WO2017094474A1 - 粘着剤組成物、粘着剤シート及び粘着剤付き光学フィルム - Google Patents

粘着剤組成物、粘着剤シート及び粘着剤付き光学フィルム Download PDF

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WO2017094474A1
WO2017094474A1 PCT/JP2016/083524 JP2016083524W WO2017094474A1 WO 2017094474 A1 WO2017094474 A1 WO 2017094474A1 JP 2016083524 W JP2016083524 W JP 2016083524W WO 2017094474 A1 WO2017094474 A1 WO 2017094474A1
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pressure
sensitive adhesive
film
meth
optical film
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PCT/JP2016/083524
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English (en)
French (fr)
Japanese (ja)
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景文 鄭
宰旭 鄭
公平 森岡
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住友化学株式会社
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Priority to KR1020187017107A priority Critical patent/KR102538808B1/ko
Priority to CN201680069936.7A priority patent/CN108291126B/zh
Publication of WO2017094474A1 publication Critical patent/WO2017094474A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • 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
    • 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
    • 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
    • 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
    • C09J7/22—Plastics; Metallised plastics
    • 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
    • C09J7/40—Adhesives in the form of films or foils characterised by release liners
    • 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
    • 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
    • G02F1/1336—Illuminating devices
    • G02F1/13362—Illuminating devices providing polarized light, e.g. by converting a polarisation component into another one
    • 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
    • G02F1/13363—Birefringent elements, e.g. for optical compensation

Definitions

  • the present invention relates to an adhesive composition suitable for an optical film, an adhesive sheet using the same, and an optical film with an adhesive.
  • the present invention also relates to an optical laminated body in which this optical film with an adhesive is laminated on a glass substrate and is suitably used for liquid crystal display.
  • a polarizing plate is widely used by being mounted on a liquid crystal display device.
  • a polarizing plate generally has a transparent protective film laminated on both sides of a polarizing film, a pressure-sensitive adhesive layer is formed on the surface of at least one protective film, and a release film is stuck on the pressure-sensitive adhesive layer. is doing.
  • a retardation film is laminated on a polarizing plate in which a protective film is bonded to both sides of the polarizing film to form an elliptical polarizing plate, and an adhesive layer / release film is attached in this order to the retardation film side.
  • an adhesive layer / release film may be stuck in this order on the surface of the retardation film.
  • the polarizing plate, the elliptically polarizing plate, the retardation film and the like provided with the pressure-sensitive adhesive layer are collectively referred to as an optical film.
  • Such an optical film with an adhesive is laminated on a glass substrate such as a liquid crystal cell to constitute a liquid crystal display device.
  • the pressure-sensitive adhesive composition for forming a pressure-sensitive adhesive layer applied to an optical film has a single amount of a acrylate ester as a main component and a polar functional group such as a hydroxyl group or a carboxyl group from the viewpoint of transparency and weather resistance.
  • Many (meth) acrylic resins produced by copolymerizing the body are used.
  • a crosslinking agent is blended with such a (meth) acrylic resin to give the required cohesive strength.
  • the adhesiveness of an adhesive layer and a glass substrate is improved by mix
  • the silane-based compound for example, 3-glycidoxypropyltrimethoxysilane is widely used (see JP 2013-181086 A).
  • An optical film with an adhesive gives, for example, an optical laminate for liquid crystal display by laminating on a glass substrate of a liquid crystal cell.
  • the optical laminate can be used under high temperature conditions and wet heat. Under conditions and in an environment where heating and cooling are repeated, the pressure-sensitive adhesive layer absorbs and relaxes the stress caused by the dimensional change of the optical film and the glass substrate. Lifting and peeling of the pressure-sensitive adhesive layer are suppressed. That is, the durability is excellent.
  • the adhesive layer of the optical film with an adhesive is required to have an appropriate adhesive strength as described above.
  • the optical film with an adhesive is bonded to a liquid crystal cell, the optical film Since the film is once peeled off and then a new film is attached again, it is also required that the peelability at that time is good. If the peelability is low, problems such as the adhesive remaining on the glass substrate occur.
  • the present invention has a novel pressure-sensitive adhesive composition that has an appropriate adhesive force to the glass substrate and can improve releasability by adding water to the interface between the pressure-sensitive adhesive layer and the glass substrate at the time of peeling,
  • the present invention also provides an adhesive sheet, an optical film with an adhesive, and an optical laminate using the same.
  • the present invention provides the following pressure-sensitive adhesive composition, pressure-sensitive adhesive sheet, optical film with pressure-sensitive adhesive, and optical laminate.
  • R 1 represents an alkyl group having 1 to 14 carbon atoms or an aralkyl group, aryl group or alkenyl group;
  • R 2 represents an alkyl group having 1 to 6 carbon atoms
  • the pressure-sensitive adhesive layer has an appropriate pressure-sensitive adhesive force to the glass substrate, and exhibits excellent releasability by adding water to the interface between the pressure-sensitive adhesive layer and the glass substrate at the time of peeling.
  • a pressure-sensitive adhesive sheet and an optical film with a pressure-sensitive adhesive using the same can be provided.
  • the pressure-sensitive adhesive composition of the present invention contains a (meth) acrylic resin (A), a crosslinking agent (B), and a silane compound (C) represented by the following formula (I).
  • R 1 is an alkyl group having 1 to 14 carbon atoms, an aralkyl group, an aryl group or an alkenyl group.
  • R 2 represents an alkyl group having 1 to 6 carbon atoms.
  • the (meth) acrylic resin (A) constituting the pressure-sensitive adhesive composition of the present invention has a structural unit derived from (meth) acrylic acid ester (A-1) as a main component and a (meth) acrylic single unit having a hydroxyl group. Those containing a structural unit derived from the monomer (A-2) are preferred. Furthermore, those containing a structural unit derived from a carboxyl group-containing (meth) acrylic acid ester (A-3) are preferred.
  • R 3 represents a hydrogen atom or a methyl group
  • R 4 represents an alkyl group or an aralkyl group having 14 or less carbon atoms, and the hydrogen atom constituting these groups is a group —O— ( C 2 H 4 O) m —R 5 may be substituted, wherein m represents 0 or an integer of 1 to 4, and R 5 represents an alkyl group or an aryl group having 12 or less carbon atoms.
  • the carboxy group-containing (meth) acrylic acid ester (A-3) is represented by the following formula (III).
  • R 6 represents a hydrogen atom or a methyl group
  • A represents a divalent organic group having 2 to 4 carbon atoms.
  • (meth) acrylic acid means that either acrylic acid or methacrylic acid may be used.
  • “(meth)” in the case of (meth) acrylate, (meth) acrylic resin, etc. is the same. This is the purpose.
  • the (meth) acrylic acid ester (A-1) represented by the above formula (I) is simply referred to as “monomer (A-1)” and a (meth) acrylic monomer having a hydroxyl group ( A-2) is simply referred to as “monomer (A-2)”, and the carboxyl group-containing (meth) acrylic acid ester (A-3) represented by the above formula (III) is simply referred to as “monomer (A— 3) ”may be called.
  • R 4 in the above formula (II) is an unsubstituted alkyl group, specifically, methyl acrylate, ethyl acrylate, propyl acrylate, n-acrylate
  • Linear alkyl acrylates such as butyl, n-octyl acrylate, and lauryl acrylate
  • branched alkyl acrylates such as isobutyl acrylate, 2-ethylhexyl acrylate, and isooctyl acrylate
  • Linear alkyl methacrylates such as methyl methacrylate, ethyl methacrylate, propyl methacrylate, n-butyl methacrylate, n-octyl methacrylate, and lauryl methacrylate
  • isobutyl methacrylate 2-methacrylic acid 2- Minutes such as ethylhexyl and isooctyl methacrylate
  • n-butyl acrylate is preferable. Specifically, among all monomers constituting the (meth) acrylic resin (A), n-butyl acrylate is 50% by weight or more. In addition, it is preferably used so as to satisfy the above-mentioned regulations regarding the monomer (A-1).
  • R 4 in the formula (II) being an aralkyl group include benzyl acrylate and benzyl methacrylate.
  • the hydrogen atom of the alkyl group or aralkyl group constituting R 4 in the formula (II) is substituted with the group —O— (C 2 H 4 O) m —R 5 .
  • m is 0 or an integer of 1 to 4 as defined above, but 0, 1 or 2 is particularly preferable.
  • R 5 is also an alkyl group or aryl group having 12 or less carbon atoms, as defined above, and may be linear or branched as long as the alkyl group has 3 or more carbon atoms.
  • aryl group constituting R 5 examples include phenyl and naphthyl, as well as nuclear alkyl-substituted phenyl including tolyl, xylyl, ethylphenyl, and biphenylyl (or phenylphenyl).
  • R 5 is particularly preferably these aryl groups.
  • R 4 in the formula (II) is an alkyl group, and the hydrogen atom is substituted with a group —O— (C 2 H 4 O) m —R 5.
  • 2-methoxyethyl acrylate, ethoxymethyl acrylate, 2-phenoxyethyl acrylate, 2- (2-phenoxyethoxy) ethyl acrylate, and 2- (o-phenylphenoxy) ethyl acrylate Such as alkoxyalkyl-, aryloxyalkyl- or aryloxyethoxyalkyl-esters of acrylic acid; 2-methoxyethyl methacrylate, ethoxymethyl methacrylate, 2-phenoxyethyl methacrylate, 2- (2-phenoxyethoxy) methacrylate Alcohols of methacrylic acid such as ethyl and 2- (o-phenylphenoxy) ethyl methacrylate Shiarukiru -, aryl
  • monomers (A-1) can be used alone or in combination with a plurality of different monomers.
  • the monomer (A-1) is particularly preferably composed mainly of n-butyl acrylate, but in addition, other (meth) acrylic acid esters corresponding to the formula (II) Copolymerization is also effective.
  • n-butyl acrylate is 50% by weight or more
  • a hydrogen atom represented by the above formula (II) and constituting R 4 in the formula is a group —O— (C 2 H 4 O) m —R 5 (where m and R 5 are Is as defined above) and is a mixture of 3 to 15% by weight of a (meth) acrylic acid ester substituted with an alkyl group.
  • Examples of the (meth) acrylic monomer (A-2) having a hydroxyl group include 2-hydroxyethyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, and 4-hydroxy (meth) acrylate. Examples include butyl and 2- (2-hydroxyethoxy) ethyl (meth) acrylate. Of these, 2-hydroxyethyl acrylate is preferably used as one of the monomers (A-2) constituting the (meth) acrylic resin (A).
  • the carboxyl group-containing (meth) acrylic acid ester (A-3) is represented by the above formula (III).
  • R 6 is a hydrogen atom or a methyl group
  • A is a divalent organic group having 2 to 4 carbon atoms.
  • the divalent organic group represented by A is typically alkylene, which is also preferably linear alkylene, but the (meth) acrylic acid moiety CH 2 ⁇ C (R 6 ) COO— Assuming that the carbon chain connecting the terminal carboxyl group —COOH is at least 2 in series, the chain may be branched as long as it has 3 or more carbon atoms.
  • Examples thereof include 2-carboxyethyl acrylate, 3-carboxypropyl acrylate, 4-carboxy acrylate. Examples include butyl.
  • compounds obtained by changing these acrylic acid esters to methacrylic acid esters can also be the monomer (A-3).
  • the above-mentioned 2-carboxyethyl acrylate is usually produced by dimerization of acrylic acid, and in that case, in addition to 2-carboxyethyl acrylate, which is the main component, acrylic acid itself or a trimer of acrylic acid. It is often obtained as a mixture with the above oligomers and sold as such in the state of a mixture.
  • other carboxyl group-containing (meth) acrylic monomers may be copolymerized with the monomer (A-3).
  • the content of the structural unit derived from the (meth) acrylic acid ester represented by the above formula (II), that is, the monomer (A-1) is 90
  • the content of the structural unit derived from the (meth) acrylic monomer having a hydroxyl group, that is, the monomer (A-2) is 0.1 to 6% by weight
  • the content of the structural unit derived from the carboxyl group-containing (meth) acrylic acid ester represented by the formula (III), that is, the monomer (A-3) can be 0.01 to 0.4% by weight. .
  • a pressure-sensitive adhesive composition that gives a pressure-sensitive adhesive sheet with excellent processability can be prepared.
  • the total amount of structural units derived from each of the monomers (A-1), (A-2) and (A-3) does not exceed 100% by weight.
  • the (meth) acrylic resin (A) used in the present invention contains structural units derived from monomers other than the monomers (A-1), (A-2) and (A-3) described above. You may go out.
  • monomers other than monomers (A-1), (A-2) and (A-3) include monomers and molecules other than those of formula (III) having polar functional groups other than hydroxyl groups.
  • (Meth) acrylic acid ester having alicyclic structure, styrene monomer, vinyl monomer, (meth) acrylamide derivative, monomer having multiple (meth) acryloyl groups in the molecule, etc. is there.
  • a monomer other than the formula (III) having a polar functional group other than a hydroxyl group will be described.
  • the polar functional group other than the hydroxyl group here may be a free carboxyl group, a heterocyclic group including an epoxy ring, or the like.
  • the acrylic acid itself and oligomers of trimer or higher of acrylic acid described above for the monomer (A-3) correspond to monomers other than the formula (III) having a free carboxyl group.
  • Examples of the monomer having a heterocyclic group include acryloylmorpholine, vinylcaprolactam, N-vinyl-2-pyrrolidone, tetrahydrofurfuryl (meth) acrylate, caprolactone-modified tetrahydrofurfuryl acrylate, 3,4-epoxy.
  • Examples include cyclohexylmethyl (meth) acrylate and glycidyl (meth) acrylate.
  • the total amount of monomers having a polar functional group is 8% by weight or less based on the total monomers constituting the (meth) acrylic resin (A). It is preferable to do this.
  • the alicyclic structure is a cycloparaffin structure having usually 5 or more carbon atoms, preferably about 5 to 7 carbon atoms.
  • Specific examples of the acrylate ester having an alicyclic structure include isobornyl acrylate, cyclohexyl acrylate, dicyclopentanyl acrylate, cyclododecyl acrylate, methylcyclohexyl acrylate, trimethylcyclohexyl acrylate, tert-acrylate Examples include butylcyclohexyl, ⁇ -ethoxyacrylate cyclohexyl, cyclohexylphenyl acrylate, and the like.
  • methacrylic acid ester having an alicyclic structure examples include isobornyl methacrylate, cyclohexyl methacrylate, dicyclopentanyl methacrylate, cyclododecyl methacrylate, methyl cyclohexyl methacrylate, trimethyl cyclohexyl methacrylate, methacrylic acid.
  • examples include tert-butylcyclohexyl and cyclohexylphenyl methacrylate.
  • styrenic monomers examples include styrene, methyl styrene, dimethyl styrene, trimethyl styrene, ethyl styrene, diethyl styrene, triethyl styrene, propyl styrene, butyl styrene, hexyl styrene, heptyl styrene, and octyl styrene.
  • Alkyl styrenes such as fluorostyrene, chlorostyrene, bromostyrene, dibromostyrene, and iodostyrene; and nitrostyrene, acetylstyrene, methoxystyrene, divinylbenzene, and the like.
  • vinyl monomers include: vinyl acetate, vinyl propionate, vinyl butyrate, vinyl 2-ethylhexanoate, and vinyl fatty acid esters such as vinyl laurate; vinyl halides such as vinyl chloride and vinyl bromide; Vinylidene halides such as vinylidene chloride; nitrogen-containing aromatic vinyls such as vinylpyridine, vinylpyrrolidone, and vinylcarbazole; conjugated diene monomers such as butadiene, isoprene, and chloroprene; and acrylonitrile, methacrylonitrile, etc. .
  • Examples of (meth) acrylamide derivatives include N-methylol (meth) acrylamide, N- (2-hydroxyethyl) (meth) acrylamide, N- (3-hydroxypropyl) (meth) acrylamide, N- (4- Hydroxybutyl) (meth) acrylamide, N- (5-hydroxypentyl) (meth) acrylamide, N- (6-hydroxyhexyl) (meth) acrylamide, N- (methoxymethyl) (meth) acrylamide, N- (ethoxymethyl) ) (Meth) acrylamide, N- (propoxymethyl) (meth) acrylamide, N- (butoxymethyl) (meth) acrylamide, N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, N- Isopropyl (meth) acrylamide, N- (3- Methylaminopropyl) (meth) acrylamide, N- (1,1-d
  • Examples of monomers having a plurality of (meth) acryloyl groups in the molecule include 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, and 1,9-nonane.
  • Two diols in the molecule such as diol di (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, and tripropylene glycol di (meth) acrylate
  • Monomers having a meth) acryloyl group monomers having three (meth) acryloyl groups in the molecule, such as trimethylolpropane tri (meth) acrylate.
  • a monomer other than the monomers (A-1), (A-2) and (A-3) which are components of the (meth) acrylic resin (A) and having no polar functional group is copolymerized.
  • the amount is preferably 5% by weight or less based on the total monomers constituting the (meth) acrylic resin (A).
  • the resin component constituting the pressure-sensitive adhesive composition is the (meth) acrylic acid ester represented by the formula (II) described above, that is, the monomer (A-1), a (meth) acrylic monomer having a hydroxyl group.
  • Two or more types of (A) may be mixed.
  • (meth) acrylic resin (A) having a predetermined proportion of structural units derived from monomers (A-1), (A-2) and (A-3) is different from (meth) acrylic.
  • a resin may be mixed.
  • Examples of the different (meth) acrylic resin mixed in this case include those having a structural unit derived from the (meth) acrylic acid ester of the above formula (II) and having no polar functional group.
  • the (meth) acrylic resin (A) having structural units derived from the monomers (A-1), (A-2) and (A-3) in a predetermined ratio is composed of the whole (meth) acrylic resin, It is preferably 80% by weight or more, more preferably 90% by weight or more.
  • the (meth) acrylic resin (A) it is preferable to employ a resin having a weight average molecular weight Mw in the range of 500,000 to 2,000,000 in terms of standard polystyrene by gel permeation chromatography (GPC).
  • the weight average molecular weight Mw is particularly preferably 500,000 to 1,700,000.
  • the weight average molecular weight in terms of standard polystyrene is 500,000 or more, the adhesiveness under high temperature and high humidity is improved, and the possibility of occurrence of floating or peeling between the glass substrate and the pressure sensitive adhesive sheet is reduced. And reworkability tends to be improved.
  • the weight average molecular weight is 2 million or less, even if the dimension of the optical film bonded to the pressure-sensitive adhesive sheet changes, the pressure-sensitive adhesive layer fluctuates following the dimensional change, so the liquid crystal cell This is preferable because there is no difference between the brightness of the peripheral edge and the brightness of the central portion, and white spots and color unevenness tend to be suppressed.
  • the molecular weight distribution represented by the ratio Mw / Mn of the weight average molecular weight Mw and the number average molecular weight Mn is not particularly limited, but is preferably in the range of about 3 to 7, for example.
  • the (meth) acrylic resin (A) preferably has a glass transition temperature in the range of ⁇ 10 to ⁇ 60 ° C. in order to exhibit adhesiveness.
  • the glass transition temperature of the resin can be measured by a differential scanning calorimeter.
  • the (meth) acrylic resin (A) can be produced by various known methods such as a solution polymerization method, an emulsion polymerization method, a bulk polymerization method, and a suspension polymerization method.
  • a polymerization initiator is usually used in the production of this (meth) acrylic resin.
  • the polymerization initiator is used in an amount of about 0.001 to 5 parts by weight with respect to a total of 100 parts by weight of all monomers used in the production of the (meth) acrylic resin.
  • the polymerization initiator a thermal polymerization initiator, a photopolymerization initiator, or the like is used.
  • the photopolymerization initiator include 4- (2-hydroxyethoxy) phenyl (2-hydroxy-2-propyl) ketone.
  • thermal polymerization initiators examples include 2,2′-azobisisobutyronitrile, 2,2′-azobis (2-methylbutyronitrile), 1,1′-azobis (cyclohexane-1-carbonitrile), 2,2'-azobis (2,4-dimethylvaleronitrile), 2,2'-azobis (2,4-dimethyl-4-methoxyvaleronitrile), dimethyl-2,2'-azobis (2-methylpropio) And azo compounds such as 2,2′-azobis (2-hydroxymethylpropionitrile); lauryl peroxide, tert-butyl hydroperoxide, benzoyl peroxide, tert-butyl peroxybenzoate, cumene hydroper Oxide, diisopropylperoxydicarbonate, dipropylperoxydicarbonate, tert-butylperoxide Organic peroxides such as xineodecanoate, tert-butyl peroxypivalate, and (3,5,5-tri
  • the solution polymerization method is preferable among the methods shown above.
  • a specific example of the solution polymerization method will be described.
  • a desired monomer and an organic solvent are mixed, and a thermal polymerization initiator is added in a nitrogen atmosphere to about 40 to 90 ° C., preferably 50 to 80 ° C.
  • a method of stirring at about 0 ° C. for about 3 to 15 hours can be mentioned.
  • organic solvent examples include aromatic hydrocarbons such as toluene and xylene; esters such as ethyl acetate and butyl acetate; aliphatic alcohols such as propyl alcohol and isopropyl alcohol; acetone, methyl ethyl ketone, and methyl isobutyl. Ketones such as ketones can be used.
  • Crosslinking agent (B) A crosslinking agent (B) is mix
  • the crosslinking agent (B) is a compound having at least two functional groups in the molecule that can react with a hydroxyl group or a carboxyl group, which are polar functional groups in the (meth) acrylic resin (A), to crosslink the (meth) acrylic resin.
  • an isocyanate compound, an epoxy compound, a metal chelate compound, an aziridine compound and the like are exemplified.
  • Isocyanate compounds are compounds having at least two isocyanato groups (—NCO) in the molecule, such as tolylene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, xylylene diisocyanate, hydrogenated xylylene diisocyanate, diphenylmethane diisocyanate, Examples thereof include hydrogenated diphenylmethane diisocyanate, naphthalene diisocyanate, and triphenylmethane triisocyanate.
  • —NCO isocyanato groups
  • adducts obtained by reacting these isocyanate compounds with polyols such as glycerol and trimethylolpropane, and those obtained by making the isocyanate compounds into dimers, trimers, and the like can also be used as crosslinking agents for pressure-sensitive adhesives. Two or more isocyanate compounds can be mixed and used.
  • the epoxy compound is a compound having at least two epoxy groups in the molecule, for example, bisphenol A type epoxy resin, ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, glycerin diglycidyl ether, glycerin triglycidyl ether. 1,6-hexanediol diglycidyl ether, trimethylolpropane triglycidyl ether, N, N-diglycidylaniline, N, N, N ′, N′-tetraglycidyl-m-xylenediamine and the like. Two or more types of epoxy compounds can be mixed and used.
  • metal chelate compound examples include compounds in which acetylacetone or ethyl acetoacetate is coordinated to a polyvalent metal such as aluminum, iron, copper, zinc, tin, titanium, nickel, antimony, magnesium, vanadium, chromium and zirconium. Can be mentioned.
  • An aziridine-based compound is a compound having at least two 3-membered ring skeletons composed of one nitrogen atom and two carbon atoms, also called ethyleneimine, for example, diphenylmethane-4,4′-bis ( 1-aziridinecarboxamide), toluene-2,4-bis (1-aziridinecarboxamide), triethylenemelamine, isophthaloylbis-1- (2-methylaziridine), tris-1-aziridinylphosphine oxide, hexamethylene 1,6-bis (1-aziridinecarboxamide), trimethylolpropane tris- ⁇ -aziridinylpropionate, tetramethylolmethane, tris- ⁇ -aziridinylpropionate, and the like.
  • isocyanate compounds in particular, xylylene diisocyanate, tolylene diisocyanate or hexamethylene diisocyanate, or adducts obtained by reacting these isocyanate compounds with polyols such as glycerol and trimethylolpropane, and isocyanate compounds A dimer, trimer or the like, or a mixture of these isocyanate compounds is preferably used.
  • Particularly suitable isocyanate compounds include tolylene diisocyanate, adducts obtained by reacting tolylene diisocyanate with polyols, dimers of tolylene diisocyanate, and trimers of tolylene diisocyanate.
  • the crosslinking agent (B) is blended at a ratio of 0.01 to 5 parts by weight with respect to 100 parts by weight of the (meth) acrylic resin (A).
  • the blending amount of the crosslinking agent (B) is preferably about 0.1 to 3 parts by weight, more preferably about 0.1 to 1 part by weight with respect to 100 parts by weight of the (meth) acrylic resin (A).
  • the pressure-sensitive adhesive layer constituted by using the pressure-sensitive adhesive composition when the amount of the crosslinking agent (B) relative to 100 parts by weight of the (meth) acrylic resin (A) is 0.01 parts by weight or more, particularly 0.1 parts by weight or more
  • the amount of 5 parts by weight or less is preferable because white spots are not noticeable when an optical film with an adhesive is applied to a liquid crystal display device.
  • silane compound (C) When the pressure-sensitive adhesive composition of the present invention forms a pressure-sensitive adhesive sheet or an optical film with a pressure-sensitive adhesive, the silane compound (C) represented by the above formula (I) is used to improve the adhesion between the pressure-sensitive adhesive composition and the glass substrate. )including.
  • the silane compound (C) is preferably contained in the (meth) acrylic resin (A) before blending the crosslinking agent.
  • a pressure-sensitive adhesive layer having excellent adhesion with a glass substrate and having an appropriate adhesive force By containing the silane compound (C) represented by the above formula (I), it is possible to form a pressure-sensitive adhesive layer having excellent adhesion with a glass substrate and having an appropriate adhesive force, When the pressure-sensitive adhesive layer is peeled from the glass substrate, a pressure-sensitive adhesive layer having excellent peelability can be formed by adding water to the interface between the pressure-sensitive adhesive layer and the glass substrate.
  • R 1 represents an alkyl group having 1 to 14 carbon atoms, an aralkyl group, an aryl group, or an alkenyl group.
  • R 1 represents a methyl group , An ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, a pentyl group, and a hexyl group.
  • R 2 represents an alkyl group having 1 to 6 carbon atoms, and specific examples include compounds in which R 2 is a methyl group, an ethyl group, or a propyl group. Is mentioned. Among these, 3-ureidopropyltrialkoxysilane is suitable as the silane compound (C) represented by the above formula (I). In addition, you may contain the silane type compound (C) represented by 2 or more types of formula (I).
  • the silane compound (C) represented by the formula (I) described above may be contained alone, or the formula (I And a silane compound other than (C) other than the silane compound represented by formula (I) together with the silane compound (C) represented by formula (I).
  • silane compounds other than the silane compound (C) represented by the formula (I) include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, 3-glycidoxypropyltri Methoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltri Methoxysilane, 3-mercaptopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropyldimethoxymethylsilane, 3-glycidoxypropyl ethoxy Sidimethylsilane and the like, and may
  • Silane compounds are often liquids.
  • the compounding amount of the silane compound (C) represented by the formula (I) in the pressure-sensitive adhesive composition is 0.01 to 10 parts by weight with respect to 100 parts by weight of the solid content of the (meth) acrylic resin (A). Yes, preferably 0.03 to 2 parts by weight, more preferably 0.2 to 1 part by weight.
  • (meth) acrylic resin when containing silane type compounds other than the silane type compound (C) represented by Formula (I), together with the silane type compound (C) represented by Formula (I), (meth) acrylic resin ( The amount is about 0.01 to 10 parts by weight, preferably 0.03 to 2 parts by weight, and more preferably 0.2 to 1 part by weight with respect to 100 parts by weight of the solid content of A).
  • the amount of the silane compound (C) represented by the formula (I) with respect to 100 parts by weight of the solid content of the (meth) acrylic resin (A) is 0.01 parts by weight or more, particularly 0.03 parts by weight or more, It is preferable because the adhesion and durability between the pressure-sensitive adhesive layer and the glass substrate are improved. Further, it is preferably 0.2 parts by weight or more, since the adhesive force when water is added to the interface between the pressure-sensitive adhesive layer and the glass substrate can be greatly reduced, and the peelability can be further improved.
  • the content of the silane compound (C) represented by formula (I) and the other silane compound is 10 parts by weight or less, particularly 2 parts by weight or less, or 1 part by weight or less, It is preferable because the silane compound tends to be suppressed from bleeding out from the pressure-sensitive adhesive layer.
  • the pressure-sensitive adhesive composition may further contain an ionic compound as an antistatic agent for imparting antistatic properties to the pressure-sensitive adhesive layer.
  • the ionic compound is a compound having an inorganic cation or an organic cation and an inorganic anion or an organic anion. Two or more ionic compounds may be used.
  • Examples of the inorganic cation include alkali metal ions such as lithium cation [Li + ], sodium cation [Na + ], and potassium cation [K + ], beryllium cation [Be 2+ ], and magnesium cation [Mg 2+ ]. And alkaline earth metal ions such as calcium cation [Ca 2+ ].
  • organic cation examples include an imidazolium cation, a pyridinium cation, a pyrrolidinium cation, an ammonium cation, a sulfonium cation, and a phosphonium cation.
  • the organic cation component is preferably used because of its excellent compatibility with the pressure-sensitive adhesive composition.
  • organic cation components pyridinium cation and imidazolium cation are particularly preferably used from the viewpoint that they are difficult to be charged when the release film provided on the pressure-sensitive adhesive layer is peeled off.
  • inorganic anions include chloride anions [Cl ⁇ ], bromide anions [Br ⁇ ], iodide anions [I ⁇ ], tetrachloroaluminate anions [AlCl 4 ⁇ ], heptachlorodialuminate anions [Al 2 Cl 7 ⁇ ], tetrafluoroborate anion [BF 4 ⁇ ], hexafluorophosphate anion [PF 6 ⁇ ], perchlorate anion [ClO 4 ⁇ ], nitrate anion [NO 3 ⁇ ], hexafluoroarsenate anion [AsF 6] - ], Hexafluoroantimonate anion [SbF 6 ⁇ ], hexafluoro niobate anion [NbF 6 ⁇ ], hexafluoro tantalate anion [TaF 6 ⁇ ], dicyanamide anion [(CN) 2 N ⁇ ] and the
  • organic anion examples include acetate anion [CH 3 COO ⁇ ], trifluoroacetate anion [CF 3 COO ⁇ ], methanesulfonate anion [CH 3 SO 3 ⁇ ], trifluoromethanesulfonate anion [CF 3 SO 3 ⁇ ], p-toluenesulfonate anion [p-CH 3 C 6 H 4 SO 3 ⁇ ], bis (fluorosulfonyl) imide anion [(FSO 2 ) 2 N ⁇ ], bis (trifluoromethanesulfonyl) imide anion [(CF 3 SO 2 ) 2 N ⁇ ], tris (trifluoromethanesulfonyl) methanide anion [(CF 3 SO 2 ) 3 C ⁇ ], dimethyl phosphinate anion [(CH 3 ) 2 POO ⁇ ], (poly) hydrofluorofluoride anion [ F (HF) n ⁇ ] (n is about
  • an anion component containing a fluorine atom is preferably used because it gives an ionic compound having excellent antistatic performance.
  • Specific examples include a bis (fluorosulfonyl) imide anion, a hexafluorophosphate anion, or a bis (trifluoromethanesulfonyl) imide anion.
  • ionic compound can be appropriately selected from a combination of the above cation component and anion component.
  • ionic compounds having an organic cation are listed below according to the structure of the organic cation.
  • Pyridinium salt N-hexylpyridinium hexafluorophosphate, N-octylpyridinium hexafluorophosphate, N-octyl-4-methylpyridinium hexafluorophosphate, N-butyl-4-methylrupyridinium hexafluorophosphate, Tetrabutylammonium hexafluorophosphate, N-decylpyridinium bis (fluorosulfonyl) imide, N-dodecylpyridinium bis (fluorosulfonyl) imide, N-tetradecylpyridinium bis (fluorosulfonyl) imide, N-hexadecylpyridinium bis (fluorosulfonyl) imide, N-dodecyl-4-methylpyridinium bis (fluorosulfonyl) imide, N-tetradecyl-4-
  • Imidazolium salt 1-ethyl-3-methylimidazolium hexafluorophosphate, 1-ethyl-3-methylimidazolium p-toluenesulfonate, 1-ethyl-3-methylimidazolium bis (fluorosulfonyl) imide 1-ethyl-3-methylimidazolium bis (trifluoromethanesulfonyl) imide 1-butyl-3-methylimidazolium methanesulfonate, 1-butyl-3-methylimidazolium bis (fluorosulfonyl) imide.
  • Pyrrolidinium salt N-butyl-N-methylpyrrolidinium hexafluorophosphate, N-butyl-N-methylpyrrolidinium bis (fluorosulfonyl) imide N-butyl-N-methylpyrrolidinium bis (trifluoromethanesulfonyl) imide.
  • Quaternary ammonium salt Tetrabutylammonium p-toluenesulfonate, (2-hydroxyethyl) trimethylammonium bis (trifluoromethanesulfonyl) imide, (2-Hydroxyethyl) trimethylammonium dimethylphosphinate.
  • Examples of the ionic compound having an inorganic cation include the following. Lithium bromide, Lithium iodide, Lithium tetrafluoroborate, Lithium hexafluorophosphate, Lithium thiocyanate, Lithium perchlorate, Lithium trifluoromethanesulfonate, Lithium bis (fluorosulfonyl) imide lithium bis (trifluoromethanesulfonyl) imide, Lithium bis (pentafluoroethanesulfonyl) imide, Lithium tris (trifluoromethanesulfonyl) methanide, Lithium p-toluenesulfonate, Sodium hexafluorophosphate, Sodium bis (fluorosulfonyl) imide, Sodium bis (trifluoromethanesulfonyl) imide, Sodium p-toluenesulfonate
  • the ionic compound is preferably a solid at room temperature. Compared with the case of using an ionic compound that is liquid at room temperature, the antistatic performance can be maintained for a long time. From the viewpoint of such antistatic long-term stability, the ionic compound preferably has a melting point of 30 ° C. or higher, more preferably 35 ° C. or higher. On the other hand, if the melting point is too high, the compatibility with the (meth) acrylic resin (A) is deteriorated, so the melting point is preferably 90 ° C. or less, more preferably 70 ° C. or less, and even more preferably less than 50 ° C. It is.
  • the content of the ionic compound in the pressure-sensitive adhesive composition is preferably 0.2 to 8 parts by weight, more preferably 0.2 to 5 parts by weight with respect to 100 parts by weight of the (meth) acrylic resin (A). Part, more preferably 0.3 to 5 parts by weight, and particularly preferably 0.5 to 3 parts by weight.
  • the content of the ionic compound being 0.2 parts by weight or more is advantageous for improving the antistatic performance, and the content of 8 parts by weight or less is advantageous for maintaining the durability of the pressure-sensitive adhesive layer.
  • the pressure-sensitive adhesive composition is an additive such as a crosslinking catalyst, a weather stabilizer, a tackifier, a plasticizer, a softener, a dye, a pigment, an inorganic filler, a light scattering fine particle, and a resin other than the (meth) acrylic resin (A). Can be contained. If a cross-linking catalyst is blended with the cross-linking agent in the pressure-sensitive adhesive composition, the pressure-sensitive adhesive sheet can be prepared by a short time curing, and the resulting optical film with the pressure-sensitive adhesive floats between the optical film and the pressure-sensitive adhesive sheet. It is possible to suppress occurrence of peeling or foaming in the pressure-sensitive adhesive sheet.
  • an ultraviolet curable compound into the pressure-sensitive adhesive composition, form an pressure-sensitive adhesive layer, and then cure by irradiating with ultraviolet rays to form a harder pressure-sensitive adhesive layer.
  • the crosslinking catalyst include amine compounds such as hexamethylenediamine, ethylenediamine, polyethyleneimine, hexamethylenetetramine, diethylenetriamine, triethylenetetramine, isophoronediamine, trimethylenediamine, polyamino resin, and melamine resin.
  • Each component demonstrated above is mixed in the state melt
  • the solvent include aromatic hydrocarbons such as toluene and xylene; esters such as ethyl acetate and butyl acetate; aliphatic alcohols such as propyl alcohol and isopropyl alcohol; acetone, methyl ethyl ketone, and methyl isobutyl ketone. Ketones such as can be used.
  • This pressure-sensitive adhesive composition exhibits good performance, but it preferably does not contain an amino group in order to avoid strong adhesion when it comes into contact with a specific release film. In particular, it is preferable not to have a tertiary amino group.
  • the pressure-sensitive adhesive composition dissolved in the above solvent is applied onto a suitable substrate and dried to form a pressure-sensitive adhesive sheet.
  • the substrate used here is generally a plastic film, and a typical example thereof is a release film that has been subjected to a release treatment.
  • the release film is, for example, a film on which a pressure-sensitive adhesive sheet of a film made of various resins such as polyethylene terephthalate, polybutylene terephthalate, polycarbonate, and polyarylate is formed and subjected to a release treatment such as a silicone treatment. be able to.
  • the pressure-sensitive adhesive sheet of the present invention is formed into a sheet shape from the pressure-sensitive adhesive composition described above.
  • the “pressure-sensitive adhesive sheet” in the laminate may be referred to as “pressure-sensitive adhesive layer”.
  • the pressure-sensitive adhesive sheet of the present invention is preferably used after curing for a certain period of time, preferably 7 days or more, and allowing the crosslinking reaction to proceed.
  • the pressure-sensitive adhesive sheet of the present invention preferably has a gel fraction of 65 to 85% after it is coated into a sheet and left at room temperature for 7 days. By having such a gel fraction, the pressure-sensitive adhesive sheet exhibits excellent durability.
  • the gel fraction is a value measured according to the following (1) to (4).
  • An adhesive sheet having an area of about 8 cm ⁇ about 8 cm and a metal mesh made of SUS304 (about 10 cm ⁇ about 10 cm) (with a weight of Wm) are bonded.
  • (3) The mesh stapled in (2) above is placed in a glass container, and 60 mL of ethyl acetate is added and immersed, and then the glass container is stored at room temperature for 3 days. (4) The mesh is taken out from the glass container, dried at 120 ° C. for 24 hours, weighed, and its weight is defined as Wa.
  • Gel fraction (% by weight) [ ⁇ Wa ⁇ (Wb ⁇ Ws) ⁇ Wm ⁇ / (Ws ⁇ Wm)] ⁇ 100 Calculate the gel fraction based on
  • the gel fraction after leaving for 7 days can be adjusted with the kind of (meth) acrylic resin (A) which is an active ingredient of the adhesive composition which forms it, and the quantity of a crosslinking agent, for example. Specifically, the amount of the monomer having a polar functional group including the monomer (A-2) and the monomer (A-3) in the (meth) acrylic resin (A) is increased, or If the amount of the crosslinking agent (B) in the pressure-sensitive adhesive composition is increased, the gel fraction is increased. Therefore, the gel fraction may be adjusted by adjusting these amounts.
  • the adhesive strength of the adhesive sheet to glass is preferably 1.0 to 8.0 N / 25 mm. When it is 1.0 N / 25 mm, the adhesive force is too low, and it becomes easy to peel between the glass substrate and the adhesive sheet. If it exceeds 8.0 N / 25 mm, the followability of the pressure-sensitive adhesive sheet with respect to the dimensional change of the optical film may be lowered, and the durability may be lowered.
  • the adhesive strength to glass of the pressure-sensitive adhesive sheet can be controlled by adjusting the elasticity of the base polymer of the pressure-sensitive adhesive composition or by adjusting the blending amount of an additive (for example, a silane compound).
  • the pressure-sensitive adhesive strength of the pressure-sensitive adhesive sheet is greatly reduced when water is added to the interface between the pressure-sensitive adhesive sheet and the glass substrate.
  • the adhesive strength of the pressure-sensitive adhesive sheet to the glass substrate when water is not added is P 1
  • the adhesive strength of the pressure-sensitive adhesive sheet to the glass substrate when water is added is P 2
  • the following formula: Decrease rate of adhesive strength when water added (%) (P 1 ⁇ P 2 ) / P 1 ⁇ 100
  • optical film with adhesive The optical film with pressure-sensitive adhesive of the present invention is obtained by bonding a pressure-sensitive adhesive sheet formed from the above pressure-sensitive adhesive composition to at least one surface of an optical film.
  • the optical film used for the optical film with an adhesive is a film having optical properties, and examples thereof include a polarizing plate and a retardation film.
  • a polarizing plate is an optical film having a function of emitting polarized light with respect to incident light such as natural light.
  • the polarizing plate absorbs linearly polarized light having a vibrating surface in a certain direction and reflects linearly polarized light having a vibrating surface in a certain direction, and reflects linearly polarized light having a vibrating surface in a certain direction.
  • a polarizing film that expresses the function of a polarizing plate, particularly a linear polarizing plate (sometimes called a polarizer)
  • two colors such as iodine and a dichroic dye are applied to a uniaxially stretched polyvinyl alcohol resin film.
  • the thing which the adsorptive orientation of the property pigment is mentioned.
  • the retardation film is an optical film exhibiting optical anisotropy, for example, polyvinyl alcohol, polycarbonate, polyester, polyarylate, polyimide, polyolefin, cyclic polyolefin, polystyrene, polysulfone, polyethersulfone, polyvinylidene fluoride.
  • Stretched film obtained by stretching a polymer film composed of polymethyl methacrylate, liquid crystal polyester, acetyl cellulose, saponified ethylene-vinyl acetate copolymer, polyvinyl chloride, etc. by about 1.01 to 6 times. It is done.
  • a polymer film obtained by uniaxially or biaxially stretching a polycarbonate film or a cyclic polyolefin film is preferable.
  • a uniaxial phase difference film a wide viewing angle phase difference film, a low photoelasticity phase difference film, etc., it is applicable to all.
  • a film that exhibits optical anisotropy by applying and orienting a liquid crystalline compound and a film that exhibits optical anisotropy by applying an inorganic layered compound can be used as the retardation film.
  • a retardation film is a so-called temperature-compensated retardation film, and a rod-like liquid crystal sold under the trade name “LC film” from JX Nippon Mining & Energy Co., Ltd. is twisted to align.
  • a transparent resin film is used, and as the transparent resin, for example, an acetyl cellulose resin typified by triacetyl cellulose or diacetyl cellulose, a methacrylic resin typified by polymethyl methacrylate, a polyester resin, or a polyolefin Resin, polycarbonate resin, polyether ether ketone resin, polysulfone resin and the like.
  • the resin constituting the protective film may contain an ultraviolet absorber such as a salicylic acid ester compound, a benzophenone compound, a benzotriazole compound, a triazine compound, a cyanoacrylate compound, and a nickel complex compound.
  • an acetyl cellulose resin film such as a triacetyl cellulose film is preferably used.
  • the linear polarizing plate is often used in a state in which a protective film is attached to one or both sides of a polarizing film constituting the polarizing film, for example, a polarizing film made of a polyvinyl alcohol-based resin.
  • a polarizing film for example, a polarizing film made of a polyvinyl alcohol-based resin.
  • the above-mentioned elliptically polarizing plate is a laminate of a linearly polarizing plate and a retardation film
  • the linearly polarizing plate is often in a state where a protective film is attached to one side or both sides of the polarizing film.
  • the adhesive sheet by this invention it is normally bonded by the phase difference film side.
  • a release film having been subjected to a release treatment as described above is attached to the surface of the adhesive layer to protect the surface of the adhesive layer until use.
  • An optical film with an adhesive provided with a release film in this way is formed, for example, by applying the above-mentioned adhesive composition to the release treatment surface of the release film to form an adhesive sheet, A method of laminating on an optical film, a method of applying a pressure-sensitive adhesive composition on an optical film to form a pressure-sensitive adhesive sheet, attaching a release film to the surface of the pressure-sensitive adhesive to protect it, and making an optical film with a pressure-sensitive adhesive Can be manufactured.
  • the thickness of the pressure-sensitive adhesive layer formed on the optical film is not particularly limited, but is usually 30 ⁇ m or less, preferably 10 ⁇ m or more, and more preferably 15 to 25 ⁇ m.
  • the thickness of the pressure-sensitive adhesive layer is 30 ⁇ m or less, the adhesiveness under high temperature and high humidity is improved, and the possibility of floating or peeling between the glass substrate and the pressure-sensitive adhesive layer tends to be reduced.
  • the optical film with pressure-sensitive adhesive of the present invention is bonded to a glass substrate to form an optical laminate, and when there is some trouble and the optical film is peeled off from the glass substrate, the adhesive film and the glass substrate at the interface.
  • the adhesive strength of the pressure-sensitive adhesive layer is greatly reduced and excellent peelability is exhibited. Therefore, the pressure-sensitive adhesive layer is peeled off along with the optical film, and almost no fogging or adhesive residue is generated on the surface of the glass substrate that is in contact with the pressure-sensitive adhesive layer. It is easy to reapply the optical film.
  • optical laminate The optical film with pressure-sensitive adhesive of the present invention can be made into an optical laminate by bonding the pressure-sensitive adhesive layer side to a glass substrate.
  • the release film is peeled off from the optical film with an adhesive obtained as described above, and the exposed adhesive layer surface is the surface of the glass substrate. You just have to stick together.
  • the glass substrate of a liquid crystal cell, the glass for glare-proof, the glass for sunglasses etc. can be mentioned, for example.
  • an optical film with an adhesive (upper polarizing plate) is laminated on the glass substrate on the front side (viewing side) of the liquid crystal cell, and another optical film with adhesive (lower polarizing plate) on the glass substrate on the back side of the liquid crystal cell.
  • an optical film with an adhesive (upper polarizing plate) is laminated on the glass substrate on the front side (viewing side) of the liquid crystal cell, and another optical film with adhesive (lower polarizing plate) on the glass substrate on the back side of the liquid crystal cell.
  • the material of the glass substrate include soda lime glass, low alkali glass, non-alkali glass, and the like, and non-alkali glass is suitably used for the liquid crystal cell.
  • a polarizing film 5 is configured by sticking a protective film 3 having a surface treatment layer 2 on one surface of a polarizing film 1 on the surface opposite to the surface treatment layer 2. ing.
  • the polarizing plate 5 is also the optical film 10 referred to in the present invention.
  • An adhesive layer 20 is provided on the surface of the polarizing film 1 opposite to the protective film 3 to form an optical film 25 with an adhesive.
  • the surface on the opposite side to the polarizing plate 5 of the adhesive layer 20 is bonded to the liquid crystal cell 30 which is a glass substrate, and the optical laminated body 40 is comprised.
  • the first protective film 3 having the surface treatment layer 2 is attached to one surface of the polarizing film 1 on the surface opposite to the surface treatment layer 2.
  • a second protective film 4 is stuck to form a polarizing plate 5.
  • the polarizing plate 5 is simultaneously the optical film 10 referred to in the present invention.
  • An adhesive layer 20 is provided on the outer side of the second protective film 4 constituting the polarizing plate 5 to form an optical film 25 with an adhesive.
  • the surface on the opposite side to the polarizing plate 5 of the adhesive layer 20 is bonded to the liquid crystal cell 30 which is a glass substrate, and the optical laminated body 40 is comprised.
  • a polarizing film 5 is formed by sticking a protective film 3 having a surface treatment layer 2 on one side of a polarizing film 1 on the surface opposite to the surface treatment layer 2. Yes.
  • a retardation film 7 is stuck via an interlayer adhesive 8 to constitute an optical film 10.
  • An adhesive layer 20 is provided on the outer side of the retardation film 7 constituting the optical film 10 to constitute an optical film 25 with an adhesive.
  • the surface on the opposite side to the optical film 10 of the adhesive layer 20 is bonded to the liquid crystal cell 30 which is a glass substrate, and the optical laminated body 40 is comprised.
  • the first protective film 3 having the surface treatment layer 2 is attached to one surface of the polarizing film 1 on the surface opposite to the surface treatment layer 2, and the polarizing film A polarizing plate 5 is configured by sticking a second protective film 4 to the other surface of 1.
  • a retardation film 7 is stuck via an interlayer adhesive 8 to constitute an optical film 10.
  • An adhesive layer 20 is provided on the outer side of the retardation film 7 constituting the optical film 10 to constitute an optical film 25 with an adhesive.
  • the surface on the opposite side to the optical film 10 of the adhesive layer 20 is bonded to the liquid crystal cell 30 which is a glass substrate, and the optical laminated body 40 is comprised.
  • the first protective film 3 and the second protective film 4 are generally composed of a triacetyl cellulose film, but may be composed of the various transparent resin films described above. it can.
  • the surface treatment layer formed on the surface of the first protective film 3 can be a hard coat layer, an antiglare layer, an antireflection layer, an antistatic layer, or the like. Of these, a plurality of layers may be provided.
  • a suitable example of the retardation film 7 is a medium-to-small liquid crystal display device.
  • a quarter-wave plate it is general that the absorption axis of the polarizing plate 5 and the slow axis of the retardation film 7 which is a quarter wavelength plate are arranged so as to intersect at about 45 degrees. Depending on the characteristics, the angle may be shifted from 45 degrees to some extent.
  • a retardation film having various retardation values in accordance with the characteristics of the liquid crystal cell 30 is used for the purpose of phase difference compensation and viewing angle compensation of the liquid crystal cell 30.
  • the polarizing plate 5 and the retardation film 7 are generally arranged so that the absorption axis and the slow axis of the retardation film 7 are substantially orthogonal or substantially parallel.
  • a uniaxial or biaxial stretched film is preferably used.
  • the retardation film 7 is provided for the purpose of retardation compensation or viewing angle compensation of the liquid crystal cell 30, in addition to the uniaxial or biaxially stretched film, it is also oriented in the thickness direction in addition to the uniaxial or biaxially stretched film.
  • an optical compensation film such as a film or a film obtained by coating and fixing a retardation-expressing substance such as liquid crystal on a support film, can also be used as the retardation film 7.
  • the interlayer adhesive 8 includes A typical acrylic pressure-sensitive adhesive is usually used, but it is of course possible to use a pressure-sensitive adhesive sheet as defined herein.
  • an adhesive that can be firmly bonded once bonded and cannot be peeled off.
  • an adhesive for example, an aqueous adhesive that is composed of an aqueous solution or an aqueous dispersion and exhibits adhesive strength by evaporating water as a solvent, ultraviolet curing that is cured by ultraviolet irradiation and exhibits adhesive strength. Examples thereof include a mold adhesive.
  • FIG. 1 can also be distributed by themselves, in which the pressure-sensitive adhesive layer 20 is formed on the retardation film 7.
  • An optical film with an adhesive with an adhesive layer formed on a retardation film can be bonded to a liquid crystal cell that is a glass substrate to form an optical laminate, and a polarizing plate is provided on the retardation film side. It can also paste and can be set as another optical film with an adhesive.
  • FIG. 1 shows an example in which the optical film 25 with an adhesive is arranged on the viewing side of the liquid crystal cell 30, but the optical film with an adhesive according to the present invention is the back side of the liquid crystal cell, that is, the back. It can also be placed on the light side.
  • a protective film having no surface treatment layer is employed instead of the protective film 3 having the surface treatment layer 2 shown in FIG.
  • Others can be configured similarly to (A) to (D) of FIG.
  • various optical films known to be disposed on the back side of the liquid crystal cell such as a brightness enhancement film, a light collecting film, and a diffusion film, may be provided outside the protective film constituting the polarizing plate. Is possible.
  • the optical layered body of the present invention can be suitably used for a liquid crystal display device.
  • the liquid crystal display device formed from the optical laminate of the present invention includes, for example, a notebook type, a desktop type, a personal computer liquid crystal display including a PDA (Personal Digital Assistant), a television, an in-vehicle display, an electronic dictionary, and a digital camera. It can be used for digital video cameras, electronic desk calculators, watches, etc.
  • PDA Personal Digital Assistant
  • HSA 2-carboxyethyl acrylate
  • A-3 monomer
  • A-1 monomers
  • A-2 monomers
  • A-2 monomers
  • A-2 monomers
  • A-2 monomers
  • A-2 monomers
  • A-2 monomers
  • A-2 monomers
  • A-2 monomers
  • A-2 monomers
  • A-2 monomers
  • A-2 monomers
  • AA Acrylic acid
  • Table 1 a monomer other than A-3
  • the internal temperature is controlled by replacing the air in the apparatus with nitrogen gas so as not to contain oxygen. Raised to 55 ° C.
  • a total amount of a solution prepared by dissolving 0.14 part of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added.
  • Examples and Comparative Examples in which pressure-sensitive adhesives were prepared using the (meth) acrylic resins produced in Polymerization Examples A to C and applied to optical films are shown.
  • those shown in Table 2 were used as the crosslinking agent (B) and the silane compound.
  • the crosslinking agent (B) and silane compound shown in Table 2 are shown below.
  • the first names listed are all product names.
  • Coronate L Trimethylolpropane adduct of tolylene diisocyanate in ethyl acetate solution (solid content: 75%), obtained from Nippon Polyurethane Co., Ltd.
  • KBM-403 3-glycidoxypropyltrimethoxysilane, liquid, manufactured by Shin-Etsu Chemical Co., Ltd.
  • KBM-4803 Glycidoxyoctyltrimethoxysilane, manufactured by Shin-Etsu Chemical Co., Ltd.
  • A100 acetoacetylpropyltrimethoxysilane, manufactured by Soken Chemical Co., Ltd.
  • KBM-573 N-phenyl-3-aminopropyltrimethoxysilane, manufactured by Shin-Etsu Chemical Co., Ltd.
  • Examples 1 to 4 and Comparative Examples 1 to 6 (A) Production of pressure-sensitive adhesive compositions of Examples 1 to 4 and Comparative Examples 1 to 6 Solid content of 20% ethyl acetate solution of (meth) acrylic resin obtained in any of Polymerization Examples A to C shown in Table 2 To 100 parts by weight, 0.5 parts by weight of the cross-linking agent and the above silane compound are mixed in the amounts shown in Table 2, and ethyl acetate is added so that the solids concentration is 13%. Thus, pressure-sensitive adhesive compositions of Examples 1 to 4 and Comparative Examples 1 to 6 were prepared.
  • Example 1 has a decrease rate of the adhesive strength as compared with Comparative Examples 1, 4, 5, and 6. It was expensive.
  • Examples 2 and 3 had a higher adhesive force reduction rate than Comparative Example 2.
  • Example 4 had a higher adhesive force reduction rate than Comparative Example 3.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nonlinear Science (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Mathematical Physics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)
  • Laminated Bodies (AREA)
  • Polarising Elements (AREA)
  • Liquid Crystal (AREA)
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