WO2025053236A1 - 粘着剤および粘着剤組成物、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 - Google Patents

粘着剤および粘着剤組成物、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 Download PDF

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Publication number
WO2025053236A1
WO2025053236A1 PCT/JP2024/031928 JP2024031928W WO2025053236A1 WO 2025053236 A1 WO2025053236 A1 WO 2025053236A1 JP 2024031928 W JP2024031928 W JP 2024031928W WO 2025053236 A1 WO2025053236 A1 WO 2025053236A1
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Prior art keywords
monomer
mass
less
adhesive
acrylate
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English (en)
French (fr)
Japanese (ja)
Inventor
好映 柿沼
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Toyochem Co Ltd
Artience Co Ltd
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Toyochem Co Ltd
Artience Co Ltd
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Priority to KR1020257041077A priority Critical patent/KR20260007355A/ko
Priority to CN202480037455.2A priority patent/CN121263494A/zh
Publication of WO2025053236A1 publication Critical patent/WO2025053236A1/ja
Anticipated expiration legal-status Critical
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00Adhesives 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
    • C09J133/04Homopolymers or copolymers of esters
    • C09J133/06Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/062Copolymers with monomers not covered by C09J133/06
    • C09J133/066Copolymers with monomers not covered by C09J133/06 containing -OH groups
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B32LAYERED PRODUCTS
    • B32BLAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00Layered products comprising a layer of synthetic resin
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B32LAYERED PRODUCTS
    • B32BLAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00Layered products comprising a layer of synthetic resin
    • B32B27/30Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/12Esters of monohydric alcohols or phenols
    • C08F220/16Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/16Nitrogen-containing compounds
    • C08K5/21Urea; Derivatives thereof, e.g. biuret
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/54Silicon-containing compounds
    • C08K5/541Silicon-containing compounds containing oxygen
    • C08K5/5415Silicon-containing compounds containing oxygen containing at least one Si—O bond
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04Homopolymers or copolymers of esters
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02Non-macromolecular additives
    • C09J11/06Non-macromolecular additives organic
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/08Macromolecular additives
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00Adhesives 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
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00Adhesives 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
    • C09J133/04Homopolymers or copolymers of esters
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00Adhesives 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
    • C09J133/04Homopolymers or copolymers of esters
    • C09J133/06Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00Adhesives 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
    • C09J133/04Homopolymers or copolymers of esters
    • C09J133/14Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04Polyurethanes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04Polyurethanes
    • C09J175/14Polyurethanes having carbon-to-carbon unsaturated bonds
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00Adhesives in the form of films or foils
    • C09J7/20Adhesives in the form of films or foils characterised by their carriers
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00Adhesives in the form of films or foils
    • C09J7/30Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38Pressure-sensitive adhesives [PSA]
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00Adhesives in the form of films or foils
    • C09J7/30Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38Pressure-sensitive adhesives [PSA]
    • C09J7/381Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C09J7/385Acrylic polymers
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00Optical elements other than lenses
    • G02B5/30Polarising elements

Definitions

  • the present disclosure relates to adhesives and adhesive compositions, adhesive sheets, laminates, and displays including the laminates.
  • Adhesive sheets with an adhesive layer formed from an adhesive are easy to handle and are used in a wide range of fields, including label applications and medical applications. They are also widely used in various optical displays, such as liquid crystal displays (LCDs) and organic electroluminescence displays (OLEDs). In addition to being used as display devices, optical displays are also used as input devices such as touch panels. A cover panel is installed on the touch panel to protect the surface. Usually, the components that make up these optical displays are bonded together via an adhesive layer. Among them, adhesives used in applications where long-term use is expected, such as marking films, window films, automotive parts, and optical displays, require high adhesive strength to the adherend to prevent peeling during use. When applying an adhesive sheet to a metallic adherend, corrosion-resistant adhesives are required because corrosion of the adherend due to the components contained in the adhesive can cause deterioration of the product.
  • adhesives are generally diluted and adjusted to a low viscosity for convenient coating when producing adhesive sheets.
  • the 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 solids 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 be made with a higher solids content.
  • Patent Documents 1 and 2 are adjusted to a solids content of about 35%. After investigations, the inventors found that with the adhesives described in Patent Documents 1 and 2, if the solids content was adjusted to 35% or more, the viscosity would become too high, making coating difficult, and it was not possible to increase the solids content. As a result, the high cost of the solvent used and the difficulty of applying a thick layer of adhesive are major issues.
  • Patent Document 3 discloses a pressure-sensitive adhesive composition having a low viscosity, but the composition has a problem in terms of adhesive strength to an adherend.
  • the depletion of petroleum resources and the emission of carbon dioxide due to the combustion of petroleum-derived products are considered problems in the industrial sector in which PSA sheets are used. Therefore, attempts are being made to conserve petroleum resources by using biologically derived materials instead of petroleum-derived materials in various industries, starting with the packaging material field, as well as in the optical and semiconductor fields.
  • One method for increasing the proportion of biologically derived materials in adhesives mainly composed of acrylic polymers is to obtain an acrylic polymer by copolymerizing a monomer mixture containing a (meth)acrylic acid alkyl ester monomer obtained by esterifying a linear alkyl alcohol produced by an organism with (meth)acrylic acid. Furthermore, there are also tackifier resins made from naturally derived ingredients, and by selectively using these, it is possible to achieve environmentally friendly products. Increasing the proportion of environmentally friendly materials can contribute to saving petroleum resources, but the current situation is that only limited environmentally friendly materials are used, and there are issues with the performance that was originally achieved, such as fixation strength and adhesive strength.
  • the problem that the present invention aims to solve is to provide an adhesive that can contribute to the conservation of petroleum resources by increasing the proportion of environmentally friendly materials, and that has high adhesive performance to adherends, excellent corrosion resistance, and a low viscosity adhesive capable of high solid division, as well as an adhesive sheet and laminate using the same, and a display equipped with the laminate.
  • the present disclosure provides a pressure-sensitive adhesive comprising an acrylic polymer (A) which is a copolymer of a monomer mixture, the monomer mixture comprising, in 100% by mass, More than 30% by mass and less than 99.5% by mass of the following monomer (a1),
  • the monomer (a2) and the monomer (a3) are contained in an amount of 0.1% by mass or more and less than 70% by mass in total
  • the pressure-sensitive adhesive may further contain at least one selected from the group consisting of 30 mass % or less of the following monomer (a4) and less than 0.5 mass % of a monomer having a carboxy group.
  • (a1) 2-octyl (meth)acrylate (a2) A monomer having a glass transition temperature of 0° C. or higher when formed into a homopolymer (excluding monomer (a3), monomers having a carboxy group, and monomers having a hydroxy group).
  • (a3) Isobornyl (meth)acrylate (a4) A monomer other than the monomer (a1), the monomer (a2), the monomer (a3), a monomer having a carboxy group, and a monomer having a hydroxy group.
  • 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.
  • the adhesive composition, adhesive sheet, laminate, and display including the laminate according to the present disclosure have the following configurations [1] to [28].
  • the pressure-sensitive adhesive contains a nitrogen-containing monomer as monomer (a2) and also contains monomer (a3) and a monomer having a hydroxy group
  • the content of at least one of the nitrogen-containing monomer, monomer (a3) and hydroxy group-containing monomer in 100 mass% of the monomer mixture is less than 10 mass%.
  • 2-octyl (meth)acrylate (a2) A monomer having a glass transition temperature of 0° C. or higher when formed into a homopolymer (excluding monomer (a3), monomers having a carboxy group, and monomers having a hydroxy group).
  • (a3) isobornyl (meth)acrylate; (a4) other monomers other than the monomer (a1), the monomer (a2), the monomer (a3), the monomer having a carboxy group, and the monomer having a hydroxy group; [3] an acrylic polymer (A) which is a copolymer of a monomer mixture, A pressure-sensitive adhesive comprising, in 100 mass% of the monomer mixture, more than 30 mass% and less than 99.5 mass% of the following monomer (a1), and a total of the following monomer (a2) and monomer (a3), which may further comprise at least one selected from the group consisting of 30 mass% or less of the following monomer (a4), less than 0.5 mass% of a monomer having a carboxy group, and a monomer having a hydroxy group, the total of which together with the monomer having the carboxy group is 0.5 mass% or more and 30 mass% or less, and in which when the monomer (a2) contains a nitrogen-containing monomer and
  • (a1) 2-octyl (meth)acrylate (a2) A monomer having a glass transition temperature of 0° C. or higher when formed into a homopolymer (excluding monomer (a3), monomers having a carboxy group, and monomers having a hydroxy group).
  • the adhesive according to any one of [1] to [3] above, containing monomer (a2) and monomer (a3) in a total amount of 0.1 mass% or more and less than 50 mass% in 100 mass% of the monomer mixture.
  • the pressure-sensitive adhesive according to [6] containing a total of 0.5% by mass or more and 30% by mass or less of a monomer having a carboxy group and a monomer having a hydroxy group, based on 100% by mass of the monomer mixture.
  • a pressure-sensitive adhesive composition comprising the pressure-sensitive adhesive according to any one of [1] to [8] above and a curing agent (B).
  • C silane coupling agent
  • the pressure-sensitive adhesive layer according to [17] having a dielectric tangent of 0.1 or less at 40 GHz.
  • composition, pressure-sensitive adhesive sheet, laminate, and display of the present disclosure will be described below, but the present disclosure is not limited thereto.
  • the term “(meth)acrylate” includes acrylate and methacrylate
  • the term “(meth)acryloxy group” includes acryloxy group and methacryloxy group
  • the term “monomer” refers to a monomer having an ethylenically unsaturated group.
  • a numerical range specified using “to” includes the numerical values written before and after "to” as the range of 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 of the present disclosure contains an acrylic polymer (A).
  • the acrylic polymer (A) is a copolymer of a monomer mixture, and contains, in 100% by mass of the monomer mixture, More than 30% by mass and less than 99.5% by mass of the following monomer (a1), The monomer (a2) and the monomer (a3) are contained in an amount of 0.1% by mass or more and less than 70% by mass in total,
  • the pressure-sensitive adhesive may further contain at least one selected from the group consisting of 30% by mass or less of the following monomer (a4) and less than 0.5% by mass of a monomer having a carboxy group.
  • (a1) 2-octyl (meth)acrylate (a2) A monomer having a glass transition temperature of 0° C.
  • Monomer (a1) refers to 2-octyl(meth)acrylate and is represented by the following formula (1):
  • Monomer (a1) is a biomass monomer.
  • the content of (a1) is more than 30% by mass and less than 99.5% by mass in 100% by mass of the monomer mixture. If the content of (a1) is less than 30% by mass, the viscosity of the adhesive increases or the adhesive strength decreases, which is not preferable.
  • the lower limit of the content of (a1) is preferably 50% by mass or more, more preferably 70% by mass or more, although the desired effect can be obtained if it is more than 30% by mass.
  • the content of (a1) may be 99.5% by mass or less, 95% by mass or less, or 91% by mass or less. For example, it may be more than 30% by mass and less than 99.5% by mass, 50 to 95% by mass, or 70 to 91% by mass.
  • the monomer (a2) is a monomer having a homopolymer glass transition temperature of 0° C. or higher. However, even if the monomer has a homopolymer glass transition temperature of 0° C. or higher, the monomer (a3) and those having a carboxy group and a hydroxy group are excluded.
  • 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 the monomer (a2) include nitrogen-containing monomers such as acrylamide, N,N-dimethylacrylamide, methacrylonitrile, acrylonitrile, and diacetone acrylamide; alkyl (meth)acrylates such as methyl (meth)acrylate, ethyl methacrylate, ter-butyl methacrylate, sec-butyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, isopropyl methacrylate, and stearyl (meth)acrylate; and (meth)acrylates having an alicyclic or aromatic ring such as cyclohexyl (meth)acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, and phenyl (meth)acrylate.
  • nitrogen-containing monomers such as acrylamide, N,N-dimethylacrylamide, methacrylonitrile, acrylonitrile, and diace
  • the monomer (a2) is preferably at least one selected from the group consisting of methyl (meth)acrylate, ethyl methacrylate, cyclohexyl (meth)acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, and phenyl (meth)acrylate.
  • the monomer mixture contains a nitrogen-containing monomer as monomer (a2), and also contains monomer (a3) and a monomer having a hydroxy group
  • the content of at least one of the nitrogen-containing monomer, monomer (a3) and hydroxy group-containing monomer is less than 10 mass%. If the content of the nitrogen-containing monomer as monomer (a2), monomer (a3) and hydroxy group-containing monomer 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 mass%.
  • the monomer mixture contains a nitrogen-containing monomer as monomer (a2) and a monomer having a hydroxy group
  • the content of at least one of the nitrogen-containing monomer and the hydroxy group-containing monomer is less than 10 mass%. If the content of the nitrogen-containing monomer and the hydroxy group-containing monomer as monomer (a2) is high, the cohesive strength becomes too high and the adhesive strength decreases, so it is important that the content of at least one is less than 10 mass%.
  • the total content of (a2) and monomer (a3) is 0.1% by mass or more and less than 70% by mass in 100% by mass of the monomer mixture. By including 0.1% by mass or more and less than 70% by mass, cohesive strength and/or adhesive strength can be ensured. It is more preferable that it is 1% by mass or more and less than 50% by mass, and even more preferable that it is 3% by mass or more and less than 30% by mass.
  • Monomer (a3) is isobornyl (meth)acrylate, a biomass monomer. In order to increase the biomass content of the PSA, it is preferred that the PSA contains a monomer (a3).
  • the monomer (a4) is a monomer other than the monomer (a1), the monomer (a2), the monomer (a3), the monomer having a carboxy group, and the monomer having a hydroxy group, and is not particularly limited.
  • a (meth)acrylate which is a biomass monomer as the monomer (a4), and it is more preferable to use a (meth)acrylate having a high biomass ratio.
  • (a4) may or may not be contained, but if it is contained, its content is 30 mass% or less in 100 mass% of the monomer mixture. By containing 30 mass% or less, it is possible to suppress an increase in viscosity of the adhesive. In order to suppress an increase in viscosity, its content is preferably 20 mass% or less, and more preferably 10 mass% or less.
  • the monomer mixture constituting the acrylic polymer (A) preferably further contains at least one of a monomer having a carboxy group and a monomer having a hydroxy group. It may contain both a monomer having a carboxy group and a monomer having a hydroxy group, or only one of them. By containing at least one of a monomer having a carboxy group and a monomer having a hydroxy group, the cohesive strength of the adhesive layer is increased, and it becomes easier to increase the adhesive strength and heat resistance. In terms of preventing corrosion of the adherend by acid, it is more preferable to contain a monomer having a hydroxy group.
  • 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; peroxy esters 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; 2,2-bis(4,4-
  • azo compounds examples include 2,2'-azobisbutyronitrile such as 2,2'-azobisisobutyronitrile (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); and 1,1'-azobis-1-alkanenitrile such as 1,1'-azobis(cyclohexane-1-carbonitrile).
  • AIBN 2,2'-azobisisobutyronitrile
  • 2-methylbutyronitrile 2,2'-azobisvaleronitrile
  • 2,2'-azobisvaleronitrile such as 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile and 2,2'-azobis(
  • 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 not particularly limited, but is preferably 2,000,000 or less, and more preferably 1,000,000 or less.
  • 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 a pressure-sensitive adhesive containing an acrylic polymer (A) and a curing agent (B). If necessary, it may also contain a silane coupling agent (C) and a tackifier resin (D).
  • the pressure-sensitive adhesive composition of the present disclosure contains a curing agent (B), and the curing agent (B) can be any agent that can bring about a crosslinked structure in the pressure-sensitive adhesive composition.
  • the incorporation of the curing agent improves the cohesive strength of the pressure-sensitive adhesive layer, and improves the adhesive strength, heat resistance, and light resistance.
  • the curing agent (B) is preferably one of an isocyanate-based curing agent and an epoxy-based curing agent, which can appropriately increase the cohesive strength of the adhesive and is less likely to adversely affect other physical properties.
  • a known curing agent other than the isocyanate-based curing agent and the epoxy-based curing agent may be used in combination.
  • 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.
  • aromatic polyisocyanates include 1,3-phenylene diisocyanate, 4,4'-diphenyl diisocyanate, 1,4-phenylene diisocyanate, 4,4'-diphenylmethane diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 4,4'-toluidine diisocyanate, 2,4,6-triisocyanate toluene, 1,3,5-triisocyanate benzene, dianisidine diisocyanate, 4,4'-diphenyl ether diisocyanate, 4,4',4"-triphenylmethane triisocyanate, etc.
  • aliphatic polyisocyanates examples include trimethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate (also known as HMDI), pentamethylene diisocyanate, 1,2-propylene diisocyanate, 2,3-butylene diisocyanate, 1,3-butylene diisocyanate, dodecamethylene diisocyanate, and 2,4,4-trimethylhexamethylene diisocyanate.
  • aromatic aliphatic polyisocyanates examples include ⁇ , ⁇ '-diisocyanate-1,3-dimethylbenzene, ⁇ , ⁇ '-diisocyanate-1,4-dimethylbenzene, ⁇ , ⁇ '-diisocyanate-1,4-diethylbenzene, 1,4-tetramethylxylylene diisocyanate, and 1,3-tetramethylxylylene diisocyanate.
  • alicyclic polyisocyanates examples include 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate (also known as IPDI, isophorone diisocyanate), 1,3-cyclopentane diisocyanate, 1,3-cyclohexane diisocyanate, 1,4-cyclohexane diisocyanate, methyl-2,4-cyclohexane diisocyanate, methyl-2,6-cyclohexane diisocyanate, 4,4'-methylenebis(cyclohexyl isocyanate), 1,4-bis(isocyanatomethyl)cyclohexane, etc.
  • IPDI isophorone diisocyanate
  • 1,3-cyclopentane diisocyanate 1,3-cyclohexane diisocyanate
  • 1,4-cyclohexane diisocyanate methyl-2,4-cyclohexane diisocyanate
  • 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 nurate is a trimer of an isocyanate monomer.
  • examples include a trimer of hexamethylene diisocyanate, a trimer of isophorone diisocyanate, and a trimer of tolylene 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 or nurate, which is a reaction product between an isocyanate monomer and a trifunctional low-molecular-weight active hydrogen-containing compound.
  • 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.
  • epoxy hardeners examples include glycerin diglycidyl ether, 1,6-hexanediol diglycidyl ether, N,N,N',N'-tetraglycidyl-m-xylylenediamine, 1,3-bis(N,N'-diglycidylaminomethyl)cyclohexane, and N,N,N',N'-tetraglycidylaminophenylmethane.
  • the hardener (B) is preferably contained in an amount of 0.02 to 4 parts by mass, and more preferably 0.04 to 1 part by mass, per 100 parts by mass of the acrylic polymer (A). If the content is 0.02 parts by mass or more, the cohesive strength is further improved, and if it is 4 parts by mass or less, it becomes easier to achieve both cohesive strength and flexibility, making it easier to obtain sufficient adhesive strength, heat resistance, and light resistance.
  • the pressure-sensitive adhesive composition of the present disclosure preferably contains a silane coupling agent (C).
  • a silane coupling agent (C) By containing the silane coupling agent (C), it is possible to improve the adhesive strength, heat resistance, wet heat whitening resistance, and light resistance.
  • the silane coupling agent (C) is preferably contained in an amount of 0.05 to 0.2 parts by mass per 100 parts by mass of the acrylic polymer (A). By making it 0.05 to 0.2 parts by mass, it becomes easy to achieve both heat resistance, outgas resistance, and light resistance.
  • Examples of the silane coupling agent (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, and an alkoxysilane compound having an epoxy group.
  • KBM-403 (3-glycidoxypropyltrimethoxysilane), KBE-403 (3-glycidoxypropyltriethoxysilane), KBM-303 (2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane) (all manufactured by Shin-Etsu Chemical Co., Ltd.), BYK-325N (polyether-modified polymethylalkylsiloxane) (manufactured by BYK Japan KK), and the like.
  • the pressure-sensitive adhesive composition of the present disclosure preferably further contains a tackifier resin (D).
  • a tackifier resin As the tackifier resin (D), all existing resins such as 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 can be used.
  • the tackifier resin may be used alone or in combination of two or more.
  • 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 content of tackifier resin (D) is preferably less than 50 parts by mass, and more preferably 40 parts by mass or less, per 100 parts by mass of acrylic polymer (A) in the adhesive composition.
  • tackifier resin (D) By including tackifier resin (D), the adhesive strength to the adherend can be improved.
  • the softening point of the tackifier resin (D) is preferably a higher softening point grade in that durability at high temperatures can be improved, and is preferably 90°C or higher, more preferably 120°C or higher, and even more preferably 140°C or higher.
  • the adhesive composition of the present disclosure may contain optional components such as various resins, chlorinated polyolefins (described below), oils, softeners, dyes, pigments, antioxidants, and UV absorbers, so long as the problem can be solved.
  • optional components such as various resins, chlorinated polyolefins (described below), oils, softeners, dyes, pigments, antioxidants, and UV absorbers, so long as the problem can be solved.
  • chlorinated polyolefins 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.).
  • the adhesive composition of the present disclosure preferably has a gel fraction of 40% or more. However, depending on the application, a gel fraction of 40% or less may also be used. The method for measuring the gel fraction is described in detail in the Examples.
  • the pressure-sensitive adhesive composition of the present disclosure contains the acrylic polymer (A), which is a copolymer of a monomer mixture containing a specific monomer, and thus has the effect of suppressing the increase in viscosity that occurs when using an acrylic polymer, and can ensure high adhesive strength to an adherend, thereby making it possible to significantly reduce the amount of organic solvent used to adjust the viscosity during application compared to conventional methods.
  • A acrylic polymer
  • 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 can be produced, for example, by peeling off the release film from a pressure-sensitive adhesive sheet having release films on both sides of the pressure-sensitive adhesive layer, and attaching the pressure-sensitive adhesive layer to a substrate such as a light-transmitting flexible substrate or a polarizing plate, to form a laminate.
  • the pressure-sensitive adhesive layer can be directly formed on the light-transmitting flexible substrate, and then an adhesive layer provided on a substrate or another pressure-sensitive adhesive sheet can be attached to the pressure-sensitive adhesive layer to form a laminate.
  • a display includes the laminate of the present disclosure, a polarizing plate, and an optical element, and thereby 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 a 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 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 a polarizing plate.
  • the pressure-sensitive adhesive layer of the present disclosure can be used as either pressure-sensitive adhesive layer 1 or pressure-sensitive adhesive layer 2 .
  • the pressure-sensitive adhesive layer 1 has higher required quality, and since the pressure-sensitive adhesive of the present disclosure has good adhesion and bonding properties 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 of the present disclosure or a conventionally known pressure-sensitive adhesive.
  • 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 adhesive and adhesive composition of the present disclosure can be made partially or entirely from biological materials by using a biomass monomer as the monomer constituting the acrylic polymer (A) or by using a biomass tackifier.
  • the biomass degree is preferably 30% or more. The higher the biomass degree, the more useful the material is as an environmentally friendly material. The method for calculating the biomass degree is described in the Examples.
  • acrylic polymers (A) were produced and evaluated so that the Mw was 400,000 to 500,000, 700,000 to 900,000, or 1,900,000 to 2,000,000.
  • the method for measuring the weight average molecular weight of the acrylic polymer is as follows.
  • the weight average molecular weight (Mw) was measured by gel permeation chromatography (GPC).
  • the apparatus used was a GPC apparatus 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.
  • the weight average molecular weight (Mw) of the acrylic polymer is measured, and the evaluation results are as follows: if it is 1.9 million to 2 million, the Mw classification is U; if it is 700,000 to 900,000, the Mw classification is H; and if it is 400,000 to 500,000, the Mw classification is L.
  • Example 1 Production of (A-1) Using a reaction apparatus equipped with a stirrer, a reflux condenser, a nitrogen inlet tube, a thermometer, and a dropping tube, ethyl acetate was added as a polymerization solvent to a reaction vessel, and a monomer mixture of 19.75 parts of 2-octyl acrylate (2-OA) as monomer (a1), 20 parts of methyl acrylate (MA) as monomer (a2), 3 parts of isobornyl acrylate (IBXA) as monomer (a3), 7 parts of 2-hydroxyethyl acrylate (HEA) and 0.25 parts of 4-hydroxybutyl acrylate (4HBA) as monomer (a3), and 0.04 parts of azobisisobutyronitrile as an initiator was reacted.
  • 2-OA 2-octyl acrylate
  • MA methyl acrylate
  • IBXA isobornyl acrylate
  • HOA 2-hydroxyethyl
  • a reaction vessel was charged with 19.75 parts of 2-octyl acrylate (2-OA), 20 parts of methyl acrylate (MA) as monomer (a2), 3 parts of isobornyl acrylate (IBXA) as monomer (a3), 7 parts of 2-hydroxyethyl acrylate (HEA), and 0.25 parts of 4-hydroxybutyl acrylate (4HBA), a monomer mixture of ethyl acetate as a polymerization solvent, and 0.02 parts of azobisisobutyronitrile as an initiator, and the resulting solution was dropped from the dropping tube over about 2 hours, and polymerized for 6 hours at about 80°C under a nitrogen atmosphere.
  • 2-OA 2-octyl acrylate
  • MA methyl acrylate
  • IBXA isobornyl acrylate
  • HOA 2-hydroxyethyl acrylate
  • 4HBA 4-hydroxybutyl acrylate
  • the obtained acrylic polymer was designated (A-1).
  • the results of measuring the weight average molecular weight (Mw) of the obtained acrylic polymer are shown in Table 1.
  • Example 8 0.2 parts of "D-165N” (a biuret of hexamethylene diisocyanate, manufactured by Mitsui Chemicals) as a curing agent (B) was mixed with 100 parts of the acrylic polymer (A-1) to obtain a pressure-sensitive adhesive composition.
  • the obtained pressure-sensitive adhesive composition was coated using a comma coater onto a 38 ⁇ m-thick release liner (SP-PET-O1-BU: manufactured by Mitsui Chemicals Tocello Inc.) as a release sheet so that the thickness after drying would be 25 ⁇ m. After drying at 110° C.
  • Example 18 An adhesive sheet was obtained in the same manner as in Example 8, except that the acrylic polymer (A-5) obtained in Example 5 was used as the adhesive.
  • the 38 ⁇ m release liner of the obtained adhesive sheet was peeled off, and the adhesive layer was attached to a PET film (Toyobo Co., Ltd., Cosmoshine A-4360, thickness 100 ⁇ m) as a substrate, and cut into a size of 30 mm wide x 100 mm long to prepare a test adhesive sheet. Furthermore, the release liner on the other side of the adhesive tape was peeled off to prepare a test piece, and the weight was measured. The test piece was immersed in ethyl acetate at 23 ° C. for 24 hours, then removed from the ethyl acetate and dried at 150 ° C. for 30 minutes.
  • Biomass ratio calculation The biomass degree of the pressure-sensitive adhesive composition was calculated using the following formula (2).
  • Biomass degree ⁇ (Aw ⁇ Ab) + (Bw ⁇ Bb) + (Cw ⁇ Cb) ⁇ / (Aw + Bw + Cw) ...
  • Aw weight of monomer A
  • Bw weight of monomer B
  • Cw weight of tackifier
  • Ab biomass degree (%) of monomer A
  • Bb biomass degree (%) of monomer B
  • Cb biomass degree (%) of monomer C
  • the minimum value was used for the above calculation.
  • ⁇ Glass adhesion strength> The 38 ⁇ m release liner of the obtained adhesive sheet was peeled off, and the adhesive layer was attached to a PET film (Toyobo Co., Ltd., Cosmoshine A-4360, thickness 100 ⁇ m) as a substrate, and cut into a size of 25 mm wide x 100 mm long to prepare a test adhesive sheet.
  • the other 75 ⁇ m release liner of this test adhesive sheet was peeled off, and the adhesive layer was attached to a glass plate in an atmosphere of 23 ° C.-relative humidity 50% (50% RH), and further pressed with a roll in accordance with JIS Z-0237.
  • peel strength (peel angle 180 °, peel speed 300 mm / min; unit N / 25 mm width) was measured with a tensile tester (Tensilon: Orientec Co., Ltd.). [Evaluation Criteria] A: Peel strength is 20N/25mm or more.: Good B: Peel strength is 10N/25mm or more and less than 20N/25mm.: Usable C: Peel strength is less than 10N/25mm.: Unusable
  • the adhesive sheet was attached to the aluminum foil and then left for 48 hours under high temperature and high humidity conditions of 60° C. and 90% RH. The adhesive sheet was then peeled off from the aluminum foil, and the aluminum foil surface was visually inspected and evaluated according to the following criteria. A: No discoloration was observed on the surface of the aluminum foil. B: Partial discoloration was observed on the surface of the aluminum foil. C: Discoloration was observed on the surface of the aluminum foil.
  • ⁇ Method of measuring refractive index> The refractive index of the adhesive layer at 23° C. is measured with an Abbe refractometer (manufacturer: ERMA, model: ER-2S). [Evaluation Criteria] A: Refractive index is 1.45 or more and less than 1.52: Usable C: Refractive index is less than 1.45 or 1.52 or more: Unusable
  • Adhesive layer 1 Adhesive layer 1, 2 Release film, 3 Substrate, 4 Polarizing plate, 5 Adhesive layer 2, 6 Barrier layer, 7 Organic EL layer, 8 Support, 9 Organic EL cell

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