WO2010079653A9 - 偏光板用粘着剤組成物およびこれを利用した偏光板 - Google Patents
偏光板用粘着剤組成物およびこれを利用した偏光板 Download PDFInfo
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- WO2010079653A9 WO2010079653A9 PCT/JP2009/070099 JP2009070099W WO2010079653A9 WO 2010079653 A9 WO2010079653 A9 WO 2010079653A9 JP 2009070099 W JP2009070099 W JP 2009070099W WO 2010079653 A9 WO2010079653 A9 WO 2010079653A9
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- sensitive adhesive
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- weight
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/625—Polymers of alpha-beta ethylenically unsaturated carboxylic acids; hydrolyzed polymers of esters of these acids
- C08G18/6254—Polymers of alpha-beta ethylenically unsaturated carboxylic acids and of esters of these acids containing hydroxy groups
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- 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
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/08—Homopolymers or copolymers of acrylic acid esters
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
- C09J7/22—Plastics; Metallised plastics
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C09J7/385—Acrylic polymers
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- 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
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- 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
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- 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
- G02B5/3041—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 comprising multiple thin layers, e.g. multilayer stacks
- G02B5/305—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 comprising multiple thin layers, e.g. multilayer stacks including organic materials, e.g. polymeric layers
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- 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
- C08G2170/00—Compositions for adhesives
- C08G2170/40—Compositions for pressure-sensitive adhesives
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
-
- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
- C09J2301/408—Additional features of adhesives in the form of films or foils characterized by the presence of essential components additives as essential feature of the adhesive layer
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- 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
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
Definitions
- the present invention relates to a pressure-sensitive adhesive composition for polarizing plates, and more specifically, a pressure-sensitive adhesive composition for polarizing plates that achieves both effective prevention of light leakage and high durability without using high-energy rays, and The present invention relates to a polarizing plate using the same.
- the liquid crystal element has a structure in which a liquid crystal material is sandwiched between two substrates, and a polarizing plate is attached to the surface of the substrate via an adhesive layer.
- the pressure-sensitive adhesive used for the polarizing plate may be foamed, peeled, crisp, or the like.
- the pressure-sensitive adhesive cannot follow the dimensional change of the polarizing plate, and there is a problem that light leakage occurs and display quality is deteriorated.
- a pressure-sensitive adhesive composition in which the molecular weight range and the ratio between the weight average molecular weight and the number average molecular weight are adjusted to a certain range is proposed (Patent Document 1).
- the adhesive composition which adjusted the refractive index and improved durability by using the solid tackifier which has a specific refractive index is proposed (patent document 2 and 3).
- the gel fraction of the pressure-sensitive adhesive composition to be used should be increased.
- the polymer which comprises an adhesive composition should be bridge
- Patent Document 4 discloses an adhesive that achieves a high gel fraction using UV light and prevents light leakage.
- the material constituting the pressure-sensitive adhesive sheet may be adversely affected by the UV light.
- the pressure-sensitive adhesive obtained by the method of Patent Document 4 is hardly sufficient in terms of durability, as shown in the examples described later.
- Patent Document 5 based on the above-mentioned aging crosslinking method, the upper limit is set to 90% in spite of the higher gel fraction being better for preventing light leakage as described above.
- the reason for this is that, as described in paragraph [0043] of this patent document, when the gel fraction is increased, the relaxability and adhesiveness are lowered and the durability is deteriorated. Therefore, in the examples, there is disclosed an example in which a positive intrinsic birefringent material is blended in the pressure-sensitive adhesive composition as a light leakage prevention component, and the pressure-sensitive adhesive composition itself of Patent Document 5 is substantially sufficient in light resistance. Leakage performance cannot be achieved, and it is judged that a light leakage prevention component is necessary for practical use.
- an object of the present invention is to provide a pressure-sensitive adhesive composition for a polarizing plate that is excellent in durability and excellent in light leakage prevention effect.
- TDI tolylene diisocyanate
- the present invention Next component (A) thru
- this invention is a polarizing plate which provides the adhesive layer formed from the said adhesive composition for polarizing plates on the at least one surface of a polarizing film.
- the pressure-sensitive adhesive composition for polarizing plates of the present invention can effectively prevent light leakage by using this as a pressure-sensitive adhesive such as a polarizing film.
- a pressure-sensitive adhesive such as a polarizing film.
- this coating film can prevent the occurrence of white turbidity.
- the component (A) acrylic polymer used in the polarizing plate pressure-sensitive adhesive composition of the present invention is at least a monomer component (a1) (meth) acrylic acid alkyl ester, a monomer component (a2) carboxyl group-containing monomer, and It is obtained by copolymerizing a benzene ring monomer as the monomer component (a3).
- the (meth) acrylic acid alkyl ester of the monomer component (a1) is not particularly limited, but preferably has an alkyl group having 1 to 12 carbon atoms which may be branched.
- Examples of the carboxyl group-containing monomer as the monomer component (a2) include (meth) acrylic acid, 2-carboxyethyl (meth) acrylate, 3-carboxypropyl (meth) acrylate, and 4-carboxybutyl (meth) acrylate. , Itaconic acid, crotonic acid, maleic acid, fumaric acid and maleic anhydride.
- the monomer component (a3) is copolymerized to improve the compatibility between the resulting component (A) acrylic polymer and component (B) TDI crosslinking agent. It has an action.
- the benzene ring-containing monomer include phenyl acrylate, phenoxyethyl (meth) acrylate, benzyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, ethylene oxide-modified nonylphenol (meth) acrylate, and hydroxyethylated ⁇ -naphthol.
- phenoxyethyl acrylate and benzyl acrylate are preferably used because they have good copolymerizability and excellent transparency when formed into a coating film.
- the content of the monomer component (a1) and the monomer component (a2) in the component (A) is 45 to 94.9% by mass, preferably 50 to 85% by mass of the monomer component (a1), and the monomer component (a2) Is 0.1 to 5% by mass, preferably 1 to 3% by mass.
- the benzene ring-containing monomer of the monomer component (a3) used in the present invention needs to be contained in a molar amount of 5 times or more with respect to the TDI-based crosslinking agent as the component (B).
- This can be represented by the molar ratio of the monomer component (a3) and the TDI-based isocyanate. If the amount is 5 times or less, an isocyanate crosslinking agent described later is not compatible with the polymer, and the coating film may become cloudy.
- the content of the monomer component (a3) in the component (A) is 5 to 50% by mass, preferably 12 to 49% by mass.
- acrylic polymer of component (A) in addition to the monomer components (a1) to (a3), other copolymerizable monomers can be contained.
- (meth) acrylic acid alkoxy ester, a hydroxyl group-containing monomer, an amino group-containing monomer, an amide-containing monomer and the like can be mentioned.
- Examples of the (meth) acrylic acid alkoxyester include 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 2-methoxypropyl (meth) acrylate, and 3-methoxypropyl (meth) acrylate.
- Examples include 2-methoxybutyl (meth) acrylate and 4-methoxybutyl (meth) acrylate.
- Examples of the hydroxyl group-containing monomer include 2-hydroxyethyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and 6-hydroxyhexyl (meth).
- Examples include acrylate, 1,4-cyclohexanedimethanol mono (meth) acrylate, chloro-2-hydroxypropyl acrylate, diethylene glycol mono (meth) acrylate, and allyl alcohol.
- amino group-containing monomer examples include dimethylaminoethyl (meth) acrylate and diethylaminoethyl (meth) acrylate.
- amide-containing monomer examples include (meth) acrylamide and (meth) N-methylolacrylamide.
- the monomer having reactivity with the TDI crosslinking agent inhibits the reaction between the carboxyl group-containing monomer and the TDI crosslinking agent and the reaction between the TDI crosslinking agent and water. Since there exists a possibility, it is preferable to set it as 2 mass% or less in all the monomers, Preferably it is 1 mass% or less.
- the component (A) of the present invention uses monomers such as the monomer components (a1) to (a3), which are obtained by a conventionally known polymerization method such as a solution polymerization method, a bulk polymerization method, an emulsion polymerization method, or a suspension polymerization method. It can be produced by polymerization. However, those prepared by a solution polymerization method or a bulk polymerization method which do not contain a polymerization stabilizer such as an emulsifier and a suspending agent are more preferable.
- the weight average molecular weight of the component (A) obtained as described above is 500 to 2,000,000, preferably 80 to 1,500,000. When the weight average molecular weight is less than 500,000, foaming or peeling is likely to occur at the time of wet heat. When the weight average molecular weight is more than 2 million, the viscosity increases and the workability deteriorates.
- a weight average molecular weight means the value calculated
- the TDI crosslinking agent of component (B) used in the present invention reacts with the carboxyl group of the acrylic polymer of component (A) to form a large amount of crosslinked amide bonds, increasing the elasticity at the molecular level, It is intended to relieve momentary stress when the polarizing plate contracts and prevent peeling.
- the TDI-based crosslinking agent include tolylene diisocyanate and tolylene diisocyanate derivatives.
- an epoxy-based crosslinking agent, a metal chelate crosslinking agent, an aziridine compound, or the like may be used in combination.
- the compounding amount of the component (B) in the pressure-sensitive adhesive composition for polarizing plates of the present invention is 4 to 12 parts with respect to 100 parts by weight of the component (A) (hereinafter sometimes simply referred to as “parts”). It is preferably 6 to 10 parts. If the amount is less than 4 parts, peeling may occur in a moist heat environment. If the amount is more than 12 parts, the coating liquid may be whitened at the time of coating, or the viscosity may increase excessively and workability may be deteriorated.
- the reaction of the isocyanate group of the TDI-based crosslinking agent and the carboxyl group of the acrylic polymer of component (A) is relatively slow, in parallel with the reaction of the isocyanate group and the carboxyl group, the pressure-sensitive adhesive composition is changed from the polarizing film.
- the moisture that has migrated inside reacts with the isocyanate groups to produce polyurethane. In this way, the durability is further improved by forming polyurethane in the highly crosslinked acrylic polymer.
- the silane coupling agent of component (C) used in the present invention is a silane coupling agent containing a group that reacts with a carboxyl group contained in the acrylic polymer of component (A).
- the pressure-sensitive adhesive can be firmly adhered to the glass, and peeling can be prevented in a moist heat environment.
- component (C) silane coupling agent examples include 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2- ( Epoxy-containing silane coupling agents such as 3,4-epoxycyclohexyl) ethyltrimethoxysilane, and amino group-containing silane coupling agents such as 3-aminopropyltrimethoxysilane and N-2 (aminoethyl) 3-aminopropyltrimethoxysilane Etc.
- the compounding amount of component (C) in the pressure-sensitive adhesive composition for polarizing plates of the present invention is 0.05 to 1 part, preferably 0.1 to 0.5 part, relative to 100 parts of component (A). is there. If the amount is less than 0.05 parts, peeling is likely to occur in a moist heat environment. If the amount is more than 1 part, the silane coupling agent bleeds in a high temperature environment, and conversely, peeling is likely to occur.
- the pressure-sensitive adhesive composition for polarizing plates of the present invention preferably has a gel fraction of 91% or more.
- the distortion of a polarizing film can be suppressed and it is effective also in processing appropriateness and dent generation.
- the gel fraction is less than 91%, light leakage occurs and the area increases, and the luminance of the light leakage increases.
- Preparation of the pressure-sensitive adhesive composition for polarizing plate of the present invention is carried out by blending the above components (A) to (C) and optional components as necessary, and mixing them according to a conventional method.
- optional components include antioxidants, ultraviolet absorbers, plasticizers, antistatic agents, and the like, and these can be blended within a range that does not impair the effects of the present invention.
- the pressure-sensitive adhesive composition was applied to at least one surface on the support according to a conventional method, and after coating,
- the pressure-sensitive adhesive layer may be formed by drying and crosslinking treatment.
- As the support a polyester film having a surface peel-treated can be used.
- the thickness of the pressure-sensitive adhesive layer is usually about 10 to 30 ⁇ m, preferably about 15 to 25 ⁇ m.
- the polarizing plate of the present invention can be obtained by providing an adhesive layer formed from the above-mentioned adhesive composition for polarizing plates on at least one surface of the polarizing film.
- the thickness of the pressure-sensitive adhesive layer provided on the polarizing film is usually about 10 to 30 ⁇ m, preferably about 15 to 25 ⁇ m.
- the pressure-sensitive adhesive composition is coated on a polarizing film having a water content of 0.5 to 5% by mass, dried and aged, or a support. It is preferable that the pressure-sensitive adhesive layer is formed by laminating the coated and dried coating film on the polarizing film.
- the pressure-sensitive adhesive layer is formed by laminating the coated and dried coating film on the polarizing film.
- the polarizing film used in the present invention layers having other functions may be laminated, and specifically, an elliptically polarizing film, a retardation film and the like are included. Among these, particularly when a polarizing film or an elliptically polarizing film is used, the stress relaxation property of the pressure-sensitive adhesive composition for polarizing plates of the present invention can be exhibited more.
- the type of liquid crystal element in which the polarizing plate of the present invention obtained as described above is used is not particularly limited, and may be any of TN mode, VA mode, IPS mode, OCB mode, Among these, since the light leakage prevention property of the polarizing plate of this invention is exhibited more, it can be used conveniently for a TN mode liquid crystal element.
- the weight average molecular weight (Mw) of the acrylic polymers produced in Production Examples 1 to 10 and the ratio (Mw / Mn) of the weight average molecular weight (Mw) to the number average molecular weight (Mn) were measured according to the following GPC measurement conditions. The values are also shown in Table 1.
- Measuring device HLC-8120GPC (manufactured by Tosoh Corporation)
- GPC column configuration The following five columns (all manufactured by Tosoh Corporation) (1) TSK-GEL HXL-H (guard column) (2) TSK-GEL G7000HXL (3) TSK-GEL GMHXL (4) TSK-GEL GMHXL (5) TSK-GEL G2500HXL Diluted with tetrahydrofuran so that the sample concentration is 1.0 mg / cm 3
- Mobile phase solvent Tetrahydrofuran Flow rate: 1 ml / min Column temperature: 40 ° C
- Example 1 Production of polarizing plate: (Preparation of adhesive composition) For 100 parts of the acrylic polymer (solid content) of the acrylic polymer solution obtained in Production Example 1, 8 parts of Coronate L (manufactured by Nippon Polyurethane) as a TDI curing agent and Tetrad X (Mitsubishi) as an epoxy curing agent 0.25 part of Gas Chemical Co., Ltd.) and 0.2 part of KBM-403 (manufactured by Shin-Etsu Chemical Co., Ltd.) as a silane coupling agent were added, and these were mixed well to obtain an adhesive composition. This was designated as Product 1 of the present invention.
- Coronate L manufactured by Nippon Polyurethane
- Tetrad X Mitsubishi Chemical Co., Ltd.
- KBM-403 manufactured by Shin-Etsu Chemical Co., Ltd.
- the obtained pressure-sensitive adhesive composition was applied to the surface of the peeled polyester film and dried to obtain a pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer having a thickness of 20 ⁇ m.
- This pressure-sensitive adhesive sheet was affixed to one side of a polarizing film having a moisture content of 2% and aged for 7 days under conditions of a temperature of 23 ° C. and a humidity of 50% RH to obtain a polarizing plate.
- Present invention 2-6, comparison 1-8 A pressure-sensitive adhesive composition was obtained in the same manner as in Example 1 except that the acrylic polymer and the tackifying resin were changed as shown in Table 2 below. These were designated as inventive products 2 to 6 and comparative products 1 to 8, respectively. Moreover, the polarizing plate was produced like Example 1 using the obtained adhesive composition.
- BA butylene acrylate
- 2HEA 2-hydroxyethyl acrylate
- AA acrylic acid
- the pressure-sensitive adhesive composition obtained above was applied to the surface of the peeled polyester and dried to obtain a pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer having a thickness of 20 ⁇ m.
- This pressure-sensitive adhesive sheet is attached to one side of a polarizing film with a discotic liquid crystal aligned, and 30 minutes after being applied, ultraviolet light (UV) is applied from the release sheet side using an electrodeless lamp / H bulb manufactured by Fusion, and an illuminance of 600 mW. / Cm 2 , and irradiation was performed under conditions of 150 mJ / cm 2 . Thereafter, the film was aged for 7 days at 23 ° C. and 50% RH to obtain a polarizing plate.
- UV ultraviolet light
- Comparative product 10 (Example 8 of 2008-144125) A reactor equipped with a stirrer, a reflux condenser, a thermometer and a nitrogen introduction tube was charged into a butyl acrylate (BA) / benzyl acrylate (BzA) / acrylic acid (AA) part by weight of 100 / 0.5 / 2. A polymerizable monomer and 239 parts of ethyl acetate (EtAc) were added, and the air in the reaction vessel was replaced with nitrogen gas. Next, the temperature was raised to 60 ° C. with stirring in a nitrogen atmosphere, 0.3 parts of azobisisobutyronitrile (AIBN) was added, and the mixture was reacted in a nitrogen gas stream for 4 hours. After completion of the reaction, an acrylic polymer solution was obtained. This was designated as Comparative Product 10.
- BA butyl acrylate
- BzA benzyl acrylate
- AA acrylic acid
- BA butyl acrylate
- BzA benzyl acrylate
- acrylic acid AA
- Test example 1 For the polarizing plates produced using the inventive product 1-6 and the comparative product 1-8 obtained above, their gel fraction, ratio of benzene ring monomer / TDI crosslinking agent, durability, light leakage prevention property and The state of the coating film was evaluated by the following evaluation method. In addition, the durability, the light leakage prevention property, and the state of the coating film of each polarizing plate obtained from the comparative product 9-11 were similarly evaluated. These results are summarized in Table 2.
- ⁇ Durability evaluation method> The polarizing plate is cut into a size of 150 mm ⁇ 250 mm, attached to one side of a glass plate using a laminator roll, and then held in an autoclave adjusted to 50 ° C. and 5 atm for 20 minutes to obtain a test plate. Created. Two similar test plates were prepared and left for 500 hours under the conditions of a temperature of 60 ° C. and a humidity of 90% RH and for 500 hours under the conditions of a temperature of 80 ° C., respectively. It was visually observed and evaluated. (Standard) ⁇ : Appearance defects such as peeling were not observed ⁇ : Appearance defects such as peeling were slightly observed ⁇ : Appearance defects such as peeling were clearly observed
- the obtained pressure-sensitive adhesive composition was applied to the surface of a polyester film that had been subjected to a release treatment so that the thickness after drying was 20 ⁇ m, and after drying, the polyester film was laminated to the other surface, and 23 ° C., 50%
- a test piece was prepared by aging in RH for 7 days. The state of the coating film on the test piece after aging was visually confirmed.
- the polarizing plate using the pressure-sensitive adhesive composition of the present invention is excellent in adhesiveness and light leakage prevention property, has no durability, and has excellent durability.
- the film was shown to be transparent.
- the polarizing plates of Comparative products 1 to 8 had defects in durability, light leakage prevention properties, or white turbidity of the coating film.
- the polarizing plate using the pressure-sensitive adhesive composition (Comparative product 9) obtained in Example 1 of 2008-31214 peeling or the like occurs and there is a defect in durability.
- the polarizing plate using the pressure-sensitive adhesive composition (Comparative products 10 and 11) obtained in Example 8 and Example 11 had a defect in light leakage prevention.
- the pressure-sensitive adhesive composition of the present invention effectively prevents light leakage, has excellent durability, and can suppress the occurrence of peeling or the like even under high temperature and high humidity conditions. Therefore, this can be suitably used as a pressure-sensitive adhesive composition for polarizing plates.
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- Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polarising Elements (AREA)
- Adhesive Tapes (AREA)
- Polyurethanes Or Polyureas (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
次の成分(A)ないし(C)
(A)少なくとも次のモノマー成分(a1)ないし(a3)を共重合する
ことにより得られ、重量平均分子量が50万~200万であり、か
つ重量平均分子量(Mw)と数平均分子量(Mn)の比(Mw/
Mn)が8以下であるアクリル系ポリマー 100重量部
(a1)(メタ)アクリル酸アルキルエステルモノマー
45~94.9質量%
(a2)カルボキシル基含有モノマー 0.1~5質量%
(a3)トリレンジイソシアネート系架橋剤に対して5倍モル以上で
あるベンゼン環含有モノマー 5~50質量%
(B)トリレンジイソシアネート系架橋剤 4~12重量部
(C)カルボキシル基と反応性を有するシランカップリング剤
0.05~1重量部
を含有し、かつゲル分率が91%以上であることを特徴とする偏光板用粘着剤組成物である。
撹拌機、還流冷却器、温度計及び窒素導入管を備えた反応装置に、それぞれ表1に示す重量部の共重合性モノマー、重合開始剤及び溶剤を加え、反応容器内の空気を窒素ガスで置換した。次いで、窒素雰囲気下で撹拌しながら68℃に昇温した後、アゾビスイソブチロニトリル(AIBN)を添加して、8時間反応させた。反応終了後、アクリル系ポリマー溶液を得た。
測定装置:HLC-8120GPC(東ソー社製)
GPCカラム構成:以下の5連カラム(すべて東ソー社製)
(1)TSK-GEL HXL-H (ガードカラム)
(2)TSK-GEL G7000HXL
(3)TSK-GEL GMHXL
(4)TSK-GEL GMHXL
(5)TSK-GEL G2500HXL
サンプル濃度:1.0mg/cm3となるように、テトラヒドロフランで希釈
移動相溶媒:テトラヒドロフラン
流量: 1ml/min
カラム温度:40℃
偏光板の作製:
(粘着剤組成物の調製)
製造例1により得られたアクリル系ポリマー溶液のアクリル系ポリマー(固形分)100部に対して、TDI系硬化剤としてコロネートL(日本ポリウレタン社製)8部、エポキシ系硬化剤としてテトラッドX(三菱ガス化学社製)0.25 部、シランカップリング剤としてKBM-403(信越化学工業株式会社製)0.2部を添加し、これらを充分混合して粘着剤組成物を得た。これを本発明品1とした。
得られた粘着剤組成物を、剥離処理したポリエステルフィルムの表面に塗布し、乾燥させることにより、厚さ20μmの粘着剤層を有する粘着シートを得た。この粘着シートを水分含有量2%の偏光フィルムの片面に貼り付け、温度23℃、湿度50%RHの条件で7日間熟成させて偏光板を得た。
アクリル系ポリマーと粘着付与樹脂を下記表2のように代えた以外は実施例1と同様にして粘着剤組成物を得た。なお、これらをそれぞれ本発明品2~6、比較品1~8とした。また、得られた粘着剤組成物を用い、実施例1と同様にして偏光板を作製した。
撹拌機、還流冷却器、温度計及び窒素導入管を備えた反応装置に、ブチレンアクリレート(BA)/2-ヒドロキシエチルアクリレート(2HEA)/アクリル酸(AA)=98/1.5/0.5である重量部の共重合性モノマー及び酢酸エチル(EtAc)90部を加え、反応容器内の空気を窒素ガスで置換した。次いで、窒素雰囲気下で撹拌しながら68℃に昇温した後、アゾビスイソブチロニトリル(AIBN)0.05部を添加して、窒素ガス気流中8時間反応させた。反応終了後、アクリル系ポリマー溶液を得た。
撹拌機、還流冷却器、温度計及び窒素導入管を備えた反応装置に、ブチルアクリレート(BA)/ベンジルアクリレート(BzA)/アクリル酸(AA)=100/0.5/2の重量部の共重合性モノマー及び酢酸エチル(EtAc)239部を加え、反応容器内の空気を窒素ガスで置換した。次いで、窒素雰囲気下で撹拌しながら60℃に昇温した後、アゾビスイソブチロニトリル(AIBN)0.3部を添加して、窒素ガス気流中4時間反応させた。反応終了後、アクリル系ポリマー溶液を得た。これを比較品10とした。
上記より得られたアクリル系ポリマー溶液のアクリル系ポリマー(固形物)100部に対して、TDI系硬化剤コロネートL(日本ポリウレタン社製)5部、アルミキレート化合物ALCH-TR(川研ファインケミカル社製)1,3部、シランカップリング剤KBM-403(信越化学工業株式会社製)0.1部を添加し、充分混合して粘着組成物を得た。また、偏光板作製方法は実施例1と同様に行い、偏光板を作成した。
撹拌機、還流冷却器、温度計及び窒素導入管を備えた反応装置に、ブチルアクリレート(BA)/ベンジルアクリレート(BzA)/アクリル酸(AA)=100/20/2の重量部の共重合性モノマー及び酢酸エチル(EtAc)285部を加え、反応容器内の空気を窒素ガスで置換した。次いで、窒素雰囲気下で撹拌しながら60℃に昇温した後、アゾビスイソブチロニトリル(AIBN)0.3部を添加して、窒素ガス気流中4時間反応させた。反応終了後、アクリル系ポリマー溶液を得た。これを比較品11とした。
上記で得た本発明品1-6及び比較品1-8を用いて作製した偏光板について、それらのゲル分率、ベンゼン環モノマー/TDI系架橋剤の比率、耐久性、光漏れ防止性および塗膜の状態を以下の評価方法で評価した。また、比較品9-11から得られたそれぞれの偏光板の耐久性、光漏れ防止性、および塗膜の状態も同様に評価した。これらの結果を表2にまとめて示す。
得られた粘着剤組成物と乾燥後の厚みが20μmになるように剥離処理したポリエステルの表面に塗布し、乾燥させた後、もう一方に面に剥離処理したポリエステルフィルムを張り合わせて、23℃、50%RHで7日間熟成させて、試験片を作製した。試験片から粘着剤約0.1gをサンプル瓶に採取し、酢酸エチル30ccを加えて24時間振とうした後、該サンプル瓶の内容物を200メッシュのステンレス製金綱でろ別し、金綱上の残留物を100℃で2時間乾燥させて、乾燥重量を測定し、次式より求めた。
ゲル分率(%)=(乾燥重量/採取した粘着剤重量)×100
以下の式により求めた。
BC / BM
ベンゼン環モノマー/架橋剤比率(%) = ----------
IC / IM
(式中、BCはベンゼン環モノマーの含有量(質量%)を、BMはベンゼン環モノマーの分子量を、ICはTDI系架橋剤の含有量(質量%)を、IMはTDI系架橋剤の分子量を表す)
偏光板を、150mm×250mmの大きさに裁断し、ガラス板の片面にラミネーターロールを用いて貼着し、次いで、50℃、5気圧に調整されたオートクレーブに20分間保持して、試験板を作成した。同様の試験板を2枚作成し、それぞれ、温度60℃、湿度90%RHの条件下で500時間放置、及び温度80℃の条件下で500時間放置し、以下の基準でハガレの発生等を目視で観察し評価した。
(基準)
○:ハガレ等の外観不良が認められなかった
△:ハガレ等の外観不良がわずかに認められた
×:ハガレ等の外観不良が明らかに認められた
偏光板2枚を、19インチワイドTNモニタ(型番:BenQ FP93VW)の表裏面に相互に直交ニコル位になるようにラミネーターロールを用いて貼着し、次いで、50℃、5気圧に調整されたオートクレーブに20分間保持して、試験板を作成した。作成した試験板を、70℃の条件下で500時間放置し、光漏れを目視で観察し、以下の基準で評価した。
(基準)
○:光漏れは全く見られなかった
△:わずかに光漏れが見られた
×:明らかな光漏れが見られた
得られた粘着剤組成物を乾燥後の厚みが20μmになるように剥離処理したポリエステルフィルムの表面に塗布し、乾燥させた後、もう一方の面にポリエステルフィルムを張り合わせて、23℃、50%RHで7日間熟成させて、試験片を作製した。熟成後の試験片の塗膜の状態を目視で確認した。
偏光フィルムを10cm×10cmの大きさに裁断し、23℃、65%RH条件下に24時間放置した後、その重量を秤量した(これを加熱前重量とする)。次いで、この偏光フィルムを120℃で1時間加熱した後、秤量した(これを加熱後重量とする)。偏光フィルムの水分含有量を下記式によって求めた。
水分含有量(%)=(加熱前重量-加熱後重量)/加熱前重量×100
本発明品2の水分含有量2%の偏光フィルムを水分量0.2%(比較品12)及び6.5%(比較品13)の偏光フィルムに代えた以外は上記方法と同様にそれぞれの偏光板を作成した。また、それらのゲル分率、ベンゼン環モノマー/TDI系架橋剤の比率、耐久性、光漏れ防止性および塗膜の状態を上記と同様の評価方法で評価した。これらの結果を表3に示す。
Claims (4)
- 次の成分(A)ないし(C)
(A)少なくとも次のモノマー成分(a1)ないし(a3)を共
重合することにより得られ、重量平均分子量が50万~2
00万であり、かつ重量平均分子量(Mw)と数平均分子
量(Mn)の比(Mw/Mn)が8以下であるアクリル系
ポリマー 100重量部
(a1)(メタ)アクリル酸アルキルエステルモノマー
45~94.9質量%
(a2)カルボキシル基含有モノマー 0.1~5質量%
(a3)トリレンジイソシアネート系架橋剤に対して5倍モル以
上であるベンゼン環含有モノマー 5~50質量%
(B)トリレンジイソシアネート系架橋剤 4~12重量部
(C)カルボキシル基と反応性を有するシランカップリング剤
0.05~1重量部
を含有し、かつゲル分率が91%以上であることを特徴とする偏光板用粘着剤組成物。 - 支持体の少なくとも一方の面に請求項1項記載の偏光板用粘着剤組成物から形成される粘着剤層を設けてなる偏光板用粘着シート。
- 偏光フィルムの少なくとも一方の面に請求項1項記載の偏光板用粘着剤組成物から形成される粘着剤層を設けてなる偏光板。
- 偏光フィルムが水分を含有しており、その含水分量が0.5~5質量%である請求項3記載の偏光板。
Priority Applications (4)
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JP2010545691A JP5435433B2 (ja) | 2009-01-09 | 2009-11-30 | 偏光板用粘着剤組成物およびこれを利用した偏光板 |
US13/143,663 US20110293953A1 (en) | 2009-01-09 | 2009-11-30 | Pressure-sensitive adhesive composition for polarizer and polarizer formed using same |
EP09837539A EP2386616A4 (en) | 2009-01-09 | 2009-11-30 | AUTOCOLLATING ADHESIVE COMPOSITION FOR POLARIZER AND POLARIZER FORMED USING THE SAME |
CN2009801540752A CN102272255A (zh) | 2009-01-09 | 2009-11-30 | 偏光片用压敏粘合剂组合物及使用其的偏光片 |
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JP2009003168 | 2009-01-09 | ||
JP2009-003168 | 2009-01-09 |
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EP (1) | EP2386616A4 (ja) |
JP (1) | JP5435433B2 (ja) |
KR (1) | KR20110119637A (ja) |
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JP5561053B2 (ja) * | 2010-09-13 | 2014-07-30 | 東洋インキScホールディングス株式会社 | 粘着剤及びそれを用いた粘着フィルム |
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JP2013224431A (ja) * | 2013-05-20 | 2013-10-31 | Toyo Ink Sc Holdings Co Ltd | 光学用粘着剤および光学用粘着シート |
DE102013020538A1 (de) * | 2013-12-12 | 2015-06-18 | Lohmann Gmbh & Co. Kg | Haftklebemasse zur feuchtigkeitsresistenten Verklebung auf Glas |
WO2016147776A1 (ja) | 2015-03-18 | 2016-09-22 | リケンテクノス株式会社 | ハードコート積層フィルム |
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US11433651B2 (en) | 2015-03-18 | 2022-09-06 | Riken Technos Corporation | Hard coat laminated film |
EP3865301A1 (en) | 2015-03-18 | 2021-08-18 | Riken Technos Corporation | Hard coat laminated film |
WO2016147733A1 (ja) | 2015-03-18 | 2016-09-22 | リケンテクノス株式会社 | 防眩性ハードコート積層フィルム |
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JP2008144125A (ja) | 2006-11-17 | 2008-06-26 | Fujifilm Corp | アクリレート系粘着剤ならびにそれを用いた偏光板および液晶表示装置 |
JP2008144126A (ja) * | 2006-11-17 | 2008-06-26 | Fujifilm Corp | アクリレート系粘着剤ならびにそれを用いた偏光板および液晶表示装置 |
KR100948778B1 (ko) * | 2007-01-23 | 2010-03-24 | 주식회사 엘지화학 | 광학 보상된 아크릴계 점착제 조성물, 이를 포함하는편광판 및 액정표시소자 |
EP2033998B1 (en) * | 2007-09-06 | 2010-11-10 | Nitto Denko Corporation | Pressure sensitive adhesive composition, product using the same, and display using the product |
EP2053109A1 (en) * | 2007-10-22 | 2009-04-29 | Nitto Denko Corporation | Pressure-sensitive adhesive composition for optical film, pressure-sensitive adhesive layer for optical film, production method thereof, pressure-sensitive adhesive optical film and image display |
JP5540394B2 (ja) * | 2008-05-12 | 2014-07-02 | サイデン化学株式会社 | 偏光板用粘着剤組成物 |
-
2009
- 2009-11-30 KR KR1020117015818A patent/KR20110119637A/ko not_active Application Discontinuation
- 2009-11-30 EP EP09837539A patent/EP2386616A4/en not_active Withdrawn
- 2009-11-30 US US13/143,663 patent/US20110293953A1/en not_active Abandoned
- 2009-11-30 CN CN201310489230.4A patent/CN103555231A/zh active Pending
- 2009-11-30 WO PCT/JP2009/070099 patent/WO2010079653A1/ja active Application Filing
- 2009-11-30 JP JP2010545691A patent/JP5435433B2/ja active Active
- 2009-11-30 CN CN2009801540752A patent/CN102272255A/zh active Pending
- 2009-12-24 TW TW098144771A patent/TWI495697B/zh not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
WO2010079653A1 (ja) | 2010-07-15 |
CN103555231A (zh) | 2014-02-05 |
US20110293953A1 (en) | 2011-12-01 |
KR20110119637A (ko) | 2011-11-02 |
TW201031724A (en) | 2010-09-01 |
JPWO2010079653A1 (ja) | 2012-06-21 |
EP2386616A4 (en) | 2012-07-04 |
TWI495697B (zh) | 2015-08-11 |
EP2386616A1 (en) | 2011-11-16 |
JP5435433B2 (ja) | 2014-03-05 |
CN102272255A (zh) | 2011-12-07 |
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