WO2022185715A1 - Composition d'agent adhésif, feuille adhésive et élément optique - Google Patents

Composition d'agent adhésif, feuille adhésive et élément optique Download PDF

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Publication number
WO2022185715A1
WO2022185715A1 PCT/JP2022/000694 JP2022000694W WO2022185715A1 WO 2022185715 A1 WO2022185715 A1 WO 2022185715A1 JP 2022000694 W JP2022000694 W JP 2022000694W WO 2022185715 A1 WO2022185715 A1 WO 2022185715A1
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Prior art keywords
mass
monomer
polymer
meth
sensitive adhesive
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PCT/JP2022/000694
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English (en)
Japanese (ja)
Inventor
恵子 近藤
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綜研化学株式会社
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Priority to CN202280017383.6A priority Critical patent/CN116997628A/zh
Priority to JP2023503600A priority patent/JPWO2022185715A1/ja
Publication of WO2022185715A1 publication Critical patent/WO2022185715A1/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
    • 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]

Definitions

  • One embodiment of the present invention relates to a pressure-sensitive adhesive composition, pressure-sensitive adhesive sheet or optical member.
  • Optical members such as polarizing plates and retardation plates are used in display devices such as liquid crystal displays. It is used by attaching it to other members such as steel. Since the display devices and the like are used in various environments, the pressure-sensitive adhesive layer used as the lamination layer can exhibit desired properties such as heat resistance, cohesiveness, and adhesiveness in various environments. It has been demanded. Among various environments, for example, the inside of a vehicle such as an automobile is exemplified as a harsh environment that can become hot and humid.
  • Patent Documents 1 and 2 disclose pressure-sensitive adhesive compositions using acrylic polymers having carboxy groups as pressure-sensitive adhesive compositions that exhibit desired properties under high temperature and high humidity conditions.
  • the pressure-sensitive adhesive layers obtained from conventional pressure-sensitive adhesive compositions such as the pressure-sensitive adhesive compositions disclosed in Patent Document 1 and Patent Document 2 have a balance between cohesion and stress relaxation in a temperature range of 115 ° C. This causes foaming due to reduced cohesion, and problems such as peeling from the adherend and light leakage due to reduced stress relaxation. Therefore, it was found that the conventional PSA compositions have room for improvement in terms of high-temperature durability.
  • the adhesive layer when used by sticking it to the adherend, it does not peel off or float from the adherend, and when it is desired to be peeled off from the adherend, it adheres without leaving any adhesive residue. In some cases, it is required to have an appropriate adhesive strength that allows it to be peeled off from the body (excellent in reworkability).
  • the pressure-sensitive adhesive layer may be used in contact with a corrodible adherend such as a metal used for electrodes or a metal oxide such as ITO (indium tin oxide). It is also required not to corrode possible adherends.
  • One embodiment of the present invention is capable of suppressing corrosion of a corrodible adherend even when it is in contact with the adherend, has an appropriate adhesive strength, and foams even under high temperature and high humidity.
  • a pressure-sensitive adhesive composition capable of forming a pressure-sensitive adhesive layer that is less likely to be peeled off from an adherend.
  • a configuration example of the present invention is as follows.
  • the total content of the structural units derived from the hydroxyl group-containing monomer (b1) and the structural units derived from the amino group-containing monomer (b2) is 0.05% by mass or less, and the acid value is 1.0 mgKOH/g or less, weight average an acrylic polymer (B) having a molecular weight (Mw) of more than 250,000 and smaller than the Mw of the acrylic polymer (A); and an isocyanate curing agent (C),
  • the acrylic polymer (B) is contained in an amount of 10 parts by mass or more with respect to 100 parts by mass of the acrylic polymer
  • the acrylic polymer (A) contains 25 to 99.99% by mass of structural units derived from at least one monomer (a3) selected from alkyl (meth)acrylates and alkoxyalkyl (meth)acrylates, [ 1].
  • the acrylic polymer (B) contains 25 to 100% by mass of constitutional units derived from at least one monomer (b3) selected from alkyl (meth)acrylates and alkoxyalkyl (meth)acrylates [1] Or the pressure-sensitive adhesive composition according to [2].
  • the acrylic polymer (A) contains 25 to 98% by mass of structural units derived from at least one monomer (a3) selected from alkyl (meth)acrylates and alkoxyalkyl (meth)acrylates, and has an alicyclic [1] to [4] containing 1 to 50% by mass of structural units derived from at least one monomer (a4) selected from hydrocarbon group-containing (meth)acrylates and aromatic hydrocarbon group-containing (meth)acrylates.
  • the pressure-sensitive adhesive composition according to any one of the above.
  • the acrylic polymer (B) contains 25 to 98% by mass of structural units derived from at least one monomer (b3) selected from alkyl (meth)acrylates and alkoxyalkyl (meth)acrylates, and has an alicyclic [1] to [5] containing 1 to 50% by mass of structural units derived from at least one monomer (b4) selected from hydrocarbon group-containing (meth)acrylates and aromatic hydrocarbon group-containing (meth)acrylates.
  • the pressure-sensitive adhesive composition according to any one of the above.
  • the present invention even when in contact with a corrodible adherend, it is possible to suppress corrosion of the adherend, have an appropriate adhesive strength, and have a high temperature and high humidity.
  • the pressure-sensitive adhesive composition according to one embodiment of the present invention (hereinafter also referred to as "this composition") is a total of the structural units derived from the hydroxyl group-containing monomer (a1) and the structural units derived from the amino group-containing monomer (a2).
  • the total content of the structural units derived from the hydroxyl group-containing monomer (b1) and the structural units derived from the amino group-containing monomer (b2) is 0.05% by mass or less, and the acid value is 1.0 mgKOH/g or less, weight average an acrylic polymer (B) having a molecular weight (Mw) of more than 250,000 and smaller than the Mw of the acrylic polymer (A);
  • a pressure-sensitive adhesive composition containing an isocyanate curing agent (C) The acrylic polymer (B) is contained in an amount of 10 parts by mass or more with respect to 100 parts by mass of the acrylic polymer (A),
  • the isocyanate curing agent (C) is contained in an amount of more than 6 parts by mass and less than 30 parts by mass
  • the "acrylic polymer” refers to a structural unit derived from acrylic acid, a structural unit derived from acrylate, a structural unit derived from acrylic acid ester, a structural unit derived from methacrylic acid, a structural unit derived from methacrylate, and A polymer in which the total amount of structural units derived from methacrylic acid ester is 50% by mass or more with respect to 100% by mass of all structural units of the acrylic polymer.
  • (meth)acrylic is used as a generic term for acrylic and methacrylic, and may be acrylic or methacrylic.
  • (Meth)acrylate is used as a generic term for acrylate and methacrylate, and may be either acrylate or methacrylate.
  • (meth)acryloyl is used as a generic term for acryloyl and methacryloyl, and may be acryloyl or methacryloyl.
  • the acrylic polymer (A) (hereinafter also referred to as “polymer (A)”) is a structural unit derived from a hydroxyl group-containing monomer (a1) (hereinafter also referred to as “monomer (a1)”) and an amino group-containing monomer (a2) (hereinafter also referred to as “monomer (a2)”) containing structural units derived in an amount exceeding 0% by mass and 0.4% by mass or less, and having an acid value of 1.0 mgKOH/g or less, and , Mw is 600,000 or more.
  • the obtained pressure-sensitive adhesive layer has a low cross-linking density, which makes it possible to easily form a pressure-sensitive adhesive layer which is excellent in stress relaxation properties and which hardly causes peeling of the adherend.
  • the stress applied to the pressure-sensitive adhesive layer can be relaxed when using the pressure-sensitive adhesive layer obtained in contact with an adherend (e.g., polarizing plate) that can shrink significantly. Furthermore, shrinkage of the adherend can be suppressed.
  • the content of structural units derived from the monomer (a1) and the monomer (a2) can be calculated from the amounts of the monomer (a1) and the monomer (a2) in the monomer component used when synthesizing the polymer (A).
  • the polymer (A) can be synthesized by polymerizing a monomer component containing at least one selected from the monomer (a1) and the monomer (a2), and the monomer component preferably contains the monomer (a1).
  • the monomer (a1) may be used alone or in combination of two or more.
  • Examples of the monomer (a1) include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, 8-hydroxyoctyl (meth)acrylate, 10-hydroxydecyl (meth)acrylate, 12-hydroxylauryl (meth)acrylate, (4-hydroxymethylcyclohexyl)methyl (meth)acrylate.
  • Polymer (A) can be synthesized by polymerizing a monomer component containing at least one selected from monomer (a1) and monomer (a2), but the monomer component preferably does not contain monomer (a2).
  • the monomer (a2) may be used alone or in combination of two or more.
  • Monomer (a2) is a monomer other than monomer (a1).
  • a monomer having an amide group or an imide group and having no amino group other than the amide group or the imide group is a monomer (a2 )is not.
  • Examples of the monomer (a2) include dialkylaminoalkyl (meth)acrylates such as dimethylaminoethyl (meth)acrylate and diethylaminoethyl (meth)acrylate.
  • Polymer (A) further contains structural units derived from at least one monomer (a3) selected from alkyl (meth)acrylates and alkoxyalkyl (meth)acrylates (hereinafter also referred to as "monomer (a3)"). is preferred, and it is particularly preferred to contain structural units derived from alkyl (meth)acrylates and alkoxyalkyl (meth)acrylates.
  • Monomer (a3) is a monomer other than monomer (a1), monomer (a2) and monomer (a4) below.
  • the adhesive strength and reworkability (reattachability) of the obtained pressure-sensitive adhesive layer can be easily adjusted.
  • the polymer (A) contains a structural unit derived from an alkoxyalkyl (meth)acrylate, the time until the physical properties (eg, gel fraction) of the resulting pressure-sensitive adhesive layer do not change is shortened (hereinafter referred to as "aging Therefore, it is possible to form a pressure-sensitive adhesive layer with excellent quality stability with good productivity.
  • the gel fraction can be measured by the method described in Examples below.
  • the content of the structural unit derived from the monomer (a3) is the total content of the polymer (A) from the viewpoint that the above effects are exhibited more. It is preferably 25 to 99.99% by mass, more preferably 50 to 99.99% by mass, based on 100% by mass of the structural units.
  • the polymer (A) contains structural units other than those derived from the monomer (a1), the monomer (a2) and the monomer (a3), particularly the monomer (a1), the monomer (a2) and the monomer (a3)
  • the upper limit of the content of the structural unit derived from the monomer (a3) is preferably 98% by mass or less, more preferably 97% by mass or less, and the lower limit is It is preferably 25% by mass or more, more preferably 50% by mass or more.
  • the content of structural units derived from the monomer (a3) can be calculated from the amount of the monomer (a3) in the monomer component used when synthesizing the polymer (A).
  • alkyl (meth)acrylates examples include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, iso-propyl (meth)acrylate, n-butyl (meth)acrylate, iso-butyl (meth)acrylate, tert-butyl (meth)acrylate, pentyl (meth)acrylate, hexyl (meth)acrylate, heptyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, n-octyl (meth)acrylate, iso-octyl (meth) acrylate, nonyl (meth) acrylate, iso-nonyl (meth) acrylate, decyl (meth) acrylate, iso-decyl (meth) acrylate, undeca (meth) acrylate, lauryl (meth) acrylate
  • alkoxyalkyl (meth)acrylates examples include methoxymethyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, 2-ethoxyethyl (meth)acrylate, 3-methoxypropyl (meth)acrylate, 3-ethoxypropyl (Meth)acrylate, 4-methoxybutyl (meth)acrylate, 4-ethoxybutyl (meth)acrylate.
  • One type of alkoxyalkyl (meth)acrylate may be used alone, or two or more types may be used.
  • the polymer (A) further contains at least one monomer (a4) selected from alicyclic hydrocarbon group-containing (meth)acrylates and aromatic hydrocarbon group-containing (meth)acrylates (hereinafter also referred to as "monomer (a4)" It may contain structural units derived from Monomer (a4) is a monomer other than monomer (a1) and monomer (a2).
  • monomer (a4) is a monomer other than monomer (a1) and monomer (a2).
  • the polymer (A) contains a structural unit derived from an aromatic hydrocarbon group-containing (meth)acrylate, it is possible to easily form a pressure-sensitive adhesive layer that has excellent adhesion to an adherend and can suppress light leakage. can be done.
  • the content of the structural unit derived from the monomer (a4) is the total content of the polymer (A) from the viewpoint that the above effects are exhibited more. It is preferably 1 to 50% by mass, more preferably 1 to 30% by mass, based on 100% by mass of the structural units.
  • the content of structural units derived from the monomer (a4) can be calculated from the amount of the monomer (a4) in the monomer component used when synthesizing the polymer (A).
  • Examples of the alicyclic hydrocarbon group-containing (meth)acrylates include cyclohexyl (meth)acrylate, 4-t-butylcyclohexyl (meth)acrylate, isobornyl (meth)acrylate, and adamantyl (meth)acrylate.
  • the alicyclic hydrocarbon group-containing (meth)acrylates may be used alone or in combination of two or more.
  • aromatic hydrocarbon group-containing (meth)acrylates examples include benzyl (meth)acrylate, phenyl (meth)acrylate, and phenoxyethyl (meth)acrylate.
  • the aromatic hydrocarbon group-containing (meth)acrylates may be used singly or in combination of two or more.
  • the polymer (A) may further contain constituent units derived from monomers other than the monomer (a1), the monomer (a2), the monomer (a3) and the monomer (a4) as long as the object of the present invention is not impaired. good.
  • the content of the structural unit derived from the other monomer is preferably 30% by mass or less, preferably 20% by mass, based on 100% by mass of the total structural units of the polymer (A), from the viewpoint that the above effect is more exhibited. % or less.
  • the content of structural units derived from other monomers can be calculated from the amount of other monomers in the monomer component used when synthesizing the polymer (A).
  • Examples of the other monomers include (meth)acrylamide; N-alkyl (meth)acrylamide such as N-methyl (meth)acrylamide, N-ethyl (meth)acrylamide, N-propyl (meth)acrylamide, N-hexyl (meth)acrylamide; N,N- N,N-dialkyl(meth)acrylamides such as dimethyl(meth)acrylamide and N,N-diethyl(meth)acrylamide; cyclic amide group-containing monomers such as N-vinylpyrrolidone, N-vinylcaprolactam and (meth)acryloylmorpholine;
  • amide group-containing monomers and nitrogen-based heterocyclic ring-containing monomers are preferable, and by using the polymer (A) containing structural units derived from these monomers, excellent aging resistance and excellent quality stability can be obtained.
  • a pressure-sensitive adhesive layer can be formed with good productivity.
  • Polymer (A) can be synthesized by polymerizing the aforementioned monomer components, and may be, for example, a random polymer, a block polymer or a graft polymer, and can be synthesized by various polymerization methods.
  • the polymerization method is not particularly limited, and examples thereof include solution polymerization, emulsion polymerization, and suspension polymerization. Among these, in producing the present composition using a mixture of copolymers obtained by polymerization, solution polymerization is preferred from the viewpoint that the processing steps are relatively simple and can be carried out in a short time. is preferred.
  • a reaction vessel is charged with other components such as a monomer component, a polymerization initiator and, if necessary, a chain transfer agent and a polymerization solvent, and the reaction initiation temperature is usually 40° C. or higher, preferably 50° C. C. or higher, usually 100.degree. C. or lower, preferably 80.degree. .
  • the reaction is performed, for example, under an inert gas atmosphere such as nitrogen gas.
  • at least one selected from monomer components, polymerization initiators, chain transfer agents and polymerization solvents may be additionally added during the polymerization reaction.
  • polymerization initiators include azo initiators and peroxide polymerization initiators.
  • azo initiators include 2,2′-azobisisobutyronitrile, 2,2′-azobis(4-methoxy-2,4-dimethylvaleronitrile), 2,2′-azobis(2- cyclopropylpropionitrile), 2,2′-azobis(2,4-dimethylvaleronitrile), 2,2′-azobis(2-methylbutyronitrile), 1,1′-azobis(cyclohexane-1-carbo nitrile), 2-(carbamoylazo)isobutyronitrile, 2-phenylazo-4-methoxy-2,4-dimethylvaleronitrile, 2,2′-azobis(2-amidinopropane) dihydrochloride, 2,2′- azobis(N,N'-dimethyleneisobutylamidine), 2,2'-azobis[2-methyl-N-(2-hydroxyethyl)-propionamide],
  • peroxide polymerization initiators examples include t-butyl hydroperoxide, cumene hydroperoxide, dicumyl peroxide, benzoyl peroxide, lauroyl peroxide, caproyl peroxide, di-i-propyl peroxide, Carbonate, di-2-ethylhexylperoxydicarbonate, t-butyl peroxypivalate, 2,2-bis(4,4-di-t-butylperoxycyclohexyl)propane, 2,2-bis(4,4 -di-t-amylperoxycyclohexyl)propane, 2,2-bis(4,4-di-t-octylperoxycyclohexyl)propane, 2,2-bis(4,4-di- ⁇ -cumylperoxy cyclohexyl)propane, 2,2-bis(4,4-di-t-butylperoxycyclohexyl)butane, and 2,2-bis(4,
  • a polymerization initiator may be used individually by 1 type, and may use 2 or more types. Also, the polymerization initiator may be added multiple times during the polymerization.
  • the amount of the polymerization initiator used is usually 0.001 parts by mass or more, preferably 0.005 parts by mass or more, and usually 5 parts by mass or less, preferably 3 parts by mass or less, relative to 100 parts by mass of the monomer component.
  • polymerization solvent used for solution polymerization examples include aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic hydrocarbons such as n-pentane, n-hexane, n-heptane and n-octane; cyclopentane, cyclohexane, 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, Halogenated hydrocarbons such as carbon tetrachloride, 1,2-dichloroethane, chlorobenzene; Esters such as ethyl acetate, propyl acetate, butyl acetate
  • ketones such as N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone; nitriles such as acetonitrile and benzonitrile; and sulfoxides such as dimethylsulfoxide and sulfolane.
  • One type of polymerization solvent may be used alone, or two or more types may be used.
  • the weight average molecular weight (Mw) of the polymer (A) measured by gel permeation chromatography (GPC) is 600,000 or more, preferably 800,000 or more, more preferably 1,000,000 or more, preferably 300. 10,000 or less, more preferably 2,500,000 or less.
  • Mw is within the above range, a pressure-sensitive adhesive layer having excellent durability and cohesion can be easily formed.
  • the Mw can be measured by the method described in Examples below.
  • the acid value of polymer (A) is 1.0 mgKOH/g or less, preferably 0.8 mgKOH/g or less, more preferably 0 mgKOH/g.
  • the acid value of the polymer (A) is within the above range, corrosion of adherends in contact with the pressure-sensitive adhesive layer formed from the obtained pressure-sensitive adhesive composition can be suppressed.
  • the acid value can be measured by the method described in Examples below.
  • the amount of the acidic group-containing monomer used is 0.12% by mass or less with respect to 100% by mass of the monomer component, or , preferably without substantially using an acidic group-containing monomer.
  • acidic group-containing monomers examples include acrylic acid, methacrylic acid, ⁇ -carboxyethyl(meth)acrylate, 5-carboxypentyl(meth)acrylate, succinic acid mono(meth)acryloyloxyethyl ester, ⁇ -carboxy Examples include carboxyl group-containing monomers such as polycaprolactone mono(meth)acrylate, crotonic acid, maleic acid, fumaric acid, itaconic acid, and citraconic acid.
  • the composition can contain one or more polymers (A).
  • the content of the polymer (A) in the composition is preferably 20% by mass or more, more preferably 25% by mass or more, preferably 70% by mass or less, and more Preferably, it is 65% by mass or less.
  • the polymer (A) has an appropriate adhesive strength, is excellent in well-balanced cohesive strength and stress relaxation even under high temperature and high humidity, and is resistant to foaming and peeling from the adherend.
  • a pressure-sensitive adhesive layer that is difficult to form can be easily formed.
  • the acrylic polymer (B) (hereinafter also referred to as “polymer (B)”) is a structural unit derived from a hydroxyl group-containing monomer (b1) (hereinafter also referred to as “monomer (b1)”) and an amino group-containing monomer (b2). (hereinafter also referred to as “monomer (b2)”), the total content of structural units derived from it is 0.05% by mass or less, the acid value is 1.0 mgKOH/g or less, and the Mw is more than 250,000; Moreover, it is a polymer smaller than the Mw of the acrylic polymer (A).
  • the present composition contains the polymer (B), even when the pressure-sensitive adhesive layer obtained from the present composition is used in contact with an adherend (e.g., polarizing plate) that shrinks significantly due to temperature changes, the It is possible to easily form a pressure-sensitive adhesive layer that exhibits sufficient shear stress against contraction of an adherend and can be relaxed without residual internal stress.
  • adherend e.g., polarizing plate
  • the total content of structural units derived from the monomer (b1) and structural units derived from the monomer (b2) in the polymer (B) is 0.05% by mass or less with respect to 100% by mass of all structural units of the polymer (B). , preferably 0.02% by mass or less, more preferably 0.01% by mass or less.
  • the lower limit of the total content is preferably 0% by mass.
  • the stress applied to the pressure-sensitive adhesive layer can be relaxed when using the pressure-sensitive adhesive layer obtained in contact with an adherend (e.g., polarizing plate) that can shrink significantly. Furthermore, shrinkage of the adherend can be suppressed.
  • the content of structural units derived from the monomer (b1) and the monomer (b2) can be calculated from the amounts of the monomer (b1) and the monomer (b2) in the monomer component used when synthesizing the polymer (B).
  • Examples of the monomer (b1) and the monomer (b2) include the same monomers as the monomer (a1) and the monomer (a2), respectively.
  • the monomer (b1) may be used alone or in combination of two or more.
  • the monomer (b2) may also be used singly or in combination of two or more.
  • Monomer (b2) is a monomer other than monomer (b1).
  • the polymer (B) preferably contains structural units derived from at least one monomer (b3) selected from alkyl (meth)acrylates and alkoxyalkyl (meth)acrylates (hereinafter also referred to as "monomer (b3)"). , alkyl (meth)acrylate and alkoxyalkyl (meth)acrylate-derived structural units are particularly preferred.
  • alkyl (meth)acrylate and alkoxyalkyl (meth)acrylate-derived structural units are particularly preferred.
  • the adhesive strength and reworkability of the obtained pressure-sensitive adhesive layer can be easily adjusted.
  • the polymer (B) contains structural units derived from alkoxyalkyl (meth)acrylate, it is possible to form a pressure-sensitive adhesive layer excellent in aging resistance and quality stability with good productivity.
  • the content of the structural unit derived from the monomer (b3) is the total content of the polymer (B) from the viewpoint that the above effects are exhibited more. It is preferably 25 to 100% by mass, more preferably 50 to 100% by mass, based on 100% by mass of the structural units.
  • the polymer (B) contains structural units other than the structural units derived from the monomer (b1), the monomer (b2) and the monomer (b3), particularly the monomer (b1), the monomer (b2) and the monomer (b3 ) and a structural unit derived from the following monomer (b4)
  • the upper limit of the content of the structural unit derived from the monomer (b3) is preferably 98% by mass or less, more preferably 97% by mass or less, and the lower limit is , preferably 25% by mass or more, more preferably 50% by mass or more.
  • the content of structural units derived from the monomer (b3) can be calculated from the amount of the monomer (b3) in the monomer component used when synthesizing the polymer (B).
  • Examples of the monomer (b3) include monomers similar to the monomer (a3).
  • the monomer (b3) may be used alone or in combination of two or more.
  • Monomer (b3) is a monomer other than monomer (b1), monomer (b2) and monomer (b4) below.
  • Polymer (B) further contains at least one monomer (b4) selected from alicyclic hydrocarbon group-containing (meth)acrylates and aromatic hydrocarbon group-containing (meth)acrylates (hereinafter also referred to as "monomer (b4)" It may contain structural units derived from When the polymer (B) contains structural units derived from an alicyclic hydrocarbon group-containing (meth)acrylate, it is possible to easily adjust the cohesive strength and stress relaxation properties of the resulting pressure-sensitive adhesive layer.
  • the polymer (B) contains a structural unit derived from an aromatic hydrocarbon group-containing (meth)acrylate, it is possible to easily form a pressure-sensitive adhesive layer that has excellent adhesion to an adherend and can suppress light leakage. can be done.
  • the content of the structural unit derived from the monomer (b4) is the total content of the polymer (B) from the viewpoint that the above effects are exhibited more. It is preferably 1 to 50% by mass, more preferably 1 to 30% by mass, based on 100% by mass of the structural units.
  • the content of structural units derived from the monomer (b4) can be calculated from the amount of the monomer (b4) in the monomer component used when synthesizing the polymer (B).
  • Examples of the monomer (b4) include monomers similar to the monomer (a4).
  • the monomer (b4) may be used alone or in combination of two or more.
  • Monomer (b4) is a monomer other than monomer (b1) and monomer (b2).
  • the polymer (B) may further contain constituent units derived from monomers other than the monomer (b1), the monomer (b2), the monomer (b3) and the monomer (b4), as long as the object of the present invention is not impaired. good.
  • the content of the structural unit derived from the other monomer is preferably 30% by mass or less, preferably 20% by mass, based on 100% by mass of the total structural units of the polymer (B), from the viewpoint that the above effect is more exhibited. % or less.
  • the content of structural units derived from other monomers can be calculated from the amount of other monomers in the monomer component used when synthesizing the polymer (B).
  • Examples of the other monomers include monomers similar to the other monomers listed in the column for polymer (A). Another monomer may be used individually by 1 type, and 2 or more types may be used.
  • Polymer (B) can be synthesized by polymerizing the aforementioned monomer components, and may be, for example, a random polymer, a block polymer or a graft polymer, and can be synthesized by various polymerization methods.
  • the polymerization method is not particularly limited, and examples thereof include solution polymerization, emulsion polymerization, and suspension polymerization. Among these, in producing the present composition using a mixture of polymers obtained by polymerization, solution polymerization is preferred from the viewpoint that the processing steps are relatively simple and can be carried out in a short period of time. preferable.
  • a reaction vessel is charged with other components such as a monomer component, a polymerization initiator and, if necessary, a chain transfer agent and a polymerization solvent, and the reaction initiation temperature is usually 40° C. or higher, preferably 50° C. C. or higher, usually 100.degree. C. or lower, preferably 80.degree. .
  • the reaction is performed, for example, under an inert gas atmosphere such as nitrogen gas.
  • at least one selected from monomer components, polymerization initiators, chain transfer agents, and polymerization solvents may be additionally added during the polymerization reaction.
  • the same polymerization initiator and polymerization solvent as those described in the section for the method for synthesizing the polymer (A) can be used. are mentioned.
  • Mw of polymer (B) measured by GPC method is greater than 250,000 and smaller than Mw of polymer (A).
  • the lower limit of Mw of the polymer (B) is preferably 300,000 or more, more preferably 500,000 or more.
  • the upper limit of the Mw of the polymer (B) is not particularly limited as long as it is smaller than the Mw of the polymer (A), preferably 1,000,000 or less.
  • the shrinkage of the adherend It is possible to easily form a pressure-sensitive adhesive layer that can be relieved without residual internal stress while exhibiting a sufficient shear stress against.
  • the Mw can be measured by the method described in Examples below.
  • the Mw of polymer (B) is smaller than the Mw of polymer (A), and the ratio of Mw of polymer (B) to Mw of polymer (A) (Mw of polymer (B)/Mw of polymer (A)) is preferably is 0.8 or less, more preferably 0.6 or less.
  • the acid value of polymer (B) is 1.0 mgKOH/g or less, preferably 0.8 mgKOH/g or less, more preferably 0 mgKOH/g.
  • the acid value of the polymer (B) is within the above range, corrosion of adherends in contact with the pressure-sensitive adhesive layer formed from the obtained pressure-sensitive adhesive composition can be suppressed.
  • the acid value can be measured by the method described in Examples below.
  • the amount of the acidic group-containing monomer used is 0.12% by mass or less with respect to 100% by mass of the monomer component, or , preferably without substantially using an acidic group-containing monomer.
  • the acidic group-containing monomer include monomers similar to the acidic group-containing monomers described in the column of polymer (A).
  • the composition can contain one or more polymers (B).
  • the content of the polymer (B) in the present composition is 10 parts by mass or more, preferably 25 parts by mass or more, more preferably 40 parts by mass or more, preferably 300 parts by mass with respect to 100 parts by mass of the polymer (A). It is not more than 200 parts by mass, more preferably not more than 200 parts by mass.
  • the content of the polymer (B) is within the above range, even when the pressure-sensitive adhesive layer obtained from the present composition is used in contact with an adherend (e.g., polarizing plate) that undergoes large shrinkage due to temperature changes, Therefore, it is possible to easily form a pressure-sensitive adhesive layer that can be relieved without residual internal stress while exhibiting sufficient shear stress against shrinkage of the adherend.
  • adherend e.g., polarizing plate
  • the composition contains an isocyanate-based curing agent (C) (hereinafter also referred to as “curing agent (C)”).
  • curing agent (C) examples include isocyanate compounds having two or more isocyanate groups in one molecule.
  • curing agent (C) examples include isocyanate monomers such as xylylene diisocyanate, tolylene diisocyanate, chlorophenylene diisocyanate, hexamethylene diisocyanate, tetramethylene diisocyanate, isophorone diisocyanate, diphenylmethane diisocyanate, and hydrogenated diphenylmethane diisocyanate; Isocyanate compounds obtained by addition reaction with divalent or higher alcohol compounds such as trimethylolpropane; buret-type isocyanate compounds; polyether polyols, polyester polyols, acrylic polyols, polybutadiene polyols, polyisoprene polyols, etc. added to isocyanate monomers. and urethane prepolymer type isocyanates; isocyanurate compounds.
  • isocyanate monomers such as xylylene diisocyanate, tolylene diisocyanate, chloropheny
  • the composition may contain one or more curing agents (C).
  • the content of the curing agent (C) in the present composition is more than 6 parts by mass and less than 30 parts by mass, preferably 7 parts by mass, with respect to a total of 100 parts by mass of the polymer (A) and the polymer (B). Above, more preferably 8 parts by mass or more, preferably 25 parts by mass or less, more preferably 20 parts by mass or less.
  • the fact that the content of the curing agent (C) is within the above range means that the amount of the curing agent (C) is such that the amount of isocyanate groups is excessive with respect to the number of crosslinkable functional groups possessed by the polymer (A). means to use in quantity.
  • the present composition may contain other components other than the polymer (A), the polymer (B) and the curing agent (C), such as a curing agent (D ), silane coupling agent (E), antistatic agent (F), tackifying resin, antioxidant, light stabilizer, metal corrosion inhibitor, plasticizer, cross-linking accelerator, surfactant, reworking agent, organic solvent may contain.
  • a curing agent (D ) silane coupling agent (E), antistatic agent (F), tackifying resin, antioxidant, light stabilizer, metal corrosion inhibitor, plasticizer, cross-linking accelerator, surfactant, reworking agent, organic solvent may contain.
  • a curing agent (D ), silane coupling agent (E), antistatic agent (F), tackifying resin, antioxidant, light stabilizer, metal corrosion inhibitor, plasticizer, cross-linking accelerator, surfactant, reworking agent, organic solvent may contain.
  • Each of these other components may be used singly or in combination of two or more.
  • the present composition may contain a curing agent (D) (hereinafter also referred to as "curing agent (D)”) other than the curing agent (C).
  • a curing agent (D) (hereinafter also referred to as "curing agent (D)") other than the curing agent (C).
  • curing agent (D) include epoxy curing agents and metal chelate curing agents.
  • epoxy-based curing agents include ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, glycerin diglycidyl ether, glycerin triglycidyl ether, 1,3-bis(N,N-diglycidylaminomethyl)cyclohexane, N, N,N',N'-tetraglydyl-m-xylylenediamine, N,N,N',N'-tetraglydylaminophenylmethane, triglycidyl isocyanurate, mN,N-diglycidylaminophenylglycidyl ether , N,N-diglycidyltoluidine, N,N-diglycidylaniline, pentaerythritol polyglycidyl ether, 1,6-hexanediol diglycidyl ether.
  • metal chelate curing agents include polyvalent metals such as aluminum, iron, copper, zinc, tin, titanium, nickel, antimony, magnesium, vanadium, chromium, and zirconium combined with alkoxides, acetylacetone, ethyl acetoacetate, and the like.
  • a compound with a Specific examples include aluminum isopropylate, aluminum secondary butyrate, aluminum ethylacetoacetate/diisopropylate, aluminum trisethylacetoacetate, and aluminum trisacetylacetonate.
  • the content of the curing agent (D) in the present composition should be the same as the polymer (A) and the polymer (B) in terms of exhibiting the above effects more. It is preferably 0.005 parts by mass or more, more preferably 0.01 parts by mass or more, preferably 6 parts by mass or less, and more preferably 3 parts by mass or less, relative to the total 100 parts by mass of .
  • the composition may contain a silane coupling agent (E).
  • a silane coupling agent (E) By including the silane coupling agent (E) in the present composition, it is possible to easily form a pressure-sensitive adhesive layer having high adhesion to an adherend.
  • Silane coupling agents (E) include, for example, vinyltrimethoxysilane, vinyltriethoxysilane, silane coupling agents containing polymerizable unsaturated groups such as methacryloxypropyltrimethoxysilane; 3-glycidoxypropyltrimethoxysilane; , 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane and other epoxy groups Containing silane coupling agent; amino such as 3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane Group-containing silane coupling agents; Hal
  • the content of the silane coupling agent (E) in the composition is It is usually 1 part by mass or less, preferably 0.01 mass part or more, more preferably 0.05 mass part or more, and preferably 1 mass part or less, more preferably 0.5 mass part or less.
  • the content of the silane coupling agent (E) is within the above range, peeling of the pressure-sensitive adhesive layer from the adherend can be easily suppressed even in a high-humidity and heat environment, and even in a high-temperature environment, the silane coupling It tends to be possible to easily form a pressure-sensitive adhesive layer in which bleeding of the agent (E) is difficult to occur.
  • the composition may contain an antistatic agent (F).
  • Antistatic agents (F) include, for example, surfactants, ionic compounds, and conductive polymers.
  • Surfactants include, for example, quaternary ammonium salts, quaternary amide quaternary ammonium salts, pyridium salts, cationic surfactants having cationic groups such as primary to tertiary amino groups; sulfonate groups, sulfate esters Anionic surfactants having anionic groups such as bases and phosphate ester bases; Amphoteric surfactants such as alkylbetaines, alkylimidazolinium betaines, alkylamine oxides, amino acid sulfate esters; , sorbitan fatty acid esters, polyoxyethylene alkylamines, polyoxyethylene alkylamine fatty acid esters, N-hydroxyethyl-N-2-hydroxyalkylamines, alkyldiethanolamides and other nonionic surfactants. be done.
  • the surfactant also includes a reactive emulsifier having a polymerizable group, and a polymer-based surfactant obtained by increasing the molecular weight of the monomer component containing the surfactant or reactive emulsifier can also be used.
  • the ionic compound is a compound composed of a cation portion and an anion portion, and may be a solid or liquid compound at room temperature (23°C) and 50% RH.
  • the cation moiety constituting the ionic compound may be either one or both of inorganic cations and organic cations.
  • inorganic cations alkali metal ions and alkaline earth metal ions are preferable, and Li + , Na + and K + which are excellent in antistatic properties are more preferable.
  • organic cations include pyridinium cations, piperidinium cations, pyrrolidinium cations, pyrroline cations, pyrrole cations, imidazolium cations, tetrahydropyrimidinium cations, dihydropyrimidinium cations, pyrazolium cations, and pyrazolium cations.
  • the anion portion constituting the ionic compound is not particularly limited as long as it can ionically bond with the cation portion to form an ionic compound.
  • Ionic compounds include lithium bis(trifluoromethanesulfonyl)imide, lithium bis(fluorosulfonyl)imide, lithium tris(trifluoromethanesulfonyl)methane, potassium bis(trifluoromethanesulfonyl)imide, potassium bis(fluorosulfonyl)imide, 1 - ethylpyridinium hexafluorophosphate, 1-butylpyridinium hexafluorophosphate, 1-hexyl-4-methylpyridinium hexafluorophosphate, 1-octyl-4-methylpyridinium hexafluorophosphate, 1-octyl-4-methylpyridinium bis(fluoro sulfonyl)imide, 1-octyl-4-methylpyridinium bis(fluoro sulfonyl)imide, 1-octyl-4-methylpyridinium bis(trifluo
  • Examples of conductive polymers include polythiophene, polyaniline, polypyrrole, and derivatives thereof.
  • the content of the antistatic agent (F) in the present composition is usually 3 parts per 100 parts by mass of the total of the polymer (A) and the polymer (B). parts by mass or less, preferably 0.01 to 3 parts by mass, more preferably 0.05 to 2.5 parts by mass.
  • the composition may contain an organic solvent as long as the effects of the present invention are not impaired.
  • the organic solvent includes, for example, the polymerization solvents described in the section of the method for synthesizing the polymer (A).
  • the composition may be prepared, for example, by mixing a polymer solution containing the polymer (A) and the polymerization solvent, a polymer solution containing the polymer (B) and the polymerization solvent, and the curing agent (C).
  • the content of the organic solvent in the present composition is, for example, 0% by mass or more, preferably 10% by mass or more, and is, for example, 90% by mass or less, preferably 80% by mass or less.
  • the present composition can be prepared, for example, by mixing the polymer (A), the polymer (B), the curing agent (C), and, if necessary, the other components by a known method using a stirring device or the like. can be manufactured by When mixing and stirring each component, each component may be mixed and stirred all at once, or may be mixed and stirred sequentially.
  • the stirring conditions are not particularly limited, but from the standpoint of workability and productivity, the stirring may be performed at room temperature for about 10 to 120 minutes.
  • the application of the present composition is not particularly limited, and it can be used without limitation in the applications in which the pressure-sensitive adhesive layer has been used. It is preferably used for bonding members, and more preferably used for bonding members constituting a display device such as a touch panel type input/output device.
  • Members (adherends) to be bonded using the present composition include, for example, polarizing films (including elliptical polarizing films), retardation films, antireflection films, brightness enhancement films, light diffusion films, and hard coats.
  • Optical films such as films, metal or metal oxide layers such as ITO layers, and substrates made of glass or resin can be used.
  • a pressure-sensitive adhesive sheet according to an embodiment of the present invention (hereinafter also referred to as “the present pressure-sensitive adhesive sheet") has a pressure-sensitive adhesive layer (hereinafter also referred to as “the present pressure-sensitive adhesive layer”) obtained from the present composition.
  • the present pressure-sensitive adhesive sheet may be a sheet consisting only of the present pressure-sensitive adhesive layer, and includes at least one adherend selected from the optical film, the metal or metal oxide layer, the substrate, etc., and the pressure-sensitive adhesive layer. It may be a laminate containing.
  • the pressure-sensitive adhesive layer contained in the laminate may be one layer or two or more layers. When there are two or more layers, these may be the same layer or different layers. The same applies to adherends (other layers such as optical films) included in the laminate.
  • the thickness of the adhesive sheet is not particularly limited.
  • the thickness is approximately the same as the thickness of the pressure-sensitive adhesive layer described below.
  • the pressure-sensitive adhesive sheet is the laminate, it varies depending on the type of the adherend and may be appropriately selected according to the application. 200 ⁇ m or less.
  • the present pressure-sensitive adhesive layer is formed from the present composition, and specifically, can be formed by subjecting the present composition to a cross-linking reaction.
  • Examples of preferred aspects of the present pressure-sensitive adhesive layer obtained by subjecting the present composition to a cross-linking reaction include an aspect including a cross-linked product of the polymer (A) with the curing agent (C). Excess self-condensate of curing agent (C) that did not contribute to the cross-linking reaction is entangled with at least one selected from polymer (A), cross-linked polymer (A) and polymer (B).
  • the gel fraction of the present pressure-sensitive adhesive layer is not particularly limited. It is preferably 50% or more, more preferably 60% or more, and preferably 90% or less, more preferably 85% or less. Specifically, the gel fraction can be measured by the method described in Examples below.
  • the thickness of the pressure-sensitive adhesive layer may be appropriately set according to the application of the pressure-sensitive adhesive sheet, and is not particularly limited, but is usually 5 ⁇ m or more, preferably 10 ⁇ m or more, and usually 125 ⁇ m or less, preferably 100 ⁇ m or less. .
  • the adhesive strength of the present pressure-sensitive adhesive layer is preferably 1.0 N/25 mm or more in terms of sufficient adhesion to the adherend, etc., and when used by adhering to the adherend, It is more preferably 2.0 to 20.0 to 2.0 to 20.0, since it does not peel off or float from the adherend, and when it is desired to be peeled off from the adherend, it has an appropriate adhesive strength that allows it to be peeled off from the adherend without leaving an adhesive residue. 0 N/25 mm. Specifically, the adhesive strength can be measured by the method described in Examples below.
  • the pressure-sensitive adhesive layer is formed on the adherend or support by, for example, applying the present composition to the adherend or support and causing a cross-linking reaction of the applied composition. can be formed. After coating the present composition on the adherend or support, if necessary, further arrange the adherend or support on the coated surface to allow the composition to undergo a cross-linking reaction. good.
  • the pressure-sensitive adhesive layer may be peeled off from the support.
  • the pressure-sensitive adhesive sheet consisting of only the pressure-sensitive adhesive layer is stored, transferred, etc. together with the support during storage, transfer, etc., and is peeled off from the support during use. Just do it.
  • the support includes a release-treated substrate.
  • the composition is applied onto the adherend, and a support is placed on the coated surface to obtain the adherend and the pressure-sensitive adhesive.
  • a laminate in which a layer and a support are laminated in this order can be obtained.
  • the laminate can be used as a pressure-sensitive adhesive sheet consisting of an adherend and the present pressure-sensitive adhesive layer after peeling off the support.
  • the substrate used as the adherend and the substrate used as the support are not particularly limited, and examples thereof include resin plates, glass plates, woven fabrics, non-woven fabrics, and paper.
  • the resin is preferably a transparent resin, and examples of the transparent resin include polycarbonate (PC), polymethyl methacrylate (PMMA), polyethylene terephthalate (PET), polypropylene (PP), acrylonitrile-butadiene-styrene copolymer ( ABS), polyamide (nylon), and the like.
  • the coating method of the composition a known method such as a spin coating method, a knife coating method, a roll coating method, a bar coating method, a blade coating method, a die coating method, or a gravure coating method can be used to obtain a predetermined pressure-sensitive adhesive layer. and a method of coating so as to have a thickness of .
  • the composition instead of coating, can be placed on the adherend or support by immersing the adherend or support in the composition.
  • the applied (arranging) composition may be dried, if necessary.
  • the drying conditions vary depending on the type of solvent, but are generally 50° C. or higher, preferably 60° C. or higher, generally 150° C. or lower, preferably 100° C. or lower, and generally 1 minute or longer, preferably 2 minutes or longer. Conditions for drying for 10 minutes or less, preferably 7 minutes or less are included.
  • the curing conditions are usually 5° C. or higher, preferably 15° C. or higher, usually 60° C. or lower, preferably 40° C. or lower, usually 5 to 70% RH, preferably 5 to 50% RH.
  • An optical member according to one embodiment of the present invention has the pressure-sensitive adhesive layer.
  • a specific example of the optical member is the laminate.
  • a liquid crystal display device including a laminate in which a polarizing plate, the present pressure-sensitive adhesive layer, a liquid crystal panel, the present pressure-sensitive adhesive layer, and a polarizing plate are laminated in this order
  • a touch panel includes a laminate in which a shatterproof film, the present pressure-sensitive adhesive layer, an ITO layer, and a glass panel are laminated in this order.
  • GPC gel permeation chromatography
  • the acid value (mgKOH/g) of each polymer refers to the amount (mg) of potassium hydroxide required to neutralize 1 g of polymer.
  • the measurement method is as follows. First, a measurement sample was prepared by adding 50 mL of a toluene/ethanol (volume ratio: 2/1) mixed solution to a sample of about 1 g of polymer and dissolving it. Next, the measurement sample is subjected to potentiometric titration with a 0.1 N potassium hydroxide ethanol solution using an automatic titrator (AUT-501, manufactured by Toa DKK Co., Ltd.). Necessary for neutralizing the measurement sample amount of potassium hydroxide ethanol solution was measured.
  • the acid value was calculated by the following formula (I).
  • Formula (I): Acid value (mgKOH/g) (B x f x 5.611)/S B: Amount (mL) of 0.1N potassium hydroxide ethanol solution used for titration f: factor of 0.1N potassium hydroxide ethanol solution S: mass (g) of solid content of measurement sample
  • Example 1 The polymer solution of the polymer (A-1) obtained in Production Example A-1 was mixed with the polymer solution of the polymer (B-1) obtained in Production Example B-1 to obtain a polymer mixture.
  • the blending amount of the polymer (B-1) is 60 parts by mass of the polymer (B-1) with respect to 100 parts by mass of the polymer (A-1) in the polymer solution obtained in Production Example A-1. is the amount.
  • an isocyanate curing agent L-45 manufactured by Soken Chemical Co., Ltd.
  • the amount of L-45 is such that the solid content of L-45 is 12 parts by mass with respect to the total of 100 parts by mass of polymer (A-1) and polymer (B-1).
  • Examples 2 to 36 and Comparative Examples 1 to 11 A pressure-sensitive adhesive composition was obtained in the same manner as in Example 1, except that the formulation composition was changed as shown in Tables 1 to 3.
  • the added amount [parts by mass] in Tables 1 to 3 is the added amount of the polymer (B) or the polymer for comparison of the polymer (B) with respect to 100 parts by mass of the polymer (A) or the polymer for comparison of the polymer (A). is.
  • the numerical values in the columns of each curing agent, silane coupling agent, and antistatic agent are polymer (A) (or polymer for comparison of polymer (A)) and polymer (B) (or polymer (B) for comparison).
  • the amount (parts by mass) of the solid content of each of these components added to a total of 100 parts by mass with the polymer) is shown.
  • the pressure-sensitive adhesive layer-attached polarizing plate thus prepared was cut into a size of 150 mm ⁇ 250 mm, the PET film was peeled off, and the plate was adhered to a glass plate having a thickness of 1.1 mm and pressure-bonded.
  • the glass plate to which the pressure-sensitive adhesive layer-attached polarizing plate was attached was autoclaved under conditions of 50° C. and 5 atm for 20 minutes, and then left in an environment of 23° C./50% RH for 24 hours.
  • ⁇ Light leakage test> The pressure-sensitive adhesive layer-attached polarizing plate having the PET film produced as described above was cut into 150 mm ⁇ 250 mm, the PET film was peeled off, and the polarizing axes were perpendicular to each other.
  • a laminated body for a light leakage test was produced by crimping. The produced laminate for light leakage test was autoclaved under conditions of 50° C. and 5 atm for 20 minutes, and then left in an environment of 80° C. for 500 hours. The obtained laminate for light leakage test was irradiated with light from a backlight of a liquid crystal monitor, and the state of light leakage at that time was visually evaluated according to the following criteria. (Evaluation criteria) A: No light leakage is observed. ⁇ : Light leakage is slightly observed, but it is practically no problem. ⁇ : Light leakage is observed, and there is a possibility that a practical problem will occur. x: Significant light leakage is observed.
  • ⁇ Adhesion test> The pressure-sensitive adhesive layer-attached polarizing plate having the PET film produced as described above was cut to a width of 25 mm, the release-treated PET film was peeled off, and the plate was laminated to a glass plate in an environment of 23°C/50% RH, Autoclave treatment was performed for 20 minutes under conditions of 50° C. and 5 atm. After that, it was taken out in an environment of 23° C./50% RH and allowed to stand still for 1 hour, and the adhesive force was measured when the polarizing plate with an adhesive layer was peeled off from the glass plate at a peeling angle of 180° and a tensile speed of 300 mm/min. did.
  • the PET film of the adhesive layer-attached polarizing plate having the PET film prepared as described above was peeled off, and an ITO vapor deposition film cut to 10 mm ⁇ 60 mm was pasted on the adhesive layer, and the pressure was applied at 50°C and 5 atm for 20 minutes. It was autoclaved. Then, it was left under an environment of 23° C./50% RH for 1 hour, and then left under an environment of 60° C./90% RH for 500 hours. Then, after being left for 1 hour in an environment of 23° C./50% RH, the resistance value of the ITO deposited film (resistance value after the test) was measured.
  • the rate of change in the resistance value after the test with respect to the resistance value before the test was obtained. was evaluated according to the criteria of Here, since the change in the resistance value is considered to be caused by corrosion of ITO, it is determined that there is ITO corrosiveness when the rate of change exceeds 120%, and ITO corrosion when the rate of change is 120% or less. determined to be non-sexual. A tester (manufactured by Sanwa Electric Instrument Co., Ltd., digital multimeter PC510) was used to measure the resistance value.
  • the pressure-sensitive adhesive layer in each example had appropriate adhesive strength, and was excellent in durability and corrosion resistance under high-temperature and high-humidity environments.
  • Comparative Examples 1 and 2 using polymer (A) and polymer (B) with oxidation exceeding 1.0 mg KOH / g had insufficient high temperature durability, wet heat durability and corrosiveness. rice field.
  • Comparative Examples 3 and 4 using a polymer (B) containing more than 0.05% by mass of structural units derived from a hydroxyl group-containing monomer or an amino group-containing monomer as a constituent show high temperature durability and wet heat durability. was insufficient.
  • Comparative Examples 9 and 10 in which the content of the curing agent (C) is 6 parts by mass or less or 30 parts by mass or more with respect to a total of 100 parts by mass of the polymer (A) and the polymer (B), are excellent in high temperature durability and The wet heat durability was insufficient.
  • Comparative Example 11 using the polymer (A) in which the structural units derived from the hydroxyl group-containing monomer and the amino group-containing monomer are 0% by mass as the constituent components has poor high temperature durability, wet heat durability, reworkability, and light leakage prevention performance. was enough.

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Abstract

Un mode de réalisation de la présente invention concerne une composition d'agent adhésif, une feuille adhésive ou un élément optique. La composition d'agent adhésif contient : un polymère acrylique (A) qui contient plus de 0 % en masse mais pas plus de 0,4 % en masse de motifs constitutifs dérivés d'un monomère contenant un groupe hydroxyle et d'un monomère contenant un groupe amino, tout en présentant un indice d'acide inférieur ou égal à 1,0 mg de KOH/g et une Mw supérieure ou égale à 600 000 ; un polymère acrylique (B) qui contient une proportion inférieure ou égale à 0,05 % en masse de motifs constitutifs dérivés d'un monomère contenant un groupe hydroxyle et d'un monomère contenant un groupe amino, tout en présentant un indice d'acide inférieur ou égal à 1,0 mg de KOH/g et une Mw supérieure à 250 000 mais inférieure à la Mw du constituant (A) ; et un agent de durcissement à base d'isocyanate (C). Dans cette composition d'agent adhésif sont présentes au moins 10 parties en masse du constituant (B) par rapport aux 100 parties en masse du constituant (A) ; et plus de 6 parties en masse mais moins de 30 parties en masse du constituant (C) par rapport à un total de 100 parties en masse des constituants (A) et (B).
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JP2015025080A (ja) * 2013-07-26 2015-02-05 日本カーバイド工業株式会社 粘着剤組成物及び光学機能性フィルム
JP2016188310A (ja) * 2015-03-30 2016-11-04 日本カーバイド工業株式会社 粘着剤組成物及び粘着シート
JP2017160383A (ja) * 2016-03-11 2017-09-14 日本カーバイド工業株式会社 粘着剤組成物及び粘着シート

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WO2024095957A1 (fr) * 2022-10-31 2024-05-10 三菱ケミカル株式会社 Composition à teneur en composé ester ainsi que procédé de fabrication de celle-ci, composition polymérisable, polymère (méth)acrylique ainsi que procédé de fabrication de celui-ci

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