WO2010018794A1 - 粘着剤付き光学フィルムとそれを用いた光学積層体 - Google Patents

粘着剤付き光学フィルムとそれを用いた光学積層体 Download PDF

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WO2010018794A1
WO2010018794A1 PCT/JP2009/064038 JP2009064038W WO2010018794A1 WO 2010018794 A1 WO2010018794 A1 WO 2010018794A1 JP 2009064038 W JP2009064038 W JP 2009064038W WO 2010018794 A1 WO2010018794 A1 WO 2010018794A1
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Prior art keywords
weight
film
optical film
pressure
sensitive adhesive
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PCT/JP2009/064038
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English (en)
French (fr)
Japanese (ja)
Inventor
流 竹厚
容演 金
廷昊 柳
陽介 太田
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住友化学株式会社
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Priority to KR1020117003978A priority Critical patent/KR101635234B1/ko
Priority to CN200980131207.XA priority patent/CN102119349B/zh
Publication of WO2010018794A1 publication Critical patent/WO2010018794A1/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
    • 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
    • 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
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • 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
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • 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
    • 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
    • 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
    • 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
    • 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
    • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
    • C09J2301/302—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
    • 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
    • C09J2433/00—Presence of (meth)acrylic polymer

Definitions

  • the present invention relates to an optical film having an adhesive layer formed thereon.
  • the optical film to be used in the present invention include a polarizing plate and a retardation film.
  • the present invention also relates to an optical laminate for liquid crystal display using an optical film in which the pressure-sensitive adhesive layer is formed.
  • a polarizing plate is mounted on a liquid crystal display device and is widely used.
  • a transparent protective film is laminated on both surfaces of a polarizer, and an adhesive layer is formed on the surface of at least one protective film. It is distributed in the state where the release film is stuck to.
  • a retardation film may be laminated on a polarizing plate in which a protective film is bonded to both surfaces of the polarizer to form an elliptical polarizing plate, and an adhesive layer / release film may be attached to the retardation film side. is there.
  • an adhesive layer / release film may be stuck on the surface of the retardation film.
  • the release film Prior to bonding to the liquid crystal cell, the release film is peeled off from these polarizing plate, elliptical polarizing plate, retardation film, etc., and bonded to the liquid crystal cell via the exposed adhesive layer.
  • a polarizing plate, elliptical polarizing plate, or retardation film generates static electricity when the release film is peeled off and bonded to a liquid crystal cell, and therefore development of a countermeasure for the prevention is desired.
  • Patent Document 1 in a polarizing plate in which a protective film is laminated on the surface of a polarizer film and an adhesive layer is provided on the surface of the protective film,
  • an adhesive it has been proposed to use an ion conductive composition comprising an electrolyte salt and an organopolysiloxane and a composition containing an acrylic copolymer.
  • Patent Document 2 discloses that an organic salt-based antistatic agent is blended with a pressure-sensitive adhesive (adhesive) to impart antistatic properties to the adhesive. It is disclosed.
  • Patent Document 3 includes a salt made of a quaternary ammonium cation having a total carbon number of 4 to 20 and a fluorine atom-containing anion in an adhesive or the like, thereby improving antistatic properties. It is described to give. Furthermore, Japanese Patent Application Laid-Open No.
  • Patent Document 4 describes that an ionic liquid that becomes liquid at room temperature (25 ° C.) is contained in an adhesive to prevent charging.
  • the polarizing plate coated with an adhesive is left for a long time, the antistatic property is still deteriorated due to a change with time. Since the distribution and storage period of a general polarizing plate is about six months at the maximum from the production, it is required to maintain the antistatic performance until the customer uses it.
  • the optical film with an adhesive as described above is bonded to a liquid crystal cell on the adhesive layer side to form a liquid crystal display device.
  • the optical film is placed under high temperature or high temperature and high humidity conditions, or heated.
  • foaming occurs in the pressure-sensitive adhesive layer as the optical film changes in size, or it floats or peels between the optical film and the pressure-sensitive adhesive layer, or between the pressure-sensitive adhesive layer and the liquid crystal cell glass. Therefore, it is also required to have excellent durability without causing such problems.
  • Patent Document 5 a ratio of the weight average molecular weight (Mw) and the number average molecular weight (Mn) of a resin obtained by copolymerizing an aromatic ring-containing monomer with an alkyl acrylate (A method for suppressing light leakage by broadening the molecular weight distribution represented by (Mw / Mn) to 10 to 50 is described.
  • an adhesive By using such an adhesive, light leakage is reduced, but it is not always sufficient, and due to the wide molecular weight distribution, foaming may occur under high temperature conditions.
  • An object of the present invention is to provide a high antistatic property, and the antistatic property hardly changes with time, and is provided with a pressure sensitive adhesive layer on the surface of an optical film that is excellent in suppressing white spots even when the size is increased. It is to provide an optical film.
  • an acrylic ester containing a structural unit derived from an unsaturated monomer having an acrylic ester as a main component and an aromatic ring in the molecule By blending a resin and a specific ionic compound and providing this composition as an adhesive layer on the surface of the optical film, an optical film with an adhesive excellent in whitening prevention, antistatic properties and durability can be obtained. As a result, the present invention was reached.
  • the present invention is an optical film with an adhesive in which an adhesive layer is formed on at least one surface of the optical film, and the adhesive layer is (A) (A-1)
  • the following formula (I) is (A) (A-1) The following formula (I)
  • R 1 represents a hydrogen atom or a methyl group
  • R 2 represents an alkyl group having 1 to 14 carbon atoms which may be substituted with an alkoxy group having 1 to 10 carbon atoms
  • (A-3) 0.1 to 5% by weight of an unsaturated monomer having a polar functional group
  • the pressure-sensitive adhesive layer is an optical film with a pressure-sensitive adhesive having a gel fraction of 70 to 99% by weight.
  • an optical laminate in which the above optical film with an adhesive is laminated on a glass substrate on the adhesive layer side.
  • an unsaturated monomer (A-2) having one olefinic double bond and at least one aromatic ring in the molecule is used as the pressure-sensitive adhesive composition for forming the pressure-sensitive adhesive layer.
  • a composition containing an acrylic resin (A) as an ingredient and an ionic compound (B) having an organic cation and a melting point of 80 ° C. or lower optical components resulting from uneven stress distribution Since white defects are prevented, charging of optical members can be effectively suppressed, and the initial antistatic performance is maintained even after storage for a long time after production. Is possible.
  • the optical film with pressure-sensitive adhesive of the present invention is once laminated on a glass substrate, and if there is any inconvenience, even if it is peeled off from the glass substrate together with the pressure-sensitive adhesive, adhesive residue or There is little fogging, and it can be used again as a glass substrate, and has excellent reworkability.
  • the optical film with pressure-sensitive adhesive of the present invention uses an acrylic resin (A) having a molecular weight distribution (Mw / Mn) of 3 to 7 as a pressure-sensitive adhesive composition for forming a pressure-sensitive adhesive layer.
  • A acrylic resin
  • Mw / Mn molecular weight distribution
  • the gel fraction of the pressure-sensitive adhesive layer is in the range of 70 to 99% by weight, the durability of the pressure-sensitive adhesive layer is improved, and this optical film with pressure-sensitive adhesive is attached to the glass substrate of the liquid crystal cell.
  • the test such as heat resistance, moisture heat resistance, heat shock resistance is performed, the appearance change is suppressed.
  • This optical film with an adhesive gives, for example, an optical laminate for liquid crystal display by being laminated on a glass substrate of a liquid crystal cell.
  • the pressure-sensitive adhesive layer absorbs and relaxes stress caused by dimensional changes of the optical film and glass substrate under wet heat conditions, so that local stress concentration is reduced and the pressure-sensitive adhesive layer floats on the glass substrate. And peeling are suppressed.
  • the optical film with pressure-sensitive adhesive of the present invention is one in which a pressure-sensitive adhesive layer is formed on at least one side of the optical film, and the pressure-sensitive adhesive composition forming the pressure-sensitive adhesive layer is (A) acrylic resin, (B) It is formed from a composition containing an ionic compound having an organic cation and a melting point of 80 ° C. or lower, and (C) a crosslinking agent.
  • A acrylic resin
  • B It is formed from a composition containing an ionic compound having an organic cation and a melting point of 80 ° C. or lower
  • C a crosslinking agent
  • the acrylic resin (A) used in the pressure-sensitive adhesive composition is mainly composed of a structural unit derived from the (meth) acrylic acid ester represented by the formula (I). Specifically, in addition to the structural unit derived from the (meth) acrylic acid ester, it is derived from an unsaturated monomer having one olefinic double bond and at least one aromatic ring in the molecule.
  • An unsaturated monomer having a polar functional group such as a structural unit, a free carboxyl group, a hydroxyl group, an amino group, a heterocyclic group such as an epoxy ring, preferably a (meth) acrylic acid compound having a polar functional group
  • (meth) acrylic acid means that either acrylic acid or methacrylic acid may be used, and “(meth)” when referred to as (meth) acrylate or the like has the same meaning.
  • R 1 is a hydrogen atom or a methyl group
  • R 2 is an alkyl group having 1 to 14 carbon atoms.
  • a hydrogen atom in each group may be substituted with an alkoxy group having 1 to 10 carbon atoms.
  • (meth) acrylic acid ester (A-1) represented by the formula (I) those in which R 2 is an unsubstituted alkyl group, specifically, methyl acrylate, ethyl acrylate, propyl acrylate, Linear alkyl acrylate esters such as n-butyl acrylate, n-octyl acrylate, lauryl acrylate; branched alkyl acrylates such as isobutyl acrylate, 2-ethylhexyl acrylate, isooctyl acrylate Esters; linear alkyl methacrylates such as methyl methacrylate, ethyl methacrylate, propyl methacrylate, n-butyl methacrylate, n-octyl methacrylate, lauryl methacrylate; isobutyl methacrylate, 2-ethylhexyl methacrylate Branches such as isooctyl methacrylate
  • n-butyl acrylate is preferable. Specifically, among all the monomers constituting the acrylic resin (A), n-butyl acrylate is 50% by weight or more, and the above-described one is used. It is preferable to use it so as to satisfy the regulations regarding (meth) acrylic acid ester (A-1).
  • the (meth) acrylic acid ester represented by the formula (I) is specifically acrylic acid. Examples include 2-methoxyethyl, ethoxymethyl acrylate, 2-methoxyethyl methacrylate, ethoxymethyl methacrylate, and the like.
  • the unsaturated monomer (A-2) having one olefinic double bond and at least one aromatic ring in the molecule has a (meth) acryloyl group as a group containing an olefinic double bond.
  • a (meth) acryloyl group as a group containing an olefinic double bond.
  • examples thereof include benzyl (meth) acrylate, neopentyl glycol benzoate (meth) acrylate, and the like, and an unsaturated monomer represented by the following formula (II) is particularly preferable.
  • R 3 represents a hydrogen atom or a methyl group
  • n represents an integer of 1 to 8
  • R 4 represents a hydrogen atom, an alkyl group, an aralkyl group, or an aryl group.
  • R 4 is an alkyl group
  • its carbon number can be about 1 to 9
  • Examples of the alkyl group having 1 to 9 carbon atoms include a methyl group, a butyl group, and a nonyl group, and examples of the aralkyl group having 6 to 11 carbon atoms include a benzyl group, a phenethyl group, and a naphthylmethyl group.
  • Examples of the aryl group include a phenyl group, a tolyl group, and a naphthyl group.
  • Specific unsaturated monomers of the formula (II) include 2-phenoxyethyl (meth) acrylate, 2- (2-phenoxyethoxy) ethyl (meth) acrylate, ethylene oxide-modified nonylphenol (meth) acrylate, 2 And-(o-phenylphenoxy) ethyl (meth) acrylate.
  • These unsaturated monomers having one olefinic double bond and at least one aromatic ring in these molecules may be used alone or in combination with a plurality of different monomers.
  • 2-phenoxyethyl (meth) acrylate or 2- (o-phenylphenoxy) ethyl (meth) acrylate is used as an aromatic ring-containing unsaturated monomer (A-2) constituting the acrylic resin (A). It is preferable to use as one of these.
  • Examples of the unsaturated monomer (A-3) having a polar functional group include unsaturated monomers having a free carboxyl group such as acrylic acid, methacrylic acid and ⁇ -carboxyethyl acrylate; (meth) acrylic acid Unsaturated monomers having a hydroxyl group, such as 2-hydroxyethyl, 2-hydroxypropyl (meth) acrylate, 2- or 3-chloro-2-hydroxypropyl (meth) acrylate, and diethylene glycol mono (meth) acrylate; Acryloylmorpholine, vinylcaprolactam, N-vinyl-2-pyrrolidone, tetrahydrofurfuryl (meth) acrylate, caprolactone-modified tetrahydrofurfuryl acrylate, 3,4-epoxycyclohexylmethyl (meth) acrylate, glycidyl (meth) acrylate, 2,5 -Dihydro Orchids such as, unsaturated
  • the polar functional group of the unsaturated monomer (A-3) is preferably a free carboxyl group, a hydroxyl group, an amino group, or an epoxy ring.
  • an unsaturated monomer having a hydroxyl group is preferably used as one of the polar functional group-containing unsaturated monomers (A-3) constituting the acrylic resin (A).
  • it is also effective to use an unsaturated monomer having another polar functional group for example, an unsaturated monomer having a free carboxyl group.
  • the content of the (meth) acrylic acid ester (A-1) represented by the formula (I) in the acrylic resin (A) is 80 to 96% by weight, preferably 82% by weight or more, and more preferably 85%. % By weight or more, preferably 94% by weight or less, and more preferably 92% by weight or less.
  • the content of the unsaturated monomer (A-2) having one olefinic double bond and at least one aromatic ring in the molecule in the acrylic resin (A) is 3 to 15% by weight.
  • 5% by weight or more Preferably 5% by weight or more, more preferably 5.5% by weight or more, especially 7% by weight or more, and preferably 12% by weight or less, more preferably 9.9% by weight or less, especially 9.5% by weight or less, More preferably, it is 9% by weight or less.
  • the content of the unsaturated monomer (A-3) having a polar functional group in the acrylic resin (A) is 0.1 to 5% by weight, preferably 0.5% by weight or more. Preferably it is 3 weight% or less.
  • the acrylic resin (A) used in the present invention comprises (meth) acrylic acid ester (A-1) represented by the formula (I) described above, at least one olefinic double bond in the molecule and at least It may contain a structural unit derived from a monomer other than the unsaturated monomer (A-2) having one aromatic ring and the unsaturated monomer (A-3) having a polar functional group.
  • examples of these include structural units derived from (meth) acrylic acid esters having an alicyclic structure in the molecule, structural units derived from styrene monomers, structural units derived from vinyl monomers, molecules Examples thereof include a structural unit derived from a monomer having a plurality of (meth) acryloyl groups.
  • 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-butyl acrylate
  • methacrylic acid esters having an alicyclic structure include isobornyl methacrylate, cyclohexyl methacrylate, dicyclopentanyl methacrylate, methacrylic acid, and the like, such as cyclohexyl, ⁇ -ethoxyacrylate cyclohexyl, and cyclohexyl phenyl acrylate.
  • styrenic monomers examples include styrene, alkyl styrene such as methyl styrene, dimethyl styrene, trimethyl styrene, ethyl styrene, diethyl styrene, triethyl styrene, propyl styrene, butyl styrene, hexyl styrene, heptyl styrene, octyl styrene.
  • alkyl styrene such as methyl styrene, dimethyl styrene, trimethyl styrene, ethyl styrene, diethyl styrene, triethyl styrene, propyl styrene, butyl styrene, hexyl styrene,
  • Halogenated styrenes such as fluorostyrene, chlorostyrene, bromostyrene, dibromostyrene, iodostyrene; and nitrostyrene, acetylstyrene, methoxystyrene, divinylbenzene and the like.
  • vinyl monomers include vinyl acetate, vinyl propionate, vinyl butyrate, vinyl 2-ethylhexanoate and vinyl laurate; vinyl halides such as vinyl chloride and vinyl bromide; vinylidene chloride And vinylidene halides such as: nitrogen-containing aromatic vinyl such as vinylpyridine, vinylpyrrolidone and vinylcarbazole; conjugated diene monomers such as butadiene, isoprene and chloroprene; and acrylonitrile and methacrylonitrile.
  • vinyl halides such as vinyl chloride and vinyl bromide
  • vinylidene chloride And vinylidene halides such as: nitrogen-containing aromatic vinyl such as vinylpyridine, vinylpyrrolidone and vinylcarbazole; conjugated diene monomers such as butadiene, isoprene and chloroprene; and acrylonitrile and methacrylonitrile.
  • 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-nonanediol.
  • Monomers other than the unsaturated monomer (A-3) having a polar functional group can be used alone or in combination of two or more.
  • These structural units derived from monomers other than (A-1) to (A-3) are usually 0 to 20 parts by weight, preferably 0 to 0 parts by weight with respect to 100 parts by weight of the nonvolatile content of the acrylic resin (A). It is contained at a ratio of 10 parts by weight.
  • the active ingredient of the pressure-sensitive adhesive is the (meth) acrylic acid ester (A-1) represented by the formula (I) as described above, having one olefinic double bond and at least one aromatic ring in the molecule. It may contain two or more kinds of acrylic resins containing structural units derived from the unsaturated monomer (A-2) having a polar functional group and the unsaturated monomer having a polar functional group (A-3). Further, the acrylic resin is mixed with an acrylic resin different from the acrylic resin, specifically, for example, an acrylic resin having a structural unit derived from the (meth) acrylic ester of the formula (I) and containing no polar functional group. It may be what you did.
  • the acrylic resin containing a structural unit derived from the unsaturated monomer (A-3) having a polar functional group is preferably 80% by weight or more, more preferably 90% by weight or more, based on the whole acrylic resin.
  • GPC gel permeation chromatography
  • the weight average molecular weight in terms of standard polystyrene is 1,000,000 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 layer 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 layer changes, the pressure-sensitive adhesive layer fluctuates following the dimensional change. This is preferable because there is no difference between the brightness of the peripheral edge and the brightness of the center, 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) to the number average molecular weight (Mn) is in the range of 3-7.
  • the acrylic resin (A) preferably has a glass transition temperature in the range of ⁇ 10 to ⁇ 60 ° C. in order to develop adhesiveness.
  • the glass transition temperature of the resin can generally be measured with a differential scanning calorimeter.
  • the acrylic resin (A) constituting the pressure-sensitive adhesive layer 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.
  • 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 for the production of the 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) Azo) compounds such as 2,2'-azobis (2-hydroxymethylpropionitrile); lauryl peroxide, tert-butyl hydroperoxide, benzoyl peroxide, tert-butyl peroxybenzoate, cumene hydroperoxide , Diisopropyl peroxydicarbonate, dipropyl peroxydicarbonate, tert-butyl peroxy Organic peroxides such as neodecanoate, tert-butyl peroxypivalate, (3,5,5-trimethyl
  • the solution polymerization method is preferable among the methods shown above.
  • a specific example of the solution polymerization method will be described below.
  • a desired monomer and an organic solvent are mixed, and a thermal polymerization initiator is added under a nitrogen atmosphere, and the temperature is about 40 to 90 ° C., preferably 60 to 80 ° C.
  • An example is a method of stirring at about 0 ° C. for about 3 to 10 hours.
  • a monomer or a thermal polymerization initiator may be added continuously or intermittently during the polymerization, or may be added in a state dissolved in an organic solvent.
  • 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 ketone. Ketones such as can be used.
  • the cation component constituting the ionic compound (B) is not particularly limited as long as it is an organic cation satisfying that it becomes an ionic compound having a melting point of 80 ° C. or lower.
  • imidazolium cation, pyridinium cation, ammonium cation, sulfonium cation, phosphonium cation, etc. are mentioned, but when used in the adhesive layer of an optical film, it is difficult to be charged when peeling the release film provided on it. From the viewpoint, a pyridinium cation and an imidazolium cation are preferable.
  • the molecular weight of the ionic compound (B) is not particularly limited, but for example, the molecular weight is preferably 700 or less, and more preferably 500 or less.
  • the anion component serving as the counter ion of the cation component is not particularly limited as long as it satisfies that the melting point is an ionic compound having a melting point of 80 ° C. or less. It may be an organic anion, and examples thereof include the following.
  • an anion component containing a fluorine atom is preferably used because it provides an ionic compound having excellent antistatic performance, and a hexafluorophosphate anion or a bis (trifluoromethanesulfonyl) imide anion is particularly preferable.
  • ionic compound used in the present invention can be appropriately selected from the combination of the cation component and the anion component.
  • Specific examples of the compound that is a combination of a cation component and an anion component include the following.
  • Such ionic compounds (B) can be used alone or in combination of two or more. Examples of the ionic compound (B) are not limited to the substances listed above.
  • the ionic compound (B) having a melting point of 80 ° C. or lower imparts antistatic properties to the pressure-sensitive adhesive layer formed from the composition containing the acrylic resin (A) and has various physical properties as a pressure-sensitive adhesive. It is effective in keeping.
  • the ionic compound preferably has a melting point of 80 ° C. or lower, more preferably 70 ° C. or lower.
  • the ionic compound (B) preferably has a melting point of preferably 30 ° C. or higher, more preferably 35 ° C. or higher.
  • the ionic compound (B) that is solid at room temperature (25 ° C.) retains the antistatic performance of the pressure-sensitive adhesive layer in which it is mixed for a long period of time compared to the ionic compound that is liquid at room temperature. Can do.
  • the ionic compound (B) is 0.2% with respect to 100 parts by weight of the nonvolatile content of the acrylic resin (A) (the total amount of structural units derived from each of the above A-1, A-2 and A-3). It is contained at a ratio of ⁇ 8 parts by weight.
  • the ionic compound (B) is contained in an amount of 0.2 parts by weight or more with respect to 100 parts by weight of the nonvolatile content of the acrylic resin (A), the antistatic performance is improved, and the amount is 8 parts by weight or less. It is preferable because durability is easy to maintain.
  • the amount of the ionic compound (B) with respect to 100 parts by weight of the acrylic resin (A) is preferably 0.5 parts by weight or more and 3 parts by weight or less.
  • Crosslinking agent (C) A crosslinking agent (C) is further blended into the acrylic resin (A) and the ionic compound (B) as described above to obtain a pressure-sensitive adhesive composition.
  • the crosslinking agent (C) is a compound having in the molecule at least two functional groups capable of crosslinking with structural units derived from the polar monomer-containing unsaturated monomer in the acrylic resin (A). Examples of the compound include an isocyanate compound, an epoxy compound, a metal chelate compound, and an aziridine compound.
  • 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 converting 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, 1,3-bis ( N, N-diglycidylaminomethyl) cyclohexane 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-tri- ⁇ -aziridinylpropionate, tetramethylolmethane-tri- ⁇ -aziridinylpropionate, and the like.
  • isocyanate compounds especially 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.
  • the polar functional group-containing unsaturated monomer (A-3) has a polar functional group selected from a free carboxyl group, a hydroxyl group, an amino group, and an epoxy ring, as at least one of the crosslinking agent (C), It is preferable to use an isocyanate compound.
  • suitable isocyanate compounds include tolylene diisocyanate, adducts obtained by reacting tolylene diisocyanate with polyols, tolylene diisocyanate dimers, and tolylene diisocyanate trimers, hexamethylene diisocyanate, and hexamethylene diisocyanate. Examples include adducts reacted with polyols, dimers of hexamethylene diisocyanate, and trimers of hexamethylene diisocyanate.
  • the crosslinking agent (C) is blended at a ratio of 0.01 to 5 parts by weight with respect to 100 parts by weight of the acrylic resin (A).
  • the blending amount of the crosslinking agent (C) is preferably about 0.1 to 5 parts by weight, more preferably about 0.2 to 3 parts by weight with respect to 100 parts by weight of the acrylic resin (A). It is preferable that the amount of the crosslinking agent (C) with respect to 100 parts by weight of the acrylic resin (A) is 0.01 parts by weight or more, particularly 0.1 parts by weight or more because the durability of the pressure-sensitive adhesive layer tends to be improved. Moreover, when it is 5 parts by weight or less, it is preferable because white spots are not noticeable when the optical film with an adhesive is applied to a liquid crystal display device.
  • the pressure-sensitive adhesive composition for forming the pressure-sensitive adhesive layer in the present invention preferably contains a silane-based compound (D) in order to improve the adhesion between the pressure-sensitive adhesive layer and the glass substrate. It is preferable to contain the silane compound (D) in the acrylic resin before blending the agent.
  • silane compound (D) examples include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- ( 2-aminoethyl) -3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3,4-epoxy (Cyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-glycidoxypropyltrime
  • the silane compound (D) may be of a silicone oligomer type.
  • silicone oligomer in the form of a copolymer include the following.
  • the compounding amount of the silane compound in the pressure-sensitive adhesive is usually about 0.01 to 10 parts by weight with respect to 100 parts by weight of the nonvolatile content of the acrylic resin (A) (the total weight when two or more types are used), preferably Is used in a proportion of 0.03 to 1 part by weight. It is preferable that the amount of the silane compound with respect to 100 parts by weight of the acrylic resin is 0.01 parts by weight or more, particularly 0.03 parts by weight or more because adhesion between the pressure-sensitive adhesive layer and the glass substrate is improved. Moreover, it is preferable for the amount to be 10 parts by weight or less, particularly 1 part by weight or less, because the silane compound tends to be suppressed from bleeding out from the pressure-sensitive adhesive layer.
  • the adhesive described above may further contain a crosslinking catalyst, weathering stabilizer, tackifier, plasticizer, softener, dye, pigment, inorganic filler, resin other than the acrylic resin (A), and the like. It is also useful to blend a UV curable compound with the pressure-sensitive adhesive and to cure it by irradiating it with ultraviolet light after forming the pressure-sensitive adhesive layer to form a harder pressure-sensitive adhesive layer. Above all, if a cross-linking catalyst and a cross-linking catalyst are added to the pressure-sensitive adhesive, the pressure-sensitive adhesive layer can be prepared by aging in a short time, and the resulting resin film with pressure-sensitive adhesive floats between the resin film and the pressure-sensitive adhesive layer.
  • the crosslinking catalyst examples include amine compounds such as hexamethylenediamine, ethylenediamine, polyethyleneimine, hexamethylenetetramine, diethylenetriamine, triethylenetetramine, isophoronediamine, trimethylenediamine, polyamino resin, and melamine resin.
  • an amine compound is added to the adhesive as a crosslinking catalyst, an isocyanate compound is suitable as the crosslinking agent.
  • Each of these components constituting the pressure-sensitive adhesive is made into a pressure-sensitive adhesive composition in a state dissolved in a solvent, applied onto a suitable base material, and dried to form a pressure-sensitive adhesive layer.
  • the pressure-sensitive adhesive layer has a gel fraction of 70 to 99% by weight.
  • the gel fraction is a value measured according to the following (I) to (IV).
  • a pressure-sensitive adhesive layer having an area of about 8 cm ⁇ about 8 cm and a metal mesh composed of SUS304 (about 10 cm ⁇ about 10 cm) (with a weight of Wm) are bonded.
  • the gel fraction of the pressure-sensitive adhesive layer should be 70 to 99% by weight. When the gel fraction is 70% by weight or more, the durability of the pressure-sensitive adhesive layer is improved, and when the gel fraction is 99% by weight or less, it is preferable because the production is easy.
  • the gel fraction of the pressure-sensitive adhesive layer can be adjusted by, for example, the type of acrylic resin (A) that is an active ingredient of the pressure-sensitive adhesive layer and the amount of the crosslinking agent. Specifically, if the amount of the unsaturated monomer (A-3) having a polar functional group in the acrylic resin (A) is increased or the amount of the crosslinking agent (C) in the pressure-sensitive adhesive composition is increased. Since the gel fraction becomes high, the gel fraction may be adjusted by the amount of the unsaturated monomer having a polar functional group and / or the crosslinking agent.
  • the amount of units derived from the unsaturated monomer (A-3) having the polar functional group in the acrylic resin (A) is determined.
  • the compounding quantity of the crosslinking agent with respect to 100 weight part (the total amount when using 2 or more types) of the non volatile matter of the acrylic resin (A) which comprises an adhesive layer is 0.1. It is preferable to select from the range of about 5 parts by weight according to the type of acrylic resin.
  • optical film with adhesive The optical film with a pressure-sensitive adhesive of the present invention is obtained by providing a pressure-sensitive adhesive layer formed of the above pressure-sensitive adhesive composition on at least one surface of an optical film.
  • the optical film used here is a film having optical characteristics, 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 dichroic dye such as iodine or a dichroic dye is added to a uniaxially stretched polyvinyl alcohol resin film.
  • a dichroic dye such as iodine or a dichroic dye is added to a uniaxially stretched polyvinyl alcohol resin film.
  • 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 made of polymethyl methacrylate, liquid crystal polyester, acetylcellulose, 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.
  • Such retardation films include what are called temperature-compensated retardation films, and films with a twisted orientation of rod-like liquid crystals sold under the trade name “LC film” by Nippon Oil Corporation.
  • LC film a film with a tilted orientation of a rod-shaped liquid crystal sold under the trade name “NH film” by Shin Nippon Oil Co., Ltd., and a disk-shaped liquid crystal sold under the trade name “WV film” by FUJIFILM Corporation.
  • VAC film a film with a tilt orientation
  • new VAC film a fully biaxially oriented film sold by Sumitomo Chemical Co., Ltd. under the name “VAC film”
  • VAC film a fully biaxially oriented film sold by Sumitomo Chemical Co., Ltd. under the name “VAC film”
  • VAC film a fully biaxially oriented film sold by Sumitomo Chemical Co., Ltd. under the name “VAC film”
  • new VAC film a product name
  • 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, or a nickel complex compound.
  • an acetyl cellulose resin film such as a triacetyl cellulose film is preferably used.
  • the linearly polarizing plate is used in a state where a protective film is attached to one or both sides of a polarizer constituting the polarizer, for example, a polarizer film made of a polyvinyl alcohol-based resin.
  • a polarizer constituting the polarizer
  • the elliptically polarizing plate described above is a laminate of a linearly polarizing plate and a retardation film, and the polarizing plate may also be in a state where a protective film is attached to one or both sides of the polarizer film.
  • the pressure-sensitive adhesive layer according to the present invention is formed on such an elliptically polarizing plate, the pressure-sensitive adhesive layer is usually formed on the retardation film side.
  • the optical film with a pressure-sensitive adhesive has a release film attached to the surface of the pressure-sensitive adhesive layer and protects the surface of the pressure-sensitive adhesive layer until use.
  • the optical film with the pressure-sensitive adhesive provided with the release film in this manner is formed by, for example, applying the above-mentioned pressure-sensitive adhesive composition on the release film to form a pressure-sensitive adhesive layer, and further optically applying the obtained pressure-sensitive adhesive layer.
  • a method of laminating a film a method of applying a pressure-sensitive adhesive composition on an optical film to form a pressure-sensitive adhesive layer, 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 release film used here is, for example, a film made of various resins such as polyethylene terephthalate, polybutylene terephthalate, polycarbonate, polyarylate, etc. It can be one that has undergone mold processing.
  • the thickness of the pressure-sensitive adhesive layer is not particularly limited, it is usually preferably 30 ⁇ m or less, more preferably 10 ⁇ m or more, and further 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 there is a tendency that the possibility of floating or peeling between the glass substrate and the pressure-sensitive adhesive layer is reduced. It is preferable because the reworkability tends to improve, and if the thickness is 10 ⁇ m or more, even if the dimension of the optical film bonded thereto changes, the adhesive layer follows the change in dimension and fluctuates.
  • the thickness of the pressure-sensitive adhesive layer adhered to the liquid crystal cell glass has been 25 ⁇ m as standard, but in the present invention, even if the thickness is 20 ⁇ m or less, sufficient performance as the pressure-sensitive adhesive layer is exhibited. To do.
  • the optical film with the pressure-sensitive adhesive of the present invention is attached to a glass substrate to form an optical laminate, and when there is some inconvenience and the optical film is peeled from the glass substrate, the pressure-sensitive adhesive layer is accompanied by the optical film. Since the surface of the glass substrate that has been peeled off and is in contact with the pressure-sensitive adhesive layer hardly causes fogging or adhesive residue, it is easy to re-attach the optical film with the pressure-sensitive adhesive again to the glass substrate after peeling. That is, it is excellent in so-called reworkability.
  • optical laminate The optical film with pressure-sensitive adhesive of the present invention can be laminated on a glass substrate with the pressure-sensitive adhesive layer to form an optical laminate.
  • the release film is peeled off from the optical film with an adhesive obtained as described above, and the exposed adhesive layer is removed from the surface of the glass substrate. You just have to stick together.
  • a glass substrate 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.
  • the optical laminated body formed by laminating is preferable because it can be used as a panel (liquid crystal panel) for a liquid crystal display device.
  • the material for the glass substrate include soda lime glass, low alkali glass, and non-alkali glass.
  • a polarizing plate 5 is configured by sticking a protective film 3 having a surface treatment layer 2 on one side of a linear polarizing film 1 on the surface opposite to the surface treatment layer 2.
  • the polarizing plate 5 is also the optical film 10 referred to in the present invention.
  • the pressure-sensitive adhesive layer 20 containing the ionic compound described above is provided on the surface of the linearly polarizing film 1 opposite to the protective film 3 to form an optical film 25 with a pressure-sensitive 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 first protective film 3 having a surface treatment layer 2 is attached to one side of a linear polarizing film 1 on the surface opposite to the surface treatment layer 2, and the linear polarizing film A polarizing plate 5 is configured by sticking a second protective film 4 to the other surface of 1. Also in this example, the polarizing plate 5 is simultaneously the optical film 10 referred to in the present invention.
  • the pressure-sensitive adhesive layer 20 containing the ionic compound described above is provided, and the optical film 25 with pressure-sensitive adhesive is formed. And 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 configured by sticking a protective film 3 having a surface treatment layer 2 on one surface of a linearly polarizing film 1 on the surface opposite to the surface treatment layer 2.
  • a retardation film 7 is stuck via an interlayer adhesive 8 to constitute an optical film 10.
  • the pressure-sensitive adhesive layer 20 containing the ionic compound described above is provided, and the optical film 25 with pressure-sensitive adhesive is formed.
  • 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 linearly polarizing film 1 on the surface opposite to the surface treatment layer 2 to form a straight line.
  • a second protective film 4 is stuck to form a polarizing plate 5.
  • a retardation film 7 is stuck via an interlayer adhesive 8 to constitute an optical film 10.
  • the pressure-sensitive adhesive layer 20 containing the ionic compound described above is provided, and the optical film 25 with pressure-sensitive adhesive is formed.
  • 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 are composed of the various transparent resin films described above. You can also.
  • 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 quarter wave plate can be mentioned.
  • 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 An antistatic agent such as the ionic compound described above can be blended and an antistatic agent can be used. However, since there is usually not much antistatic property desired in this part, It is customary to use a general acrylic adhesive that does not contain an inhibitor. Further, as in the large liquid crystal display device described above, the polarizing axis 5 and the slow axis of the retardation film 7 are arranged so that the slow axis is substantially orthogonal or substantially parallel.
  • an adhesive that, once bonded, can be firmly bonded and cannot be peeled off.
  • an adhesive include an aqueous adhesive that is composed of an aqueous solution or an aqueous dispersion and exhibits adhesive strength by evaporating water as a solvent, and UV curing that is cured by UV irradiation and exhibits adhesive strength. Examples thereof include a mold adhesive.
  • the pressure-sensitive adhesive layer 20 containing an ionic compound is formed on the retardation film 7 itself can be circulated by itself and is referred to in the present invention. It can be an optical film with an adhesive.
  • An optical film with a pressure-sensitive adhesive in which a pressure-sensitive adhesive layer containing an ionic compound is formed on a retardation film can be bonded to a liquid crystal cell as a glass substrate to form an optical laminate, and the phase difference film.
  • a polarizing plate can be bonded to the side to make 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 Assistance), 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 Assistance
  • the nonvolatile content is a value measured by a method according to JIS K5407. Specifically, the adhesive solution was taken in a petri dish at an arbitrary weight, and the residual non-volatile content after drying for 2 hours at 115 ° C. in an explosion-proof oven was expressed as a percentage of the weight of the solution first measured. It is.
  • the weight average molecular weight is measured in series on a GPC device with four “TSK gel XL” manufactured by Tosoh Corp. and one “GPC KF-802” manufactured by Shodex Corp. in series. Tetrahydrofuran was used as the eluent, and the sample concentration was 5 mg / mL, the sample introduction amount was 100 ⁇ L, the temperature was 40 ° C., and the flow rate was 1 mL / min.
  • an acrylic resin (A) defined in the present invention which is a main component of the pressure-sensitive adhesive composition, and an acrylic resin similar to the above but deviating from the definition of the present invention will be shown.
  • acrylic resin A This is designated as acrylic resin A.
  • the structural unit derived from 2-hydroxyethyl acrylate which is a hydroxyl group-containing unsaturated monomer in acrylic resin A is 1%, and the structural unit derived from acrylic acid which is a carboxyl group-containing unsaturated monomer is 0.4%.
  • the structural unit derived from 2-hydroxyethyl acrylate which is a hydroxyl group-containing unsaturated monomer in the acrylic resin B is 1%, and the structural unit derived from acrylic acid which is a carboxyl group-containing unsaturated monomer is 0.4%.
  • the structural unit derived from 2-hydroxyethyl acrylate which is a hydroxyl group-containing unsaturated monomer in the acrylic resin D is 1%, and the structural unit derived from acrylic acid which is a carboxyl group-containing unsaturated monomer is 0.4%.
  • the structural unit derived from 2-hydroxyethyl acrylate which is a hydroxyl group-containing unsaturated monomer in the acrylic resin E is 1%, and the structural unit derived from acrylic acid which is a carboxyl group-containing unsaturated monomer is 0.4%.
  • the structural unit derived from 2-hydroxyethyl acrylate which is a hydroxyl group-containing unsaturated monomer in the acrylic resin G is 1%, and the structural unit derived from acrylic acid which is a carboxyl group-containing unsaturated monomer is 0.4%.
  • Polymerization Example 8 Polymerization Example 1 except that the amount of butyl acrylate in the monomer composition was changed to 88.4 parts, the amount of 2-phenoxyethyl acrylate was 10.0 parts, and the amount of acrylic acid was 0.6 parts. In the same manner, an ethyl acetate solution of an acrylic resin was obtained. The obtained acrylic resin had a polystyrene-reduced weight average molecular weight Mw by GPC of 1,530,000 and Mw / Mn of 4.8. This is designated as acrylic resin H.
  • the structural unit derived from 2-hydroxyethyl acrylate which is a hydroxyl group-containing unsaturated monomer in the acrylic resin H is 1%, and the structural unit derived from acrylic acid which is a carboxyl group-containing unsaturated monomer is 0.6%.
  • the monomer composition is 78.4 parts of butyl acrylate and 10.0 parts of 2-methoxyethyl acrylate as (A-1), 10.0 parts of 2-phenoxyethyl acrylate as (A-2), (A -3) was changed to 1.0 part of 2-hydroxyethyl acrylate and 0.6 part of acrylic acid, and an ethyl acetate solution of acrylic resin was obtained in the same manner as in Polymerization Example 1 except that.
  • the obtained acrylic resin had a polystyrene-equivalent weight average molecular weight Mw by GPC of 1,540,000 and Mw / Mn of 4.9. This is designated as acrylic resin I.
  • the structural unit derived from 2-hydroxyethyl acrylate which is a hydroxyl group-containing unsaturated monomer in the acrylic resin I is 1%, and the structural unit derived from acrylic acid which is a carboxyl group-containing unsaturated monomer is 0.6%.
  • the inner temperature was 54 to 56 ° C. while ethyl acetate was continuously added into the reaction vessel at an addition rate of 17.3 parts / hr so that the concentration of the acrylic resin excluding the monomer was 35%. And kept warm for 4 hours. Thereafter, a total solution of 0.2 part of azobisisobutyronitrile (polymerization initiator) dissolved in 10 parts of ethyl acetate was added and kept at the same temperature for 8 hours. Finally, ethyl acetate was added to the concentration of the acrylic resin. Was adjusted to 20%.
  • the obtained acrylic resin had a polystyrene-equivalent weight average molecular weight Mw by GPC of 1,070,000 and Mw / Mn of 8.2. This is designated as acrylic resin J.
  • the structural unit derived from 2-hydroxyethyl acrylate which is a hydroxyl group-containing unsaturated monomer in the acrylic resin J is 1%, and the structural unit derived from acrylic acid which is a carboxyl group-containing unsaturated monomer is 0.4%.
  • Table 1 shows a list of monomer compositions, weight average molecular weights, and Mw / Mn of polymerization examples 1 to 10.
  • BA means butyl acrylate
  • MEA means 2-methoxyethyl acrylate
  • PEA means 2-phenoxyethyl acrylate
  • HEA means 2-hydroxyethyl acrylate
  • AA acrylic acid
  • Ionic compound 1 N-octyl-4-methylpyridinium hexafluorophosphate (having the structure of the following formula, melting point 44 ° C.)
  • Ionic compound 2 N-hexyl-4-methylpyridinium bis (trifluoromethanesulfonyl) imide (having the structure of the following formula, melting point: 18 ° C.)
  • Ionic compound 3 trioctylmethylammonium bis (trifluoromethanesulfonyl) imide (having the structure of the following formula, liquid at room temperature)
  • Ionic compound 4 tributylmethylammonium bis (trifluoromethanesulfonyl) imide (having the structure of the following formula, melting point: 28 ° C.)
  • crosslinking agent and the silane compound those shown below were used (both are trade names).
  • Coronate L Obtained from an ethyl acetate solution of trimethylolpropane adduct of tolylene diisocyanate (solid content concentration 75%), Nippon Polyurethane Co., Ltd.
  • KBM-403 Glycidoxypropyltrimethoxysilane (liquid), obtained from Shin-Etsu Chemical Co., Ltd.
  • Examples 1 to 8 and Comparative Examples 1 to 6 (A) Production of pressure-sensitive adhesive 100 parts of each of the acrylic resins A to J obtained in Polymerization Examples 1 to 10 were mixed with each amount of ionic compound shown in Table 2, 0.5 part of a silane compound ( KBM-403) and the respective amounts of the cross-linking agent shown in Table 2 (Coronate L) were mixed, and ethyl acetate was further added so that the solid content concentration was 13% to obtain a pressure-sensitive adhesive composition.
  • the cross-linking agent (Coronate L) is an ethyl acetate solution having a solid concentration of 75% as described above, but the addition amount shown in Table 2 is the solid content.
  • a polarizing plate having a three-layer structure in which both sides of a polyvinyl alcohol polarizer to which iodine is adsorbed and oriented are sandwiched by protective films made of triacetyl cellulose the surface opposite to the separator of the sheet-like adhesive obtained above ( The pressure-sensitive adhesive surface) was pasted with a laminator and then cured for 7 days under conditions of a temperature of 23 ° C. and a relative humidity of 65% to obtain a polarizing plate with a pressure-sensitive adhesive.
  • a heat resistance test is performed for 300 hours under dry conditions at a temperature of 80 ° C. (indicated as “heat resistance” in Table 2)
  • a heat resistance test is performed for 300 hours at a temperature of 60 ° C. and a relative humidity of 90%.
  • moisture-resistant heat the process of lowering the temperature from ⁇ 70 ° C. to ⁇ 30 ° C. and then raising the temperature to 70 ° C. is defined as 1 cycle (1 hour).
  • the repeated heat shock resistance test was performed (indicated as “HS resistance” in Table 2), the optical laminate after the test was visually observed. The results were classified according to the following criteria and summarized in Table 2.
  • (E) Reworkability evaluation of optical film with adhesive The reworkability was evaluated as follows. First, the polarizing plate with the adhesive obtained in (b) was cut into a test piece having a size of 25 mm ⁇ 150 mm. Next, the test piece was attached to the glass substrate for liquid crystal cell on the adhesive side using a sticking device ["Lami Packer” (trade name) manufactured by Fuji Plastics Co., Ltd.], 50 ° C., 5 kg / cm 2 ( 490.3 kPa) for 20 minutes. Next, it was heat-treated at 70 ° C. for 2 hours, and subsequently stored in an oven at 50 ° C.
  • Example 1 to 8 in which a predetermined amount of an ionic compound and a crosslinking agent were blended with the acrylic resin specified in the present invention to form an adhesive were antistatic properties and anti-whitening properties. In addition, it was excellent in reworkability, and almost satisfactory results were obtained in heat resistance, moist heat resistance and heat shock resistance. In particular, Example 2 has excellent performance in all of antistatic properties, anti-whitening properties, rework properties, heat resistance, moist heat resistance and heat shock resistance.
  • Comparative Examples 1 to 3 using an acrylic resin containing 20 parts by weight or more of a structural unit derived from an unsaturated monomer having an aromatic ring, and a structural unit derived from an unsaturated monomer having an aromatic ring The comparative example 4 using the acrylic resin which does not contain is insufficient in white spot prevention. Further, Comparative Example 5, which did not reach the gel fraction as defined in the present invention, resulted in conspicuous changes in appearance such as floating, peeling and foaming in the heat resistance test, heat resistance test and heat shock test. On the other hand, in Comparative Example 6 using an acrylic resin having a large molecular weight distribution, a result that white spot prevention property was insufficient was obtained.
  • the optical film with a pressure-sensitive adhesive of the present invention is imparted with high antistatic property, and the antistatic property is maintained for a long period of time, and is excellent in durability.
  • This optical film with an adhesive is suitably used for a liquid crystal display device.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)
  • Polarising Elements (AREA)
  • Liquid Crystal (AREA)
  • Laminated Bodies (AREA)
PCT/JP2009/064038 2008-08-11 2009-08-07 粘着剤付き光学フィルムとそれを用いた光学積層体 WO2010018794A1 (ja)

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JP2022130601A (ja) * 2019-09-03 2022-09-06 藤森工業株式会社 粘着フィルム
JP7333852B2 (ja) 2019-09-03 2023-08-25 藤森工業株式会社 粘着フィルム

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