WO2013081032A1 - Adhésif, feuille adhésive, et stratifié optique - Google Patents

Adhésif, feuille adhésive, et stratifié optique Download PDF

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WO2013081032A1
WO2013081032A1 PCT/JP2012/080862 JP2012080862W WO2013081032A1 WO 2013081032 A1 WO2013081032 A1 WO 2013081032A1 JP 2012080862 W JP2012080862 W JP 2012080862W WO 2013081032 A1 WO2013081032 A1 WO 2013081032A1
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Prior art keywords
pressure
sensitive adhesive
cation
acrylic polymer
weight
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PCT/JP2012/080862
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English (en)
Japanese (ja)
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享尚 赤松
山本　真之
中村　洋平
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新タック化成株式会社
王子ホールディングス株式会社
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Priority to JP2013540136A priority Critical patent/JP5545416B2/ja
Publication of WO2013081032A1 publication Critical patent/WO2013081032A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group

Definitions

  • the present invention relates to an acrylic pressure-sensitive adhesive and a pressure-sensitive adhesive sheet excellent in unevenness followability. Moreover, this invention relates also to the optical laminated body manufactured using these.
  • An acrylic pressure-sensitive adhesive mainly composed of an acrylic polymer and a pressure-sensitive adhesive sheet formed using an acrylic pressure-sensitive adhesive are widely used for bonding various articles such as plastic films and panels.
  • articles to be bonded have become more diversified, and demands for properties at the time of bonding and after bonding have become more severe as industrial products have become more sophisticated and complicated. For this reason, various attempts have been made to improve the performance as a pressure-sensitive adhesive by adding an additive to the acrylic pressure-sensitive adhesive.
  • Patent Document 1 Japanese Patent Application Laid-Open No. 2005-255877 includes an acrylic having a cyclic structure containing 3 to 10% by weight of a carboxyl group-containing crosslinkable monomer unit and having a weight average molecular weight of 3000 to 6000. It is described that a pressure-sensitive adhesive in which a polymerization oligomer is added to an acrylic polymer or a crosslinking agent as a main component has high transparency after bonding, and can prevent floating, peeling and warping.
  • Patent Document 2 Japanese Patent Publication No. 2009-215522
  • a pressure-sensitive adhesive sheet with a specific thickness unevenness using a polymer oligomer added to an acrylic polymer or cross-linking agent as a main component is used for the transparency, adhesion, and foam resistance after bonding. It is described that it has excellent properties and the thickness unevenness of the pressure-sensitive adhesive layer is small.
  • Patent Document 3 Japanese Patent Laid-Open No. 2011-157458 discloses an acrylic polymerized oligomer containing 1 to 10% by weight of a carboxyl group-containing crosslinkable monomer unit and having a weight average molecular weight of 3000 to 10,000.
  • the adhesive added to the acrylic polymer and cross-linking agent, which is the main component, does not generate voids on the end face when applied to uneven parts or thick printed layers, and has followability to steps, and is durable. It is described that the adhesiveness is also high.
  • Patent Document 4 Japanese Patent No. 3272721 is formed by using a pressure-sensitive adhesive in which a liquid resin such as process oil, liquid polyether, or liquid polyterpene is added to an acrylic polymer or a crosslinking agent as a main component. It is described that the pressure-sensitive adhesive layer has appropriate elasticity and flexibility and can absorb the shrinkage stress of the substrate.
  • a liquid resin such as process oil, liquid polyether, or liquid polyterpene is added to an acrylic polymer or a crosslinking agent as a main component. It is described that the pressure-sensitive adhesive layer has appropriate elasticity and flexibility and can absorb the shrinkage stress of the substrate.
  • Patent Document 5 Japanese Patent Application Laid-Open No. 2002-047468
  • Patent Document 6 Japanese Patent Application Laid-Open No. 2002-129123
  • Patent Document 7 Japanese Patent Application Laid-Open No. 2003-049141
  • Patent Document 5 Japanese Patent Application Laid-Open No. 2002-047468
  • Patent Document 6 Japanese Patent Application Laid-Open No. 2002-129123
  • Patent Document 7 Japanese Patent Application Laid-Open No. 2003-049141
  • Patent Document 5 Japanese Patent Application Laid-Open No. 2002-047468
  • Patent Document 6 Japanese Patent Application Laid-Open No. 2002-129123
  • Patent Document 7 Japanese Patent Application Laid-Open No. 2003-049141
  • a low molecular weight non-functional acrylic polymer of 1.0 to 2.5 and an adhesive containing a cross-linking agent exhibit excellent adhesiveness even under high-temperature and high-humidity conditions, and do not cause foaming or peeling due to dimensional changes. And the like.
  • the acrylic pressure-sensitive adhesive described in these patent documents can exhibit a desired function when applied and bonded onto a surface having a smooth flat surface.
  • the adhesive cannot sufficiently follow the irregularities, and bubbles remain in the concave portions, which causes a decrease in adhesive force, adhesive holding force and transparency.
  • the present inventors have attempted to develop a pressure-sensitive adhesive that solves such technical problems. That is, the present inventors have intensively studied for the purpose of providing a pressure-sensitive adhesive having excellent unevenness followability, high adhesive strength and adhesive retention, and excellent high temperature and high humidity durability.
  • the inventors of the present invention made a new pressure-sensitive adhesive by adding oligomers and additives having various functional groups to the acrylic polymer, and repeated tests. However, it has not been easy to find a pressure-sensitive adhesive that has excellent unevenness followability, high adhesive strength and adhesive retention, and excellent high-temperature and high-humidity durability.
  • the inventors of the present invention have found that a pressure-sensitive adhesive that solves the above problems can be provided by adding a non-functional acrylic polymer that satisfies a specific condition after repeated trial and error.
  • the present invention has been provided based on such knowledge, and includes the following configurations.
  • the pressure-sensitive adhesive sheet according to any one of [8] to [10], wherein the pressure-sensitive adhesive layer has a laminated structure.
  • the pressure-sensitive adhesive of the present invention is excellent in uneven followability, has high adhesive strength and adhesive retention, and is excellent in high temperature and high humidity durability. For this reason, even if it is the uneven
  • a numerical range represented by using “to” means a range including numerical values described before and after “to” as a lower limit value and an upper limit value.
  • the pressure-sensitive adhesive of the present invention is characterized by containing a cross-linkable acrylic polymer as a main component and a non-functional acrylic polymer having a weight average molecular weight of 1000 to 5000 and Tg of 0 ° C. or less.
  • Non-functional acrylic polymer The pressure-sensitive adhesive of the present invention contains a non-functional acrylic polymer.
  • non-functional acrylic polymer as used herein means a polymer consisting only of an acrylic monomer unit having no functional group other than an acrylate group, an acrylic monomer unit having no functional group other than an acrylate group, and It means a polymer composed of non-acrylic monomer units having no functional group.
  • “Monomer unit” means a repeating unit constituting a polymer.
  • An “acrylic monomer” is a compound having a (meth) acryloyl group.
  • (Meth) acryloyl group means an acryloyl group or a methacryloyl group.
  • the (meth) acrylic acid ester unit which substituted the hydrogen atom of the carboxyl group of (meth) acrylic acid with the hydrocarbon group is mentioned, for example.
  • the hydrocarbon group preferably has 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms.
  • the (meth) acrylic acid ester examples include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, Isobutyl (meth) acrylate, t-butyl (meth) acrylate, n-pentyl (meth) acrylate, n-hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n- (meth) acrylate Octyl, isooctyl (meth) acrylate, n-nonyl (meth) acrylate, isononyl (meth) acrylate, n-decyl (meth) acrylate, isodecyl (meth) acrylate, n-undecyl (meth) acrylate, N-do
  • non-acrylic monomer having no functional group examples include a non-functional monomer having a polymerizable ethylene group.
  • the number of carbon atoms of the atomic group other than the polymerizable ethylene group of the monomer is preferably from 0 to 18, and more preferably from 0 to 8.
  • Specific examples of the non-acrylic monomer having no functional group include ethylene, propylene, and styrene.
  • the content of the acrylic monomer unit having no functional group other than the acrylate group in the non-functional acrylic polymer is preferably 70 to 100% by weight, more preferably 80 to 100% by weight, More preferably, it is ⁇ 100% by weight.
  • the non-functional acrylic polymer contained in the pressure-sensitive adhesive of the present invention is a non-functional acrylic polymer having a weight average molecular weight of 1000 to 5000.
  • the weight average molecular weight is preferably 1000 or more, and more preferably 2000 or more. Moreover, it is preferable that it is 5000 or less, and it is more preferable that it is 4000 or less.
  • the weight average molecular weight is less than 1000, a pressure-sensitive adhesive having sufficient unevenness followability and high temperature and high humidity durability cannot be obtained.
  • the weight average molecular weight is more than 5000, a pressure-sensitive adhesive having sufficient unevenness followability and adhesive force cannot be obtained.
  • the non-functional acrylic polymer contained in the pressure-sensitive adhesive of the present invention is a non-functional acrylic polymer having a glass transition temperature (Tg) of 0 ° C. or lower.
  • Tg is preferably 0 ° C. or lower, more preferably ⁇ 30 ° C. or lower, and further preferably ⁇ 50 ° C. or lower.
  • Tg is higher than 0 ° C., a pressure-sensitive adhesive having sufficient unevenness followability cannot be obtained.
  • the non-functional acrylic polymer contained in the pressure-sensitive adhesive of the present invention preferably has a viscosity at 25 ° C. of 4800 mPa ⁇ s or less.
  • the viscosity at 25 ° C. here is a value measured using a B-type viscometer.
  • the viscosity at 25 ° C. of the non-functional acrylic polymer is more preferably 4800 mPa ⁇ s or less, and further preferably 3000 mPa ⁇ s or less.
  • it is preferable that the viscosity at 25 degrees C of a nonfunctional acrylic polymer is 500 mPa * s or more.
  • the pressure-sensitive adhesive (excluding the solvent) of the present invention preferably contains 1.0% by weight or more of a non-functional acrylic polymer, more preferably 5.0% by weight or more, and 40% by weight or less. It is preferably contained, and more preferably 30% by weight or less.
  • a non-functional acrylic polymer is equal to or higher than the lower limit, a pressure-sensitive adhesive having sufficient unevenness followability is easily obtained.
  • a non-functional acrylic polymer is below the said upper limit, it will become easy to obtain the adhesive which has high temperature high-humidity durability.
  • the pressure-sensitive adhesive of the present invention contains a crosslinkable acrylic polymer as a main component.
  • the “main component” here means 40% by weight or more of the pressure-sensitive adhesive (excluding the solvent).
  • the pressure-sensitive adhesive of the present invention preferably contains 50% by weight or more of a crosslinkable acrylic polymer, and more preferably 70% by weight or more.
  • the crosslinkable acrylic polymer is a polymer having a non-crosslinkable acrylic monomer unit and a crosslinkable monomer unit.
  • the non-crosslinkable acrylic monomer is an acrylic monomer having no crosslinkable group
  • the crosslinkable monomer is a monomer having a crosslinkable group.
  • the crosslinkable monomer may be an acrylic monomer or a non-acrylic monomer as long as it is polymerizable with the non-crosslinkable acrylic monomer, and is preferably an acrylic monomer.
  • the crosslinkable group include a carboxyl group, a hydroxy group, an amino group, an epoxy group, and a glycidyl group, and a carboxyl group and a hydroxy group are preferable.
  • non-crosslinkable acrylic monomer unit examples include a (meth) acrylic acid ester unit in which a hydrogen atom of a carboxyl group of (meth) acrylic acid is substituted with a hydrocarbon group.
  • the hydrocarbon group preferably has 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms.
  • the hydrocarbon group may have a substituent.
  • the substituent is not particularly limited as long as it does not contain a crosslinkable group, and examples thereof include alkoxy groups such as methoxy group and ethoxy group.
  • the (meth) acrylic acid ester examples include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, Isobutyl (meth) acrylate, t-butyl (meth) acrylate, n-pentyl (meth) acrylate, n-hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n- (meth) acrylate Octyl, isooctyl (meth) acrylate, n-nonyl (meth) acrylate, isononyl (meth) acrylate, n-decyl (meth) acrylate, isodecyl (meth) acrylate, n-undecyl (meth) acrylate, N-do
  • the crosslinkable monomer unit includes a carboxyl group-containing copolymerizable monomer unit, a hydroxy group-containing copolymerizable monomer unit, an amino group-containing copolymerizable monomer unit, and a glycidyl group-containing copolymerizable monomer.
  • Examples include body units.
  • Examples of the carboxyl group-containing copolymerizable monomer include ⁇ , ⁇ -unsaturated carboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, maleic acid, fumaric acid, itaconic acid, citraconic acid, and grataconic acid, and anhydrides thereof. Such as things.
  • hydroxy group-containing copolymerizable monomer examples include (meth) acrylic acid such as 2-hydroxyethyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, and 2-hydroxypropyl (meth) acrylate.
  • Hydroxyalkyl, (meth) acrylic acid such as mono (diethylene glycol) (meth) acrylic acid [(mono, di or poly) alkylene glycol]
  • (meth) acrylic acid lactone such as monocaprolactone (meth) acrylic acid, N-methylol (Meth) acrylamide is mentioned.
  • Examples of the amino group-containing copolymerizable monomer include (meth) acrylamide, allylamide, N, N-dimethyl (meth) acrylamide, N-tertbutyl (meth) acrylamide, dimethylaminoethyl (meth) acrylate, ( Examples include diethylaminoethyl methacrylate) and tertbutylaminoethyl (meth) acrylate.
  • Examples of the glycidyl group-containing copolymerizable monomer include glycidyl (meth) acrylate.
  • hydroxy group-containing copolymerizable monomer Is preferred, hydroxyalkyl (meth) acrylate is more preferred, 2-hydroxyethyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate is particularly preferred.
  • a carboxyl group-containing copolymerizable monomer unit when a carboxyl group-containing copolymerizable monomer unit is contained as a crosslinkable monomer unit, the acidity becomes strong, so when a corrosive film such as a tin-doped indium oxide film or a metal film is in contact with these, May corrode the film. Therefore, when applying the pressure-sensitive adhesive of the present invention to such an object having corrosivity, from the viewpoint of corrosion prevention, a carboxyl group-containing copolymerizable monomer unit as a crosslinkable monomer unit The content of is preferably less than 0.5% by weight, and more preferably not contained at all.
  • the content of the crosslinkable monomer unit in the crosslinkable acrylic polymer is preferably 0.01 to 20% by weight, and more preferably 0.5 to 10% by weight. If the content of the crosslinkable monomer unit is not less than the above lower limit value, it can be sufficiently cross-linked, and the swelling prevention and punching performance can be further improved. There is a tendency to ensure performance and curl prevention performance.
  • the crosslinkable acrylic polymer may have other monomer units other than the non-crosslinkable acrylic monomer unit and the crosslinkable monomer unit.
  • examples of other monomers include (meth) acrylonitrile, vinyl acetate, styrene, vinyl chloride, vinyl pyrrolidone, vinyl pyridine, and acrylamide.
  • the content of other monomer units in the crosslinkable acrylic polymer is preferably 0.1 to 20% by weight, and more preferably 0.5 to 10% by weight. If the content of other monomer units is not less than the lower limit, the physical properties can be easily adjusted, and if it is not more than the upper limit, yellowing due to deterioration with time can be prevented.
  • a preferable polymerization initiator that can be used includes a polymerization initiator having no repeating unit. Examples thereof include azo polymerization initiators such as azobisisobutyronitrile and azobisvaleronitrile, and peroxide polymerization initiators such as benzoyl peroxide and lauryl peroxide. These polymerization initiators can be used more preferably than, for example, a polymer azo polymerization initiator having a polymer segment and an azo group.
  • the molecular weight of the polymerization initiator used in the present invention is preferably 1000 or less, more preferably 700 or less, and even more preferably 500 or less. About a lower limit, it can be set as 100 or more, for example.
  • the weight average molecular weight of the crosslinkable acrylic polymer is preferably 100,000 or more, more preferably 200,000 or more, further preferably 300,000 or more, and further preferably 350,000 or more, Further, it is preferably 2 million or less, more preferably 1.5 million or less, further preferably 1 million or less, and even more preferably 750,000 or less.
  • the pressure-sensitive adhesive of the present invention contains a crosslinking agent.
  • the crosslinking agent include isocyanate compounds, epoxy compounds, oxazoline compounds, aziridine compounds, metal chelate compounds, melamine compounds, and the like.
  • an isocyanate compound and an epoxy compound are preferable because the acrylic polymer can be easily crosslinked.
  • an isocyanate compound from the reactivity of the hydroxy group it is preferable to use an isocyanate compound from the reactivity of the hydroxy group.
  • an isocyanate compound when an acrylic polymer contains only a carboxyl group-containing copolymerizable monomer unit as a crosslinkable monomer unit, an isocyanate compound, an epoxy compound, an aziridine compound, or a melamine compound may be used due to the reactivity of the carboxyl group. It is particularly preferable to use an epoxy compound or an isocyanate compound.
  • Examples of the epoxy compound include ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, bisphenol A / epichlorohydrin type epoxy resin, N, N, N ′, N′— And polyfunctional epoxy compounds such as tetraglycidyl-m-xylenediamine, 1,3-bis (N, N-diglycidylaminomethyl) cyclohexane, N, N-diglycidylaniline, N, N-diglycidyltoluidine, etc.
  • Examples of the isocyanate compound include tolylene diisocyanate, xylylene diisocyanate, hexamethylene diisocyanate, and isophorone diisocyanate.
  • crosslinking agents other than epoxy compounds and isocyanate compounds examples include 2,2'-bishydroxymethylbutanol tris [3- (1-aziridinyl) propionate], 4,4'-bis (ethyleneiminocarbonylamino) diphenylmethane, and the like.
  • Functional aziridine compounds for example, metal chelates such as coordination compounds of polyvalent metals such as aluminum, iron, copper, zinc, tin, titanium, nickel, antimony, magnesium, vanadium, chromium and zirconium with acetylacetone and ethyl acetoacetate Is mentioned.
  • the content of the crosslinking agent is appropriately selected according to the desired adhesive properties. Usually, it is preferably 0.01% by weight or more of the pressure-sensitive adhesive of the present invention (excluding the solvent), more preferably 0.02% by weight or more, and further preferably 0.04% by weight or more. It is preferably 0.20% by weight or less, more preferably 0.18% by weight or less, and further preferably 0.14% by weight or less.
  • [Other components of adhesive] Components other than the above may be contained in the pressure-sensitive adhesive of the present invention.
  • a polyester resin, amino resin, epoxy resin, or polyurethane resin may be used in combination as a resin other than the main component acrylic polymer or non-functional acrylic polymer.
  • the amount of such resin added is preferably 40% by weight or less of the pressure-sensitive adhesive (excluding the solvent), more preferably 35% by weight or less, and further preferably 30% by weight or less. .
  • the pressure-sensitive adhesive of the present invention includes an antioxidant, a metal corrosion inhibitor, a tackifier, a silane coupling agent, an ultraviolet absorber, a light stabilizer such as a hindered amine compound, a filler, an ionic property as necessary.
  • Additives such as liquids may be included.
  • the antioxidant include phenolic antioxidants, amine-based antioxidants, lactone-based antioxidants, phosphorus-based antioxidants, sulfur-based antioxidants, and the like. These antioxidants may be used alone or in combination of two or more.
  • a benzotriazole-based resin is preferable because of the compatibility and high effect of the pressure-sensitive adhesive.
  • Examples of the tackifier include rosin resin, terpene resin, terpene phenol resin, coumarone indene resin, styrene resin, xylene resin, phenol resin, and petroleum resin.
  • Examples of the silane coupling agent include mercaptoalkoxysilane compounds (for example, mercapto group-substituted alkoxy oligomers).
  • Examples of the ultraviolet absorber include benzotriazole compounds and benzophenone compounds.
  • Examples of the ionic liquid include ionic liquids such as a nitrogen-containing onium salt, a sulfur-containing onium salt, or a phosphorus-containing onium salt, and are preferably described in paragraph numbers 0018 to 0028 of JP2011-89138A.
  • Ionic liquids to be used.
  • the description of paragraph numbers 0018 to 0028 in Japanese Patent Laid-Open No. 2011-89138 is incorporated herein as a part of this specification.
  • the blending amount when these additives are used is preferably 0.01% by weight or more, more preferably 0.05% by weight or more, still more preferably 0.1% by weight or more of the pressure-sensitive adhesive (excluding the solvent). It is preferably 10% by weight or less, more preferably 5% by weight or less, and further preferably 3% by weight or less. Note that the materials and modes described in paragraph numbers 0021 to 0105 of JP2011-148965A can also be used in the present invention, and these descriptions are cited here as a part of this specification.
  • an ionic liquid such as a nitrogen-containing onium salt, a sulfur-containing onium salt, or a phosphorus-containing onium salt, preferably from the group consisting of the following formulas (A), (B), (C) and (D)
  • the pressure-sensitive adhesive can have antistatic properties.
  • the ionic salt is liquid or solid at 25 ° C.
  • R 1 in the formula (A) represents a hydrocarbon group having 4 to 20 carbon atoms and may contain a heteroatom
  • R 2 and R 3 may be the same or different and represent hydrogen or a carbon atom having 1 to 16 carbon atoms.
  • R 4 in the formula (B) represents a hydrocarbon group having 2 to 20 carbon atoms and may contain a hetero atom
  • R 5 , R 6 , and R 7 are the same or different and each represents hydrogen or carbon number 1 Represents ⁇ 16 hydrocarbon groups and may contain heteroatoms.
  • R 8 in the formula (C) represents a hydrocarbon group having 2 to 20 carbon atoms and may contain a hetero atom
  • R 9 , R 10 , and R 11 are the same or different and each represents hydrogen or 1 carbon atom.
  • X in the formula (D) represents a nitrogen, sulfur, or phosphorus atom
  • R 12 , R 13 , R 14 , and R 15 are the same or different and each represents a hydrocarbon group having 1 to 20 carbon atoms; Hetero atoms may be included. However, if X is a sulfur atom, R 12 is not. ]
  • Examples of the cation represented by the formula (A) include a pyridinium cation, a piperidinium cation, a pyrrolidinium cation, a cation having a pyrroline skeleton, and a cation having a pyrrole skeleton.
  • Specific examples include 1-ethylpyridinium cation, 1-butylpyridinium cation, 1-hexylpyridinium cation, 1-butyl-3-methylpyridinium cation, 1-butyl-4-methylpyridinium cation, 1-hexyl-3 -Methylpyridinium cation, 1-butyl-3,4-dimethylpyridinium cation, 1,1-dimethylpyrrolidinium cation, 1-ethyl-1-methylpyrrolidinium cation, 1-methyl-1-propylpyrrolidinium cation 2-methyl-1-pyrroline cation, 1-ethyl-2-phenylindole cation, 1,2-dimethylindole cation, and 1-ethylcarbazole cation.
  • Examples of the cation represented by the formula (B) include an imidazolium cation, a tetrahydropyrimidinium cation, and a dihydropyrimidinium cation.
  • Specific examples include 1,3-dimethylimidazolium cation, 1,3-diethylimidazolium cation, 1-ethyl-3-methylimidazolium cation, 1-butyl-3-methylimidazolium cation, 1-hexyl- 3-methylimidazolium cation, 1-octyl-3-methylimidazolium cation, 1-decyl-3-methylimidazolium cation, 1-dodecyl-3-methylimidazolium cation, 1-tetradecyl-3-methylimidazolium cation 1,2-dimethyl-3-propylimidazolium cation, 1-ethyl-2,3-dimethylimidazolium cation, 1-but
  • Examples of the cation represented by the formula (C) include a pyrazolium cation and a pyrazolinium cation. Specific examples include 1-methylpyrazolium cation, 3-methylpyrazolium cation, 1-ethyl-2-methylpyrazolinium cation and the like.
  • Examples of the cation represented by the formula (D) include a tetraalkylammonium cation, a trialkylsulfonium cation, a tetraalkylphosphonium cation, and those in which a part of the alkyl group is substituted with an alkenyl group, an alkoxyl group, or an epoxy group.
  • tetramethylammonium cation tetraethylammonium cation, tetrabutylammonium cation, tetrahexylammonium cation, triethylmethylammonium cation, tributylethylammonium cation, trimethyldecylammonium cation, N, N-diethyl -N-methyl-N- (2-methoxyethyl) ammonium cation, glycidyltrimethylammonium cation, N, N-dimethyl-N, N-di Propylammonium cation, N, N-dimethyl-N, N-dihexylammonium cation, N, N-dipropyl-N, N-dihexylammonium cation, trimethylsulfonium cation, triethylsulfonium cation, tribut
  • the anion component is not particularly limited as long as it satisfies that it becomes an ionic liquid.
  • Cl ⁇ , Br ⁇ , I ⁇ , AlCl 4 ⁇ , Al 2 Cl 7 ⁇ , BF 4 ⁇ , PF 6 ⁇ , ClO 4 ⁇ , NO 3 ⁇ , CH 3 COO ⁇ , CF 3 COO ⁇ , CH 3 SO 3 ⁇ , CF 3 SO 3 ⁇ , (CF 3 SO 2 ) 2 N ⁇ , (CF 3 SO 2 ) 3 C ⁇ , AsF 6 ⁇ , SbF 6 ⁇ , NbF 6 ⁇ , TaF 6 ⁇ , F (HF) n ⁇ , (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 ⁇ and the like are
  • the ionic salt may be a commercially available one, but can be synthesized as appropriate.
  • the method for synthesizing the liquid ionic salt is not particularly limited as long as the target ionic liquid can be obtained.
  • the document “ionic liquids—the forefront and future of development” [ Use the halide method, hydroxide method, acid ester method, complex formation method, and neutralization method described in [Published by CMC Publishing Co., Ltd.], a method according to this, or a method combining these with conventional methods. be able to.
  • the pressure-sensitive adhesive of the present invention can be directly applied to a material to be adhered.
  • the applicable law is not particularly limited.
  • it may be dissolved in a solvent and applied as a solution and then dried (solution method), or may be formed into a sheet and stacked (sheet method).
  • solution method solution method
  • sheet method sheet method
  • transfer method an adhesive object
  • you may make an adhesion target object contact the adhesion layer which peeled the peeling film (adhesive sheet method).
  • the solvent examples include methyl ethyl ketone, ethyl acetate, toluene, xylene, acetone, benzene, dioxane, acetonitrile, tetrahydrofuran, diglyme, dimethyl sulfoxide, N-methylpyrrolidone, dimethylformamide, etc. Can be used.
  • the pressure-sensitive adhesive layer can be formed by removing the solvent at high temperature or under reduced pressure.
  • the thickness in particular of an adhesive layer is not restrict
  • the pressure-sensitive adhesive layer may have a laminated structure of two or more layers. When it has a laminated structure of two or more layers, at least one layer is required to be an adhesive layer that satisfies the conditions of the present invention.
  • a two-layer laminated structure composed of a layer satisfying the conditions of the present invention / a layer not satisfying the conditions of the present invention, a layer satisfying the conditions of the present invention / a two-layer laminated structure composed of another layer satisfying the conditions of the present invention
  • Specific examples include a three-layered structure composed of a layer that satisfies the conditions of the present invention / a layer that does not satisfy the conditions of the present invention / a layer that satisfies the conditions of the present invention.
  • the pressure-sensitive adhesive layer satisfying the conditions of the present invention has a thickness in the above-mentioned preferable range.
  • the thickness of the layer satisfying the conditions of the present invention is 50% or more of the total thickness of the pressure-sensitive adhesive layer. Preferably, it is 70% or more, more preferably 85% or more.
  • the pressure-sensitive adhesive layer satisfying the conditions of the present invention is configured so as to be in direct contact with the uneven adhesion object.
  • the weight average of the crosslinkable acrylic polymer that is the main component contained in the layer that satisfies the conditions of the present invention It is preferable to increase the weight average molecular weight of the crosslinkable acrylic polymer as the main component contained in the layer that does not satisfy the conditions of the present invention, rather than the molecular weight.
  • the latter weight average molecular weight can be increased by 200,000 or more, or can be increased by 400,000 or more.
  • the pressure-sensitive adhesive of the present invention can be formed into a sheet to form a pressure-sensitive adhesive sheet.
  • the pressure-sensitive adhesive sheet can be produced, for example, by dissolving a pressure-sensitive adhesive in a solvent and removing the solvent after coating.
  • the coating method can be appropriately selected from knife coaters, micro bar coaters, air knife coaters, reverse roll coaters, reverse gravure coaters, bario gravure coaters, die coaters, curtain coaters and the like.
  • the pressure-sensitive adhesive sheet of the present invention is prepared, for example, by preparing a release film provided with a release agent layer on a substrate such as a polymer film, and applying and drying the pressure-sensitive adhesive coating liquid of the present invention on the release agent layer. Obtainable.
  • the release sheet preferably has a structure in which the upper and lower sides of the pressure-sensitive adhesive layer 112 are sandwiched between two release films 114 each having a release agent layer 115 provided on a base material 116.
  • the pressure-sensitive adhesive sheet of the present invention having such a structure is obtained by applying and drying the pressure-sensitive adhesive coating liquid on the release layer surface of the first release film in which the release agent layer is provided on the polymer film, and then the first release film and Can be obtained by bonding and pressure-bonding the release layer surface of the second release film composed of release agent layers having different release forces to the pressure-sensitive adhesive layer surface.
  • the peel force of the release film on the heavy peel force side is preferably 0.5 N / 50 mm to 1.5 N / 50 mm, and the peel force of the peel film on the light peel force side is 0.01 N / 50 mm to 0.4 N. / 50 mm is preferable. Further, the value of heavy peeling force / light peeling force is preferably 1.5 or more, and more preferably 2.0 or more.
  • a 1st peeling film may be bonded and pressure-bonded.
  • the shape of the pressure-sensitive adhesive sheet may be a sheet shape or may be wound up in a roll shape.
  • a pressure-sensitive adhesive sheet is used, there is no need for the application of a pressure-sensitive adhesive at the bonding stage and a drying step, and it is easy to apply pressure by laminating a pressure-sensitive adhesive sheet between two pressure-sensitive adhesive objects and pressing it. . That is, two adhesion objects can be easily adhered by laminating the first adhesion object, the adhesive sheet, and the second adhesion object in this order, and pressurizing the obtained laminate. .
  • the pressure-sensitive adhesive object 110 with the pressure-sensitive adhesive layer can be manufactured by laminating the pressure-sensitive adhesive of the present invention on the surface of the pressure-sensitive adhesive object 111 as the pressure-sensitive adhesive layer 112.
  • a method of applying the pressure-sensitive adhesive to the surface of the pressure-sensitive adhesive object the above-described solution method, sheet method, or the like can be used.
  • the pressure-sensitive adhesive object with the pressure-sensitive adhesive layer is easily bonded to the pressure-sensitive adhesive object 113 to which the pressure-sensitive adhesive object 111 is to be attached by pressing the pressure-sensitive adhesive layer 112 so that the pressure-sensitive adhesive layer 112 is in contact with the pressure-sensitive adhesive object. Can be attached to objects.
  • the pressure-sensitive adhesive 111 is pressure-bonded to the pressure-sensitive adhesive layer 112 as shown in FIG. A layered adhesive object can be produced.
  • the release film should be peeled off just before trying to bond as much as possible.
  • a pressure-sensitive adhesive object with a pressure-sensitive adhesive layer can be produced by directly pressing the pressure-sensitive adhesive object,
  • the manufacturing method can be properly used for convenience.
  • known surface treatment such as corona treatment or plasma treatment
  • the adhesiveness between the pressure-sensitive adhesive layer and the adhesion target object can be further improved.
  • a pressure-sensitive adhesive-attached object may have a sheet shape or a roll shape.
  • the pressure-sensitive adhesive layer-attached adhesive object can be easily obtained by stacking and pressing the second pressure-sensitive adhesive object 113 to be bonded to the pressure-sensitive adhesive layer 112 from which the release film has been peeled. It can stick to the 2nd adhesion target object 113. At this time, in order to prevent the adhesive from sticking to an unintended object or being deteriorated by exposure to air, the release film should be peeled off immediately before trying to bond it as much as possible. . Moreover, as a means for suppressing such a case, a mode in which a release film 114 is further formed on the pressure-sensitive adhesive layer 112 as shown in FIG. 4 can be cited as a preferred example.
  • the release film 114 preferably includes a base material 116 and a release agent layer 115. At this time, lamination is performed such that the release film 115 side of the release film contacts the surface of the pressure-sensitive adhesive layer 112.
  • the embodiment shown in FIG. 5 can be cited.
  • the adhesive layer exposed by peeling off one release film is superimposed on the adhesive object, and the other adhesive layer exposed by peeling the other release film is used as another adhesive object. It is possible to adhere by pressurizing the whole.
  • the release film substrate for example, various polymer films can be used, and polyethylene terephthalate is particularly preferable from the viewpoint of surface smoothness and processability.
  • the release agent constituting the release agent layer for example, a general-purpose addition type or condensation type silicone release agent or a long-chain alkyl group-containing compound is used.
  • an addition type silicone release agent having high reactivity is preferably used.
  • Specific examples of silicone release agents include BY24-4527 and SD-7220 manufactured by Toray Dow Corning Silicone, KS-3600, KS-774, and X62-2600 manufactured by Shin-Etsu Chemical Co., Ltd. Is mentioned.
  • the silicone-based release agent may contain a silicone resin that is an organosilicon compound having a SiO 2 unit and (CH 3 ) 3 SiO 1/2 unit or CH 2 ⁇ CH (CH 3 ) SiO 1/2 unit. preferable.
  • Specific examples of the silicone resin include BY24-843, SD-7292, SHR-1404 manufactured by Toray Dow Corning Silicone, KS-3800, X92-183 manufactured by Shin-Etsu Chemical Co., Ltd., and the like.
  • the adhesion target object which adheres using the adhesive of this invention is not restrict
  • glass, a film, etc. can be mentioned.
  • the pressure-sensitive adhesive of the present invention it is possible to realize adhesion with low haze and high transparency. Therefore, the surface protection plate of the display device and the adhesion of the touch panel module, the surface protection plate and the image display module, or the touch panel module It can be preferably used for adhesion of an image display module.
  • the surface protective plate include a glass plate and a resin plate subjected to frame printing, and the material is not particularly limited as long as transparency is ensured.
  • transparent resins such as polyethylene terephthalate resin, polycarbonate resin, and polymethyl methacrylate resin are desirable.
  • adhesive objects of touch panel modules include sensor glass and sensor films that have been subjected to conductive treatment, protective films on the top of the conductive layer, or glass that is opposite to sensor glass and sensor films that have been subjected to conductive treatment, Examples thereof include a film and a hard coat layer on the surface thereof.
  • the film subjected to the conductive treatment include polyethylene terephthalate, polycarbonate, and cycloolefin resin.
  • Examples of the adhesive object of the image display module include an optical film and a display panel, and it is preferable to provide an optical laminate by bonding them using the adhesive of the present invention.
  • an optical film for example, it has optical anisotropy and is formed to protect a retardation film (optical compensation film) having a retardation in a specific in-plane direction and a retardation in a specific thickness direction, and a polarizer.
  • Polarizer protective film sometimes called a polarizing plate protective film
  • a polarizing plate base material that functions as a support for the polarizer in the polarizing plate
  • an antireflection film that suppresses reflection of light incident from the outside, and the like be able to.
  • Examples of materials constituting such an optical film include cellulose acetate, cellulose propionate, cellulose butyrate, cellulose acetate propionate, cellulose acetate butyrate, cellulose acetate propionate butyrate, and cellulose propionate butyrate.
  • Examples include cellulose acylate; cycloolefin resin.
  • Arton manufactured by JSR
  • Zeonore manufactured by Nippon Zeon
  • glass etc. can be mentioned as a display panel.
  • Examples of typical display devices include a liquid crystal display device (liquid crystal display panel), a plasma display device (plasma display panel), and an organic electroluminescence display device (organic EL panel).
  • the surface protective plate, the touch panel module, and the image display module can be effectively adhered using the adhesive of the present invention, in addition to the stationary image display device, a mobile phone, a smartphone, or a tablet terminal as a mobile terminal A mobile personal computer can be preferably manufactured. Since the adhesive of this invention is excellent in uneven
  • the pressure-sensitive adhesive of the present invention can be preferably used for pasting and the like.
  • member having irregularities on the surface means a member having irregularities with a height difference (step) of 5 ⁇ m or more on the surface of the member to be bonded.
  • a surface protective plate subjected to frame printing can be cited as a desirable example.
  • the printing step of the surface protection plate tends to be thicker from about 10 ⁇ m until recently due to the necessity of decoration and concealment to 15 ⁇ m to 60 ⁇ m, and the pressure-sensitive adhesive of the present invention has excellent unevenness followability and is suitable for bonding.
  • the display device after bonding can be used for a long time or when used outdoors. Even when the is placed under high humidity, it is possible to prevent the generation of bubbles and maintain a stable display function. That is, even when left under a high temperature and high humidity for a long time, the pressure-sensitive adhesive of the present invention causes the display color to change, whitening progresses, and distortion and display unevenness occur due to the generation of bubbles. Can be prevented.
  • the glass transition temperature (Tg) was measured by using DSC (simultaneous differential thermogravimetric measuring device) manufactured by SII.
  • the viscosity at 25 ° C. was measured using a B-type viscometer manufactured by TOKIMEC.
  • Comparative Example 1 An agent solution was prepared.
  • Comparative Example 1 no low molecular weight acrylic polymer was added.
  • the low molecular weight acrylic polymers added in Examples 1 to 4 and Comparative Examples 2 to 5 are all liquid at 25 ° C., the non-volatile content is 98% or more, and the specific gravity is 1.02 to 1.12. Within the range, the refractive index is 1.46 to 1.47, and it is a 100% polymer of a crosslinkable acrylic monomer.
  • a release film [A50 # 50, manufactured by Teijin DuPont Films Co., Ltd.] provided with a release agent layer on a PET film is prepared, and the release layer side is on the coated surface of the adhesive solution. After heating at 40 ° C. for 2 minutes, it was further heated at 110 ° C. for 2 minutes. This produced the adhesive sheet which has an adhesive layer of the thickness shown in Table 2 between the 1st release sheet and the 2nd release sheet.
  • the pressure-sensitive adhesive sheet produced in the pressure- sensitive adhesive strength test (2) is cut into a size of 25 mm ⁇ 100 mm, the second pressure-sensitive adhesive layer is peeled off, and the pressure-sensitive adhesive layer exposed is attached to a clean glass plate surface.
  • Two reciprocating pressures were applied with a roller. Adhesion when the adhesive layer is peeled off from the glass plate at a pulling rate of 300 mm / min by the 180 degree peeling method (peel method) specified in JIS-Z-0237 after 24 hours from the time of pressure bonding.
  • the force was measured with a Tensilon tensile tester [manufactured by Shimadzu Corporation: Autograph].
  • the adhesive residue on the glass surface after peeling was evaluated in the following four stages.
  • the pressure-sensitive adhesive sheet produced in the holding power test (2) was cut into a size of 25 mm ⁇ 100 mm, the second pressure-sensitive adhesive layer was peeled off, and the pressure-sensitive adhesive layer that was exposed was attached to a clean SUS board surface.
  • the holding power test specified in 0237: 2000 was performed and evaluated according to the following criteria. The results are shown in Table 2.
  • the total light transmittance (Tt) and haze (Hz) of each sample were measured using a turbidimeter [manufactured by Nippon Denshoku Industries Co., Ltd .: Haze Meter NDH2000], and the lightness (L *) and chromaticity (a *, b) *) was measured using a color difference meter [manufactured by Nippon Denshoku Industries Co., Ltd .: Spectro Color Meter SE2000]. Thereafter, each sample was put in an oven set at 85 ° C. and relative humidity 85%, taken out after 250 hours, and again after 30 minutes haze (Hz), total light transmittance (Tt), lightness (L *), color The degree (a *, b *) was measured.
  • haze (Hz) was also measured after 24 hours from the removal. The results are shown in Table 3 below. As shown in Table 3, Examples 1B to 4B all had high temperature and high humidity durability. In contrast, Comparative Example 3B had a high untreated Hz value.
  • the adhesive layer was changed into 175 micrometers and the uneven
  • the pressure-sensitive adhesive layer exposed by peeling off the first release sheet of the glass with the pressure-sensitive adhesive layer and the rugged surface of the glass with the ruggedness were vacuum-bonded using a vacuum bonding machine [Crim Products Co., Ltd .: V-SE160H].
  • a pressure of 0.6 MPa was applied for 30 seconds in an environment of 100 Pa and a temperature of 30 ° C.
  • a pressure of 0.5 MPa was applied to the obtained transparent laminate for 20 minutes in a pressure degassing apparatus (manufactured by Kurihara Seisakusho: YK-350S) at 50 ° C.
  • Example 4D-1, Example 4D-2, and Example 4D-3 are good even when the crosslinking agent of the non-functional acrylic polymer is changed, and the unevenness followability is improved. is doing. In particular, the unevenness followability of Example 4D-3 is remarkably improved (the evaluation is AA).
  • Example 4 and Comparative Example 1 were changed to an epoxy cross-linking agent [manufactured by Soken Chemical Co., Ltd .: E-5C], and the thickness of the adhesive layer was changed to 75 ⁇ m.
  • Samples of Example 4D-4 and Comparative Example 1D-1 were produced. About each of these samples, the adhesive force test of (3) was done. Further, the thickness of the pressure-sensitive adhesive layer was changed to 175 ⁇ m, and the unevenness followability tests 3 and 4 of (8) were performed. The results are shown in Table 6. As shown in Table 6, even when the crosslinking agent was changed, the adhesive strength of Example 4D-4 was good, and the unevenness followability was improved.
  • Double layer test of pressure-sensitive adhesive layer [synthesis of pressure-sensitive adhesive solution of first pressure-sensitive adhesive layer] After nitrogen gas was sealed in a reactor equipped with a stirrer, thermometer, reflux condenser, dropping device, and nitrogen introduction tube, 105 parts by weight of ethyl acetate as a solvent was added.
  • AIBN nitrile
  • Each pressure-sensitive adhesive solution E-1 for Example 5 was diluted with 5.0 parts by weight of the low molecular weight acrylic polymer used in Example 1 to a solution having a concentration of 35% by weight with ethyl acetate. Obtained. In the adhesive solution E-2 for Comparative Example 6, no low molecular weight acrylic polymer was added.
  • a release film 38 ⁇ RL-07 (2) manufactured by Oji Specialty Paper Co., Ltd.
  • the pressure-sensitive adhesive solution (E-1 or E-2) for the first pressure-sensitive adhesive layer was applied with a knife coater and heated at 100 ° C. for 3 minutes to form a first pressure-sensitive adhesive layer.
  • the 1st adhesive sheet for Comparative Example 6 was obtained.
  • the second release sheet there is prepared a release film [38 ⁇ RL-07 (L)] manufactured by Oji Specialty Paper Co., Ltd., which has a PET film and a release agent layer having higher release properties than the first release sheet.
  • the solution of the adhesive solution F-1 for the second adhesive layer was applied to the release agent layer of the second release sheet with a knife coater, heated at 100 ° C. for 3 minutes, and the second adhesive A layer was formed to obtain a second pressure-sensitive adhesive sheet.
  • the first pressure-sensitive adhesive sheet and the second pressure-sensitive adhesive sheet are stacked so that the first pressure-sensitive adhesive layer and the second pressure-sensitive adhesive layer are in contact with each other, and are pressure-bonded to form the first release sheet and the second release sheet.
  • a pressure-sensitive adhesive sheet having a thickness of the pressure-sensitive adhesive layer shown in Table 7 was produced between the sheets, and pressure-sensitive adhesive sheets of Example 5 and Comparative Example 6 were obtained.
  • Example 5D and Comparative Example 6D were manufactured according to the following procedure using each of the pressure-sensitive adhesive sheets of Example 5 and Comparative Example 6 manufactured above.
  • the unevenness followability test 3 was performed according to the following procedure. Printing was performed on one side of the glass (thickness: about 0.9 mm) so that unevenness with an elevation difference of 30 ⁇ m was formed, whereby uneven glass was obtained. Next, the 2nd adhesive layer which peeled and exposed the 2nd peeling sheet of the adhesive sheet of a sample was stuck on glass [Matsunami Glass Industrial Co., Ltd. product: slide glass S9111], and the glass with an adhesive layer was obtained. It was.
  • the first adhesive sheet exposed by peeling the first release sheet of the glass with the pressure-sensitive adhesive layer and the uneven surface of the glass with the unevenness were used with a vacuum bonding machine [Crim Products Co., Ltd .: V-SE160H]. Then, a pressure of 0.6 MPa was applied for 30 seconds in an environment of a degree of vacuum of 100 Pa and a temperature of 30 ° C. A pressure of 0.5 MPa was applied to the obtained transparent laminate for 20 minutes in a pressure degassing apparatus (manufactured by Kurihara Seisakusho: YK-350S) at 50 ° C.
  • a pressure degassing apparatus manufactured by Kurihara Seisakusho: YK-350S
  • the degree of adhesion of the glass with unevenness was evaluated according to the following criteria by observing the generation of bubbles using a microscope (magnification: 25 times).
  • corrugated followability test 4 the transparent laminated body bonded according to the same procedure as (8) was evaluated on the same basis as the above. The results are shown in Table 5. As shown in Table 7, even if the pressure-sensitive adhesive layer is changed to two layers, the adhesive strength of Example 5D is good, and the unevenness followability is improved.
  • the pressure-sensitive adhesive of the present invention is excellent in uneven followability, has high adhesive strength and adhesive retention, and is excellent in high temperature and high humidity durability. For this reason, even if it is the uneven
  • Adhesive Object with Adhesive Layer 111
  • Second Adhesive Object 114 Release Film 115 Release Agent Layer 116 Base Material

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Adhesive Tapes (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Laminated Bodies (AREA)

Abstract

L'invention concerne un adhésif qui est caractéristique en ce qu'il comprend en tant que composant principal un polymère acrylique réticulable, et en ce qu'il comprend en outre un agent de réticulation, et un polymère acrylique non-fonctionnel dont la masse moléculaire moyenne en poids est comprise entre 1000 et 5000, et la valeur Tg est inférieure ou égale à 0°C.
PCT/JP2012/080862 2011-12-01 2012-11-29 Adhésif, feuille adhésive, et stratifié optique WO2013081032A1 (fr)

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JP2017101249A (ja) * 2017-01-18 2017-06-08 藤森工業株式会社 光拡散粘着剤層、及び光拡散粘着フィルム
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