WO2022065483A1 - 電気剥離性粘着剤組成物、電気剥離性粘着シート、及び電気剥離性粘着シートの使用方法 - Google Patents

電気剥離性粘着剤組成物、電気剥離性粘着シート、及び電気剥離性粘着シートの使用方法 Download PDF

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Publication number
WO2022065483A1
WO2022065483A1 PCT/JP2021/035369 JP2021035369W WO2022065483A1 WO 2022065483 A1 WO2022065483 A1 WO 2022065483A1 JP 2021035369 W JP2021035369 W JP 2021035369W WO 2022065483 A1 WO2022065483 A1 WO 2022065483A1
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Prior art keywords
sensitive adhesive
pressure
mass
adhesive composition
component
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PCT/JP2021/035369
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English (en)
French (fr)
Japanese (ja)
Inventor
慎弥 高岡
健太 西嶋
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Lintec Corp
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Lintec Corp
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Priority to JP2022552100A priority Critical patent/JP7784382B2/ja
Priority to KR1020237010876A priority patent/KR20230073226A/ko
Priority to CN202180065203.7A priority patent/CN116194542B/zh
Publication of WO2022065483A1 publication Critical patent/WO2022065483A1/ja
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
    • C09J9/02—Electrically-conducting adhesives
    • 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
    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material 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
    • C09J11/04—Non-macromolecular additives inorganic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • 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
    • C09J193/00—Adhesives based on natural resins; Adhesives based on derivatives thereof
    • C09J193/04—Rosin
    • 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
    • C09J201/00—Adhesives based on unspecified macromolecular compounds
    • 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
    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C09J7/385—Acrylic polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
    • C09J2301/312—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier parameters being the characterizing feature
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
    • C09J2301/314—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive layer and/or the carrier being conductive
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/50—Additional features of adhesives in the form of films or foils characterized by process specific features
    • C09J2301/502—Additional features of adhesives in the form of films or foils characterized by process specific features process for debonding adherents

Definitions

  • the present invention relates to an electro-peelable pressure-sensitive adhesive composition, an electro-peelable pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer formed from the electro-peelable pressure-sensitive adhesive composition, and a method of using the electro-peelable pressure-sensitive adhesive sheet.
  • removability may be required in applications such as temporary fixing tape, surface protective film, masking tape for painting or decoration, and removable memo.
  • the removable adhesive sheet is required to have an adhesive strength that does not peel off from the adherend during transportation, storage, processing, etc. when it is attached to the adherend, but after it has finished functioning. , Removability that can be easily removed is required.
  • Patent Document 1 discloses a composition for energization peeling containing an ionic liquid as a pressure-sensitive adhesive that can be easily peeled off from an adherend after use.
  • the present invention is an electrically peelable pressure-sensitive adhesive composition
  • a base polymer comprising a base polymer, an ionic compound, and a rosin-containing diol
  • an electrically peelable pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer formed from the electro-peelable pressure-sensitive adhesive composition.
  • Specific embodiments of the present invention are as follows [1] to [14].
  • An electropeeling pressure-sensitive adhesive composition comprising a base polymer (A), an ionic compound (B), and a rosin-containing diol (C).
  • N is an integer of 1 or more.
  • Sexual pressure-sensitive adhesive composition [8] Any of the above [1] to [7], wherein the content of the active ingredient that is liquid at 25 ° C. is 1 to 50% by mass with respect to the total amount of the active ingredient in the pressure-sensitive adhesive composition.
  • the electrically peelable pressure-sensitive adhesive composition of one preferred embodiment of the present invention has high adhesiveness before voltage application, but can easily reduce the adhesiveness by voltage application.
  • the upper limit value and the lower limit value can be arbitrarily combined.
  • the range of "20 to 90” and the range of "40 to 120” are also described in the present specification. It is included in the numerical range.
  • the numerical range is described as "preferably 20 or more, more preferably 40 or more, preferably 120 or less, more preferably 90 or less", it is referred to as "20 to 90”.
  • the range and the range of "40 to 120” are also included in the numerical range described herein.
  • the description of "60 to 100” means that the range is "60 or more and 100 or less”.
  • the "active ingredient" of the electro-removable pressure-sensitive adhesive composition means a component contained in the electro-removable pressure-sensitive adhesive composition excluding a diluting solvent of water or an organic solvent.
  • the mass average molecular weight (Mw) is a polystyrene-equivalent value measured by a gel permeation chromatography (GPC) method, and specifically, a value measured based on the method described in Examples. Is.
  • the electroremovable pressure-sensitive adhesive composition of the present invention (hereinafter, also simply referred to as “taste-sensitive adhesive composition”) is a base polymer (A) (hereinafter, also referred to as “component (A)”), an ionic compound (B) ( Hereinafter, it is also referred to as “component (B)”) and a rosin-containing diol (C) (hereinafter, also referred to as “component (C)”).
  • a pressure-sensitive adhesive composition comprising a component (A), a component (B), and a component (C) is a component (A) as a raw material of the pressure-sensitive adhesive composition.
  • Component (B), and component (C) are used. Therefore, for example, an embodiment in which the component (B) is ionized into a cation and an anion in the pressure-sensitive adhesive composition is also included.
  • a general electro-removable pressure-sensitive adhesive composition an ionic compound is blended with a base polymer to impart a property of reducing the pressure-sensitive adhesive by applying electric power.
  • the electrically peelable pressure-sensitive adhesive composition containing an ionic compound has insufficient tackiness as compared with the pressure-sensitive adhesive composition containing no ionic compound.
  • a pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer formed from such an electrically peelable pressure-sensitive adhesive composition is particularly required to have improved adhesive strength against a metal adherend such as a stainless steel plate or an aluminum plate.
  • a pressure-sensitive adhesive is often added in order to improve the stickiness.
  • a tackifier when blended with an electroleapable pressure-sensitive adhesive composition composed of a base polymer and an ionic compound, depending on the type of the tackifier, it depends on the type of the tackifier.
  • Adhesive composition that has poor compatibility with ionic compounds (particularly ionic liquids) and whose adhesiveness does not sufficiently improve before voltage application, or adhesiveness that does not easily decrease even when voltage is applied. In some cases, it became a sexual composition.
  • a tacky composition containing a rosin-containing diol, which is a tackifier, together with a base polymer and an ionic compound has high tackiness before applying a voltage. It was found that while having a property, it has a property that the adhesiveness can be easily lowered by applying a voltage.
  • the pressure-sensitive adhesive composition of the present invention has been completed based on the findings.
  • the pressure-sensitive adhesive composition according to one aspect of the present invention is further blended with one or more selected from the cross-linking agent (D) and the compound (E) represented by the general formula (e-1). It is preferably a composition, and more preferably a pressure-sensitive adhesive composition in which the components (D) and (E) are blended together. Further, the pressure-sensitive adhesive composition according to one aspect of the present invention may be a pressure-sensitive adhesive composition containing additives other than the components (A) to (E).
  • the components (A) and the components (C) is preferably 65 to 100% by mass, more preferably 70 to 100% by mass, based on the total amount (100% by mass) of the active ingredient of the pressure-sensitive adhesive composition. It is more preferably 80 to 100% by mass, still more preferably 85 to 100% by mass, and particularly preferably 90 to 100% by mass.
  • the total blending amount of the component (A), the component (B), the component (C), the component (D) and the component (E) is the said.
  • the total amount (100% by mass) of the active ingredient of the pressure-sensitive adhesive composition preferably 70 to 100% by mass, more preferably 80 to 100% by mass, still more preferably 85 to 100% by mass, still more preferably 90 to 90 to 100% by mass. It is 100% by mass, particularly preferably 95 to 100% by mass.
  • the content of the active ingredient which is liquid at 25 ° C. is determined in the pressure-sensitive adhesive composition. 1 to 50% by mass, more preferably 3 to 40% by mass, still more preferably 5 to 30% by mass, still more preferably 7 to 25% by mass, based on the total amount (100% by mass) of the active ingredient of. Particularly preferably, it is 10 to 20% by mass.
  • a pressure-sensitive adhesive composition containing a large amount of liquid components may have insufficient adhesiveness.
  • the pressure-sensitive adhesive composition of one aspect of the present invention since the rosin-based diol (C) having good compatibility with the liquid component is blended, the pressure-sensitive adhesive composition has further improved adhesiveness. be able to.
  • the above-mentioned "liquid component” is an active ingredient of a liquid at 25 ° C. other than a solvent, and specifically, an ionic liquid (B3) used as the component (B) and a compound (E) used as the component (E). ) Etc. can be mentioned.
  • the base polymer (A) used in one embodiment of the present invention may be any polymer having adhesiveness, for example, an acrylic polymer, a urethane polymer, a rubber polymer, an olefin polymer, a silicone polymer, and these. Examples thereof include a curable polymer having a polymerizable functional group in the polymer. These base polymers (A) may be used alone or in combination of two or more. Further, the base polymer (A) used in one aspect of the present invention may be an emulsion type polymer or a non-emulsion type polymer.
  • the mass average molecular weight of the base polymer (A) used in one embodiment of the present invention is preferably 10,000 to 2 million, more preferably 20,000 to 2, from the viewpoint of obtaining a pressure-sensitive adhesive composition having high adhesiveness before applying a voltage. It is 1.8 million, more preferably 30,000 to 1.5 million.
  • the mass average molecular weight is a polystyrene-equivalent value measured by a gel permeation chromatography (GPC) method, and specifically, a value measured based on the method described in Examples. be.
  • the base polymer (A) used in one embodiment of the present invention is acrylic from the viewpoint of making a pressure-sensitive adhesive composition which has high adhesiveness before voltage application and can easily reduce the adhesiveness by voltage application. It is preferable to include a system polymer (A1).
  • the content ratio of the acrylic polymer (A1) in the component (A) is the total amount (100) of the component (A) contained in the pressure-sensitive adhesive composition. Mass%), preferably 30 to 100% by mass, more preferably 50 to 100% by mass, more preferably 70 to 100% by mass, still more preferably 80 to 100% by mass, still more preferably 90 to 100% by mass. %, Especially preferably 95 to 100% by mass.
  • acrylic polymer (A1) used in one embodiment of the present invention examples include polymers having a structural unit (a1) derived from an alkyl (meth) acrylate (hereinafter, also referred to as “monomer (a1 ′)”). From the viewpoint of making a pressure-sensitive adhesive composition which has high adhesiveness before applying a voltage and can easily reduce the adhesiveness by applying a voltage, a functional group-containing monomer (hereinafter, "monomer (a2')" is used together with the structural unit (a1). ) ”), It is preferable that the copolymer has a structural unit (a2).
  • the form of the copolymer is not particularly limited and may be any of a random copolymer, a block copolymer, and a graft copolymer.
  • the acrylic polymer (A1) used in one aspect of the present invention may be used alone or in combination of two or more.
  • the mass average molecular weight of the acrylic polymer (A1) is preferably 50,000 to 2 million, more preferably 100,000 to 1,500,000, still more preferably 100,000 to 1,500,000, from the viewpoint of obtaining a pressure-sensitive adhesive composition having high adhesiveness before applying a voltage.
  • the acrylic polymer (A1) used in one embodiment of the present invention is a structural unit (a3) derived from a monomer other than the monomer (a1') and (a2') (hereinafter, also referred to as "monomer (a3')"). ) May be a copolymer.
  • the content ratio of the structural units (a1) and (a2) is based on the total amount (100% by mass) of the structural units of the acrylic polymer (A1). It may be 55% by mass or more, 60% by mass or more, 65% by mass or more, 70% by mass or more, 75% by mass or more, 80% by mass or more, 85% by mass or more, 90% by mass or more, or 95% by mass or more. Further, it may be 100% by mass or less, 99% by mass or less, 95% by mass or less, 90% by mass or less, or 85% by mass or less.
  • the monomers and constituent units constituting the acrylic polymer (A1) will be described.
  • the alkyl group of the monomer (a1') preferably has 1 to 30, more preferably 1 to 20, more preferably 1 to 16, still more preferably 1 to 12, still more preferably 1 to 8, etc. Particularly preferably, it is 4 to 8.
  • the alkyl group of the monomer (a1') may be a linear alkyl group or a branched chain alkyl group.
  • the monomer (a1') examples include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate (n-propyl (meth) acrylate, i-propyl (meth) acrylate), and butyl (.
  • the monomer (a1') may be used alone or in combination of two or more.
  • the monomer (a1') preferably contains at least an alkyl (meth) acrylate having an alkyl group having 4 to 8 carbon atoms, and is preferably a butyl (meth) acrylate, a pentyl (meth) acrylate, or a hexyl (meth) acrylate.
  • Heptyl (meth) acrylate, and 2-ethylhexyl (meth) acrylate are more preferably contained
  • butyl (meth) acrylate or 2-ethylhexyl (meth) acrylate is further preferably contained. It is even more preferable to contain at least (meth) acrylate.
  • the acrylic polymer (A1) used in one embodiment of the present invention has, as the structural unit (a1), a structural unit (a1-1) derived from an alkyl (meth) acrylate having an alkyl group having 4 to 8 carbon atoms. It is also preferable to have a structural unit (a1-2) derived from an alkyl (meth) acrylate having an alkyl group having 1 to 3 carbon atoms together with the structural unit (a1-1).
  • the content ratio of the structural unit (a1-1) is based on the total amount (100% by mass) of the structural unit (a1) contained in the acrylic polymer (A1).
  • It is preferably 40% by mass or more, more preferably 50% by mass or more, more preferably 55% by mass or more, still more preferably 60% by mass or more, still more preferably 65% by mass or more, and particularly preferably 70% by mass or more. Further, it may be 100% by mass or less, 99% by mass or less, 98% by mass or less, 95% by mass or less, 90% by mass or less, 85% by mass or less, 80% by mass or less, or 76% by mass.
  • the content ratio of the structural unit (a1) is the total amount (100% by mass) of the structural units of the acrylic polymer (A1) before applying a voltage. From the viewpoint of obtaining a pressure-sensitive adhesive composition having better adhesiveness, it is preferably 30% by mass or more, more preferably 40% by mass or more, still more preferably 50% by mass or more, still more preferably 60% by mass or more, and particularly preferably. Is 70% by mass or more, and is preferably 99.99% by mass or less, from the viewpoint of obtaining a pressure-sensitive adhesive composition capable of securing the content ratio of the above-mentioned structural unit (a2) and further improving the cohesive force.
  • Examples of the monomer (a2') include a hydroxy group-containing monomer, a carboxy group-containing monomer, an epoxy group-containing monomer, and the like. These monomers (a2') may be used alone or in combination of two or more.
  • hydroxy-containing monomer examples include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and 3-hydroxybutyl (meth).
  • Hydroxyalkyl (meth) acrylates such as acrylates and 4-hydroxybutyl (meth) acrylates; unsaturated alcohols such as vinyl alcohols and allyl alcohols may be mentioned.
  • the alkyl group of the hydroxyalkyl (meth) acrylates has preferably 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms, still more preferably 1 to 6 carbon atoms, and even more preferably 2 to 4 carbon atoms.
  • the alkyl group may be a straight chain alkyl group or a branched chain alkyl group.
  • carboxy group-containing monomer examples include ethylenically unsaturated monocarboxylic acids such as (meth) acrylic acid and crotonic acid; ethylenically unsaturated dicarboxylic acids such as fumaric acid, itaconic acid, maleic acid and citraconic acid; 2-carboxyl. Examples thereof include ethyl (meth) acrylate.
  • epoxy-containing monomer examples include glycidyl (meth) acrylate, ⁇ -methylglycidyl (meth) acrylate, (3,4-epoxycyclohexyl) methyl (meth) acrylate, and 3-epoxycyclo-2-hydroxypropyl (meth) acrylate.
  • Epoxy group-containing (meth) acrylic acid esters such as glycidyl crotonate, allyl glycidyl ether and the like.
  • the acrylic polymer (A1) used in one embodiment of the present invention is preferably a copolymer having a structural unit (a2-1) derived from a hydroxy group-containing monomer as a structural unit (a2). ..
  • the content ratio of the structural unit (a2-1) is the total amount (100 mass) of the structural unit (a2) contained in the acrylic polymer (A1). %), More preferably 60 to 100% by mass, more preferably 70 to 100% by mass, still more preferably 80 to 100% by mass, still more preferably 90 to 100% by mass, and particularly preferably 95 to 100% by mass. Is.
  • the content ratio of the structural unit (a2) is such that the cohesive force is higher than the total amount (100% by mass) of the structural units of the acrylic polymer (A1).
  • it is preferably 0.01% by mass or more, more preferably 0.10% by mass or more, still more preferably 1.0% by mass or more, still more preferably 3.0% by mass.
  • the above is particularly preferably 4.0% by mass or more, and further 5.0% by mass or more, 7.0% by mass or more, 10.0% by mass or more, 12.0% by mass or more, or 15.0% by mass.
  • the above may be sufficient, and from the viewpoint of ensuring the content of the structural unit (a1) and obtaining a pressure-sensitive adhesive composition having better adhesiveness before applying a voltage, it is preferably 60% by mass or less, more preferably 50. It is mass% or less, more preferably 40% by mass or less, still more preferably 30% by mass or less, and particularly preferably 25% by mass or less.
  • the monomer (a3') other than the monomers (a1') and (a2') is not particularly limited, but for example, olefins such as ethylene, propylene and isobutylene, halogenated olefins such as vinyl chloride and vinylidene chloride, and the like.
  • Diene-based monomers such as butadiene, isoprene, and chloroprene, styrene, ⁇ -methylstyrene, vinyltoluene, vinyl formate, vinyl acetate, acrylonitrile, (meth) acrylamide, (meth) acrylonitrile, (meth) acryloylmorpholin, N-vinylpyrrolidone. And so on.
  • Diene-based monomers such as butadiene, isoprene, and chloroprene, styrene, ⁇ -methylstyrene, vinyltoluene, vinyl formate, vinyl acetate, acrylonitrile, (meth) acrylamide, (meth) acrylonitrile, (meth) acryloylmorpholin, N-vinylpyrrolidone. And so on.
  • These monomers (a3') may be used alone or in combination of two or more.
  • the content ratio of the structural unit (a3) is 0% by mass or more with respect to the total amount (100% by mass) of the structural units of the acrylic polymer (A1). It may be 1% by mass or more, 5% by mass or more, 10% by mass or more, or 15% by mass, and 45% by mass or less, 40% by mass or less, 35% by mass or less, 30% by mass or less, 25% by mass or less. , 20% by mass or less, 15% by mass or less, 10% by mass or less, or 5% by mass or less.
  • the blending amount of the component (A) is such that the pressure-sensitive adhesive composition has high adhesiveness before applying a voltage and can easily reduce the adhesiveness by applying a voltage.
  • the (content) is preferably 25% by mass or more, more preferably 30% by mass or more, more preferably 35% by mass or more, still more preferably 35% by mass or more, based on the total amount (100% by mass) of the active ingredient of the pressure-sensitive adhesive composition. Is 40% by mass or more, more preferably 45% by mass or more, still more preferably 50% by mass or more, particularly preferably 55% by mass or more, and preferably 98% by mass or less, more preferably 95% by mass or less.
  • ionic compound (B) used in one embodiment of the present invention include one or more selected from an alkali metal salt (B1), an organic quaternary ammonium salt (B2), and an ionic liquid (B3). ..
  • the component (B) used in one embodiment of the present invention preferably contains at least one selected from an alkali metal salt (B1) and an ionic liquid (B3). Further, as the component (B) used in one embodiment of the present invention, it is preferable to use an alkali metal salt (B1) or an ionic liquid (B3) as a main component.
  • the above-mentioned "main component” means the component having the highest content among the components constituting the component (B). Further, a pressure-sensitive adhesive composition having a large amount of a liquid component such as an ionic liquid (B3) may have insufficient adhesiveness.
  • the pressure-sensitive adhesive composition of one aspect of the present invention since the rosin-based diol (C) having good compatibility with the ionic liquid (B3) is blended, the pressure-sensitive adhesiveness is further improved and a voltage is applied. It is possible to obtain a pressure-sensitive adhesive composition that can easily reduce the stickiness.
  • the content of the component (B) other than the alkali metal salt (B1) is 100 parts by mass with respect to the total amount of the alkali metal salt (B1). Less than 100 parts by mass, 0 to 90 parts by mass, 0 to 50 parts by mass, 0 to 30 parts by mass, 0 to 20 parts by mass, 0 to 10 parts by mass, 0 to 5 parts by mass, 0 to 1 part by mass, 0 to 0 .1 part by mass, 0 to 0.01 part by mass, 0 to 0.001 part by mass, or 0 to 0.0001 part by mass.
  • the content of the component (B) other than the ionic liquid (B3) is 100 parts by mass with respect to 100 parts by mass of the total amount of the ionic liquid (B3). Less than, 0 to 90 parts by mass, 0 to 50 parts by mass, 0 to 30 parts by mass, 0 to 20 parts by mass, 0 to 10 parts by mass, 0 to 5 parts by mass, 0 to 1 part by mass, 0 to 0.1 parts by mass. It may be 0 to 0.01 parts by mass, 0 to 0.001 parts by mass, or 0 to 0.0001 parts by mass.
  • the blending ratio of the component (B) with respect to 100 parts by mass of the total amount of the component (A) is a viewpoint of obtaining a pressure-sensitive adhesive composition that can easily reduce the adhesiveness by applying a voltage. Therefore, it is preferably 1.0 part by mass or more, more preferably 3.0 part by mass or more, more preferably 5.0 part by mass or more, still more preferably 7.0 part by mass or more, still more preferably 9.0 part by mass or more.
  • the pressure-sensitive adhesive composition is particularly preferably 11.0 parts by mass or more, further may be 13.0 parts by mass or more, or 16.0 parts by mass or more, and has high adhesiveness before applying a voltage.
  • the blending amount (content) of the component (B) is easily adhered to the total amount (100% by mass) of the active component of the pressure-sensitive adhesive composition by applying a voltage.
  • it is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, more preferably 1.0% by mass or more, still more preferably 3.0% by mass.
  • % Or more more preferably 5.0% by mass or more, particularly preferably 7.0% by mass or more, and preferably 50% by mass from the viewpoint of obtaining a pressure-sensitive adhesive composition having high adhesiveness before applying a voltage.
  • % Or less more preferably 40% by mass or less, more preferably 30% by mass or less, still more preferably 25% by mass or less, still more preferably 20% by mass or less, and particularly preferably 15% by mass or less.
  • the alkali metal salt (B1) used in one embodiment of the present invention is solid at room temperature (25 ° C.), but may be a compound that ionizes cations (alkali metal ions) and anions in a liquid.
  • Specific alkali metal salts (B1) include, for example, MCl, MBr, MI, MAlCl 4 , MAL 2 Cl 7 , MBF 4 , MPF 6 , MSCN, MClO 4 , MNO 3 , CH 3 COOM, C 9 H 19 .
  • the alkali metal salt (B1) used as the component (B) in one aspect of the present invention preferably contains the alkali metal salt (B11) represented by the following general formula (b-1).
  • RF is independently a fluorine atom or a fluorinated alkyl group.
  • the number of carbon atoms of the fluorinated alkyl group is preferably 1 to 10, more preferably 1 to 8, still more preferably 1 to 4, still more preferably 1 to 3, and particularly preferably 1 to 2.
  • fluorinated alkyl group means a group in which at least one hydrogen atom of an alkyl group is substituted with a fluorine atom, and may be a straight chain or a branched chain. good.
  • the RF is preferably a fluorine atom or a perfluoroalkyl group, which is a fluorine atom, -CF 3 , -C 2 F 5 , -C 3 F 7 , or -C 4 F 9 . Is more preferable, and it is further preferable that it is a fluorine atom or ⁇ CF3 .
  • M is an alkali metal atom (lithium atom (Li), sodium atom (Na), potassium atom (K), rubidium atom (Rb), cesium atom (Cs), francium atom (Fr)), but Li, Na.
  • Li lithium atom (Li), sodium atom (Na), potassium atom (K), rubidium atom (Rb), cesium atom (Cs), francium atom (Fr)
  • Li Na.
  • it is preferably K, more preferably Na or K, and even more preferably Na.
  • the organic quaternary ammonium salt (B2) used in one embodiment of the present invention may be a compound represented by the following general formula (b-2), which is a solid at room temperature (25 ° C.).
  • the organic quaternary ammonium salt (B2) may be used alone or in combination of two or more.
  • R 11 to R 14 are independently alkyl groups having 1 to 4 carbon atoms.
  • X is F, Cl, Br, I, ClO 4 , BF 4 , PF 6 , or [(R 15 ) 4 N] 2 SO 4 (R 15 is an independently alkyl group having 1 to 4 carbon atoms. )be.
  • Specific organic quaternary ammonium salts (B2) include, for example, ammonium bromide or ammonium chloride such as tetrabutyl, tetrapropyl, tetraethyl, tetramethyl, triethylbutyl, triethylpropyl, triethylmethyl; tetrabutyl, tetrapropyl, tetraethyl, Ammonium tetrafluoroborate such as tetramethyl, triethylbutyl, triethylpropyl, triethylmethyl; ammonium hexafluorophosphate such as tetrabutyl, tetrapropyl, tetraethyl, tetramethyl, triethylbutyl, triethylpropyl, triethylmethyl; tetrabutyl, tetrapropyl, tetraethyl ,
  • the ionic liquid (B3) used in one embodiment of the present invention may be a molten salt that is liquid at room temperature (25 ° C.) and may be a compound composed of an organic cation and its counterion, an anion.
  • Examples of the organic cation constituting the ionic liquid (B3) include cations represented by any of the following general formulas (b-3-i) to (b-3-viii).
  • the organic cation constituting the ionic liquid (B3) is preferably a cation represented by the following general formula (b-3-ii).
  • Ra is independently an alkyl group having 1 to 20 carbon atoms or an alkenyl group having 1 to 20 carbon atoms.
  • R b is independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, and-(C 2 H 4 O). It is a group represented by n —R c (n is an integer of 1 to 20, R c is an alkyl group having 1 to 20 carbon atoms), or an amino group.
  • the alkyl groups that can be selected by R a , R b and R c include, for example, a methyl group, an ethyl group, a propyl group (n-propyl group, i-propyl group), a butyl group (n-butyl group, etc.).
  • alkyl group may be a linear alkyl group or a branched chain alkyl group.
  • Examples of the alkenyl group that can be selected as R a and R b include an ethenyl group (vinyl group), a propenyl group, a butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, a nonenyl group and a decenyl group. , Dodecenyl group, tridecenyl group, tetradecenyl group, pentadecenyl group, hexadecenyl group, octadecenyl group and the like.
  • the alkenyl group may be a linear alkyl group or a branched chain alkyl group.
  • At least one hydrogen atom bonded to the carbon atom of the cation represented by any of the general formulas (b-3-i) to (b-3-ii) is an alkyl having 1 to 20 carbon atoms. It may be substituted with a group. Specific examples of the alkyl group are as described above.
  • Examples of the cation represented by the general formula (b-3-i) and the cation in which at least one hydrogen atom of the cation is substituted with the alkyl group include the following formula (b-3-i-1). )-(B-3-i-11).
  • Examples of the cation represented by the general formula (b-3-ii) and the cation in which at least one hydrogen atom of the cation is substituted with the alkyl group include the following formula (b-3-ii-1). )-(B-3-ii-26), and the cations represented by any of the following formulas (b-3-ii-1) to (b-3-ii-15).
  • the cation is preferably one of the following formulas (b-3-ii-1) to (b-3-ii-3) and (b-3-ii-9) to (b-3-ii-10).
  • the represented cation is more preferable, and the cation represented by any of the following formulas (b-3-ii-1) to (b-3-ii-3) is more preferable, and the following formula (b-3-ii-) is more preferable.
  • the cation represented by 2) is even more preferable.
  • a cation represented by the general formula (b-3-iii) for example, a cation represented by any of the following formulas (b-3-iii-1) to (b-3-iii-6) can be used. Can be mentioned.
  • a cation represented by the general formula (b-3-iv) for example, a cation represented by any of the following formulas (b-3-iv-1) to (b-3-iv-6) can be used. Can be mentioned.
  • Examples of the cation represented by any of the general formulas (b-3-v) to (b-3-viii) include cations represented by any of the following formulas.
  • Examples of the anions constituting the ionic liquid (B3) include Cl- , Br- , I- , AlCl 4- , Al 2 Cl 7- , BF 4- , PF 6- , SCN- , ClO 4- , NO 3 - , CH 3 COO- , CF 3 COO- , CH 3 SO 3- , CF 3 SO 3- , C 4 F 9 SO 3- , (CF 3 SO 2 ) 2 N- , (C 2 F 5 SO 2 ) 2 N- , (C 3 F 7 SO 2 ) 2 N- , (C 4 F 9 SO 2 ) 2 N- , (CF 3 SO 2 ) 3 C- , AsF 6- , SbF 6- , NbF 6- , TaF 6- , (CN) 2 N- , C 4 F 9 SO 3- , (C 2 F 5 SO 2 ) 2 N- , C 3 F 7 COO- , (CF 3 SO 2 ) (CF 3 CO) N - , C 9 H 19 COO-
  • the rosin-containing diol (C) used in one embodiment of the present invention may be any diol having a rosin-derived skeleton, and examples thereof include a reaction product of rosin and an epoxy compound.
  • the rosin-containing diol (C) may be used alone or in combination of two or more.
  • the rosin constituting the rosin-containing diol (C) means a residual resin obtained from a resin oil obtained from a Pinaceae plant as a raw material and after distilling off a volatile substance such as an essential oil. Usually, it is a mixture containing a resinic acid containing abietic acid and its relatives as main components and a small amount of neutral components.
  • the resin acid include abietic acid, dehydroabietic acid, dihydroabietic acid, tetrahydroabietic acid, diavietic acid, neoavietic acid, levopipial acid, hydrogenated hydrogenated rosin, and disproportionated rosin obtained by hydrogenating these. And so on.
  • Examples of the epoxy compound include ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, dipropylene glycol diglycidyl ether, and tripropylene glycol diglycidyl.
  • Acyclic aliphatic diglycidyl ethers such as ether, polypropylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether; 2,2-bis (4-hydroxyphenyl) propan diglycidyl ether.
  • Aromatic diglycidyl ethers such as 5,5'-tetramethyl-4,4'-dihydroxybiphenyl diglycidyl ether, 2,2'-bis (4- ( ⁇ -hydroxypropoxy) phenyl) propan diglycidyl ether or cyclic Examples thereof include aliphatic diglycidyl ethers; cyclic aliphatic cyclic oxylanes such as 3,4-epoxycyclohexylmethyl, 3,4-epoxycyclohexanecarboxylate and vinylcyclohexendioxide; and the like. These epoxy compounds may be used alone or in combination of two or more.
  • the rosin-containing diol (C) used in one embodiment of the present invention is preferably a compound having two rosin-derived skeletons and two hydroxyl groups in the molecule.
  • the softening point of the rosin-containing diol (C) used in one embodiment of the present invention is a voltage obtained by improving the compatibility with the components (A) and (B) (particularly, the compatibility with the component (B)).
  • a pressure-sensitive adhesive composition which has high adhesiveness before application but can easily reduce the adhesiveness by applying a voltage
  • it is preferably 60 ° C. or higher, more preferably 65 ° C. or higher, still more preferably 70 ° C. or higher. More preferably 75 ° C. or higher, particularly preferably 80 ° C. or higher, and more preferably 160 ° C. or lower, more preferably 150 ° C. or lower, still more preferably 140 ° C.
  • the softening point means a value measured according to the ring ball method specified by JIS K5902.
  • the acid value of the rosin-containing diol (C) used in one embodiment of the present invention is a voltage due to the good compatibility with the components (A) and (B) (particularly, the compatibility with the component (B)).
  • it is preferably 0 to 10.0 mgKOH / g, more preferably 0 to 4.9 mgKOH /. g, more preferably 0 to 1.9 mgKOH / g, even more preferably 0 to 1.4 mgKOH / g, and particularly preferably 0 to 1.1 mgKOH / g.
  • the hydroxyl value of the rosin-containing diol (C) used in one embodiment of the present invention has good compatibility with the components (A) and (B) (particularly, compatibility with the component (B)).
  • it is preferably 30 mgKOH / g or more, more preferably 50 mgKOH / g or more, still more preferable.
  • the acid value and the hydroxyl value mean the values measured according to the potentiometric titration method specified by JIS K0070.
  • the blending ratio of the component (C) with respect to 100 parts by mass of the total amount of the component (A) is a viewpoint of obtaining a pressure-sensitive adhesive composition that can easily reduce the adhesiveness by applying a voltage. Therefore, it is preferably 2.0 parts by mass or more, more preferably 5.0 parts by mass or more, more preferably 8.0 parts by mass or more, still more preferably 12.0 parts by mass or more, still more preferably 18.0 parts by mass.
  • the above is particularly preferably 22.0 parts by mass or more, further may be 25.0 parts by mass or more, or 30.0 parts by mass or more, and is compatible with the components (A) and (B) (particularly).
  • Compatibility with the component (B)) is good, and from the viewpoint of obtaining a pressure-sensitive adhesive composition having high adhesiveness before applying a voltage, it is preferably 300 parts by mass or less, more preferably 200 parts by mass or less, and more preferably. 150 parts by mass or less, more preferably 130 parts by mass or less, still more preferably 120 parts by mass or less, particularly preferably 110 parts by mass or less, and further 100 parts by mass or less, 90 parts by mass or less, 80 parts by mass or less, 70. It may be 5 parts by mass or less, 60 parts by mass or less, or 50 parts by mass or less.
  • the blending amount (content) of the component (C) is easily adhered to the total amount (100% by mass) of the active component of the pressure-sensitive adhesive composition by applying a voltage. From the viewpoint of making a pressure-sensitive adhesive composition capable of reducing the properties, it is preferably 0.2% by mass or more, more preferably 1.2% by mass or more, more preferably 3.0% by mass or more, and more preferably 5.0% by mass.
  • % Or more more preferably 7.0% by mass or more, still more preferably 9.0% by mass or more, still more preferably 11.0% by mass or more, particularly preferably 16.0% by mass or more, and the components ( From the viewpoint of making a pressure-sensitive adhesive composition having good compatibility with A) and (B) (particularly, compatibility with component (B)) and high adhesiveness before applying a voltage, it is preferably 60% by mass or less. , More preferably 55% by mass or less, more preferably 50% by mass or less, still more preferably 45% by mass or less, still more preferably 40% by mass or less, particularly preferably 35% by mass or less, and further preferably 30% by mass or less. , 27% by mass or less, or 25% by mass or less.
  • a component with respect to the component (B) from the viewpoint of making a pressure-sensitive adhesive composition which has high adhesiveness before voltage application but can easily reduce the adhesiveness by voltage application.
  • the compounding amount ratio [(C) / (B)] of (C) is preferably 0.10 or more, more preferably 0.30 or more, more preferably 0.50 or more, still more preferably 0. 80 or more, more preferably 1.00 or more, still more preferably 1.20 or more, particularly preferably 1.50 or more, and preferably 20.0 or less, more preferably 15.0 or less, more preferably. It is 10.0 or less, more preferably 8.0 or less, still more preferably 6.0 or less, still more preferably 5.0 or less, and particularly preferably 4.0 or less.
  • the pressure-sensitive adhesive composition according to one aspect of the present invention may contain a pressure-sensitive adhesive other than the component (C) as long as the effects of the present invention are not impaired.
  • Such other tackifiers include rosin-based resins other than the component (C); hydrogenated rosin-based resins obtained by hydrogenating rosin-based resins other than the component (C); terpene-based resins, terpenephenol-based resins, and fragrances.
  • Terpen-based resins such as group-modified terpene-based resins; Hydrogenated terpene-based resins obtained by hydrogenating these terpene-based resins; C5 based petroleum resin obtained by copolymerization and hydrogenated petroleum resin of this C5 based petroleum resin; C9 fractions such as inden, vinyltoluene, ⁇ -methylstyrene, ⁇ -methylstyrene produced by thermal decomposition of petroleum naphtha Examples thereof include a C9-based petroleum resin obtained by copolymerization and a hydrogenated petroleum resin of the C9-based petroleum resin. These other tackifiers may be used alone or in combination of two or more.
  • the component (C) contained in the pressure-sensitive adhesive composition of one aspect of the present invention is obtained from the viewpoint of obtaining a pressure-sensitive adhesive composition which has high adhesiveness before voltage application and can easily reduce the adhesiveness by voltage application. ),
  • the content of the tackifier other than the specific component (C) is preferably less than 10 parts by mass, more preferably less than 100 parts by mass, based on 100 parts by mass of the total amount of the component (C) contained in the pressure-sensitive adhesive composition. It is less than 5 parts by mass, more preferably less than 1 part by mass, still more preferably less than 0.1 parts by mass, and particularly preferably less than 0.01 parts by mass.
  • the pressure-sensitive adhesive composition according to one aspect of the present invention is preferably a pressure-sensitive adhesive composition further containing a cross-linking agent (D).
  • a cross-linking agent (D) By blending the cross-linking agent (D), it becomes easy to prepare a pressure-sensitive adhesive composition which has high adhesiveness before voltage application but can easily reduce the adhesiveness by voltage application.
  • the cross-linking agent (D) may be used alone or in combination of two or more.
  • cross-linking agent (D) used in one aspect of the present invention examples include isocyanate-based cross-linking agents, epoxy-based cross-linking agents, imine-based cross-linking agents, and metal chelate-based cross-linking agents.
  • isocyanate-based cross-linking agent examples include tolylene diisocyanate compounds such as 2,4-tolylene diisocyanate and 2,6-tolylene diisocyanate; Range isocyanate compounds; diphenylmethane-4,4'-diisocyanate, diphenylmethane-2,4'-diisocyanate, 3-methyldiphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, dicyclohexylmethane-4,4'-diisocyanate, dicyclohexylmethane-2 , 4'-diisocyanate, lysine isocyanate and the like.
  • a trimer of these organic polyvalent isocyanate compounds, a terminal isocyanate urethane prepolymer obtained by reacting these organic polyvalent isocyanate compounds with a polyol compound, and the like can also be used.
  • epoxy-based cross-linking agent examples include bisphenol A type epoxy compound, bisphenol F type epoxy compound, 1,3-bis (N, N-diglycidylaminomethyl) toluene, N, N, N', N'-tetraglycidyl. -4,4-diaminodiphenylmethane and the like can be mentioned.
  • imine-based cross-linking agent examples include N, N'-diphenylmethane-4,4'-bis (1-aziridinecarboxyamide), trimethylolpropane-tri- ⁇ -aziridinylpropionate, and trimethylolmethane-tri.
  • imine-based cross-linking agent examples include N, N'-diphenylmethane-4,4'-bis (1-aziridinecarboxyamide), trimethylolpropane-tri- ⁇ -aziridinylpropionate, and trimethylolmethane-tri.
  • examples thereof include - ⁇ -aziridinyl propionate, N, N'-toluene-2,4-bis (1-aziridinecarboxyamide) triethylene melamine and the like.
  • metal chelate-based cross-linking agent examples include polyvalent metal coordinating compounds such as aluminum chelate-based compounds such as trisethylacetacetate aluminum, ethylacetate acetate aluminum diisopropyrate, and trisacetylacetonate aluminum.
  • the component (A) is easy to prepare with a pressure-sensitive adhesive composition which has high adhesiveness before application of voltage and can easily reduce the adhesiveness by application of voltage.
  • the mixing ratio of the component (D) with respect to 100 parts by mass of the total amount of) is preferably 0.001 to 10.0 parts by mass, more preferably 0.005 to 7.0 parts by mass, and further preferably 0.010 to 5 parts. It is 0.0 part by mass, more preferably 0.050 to 2.0 parts by mass, and particularly preferably 0.100 to 1.0 part by mass.
  • the pressure-sensitive adhesive composition according to one aspect of the present invention is preferably a pressure-sensitive adhesive composition further containing the compound (E) represented by the following general formula (e-1).
  • e-1 the compound represented by the following general formula (e-1)
  • the pressure-sensitive adhesive composition can be obtained even before the voltage is applied.
  • the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition containing the compound (E) is applied to the aluminum plate before the voltage is applied. It is possible to develop high adhesive strength.
  • the compound (E) may be used alone or in combination of two or more.
  • R 1 is an alkylene group having 1 to 8 carbon atoms (preferably 1 to 6, more preferably 1 to 4, still more preferably 2 or 3).
  • R2 is a hydrogen atom, an alkyl group having 1 to 12 carbon atoms (preferably 1 to 8, more preferably 1 to 6, still more preferably 1 to 3), or a hydroxy group.
  • R 3 is a hydrogen atom or an alkyl group having 1 to 12 carbon atoms (preferably 1 to 8, more preferably 1 to 6, still more preferably 1 to 3).
  • n is an integer of 1 or more.
  • alkylene group examples include a methylene group (-CH 2- ), an ethylene group (-CH 2 CH 2- ), an ethylidene group (-CH (CH 3 )-), and a trimethylene group (-CH (CH 3)-).
  • R 1 is preferably an ethylene group or a propylene group, and more preferably an ethylene group.
  • the alkyl groups that can be selected as R 2 and R 3 include methyl group, ethyl group, propyl group (n-propyl group, i-propyl group), butyl group (n-butyl group, i-butyl group, s). -Butyl group, t-butyl group), pentyl group (n-pentyl group, i-pentyl group, neopentyl group), hexyl group, heptyl group, octyl group, 2-ethylhexyl group, nonyl group, decyl group, undecyl group, Dodecyl group and the like can be mentioned.
  • the compound (E) used in one embodiment of the present invention is preferably polyalkylene glycol in which R 2 in the general formula (e-1) is a hydroxy group and R 3 is a hydrogen atom, and polyethylene glycol or polypropylene glycol is more preferable.
  • polyethylene glycol is even more preferred.
  • the mass average molecular weight (Mw) of the compound (E) used in one embodiment of the present invention is preferably 50 to 2,000, more preferably 90 to 1,000, still more preferably 130 to 500, still more preferably 170 to. It is 300.
  • the blending ratio of the component (E) with respect to 100 parts by mass of the total amount of the component (A) is preferably 0.1 to 30 parts by mass, more preferably 0.5 to 25 parts by mass, and further preferably 1. It is 0 to 20 parts by mass, more preferably 2.5 to 16 parts by mass, and particularly preferably 4.0 to 12.0 parts by mass.
  • the pressure-sensitive adhesive composition according to one aspect of the present invention may contain or contain additives other than the components (A) to (E).
  • additives are appropriately selected depending on the use of the pressure-sensitive adhesive sheet using the pressure-sensitive adhesive composition, and for example, a compatibilizer, a wetting agent, a thickener, a defoaming agent, and an antioxidant. Examples thereof include agents, ultraviolet absorbers, softeners (plasticizers), fillers, rust preventives, pigments, dyes and the like.
  • additives used in general pressure-sensitive adhesive compositions can be used.
  • each additive may be used alone or in combination of two or more.
  • the blending amount of each of these other additives is appropriately set according to the type of the additive, but is preferably 0.01 to 50 parts by mass with respect to 100 parts by mass of the total amount of the component (A). It is preferably 0.05 to 40 parts by mass, more preferably 0.1 to 30 parts by mass, and even more preferably 0.2 to 20 parts by mass.
  • the pressure-sensitive adhesive composition according to one aspect of the present invention may be further diluted with an organic solvent to form a solution from the viewpoint of facilitating application to a substrate or the like described later and improving workability.
  • organic solvent include methyl ethyl ketone, acetone, ethyl acetate, tetrahydrofuran, dioxane, cyclohexane, n-hexane, toluene, xylene, n-propanol, isopropanol and the like.
  • the organic solvent used at the time of synthesizing the component (A) may be used as it is, or one or more organic solvents other than the organic solvent used at the time of synthesizing the component (A) may be added. You may.
  • the electrically peelable pressure-sensitive adhesive sheet of the present invention (hereinafter, also simply referred to as “adhesive sheet”) has a pressure-sensitive adhesive layer formed from the above-mentioned electro-removable pressure-sensitive adhesive composition of the present invention.
  • the pressure-sensitive adhesive sheet according to one aspect of the present invention is not particularly limited as long as it has the pressure-sensitive adhesive layer, and may be, for example, a pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer on at least one side of the base material. It may be an adhesive sheet having a structure sandwiched between two release sheets.
  • FIG. 1 is a schematic cross-sectional view of the pressure-sensitive adhesive sheet showing an example of the configuration of the electrically peelable pressure-sensitive adhesive sheet according to one aspect of the present invention.
  • a specific configuration of the pressure-sensitive adhesive sheet according to one aspect of the present invention for example, as shown in FIG. 1 (a), an electric peeling with a base material having a pressure-sensitive adhesive layer 3 on one surface side of the base material 2 is provided.
  • the sex adhesive sheet 1a can be mentioned.
  • FIG. 1 (b) there is a configuration such as an electrically peelable pressure-sensitive adhesive sheet 1b with a base material having a pressure-sensitive adhesive layer 3 and a pressure-sensitive adhesive layer 3'on both surface sides of the base material 2. It may be.
  • the base material 2 and the pressure-sensitive adhesive layer 3 may be directly laminated as shown in the electrically peelable pressure-sensitive adhesive sheet 1a shown in FIG. 1 (a).
  • Another layer may be provided between the material 2 and the pressure-sensitive adhesive layer 3. This also applies to the base material 2 and the pressure-sensitive adhesive layer 3 and the base material 2 and the pressure-sensitive adhesive layer 3'in the electrically peelable pressure-sensitive adhesive sheet 1b shown in FIG. 1 (b).
  • the pressure-sensitive adhesive sheet has a structure such as the electrically peelable pressure-sensitive adhesive sheet 1c with a substrate in which the release sheet 4 is further laminated on the pressure-sensitive adhesive surface of the pressure-sensitive adhesive layer 3 shown in FIG. 1 (c). It may be.
  • the release sheet in the electrically peelable pressure-sensitive adhesive sheet 1b, can be laminated on the pressure-sensitive adhesive surfaces of the pressure-sensitive adhesive layer 3 and the pressure-sensitive adhesive layer 3', respectively.
  • the pressure-sensitive adhesive sheet according to one aspect of the present invention has a structure in which the pressure-sensitive adhesive layer 3 is sandwiched between two release sheets 4 and 4'without using a base material as shown in FIG. 1 (d). It may have a structure such as the baseless electrically peelable pressure-sensitive adhesive sheet 1d.
  • the materials of the release sheets 4 and 4'of the electrically peelable adhesive sheet 1d may be the same or different, but the materials are adjusted so that the release forces of the release sheet 4 and the release sheet 4'are different. It is preferable to have.
  • the pressure-sensitive adhesive layer of the pressure-sensitive adhesive sheet of the present invention is a layer formed from the above-mentioned electro-peelable pressure-sensitive adhesive composition of the present invention, and has a property that the pressure-sensitive adhesive force can be reduced by applying a voltage.
  • the thickness of the pressure-sensitive adhesive layer of the pressure-sensitive adhesive sheet according to one aspect of the present invention is appropriately adjusted depending on the intended use, etc., but is preferably 0.5 to 120 ⁇ m, more preferably 1 to 100 ⁇ m, and further preferably 3 to 80 ⁇ m. , More preferably 5 to 80 ⁇ m, and particularly preferably 10 to 60 ⁇ m.
  • the pressure-sensitive adhesive sheet can be an electrically peelable pressure-sensitive adhesive sheet which is advantageous in terms of productivity and is also good in terms of handleability.
  • the base material of the pressure-sensitive adhesive sheet according to one aspect of the present invention is preferably a conductive base material from the viewpoint of applying a voltage to the pressure-sensitive adhesive layer of the pressure-sensitive adhesive sheet when it is desired to be peeled off from the adherend. That is, it is preferable that the pressure-sensitive adhesive sheet according to one aspect of the present invention has a conductive base material and a pressure-sensitive adhesive layer on at least one surface side of the conductive base material.
  • the material constituting the conductive substrate include metals such as aluminum, tin-doped indium oxide, copper, iron, silver, platinum, and gold, and alloys of these metals.
  • a metal vapor deposition body obtained by depositing the above metal on a resin film such as polyethylene terephthalate may be used as a base material.
  • a resin film such as polyethylene terephthalate
  • the thickness of the base material is preferably 5 to 300 ⁇ m, more preferably 10 to 150 ⁇ m, and even more preferably 20 to 100 ⁇ m.
  • the release sheet of the pressure-sensitive adhesive sheet according to one aspect of the present invention can be obtained by applying a release agent to one side or both sides of the base material for a release sheet.
  • the base material for the release sheet include polyethylene such as polyethylene terephthalate, polybutylene terephthalate, and polyethylene naphthalate, polyethylene, polypropylene, polybutene, polybutadiene, polymethylpentene, polyvinyl chloride, and vinyl chloride copolymer, polyurethane, and ethylene-.
  • Resin films such as vinyl acetate copolymer, ionomer resin, ethylene (meth) acrylic acid copolymer, polystyrene, polycarbonate, fluororesin, low-density polyethylene, linear low-density polyethylene, triacetyl cellulose, high-quality paper, coated paper , Paper base material such as glassin paper, laminated paper obtained by laminating a thermoplastic resin such as polyethylene on these paper base materials and the like.
  • Examples of the release agent used in one embodiment of the present invention include silicone-based resins, olefin-based resins, long-chain alkyl-based resins, alkyd-based resins, fluororesins, isoprene-based resins, butadiene-based resins, and other rubber-based elastomers. Can be mentioned.
  • the thickness of the release sheet is not particularly limited, but is preferably 5 to 300 ⁇ m, more preferably 10 to 200 ⁇ m.
  • a polyester film is used as the base material for the release sheet, it is preferably 10 to 100 ⁇ m.
  • the method for producing the electrically peelable pressure-sensitive adhesive sheet of the present invention is not particularly limited, and the pressure-sensitive adhesive composition of one aspect of the present invention prepared by the above-mentioned method is applied onto the above-mentioned base material or the above-mentioned release sheet by a known coating method. Can be applied and manufactured. From the viewpoint of improving the coatability on the substrate or the release sheet, it is preferable that the pressure-sensitive adhesive composition according to one aspect of the present invention is diluted with an organic solvent and used in the form of a solution.
  • Examples of the method for applying the pressure-sensitive adhesive composition onto a substrate or a release sheet include a spin coating method, a spray coating method, a bar coating method, a knife coating method, a roll coating method, a blade coating method, a die coating method, and a gravure coating method. And so on.
  • the pressure-sensitive adhesive composition On the base material or the release sheet to form a coating film, and then perform a drying treatment.
  • As the drying condition of the formed coating film it is preferable to heat it at a temperature of 80 ° C. to 150 ° C. for 30 seconds to 5 minutes (preferably 40 seconds to 3 minutes, more preferably 45 seconds to 2 minutes) and dry it. ..
  • an adhesive layer can be formed on the base material or the release sheet.
  • a seasoning step of holding the cross-linking agent for a certain period of time (for example, about 1 to 14 days) is performed in order to complete the cross-linking. It is preferable to go through.
  • the pressure-sensitive adhesive composition used does not contain a cross-linking agent, it is not necessary to carry out the seasoning step.
  • the electrically peelable pressure-sensitive adhesive sheet 1a having the pressure-sensitive adhesive layer 3 on one side of the base material 2 as shown in FIG. 1A is, for example, a solution of the above-mentioned pressure-sensitive adhesive composition on one surface of the base material 2. Can be directly applied to form the pressure-sensitive adhesive layer 3. Further, a solution of the above-mentioned pressure-sensitive adhesive composition is directly applied onto the peel-processed surface of the release sheet to form the pressure-sensitive adhesive layer 3, and then the pressure-sensitive adhesive layer 3 and the base material 2 are bonded to each other to form a release sheet. May be produced by removing.
  • the solution of the above-mentioned pressure-sensitive adhesive composition is directly applied to both sides of the base material 2. It can be applied to form pressure-sensitive adhesive layers 3, 3'and produced. Further, two sheets having a pressure-sensitive adhesive layer formed by directly applying the solution of the above-mentioned pressure-sensitive adhesive composition on the peel-off surface of the release sheet are prepared, and each pressure-sensitive adhesive layer is applied to both surfaces of the base material 2. It may be produced by laminating and removing the release sheet.
  • the electrically peelable pressure-sensitive adhesive sheet 1c having the pressure-sensitive adhesive layer 3 and the release sheet 4 on the base material 2 as shown in FIG. 1 (c) in this order is, for example, the electrically peelable pressure-sensitive adhesive sheet 1a obtained as described above.
  • the release sheet 4 can be laminated on the surface of the pressure-sensitive adhesive layer 3 of the above. Further, a solution of the above-mentioned pressure-sensitive adhesive composition is directly applied onto the peel-processed surface of the peel-off sheet 4 to form the pressure-sensitive adhesive layer 3, and then the pressure-sensitive adhesive layer 3 and the base material 2 are bonded together. You may.
  • the electrically peelable pressure-sensitive adhesive sheet 1d having a structure in which the pressure-sensitive adhesive layer 3 is sandwiched between two release sheets 4 and 4'without using a base material as shown in FIG. 1 (d) is, for example, the release sheet 4.
  • a solution of the above-mentioned pressure-sensitive adhesive composition is directly applied onto the surface to be peeled off to form a pressure-sensitive adhesive layer 3, and then another release sheet 4'is laminated on the surface of the pressure-sensitive adhesive layer 3. can do.
  • the pressure-sensitive adhesive sheet according to one aspect of the present invention has a property of peeling off on the cathode side when a voltage is applied to the pressure-sensitive adhesive layer. That is, the adhesive surface of the adhesive layer connected to the cathode side is peeled off from the adherend or the base material attached to the adhesive surface.
  • the electrically peelable pressure-sensitive adhesive sheet 1a according to one aspect of the present invention is to be peeled off from the adherend 11 as shown in FIG. 2A. In FIG.
  • the pressure-sensitive adhesive layer 3 is sandwiched between the adherend 11 and the base material 2a, the anode terminal 51 of the voltage applying device 50 is connected to the base material 2a, and the cathode terminal 52 is adhered.
  • a voltage can be applied between both surfaces of the pressure-sensitive adhesive layer 3.
  • the configuration of the "base material 2a" in FIG. 2 becomes another "adhesive", and the pressure-sensitive adhesive is used.
  • the layer 3 is sandwiched between two adherends, and by connecting the anode terminal 51 and the cathode terminal 52 of the voltage applying device 50 to the respective adherends, the layers 3 are formed on both sides of the pressure-sensitive adhesive layer 3. A voltage can be applied between them.
  • FIG. 2A When a voltage is applied in the state shown in FIG. 2A, the adhesive surface 3a of the adhesive layer connected to the cathode side and the adhesive surface 3a are attached as shown in FIG. 2B.
  • the adhesive strength is reduced between the adherend and the adherend 11, and the electrically peelable adhesive sheet 1a can be easily peeled off from the adherend.
  • the applied voltage (applied voltage) is preferably 1 to 200 V, more preferably 3 to 140 V, still more preferably 6 to 120 V, and the time (applied time) for applying the voltage in the range is preferably 1 to 180. Seconds, more preferably 5 to 120 seconds, even more preferably 10 to 90 seconds.
  • the adhesive strength before applying a voltage is preferably 5.0 N / 25 mm or more, more preferably 6.0 N. / 25 mm or more, more preferably 7.5 N / 25 mm or more, still more preferably 8.0 N / 25 mm or more, still more preferably 8.5 N / 25 mm or more, still more preferably 9.0 N / 25 mm or more, and particularly preferably 11. It may be 0N / 25mm or more, and may be 13.0N / 25mm or more, 15.0N / 25mm or more, 20.0N / 25mm or more, or 25.0N / 25mm or more.
  • the adhesive force of the pressure-sensitive adhesive layer of the pressure-sensitive adhesive sheet according to the present invention is preferably 0.20 N / 25 mm or less after the pressure-sensitive adhesive layer is attached to an aluminum plate as an adherend and a voltage is applied at 10 V for 60 seconds. , More preferably 0.10 N / 25 mm or less, still more preferably 0.05 N / 25 mm or less, still more preferably 0.01 N / 25 mm or less, and particularly preferably 0.005 N / 25 mm or less.
  • the adhesive strength before applying a voltage is preferably 3.0 N / 25 mm or more, more preferably 5.0 N. It is / 25 mm or more, more preferably 10.0 N / 25 mm or more, further preferably 12.0 N / 25 mm or more, still more preferably 15.0 N / 25 mm or more, and particularly preferably 20.0 N / 25 mm or more.
  • the adhesive force of the adhesive sheet of one aspect of the present invention is preferably 1.10 N / 25 mm or less after the adhesive layer is attached to a stainless steel plate as an adherend and a voltage is applied at 10 V for 60 seconds.
  • the electrically peelable adhesive sheet of the present invention can be used by being attached to any adherend.
  • the adherend is not particularly limited and may or may not have conductivity. However, from the viewpoint of easily applying a voltage to the pressure-sensitive adhesive layer, the adherend can be used as an electrode as it is. In addition, it is preferable that the adherend has conductivity.
  • the conductive adherend include metals such as aluminum, tin-doped indium oxide, copper, iron, silver, platinum, and gold, and alloys of these metals (for example, stainless steel).
  • the present invention also provides the usage method described in the following [i].
  • [I] A method for using an electrically peelable pressure-sensitive adhesive sheet, wherein the electrically peelable pressure-sensitive adhesive sheet according to one aspect of the present invention is attached to a conductive adherend.
  • a voltage is applied to the pressure-sensitive adhesive layer. Then, it can be peeled off from the adherend.
  • the voltage is applied by connecting the adhesive sheet so that the adherend side from which the pressure-sensitive adhesive sheet is peeled off serves as a cathode.
  • each physical property value is a value measured by the method shown below.
  • Mass average molecular weight (Mw) It was measured under the following conditions using a gel permeation chromatograph device (manufactured by Tosoh Corporation, product name "HLC-8020"), and the value measured in terms of standard polystyrene was used. (Measurement condition) -Column: "TSK guard group HXL-L", “TSK gel G2500HXL”, “TSK gel G2000HXL” and “TSK gel G1000HXL” are connected in sequence (all manufactured by Tosoh Corporation).
  • Acrylic Polymer 3 A copolymer having a structural unit derived from n-butyl acrylate (BA), methyl acrylate (MA), 2-hydroxyethyl acrylate (2-HEA) (constituent unit ratio: BA / MA).
  • "Acrylic Polymer 4" A copolymer having a structural unit derived from n-butyl acrylate (BA), methyl acrylate (MA), 2-hydroxyethyl acrylate (2-HEA) (constituent unit ratio: BA / MA).
  • Component (E): Compound> "PEG”: polyethylene glycol with Mw 200 (a compound in which R 1 is an ethylene group, R 2 is a hydroxy group, and R 3 is a hydrogen atom in the general formula (e-1)), at room temperature (25 ° C.). liquid.
  • the prepared pressure-sensitive adhesive composition was placed in a transparent container, and the appearance was visually observed to evaluate the compatibility of the components constituting the pressure-sensitive adhesive composition based on the following criteria.
  • ⁇ F Separation was seen.
  • the pressure-sensitive adhesive compositions prepared in Examples 1 to 7 had good compatibility.
  • the pressure-sensitive adhesive composition prepared in Comparative Example 1 was confirmed to be separated to the extent that it was difficult to form a pressure-sensitive adhesive layer, so that the pressure-sensitive adhesive composition was completed without producing a pressure-sensitive adhesive sheet.
  • Adhesive Sheet Dry on the peeled surface of a peeling sheet (manufactured by Lintec Corporation, product name "SP-PET38131", thickness: 38 ⁇ m, polyethylene terephthalate (PET) film whose surface has been treated with silicone peeling).
  • the pressure-sensitive adhesive composition prepared in the examples is applied to form a coating film so that the subsequent thickness becomes 50 ⁇ m, and the coating film is dried at 100 ° C. for 2 minutes to form a pressure-sensitive adhesive layer on a release sheet. Formed.
  • the exposed surface of the formed pressure-sensitive adhesive layer is coated with a PET film with an aluminum foil (manufactured by Asia Aluminum Co., Ltd., thickness: 23 ⁇ m, PET film, adhesive layer, and aluminum foil) as a base material in this order.
  • a pressure-sensitive adhesive sheet with a base material having the same structure as that of the electro-peelable pressure-sensitive adhesive sheet 1c shown in FIG.
  • the value (unit: N / 25 mm) measured when the test sheet of the sample for measuring the adhesive strength was peeled off was taken as the adhesive strength of the test sheet before the voltage was applied.
  • the adhesive strength was measured when the adherend was an aluminum plate and a stainless steel plate, respectively.
  • the above-mentioned sample for measuring the adhesive strength is used with a voltage application device 50 (manufactured by Takasago Seisakusho Co., Ltd., product name “KH-100H”), and the anode terminal 51 is based on an aluminum foil.
  • a cathode terminal 52 was connected to the adherend 11 to the material 2a, and a voltage of 10 V was applied for 60 seconds.
  • the peeling speed is 300 mm / min using a tensile tester (manufactured by Orientec Co., Ltd., trade name "Tencilon”) in an environment of 23 ° C.
  • the adhesive strength was measured when the adherend was an aluminum plate and a stainless steel plate, respectively. Then, from the values of the adhesive strength of the test sheet before and after the voltage was applied, the adhesive strength reduction rate was calculated by the following formula.
  • the adhesive sheets produced in Examples 1 to 8 have high adhesive strength before the voltage is applied to both the aluminum plate and the stainless steel plate, but they are adhered by the voltage application. The result was a decrease in power.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)
PCT/JP2021/035369 2020-09-28 2021-09-27 電気剥離性粘着剤組成物、電気剥離性粘着シート、及び電気剥離性粘着シートの使用方法 Ceased WO2022065483A1 (ja)

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KR1020237010876A KR20230073226A (ko) 2020-09-28 2021-09-27 전기 박리성 점착제 조성물, 전기 박리성 점착 시트, 및 전기 박리성 점착 시트의 사용 방법
CN202180065203.7A CN116194542B (zh) 2020-09-28 2021-09-27 电剥离性粘合剂组合物、电剥离性粘合片及电剥离性粘合片的使用方法

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WO2023054478A1 (ja) * 2021-09-30 2023-04-06 日東電工株式会社 粘着剤組成物、粘着シート、及び接合体
WO2023054480A1 (ja) * 2021-09-30 2023-04-06 日東電工株式会社 粘着剤組成物、粘着シート、及び接合体
WO2023054484A1 (ja) * 2021-09-30 2023-04-06 日東電工株式会社 粘着剤組成物、粘着シート、及び接合体
EP4474440A1 (en) 2023-06-06 2024-12-11 Henkel AG & Co. KGaA Debondable adhesive tape
WO2025141478A1 (en) * 2023-12-27 2025-07-03 3M Innovative Properties Company Electrically de-bondable, chemically resistant adhesives

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