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WO2025063181A1 - Composition adhésive, feuille adhésive, stratifié et afficheur comprenant ledit stratifié - Google Patents

Composition adhésive, feuille adhésive, stratifié et afficheur comprenant ledit stratifié Download PDF

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Publication number
WO2025063181A1
WO2025063181A1 PCT/JP2024/033159 JP2024033159W WO2025063181A1 WO 2025063181 A1 WO2025063181 A1 WO 2025063181A1 JP 2024033159 W JP2024033159 W JP 2024033159W WO 2025063181 A1 WO2025063181 A1 WO 2025063181A1
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WO
WIPO (PCT)
Prior art keywords
mass
parts
monomer
content
pressure
Prior art date
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Application number
PCT/JP2024/033159
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English (en)
Japanese (ja)
Inventor
寛之 古野
洋平 金塚
岳 柏村
好映 柿沼
明日香 濱口
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Toyochem Co Ltd
Artience Co Ltd
Original Assignee
Toyochem Co Ltd
Artience Co Ltd
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Publication of WO2025063181A1 publication Critical patent/WO2025063181A1/fr
Pending legal-status Critical Current
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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements

Definitions

  • the present disclosure relates to an adhesive composition, an adhesive sheet, a laminate, and a display including the laminate that are suitable for fixing polarizing plates.
  • Display devices such as liquid crystal displays used in a variety of devices, including electronic calculators, electronic clocks, mobile phones, televisions, and other home and commercial electrical appliances, are becoming larger, with LCD and plasma televisions being particularly notable.
  • touch panel type LCD displays including those used in smartphones and tablets, have rapidly spread in popularity, and this market is expected to continue to expand significantly in the future.
  • LCD displays are also used in in-vehicle devices such as car navigation systems, and they must be durable enough to be used in harsh in-vehicle environments, including high temperature and humidity.
  • LCD displays use polarizing plates and retardation plates with various optical functions, which are attached to substrates such as glass or transparent plastic liquid crystal cells via adhesives.
  • the polarizing plate is generally a laminate in which a polyvinyl alcohol film is sandwiched between a triacetyl cellulose film or a cycloolefin film. These films have different mechanical properties and therefore different rates of dimensional change when heated. Therefore, when placed in a high-temperature atmosphere, the laminate often warps.
  • a liquid crystal cell component consisting of polarizing plate/adhesive layer/glass (glass is the surface component of the liquid crystal cell)
  • problems such as warping due to the dimensional change rate between the components of the polarizing plate, air bubbles (foaming) at the bonding interface between the adhesive layer and the glass, and the polarizing plate lifting off the glass and peeling off may occur.
  • warping can cause the stress distribution in the liquid crystal cell component to become uneven, with stress concentrating on the peripheral edges of the liquid crystal cell component, resulting in a problem known as "light leakage,” in which light leaks from the four corners and peripheral edges of the liquid crystal cell component.
  • the above problems also occur in high-temperature, high-humidity atmospheres.
  • adhesives are generally diluted and adjusted to a low viscosity for convenient coating when creating adhesive sheets.
  • solvent used in adjusting the viscosity it is required to reduce the content as much as possible from the standpoint of cost and handling.
  • the non-volatile content of the adjusted solution is low, it tends to be difficult to apply the adhesive thickly and evenly, so there is a demand for low-viscosity adhesives that can have a higher non-volatile content.
  • Patent Document 1 discloses a technology that enhances stress relaxation properties and prevents light leakage by incorporating an acrylic copolymer that uses an aromatic ring-containing monomer.
  • the adhesive that uses the aromatic ring-containing monomer listed in Patent Document 1 has problems with white spots occurring in light leakage evaluations and poor optical properties.
  • the inventors' investigations revealed that if the non-volatile content was set to 25%, the viscosity would be too high, making coating difficult, and so it was not possible to increase the non-volatile content.
  • Patent Document 2 discloses a technique for blending a low molecular weight acrylic polymer with a high acid value and a weight average molecular weight of 0.2 to 100,000 with a high molecular weight acrylic polymer with a weight average molecular weight of 500,000 or more to impart removability.
  • the adhesive described in Patent Document 2 has a problem in that the drying conditions for the adhesive are limited.
  • Patent Document 3 discloses a technology that uses a block polymer made of two or more monomers to improve durability and adhesive properties under heated and humid conditions.
  • the adhesive described in Patent Document 3 has a problem in that its transmittance decreases under heated and/or humid conditions.
  • Patent Document 4 discloses a technology that uses a water-dispersible adhesive that is less prone to depolarization and also provides reworkability and recyclability, and that contains an acrylic copolymer with a glass transition temperature of -55°C or higher and less than 0°C, and an acrylic copolymer with a glass transition temperature of 0°C or higher and 180°C or lower.
  • the adhesive described in Patent Document 4 has a problem in that it lacks reworkability after being applied for a long period of time due to the various additives used in the adhesive.
  • Patent Document 5 discloses a technology that suppresses peeling in high temperature and high humidity environments by constructing an interpenetrating network structure in the cured state using an acrylic copolymer containing hydroxyl groups and alkylene oxide groups, and a polyfunctional isocyanate curing agent.
  • the adhesive described in Patent Document 5 has the problem that when left in a high temperature and high humidity environment for a long period of time, the alkylene oxide groups decompose, causing peeling and lifting.
  • Patent Document 6 discloses a technology that uses an acrylic copolymer containing hydroxyl and carboxyl groups, a mercapto group-containing silane compound, and alcohol to prevent the adhesive sheet from lifting or peeling when placed in a high-temperature, high-humidity environment for a long period of time.
  • the adhesive described in Patent Document 6 uses a highly volatile silane compound, and so when the adhesive is applied and dried, the silane compound volatilizes, and there is not a sufficient amount of silane compound remaining in the adhesive layer after application, resulting in the problem of lifting and peeling.
  • the problem that the present invention aims to solve is to provide an adhesive composition that has excellent low viscosity when adjusted to a specified non-volatile content, has excellent peelability when used in an adhesive sheet, and is unlikely to lift or peel off from an adherend after exposure to a high temperature environment or a high temperature and high humidity environment, and an adhesive sheet using the same, in order to solve the above problems.
  • the present invention aims to provide an adhesive composition and an adhesive sheet using the same that, when used to fix a polarizing plate, has extremely low light leakage evaluation, has good adhesive strength that can maintain high transparency even when exposed to a high temperature and high humidity environment, and does not contaminate adherends such as glass.
  • the present invention relates to a pressure-sensitive adhesive composition
  • a pressure-sensitive adhesive composition comprising an acrylic polymer (A) and a curing agent (B), wherein the acrylic polymer (A) is a copolymer of a monomer mixture comprising the following monomers (a1), (a2), (a3), and (a4), and other monomers, and wherein the pressure-sensitive adhesive composition satisfies the following formula (1), wherein the content of (a2) is 40 to 95 parts by mass in 100 parts by mass of the monomer mixture, the content of (a3) is 10 parts by mass or less in 100 parts by mass of the monomer mixture, the content of (a4) is 0.1 to 20 parts by mass in 100 parts by mass of the monomer mixture, the content of the other monomers is 15 parts by mass or less in 100 parts by mass of the monomer mixture, the amount of the curing agent (B) added is 0.01 to 5 parts by mass relative to 100 parts by mass of the acrylic polymer (A),
  • the present disclosure also provides a pressure-sensitive adhesive composition
  • a pressure-sensitive adhesive composition comprising an acrylic polymer (A) and a curing agent (B), wherein the acrylic polymer (A) is a copolymer of a monomer mixture comprising the following monomers (a1), (a2), (a3), and (a4), and other monomers, and satisfies the following formula (1), the content of (a2) is 40 to 95 parts by mass in 100 parts by mass of the monomer mixture, the content of (a3) is 10 parts by mass or less in 100 parts by mass of the monomer mixture, the content of (a4) is 0.1 to 20 parts by mass in 100 parts by mass of the monomer mixture, and the content of the other monomers is 0.1 to 20 parts by mass in 100 parts by mass of the monomer mixture.
  • the acrylic polymer (A) is a copolymer of a monomer mixture comprising the following monomers (a1), (a2), (a3), and (a4), and other monomers, and satis
  • the content of isobornyl (meth)acrylate in 100 parts by mass of the monomer mixture is 15 parts by mass or less, and when isobornyl (meth)acrylate is contained as monomer (a1) and a nitrogen-containing monomer is contained as other monomer, the content of at least one of isobornyl (meth)acrylate, the nitrogen-containing monomer and monomer (a4) in 100 parts by mass of the monomer mixture is less than 10 parts by mass, the amount of curing agent (B) added is 0.01 to 5 parts by mass relative to 100 parts by mass of acrylic polymer (A), and the gel fraction of the pressure-sensitive adhesive layer made of the pressure-sensitive adhesive composition is 55 to 90%.
  • the present disclosure also provides a pressure-sensitive adhesive composition
  • a pressure-sensitive adhesive composition comprising an acrylic polymer (A) and a curing agent (B), wherein the acrylic polymer (A) is a copolymer of a monomer mixture comprising the following monomers (a1), (a2), (a3), and (a4), and other monomers, and satisfies the following formula (1), in which the content of (a2) is 40 to 95 parts by mass in 100 parts by mass of the monomer mixture, the content of (a3) is 10 parts by mass or less in 100 parts by mass of the monomer mixture, and the content of (a4) is 10 parts by mass or less in 100 parts by mass of the monomer mixture.
  • the content of the other monomer is 15 parts by mass or less in 100 parts by mass of the monomer mixture; when a nitrogen-containing monomer is contained as the other monomer, the content of at least one of the nitrogen-containing monomer and the monomer (a4) in 100 parts by mass of the monomer mixture is less than 10 parts by mass; the amount of the curing agent (B) added is 0.01 to 5 parts by mass relative to 100 parts by mass of the acrylic polymer (A); and the gel fraction of the pressure-sensitive adhesive layer made of the pressure-sensitive adhesive composition is 55 to 90%.
  • (a1) A (meth)acrylic acid ester monomer having no functional group and having a glass transition temperature of a homopolymer of 0° C. or higher.
  • the present disclosure also relates to the pressure-sensitive adhesive composition, in which the content of monomer (a4) is 0.1 to 5 parts by mass per 100 parts by mass of the monomer mixture.
  • the present disclosure also relates to the pressure-sensitive adhesive composition in which the curing agent (B) contains an isocyanate-based curing agent.
  • the present disclosure also relates to the pressure-sensitive adhesive composition further comprising an organosilane (C).
  • the present disclosure also relates to the pressure-sensitive adhesive composition, in which the content of the monomer (a3) having a carboxy group in 100 parts by mass of the monomer mixture constituting the acrylic polymer (A) is 10 parts by mass or less.
  • the present disclosure also relates to the pressure-sensitive adhesive composition used for fixing polarizing plates.
  • the present disclosure also relates to an adhesive sheet having an adhesive layer made of the adhesive composition.
  • the present disclosure also relates to a laminate comprising a pressure-sensitive adhesive layer made of the pressure-sensitive adhesive composition and a light-transmitting substrate.
  • the present disclosure also relates to a polarizing plate with an adhesive layer that includes an adhesive layer made of the adhesive composition.
  • the present disclosure also relates to a display comprising a pressure-sensitive adhesive layer made of the pressure-sensitive adhesive composition, a light-transmitting substrate, a polarizing plate, and an optical element.
  • the present disclosure makes it possible to provide an adhesive composition that has excellent low viscosity when adjusted to a specified non-volatile content, has excellent removability when used in an adhesive sheet, and is unlikely to lift or peel off from adherends, such as glass or plastics, after exposure to high temperature or high temperature/high humidity environments, and is unlikely to cause light leakage.
  • FIG. 1 is a schematic cross-sectional view partially illustrating an example of a laminate according to the present disclosure.
  • FIG. 1 is a schematic cross-sectional view partially illustrating a display, which is an example of the use of an example of a laminate according to the present disclosure.
  • 1 is a schematic cross-sectional view partially illustrating an example of a pressure-sensitive adhesive sheet according to the present disclosure.
  • (meth)acrylic acid ester includes acrylic acid ester and methacrylic acid ester
  • (meth)acryloxy group includes acryloxy group and methacryloxy group.
  • monomer refers to a monomer having an ethylenically unsaturated group.
  • a numerical range specified by using “to” includes the numerical values written before and after "to” as the range of the lower and upper limits.
  • film and “sheet” are not distinguished by thickness.
  • a "sheet” includes a thin film-like material
  • a "film” includes a thick sheet-like material
  • the adherend refers to a counterpart to which the pressure-sensitive adhesive layer of the pressure-sensitive adhesive sheet is attached.
  • the various components appearing in this specification may be used independently as a single type or as a combination of two or more types.
  • the pressure-sensitive adhesive composition of the present disclosure contains an acrylic polymer (A) and a curing agent (B).
  • the acrylic polymer (A) is a copolymer of a monomer mixture containing the monomer (a1) and the monomer (a2) described below.
  • the monomer (a1) is a (meth)acrylate monomer having no functional group and having a glass transition temperature of 0° C. or higher as a homopolymer.
  • the glass transition temperature (° C.) of a homopolymer can be obtained from information provided by the vendor of each monomer, or from values listed in "Polymer Handbook 3rd Edition" (A WILEY-INTERSCIENCE PUBLICATION, 1989).
  • Examples of monomer (a1) include methyl (meth)acrylate, ethyl methacrylate, tert-butyl methacrylate, sec-butyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, isopropyl methacrylate, stearyl (meth)acrylate, isobornyl (meth)acrylate, cyclohexyl (meth)acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, and phenyl (meth)acrylate.
  • the monomer (a1) is preferably at least one selected from the group consisting of methyl (meth)acrylate, ethyl methacrylate, isobornyl (meth)acrylate, cyclohexyl (meth)acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, and phenyl (meth)acrylate.
  • the acrylic polymer (A) satisfies the following formula (1).
  • MA Content (parts by mass) of (a1) in 100 parts by mass of monomer mixture
  • the lower limit of formula (1) is preferably 3900, and more preferably 7100.
  • the upper limit of formula (1) is preferably 32000, and more preferably 24000.
  • the monomer (a2) is 2-octyl (meth)acrylate. Since the monomer (a2) is available as a biologically derived material, the ratio of the biologically derived material can be increased by using the monomer (a2). In addition, the flexibility of the adhesive layer is improved, the adhesion of the adhesive layer to the substrate is further improved, and lifting and peeling can be further suppressed when exposed to a high temperature atmosphere or a high temperature and high humidity atmosphere.
  • the viscosity tends to be lower than that of a polymer not containing the monomer (a2) of the same molecular weight, and even if the adhesive composition has a high non-volatile content, the viscosity does not increase too much and the adhesive composition is easy to handle.
  • the content of monomer (a2) is 40 to 95 parts by mass per 100 parts by mass of the monomer mixture. It is preferably 50 to 95 parts by mass, more preferably 60 to 90 parts by mass, and most preferably 70 to 85 parts by mass.
  • the monomer mixture constituting the acrylic polymer (A) may further contain a monomer having a carboxy group as the monomer (a3).
  • the content of (a3) is 10 parts by mass or less in 100 parts by mass of the monomer mixture, preferably 5 parts by mass or less, more preferably less than 0.5 parts by mass, and most preferably 0.1 parts by mass or less.
  • the monomer (a3) having a carboxy group is not limited as long as it has a carboxy group in the molecule, and specific examples include (meth)acrylic acid, p-carboxybenzyl acrylate, ⁇ -carboxyethyl acrylate, maleic acid, monoethyl maleic acid, itaconic acid, citraconic acid, fumaric acid, etc.
  • (meth)acrylic acid is preferred from the viewpoint of adhesive strength, and acrylic acid is more preferred.
  • the monomer mixture constituting the acrylic polymer (A) further contains a monomer having a hydroxy group as the monomer (a4).
  • a monomer having a hydroxy group By containing a monomer having a hydroxy group, the viscosity increase of the pressure-sensitive adhesive can be suppressed, and it becomes easy to achieve both adhesion and durability when exposed to a high temperature atmosphere or a high temperature and high humidity atmosphere.
  • the monomer having a hydroxy group (a4) is not limited as long as it is a monomer having a hydroxy group in the molecule, and specifically includes 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, etc., and these can be used alone or in combination of two or more kinds.
  • the average number of carbon atoms in the alkyl chain of the monomer (a4) having a hydroxy group is preferably 2.5 or more, and more preferably 3 or more.
  • the content of the hydroxyl group-containing monomer (a4) is 0.1 to 20 parts by mass, preferably 0.1 to 5 parts by mass, and most preferably 0.2 to 1.5 parts by mass, per 100 parts by mass of the monomer mixture.
  • the monomer mixture constituting the acrylic polymer (A) contains other monomers in addition to the above (a1) to (a4).
  • Examples include (meth)acrylic acid ester monomers having no functional group and having a homopolymer glass transition temperature (Tg) of less than 0° C.
  • nitrogen atom-containing monomer examples include N-vinyl lactams, cyclic amides such as vinylpyridine, vinylpyrimidine, vinylpiperazine, vinylpyrazine, vinylpyrrole, vinylimidazole, vinyloxazole, vinylmorpholine, and (meth)acryloylmorpholine, N-vinyl carboxylic acid amides such as N-vinylformamide and N-vinylacetamide, acrylonitrile, acrylamide, N,N-dimethylacrylamide, etc.
  • N-vinyl lactams examples include N-vinyl lactams, cyclic amides such as vinylpyridine, vinylpyrimidine, vinylpiperazine, vinylpyrazine, vinylpyrrole, vinylimidazole, vinyloxazole, vinylmorpholine, and (meth)acryloylmorpholine, N-vinyl carboxylic acid amides such as N-vinylformamide and N-vinylacetamide, acrylonit
  • N-vinyl lactams are monomers having a cyclic lactam ring, and examples thereof include N-vinyl-2-pyrrolidone, N-vinyl-2-piperidone, N-vinyl- ⁇ -caprolactam, and compounds having a structure in which one or more of the hydrogen atoms of these are substituted with a substituent.
  • substituents examples include an alkyl group having 1 to 20 carbon atoms, an alkyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a carboxy ester group having 3 to 20 carbon atoms, and an amino group having 1 to 20 carbon atoms, but do not include acidic groups such as a hydroxy group, a carboxylic acid (salt) group, a sulfonic acid (salt) group, or a hypophosphorous acid (salt) group.
  • acidic groups such as a hydroxy group, a carboxylic acid (salt) group, a sulfonic acid (salt) group, or a hypophosphorous acid (salt) group.
  • cyclic amides and N-vinyl lactams are preferred, and N-vinyl lactams are more preferred.
  • the content of other monomers is 15 parts by mass or less per 100 parts by mass of the monomer mixture. It is preferably 10 parts by mass or less, and most preferably 5 parts by mass or less.
  • the content of at least one of isobornyl (meth)acrylate, the nitrogen-containing monomer, and monomer (a4) is less than 10 parts by mass per 100 parts by mass of the monomer mixture. If the content of isobornyl (meth)acrylate, the nitrogen-containing monomer, or monomer (a4) is high, the cohesive strength becomes too high and the adhesive strength decreases, so it is important that the content of at least one of the above three types is less than 10 parts by mass.
  • the content of at least one of the nitrogen-containing monomer and monomer (a4) is less than 10 parts by mass per 100 parts by mass of the monomer mixture. If the content of the nitrogen-containing monomer and monomer (a4) is high, the cohesive strength becomes too high, resulting in a decrease in adhesive strength, so it is important that the content of at least one of them is less than 10 parts by mass.
  • the acrylic polymer (A) can be produced by polymerizing the monomer mixture.
  • the polymerization can be carried out by known polymerization methods such as solution polymerization, bulk polymerization, emulsion polymerization, and suspension polymerization, but solution polymerization is preferred.
  • the solvent used in the solution polymerization is preferably, for example, acetone, methyl acetate, ethyl acetate, toluene, xylene, anisole, methyl ethyl ketone, cyclohexanone, etc.
  • the polymerization temperature is preferably a boiling point reaction at 60 to 120°C.
  • the polymerization time is preferably about 5 to 12 hours.
  • the polymerization initiator used in the polymerization is preferably a radical polymerization initiator, and the radical polymerization initiator is generally a peroxide or an azo compound.
  • the peroxide include dialkyl peroxides such as di-t-butyl peroxide, dicumyl peroxide, t-butylcumyl peroxide, ⁇ , ⁇ '-bis(t-butylperoxy-m-isopropyl)benzene, and 2,5-di(t-butylperoxy)hexyne-3; Peroxyesters such as t-butyl peroxybenzoate, t-butyl peroxyacetate, and 2,5-dimethyl-2,5-di(benzoylperoxy)hexane; ketone peroxides such as cyclohexanone peroxide, 3,3,5-trimethylcyclohexanone peroxide, and methylcyclohexanone peroxide; Peroxyketals such as 2,
  • Examples of the azo compound include 2,2'-azobisbutyronitrile such as 2,2'-azobisisobutyronitrile (abbreviation: AIBN) and 2,2'-azobis(2-methylbutyronitrile); 2,2'-azobisvaleronitrile such as 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile) and 2,2'-azobis(2,4-dimethylvaleronitrile); 2,2'-azobispropionitrile such as 2,2'-azobis(2-hydroxymethylpropionitrile); Examples of the compound include 1,1'-azobis-1-alkanenitriles such as 1,1'-azobis(cyclohexane-1-carbonitrile).
  • the polymerization initiator is preferably used in an amount of 0.01 to 10 parts by mass, more preferably 0.1 to 2 parts by mass, per 100 parts by mass of the monomer mixture.
  • the weight average molecular weight of the acrylic polymer (A) is preferably 800,000 to 1,800,000, more preferably 1,000,000 to 1,700,000. By setting the weight average molecular weight within the above range, it becomes easier to ensure adhesion to optical members, removability, and durability when exposed to a high temperature atmosphere.
  • the weight average molecular weight is a value calculated in terms of polystyrene measured by gel permeation chromatography (GPC).
  • the pressure-sensitive adhesive composition of the present disclosure contains 0.01 to 5 parts by mass of the curing agent (B) relative to 100 parts by mass of the acrylic polymer (A).
  • the curing agent to be blended in the pressure-sensitive adhesive composition is preferably one that reacts with the carboxy group of the monomer (a3) and/or the hydroxy group of the monomer (a4) by heat or the like to form a bond. Blending the curing agent in the above ratio improves the cohesive strength of the pressure-sensitive adhesive layer, and can achieve both adhesion to optical members, removability, and durability when exposed to a high-temperature atmosphere or a high-temperature, high-humidity atmosphere.
  • the blending amount of the curing agent (B) is preferably 0.1 to 2 parts by mass relative to 100 parts by mass of the acrylic polymer (A).
  • one or more types can be appropriately selected from known curing agents such as epoxy-based curing agents, isocyanate-based curing agents, oxazoline-based curing agents, aziridine-based curing agents, carbodiimide-based curing agents, metal chelate-based curing agents, and melamine-based curing agents, taking into consideration the reactivity with the functional groups of the polymer in the adhesive composition, but it is preferable to include an isocyanate-based curing agent from the viewpoint of removability.
  • known curing agents such as epoxy-based curing agents, isocyanate-based curing agents, oxazoline-based curing agents, aziridine-based curing agents, carbodiimide-based curing agents, metal chelate-based curing agents, and melamine-based curing agents, taking into consideration the reactivity with the functional groups of the polymer in the adhesive composition, but it is preferable to include an isocyanate-based curing agent from the viewpoint of removability.
  • Epoxy curing agents include, for example, N,N,N',N'-tetraglycidyl-m-xylylenediamine, tetraglycidyl-3,3'-diaminodiphenylsulfone, tetraglycidyldiaminodiphenylmethane, 1,3-bis(N,N'-diglycidylaminomethyl)cyclohexane, N,N,N',N'-tetraglycidylaminophenylmethane (all of which are examples of tetrafunctional epoxy compounds), glycerin diglycidyl ether, 1,6-hexanediol diglycidyl ether, etc., and one or more of these can be selected as appropriate.
  • the isocyanate-based curing agent is an isocyanate having two or more isocyanate groups.
  • isocyanates that are preferred include aromatic polyisocyanates, aliphatic polyisocyanates, araliphatic polyisocyanates, alicyclic polyisocyanates, and their biuret forms, nurate forms, and adduct forms. From the viewpoint of yellowing resistance, aliphatic polyisocyanates, alicyclic polyisocyanates, and their biuret forms, nurate forms, and adduct forms are even more preferred.
  • the biuret compound is a self-condensation product having a biuret bond formed by the self-condensation of an isocyanate monomer.
  • An example of the biuret compound is the biuret compound of hexamethylene diisocyanate.
  • the adduct is a bifunctional or higher isocyanate compound formed by reacting an isocyanate monomer with a bifunctional or higher low-molecular-weight active hydrogen-containing compound.
  • examples of the adduct include a compound formed by reacting trimethylolpropane with hexamethylene diisocyanate, a compound formed by reacting trimethylolpropane with tolylene diisocyanate, a compound formed by reacting trimethylolpropane with xylylene diisocyanate, a compound formed by reacting trimethylolpropane with isophorone diisocyanate, and a compound formed by reacting 1,6-hexanediol with hexamethylene diisocyanate.
  • the isocyanate compound is preferably a trifunctional isocyanate compound from the viewpoint of forming a sufficient crosslinked structure.
  • the isocyanate compound is more preferably an adduct which is a reaction product between an isocyanate monomer and a trifunctional low-molecular active hydrogen-containing compound, or a nurate.
  • the isocyanate compound is preferably a trimethylolpropane adduct of hexamethylene diisocyanate, a nurate of hexamethylene diisocyanate, a trimethylolpropane adduct of tolylene diisocyanate, a nurate of tolylene diisocyanate, a trimethylolpropane adduct of isophorone diisocyanate, or a nurate of isophorone diisocyanate, and more preferably a trimethylolpropane adduct of hexamethylene diisocyanate, a trimethylolpropane adduct of tolylene diisocyanate, or a trimethylolpropane adduct of isophorone diisocyanate.
  • Oxazoline-based hardeners have two or more oxazoline groups in the molecule and may be low molecular weight compounds or polymers.
  • low molecular weight compounds of oxazoline-based hardeners include 2-vinyl-2-oxazoline, 2-vinyl-4-methyl-2-oxazoline, 2-vinyl-5-methyl-2-oxazoline, 2-isopropenyl-2-oxazoline, 2-isopropenyl-4-methyl-2-oxazoline, 2-isopropenyl-5-ethyl-2-oxazoline, 2,2'-bis-(2-oxazoline), 2,2'-methylene-bis-(2-oxazoline), 2,2'-ethylene-bis-(2-oxazoline), 2,2'-trimethylene-bis-(2-oxazoline), and 2,2'-tetramethylene-bis-(2-oxazoline).
  • Examples of the oxazoline-based curing agent of a polymer include a polymer having an addition polymerizable oxazoline as an essential component.
  • Examples of the addition-polymerizable oxazoline include 2-vinyl-2-oxazoline, 2-vinyl-4-methyl-2-oxazoline, 2-vinyl-5-methyl-2-oxazoline, 2-isopropenyl-2-oxazoline, 2-isopropenyl-4-methyl-2-oxazoline, 2-isopropenyl-5-methyl-2-oxazoline, and 2-isopropenyl-5-ethyl-2-oxazoline.
  • aziridine-based curing agents examples include N,N'-diphenylmethane-4,4'-bis(1-aziridinecarboxite), tris-2,4,6-(1-aziridinyl)-1,3,5-triazine, and 4,4'-bis(ethyleneiminocarbonylamino)diphenylmethane.
  • the carbodiimide compound is preferably a high molecular weight polycarbodiimide produced by a decarboxylation condensation reaction of a diisocyanate compound in the presence of a carbodiimide catalyst.
  • the commercially available high molecular weight polycarbodiimide is preferably the Carbodilite series from Nisshinbo Industries. Among these, Carbodilite V-03, 07, and 09 are preferred because of their excellent compatibility with organic solvents.
  • the metal chelate is preferably a coordination compound of a polyvalent metal such as aluminum, iron, copper, zinc, tin, titanium, nickel, antimony, magnesium, vanadium, chromium, or zirconium with acetylacetone or ethyl acetoacetate.
  • a polyvalent metal such as aluminum, iron, copper, zinc, tin, titanium, nickel, antimony, magnesium, vanadium, chromium, or zirconium with acetylacetone or ethyl acetoacetate.
  • the metal chelate include aluminum ethyl acetoacetate diisopropylate, aluminum trisacetylacetonate, aluminum bisethyl acetoacetate monoacetylacetonate, and aluminum alkyl acetoacetate diisopropylate.
  • Typical examples of melamine-based hardeners include fully alkyl etherified melamine resins, methylol group-type melamine resins, and imino group-type melamine resins that contain some imino groups.
  • the pressure-sensitive adhesive composition of the present disclosure preferably contains an organic silane (C).
  • an organic silane (C) By containing the organic silane (C), it becomes easier to achieve both adhesion to optical members, removability, and durability when exposed to a high-temperature atmosphere or a high-temperature, high-humidity atmosphere.
  • the organic silane (C) is preferably contained in an amount of 0.001 to 1 part by mass, more preferably 0.005 to 0.8 parts by mass, per 100 parts by mass of the acrylic polymer (A). By setting the amount within the above range, it becomes easier to achieve both adhesion to optical members, removability, and durability when exposed to a high-temperature atmosphere or a high-temperature, high-humidity atmosphere.
  • Examples of the organic silane (C) include an alkoxysilane compound having a (meth)acryloxy group, an alkoxysilane compound having a vinyl group, an alkoxysilane compound having an amino group, an alkoxysilane compound having a mercapto group, or an alkoxysilane compound having an epoxy group. Of these, an alkoxysilane compound having an epoxy group is preferred.
  • alkoxysilane compounds having an epoxy group such as KBM-403 (3-glycidoxypropyltrimethoxysilane), KBE-403 (3-glycidoxypropyltriethoxysilane), and KBM-303 (2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane) (all manufactured by Shin-Etsu Chemical Co., Ltd.), and other organic amines such as BYK-325N (polyether-modified polymethylalkylsiloxane) (manufactured by BYK Japan KK).
  • the adhesive composition of the present disclosure may also contain other compounds to the extent that the effects of the invention are not impaired.
  • other compounds include chlorinated polyolefins, antistatic agents, silicone oils, tackifier resins, etc.
  • chlorinated polyolefin examples include chlorinated polypropylene, acid-modified chlorinated polypropylene, acrylic-modified chlorinated polypropylene, chlorinated polyethylene, and chlorinated ethylene-vinyl acetate copolymer. From the viewpoints of good compatibility with acrylic polymers and the like and effective reduction in polarity, chlorinated polypropylene and chlorinated ethylene-vinyl acetate copolymer are preferred. Specific examples of commercially available products include Superchlorine 390S (chlorinated polypropylene, chlorine content 36%) and Superchlorine BX (chlorinated EVA, chlorine content 18%) (both manufactured by Nippon Paper Industries Co., Ltd.).
  • antistatic agents examples include inorganic salts, ionic liquids, ionic solids, surfactants, etc. Among these, ionic liquids are preferred. Note that “ionic liquids” are also called room temperature molten salts, and exhibit liquid properties at 25°C.
  • inorganic salts include sodium chloride, potassium chloride, lithium chloride, lithium perchlorate, ammonium chloride, potassium chlorate, aluminum chloride, copper chloride, ferrous chloride, ferric chloride, ammonium sulfate, potassium nitrate, sodium nitrate, sodium carbonate, and sodium thiocyanate.
  • the ionic liquid is a salt of a cation and an anion, and the cation is preferably, for example, an imidazolium ion, a pyridinium ion, an ammonium ion, or the like.
  • ionic liquids containing imidazolium ions include 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, 1,3-dimethylimidazolium bis(trifluoromethylsulfonyl)imide, and 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide.
  • ionic liquids containing pyridinium ions include 1-methylpyridinium bis(trifluoromethylsulfonyl)imide, 1-butylpyridinium bis(trifluoromethylsulfonyl)imide, 1-hexylpyridinium bis(trifluoromethylsulfonyl)imide, 1-octylpyridinium bis(trifluoromethylsulfonyl)imide, 1-hexyl-4-methylpyridinium bis(trifluoromethylsulfonyl)imide, 1-hexyl-4-methylpyridinium hexafluorophosphate, 1-octyl-4-methylpyridinium bis(trifluoromethylsulfonyl)imide, 1-octyl-4-methylpyridinium bis(fluorosulfonyl)imide, 1-methylpyridinium bis(perfluoroethylsulfonyl)imide, and 1-methyl
  • ionic liquids containing ammonium ions include trimethylheptylammonium bis(trifluoromethanesulfonyl)imide, N,N-diethyl-N-methyl-N-propylammonium bis(trifluoromethanesulfonyl)imide, N,N-diethyl-N-methyl-N-pentylammonium bis(trifluoromethanesulfonyl)imide, N,N-diethyl-N-methyl-N-heptylammonium bis(trifluoromethanesulfonyl)imide, and tri-n-butylmethylammonium bistrifluoromethanesulfonimide.
  • ionic liquids whose cations are pyrrolidinium ions, phosphonium ions, sulfonium ions, etc. can be used as appropriate.
  • Ionic solids like ionic liquids, are salts of cations and anions, but they exhibit the properties of a solid at normal pressure and 25°C.
  • Preferred cations are, for example, alkali metal ions, phosphonium ions, pyridinium ions, ammonium ions, etc.
  • Ionic solids containing alkali metal ions include, for example, lithium bisfluorosulfonylimide, lithium bistrifluoromethylsulfonylimide, lithium bispentafluoroethylsulfonylimide, lithium bisheptafluoropropylsulfonylimide, lithium bisnonanefluorobutylsulfonylimide, sodium bisfluorosulfonylimide, sodium bistrifluoromethylsulfonylimide, sodium bispentafluoroethylsulfonylimide, sodium bisheptafluoropropylsulfonylimide, sodium bisnonanefluorobutylsulfonylimide, potassium bisfluorosulfonylimide, potassium bistrifluoromethylsulfonylimide, potassium bispentafluoroethylsulfonylimide, potassium bisheptafluoropropylsulfonylimide
  • ionic solids containing phosphonium ions include tetrabutylphosphonium bisfluorosulfonylimide, tetrabutylphosphonium bistrifluoromethylsulfonylimide, tetrabutylphosphonium bispentafluoroethylsulfonylimide, tetrabutylphosphonium bisheptafluoropropylsulfonylimide, tetrabutylphosphonium bisnonanefluorobutylsulfonylimide, tributylhexadecylphosphonium bisfluorosulfonylimide, tributylhexadecylphosphonium bistrifluoromethylsulfonylimide, tributylhexadecylphosphonium bispentafluoroethylsulfonylimide, tributylhexadecylphosphonium bishepta
  • Examples of ionic solids containing pyridinium ions include 1-hexadecyl-4-methylpyridinium bisfluorosulfonylimide, 1-hexadecyl-4-methylpyridinium bistrifluoromethylsulfonylimide, 1-hexadecyl-4-methylpyridinium bispentafluoroethylsulfonylimide, 1-hexadecyl-4-methylpyridinium bisheptafluoropropylsulfonylimide, and 1-hexadecyl-4-methylpyridinium bisnonanefluorobutylsulfonylimide.
  • ionic solid containing ammonium ions examples include tributylmethyl bistrifluoromethylsulfonylimide, tributylmethyl bispentafluoroethylsulfonylimide, tributylmethyl bisheptafluoropropylsulfonylimide, tributylmethyl bisnonanefluorobutylsulfonylimide, octyltributyl bistrifluoromethylsulfonylimide, octyltributyl bispentafluoroethylsulfonylimide, octyltributyl bisheptafluoropropylsulfonylimide, octyltributyl bisnonanefluorobutylsulfonylimide, tetrabutyl bisfluorosulfonylimide, tetrabutyl bistrifluoromethylsulfonylim
  • Surfactants can be classified into nonionic, anionic, cationic, and amphoteric types.
  • nonionic surfactants include glycerin fatty acid esters, polyoxyalkylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene alkylamines, polyoxyethylene alkylamine fatty acid esters, fatty acid diethanolamides, polyether ester amide types, ethylene oxide-epichlorohydrin types, and polyether ester types.
  • anionic surfactants include alkylsulfonates, alkylbenzenesulfonates, alkylphosphates, and polystyrenesulfonate types.
  • examples of the cationic surfactant include tetraalkylammonium salts, trialkylbenzylammonium salts, and quaternary ammonium base-containing acrylate polymers.
  • amphoteric surfactants include amino acid type amphoteric surfactants such as alkyl betaines and alkyl imidazolium betaines, higher alkyl aminopropionates, and betaine type amphoteric surfactants such as higher alkyl dimethyl betaines and higher alkyl dihydroxyethyl betaines.
  • Antistatic agents can be used alone or in combination of two or more types.
  • the amount is preferably 0.01 to 3 parts by mass, more preferably 0.03 to 2 parts by mass, and even more preferably 0.06 to 1 part by mass, per 100 parts by mass of the acrylic polymer (A).
  • the removability is less likely to decrease when exposed to a high-temperature, high-humidity atmosphere, and the yield when manufacturing the adhesive sheet is improved.
  • silicone oils examples include dimethyl silicone oil, methylphenyl silicone oil, methylhydrogen silicone oil, side-chain type polyether-modified silicone oil, aralkyl-modified silicone oil, fluoroalkyl-modified silicone oil, long-chain alkyl-modified silicone oil, higher fatty acid ester-modified silicone oil, higher fatty acid amide-modified silicone oil, polyether-long-chain alkyl-modified silicone oil-aralkyl-modified silicone oil, phenyl-modified silicone oil, both-end type polyether-modified silicone oil, and polyether-methoxy-modified silicone oil.
  • silicone oil When silicone oil is added, the amount is preferably 1 to 10 parts by mass, and more preferably 1 to 5 parts by mass, per 100 parts by mass of the acrylic polymer (A). Adding an appropriate amount of silicone oil makes it difficult for the removability to decrease when exposed to a high-temperature, high-humidity atmosphere, improving the yield when manufacturing the adhesive sheet.
  • tackifying resin examples include aliphatic petroleum resins, aromatic petroleum resins, synthetic hydrocarbon resins, terpene resins, rosin resins (rosin, polymerized rosin, hydrogenated rosin, and their esters with glycerin, pentaerythritol, etc., resin acid dimers, etc.), and acrylic resins.
  • the amount is preferably 20 parts by mass or less per 100 parts by mass of the acrylic polymer (A), more preferably 15 parts by mass or less, even more preferably 10 parts by mass or less, and most preferably substantially none.
  • Aliphatic petroleum resins include Quinton B170 manufactured by Zeon Corporation, aromatic petroleum resins include Nisseki Neopolymer L-90 manufactured by ENEOS Materials Corporation, aliphatic/aromatic petroleum resins include FTR6100 manufactured by Mitsui Chemicals, Inc., and rosin derivatives include SylvatacRE85 manufactured by Arizona Chemical Company and Superester A-75 manufactured by Arakawa Chemical Industries, Ltd.
  • Examples of synthetic hydrocarbon resins include aliphatic petroleum resins, aromatic petroleum resins, aliphatic/aromatic petroleum resins, hydrogenated petroleum resins, coumarone-indene resins, and phenolic resins.
  • Terpene resins include, for example, ⁇ -pinene resin, ⁇ -pinene resin, dipentene resin, aromatic modified terpene resin, hydrogenated terpene resin, terpene phenol resin, acid modified terpene resin, styrenated terpene resin, and styrene-aliphatic hydrocarbon copolymer resin.
  • rosin-based resins examples include rosin esters, polymerized rosin, hydrogenated rosin, disproportionated rosin, maleic acid modified rosin, fumaric acid modified rosin, rosin phenolic resin, and natural rosin.
  • the viscosity of the pressure-sensitive adhesive composition is not particularly limited, but it is preferable that the viscosity when adjusted to a predetermined non-volatile content according to the weight average molecular weight of the acrylic polymer (A) contained is 7000 mPa ⁇ s or less.
  • the viscosity at 20.0 ⁇ 0.5% nonvolatile content is preferably less than 7000 mPa ⁇ s
  • the viscosity at 25.0 ⁇ 0.5% nonvolatile content is preferably less than 7000 mPa ⁇ s
  • the viscosity at 30.0 ⁇ 0.5% nonvolatile content is preferably less than 7000 mPa ⁇ s.
  • the pressure-sensitive adhesive layer of the present disclosure has a gel fraction of 55 to 90% by mass. 60 to 80% by mass is more preferable. When the gel fraction is 55% by mass or more, the cohesive strength of the pressure-sensitive adhesive composition is improved, a strong pressure-sensitive adhesive layer is obtained, and the pressure-sensitive adhesive layer is less likely to protrude from the edge when folded. When the gel fraction is 55% by mass or more, the cohesive strength of the pressure-sensitive adhesive is improved and a strong pressure-sensitive adhesive layer is obtained, so that lifting and peeling can be suppressed when exposed to a high-temperature atmosphere, and the removability required when reattaching to an optical member can be secured.
  • the gel fraction of a polymer is equal to the degree of crosslinking, and the more crosslinked parts in the polymer, the higher the gel fraction.
  • the gel fraction (amount of crosslinked structure introduced) can be adjusted to a desired range by the method of introducing the crosslinked structure, the type and amount of the crosslinking agent, etc. The method for measuring the gel fraction will be described in detail in the Examples.
  • the pressure-sensitive adhesive sheet includes a pressure-sensitive adhesive layer made of the pressure-sensitive adhesive composition of the present disclosure.
  • the adhesive sheet of the present disclosure preferably has a configuration in which a release film is attached to at least one side of the adhesive layer.
  • the adhesive sheet has either a configuration in which a release film is formed on both sides of the adhesive layer, or a configuration in which a release film is formed on one side of the adhesive layer and a light-transmitting substrate is provided on the other side of the adhesive, and the adhesive layer is an adhesive layer formed from the adhesive composition of the present disclosure.
  • the release film is not particularly limited, but a transparent plastic substrate can be suitably used.
  • a transparent plastic substrate can be suitably used.
  • the material of the transparent plastic substrate include polyesters such as polyethylene terephthalate (PET), acrylic resins such as polymethyl methacrylate (PMMA), polycarbonate, triacetyl cellulose, polysulfone, polyarylate, polycycloolefin, and other plastic materials.
  • PET polyethylene terephthalate
  • PMMA polymethyl methacrylate
  • PMMA polymethyl methacrylate
  • polycarbonate triacetyl cellulose
  • polysulfone polysulfone
  • polyarylate polycycloolefin
  • polycycloolefin polycycloolefin
  • a transparent plastic substrate with excellent heat resistance i.e., a transparent plastic substrate in which deformation is suppressed or prevented under harsh conditions such as high temperature or high temperature and high humidity
  • PET film or sheet is particularly suitable as a transparent plastic substrate.
  • the thickness of the transparent plastic substrate is not particularly limited, but is preferably 10 to 200 ⁇ m, and more preferably 25 to 150 ⁇ m, for example.
  • the adhesive sheet of the present disclosure has adhesion to optical components, removability, and durability when exposed to high temperature or high temperature/high humidity atmospheres, and is therefore suitable as an adhesive for forming optical display components such as displays such as LCDs and OLEDs and input devices such as touch panels, and for bonding these components together; however, since it has excellent durability in high temperature/high humidity environments when attached to a polarizing plate, it is preferable that at least one side of the adhesive layer is attached to a polarizing plate.
  • optical components include, but are not limited to, PET films, COP films, polarizing plates, retardation plates, elliptical polarizing plates, optical compensation films, brightness-enhancing films, infrared/electromagnetic wave-cutting films, front-face anti-reflection films, surface protection films, films having an ITO (indium tin oxide) layer, films having a zinc oxide (ZnO) layer, films obtained by coating or printing metal nanoparticles, films obtained by coating or printing a dispersion containing carbon nanotubes, films obtained by coating or printing a dispersion containing graphene, films obtained by coating or printing a dispersion containing a conductive polymer, metal plates made of SUS or the like, metal meshes, and laminates of these.
  • ITO indium tin oxide
  • ZnO zinc oxide
  • the viscosity can be adjusted by adding an appropriate liquid medium.
  • liquid medium include hydrocarbon solvents such as toluene, xylene, hexane, and heptane; ester solvents such as ethyl acetate and butyl acetate; ketone solvents such as acetone and methyl ethyl ketone; halogenated hydrocarbon solvents such as dichloromethane and chloroform; ether solvents such as diethyl ether, methoxytoluene, and dioxane, and other hydrocarbon solvents.
  • water and alcohol must be used with caution, as they may inhibit the reaction between the acrylic polymer (A) and the isocyanate curing agent (B).
  • coating method there are no particular limitations on the coating method, and various coating methods can be used, such as with a Mayer bar, applicator, brush, spray, roller, gravure coater, die coater, lip coater, comma coater, knife coater, reverse coater, and spin coater.
  • drying and curing method there are also no particular limitations on the drying and curing method, and examples include hot air drying, infrared rays, reduced pressure methods, and methods using active energy rays, but from the perspective of outgassing resistance, hot air or steam heating at 60 to 180°C is preferred.
  • the thickness of the adhesive layer is preferably 2 to 1000 ⁇ m, more preferably 5 to 500 ⁇ m, even more preferably 10 to 100 ⁇ m, and most preferably 20 to 50 ⁇ m.
  • the adhesive layer may be in the form of a single layer or a laminate of two or more layers.
  • the laminate includes a light-transmitting substrate and a pressure-sensitive adhesive layer, and the pressure-sensitive adhesive layer is formed using the pressure-sensitive adhesive sheet of the present disclosure.
  • the laminate can be formed by peeling off the release film from the pressure-sensitive adhesive sheet of the present disclosure and attaching the pressure-sensitive adhesive layer to the light-transmitting substrate.
  • a transparent plastic substrate is used as the light-transmitting substrate.
  • the material of such a light-transmitting substrate include acrylic resins such as polyethylene terephthalate (PET), polyethylene naphthalate, and polymethyl methacrylate (PMMA), and plastic materials such as polycarbonate (PC), polycycloolefin (COP), polyimide, polyphenylene ether, polysulfone, polyethersulfone, polystyrene, and polypropylene.
  • PET film or PC is preferred, and PC is even more preferred in terms of durability.
  • the plastic materials can be used alone or in combination of two or more kinds.
  • the light-transmitting substrate may be subjected to an appropriate surface treatment, for example, a physical treatment such as a corona discharge treatment or a plasma treatment, or a chemical treatment such as an undercoat treatment.
  • the polarizing plate with a pressure-sensitive adhesive layer includes a polarizing plate and a pressure-sensitive adhesive layer, and the pressure-sensitive adhesive layer is formed by using the pressure-sensitive adhesive sheet of the present disclosure.
  • the polarizing plate with a pressure-sensitive adhesive layer can be formed by peeling the release film from the pressure-sensitive adhesive sheet of the present disclosure and attaching the pressure-sensitive adhesive layer to the polarizing plate.
  • FIG. 1 shows an example of a schematic cross-sectional view partially illustrating the laminate of the present disclosure.
  • 3 is a light-transmitting substrate (cover panel)
  • 1 is an adhesive layer
  • 4 is a polarizing plate.
  • the light-transmitting substrate (cover panel) is attached to the polarizing plate via an adhesive layer.
  • the light-transmitting substrate (cover panel) is attached to the polarizing plate via an adhesive layer.
  • FIG. 3 shows a schematic cross-sectional view partially illustrating an example of the adhesive sheet of the present disclosure.
  • 3 is a light-transmitting substrate (cover panel)
  • 1 is an adhesive layer
  • 2 is a release film.
  • the release film 2 can be peeled off, and the light-transmitting substrate (cover panel) 1 can be attached to a polarizing plate or the like via the adhesive layer 1.
  • the laminate and the polarizing plate with adhesive can be manufactured, for example, by peeling off the release film from an adhesive sheet having a release film on both sides of the adhesive layer, and attaching the adhesive layer to a light-transmitting substrate or a polarizing plate.
  • the laminate can be manufactured by peeling off the release film from an adhesive sheet having a release film on one side of the adhesive layer and a light-transmitting substrate on the other side, and attaching the adhesive layer to a light-transmitting substrate or a polarizing plate.
  • the laminate can be manufactured by directly forming an adhesive layer on a light-transmitting substrate, and then attaching an adhesive layer provided on an adherend or another adhesive sheet to the adhesive layer.
  • the display of the present disclosure includes a light-transmitting substrate, a pressure-sensitive adhesive layer, a polarizing plate, and an optical element, and thus has excellent visibility.
  • the optical element is not particularly limited, and examples thereof include a liquid crystal element and an organic EL element.
  • FIG. 2 shows an example of a schematic cross-sectional view partially illustrating a display, which is an example of the use of an example of the adhesive sheet of the present disclosure.
  • 3 is a light-transmitting substrate (cover panel)
  • 1 is adhesive layer 1
  • 4 is a polarizing plate
  • 5 is adhesive layer 2
  • 6 is a barrier layer such as silicon nitride
  • 7 is an organic EL layer
  • 8 is a support such as polyimide
  • 9 is an organic EL cell. Note that the configuration of the display is not limited to that shown in FIG. 2.
  • a light-transmitting substrate (cover panel) is attached to a polarizing plate via the pressure-sensitive adhesive layer (pressure-sensitive adhesive layer 1) of the present disclosure, and is further attached to an organic EL cell via a pressure-sensitive adhesive layer for polarizing plate (pressure-sensitive adhesive layer 2).
  • the pressure-sensitive adhesive sheet of the present disclosure can be used in a form in which a transparent pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition is attached to a light-transmitting substrate (cover panel) and a polarizing plate, and the laminate is further attached to an organic EL cell via a pressure-sensitive adhesive layer for polarizing plate.
  • a transparent pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition is attached to a light-transmitting substrate (cover panel) and a polarizing plate
  • the laminate is further attached to an organic EL cell via a pressure-sensitive adhesive layer for polarizing plate.
  • the pressure-sensitive adhesive composition of the present disclosure can be used for both pressure-sensitive adhesive layer 1 and pressure-sensitive adhesive layer 2 .
  • the pressure-sensitive adhesive layer 1 has higher required quality, and since the pressure-sensitive adhesive composition of the present disclosure has good adhesion and bonding to the substrate, it is preferably used for the pressure-sensitive adhesive layer 1.
  • the pressure-sensitive adhesive for forming the pressure-sensitive adhesive layer 2 may be the pressure-sensitive adhesive composition of the present disclosure, or a conventionally known pressure-sensitive adhesive may be used.
  • displays There are no particular limitations on how the displays can be used, but examples include OLED televisions, OLED smartphones, OLED tablets, and OLED smartwatches.
  • the weight average molecular weight (Mw) was measured by gel permeation chromatography (GPC).
  • the equipment used was a GPC equipment manufactured by Shimadzu Corporation: LC-GPC system "Prominence”.
  • the column used was a TSKgel ⁇ -M manufactured by Tosoh Corporation, two of which were connected in series.
  • the eluent was N,N-dimethylformamide (DMF), and the measurement was performed at 40°C.
  • the Mw was determined by conversion using polystyrene with a known Mw as the standard substance. Based on the results of the weight average molecular weight measurements, the polymers were classified into H, M and L categories according to the following criteria.
  • L Molecular weight less than 1 million
  • Acrylic Polymers (A-2 to A-34, A'-1 to A'-4)) Acrylic polymers (A-2 to A-33, A'-1 to A'-4) were synthesized in the same manner as for the production of acrylic polymer (A-1), except that the compositions and blending amounts (parts by mass) were changed to those shown in Tables 1 to 4. The weight average molecular weights of the obtained acrylic polymers are shown in Tables 1 to 3.
  • KBE-403 (3-glycidoxypropyltriethoxysilane, manufactured by Shin-Etsu Chemical Co., Ltd.)
  • KBM-303 ([2-(3,4-epoxycyclohexyl)ethyl]trimethoxysilane, manufactured by Shin-Etsu Chemical Co., Ltd.)
  • ⁇ Tackifying Resin> SE10 (Haritac SE10, hydrogenated rosin, manufactured by Harima Chemicals Co., Ltd.)
  • FTR6100 (FTR6100, aliphatic/aromatic petroleum resin, manufactured by Mitsui Chemicals, Inc.)
  • A-100 (Super Ester A-100, rosin resin, manufactured by Arakawa Chemical Industries, Ltd.)
  • T130 (YS Polystar T130, terpene phenol resin, manufactured by Yasuhara Chemical Co., Ltd.)
  • Example 1 A pressure-sensitive adhesive composition was obtained by blending 100 parts of the acrylic polymer (A-1) with 0.4 parts of B-1 ("NP-1200", manufactured by Mitsui Chemicals, Inc., a biuret of hexamethylene diisocyanate) as the curing agent (B) and 0.1 parts of KBE-403 (3-glycidoxypropyltriethoxysilane, manufactured by Shin-Etsu Chemical Co., Ltd.) as the organosilane (C), and diluting with ethyl acetate to a nonvolatile content of 25.0 ⁇ 0.5%.
  • B-1 NP-1200
  • NP-1200 a biuret of hexamethylene diisocyanate
  • KBE-403 3-glycidoxypropyltriethoxysilane, manufactured by Shin-Etsu Chemical Co., Ltd.
  • the obtained adhesive composition was applied to a 38 ⁇ m thick polyethylene terephthalate release sheet (Therapeel MF: manufactured by Toray Film Processing Co., Ltd.) using a comma coater so that the thickness after drying would be 25 ⁇ m, and dried at 100° C. for 2 minutes to obtain an adhesive sheet.
  • a 100 ⁇ m thick polyethylene terephthalate film hereinafter referred to as PET film, product name: A-4300, manufactured by Toyobo Co., Ltd.
  • PET film product name: A-4300, manufactured by Toyobo Co., Ltd.
  • laminate A a laminate (hereinafter referred to as laminate A).
  • a polarizing plate layer structure: triacetyl cellulose film/polyvinyl alcohol film/polymethyl methacrylate film) was used instead of the PET film, and the adhesive layer was attached to the polymethyl methacrylate film surface of the polarizing plate so as to be in contact with the polarizing plate, thereby obtaining an adhesive-attached polarizing plate having a structure of "peeling sheet/adhesive layer/polarizing plate.”
  • the obtained adhesive-attached polarizing plate was then aged for one week under conditions of a temperature of 25°C and a relative humidity of 55%. This was designated as laminate B.
  • Examples 18, 24, 28, and 29 are reference examples.
  • the adhesive composition of the present disclosure was evaluated for its low viscosity, adhesion to laminates (glass, acrylic plate, ITO/PET), heat resistance, moist heat resistance, corrosion resistance, light leakage, and removability by the following methods. The results are shown in Table 5.
  • Viscosity is less than 7000 mPa ⁇ s (excellent)
  • Viscosity is 7000 mPa ⁇ s or more and less than 8000 mPa ⁇ s (good)
  • Viscosity is 8000 mPa ⁇ s or more and less than 9000 mPa ⁇ s (fairly good)
  • Viscosity is 9000 mPa ⁇ s or more and less than 10000 mPa ⁇ s (usable)
  • Viscosity is 10,000 mPa ⁇ s or more (unusable)
  • the laminate A obtained above was prepared to a size of 25 mm wide x 100 mm long to prepare a test laminate A.
  • the release sheet of the test laminate A was peeled off, and the adhesive layer was attached to a glass plate in an atmosphere of 23°C and 50% relative humidity, and pressure-bonded with a roll in accordance with JIS Z-0237.
  • the adhesive strength (peel angle 180°, peel speed 300 mm/min; unit N/25 mm width) was measured with a universal tensile tester. Separately, the adhesive strength was measured in the same manner as above, except that the adherend was replaced from the glass plate to an acrylic plate and an ITO/PET film.
  • the ITO/PET film was a PET film on which indium tin oxide was vapor-deposited, and a test adhesive sheet was attached to the ITO-vaporized surface.
  • the adhesiveness was evaluated based on the adhesive strength according to the following criteria. [Evaluation Criteria] ⁇ : Adhesive strength is 5.0N/25mm or more (Excellent) ⁇ : Adhesive strength is 3.0 N/25 mm or more and less than 5.0 N/25 mm (good). ⁇ : Adhesive strength is 2.0 N/25 mm or more and less than 3.0 N/25 mm (fairly good). ⁇ : Adhesive strength is 1.0N/25mm or more and less than 2.0N/25mm. (Usable) ⁇ : Adhesive strength is less than 1.0 N/25 mm (poor).
  • ⁇ Heat resistance and moist heat resistance evaluation 1> The laminate A obtained above was cut into a size of 930 mm wide and 523 mm long (equivalent to 42 inches). Next, the release sheet was peeled off from the cut laminate A, and the laminate was attached to an ITO sputtered glass plate (80 ⁇ : manufactured by Nippon Sheet Glass Co., Ltd.) using a laminator. Next, the glass plate to which the laminate A was attached was held in an autoclave at 50° C. and 5 atm for 20 minutes to bring each member into close contact, thereby obtaining a measurement sample. The heat resistance of this measurement sample was evaluated as a resistance evaluation in a high-temperature atmosphere. That is, the measurement sample was left at 105° C.
  • a PET film (IPF-05H125: manufactured by Gunze Co., Ltd.) having a 5 ⁇ m thick ITO transparent conductive film was cut to a width of 40 mm and a length of 100 mm, and attached to a 40 mm wide and 160 mm long ITO transparent conductive film by peeling off the release sheet from the laminate A.
  • this laminate was held in an autoclave at 50° C. and 5 atm for 20 minutes to bond each member together, thereby obtaining a measurement sample having a layer structure of PET film/adhesive layer/ITO film. Electrodes were connected to both ends of the measurement sample, and the initial electrical resistance value was measured.
  • the measurement sample was then left to stand for 1000 hours at 85°C and 85% relative humidity, and the electrical resistance value after aging was measured in the same manner as above.
  • the corrosion resistance was evaluated based on the following criteria.
  • the electrical resistance value was measured using Laresta-GP MCP-T600 (manufactured by Mitsubishi Chemical Corporation).
  • Electrical resistance increase rate ((electrical resistance value after aging ⁇ initial electrical resistance value)/initial electrical resistance value) [evaluation criteria]
  • ⁇ The electrical resistance increase rate is less than 0.5 (excellent).
  • the electrical resistance increase rate is 0.5 or more and less than 1.0 (good).
  • ⁇ The electrical resistance increase rate is 1.0 or more and less than 1.5 (fairly good).
  • the electrical resistance increase rate is 1.5 or more and less than 2.0. (Usable)
  • the electrical resistance increase rate is 2.0 or more (unusable).
  • the laminate B obtained above was cut into a size of 930 mm wide and 523 mm long (equivalent to 42 inches).
  • the release sheet was peeled off from the cut laminate B, and the laminate was attached to an ITO sputtered glass plate (80 ⁇ : manufactured by Nippon Sheet Glass Co., Ltd.) using a laminator.
  • the glass plate to which the laminate B was attached was held in an autoclave at 50° C. and 5 atm for 20 minutes to bring each member into close contact, thereby obtaining a measurement sample.
  • the heat resistance of this measurement sample was evaluated as a resistance evaluation in a high-temperature atmosphere. That is, the measurement sample was left at 105° C.
  • the laminate B obtained above was cut into a size of 930 mm wide and 523 mm long (equivalent to 42 inches).
  • the release sheet was peeled off from the cut laminate B, and two sheets of the laminate B were attached to both sides of an ITO sputtered glass plate (80 ⁇ : manufactured by Nippon Sheet Glass Co., Ltd.) using a laminator so that the absorption axes of the polarizing plates were perpendicular to each other to obtain a pressure-bonded product.
  • the pressure-bonded product was held in an autoclave at 50° C. and 5 atm for 20 minutes to bring each member into close contact, thereby obtaining a measurement sample. This measurement sample was left at 105° C.
  • the laminate B obtained above was cut into a size of 100 mm wide and 100 mm long.
  • the release sheet was peeled off from the cut laminate B and attached to an ITO sputtered glass plate (80 ⁇ : manufactured by Nippon Sheet Glass Co., Ltd.) using a laminator.
  • the members were held in an autoclave at 50°C and 5 atm for 20 minutes to adhere to each other, thereby obtaining a measurement sample.
  • ⁇ Of the five samples, two samples had glue residue or cloudiness of 5% or less of the measured area (fairly good). ⁇ : Of the five samples, three samples had glue residue or cloudiness of 5% or less of the measured area (usable). ⁇ : Of the five samples, four or more samples had adhesive residue of 5% or less of the measured area, or one or more samples had adhesive residue or cloudiness of more than 5% (unusable).
  • the pressure-sensitive adhesive composition of the present disclosure exhibited excellent results in terms of low viscosity, adhesion (glass, acrylic plate, ITO/PET), heat resistance and moist heat resistance evaluation, corrosion resistance, light leakage, and removability.
  • the pressure-sensitive adhesive composition of the comparative example did not satisfy all of the low viscosity, adhesion (glass, acrylic plate, ITO/PET), heat resistance and moist heat resistance evaluation, corrosion resistance, light leakage, and removability. From these results, it can be said that the pressure-sensitive adhesive composition of the present disclosure can be suitably used for bonding optical members.

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

Abstract

L'invention concerne une composition adhésive comprenant un polymère acrylique (A) et un agent de durcissement (B), le polymère acrylique (A) étant un copolymère d'un mélange de monomères contenant le monomère (a1), le monomère (a2), le monomère (a3) suivants et d'autres monomères, et satisfaisant l'expression (1) ; la teneur en (a2) étant de 40 à 95 parties en masse dans 100 parties en masse du mélange de monomères ; la teneur en (a3) étant d'au plus 10 parties en masse dans 100 parties en masse du mélange de monomères ; la teneur en (a4) étant de 0,1 à 20 parties en masse dans 100 parties en masse du mélange de monomères ; la teneur des autres monomères étant d'au plus 15 parties en masse dans 100 parties en masse du mélange de monomères ; la quantité de l'agent de durcissement (B) ajoutée étant de 0,01 à 5 parties en masse par rapport à 100 parties en masse du polymère acrylique (A) ; et la fraction de gel d'une couche adhésive composée de la composition adhésive étant de 55 à 90 %. Ici, (a1) est un monomère d'ester d'acide (méth)acrylique qui a une température de transition vitreuse d'un homopolymère d'au moins 0 °C et n'a pas de groupe fonctionnel, (a2) est le (méth)acrylate de 2-octyle, (a3) est un monomère contenant un groupe carboxy, (a4) est un monomère contenant un groupe hydroxy, et l'expression (1) est 1 500 ≤ Σ(T2×MA/100) ≤ 38 000, où T est la température de transition vitreuse (K) de l'homopolymère de (a1), et MA est la teneur (parties en masse) de (a1) dans 100 parties en masse du mélange de monomères.
PCT/JP2024/033159 2023-09-19 2024-09-17 Composition adhésive, feuille adhésive, stratifié et afficheur comprenant ledit stratifié Pending WO2025063181A1 (fr)

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JP7586263B1 (ja) 2023-09-19 2024-11-19 ａｒｔｉｅｎｃｅ株式会社 粘着剤組成物、粘着シート、積層体および該積層体を備えるディスプレイ
JP7691791B1 (ja) * 2024-11-06 2025-06-12 サイデン化学株式会社 再剥離用粘着剤組成物、表面保護フィルム、及び粘着剤層付き光学部材
JP7708474B1 (ja) * 2024-12-19 2025-07-15 サイデン化学株式会社 再剥離用粘着剤組成物及び粘着シート

Citations (5)

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JP2011231190A (ja) * 2010-04-26 2011-11-17 Nippon Carbide Ind Co Inc 偏光板用粘着剤組成物、並びにそれを用いた粘着剤付偏光板及び液晶表示装置
EP4155330A1 (fr) * 2022-09-13 2023-03-29 Basf Se Procédé pour la préparation d'un polymère adhésif sensible à la pression dispersé
JP2023538015A (ja) * 2020-08-14 2023-09-06 テーザ・ソシエタス・ヨーロピア 感圧接着剤組成物
WO2024143341A1 (fr) * 2022-12-27 2024-07-04 積水化学工業株式会社 Ruban adhésif
JP7586263B1 (ja) * 2023-09-19 2024-11-19 ａｒｔｉｅｎｃｅ株式会社 粘着剤組成物、粘着シート、積層体および該積層体を備えるディスプレイ

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US20100151241A1 (en) * 2008-04-14 2010-06-17 3M Innovative Properties Company 2-Octyl (Meth)acrylate Adhesive Composition

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Publication number Priority date Publication date Assignee Title
JP2011231190A (ja) * 2010-04-26 2011-11-17 Nippon Carbide Ind Co Inc 偏光板用粘着剤組成物、並びにそれを用いた粘着剤付偏光板及び液晶表示装置
JP2023538015A (ja) * 2020-08-14 2023-09-06 テーザ・ソシエタス・ヨーロピア 感圧接着剤組成物
EP4155330A1 (fr) * 2022-09-13 2023-03-29 Basf Se Procédé pour la préparation d'un polymère adhésif sensible à la pression dispersé
WO2024143341A1 (fr) * 2022-12-27 2024-07-04 積水化学工業株式会社 Ruban adhésif
JP7586263B1 (ja) * 2023-09-19 2024-11-19 ａｒｔｉｅｎｃｅ株式会社 粘着剤組成物、粘着シート、積層体および該積層体を備えるディスプレイ

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