WO2022130747A1 - Composition adhésive et plaque de polarisation contenant une couche adhésive - Google Patents

Composition adhésive et plaque de polarisation contenant une couche adhésive Download PDF

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Publication number
WO2022130747A1
WO2022130747A1 PCT/JP2021/037361 JP2021037361W WO2022130747A1 WO 2022130747 A1 WO2022130747 A1 WO 2022130747A1 JP 2021037361 W JP2021037361 W JP 2021037361W WO 2022130747 A1 WO2022130747 A1 WO 2022130747A1
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pressure
sensitive adhesive
adhesive layer
mass
meth
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PCT/JP2021/037361
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English (en)
Japanese (ja)
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翔 黒澤
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綜研化学株式会社
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Publication of WO2022130747A1 publication Critical patent/WO2022130747A1/fr

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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
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements

Definitions

  • One embodiment of the present invention relates to a pressure-sensitive adhesive composition or a pressure-sensitive adhesive layer-containing polarizing plate.
  • a liquid crystal display device has a liquid crystal panel member in which polarizing plates are bonded to both sides of a liquid crystal cell with an adhesive, and display is performed by controlling light from a backlight member or the like with the liquid crystal panel member.
  • Such liquid crystal displays are widely used in televisions, notebook computers, monitors, smartphones, etc. because they are thin, lightweight, and have low power consumption, and some of these applications are exposed to high temperatures. There is also.
  • Polarizing plates used for applications that can be exposed to such high temperatures are prone to foaming and deformation (eg, shrinkage, expansion, warpage) due to heat and the like, and this foaming and deformation causes Since the pressure-sensitive adhesive layer does not exhibit the desired optical characteristics, the pressure-sensitive adhesive layer is required to have excellent durability in which foaming and deformation are unlikely to occur even at a high temperature (eg, 100 ° C.).
  • a high temperature eg, 100 ° C.
  • Patent Document 1 discloses a pressure-sensitive adhesive composition capable of forming such a pressure-sensitive adhesive layer having excellent durability.
  • the conventional pressure-sensitive adhesive composition capable of forming a pressure-sensitive adhesive layer having excellent durability as described in Patent Document 1 has a high viscosity, the pressure-sensitive adhesive layer can be easily formed by coating or the like.
  • One embodiment of the present invention provides a pressure-sensitive adhesive composition capable of forming a pressure-sensitive adhesive layer having excellent durability while being a pressure-sensitive adhesive composition having a high non-volatile content and a low viscosity.
  • the configuration example of the present invention is as follows.
  • a polarizing plate containing a pressure-sensitive adhesive layer which comprises a polarizing plate and a pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition according to any one of [1] to [5].
  • a pressure-sensitive adhesive layer having excellent durability while being a pressure-sensitive adhesive composition having a high non-volatile content and a low viscosity.
  • the adherend of the pressure-sensitive adhesive layer such as a liquid crystal panel (liquid crystal cell) may be reused.
  • the adhesive layer used for such applications has adhesiveness that allows it to adhere with a certain degree of adhesive force when it is desired to adhere to the adherend, and reworkability that allows it to be peeled off when it is about to be peeled off from the adherend (reworkability). (Removability) is required, but according to one embodiment of the present invention, it is possible to form an adhesive layer having an excellent balance between such adhesiveness and reworkability.
  • the pressure-sensitive adhesive composition according to one embodiment of the present invention (hereinafter, also referred to as “the present composition”) is also referred to as an amine-based monomer having an acid dissociation constant (pKa) of 9 or more (hereinafter, also referred to as “monomer (a)”). ) Is copolymerized with a monomer component containing 0.5 to 10% by mass of a (meth) acrylic copolymer (hereinafter, also referred to as “copolymer (A)”), and an organic solvent is contained in the copolymer. The content of (A) is 20% by mass or more.
  • Such a composition can form a pressure-sensitive adhesive layer having excellent durability while being a pressure-sensitive adhesive composition having a high non-volatile content and a low viscosity.
  • the amino group of the monomer (a) behaves as a chain transfer agent, so that the degree of branching of the obtained copolymer (A) is increased, so that the composition becomes a low viscosity composition. It is considered that a pressure-sensitive adhesive layer having sufficient cohesive force and excellent durability can be formed. In particular, it is considered that the larger the pKa of the monomer (a), the higher the degree of branching.
  • the content of the non-volatile component in the present composition is preferably as high as possible, but is preferably 20 to 50% by mass, more preferably 20 to 40% by mass, considering the formability of the pressure-sensitive adhesive layer.
  • a composition having a non-volatile content in the above range can be said to be a composition having a high non-volatile content.
  • the present composition has a low viscosity even if the non-volatile content is in the above range, and the pressure-sensitive adhesive layer can be easily formed by coating or the like.
  • the content of the non-volatile component in the present composition can be measured based on the method described in the following Examples.
  • the present composition has a low viscosity and is excellent in coatability, a desired pressure-sensitive adhesive layer can be formed without diluting or the like. Therefore, it is preferable to use this composition without diluting it, but in some cases, it may be used after diluting it.
  • the description of the present specification relates to the composition before being diluted in this way.
  • the viscosity of this composition at room temperature (23 ° C.) measured with a B-type viscometer is preferably 1 Pa ⁇ s or more, more preferably 2 Pa ⁇ s or more, still more preferably 3 Pa ⁇ s or more, preferably 50 Pa ⁇ s or more. It is s or less, more preferably 30 Pa ⁇ s or less, still more preferably 15 Pa ⁇ s or less.
  • a composition having a viscosity in the above range can be said to be a composition having a low viscosity.
  • the present composition can be a composition having a high non-volatile content even if the viscosity is in the above range, and a pressure-sensitive adhesive layer having excellent durability can be easily formed.
  • This composition is suitably used for a polarizing plate. Specifically, it is suitably used as a composition for forming a pressure-sensitive adhesive layer used in contact with a polarizing element of a polarizing plate and a pressure-sensitive adhesive layer used in contact with a protective film of a polarizing plate.
  • polarizing plate is used to include “polarizing film”, and in this specification, there is no particular distinction between a plate, a film, a sheet and the like.
  • the copolymer (A) is copolymerized with a monomer component containing 0.5 to 10% by mass of the monomer (a), for example, a conventional solution polymerization method, a bulk polymerization method, an emulsion polymerization method, a suspension polymerization method and the like.
  • the (meth) acrylic copolymer obtained by copolymerizing by a known polymerization method is not particularly limited.
  • the copolymer (A) contained in the present composition may be one kind or two or more kinds.
  • (meth) acrylic in this specification means acrylic and / or methacrylic. Similar expressions have the same meaning.
  • the weight average molecular weight (Mw) of the copolymer (A) is preferably 300,000 or more, more preferably 500,000 or more, from the viewpoint that a pressure-sensitive adhesive layer having better durability can be easily formed. It is preferably 3 million or less, more preferably 2 million or less. Specifically, the Mw can be measured by the method described in the following Examples.
  • the content of the copolymer (A) in the present composition is 20% by mass or more, the balance of performance as a pressure-sensitive adhesive is excellent, and a pressure-sensitive adhesive layer having particularly excellent pressure-sensitive adhesive properties can be easily obtained. From the point of view, it is preferably 20 to 50% by mass, more preferably 20 to 40% by mass.
  • a composition having a copolymer (A) content in the above range can be said to be a composition having a high non-volatile content. Further, the present composition has a low viscosity even if the content of the copolymer (A) is in the above range, and the pressure-sensitive adhesive layer can be easily formed by coating or the like.
  • the monomer component preferably contains (meth) acrylic acid alkyl ester (b), a hydroxyl group-containing monomer (c), and, if necessary, another monomer (d) as a monomer other than the monomer (a). It is preferable that the acid group-containing monomer (e) is not substantially contained. Further, when copolymerizing the above-mentioned monomer components, it is preferable to prepare a monomer mixture containing these monomer components, a polymerization initiator and a polymerization solvent, and the monomer mixture may further include a chain transfer agent or the like, if necessary. It may contain a conventionally known additive.
  • the monomer (a) is an amine-based monomer having a pKa of 9 or more, and the amine-based monomer is preferably a monomer having an ethylenically unsaturated bond and an amino group, and has a (meth) acryloyl group and an amino group. It is more preferable that the monomer has.
  • Specific examples of the monomer (a) include diethylaminoethyl acrylate (pKa: 9.2), dimethylaminopropyl acrylate (pKa: 10.4), diethylaminopropyl acrylate (pKa: 9.2), and dimethylaminopropylacrylamide (pKa: 9.2).
  • pKa: 10.4 diethylaminoethyl methacrylate (pKa: 9.2), dimethylaminopropyl methacrylate (pKa: 9.2), diethylaminopropyl methacrylate (pKa: 10.0), t-butylaminoethyl methacrylate (pKa:: 9.0) can be mentioned.
  • the monomer (a) one type may be used, or two or more types may be used.
  • the pKa of the monomer (a) is preferably 10 or more from the viewpoint that a pressure-sensitive adhesive composition having a higher non-volatile content and a lower viscosity can easily form a pressure-sensitive adhesive layer having better durability. Is.
  • the upper limit of the pKa is not particularly limited, but is, for example, 12 or less.
  • the pKa is an acid dissociation constant in an aqueous solution at room temperature (25 ° C.).
  • the content of the monomer (a) in the monomer component is such that a pressure-sensitive adhesive layer having higher durability can be easily formed while the pressure-sensitive adhesive composition has a higher non-volatile content and a lower viscosity. , It is preferably 0.5 to 8% by mass, more preferably 0.5 to 6% by mass, based on 100% by mass of the total amount of the monomers in the monomer component.
  • (meth) Acrylic Acid Alkyl Ester (b) examples include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, and iso-butyl (meth) acrylate.
  • t-butyl (meth) acrylate hexyl (meth) acrylate, heptyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, iso-octyl (meth) acrylate, nonyl (meth) acrylate, Examples thereof include decyl (meth) acrylate, undecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, and isostearyl (meth) acrylate.
  • the (meth) acrylic acid alkyl ester (b) may be used alone or in combination of two or more.
  • the content of the (meth) acrylic acid alkyl ester (b) can easily form a pressure-sensitive adhesive layer having excellent stress relaxation characteristics. From the point of view, it is preferably 50 to 99.4% by mass, more preferably 50 to 98% by mass, based on 100% by mass of the total amount of the monomers in the monomer component.
  • hydroxyl group-containing monomer (c) examples include 2-hydroxyethyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, and 8-. Hydroxyoctyl (meth) acrylates may be mentioned. As the hydroxyl group-containing monomer (c), one type may be used, or two or more types may be used.
  • the content of the hydroxyl group-containing monomer (c) can easily form a pressure-sensitive adhesive layer having excellent heat resistance, strength and stress relaxation characteristics. It is preferably 0.1 to 7% by mass, more preferably 0.1 to 5% by mass, based on 100% by mass of the total amount of the monomers in the monomer component.
  • Examples of the other monomer (d) include, for example. Methoxymethyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 3-methoxypropyl (meth) acrylate, 3-ethoxypropyl (meth) acrylate, 4-methoxybutyl (meth) Alkoxyalkyl (meth) acrylates such as acrylates and 4-ethoxybutyl (meth) acrylates; Ekoxypolyalkylenes such as methoxydiethylene glycol mono (meth) acrylate, methoxydipropylene glycol mono (meth) acrylate, ethoxytriethylene glycol mono (meth) acrylate, ethoxydiethylene glycol mono (meth) acrylate, and methoxytriethylene glycol mono (meth) acrylate.
  • Glycol mono (meth) acrylate Alicyclic or aromatic ring-containing (meth) acrylates such as cyclohexyl (meth) acrylate, benzyl (meth) acrylate, and phenyl (meth) acrylate; Styrene, methylstyrene, dimethylstyrene, trimethylstyrene, propylstyrene, butylstyrene, hexylstyrene, heptylstyrene, octylstyrene, fluorostyrene, chlorostyrene, bromostyrene, dibromostyrene, iodide styrene, nitrostyrene, acetylstyrene, methoxy Styrene-based monomers such as styrene; Vinyl acetate; Can be mentioned.
  • the other monomer (d) one kind may be used, or two or
  • the content of the other monomer (d) in the monomer component is based on 100% by mass of the total amount of the monomers in the monomer component from the viewpoint that the adhesive force to the adherend used can be adjusted. It is preferably 0 to 49.4% by mass, and more preferably 0 to 25% by mass.
  • acid group-containing monomer (e) examples include (meth) acrylic acid ⁇ -carboxyethyl, (meth) acrylic acid 5-carboxypentyl, crotonic acid mono (meth) acryloyloxyethyl ester, and ⁇ -carboxypolycaprolactone mono.
  • (Meta) carboxyl group-containing monomers such as acrylate, acrylic acid, methacrylic acid, itaconic acid, crotonic acid, fumaric acid, and maleic acid; Acid anhydride group-containing monomers such as maleic anhydride and itaconic anhydride; Phosphoric acid group-containing monomers such as (meth) acrylic monomers having a phosphoric acid group; Sulfate group-containing monomers such as (meth) acrylic monomers having a sulfate group; Can be mentioned.
  • the monomer component does not substantially contain the acidic group-containing monomer (e), and the fact that the acidic group-containing monomer (e) is not substantially contained means that the acidic group-containing monomer (e) is artificially contained during the copolymerization.
  • the content thereof is preferably 0 to 0.2% by mass, more preferably 0 to 0.05% by mass, based on 100% by mass of the total amount of the monomers in the monomer component. .. Since the monomer component does not substantially contain the acidic group-containing monomer (e), for example, when this composition is used for a touch panel or the like, a member made of a metal or a metal oxide of the touch panel or the like (eg, a conductive film). ) Corrosion can be suppressed.
  • the polymerization initiator is not particularly limited, and conventionally known polymerization initiators can be used.
  • Examples of the polymerization initiator include a radical polymerization initiator, and specific examples of the radical polymerization initiator include 2,2'-azobis (2-methylbutyronitrile) and 2,2'-azobis.
  • Isobutyronitrile (1-phenylethyl) azodiphenylmethane, 2,2'-azobis (2,4-dimethylvaleronitrile), 2,2'-azobis (2-cyclopropylpropionitrile), 2,2' -Azobis (4-methoxy-2,4-dimethylvaleronitrile) and other azo-based polymerization initiators; benzoyl peroxide, lauroyl peroxide, t-butyl peroxypivalate, t-hexyl peroxypivalate, t-hexyl peroxyneo Examples thereof include peroxide-based polymerization initiators such as decanoate, diisopropylperoxycarbonate, and diisobutyrylperoxide.
  • the polymerization initiator may be used alone or in combination of two or more.
  • the azo-based polymerization initiator is preferable, and the copolymer (A) is a polymer obtained by using the azo-based polymerization initiator from the viewpoint that an appropriate cohesive force can be obtained. preferable.
  • the content of the polymerization initiator is based on 100 parts by mass of the total amount of the monomers in the monomer mixture from the viewpoint that the monomer components can be sufficiently polymerized. It is preferably 0.005 part by mass or more, more preferably 0.01 part by mass or more, preferably 0.5 part by mass or less, and more preferably 0.3 part by mass or less.
  • polymerization solvent examples include aromatic hydrocarbons such as benzene and toluene; aliphatic hydrocarbons such as n-pentane, n-hexane, n-heptane and n-octane; cyclopentane, cyclohexane and cycloheptane.
  • Alicyclic hydrocarbons such as cyclooctane; ethers such as diethyl ether, diisopropyl ether, 1,2-dimethoxyethane, dibutyl ether, tetrahydrofuran, dioxane, anisole, phenylethyl ether, diphenyl ether; chloroform, carbon tetrachloride, 1 , 2-Dichloroethane, halogenated hydrocarbons such as chlorobenzene; esters such as methyl acetate, ethyl acetate, propyl acetate, butyl acetate, methyl propionate; ketones such as acetone, methyl ethyl ketone, diethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.
  • ethers such as diethyl ether, diisopropyl ether, 1,2-dimethoxyethane, dibutyl
  • Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone; nitriles such as acetonitrile and benzonitrile; sulfoxides such as dimethylsulfoxide and sulfolanes.
  • the polymerization solvent one kind may be used, or two or more kinds may be used.
  • the total amount of the monomers in the monomer mixture is preferably 20% by mass or more, more preferably 30% by mass or more, preferably 80% by mass or less, and more preferably 70% by mass or less. It is desirable to use the polymerization solvent in such an amount.
  • the monomer component is copolymerized using a polymerization solvent, it is preferable to use the solution obtained by this polymerization as it is in the present composition.
  • the polymerization solvent is used in the above amount, the present composition having a high non-volatile content can be easily obtained even if the solution obtained by copolymerizing the monomer components is used as it is in the present composition.
  • Organic solvent contained in the present composition examples include the same solvents as those mentioned in the column of the polymerization solvent.
  • the organic solvent contained in the present composition may be one kind or two or more kinds.
  • the content of the organic solvent in the present composition is preferably the minimum amount having a viscosity such that a desired pressure-sensitive adhesive layer can be easily formed, specifically, a pressure-sensitive adhesive layer can be formed by coating.
  • the content of the non-volatile component in the present composition is an amount within the above range.
  • the present composition may optionally contain a cross-linking agent, and preferably contains a cross-linking agent from the viewpoint that a more durable pressure-sensitive adhesive layer can be easily formed.
  • a cross-linking agent is preferably a cross-linking agent capable of reacting with a (meth) acrylic polymer at room temperature or heating to form a cross-linked structure.
  • the cross-linking agent is not particularly limited, and examples thereof include an isocyanate-based cross-linking agent, an epoxy-based cross-linking agent, a metal chelate-based cross-linking agent, and an aziridine-based cross-linking agent. Of these, isocyanate-based cross-linking agents are particularly preferable.
  • the cross-linking agent used may be one kind or two or more kinds.
  • isocyanate-based cross-linking agent examples include isocyanate compounds such as xylylene diisocyanate, tolylene diisocyanate, chlorophenylenedi isocyanate, hexamethylene diisocyanate, tetramethylene diisocyanate, isophorone diisocyanate, diphenylmethane diisocyanate, and hydrogenated diphenylmethane diisocyanate, and isocyanates thereof.
  • isocyanate group-containing reaction products obtained by reacting a compound with dihydric or higher alcohols such as trimethylolpropane, and derivatives such as isocyanurates of these isocyanates.
  • the content of the cross-linking agent is 100 parts by mass of the copolymer (A) in the present composition from the viewpoint that a pressure-sensitive adhesive layer having more durability can be easily formed.
  • it is preferably 0.05 to 5 parts by mass, and more preferably 0.05 to 2 parts by mass.
  • the present composition may optionally contain other components as long as the effects of the present invention are not impaired.
  • specific examples of such other components include silane coupling agents, antistatic agents, tackifying resins, adhesive strength reducing agents, antioxidants, ultraviolet absorbers, metal corrosion inhibitors, and cross-linking accelerators. Examples thereof include plasticizers, organic particles, and inorganic particles.
  • plasticizers organic particles, and inorganic particles.
  • one kind may be used for each, or two or more kinds may be used.
  • the pressure-sensitive adhesive layer-containing polarizing plate has a polarizing plate and a pressure-sensitive adhesive layer formed from the present composition (hereinafter, also referred to as “the present pressure-sensitive adhesive layer”).
  • the pressure-sensitive adhesive layer may be in contact with the polarizing element of the polarizing plate, or may be in contact with the protective film of the polarizing plate, for example.
  • the pressure-sensitive adhesive layer-containing polarizing plate may have two or more of the present pressure-sensitive adhesive layers. In this case, the two or more layers of the present pressure-sensitive adhesive layer may be the same layer or different layers.
  • the thickness of the pressure-sensitive adhesive layer is not particularly limited, but is usually 5 ⁇ m or more, preferably 10 ⁇ m or more, and usually 75 ⁇ m or less from the viewpoint that a pressure-sensitive adhesive layer having sufficient adhesiveness can be easily obtained. It is preferably 50 ⁇ m or less.
  • the adhesive strength of this adhesive layer is the adhesiveness that can be adhered to the adherend with a certain degree of adhesive strength and the reworkability (removability) that can be peeled off when trying to peel off from the adherend. It is preferably 2 to 6 N / 25 mm, more preferably 2 to 4 N / 25 mm, from the viewpoint of forming an excellent pressure-sensitive adhesive layer in a well-balanced manner. Specifically, the adhesive strength can be measured by the method described in the following Examples.
  • the minute creep value of this pressure-sensitive adhesive layer at 23 ° C. is preferably 0.6 mm or less, from the viewpoint of more reliably preventing light leakage and providing a pressure-sensitive adhesive layer having an excellent balance of adhesive strength and durability. It is preferably 0.5 mm or less. Specifically, the minute creep value can be measured by the method described in the following Examples.
  • the gel fraction of the present pressure-sensitive adhesive layer is preferably 50% by mass or more, more preferably 60% by mass or more, preferably 99% by mass or less, and more, from the viewpoint of forming a pressure-sensitive adhesive layer having more excellent durability. It is preferably 90% by mass or less. Specifically, the gel fraction can be measured by the method described in the following Examples.
  • the method for forming the present pressure-sensitive adhesive layer is not particularly limited.
  • a method of applying the present composition to an adherend on which the present pressure-sensitive adhesive layer is to be formed, drying and, if necessary, aging, a method of preliminarily applying a pressure-sensitive adhesive from the present composition examples thereof include a method of forming a layer, attaching or transferring the pressure-sensitive adhesive layer to an adherend on which the present pressure-sensitive adhesive layer is to be formed, and aging it if necessary.
  • Examples of the method of forming the pressure-sensitive adhesive layer from the present composition in advance include a method of applying the present composition to a support that has been subjected to a mold release treatment or the like, drying the composition, and aging it if necessary.
  • a known method for example, a spin coating method, a knife coating method, a roll coating method, a bar coating method, a blade coating method, a die coating method, a gravure coating method, or the like, has a predetermined thickness.
  • a method of applying so as to obtain the pressure-sensitive adhesive layer of Since the present composition has a low viscosity and is excellent in coatability, the present pressure-sensitive adhesive layer can be formed by various known methods without diluting or the like.
  • the drying conditions may be appropriately selected depending on the type of the organic solvent, and are, for example, 50 ° C. or higher, preferably 60 ° C. or higher, for example 150 ° C. or lower, preferably 100 ° C. or lower, usually 1 minute or longer. Conditions such as drying for 2 minutes or more, usually 10 minutes or less, preferably 7 minutes or less can be mentioned.
  • the aging conditions are usually 5 ° C. or higher, preferably 15 ° C. or higher, usually 60 ° C. or lower, preferably 40 ° C. or lower, usually 30 to 70% RH, preferably 40 to 70% RH.
  • the conditions for aging usually 3 days or more, preferably 7 days or more, preferably 10 days or less, and the like can be mentioned.
  • the polarizing plate may be any conventionally known polarizing plate, and is not particularly limited, but usually has a polarizing element and a (polarizer) protective film.
  • the polarizing plate may contain one layer each of these, or may contain two or more layers. Further, the polarizing plate may have other layers such as an antiglare layer, a retardation layer, and a viewing angle improving layer.
  • the thickness of the polarizing plate is not particularly limited, but is usually 10 ⁇ m or more, preferably 30 ⁇ m or more, and usually 200 ⁇ m or less, preferably 100 ⁇ m or less.
  • the polarizing element is not particularly limited, and conventionally known polarizing elements can be used. Examples thereof include a stretched film obtained by incorporating a polarizing component into a film made of a polyvinyl alcohol-based resin and stretching the film. .. Examples of the polyvinyl alcohol-based resin include saponified products of polyvinyl alcohol, polyvinylformal, polyvinyl acetal, and ethylene-vinyl acetate copolymer. Polarizing components include, for example, iodine and / or dichroic dyes.
  • the protective film examples include a film made of a thermoplastic resin.
  • the thermoplastic resin include cellulose resins such as triacetyl cellulose, polyester resins, polyether sulfone resins, polysulfone resins, polycarbonate resins, polyamide resins, polyimide resins, polyolefin resins, (meth) acrylic resins, and cyclic polyolefin resins ( Examples include norbornene-based resins), polyarylate resins, polystyrene resins, polyvinyl alcohol resins, and mixtures of two or more selected from these resins.
  • Example 1 97 parts by mass of n-butyl acrylate (BA), 1 part by mass of 4-hydroxybutyl acrylate (4-HBA), dimethylaminopropylacrylamide ( DMAPAA, pKa: 10.4) 2 parts by mass and 100 parts by mass of an ethyl acetate solvent were charged, and the temperature was raised to 67 ° C. while introducing nitrogen gas. Next, 0.05 parts by mass of 2,2'-azobisisobutyronitrile was added, and a polymerization reaction was carried out at 67 ° C. under a nitrogen gas atmosphere. After 1 hour from the start of the reaction, 50 parts by mass of ethyl acetate was added dropwise over 1 hour and 30 minutes. Further, 6 hours after the start of the reaction, 100 parts by mass of ethyl acetate was added to obtain a polymer solution.
  • BA n-butyl acrylate
  • 4-HBA 4-hydroxybutyl acrylate
  • Non-volatile content 100 ⁇ [mass after heating (n3-n1) / mass before heating (n2-n1)]
  • the pressure-sensitive adhesive composition obtained by adding 0.29 parts by mass of an isocyanate cross-linking agent (“TD-75” manufactured by Soken Chemical Co., Ltd.) to the obtained polymer solution was applied onto the peeled liner. Then, it was dried at 90 ° C. for 5 minutes to form a pressure-sensitive adhesive layer having a thickness of 20 ⁇ m.
  • a polarizing plate was laminated on the formed pressure-sensitive adhesive layer and aged at 40 ° C. for 7 days to prepare a polarizing plate with a pressure-sensitive adhesive layer.
  • ⁇ Adhesive strength> The prepared polarizing plate with an adhesive layer is cut to a width of 25 mm, the peeled liner is peeled off, and then the adhesive layer is attached to glass under a 23 ° C./50% RH environment, and the pressure is 50 ° C. and 5 atm. It was crimped for 20 minutes in the environment of. Then, the adhesive force when the polarizing plate was peeled off was measured at a peeling angle of 180 ° and a tensile speed of 300 mm / min under a 23 ° C./50% RH environment. The results are shown in Table 1.
  • Example 1 The polymer solution was used in the same manner as in Example 1 except that the monomers shown in Table 1 were used in the amounts (parts by mass) shown in Table 1 and the amount of ethyl acetate added 6 hours after the start of the reaction was changed to 230 parts by mass.
  • the obtained polymer solution was used to measure the non-volatile content and the viscosity in the same manner as in Example 1. The results are shown in Table 1.
  • the pressure-sensitive adhesive was obtained in the same manner as in Example 1 except that the pressure-sensitive adhesive composition obtained by adding the amount (part by mass) of TD-75 shown in Table 1 to the obtained polymer solution was used.
  • a layered polarizing plate was produced. Using the prepared polarizing plate with an adhesive layer, the gel fraction, adhesive strength, microcreep, heat resistance, and moist heat shock resistance were measured in the same manner as in Example 1. The results are shown in Table 1.
  • Example 1 the non-volatile content and viscosity were measured in the same manner as in Example 1. The results are shown in Table 1. Further, the pressure-sensitive adhesive was obtained in the same manner as in Example 1 except that the pressure-sensitive adhesive composition obtained by adding the amount (part by mass) of TD-75 shown in Table 1 to the obtained polymer solution was used. A layered polarizing plate was produced. Using the prepared polarizing plate with an adhesive layer, the gel fraction, adhesive strength, microcreep, heat resistance, and moist heat shock resistance were measured in the same manner as in Example 1. The results are shown in Table 1.
  • -Measuring device HLC-8220GPC (manufactured by Tosoh Corporation) ⁇ GPC column configuration: The following 5-column column (all manufactured by Tosoh Corporation) (1) TSK-GEL HXL-H (guard column), (2) TSK-GEL G7000HXL, (3) TSK-GEL GMHXL, (4) TSK-GEL GMHXL, (5) TSK-GEL G2500HXL ⁇ Dilute with tetrahydrofuran so that the sample concentration is 1.0 mg / cm 3 ⁇ Mobile phase solvent: Tetrahydrofuran ⁇ Flow rate: 1.0 cm 3 / min -Column temperature: 40 ° C
  • the amount of the cross-linking agent used differs between the examples and the comparative examples because the gel fraction is 70 to 75% by mass in order to appropriately compare and evaluate the physical properties of the pressure-sensitive adhesive layer obtained from each pressure-sensitive adhesive composition. This is because it was unified so that it would be.
  • the non-volatile content and viscosity were measured in the polymer solution, but even if a cross-linking agent was added to the polymer solution, the non-volatile content increased only by adding the cross-linking agent, and the cross-linking agent was added. However, since the viscosities do not change substantially, the non-volatile content and viscosity of the polymer solution have a great influence on the non-volatile content and viscosity of the pressure-sensitive adhesive composition.
  • Example 1 From the results of the non-volatile content and the viscosity, it was found that the Mw of the copolymer in the polymer solution obtained in Example 1 was about the same as the Mw of the copolymer in the polymer solution obtained in Comparative Example 3 or 4. Conceivable.
  • Example 1 a polymer solution having a low viscosity and a high non-volatile content was obtained even though the copolymer was synthesized under the same conditions as in Comparative Examples 1 and 2.
  • the pressure-sensitive adhesive layer obtained in Example 1 showed durability (heat resistance and wet heat shock resistance) higher than that of the pressure-sensitive adhesive layer obtained in Comparative Examples 1 and 2 containing a higher molecular weight copolymer. ..
  • the present composition has a low viscosity and a high non-volatile content, is excellent in workability at the time of forming a pressure-sensitive adhesive layer, and the pressure-sensitive adhesive layer obtained from the present composition contains a higher molecular weight copolymer. It showed durability (heat resistance and moist heat shock resistance) comparable to that of the pressure-sensitive adhesive layer obtained from the pressure-sensitive adhesive composition and even higher than that of the pressure-sensitive adhesive layer obtained from the pressure-sensitive adhesive composition containing a higher polymer. .. Further, the pressure-sensitive adhesive layer obtained in Example 1 can be adhered with a certain degree of adhesive force when it is desired to be adhered to the adherend, and can be peeled off when it is to be peeled off from the adherend. It has an excellent balance of adhesiveness and reworkability.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Polarising Elements (AREA)

Abstract

Un mode de réalisation de la présente invention concerne une composition adhésive ou une plaque de polarisation contenant une couche adhésive. Cette composition adhésive contient un solvant organique et un copolymère (méth)acrylique provenant de la copolymérisation d'un ingrédient monomère contenant de 0,5 à 10 % en masse d'un monomère à base d'amine ayant une constante de dissociation acide (pKa) de 9 ou plus, la teneur en copolymère (méth)acrylique dans la composition adhésive étant de 20 % en masse ou plus.
PCT/JP2021/037361 2020-12-14 2021-10-08 Composition adhésive et plaque de polarisation contenant une couche adhésive WO2022130747A1 (fr)

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Citations (7)

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Publication number Priority date Publication date Assignee Title
JP2012111937A (ja) * 2010-11-05 2012-06-14 Kohjin Co Ltd 帯電防止粘着剤組成物及びそれを用いて得られる帯電防止粘着剤、帯電防止粘着シート
JP2012242473A (ja) * 2011-05-17 2012-12-10 Soken Chem & Eng Co Ltd 光学部材用粘着剤組成物およびその加工製品
JP2014152305A (ja) * 2013-02-13 2014-08-25 Fujimori Kogyo Co Ltd 粘着剤組成物及び粘着フィルム、表面保護フィルム、光学フィルム
JP2015110723A (ja) * 2013-11-05 2015-06-18 日東電工株式会社 携帯電子機器部材固定用両面粘着シートおよび携帯電子機器の製造方法
JP2016199701A (ja) * 2015-04-13 2016-12-01 日東電工株式会社 粘着シートおよび接合体製造方法
WO2016199602A1 (fr) * 2015-06-11 2016-12-15 綜研化学株式会社 Composition adhésive pour plaque polarisante, couche adhésive, feuille adhésive, et plaque polarisante comprenant une couche adhésive
JP2019206629A (ja) * 2018-05-29 2019-12-05 綜研化学株式会社 粘着剤組成物、粘着シートおよび画像表示装置

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012111937A (ja) * 2010-11-05 2012-06-14 Kohjin Co Ltd 帯電防止粘着剤組成物及びそれを用いて得られる帯電防止粘着剤、帯電防止粘着シート
JP2012242473A (ja) * 2011-05-17 2012-12-10 Soken Chem & Eng Co Ltd 光学部材用粘着剤組成物およびその加工製品
JP2014152305A (ja) * 2013-02-13 2014-08-25 Fujimori Kogyo Co Ltd 粘着剤組成物及び粘着フィルム、表面保護フィルム、光学フィルム
JP2015110723A (ja) * 2013-11-05 2015-06-18 日東電工株式会社 携帯電子機器部材固定用両面粘着シートおよび携帯電子機器の製造方法
JP2016199701A (ja) * 2015-04-13 2016-12-01 日東電工株式会社 粘着シートおよび接合体製造方法
WO2016199602A1 (fr) * 2015-06-11 2016-12-15 綜研化学株式会社 Composition adhésive pour plaque polarisante, couche adhésive, feuille adhésive, et plaque polarisante comprenant une couche adhésive
JP2019206629A (ja) * 2018-05-29 2019-12-05 綜研化学株式会社 粘着剤組成物、粘着シートおよび画像表示装置

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