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WO2015141986A1 - Composition adhésive et plaque polarisante la comprenant - Google Patents

Composition adhésive et plaque polarisante la comprenant Download PDF

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Publication number
WO2015141986A1
WO2015141986A1 PCT/KR2015/002435 KR2015002435W WO2015141986A1 WO 2015141986 A1 WO2015141986 A1 WO 2015141986A1 KR 2015002435 W KR2015002435 W KR 2015002435W WO 2015141986 A1 WO2015141986 A1 WO 2015141986A1
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WO
WIPO (PCT)
Prior art keywords
formula
group
adhesive composition
acrylic copolymer
weight
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/KR2015/002435
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English (en)
Korean (ko)
Inventor
최한영
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Dongwoo Fine Chem Co Ltd
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Dongwoo Fine Chem Co Ltd
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Publication of WO2015141986A1 publication Critical patent/WO2015141986A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
    • G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6283—Polymers of nitrogen containing compounds having carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
    • C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
    • C08G18/8009—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203
    • C08G18/8022—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203 with polyols having at least three hydroxy groups
    • C08G18/8029—Masked aromatic polyisocyanates
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/062—Copolymers with monomers not covered by C09J133/06
    • C09J133/066—Copolymers with monomers not covered by C09J133/06 containing -OH groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
    • 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
    • G02F1/133528—Polarisers
    • 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
    • G02F2202/00—Materials and properties
    • G02F2202/28—Adhesive materials or arrangements

Definitions

  • the present invention relates to an adhesive composition and a polarizing plate including the same, and more particularly, to an adhesive composition having high adhesive strength and excellent durability, a polarizing plate and a liquid crystal display device including the same.
  • a liquid crystal display device includes a liquid crystal panel including a liquid crystal cell and a polarizing plate bonded to both surfaces of the liquid crystal cell via an adhesive layer.
  • the pressure-sensitive adhesive for bonding the liquid crystal cell and the polarizing plate is light leakage caused by the durability of heat resistance, moisture heat resistance, thermal shock resistance, cold resistance, etc.
  • the antistatic property for the prevention of static electricity generated when the release film is removed for the polarizing plate bonding must be satisfied at the same time.
  • Japanese Laid-Open Patent Publication No. 2008-285670 discloses an adhesive composition containing an acrylic resin obtained by copolymerizing an (meth) acrylic acid alkyl ester with an ionic liquid containing a polymerizable unsaturated group. It is described as having excellent performance.
  • the ionic liquid containing a polymerizable unsaturated group is insufficient in solubility in an organic solvent, making it difficult to copolymerize various ionic compounds, and the copolymer is uniformly produced when using an ionic monomer having insufficient solubility. There is a problem that the coating is non-uniform because it is not manufactured.
  • the present invention is to solve the above problems, one object of the present invention is to provide a pressure-sensitive adhesive composition with high adhesive strength and excellent durability.
  • Another object of the present invention is to provide a polarizing plate in which the pressure-sensitive adhesive layer made of the pressure-sensitive adhesive composition is laminated.
  • Still another object of the present invention is to provide a liquid crystal display device having the polarizing plate on at least one side of a liquid crystal cell.
  • Another object of the present invention is to provide a method for uniformly preparing an acrylic copolymer containing various ionic functional groups.
  • the present invention provides a pressure-sensitive adhesive composition
  • a pressure-sensitive adhesive composition comprising an acrylic copolymer containing a tertiary amine group and an ionic functional group-containing acrylic copolymer prepared by a nucleophilic substitution reaction of a compound containing a leaving group.
  • the acrylic copolymer containing the tertiary amine group may be prepared by copolymerization of a (meth) acrylate monomer and a monomer simultaneously containing an unsaturated double bond and a tertiary amine group in a molecule.
  • the compound containing a leaving group may be a compound of formula (I).
  • R is an alkyl group of C 1 -C 6 , an alkenyl group or an aralkyl group of C 2 -C 6 ,
  • X is a leaving group
  • the present invention provides a polarizing plate in which the pressure-sensitive adhesive layer made of the pressure-sensitive adhesive composition is laminated.
  • the present invention provides a liquid crystal display device having the polarizing plate on at least one side of the liquid crystal cell.
  • the present invention provides a method for producing an ionic functional group-containing acrylic copolymer comprising the step of nucleophilic substitution reaction of the acrylic copolymer containing the tertiary amine group and the compound containing the leaving group.
  • the pressure-sensitive adhesive composition comprising an ionic functional group-containing acrylic copolymer according to the present invention can be introduced into a variety of ionic functional groups in the acrylic copolymer, the copolymer is uniformly produced, the coating can be formed uniformly, the adhesive force is high Excellent durability
  • One embodiment of the present invention relates to a pressure-sensitive adhesive composition
  • a pressure-sensitive adhesive composition comprising an ionic functional group-containing acrylic copolymer prepared by the nucleophilic substitution reaction of an acrylic copolymer containing a tertiary amine group and a compound containing a leaving group.
  • the acrylic copolymer containing the tertiary amine group may be prepared by copolymerization of a (meth) acrylate monomer and a monomer simultaneously containing an unsaturated double bond and a tertiary amine group in a molecule.
  • the monomer containing the unsaturated double bond and the tertiary amine group simultaneously in the molecule may be a (meth) acrylate containing a tertiary amine group.
  • Specific examples may be one or more selected from compounds of Formulas 1 to 6 below.
  • the monomer containing the unsaturated double bond and the tertiary amine group at the same time in the molecule is preferably contained in 1 to 20% by weight, based on 100% by weight of the acrylic copolymer containing the tertiary amine group, it is 2 to 10% by weight More preferred. If the content is less than 1% by weight, the content of the resulting ionic functional groups are insufficient to secure durability, and if the content is more than 20% by weight, the stability of the coating solution may be insufficient due to the remaining amine groups.
  • the (meth) acrylate monomer may be a (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms.
  • Specific examples include n-butyl (meth) acrylate, 2-butyl (meth) acrylate, t-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, 2-ethylbutyl (meth) acrylate, Ethyl (meth) acrylate, methyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, pentyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl ( Meth) acrylate, n-nonyl (meth) acrylate, isononyl (meth) acrylate, decyl (meth) acrylate, la
  • the (meth) acrylate monomer is preferably contained in 80 to 99% by weight, more preferably 90 to 95% by weight relative to 100% by weight of the total monomers used in the production of the acrylic copolymer. If the content is less than 80% by weight, the adhesive force is not sufficient, and when the content is more than 99% by weight, cohesion may be lowered.
  • the acrylic copolymer containing a tertiary amine group has a (meth) acrylate monomer, a monomer containing an unsaturated double bond and a tertiary amine group simultaneously in a molecule, and a functional group capable of crosslinking with these. It may be a copolymer of monomers.
  • Examples of the monomer having a crosslinkable functional group include a monomer having a hydroxy group, a monomer having a carboxyl group, a monomer having an amide group, and the like as a component that imparts cohesion or adhesive strength by chemical bonding with a crosslinking agent. It can mix and use species.
  • 2-hydroxyethyl (meth) acrylate As a monomer which has a hydroxyl group, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 2-hydroxyethylene glycol (meth) acrylate, 2-hydroxypropylene glycol (meth) acrylate, hydroxyalkylene glycol having 2 to 4 carbon atoms of an alkylene group ( Methacrylate, etc. are mentioned, Among these, 2-hydroxyethyl (meth) acrylate is preferable.
  • Monovalent acids such as (meth) acrylic acid and a crotonic acid; Diacids such as maleic acid, itaconic acid and fumaric acid, and monoalkyl esters thereof; 3- (meth) acryloylpropionic acid; Amberic anhydride ring-opening adduct of 2-hydroxyalkyl (meth) acrylate of 2-3 carbon atoms of alkyl group, Ambernoic acid ring-opening adduct of hydroxyalkylene glycol (meth) acrylate of 2-4 carbon atoms of alkylene group And the compound which ring-opened and added amber acid anhydride to the caprolactone adduct of 2-hydroxyalkyl (meth) acrylate of 2-3 carbon atoms of an alkyl group, Among these, (meth) acrylic acid is preferable.
  • Examples of the monomer having an amide group include (meth) acrylamide, N-isopropylacrylamide, N-tert-butylacrylamide, and of these, (meth) acrylamide is preferable.
  • the monomer which has a crosslinkable functional group is contained in 1 to 20 weight% with respect to 100 weight% of total monomers used for manufacture of an acryl-type copolymer, and it is more preferable that it is 1 to 10 weight%. If the content is less than 1% by weight cohesion may be lowered, if more than 20% by weight may be reduced cohesion.
  • polymerizable monomers in addition to the monomers may be further included in a range that does not lower the adhesion, such as 10% by weight or less, preferably 5% by weight or less.
  • the production method of the copolymer is not particularly limited, and may be prepared using a method such as bulk polymerization, solution polymerization, emulsion polymerization or suspension polymerization, which are commonly used in the art, and solution polymerization is preferable.
  • a solvent, a polymerization initiator, a chain transfer agent for molecular weight control, and the like, which are usually used in the polymerization may be used.
  • the acrylic copolymer has a weight average molecular weight (polystyrene equivalent) measured by gel permeation chromatography (GPC) in general of 50,000 to 2,000,000, preferably 1,000,000 to 2,000,000.
  • GPC gel permeation chromatography
  • the compound containing a leaving group may be a compound of formula (I).
  • R is an alkyl group of C 1 -C 6 , an alkenyl group or an aralkyl group of C 2 -C 6 ,
  • X is a leaving group
  • an alkyl group of C 1 -C 6 means a straight or branched monovalent hydrocarbon having 1 to 6 carbon atoms, for example methyl, ethyl, n-propyl, i-propyl, n-butyl , i-butyl, t-butyl, n-pentyl, n-hexyl and the like.
  • an alkenyl group of C 2 -C 6 means a straight or branched unsaturated hydrocarbon composed of 2 to 6 carbon atoms having one or more carbon-carbon double bonds, for example ethyleneyl, propenyl, moiety. Tenyl, pentenyl, and the like, but are not limited thereto.
  • an aralkyl group refers to a complex group in which an aryl group (aromatic hydrocarbon group) is bonded to carbon of an alkyl group, and examples thereof include, but are not limited to, benzyl, phenethyl, and the like.
  • the C 1 -C 6 alkyl group, C 2 -C 6 alkenyl group and aralkyl group is one or more hydrogen is C 1 -C 6 alkyl group, C 2 -C 6 alkenyl group, C 2 -C 6 Alkynyl group, C 3 -C 10 cycloalkyl group, C 3 -C 10 heterocycloalkyl group, C 3 -C 10 heterocycloalkyloxy group, C 1 -C 6 haloalkyl group, C 1 -C 6 It may be substituted with an alkoxy group, a C 1 -C 6 thioalkoxy group, an aryl group, an acyl group, hydroxy, thio, halogen, amino, alkoxycarbonyl, carboxy, carbamoyl, cyano, nitro and the like. .
  • R is a C 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, or benzyl, optionally substituted with halogen,
  • X is halide, methanesulfonate, trifluoromethanesulfonate, benzenesulfonate or p-toluenesulfonate.
  • Representative compounds of the compound containing the leaving group may be selected from the compounds of the formulas (7) to (14).
  • One embodiment of the present invention relates to a method for producing an ionic functional group-containing acrylic copolymer comprising nucleophilic substitution reaction of an acrylic copolymer containing a tertiary amine group and a compound containing a leaving group.
  • the nucleophilic substitution reaction of the acryl-based copolymer containing the tertiary amine group and the compound containing the leaving group is carried out, for example, as shown in Scheme 1 below. Copolymers are prepared.
  • the nucleophilic substitution reaction can be easily carried out according to methods known in the art.
  • the pressure-sensitive adhesive composition according to an embodiment of the present invention may further include a crosslinking agent and a silane coupling agent.
  • the said crosslinking agent is a component for strengthening the cohesion force of an adhesive by crosslinking a copolymer suitably,
  • the kind is not specifically limited.
  • an isocyanate type compound, an epoxy type compound, etc. are mentioned, These can be used individually or in mixture of 2 or more types.
  • isocyanate compound tolylene diisocyanate, xylene diisocyanate, 2,4-diphenylmethane diisocyanate, 4,4-diphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, tetramethyl xylene diisocyanate, naphthalene Diisocyanate compounds such as diisocyanate; Diisocyanate obtained from 2 moles of an adduct obtained by reacting 3 moles of a diisocyanate compound with 1 mole of a polyhydric alcohol compound such as trimethylolpropane, an isocyanurate obtained by self-condensing 3 moles of the diisocyanate compound, and 3 moles of the diisocyanate compound And polyfunctional isocyanate compounds containing three functional groups such as biuret, triphenylmethanetriisocyanate, and methylenebistriisocyanate, in which the remaining 1
  • epoxy compounds examples include ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, and polypropylene glycol.
  • melamine type compound can be used individually or in mixture of 2 or more types together with an isocyanate type compound and an epoxy type compound.
  • Hexamethylol melamine, hexamethoxymethylmelamine, hexabutoxymethylmelamine, etc. are mentioned as a melamine type compound.
  • the crosslinking agent may be included in an amount of 0.1 to 15 parts by weight, and more preferably 0.1 to 5 parts by weight, based on 100 parts by weight of the acrylic copolymer based on the solid content. If the content is less than 0.1 part by weight, the cohesion force becomes small due to insufficient crosslinking degree, which may cause durability deterioration such as lifting and damage of cutting property. If the content is more than 15 parts by weight, problem of relaxation of residual stress may occur due to excessive crosslinking reaction. have.
  • the type of the silane coupling agent is not particularly limited, and for example, vinylchlorosilane, vinyltrimethoxysilane, vinyltriethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltri Methoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, p-sty Aryltrimethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-acryloxypropyltrimethoxysilane, N-2- (aminoethyl) -3-amin
  • the silane coupling agent is preferably included in an amount of 0.01 to 5 parts by weight, and more preferably 0.05 to 2.5 parts by weight based on 100 parts by weight of the acrylic copolymer based on the solid content. If the content is less than 0.01 parts by weight, the adhesion with the substrate to be bonded under a damp-heat environment may be lowered. If the content is more than 5 parts by weight, bubbles or peeling may occur, which may lower durability.
  • the pressure-sensitive adhesive composition according to an embodiment of the present invention in addition to the components described above, in order to adjust the adhesion, cohesion, viscosity, elastic modulus, glass transition temperature, antistatic properties, etc. required according to the use, tackifying resin, antioxidant, It may further include additives such as corrosion inhibitors, leveling agents, surface lubricants, dyes, pigments, antifoaming agents, fillers, light stabilizers, antistatic agents.
  • the adhesive composition of this invention can be used also as an adhesive for surface protection films as well as the adhesive for polarizing plates for bonding with a liquid crystal cell.
  • it can be used as a protective film, a reflective sheet, a structural adhesive sheet, a photo adhesive sheet, a lane display adhesive sheet, an optical adhesive product, an adhesive for an electronic component, as well as a general commercial adhesive sheet product and a medical patch.
  • One embodiment of the present invention relates to a polarizing plate in which a pressure-sensitive adhesive layer made of the pressure-sensitive adhesive composition is laminated.
  • the thickness of the pressure-sensitive adhesive layer can be adjusted according to the adhesive force, it is usually preferably from 3 to 100 ⁇ m, more preferably from 10 to 100 ⁇ m.
  • Such a polarizing plate can be applied to all conventional liquid crystal display devices, and in particular, a liquid crystal display device including a liquid crystal panel in which the polarizing plate on which the pressure-sensitive adhesive layer is laminated is bonded to at least one surface of a liquid crystal cell can be configured.
  • one embodiment of the present invention relates to a liquid crystal display device having the polarizing plate on at least one side of a liquid crystal cell.
  • n-butyl acrylate BA
  • HOA hydroxyethyl acrylate
  • dimethylaminoethyl acrylate 100 parts by weight was added.
  • purging nitrogen gas for 1 hour to remove oxygen it was maintained at 62 °C.
  • AIBN azobisisobutyronitrile
  • An ionic functional group-containing acrylic copolymer was prepared in the same manner as in Preparation Example 1, except that 5 parts by weight of methyl trifluoromethanesulfonate was used.
  • An ionic functional group-containing acrylic copolymer was prepared in the same manner as in Preparation Example 1, except that 3 parts by weight of methyl trifluoromethanesulfonate was used.
  • An ionic functional group-containing acrylic copolymer was prepared in the same manner as in Preparation Example 1, except that 1 part by weight of methyl trifluoromethanesulfonate was used.
  • An ionic functional group-containing acrylic copolymer was prepared in the same manner as in Preparation Example 4, except that 1 part by weight of iodine methane of Formula 7 was used instead of 1 part by weight of methyl trifluoromethanesulfonate.
  • An ionic functional group-containing acrylic copolymer was prepared in the same manner as in Preparation Example 1, except that 7 parts by weight of the compound of Formula 13 was used instead of 7 parts by weight of methyl trifluoromethanesulfonate.
  • n-butyl acrylate (BA) 90 parts by weight of n-butyl acrylate (BA), 2 parts by weight of hydroxyethyl acrylate (HEA), 90 parts by weight of n-butyl acrylate (BA) instead of 8 parts by weight of dimethylaminoethyl acrylate, hydroxyethyl acryl 2 parts by weight of HEA, Using 8 parts by weight, but proceeding in the same manner as in Preparation Example 1, the ionization reaction did not proceed further.
  • Each component was mixed in the composition shown in Table 1 below (unit: parts by weight), and diluted with ethyl acetate to prepare a pressure-sensitive adhesive composition having a solid content concentration of 15%.
  • the pressure-sensitive adhesive composition prepared above was applied on a release film coated with a silicone release agent to have a thickness of 25 ⁇ m, and dried at 100 ° C. for 1 minute to form a pressure-sensitive adhesive layer.
  • a pressure-sensitive adhesive polarizing plate was prepared by laminating the pressure-sensitive adhesive layer prepared above on an iodine-based polarizing plate having a thickness of 185 ⁇ m by adhesive processing.
  • Crosslinking agent Coronate-L (Japan Urethane Co., Ltd.)
  • Silane coupling agent KBM-403 (Shin-Etsu Corporation)
  • the polarizing plates of Examples 1 to 11 including the ionic functional group-containing acrylic copolymer according to the present invention are compared to the polarizing plates of Comparative Examples 1 and 3 including the acrylic copolymer in which the ionization reaction was not performed.
  • the heat resistance and the heat and humidity resistance were remarkably excellent.
  • Comparative Example 2 including the ionic functional group-containing acrylic copolymer prepared by polymerizing the ionic monomer, the heat resistance and the heat and humidity resistance was low. This is interpreted because the copolymer is not uniformly prepared, so that the coating is nonuniform and bubbles and peeling are likely to be generated.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polarising Elements (AREA)

Abstract

La présente invention concerne : une composition adhésive, qui contient un copolymère acrylique contenant un groupe fonctionnel ionique préparé par la réaction de substitution nucléophile d'un copolymère acrylique contenant un groupe amine tertiaire et d'un composé contenant un groupe partant ; une plaque polarisante comprenant cette dernière ; et un dispositif d'affichage à cristaux liquides. La composition adhésive selon la présente invention a une force d'adhérence élevée et une excellente durabilité.
PCT/KR2015/002435 2014-03-19 2015-03-13 Composition adhésive et plaque polarisante la comprenant Ceased WO2015141986A1 (fr)

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KR10-2014-0032374 2014-03-19
KR1020140032374A KR102145806B1 (ko) 2014-03-19 2014-03-19 점착제 조성물 및 이를 포함하는 편광판

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06322342A (ja) * 1993-05-12 1994-11-22 Konishi Kk 二液型接着剤組成物
JP2005325180A (ja) * 2004-05-12 2005-11-24 Denki Kagaku Kogyo Kk 粘着剤組成物及び粘着シート
JP2007046018A (ja) * 2005-08-12 2007-02-22 Denki Kagaku Kogyo Kk 粘着剤、それを用いた粘着シート、及び粘着シートを用いた電子部品製造方法。
KR20080047031A (ko) * 2006-11-24 2008-05-28 동우 화인켐 주식회사 설폰 또는 설폭사이드 화합물을 포함하는 대전방지성점착제 조성물 및 이를 포함한 편광판
KR20090016241A (ko) * 2007-08-10 2009-02-13 동우 화인켐 주식회사 점착제 조성물 및 이를 포함하는 편광판

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JPH06322342A (ja) * 1993-05-12 1994-11-22 Konishi Kk 二液型接着剤組成物
JP2005325180A (ja) * 2004-05-12 2005-11-24 Denki Kagaku Kogyo Kk 粘着剤組成物及び粘着シート
JP2007046018A (ja) * 2005-08-12 2007-02-22 Denki Kagaku Kogyo Kk 粘着剤、それを用いた粘着シート、及び粘着シートを用いた電子部品製造方法。
KR20080047031A (ko) * 2006-11-24 2008-05-28 동우 화인켐 주식회사 설폰 또는 설폭사이드 화합물을 포함하는 대전방지성점착제 조성물 및 이를 포함한 편광판
KR20090016241A (ko) * 2007-08-10 2009-02-13 동우 화인켐 주식회사 점착제 조성물 및 이를 포함하는 편광판

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