WO2015141382A1 - Composition d'adhésif pour plaque de polarisation, couche adhésive, feuille adhésive, et plaque de polarisation avec couche adhésive - Google Patents

Composition d'adhésif pour plaque de polarisation, couche adhésive, feuille adhésive, et plaque de polarisation avec couche adhésive Download PDF

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Publication number
WO2015141382A1
WO2015141382A1 PCT/JP2015/054777 JP2015054777W WO2015141382A1 WO 2015141382 A1 WO2015141382 A1 WO 2015141382A1 JP 2015054777 W JP2015054777 W JP 2015054777W WO 2015141382 A1 WO2015141382 A1 WO 2015141382A1
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Prior art keywords
sensitive adhesive
pressure
meth
polarizing plate
mass
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PCT/JP2015/054777
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English (en)
Japanese (ja)
Inventor
佐知 室井
雄太 紺野
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綜研化学株式会社
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Priority to CN201580014225.5A priority Critical patent/CN106164718A/zh
Priority to JP2016508614A priority patent/JPWO2015141382A1/ja
Priority to KR1020167025371A priority patent/KR20160134681A/ko
Publication of WO2015141382A1 publication Critical patent/WO2015141382A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
    • C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
    • C08G18/6225—Polymers of esters of acrylic or methacrylic acid
    • C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
    • C08G18/625—Polymers of alpha-beta ethylenically unsaturated carboxylic acids; hydrolyzed polymers of esters of these acids
    • C08G18/6254—Polymers of alpha-beta ethylenically unsaturated carboxylic acids and of esters of these acids containing hydroxy groups
    • 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
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0025—Crosslinking or vulcanising agents; including accelerators
    • 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
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • 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
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • 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
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • 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
    • C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
    • 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
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • 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 
    • G02F1/13—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  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors

Definitions

  • the present invention relates to a pressure-sensitive adhesive composition for polarizing plates.
  • the liquid crystal cell has a structure in which a liquid crystal layer is sandwiched between two substrates (eg, a glass plate), and a polarizing plate is attached to the surface of the substrate via an adhesive layer.
  • a polarizing plate is likely to be thermally contracted in a high temperature and high humidity environment, so that it lacks dimensional stability and may cause warpage in a liquid crystal cell.
  • the thinning of liquid crystal cells eg, thinning of the substrate constituting the liquid crystal cell
  • the thinning of the polarizing plate the warpage of the liquid crystal cell under a high temperature and high humidity environment has become a larger problem.
  • the pressure-sensitive adhesive layer cannot follow the thermal contraction (dimensional change) of the polarizing plate, and the stress relaxation property of the pressure-sensitive adhesive layer is low.
  • a pressure-sensitive adhesive layer is prepared by subjecting a pressure-sensitive adhesive for an optical film containing a specific (meth) acrylic polymer, a peroxide and an isocyanate compound to a crosslinking reaction.
  • a method of forming is disclosed.
  • a cross-linking method using a thermal decomposition cross-linking reaction with a peroxide and a cross-linking method using a urethane bond formation with an isocyanate-based compound are used in combination, so that stress associated with dimensional change of an optical film can be reduced.
  • high durability can be maintained while maintaining sufficient stress relaxation characteristics.
  • Patent Document 2 polymerizes (meth) acrylic monomer, macromonomer, and (meth) acrylate monomer having a crosslinkable functional group for reworkability and durability under high temperature and high humidity conditions.
  • An adhesive composition containing a (meth) acrylic polymer and a curing agent having a functional group that reacts with the crosslinkable functional group and having a gel fraction of 55% to 80% is disclosed. .
  • Patent Document 2 does not describe the suppression of warpage of the liquid crystal cell, and since the gel fraction of the pressure-sensitive adhesive layer is relatively high, it is presumed that the stress relaxation property is also low.
  • the subject of this invention is the adhesive composition for polarizing plates which can suppress the curvature (bending) of a liquid crystal cell, and can form the adhesive layer excellent in durability,
  • the adhesive formed from the said composition It is providing the polarizing plate with an adhesive layer which has a layer, the adhesive sheet for polarizing plates which has the said adhesive layer, and the said adhesive layer.
  • the present inventors diligently studied to solve the above problems. As a result, a (meth) acrylic copolymer having a degree of branching in a specific range obtained by copolymerizing a (meth) acrylic acid alkyl ester having an alkyl group with 4 to 18 carbon atoms and a polymerizable macromonomer is obtained. It has been found that, when used, it is possible to form a pressure-sensitive adhesive layer that is capable of suppressing warping (bending) of the liquid crystal cell and having excellent durability while having a low gel fraction. That is, the present inventors have found that the above problems can be solved by using a polarizing plate pressure-sensitive adhesive composition having the following specific configuration, and have completed the present invention.
  • the present invention includes, for example, the following [1] to [10].
  • GPC-MALS angle laser light scattering detector
  • the (meth) acrylic copolymer (A) is a copolymer obtained by copolymerizing a polar group-containing monomer together with the (meth) acrylic acid alkyl ester and a polymerizable macromonomer.
  • the weight average molecular weight (Mw) measured by the gel permeation chromatography method (GPC method) of the (meth) acrylic copolymer (A) is 200,000 to 1,500,000.
  • the adhesive composition for polarizing plates according to any one of to [3].
  • the content of the crosslinking agent (B) is 5 parts by mass or less with respect to 100 parts by mass of the (meth) acrylic copolymer (A), according to the above [5] or [6].
  • a pressure-sensitive adhesive for polarizing plates which is formed from the pressure-sensitive adhesive composition for polarizing plates according to any one of [1] to [7], and has a gel fraction of 30% by mass or less. layer.
  • a pressure-sensitive adhesive sheet for polarizing plates comprising the pressure-sensitive adhesive layer according to [8].
  • a polarizing plate with an adhesive layer characterized by having the polarizing plate and the adhesive layer described in [8] on at least one surface of the polarizing plate.
  • the adhesive composition for polarizing plates which can suppress the curvature (bending) of a liquid crystal cell and can form the adhesive layer excellent in durability
  • the adhesive formed from the said composition A polarizing plate having a pressure-sensitive adhesive layer, a pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer, and a pressure-sensitive adhesive layer-attached polarizing plate having the pressure-sensitive adhesive layer can be provided.
  • the pressure-sensitive adhesive composition for polarizing plate is also simply referred to as “pressure-sensitive adhesive composition”
  • the pressure-sensitive adhesive layer for polarizing plates of the present invention is also simply referred to as “pressure-sensitive adhesive layer”.
  • the sheet is also simply referred to as “adhesive sheet”.
  • the pressure-sensitive adhesive composition for polarizing plates of the present invention contains a (meth) acrylic copolymer (A).
  • the pressure-sensitive adhesive composition preferably further contains a cross-linking agent (B), and if necessary, at least selected from a silane coupling agent (C), an antistatic agent (D), and an organic solvent (E). You may contain 1 type.
  • the pressure-sensitive adhesive formed from the pressure-sensitive adhesive composition for polarizing plates of the present invention has a gel fraction of 30% by mass or less, preferably 0 to 25% by mass, more preferably 0 to 20% by mass. Even if the gel fraction is within the above range, the copolymer (A) is obtained because the (meth) acrylic copolymer (A) has a highly branched chain derived from the polymerizable macromonomer as described later. The branched chains can be appropriately entangled with each other, and the durability and workability of the pressure-sensitive adhesive layer are not deteriorated.
  • the pressure-sensitive adhesive layer may not be able to sufficiently absorb or relax the stress caused by the dimensional change of the polarizing plate under a high temperature / high humidity heat environment.
  • the said gel fraction is a value measured about the adhesive extract
  • the (meth) acrylic copolymer (A) is a copolymer obtained by copolymerizing a copolymer component containing a (meth) acrylic acid alkyl ester having an alkyl group having 4 to 18 carbon atoms and a polymerizable macromonomer. It is a coalescence.
  • a copolymerization component of the copolymer (A) at least one selected from polar group-containing monomers and other monomers other than these may be further used.
  • acrylic and methacryl are collectively referred to as “(meth) acryl”.
  • structural unit derived from a certain monomer a contained in the polymer is also referred to as “monomer a unit”.
  • the (meth) acrylic copolymer (A) has a degree of branching of 0.55 or less, preferably 0 as measured by gel permeation chromatography / multi-angle laser light scattering detector (GPC-MALS). .10 to 0.54, more preferably 0.20 to 0.53, and particularly preferably 0.30 to 0.53. Details of measurement conditions for the degree of branching are described in the examples.
  • the degree of branching is an index indicating a branched polymer when it is 0.55 or less and a linear polymer when it exceeds 0.55.
  • a branched polymer when the degree of branching is small, it indicates that the polymer molecule has many branches and has a high degree of branching, and when the degree of branching is large, the polymer molecule has little branching and low degree of branching. It shows having.
  • the (meth) acrylic copolymer (A) having a degree of branching in the above range (1) is often entangled due to the branched chain between polymer molecules at about room temperature, resulting in the molecular weight of the polymer and the pressure-sensitive adhesive.
  • Adhesive layer with excellent storability such as adhesive properties, processability such as punching out the adhesive layer, and less deformation and protrusion of the adhesive layer, even in designs with a low gel fraction of the layer (2)
  • a high temperature eg, 60 ° C.
  • the entanglement between the polymer molecules is partially relaxed, so that the pressure-sensitive adhesive layer exhibits excellent flexibility, and is excellent in suppressing warping (bending) of the polarizing plate, Due to the remaining entanglement, the pressure-sensitive adhesive layer exhibits excellent durability.
  • the reason why the warpage of the polarizing plate is suppressed is as follows.
  • a case where a glass plate is used as the adherend will be described as an example.
  • the polarizing plate and the glass plate have different heat shrinkage rates, and the polarizing plate usually has a larger heat shrinkage rate (dimensional change) than the glass plate.
  • the pressure-sensitive adhesive layer lacks flexibility under a high-temperature, high-humidity heat environment, the pressure-sensitive adhesive layer cannot follow the dimensional change of the polarizing plate, and the pressure-sensitive adhesive layer cannot relieve stress. Stress concentrates on the glass plate, which causes warpage of the glass plate.
  • the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition of the present invention contains a highly branched polymer, and the entanglement partly loosens in a high temperature / high humidity environment. Can follow. Therefore, no stress is generated and the stress is not concentrated on the glass plate. Further, the polarizing plate can also be thermally contracted uniformly without anisotropy, and does not induce birefringence of the polarizing plate. As described above, in the present invention, the pressure-sensitive adhesive layer can absorb and relieve the stress accompanying the dimensional change of the polarizing plate, and therefore, no excessive stress (load) is applied to the glass plate. It is presumed that this will lead to suppression of warpage of the plate.
  • the pressure-sensitive adhesive composition of the present invention has the above properties, it is suitable for use in bonding a substrate constituting a liquid crystal cell and a polarizing plate.
  • the thickness of the glass plate constituting the thinned liquid crystal cell is as small as about 0.10 to 1.0 mm, it is suitable for the purpose of bonding the substrate and the polarizing plate.
  • (Meth) acrylic acid alkyl ester As the (meth) acrylic acid alkyl ester, a (meth) acrylic acid alkyl ester having an alkyl group having 4 to 18 carbon atoms (CH 2 ⁇ CR 1 —COOR 2 ; R 1 is a hydrogen atom or a methyl group, R 2 Is an alkyl group having 4 to 18 carbon atoms), and the alkyl group preferably has 4 to 12 carbon atoms.
  • Examples of the (meth) acrylic acid alkyl ester having 4 to 18 carbon atoms in the alkyl group include, for example, n-butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, pentyl (meth) acrylate, Hexyl (meth) acrylate, heptyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, undeca (meth) acrylate, Examples include lauryl (meth) acrylate, stearyl (meth) acrylate, and isostearyl (meth) acrylate. These may be used alone or in combination of two or more.
  • the total amount of (meth) acrylic acid alkyl ester having 4 to 18 carbon atoms in the alkyl group is good adhesive strength and durability. From the standpoint of expression, it is preferably 99.7 to 20% by mass, more preferably 99.4 to 30% by mass, and still more preferably 98.7 to 50% by mass.
  • a (meth) acrylic acid alkyl ester having an alkyl group having 1 to 3 carbon atoms (CH 2 ⁇ CR 3 —COOR 4 ;
  • R 3 is a hydrogen atom or It is also possible to use a methyl group and R 4 is an alkyl group having 1 to 3 carbon atoms.
  • Examples of the (meth) acrylic acid alkyl ester having 1 to 3 carbon atoms in the alkyl group include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, and isopropyl (meth) acrylate. . These may be used alone or in combination of two or more.
  • the amount of (meth) acrylic acid alkyl ester having 1 to 3 carbon atoms in the alkyl group is preferably 60% by mass or less, more preferably 50% by mass in 100% by mass of the copolymer component from the viewpoint of stress relaxation characteristics. Or less, more preferably 40% by mass or less.
  • the polymerizable macromonomer is a monomer having a high molecular weight having a polymerizable unsaturated group copolymerizable with the above (meth) acrylic acid alkyl ester.
  • the polymer chain (main chain) portion constituting the polymerizable macromonomer is not particularly limited as long as it has a polymerizable unsaturated group copolymerizable with the above (meth) acrylic acid alkyl ester.
  • a repeating structural unit derived from at least one selected from alkyl acrylate, styrene and acrylonitrile is a main component
  • a repeating structural unit derived from (meth) acrylic acid alkyl ester is a main component.
  • the main component means a content exceeding 50% by mass with respect to the total repeating unit amount.
  • the polymer chain part is derived from (meth) acrylic acid alkyl ester having 1 to 8 carbon atoms in the alkyl group.
  • a polymer chain mainly composed of repeating structural units is particularly preferred.
  • the (meth) acrylic acid alkyl ester include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, and tert-butyl (meth) acrylate.
  • the content of (meth) acrylic acid alkyl ester unit having 1 to 8 carbon atoms in the alkyl group in the polymer chain part Is usually 60% by mass or more, preferably 80% by mass or more. If the content is within this range, it may have a repeating structural unit derived from styrene, acrylonitrile or the like.
  • the repeating structural unit constituting the polymer chain (main chain) portion may be composed of one type of repeating structural unit or may be composed of two or more types of repeating structural units. In the latter case, the polymer chain portion may be a random copolymer chain, a block copolymer chain, or an alternating copolymer chain.
  • the polymerizable macromonomer reacts with the above (meth) acrylic acid alkyl ester used as a copolymerization component to form a side chain derived from the macromonomer in the (meth) acrylic copolymer (A). .
  • the (meth) acrylic copolymer (A) is a highly branched polymer having a highly branched structure.
  • the polymerizable unsaturated group possessed by the polymerizable macromonomer is preferably a group having an ethylenically unsaturated double bond, such as a (meth) acryloyl group, an allyl group, a propenyl group, a vinyl group, a vinylidene group, or a vinylene group.
  • (Meth) acryloyl group or vinyl group is preferable, and (meth) acryloyl group is particularly preferable.
  • the polymerizable unsaturated group may be present at the end of the polymer chain portion or at the side chain, but is preferably present at the end.
  • the polymerizable unsaturated group may be present only at one end of the polymer chain portion or at both ends. From the viewpoint of stability during polymerization, one of the polymer chain portions may be present. It is preferably present only at the ends.
  • a (meth) acrylic macromonomer As the polymerizable macromonomer, a (meth) acrylic macromonomer is preferable.
  • the (meth) acrylic macromonomer include polymethyl (meth) acrylate, polybutyl (meth) acrylate, and polyisobutyl (meth) acrylate having a (meth) acryloyl group at the terminal. Polymethyl (meth) acrylate having a (meth) acryloyl group is preferred.
  • the number average molecular weight of the polymerizable macromonomer is usually 500 or more, preferably 1,000 to 10,000, and more preferably 3,000 to 8,000.
  • the number average molecular weight (Mn) of the polymerizable macromonomer is a value in terms of polystyrene measured by gel permeation chromatography.
  • the glass transition temperature (Tg) of the polymerizable macromonomer is preferably ⁇ 60 to 150 ° C., more preferably ⁇ 30 to 130 ° C., from the viewpoint of securing sufficient cohesive force and elastic performance suitable for workability and durability. More preferably, it is 0 to 120 ° C.
  • the glass transition temperature (Tg) of the polymerizable macromonomer can be calculated, for example, from the monomer unit constituting the macromonomer and the content ratio thereof according to the Fox formula described later.
  • a macromonomer for example, as a product manufactured by Toagosei Co., Ltd., a macromonomer (product name) whose terminal functional group is a (meth) acryloyl group and whose polymer chain portion is polymethylmethacrylate. : 45% AA-6, AA-6SR, AA-6), a macromonomer (product name: AB-6) whose polymer chain part is polybutyl acrylate, and a macromonomer whose polymer chain part is polyisobutyl methacrylate ( Product name: AW-6S).
  • the said polymerizable macromonomer may be used individually by 1 type, and may use 2 or more types.
  • 100% by mass of the copolymer component forming the (meth) acrylic copolymer (A) the total amount of the polymerizable macromonomer is usually 0.3 to 20% by mass, preferably 0.5 to 12% by mass, More preferably, it is 0.8 to 10% by mass.
  • the amount of copolymerization of the macromonomer is within the above range, it is preferable in that the cohesiveness of the copolymer can be obtained.
  • the amount of macromonomer copolymerization exceeds the above range, the viscosity increase during copolymerization may become severe, and if the viscosity of the coating solution containing the copolymer is too high, good coating properties to the substrate May not be obtained.
  • polar group-containing monomer examples include a hydroxyl group-containing monomer, an acid group-containing monomer, an amino group-containing monomer, an amide group-containing monomer, a nitrogen-based heterocyclic ring-containing monomer, and a cyano group-containing monomer.
  • the acid group examples include a carboxyl group, an acid anhydride group, a phosphoric acid group, and a sulfuric acid group.
  • the polar group-containing monomer it is preferable to use a monomer having a polar group (crosslinkable functional group) capable of reacting with the crosslinkable functional group of the crosslinking agent (B).
  • a monomer whose polar group is a carboxyl group and / or a hydroxyl group is used, that is, selected from a carboxyl group-containing monomer and a hydroxyl group-containing monomer. It is preferable to use at least one kind.
  • hydroxyl group-containing monomer examples include a hydroxyl group-containing (meth) acrylate, and specific examples include 2-hydroxyethyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate.
  • hydroxyalkyl (meth) acrylates such as 6-hydroxyhexyl (meth) acrylate and 8-hydroxyoctyl (meth) acrylate.
  • the number of carbon atoms of the hydroxyalkyl group in the hydroxyalkyl (meth) acrylate is usually 2 to 8, preferably 2 to 6.
  • a hydroxyl-containing monomer may be used individually by 1 type, and may use 2 or more types.
  • Examples of the carboxyl group-containing monomer include ⁇ -carboxyethyl (meth) acrylate, 5-carboxypentyl (meth) acrylate, mono (meth) acryloyloxyethyl ester succinate, and ⁇ -carboxypolycaprolactone mono (meth) acrylate.
  • Carboxyl group-containing (meth) acrylates such as acrylic acid, methacrylic acid, itaconic acid, crotonic acid, fumaric acid, and maleic acid.
  • Examples of the acid anhydride group-containing monomer include maleic anhydride and itaconic anhydride.
  • Examples of the phosphate group-containing monomer include (meth) acrylic monomers having a phosphate group in the side chain, and examples of the sulfate group-containing monomer include (meth) acrylic monomers having a sulfate group in the side chain.
  • the acid value of the (meth) acrylic copolymer (A) is preferably 117 mgKOH / g or less, more preferably 78 mgKOH / g or less.
  • the amino group-containing monomer include amino group-containing (meth) acrylates such as dimethylaminoethyl (meth) acrylate and diethylaminoethyl (meth) acrylate.
  • the amide group-containing monomer include (meth) acrylamide, N-methyl (meth) acrylamide, N-ethyl (meth) acrylamide, N-propyl (meth) acrylamide, and N-hexyl (meth) acrylamide.
  • nitrogen heterocycle-containing monomer examples include vinyl pyrrolidone, acryloyl morpholine, and vinyl caprolactam.
  • cyano group-containing monomer examples include cyano (meth) acrylate and (meth) acrylonitrile.
  • the amount of the polar group-containing monomer used is preferably 10% by mass or less, more preferably 0.1 to 9% by mass, and further preferably 0.5 to 8% by mass in 100% by mass of the copolymer component.
  • the use amount of the polar group-containing monomer is not more than the above upper limit value, the crosslinking density formed by the (meth) acrylic copolymer (A) and the crosslinking agent (B) does not become too high, and the stress relaxation property is obtained. An excellent pressure-sensitive adhesive layer is obtained.
  • a highly branched (meth) acrylic copolymer (A) having a structural unit derived from a (meth) acrylic macromonomer is used, even if the crosslinking density is lowered, that is, an adhesive. Even in a design where the gel fraction of the layer is as low as 30% by mass or less, a pressure-sensitive adhesive layer having high processability, storage property and durability can be obtained.
  • a polar group containing monomer may be used individually by 1 type, and may use 2 or more types.
  • ⁇ Other monomers As a copolymerization component which forms (meth) acrylic-type copolymer (A), in the range which does not impair the physical property of (meth) acrylic-type copolymer (A), for example, alkoxyalkyl (meth) acrylate, alkoxy poly Other (meth) acrylic acid esters such as alkylene glycol mono (meth) acrylates, alicyclic groups or aromatic ring-containing (meth) acrylates can be included.
  • alkoxyalkyl (meth) acrylate examples include methoxymethyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 3-methoxypropyl (meth) acrylate, 3-ethoxypropyl ( And (meth) acrylate, 4-methoxybutyl (meth) acrylate, and 4-ethoxybutyl (meth) acrylate.
  • alkoxypolyalkylene glycol mono (meth) acrylate examples include methoxydiethylene glycol mono (meth) acrylate, methoxydipropylene glycol mono (meth) acrylate, ethoxytriethylene glycol mono (meth) acrylate, ethoxydiethylene glycol mono (meth) acrylate, And methoxytriethylene glycol mono (meth) acrylate.
  • Examples of the alicyclic group or aromatic ring-containing (meth) acrylate include cyclohexyl (meth) acrylate, benzyl (meth) acrylate, and phenyl (meth) acrylate.
  • the total amount of the other (meth) acrylic ester used is preferably 60% by mass or less, more preferably 40% by mass or less, in 100% by mass of the copolymer component.
  • the physical properties of the (meth) acrylic copolymer (A) are not impaired, for example, styrene, methylstyrene, dimethylstyrene, trimethylstyrene, propylstyrene, butylstyrene, hexylstyrene, heptylstyrene and octylstyrene.
  • Styrenic monomers such as alkyl styrene, fluoro styrene, chloro styrene, bromo styrene, dibromo styrene, iodinated styrene, nitro styrene, acetyl styrene and methoxy styrene, etc .; copolymerizable monomers such as vinyl acetate can also be used it can.
  • the total amount of the copolymerizable monomer used in the copolymerization is preferably 40% by mass or less, more preferably 20% by mass or less, in 100% by mass of the copolymerization component.
  • Other monomers may be used alone or in combination of two or more.
  • the (meth) acrylic copolymer (A) can be produced by, for example, a conventionally known polymerization method such as a solution polymerization method, a bulk polymerization method, an emulsion polymerization method, a suspension polymerization method, etc. Legal is preferred. Specifically, a polymerization solvent and a copolymer component are charged into a reaction vessel, a polymerization initiator is added in an inert gas atmosphere such as nitrogen gas, and the reaction start temperature is usually 40 to 100 ° C., preferably 50 to 80 ° C. The reaction system is maintained at a temperature of usually 50 to 90 ° C., preferably 70 to 90 ° C. for 4 to 20 hours.
  • a conventionally known polymerization method such as a solution polymerization method, a bulk polymerization method, an emulsion polymerization method, a suspension polymerization method, etc. Legal is preferred.
  • a polymerization solvent and a copolymer component are charged into a reaction vessel,
  • the (meth) acrylic copolymer (A) is preferably a copolymer obtained by the above copolymerization in the presence of a polymerization initiator.
  • a polymerization initiator include azo initiators and peroxide polymerization initiators.
  • azo initiator examples include 2,2′-azobisisobutyronitrile, 2,2′-azobis (4-methoxy-2,4-dimethylvaleronitrile), 2,2′-azobis (2- Cyclopropylpropionitrile), 2,2′-azobis (2,4-dimethylvaleronitrile), 2,2′-azobis (2-methylbutyronitrile), 1,1′-azobis (cyclohexane-1-carbohydrate) Nitrile), 2- (carbamoylazo) isobutyronitrile, 2-phenylazo-4-methoxy-2,4-dimethylvaleronitrile, 2,2′-azobis (2-amidinopropane) dihydrochloride, 2,2′- Azobis (N, N'-dimethyleneisobutylamidine), 2,2'-azobis [2-methyl-N- (2-hydroxyethyl) -propionamide], 2,2'-a Bis (isobutyramide) dihydrate, 4,4′-
  • peroxide polymerization initiators examples include t-butyl hydroperoxide, cumene hydroxide, dicumyl peroxide, benzoyl peroxide, lauroyl peroxide, caproyl peroxide, and di-i-propyl peroxydicarbonate.
  • polymerization initiators may be used alone or in combination of two or more.
  • the polymerization initiator is usually in the range of 0.001 to 5 parts by mass, preferably 0.005 to 3 parts by mass with respect to 100 parts by mass of the copolymer component forming the (meth) acrylic copolymer (A). Used in quantity.
  • polymerization solvent used for the solution polymerization examples include aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic hydrocarbons such as n-pentane, n-hexane, n-heptane and n-octane; cyclopentane, Cycloaliphatic hydrocarbons such as cyclohexane, cycloheptane, cyclooctane; ethers such as diethyl ether, diisopropyl ether, 1,2-dimethoxyethane, dibutyl ether, tetrahydrofuran, dioxane, anisole, phenylethyl ether, diphenyl ether; chloroform, Halogenated hydrocarbons such as carbon tetrachloride, 1,2-dichloroethane, chlorobenzene; esters such as ethyl acetate, propyl acetate, butyl a
  • the weight average molecular weight (Mw) measured by the GPC method of the (meth) acrylic copolymer (A) is usually 200,000 to 1,500,000, preferably 400,000 to 1,300,000, more preferably in terms of polystyrene. Is between 500,000 and 1.1 million. Since the copolymer (A) has highly branched chains derived from the polymerizable macromonomer even if Mw is in the above range, the branched chains of the copolymer (A) are appropriately entangled with each other. The durability and workability of the pressure-sensitive adhesive layer are not deteriorated. In particular, when the Mw is 400,000 or more, a highly cohesive pressure-sensitive adhesive layer can be obtained.
  • the molecular weight distribution (Mw / Mn) measured by the GPC method of the (meth) acrylic copolymer (A) is usually 50 or less, preferably 30 or less, more preferably 20 or less.
  • the glass transition temperature (Tg) of the (meth) acrylic copolymer (A) can be calculated by, for example, the Fox formula from the monomer units constituting the polymer and the content ratio thereof.
  • the (meth) acrylic copolymer (A) is synthesized so that the glass transition temperature (Tg) determined by the Fox equation is usually ⁇ 70 to 0 ° C., preferably ⁇ 60 to ⁇ 30 ° C. Can do.
  • Tg is a glass transition temperature of the (meth) acrylic copolymer (A)
  • Tg 1 , Tg 2 ,..., Tg m are glass transition temperatures of homopolymers composed of the respective monomers
  • W 1 , W 2 ,..., W m are weight fractions of the structural units derived from the respective monomers in the copolymer (A).
  • glass transition temperature of the homopolymer composed of each monomer in the Fox formula for example, a value described in Polymer Handbook Fourth Edition (Wiley-Interscience 1999) can be used.
  • the content of the (meth) acrylic copolymer (A) in the pressure-sensitive adhesive composition of the present invention is usually 50 to 100% by mass in 100% by mass of the solid content excluding the organic solvent (E) in the composition. More preferably, it is 60 to 99.999% by mass, and particularly preferably 80 to 99.99% by mass.
  • the content of the (meth) acrylic copolymer (A) is in the above range, the performance as an adhesive is balanced and the adhesive properties are excellent.
  • the pressure-sensitive adhesive composition for polarizing plates of the present invention preferably further contains a crosslinking agent (B).
  • the crosslinking agent (B) is not particularly limited as long as it is a component that can be included in the (meth) acrylic copolymer (A) and can cause a crosslinking reaction with a polar group derived from a polar group-containing monomer. , Isocyanate compound (B1), metal chelate compound (B2), and epoxy compound (B3).
  • the crosslinking agent (B) is not used or only a small amount is used. That is, even in a low design where the gel fraction of the pressure-sensitive adhesive layer is 30% by mass or less, a pressure-sensitive adhesive layer having high processability, storage property and durability can be obtained.
  • a crosslinking agent (B) may be used individually by 1 type, and may use 2 or more types.
  • the crosslinking agents (B) it is preferable to use an isocyanate compound (B1) and / or a metal chelate compound (B2). It is preferable to form a crosslink by a covalent bond based on the isocyanate compound (B1) and / or a pseudo-crosslink by a coordinate bond based on the metal chelate compound (B2) with respect to the (meth) acrylic copolymer (A). .
  • the total content of the crosslinking agent (B) is preferably 5 parts by mass or less, more preferably 2.10 parts by mass with respect to 100 parts by mass of the (meth) acrylic copolymer (A).
  • the amount is 5 parts by mass or less, more preferably 0.001 to 1 part by mass, and particularly preferably 0.01 to 0.5 part by mass.
  • isocyanate compound (B1) As the isocyanate compound (B1), an isocyanate compound having 2 or more isocyanate groups in one molecule is usually used. By crosslinking the (meth) acrylic copolymer (A) with the isocyanate compound (B1), a crosslinked body (network polymer) can be formed.
  • the number of isocyanate groups in the isocyanate compound (B1) is usually 2 or more, preferably 2 to 8, and more preferably 3 to 6. When the number of isocyanate groups is within the above range, it is preferable from the viewpoint of the crosslinking reaction efficiency between the (meth) acrylic copolymer (A) and the isocyanate compound (B1) and the flexibility of the pressure-sensitive adhesive layer.
  • diisocyanate compound having 2 isocyanate groups in one molecule examples include aliphatic diisocyanate, alicyclic diisocyanate, and aromatic diisocyanate.
  • Aliphatic diisocyanates include ethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, 2-methyl-1,5-pentane diisocyanate, 3-methyl-1,5-pentane diisocyanate, 2,2,4-trimethyl
  • aliphatic diisocyanates having 4 to 30 carbon atoms such as -1,6-hexamethylene diisocyanate.
  • alicyclic diisocyanates include alicyclic rings having 7 to 30 carbon atoms such as isophorone diisocyanate, cyclopentyl diisocyanate, cyclohexyl diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated tolylene diisocyanate, hydrogenated diphenylmethane diisocyanate, and hydrogenated tetramethylxylylene diisocyanate.
  • Group diisocyanates are examples of alicyclic rings having 7 to 30 carbon atoms such as isophorone diisocyanate, cyclopentyl diisocyanate, cyclohexyl diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated tolylene diisocyanate, hydrogenated diphenylmethane diisocyanate, and hydrogenated tetramethylxylylene diisocyanate.
  • aromatic diisocyanate examples include aromatic diisocyanates having 8 to 30 carbon atoms such as phenylene diisocyanate, tolylene diisocyanate, xylylene diisocyanate, naphthylene diisocyanate, diphenyl ether diisocyanate, diphenylmethane diisocyanate, and diphenylpropane diisocyanate.
  • isocyanate compound having 3 or more isocyanate groups in one molecule examples include aromatic polyisocyanate, aliphatic polyisocyanate, and alicyclic polyisocyanate. Specific examples include 2,4,6-triisocyanate toluene, 1,3,5-triisocyanate benzene, and 4,4 ', 4 "-triphenylmethane triisocyanate.
  • Examples of the isocyanate compound (B1) include multimers (for example, dimers or trimers, biurets, isocyanurates), derivatives (for example, many) of the above isocyanate compounds having 2 or 3 or more isocyanate groups. Addition reaction product of a dihydric alcohol and two or more molecules of a diisocyanate compound), and a polymer.
  • polyhydric alcohol in the derivative examples include trivalent or higher alcohols such as trimethylolpropane, glycerin and pentaerythritol as low molecular weight polyhydric alcohols; high molecular weight polyhydric alcohols such as polyether polyols, Examples include polyester polyol, acrylic polyol, polybutadiene polyol, and polyisoprene polyol.
  • isocyanate compounds include diphenylmethane diisocyanate trimer, polymethylene polyphenyl polyisocyanate, hexamethylene diisocyanate or tolylene diisocyanate biuret or isocyanurate, trimethylolpropane and tolylene diisocyanate or xylylene diisocyanate.
  • Reaction product for example, a trimolecular adduct of tolylene diisocyanate or xylylene diisocyanate
  • reaction product of trimethylolpropane and hexamethylene diisocyanate for example, a trimolecular adduct of hexamethylene diisocyanate
  • polyether polyisocyanate for example, a polyether polyisocyanate
  • Polyester polyisocyanate is mentioned.
  • isocyanate compounds (B1) the reaction product of trimethylolpropane and tolylene diisocyanate or xylylene diisocyanate (L-45, Soken Chemical Co., Ltd.) TD-75 manufactured by KK), isocyanurate of hexamethylene diisocyanate or tolylene diisocyanate (TSE-100 manufactured by Asahi Kasei Kogyo Co., Ltd., 2050 manufactured by Nippon Polyurethane Co., Ltd.).
  • An isocyanate compound (B1) may be used individually by 1 type, and may use 2 or more types.
  • the content of the isocyanate compound (B1) is preferably 5 parts by mass or less, more preferably 2.5 parts with respect to 100 parts by mass of the (meth) acrylic copolymer (A). It is not more than part by mass, more preferably not more than 1 part by mass, particularly preferably not more than 0.5 part by mass. When the content is within the above range, it is preferable in terms of easy balance between durability and stress relaxation characteristics.
  • the lower limit when using (B1) is, for example, 0.001 part by mass, preferably 0.01 part by mass.
  • Metal chelate compound (B2) examples include polyvalent metals such as aluminum, iron, copper, zinc, tin, titanium, nickel, antimony, magnesium, vanadium, chromium, and zirconium, alkoxide, acetylacetone, and ethyl acetoacetate. Examples include a coordinated compound. Among these, an aluminum chelate compound (M-12AT manufactured by Soken Chemical Co., Ltd.) is particularly preferable. Specific examples include aluminum isopropylate, aluminum secondary butyrate, aluminum ethyl acetoacetate / diisopropylate, aluminum trisethyl acetoacetate, and aluminum trisacetylacetonate.
  • polyvalent metals such as aluminum, iron, copper, zinc, tin, titanium, nickel, antimony, magnesium, vanadium, chromium, and zirconium, alkoxide, acetylacetone, and ethyl acetoacetate. Examples include a coordinated compound.
  • a metal chelate compound (B2) may be used individually by 1 type, and may use 2 or more types.
  • the metal chelate compound (B2) crosslinks the (meth) acrylic copolymer (A) by coordination bond (pseudocrosslinking).
  • the metal chelate compound (B2) is used as the cross-linking agent (B)
  • the cross-linking is maintained at room temperature, and the polymer exhibits cohesiveness. Shows greater flexibility.
  • the content of the metal chelate compound (B2) is preferably 5 parts by mass or less, more preferably 2.10 parts by mass with respect to 100 parts by mass of the (meth) acrylic copolymer (A). 5 parts by mass or less, more preferably 1 part by mass or less, and particularly preferably 0.5 parts by mass or less.
  • the lower limit when using the (B2) is, for example, 0.001 part by mass, preferably 0.01 part by mass.
  • the content of the (B2) is 100 parts by mass of the (B1). On the other hand, it is usually more than 0 parts by mass and 1000 parts by mass or less, more preferably more than 0 parts by mass and 600 parts by mass or less, still more preferably more than 0 parts by mass and 400 parts by mass or less.
  • the content is within the above range, it is preferable in terms of suppressing the bending amount and improving the adhesion of the substrate to an optical film such as a polarizing plate.
  • Epoxy compound (B3) an epoxy compound having 2 or more epoxy groups in one molecule is usually used.
  • the content of the epoxy compound (B3) is preferably 2 parts by mass or less, more preferably 1 part by mass with respect to 100 parts by mass of the (meth) acrylic copolymer (A).
  • it is more preferably 0.5 parts by mass or less.
  • the lower limit when using (B3) is, for example, 0.001 part by mass, preferably 0.01 part by mass.
  • the pressure-sensitive adhesive composition for polarizing plates of the present invention preferably further contains a silane coupling agent (C).
  • a silane coupling agent (C) contributes to the point which adheres an adhesive layer firmly to adherends, such as a glass plate, and prevents peeling in a high-humidity heat environment.
  • silane coupling agent (C) examples include polymerizable unsaturated group-containing silane coupling agents such as vinyltrimethoxysilane, vinyltriethoxysilane, and methacryloxypropyltrimethoxysilane; 3-glycidoxypropyltrimethoxysilane Epoxy groups such as 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane Containing silane coupling agent; amino such as 3-aminopropyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane Group-containing silane coupling Grayed
  • the content of the silane coupling agent (C) in the pressure-sensitive adhesive composition for polarizing plates of the present invention is usually 1 part by mass or less, preferably 0 with respect to 100 parts by mass of the (meth) acrylic copolymer (A). 0.01 to 1 part by mass, more preferably 0.05 to 0.5 part by mass. When the content is in the above range, peeling of the polarizing plate in a high humidity environment and bleeding of the silane coupling agent (C) in a high temperature environment tend to be prevented.
  • An antistatic agent (D) can be used in order to reduce the surface resistance value of the adhesive composition for polarizing plates of this invention, for example.
  • examples of the antistatic agent (D) include a surfactant, an ionic compound, and a conductive polymer.
  • surfactant examples include cationic surfactants having cationic groups such as quaternary ammonium salts, amide quaternary ammonium salts, pyridium salts, primary to tertiary amino groups; sulfonate groups, sulfate esters Anionic surfactants having an anionic group such as a base or a phosphate ester base; amphoteric surfactants such as alkylbetaines, alkylimidazolinium betaines, alkylamine oxides, amino acid sulfates, glycerin fatty acid esters
  • Nonionic surfactants such as sorbitan fatty acid esters, polyoxyethylene alkylamines, polyoxyethylene alkylamine fatty acid esters, N-hydroxyethyl-N-2-hydroxyalkylamines and alkyldiethanolamides It is done.
  • a reactive emulsifier having a polymerizable group is also exemplified as the surfactant, and a polymer surfactant obtained by increasing the molecular weight of the monomer component containing the above surfactant or reactive emulsifier can also be used.
  • the ionic compound is composed of a cation part and an anion part, and may be either solid or liquid at room temperature (23 ° C./50% RH).
  • the cation portion constituting the ionic compound may be either an inorganic cation or an organic cation, or both.
  • the inorganic cation alkali metal ions and alkaline earth metal ions are preferable, and Li + , Na + and K + having excellent antistatic properties are more preferable.
  • organic cation examples include pyridinium cation, piperidinium cation, pyrrolidinium cation, pyrroline cation, pyrrole cation, imidazolium cation, tetrahydropyrimidinium cation, dihydropyrimidinium cation, pyrazolium cation, and pyrazolinium.
  • examples include cations, tetraalkylammonium cations, trialkylsulfonium cations, tetraalkylphosphonium cations, and derivatives thereof.
  • the anion moiety constituting the ionic compound is not particularly limited as long as it can form an ionic compound by ionic bonding with the cation moiety.
  • Examples of the ionic compound include lithium bis (trifluoromethanesulfonyl) imide, lithium bis (difluorosulfonyl) imide, lithium tris (trifluoromethanesulfonyl) methane, potassium bis (trifluoromethanesulfonyl) imide, potassium bis (difluorosulfonyl) imide, 1 -Ethylpyridinium hexafluorophosphate, 1-butylpyridinium hexafluorophosphate, 1-hexyl-4-methylpyridinium hexafluorophosphate, 1-octyl-4-methylpyridinium hexafluorophosphate, 1-octyl-4-methylpyridinium bis (fluoro Sulfonyl) imide, 1-octyl-4-methylpyridinium bis (trifluoromethanesulfonyl) imide, (N, N-die) -N
  • the conductive polymer examples include polythiophene, polyaniline, polypyrrole, and derivatives thereof.
  • the content of the antistatic agent (D) in the pressure-sensitive adhesive composition for polarizing plates of the present invention is usually 3 parts by mass or less, preferably 0.8 parts per 100 parts by mass of the (meth) acrylic copolymer (A). The amount is from 01 to 3 parts by mass, more preferably from 0.05 to 2.5 parts by mass.
  • the pressure-sensitive adhesive composition of the present invention preferably contains an organic solvent (E) in order to adjust its coatability.
  • an organic solvent the polymerization solvent demonstrated in the column of the (meth) acrylic-type copolymer (A) is mentioned.
  • the pressure-sensitive adhesive composition can be prepared by mixing the polymer solution containing the (meth) acrylic copolymer (A) and the polymerization solvent obtained by the above copolymerization and the crosslinking agent (B). it can.
  • the content of the organic solvent is usually 50 to 90% by mass, preferably 60 to 85% by mass.
  • solid content refers to all components excluding the organic solvent (E) among the components contained in the pressure-sensitive adhesive composition
  • solid content concentration refers to the pressure-sensitive adhesive composition 100. The ratio of the said solid content with respect to the mass% is said.
  • the pressure-sensitive adhesive composition of the present invention includes an antioxidant, a light stabilizer, a metal corrosion inhibitor, a tackifier, a plasticizer, a crosslinking accelerator, You may contain the 1 type (s) or 2 or more types selected from the (meth) acrylic-type polymer and rework agents other than A).
  • the pressure-sensitive adhesive composition for polarizing plates of the present invention can be prepared by mixing the (meth) acrylic copolymer (A) and other components as required by a conventionally known method.
  • the polymer solution containing the polymer obtained when the (meth) acrylic copolymer (A) is synthesized may be blended with the crosslinking agent (B) and other components as necessary. It is done.
  • the pressure-sensitive adhesive layer of the present invention can be obtained, for example, by applying and drying the above-mentioned pressure-sensitive adhesive composition; or, specifically, by proceeding with a crosslinking reaction in the above-mentioned pressure-sensitive adhesive composition, specifically (meth) It can be obtained by crosslinking the acrylic copolymer (A) with a crosslinking agent (B).
  • the conditions for forming the pressure-sensitive adhesive layer are, for example, as follows.
  • the pressure-sensitive adhesive composition of the present invention is applied on a support and varies depending on the type of solvent, but is usually 50 to 150 ° C., preferably 60 to 100 ° C., usually 1 to 10 minutes, preferably 2 to 7 minutes. Then, the solvent is removed and a coating film is formed.
  • the film thickness of the dried coating film is usually 5 to 75 ⁇ m, preferably 10 to 50 ⁇ m.
  • the pressure-sensitive adhesive layer is preferably formed under the following conditions. After applying the pressure-sensitive adhesive composition of the present invention on a support and applying a cover film on the coating film formed under the above conditions, usually 3 days or more, preferably 7 to 10 days, usually 5 to 60 ° C., It is preferably cured in an environment of 15 to 40 ° C., usually 30 to 70% RH, preferably 40 to 70% RH. When crosslinking is performed under the aging conditions as described above, a crosslinked body (network polymer) can be efficiently formed.
  • a predetermined thickness is obtained by a known method such as spin coating, knife coating, roll coating, bar coating, blade coating, die coating, or gravure coating.
  • a method of applying and drying can be used.
  • polyester films such as polyethylene terephthalate (PET); plastic films such as polyolefin films such as polyethylene, polypropylene, and ethylene-vinyl acetate copolymer.
  • PET polyethylene terephthalate
  • plastic films such as polyolefin films such as polyethylene, polypropylene, and ethylene-vinyl acetate copolymer.
  • the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition of the present invention has a gel fraction of 30% by mass or less, preferably 0 from the viewpoints of distortion suppression of the polarizing plate, cohesion, adhesion, and removability. -25% by mass, more preferably 0-20% by mass. Since the (meth) acrylic copolymer (A) has highly branched chains derived from the polymerizable macromonomer even if the gel fraction is in the above range, the branched chains of the copolymer (A) are They can be appropriately entangled with each other, and the durability and workability of the pressure-sensitive adhesive layer do not deteriorate. When the gel fraction exceeds the above range, the pressure-sensitive adhesive layer may not be able to sufficiently absorb or relax the stress caused by the dimensional change of the polarizing plate under a high temperature / high humidity heat environment.
  • the pressure-sensitive adhesive sheet for polarizing plates of the present invention has a pressure-sensitive adhesive layer formed from the above-mentioned pressure-sensitive adhesive composition for polarizing plates.
  • the pressure-sensitive adhesive sheet include a double-sided pressure-sensitive adhesive sheet having only the pressure-sensitive adhesive layer, a base material, and a double-sided pressure-sensitive adhesive sheet having the pressure-sensitive adhesive layer formed on both surfaces of the base material, the base material, and one of the base materials.
  • Examples thereof include a single-sided pressure-sensitive adhesive sheet having the above-mentioned pressure-sensitive adhesive layer formed on the surface, and a pressure-sensitive adhesive sheet having a peel-treated cover film attached to the surface of the pressure-sensitive adhesive sheet that is not in contact with the base material.
  • polyester films such as polyethylene terephthalate (PET); plastic films such as polyolefin films such as polyethylene, polypropylene, and ethylene-vinyl acetate copolymer.
  • PET polyethylene terephthalate
  • plastic films such as polyolefin films such as polyethylene, polypropylene, and ethylene-vinyl acetate copolymer.
  • the conditions for forming the pressure-sensitive adhesive layer and the gel fraction are the same as the conditions described in the column [Pressure-sensitive adhesive layer].
  • the thickness of the pressure-sensitive adhesive layer is usually 5 to 75 ⁇ m, preferably 10 to 50 ⁇ m, from the viewpoint of maintaining adhesive performance.
  • the film thickness of the substrate and the cover film is not particularly limited, but is usually 10 to 125 ⁇ m, preferably 25 to 75 ⁇ m.
  • the polarizing plate with a pressure-sensitive adhesive layer of the present invention comprises a polarizing plate and a pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition for a polarizing plate of the present invention on at least one surface of the polarizing plate.
  • polarizing plate is used to include “polarizing film”.
  • a conventionally known polarizing film can be used as the polarizing plate.
  • a multilayer film having a stretched film obtained by adding a polarizing component to a film made of a polyvinyl alcohol-based resin and stretching, and a protective film disposed on the stretched film can be mentioned.
  • the polyvinyl alcohol-based resin include polyvinyl alcohol, polyvinyl formal, polyvinyl acetal, and a saponified product of an ethylene / vinyl acetate copolymer.
  • the polarization component include iodine or a dichroic dye.
  • the protective film include cellulose films such as triacetyl cellulose, polycarbonate films, and polyethersulfone films.
  • the thickness of the polarizing plate is usually 30 to 250 ⁇ m, preferably 50 to 200 ⁇ m.
  • the adhesive sheet for polarizing plates of this invention has A method of transferring the pressure-sensitive adhesive layer to the surface of the polarizing plate and aging is mentioned.
  • the conditions for drying and aging, the range of the gel fraction, and the like are the same as the conditions described in the [Adhesive layer] column.
  • the thickness of the pressure-sensitive adhesive layer formed on the polarizing plate is usually 5 to 75 ⁇ m, preferably 10 to 50 ⁇ m in terms of dry film thickness.
  • the adhesive layer should just be formed in at least one surface of a polarizing plate, the aspect in which an adhesive layer is formed only in the single side
  • the layer which has other functions such as a protective layer, a glare-proof layer, a phase difference layer, a viewing angle improvement layer, for example may be laminated
  • a liquid crystal element is produced by providing the polarizing plate with the pressure-sensitive adhesive layer of the present invention obtained as described above on the substrate surface of the liquid crystal cell.
  • the liquid crystal cell has a structure in which a liquid crystal layer is sandwiched between two substrates.
  • the substrate of the liquid crystal cell examples include a glass plate.
  • the thickness of the substrate is usually 0.1 to 1 mm, preferably 0.15 to 0.8 mm.
  • substrate can be suppressed by using the said adhesive composition. Therefore, even when the thickness of the substrate is small (eg, 0.8 mm or less, preferably 0.15 to 0.7 mm), the above-mentioned pressure-sensitive adhesive composition is suitably used for bonding the polarizing plate and the substrate. be able to.
  • GPC and GPC-MALS For the (meth) acrylic copolymer, the gel permeation chromatography method (GPC method) is used to determine the weight average molecular weight (Mw) and the number average molecular weight (Mn) under the following conditions. The degree of branching was determined using a laser light scattering detector (GPC-MALS) under the following conditions.
  • HLC-8320GPC manufactured by Tosoh Corporation
  • -GPC column configuration The following four columns (all manufactured by Tosoh Corporation) (1) TSKgel HxL-H (guard column) (2) TSKgel GMHxL (3) TSKgel GMHxL (4) TSKgel G2500HxL ⁇ Flow rate: 1.0 mL / min -Column temperature: 40 ° C Sample concentration: 1.5% (w / v) (diluted with tetrahydrofuran) ⁇ Mobile phase solvent: Tetrahydrofuran ⁇ Detector: DAWN HELEOS (MALS detector) + Optilab rEX (RI detector) ⁇ Standard polystyrene conversion (when measuring Mw and Mn)
  • the obtained (meth) acrylic copolymer A has a weight average molecular weight (Mw) of 700,000, a molecular weight distribution (Mw / Mn) of 7.2, a degree of branching of 0.54, and an acid value.
  • Mw weight average molecular weight
  • Mw / Mn molecular weight distribution
  • MMA macromonomer is methyl methacrylate macromonomer having a methacryloyl group at the end (trade name: AA-6, manufactured by Toa Gosei Co., Ltd., Tg: 105 ° C., Mn: 6,000), and BA macromonomer. Represents a butyl acrylate macromonomer having a terminal acryloyl group (trade name: AB-6, manufactured by Toa Gosei Co., Ltd., Tg: -50 ° C., Mn: 6,000).
  • Example 1 (1) Preparation of pressure-sensitive adhesive composition (meth) acrylic polymer solution obtained in Synthesis Example 1 (solid content concentration: 30% by mass) and 100 parts (meth) acrylic polymer contained in the solution (solid content) In contrast, 0.08 parts (solid content) of “TD-75” (solid content: 75% by mass, ethyl acetate solution) manufactured by Soken Chemical Co., Ltd. as an isocyanate compound and Shin-Etsu Chemical Co., Ltd. as a silane coupling agent "KBM-403" (solid content 100%) 0.2 parts made by Daiichi Kogyo Seiyaku Co., Ltd. "AS-804" (solid content 100%) 1 part was mixed as an antistatic agent An agent composition was obtained.
  • the pressure-sensitive adhesive composition obtained in (1) above was applied onto a polyethylene terephthalate film (PET film) subjected to a release treatment using a doctor blade, It dried at 90 degreeC for 3 minute (s), and obtained the sheet
  • the sheet and the polarizing plate (thickness: 110 ⁇ m, layer structure: triacetyl cellulose film / polyvinyl alcohol film / triacetyl cellulose film) were bonded together so that the coating film and the polarizing plate were in contact with each other, and 23 ° C./50%.
  • the plate was allowed to stand and matured for 7 days under the conditions of RH to obtain a polarizing plate with a pressure-sensitive adhesive layer having a PET film, a pressure-sensitive adhesive layer having a thickness of 20 ⁇ m, and a polarizing plate.
  • Example 1 is different from Example 1 except that the (meth) acrylic polymer solution is changed to the polymer solution obtained in Synthesis Examples 2 to 14 and / or the composition is changed as shown in Table 2. Similarly, a pressure-sensitive adhesive composition, a pressure-sensitive adhesive sheet, and a polarizing plate with a pressure-sensitive adhesive layer were obtained.
  • M-12AT represents “M-12AT” (solid content: 10% by mass, toluene, acetylacetone solution) manufactured by Soken Chemical Co., Ltd., which is a metal chelate compound.
  • the polarizing plate with a pressure-sensitive adhesive layer obtained in Examples and Comparative Examples was cut into a width of 10 mm and a length of 100 mm, and the peeled PET film was peeled off. And it bonded together so that the said adhesive layer might contact the said glass plate and it might become a bonding area of 10 mm x 10 mm on the alkali treatment glass plate, and the adhesion processing polarizing plate test piece for evaluation was obtained.
  • the adhesion processing polarizing plate test piece for evaluation, it autoclaved (50 degreeC, 5 atm), and left still for 24 hours in 23 degreeC / 50% RH atmosphere.
  • the test piece was set in a chamber BOX of a minute creep measuring machine with a fixing chuck portion having a length of 15 mm.
  • the evaluation-treated pressure-sensitive adhesive polarizing plate in the test piece was pulled in parallel with the adhesive surface between the polarizing plate and the glass plate and in the length direction of the polarizing plate, The distance ( ⁇ m) of the gap between the glass plate and the polarizing plate in the test piece was measured as the creep value.
  • a polarizing plate with a pressure-sensitive adhesive layer obtained in Examples and Comparative Examples (a laminate comprising PET film / pressure-sensitive adhesive layer / polarizing plate) was cut into a size of 70 mm ⁇ 25 mm to prepare a test piece.
  • the PET film was peeled from the test piece, and a laminate composed of the pressure-sensitive adhesive layer / polarizing plate was attached to one side of a 2 mm thick glass plate so that the pressure-sensitive adhesive layer and the glass plate were in contact with each other using a laminator roll. .
  • the obtained laminate was held in an autoclave adjusted to 50 ° C./5 atm for 20 minutes.
  • the end of the polarizing plate was pulled at a rate of 300 mm / min in the 90 ° direction with respect to the glass plate surface, and the adhesive strength (peel strength) was measured.
  • a test piece was prepared by cutting the polarizing plate with the pressure-sensitive adhesive layer (PET film / pressure-sensitive adhesive layer / laminate comprising the polarizing plate) obtained in Examples and Comparative Examples into a size of 35 mm ⁇ 400 mm (stretching axis direction). did.
  • the PET film is peeled off from the test piece, and the laminate composed of the pressure-sensitive adhesive layer / polarizing plate is laminated on one side of a glass plate having a thickness of 0.7 mm and 40 mm ⁇ 410 mm using a laminator roll. Affixed to touch.
  • the obtained laminate was allowed to stand in a 23 ° C./50% RH environment for 24 hours, and then held in an oven at 60 ° C. for 72 hours. One end was fixed to a wall surface perpendicular to the floor surface, and the amount of lifting at the opposite end was measured with a ruler. Measurements were taken immediately after removal from the oven and after 24 hours.
  • a polarizing plate with a pressure-sensitive adhesive layer obtained in Examples and Comparative Examples (a laminate comprising PET film / pressure-sensitive adhesive layer / polarizing plate) was cut into a size of 150 mm ⁇ 250 mm to prepare a test piece.
  • the PET film was peeled from the test piece, and a laminate composed of the pressure-sensitive adhesive layer / polarizing plate was attached to one side of a 2 mm thick glass plate so that the pressure-sensitive adhesive layer and the glass plate were in contact with each other using a laminator roll. .
  • the obtained laminate was held in an autoclave adjusted to 50 ° C./5 atm for 20 minutes to prepare a test plate. Two similar test plates were prepared.
  • test plate is allowed to stand for 500 hours under conditions of a temperature of 80 ° C. (heat resistance) or a temperature of 60 ° C./humidity of 90% RH (humid heat resistance), and the occurrence of foaming and tearing in the adhesive layer according to the following criteria: Was observed and evaluated. Foaming occurs when cohesion is insufficient, and tearing occurs when stress relaxation is insufficient.
  • (Foam) -AA Foaming is not seen at all.
  • -BB The area of foaming is less than 5% of the whole.
  • -CC The area of foaming is 5% or more of the whole.
  • Comparative Example 1 a (meth) acrylic copolymer having a degree of branching of 0.54 is used, but because the gel fraction is designed as high as 65% by mass, bending evaluation after 24 hours is performed. Was not satisfactory (5.0 mm or more), and although no foaming was observed in the durability evaluation, many tears occurred.
  • the composition of the example uses a (meth) acrylic copolymer having a structural unit derived from a (meth) acrylic macromonomer and having a degree of branching of 0.55 or less, and a gel fraction of 30. Since it was designed at a mass% or less, the bending evaluation after 24 hours was high (3.5 mm or less), and the occurrence of foaming and tearing was in an acceptable range in the durability evaluation.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Nonlinear Science (AREA)
  • Mathematical Physics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Adhesive Tapes (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Polarising Elements (AREA)

Abstract

L'invention fournit une composition d'adhésif pour plaque de polarisation permettant d'empêcher le gauchissement (pliage) d'une cellule de cristaux liquides, et permettant de former une couche adhésive d'une excellente durabilité. Plus précisément, l'invention concerne une composition d'adhésif pour plaque de polarisation qui comprend (A) un copolymère (méth)acrylique qui est obtenu par copolymérisation d'un ester alkylique d'acide (méth)acrylique dont le nombre d'atomes de carbone d'un groupe alkyle est compris entre 4 et 18, et d'un composant copolymère contenant un macromère polymérisable, et qui présente un degré de ramification mesuré par un procédé de chromatographie par perméation de gel (GPC) à l'aide d'un détecteur de diffusion de la lumière multi-angles (MALS), inférieur ou égal à 0,55. Cette composition d'adhésif pour plaque de polarisation est caractéristique en ce que la fraction de gel d'un adhésif qu'elle forme, est inférieure ou égale à 30% en masse.
PCT/JP2015/054777 2014-03-18 2015-02-20 Composition d'adhésif pour plaque de polarisation, couche adhésive, feuille adhésive, et plaque de polarisation avec couche adhésive WO2015141382A1 (fr)

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JP2018065947A (ja) * 2016-10-20 2018-04-26 東洋インキＳｃホールディングス株式会社 アクリル系樹脂組成物、アクリル系フィルム、加飾フィルム及び加飾成型体
JP2018172537A (ja) * 2017-03-31 2018-11-08 リンテック株式会社 粘着性組成物、粘着剤および粘着シート
JP2019085479A (ja) * 2017-11-06 2019-06-06 東洋インキＳｃホールディングス株式会社 光学用粘着剤および光学粘着シート
KR20190124137A (ko) 2018-04-25 2019-11-04 후지모리 고교 가부시키가이샤 점착제 조성물 및 점착 필름
JP2020083936A (ja) * 2018-11-16 2020-06-04 東洋インキＳｃホールディングス株式会社 粘着シート、積層体、およびディスプレイ
CN111742023A (zh) * 2018-03-27 2020-10-02 综研化学株式会社 粘合带
JP2021033164A (ja) * 2019-08-28 2021-03-01 日東電工株式会社 粘着剤層付偏光フィルム積層体、及び、該粘着剤層付偏光フィルム積層体が使用される光学表示パネル
JP2021080421A (ja) * 2019-11-22 2021-05-27 三菱ケミカル株式会社 粘着剤組成物、粘着剤、偏光板用粘着剤、ならびに画像表示装置
JP2021080422A (ja) * 2019-11-22 2021-05-27 三菱ケミカル株式会社 粘着剤組成物、粘着剤、偏光板用粘着剤、ならびに画像表示装置
WO2022102395A1 (fr) * 2020-11-13 2022-05-19 住友化学株式会社 Procédé de fabrication de plaque de polarisation équipée d'une couche adhésive

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WO2016129353A1 (fr) * 2015-02-12 2016-08-18 綜研化学株式会社 Composition d'adhésif pour plaque polarisante et son application
JP2018065947A (ja) * 2016-10-20 2018-04-26 東洋インキＳｃホールディングス株式会社 アクリル系樹脂組成物、アクリル系フィルム、加飾フィルム及び加飾成型体
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JP7460315B2 (ja) 2017-03-31 2024-04-02 リンテック株式会社 粘着性組成物、粘着剤および粘着シート
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JP2019085479A (ja) * 2017-11-06 2019-06-06 東洋インキＳｃホールディングス株式会社 光学用粘着剤および光学粘着シート
CN111742023A (zh) * 2018-03-27 2020-10-02 综研化学株式会社 粘合带
KR20190124137A (ko) 2018-04-25 2019-11-04 후지모리 고교 가부시키가이샤 점착제 조성물 및 점착 필름
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JP2020083936A (ja) * 2018-11-16 2020-06-04 東洋インキＳｃホールディングス株式会社 粘着シート、積層体、およびディスプレイ
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JP2021033164A (ja) * 2019-08-28 2021-03-01 日東電工株式会社 粘着剤層付偏光フィルム積層体、及び、該粘着剤層付偏光フィルム積層体が使用される光学表示パネル
JP7309522B2 (ja) 2019-08-28 2023-07-18 日東電工株式会社 粘着剤層付偏光フィルム積層体、及び、該粘着剤層付偏光フィルム積層体が使用される光学表示パネル
JP2021080421A (ja) * 2019-11-22 2021-05-27 三菱ケミカル株式会社 粘着剤組成物、粘着剤、偏光板用粘着剤、ならびに画像表示装置
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WO2022102395A1 (fr) * 2020-11-13 2022-05-19 住友化学株式会社 Procédé de fabrication de plaque de polarisation équipée d'une couche adhésive

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