CN109328198B - Active energy ray-curable composition and film using same - Google Patents
Active energy ray-curable composition and film using same Download PDFInfo
- Publication number
- CN109328198B CN109328198B CN201780039288.5A CN201780039288A CN109328198B CN 109328198 B CN109328198 B CN 109328198B CN 201780039288 A CN201780039288 A CN 201780039288A CN 109328198 B CN109328198 B CN 109328198B
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- Prior art keywords
- meth
- acrylate
- active energy
- energy ray
- mass
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 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
- 239000011342 resin composition Substances 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
- 239000010959 steel Substances 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
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-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
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 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
-
- 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
-
- 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
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- 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
- 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
-
- 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
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Paints Or Removers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
Abstract
The invention provides an active energy ray-curable composition capable of forming a hard coat layer having excellent antistatic properties, and a film using the active energy ray-curable composition. The present invention uses an active energy ray-curable composition characterized by containing an active energy ray-curable compound (a), a resin (B) having an alicyclic structure and a quaternary ammonium salt, and an organic solvent (C). Further, as the resin (B) having an alicyclic structure and a quaternary ammonium salt, a polymer using 5 to 40 mass% of a polymerizable monomer having an alicyclic structure as a raw material thereof is used. The organic solvent (C) 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)0.5A 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 excellent 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
Various resin films are used for various applications such as a film for preventing damage on the surface of a Flat Panel Display (FPD) such as a Liquid Crystal Display (LCD), an organic EL display (OLED), and a Plasma Display (PDP), a decorative film (sheet) for interior and exterior applications of automobiles, a low reflection film for windows, and a heat ray cut film. However, since the surface of the resin film is soft and has low scratch resistance, in order to compensate for this, a hard coating agent containing a UV curable composition or the like is generally applied to the surface of the film and cured to provide a hard coat layer on the surface of the film. To summarize the step of providing the hard coat layer, a film material wound in a roll shape is fed to a coating machine, coated with a hard coat agent, cured by ultraviolet irradiation to form a hard coat layer, and then wound in a roll shape again.
In this winding step, static electricity is generated on the film surface by friction between the films, and therefore, there are problems that the films adhere to each other when the films are unwound from the roll at the time of rework, and that dust and the like easily adhere to the film surface by static electricity. In addition, when the film is used for a liquid crystal display or the like, there is a problem that the display is erroneously operated due to static electricity generated.
In order to suppress the generation of static electricity on the film surface, a method of blending an antistatic agent into a hard coating agent is generally employed. For example, a method of blending a compound having a polyoxyethylene chain and a quaternary ammonium salt as an antistatic agent into a hard coat agent has been proposed (for example, see patent document 1).
In addition, a method of blending two kinds of copolymers, which are obtained by using a polymerizable monomer having a quaternary ammonium salt as a raw material, as an antistatic agent into a hard coating agent has been proposed (for example, see patent document 2).
However, these hard coating agents containing an antistatic agent have insufficient antistatic performance. Accordingly, an active energy ray-curable composition capable of forming a hard coat layer having more excellent antistatic properties is required.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. 2004-143303
Patent document 2: japanese laid-open patent publication No. 2004-123924
Disclosure of Invention
Technical problem to be solved by the invention
The present invention has been made to solve the above problems, and an object of the present invention is to provide an active energy ray-curable composition capable of forming a hard coat layer having excellent antistatic properties, and a film using the active energy ray-curable composition.
Means for solving the problems
The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, have found that a hard coat layer having excellent antistatic properties can be formed by blending a resin having an alicyclic structure and a quaternary ammonium salt or 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 characterized by containing an active energy ray-curable compound (a), a resin (B) having an alicyclic structure and a quaternary ammonium salt, and an organic solvent (C), and a film using the same.
Effects of the invention
The active energy ray-curable composition of the present invention can form a hard coat layer having excellent antistatic properties by being applied to a film surface and cured. Therefore, the cured coating film of the active energy ray-curable composition of the present invention can suppress the generation of static electricity on the film surface. Therefore, various films can be provided with functions such as adhesion prevention and prevention of adhesion of dust or the like due to static electricity. Therefore, the film having the cured coating film of the active energy ray-curable composition of the present invention becomes an environmentally friendly film, and when the film is wound into a roll, troubles such as adhesion and adhesion of dust can be avoided even when the film is unwound from the roll, and therefore a film excellent in handling after the winding can be provided.
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, since the antistatic property is excellent when the resin composition is used for these applications, 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 an active energy ray-curable compound (a), a resin (B) having an alicyclic structure and a quaternary ammonium salt, and an organic solvent (C).
Examples of the active energy ray-curable compound (a) include polyfunctional (meth) acrylate (a1) and urethane (meth) acrylate (a 2). These may be used in 1 kind, or two or more kinds may be used in combination.
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 polyfunctional (meth) acrylate (a1) is a compound having 2 or more (meth) acryloyl groups in 1 molecule. Specific examples of the polyfunctional (meth) acrylate (a1) include di (meth) acrylates of dihydric alcohols such as 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, tricyclodecanedimethanol 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 the like, Polyethylene glycol di (meth) 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 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, 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 (meth) acrylates (A1) may be used in 1 kind, or two or more kinds may be used in combination. Among these polyfunctional (meth) acrylates (a1), dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate, pentaerythritol tetra (meth) acrylate, and pentaerythritol tri (meth) acrylate are preferable in terms of improving the scratch resistance of the cured coating film of the active energy ray-curable composition of the present invention.
The urethane (meth) acrylate (A2) is obtained by reacting a polyisocyanate (a2-1) with a (meth) acrylate (a2-2) having a hydroxyl group.
Examples of the polyisocyanate (a2-1) include aliphatic polyisocyanates and aromatic polyisocyanates, and aliphatic polyisocyanates are preferable in that the coloring of the cured coating film of the active energy ray-curable composition of the present invention can be reduced.
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, methylene bis (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 (a2-2) is a compound having a hydroxyl group and a (meth) acryloyl group. Specific examples of the (meth) acrylate (a2-2) include mono (meth) acrylates of dihydric alcohols 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 (a2-2) may be used in 1 kind or in combination of two or more kinds.
Among the urethane (meth) acrylates (a2), 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 (a2) a urethane (meth) acrylate having 4 or more (meth) acryloyl groups in 1 molecule, a (meth) acrylate having 2 or more (meth) acryloyl groups is preferable as the (meth) acrylate (a 2-2). Examples of such (meth) acrylic acid esters (a2-2) 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 esters (a2-2) 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 (a2-2), pentaerythritol tri (meth) acrylate and dipentaerythritol penta (meth) acrylate are preferable because scratch resistance can be improved.
The reaction of the above polyisocyanate (a2-1) with the above (meth) acrylic acid ester (a2-2) 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.
As the active energy ray-curable compound (a) other than the above-mentioned polyfunctional (meth) acrylate (a1) and urethane (meth) acrylate (a2), epoxy (meth) acrylate, polyester (meth) acrylate, polyether (meth) acrylate, or the like can be used as needed. 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) has an alicyclic structure and a quaternary ammonium salt.
Examples of the method for producing the resin (B) include the following methods: the polymerizable monomer (b1) and the polymerizable monomer (b2) are copolymerized with a copolymerizable polymerizable monomer (b3) using a polymerizable monomer (b1) having an alicyclic structure and a polymerizable monomer (b2) having a quaternary ammonium salt as essential components.
The polymerizable monomer (b1) 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 and 1, 4-cyclohexanedimethanol mono (meth) acrylateEsters, isobornyl (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, dicyclopentanyl (meth) acrylate, and the like. These polymerizable monomers (b1) may be used in 1 kind, or two or more kinds may be used in combination.
Examples of the polymerizable monomer (b2) 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 (b2) may be used in 1 kind, or two or more kinds may be used in combination.
Examples of the polymerizable monomer (b3) 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 may be used in 1 kind, or two or more kinds may be used in combination.
Among the polymerizable monomers (b3), 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, a polyalkylene glycol mono (meth) acrylate is preferable, and a methoxypolyethylene glycol mono (meth) acrylate is more preferable. 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 (B1) in the total amount of the raw materials of the resin (B) 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 (B2) in the total amount of the raw materials of the resin (B) 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 (B3), the proportion of the polyalkylene glycol mono (meth) acrylate in the total amount of the raw materials of the resin (B) 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 the case where the (meth) acrylate having a fluoroalkyl group is used as the polymerizable monomer (B3), the proportion of the (meth) acrylate having a fluoroalkyl group in the total amount of the raw materials of the resin (B) is preferably in the range of 0.1 to 20% by mass, more preferably in the range of 0.5 to 10% by mass, and still more preferably in the range of 1 to 5% by 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 (B) 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 (B) to be blended is preferably in the range of 0.1 to 30 parts by mass, more preferably 0.5 to 20 parts by mass, still 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 active energy ray-curable composition (a), 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 organic solvent (C) 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 (C) 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 (C), examples of the 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 (C) 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 MPa0.5、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 cured coating film can be prevented from cracking and has an excellent appearance.
The amount of the organic solvent (C) 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 (D) to the active energy ray-curable composition of the present invention to improve curability. If necessary, a photosensitizer (E) 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 (D) or the photosensitizer (E), and therefore, it is not necessary to add the photopolymerization initiator (D) or the photosensitizer (E) in particular.
Examples of the photopolymerization initiator (D) 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 (D) may be used in 1 kind, or two or more kinds may be used in combination.
Examples of the photosensitizer (E) 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 (D) and the photosensitizer (E) used are preferably 0.05 to 20 parts by mass, and more preferably 0.5 to 10 parts by mass, respectively, based on 100 parts by mass of the active energy ray-curable composition (a) 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 (E), 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 Synthesis of urethane acrylate (A2-1)
In a flask equipped with a stirrer, a gas inlet tube, a condenser and a thermometer, 55.5 parts by mass of butyl acetate, 222 parts by mass of IPDI, 0.5 parts by mass of p-methoxyphenol and 0.5 parts by mass of dibutyltin diacetate were charged, the temperature was raised to 70 ℃, then 823.6 parts by mass of a butyl acetate solution containing 80% by mass of nonvolatile components in a mixture of bis (2-acryloyloxyethyl) hydroxyethyl isocyanurate (hereinafter referred to as "BAHIC")/tris (2-acryloyloxyethyl) isocyanurate (hereinafter referred to as "TAIC") (mixture having a mass ratio of 56/44) was added dropwise over 1 hour, and the mixture was reacted at 70 ℃ for 3 hours after completion of the dropwise addition. Thereafter, 496.6 parts by mass of a butyl acetate solution containing 80% by mass of nonvolatile components of a PE3A/PE4A mixture (mixture having a mass ratio of 75/25) was added dropwise over 1 hour, and after completion of the addition, the mixture was reacted at 70 ℃ for 3 hours, followed by further reaction to 2250cm of a mixture containing isocyanate groups-1The infrared absorption spectrum of (A) was disappeared to obtain a mixture of urethane acrylate (A2-1)/TAIC/PE4A (a mixture having a mass ratio of 69/23/8, a butyl acetate solution having a nonvolatile content of 80 mass%). The molecular weight of the urethane acrylate (A2-1) was 889.
Production example 2 Synthesis of urethane acrylate (A2-2)
In a flask equipped with a stirrer, a gas inlet tube, a condenser and a thermometer, 55.5 parts by mass of butyl acetate, 222 parts by mass of isophorone diisocyanate (hereinafter referred to as "IPDI"), 0.5 part by mass of p-methoxyphenol and 0.5 part by mass of dibutyltin diacetate were put, and after the temperature was raised to 70 ℃, 80 parts by mass of a butyl acetate solution 993.4 parts by mass of a mixture of pentaerythritol triacrylate (hereinafter referred to as "PE 3A")/pentaerythritol tetraacrylate (hereinafter referred to as "PE 4A") (mixture having a mass ratio of 75/25) was added dropwise over 1 hour. After completion of the dropwise addition, the reaction was carried out at 70 ℃ for 3 hours, and the reaction was further carried out to 2250cm of an isocyanate group-1The infrared absorption spectrum of (A) was disappeared to obtain a urethane acrylate (A2-2)/PE4A mixture (mixture having a mass ratio of 80/20, a butyl acetate solution having a nonvolatile content of 80 mass%). The urethane acrylate isThe molecular weight of the ester (A2-2) was 818.
Production example 3 production of resin (B-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 part by mass of methacrylic acid, 50 parts by mass of methanol, and 10 parts by mass of propylene glycol monomethyl ether 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 propylene glycol monomethyl ether 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 (B-1) having an alicyclic structure and a quaternary ammonium salt. The weight-average molecular weight of the resulting resin (B-1) was 1 ten thousand.
Production example 4 production of resin (B-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, 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 (B-2) having an alicyclic structure and a quaternary ammonium salt. The weight-average molecular weight of the resulting resin (B-2) was 1 ten thousand.
Production example 5 production of resin (B' -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 (B' -1) having an alicyclic structure and a quaternary ammonium salt. The weight average molecular weight of the resulting resin (B' -1) was 1 ten thousand.
Production example 6 production of resin (B' -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. 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 to dilute the solution to obtain a 45 mass% solution of the resin (B' -2) having an alicyclic structure and a quaternary ammonium salt. The weight average molecular weight of the resulting resin (B' -2) was 1 ten thousand.
The weight average molecular weights of the resins (B-1), (B-2), (B '-1) and (B' -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)
A polyfunctional acrylate mixture (a mixture of 64 mass% of dipentaerythritol hexaacrylate, 17 mass% of dipentaerythritol pentaacrylate and 19 mass% of dipentaerythritol tetraacrylate; hereinafter abbreviated as "polyfunctional acrylate (A1)") 100 parts by mass, 11.11 parts by mass of a 45 mass% solution of the resin (B-2) obtained in production example 4 (5 parts by mass of the resin (B-2), a photopolymerization initiator (IRGACURE 184, 1-hydroxycyclohexylphenylketone, BASF Japan K., Ltd.) (5 parts by mass), 60 parts by mass of methyl ethyl ketone (hereinafter abbreviated as "MEK"), and 40 parts by mass of PGME) were uniformly mixed to obtain an active energy ray-curable composition (1) having a nonvolatile content of 50 mass%.
(reference examples 1 to 3)
Active energy ray-curable compositions (2) to (4) were obtained in the same manner as in example 1, except that the compositions shown in tables 1 to 2 were changed.
Comparative examples 1 to 3
Active energy ray-curable compositions (R3) to (R5) were obtained in the same manner as in example 1, except that the compositions shown in tables 2 to 3 were changed.
The following tests and measurements were carried out using the active energy ray-curable compositions (1) to (4), (R3) to (R5) obtained in the above-described example 1, reference examples 1 to 3, and comparative examples 1 to 3.
[ 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.
[ evaluation of scratch resistance ]
The surface of the cured coating film of the film for evaluation obtained above was tested by using a clock counter type friction tester ("plane friction tester" manufactured by Toyo Seiki Seisaku-Sho K.K., measurement conditions: a circular friction material having a diameter of 25mm, steel wool #0000, a load of 500g, and 10 cycles), and the scratch resistance was evaluated by the following criteria, by visually confirming that the surface of the cured coating film after the test had no damage.
Very good: there was no damage.
O: the number of the damages is 1-2.
Δ: the number of the damages is 3-10.
X: the number of lesions exceeded 10.
[ measurement of haze (evaluation of transparency) ]
The haze value of the evaluation sample obtained above was measured using a haze meter (NDH 2000, manufactured by Nippon Denshoku industries Co., Ltd.) according to JIS test method K7136: 2000.
[ measurement of refractive index ]
The refractive index of the above-obtained sample for evaluation was measured by using an Abbe refractometer (Atago Co., Ltd. "DR-M2" manufactured by Ltd.) according to method A of JIS test method K7142: 2014.
[ 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 table 1, it can be confirmed that: the cured coating film of the active energy ray-curable composition of the present invention of example 1 had a surface resistance value of 9 th power order of 10 and also had high antistatic properties.
On the other hand, comparative examples 1 to 3 are examples using a resin having no alicyclic structure and having a quaternary ammonium salt. It can be confirmed that: their surface resistance values exceed the 13 th power of 10, and antistatic properties are poor.
Claims (5)
1. An active energy ray-curable composition comprising an active energy ray-curable compound (A), a resin (B) having an alicyclic structure and a quaternary ammonium salt, and an organic solvent (C), wherein the organic solvent (C) contains an alcohol solvent, a ketone solvent, and other solvents having a boiling point of 100 ℃ to 180 ℃, the organic solvent (C) contains 3 to 40 mass% of the solvents having a boiling point of 100 ℃ to 180 ℃, and the organic solvent (C) has a dispersion term δ D of 15.5MPa in terms of a 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).
2. The active energy ray-curable composition according to claim 1, wherein the resin (B) 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 amount of the resin (B) is in the range of 0.1 to 30 parts by mass per 100 parts by mass of the active energy ray-curable compound (a).
4. A cured product of the active energy ray-curable composition according to any one of claims 1 to 3.
5. A film comprising a cured coating film of the active energy ray-curable composition according to any one of claims 1 to 3.
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| JP2016126588 | 2016-06-27 | ||
| JP2016-126588 | 2016-06-27 | ||
| PCT/JP2017/017496 WO2018003294A1 (en) | 2016-06-27 | 2017-05-09 | Active-energy-beam-curable composition and film using same |
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| CN109328198B true CN109328198B (en) | 2021-09-14 |
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| KR (1) | KR20190011755A (en) |
| CN (1) | CN109328198B (en) |
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| WO2022186019A1 (en) * | 2021-03-02 | 2022-09-09 | Dic株式会社 | Actinic-ray-curable composition, cured object, and film |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102212280A (en) * | 2010-04-01 | 2011-10-12 | 东洋油墨制造股份有限公司 | Antistatic coating composition |
| 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 |
| CN104017138A (en) * | 2013-02-04 | 2014-09-03 | 荒川化学工业株式会社 | Active energy ray gel-type resin composition, antistatic agent used for composition, solidified membrane, and anti-static processing optical film |
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| 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 |
| JP4595925B2 (en) * | 2006-11-06 | 2010-12-08 | 凸版印刷株式会社 | Antiglare antistatic hard coat resin composition, hard coat film and hard coat film-formed article |
| JP5230313B2 (en) * | 2008-09-10 | 2013-07-10 | 株式会社日本触媒 | Laminated plate and front plate for display device |
| JP5122680B2 (en) * | 2009-11-12 | 2013-01-16 | 凸版印刷株式会社 | Antireflection film |
| JP4678451B1 (en) * | 2010-11-05 | 2011-04-27 | 東洋インキ製造株式会社 | Antistatic coating composition |
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- 2017-05-09 CN CN201780039288.5A patent/CN109328198B/en active Active
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102212280A (en) * | 2010-04-01 | 2011-10-12 | 东洋油墨制造股份有限公司 | Antistatic coating composition |
| 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 |
| CN104017138A (en) * | 2013-02-04 | 2014-09-03 | 荒川化学工业株式会社 | Active energy ray gel-type resin composition, antistatic agent used for composition, solidified membrane, and anti-static processing optical film |
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| JP6418474B2 (en) | 2018-11-07 |
| TWI740952B (en) | 2021-10-01 |
| CN109328198A (en) | 2019-02-12 |
| JPWO2018003294A1 (en) | 2018-07-12 |
| WO2018003294A1 (en) | 2018-01-04 |
| TW201819423A (en) | 2018-06-01 |
| KR20190011755A (en) | 2019-02-07 |
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