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WO2016072199A1 - Composition adhésive pour plaques polarisantes et plaque polarisante comprenant une couche adhésive - Google Patents

Composition adhésive pour plaques polarisantes et plaque polarisante comprenant une couche adhésive Download PDF

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Publication number
WO2016072199A1
WO2016072199A1 PCT/JP2015/078304 JP2015078304W WO2016072199A1 WO 2016072199 A1 WO2016072199 A1 WO 2016072199A1 JP 2015078304 W JP2015078304 W JP 2015078304W WO 2016072199 A1 WO2016072199 A1 WO 2016072199A1
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WO
WIPO (PCT)
Prior art keywords
sensitive adhesive
pressure
adhesive layer
mass
meth
Prior art date
Application number
PCT/JP2015/078304
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English (en)
Japanese (ja)
Inventor
雄也 米川
隆祐 田中
Original Assignee
綜研化学株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 綜研化学株式会社 filed Critical 綜研化学株式会社
Priority to CN201580057978.4A priority Critical patent/CN107148586A/zh
Priority to KR1020177011075A priority patent/KR20170082517A/ko
Priority to JP2016557507A priority patent/JPWO2016072199A1/ja
Publication of WO2016072199A1 publication Critical patent/WO2016072199A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/10—Adhesives in the form of films or foils without carriers
    • 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
    • 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
    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • C09J7/29—Laminated material
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • 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
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/318—Applications 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.
  • the warpage of the liquid crystal cell under a high temperature and high humidity environment has become a big problem.
  • the conventional pressure-sensitive adhesive layer has low stress relaxation characteristics, and the stress due to thermal contraction (dimensional change) of the polarizer cannot be sufficiently relaxed.
  • Patent Document 1 is obtained by polymerizing a monomer component containing 19 to 99.5% by mass of an alkyl (meth) acrylate having a branched alkyl group having 10 to 24 carbon atoms at the terminal of the ester group (meth).
  • a pressure-sensitive adhesive containing an acrylic polymer is described.
  • Patent Document 2 is an adhesive polarizing plate having a polarizing plate and an adhesive layer provided on the polarizing plate, the polarizing plate having a transparent protective film only on one side of the polarizer, The structure provided in the polarizer of the side which does not have the said transparent protective film is described for the adhesive layer. However, no particular mention is made of the problem of warpage associated with the omission of the transparent protective film.
  • An object of the present invention is an adhesive that can be applied to a configuration in which at least one of the polarizer protective films usually formed on both sides of the polarizer is omitted, and can suppress the bending (bending) of the liquid crystal cell and has excellent durability. It is providing the adhesive composition for polarizing plates which can form an agent layer.
  • the present inventors diligently studied to solve the above problems. As a result, when a specific (meth) acrylic copolymer is used and a crosslinking agent is used, the above-described liquid crystal cell can be prevented from warping (bending) and a pressure-sensitive adhesive layer having excellent durability can be formed. I found that I can do it.
  • the present invention includes, for example, the following [1] to [5].
  • a pressure-sensitive adhesive composition for polarizing plates which comprises a (meth) acrylic copolymer and (B) a crosslinking agent, and is used for forming 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].
  • the storage elastic modulus at 23 ° C. is 0.10 MPa or more, the storage elastic modulus at 85 ° C. is 0.05 MPa or less, and the storage elastic modulus at a certain temperature T ° C. is stored at G ′ T and T + 1 ° C.
  • G ′ T / G ′ T + 1 ⁇ 1.07 is always satisfied when the elastic modulus is G ′ T + 1 and the temperature T is in the range of 23 to 50 ° C.
  • Adhesive layer for the polarizing plate according to [2], wherein G ′ T / G ′ T + 1 ⁇ 1.07 is always satisfied when the elastic modulus is G ′ T + 1 and the temperature T is in the range of 23 to 50 ° C. Adhesive layer.
  • a pressure-sensitive adhesive sheet for polarizing plate having the pressure-sensitive adhesive layer according to [2] or [3].
  • omitted was excellent in durability.
  • the adhesive composition for polarizing plates which can form an agent layer can be provided.
  • 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 a 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 homopolymer having a glass transition temperature (Tg) of less than ⁇ 30 ° C. and a methacrylic acid alkyl ester (a1) of 30% by mass to less than 90% by mass. 10% by mass or more and less than 70% by mass of methacrylic acid alkyl ester (a2) having a temperature (Tg) of ⁇ 30 ° C. or more, and an amount of crosslinkable functional group-containing monomer (a3) of more than 0% by mass and 10% by mass or less
  • the monomer component is a copolymer obtained by copolymerizing the monomer component.
  • the copolymer (A) is usually a structural unit derived from an alkyl methacrylate ester (a1), a structural unit derived from an alkyl methacrylate ester (a2), and a structural unit derived from a crosslinkable functional group-containing monomer (a3). And have.
  • 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”.
  • (a1), (a2) and (a3) are also referred to as “monomer (a1)”, “monomer (a2)” and “monomer (a3)”, respectively.
  • Tg glass transition temperature
  • the monomer (a1) is a methacrylic acid alkyl ester having a homopolymer Tg of less than ⁇ 30 ° C.
  • the monomer having a Tg of the homopolymer of ⁇ 80 to ⁇ 40 ° C. is preferable, and the monomer having a Tg of ⁇ 70 to ⁇ 50 ° C. is more preferable.
  • Examples of the monomer (a1) include compounds having a homopolymer Tg of less than ⁇ 30 ° C. among compounds represented by CH 2 ⁇ C (CH 3 ) —COOR 1 .
  • R 1 is an alkyl group having 6 to 18 carbon atoms.
  • the alkyl group preferably has 6 to 14 carbon atoms, and more preferably 8 to 14 from the viewpoint of obtaining a hydrophobic pressure-sensitive adhesive layer capable of preventing moisture from entering the polarizer.
  • Examples of the monomer (a1) include isooctyl methacrylate ( ⁇ 45 ° C.), isodecyl methacrylate ( ⁇ 41 ° C.), lauryl methacrylate ( ⁇ 65 ° C.), and tetradecyl methacrylate ( ⁇ 72 ° C.).
  • the numerical value in parenthesis shows Tg of the homopolymer of each monomer.
  • Monomers (a1) may be used alone or in combination of two or more.
  • the amount of the monomer (a1) used is 30% by mass or more and less than 90% by mass, preferably 30 to 70% by mass, more preferably 30 to 50% by mass. %.
  • the usage-amount of a monomer (a1) exists in the said range, it is preferable at the point (the balance of a softness
  • the monomer (a2) is a methacrylic acid alkyl ester having a homopolymer Tg of ⁇ 30 ° C. or higher.
  • the monomer having a Tg of the homopolymer of ⁇ 30 to 30 ° C. is preferable, and the monomer having a ⁇ 20 to 0 ° C. is more preferable.
  • Appropriate processability can be imparted to the pressure-sensitive adhesive layer by using the copolymer (A) obtained by copolymerizing the monomer (a2) having a Tg of ⁇ 30 ° C. or higher.
  • Examples of the monomer (a2) include compounds having a homopolymer Tg of ⁇ 30 ° C. or more among compounds represented by CH 2 ⁇ C (CH 3 ) —COOR 2 .
  • R 2 is an alkyl group having 1 to 18 carbon atoms.
  • the alkyl group preferably has 1 to 8 carbon atoms, and more preferably 4 to 8 in view of obtaining a hydrophobic pressure-sensitive adhesive layer capable of preventing moisture from entering the polarizer.
  • Examples of the monomer (a2) include methyl methacrylate (105 ° C.), ethyl methacrylate (65 ° C.), propyl methacrylate (35 ° C.), isopropyl methacrylate (81 ° C.), tert-butyl methacrylate (118 ° C.), and n-butyl methacrylate.
  • the adhesive layer When a (meth) acrylic copolymer containing a structural unit derived from a methacrylic acid alkyl ester having a high homopolymer Tg is used, suitable processability can be imparted to the pressure-sensitive adhesive layer.
  • the alkyl group of the methacrylic acid alkyl ester has a long chain, hydrophobicity can be imparted in addition to processability.
  • the adhesive has a storage elastic modulus at 23 ° C. of not less than 0.10 MPa and is hard, and has a hydrophobic property capable of preventing moisture from entering the polarizer. The agent layer tends to be obtained.
  • Monomer (a2) may be used alone or in combination of two or more.
  • the amount of the monomer (a2) used is 10% by mass or more and less than 70% by mass, preferably 30 to 65% by mass, more preferably 40 to 60% by mass. %.
  • the usage-amount of a monomer (a2) exists in the said range, it is preferable at the point (the balance of a softness
  • the methacrylic acid alkyl ester (a1) having a Tg of less than ⁇ 30 ° C. and the methacrylic acid alkyl ester (a2) having a Tg of ⁇ 30 ° C. or more are copolymerized, so that the Tg is less than ⁇ 30 ° C.
  • this is superior in that the adhesive performance can be expressed while having hydrophobicity.
  • the monomer component forming the copolymer (A) further includes a monomer having a crosslinkable functional group capable of reacting with the crosslinker (B), that is, a crosslinkable functional group-containing monomer (a3).
  • Examples of the monomer (a3) 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.
  • hydroxyl group-containing monomer examples include a hydroxyl group-containing (meth) acrylate, and specific examples include 2-hydroxyethyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate.
  • hydroxyalkyl (meth) acrylates such as 6-hydroxyhexyl (meth) acrylate and 8-hydroxyoctyl (meth) acrylate.
  • the number of carbon atoms of the hydroxyalkyl group in the hydroxyalkyl (meth) acrylate is usually 2 to 8, preferably 2 to 6.
  • 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.
  • acid anhydride group-containing monomer examples 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.
  • the monomer (a3) is at least selected from a hydroxyl group-containing monomer (however, a hydroxyl group-containing monomer excludes a monomer having a carboxyl group) and a carboxyl group-containing monomer from the viewpoint of crosslinkability with the crosslinking agent (B).
  • a hydroxyl group-containing monomer excludes a monomer having a carboxyl group
  • a carboxyl group-containing monomer from the viewpoint of crosslinkability with the crosslinking agent (B).
  • One type is preferable, and a hydroxyl group-containing monomer is more preferable.
  • Monomer (a3) may be used alone or in combination of two or more.
  • the amount of the monomer (a3) used is more than 0% by mass and 10% by mass or less, preferably 2 to 8% by mass, more preferably 4 to 6% by mass.
  • the amount of the monomer (a3) used is less than or equal to the above upper limit, the crosslinking density formed by the copolymer (A) and the crosslinking agent (B) does not become too high, and an adhesive layer excellent in stress relaxation properties is obtained. can get.
  • the usage-amount of a monomer (a3) is more than the said lower limit, a crosslinked structure is formed effectively and the adhesive layer which has appropriate intensity
  • ⁇ Other monomers As a monomer component which forms a copolymer (A), in the range which does not impair the physical property of a copolymer (A), for example, acrylic acid alkylester, alkoxyalkyl (meth) acrylate, alkoxy polyalkylene glycol mono (meth) Other (meth) acrylic acid esters such as acrylate, alicyclic group or aromatic ring-containing (meth) acrylate can also be used. That is, the copolymer (A) may further have a structural unit derived from the other (meth) acrylic acid ester.
  • the acrylic acid alkyl ester is represented, for example, by the formula: CH 2 ⁇ CH—COOR 3 .
  • R 3 is an alkyl group having 1 to 18 carbon atoms.
  • 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.
  • 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 other monomers eg, other (meth) acrylic acid ester, copolymerizable monomer
  • the total amount of other monomers is 0 to 10% by mass.
  • it is 0 to 5% by mass.
  • (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 are charged into a reaction vessel, a polymerization initiator is added in an inert gas atmosphere such as nitrogen gas, and the reaction start temperature is usually 40 to 100 ° C., preferably 50 to 80 ° C. The reaction system is maintained at a temperature of usually 50 to 90 ° C., preferably 70 to 90 ° C., and allowed to react for 4 to 20 hours.
  • a polymerization solvent and a monomer component are charged into a reaction vessel, a polymerization initiator is added in an inert gas atmosphere such as nitrogen gas, and the reaction start temperature is usually 40 to 100 ° C., preferably 50 to 80 ° C.
  • the reaction system is maintained at a temperature of usually 50 to 90 ° C., preferably 70 to 90 ° C., and allowed to react for 4 to 20 hours.
  • polymerization solvent used for the solution polymerization examples include aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic hydrocarbons such as n-pentane, n-hexane, n-heptane and n-octane; cyclopentane, Cycloaliphatic hydrocarbons such as cyclohexane, cycloheptane, cyclooctane; ethers such as diethyl ether, diisopropyl ether, 1,2-dimethoxyethane, dibutyl ether, tetrahydrofuran, dioxane, anisole, phenylethyl ether, diphenyl ether; chloroform, Halogenated hydrocarbons such as carbon tetrachloride, 1,2-dichloroethane, chlorobenzene; esters such as ethyl acetate, propyl acetate, butyl a
  • Examples of the polymerization initiator used for solution polymerization 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. 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 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.
  • monomers (a1) and (a2) having a glass transition temperature (Tg) of the homopolymer in the above range are used in combination, and the glass transition temperature (Tg) determined by the Fox equation is usually ⁇ 70 to ⁇ 20 ° C.
  • the (meth) acrylic copolymer (A) can be synthesized so that the temperature is preferably ⁇ 60 to ⁇ 30 ° C.
  • 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 99.99% by mass in 100% by mass of the solid content excluding the organic solvent in the composition.
  • the amount is preferably 70 to 99.95% by mass, particularly preferably 80 to 99.90% by mass.
  • the pressure-sensitive adhesive composition of the present invention further contains a crosslinking agent (B).
  • the crosslinking agent (B) is particularly limited as long as it is a component capable of causing a crosslinking reaction with the crosslinking functional group derived from the crosslinking functional group-containing monomer (a3) of the (meth) acrylic copolymer (A).
  • an isocyanate compound (B1), a metal chelate compound (B2), and an epoxy compound (B3) can be mentioned.
  • the content of the crosslinking agent (B) is usually 0.01 to 5 parts by mass, more preferably 0, relative to 100 parts by mass of the (meth) acrylic copolymer (A). .05 to 2.5 parts by mass, more preferably 0.1 to 1 part by mass.
  • the content is within the above range, it is preferable in terms of easy balance between durability and stress relaxation characteristics.
  • Isocyanate compound (B1) 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 compound (B1).
  • the number of isocyanate groups in the isocyanate compound (B1) is usually 2 or more, preferably 2 to 8, and more preferably 3 to 6. When the number of isocyanate groups is within the above range, it is preferable from the viewpoint of the crosslinking reaction efficiency between the (meth) acrylic copolymer (A) and the isocyanate compound (B1) and the flexibility of the pressure-sensitive adhesive layer.
  • diisocyanate compound having 2 isocyanate groups in one molecule examples include aliphatic diisocyanate, alicyclic diisocyanate, and aromatic diisocyanate.
  • Aliphatic diisocyanates include ethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, 2-methyl-1,5-pentane diisocyanate, 3-methyl-1,5-pentane diisocyanate, 2,2,4-trimethyl
  • aliphatic diisocyanates having 4 to 30 carbon atoms such as -1,6-hexamethylene diisocyanate.
  • alicyclic diisocyanates include alicyclic rings having 7 to 30 carbon atoms such as isophorone diisocyanate, cyclopentyl diisocyanate, cyclohexyl diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated tolylene diisocyanate, hydrogenated diphenylmethane diisocyanate, and hydrogenated tetramethylxylylene diisocyanate.
  • Group diisocyanates are examples of alicyclic rings having 7 to 30 carbon atoms such as isophorone diisocyanate, cyclopentyl diisocyanate, cyclohexyl diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated tolylene diisocyanate, hydrogenated diphenylmethane diisocyanate, and hydrogenated tetramethylxylylene diisocyanate.
  • aromatic diisocyanate examples include aromatic diisocyanates having 8 to 30 carbon atoms such as phenylene diisocyanate, tolylene diisocyanate, xylylene diisocyanate, naphthylene diisocyanate, diphenyl ether diisocyanate, diphenylmethane diisocyanate, and diphenylpropane diisocyanate.
  • isocyanate compound having 3 or more isocyanate groups in one molecule examples include aromatic polyisocyanate, aliphatic polyisocyanate, and alicyclic polyisocyanate. Specific examples include 2,4,6-triisocyanate toluene, 1,3,5-triisocyanate benzene, and 4,4 ', 4 "-triphenylmethane triisocyanate.
  • Examples of the isocyanate compound (B1) include multimers (for example, dimers or trimers, biurets, isocyanurates), derivatives (for example, many) of the above isocyanate compounds having 2 or 3 or more isocyanate groups. Addition reaction product of a dihydric alcohol and two or more molecules of a diisocyanate compound), and a polymer.
  • Reaction product for example, a trimolecular adduct of tolylene diisocyanate or xylylene diisocyanate
  • reaction product of trimethylolpropane and hexamethylene diisocyanate for example, a trimolecular adduct of hexamethylene diisocyanate
  • polyether polyisocyanate for example, a polyether polyisocyanate
  • Polyester polyisocyanate is mentioned.
  • isocyanate compounds (B1) reaction products of trimethylolpropane and tolylene diisocyanate or xylylene diisocyanate (L-45 manufactured by Soken Chemical Co., Ltd., Soken Chemical Co., Ltd.) can improve the aging property.
  • TD-75 isocyanurate of hexamethylene diisocyanate or tolylene diisocyanate (TSE-100 manufactured by Asahi Kasei Corporation, 2050 manufactured by Nippon Polyurethane Industry Co., Ltd.).
  • the isocyanate compound (B1) may be used alone or in combination of two or more.
  • Metal chelate compound (B2) examples include polyvalent metals such as aluminum, iron, copper, zinc, tin, titanium, nickel, antimony, magnesium, vanadium, chromium, and zirconium, alkoxide, acetylacetone, and ethyl acetoacetate. Examples include a coordinated compound.
  • an aluminum chelate compound (M-12AT manufactured by Soken Chemical Co., Ltd.) is particularly preferable.
  • Specific examples include aluminum isopropylate, aluminum secondary butyrate, aluminum ethyl acetoacetate / diisopropylate, aluminum trisethyl acetoacetate, and aluminum trisacetylacetonate.
  • the metal chelate compound (B2) may be used alone or in combination of two or more.
  • the metal chelate compound (B2) crosslinks the (meth) acrylic copolymer (A) by coordination bond (pseudocrosslinking).
  • the metal chelate compound (B2) is used as the cross-linking agent (B)
  • the cross-linking is maintained at room temperature, and the polymer exhibits cohesiveness. Shows greater flexibility.
  • Epoxy compound (B3) an epoxy compound having 2 or more epoxy groups in one molecule is usually used.
  • 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).
  • 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.
  • the pressure-sensitive adhesive composition can be prepared by mixing the polymer solution containing the (meth) acrylic copolymer (A) and the polymerization solvent obtained by the above copolymerization and the crosslinking agent (B). it can.
  • the content of the organic solvent (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 the (meth) acrylic copolymer (A), the cross-linking agent (B), and other components as required by a conventionally known method. Can do.
  • the cross-linking agent (B) and, if necessary, other components may be added to the polymer solution containing the polymer obtained when the (meth) acrylic copolymer (A) is synthesized. It is done.
  • the pressure-sensitive adhesive composition of the present invention is suitable for use in bonding a substrate constituting a liquid crystal cell and a polarizer.
  • a substrate constituting a liquid crystal cell and a polarizer Even when the thickness of the glass plate constituting the thinned liquid crystal cell is as small as about 0.05 to 1.0 mm, it is suitable for use in bonding the substrate and the polarizer.
  • the gel fraction of the pressure-sensitive adhesive formed from the pressure-sensitive adhesive composition of the present invention is preferably 40% by mass or more, more preferably 50 to 80% by mass, and further preferably 55 to 70% by mass.
  • the said gel fraction is a value measured about the adhesive extract
  • 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 0.10 MPa or more, more preferably 0.10 to 0.20 MPa, particularly preferably 0.10 to 0.15 MPa. Yes; Storage elastic modulus (G′2) at 85 ° C. is preferably 0.05 MPa or less, more preferably 0.01 to 0.04 MPa, and particularly preferably 0.01 to 0.03 MPa.
  • Pressure-sensitive adhesive layer of the present invention is the temperature T of the storage modulus at ° C. G when 'T, the storage modulus at T + 1 ° C. G' and T + 1, in a range of temperature T is 23 ⁇ 50 °C, G ' It is preferable to always satisfy T / G ′ T + 1 ⁇ 1.07, and it is more preferable to always satisfy 1 ⁇ G ′ T / G ′ T + 1 ⁇ 1.06.
  • 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 of the present invention has sufficient flexibility in a high temperature environment, and therefore the thermal contraction (dimensions) of the polarizer.
  • the stress caused by (change) can be sufficiently relaxed. For this reason, even if it exposes to a high temperature environment, the curvature of a to-be-adhered body is reduced, and also a tear of an adhesive layer and peeling of an adhesive layer from a polarizer do not occur easily.
  • the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition of the present invention has a gel fraction of preferably 40% by mass or more, more preferably from the viewpoints of distortion suppression, cohesive strength, adhesive strength, and removability of the polarizing plate. 50 to 80% by mass, more preferably 55 to 70% 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 specifically cross-links the (meth) acrylic copolymer (A) with the cross-linking agent (B) by, for example, advancing the crosslinking reaction in the above-mentioned pressure-sensitive adhesive composition. Is 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 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.
  • the substrate of the liquid crystal cell examples include a glass plate.
  • the thickness of the substrate is usually 0.05 to 3 mm, preferably 0.2 to 1 mm.
  • substrate can be suppressed. Therefore, even when the thickness of the substrate is small (eg, 1 mm or less, preferably 0.2 to 1 mm), the above-mentioned pressure-sensitive adhesive composition can be suitably used for bonding the polarizing plate and 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
  • a reactor equipped with a stirrer, reflux condenser, thermometer and nitrogen inlet tube was charged with 39 parts of lauryl methacrylate, 56 parts of 2-ethylhexyl methacrylate, 5 parts of 2-hydroxyethyl methacrylate and 100 parts of ethyl acetate solvent, and nitrogen gas The temperature was raised
  • the obtained (meth) acrylic copolymer A1 had a weight average molecular weight (Mw) of 910,000 and a molecular weight distribution (Mw / Mn) of 6.2.
  • 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 compound, 0.2 part (solid content) of “TD-75” (solid content: 75% by mass, ethyl acetate solution) manufactured by Soken Chemical Co., Ltd. and Shin-Etsu Chemical Co., Ltd.
  • a pressure-sensitive adhesive composition was obtained by mixing 0.2 parts of “KBM-403” (solid content: 100% by mass).
  • Example 2 Comparative Examples 1 to 3
  • the pressure-sensitive adhesive composition was changed in the same manner as in Example 1 except that the polymer solution was changed to the polymer solution obtained in Synthesis Examples 2 to 5 and the blending composition was changed as shown in Table 2.
  • the polarizing plate with an adhesive sheet and an adhesive layer was 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 water vapor transmission rate was measured as follows according to JIS Z0208.
  • a pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer having a thickness of 50 ⁇ m was prepared in the same manner as described in the column “(2) Preparation of pressure-sensitive adhesive sheet”.
  • the PET film was peeled from this pressure-sensitive adhesive sheet, and a nonwoven fabric was bonded to both sides of the pressure-sensitive adhesive layer (the obtained laminate was referred to as “sheet A”), and cut according to the diameter of the moisture permeable cup.
  • 10 g of calcium chloride was put in a moisture permeable cup (inner diameter 60 mm), and the cut sheet A, rubber packing, and cover ring were set and fixed with bolts.
  • 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.
  • a PET film is peeled from a test piece, and a laminate composed of an adhesive layer / polarizer / polarizer protective film is laminated on one surface of a glass plate having a thickness of 0.7 mm and 40 mm ⁇ 410 mm using a laminator roll. It stuck so that a layer and a glass plate might contact.
  • the obtained laminate was allowed to stand in a 23 ° C./50% RH environment for 24 hours, and then held in an oven at 60 ° C. for 72 hours. One end was fixed to a wall surface perpendicular to the floor surface, and the amount of lifting at the opposite end was measured with a ruler. The warping (bending) was observed according to the following criteria.
  • AA Terminal lift is 3 mm or less
  • BB Terminal lift is more than 3 mm and less than 5 mm
  • CC Terminal lift is 5 mm or more [workability (cutting property)]

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Abstract

L'invention vise à fournir une composition adhésive pour plaques polarisantes, appropriée pour des configurations par lesquelles au moins un film de protection de polariseur normalement formé sur les deux surfaces d'un polariseur est omis, par lesquelles un gauchissement (déformation) de cellules à cristaux liquides peut être supprimé et une couche adhésive ayant une excellente durabilité peut être formée. À cet effet, l'invention concerne une composition adhésive pour plaques polarisantes, caractérisée par le fait qu'elle contient un copolymère de méthacrylate et un agent de réticulation (B) et qu'elle est utilisée pour former une couche adhésive qui vient directement en contact avec des polariseurs. Le copolymère de méthacrylate est obtenu par copolymérisation de composants monomères comprenant : au moins 30 % en masse et moins de 90 % en masse d'un ester d'alkyle méthacrylate (a1) ayant une température de transition vitreuse d'homopolymère inférieure à -30 °C ; au moins 10 % en masse et moins de 70 % en masse d'un ester d'alkyle méthacrylate (a2) ayant une température de transition vitreuse d'homopolymère d'au moins -30 °C; et plus de 0 % en masse et pas plus de 10 % en masse de monomère contenant un groupe fonctionnel de réticulation (a3).
PCT/JP2015/078304 2014-11-04 2015-10-06 Composition adhésive pour plaques polarisantes et plaque polarisante comprenant une couche adhésive WO2016072199A1 (fr)

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KR1020177011075A KR20170082517A (ko) 2014-11-04 2015-10-06 편광판용 점착제 조성물 및 점착제층 부착 편광판
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CN111742023A (zh) * 2018-03-27 2020-10-02 综研化学株式会社 粘合带
JP7585685B2 (ja) 2020-09-24 2024-11-19 三菱ケミカル株式会社 粘着剤組成物、粘着剤および粘着シート

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KR102306382B1 (ko) 2017-04-10 2021-09-29 소켄 케미칼 앤드 엔지니어링 캄파니, 리미티드 점착제 조성물 및 점착 시트
CN111742023A (zh) * 2018-03-27 2020-10-02 综研化学株式会社 粘合带
JP7585685B2 (ja) 2020-09-24 2024-11-19 三菱ケミカル株式会社 粘着剤組成物、粘着剤および粘着シート

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