WO2015041035A1 - 携帯電子機器用粘着シート - Google Patents

携帯電子機器用粘着シート Download PDF

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Publication number
WO2015041035A1
WO2015041035A1 PCT/JP2014/072907 JP2014072907W WO2015041035A1 WO 2015041035 A1 WO2015041035 A1 WO 2015041035A1 JP 2014072907 W JP2014072907 W JP 2014072907W WO 2015041035 A1 WO2015041035 A1 WO 2015041035A1
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Prior art keywords
pressure
sensitive adhesive
adhesive sheet
polymer
weight
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English (en)
French (fr)
Japanese (ja)
Inventor
将嗣 古曾
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Nitto Denko Corp
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Nitto Denko Corp
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Priority to CN201480050752.7A priority Critical patent/CN105555891A/zh
Priority to US15/021,842 priority patent/US20160222255A1/en
Publication of WO2015041035A1 publication Critical patent/WO2015041035A1/ja
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
    • C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
    • C08G18/6225—Polymers of esters of acrylic or methacrylic acid
    • C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B27/08—Layered products comprising a layer of synthetic resin 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • B32B27/308—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers comprising acrylic (co)polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/36—Layered products comprising a layer of synthetic resin comprising polyesters
    • B32B27/365—Layered products comprising a layer of synthetic resin comprising polyesters comprising polycarbonates
    • 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
    • B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
    • B32B7/04—Interconnection of layers
    • B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
    • C08G18/625—Polymers of alpha-beta ethylenically unsaturated carboxylic acids; hydrolyzed polymers of esters of these acids
    • C08G18/6254—Polymers of alpha-beta ethylenically unsaturated carboxylic acids and of esters of these acids containing hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/08—Homopolymers or copolymers of acrylic acid 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
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • C09J7/22—Plastics; Metallised plastics
    • 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
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/50—Properties of the layers or laminate having particular mechanical properties
    • B32B2307/558—Impact strength, toughness
    • 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
    • B32B2405/00—Adhesive articles, e.g. adhesive tapes
    • 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
    • B32B2457/00—Electrical equipment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2312/00—Crosslinking
    • 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
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
    • 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
    • C09J2301/10—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet
    • C09J2301/12—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet by the arrangement of layers
    • C09J2301/124—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet by the arrangement of layers the adhesive layer being present on both sides of the carrier, e.g. double-sided adhesive tape
    • 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
    • C09J2301/302—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 being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
    • 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
    • C09J2433/00—Presence of (meth)acrylic polymer

Definitions

  • the double-sided adhesive sheet is widely used for bonding and fixing purposes in various fields because of its excellent workability and workability.
  • a portable electronic device such as a mobile phone or a smartphone
  • it is preferably used for joining constituent members such as a display panel and a casing.
  • the portable electronic device is assumed to fall during use because of its use form such as picking up and using it. Therefore, the portable electronic device is required to have a performance (drop impact resistance) that does not cause damage or malfunction of the main body against an impact when dropped.
  • Patent document 1 is mentioned as a technical document regarding the adhesive sheet applied to a portable electronic device.
  • a pressure-sensitive adhesive formed from a water-dispersed pressure-sensitive adhesive composition it is not easy for a pressure-sensitive adhesive formed from a water-dispersed pressure-sensitive adhesive composition to achieve performance equal to or higher than that of a pressure-sensitive adhesive formed from a solvent-type pressure-sensitive adhesive composition. It would be beneficial if a water-dispersed pressure-sensitive adhesive capable of exhibiting good holding power in addition to excellent drop impact resistance is provided.
  • the present invention has been made in view of such circumstances, and an object of the present invention is to provide a pressure-sensitive adhesive sheet for portable electronic devices that has excellent drop impact resistance and can exhibit good holding power.
  • a double-sided adhesive sheet used for fixing a member constituting a portable electronic device.
  • This pressure-sensitive adhesive sheet includes a pressure-sensitive adhesive layer formed from a water-dispersed pressure-sensitive adhesive composition.
  • the water-dispersed pressure-sensitive adhesive composition includes a pressure-sensitive adhesive polymer as a base polymer and a crosslinking agent. Further, the glass transition temperature of the adhesive polymer is ⁇ 60 ° C. or lower.
  • the pressure-sensitive adhesive sheet having such a configuration is excellent in drop impact resistance and can exhibit good holding power.
  • the Tg of an adhesive polymer refers to the Tg of a homopolymer of each monomer (homopolymer) and the weight fraction of the monomer (copolymerization ratio on a weight basis) for the monomer composition corresponding to the polymer. Is a value calculated from the formula of Fox. In the present specification, the unit of numerical values representing Tg is “° C.” unless otherwise specified.
  • Said G A can be adjusted by tackiness molecular weight and monomer composition of the polymer, kind and amount of the polymerization initiator, the type and amount of surfactant, the type of chain transfer agent and amount, and the like. It said G A is determined by the following methods. This also applies to G A in the examples below.
  • G A [(W4-W2-W3) / W1] ⁇ 100
  • PTFE porous polytetrafluoroethylene
  • Examples of the adhesive polymer disclosed herein include acrylic polymers, rubber polymers, polyester polymers, urethane polymers, polyether polymers, silicone polymers, polyamide polymers, and fluorine polymers known in the field of adhesives. 1 type, or 2 or more types of various polymers, such as these, can be used. From the viewpoint of adhesive properties, cost, etc., a rubber polymer or an acrylic polymer can be preferably employed as the adhesive polymer. Of these, acrylic polymers are particularly preferable.
  • the acrylic polymer in this specification is defined as a polymer containing monomer units derived from an acrylic monomer.
  • a typical example of such an acrylic polymer is an acrylic polymer in which the proportion of the acrylic monomer in the monomer composition of the acrylic polymer is more than 50% by weight.
  • the term “(meth) acryloyl” means acryloyl and methacryloyl comprehensively.
  • (meth) acrylate” means acrylate and methacrylate
  • (meth) acryl” generically means acrylic and methacryl.
  • “(Cyclo) alkyl” is a generic term for chain alkyl and cycloalkyl.
  • alkyl (meth) acrylate for example, a compound represented by the following formula (1) can be preferably used.
  • CH 2 C (R 1 ) COOR 2 (1)
  • R 1 in the above formula (1) is a hydrogen atom or a methyl group.
  • R 2 is a chain alkyl group having 1 to 20 carbon atoms (hereinafter, such a range of the number of carbon atoms may be represented as “C 1-20 ”).
  • an alkyl (meth) acrylate in which R 2 is a chain alkyl group of C 1-14 for example, C 1-10 , typically C 4-10 ) is preferable.
  • alkyl (meth) acrylates can be used alone or in combination of two or more.
  • Preferred alkyl (meth) acrylates include n-butyl acrylate (BA) and 2-ethylhexyl acrylate (2EHA). Of these, 2EHA is particularly preferable.
  • a submonomer having copolymerizability with the main monomer, alkyl (meth) acrylate can be useful for introducing a crosslinking point into the acrylic polymer or increasing the cohesive strength of the acrylic polymer.
  • the following functional group-containing monomer components can be used alone or in combination of two or more.
  • Carboxyl group-containing monomers ethylenically unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid and crotonic acid; ethylenically unsaturated dicarboxylic acids such as maleic acid, itaconic acid and citraconic acid and anhydrides thereof (maleic anhydride, anhydrous) Itaconic acid).
  • Hydroxyl group-containing monomers hydroxyalkyl (meth) acrylates such as 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate; Unsaturated alcohols such as vinyl alcohol and allyl alcohol.
  • Monomers having a nitrogen atom-containing ring for example, N-vinyl-2-pyrrolidone, N-methylvinylpyrrolidone, N-vinylpyridine, N-vinylpiperidone, N-vinylpyrimidine, N-vinylpiperazine, N-vinylpyrazine, N-vinyl Pyrrole, N-vinylimidazole, N-vinyloxazole, N-vinylmorpholine, N-vinylcaprolactam, N- (meth) acryloylmorpholine.
  • Alkoxysilyl group-containing monomer for example, 3- (meth) acryloxypropyltrimethoxysilane, 3- (meth) acryloxypropyltriethoxysilane, 3- (meth) acryloxypropylmethyldimethoxysilane, 3- (meth) acryloxy Propylmethyldiethoxysilane.
  • a carboxyl group-containing monomer is preferably used, and the carboxyl group-containing monomer is more preferably acrylic acid or methacrylic acid.
  • the technique disclosed herein can be used even when the monomer raw material used for the polymerization of the acrylic polymer does not include a hydroxyl group-containing monomer and / or a monomer containing a nitrogen atom (for example, a monomer having a nitrogen atom-containing ring).
  • the invention can be implemented in a manner that can achieve the desired effect.
  • the amount of the submonomer is not particularly limited as long as it is appropriately selected so as to realize a desired cohesive force.
  • the amount of secondary monomer is suitably 0.5% by weight or more based on the total monomer components of the acrylic polymer. And preferably 1% by weight or more.
  • the amount of the submonomer is suitably 30% by weight or less, preferably 10% by weight or less (for example, 5% by weight or less) in the total monomer components.
  • copolymer components for the purpose of increasing the cohesive strength of the acrylic polymer, other copolymer components other than the above-mentioned secondary monomer can be used.
  • copolymer components include vinyl ester monomers such as vinyl acetate and vinyl propionate; aromatic vinyl compounds such as styrene, substituted styrene ( ⁇ -methylstyrene, etc.), vinyltoluene; cyclohexyl (meth) acrylate, cyclopentyl di Cycloalkyl (meth) acrylates such as (meth) acrylate, isobornyl (meth) acrylate, etc .; aryl (meth) acrylate (eg, phenyl (meth) acrylate), aryloxyalkyl (meth) acrylate (eg, phenoxyethyl (meth) acrylate) Aromatic ring-containing (meth) acrylates such as arylalkyl (meth) acrylates
  • the method for polymerizing the monomer or a mixture thereof is not particularly limited, and a conventionally known general polymerization method can be employed. As such a polymerization method, for example, emulsion polymerization can be preferably employed.
  • the mode of polymerization is not particularly limited, and a conventionally known monomer supply method, polymerization conditions (temperature, time, pressure, etc.), use components other than the monomer (polymerization initiator, surfactant (emulsifier), etc.) are appropriately selected. It can be carried out.
  • a monomer supply method the entire monomer mixture may be supplied to the reaction vessel at a time (collective supply), or may be gradually dropped and supplied (continuous supply), or divided into several times for a predetermined time. Each quantity may be supplied (divided supply) every time. It is preferable to supply a part or all of the monomer or a mixture thereof as a dispersion emulsified in water.
  • Polymerization initiator For the polymerization of the adhesive polymer (preferably an acrylic polymer), a known or commonly used polymerization initiator can be appropriately selected and used depending on the type of polymerization method. From the viewpoint of stress relaxation of the pressure-sensitive adhesive, an azo polymerization initiator can be preferably used in the emulsion polymerization method.
  • azo polymerization initiator examples include 2,2′-azobisisobutyronitrile (AIBN), 2,2′-azobis (2-methylpropionamidine) disulfate, 2,2′-azobis ( 2-Amidinopropane) dihydrochloride, 2,2′-azobis [2- (5-methyl-2-imidazolin-2-yl) propane] dihydrochloride, 2,2′-azobis (N, N′-dimethyleneisobutyl) Amidine), 2,2′-azobis [N- (2-carboxyethyl) -2-methylpropionamidine] hydrate, 2,2′-azobis (4-methoxy-2,4-dimethylvaleronitrile), 2, 2'-azobis (2,4-dimethylvaleronitrile), 2,2'-azobis (2-methylbutyronitrile), 1,1'-azobis (cyclohexane-1-carbonitri ), 2,2'-azobis (2,4,4-trimethylpentane), dimethyl-2
  • polymerization initiators include persulfates such as potassium persulfate (KPS) and ammonium persulfate (APS); benzoyl peroxide, t-butyl hydroperoxide, di-t-butyl peroxide, t-butyl Peroxybenzoate, dicumyl peroxide, 1,1-bis (t-butylperoxy) -3,3,5-trimethylcyclohexane, 1,1-bis (t-butylperoxy) cyclododecane, hydrogen peroxide, etc.
  • KPS potassium persulfate
  • APS ammonium persulfate
  • benzoyl peroxide t-butyl hydroperoxide
  • di-t-butyl peroxide di-t-butyl peroxide
  • t-butyl Peroxybenzoate dicumyl peroxide
  • 1,1-bis (t-butylperoxy) -3,3,5-trimethylcyclohexane
  • Peroxy group-based initiators substituted ethane-based initiators such as phenyl-substituted ethane; carbonyl-based initiators such as aromatic carbonyl compounds; and the like.
  • Still another example of the polymerization initiator includes a redox initiator based on a combination of a peroxide and a reducing agent. Examples of such redox initiators include a combination of a peroxide (hydrogen peroxide solution and the like) and ascorbic acid, a combination of a persulfate and sodium bisulfite, and the like.
  • Such a polymerization initiator can be used individually by 1 type or in combination of 2 or more types.
  • the amount of polymerization initiator used is not particularly limited.
  • the amount of the polymerization initiator used with respect to 100 parts by weight of the monomer raw material can be typically selected from the range of about 0.005 to 1 part by weight, preferably about 0.01 to 1 part by weight.
  • the polymerization temperature can be appropriately selected according to the type of monomer used, the type of polymerization initiator, and the like. Usually, the polymerization temperature is suitably about 20 to 100 ° C., preferably about 40 to 80 ° C.
  • Emulsion polymerization of the monomer raw material is usually performed in the presence of a surfactant (emulsifier).
  • a surfactant emulsifier
  • known anionic surfactants, nonionic surfactants and the like can be used.
  • a surfactant having a radical polymerizable functional group may be used.
  • the surfactant having a radical polymerizable functional group is also referred to as a reactive (polymerizable) surfactant.
  • a general surfactant having no radical polymerizable functional group is sometimes referred to as a non-reactive (non-polymerizable) surfactant.
  • Surfactant can be used individually by 1 type or in combination of 2 or more types.
  • non-reactive nonionic surfactants include polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether and polyoxyethylene stearyl ether; polyoxyethylenes such as polyoxyethylene octyl phenyl ether and polyoxyethylene nonyl phenyl ether Sorbitan monolaurate, sorbitan monostearate, sorbitan fatty acid ester such as polyoxyethylene sorbitan monolaurate; polyoxyethylene glyceryl ether fatty acid ester; polyoxyethylene-polyoxypropylene block copolymer; .
  • polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether and polyoxyethylene stearyl ether
  • polyoxyethylenes such as polyoxyethylene octyl phenyl ether and polyoxyethylene nonyl phenyl ether
  • Sorbitan monolaurate, sorbitan monostearate, sorbitan fatty acid ester such as polyoxyethylene sorbit
  • the reactive surfactant is not particularly limited as long as it has a radical polymerizable functional group.
  • it may be a reactive surfactant having a structure in which a radical polymerizable functional group is introduced into the anionic surfactant or the nonionic surfactant as described above.
  • an anionic reactive surfactant can be preferably employed.
  • the kind of radically polymerizable functional group is not particularly limited, and may be, for example, an alkenyl group, an acryloyl group, a methacryloyl group, or the like. Specific examples of the alkenyl group include a propenyl group and an isopropenyl group (CH 2 ⁇ C (CH 3 ) —).
  • the concept of the propenyl group herein includes a 1-propenyl group (CH 3 —CH ⁇ CH—) and a 2-propenyl group (CH 2 ⁇ CH—CH 2 —; sometimes referred to as an allyl group). included.
  • the radical polymerizable functional group is preferably an allyl group.
  • anionic reactive surfactants include polyoxyethylene (allyloxymethyl) alkyl ether ammonium sulfate, polyoxyethylene nonylpropenyl phenyl ether ammonium sulfate, sodium alkylallylsulfosuccinate, sodium methacryloxypolyoxypropylene sulfate, poly Examples thereof include ammonium oxyalkylene alkenyl ether sulfate (for example, a compound in which the terminal of the alkenyl group is an isopropenyl group).
  • the anionic reactive surfactant forms a salt
  • the salt may be, for example, a metal salt such as a sodium salt, an ammonium salt, an amine salt, or the like.
  • adhesive polymer e.g. acrylic polymer
  • sodium alkyl allyl sulfosuccinate is preferable.
  • nonionic reactive surfactants include polyoxyethylene nonylpropenyl phenyl ether.
  • reactive surfactants include “AQUALON HS-10”, “AQUALON HS-1025”, “AQUALON HS-20”, “AQUALON KH-10”, “AQUALON” manufactured by Daiichi Kogyo Seiyaku Co., Ltd.
  • the water-dispersed pressure-sensitive adhesive composition disclosed herein contains an acrylic polymer as a base polymer, it may contain a polymer other than the acrylic polymer in addition to the acrylic polymer.
  • the polymer other than the acrylic polymer include those other than the acrylic polymer among the various polymers exemplified as the adhesive polymer.
  • the pressure-sensitive adhesive layer (or water-dispersed pressure-sensitive adhesive composition) disclosed herein contains a polymer other than the acrylic polymer in addition to the acrylic polymer, the content of the polymer other than the acrylic polymer is acrylic.
  • a water dispersion-type adhesive composition contains an isocyanate type crosslinking agent.
  • the pressure-sensitive adhesive formed from the water-dispersed pressure-sensitive adhesive composition the releasability is improved in addition to the improvement of the holding power by introducing chemical crosslinking by the isocyanate-based crosslinking agent at a predetermined ratio.
  • the adhesive layer formed by applying the water-dispersed adhesive composition disclosed herein to a resin film substrate such as polyester (typically polyethylene terephthalate (PET)) is an excellent anchor.
  • PET polyethylene terephthalate
  • the technique disclosed here can also be preferably implemented in an embodiment that does not substantially contain any other crosslinking agent other than the isocyanate-based crosslinking agent.
  • the isocyanate-based crosslinking agent includes two or more isocyanate groups per molecule (an isocyanate group having a protective group; for example, an isocyanate regeneration type in which the isocyanate group is temporarily protected by treatment with a blocking agent, quantification, etc. It is desirable to use a polyisocyanate crosslinking agent having a functional group).
  • the number of isocyanate groups per molecule of the polyisocyanate-based crosslinking agent is preferably 2 to 10 (eg 2 to 4, typically 2 or 3).
  • polyisocyanate-based crosslinking agent examples include aromatic polyisocyanates such as tolylene diisocyanate and xylene diisocyanate; alicyclic isocyanates such as isophorone diisocyanate, and aliphatic polyisocyanates such as hexamethylene diisocyanate.
  • water-stable isocyanate-based crosslinking agent trade names “Bernock DNW-5000”, “Bernock DNW-5010”, “Bernock DNW-5100”, “Bernock DNW-5200”, “Burnock DNW-5500” manufactured by DIC Corporation are available. Trade names “Aquanate 100”, “Aquanate 105”, “Aquanate 110”, “Aquanate 120”, “Aquanate 130”, “Aquanate 200”, “Aquanate 210” manufactured by Nippon Polyurethane Industry Co., Ltd.
  • the amount of the crosslinking agent disclosed herein is not particularly limited, and 0.001 to 100 parts by weight of the adhesive polymer from the viewpoint of improving the adhesive properties such as removability, repulsion resistance and holding power in a well-balanced manner.
  • the amount is suitably from 10 to 10 parts by weight, and preferably from 0.01 to 5 parts by weight (eg 0.05 to 3 parts by weight, typically 0.1 to 2 parts by weight).
  • the water-dispersed pressure-sensitive adhesive composition disclosed herein contains an aqueous solvent as a solvent.
  • the water-dispersed pressure-sensitive adhesive composition is typically a pressure-sensitive adhesive composition in which a pressure-sensitive polymer is dispersed in an aqueous solvent.
  • the aqueous solvent contained in the water-dispersed pressure-sensitive adhesive composition disclosed herein refers to water or a mixed solvent containing water as a main component (a component contained in excess of 50% by weight).
  • the solvent other than water constituting the mixed solvent may be one or more selected from various organic solvents (such as lower alcohols) that can be uniformly mixed with water.
  • the aqueous solvent in this specification typically has a water ratio of 90% by weight or more, preferably 95 to 100% by weight.
  • the pressure-sensitive adhesive composition may contain an acid or a base (such as aqueous ammonia) used for the purpose of adjusting pH, if necessary.
  • Other optional components that can be contained in the composition include a viscosity modifier, a leveling agent, a plasticizer, a filler, a colorant such as a pigment and a dye, a stabilizer, an antiseptic, an anti-aging agent, and the like in a water dispersion type.
  • a viscosity modifier such as a leveling agent, a plasticizer, a filler, a colorant such as a pigment and a dye, a stabilizer, an antiseptic, an anti-aging agent, and the like in a water dispersion type.
  • various additives that are common in the field of pressure-sensitive adhesive compositions are exemplified. About such various additives, conventionally well-known things can be used by a conventional method, and since it does not characterize this invention in particular, detailed description is abbreviate
  • the pressure-sensitive adhesive disclosed herein preferably satisfies the formula: G B (%) ⁇ G A (%) ⁇ W P (%) ⁇ 10 ⁇ 2 >0; from the viewpoint of improving removability. .
  • G A (%) and G B (%) is as described above
  • W P is the weight percentage of the adhesive polymer occupied in solid content of the adhesive composition (typically pressure-sensitive adhesive layer) (%). It is more preferable that G B (%) ⁇ G A (%) ⁇ W P (%) ⁇ 10 ⁇ 2 is larger than 1 (for example, 3, typically 5).
  • isocyanate crosslinking agent water-dispersed polyisocyanate (trade name “Bernock DNW-5010” manufactured by DIC Corporation) was used.
  • tackifier the trade name “Tamanol E-200NT” manufactured by Arakawa Chemical Industries, Ltd. was used.
  • the water-dispersed pressure-sensitive adhesive composition obtained above was applied onto a PET release film (trade name “Diafoil MRF-38” manufactured by Mitsubishi Plastics, Inc.) and dried at 120 ° C. for 3 minutes. A first pressure-sensitive adhesive layer having a thickness of 13 ⁇ m was formed. The first pressure-sensitive adhesive layer was bonded to the first surface of a PET film substrate having a thickness of 5 ⁇ m (trade name “Lumirror 5AF53” manufactured by Toray Industries, Inc.), and then the second surface of the PET film substrate was bonded to the first surface. The water-dispersed pressure-sensitive adhesive composition was applied and dried at 120 ° C.
  • a PET film (trade name “Lumirror S10” manufactured by Toray Industries, Inc.) having a thickness of 25 ⁇ m is bonded to the first adhesive surface (adhesive surface of the first adhesive layer) of the double-sided adhesive sheet according to each example, and the width is 10 mm.
  • a test piece was prepared by cutting into a size of 100 mm in length. The second adhesive surface of the test piece (adhesive surface of the second pressure-sensitive adhesive layer) is exposed, and at room temperature (23 ° C.), a width of 10 mm is applied to a bakelite plate (phenol resin plate) as the adherend. A 2 kg roller was reciprocated once in a contact area of 20 mm in length, and the pressure was applied.
  • the double-sided PSA sheet according to each example was punched into a frame shape having an outer shape of 40 mm ⁇ 60 mm and a width of 2 mm as shown in FIG.
  • a sample for evaluation was prepared by joining a polymethyl methacrylate resin plate (acrylic plate) and a polycarbonate plate (PC plate) with this frame-shaped double-sided pressure-sensitive adhesive sheet.
  • the first pressure-sensitive adhesive surface of the frame-shaped double-sided pressure-sensitive adhesive sheet was bonded to an acrylic plate having a width of 40 mm, a length of 60 mm, and a thickness of 1 mm by reciprocating a 2 kg roller. After this was left at 23 ° C.
  • a 25 ⁇ m-thick PET film (trade name “Lumirror S10” manufactured by Toray Industries, Inc.) is bonded to the first adhesive surface of the double-sided adhesive sheet according to each example, and this is cut into a size of 20 mm in width and 100 mm in length.
  • a measurement sample was prepared. Under an environment of 23 ° C. and 50% RH, the second adhesive surface of the measurement sample was exposed, and a 2 kg rubber roller was reciprocated once on a stainless steel plate (SUS304BA plate) as an adherend. Crimped. After holding this measurement sample at 80 ° C.
  • the above weight was converted to a weight ( ⁇ g) per 1 g of the double-sided pressure-sensitive adhesive sheet (excluding the release liner) and adopted as a VOC emission amount (toluene) ( ⁇ g / g). Therefore, this test is a VOC measurement test using toluene as an indicator gas.
  • the weight of toluene gas was determined from a conversion value from a calibration curve of acetone (which may be toluene) prepared in advance. HSS and GC settings were as follows. In addition, when measuring the total amount of VOC, what is necessary is just to measure not only toluene gas but the total weight of generated gas similarly to the case of the said toluene gas.
  • Example 1 As shown in Table 1, in Examples 1 to 3 using an adhesive polymer having a Tg of ⁇ 60 ° C. or less and a crosslinking agent, excellent drop impact resistance and good holding force were realized. On the other hand, in Example 4 where no cross-linking agent was used, the holding power decreased. Further, in Example 5 in which an adhesive polymer having a Tg higher than ⁇ 60 ° C. was used, the drop impact resistance was inferior.
  • the VOC emission amount (toluene) of the pressure-sensitive adhesive sheets according to Examples 1 and 2 was about 0.7 ⁇ g per 1 g of the double-sided pressure-sensitive adhesive sheet (excluding the release liner).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesive Tapes (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Laminated Bodies (AREA)
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JP6278085B2 (ja) * 2016-09-20 2018-02-14 三菱ケミカル株式会社 光学部材の製造方法
JP2016218482A (ja) * 2016-09-20 2016-12-22 三菱樹脂株式会社 光学部材
JP2018159929A (ja) * 2018-05-08 2018-10-11 三菱ケミカル株式会社 光学部材
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