WO2016143435A1 - Agent de réticulation, composition de résine durcissable, film polarisant, procédé de production dudit film polarisant, film optique et dispositif d'affichage d'image - Google Patents

Agent de réticulation, composition de résine durcissable, film polarisant, procédé de production dudit film polarisant, film optique et dispositif d'affichage d'image Download PDF

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Publication number
WO2016143435A1
WO2016143435A1 PCT/JP2016/053516 JP2016053516W WO2016143435A1 WO 2016143435 A1 WO2016143435 A1 WO 2016143435A1 JP 2016053516 W JP2016053516 W JP 2016053516W WO 2016143435 A1 WO2016143435 A1 WO 2016143435A1
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Prior art keywords
group
curable resin
meth
resin composition
polarizer
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PCT/JP2016/053516
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English (en)
Japanese (ja)
Inventor
武士 斉藤
良宏 西谷
池田　哲朗
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日東電工株式会社
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Priority to KR1020177026678A priority Critical patent/KR20170127471A/ko
Priority to CN201680014909.XA priority patent/CN107428996A/zh
Publication of WO2016143435A1 publication Critical patent/WO2016143435A1/fr

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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
    • C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
    • C08F230/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing boron
    • C08F230/065—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing boron the monomer being a polymerisable borane, e.g. dimethyl(vinyl)borane
    • 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
    • C08F220/22—Esters containing halogen
    • 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
    • C08F220/52—Amides or imides
    • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • 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
    • C08F246/00—Copolymers in which the nature of only the monomers in minority is defined
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/55—Boron-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
    • G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 

Definitions

  • the present invention relates to a crosslinking agent and a curable resin composition containing the crosslinking agent.
  • the present invention also relates to a polarizing film comprising a curable resin layer obtained by curing a curable resin composition on at least one surface of a polarizer.
  • the polarizing film can form an image display device such as a liquid crystal display device (LCD), an organic EL display device, a CRT, or a PDP alone or as an optical film obtained by laminating the polarizing film.
  • Active energy ray-curable functional groups such as vinyl groups, (meth) acrylic groups, styryl groups, (meth) acrylamide groups, vinyl ether groups, epoxy groups, oxetane groups, and mercapto groups are industrially useful in various applications. Since it can be polymerized and crosslinked with active energy rays and is excellent in productivity, it is used in all industries such as architecture, electricity, electronics, information, printing, coating, paint, adhesive, and resist.
  • a monomer having an active energy ray-curable functional group is irradiated with active energy rays to obtain a three-dimensionally cross-linked cured product.
  • Examples include a method of crosslinking the oligomer / polymer by irradiating the oligomer / polymer with active energy rays.
  • the compound having an active energy ray-curable group is, for example, a compound having an active energy ray-curable group and a reactive group such as a carboxyl group, acid chloride, isocyanate, or glycidyl group, and a functional group capable of reacting with the reactive group. It is manufactured by the method of making it react with the compound which has this.
  • the conventional method requires a high heating temperature and a long reaction time, and there is a problem in that the active energy ray-curable group causes a runaway reaction or the reaction product is colored.
  • cross-linking polymers include water resistance of water-soluble resins, in particular, polyvinyl alcohol resins having high industrial utility value for polarizing films and adhesives.
  • Examples of industrial applications using crosslinkable groups introduced into polyvinyl alcohol resins include acetoacetyl groups, carbonyl groups, carboxyl groups, acryloyl groups, etc.
  • Patent Document 1 There has been a demand for a method of introducing a crosslinkable group.
  • the present invention has been developed in view of the above circumstances, and is a crosslinking agent capable of crosslinking two different polymers, a crosslinking agent applicable to various uses, and a curable resin containing the crosslinking agent.
  • An object is to provide a composition.
  • the present invention is a polarizing film comprising a curable resin layer obtained by curing the curable resin composition, wherein the adhesive property between the polarizer and the curable resin layer is good, and under a dew condensation environment.
  • Another object is to provide a polarizing film including a curable resin layer having excellent water resistance even under severe conditions such as immersion in water.
  • the curable resin layer is an adhesive layer
  • a transparent protective film is provided on at least one surface of the polarizer via the adhesive layer, the polarizer and the transparent film It aims at providing the polarizing film excellent in adhesiveness with a protective film, and excellent in the water resistance of an adhesive bond layer. Furthermore, it aims at providing the optical film using the said polarizing film, and providing the image display apparatus using the said polarizing film or optical film.
  • the present inventors have found that the above object can be achieved by using a crosslinking agent having a specific structure, and have solved the present invention.
  • the present invention provides the following general formula (1): (However, X contains at least one reactive group selected from the group consisting of vinyl group, (meth) acryl group, styryl group, (meth) acrylamide group, vinyl ether group, epoxy group, oxetane group and mercapto group) A functional group, and R 1 and R 2 each independently represent a hydrogen atom, an optionally substituted aliphatic hydrocarbon group, an aryl group, or a heterocyclic group), About.
  • R 1 and R 2 of the compound represented by the general formula (1) are both hydrogen atoms.
  • the functional group X is represented by the following general formula (2): (Wherein R 3 is a hydrogen atom or a methyl group, and n is an integer of 1 to 4).
  • the functional group X is represented by the following general formula (3): (Wherein R 3 is a hydrogen atom or a methyl group, and m is an integer of 1 to 4).
  • the present invention also relates to a curable resin composition containing the above-described crosslinking agent, the composition comprising 0.01 to 10% by weight of the crosslinking agent relative to the total amount of the composition.
  • the product preferably further contains a compound having a (meth) acryloyl group.
  • the present invention is a polarizing film comprising a curable resin layer obtained by curing a curable resin composition on at least one surface of a polarizer, wherein the curable resin composition is the cured product described above.
  • the polarizing film is characterized in that the curable resin layer is an adhesive layer, and the polarizing film is disposed on at least one surface of the polarizer via the adhesive layer. It is preferable that a transparent protective film is provided.
  • the present invention is characterized in that at least one polarizing film described above is laminated, and the polarizing film described above or the optical film described above is used.
  • the present invention relates to an image display device.
  • the present invention is a method for producing a polarizing film comprising a curable resin layer obtained by curing a curable resin composition on at least one surface of a polarizer
  • the curable resin composition has the following general formula (1): (However, X contains at least one reactive group selected from the group consisting of vinyl group, (meth) acryl group, styryl group, (meth) acrylamide group, vinyl ether group, epoxy group, oxetane group and mercapto group) A functional group, and R 1 and R 2 each independently represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group, or a heterocyclic group which may have a substituent.
  • the present invention relates to a method for producing a polarizing film comprising a curing step of irradiating active energy rays from the polarizer surface side or the coating surface side of the curable resin composition to cure the curable resin composition.
  • the curable resin layer is an adhesive layer
  • the transparent film is provided on at least one surface of the polarizer via the adhesive layer.
  • the crosslinking agent according to the present invention When the crosslinking agent according to the present invention is added to a water-soluble resin such as polyvinyl alcohol, the crosslinking agent has a boric acid group and / or a boric acid ester group in the structure. To form an ester bond.
  • active energy ray-curable functional groups such as (meth) acrylic groups can be easily introduced into water-soluble resins such as polyvinyl alcohol.
  • the active energy ray-curable functional group is polymerized, and a water-soluble resin having excellent water resistance can be obtained.
  • the curable resin layer obtained by curing the curable resin composition containing the crosslinking agent according to the present invention is excellent in adhesiveness with a water-soluble resin film, particularly a polyvinyl alcohol film.
  • a polarizing film in which the curable resin layer is an adhesive layer and a transparent protective film is provided on at least one surface of the polyvinyl alcohol polarizer via the adhesive layer will be described as an example. .
  • the mechanism that causes adhesive peeling between the curable resin layer and the polarizer can be estimated as follows. . First, moisture diffuses into the curable resin layer, and the moisture diffuses to the polarizer interface side.
  • the contribution of hydrogen bonds and / or ionic bonds is large with respect to the adhesive force between the curable resin layer and the polarizer.
  • the hydrogen bond and the ionic bond at are dissociated, and as a result, the adhesive force between the curable resin layer and the polarizer is reduced. As a result, delamination between the curable resin layer and the polarizer may occur in a condensation environment.
  • the adhesive layer is formed by curing the curable resin composition containing the crosslinking agent according to the present invention (crosslinking agent described in the general formula (1)), Since it has an acid group and / or a borate ester group, an ester bond is easily formed particularly with a hydroxyl group of a polyvinyl alcohol polarizer.
  • the crosslinking agent according to the present invention further has a reactive group X, and reacts with other curable components contained in the curable resin composition via the reactive group X. That is, the boric acid group and / or boric acid ester group that the curable resin layer has are firmly bonded to the hydroxyl group that the polarizer has through a covalent bond.
  • the optical durability is good even in a severe humidification environment (for example, 85 ° C. ⁇ 85% RH). Therefore, the polarizing film of the present invention can suppress a decrease (change) in the transmittance and the degree of polarization of the polarizing film even when the polarizing film is placed in the severe humidified environment.
  • the polarizing film of the present invention can suppress a decrease in adhesive force even under a harsh environment such as being immersed in water, and the polarizer and the transparent protective film even under conditions where the contact environment with water is severe It is possible to suppress a decrease in the adhesive strength between the layers (the polarizer and the adhesive layer).
  • the crosslinking agent according to the present invention has the following general formula (1): (However, X contains at least one reactive group selected from the group consisting of vinyl group, (meth) acryl group, styryl group, (meth) acrylamide group, vinyl ether group, epoxy group, oxetane group and mercapto group)
  • R 1 and R 2 each independently represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group, or a heterocyclic group which may have a substituent.
  • Examples of the aliphatic hydrocarbon group include a linear or branched alkyl group which may have a substituent having 1 to 20 carbon atoms, a cyclic alkyl group which may have a substituent having 3 to 20 carbon atoms, carbon
  • Examples of the aryl group include a phenyl group which may have a substituent having 6 to 20 carbon atoms, a naphthyl group which may have a substituent having 10 to 20 carbon atoms, and the like.
  • Examples of the heterocyclic group include, for example, a 5-membered or 6-membered ring group which has at least one hetero atom and may have a substituent. These may be connected to each other to form a ring.
  • R 1 and R 2 are preferably a hydrogen atom or a linear or branched alkyl group having 1 to 3 carbon atoms, and most preferably a hydrogen atom.
  • the functional group X of the compound represented by the general formula (1) includes a reactive group, and examples of the reactive group include a hydroxyl group, an amino group, an aldehyde, a carboxyl group, a vinyl group, a (meth) acryl group, Examples include a styryl group, a (meth) acrylamide group, a vinyl ether group, an epoxy group, and an oxetane group.
  • the reactive group X is a vinyl group, (meth) acryl group, styryl group, (meth) acrylamide group, vinyl ether group, epoxy group.
  • the reactive group X is (meth) acrylic. It is preferably at least one reactive group selected from the group consisting of a group, a styryl group and a (meth) acrylamide group, and when the compound represented by the general formula (1) has a (meth) acrylamide group, Since reactivity is high and a copolymerization rate with an active energy ray curable resin composition increases, it is more preferable.
  • the reactive group X is selected from a hydroxyl group, amino group, aldehyde, carboxyl group, vinyl ether group, epoxy group, oxetane group, and mercapto group. It is preferable to have at least one functional group, particularly when it has an epoxy group, because it is excellent in adhesion between the curable resin layer to be obtained and the adherend, and when it has a vinyl ether group, the curable resin composition is cured. It is preferable because of its excellent properties.
  • the functional group X possessed by the crosslinking agent is represented by the following general formula (2): (Wherein R 3 is a hydrogen atom or a methyl group and n is an integer of 1 to 4), the curability obtained by curing the curable resin composition containing the crosslinking agent
  • the resin layer is excellent in compatibility with a water-soluble resin such as polyvinyl alcohol, can efficiently introduce an active energy ray-curable functional group such as a (meth) acryloyl group into the water-soluble resin, and contains the crosslinking agent.
  • the curable resin layer is disposed so as to be in contact with the water-soluble resin, the adhesiveness is excellent.
  • R 3 is a hydrogen atom or a methyl group, and R 3 is preferably a hydrogen atom because of excellent curability.
  • n is preferably 1 to 4. When n is 5 or more, the compatibility with the water-soluble resin is lowered and it becomes difficult to obtain a crosslinked structure of the water-soluble resin, which is the effect of the present invention, or the distance between cross-linking points is increased, resulting in the effect of water resistance. Since it becomes difficult to obtain, it is not preferable.
  • hydroxyethyl acrylamide and boric acid ester, methylol acrylamide and boric acid ester are particularly suitable.
  • the functional group X which a crosslinking agent has is the following general formula (3): (Wherein R 3 is a hydrogen atom or a methyl group, and m is an integer of 1 to 4), the curable resin composition containing the crosslinking agent is cured as described above.
  • the curable resin layer obtained is excellent in compatibility with a water-soluble resin such as polyvinyl alcohol, and can efficiently introduce an active energy ray-curable functional group such as a (meth) acryloyl group into the water-soluble resin.
  • the curable resin layer containing a crosslinking agent is disposed so as to be in contact with the water-soluble resin, the adhesiveness is excellent.
  • R 3 is a hydrogen atom or a methyl group, and R 3 is preferably a hydrogen atom because of excellent curability.
  • n is preferably 1 to 4.
  • n is 5 or more, the compatibility with the water-soluble resin is lowered and it becomes difficult to obtain a crosslinked structure of the water-soluble resin, which is the effect of the present invention, or the distance between cross-linking points is increased, resulting in the effect of water resistance. Since it becomes difficult to obtain, it is not preferable.
  • hydroxyethyl acrylate and boric acid ester and hydroxybutyl acrylate and boric acid ester are particularly suitable.
  • the resin composition may contain 0.01% by weight or more of the crosslinking agent of the present invention. Preferably, it is contained at 1% by weight or more. Since the boric acid group acts on the surface of the water-soluble resin film in the crosslinking agent of the present invention, it can exhibit the effect of improving the adhesion with a very small addition amount, but the adhesion is too small when the content ratio is too small. It is difficult to obtain the effect of improving the.
  • the upper limit of the crosslinking agent in the curable resin composition can be exemplified by, for example, 80% by weight, preferably 50% by weight or less, more preferably 30% by weight or less, and most preferably 10% by weight or less.
  • the different type reactive crosslinking agent of this invention can also be used independently as an adhesive agent of a water-soluble resin film.
  • the curable resin composition of the present invention preferably contains at least the crosslinking agent represented by the general formula (1) and further contains other curable components.
  • Forms for curing the curable resin composition can be broadly classified into thermal curing and active energy ray curing.
  • the thermosetting resin include polyvinyl alcohol resin, epoxy resin, unsaturated polyester, urethane resin, acrylic resin, urea resin, melamine resin, phenol resin, and the like, and a curing agent is used in combination as necessary.
  • a thermosetting resin a polyvinyl alcohol resin and an epoxy resin can be used more preferably.
  • the active energy ray curable resins can be roughly classified into electron beam curable properties, ultraviolet ray curable properties, and visible light curable properties as classified by active energy rays. Moreover, as a form of hardening, it can be divided into a radical polymerization curable resin composition and a cationic polymerizable resin composition.
  • active energy rays having a wavelength range of 10 nm to less than 380 nm are expressed as ultraviolet rays
  • active energy rays having a wavelength range of 380 nm to 800 nm are expressed as visible rays.
  • the polarizing film according to the present invention it is preferably active energy ray curable as described above. Furthermore, visible light curable using visible light of 380 nm to 450 nm is particularly preferable.
  • Examples of the curable component other than the crosslinking agent represented by the general formula (1) include a radical polymerizable compound used in a radical polymerization curable resin composition.
  • Examples of the radical polymerizable compound include compounds having a radical polymerizable functional group of a carbon-carbon double bond such as a (meth) acryloyl group and a vinyl group.
  • these curable components either a monofunctional radical polymerizable compound or a bifunctional or higher polyfunctional radical polymerizable compound can be used.
  • these radically polymerizable compounds can be used individually by 1 type or in combination of 2 or more types.
  • (meth) acryloyl means an acryloyl group and / or methacryloyl group
  • (meth)” has the same meaning hereinafter.
  • the compound having a (meth) acryloyl group include a (meth) acrylamide derivative having a (meth) acrylamide group and a (meth) acrylate having a (meth) acryloyloxy group.
  • Examples of the compound having a (meth) acryloyl group are shown below, but various compounds can be selected and used without any particular limitation.
  • the content of the radical polymerizable compound is preferably 10% by weight or more.
  • ⁇ Monofunctional radical polymerizable compound As a monofunctional radically polymerizable compound, for example, the following general formula (6): Wherein R 9 is a hydrogen atom or a methyl group, and R 10 and R 11 are each independently a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxyalkyl group or a cyclic ether group, R 10 and R 11 may form a cyclic heterocyclic ring).
  • the number of carbon atoms in the alkyl moiety of the alkyl group, hydroxyalkyl group, and / or alkoxyalkyl group is not particularly limited, and examples thereof include 1 to 4 carbon atoms.
  • examples of the cyclic heterocycle that R 10 and R 11 may form include N-acryloylmorpholine.
  • a compound satisfying both the structure represented by the general formula (1) and the structure represented by the general formula (6) is a compound represented by the general formula (1).
  • Specific examples of the compound represented by the general formula (6) include, for example, N-methyl (meth) acrylamide, N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, N-isopropyl ( N-alkyl group-containing (meth) acrylamide derivatives such as (meth) acrylamide, N-butyl (meth) acrylamide, N-hexyl (meth) acrylamide; N-methylol (meth) acrylamide, N-hydroxyethyl (meth) acrylamide, N -N-hydroxyalkyl group-containing (meth) acrylamide derivatives such as methylol-N-propane (meth) acrylamide; N-alkoxy group-containing (meth) acrylamide derivatives such as N-methoxymethylacrylamide and N-ethoxymethylacrylamide It is done.
  • Examples of the cyclic ether group-containing (meth) acrylamide derivative include a heterocycle-containing (meth) acrylamide derivative in which the nitrogen atom of the (meth) acrylamide group forms a heterocycle, such as N-acryloylmorpholine, N -Acryloylpiperidine, N-methacryloylpiperidine, N-acryloylpyrrolidine and the like.
  • N-hydroxyethylacrylamide and N-acryloylmorpholine are preferably used from the viewpoints of excellent reactivity, a cured product having a high modulus of elasticity, and excellent adhesion to a polarizer. it can.
  • the content of the compound represented by the general formula (6) in the curable resin composition is preferably 1 to 50% by weight, and preferably 3 to 20% by weight. Is more preferable.
  • the content of the compound described in the general formula (6) is too large, the water absorption of the cured product is increased, and the water resistance may be deteriorated.
  • the curable resin composition used in the present invention may contain other monofunctional radically polymerizable compound as a curable component in addition to the compound represented by the general formula (6).
  • the monofunctional radically polymerizable compound include various (meth) acrylic acid derivatives having a (meth) acryloyloxy group.
  • Examples of the (meth) acrylic acid derivative include cycloalkyl (meth) acrylates such as cyclohexyl (meth) acrylate and cyclopentyl (meth) acrylate; aralkyl (meth) acrylates such as benzyl (meth) acrylate; 2-isobornyl (Meth) acrylate, 2-norbornylmethyl (meth) acrylate, 5-norbornen-2-yl-methyl (meth) acrylate, 3-methyl-2-norbornylmethyl (meth) acrylate, dicyclopentenyl (meth) ) Polycyclic (meth) acrylates such as acrylate, dicyclopentenyloxyethyl (meth) acrylate, dicyclopentanyl (meth) acrylate; 2-methoxyethyl (meth) acrylate, 2-ethoxy Ethyl (meth) acrylate Alkoxy groups such as 2-methoxymethoxyeth
  • the resin composition of the present invention When used as an adhesive for a polarizing film, it contains an alkoxy group or a phenoxy group such as phenoxyethyl (meth) acrylate and alkylphenoxypolyethylene glycol (meth) acrylate from the viewpoint of adhesion to a protective film. It is preferable to contain (meth) acrylate.
  • the content is preferably 1% by weight to 30% by weight with respect to the resin composition.
  • Examples of the (meth) acrylic acid derivative include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4- Hydroxyalkyl (meth) acrylates such as hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 8-hydroxyoctyl (meth) acrylate, 10-hydroxydecyl (meth) acrylate, 12-hydroxylauryl (meth) acrylate And [4- (hydroxymethyl) cyclohexyl] methyl acrylate, cyclohexanedimethanol mono (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, and other hydroxy acids Containing (meth) acrylate; glycidyl (meth) acrylate, epoxy group-containing (meth) acrylate such as 4-hydroxybuty
  • examples of the monofunctional radically polymerizable compound include carboxyl group-containing monomers such as (meth) acrylic acid, carboxyethyl acrylate, carboxypentyl acrylate, itaconic acid, maleic acid, fumaric acid, crotonic acid, and isocrotonic acid.
  • carboxyl group-containing monomers such as (meth) acrylic acid, carboxyethyl acrylate, carboxypentyl acrylate, itaconic acid, maleic acid, fumaric acid, crotonic acid, and isocrotonic acid.
  • Examples of the monofunctional radical polymerizable compound include lactam vinyl monomers such as N-vinylpyrrolidone, N-vinyl- ⁇ -caprolactam, and methylvinylpyrrolidone; vinylpyridine, vinylpiperidone, vinylpyrimidine, vinylpiperazine, vinylpyrazine, Examples thereof include vinyl monomers having a nitrogen-containing heterocyclic ring such as vinyl pyrrole, vinyl imidazole, vinyl oxazole, and vinyl morpholine.
  • lactam vinyl monomers such as N-vinylpyrrolidone, N-vinyl- ⁇ -caprolactam, and methylvinylpyrrolidone
  • vinylpyridine vinylpiperidone
  • vinylpyrimidine vinylpiperazine
  • vinylpyrazine examples thereof include vinyl monomers having a nitrogen-containing heterocyclic ring such as vinyl pyrrole, vinyl imidazole, vinyl oxazole, and vinyl morpholine.
  • the resin composition contains a hydroxyl group-containing (meth) acrylate, carboxyl group-containing (meth) acrylate, phosphoric acid group-containing (meth) acrylate or the like having high polarity in the above compound, adhesion to various substrates is improved.
  • the content of the hydroxyl group-containing (meth) acrylate is preferably 1% by weight to 30% by weight with respect to the resin composition.
  • the content of the carboxyl group-containing (meth) acrylate is preferably 1% by weight to 20% by weight with respect to the resin composition.
  • Examples of the phosphoric acid group-containing (meth) acrylate include 2- (meth) acryloyloxyethyl acid phosphate, and the content is 0.1% by weight to 10% by weight with respect to the resin composition. preferable. When there is too much content, since the optical durability of a polarizing film falls, it is unpreferable.
  • a radically polymerizable compound having an active methylene group can be used as the monofunctional radically polymerizable compound.
  • the radical polymerizable compound having an active methylene group is a compound having an active methylene group having an active double bond group such as a (meth) acryl group at the terminal or in the molecule.
  • the active methylene group include an acetoacetyl group, an alkoxymalonyl group, and a cyanoacetyl group.
  • the active methylene group is preferably an acetoacetyl group.
  • radical polymerizable compound having an active methylene group examples include 2-acetoacetoxyethyl (meth) acrylate, 2-acetoacetoxypropyl (meth) acrylate, 2-acetoacetoxy-1-methylethyl (meth) acrylate, and the like.
  • Examples include acrylamide, N- (4-acetoacetoxymethylbenzyl) acrylamide, and N- (2-acetoacetylaminoethyl) acrylamide.
  • the radical polymerizable compound having an active methylene group is preferably acetoacetoxyalkyl (meth) acrylate.
  • Examples of the bifunctional or higher polyfunctional radical polymerizable compound include N, N′-methylenebis (meth) acrylamide, tripropylene glycol di (meth) acrylate, and tetraethylene glycol diester which are polyfunctional (meth) acrylamide derivatives.
  • Radical polymerizable compounds should be used in combination with monofunctional radical polymerizable compounds and polyfunctional radical polymerizable compounds from the viewpoint of achieving both adhesion to polarizers and various transparent protective films and optical durability in harsh environments. Is preferred.
  • a monofunctional radically polymerizable compound has comparatively low liquid viscosity, the liquid viscosity of a resin composition can be reduced by making it contain in a resin composition.
  • monofunctional radically polymerizable compounds often have functional groups that exhibit various functions, and by incorporating them into the resin composition, various functions are expressed in the resin composition and / or the cured product of the resin composition. Can be made.
  • the polyfunctional radical polymerizable compound is preferably contained in the resin composition.
  • the ratio of the monofunctional radical polymerizable compound to the polyfunctional radical polymerizable compound is such that the polyfunctional radical polymerizable compound is mixed in the range of 10 parts by weight to 1000 parts by weight with respect to 100 parts by weight of the monofunctional radical polymerizable compound. Is preferred.
  • the curable resin composition used in the present invention can be used as an active energy ray-curable resin composition when a curable component is used as the active energy ray-curable component.
  • the active energy ray-curable resin composition uses an electron beam or the like as the active energy ray
  • the active energy ray-curable resin composition does not need to contain a photopolymerization initiator.
  • ultraviolet rays or visible rays are used for the lines, it is preferable to contain a photopolymerization initiator.
  • the photopolymerization initiator in the case of using the radical polymerizable compound is appropriately selected depending on the active energy ray.
  • a photopolymerization initiator for ultraviolet light or visible light cleavage is used.
  • photopolymerization initiator examples include benzophenone compounds such as benzyl, benzophenone, benzoylbenzoic acid, 3,3′-dimethyl-4-methoxybenzophenone; 4- (2-hydroxyethoxy) phenyl (2-hydroxy-2 -Propyl) ketone, aromatic ketone compounds such as ⁇ -hydroxy- ⁇ , ⁇ '-dimethylacetophenone, 2-methyl-2-hydroxypropiophenone, ⁇ -hydroxycyclohexyl phenyl ketone; methoxyacetophenone, 2,2-dimethoxy- Acetophenone compounds such as 2-phenylacetophenone, 2,2-diethoxyacetophenone, 2-methyl-1- [4- (methylthio) -phenyl] -2-morpholinopropane-1; benzoin methyl ether; Benzoin ethyl ether, benzoin Benzoin ether compounds such as isopropyl ether, benzoin butyl ether and ani
  • the blending amount of the photopolymerization initiator is 20% by weight or less with respect to the total amount of the curable resin composition.
  • the blending amount of the photopolymerization initiator is preferably 0.01 to 20% by weight, more preferably 0.05 to 10% by weight, and further preferably 0.1 to 5% by weight.
  • a photopolymerization initiator that is particularly sensitive to light of 380 nm or more is used. It is preferable to use it.
  • a photopolymerization initiator that is highly sensitive to light of 380 nm or more will be described later.
  • the compound represented by following General formula (4) (Wherein R 4 and R 5 represent —H, —CH 2 CH 3 , —iPr or Cl, and R 4 and R 5 may be the same or different), either alone or in general formula ( It is preferable to use together the compound represented by 4) and a photopolymerization initiator that is highly sensitive to light of 380 nm or more, which will be described later.
  • the adhesiveness is excellent as compared with a case where a photopolymerization initiator having high sensitivity to light of 380 nm or more is used alone.
  • the composition ratio of the compound represented by the general formula (4) in the curable resin composition is preferably 0.1 to 5% by weight with respect to the total amount of the curable resin composition, 0.5 to It is more preferably 4% by weight, still more preferably 0.9 to 3% by weight.
  • polymerization initiators include triethylamine, diethylamine, N-methyldiethanolamine, ethanolamine, 4-dimethylaminobenzoic acid, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, etc. Among them, ethyl 4-dimethylaminobenzoate is particularly preferable.
  • the amount added is usually 0 to 5% by weight, preferably 0 to 4% by weight, most preferably 0 to 3% by weight, based on the total amount of the curable resin composition. .
  • a known photopolymerization initiator can be used in combination as necessary. Since the transparent protective film having UV absorbing ability does not transmit light of 380 nm or less, it is preferable to use a photopolymerization initiator that is highly sensitive to light of 380 nm or more as the photopolymerization initiator.
  • 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] -1-butanone, 2,4,6-trimethylbenzoyl-diphenyl-phosphine Oxide, bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide, bis ( ⁇ 5-2,4-cyclopentadien-1-yl) -bis (2,6-difluoro-3- (1H-pyrrole) 1-yl) -phenyl) titanium and the like.
  • a photopolymerization initiator in addition to the photopolymerization initiator of the general formula (4), a compound represented by the following general formula (5); (Wherein R 6 , R 7 and R 8 represent —H, —CH 3 , —CH 2 CH 3 , —iPr or Cl, and R 6 , R 7 and R 8 may be the same or different). It is preferable to use it.
  • the compound represented by the general formula (5) commercially available 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one (trade name: IRGACURE907 manufacturer: BASF) is preferable. Can be used.
  • 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1 (trade name: IRGACURE369 manufacturer: BASF)
  • 2- (dimethylamino) -2-[(4-methylphenyl) Methyl] -1- [4- (4-morpholinyl) phenyl] -1-butanone (trade name: IRGACURE379 manufacturer: BASF) is preferred because of its high sensitivity.
  • a radical polymerizable compound having an active methylene group when used as the radical polymerizable compound, it is preferably used in combination with a radical polymerization initiator having a hydrogen abstracting action. According to such a configuration, the adhesiveness of the adhesive layer of the polarizing film is remarkably improved even in a high humidity environment or immediately after being taken out from water (non-dried state). The reason for this is not clear, but the following causes are considered.
  • the radical polymerizable compound having an active methylene group is taken into the main chain and / or side chain of the base polymer in the adhesive layer while polymerizing together with other radical polymerizable compounds constituting the adhesive layer.
  • An agent layer is formed.
  • a radical polymerization initiator having a hydrogen abstracting action is present, a base polymer constituting the adhesive layer is formed, while hydrogen is extracted from the radical polymerizable compound having an active methylene group to form a methylene group. Radicals are generated. And the methylene group which the radical generate
  • the adhesiveness of the adhesive layer of the polarizing film is remarkably improved even in a non-dry state.
  • examples of the radical polymerization initiator having a hydrogen abstracting action include thioxanthone radical polymerization initiators and benzophenone radical polymerization initiators.
  • the radical polymerization initiator is preferably a thioxanthone radical polymerization initiator.
  • examples of the thioxanthone radical polymerization initiator include compounds represented by the above general formula (4).
  • Specific examples of the compound represented by the general formula (4) include thioxanthone, dimethylthioxanthone, diethylthioxanthone, isopropylthioxanthone, chlorothioxanthone, and the like.
  • diethylthioxanthone in which R 1 and R 2 are —CH 2 CH 3 is particularly preferable.
  • the total amount of the curable component is 100% by weight.
  • the radical polymerizable compound having an active methylene group is preferably contained in an amount of 1 to 50% by weight, and the radical polymerization initiator is preferably contained in an amount of 0.1 to 10% by weight based on the total amount of the curable resin composition.
  • a radical is generated in the methylene group of a radical polymerizable compound having an active methylene group in the presence of a radical polymerization initiator having a hydrogen abstraction function, and the methylene group and a polarizer such as PVA are used. React with a hydroxyl group to form a covalent bond. Therefore, in order to generate radicals in the methylene group of the radical polymerizable compound having an active methylene group and to sufficiently form such a covalent bond, when the total amount of the curable component is 100% by weight, the radical having an active methylene group.
  • the content of the polymerizable compound is preferably 1 to 50% by weight, and more preferably 3 to 30% by weight.
  • the radical polymerizable compound having an active methylene group is preferably 1% by weight or more. On the other hand, if it exceeds 50% by weight, the adhesive layer may be poorly cured.
  • the radical polymerization initiator having a hydrogen abstracting action is preferably contained in an amount of 0.1 to 10% by weight, more preferably 0.3 to 9% by weight, based on the total amount of the curable resin composition. preferable. In order to sufficiently advance the hydrogen abstraction reaction, it is preferable to use a radical polymerization initiator in an amount of 0.1% by weight or more. On the other hand, if it exceeds 10% by weight, it may not completely dissolve in the composition.
  • the cationic polymerizable compound used in the cationic polymerization curable resin composition includes a monofunctional cationic polymerizable compound having one cationic polymerizable functional group in the molecule and two or more cationic polymerizable functional groups in the molecule. And having a polyfunctional cationically polymerizable compound. Since the monofunctional cation polymerizable compound has a relatively low liquid viscosity, the liquid viscosity of the resin composition can be reduced by containing it in the resin composition.
  • monofunctional cationically polymerizable compounds often have functional groups that develop various functions, and by incorporating them into the resin composition, various functions are exhibited in the resin composition and / or the cured product of the resin composition. Can be made.
  • the polyfunctional cation polymerizable compound is preferably contained in the resin composition because the cured product of the resin composition can be three-dimensionally crosslinked.
  • the ratio of the monofunctional cation polymerizable compound to the polyfunctional cation polymerizable compound is such that the polyfunctional cation polymerizable compound is mixed in the range of 10 to 1000 parts by weight with respect to 100 parts by weight of the monofunctional cation polymerizable compound. Is preferred.
  • Examples of the cationic polymerizable functional group include an epoxy group, an oxetanyl group, and a vinyl ether group.
  • Examples of the compound having an epoxy group include an aliphatic epoxy compound, an alicyclic epoxy compound, and an aromatic epoxy compound, and the cationic polymerization curable resin composition of the present invention is excellent in curability and adhesiveness. It is particularly preferable to contain an alicyclic epoxy compound.
  • Examples of the alicyclic epoxy compounds include 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate caprolactone-modified products and trimethylcaprolactone-modified products.
  • valerolactone-modified products specifically, Celoxide 2021, Celoxide 2021A, Celoxide 2021P, Celoxide 2081, Celoxide 2083, Celoxide 2085 (above, Daicel Chemical Industries, Ltd., Cyracure UVR-6105, Cyracure UVR) -6107, Cyracure 30, R-6110 (above, manufactured by Dow Chemical Japan Co., Ltd.), etc.
  • the compound having an oxetanyl group is a cationic polymerization compound of the present invention.
  • the compound having an oxetanyl group is preferably contained because it has the effect of improving the curability of the curable resin composition or lowering the liquid viscosity of the composition, such as 3-ethyl-3-hydroxymethyloxetane, 1,4-bis [(3-ethyl-3-oxetanyl) methoxymethyl] benzene, 3-ethyl-3- (phenoxymethyl) oxetane, di [(3-ethyl-3-oxetanyl) methyl] ether, 3-ethyl -3- (2-ethylhexyloxymethyl) oxetane, phenol novolac oxetane, and the like, including Aron Oxetane OXT-101, Aron Oxetane OXT-121, Aron Oxetane OXT-211, Aron Oxetane OXT-221, Aron Oxetane OXT-212 (Above, manufactured
  • 2-hydroxyethyl vinyl ether diethylene glycol monovinyl ether, 4-hydroxybutyl vinyl ether, vinyl ether of diethylene glycol, triethylene glycol divinyl ether, cyclohexanedimethanol divinyl ether, cyclohexanedimethanol monovinyl ether, tricyclodecane vinyl ether, cyclohexyl vinyl ether, methoxy Examples thereof include ethyl vinyl ether, ethoxyethyl vinyl ether, and pentaerythritol type tetravinyl ether.
  • the cationic polymerization curable resin composition contains at least one compound selected from a compound having an epoxy group, a compound having an oxetanyl group, and a compound having a vinyl ether group as described above as a curable component. Therefore, a cationic photopolymerization initiator is blended. This cationic photopolymerization initiator generates a cationic species or a Lewis acid by irradiation with active energy rays such as visible light, ultraviolet rays, X-rays, and electron beams, and starts a polymerization reaction of an epoxy group or an oxetanyl group.
  • the photocationic polymerization initiator a photoacid generator described later is preferably used.
  • a photocationic polymerization initiator that is highly sensitive to light of 380 nm or more. Is generally a compound that exhibits maximum absorption in the vicinity of 300 nm or shorter, and therefore, a photosensitizer that exhibits maximum absorption in light having a wavelength longer than that, specifically, longer than 380 nm should be blended. Thus, it is possible to respond to light having a wavelength in the vicinity and promote generation of cationic species or acid from the photocationic polymerization initiator.
  • the photosensitizer examples include anthracene compounds, pyrene compounds, carbonyl compounds, organic sulfur compounds, persulfides, redox compounds, azo and diazo compounds, halogen compounds, photoreducible dyes, and the like. Two or more types may be mixed and used.
  • anthracene compounds are preferable because of their excellent photosensitization effect, and specific examples include anthracure UVS-1331 and anthracure UVS-1221 (manufactured by Kawasaki Kasei Co., Ltd.).
  • the content of the photosensitizer is preferably 0.1% by weight to 5% by weight, and more preferably 0.5% by weight to 3% by weight.
  • the curable resin composition used in the present invention preferably contains the following components.
  • the active energy ray-curable resin composition used in the present invention can contain an acrylic oligomer obtained by polymerizing a (meth) acrylic monomer, in addition to the curable component related to the radical polymerizable compound.
  • an acrylic oligomer obtained by polymerizing a (meth) acrylic monomer in addition to the curable component related to the radical polymerizable compound.
  • the content of the acrylic oligomer is preferably 20% by weight or less based on the total amount of the curable resin composition. More preferably, it is less than or equal to weight percent.
  • the acrylic oligomer is preferably contained in an amount of 3% by weight or more, more preferably 5% by weight or more based on the total amount of the curable resin composition.
  • the active energy ray-curable resin composition preferably has a low viscosity in consideration of the workability and uniformity during coating. Therefore, an acrylic oligomer obtained by polymerizing a (meth) acrylic monomer also has a low viscosity. Preferably there is.
  • the acrylic oligomer having a low viscosity and capable of preventing curing shrinkage of the adhesive layer preferably has a weight average molecular weight (Mw) of 15000 or less, more preferably 10,000 or less, and particularly preferably 5000 or less. preferable.
  • the weight average molecular weight (Mw) of the acrylic oligomer is preferably 500 or more, more preferably 1000 or more, It is especially preferable that it is 1500 or more.
  • the (meth) acrylic monomer constituting the acrylic oligomer include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, 2-methyl- 2-nitropropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, S-butyl (meth) acrylate, t-butyl (meth) acrylate, n-pentyl (meth) acrylate, t-pentyl (Meth) acrylate, 3-pentyl (meth) acrylate, 2,2-dimethylbutyl (meth) acrylate, n-hexyl (meth) acrylate, cetyl (meth) acrylate, n-octyl (meth) acrylate, 2-ethylhexyl (
  • acrylic oligomer examples include “ARUFON” manufactured by Toagosei Co., Ltd., “Act Flow” manufactured by Soken Chemical Co., Ltd., “JONCRYL” manufactured by BASF Japan.
  • a photoacid generator In the active energy ray-curable resin composition, a photoacid generator can be contained. When the active energy ray-curable resin composition contains a photoacid generator, the water resistance and durability of the adhesive layer can be dramatically improved as compared to the case where no photoacid generator is contained. .
  • the photoacid generator can be represented by the following general formula (7).
  • L + represents any onium cation.
  • X ⁇ represents PF6 6 ⁇ , SbF 6 ⁇ , AsF 6 ⁇ , SbCl 6 ⁇ , BiCl 5 ⁇ , SnCl 6 ⁇ , ClO 4 ⁇ , dithiocarbamate.
  • counter anion X in - are but are not theoretically limited to, non-nucleophilic anion is preferred.
  • the counter anion X ⁇ is a non-nucleophilic anion, a nucleophilic reaction is unlikely to occur in cations coexisting in the molecule and various materials used in combination, and as a result, the photoacid generator itself represented by the general formula (4) It is possible to improve the aging stability of a composition using the same.
  • the non-nucleophilic anion here refers to an anion having a low ability to cause a nucleophilic reaction.
  • Examples of such anions include PF 6 ⁇ , SbF 6 ⁇ , AsF 6 ⁇ , SbCl 6 ⁇ , BiCl 5 ⁇ , SnCl 6 ⁇ , ClO 4 ⁇ , dithiocarbamate anion, SCN ⁇ and the like.
  • the content of the photoacid generator is 10% by weight or less, preferably 0.01 to 10% by weight, and preferably 0.05 to 5% by weight with respect to the total amount of the curable resin composition. Is more preferable, and 0.1 to 3% by weight is particularly preferable.
  • a compound containing either alkoxy group or epoxy group in the active energy ray-curable resin composition, a compound containing a photoacid generator, an alkoxy group, or an epoxy group can be used in the active energy ray-curable resin composition.
  • Compound having epoxy group and polymer When using a compound having one or more epoxy groups in the molecule or a polymer (epoxy resin) having two or more epoxy groups in the molecule, two functional groups having reactivity with the epoxy group are contained in the molecule. Two or more compounds may be used in combination.
  • the functional group having reactivity with an epoxy group include a carboxyl group, a phenolic hydroxyl group, a mercapto group, and a primary or secondary aromatic amino group. It is particularly preferable to have two or more of these functional groups in one molecule in consideration of three-dimensional curability.
  • Examples of the polymer having one or more epoxy groups in the molecule include epoxy resins, bisphenol A type epoxy resins derived from bisphenol A and epichlorohydrin, bisphenol F type epoxy derived from bisphenol F and epichlorohydrin. Resin, bisphenol S type epoxy resin, phenol novolak type epoxy resin, cresol novolak type epoxy resin, bisphenol A novolak type epoxy resin, bisphenol F novolak type epoxy resin, alicyclic epoxy resin, diphenyl ether type epoxy resin, hydroquinone type epoxy resin, Multifunctional epoxy resin such as naphthalene type epoxy resin, biphenyl type epoxy resin, fluorene type epoxy resin, trifunctional type epoxy resin and tetrafunctional type epoxy resin , Glycidyl ester type epoxy resin, glycidyl amine type epoxy resin, hydantoin type epoxy resin, isocyanurate type epoxy resin, aliphatic chain epoxy resin, etc.
  • epoxy resins may be halogenated and hydrogenated It may be.
  • resin products for example, JER Coat 828, 1001, 801N, 806, 807, 152, 604, 630, 871, YX8000, YX8034, YX4000 manufactured by Japan Epoxy Resin Co., Ltd., Epicron manufactured by DIC Corporation 830, EXA835LV, HP4032D, HP820, EP4100 series, EP4000 series, EPU series, manufactured by ADEKA Co., Ltd., Celoxide series (2021, 2021P, 2083, 2085, 3000, etc.) manufactured by Daicel Chemical Co., Ltd., Epolide series, EHPE Series, YD series, YDF series, YDCN series, YDB series, phenoxy resins (polysynthesized from bisphenols and epichlorohydrin) Mud carboxymethyl at both ends with polyether having an epoxy group; and YP series), Nagase Chel Chel Che
  • any compound having one or more alkoxyl groups in the molecule can be used without particular limitation.
  • Representative examples of such compounds include melamine compounds, amino resins, and silane coupling agents.
  • the compounding amount of the compound containing either an alkoxy group or an epoxy group is usually 30% by weight or less based on the total amount of the curable resin composition, and if the content of the compound in the composition is too large, the adhesiveness May decrease, and the impact resistance to the drop test may deteriorate.
  • the content of the compound in the composition is more preferably 20% by weight or less.
  • the compound preferably contains 2% by weight or more, more preferably 5% by weight or more in the composition.
  • ⁇ Silane coupling agent> When the curable resin composition used in the present invention is active energy ray curable, it is preferable to use an active energy ray curable compound as the silane coupling agent. Even if not, the same water resistance can be imparted.
  • silane coupling agents include vinyltrichlorosilane, vinyltrimethoxysilane, vinyltriethoxysilane, 2- (3,4 epoxycyclohexyl) ethyltrimethoxysilane, and 3-glycid as active energy ray-curable compounds.
  • Xylpropyltrimethoxysilane 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, p-styryltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxy Examples thereof include silane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, and 3-acryloxypropyltrimethoxysilane.
  • a silane coupling agent (D1) having an amino group is preferable.
  • the silane coupling agent (D1) having an amino group include ⁇ -aminopropyltrimethoxysilane, ⁇ -aminopropyltriethoxysilane, ⁇ -aminopropyltriisopropoxysilane, ⁇ -aminopropylmethyldimethoxysilane, ⁇ -aminopropylmethyldiethoxysilane, ⁇ - (2-aminoethyl) aminopropyltrimethoxysilane, ⁇ - (2-aminoethyl) aminopropylmethyldimethoxysilane, ⁇ - (2-aminoethyl) aminopropyltriethoxysilane ⁇ - (2-aminoethyl) aminopropylmethyldiethoxysilane, ⁇ - (2-aminoeth
  • the silane coupling agent (D1) having an amino group may be used alone or in combination of two or more.
  • the blending amount of the silane coupling agent is preferably in the range of 0.01 to 20% by weight, preferably 0.05 to 15% by weight, and preferably 0.1 to 10% with respect to the total amount of the curable resin composition. More preferably, it is% by weight. This is because when the blending amount exceeds 20% by weight, the storage stability of the curable resin composition is deteriorated, and when it is less than 0.1% by weight, the effect of adhesion water resistance is not sufficiently exhibited.
  • silane coupling agents that are not active energy ray-curable other than the above include 3-ureidopropyltriethoxysilane, 3-chloropropyltrimethoxysilane, 3-mercaptopropylmethyldimethoxysilane, 3-mercaptopropyltrimethoxy.
  • Examples include silane, bis (triethoxysilylpropyl) tetrasulfide, 3-isocyanatopropyltriethoxysilane, and imidazolesilane.
  • the curable resin composition used in the present invention contains a compound having a vinyl ether group, it is preferable because the adhesion water resistance between the polarizer and the adhesive layer is improved.
  • the reason why such an effect is obtained is not clear, but it is presumed that one of the reasons is that the adhesive force between the polarizer and the adhesive layer is increased by the interaction of the vinyl ether group of the compound with the polarizer.
  • the compound is preferably a radical polymerizable compound having a vinyl ether group.
  • the content of the compound is preferably 0.1 to 19% by weight with respect to the total amount of the curable resin composition.
  • the curable resin composition used in the present invention may contain a compound that causes keto-enol tautomerism.
  • a curable resin composition containing a crosslinking agent or a curable resin composition that can be used by blending a crosslinking agent an embodiment containing a compound that produces the keto-enol tautomerism can be preferably employed.
  • an excessive viscosity increase and gelation of the curable resin composition after blending the organometallic compound and the formation of a microgel product can be suppressed, and the effect of extending the pot life of the composition can be realized.
  • ⁇ -dicarbonyl compounds can be used as the compound that causes keto-enol tautomerism.
  • Specific examples include acetylacetone, 2,4-hexanedione, 3,5-heptanedione, 2-methylhexane-3,5-dione, 6-methylheptane-2,4-dione, 2,6-dimethylheptane- ⁇ -diketones such as 3,5-dione; acetoacetates such as methyl acetoacetate, ethyl acetoacetate, isopropyl acetoacetate, tert-butyl acetoacetate; ethyl propionyl acetate, ethyl propionyl acetate, isopropyl propionyl acetate, propionyl acetate propionyl acetates such as tert-butyl; isobutyryl acetates such as ethyl isobutyryl acetate
  • the amount of the compound that generates keto-enol tautomerism is, for example, 0.05 to 10 parts by weight, preferably 0.2 to 3 parts by weight (for example, 0.3 parts by weight) with respect to 1 part by weight of the organometallic compound. Parts by weight to 2 parts by weight). If the amount of the compound used is less than 0.05 parts by weight relative to 1 part by weight of the organometallic compound, it may be difficult to achieve a sufficient use effect. On the other hand, when the amount of the compound used exceeds 10 parts by weight with respect to 1 part by weight of the organometallic compound, it may be difficult to express the desired water resistance due to excessive interaction with the organometallic compound.
  • additives can be mix
  • additives include epoxy resin, polyamide, polyamideimide, polyurethane, polybutadiene, polychloroprene, polyether, polyester, styrene-butadiene block copolymer, petroleum resin, xylene resin, ketone resin, cellulose resin, fluorine-based oligomer, Polymers or oligomers such as silicone oligomers and polysulfide oligomers; polymerization inhibitors such as phenothiazine and 2,6-di-t-butyl-4-methylphenol; polymerization initiators; leveling agents; wettability improvers; Plasticizers; UV absorbers; inorganic fillers; pigments; dyes and the like.
  • the above-mentioned additives are usually 0 to 10% by weight, preferably 0 to 5% by weight, and most preferably 0 to 3% by weight, based on the total amount of the curable resin composition.
  • the curable resin composition used in the present invention uses a material having low skin irritation as the curable component from the viewpoint of safety.
  • Skin irritation is P.I. I.
  • Judgment can be made with the index I.
  • P. I. I is widely used to indicate the degree of skin injury and is measured by the Draise method. The measured value is displayed in the range of 0 to 8, and it is determined that the irritation is lower as the value is smaller.
  • P. I. I is preferably 4 or less, more preferably 3 or less, and most preferably 2 or less.
  • the curable resin composition of the present invention can be suitably used as an adhesive for producing a polarizing film by laminating a polarizer and a protective film.
  • the polarizing film according to the present invention is formed by laminating a protective film on one or both sides of a polarizer via an adhesive layer.
  • the polarizing film which concerns on this invention has the process of apply
  • cured material layer of a resin composition can also be created by the method of peeling a protective film after performing the said process sequentially.
  • the thickness of the polarizing film is preferably 100 ⁇ m or less, more preferably 50 ⁇ m or less. When the thickness of the polarizing film is too thick, the dimensional change under high temperature and high humidity becomes large, and a problem of display unevenness occurs, which is not preferable.
  • the thickness of the curable resin layer formed of the curable resin composition, particularly the adhesive layer is preferably 0.01 to 3.0 ⁇ m.
  • the thickness of the curable resin layer is more preferably 0.1 to 2.5 ⁇ m, and most preferably 0.5 to 1.5 ⁇ m.
  • the curable resin composition is preferably selected so that the Tg of the curable resin layer formed thereby, particularly the adhesive layer, is 60 ° C. or higher, and more preferably 70 ° C. or higher. More preferably, it is 75 ° C. or higher, more preferably 100 ° C. or higher, and further preferably 1 ⁇ BR> Q 0 ° C. or higher.
  • the Tg of the adhesive layer is preferably 300 ° C. or lower, more preferably 240 ° C. or lower, and further preferably 180 ° C. or lower.
  • Tg ⁇ glass transition temperature> is measured under the following measurement conditions using a TA Instruments dynamic viscoelasticity measuring apparatus RSAIII. Sample size: width 10mm, length 30mm, Clamp distance 20mm, Measurement mode: Tensile, Frequency: 1 Hz, Temperature rising rate: 5 ° C./min Dynamic viscoelasticity was measured and adopted as the temperature Tg of tan ⁇ peak top.
  • the curable resin composition preferably has a storage elastic modulus of the curable resin layer formed by this, particularly the adhesive layer, of 1.0 ⁇ 10 7 Pa or more at 25 ° C. More preferably, it is 10 8 Pa or more.
  • the storage elastic modulus of the pressure-sensitive adhesive layer is 1.0 ⁇ 10 3 Pa to 1.0 ⁇ 10 6 Pa, which is different from the storage elastic modulus of the adhesive layer.
  • the storage elastic modulus of the adhesive layer affects the polarizer cracks when the polarizing film is subjected to a heat cycle (-40 ° C to 80 ° C, etc.). If the storage elastic modulus is low, defects in the polarizer cracks occur. Cheap.
  • the temperature region having a high storage elastic modulus is more preferably 80 ° C.
  • the storage elastic modulus is measured under the same measurement conditions using a dynamic viscoelasticity measuring device RSAIII manufactured by TA Instruments simultaneously with Tg ⁇ glass transition temperature>. The dynamic viscoelasticity was measured and the value of the storage elastic modulus (E ′) was adopted.
  • the polarizing film according to the present invention comprises the following production method:
  • a coating process for coating the curable resin composition containing at least the crosslinking agent according to the present invention on at least one surface of the polarizer, and active energy rays from the polarizer surface side or the coating surface side of the curable resin composition Can be suitably produced by a production method including a curing step of curing the curable resin composition.
  • the moisture content of the polarizer in the bonding step is preferably 8 to 19%.
  • a polarizing film in which a transparent protective film is provided on at least one surface of a polarizer via an adhesive layer is produced by the following production method;
  • Adhesion step of bonding the polarizer and the transparent protective film through the adhesive layer obtained by irradiating the active energy ray from the polarizer surface side or the transparent protective film surface side and curing the curable resin composition Can be manufactured by a manufacturing method including:
  • the polarizer and the transparent protective film may be subjected to surface modification treatment before applying the curable resin composition.
  • the polarizer is preferably subjected to surface modification treatment on the surface of the polarizer before the curable resin composition is applied or bonded.
  • the surface modification treatment include treatment such as corona treatment, plasma treatment, and intro treatment, and corona treatment is particularly preferable.
  • corona treatment By performing the corona treatment, polar functional groups such as a carbonyl group and an amino group are generated on the surface of the polarizer, and adhesion with the curable resin layer is improved.
  • the foreign material on the surface is removed by the ashing effect, or the unevenness on the surface is reduced, so that a polarizing film having excellent appearance characteristics can be created.
  • the method for applying the curable resin composition is appropriately selected depending on the viscosity of the curable resin composition and the desired thickness.
  • a reverse coater for example, a reverse coater, a gravure coater (direct, reverse or offset), a bar reverse coater, or a roll coater. , Die coater, bar coater, rod coater and the like.
  • the viscosity of the curable resin composition used in the present invention is preferably 3 to 100 mPa ⁇ s, more preferably 5 to 50 mPa ⁇ s, and most preferably 10 to 30 mPa ⁇ s.
  • the curable resin composition used in the present invention can be applied by adjusting the viscosity to a preferred range by heating or cooling the composition.
  • a polarizer and a transparent protective film are bonded together through the curable resin composition coated as described above. Bonding of the polarizer and the transparent protective film can be performed with a roll laminator or the like.
  • the curable resin composition used in the present invention is preferably used as an active energy ray-curable resin composition.
  • the active energy ray-curable resin composition can be used in an electron beam curable, ultraviolet curable, or visible light curable mode.
  • the aspect of the curable resin composition is preferably a visible light curable resin composition from the viewpoint of productivity.
  • the active energy ray (electron beam, ultraviolet ray, visible light, etc.) is irradiated to cure the active energy ray curable resin composition.
  • the irradiation direction of active energy rays (electron beam, ultraviolet ray, visible light, etc.) can be irradiated from any appropriate direction. Preferably, it irradiates from the transparent protective film side.
  • the polarizer may be deteriorated by active energy rays (electron beam, ultraviolet ray, visible light, etc.).
  • the acceleration voltage is preferably 5 kV to 300 kV, and more preferably 10 kV to 250 kV. If the acceleration voltage is less than 5 kV, the electron beam may not reach the adhesive and may be insufficiently cured. If the acceleration voltage exceeds 300 kV, the penetration force through the sample is too strong and damages the transparent protective film and the polarizer. There is a risk of giving.
  • the irradiation dose is 5 to 100 kGy, more preferably 10 to 75 kGy.
  • the adhesive becomes insufficiently cured, and when it exceeds 100 kGy, the transparent protective film and the polarizer are damaged, resulting in a decrease in mechanical strength and yellowing, thereby obtaining predetermined optical characteristics. I can't.
  • the electron beam irradiation is usually performed in an inert gas, but if necessary, it may be performed in the atmosphere or under a condition where a little oxygen is introduced. Depending on the material of the transparent protective film, by appropriately introducing oxygen, the transparent protective film surface where the electron beam first hits can be obstructed to prevent oxygen damage and prevent damage to the transparent protective film. An electron beam can be irradiated efficiently.
  • active energy rays containing visible light having a wavelength range of 380 nm to 450 nm particularly active energy rays having the largest irradiation amount of visible light having a wavelength range of 380 nm to 450 nm are used as active energy rays. It is preferable.
  • a transparent protective film ultraviolet non-transparent type transparent protective film
  • ultraviolet absorbing ability in ultraviolet curable property and visible light curable property light having a wavelength shorter than 380 nm is absorbed, so that the wavelength shorter than 380 nm is absorbed.
  • Light does not reach the active energy ray-curable resin composition and does not contribute to the polymerization reaction. Furthermore, light having a wavelength shorter than 380 nm absorbed by the transparent protective film is converted into heat, and the transparent protective film itself generates heat, which causes defects such as curling and wrinkling of the polarizing film. Therefore, when ultraviolet curable and visible light curable are employed in the present invention, it is preferable to use an apparatus that does not emit light having a wavelength shorter than 380 nm as an active energy ray generator, and more specifically, a wavelength range of 380.
  • the ratio of the integrated illuminance of ⁇ 440 nm to the integrated illuminance of the wavelength range of 250 to 370 nm is preferably 100: 0 to 100: 50, and more preferably 100: 0 to 100: 40.
  • a gallium-encapsulated metal halide lamp and an LED light source that emits light in the wavelength range of 380 to 440 nm are preferable.
  • low pressure mercury lamp medium pressure mercury lamp, high pressure mercury lamp, ultra high pressure mercury lamp, incandescent lamp, xenon lamp, halogen lamp, carbon arc lamp, metal halide lamp, fluorescent lamp, tungsten lamp, gallium lamp, excimer laser or sunlight
  • a light source including visible light can be used, and ultraviolet light having a wavelength shorter than 380 nm can be blocked using a band pass filter.
  • a gallium-encapsulated metal halide lamp can be used and light with a wavelength shorter than 380 nm can be blocked. It is preferable to use an active energy ray obtained through a band pass filter or an active energy ray having a wavelength of 405 nm obtained using an LED light source.
  • ultraviolet curable or visible light curable it is preferable to heat the active energy ray-curable resin composition before irradiation with ultraviolet light or visible light (heating before irradiation), in which case the temperature is increased to 40 ° C. or higher. It is preferable to heat to 50 ° C. or higher.
  • the active energy ray-curable resin composition according to the present invention can be suitably used particularly for forming an adhesive layer that adheres a polarizer and a transparent protective film having a light transmittance of a wavelength of 365 nm of less than 5%. is there.
  • the active energy ray-curable resin composition according to the present invention contains the above-described photopolymerization initiator of the general formula (4), so that it is irradiated with ultraviolet rays through a transparent protective film having UV absorption ability.
  • the adhesive layer can be formed by curing. Therefore, an adhesive bond layer can be hardened also in a polarizing film which laminated a transparent protective film which has UV absorption ability on both sides of a polarizer.
  • the adhesive layer can also be cured in a polarizing film in which a transparent protective film having no UV absorbing ability is laminated.
  • the transparent protective film which has UV absorption ability means the transparent protective film whose transmittance
  • Examples of the method for imparting UV absorbing ability to the transparent protective film include a method of containing an ultraviolet absorber in the transparent protective film and a method of laminating a surface treatment layer containing an ultraviolet absorber on the surface of the transparent protective film.
  • ultraviolet absorber examples include conventionally known oxybenzophenone compounds, benzotriazole compounds, salicylic acid ester compounds, benzophenone compounds, cyanoacrylate compounds, nickel complex compounds, triazine compounds, and the like.
  • the active energy ray (electron beam, ultraviolet ray, visible light, etc.) is irradiated to cure the active energy ray curable resin composition to form an adhesive layer.
  • the irradiation direction of active energy rays can be irradiated from any appropriate direction. Preferably, it irradiates from the transparent protective film side.
  • the polarizer may be deteriorated by active energy rays (electron beam, ultraviolet ray, visible light, etc.).
  • the line speed depends on the curing time of the curable resin composition, but is preferably 1 to 500 m / min, more preferably 5 to 300 m / min, and still more preferably 10 ⁇ 100 m / min.
  • the line speed is too low, the productivity is poor, or the damage to the transparent protective film is too great, and a polarizing film that can withstand the durability test cannot be produced.
  • the line speed is too high, the curable resin composition may not be sufficiently cured, and the target adhesiveness may not be obtained.
  • the polarizer and the transparent protective film are bonded via an adhesive layer formed by a cured layer of the active energy ray-curable resin composition.
  • An easy-adhesion layer can be provided between the transparent protective film and the adhesive layer.
  • the easy adhesion layer can be formed of, for example, various resins having a polyester skeleton, a polyether skeleton, a polycarbonate skeleton, a polyurethane skeleton, a silicone-based, a polyamide skeleton, a polyimide skeleton, a polyvinyl alcohol skeleton, and the like. These polymer resins can be used alone or in combination of two or more. Moreover, you may add another additive for formation of an easily bonding layer. Specifically, a stabilizer such as a tackifier, an ultraviolet absorber, an antioxidant, and a heat resistance stabilizer may be used.
  • the easy-adhesion layer is usually provided in advance on a transparent protective film, and the easy-adhesion layer side of the transparent protective film and the polarizer are bonded together with an adhesive layer.
  • the easy-adhesion layer is formed by coating and drying the material for forming the easy-adhesion layer on the transparent protective film by a known technique.
  • the material for forming the easy-adhesion layer is usually adjusted as a solution diluted to an appropriate concentration in consideration of the thickness after drying and the smoothness of coating.
  • the thickness of the easy-adhesion layer after drying is preferably 0.01 to 5 ⁇ m, more preferably 0.02 to 2 ⁇ m, and still more preferably 0.05 to 1 ⁇ m. Note that a plurality of easy-adhesion layers can be provided, but also in this case, the total thickness of the easy-adhesion layers is preferably in the above range.
  • the polarizer is not particularly limited, and various types can be used.
  • the polarizer include hydrophilic polymer films such as polyvinyl alcohol film, partially formalized polyvinyl alcohol film, and ethylene / vinyl acetate copolymer partially saponified film, and two colors such as iodine and dichroic dye.
  • polyene-based oriented films such as those obtained by adsorbing a functional material and uniaxially stretched, polyvinyl alcohol dehydrated products and polyvinyl chloride dehydrochlorinated products.
  • a polarizer composed of a polyvinyl alcohol film and a dichroic material such as iodine is preferable.
  • the thickness of these polarizers is preferably 2 to 30 ⁇ m, more preferably 4 to 20 ⁇ m, and most preferably 5 to 15 ⁇ m.
  • the thickness of the polarizer is thin, the optical durability is not preferable.
  • the thickness of the polarizer is thick, the dimensional change under high temperature and high humidity becomes large, and a problem of display unevenness occurs, which is not preferable.
  • a polarizer obtained by dyeing a polyvinyl alcohol film with iodine and uniaxially stretching it can be produced, for example, by dyeing polyvinyl alcohol in an aqueous iodine solution and stretching it 3 to 7 times the original length. If necessary, it can be immersed in an aqueous solution of boric acid or potassium iodide. Further, if necessary, the polyvinyl alcohol film may be immersed in water and washed before dyeing. In addition to washing the polyvinyl alcohol film surface with dirt and anti-blocking agents by washing the polyvinyl alcohol film with water, it also has the effect of preventing unevenness such as uneven coloring by swelling the polyvinyl alcohol film. is there.
  • Stretching may be performed after dyeing with iodine, may be performed while dyeing, or may be dyed with iodine after stretching.
  • the film can be stretched in an aqueous solution of boric acid or potassium iodide or in a water bath.
  • the active energy ray-curable resin composition used in the present invention has an effect (optical durability in a severe environment under high temperature and high humidity) when a thin polarizer having a thickness of 10 ⁇ m or less is used as the polarizer. Satisfied) can be remarkably expressed.
  • the polarizer having a thickness of 10 ⁇ m or less is relatively more affected by moisture than a polarizer having a thickness exceeding 10 ⁇ m, and has insufficient optical durability in a high-temperature and high-humidity environment, resulting in increased transmittance and degree of polarization. Decline is likely to occur.
  • the polarizer of 10 ⁇ m or less when the polarizer of 10 ⁇ m or less is laminated with the adhesive layer having a bulk water absorption of 10% by weight or less according to the present invention, the movement of water to the polarizer is suppressed in a severe environment of high temperature and high humidity. Thus, deterioration of optical durability such as an increase in transmittance of the polarizing film and a decrease in the degree of polarization can be remarkably suppressed.
  • the thickness of the polarizer is preferably 1 to 7 ⁇ m from the viewpoint of thinning. Such a thin polarizer is preferable in that the thickness unevenness is small, the visibility is excellent, the dimensional change is small, and the thickness of the polarizing film can be reduced.
  • These thin polarizing films can be obtained by a production method including a step of stretching a polyvinyl alcohol-based resin (hereinafter also referred to as PVA-based resin) layer and a stretching resin base material in a laminated state and a step of dyeing.
  • PVA-based resin polyvinyl alcohol-based resin
  • the thin polarizing film among the production methods including the step of stretching in the state of a laminate and the step of dyeing, WO2010 / 100917 pamphlet, PCT / JP 2010/001460 specification, or Japanese Patent Application No. 2010-269002 and Japanese Patent Application No. 2010-263692, the one obtained by a production method including a step of stretching in a boric acid aqueous solution is preferable. What is obtained by the manufacturing method including the process of extending
  • Transparent protective film As the transparent protective film, those excellent in transparency, mechanical strength, thermal stability, moisture barrier property, isotropy and the like are preferable.
  • polyester polymers such as polyethylene terephthalate and polyethylene naphthalate
  • cellulose polymers such as diacetyl cellulose and triacetyl cellulose
  • acrylic polymers such as polymethyl methacrylate
  • styrene such as polystyrene and acrylonitrile / styrene copolymer (AS resin)
  • AS resin acrylonitrile / styrene copolymer
  • polyethylene, polypropylene, polyolefins having a cyclo or norbornene structure polyolefin polymers such as ethylene / propylene copolymers, vinyl chloride polymers, amide polymers such as nylon and aromatic polyamide, imide polymers, sulfone polymers , Polyether sulfone polymer, polyether ether ketone polymer, polyphenylene sulfide polymer, vinyl alcohol polymer, vinylidene chloride polymer, vinyl butyral polymer, arylate polymer, polyoxymethylene polymer, epoxy polymer, or the above
  • the polymer that forms the transparent protective film include polymer blends. One or more kinds of arbitrary appropriate additives may be contained in the transparent protective film.
  • the additive examples include an ultraviolet absorber, an antioxidant, a lubricant, a plasticizer, a mold release agent, an anti-coloring agent, a flame retardant, a nucleating agent, an antistatic agent, a pigment, and a coloring agent.
  • the content of the thermoplastic resin in the transparent protective film is preferably 50 to 100% by weight, more preferably 50 to 99% by weight, still more preferably 60 to 98% by weight, and particularly preferably 70 to 97% by weight. .
  • content of the said thermoplastic resin in a transparent protective film is 50 weight% or less, there exists a possibility that the high transparency etc. which a thermoplastic resin originally has cannot fully be expressed.
  • the transparent protective film examples include a polymer film described in JP-A-2001-343529 (WO01 / 37007), for example, (A) a thermoplastic resin having a substituted and / or unsubstituted imide group in the side chain, and a side film.
  • a thermoplastic resin having a substituted and / or unsubstituted imide group in the side chain examples thereof include a resin composition containing a thermoplastic resin having a substituted and / or unsubstituted phenyl and nitrile group in the chain.
  • Specific examples include a film of a resin composition containing an alternating copolymer composed of isobutylene and N-methylmaleimide and an acrylonitrile / styrene copolymer.
  • the film a film made of a mixed extruded product of the resin composition or the like can be used. Since these films have a small phase difference and a small photoelastic coefficient, problems such as unevenness due to the distortion of the polarizing film can be eliminated, and since the moisture permeability is small, the humidification durability is excellent.
  • moisture permeability of the transparent protective film is not more than 150g / m 2 / 24h. According to such a configuration, it is difficult for moisture in the air to enter the polarizing film, and a change in the moisture content of the polarizing film itself can be suppressed. As a result, the curling and dimensional change of the polarizing film caused by the storage environment can be suppressed.
  • the moisture permeability is 150 g / m 2 /. more preferably not more 24h or less, particularly preferably those following 140 g / m 2 / 24h, more preferably the following 120g / m 2 / 24h.
  • the moisture permeability is determined by the method described in the examples.
  • polyester resins such as polyethylene terephthalate and polyethylene naphthalate
  • polycarbonate resins arylate resins
  • amide resins such as nylon and aromatic polyamide
  • Polyolefin polymers such as ethylene / propylene copolymers, cyclic olefin resins having a cyclo or norbornene structure, (meth) acrylic resins, or a mixture thereof can be used.
  • the resins polycarbonate resins, cyclic polyolefin resins, and (meth) acrylic resins are preferable, and cyclic polyolefin resins and (meth) acrylic resins are particularly preferable.
  • the thickness of the transparent protective film can be determined as appropriate, but is generally preferably 5 to 100 ⁇ m from the viewpoints of workability such as strength and handleability and thin layer properties. 10 to 60 ⁇ m is particularly preferable, and 20 to 40 ⁇ m is more preferable.
  • a roll laminator can be used as a method of bonding the polarizer and the protective film.
  • a method of laminating a protective film on both sides of a polarizer is a method of laminating a polarizer and one protective film and then bonding another protective film, and a method of attaching a polarizer and two protective films simultaneously. It is selected from the method of combining. Clogging bubbles generated when bonding are significantly reduced by adopting the former method, that is, a method of bonding another protective film after bonding a polarizer and one protective film. Is preferable.
  • the method for curing the curable resin composition can be appropriately selected depending on the curing form of the curable resin composition.
  • the curable resin composition is thermosetting, it can be cured by heat treatment.
  • a heat treatment method a conventionally known method such as a hot air oven or an IR oven can be employed.
  • active energy rays such as an electron beam, ultraviolet rays and visible rays.
  • the methods can be appropriately combined and employed.
  • the curable resin composition according to the present invention is preferably active energy ray curable.
  • the curable resin composition of this invention does not contain a volatile solvent substantially. By substantially not containing a volatile solvent, heat treatment becomes unnecessary, which is not only excellent in productivity, but also preferable because it can suppress deterioration of the optical characteristics of the polarizer due to heat.
  • the polarizing film of the present invention can be used as an optical film laminated with another optical layer in practical use.
  • the optical layer is not particularly limited.
  • a liquid crystal display device such as a reflection plate, a semi-transmission plate, a retardation plate (including wavelength plates such as 1/2 and 1/4), and a viewing angle compensation film.
  • One or more optical layers that may be used can be used.
  • a reflective polarizing film or semi-transmissive polarizing film in which a polarizing plate or a semi-transmissive reflecting plate is further laminated on the polarizing film of the present invention an elliptical polarizing film or circularly polarizing film in which a retardation film is further laminated on a polarizing film.
  • a wide viewing angle polarizing film obtained by further laminating a viewing angle compensation film on a film or a polarizing film, or a polarizing film obtained by further laminating a brightness enhancement film on the polarizing film is preferred.
  • An optical film obtained by laminating the above optical layer on a polarizing film can be formed by a method of sequentially laminating separately in the manufacturing process of a liquid crystal display device or the like. It is excellent in stability and assembly work, and has the advantage of improving the manufacturing process of a liquid crystal display device and the like.
  • Appropriate bonding means such as an adhesive layer can be used for lamination.
  • the pressure-sensitive adhesive layer for adhering to other members such as a liquid crystal cell can be provided on the polarizing film described above or an optical film in which at least one polarizing film is laminated.
  • the pressure-sensitive adhesive forming the pressure-sensitive adhesive layer is not particularly limited.
  • an acrylic polymer, silicone-based polymer, polyester, polyurethane, polyamide, polyether, fluorine-based or rubber-based polymer is appropriately selected.
  • those having excellent optical transparency such as an acrylic pressure-sensitive adhesive, exhibiting appropriate wettability, cohesiveness, and adhesive pressure-sensitive adhesive properties, and being excellent in weather resistance, heat resistance and the like can be preferably used.
  • the adhesive layer can be provided on one side or both sides of a polarizing film or an optical film as a superimposed layer of different compositions or types. Moreover, when providing in both surfaces, it can also be set as adhesive layers, such as a different composition, a kind, and thickness, in the front and back of a polarizing film or an optical film.
  • the thickness of the pressure-sensitive adhesive layer can be appropriately determined according to the purpose of use and adhesive force, and is generally 1 to 500 ⁇ m, preferably 1 to 200 ⁇ m, and particularly preferably 1 to 100 ⁇ m.
  • the exposed surface of the adhesive layer is temporarily covered with a separator for the purpose of preventing contamination until it is put to practical use. Thereby, it can prevent contacting an adhesion layer in the usual handling state.
  • a separator for example, an appropriate thin leaf body such as a plastic film, rubber sheet, paper, cloth, non-woven fabric, net, foamed sheet, metal foil, or a laminate thereof, and a silicone-based or long sheet as necessary.
  • an appropriate release agent such as a chain alkyl type, fluorine type or molybdenum sulfide, can be used.
  • the polarizing film or the optical film of the present invention can be preferably used for forming various devices such as a liquid crystal display device.
  • the liquid crystal display device can be formed according to the conventional method. That is, a liquid crystal display device is generally formed by appropriately assembling components such as a liquid crystal cell, a polarizing film or an optical film, and an illumination system as necessary, and incorporating a drive circuit. There is no limitation in particular except the point which uses the polarizing film or optical film by invention, and it can apply according to the former.
  • the liquid crystal cell any type such as a TN type, an STN type, or a ⁇ type can be used.
  • liquid crystal display devices such as a liquid crystal display device in which a polarizing film or an optical film is disposed on one side or both sides of a liquid crystal cell, or a backlight or a reflector used in an illumination system can be formed.
  • the polarizing film or optical film by this invention can be installed in the one side or both sides of a liquid crystal cell.
  • polarizing film or an optical film on both sides they may be the same or different.
  • liquid crystal display device for example, a single layer or a suitable layer such as a diffusing plate, an antiglare layer, an antireflection film, a protective plate, a prism array, a lens array sheet, a light diffusing plate, a backlight, etc. Two or more layers can be arranged.
  • the obtained active energy ray-curable polyvinyl alcohol aqueous solution was cast on a glass plate and then heated at 120 ° C. for 2 hours to obtain an active energy ray-curable polyvinyl alcohol film having a thickness of 100 ⁇ m. Then, the active energy ray was irradiated and the crosslinked polyvinyl alcohol film was obtained.
  • Example 1 The state after the polyvinyl alcohol obtained in Production Example 1 was immersed in warm water at 60 ° C. for 6 hours was observed. The polyvinyl alcohol film swelled but kept the film shape.
  • Example 2 The polyvinyl alcohol obtained in Production Example 2 was immersed in warm water at 60 ° C. for 6 hours. Although the polyvinyl alcohol film obtained in Production Example 2 swelled, the film shape was maintained.
  • Protective film A 100 parts by weight of imidized MS resin described in Production Example 1 of JP-A-2010-284840 and 0.62 parts by weight of a triazine-based ultraviolet absorber (trade name: T-712 manufactured by Adeka) It mixed at 220 degreeC with the biaxial kneader, and produced the resin pellet.
  • the obtained resin pellets were dried at 100.5 kPa and 100 ° C. for 12 hours, extruded from a T-die at a die temperature of 270 ° C. with a single screw extruder, and formed into a film (thickness: 160 ⁇ m). Further, the film is stretched in the conveyance direction in a 150 ° C.
  • a transparent protective film a having a thickness of 40 [mu] m (moisture permeability 58g / m 2 / 24h).
  • Protection Film B a cyclic polyolefin film having a thickness of 55 .mu.m: was used after subjected to a corona treatment (manufactured by Zeon Corporation ZEONOR, moisture permeability 11g / m 2 / 24h).
  • the moisture permeability was measured according to a moisture permeability test (cup method) of JIS Z0208.
  • a sample cut to a diameter of 60 mm was set in a moisture permeable cup containing about 15 g of calcium chloride, and the temperature was 40 ° C. and the humidity was 90% R.D. H.
  • active energy rays As an active energy ray, visible light (gallium filled metal halide lamp) Irradiation device: Fusion UV Systems, Inc. Light HAMMER10 bulb: V bulb Peak illuminance: 1600 mW / cm 2 , integrated irradiation amount 1000 / mJ / cm 2 (wavelength 380 ⁇ 440 nm) was used. The illuminance of visible light was measured using a Sola-Check system manufactured by Solatell.
  • ⁇ Curable resin composition> In accordance with the formulation table shown in Table 1, the components were mixed and stirred for 1 hour to obtain active energy ray-curable adhesive resin compositions according to Examples 3 to 6 and Comparative Examples 2 to 3.
  • ⁇ Polarizing film> The curable adhesive composition according to Examples 1 and 2 or Comparative Example 1 is applied to the bonding surface of the protective film A and the protective film B with an MCD coater (manufactured by Fuji Machinery Co., Ltd.) (cell shape: honeycomb, gravure roll wire). (Number: 1000 / inch, rotational speed 140% / vs. Line speed) was applied to a thickness of 0.7 ⁇ m, and was bonded to both sides of the polarizer with a roll machine.
  • MCD coater manufactured by Fuji Machinery Co., Ltd.
  • Number 1000 / inch, rotational speed 140% / vs. Line speed
  • ⁇ Adhesive strength> The polarizing film obtained in each example was cut out to a size of 200 mm parallel to the stretching direction of the polarizer and 20 mm in the perpendicular direction, and a slit was cut between the transparent protective film and the polarizer with a cutter knife. Laminated to the board. Using Tensilon, the transparent protective film and the polarizer were peeled in the 90-degree direction at a peeling speed of 10 m / min, and the peel strength was measured. Moreover, the infrared absorption spectrum of the peeling surface after peeling was measured by ATR method, and the peeling interface was evaluated based on the following reference
  • A Cohesive failure of transparent protective film
  • B Interfacial peeling between transparent protective film / adhesive layer
  • C Interfacial peeling between adhesive layer / polarizer
  • D Cohesive failure of polarizer
  • a and D are adhesive strengths Is greater than the cohesive strength of the film, which means that the adhesive strength is very excellent.
  • B and C mean that the adhesive force at the transparent protective film / adhesive layer (adhesive layer / polarizer) interface is insufficient (adhesive strength is poor).
  • the adhesive strength in the case of A or D is ⁇
  • a ⁇ B cohesive failure of transparent protective film” and “interfacial peeling between transparent protective film / adhesive layer” occur simultaneously
  • a -Adhesive strength in the case of C cohesive failure of transparent protective film” and “interfacial peeling between adhesive layer / polarizer” occur simultaneously
  • adhesive strength in the case of B or C as x To do is ⁇
  • ⁇ Hot water immersion test> The polarizing film obtained in each example was cut into a rectangle of 50 mm in the stretching direction of the polarizer and 25 mm in the vertical direction. This polarizing film was immersed in warm water at 60 ° C. for 6 hours, and then the peeled length was visually measured with a magnifier. The measurement was taken as the maximum value of the vertical distance from the cross section of the part where peeling occurred (mm). If the peeled length was within 5 mm, it was evaluated that there was no problem in actual use.
  • ⁇ Hot water immersion peel test> The polarizing film obtained in each example was cut into a size of 200 mm in parallel with the stretching direction of the polarizer and 20 mm in the orthogonal direction.
  • the polarizing film was immersed in warm water at 60 ° C. for 6 hours, taken out, wiped with a dry cloth, cut with a cutter knife between the protective film and the polarizer, and the polarizing film was bonded to a glass plate.
  • the evaluation was carried out within 1 minute after taking out from the pure water. Thereafter, the same evaluation as in the above ⁇ Adhesive strength> was performed.
  • the amount of change ⁇ P in polarization degree is preferably less than 3.0%, more preferably 1.0% or less, and further preferably 0.5% or less.
  • the degree of polarization P is the transmittance when two identical polarizing plates are stacked so that their transmission axes are parallel (parallel transmittance: Tp), and the two polarizing axes are stacked so that their transmission axes are orthogonal to each other. It is calculated
  • Polarization degree P (%) ⁇ (Tp ⁇ Tc) / (Tp + Tc) ⁇ 1/2 ⁇ 100
  • Light acrylate DCP-A Polymerization initiator: IRGACURE 907 (manufactured by BASF); : KAYACURE DETX-S (manufactured by Nippon Kayaku Co., Ltd.); Indicates.

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Abstract

La présente invention concerne un agent de réticulation qui est représenté par la formule générale (1). (Dans la formule, X représente un groupe fonctionnel qui contient au moins un groupe réactif choisi dans le groupe constitué par un groupe vinyle, un groupe (méth)acryle, un groupe styryle, un groupe (méth)acrylamide, un groupe éther vinylique, un groupe époxy, un groupe oxétane et un groupe mercapto ; et R1 et R2 représentent chacun indépendamment un atome d'hydrogène, ou un groupe hydrocarbure aliphatique, un groupe aryle ou un groupe hétérocyclique éventuellement substitué).
PCT/JP2016/053516 2015-03-12 2016-02-05 Agent de réticulation, composition de résine durcissable, film polarisant, procédé de production dudit film polarisant, film optique et dispositif d'affichage d'image WO2016143435A1 (fr)

Priority Applications (2)

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KR1020177026678A KR20170127471A (ko) 2015-03-12 2016-02-05 가교제 및 경화성 수지 조성물, 편광 필름 및 그 제조 방법, 광학 필름 그리고 화상 표시 장치
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CN112444906A (zh) * 2019-09-04 2021-03-05 日东电工株式会社 偏振膜的制造方法
CN114302924A (zh) * 2019-08-29 2022-04-08 日东电工株式会社 偏光件保护用树脂组合物及具备由该组合物形成的保护层的偏光板
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WO2018003662A1 (fr) * 2016-06-27 2018-01-04 富士フイルム株式会社 Copolymère et composition
WO2018003664A1 (fr) * 2016-06-27 2018-01-04 富士フイルム株式会社 Film fonctionnel, plaque de polarisation et dispositif d'affichage
JP6740144B2 (ja) 2016-06-27 2020-08-12 富士フイルム株式会社 共重合体、及び組成物
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CN114616298A (zh) * 2019-10-30 2022-06-10 日东电工株式会社 偏光件保护用树脂组合物及具备由该组合物形成的保护层的偏光板

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