WO2014168178A1 - 積層体 - Google Patents

積層体 Download PDF

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Publication number
WO2014168178A1
WO2014168178A1 PCT/JP2014/060290 JP2014060290W WO2014168178A1 WO 2014168178 A1 WO2014168178 A1 WO 2014168178A1 JP 2014060290 W JP2014060290 W JP 2014060290W WO 2014168178 A1 WO2014168178 A1 WO 2014168178A1
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WO
WIPO (PCT)
Prior art keywords
monomer
mass
less
component
sensitive adhesive
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PCT/JP2014/060290
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English (en)
French (fr)
Japanese (ja)
Inventor
恵子 喜多
雄也 米川
Original Assignee
綜研化学株式会社
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Application filed by 綜研化学株式会社 filed Critical 綜研化学株式会社
Priority to CN201480020669.5A priority Critical patent/CN105121157B/zh
Priority to JP2015511282A priority patent/JP6283355B2/ja
Priority to KR1020157032057A priority patent/KR102071103B1/ko
Publication of WO2014168178A1 publication Critical patent/WO2014168178A1/ja

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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
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
    • B32B17/10009—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the number, the constitution or treatment of glass sheets
    • B32B17/10018—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the number, the constitution or treatment of glass sheets comprising only one glass sheet
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
    • B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
    • B32B17/10743—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer containing acrylate (co)polymers or salts thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/32—Layered products comprising a layer of synthetic resin comprising polyolefins
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
    • C03C17/34—Surface treatment of glass, not in the form of fibres or filaments, by coating with at least two coatings having different compositions
    • C03C17/3405—Surface treatment of glass, not in the form of fibres or filaments, by coating with at least two coatings having different compositions with at least two coatings of organic materials
    • 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
    • C08G18/6266—Polymers of amides or imides from alpha-beta ethylenically unsaturated carboxylic acids
    • 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
    • C09J133/062—Copolymers with monomers not covered by C09J133/06
    • C09J133/066—Copolymers with monomers not covered by C09J133/06 containing -OH groups
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2323/00—Polyalkenes
    • 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

Definitions

  • the present invention relates to a laminate.
  • image display devices have been used under various applications and conditions. For example, they are often used not only under room temperature conditions but also under severe conditions such as high temperature and high temperature and humidity. .
  • high temperature or high temperature and humidity condition examples include use in a tropical region, use inside a vehicle, and inside an outdoor measuring instrument.
  • an optical film such as a polarizing film constituting the image display device is produced by adsorbing a dichroic dye to a polymer film such as polyvinyl alcohol, and stretching and orienting the film.
  • a protective film is usually provided on the surface of the polyvinyl alcohol film.
  • a triacetyl cellulose (TAC) film has been often used as a protective film for polyvinyl alcohol.
  • TAC triacetyl cellulose
  • COP polycycloolefin-based film
  • the pressure-sensitive adhesive used for bonding the TAC film and the adherend is used for bonding the polycycloolefin film and the adherend. There is a problem of poor adhesion.
  • Patent Document 1 discloses an acrylic pressure-sensitive adhesive composition containing a nuclear hydrogenated terpene phenol resin for the purpose of improving the fixability to polyolefin and cyclic polyolefin in a high temperature atmosphere.
  • Patent Document 2 discloses a low-polarity film pressure-sensitive adhesive containing an alicyclic monomer or an aromatic ring-containing monomer.
  • the pressure-sensitive adhesive having these alicyclic compounds or aromatic ring-containing compounds may not have sufficient durability and adhesion to a polycycloolefin-based film.
  • Patent Document 1 JP 2007-225458 A
  • Patent Document 2 JP 2005-53976 A
  • the present invention provides a laminate that exhibits excellent durability under high temperature and high humidity conditions, can reduce light leakage, and has excellent adhesion to a polycycloolefin film.
  • the present inventors have added (a1) an alkylene oxide chain-containing monomer, (a2) a hydroxyl group-containing monomer, and (a3) an amide group-containing monomer to a predetermined ratio.
  • the laminate according to one embodiment of the present invention is provided.
  • the pressure-sensitive adhesive layer comprises (A) a monomer comprising the following monomer (a1), monomer (a2), monomer (a3), monomer (a4) component and monomer (a5)
  • the copolymer is formed from a pressure-sensitive adhesive composition containing a copolymer of the composition and (B) an isocyanate-based crosslinking agent, and the copolymer has a weight average molecular weight of 400,000 or more and 2 million or less, and an acid value of 1 or less. It is.
  • the glass substrate and the polycycloolefin-based film may be bonded via the pressure-sensitive adhesive layer.
  • the laminate according to 1 or 2 may further include a polarizing film, and the polarizing film may include the polycycloolefin-based film.
  • the laminate according to 1 or 2 may further include a retardation film, and the retardation film may include the polycycloolefin film.
  • the glass substrate may be a glass substrate used for an image display device.
  • the laminate according to another embodiment of the present invention is A first polycycloolefin-based film; A second polycycloolefin-based film; An adhesive layer provided between the first polycycloolefin-based film and the second polycycloolefin-based film,
  • the pressure-sensitive adhesive layer comprises (A) a monomer (a1), a monomer (a2), a monomer (a3), a monomer (a4) component, and a monomer (a5).
  • a pressure-sensitive adhesive composition comprising a copolymer of a monomer composition and (B) an isocyanate-based crosslinking agent; (A1) Alkylene oxide chain-containing monomer 30% by mass or more and 98.8% by mass or less: (A2) Hydroxyl group-containing monomer 0.1 mass% or more and 10 mass% or less: (A3) Amide group or amino group-containing monomer 0.1% by mass or more and 10% by mass or less: (A4) (Meth) acrylic acid alkyl ester monomer 1 mass% or more and 69.8 mass% or less: (A5) Copolymerizable monomer other than the monomer (a1), the monomer (a2), the monomer (a3), and the monomer (a4) component 0% by mass to 30% by mass % Or less: However, the monomer (a1), the monomer (a2), the monomer (a3), the monomer (a4) component, and the monomer (a5) are added together. 100% by mass.
  • the copolymer has
  • the loss tangent of the pressure-sensitive adhesive layer may be 0.2 or more.
  • the gel fraction of the pressure-sensitive adhesive composition may be 50% or more and 90% or less.
  • the content of the (B) isocyanate-based crosslinking agent in the pressure-sensitive adhesive composition may be 0.1% by mass or more and 5% by mass or less.
  • the content of the (C) silane coupling agent in the pressure-sensitive adhesive composition may be 0.1% by mass or more and 5% by mass or less.
  • the content of the antistatic agent (D) in the pressure-sensitive adhesive composition may be 0% by mass or more and 10% by mass or less.
  • the copolymer has a content of a monomer having an alicyclic hydrocarbon group and / or an aromatic hydrocarbon group of 30% by mass or less. Can be.
  • the laminate exhibits excellent durability under high-temperature conditions or high-temperature and high-humidity conditions. Adhesion between the glass substrate and the polycycloolefin film via the pressure-sensitive adhesive layer or the polycycloolefin film It is excellent in adhesion between each other and light leakage can be reduced.
  • FIG. 1 is a cross-sectional view schematically showing an example of a laminate according to an embodiment of the present invention.
  • FIG. 2 is a cross-sectional view schematically showing an example of a laminate according to an embodiment of the present invention.
  • part means “mass%” and “%” means “mass%” unless otherwise specified.
  • the laminate according to an embodiment of the present invention includes a glass substrate, a polycycloolefin film, and an adhesive layer provided between the glass substrate and the polycycloolefin film,
  • the pressure-sensitive adhesive layer comprises (A) a monomer comprising the following monomer (a1), monomer (a2), monomer (a3), monomer (a4) component and monomer (a5)
  • the copolymer is formed from a pressure-sensitive adhesive composition containing a copolymer of the composition and (B) an isocyanate-based crosslinking agent, and the copolymer has a weight average molecular weight of 400,000 or more and 2 million or less, and an acid value of 1 or less. It is.
  • FIG. 1 is a cross-sectional view schematically showing an example (laminated body 100) of a laminated body according to an embodiment of the present invention.
  • the laminate 100 includes a glass substrate 10, a polycycloolefin-based film 32, and an adhesive layer 20 provided between the glass substrate 10 and the polycycloolefin-based (COP) film 32. And including.
  • the laminate 100 further includes a polarizing film 30, and the polarizing film 30 can include a polycycloolefin-based film 32.
  • the laminate 100 includes a glass substrate 10, a pressure-sensitive adhesive layer 20 provided on the glass substrate 10, and a polarizing film 30 provided on the glass substrate 10 via the pressure-sensitive adhesive layer 20.
  • the polarizing film 30 includes a polycycloolefin film 32, a polyvinyl alcohol film 34 provided on the polycycloolefin film 32, and a TAC film 36 provided on the polyvinyl alcohol film 34.
  • the glass substrate 10 and the polycycloolefin film 32 are bonded via the pressure-sensitive adhesive layer 20.
  • FIG. 2 is a cross-sectional view schematically showing another example (laminate 200) of the laminate according to one embodiment of the present invention.
  • the laminate 200 includes a glass substrate 10, a polycycloolefin film (retardation film) 32, and a polarizing film 130, and includes the glass substrate 10, the polycycloolefin film 32, and The polarizing film 130 is laminated in this order.
  • the polycycloolefin-based film 32 can be a retardation film.
  • the polycycloolefin film 32 and the polarizing film 130 are bonded via the pressure-sensitive adhesive layer 20. Further, the glass substrate 10 and the polycycloolefin-based film 32 are bonded via the pressure-sensitive adhesive layer 22.
  • the polarizing film 130 includes a layer (second polycycloolefin film) 38 that is a polycycloolefin film or TAC film, a polyvinyl alcohol film 34 provided on the layer 38, and a polyvinyl alcohol film 34. And a TAC film 36 provided.
  • the polycycloolefin-based film (first polycycloolefin-based film) 32 and the layer (second polycycloolefin-based film) 38 are bonded via the pressure-sensitive adhesive layer 20.
  • the adhesive layers 20 and 22 in FIGS. 1 and 2 are coated with an adhesive composition (described later) according to the present embodiment (the adhesive layer 20 in FIG. 1 and the adhesive layer 22 in FIG. 2).
  • the adherend is the glass substrate 10 or the polycycloolefin-based film 32, and the adherend is formed on the surface of the polycycloolefin-based film 32 or the layer 38) in the pressure-sensitive adhesive layer 20 in FIG.
  • the pressure-sensitive adhesive composition is applied to the surface of a release film (separator) having good smoothness, and the coating film is dried. And a transfer method for transferring the coating film onto the surface of a specific resin film.
  • the loss tangent of the pressure-sensitive adhesive layer is 0.2 or more (usually 0.20 or more and 0.40 or less) from the viewpoint of improving the adhesion between the adherend and the polycycloolefin-based film. It is preferable that it is 0.28 or more and 0.40 or less.
  • the loss tangent of an adhesive layer is the value measured by the method described in the Example mentioned later.
  • the laminate according to the present embodiment is included in, for example, an image display device (particularly a liquid crystal display device). More specifically, the laminate according to the present embodiment can be used for an image display device for a touch panel, for example.
  • the glass substrate included in the laminate according to the present embodiment is a glass substrate for a liquid crystal display device.
  • the glass substrate which comprises the laminated body which concerns on this embodiment can be a glass substrate used for image display apparatuses.
  • the image display device can be, for example, a TFT (thin film transistor) liquid crystal display device used for a liquid crystal television, a computer monitor, a mobile phone, a tablet, and the like.
  • the “polycycloolefin film” includes at least 50% of a skeleton derived from polycycloolefin in a structural unit.
  • the polycycloolefin-based film may be a polycycloolefin copolymer.
  • the polycycloolefin copolymer may be formed by, for example, ethylene and polycycloolefin (for example, tetracyclododecene) under a Ziegler catalyst. It can be obtained by copolymerization.
  • a commercially available polycycloolefin film can be used as the polycycloolefin film.
  • Examples of commercially available polycycloolefin-based films include ZEONOR films (manufactured by ZEON CORPORATION) and ARTON films (manufactured by JSR).
  • the pressure-sensitive adhesive layer constituting the laminate according to the present embodiment comprises: (A) the following monomer (a1), monomer (a2), monomer (a3), monomer (a4) component And a monomer composition copolymer comprising monomer (a5) (hereinafter sometimes simply referred to as “component (A)”) and (B) an isocyanate-based crosslinking agent (hereinafter simply referred to as “( B) component ”(sometimes referred to as“ component ”)) (hereinafter also referred to simply as“ pressure-sensitive adhesive composition ”).
  • component (a1) 30% by mass or more and 98.8% by mass or less of an alkylene oxide chain-containing monomer (hereinafter sometimes simply referred to as “component (a1)”)
  • component (a2) 0.1% by mass or more and 10% by mass or less of the hydroxyl group-containing monomer (hereinafter sometimes referred to simply as “component (a2)”)
  • component (a3) Amide group-containing monomer 0.1% by mass or more and 10% by mass or less (hereinafter sometimes simply referred to as “component (a3)”)
  • component (a4) (Meth) acrylic acid alkyl ester monomer 1% by mass to 69.8% by mass (hereinafter sometimes simply referred to as “component (a4)”)
  • component (a5) Copolymerizable monomer other than the monomer (a1), the monomer (a2), the monomer (a3), and the monomer (a4) component 0% by mass to 30% by mass % Or less (hereinafter sometimes referred to simply as “component (a5)”)
  • the component (A) includes the monomer (a1), the monomer (a2), the monomer (a3), the monomer (a4) component, and the monomer (a5). It is a copolymer of the monomer composition consisting of and is preferably an acrylic polymer.
  • the “acrylic polymer” means at least one selected from acrylic acid, acrylic acid salt, acrylic acid ester, methacrylic acid, methacrylic acid salt, and methacrylic acid ester in a constituent unit of 50 mass%. The polymer containing above is said.
  • (meth) acrylic acid is a concept including both acrylic acid and methacrylic acid
  • (meth) acrylate is a concept including both acrylate and methacrylate.
  • the alkylene oxide chain-containing monomer as component (a1) is a monomer containing an alkylene oxide chain.
  • the “alkylene oxide chain” means R 2 — (O—R 1 —) n (wherein R 1 represents an alkylene group, R 2 represents an alkyl group, and n represents an integer of 1 or more) Represents a group represented by:
  • the alkylene group represented by R 1 may be linear, branched or cyclic, and is, for example, an alkylene group having 1 to 5 carbon atoms (preferably 2 to 4 carbon atoms).
  • R 2 represents an alkyl group, and n represents an integer of 1 or more.
  • the alkyl group represented by R 2 may be linear, branched or cyclic, and is, for example, an alkyl group having 1 to 10 carbon atoms (preferably 1 to 4 carbon atoms).
  • n is preferably an integer of 1 or more and 3 or less.
  • Examples of the (a1) component alkylene oxide chain-containing monomer include alkylene oxide chain such as 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, and 2-propoxyethyl (meth) acrylate.
  • the content of the component (a1) in the monomer composition is 30% by mass or more and 98.8% by mass. Or less, more preferably 50% by mass or more and 98.8% by mass or less.
  • Component (a2) The hydroxyl group-containing monomer that is component (a2) is a component that crosslinks with the isocyanate-based crosslinking agent that is component (B). From the viewpoint of constructing an appropriate crosslinked structure, the content of the component (a2) in the monomer composition is preferably 0.1% by mass or more and 10% by mass or less, and more preferably 0.1% by mass or more and 2% by mass. The following is more preferable.
  • hydroxyl group-containing monomer as component (a2) examples include 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate, and 3-hydroxypropyl.
  • the component (a2) is preferably a hydroxyalkyl group-containing (meth) acrylic acid ester having 1 to 4 carbon atoms.
  • Component (a3) The amide group or amino group-containing monomer as the component (a3) is a component that imparts cohesive force to the pressure-sensitive adhesive composition.
  • a hydrogen atom bonded to a nitrogen atom constituting an amide group or an amino group participates in the formation of a hydrogen bond in the pressure-sensitive adhesive composition, whereby a high cohesive force can be expressed.
  • the content of the component (a3) in the monomer composition is preferably 0.1% by mass or more and 10% by mass or less, and 0.1% by mass or more and 2% by mass or less. It is more preferable that
  • Examples of the amide group or amino group-containing monomer as the component (a3) include N, N-dimethylaminoethyl acrylate, N, N-dimethylaminoethyl methacrylate, N, N-diethylaminoethyl methacrylate, N, N— Dimethylaminopropylacrylamide N, N′-dimethylacrylamide, N, N′-diethylacrylamide, N, N′-dimethylaminoethylacrylamide, N, N′-dimethylaminopropylacrylamide, N-isopropylacrylamide, tert-octyl (meta ) Amide group-containing (meth) acrylic acid esters such as acrylamide and diacetone acrylamide, acryloylmorpholine, or acrylamide.
  • the (meth) acrylic acid alkyl ester monomer as the component (a4) does not contain any alkylene oxide chain, hydroxyl group, amide group, or amino group.
  • Examples of the (meth) acrylic acid alkyl ester monomer as component (a4) include methyl acrylate, ethyl acrylate, methyl methacrylate, ethyl methacrylate, n-propyl acrylate, n-propyl methacrylate, n-butyl acrylate, n- Butyl methacrylate, n-pentyl acrylate, n-hexyl acrylate, n-hexyl methacrylate, n-heptyl acrylate, n-octyl acrylate, n-octyl methacrylate, n-nonyl acrylate, n-lauryl methacrylate, n-lauryl acrylate, n- Linear alkyl groups such as tetradecyl methacrylate, n-hexadecyl acrylate, n-hexadecyl methacrylate, stearyl
  • (Meth) acrylic acid alkyl ester having a branched alkyl group alkyl (meth) acrylate having an alicyclic alkyl group such as cyclohexyl acrylate, cyclohexyl methacrylate, isobornyl acrylate, isobornyl methacrylate, dicyclopentanyl acrylate, etc. Esters are included, and one of these is used alone or in combination of two or more Rukoto can.
  • the component (a4) preferably has a linear or branched alkyl group. It is more preferable to have an alkyl group having a shape. In this case, the number of carbon atoms of the alkyl group is 1 or more and 20 or less (preferably, because the pressure-sensitive adhesive layer formed using the pressure-sensitive adhesive composition according to this embodiment can further reduce the light leakage of the image display device. More preferably, it is 1 or more and 10 or less.
  • the content of the component (a4) in the monomer composition is 0.1% by mass or more and 69.8% by mass. Or less, more preferably 0.1% by mass or more and 50% by mass or less.
  • Component (a5) The monomer mixture contains a copolymerizable monomer other than the component (a1), the component (a2), the component (a3) and the component (a4) which are the component (a5). May be.
  • Component (a5) is, for example, (meth) acrylic acid ester having an aromatic ring group such as carboxyethyl acrylate, acrylonitrile, pentamethylpiperidine methacrylate, benzyl methacrylate, benzyl acrylate, 2-naphthyl acrylate, phenoxyethyl acrylate, etc .; (Meth) acrylates having an ether group such as pentenyloxyethyl acrylate, glycidyl methacrylate, tetrahydrofurfuryl methacrylate, styrene monomers such as styrene, ⁇ -methylstyrene, o-methylstyrene, p-methylstyren
  • the component (a1) in the monomer mixture for obtaining the copolymer as the component (A), can be 70% by mass or more and 100% by mass or less, and preferably 80% by mass or more and 100% by mass or less.
  • the alicyclic ring in the monomer mixture is preferably 30% by mass or less, and more preferably 20% by mass or less.
  • the component (A) has a weight average molecular weight (Mw) of 400,000 or more and 2 million or less.
  • Mw weight average molecular weight
  • durability may be inferior.
  • light leakage may not be sufficiently reduced.
  • the weight average molecular weight of the component (A) Is preferably 400,000 or more and 2 million or less, and more preferably 750,000 or more and 1.5 million or less.
  • the weight average molecular weight and number average molecular weight of the component (A) are GPC (gel permeation chromatography), and the weight average molecular weight (Mw) and number average molecular weight (Mn) in terms of standard polystyrene are as follows. It is what I have sought.
  • Measuring device HLC-8120GPC (manufactured by Tosoh Corporation)
  • GPC column configuration The following five columns (all manufactured by Tosoh Corporation) (I) TSK-GEL HXL-H (guard column) (Ii) TSK-GEL G7000HXL (Iii) TSK-GEL GMHXL (Iv) TSK-GEL GMHXL (V) TSK-GEL G2500HXL Sample concentration: diluted with tetrahydrofuran to 1.0 mg / cm 3 Mobile phase solvent: tetrahydrofuran Flow rate: 1.0 cm 3 / min Column temperature: 40 ° C.
  • the dispersion index (Mw / Mn) of the component (A) is preferably 1 or more and 20 or less.
  • the component (A) has an acid value of 1 or less.
  • the acid value of component (A) refers to the number of mg of potassium hydroxide required to neutralize free fatty acids and / or resin acids present in 1 g of component (A).
  • the acid value of the component (A) is 1 or less, corrosion of the adherend can be prevented.
  • the measuring method of an acid value it describes in the Example mentioned later.
  • the acid value of the component (A) is 1 or less, a monomer having a carboxyl group (for example, an acrylic that can be used as the component (a5) in the monomer mixture for producing the component (A) It is preferable that the copolymerizable monomer having a carboxyl group such as acid and methacrylic acid is not substantially contained.
  • the fact that the monomer mixture for producing the component (A) does not substantially contain the carboxyl group-containing monomer means that the monomer mixture for producing the component (A) contains a carboxyl group. It means that the monomer content is 0.2% by mass or less, and more specifically, it is more preferable that the carboxyl group-containing monomer is not blended in the monomer mixture for producing the component (A).
  • metal oxides such as an ITO layer used for transparent electrodes are often used in image display devices.
  • the adherend contains a metal oxide
  • the metal oxide is corroded by an acid component, causing a problem that the resistance value is increased.
  • the acid value of the component (A) contained in the pressure-sensitive adhesive composition used for the pressure-sensitive adhesive layer is 1 or less, so that the metal including the ITO layer can be used. Oxide corrosion can be prevented, and an increase in resistance can be suppressed.
  • the content of the component (A) in the pressure-sensitive adhesive composition according to this embodiment is 90 masses of the pressure-sensitive adhesive composition (when the pressure-sensitive adhesive composition is 100 mass%). % To 99.8% by mass, preferably 95% to 99.8% by mass.
  • the gel fraction of the pressure-sensitive adhesive composition according to this embodiment is preferably 50% or more and 90% or less, and more preferably 60% or more and 80% or less.
  • the gel fraction is, for example, the types and amounts of the components (a2) and (a3) in the monomer mixture used when preparing the pressure-sensitive adhesive composition, (B ) Can be adjusted according to the type and amount of the crosslinking agent.
  • the gel fraction 0.1 g (dry weight (1)) of the crosslinked adhesive was collected in a sample bottle, and 30 cc of ethyl acetate was further added to the sample bottle and shaken for 24 hours. After that, the contents of the sample bottle were filtered with a 200 mesh stainless steel wire mesh, the residue on the wire mesh was dried at 100 ° C. for 2 hours, and the dry weight (dry weight (2)) was measured. 1).
  • Gel fraction (%) (dry weight (2) / dry weight (1)) ⁇ 100 (1)
  • Tg of the component (A) is ⁇ from the viewpoint of preventing light leakage and enhancing durability and adhesion between the adherend and the polycycloolefin film. It is preferably 70 ° C. or higher and 0 ° C. or lower, and more preferably ⁇ 60 ° C. or higher and ⁇ 10 ° C. or lower.
  • the Tg of the component (A) is a value calculated by the following formula (2) (FOX formula).
  • Tg A W a1 / Tg a1 + W a2 / Tg a2 + W a3 / Tg a3 + W a4 / Tg a4 + W a5 / Tg a5 (2)
  • Tg A represents the glass transition temperature (K) of the component (A)
  • Tg a1 , Tg a2 , Tg a3 , Tg a4 , and Tg a5 are the constituent monomers (a1) and (a2), respectively.
  • Tg A glass transition temperatures (K)) of homopolymers
  • W a1 , W a2 , W a3 , W a4 , and W a5 are (A The weight fractions of the constituent monomers (a1), (a2), (a3), (a4) and (a5) contained in the component are shown.
  • Tg A is calculated as an absolute temperature (K) by the above formula (2), it is converted to a Celsius temperature (° C.) as necessary.
  • the glass transition temperatures of homopolymers prepared from typical monomers are shown in Table 1 below. More specifically, for example, Polymer Handbook 4th Edition (Polymer Handbook Third Edition, Wiley-Interscience, 2003) It is described in.
  • the viscosity of the component (A) is preferably 1 Pa ⁇ s or more and 10 Pa ⁇ s or less, and preferably 3 Pa ⁇ s or more and 7 Pa ⁇ s or less. It is more preferable.
  • the viscosity of the component (A) is a value measured with a B-type viscometer.
  • the heating residue of component (A) is preferably 15% or more and 50% or less, and 20% or more and 30% or less. It is more preferable.
  • the heating residue of the component (A) means a ratio remaining after the component (A) is heated.
  • the isocyanate-based cross-linking agent that is the (B) component is not particularly limited as long as it is a cross-linking agent that can cross-link with the (A) component at room temperature or under heating.
  • isocyanate monomers such as xylylene diisocyanate, tolylene diisocyanate, chlorophenylene diisocyanate, hexamethylene diisocyanate, tetramethylene diisocyanate, isophorone diisocyanate, diphenylmethane diisocyanate, hydrogenated diphenylmethane diisocyanate, and divalent or higher divalents such as trimethylolpropane
  • isocyanate compound or an isocyanurate obtained by addition reaction with an alcohol compound or the like is exemplified.
  • urethane prepolymer type isocyanates obtained by addition reaction of isocyanate compounds with known polyether polyols, polyester polyols, acrylic polyols, polybutadiene polyols, polyisoprene polyols, and the like can be mentioned. Of these, xylylene diisocyanate and its derivatives are preferably used.
  • the content of the component (B) in the pressure-sensitive adhesive composition according to this embodiment is a pressure-sensitive adhesive composition (pressure-sensitive adhesive) according to this embodiment from the viewpoint of achieving a predetermined gel fraction (for example, 50% to 90%).
  • a predetermined gel fraction for example, 50% to 90%.
  • the agent composition 100% by mass
  • it can be 0.1% by mass or more and 5% by mass or less, and preferably 0.2% by mass or more and 1% by mass or less.
  • the pressure-sensitive adhesive composition according to this embodiment can further contain components other than the component (A) and the component (B) as necessary.
  • the pressure-sensitive adhesive composition according to the present embodiment includes (C) a silane coupling agent (hereinafter sometimes simply referred to as “component (C)”), as long as the effects of the present invention are not impaired.
  • component (D) An ionic compound (hereinafter sometimes simply referred to as “component (D)”), an antioxidant, an ultraviolet absorber, a tackifier, a plasticizer, and the like may be blended.
  • Component (C) is, for example, a polymerizable unsaturated group-containing silicon compound such as vinyltrimethoxysilane, vinyltriethoxysilane, and methacryloxypropyltrimethoxysilane; 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyl Silicon compounds having an epoxy structure such as methyldimethoxysilane and 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane; 3-aminopropyltrimethoxysilane, N- (2-aminoethyl) 3-aminopropyltrimethoxysilane And amino group-containing silicon compounds such as N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane; and 3-chloropropyltrimethoxysilane; oligomer-type silane coupling agents, etc. (Meth) acrylic Silane coupling agents having a functional
  • the content of the component (C) in the pressure-sensitive adhesive composition according to this embodiment is the pressure-sensitive adhesive composition (pressure-sensitive adhesive composition) according to this embodiment from the viewpoint of maintaining good adhesion with the adherend. 0.1 mass% or more and 5 mass% or less, and preferably 0.2 mass% or more and 1 mass% or less with respect to 100 mass%).
  • the adhesive composition which concerns on this embodiment may contain the ionic compound (D).
  • the component (D) include an ionic compound that is composed of an anion and a cation and is liquid or solid at 25 ° C., specifically, an alkali metal salt, an ionic liquid (liquid at 25 ° C. Shape), surfactants and the like.
  • the pressure-sensitive adhesive composition according to this embodiment contains the component (D)
  • the oxygen atom of the alkylene oxide chain derived from the component (a1) constituting the component (A) is distributed to the cation constituting the component (D). Therefore, high antistatic performance can be realized.
  • alkali metal salt examples include compounds comprising an alkali metal cation such as lithium, sodium and potassium and an anion.
  • cation constituting the ionic liquid piperidinium cation, pyrrolidinium cation, cation having pyrroline skeleton, cation having pyrrole skeleton, imidazolium cation, tetrahydropyrimidinium cation, dihydropyrimidinium cation, pyra Zolium cation, pyrazolinium cation, tetraalkylammonium cation, trialkylsulfonium cation, tetraalkylphosphonium cation and the like.
  • anions constituting the ionic liquid include Cl ⁇ , Br ⁇ , I ⁇ , AlCl 4.
  • ionic compound it is comprised from these cations and anions, and a liquid ionic compound is mentioned at 25 degreeC.
  • ionic compounds include 2-methyl-1-pyrroline tetrafluoroborate, 1-ethyl-2-phenylindole tetrafluoroborate, 1,2-dimethylindole tetrafluoroborate, and 1-ethyl.
  • Carbazole tetrafluoroborate 1-ethyl-3-methylimidazolium tetrafluoroborate, 1-ethyl-3-methylimidazolium acetate, 1-ethyl-3-methylimidazolium trifluoroacetate, 1-ethyl-3-methylimidazole Lithium heptafluorobutyrate, 1-ethyl-3-methylimidazolium trifluoromethanesulfonate, 1-ethyl-3-methylimidazolium perfluorobutanesulfonate, 1-ethyl-3-methylimidazolium dicyanamide, 1 Ethyl-3-methylimidazolium bis (trifluoromethanesulfonyl) imide, 1-ethyl-3-methylimidazolium bis (pentafluoroethanesulfonyl) imide, 1-ethyl-3-methylimidazolium tris (trifluoromethanesulf
  • any of nonionic surfactants, cationic surfactants, anionic surfactants and amphoteric surfactants can be used.
  • nonionic surfactant examples include polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether and polyoxyethylene stearyl ether, polyoxyethylene alkylphenyls such as polyoxyethylene octylphenyl ether and polyoxyethylene nonielphenyl ether.
  • Sorbitan higher fatty acid esters such as ethers, sorbitan monolaurate, sorbitan monostearate, sorbitan trioleate, polyoxyethylene sorbitan higher fatty acid esters such as polyoxyethylene sorbitan monolaurate, polyoxyethylene monolaurate, poly Polyoxyethylene higher fatty acid esters such as oxyethylene monostearate; for example, oleic acid monoglyceride, stearic acid monoglyceride Glycerine higher fatty acid esters such as id, polyoxyethylene, polyoxypropylene, polyoxyalkylenes and their block copolymers of polyoxybutylene and the like.
  • cationic surfactant examples include alkyltrimethylammonium chloride, dialkyldimethylammonium chloride, benzalkonium chloride, alkyldimethylammonium ethosulphate and the like.
  • anionic surfactant examples include sodium laurate, sodium oleate, N-acyl-N-methylglycine sodium salt, sodium carboxylate such as sodium polyoxyethylene lauryl ether carboxylate, sodium dodecylbenzenesulfonate, dialkylsulfosuccinate.
  • amphoteric surfactant examples include carboxybetaine surfactants, aminocarboxylates, imidazolinium petines, lecithins, and alkylamine oxides.
  • conductive polymers, conductive carbon, ammonium chloride, aluminum chloride, copper chloride, iron chloride, ammonium sulfate, and the like can be used.
  • alkali metal salts are preferred.
  • content of the (D) component in the adhesive composition which concerns on this embodiment is the adhesive composition (adhesive composition) which concerns on this embodiment.
  • adhesive composition adhesive composition
  • the polymerization method of component (A) is not particularly limited and can be polymerized by known methods such as solution polymerization, emulsion polymerization, suspension polymerization, etc. In producing the pressure-sensitive adhesive composition of the present invention using a mixture of coalesces, it is preferable to perform polymerization by solution polymerization from the viewpoint that the treatment process is relatively simple and can be performed in a short time.
  • solution polymerization generally, a predetermined organic solvent, each monomer, a polymerization initiator, a chain transfer agent used as necessary, and the like are charged in a polymerization tank, under a nitrogen stream or a reflux temperature of the organic solvent, The reaction is carried out by heating for several hours with stirring.
  • the organic solvent include aromatic hydrocarbons such as benzene, toluene, ethylbenzene, n-propylbenzene, tert-butylbenzene, o-xylene, m-xylene, p-xylene, tetralin, decalin, aromatic naphtha;
  • aromatic hydrocarbons such as benzene, toluene, ethylbenzene, n-propylbenzene, tert-butylbenzene, o-xylene, m-xylene, p-xylene, tetralin, decalin, aromatic naphtha
  • aliphatic or alicyclic hydrocarbons such as n-hexane, n-heptane, n-octane, isooctane, n-decane, dipentene, petroleum spirit, petroleum naphtha, turpentine oil;
  • Esters such
  • organic solvents for polymerization in the polymerization of the component (A), it is preferable to use an organic solvent that hardly causes chain transfer during the polymerization reaction, for example, esters and ketones.
  • an organic solvent that hardly causes chain transfer during the polymerization reaction for example, esters and ketones.
  • use of ethyl acetate, methyl ethyl ketone, acetone or the like is preferable.
  • organic peroxides and azo compounds that can be used in ordinary solution polymerization.
  • organic peroxides include tert-butyl hydroperoxide, cumene hydroxide, dicumyl peroxide, benzoyl peroxide, lauroyl peroxide, caproyl peroxide, diisopropyl peroxydicarbonate, and di-2.
  • Examples of the azo compound include 2,2′-azobis-isobuty Examples include rhonitrile, 2,2′-azobis-2,4-dimethylvaleronitrile, 2,2′-azobis-4-methoxy-2,4-dimethylvaleronitrile, and the like.
  • polymerization initiators that do not cause a graft reaction during the polymerization reaction of component (A) are preferable, and azo-based compounds are particularly preferable.
  • the amount used is usually 0.01 parts by mass or more and 2 parts by mass or less, preferably 0.1 parts by mass or more and 1.0 parts by mass or less, with respect to 100 parts by mass of the total amount of monomers.
  • the component (A) contained in the pressure-sensitive adhesive composition of the present invention it is normal not to use a chain transfer agent, but as long as it does not impair the purpose and effect of the present invention. It is possible to use.
  • chain transfer agents examples include cyanoacetic acid; alkyl esters having 1 to 8 carbon atoms of cyanoacetic acid; bromoacetic acid; alkyl esters having 1 to 8 carbon atoms of bromoacetic acid; anthracene and phenanthrene.
  • Aromatic compounds such as p-nitroaniline, nitrobenzene, dinitrobenzene, p-nitrobenzoic acid, p-nitrophenol, p-nitrotoluene; benzoquinone, 2, Benzoquinone derivatives such as 3,5,6-tetramethyl-p-benzoquinone; borane derivatives such as tributylborane; carbon tetrabromide, carbon tetrachloride, 1,1,2,2-tetrabromoethane, tribromoethylene, Trichlorethylene, bromotrichloromethane, tribromometa Halogenated hydrocarbons such as 3-chloro-1-propene; aldehydes such as chloral and furaldehyde; alkyl mercaptans having 1 to 18 carbon atoms; aromatic mercaptans such as thiophenol and toluene mercaptan; mercaptoacetic acid And alkyl esters of mercaptoacetic acid having
  • the polymerization temperature of the component (A) is generally about 30 ° C. or higher and 180 ° C. or lower, preferably 40 ° C. or higher and 150 ° C. or lower, more preferably 50 ° C. or higher and 90 ° C. or lower.
  • an unreacted monomer is contained in a polymer obtained by a solution polymerization method or the like, it can be purified by a reprecipitation method using methanol or the like in order to remove the monomer.
  • the adhesive composition which concerns on this embodiment is normally prepared by mixing the said (A) and (B) component and arbitrary components as needed simultaneously or in arbitrary orders. Moreover, when mixing (A) component and (B) component, when preparing (A) component by solution polymerization, (B) component is added to the solution containing (A) component after the completion of polymerization. In addition, when the component (A) is prepared by bulk polymerization, uniform mixing becomes difficult after the completion of the polymerization. Therefore, it is preferable to add and mix the component (B) during the polymerization.
  • the said adhesive layer is generally formed by providing an adhesive layer on a peeling film and transferring this to the said adherend. It is.
  • the thickness of the pressure-sensitive adhesive layer is usually 1 ⁇ m or more and 50 ⁇ m or less, preferably about 5 ⁇ m or more and 30 ⁇ m or less.
  • a polymer constituting a polycycloolefin-based film is mainly composed of a low-polar group, and therefore has a low polarity. Therefore, an acrylic pressure-sensitive adhesive is difficult to adhere to the polycycloolefin-based film. For this reason, attempts have been made to improve the adhesion between the polycycloolefin film and the pressure-sensitive adhesive layer by matching the polarities of the polycycloolefin film and the pressure-sensitive adhesive layer.
  • a pressure-sensitive adhesive layer containing a polymer having a low polarity group for example, an aromatic hydrocarbon group or an alicyclic hydrocarbon group
  • a polycycloolefin film for example, a polycycloolefin film
  • Patent Documents 1 and 2). reference for example, the pressure-sensitive adhesive layer obtained from a pressure-sensitive adhesive composition containing a polymer having these low polar groups has durability and adhesion to a polycycloolefin film. May not be enough.
  • the component (a1) provides an appropriate elastic modulus and light leakage prevention effect to the pressure-sensitive adhesive layer. That is, in the present invention, an adhesive layer having an elastic modulus corresponding to a polycycloolefin film can be obtained from the alkylene oxide chain-containing monomer as the component (a1). This is based on a novel and original idea that the adhesion can be improved and the light leakage prevention effect can be obtained.
  • the laminate according to this embodiment includes a glass substrate, a polycycloolefin film, and an adhesive layer provided between the glass substrate and the polycycloolefin film.
  • the pressure-sensitive adhesive composition for forming the pressure-sensitive adhesive layer comprises a component (A): a single component comprising the component (a1), component (a2), component (a3), component (a4), and component (a5).
  • the component (a1) brings an appropriate elastic modulus and light leakage prevention effect to the pressure-sensitive adhesive layer.
  • the pressure-sensitive adhesive layer is easily adapted to the surface of the polycycloolefin-based film, and the glass substrate and the polycycloolefin-based film It is possible to improve the adhesion.
  • the pressure-sensitive adhesive layer can exhibit excellent durability under high temperature and high humidity conditions, and can reduce light leakage.
  • the laminate according to this embodiment includes a first polycycloolefin film, a second polycycloolefin film, the first polycycloolefin film, and the second polycycloolefin film.
  • a pressure-sensitive adhesive layer provided between the film and the pressure-sensitive adhesive composition for forming the pressure-sensitive adhesive layer comprises: (A) component: (a1) component, (a2) component, (a3) A copolymer of a monomer composition comprising the component (a), the component (a4), and the component (a5) and the component (B): an isocyanate-based crosslinking agent, and the component (a1), the component (a2), By including the (a3) component, the (a4) component, and the (a5) component at a predetermined ratio, the (a1) component brings an appropriate elastic modulus and light leakage prevention effect to the pressure-sensitive adhesive layer.
  • the pressure-sensitive adhesive layer since the loss tangent of the pressure-sensitive adhesive layer is high and the pressure-sensitive adhesive layer has an appropriate elasticity, the pressure-sensitive adhesive layer is easily adapted to the surface of the polycycloolefin-based film, and the adhesion between the polycycloolefin-based films is Can be increased. In addition, the pressure-sensitive adhesive layer can exhibit excellent durability under high temperature and high humidity conditions, and can reduce light leakage.
  • the heating residue (nV%) at 105 ° C. of the obtained acrylic polymer 1 was 25.0%.
  • the weight average molecular weight measured by gel permeation chromatography (GPC) about the obtained acrylic polymer 1 is 89,990,000, the dispersion index of the acrylic polymer 1 is 11, and it can stand at 23 degreeC.
  • the viscosity was 5.1 (Pa ⁇ s).
  • the heating residue (nV%) at 105 ° C. of the obtained acrylic polymer 2 was 24.9%.
  • the weight average molecular weight measured by the gel permeation chromatography (GPC) about the obtained acrylic polymer 2 is 903,000, the dispersion index of the acrylic polymer 2 is 11, and it can stand at 23 degreeC.
  • the viscosity was 5.4 (Pa ⁇ s).
  • the heating residue (nV%) at 105 ° C. of the obtained acrylic polymer 3 was 25.2%. Moreover, the weight average molecular weight measured by gel permeation chromatography (GPC) about the obtained acrylic polymer 3 is 902,000, the dispersion index of the acrylic polymer 2 is 12, and it can stand at 23 degreeC. The viscosity was 5.2 (Pa ⁇ s).
  • the heating residue (nV%) at 105 ° C. of the obtained acrylic polymer 4 was 25.1%.
  • the weight average molecular weight measured by the gel permeation chromatography (GPC) about the obtained acrylic polymer 4 is 903,000, the dispersion index of the acrylic polymer 4 is 11, and it can stand at 23 degreeC.
  • the viscosity was 5.1 (Pa ⁇ s).
  • the heating residue (nV%) at 105 ° C. of the obtained acrylic polymer 5 was 25.2%. Moreover, the weight average molecular weight measured by the gel permeation chromatography (GPC) about the obtained acrylic polymer 5 is 902,000, the dispersion index of the acrylic polymer 5 is 11, and it can stand at 23 degreeC. The viscosity was 4.8 (Pa ⁇ s).
  • the heating residue (nV%) at 105 ° C. of the obtained acrylic polymer 6 was 25.0%. Moreover, the weight average molecular weight measured by the gel permeation chromatography (GPC) about the obtained acrylic polymer 6 is 915,000, the dispersion index of the acrylic polymer 6 is 11, and it can stand at 23 degreeC. The viscosity was 5.8 (Pa ⁇ s).
  • the heating residue (nV%) at 105 ° C. of the obtained acrylic polymer 7 was 24.9%.
  • the weight average molecular weight measured by gel permeation chromatography (GPC) about the obtained acrylic polymer 7 is 931,000, the dispersion index of the acrylic polymer 7 is 11, and it can stand at 23 degreeC.
  • the viscosity was 4.9 (Pa ⁇ s).
  • the heating residue (nV%) at 105 ° C. of the obtained acrylic polymer 8 was 35.5%.
  • the weight average molecular weight measured by the gel permeation chromatography (GPC) about the obtained acrylic polymer 8 is 36.0 million, the dispersion index of the acrylic polymer 8 is 10, and it is 23 degreeC.
  • the viscosity was 3.5 (Pa ⁇ s).
  • the heating residue (nV%) at 105 ° C. of the obtained acrylic polymer 9 was 25.0%.
  • the acrylic polymer 9 obtained had a weight average molecular weight of 891,000 measured by gel permeation chromatography (GPC), and the acrylic polymer 9 had a dispersion index of 11 at 23 ° C.
  • the viscosity was 5.3 (Pa ⁇ s).
  • the heating residue (nV%) at 105 ° C. of the obtained acrylic polymer 10 was 24.8%.
  • the weight average molecular weight measured by the gel permeation chromatography (GPC) about the obtained acrylic polymer 10 is 908,000, the dispersion index of the acrylic polymer 10 is 13, and it can stand at 23 degreeC.
  • the viscosity was 5.4 (Pa ⁇ s).
  • the heating residue (nV%) at 105 ° C. of the obtained acrylic polymer 1 was 25.1%.
  • the weight average molecular weight measured by the gel permeation chromatography (GPC) about the obtained acrylic polymer 1 is 931,000, the dispersion index of the acrylic polymer 1 is 12, and it can stand at 23 degreeC.
  • the viscosity was 5.1 (Pa ⁇ s).
  • this polarizing plate was cut into an appropriate size and bonded to a glass plate to produce laminates (glass plate and polarizing plate with an adhesive layer) of Examples 1 to 6 and Comparative Examples 1 to 5. .
  • a glass plate, an adhesive layer, and a polarizing plate are laminated in this order, and the glass plate and the polarizing plate are bonded via the adhesive layer.
  • the laminate was subjected to a 500 hour durability test, a light leakage measurement test, and a surface resistance value measurement under two conditions of 85 ° C./95 RH% and 60 ° C./95 RH%.
  • Test method 2.2.1 Gel fraction 1 g of a sample was placed in 50 ml of ethyl acetate and applied to a shaker (type name: Shaker SA-300, manufactured by Yamato Scientific Co., Ltd.). The gel content was filtered through a 200 mesh stainless steel net and dried. Then, the value which remove
  • the laminate glass plate and polarizing plate with pressure-sensitive adhesive layer
  • the laminate was cut into a size of 150 mm ⁇ 250 mm, attached to one side of the glass plate using a laminator roll, and then adjusted to 5 atm at 50 ° C.
  • a test plate was prepared by holding in an autoclave for 20 minutes. Two similar test plates were prepared and left for 500 hours under the conditions of 60 ° C. and 95% humidity, respectively, and left for 500 hours under the conditions of 80 ° C. The peeling of the interface of the layer, the occurrence of foaming, etc. were confirmed visually.
  • Two laminated bodies (glass plate and polarizing plate with adhesive layer) are cut to a size of 80 mm ⁇ 140 mm in a state where they are perpendicular to each other, so that they are perpendicular to each other on both sides of the glass plate.
  • a test plate was prepared by sticking using a laminator roll and then holding it in an autoclave adjusted to 50 ° C. and 5 atm for 20 minutes. This test plate was allowed to stand for 500 hours at 80 ° C., and light leakage was observed according to the following criteria.
  • the laminated body (glass plate and polarizing plate with adhesive layer) obtained in Examples 1 to 6 and Comparative Examples 1 to 5 was cut to 10 mm ⁇ 60 mm on an ITO vapor-deposited PET film cut to 10 mm ⁇ 100 mm. And then autoclaved at 50 ° C. ⁇ 5 atm for 20 minutes. Next, after standing at room temperature for 1 hour, placing it in an environment of 60 ° C. and 90% RH for 500 hours, standing at 23 ° C. and humidity of 65% RH for 1 hour, then the resistance of the ITO deposited film The value was measured and compared with the resistance value before the test measured in advance, and the rate of change of the resistance value with respect to the resistance value before the test was obtained.
  • -Titration solution 0.1 mol / l, ethanolic potassium hydroxide solution-Electrode: glass electrode, comparative electrode; calomel electrode
  • the pressure-sensitive adhesive layer is formed from a pressure-sensitive adhesive composition containing the component (A) and the component (B), and the weight of the component (A).
  • the average molecular weight is 400,000 or more and 2 million or less, and the acid value is 1 or less
  • the adhesiveness between the glass substrate and the polycycloolefin-based film and the polycycloolefin-based film between the pressure-sensitive adhesive layers It can be understood that the adhesiveness is excellent, high durability is realized, and light leakage can be reduced.
  • the laminate of Comparative Example 1 was corroded to ITO because the acid value of the component (A) exceeded 1.
  • the laminate of Comparative Example 2 does not contain the component (a1) in the pressure-sensitive adhesive composition that is the raw material of the component (A), so that the durability and light leakage prevention performance are inferior, and the adhesion to the COP It can be understood that the property is also low.
  • the laminated body of the said comparative example 3 has low molecular weight, it can be understood that it is inferior to durability.
  • the laminate of Comparative Example 4 is an example in which 30% by mass of benzyl acrylate is used as the component (a4) instead of the component (a1) in the pressure-sensitive adhesive composition that is the raw material of the component (A). It can be understood that the durability and adhesion to the COP are not good and the light leakage prevention performance is poor.
  • the laminate of Comparative Example 5 is an example in which 30% by mass of cyclohexyl acrylate is used as the component (a5) instead of the component (a1) in the pressure-sensitive adhesive composition that is the raw material of the component (A). It can be understood that the durability is not good and the adhesion to the COP is inferior.
  • the laminate of Comparative Example 6 is an example in which the content of the component (a1) in the pressure-sensitive adhesive composition that is the raw material of the component (A) is less than 30% by mass. It can be understood that the adhesion is not good.

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JPWO2014168178A1 (ja) 2017-02-16
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