WO2016072197A1 - 偏光板用粘着剤組成物および粘着剤層付き偏光板 - Google Patents

偏光板用粘着剤組成物および粘着剤層付き偏光板 Download PDF

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WO2016072197A1
WO2016072197A1 PCT/JP2015/078302 JP2015078302W WO2016072197A1 WO 2016072197 A1 WO2016072197 A1 WO 2016072197A1 JP 2015078302 W JP2015078302 W JP 2015078302W WO 2016072197 A1 WO2016072197 A1 WO 2016072197A1
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Prior art keywords
sensitive adhesive
pressure
adhesive layer
meth
mass
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PCT/JP2015/078302
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English (en)
French (fr)
Japanese (ja)
Inventor
雄也 米川
隆祐 田中
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綜研化学株式会社
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Priority to KR1020177011060A priority Critical patent/KR102135645B1/ko
Priority to JP2016557505A priority patent/JP6644698B2/ja
Priority to CN201580057989.2A priority patent/CN107148587B/zh
Publication of WO2016072197A1 publication Critical patent/WO2016072197A1/ja

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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00Adhesives in the form of films or foils
    • C09J7/10Adhesives in the form of films or foils without carriers
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00Adhesives 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
    • C09J133/04Homopolymers or copolymers of esters
    • C09J133/06Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B32LAYERED PRODUCTS
    • B32BLAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00Layered products comprising a layer of synthetic resin
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B32LAYERED PRODUCTS
    • B32BLAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00Layered products comprising a layer of synthetic resin
    • B32B27/30Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04Polyurethanes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00Adhesives in the form of films or foils
    • C09J7/20Adhesives in the form of films or foils characterised by their carriers
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00Adhesives in the form of films or foils
    • C09J7/20Adhesives in the form of films or foils characterised by their carriers
    • C09J7/29Laminated material
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00Optical elements other than lenses
    • G02B5/30Polarising elements
    • GPHYSICS
    • G02OPTICS
    • G02FOPTICAL 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
    • G02F1/00Devices 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
    • G02F1/01Devices 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 
    • G02F1/13Devices 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
    • G02F1/133Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333Constructional arrangements; Manufacturing methods
    • G02F1/1335Structural association of cells with optical devices, e.g. polarisers or reflectors
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2203/00Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/318Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays

Definitions

  • the present invention relates to a pressure-sensitive adhesive composition for a polarizing plate, a polarizing plate with a pressure-sensitive adhesive layer, and the like.
  • the liquid crystal cell has a structure in which a liquid crystal layer is sandwiched between two substrates (eg, a glass plate).
  • a polarizing plate is attached to the surface of the substrate constituting the liquid crystal cell via an adhesive layer.
  • a polarizing plate generally has a structure in which a polarizer protective film such as a triacetyl cellulose film is laminated on both sides of a polarizer having a polarizing function. Has been.
  • Patent Document 1 an adhesive layer that also functions as a polarizer protective film is provided on at least one surface of a polarizer, and the adhesive layer includes an acrylic copolymer having a reactive functional group,
  • the polarizing plate with an adhesive layer formed including the reaction product with the crosslinking agent which has the functional group which reacts with the said reactive functional group is described.
  • the heat resistance and moist heat resistance of the pressure-sensitive adhesive layer are not sufficient, and further improvement is desired.
  • An object of the present invention is to provide a pressure-sensitive adhesive composition for a polarizing plate, which can be applied to a configuration in which at least one of the polarizer protective films usually formed on both sides of a polarizer is omitted, and is excellent in durability. To provide things.
  • the present invention includes, for example, the following [1] to [6].
  • a pressure-sensitive adhesive composition for polarizing plates comprising 40 parts by mass and used to form a pressure-sensitive adhesive layer in direct contact with a polarizer.
  • a pressure-sensitive adhesive layer for polarizing plates formed from the pressure-sensitive adhesive composition according to [1].
  • a pressure-sensitive adhesive sheet for polarizing plate having the pressure-sensitive adhesive layer according to any one of [2] to [4].
  • the adhesive composition for polarizing plates which can form the adhesive layer excellent in durability applicable to the structure by which at least one of the polarizer protective film normally formed on both surfaces of a polarizer was abbreviate
  • the adhesive layer for polarizing plates formed from the said composition, the adhesive sheet for polarizing plates which has the said adhesive layer, and the polarizing plate with an adhesive layer which has the said adhesive layer can be provided.
  • the pressure-sensitive adhesive composition for polarizing plate, the pressure-sensitive adhesive layer for polarizing plate, the pressure-sensitive adhesive sheet for polarizing plate and the polarizing plate with the pressure-sensitive adhesive layer will be described.
  • the pressure-sensitive adhesive composition for polarizing plate, the pressure-sensitive adhesive layer for polarizing plate and the pressure-sensitive adhesive sheet for polarizing plate of the present invention are also referred to as “pressure-sensitive adhesive composition”, “pressure-sensitive adhesive layer” and “pressure-sensitive adhesive sheet”, respectively.
  • the pressure-sensitive adhesive composition for polarizing plates of the present invention contains a (meth) acrylic copolymer (A) and an isocyanate-based crosslinking agent (B) described below.
  • the composition may contain at least one selected from a silane coupling agent (C) and an antistatic agent (D) as necessary, and may contain an organic solvent (E).
  • the (meth) acrylic copolymer (A) is a cross-link containing a (meth) acrylic acid alkyl ester (a1) having a glass transition temperature (Tg) of a homopolymer of 0 ° C. or higher, a hydroxyl group-containing monomer, and a carboxyl group-containing monomer.
  • Tg glass transition temperature
  • Copolymer of a monomer component containing a functional functional group-containing monomer (a2) and obtained by copolymerizing the monomer component.
  • the copolymer (A) usually has a structural unit derived from the (meth) acrylic acid alkyl ester (a1) and a structural unit derived from the crosslinkable functional group-containing monomer (a2).
  • acrylic and methacryl are collectively referred to as “(meth) acryl”.
  • the structural unit derived from a certain monomer a contained in the polymer is also referred to as “monomer a unit”.
  • the (meth) acrylic acid alkyl ester (a1) and the crosslinkable functional group-containing monomer (a2) are also referred to as “monomer (a1)” and “monomer (a2)”, respectively.
  • Tg glass transition temperature
  • the monomer (a1) is a (meth) acrylic acid alkyl ester having a homopolymer Tg of 0 ° C. or higher.
  • the monomer having a Tg of the homopolymer of 0 to 200 ° C. is preferable, and the monomer having a Tg of 0 to 50 ° C. is more preferable.
  • Examples of the monomer (a1) include compounds having a homopolymer Tg of 0 ° C. or higher among compounds represented by CH 2 ⁇ CR 1 —COOR 2 .
  • R 1 is a hydrogen atom or a methyl group
  • R 2 is an alkyl group having 1 to 16 carbon atoms.
  • the alkyl group preferably has 1 to 4 carbon atoms.
  • Acrylic acid alkyl esters such as (35 ° C); methyl methacrylate (105 ° C), ethyl methacrylate (65 ° C), propyl methacrylate (35 ° C), isopropyl methacrylate (81 ° C), tert-butyl methacrylate (118 ° C), n- Examples include methacrylic acid alkyl esters such as butyl methacrylate (20 ° C.), isobutyl methacrylate (48 ° C.), and hexadecyl methacrylate (15 ° C.).
  • the numerical value in parenthesis shows Tg
  • the amount of the monomer (a1) used is 10 to 30% by mass, preferably 15 to 25% by mass, more preferably 18 to 22% by mass.
  • Forming a pressure-sensitive adhesive layer having a high storage modulus by curing the copolymer (A) obtained by copolymerizing the monomer (a1) within the above range with a large amount of an isocyanate-based crosslinking agent (B). Can do.
  • the monomer component forming the copolymer (A) further includes a monomer having a crosslinkable functional group capable of reacting with the isocyanate-based crosslinker (B), that is, a crosslinkable functional group-containing monomer (a2).
  • Examples of the crosslinkable functional group-containing monomer (a2) 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.
  • examples of the acid group include a carboxyl group, an acid anhydride group, a phosphoric acid group, and a sulfuric acid group.
  • the monomer (a2) is preferably a hydroxyl group-containing monomer and a carboxyl group-containing monomer.
  • the pressure-sensitive adhesive layer having a high storage elastic modulus may deteriorate the adhesion to the polarizer (the wettability of the pressure-sensitive adhesive composition to the polarizer).
  • the copolymer (A) is obtained by copolymerization using a hydroxyl group-containing monomer and a carboxyl group-containing monomer in combination, it is possible to suppress a decrease in the adhesiveness (wetting property) of the resulting pressure-sensitive adhesive layer. Can do.
  • Examples of the hydroxyl group-containing monomer include, for example, a hydroxyl group-containing (meth) acrylate, specifically 2-hydroxyethyl (meth) acrylate, 3 Examples thereof include hydroxyalkyl (meth) acrylates such as hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 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.
  • carboxyl group-containing monomer examples 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.
  • Examples of the amino group-containing monomer include amino group-containing (meth) acrylates such as dimethylaminoethyl (meth) acrylate and diethylaminoethyl (meth) acrylate.
  • Examples of 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.
  • Examples of the nitrogen heterocycle-containing monomer include vinyl pyrrolidone, acryloyl morpholine, and vinyl caprolactam.
  • Examples of the cyano group-containing monomer include cyano (meth) acrylate and (meth) acrylonitrile. Two or more monomers (a2) may be used, or three or more monomers may be used.
  • the amount of the crosslinkable functional group-containing monomer (a2) used is 0.1 to 5% by mass, preferably 1 to 5% by mass, more preferably 2%. Is 4% by mass.
  • the amount of the monomer (a2) used is less than or equal to the above upper limit, the crosslink density formed by the copolymer (A) and the crosslinker (B) does not become too high, and the pressure-sensitive adhesive layer is excellent in stress relaxation characteristics. can get.
  • the usage-amount of a monomer (a2) is more than the said lower limit, a crosslinked structure is formed effectively and the adhesive layer which has appropriate intensity
  • the amount of the carboxyl group-containing monomer used is preferably 300 to 2400 parts by mass, more preferably 500 to 2200 parts by mass, and still more preferably 800 to 2000 parts by mass with respect to 100 parts by mass of the hydroxyl group-containing monomer.
  • the monomer component forming the copolymer (A) preferably further contains a (meth) acrylic acid alkyl ester (a3) having a Tg of less than 0 ° C. from the viewpoint of maintaining wettability as an adhesive. . That is, it is preferable that the copolymer (A) further has a structural unit derived from the (meth) acrylic acid alkyl ester (a3).
  • the (meth) acrylic acid alkyl ester (a3) is also referred to as “monomer (a3)”.
  • Examples of the monomer (a3) include compounds having a homopolymer Tg of less than 0 ° C. among compounds represented by CH 2 ⁇ CR 3 —COOR 4 .
  • R 3 is a hydrogen atom or a methyl group
  • R 4 is an alkyl group having 2 to 16 carbon atoms.
  • the alkyl group preferably has 2 to 8 carbon atoms.
  • Examples of the monomer (a3) include ethyl acrylate ( ⁇ 24 ° C.), isopropyl acrylate ( ⁇ 3 ° C.), n-butyl acrylate ( ⁇ 50 ° C.), isobutyl acrylate ( ⁇ 40 ° C.), and hexyl acrylate ( ⁇ 57 ° C.).
  • Alkyl acrylates such as octyl acrylate (-65 ° C), isooctyl acrylate (-58 ° C), 2-ethylhexyl acrylate (-70 ° C), nonyl acrylate (-58 ° C), lauryl acrylate (-3 ° C); Pentyl methacrylate ( ⁇ 5 ° C.), hexyl methacrylate ( ⁇ 5 ° C.), octyl methacrylate ( ⁇ 20 ° C.), isooctyl methacrylate ( ⁇ 45 ° C.), 2-ethylhexyl methacrylate ( ⁇ 10 ° C.), isodecyl methacrylate ( ⁇ 41 ° C.) ), Lauryl methacrylate Doo (-65 ° C.), methacrylic acid alkyl esters such as tetradecyl methacrylate (-72 ° C.) and the like. The numerical value in parenthesis
  • the amount of the monomer (a3) used is preferably 65 to 89.9% by mass, more preferably from the viewpoint of maintaining wettability as an adhesive. 70 to 84% by mass, more preferably 75 to 80% by mass.
  • the monomer component forming the copolymer (A) is, for example, an alkoxyalkyl (meth) acrylate, an alkoxypolyalkylene glycol mono (meth) acrylate, an alicyclic ring as long as the physical properties of the copolymer (A) are not impaired.
  • Other (meth) acrylic esters such as formula groups or aromatic ring-containing (meth) acrylates can be included. That is, the copolymer (A) may further have a structural unit derived from the other (meth) acrylic acid ester.
  • 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.
  • aromatic ring-containing (meth) acrylate By using the aromatic ring-containing (meth) acrylate, the light leakage resistance of the pressure-sensitive adhesive layer can be improved.
  • the total amount of the other (meth) acrylic acid esters is preferably 40% by mass or less, more preferably 20% by mass or less.
  • the monomer component forming the copolymer (A) contains a copolymerizable monomer such as a styrene monomer or vinyl acetate as long as the physical properties of the copolymer (A) are not impaired. Can do. That is, the copolymer (A) may further have a structural unit derived from the copolymerizable monomer.
  • styrenic monomer examples include styrene; methyl styrene, dimethyl styrene, trimethyl styrene, propyl styrene, butyl styrene, hexyl styrene, heptyl styrene, octyl styrene, and other alkyl styrenes; fluorostyrene, chlorostyrene, bromostyrene, Halogenated styrene such as dibromostyrene and iodinated styrene; nitrostyrene, acetylstyrene, and methoxystyrene.
  • the total amount of the copolymerizable monomer used is preferably 40% by mass or less, more preferably 20% by mass or less.
  • (meth) acrylic copolymer (A) is not specifically limited, For example, it can manufacture by a solution polymerization method. Specifically, a polymerization solvent and a monomer component and, if necessary, a chain transfer agent are charged in 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 The reaction system is maintained at a temperature of 100 ° C., preferably 50 to 80 ° C., usually 50 to 90 ° C., preferably 70 to 90 ° C., and allowed to react for 4 to 20 hours. Moreover, you may add suitably a polymerization initiator, a chain transfer agent, a monomer component, and a polymerization solvent during the said polymerization reaction.
  • the copolymer (A) is obtained, for example, by copolymerizing the monomer components described above, but may be a random copolymer or a block copolymer. Among these, a random copolymer is preferable.
  • polymerization solvent examples include aromatic hydrocarbons such as benzene, toluene, and xylene; aliphatic hydrocarbons such as n-pentane, n-hexane, n-heptane, and n-octane; cyclopentane, cyclohexane, and cycloheptane.
  • Cycloaliphatic hydrocarbons such as cyclooctane; ethers such as diethyl ether, diisopropyl ether, 1,2-dimethoxyethane, dibutyl ether, tetrahydrofuran, dioxane, anisole, phenylethyl ether, diphenyl ether; chloroform, carbon tetrachloride, Halogenated hydrocarbons such as 1,2-dichloroethane and chlorobenzene; esters such as ethyl acetate, propyl acetate, butyl acetate and methyl propionate; acetone, methyl ethyl ketone, diethyl ketone, methyl isobutyl ketone, cyclohexane Ketones such as Sanone; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidone; Nitriles such as aceton
  • chain transfer agent examples include normal dodecyl mercaptan and ⁇ -methylstyrene dimer.
  • chain transfer agent By using a chain transfer agent, the molecular weight of the produced copolymer (A) can be controlled.
  • chain transfer agents may be used individually by 1 type, and may use 2 or more types.
  • the chain transfer agent is usually 0.1 parts by mass or less, preferably in the range of 0.01 to 0.09 parts by mass with respect to 100 parts by mass of the monomer component forming the (meth) acrylic copolymer (A). Can be used in any amount.
  • Examples of the polymerization initiator include azo initiators and peroxide initiators. Specific examples include azo compounds such as 2,2′-azobisisobutyronitrile, and peroxides such as benzoyl peroxide and lauroyl peroxide. Among these, an azo compound is preferable. Examples of the azo compound include 2,2′-azobisisobutyronitrile, 2,2′-azobis (4-methoxy-2,4-dimethylvaleronitrile), 2,2′-azobis (2-cyclopropyl).
  • the polymerization initiator is usually in the range of 0.01 to 5 parts by mass, preferably 0.1 to 3 parts by mass with respect to 100 parts by mass of the monomer component forming the (meth) acrylic copolymer (A). Used in quantity.
  • the weight average molecular weight (Mw) measured by the gel permeation chromatography (GPC) method of the (meth) acrylic copolymer (A) is 600,000 or less, preferably 300,000 to 58 in terms of polystyrene. 10,000, more preferably 400,000 to 550,000.
  • the pressure-sensitive adhesive layer having a high storage elastic modulus may deteriorate the adhesion to the polarizer (the wettability of the pressure-sensitive adhesive composition to the polarizer).
  • the copolymer (A) since the copolymer (A) has Mw in the above range, it is possible to suppress a decrease in the adhesiveness (wetting property) of the obtained pressure-sensitive adhesive layer.
  • the molecular weight distribution (Mw / Mn) of the (meth) acrylic copolymer (A) measured by the GPC method is usually 10 or less, preferably 1 to 5, more preferably 1 to 3.
  • 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 copolymer and the content ratio thereof.
  • the (meth) acrylic copolymer (A) is synthesized so that the glass transition temperature (Tg) obtained by the Fox equation is usually ⁇ 80 to 0 ° C., preferably ⁇ 60 to ⁇ 30 ° C. Can do.
  • Tg glass transition temperature
  • Tg is the glass transition temperature (unit: K) of the (meth) acrylic copolymer (A)
  • Tg 1 , Tg 2 ,..., Tg m are the glass transition temperatures of homopolymers composed of the respective monomers ( Unit: K)
  • W 1 , W 2 ,..., W m are weight fractions of the structural units derived from the respective monomers in the copolymer (A).
  • the charging ratio of each monomer to the total monomers at the time of copolymer synthesis can be used.
  • 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 2003) can be used.
  • the content of the (meth) acrylic copolymer (A) is usually 60 to 90% by mass in 100% by mass of the solid content excluding the organic solvent (E) in the composition. More preferably, it is 70 to 89.9% by mass, and particularly preferably 80 to 89.5% 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 of the present invention further contains an isocyanate-based crosslinking agent (B).
  • an isocyanate compound having 2 or more isocyanate groups in one molecule is usually used.
  • a crosslinked body (network polymer) can be formed by crosslinking the (meth) acrylic copolymer (A) with the isocyanate-based crosslinking agent (B).
  • the number of isocyanate groups in the isocyanate-based crosslinking agent (B) is usually 2 or more, preferably 2 to 8, 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 crosslinking agent (B) 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-based crosslinking agent (B) include multimers (for example, dimers or trimers, biurets, isocyanurates) and derivatives (for example, dimers or trimers) of the above isocyanate compounds having 2 or more isocyanate groups. Addition reaction product of polyhydric alcohol and two or more molecules of diisocyanate compound), 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.
  • the isocyanate-based crosslinking agent (B) includes aromatic diisocyanates, aromatic diisocyanate multimers and derivatives, polymers, and aromatic polyisocyanates.
  • isocyanate-based crosslinking agents (B) the reaction product of trimethylolpropane and tolylene diisocyanate or xylylene diisocyanate (L-manufactured by Soken Chemical Co., Ltd.) is that it can improve aging properties and light leakage resistance. 45, TD-75 manufactured by Soken Chemical Co., Ltd.) and isocyanurate of tolylene diisocyanate (2050 manufactured by Nippon Polyurethane Industry Co., Ltd.) are preferable.
  • the isocyanate-based crosslinking agent (B) may be used alone or in combination of two or more.
  • the content of the isocyanate-based crosslinking agent (B) is 10 to 40 parts by mass, preferably 10 to 100 parts by mass of the (meth) acrylic copolymer (A). ⁇ 15 parts by mass.
  • this content is in the above range, a highly rigid pressure-sensitive adhesive layer can be formed, and a phenomenon such as lifting or peeling of the pressure-sensitive adhesive layer when the polarizer is thermally contracted can be suppressed.
  • the pressure-sensitive adhesive composition 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) is usually 1 part by mass or less, preferably 0.01 with respect to 100 parts by mass of the (meth) acrylic copolymer (A). 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.
  • the antistatic agent (D) can be used, for example, to reduce the surface resistance value of the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition of the present invention.
  • 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 cations include pyridinium cation, piperidinium cation, pyrrolidinium cation, pyrroline cation, pyrrole cation, imidazolium cation, tetrahydropyrimidinium cation, dihydropyrimidinium cation, pyrazolium cation, pyrazoli Examples thereof include a nium cation, a tetraalkylammonium cation, a trialkylsulfonium cation, a tetraalkylphosphonium cation, 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
  • Examples of the conductive polymer include polythiophene, polyaniline, polypyrrole, and derivatives thereof.
  • the content of the antistatic agent (D) is usually 3 parts by mass or less, preferably 0.01 to 100 parts by mass with respect to 100 parts by mass of the (meth) acrylic copolymer (A). 3 parts by mass, more preferably 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 applicability.
  • an organic solvent the polymerization solvent demonstrated in the column of the (meth) acrylic-type copolymer (A) is mentioned.
  • a polymer solution containing the (meth) acrylic copolymer (A) and the polymerization solvent obtained by the above copolymerization and an isocyanate crosslinking agent (B) are mixed to prepare an adhesive composition. be able to.
  • the content of the organic solvent (E) 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 of the present invention is prepared by mixing a (meth) acrylic copolymer (A), an isocyanate-based cross-linking agent (B), and other components as required by a conventionally known method. can do.
  • the isocyanate-based crosslinking agent (B) and other components as necessary are blended into the polymer solution containing the polymer obtained when the (meth) acrylic copolymer (A) is synthesized. Is mentioned.
  • the pressure-sensitive adhesive composition of the present invention is used for forming a pressure-sensitive adhesive layer in direct contact with a polarizer.
  • the composition is suitable for bonding a substrate constituting a liquid crystal cell, such as a glass plate, and a polarizer.
  • the pressure-sensitive adhesive layer for polarizing plates of the present invention is formed from the above-mentioned pressure-sensitive adhesive composition.
  • a pressure-sensitive adhesive layer having the following storage elastic modulus characteristics can be formed.
  • the pressure-sensitive adhesive layer of the present invention has a storage elastic modulus (G′1) at 23 ° C. of preferably 0.50 MPa or more, more preferably 0.60 to 1.50 MPa, particularly preferably 0.70 to 1.20 MPa. Yes; Storage elastic modulus (G′2) at 85 ° C. is preferably 0.10 MPa or more, more preferably 0.20 to 0.80 MPa, and particularly preferably 0.30 to 0.50 MPa.
  • the storage elastic modulus is, for example, a value calculated from a dynamic viscoelastic spectrum measured for the laminate by laminating the adhesive layers a plurality of times to produce a laminate having a thickness of about 1.0 mm. .
  • the pressure-sensitive adhesive layer of the present invention is excellent in hardness at room temperature and has improved workability. For example, when the pressure-sensitive adhesive layer is cut, adhesion of the pressure-sensitive adhesive to the cutting blade, stringing of the pressure-sensitive adhesive layer, and the like are prevented.
  • the pressure-sensitive adhesive layer directly laminated on the polarizer is subject to large stress due to the thermal contraction of the polarizer under a high temperature and high humidity heat environment, and is liable to cause problems such as lifting and peeling from the polarizing plate.
  • the storage elastic modulus (G′2) at 85 ° C. is in the above range, such a problem can be prevented even when the polarizer is thermally contracted.
  • the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition of the present invention has a gel fraction of preferably 80% by mass or more, more preferably, from the viewpoints of distortion suppression of the polarizing plate, cohesion, adhesion, and removability. 80 to 98% by mass, more preferably 85 to 95% by mass. When the gel fraction is in the above range, the pressure-sensitive adhesive layer exhibits excellent durability.
  • the pressure-sensitive adhesive layer of the present invention cross-links the (meth) acrylic copolymer (A) with the isocyanate-based cross-linking agent (B), for example, by proceeding with the cross-linking reaction in the above-mentioned pressure-sensitive adhesive composition. Can be obtained.
  • 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 sheet for polarizing plates of the present invention has a pressure-sensitive adhesive layer formed from the above-mentioned pressure-sensitive adhesive composition.
  • 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 are the same as the conditions described in the column “Plastic adhesive layer for polarizing plate”.
  • the thickness of the pressure-sensitive adhesive layer is usually 5 to 75 ⁇ m, preferably 10 to 50 ⁇ m, from the viewpoint of maintaining the 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 the pressure-sensitive adhesive layer of the present invention has a pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition of the present invention, which is directly laminated on at least one surface of a polarizer.
  • polarizing plate is used to include “polarizing film”.
  • the polarizing plate As the polarizing plate, a conventionally known polarizing film can be used.
  • positioned on a polarizer is mentioned.
  • the polarizer protective film since the pressure-sensitive adhesive layer is disposed in direct contact with the polarizer, the polarizer protective film is disposed only on one side of the polarizer, and the polarizer protective film is disposed on both sides of the polarizer. There is no configuration.
  • Examples of the polarizer include a stretched film obtained by stretching a film made of a polyvinyl alcohol-based resin containing a polarizing component.
  • Examples of the polyvinyl alcohol-based resin include polyvinyl alcohol, polyvinyl formal, polyvinyl acetal, and a saponified product of an ethylene / vinyl acetate copolymer.
  • Examples of the polarizing component include iodine or a dichroic dye.
  • the polarizer protective film examples include a film made of a thermoplastic resin.
  • the thermoplastic resin include cellulose resin such as triacetyl cellulose, polyester resin, polyethersulfone resin, polysulfone resin, polycarbonate resin, polyamide resin, polyimide resin, polyolefin resin, (meth) acrylic resin, cyclic polyolefin resin (norbornene) Resin), polyarylate resin, polystyrene resin, polyvinyl alcohol resin, and a mixture of two or more selected from these resins.
  • cellulose resin such as triacetyl cellulose, polyester resin, polyethersulfone resin, polysulfone resin, polycarbonate resin, polyamide resin, polyimide resin, polyolefin resin, (meth) acrylic resin, cyclic polyolefin resin (norbornene) Resin), polyarylate resin, polystyrene resin, polyvinyl alcohol resin, and a mixture of two or more selected from these resins.
  • the thickness of the polarizing plate is usually 10 to 200 ⁇ m, preferably 50 to 100 ⁇ m.
  • a polarizing plate can be reduced in thickness.
  • the pressure-sensitive adhesive layer is formed in direct contact with the polarizer.
  • a polarizing plate with an adhesive layer of the present invention for example, a polarizer protective film, a polarizer, and the adhesive layer are laminated in this order, the adhesive layer, the polarizer protective film, the polarizer, and the above
  • the cover film mentioned above may be arrange
  • the method for forming the pressure-sensitive adhesive layer on the surface of the polarizer is not particularly limited.
  • the method for applying the pressure-sensitive adhesive composition directly to the surface of the polarizer using a bar coater, drying and aging, the pressure-sensitive adhesive sheet for polarizing plate of the present invention There is a method in which the pressure-sensitive adhesive layer possessed by is transferred to the polarizer surface and aged.
  • the conditions for drying and aging, the range of the gel fraction, and the like are the same as the conditions described in the section of [PSA layer for polarizing plate].
  • the thickness of the pressure-sensitive adhesive layer is usually 5 to 75 ⁇ m, preferably 10 to 50 ⁇ m, in terms of dry film thickness.
  • the pressure-sensitive adhesive layer only needs to be formed in contact with the polarizer on at least one surface of the polarizer, and the pressure-sensitive adhesive layer is formed only on one side of the polarizer, and the pressure-sensitive adhesive is formed on both sides of the polarizer.
  • the aspect in which a layer is formed is mentioned.
  • the polarizing plate may be laminated with layers having other functions such as a protective layer, an antiglare layer, a retardation layer, and a viewing angle improving layer.
  • a liquid crystal element is produced by providing the polarizing plate with an 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.
  • Examples of the substrate of the liquid crystal cell include a glass plate.
  • the thickness of the substrate is usually 0.05 to 3 mm, preferably 0.2 to 1 mm.
  • the pressure-sensitive adhesive layer formed using the pressure-sensitive adhesive composition is excellent in adhesion to the substrate (wetting property of the pressure-sensitive adhesive composition to the substrate).
  • 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-Standard polystyrene conversion [Synthesis Example 1] In a reactor equipped with a stirrer, reflux condenser, thermometer and nitrogen inlet tube, 20 parts of methyl acrylate, 0.2 part of 2-hydroxyethyl acrylate, 3 parts of acrylic acid, 76.8 parts of n-butyl acrylate, normal 0.045 part of dodecyl mercaptan and
  • the obtained (meth) acrylic copolymer A1 had a weight average molecular weight (Mw) of 520,000 and a molecular weight distribution (Mw / Mn) of 2.4.
  • Example 1 (1) Preparation of pressure-sensitive adhesive composition
  • the polymer solution obtained in Synthesis Example 1 solid content concentration 30% by mass
  • 100 parts (solid content) of (meth) acrylic copolymer A1 contained in the solution As an isocyanate-based crosslinking agent, 12 parts (solid content) “L-45” (solid content: 45 mass%) manufactured by Soken Chemical Co., Ltd. and “KBM-403” manufactured by Shin-Etsu Chemical Co., Ltd. as a silane coupling agent. (0.2 parts by mass of solid content: 100 parts by mass), and an ethyl acetate solvent was added so that the solid content concentration was 25% by mass to obtain a pressure-sensitive adhesive composition.
  • Examples 2 to 3 Comparative Examples 1 to 7
  • Example 2 In the same manner as in Example 1 except that the polymer solution in Example 1 was changed to the polymer solution obtained in Synthesis Examples 2 to 8 and / or the composition was changed as described in Table 2, An adhesive composition, an adhesive sheet and a polarizing plate with an adhesive layer were obtained.
  • the polarizing plate with the pressure-sensitive adhesive layer obtained in Examples and Comparative Examples (laminated body composed of PET film / pressure-sensitive adhesive layer / polarizer / polarizer protective film) was cut into a size of 70 mm ⁇ 25 mm, and the test piece was cut. Created.
  • the PET film is peeled from the test piece, and the laminate composed of the pressure-sensitive adhesive layer / polarizer / polarizer protective film is laminated on one side of a 2 mm thick glass plate using a laminator roll. Affixed to touch.
  • 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.
  • the PET film is peeled from the test piece, and a laminate composed of an adhesive layer / polarizer / polarizer protective film is laminated on one side of a 0.5 mm thick glass plate using a laminator roll. I stuck it so that it touched.
  • 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. The 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./90% humidity (humidity heat resistance), and the occurrence of foaming, floating and peeling is observed according to the following criteria. And evaluated.
  • AA Appearance defects such as foaming, floating, and peeling were not observed.
  • BB Appearance defects such as foaming, floating, and peeling were slightly observed.
  • CC Appearance defects such as foaming, floating, and peeling were clearly recognized.
  • the PET film is peeled from the test piece, and a laminate composed of an adhesive layer / polarizer / polarizer protective film is laminated on both sides of a 0.5 mm thick glass plate using a laminator roll so that the polarization axes are orthogonal to each other. And it stuck so that an adhesive layer and a glass plate might contact
  • the obtained laminate was held in an autoclave adjusted to 50 ° C./5 atm for 20 minutes to prepare a test plate. This test plate was allowed to stand for 500 hours at a temperature of 80 ° C., and light leakage was observed according to the following criteria.

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