, the following test was performed according to JIS test method K7136: the haze value was measured using a haze meter ("NDH 2000", manufactured by Nippon Denshoku industries Co., Ltd.).
[ measurement of refractive index ]
For the above-obtained evaluation samples, the following were measured according to JIS test method K7142: 2014, refractive index was measured by using an Abbe refractive index meter (Atago Co., Ltd. "DR-M2" manufactured by Ltd.).
[ measurement of surface resistance value (evaluation of antistatic Property) ]
The surface resistance value of the cured coating film of the above-obtained evaluation sample was measured with a voltage of 500V for a measurement time of 10 seconds using a high resistivity meter (HIRESTA-UP MCP-HT450 manufactured by Mitsubishi Chemical Analyticech Co., Ltd.) in accordance with JIS test method K6911-1995.
The results of the above measurements are shown in tables 1 to 3.
[ Table 1]
[ Table 2]
[ Table 3]
From the evaluation results shown in tables 1 to 3, it can be confirmed that: the cured coatings of the active energy ray-curable compositions of examples 1 to 7 of the present invention had a high refractive index, a surface resistance value of the order of 9 to 10 times that of 10, and a high antistatic property.
On the other hand, comparative examples 1 and 2 are examples in which a resin having no alicyclic structure and having a quaternary ammonium salt is used. It can be confirmed that: they also have high refractive indices, but have surface resistance values exceeding the 13 th power of 10, and are poor in antistatic properties.
Claims (6)
1. An active energy ray-curable composition comprising a high-refractive-index polymerizable monomer (A) having a refractive index of 1.55 or more, a polyfunctional polymerizable monomer (B), a resin (C) having an alicyclic structure and a quaternary ammonium salt, and an organic solvent (D),
the high refractive index polymerizable monomer (A) is a compound represented by the following general formula (1) and/or a (meth) acrylate compound having a phenylbenzyl group,
the polyfunctional polymerizable monomer (B) is selected from the group consisting of 1, 4-butanediol di (meth) acrylate, 3-methyl-1, 5-pentanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 2-methyl-1, 8-octanediol di (meth) acrylate, 2-butyl-2-ethyl-1, 3-propanediol di (meth) acrylate, tricyclodecane dimethanol di (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, and mixtures thereof, Polypropylene glycol di (meth) acrylate, di (meth) acrylate of tris (2-hydroxyethyl) isocyanurate, di (meth) acrylate of diol obtained by adding 4 or more moles of ethylene oxide or propylene oxide to 1 mole of neopentyl glycol, di (meth) acrylate of diol obtained by adding 2 or more moles of ethylene oxide or propylene oxide to 1 moles of bisphenol a, trimethylolpropane tri (meth) acrylate, ethylene oxide-modified trimethylolpropane tri (meth) acrylate, propylene oxide-modified trimethylolpropane tri (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, tris (2- (meth) acryloyloxyethyl) isocyanurate, pentaerythritol tri (meth) acrylate, propylene oxide, and propylene oxide, and the like, At least one of pentaerythritol tetra (meth) acrylate, dipentaerythritol tri (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, and dipentaerythritol hexa (meth) acrylate,
in the formula (1), R1、R2Each represents a hydrogen group or a methyl group, and m and n each represents an integer of 0 to 5.
2. The active energy ray-curable composition according to claim 1, wherein the resin (C) is a polymer obtained by using 5 to 40 mass% of a polymerizable monomer having an alicyclic structure as a raw material.
3. The active energy ray-curable composition according to claim 1 or 2, wherein the organic solvent (D) has a dispersion term δ D of 15.5MPa in terms of hansen solubility parameter0.5～16.1MPa0.5In the range of 6.3MPa for the polarity term deltaP0.5～10.4MPa0.5In the range of 5.1MPa for the hydrogen bond term delta H0.5～11.6MPa0.5A solvent in the range of (1).
4. The active energy ray-curable composition according to claim 1 or 2, wherein the amount of the resin (C) is in the range of 0.1 to 30 parts by mass relative to 100 parts by mass of the total of the polymerizable monomer (a) and the polymerizable monomer (B).
5. A cured product of the active energy ray-curable composition according to any one of claims 1 to 4.
6. A film comprising a cured coating film of the active energy ray-curable composition according to any one of claims 1 to 4.
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| PCT/JP2017/017495 WO2018003293A1 (en) | 2016-06-27 | 2017-05-09 | Active-energy-beam curable composition and film using same |
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| JP2008164854A (en) * | 2006-12-27 | 2008-07-17 | Jsr Corp | Film-like light waveguide |
| JP5376770B2 (en) | 2007-04-03 | 2013-12-25 | 三菱樹脂株式会社 | Polyester film for surface protection film and polyester film for surface protection of optical member |
| JP5230313B2 (en) * | 2008-09-10 | 2013-07-10 | 株式会社日本触媒 | Laminated plate and front plate for display device |
| JP2012031297A (en) * | 2010-07-30 | 2012-02-16 | Arakawa Chem Ind Co Ltd | Antistatic agent for active energy ray-curable type resin composition, active energy ray-curable type composition, cured coating film, and antistatic-treated optical film |
| JP6287615B2 (en) * | 2014-06-17 | 2018-03-07 | 荒川化学工業株式会社 | Active energy ray-curable resin composition, cured film and antistatic treatment optical film |
| JP6365239B2 (en) * | 2014-10-29 | 2018-08-01 | 三菱ケミカル株式会社 | Curable composition, cured product, optical film and laminate |
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- 2017-05-09 KR KR1020187035874A patent/KR102148790B1/en active IP Right Grant
- 2017-05-09 WO PCT/JP2017/017495 patent/WO2018003293A1/en active Application Filing
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| JP2000187102A (en) * | 1998-10-14 | 2000-07-04 | Tomoegawa Paper Co Ltd | Antireflection material and polarizing film using the same |
| JP2007269993A (en) * | 2006-03-31 | 2007-10-18 | Toppan Printing Co Ltd | Glare-proof antistatic hard coat resin composition and glare-proof antistatic hard coat film formed body coated with the same |
| CN102667536A (en) * | 2009-11-12 | 2012-09-12 | 凸版印刷株式会社 | Anti-reflection film and method for producing same |
| JP2012102166A (en) * | 2010-11-05 | 2012-05-31 | Toyo Ink Sc Holdings Co Ltd | Antistatic coating composition |
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| KR20190008293A (en) | 2019-01-23 |
| KR102148790B1 (en) | 2020-08-27 |
| JP6288538B1 (en) | 2018-03-07 |
| JPWO2018003293A1 (en) | 2018-07-05 |
| TWI731090B (en) | 2021-06-21 |
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| TW201819424A (en) | 2018-06-01 |
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