WO2022190937A1 - ハードコート用硬化性組成物 - Google Patents
ハードコート用硬化性組成物 Download PDFInfo
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- WO2022190937A1 WO2022190937A1 PCT/JP2022/008351 JP2022008351W WO2022190937A1 WO 2022190937 A1 WO2022190937 A1 WO 2022190937A1 JP 2022008351 W JP2022008351 W JP 2022008351W WO 2022190937 A1 WO2022190937 A1 WO 2022190937A1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/08—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
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- B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
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- C—CHEMISTRY; METALLURGY
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and 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
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/22—Esters containing halogen
- C08F20/24—Esters containing halogen containing perhaloalkyl radicals
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F22/00—Homopolymers and 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
- C08F22/10—Esters
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
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- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
-
- 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
- C08J7/042—Coating with two or more layers, where at least one layer of a composition contains a polymer binder
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- 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
- C08J7/046—Forming abrasion-resistant coatings; Forming surface-hardening coatings
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D135/00—Coating compositions based on homopolymers or 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 another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D135/02—Homopolymers or copolymers of esters
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
Definitions
- the present invention relates to a curable composition useful as a material for forming a hard coat layer applied to the surface of various display elements, and capable of forming a hard coat layer excellent in slipperiness, scratch resistance, abrasion resistance and water repellency. , relates to homogeneous curable compositions free of suspensions and sediments.
- touch panels have been introduced into various devices such as portable information terminal devices such as mobile phones and tablet computers, laptop computers, home appliances, and automobile interior and exterior parts. is often operated by touching with a finger or a pen.
- the surface of the touch panel is required to be water and oil repellent in order to facilitate the removal of fingerprints, and the water and oil repellency is maintained even after repeated finger rubbing.
- Abrasion resistance is required.
- the surface of the touch panel is operated with a finger or a pen, the surface is required to have smoothness from the viewpoint of the touch feeling of the finger or the pen.
- the surface of the touch panel is required to have scratch resistance in order to prevent scratches.
- a surface coat layer such as a hard coat layer is provided.
- Fluorine-containing compounds exhibit high lubricity and water and oil repellency, and are therefore used as materials for forming hard coat layers. method is used. Fluorine-based surface modifiers are known to segregate on the surface of the hard coat layer due to the low surface energy of fluorine atoms.
- a method in which a high-density crosslinked structure is formed to increase the surface hardness of the hard coat layer and provide resistance to external force.
- a material for forming such a hard coat layer at present, polyfunctional acrylate materials that are three-dimensionally crosslinked by radicals generated by irradiation with active energy rays are most used.
- a material having an active energy ray-polymerizable group is generally used as the fluorine-based surface modifier added to the coating liquid for forming the hard coat layer in order to impart scratch resistance and abrasion resistance to the hard coat layer. (Patent Document 1).
- Patent Document 2 in order to obtain durability properties such as scratch resistance and wear resistance in the hard coat layer, for example, when a fluorine-based surface modifier having a crosslinkable group is used, fluorine atoms are added. The molecular chains contained therein are immobilized, and the slipperiness of the hard coat layer is reduced. In other words, there is a trade-off relationship between durability properties such as scratch resistance and wear resistance, and slipperiness, and it is difficult to achieve both high levels of properties.
- the fluorine-based surface modifier aggregates in the coating liquid for forming the hard coat layer
- the molecular chains containing fluorine atoms are sufficiently formed on the surface of the hard coat layer when the hard coat layer is formed using the coating liquid. Segregation does not occur, and the original characteristics of slipperiness, water repellency, and scratch resistance cannot be expressed.
- Patent Document 3 discloses a fluorine-containing polyether that becomes aggregates when obtaining a hard coating agent composition and causes cloudiness of the composition, and the composition. have reported the combined use of a fluorine-containing block copolymer with excellent compatibility with
- An object of the present invention is to provide a homogeneous curable composition free of suspended solids and sediments, capable of forming a hard coat layer having both durability and lubricity, which are in a trade-off relationship, at a high level of properties. do. In addition to these, it is necessary for the hard coat layer to have high liquid repellency in consideration of actual use.
- the first aspect of the present invention comprises (a) 100 parts by mass of an active energy ray-curable polyfunctional monomer having two or more (meth)acryloyl groups in one molecule, and (b) a poly(oxyperfluoroalkylene) group. 0.05 to 2 parts by mass of a perfluoropolyether having an active energy ray polymerizable group only at one end of the molecular chain via a poly(oxyalkylene) group and having a weight average molecular weight of 1500 to 3500; and (c) a curable composition containing 1 to 20 parts by mass of a polymerization initiator that generates radicals by active energy rays.
- Another aspect of the present invention includes (a) 100 parts by mass of an active energy ray-curable polyfunctional monomer having two or more (meth)acryloyl groups in one molecule, and (b) a poly(oxyperfluoroalkylene) group.
- the (b) perfluoropolyether has the active energy ray-polymerizable group via the poly(oxyalkylene) group only at one end of the molecular chain containing the poly(oxyperfluoroalkylene) group, and a weight average molecular weight of 1,500 to 3,500.
- the (b) perfluoropolyether has the active energy ray-polymerizable group via a urethane bond bonded to the poly(oxyalkylene) group.
- the poly(oxyalkylene) group is a poly(oxyethylene) group.
- the poly(oxyperfluoroalkylene) group has repeating units -(CF 2 O)- and/or repeating units -(CF 2 CF 2 O)- and has both repeating units, these repeating units It is a group formed by combining units by block bonding, random bonding, or block bonding and random bonding.
- a molecular chain containing the poly(oxyperfluoroalkylene) group has a structure represented by the following formula [1].
- m is the number of repeating units -(CF 2 CF 2 O)-
- n is the number of repeating units -(CF 2 O)-
- 5 ⁇ (m + n) ⁇ 30 m and n each independently represent an integer of 0 or more
- q is the number of oxyethylene groups and represents an integer of 2 to 20.
- n each independently represent an integer of 1 or more.
- the (b) perfluoropolyether is a compound represented by the following formula [2].
- m, n and q have the same definitions as in the above formula [1]
- A represents the terminal group having the active energy ray-polymerizable group.
- the terminal group A is a group represented by the following formula [A1] or [A2].
- R 1 and R 2 each independently represent a hydrogen atom or a methyl group
- * is a bond with the urethane bond of the compound represented by the above formula [2] represents.
- the curable composition of the present invention further comprises (d) a solvent.
- Another aspect of the present invention is a cured film obtained from the curable composition of the present invention.
- Another aspect of the present invention is a hard coat film comprising a hard coat layer on at least one surface of a film substrate, wherein the hard coat layer comprises the cured film.
- a lower layer of a hard coat layer is provided between the surface of the film substrate and the hard coat layer, and the film substrate is a resin film.
- the hard coat layer has a thickness of 1 ⁇ m to 20 ⁇ m.
- Another aspect of the present invention is a step of applying the curable composition of the present invention on a film substrate to form a coating film, and irradiating the coating film with an active energy ray and curing it to form a hard coat layer.
- a method for producing a hard coat film comprising steps.
- Another aspect of the present invention is the steps of applying the curable composition of the present invention on a film substrate to form a coating film, removing the solvent from the coating film by heating, and A method for producing a hard coat film, comprising the step of forming a hard coat layer by irradiating with energy rays and curing.
- a hard coat film further comprising the step of forming a lower layer of a hard coat layer on the surface of the film substrate, wherein the film substrate is a resin film, and the coating film is formed on the lower layer of the hard coat layer. is a manufacturing method.
- Another aspect of the present invention has an active energy ray-polymerizable group via a poly(oxyalkylene) group only at one end of a molecular chain containing a poly(oxyperfluoroalkylene) group, and a weight average molecular weight of It is a perfluoropolyether compound of 1500 to 3500.
- Another aspect of the present invention is a raw material perfluoropoly having a number average molecular weight of 1500 to 3000, which has a hydroxyl group bonded to a poly(oxyperfluoroalkylene) group only at one end of a molecular chain containing a poly(oxyperfluoroalkylene) group.
- It is a perfluoropolyether compound which is a reaction product of an ether and a compound having a functional group capable of reacting with the hydroxy group and an active energy ray-polymerizable group.
- the perfluoropolyether compound has the active energy ray-polymerizable group via the poly(oxyalkylene) group only at one end of the molecular chain containing the poly(oxyperfluoroalkylene) group, and has a weight It has an average molecular weight of 1,500 to 3,500.
- the molecular chain containing the poly(oxyperfluoroalkylene) group has a structure represented by the following formula [1].
- m is the number of repeating units -(CF 2 CF 2 O)-
- n is the number of repeating units -(CF 2 O)-
- 5 ⁇ (m + n) ⁇ 30 and m and n each independently represent an integer of 0 or more, and when both repeating units are present, these repeating units are bound by block bonding, random bonding, or block bonding and random bonding.
- q is the number of oxyethylene groups and represents an integer of 2 to 20.
- n each independently represent an integer of 1 or more.
- the perfluoropolyether compound is a compound represented by the following formula [2].
- m, n and q have the same definitions as in the above formula [1]
- A is represented by the following formula [A1] or [A2] having the active energy ray-polymerizable group. represents the terminal group that (In the above formulas [A1] and [A2], R 1 and R 2 each independently represent a hydrogen atom or a methyl group, * is a bond with the urethane bond of the compound represented by the above formula [2] represents.)
- a curable composition can be provided.
- a curable composition useful for forming a cured film and a hard coat layer imparting high water repellency in addition to achieving both of the above properties, and a hard coat layer excellent in these properties are provided.
- a hard coat film can be provided.
- the active energy ray-curable polyfunctional monomer having two or more (meth)acryloyl groups in one molecule is an active It refers to a monomer that undergoes a polymerization reaction and cures when irradiated with energy rays.
- Preferred (a) polyfunctional monomers in the curable composition of the present invention include monomers selected from the group consisting of polyfunctional (meth)acrylate compounds, and polyfunctional urethane (meth)acrylate compounds described later. and monomers selected from the group consisting of lactone-modified polyfunctional (meth)acrylate compounds.
- the polyfunctional monomer (a) one of the above polyfunctional (meth)acrylate compounds can be used alone, or two or more of them can be used in combination.
- the (meth)acrylate compound includes both an acrylate compound and a methacrylate compound.
- (meth)acrylic acid includes acrylic acid and methacrylic acid.
- the (a) polyfunctional monomer may be an oxyalkylene-modified polyfunctional monomer, and examples of the oxyalkylene-modified monomer include oxymethylene-modified, oxyethylene-modified, and oxypropylene-modified.
- examples of the oxyalkylene-modified polyfunctional monomer include oxyalkylene-modified compounds of the polyfunctional (meth)acrylate compound or polyfunctional urethane (meth)acrylate compound.
- the oxyalkylene-modified polyfunctional monomers may also be used singly or in combination of two or more.
- polyfunctional monomer (a) preferred in the present invention, a polyfunctional monomer having at least 2 (meth)acryloyl groups per molecule, preferably at least 3 per molecule, more preferably at least 4 per molecule Mention may be made of monomers.
- Examples of the polyfunctional (meth)acrylate compound include trimethylolpropane tri(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, pentaerythritol di(meth)acrylate, Pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, glycerin tri(meth)acrylate, ethoxylated trimethylolpropane tri(meth) Acrylates, ethoxylated pentaerythritol tetra(meth)acrylate, ethoxylated dipentaerythritol hexa(meth)acrylate, ethoxylated glycerin
- preferred polyfunctional (meth)acrylate compounds include pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, and dipentaerythritol hexa(meth)acrylate. can be mentioned.
- Examples of the oxyalkylene-modified polyfunctional (meth)acrylate compound include oxyalkylene-modified polyol (meth)acrylate compounds.
- Examples of the polyols include glycerin, diglycerin, triglycerin, tetraglycerin, pentaglycerin, hexaglycerin, decaglycerin, polyglycerin, trimethylolpropane, ditrimethylolpropane, pentaerythritol, and dipentaerythritol.
- polyfunctional urethane (meth)acrylate compound for example, a compound obtained by reacting a polyfunctional isocyanate and a (meth)acrylate having a hydroxy group, and a compound obtained by reacting a polyfunctional isocyanate and a (meth)acrylate having a hydroxy group with a polyol
- examples include compounds obtained by reaction, but the polyfunctional urethane (meth)acrylate compounds that can be used in the present invention are not limited to these examples.
- polyfunctional isocyanates examples include tolylene diisocyanate, isophorone diisocyanate, xylylene diisocyanate, and hexamethylene diisocyanate.
- (meth)acrylates having a hydroxy group examples include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, pentaerythritol tri(meth)acrylate, and dipentaerythritol penta(meth)acrylate. , and tripentaerythritol hepta(meth)acrylate.
- polystyrene resin examples include diols such as ethylene glycol, propylene glycol, neopentyl glycol, 1,4-butanediol, 1,6-hexanediol, diethylene glycol and dipropylene glycol; these diols and succinic acid and maleic acid.
- polyester polyols which are reaction products with aliphatic dicarboxylic acids or dicarboxylic anhydrides such as adipic acid; polyether polyols; and polycarbonate diols.
- the polyfunctional monomer may be a lactone-modified polyfunctional (meth)acrylate compound, and the lactone to be modified is preferably ⁇ -caprolactone.
- the lactone-modified polyfunctional (meth)acrylate compound include ⁇ -caprolactone-modified pentaerythritol tri(meth)acrylate, ⁇ -caprolactone-modified pentaerythritol tetra(meth)acrylate, and ⁇ -caprolactone-modified dipentaerythritol penta(meth)acrylate. , and ⁇ -caprolactone-modified dipentaerythritol hexa(meth)acrylate.
- the perfluoropolyether has, for example, a hydroxy group bonded to a poly(oxyalkylene) group only at one end of the molecular chain containing the poly(oxyperfluoroalkylene) group, and has a number average molecular weight of 1500 to 3000. It is obtained by reacting a raw material perfluoropolyether with a compound having a functional group that reacts with the hydroxy group and the active energy ray-polymerizable group.
- the functional group that reacts with the hydroxy group include a hydroxy group, a carboxy group and an isocyanate group.
- the (b) perfluoropolyether preferable in the curable composition of the present invention has a urethane bond bonded to the poly(oxyperfluoroalkylene) group only at one end of the molecular chain containing the poly(oxyperfluoroalkylene) group. It has the active energy ray-polymerizable group via the active energy ray-polymerizable group.
- Perfluoropolyether has a poly(oxyalkylene) group, so (a) it has excellent compatibility with polyfunctional monomers, and (b) only perfluoropolyether is used to form the curable composition of the present invention. can serve as a surface modifier in a hard coat layer formed from As the poly(oxyalkylene) group, a poly(oxyethylene) group is preferred.
- the perfluoropolyether is not limited to those having one active energy ray-polymerizable group via the poly(oxyalkylene) group only at one end of the molecular chain containing the poly(oxyperfluoroalkylene) group. , may have two or more active energy ray-polymerizable groups.
- the active energy ray-polymerizable group include (meth)acryloyl groups and vinyl groups. group. Among these terminal groups, a group having two active energy ray-polymerizable groups and represented by the formula [A2] is preferable.
- poly(oxyperfluoroalkylene) group -[CF 2 O]-(oxyperfluoromethylene group) and -[CF 2 CF 2 O]- from the viewpoint of obtaining a cured film having good scratch resistance.
- a group having both (oxyperfluoroethylene groups) as repeating units is preferred. In that case, the bonding of these oxyperfluoroalkylene groups may be either block bonding or random bonding.
- the perfluoropolyether preferably has a fluorine atom content of 35% by mass or more and 60% by mass or less, more preferably 40% by mass or more and 55% by mass or less.
- a fluorine atom content is 35% by mass or more, a hard coat layer having excellent water repellency and slipperiness can be obtained. , a hard coat layer with little cloudiness can be obtained.
- the perfluoropolyether has a weight average molecular weight of 1,500 to 3,500, preferably 1,600 to 3,500, and more preferably 1,700 to 3,000.
- the weight average molecular weight of the (b) perfluoropolyether is within the above range, the (b) perfluoropolyether tends to stay on the surface of the hard coat layer obtained from the curable composition of the present invention, and the layer surface Since the shear stress is sufficiently reduced, a hard coat layer with excellent slipperiness can be obtained.
- the weight-average molecular weight of (b) the perfluoropolyether is within the above range, the hardness of the layer surface is appropriately adjusted, and a hard coat layer having excellent durability such as scratch resistance can be obtained. . That is, when the weight average molecular weight of (b) the perfluoropolyether is within the above range, it is possible to achieve both lubricity and durability.
- the content of the (b) perfluoropolyether in the curable composition of the present invention is 0.05 to 2 parts by mass with respect to 100 parts by mass of the (a) polyfunctional monomer.
- the content of the (b) perfluoropolyether is 0.05 parts by mass or more, the (b) perfluoropolyether is sufficiently present on the surface of the hard coat layer obtained from the curable composition of the present invention. Therefore, a hard coat layer having excellent lubricity can be obtained.
- the content of (b) perfluoropolyether is 2 parts by mass or less, it is sufficiently compatible with (a) the polyfunctional monomer, and a hard coat layer with little cloudiness can be obtained.
- Perfluoropolyethers can be used singly or in combination of two or more.
- the (c) polymerization initiator that is preferable in the curable composition of the present invention is a polymerization initiator that generates radicals upon exposure to active energy rays such as electron beams, ultraviolet rays, and X-rays, particularly ultraviolet irradiation.
- polymerization initiators such as benzoins, alkylphenones, thioxanthones, azos, azides, diazos, o-quinonediazides, acylphosphine oxides, oxime esters, organic peroxides, benzophenones , biscoumarins, bisimidazoles, titanocenes, thiols, halogenated hydrocarbons, trichloromethyltriazines, and onium salts such as iodonium salts and sulfonium salts.
- polymerization initiators may be used alone or in combination of two or more.
- alkylphenones As the polymerization initiator (c), it is preferable to use alkylphenones as the polymerization initiator (c). By using alkylphenones, a cured film with improved scratch resistance can be obtained.
- alkylphenones examples include 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-1-(4-(2-hydroxyethoxy)phenyl)- ⁇ -hydroxyalkyl such as 2-methylpropan-1-one, 2-hydroxy-1-(4-(4-(2-hydroxy-2-methylpropionyl)benzyl)phenyl)-2-methylpropan-1-one Phenones; 2-methyl-1-(4-(methylthio)phenyl)-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butan-1-one, etc. 2,2-dimethoxy-1,2-diphenylethan-1-one; and methyl phenylglyoxylate.
- the content of the polymerization initiator (c) in the curable composition of the present invention is 1 part by mass to 20 parts by mass, preferably 2 parts by mass to 10 parts by mass, relative to 100 parts by mass of the (a) polyfunctional monomer. is.
- the curable composition of the present invention may contain (d) a solvent as an optional component, that is, it may be in the form of a varnish.
- a solvent As the solvent, the solubility and dispersibility of the components (a) to (c), and the workability during coating of the curable composition related to the formation of the cured film (hard coat layer) described later, It may be appropriately selected in consideration of the drying properties before and after curing.
- the (d) solvent examples include aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene and tetralin; aliphatic or alicyclic hydrocarbons such as n-hexane, n-heptane, mineral spirits and cyclohexane; Halides such as methyl chloride, methyl bromide, methyl iodide, dichloromethane, chloroform, carbon tetrachloride, trichlorethylene, perchlorethylene, o-dichlorobenzene; ethyl acetate, propyl acetate, butyl acetate, methoxybutyl acetate, methyl cellosolve Esters or ester ethers such as acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether acetate (PGMEA); diethyl ether, tetrahydrofuran (THF), 1,4-
- the content of (d) the solvent in the curable composition of the present invention is not particularly limited. It is the concentration that becomes mass %.
- the solid content concentration also referred to as non-volatile content concentration refers to the solid content ( excluding the solvent component from all components) content.
- the curable composition of the present invention may generally contain additives, such as polymerization inhibitors, photosensitizers, leveling agents, surfactants, which are generally added as necessary, as long as they do not impair the effects of the present invention.
- additives such as polymerization inhibitors, photosensitizers, leveling agents, surfactants, which are generally added as necessary, as long as they do not impair the effects of the present invention.
- Agents, adhesion imparting agents, plasticizers, ultraviolet absorbers, storage stabilizers, antistatic agents, inorganic fillers, pigments, dyes, etc. may be used singly or in combination of two or more thereof.
- the curable composition of the present invention can form a cured film by coating (coating) a substrate to form a coating film, and irradiating the coating film with an active energy ray to polymerize (cure) it,
- the cured film is also an object of the present invention.
- the hard coat layer in the hard coat film to be described later the cured film can be used.
- the base material examples include various resins (polyesters such as polycarbonate, polymethacrylate, polystyrene, polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), polyurethanes, thermoplastic polyurethanes (TPU), polyolefins, polyamides, polyimides, epoxy resins, , melamine resin, triacetyl cellulose (TAC), acrylonitrile-butadiene-styrene copolymer (ABS), acrylonitrile-styrene copolymer (AS), norbornene resin), metal, wood, paper, glass, slate can be done.
- the shape of these substrates may be plate-like, film-like or three-dimensional molded body.
- a primer layer an ultraviolet absorbing layer, an infrared absorbing layer, a near-infrared absorbing layer, an electromagnetic wave absorbing layer, a color correction layer, a refractive index adjusting layer, a weather resistant layer, an antireflection layer, and an antistatic layer may be added to the surface of the base material.
- a layer, an anti-discoloration layer, a gas barrier layer, a water vapor barrier layer, a light scattering layer, an electrode layer, etc. may be formed as a lower layer of the hard coat layer, and a plurality of lower layers of the hard coat layer may be laminated.
- the layer formed on the surface of the substrate is not particularly limited as long as it does not impair the effects of the present invention.
- the coating method on the substrate includes cast coating method, spin coating method, blade coating method, dip coating method, roll coating method, spray coating method, bar coating method, die coating method, inkjet method, printing method (letterpress printing method , Intaglio printing method, lithographic printing method, screen printing method, etc.) can be appropriately selected, among which roll-to-roll method can be used, and from the viewpoint of thin film coating, letterpress printing method In particular, it is desirable to use the gravure coating method. It is preferable that the curable composition of the present invention is filtered in advance using a filter having a pore size of about 0.2 ⁇ m, and then applied. When applying, a solvent may be added to the curable composition, if necessary. Examples of the solvent in this case include various solvents listed in the above [(e) solvent].
- the coating film is pre-dried with a heating means such as a hot plate or an oven to remove the solvent (solvent removal step).
- a heating means such as a hot plate or an oven to remove the solvent (solvent removal step).
- the heat drying conditions are preferably, for example, 40° C. to 120° C. and about 30 seconds to 10 minutes.
- the coating film is cured by irradiation with active energy rays such as ultraviolet rays. Active energy rays include, for example, ultraviolet rays, electron beams and X-rays, and ultraviolet rays are particularly preferred.
- the polymerization may be completed by performing post-baking, specifically by heating using a heating means such as a hot plate or an oven.
- the thickness of the cured film formed is usually 0.1 ⁇ m to 20 ⁇ m, preferably 0.5 ⁇ m to 10 ⁇ m after drying and curing.
- a hard coat film having a hard coat layer on at least one side (surface) of a film substrate can be produced using the curable composition of the present invention.
- the hard coat film is also an object of the present invention, and the hard coat film is suitably used for protecting the surface of various display elements such as touch panels and liquid crystal displays.
- the hard coat layer in the hard coat film of the present invention comprises the steps of applying the curable composition of the present invention onto a film substrate to form a coating film, optionally removing the solvent by heating, and It can be formed by a method including a step of irradiating the film with an active energy ray such as ultraviolet rays to cure the coating film.
- the present invention also includes a method for producing a hard coat film having a hard coat layer on at least one surface of a film substrate, including these steps.
- polyesters such as polyethylene terephthalate (PET), polybutylene terephthalate (PBT) and polyethylene naphthalate (PEN), polyurethanes, thermoplastic polyurethanes (TPU), polycarbonates, polymethacrylates, polystyrenes, polyolefins, Films such as polyamide, polyimide, and triacetyl cellulose (TAC) can be used.
- PET polyethylene terephthalate
- PBT polybutylene terephthalate
- PEN polyethylene naphthalate
- TPU thermoplastic polyurethanes
- TPU thermoplastic polyurethanes
- Films such as polyamide, polyimide, and triacetyl cellulose (TAC) can be used.
- the film substrate may be formed by laminating a plurality of layers.
- a primer layer an ultraviolet absorption layer, an infrared absorption layer, a near-infrared absorption layer, an electromagnetic wave absorption layer, a color correction layer, a refractive index adjustment layer, a weather resistant layer, an antireflection layer, and an antistatic layer may be added to the surface of the resin film.
- a discoloration prevention layer, a gas barrier layer, a water vapor barrier layer, a light scattering layer, an electrode layer, and the like, which are different from the resin film may be laminated as a lower layer of the hard coat layer, and the hard coat layer may be under the A plurality of layers may be laminated.
- the layer laminated on the surface of the resin film is not particularly limited as long as it does not impair the effects of the present invention.
- the method of applying the curable composition of the present invention on the film substrate (coating film forming step) and the method of irradiating the active energy ray to the coating film (curing step) are listed in the above-mentioned ⁇ cured film>.
- method can be used.
- the curable composition of the present invention contains a solvent (in the form of a varnish)
- a step of drying the coating film to remove the solvent can be included after the coating film forming step, if necessary.
- the method of drying the coating film (solvent removal step) mentioned in the above ⁇ Cured film> can be used.
- the layer thickness (film thickness) of the hard coat layer thus obtained is, for example, 1 ⁇ m to 20 ⁇ m, preferably 1 ⁇ m to 10 ⁇ m.
- ⁇ Perfluoropolyether compound A raw perfluoropolyether having a hydroxy group bonded to a poly(oxyalkylene) group only at one end of a molecular chain containing a poly(oxyperfluoroalkylene) group and having a number average molecular weight of 1,500 to 3,000 reacts with the hydroxy group.
- a perfluoropolyether compound which is a reaction product with a compound having a functional group and an active energy ray polymerizable group is also subject of the present invention.
- Coating device by bar coater PM-9050MC manufactured by SMT Co., Ltd. Bar: OSG System Products Co., Ltd. A-Bar OSP-30 maximum wet film thickness 30 ⁇ m (after drying film thickness 6 ⁇ m) or OSP-15 maximum wet film thickness 15 ⁇ m (after drying film thickness 3 ⁇ m) Coating speed: 4 m / min
- Film thickness measurement device F20 film thickness measurement system manufactured by Filmetrics Co., Ltd.
- Oven device Two-layer clean oven (upper and lower type) PO- manufactured by Sanki Keiso Co., Ltd. 250-45-D (4) UV curing device: CV-110QC-G manufactured by Heraeus Co., Ltd.
- Lamp Electrodeless lamp H-bulb manufactured by Heraeus Co., Ltd.
- Scratch resistance test and abrasion resistance test Apparatus Reciprocating abrasion tester TRIBOGEAR TYPE: 30S manufactured by Shinto Kagaku Co., Ltd. Scanning speed: 3200 mm/min Scanning distance: 50 mm (6)
- Contact angle measurement device DropMaster DM-501 manufactured by Kyowa Interface Science Co., Ltd. Measurement temperature: 23°C (7)
- Dynamic Friction Coefficient Measurement Apparatus Variable Load Friction and Abrasion Test System TRIBOGEAR (registered trademark) TYPE: HHS2000 manufactured by Sintokagaku Co., Ltd.
- Probe 0.6mmR sapphire pin Load: 200g Scanning speed: 2 mm/sec Scanning distance: 10 mm (8) Total light transmittance, haze measurement device: Haze meter NDH5000 manufactured by Nippon Denshoku Industries Co., Ltd.
- Polyfunctional acrylate PA1 dipentaerythritol pentaacrylate/hexaacrylate mixture [Aronix (registered trademark) M-403 manufactured by Toagosei Co., Ltd.]
- Multifunctional acrylate PA2 Oxyethylene-modified multifunctional acrylate [Daiichi Kogyo Seiyaku Co., Ltd.
- PFPE2 A perfluoropolyether of the following structure having one hydroxy group at only one end without intervening a poly(oxyalkylene) group [manufactured by Solvay Specialty Polymers, Inc. 7324X 19 F-NMR and 1 H-NMR calculated from the analysis results.
- PFPE3 A perfluoropolyether of the following structure having one hydroxy group only at one end without a poly(oxyalkylene) group [FO2, molecular weight 978.15 manufactured by Apollo Scientific]
- PFPE4 Perfluoropolyether having the following structure having one hydroxy group at one end only without a poly(oxyalkylene) group (1H,1H-perfluoro-3,6,9-trioxatridecan-1-ol ) [C10GOL manufactured by Exfluor Research, molecular weight 548.1]
- N1 1,1-bis (acryloyloxymethyl) ethyl isocyanate [Kalenz (registere
- Neostan (registered trademark) U-830]
- SMA7 A perfluoropolyether having a total of four active energy ray-polymerizable groups at both ends of a molecular chain containing a poly(oxyperfluoroalkylene) group
- Fluorolink (registered trademark) AD-1700 manufactured by Solvay Specialty Polymers, non-volatile 70% by mass solution, weight average molecular weight measured in terms of polystyrene by GPC: Mw is 3973, degree of dispersion: Mw/Mn is 2.1 (Mn is number average molecular weight), perfluoropolymer calculated by combustion ion chromatography Content ratio of fluorine atoms in the ether compound 29% by mass]
- MEK methyl ethyl ketone
- PGME propylene glycol monomethyl ether
- PGMEA propylene glycol monomethyl ether acetate
- O2959 2-hydroxy-1-(4-(2-hydroxyethoxy
- the weight average molecular weight Mw of the resulting SMA1 measured in terms of polystyrene by GPC was 1908, and the degree of dispersion Mw/Mn was 1.0. Further, the content of fluorine atoms in SMA1 calculated by combustion ion chromatography was 47% by mass.
- the weight average molecular weight Mw of the resulting SMA5 measured in terms of polystyrene by GPC was 1299, and the degree of dispersion Mw/Mn was 1.0.
- the fluorine atom content in SMA5 calculated by combustion ion chromatography is 51% by mass, which is about the same as the fluorine atom content of 51% by mass theoretically calculated from the structure of SMA5. rice field.
- the fluorine atom content in SMA5 calculated by combustion ion chromatography is 46% by mass, which is about the same as the fluorine atom content of 47% by mass theoretically calculated from the structure of SMA5. rice field.
- Examples 1 to 8, Comparative Examples 1 to 4 Each component shown in Table 1 was mixed to prepare a curable composition having a solid concentration shown in Table 1.
- the solid content refers to components other than the solvent.
- [parts] represents [parts by mass]
- [%] represents [% by mass].
- the polyfunctional acrylate and the surface modifier in Table 1 each represent the solid content.
- curable compositions are applied to an A4 size PET film [Lumirror (registered trademark) U403 (also known as U40) manufactured by Toray Industries, Inc., thickness 100 ⁇ m] having a primer layer formed on both sides by a bar coater. to obtain a coating film.
- the coating film was dried in an oven at 60° C. for 8 minutes to remove the solvent.
- a hard coat film having a hard coat layer (cured film) with a thickness of 3 ⁇ m or 6 ⁇ m was produced by exposing the obtained film to UV light at an exposure dose of 300 mJ/cm 2 in a nitrogen atmosphere.
- [Water repellency] 1 ⁇ L of water was applied to the surface of the hard coat layer, and after 10 seconds, the contact angle ⁇ was measured five times, and the average value was evaluated according to the following criteria. Assuming actual use as a hard coat layer, at least B is required, and A is desirable.
- the surface of the hard coat layer was rubbed back and forth 2,500 times with a load of 1 kg using a cylindrical eraser [RUBBER STICK manufactured by Minoan, ⁇ 6.0 mm] attached to a reciprocating abrasion tester. 1 ⁇ L of water was applied to the rubbed portion, and the contact angle ⁇ after 5 seconds was measured at 5 points.
- the coefficient of dynamic friction ⁇ ' was measured at five points on the surface of the hard coat layer, and the average value was evaluated according to the following criteria. Note that the smaller the value of the coefficient of dynamic friction, the smaller the friction with the probe used, which is a measure of the slipperiness. Since the smaller the dynamic friction coefficient value, the better the slipperiness when touched, the smaller the dynamic friction coefficient value, the better.
- the haze was measured at three points on the surface of the hard coat layer, and the average value was calculated.
- the haze of the PET film [Lumirror (registered trademark) U403 (also known as U40) manufactured by Toray Industries, Inc., thickness 100 ⁇ m] used this time as the base material is 1.6.
- the curable compositions of Examples 1 to 8 had poly(oxyethylene ) obtained by reacting any one of the isocyanate compound groups N1 to N3 having the active energy ray-polymerizable group with a perfluoropolyether PFPE1 having a number average molecular weight of 1900 having one hydroxy group bonded to a group.
- the curable compositions of Examples 1 to 8 exhibited excellent homogeneity, and the hard coat films provided with the hard coat layers obtained from the curable compositions exhibited excellent It exhibited slipperiness, scratch resistance, water repellency and abrasion resistance.
- the curable composition of Comparative Example 1 has a poly(oxyalkylene) group at only one end of the molecular chain containing the polyfunctional acrylate PA1 and the poly(oxyperfluoroalkylene) group.
- SMA4 with a weight average molecular weight of 1710 obtained by reacting the perfluoropolyether compound PFPE2 with a number average molecular weight of 1750 to 1950 having one hydroxy group with the isocyanate compound N1 having the active energy ray polymerizable group.
- the curable compositions of Comparative Examples 1 and 2 had poor homogeneity, and in addition, the hard coat films provided with the hard coat layers obtained from the curable compositions were SMA4 and Since the cohesive force of SMA5 is high and SMA4 and SMA5 cannot be sufficiently segregated on the surface of the hard coat layer, compared with hard coat films provided with hard coat layers obtained from the curable compositions of Examples 1 to 8, , resulting in poor slipperiness and wear resistance.
- the curable composition of Comparative Example 3 has a poly(oxyalkylene) group at only one end of the molecular chain containing the polyfunctional acrylate PA1 and the poly(oxyperfluoroalkylene) group.
- SMA6 having a weight average molecular weight of 1029 obtained by reacting the isocyanate compound N1 having the active energy ray-polymerizable group with the perfluoropolyether compound PFPE4 having a molecular weight of 548.1 and having one hydroxy group.
- the hard coat film provided with the hard coat layer obtained from the curable composition is SMA6 poly(oxyperfluoro alkylene) group, compared with the hard coat film having a hard coat layer obtained from the curable compositions of Examples 1 to 8, sliding, scratch resistance and abrasion resistance resulted in inferior results.
- the curable composition of Comparative Example 4 has an active energy ray-polymerizable group at both ends of the molecular chain containing the polyfunctional acrylate PA1 and the poly(oxyperfluoroalkylene) group. It contains a perfluoropolyether compound SMA7 with an average molecular weight of 3973.
- the hard coat film having the hard coat layer obtained from the curable composition had SMA7 of poly(oxyperfluoro alkylene) group because it has actinic ray energy polymerizable groups at both ends of the molecular chain containing the group, the molecular mobility of the poly (oxyperfluoroalkylene) chain is reduced, from the curable compositions of Examples 1 to 8 As compared with the hard coat film provided with the obtained hard coat layer, the result was inferior in slipperiness and abrasion resistance.
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Abstract
Description
本発明では、トレードオフ関係にある耐久特性と滑り性とを高い特性水準で両立するハードコート層が形成可能な、浮遊物及び沈降物のない均質な硬化性組成物を提供することを課題とする。これらに加え、実使用を想定する上で、ハードコート層が高い撥液特性を兼ね備えることが必要となる。
本発明の硬化性組成物の各成分について、以下に説明する。
(a)成分の(メタ)アクリロイル基を1分子中に2個以上有する活性エネルギー線硬化性多官能モノマー(以下、単に「(a)多官能モノマー」とも称する。)とは、紫外線等の活性エネルギー線を照射することで重合反応が進行し、硬化するモノマーを指す。
(b)成分のポリ(オキシパーフルオロアルキレン)基を含む分子鎖の片末端のみに、ポリ(オキシアルキレン)基を介して活性エネルギー線重合性基を有し、且つ重量平均分子量が1500乃至3500のパーフルオロポリエーテルを以下、単に「(b)パーフルオロポリエーテル」とも称する。(b)パーフルオロポリエーテルは、例えば、前記ポリ(オキシパーフルオロアルキレン)基を含む分子鎖の片末端のみにポリ(オキシアルキレン)基と結合したヒドロキシ基を有する数平均分子量が1500乃至3000の原料パーフルオロポリエーテルと、該ヒドロキシ基と反応する官能基及び前記活性エネルギー線重合性基を有する化合物とを反応させて得られる。前記ヒドロキシ基と反応する官能基として、例えば、ヒドロキシ基、カルボキシ基及びイソシアネート基が挙げられる。本発明の硬化性組成物において好ましい(b)パーフルオロポリエーテルは、前記ポリ(オキシパーフルオロアルキレン)基を含む分子鎖の片末端のみに、前記ポリ(オキシアルキレン)基と結合したウレタン結合を介して、前記活性エネルギー線重合性基を有する。
本発明の硬化性組成物において好ましい(c)重合開始剤は、例えば、電子線、紫外線、X線等の活性エネルギー線により、特に紫外線照射によりラジカルを発生する重合開始剤である。
本発明の硬化性組成物は、任意成分として(d)溶媒を含有してもよく、すなわちワニスの形態としてもよい。(d)溶媒としては、前記(a)成分乃至(c)成分の溶解・分散性、また、後述する硬化膜(ハードコート層)の形成に係る硬化性組成物の塗工時の作業性、硬化前後の乾燥性等を考慮して適宜選択すればよい。
また、本発明の硬化性組成物には、本発明の効果を損なわない限り、必要に応じて一般的に添加される添加剤、例えば、重合禁止剤、光増感剤、レベリング剤、界面活性剤、密着性付与剤、可塑剤、紫外線吸収剤、貯蔵安定剤、帯電防止剤、無機充填剤、顔料、染料等のうち一種を単独で、或いは二種以上を組み合わせて適宜配合してよい。
本発明の硬化性組成物は、基材上に塗布(コーティング)して塗膜を形成し、該塗膜に活性エネルギー線を照射して重合(硬化)させることにより、硬化膜を形成でき、該硬化膜も本発明の対象である。また後述するハードコートフィルムにおけるハードコート層として、上記硬化膜からなるものを用いることができる。
本発明の硬化性組成物を用いて、フィルム基材の少なくとも一方の面(表面)にハードコート層を備えるハードコートフィルムを製造することができる。該ハードコートフィルムも本発明の対象であり、該ハードコートフィルムは、例えば、タッチパネル、液晶ディスプレイ等の各種表示素子の表面を保護するために好適に用いられる。
ポリ(オキシパーフルオロアルキレン)基を含む分子鎖の片末端のみにポリ(オキシアルキレン)基と結合したヒドロキシ基を有する数平均分子量が1500乃至3000の原料パーフルオロポリエーテルと、該ヒドロキシ基と反応する官能基及び活性エネルギー線重合性基を有する化合物との反応生成物であるパーフルオロポリエーテル化合物も、本発明の対象である。
装置:(株)エスエムテー製 PM-9050MC
バー:オーエスジーシステムプロダクツ(株)製 A-Bar OSP-30 最大ウエット膜厚30μm(乾燥後膜厚6μm)又は OSP-15 最大ウエット膜厚15μm(乾燥後膜厚3μm)
塗布速度:4m/分
(2)膜厚測定
装置:フィルメトリクス(株)製 F20 膜厚測定システム
(3)オーブン
装置:三基計装(株)製 2層式クリーンオーブン(上下式)PO-250-45-D
(4)UV硬化
装置:ヘレウス(株)製 CV-110QC-G
ランプ:ヘレウス(株)製 無電極ランプH-bulb
(5)耐擦傷性試験及び耐摩耗性試験
装置:新東科学(株)製 往復摩耗試験機 TRIBOGEAR TYPE:30S
走査速度:3200mm/分
走査距離:50mm
(6)接触角測定
装置:協和界面科学(株)製 DropMaster DM-501
測定温度:23℃
(7)動摩擦係数測定
装置:新東科学(株)製 荷重変動型摩擦磨耗試験システム TRIBOGEAR(登
録商標)TYPE:HHS2000
プローブ:0.6mmR サファイアピン
荷重:200g
走査速度:2mm/秒
走査距離:10mm
(8)全光線透過率、ヘーズ測定
装置:日本電色工業(株)製 ヘーズメーターNDH5000
(9)重量平均分子量測定
ゲル浸透クロマトグラフィー(GPC)
装置:東ソー(株)製 HLC-8420GPC
カラム:東ソー(株)製 TSKgelG2000HXL、TSKgelG3000HXL
測定温度:40℃
溶離液:テトラヒドロフラン
検出:RI
(10)燃焼イオンクロマトグラフィー
自動試料燃焼装置システム:日東精工アナリテック(株)(旧(株)三菱ケミカルアナリテック)製 AQF-2100 H
イオンクロマトグラフ:サーモフィッシャーサイエンティフィック(株)製 Dionex Integrion
試料:2mg
吸収液:2.7mM炭酸ナトリウム+0.3mM炭酸水素ナトリウム水溶液
溶離液:2.7mM炭酸ナトリウム+0.3mM炭酸水素ナトリウム水溶液
カラム:サーモフィッシャーサイエンティフィック(株)製 AG-12A/AS-12A
流量:1.5mL/分
検出器:電気伝導度(サプレッサー使用)
標準試料:ふっ化物イオン標準液(F-1000)富士フイルム和光純薬(株)(旧和光純薬工業(株))製
試料中の溶媒にフッ素原子を含む溶媒を含まない場合は、溶媒を含んだ状態のままフッ素濃度を測定し、固形分濃度から溶質のフッ素濃度を換算し、算出した。
多官能アクリレートPA1:ジペンタエリスリトールペンタアクリレート/ヘキサアクリレート混合物[東亞合成(株)製 アロニックス(登録商標)M-403]
多官能アクリレートPA2:オキシエチレン変性多官能アクリレート[第一工業製薬(株)製 ニューフロンティア(登録商標)MF-001]
多官能アクリレートPA3:多官能ウレタンアクリレート[根上工業(株)製 アートレジン(登録商標)UN-3320HS]
多官能アクリレートPA4:ペンタエリスリトールトリアクリレート/ペンタエリスリトールテトラアクリレート[日本化薬(株)製 PET30]
PFPE1:片末端のみにポリ(オキシエチレン)基を介し、ヒドロキシ基を1つ有する下記構造のパーフルオロポリエーテル[ソルベイスペシャルティポリマーズ社製 Fomblin(登録商標)4102X 19F-NMR及び1H-NMRによる分析結果から算出された数平均分子量1900]
PFPE2:片末端のみにポリ(オキシアルキレン)基を介さずヒドロキシ基を1つ有する下記構造のパーフルオロポリエーテル[ソルベイスペシャルティポリマーズ社製 7324X 19F-NMR及び1H-NMRによる分析結果から算出された数平均分子量1750~1950]
PFPE3:片末端のみにポリ(オキシアルキレン)基を介さずヒドロキシ基を1つ有する下記構造のパーフルオロポリエーテル[Apollo Scientific社製 FO2 分子量978.15]
N2:2-アクリロイルオキシエチルイソシアナート[昭和電工(株)製 カレンズ(登録商標)AOI]
N3:2-メタクリロイルオキシエチルイソシアネート[昭和電工(株)製 カレンズ(登録商標)MOI]
DOTDD:ジネオデカン酸ジオクチル錫[日東化成(株)製 ネオスタン(登録商標)U-830]
SMA7:ポリ(オキシパーフルオロアルキレン)基を含む分子鎖の両末端に活性エネルギー線重合性基を合計4つ有するパーフルオロポリエーテル[ソルベイスペシャルティポリマーズ社製 Fluorolink(登録商標)AD-1700、不揮発分70質量%溶液、GPCによるポリスチレン換算で測定される重量平均分子量:Mwは3973、分散度:Mw/Mnは2.1(Mnは数平均分子量)、燃焼イオンクロマトグラフィーにより算出されたパーフルオロポリエーテル化合物中のフッ素原子の含有割合29質量%]
MEK:メチルエチルケトン
PGME:プロピレングリコールモノメチルエーテル
PGMEA:プロピレングリコールモノメチルエーテルアセテート
O2959:2-ヒドロキシ-1-(4-(2-ヒドロキシエトキシ)フェニル)-2-メチルプロパン-1-オン[IGM Resins社製 OMNIRAD(登録商標)2959]
スクリュー管に、PFPE1 3.08g(1.6mmol)、N1 0.39g(1.6mmol)、DOTDD 0.035g(PFPE1及びN1の合計質量の0.01倍量)、及びPGMEA 3.5gを仕込んだ。この混合物を、スターラーチップを用いて室温(およそ23℃)で72時間撹拌して、目的のパーフルオロポリエーテル化合物SMA1の50質量%PGMEA溶液を得た。得られたSMA1のGPCによるポリスチレン換算で測定される重量平均分子量:Mwは1908、分散度:Mw/Mnは1.0であった。また、燃焼イオンクロマトグラフィーにより算出されたSMA1中のフッ素原子の含有割合は47質量%であった。
スクリュー管に、PFPE1 3.23g(1.7mmol)、N2 0.24g(1.7mmol)、DOTDD 0.035g(PFPE1及びN2の合計質量の0.01倍量)、及びPGMEA 3.5gを仕込んだ。この混合物を、スターラーチップを用いて室温(およそ23℃)で72時間撹拌して、目的のパーフルオロポリエーテル化合物SMA2の50質量%PGMEA溶液を得た。得られたSMA2のGPCによるポリスチレン換算で測定される重量平均分子量:Mwは1894、分散度:Mw/Mnは1.1であった。
スクリュー管に、PFPE1 3.20g(1.7mmol)、N3 0.26g(1.7mmol)、DOTDD 0.035g(PFPE1及びN3の合計質量の0.01倍量)、及びPGMEA 3.5gを仕込んだ。この混合物を、スターラーチップを用いて室温(およそ23℃)で72時間撹拌して、目的のパーフルオロポリエーテル化合物SMA3の50質量%PGMEA溶液を得た。得られたSMA3のGPCによるポリスチレン換算で測定される重量平均分子量:Mwは1868、分散度:Mw/Mnは1.1であった。
スクリュー管に、PFPE2 2.20g(1.2mmol)、N1 0.28g(1.2mmol)、DOTDD 0.025g(PFPE2及びN1の合計質量の0.01倍量)、及びMEK 0.6gを仕込んだ。この混合物を、スターラーチップを用いて室温(およそ23℃)で72時間撹拌して、目的のパーフルオロポリエーテル化合物SMA4の80質量%MEK溶液を得た。得られたSMA4のGPCによるポリスチレン換算で測定される重量平均分子量:Mwは1710、分散度:Mw/Mnは1.0であった。また、燃焼イオンクロマトグラフィーにより算出されたSMA4中のフッ素原子の含有割合は63質量%であった。
スクリュー管に、PFPE3 2.78g(2.9mmol)、N1 0.68g(2.9mmol)、DOTDD 0.035g(PFPE3及びN1の合計質量の0.01倍量)、及びPGMEA 3.5gを仕込んだ。この混合物を、スターラーチップを用いて室温(およそ23℃)で72時間撹拌して、目的のパーフルオロポリエーテル化合物SMA5の50質量%PGMEA溶液を得た。得られたSMA5のGPCによるポリスチレン換算で測定される重量平均分子量:Mwは1299、分散度:Mw/Mnは1.0であった。また、燃焼イオンクロマトグラフィーにより算出されたSMA5中のフッ素原子の含有割合は51質量%であり、SMA5の構造から理論的に算出されるフッ素原子の含有割合51質量%と同程度の値を示した。
スクリュー管に、PFPE4 2.41g(4.4mmol)、N1 1.05g(4.4mmol)、DOTDD 0.035g(PFPE4及びN1の合計質量の0.01倍量)、及びPGMEA 3.5gを仕込んだ。この混合物を、スターラーチップを用いて室温(およそ23℃)で72時間撹拌して、目的のパーフルオロポリエーテル化合物SMA6の50質量%PGMEA溶液を得た。得られたSMA6のGPCによるポリスチレン換算で測定される重量平均分子量:Mwは1029、分散度:Mw/Mnは1.0であった。また、燃焼イオンクロマトグラフィーにより算出されたSMA5中のフッ素原子の含有割合は46質量%であり、SMA5の構造から理論的に算出されるフッ素原子の含有割合47質量%と同程度の値を示した。
表1に記載の各成分を混合し、表1に記載の固形分濃度の硬化性組成物を調製した。ここで固形分とは溶媒以外の成分を指す。また、表2中、[部]とは[質量部]を、[%]は[質量%]を表す。なお、表1中の多官能アクリレート及び表面改質剤はそれぞれ固形分を表す。
[組成物均質性]
調製した各硬化性組成物の外観を目視で確認し、以下の基準に従い評価した。
A:透明溶液(浮遊物、沈降物及び相分離何れも無し)
C:浮遊物、沈降物及び相分離のうち何れか有り
[耐擦傷性]
得られたハードコートフィルムのハードコート層表面を、往復摩耗試験機に取り付けたスチールウール[ボンスター(BONSTAR)(登録商標)#0000(超極細)]で1kgの荷重を掛けてストローク50mmで2500往復擦った。その後、前記ストローク50mmの両端5mm幅の範囲を除いた領域内における傷の程度を目視で確認、加えて傷がハードコート層表面であることをマイクロスコープ (キーエンス株式会社)で確認し、以下の基準A、B及びCに従い評価した。なお、ハードコート層として実際の使用を想定した場合、少なくともBであることが求められ、Aであることが望ましい。
A:傷無し(傷0本)
B:傷発生(長さ1mm乃至9mmの傷1本乃至4本)
C:傷発生(長さ1mm乃至9mmの傷5本以上、又は長さ1cm以上の傷1本以上)
[撥水性]
水1μLをハードコート層表面に付着させ、その10秒後の接触角θを5回測定し、その平均値から以下の基準に従い評価した。なお、ハードコート層として実際の使用を想定した場合、少なくともBであることが求められ、Aであることが望ましい。
A:θ≧105°
B:90°≦θ<105°
C:θ<90°
[耐摩耗性]
ハードコート層表面を、往復摩耗試験機に取り付けた円筒形消しゴム[Minoan社製 RUBBER STICK、φ6.0mm]で1kgの荷重を掛けて2,500往復擦った。その擦った部分に水1μLを付着させ、その5秒後の接触角θを5点測定し、その平均値を接触角値とし、以下の基準に従い評価した。なお、ハードコート層として実際の使用を想定した場合、Aであることが望ましい。
A:θ≧90°
B:80°≦θ<90°
C:80°<θ
[滑り性]
ハードコート層表面の5箇所の動摩擦係数μ´を測定し、その平均値から以下の基準に従い評価した。なお、動摩擦係数値は、その値が小さいほど使用プローブとの摩擦が小さいことを示し、滑り性の一目安となる。動摩擦係数値が小さいほど触った際の滑り性が良好となるため、動摩擦係数値が小さいほど好ましい。
A:μ´≦0.035
B:0.035<μ´≦0.050
C:μ´>0.050
[ヘーズ]
参考値として、ハードコート層表面の3箇所のヘーズを測定し、その平均値を算出した。尚、基材として、今回使用したPETフィルム[東レ(株)製 ルミラー(登録商標)U403(別称U40)、厚み100μm]のヘーズは1.6である。
Claims (24)
- (a)(メタ)アクリロイル基を1分子中に2個以上有する活性エネルギー線硬化性多官能モノマー100質量部、
(b)ポリ(オキシパーフルオロアルキレン)基を含む分子鎖の片末端のみに、ポリ(オキシアルキレン)基を介して活性エネルギー線重合性基を有し、且つ重量平均分子量が1500乃至3500のパーフルオロポリエーテル0.05質量部乃至2質量部、及び
(c)活性エネルギー線によりラジカルを発生する重合開始剤1質量部乃至20質量部を含む、硬化性組成物。 - (a)(メタ)アクリロイル基を1分子中に2個以上有する活性エネルギー線硬化性多官能モノマー100質量部、
(b)ポリ(オキシパーフルオロアルキレン)基を含む分子鎖の片末端のみにポリ(オキシアルキレン)基と結合したヒドロキシ基を有する数平均分子量が1500乃至3000の原料パーフルオロポリエーテルと、該ヒドロキシ基と反応する官能基及び活性エネルギー線重合性基を有する化合物との反応生成物であるパーフルオロポリエーテル0.05質量部乃至2質量部、及び
(c)活性エネルギー線によりラジカルを発生する重合開始剤1質量部乃至20質量部を含む、硬化性組成物。 - 前記(b)パーフルオロポリエーテルが、前記ポリ(オキシパーフルオロアルキレン)基を含む分子鎖の片末端のみに、前記ポリ(オキシアルキレン)基を介して前記活性エネルギー線重合性基を有し、且つ重量平均分子量が1500乃至3500である、請求項2に記載の硬化性組成物。
- 前記(b)パーフルオロポリエーテルが、前記ポリ(オキシアルキレン)基と結合したウレタン結合を介して、前記活性エネルギー線重合性基を有する、請求項1乃至請求項3のうち何れか一項に記載の硬化性組成物。
- 前記ポリ(オキシアルキレン)基がポリ(オキシエチレン)基である、請求項1乃至請求項4のうち何れか一項に記載の硬化性組成物。
- 前記ポリ(オキシパーフルオロアルキレン)基が、繰り返し単位-(CF2O)-及び/又は繰り返し単位-(CF2CF2O)-を有し、双方の繰り返し単位を有する場合には、これら繰り返し単位をブロック結合、ランダム結合、又は、ブロック結合及びランダム結合にて結合してなる基である、請求項1乃至請求項5のうち何れか一項に記載の硬化性組成物。
- 前記式[1]中、m及びnはそれぞれ独立して1以上の整数を表す、請求項7に記載の硬化性組成物。
- (d)溶媒をさらに含む、請求項1乃至請求項10のうち何れか一項に記載の硬化性組成物。
- 請求項1乃至請求項11のうち何れか一項に記載の硬化性組成物より得られる硬化膜。
- フィルム基材の少なくとも一方の面にハードコート層を備えるハードコートフィルムであって、該ハードコート層が請求項12に記載の硬化膜からなる、ハードコートフィルム。
- 前記フィルム基材の表面と前記ハードコート層との間にハードコート層の下層を有し、該フィルム基材が樹脂製フィルムである、請求項13に記載のハードコートフィルム。
- 前記ハードコート層が1μm乃至20μmの膜厚を有する、請求項13又は請求項14に記載のハードコートフィルム。
- 請求項1乃至請求項11のうち何れか一項に記載の硬化性組成物をフィルム基材上に塗布し塗膜を形成する工程と、該塗膜に活性エネルギー線を照射し硬化させてハードコート層を形成する工程を含む、ハードコートフィルムの製造方法。
- 請求項11に記載の硬化性組成物をフィルム基材上に塗布し塗膜を形成する工程と、加熱により該塗膜から前記溶媒を除去する工程と、該塗膜に活性エネルギー線を照射し硬化させてハードコート層を形成する工程を含む、ハードコートフィルムの製造方法。
- 前記フィルム基材の表面にハードコート層の下層を形成する工程をさらに含み、該フィルム基材が樹脂製フィルムであって、該ハードコート層の下層上に前記塗膜を形成する、請求項16又は請求項17に記載のハードコートフィルムの製造方法。
- ポリ(オキシパーフルオロアルキレン)基を含む分子鎖の片末端のみに、ポリ(オキシアルキレン)基を介して前記活性エネルギー線重合性基を有し、且つ重量平均分子量が1500乃至3500であるパーフルオロポリエーテル化合物。
- ポリ(オキシパーフルオロアルキレン)基を含む分子鎖の片末端のみにポリ(オキシアルキレン)基と結合したヒドロキシ基を有する数平均分子量が1500乃至3000の原料パーフルオロポリエーテルと、該ヒドロキシ基と反応する官能基及び活性エネルギー線重合性基を有する化合物との反応生成物であるパーフルオロポリエーテル化合物。
- 前記ポリ(オキシパーフルオロアルキレン)基を含む分子鎖の片末端のみに、前記ポリ(オキシアルキレン)基を介して前記活性エネルギー線重合性基を有し、且つ重量平均分子量が1500乃至3500である、請求項20に記載のパーフルオロポリエーテル化合物。
- 前記式[1]中、m及びnはそれぞれ独立して1以上の整数を表す、請求項22に記載のパーフルオロポリエーテル化合物。
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JP2001187796A (ja) * | 1999-12-28 | 2001-07-10 | Hitachi Ltd | 含フッ素化合物、及び磁気ディスク、磁気ディスク装置 |
JP2001209924A (ja) * | 1999-11-19 | 2001-08-03 | Showa Denko Kk | 磁気記録媒体およびその製造方法 |
JP2008040262A (ja) * | 2006-08-08 | 2008-02-21 | Daikin Ind Ltd | 反射防止膜形成用の硬化性組成物 |
JP2013076029A (ja) * | 2011-09-30 | 2013-04-25 | Tdk Corp | ハードコート剤組成物及びこれを用いたハードコートフィルム |
WO2015060458A1 (ja) * | 2013-10-25 | 2015-04-30 | 日産化学工業株式会社 | ヒドロキシ基を有するパーフルオロポリエーテルを含む重合性組成物 |
WO2017200105A1 (ja) * | 2016-05-19 | 2017-11-23 | ダイキン工業株式会社 | フッ素含有共重合体 |
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JP2001209924A (ja) * | 1999-11-19 | 2001-08-03 | Showa Denko Kk | 磁気記録媒体およびその製造方法 |
JP2001187796A (ja) * | 1999-12-28 | 2001-07-10 | Hitachi Ltd | 含フッ素化合物、及び磁気ディスク、磁気ディスク装置 |
JP2008040262A (ja) * | 2006-08-08 | 2008-02-21 | Daikin Ind Ltd | 反射防止膜形成用の硬化性組成物 |
JP2013076029A (ja) * | 2011-09-30 | 2013-04-25 | Tdk Corp | ハードコート剤組成物及びこれを用いたハードコートフィルム |
WO2015060458A1 (ja) * | 2013-10-25 | 2015-04-30 | 日産化学工業株式会社 | ヒドロキシ基を有するパーフルオロポリエーテルを含む重合性組成物 |
WO2017200105A1 (ja) * | 2016-05-19 | 2017-11-23 | ダイキン工業株式会社 | フッ素含有共重合体 |
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