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WO2014103964A1 - Couche antistatique, feuille adhésive antistatique et film optique - Google Patents

Couche antistatique, feuille adhésive antistatique et film optique Download PDF

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Publication number
WO2014103964A1
WO2014103964A1 PCT/JP2013/084359 JP2013084359W WO2014103964A1 WO 2014103964 A1 WO2014103964 A1 WO 2014103964A1 JP 2013084359 W JP2013084359 W JP 2013084359W WO 2014103964 A1 WO2014103964 A1 WO 2014103964A1
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Prior art keywords
meth
antistatic
alkyl
sensitive adhesive
pressure
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PCT/JP2013/084359
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English (en)
Japanese (ja)
Inventor
真人 山形
昌之 岡本
紀二 大學
浩司 設樂
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Nitto Denko Corp
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Nitto Denko Corp
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Priority to CN201380060856.1A priority Critical patent/CN104812866B/zh
Priority to KR1020157011475A priority patent/KR102132619B1/ko
Publication of WO2014103964A1 publication Critical patent/WO2014103964A1/fr
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
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/04—Acids; Metal salts or ammonium salts thereof
    • C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/38—Esters containing sulfur
    • C08F220/387—Esters containing sulfur and containing nitrogen and 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
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/20—Properties of the layers or laminate having particular electrical or magnetic properties, e.g. piezoelectric
    • B32B2307/21—Anti-static
    • 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

Definitions

  • N, N, N-trialkyl-N-vinylammonium tetrafluoroborate N, N, N-trialkyl-N-vinylammonium trifluoroacetate, N, N, N-trialkyl-N-vinylammonium heptafluorobuty Rate, N, N, N-trialkyl-N-vinylammonium trifluoromethanesulfonate, N, N, N-trialkyl-N-vinylammonium perfluorobutanesulfonate, N, N, N-trialkyl-N-vinylammonium bis (Trifluoromethanesulfonyl) imide, N, N, N-trialkyl-N-vinylammonium bis (pentafluoroethanesulfonyl) imide, N, N, N-trialkyl-N-N-vinylammonium bis (pentafluoroethane
  • crosslinking agent used when forming the antistatic layer examples include isocyanate compounds, epoxy compounds, melamine resins, aziridine derivatives, oxazoline crosslinking agents, silicone crosslinking agents, silane crosslinking agents, and metal chelate compounds. .
  • isocyanate compounds and epoxy compounds are more preferably used mainly from the viewpoint of obtaining an appropriate cohesive force, and isocyanate compounds (isocyanate-based crosslinking agents) are particularly preferred. These compounds may be used alone or in combination of two or more.
  • a polyfunctional monomer having two or more radiation-reactive unsaturated bonds can be added as a crosslinking agent.
  • the antistatic agent composition is crosslinked by irradiating with radiation or the like.
  • a polyfunctional monomer having two or more radiation-reactive unsaturated bonds in one molecule for example, it can be crosslinked (cured) by irradiation with radiation such as vinyl group, acryloyl group, methacryloyl group, vinylbenzyl group. Examples thereof include a polyfunctional monomer component having two or more radiation reactive groups of one kind or two or more kinds.
  • the polyfunctional monomer generally, those having 10 or less radiation-reactive unsaturated bonds are preferably used. These compounds may be used alone or in combination of two or more.
  • photo radical polymerization initiator examples include benzoins such as benzoin, benzoin methyl ether, benzoin ethyl ether, methyl o-benzoylbenzoate-p-benzoin ethyl ether, benzoin isopropyl ether, ⁇ -methylbenzoin, benzyl dimethyl ketal, Acetophenones such as trichloroacetophenone, 2,2-diethoxyacetophenone, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methylpropiophenone, 2-hydroxy-4'-isopropyl-2-methylpropiophenone, etc.
  • benzoins such as benzoin, benzoin methyl ether, benzoin ethyl ether, methyl o-benzoylbenzoate-p-benzoin ethyl ether, benzoin isopropyl ether, ⁇ -methylbenzoin, benzyl dimethyl ketal,
  • photocationic polymerization initiator examples include onium salts such as aromatic diazonium salts, aromatic iodonium salts, and aromatic sulfonium salts, and organometallic complexes such as iron-allene complexes, titanocene complexes, and arylsilanol-aluminum complexes. Nitrobenzyl ester, sulfonic acid derivative, phosphoric acid ester, phenol sulfonic acid ester, diazonaphthoquinone, N-hydroxyimide sulfonate and the like. These compounds may be used alone or in combination of two or more.
  • onium salts such as aromatic diazonium salts, aromatic iodonium salts, and aromatic sulfonium salts
  • organometallic complexes such as iron-allene complexes, titanocene complexes, and arylsilanol-aluminum complexes.
  • the antistatic agent composition may contain other known additives such as powders such as colorants and pigments, surfactants, plasticizers, tackifiers, low molecular weight polymers, and the like.
  • powders such as colorants and pigments, surfactants, plasticizers, tackifiers, low molecular weight polymers, and the like.
  • Surface lubricants, leveling agents, antioxidants, corrosion inhibitors, light stabilizers, UV absorbers, polymerization inhibitors, silane coupling agents, inorganic or organic fillers, metal powders, particles, foils Or the like can be added as appropriate according to the use for which the material is used.
  • organic solvent examples include esters such as ethyl acetate, butyl acetate, and 2-hydroxyethyl acetate; ketones such as methyl ethyl ketone, acetone, cyclohexanone, methyl isobutyl ketone, diethyl ketone, methyl-n-propyl ketone, and acetylacetone; Cyclic ethers such as tetrahydrofuran (THF) and dioxane; aliphatic or alicyclic hydrocarbons such as n-hexane and cyclohexane; aromatic hydrocarbons such as toluene and xylene; methanol, ethanol, n-propanol, isopropanol, Aliphatic or alicyclic alcohols such as cyclohexanol; Glycol ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monoe
  • the base film may be subjected to release treatment and antifouling treatment with a silicone-based, fluorine-based, long-chain alkyl-based or fatty acid amide-based release agent, silica powder, acid treatment, alkali treatment, if necessary
  • release treatment and antifouling treatment with a silicone-based, fluorine-based, long-chain alkyl-based or fatty acid amide-based release agent, silica powder, acid treatment, alkali treatment, if necessary
  • easy adhesion treatment such as primer treatment, corona treatment, plasma treatment, and ultraviolet treatment
  • antistatic treatment such as coating type, kneading type, and vapor deposition type can also be performed.
  • the base film is a plastic film that has been subjected to antistatic treatment.
  • the surface protection film itself is more effectively prevented from being charged when it is peeled off. Therefore, charging and contamination are particularly serious problems. It becomes very useful as a surface protective film.
  • the base film is a plastic film, and the antistatic treatment is performed on the plastic film, thereby reducing the charge of the surface protective film itself, and in the antistatic ability to the adherend (protected body). , A better one is obtained.
  • the antistatic treatment to be applied to the plastic film is not particularly limited, but apart from the antistatic layer formed from the antistatic agent composition described above, at least one of the commonly used films.
  • a method of separately providing an antistatic layer on one surface a method of kneading a kneading type antistatic agent into a plastic film, or the like is used.
  • an antistatic resin or conductive polymer comprising an antistatic agent and a resin component a method of applying a conductive resin containing a conductive substance, or a conductive material may be used.
  • the pressure-sensitive adhesive sheet of the present invention include configurations such as a base film (plastic film and antistatic layer), an antistatic layer, and a pressure-sensitive adhesive layer.
  • the cationic antistatic agent examples include a quaternary ammonium group such as alkyltrimethylammonium salt, acyloylamidopropyltrimethylammonium methosulfate, alkylbenzylmethylammonium salt, acylcholine chloride, polydimethylaminoethyl methacrylate (meta ) Acrylate copolymer, styrene copolymer having quaternary ammonium group such as polyvinylbenzyltrimethylammonium chloride, diallylamine copolymer having quaternary ammonium group such as polydiallyldimethylammonium chloride. These compounds may be used alone or in combination of two or more.
  • a quaternary ammonium group such as alkyltrimethylammonium salt, acyloylamidopropyltrimethylammonium methosulfate, alkylbenzylmethylammonium salt, acylcholine chloride, polydi
  • anionic antistatic agent examples include alkyl sulfonate, alkyl benzene sulfonate, alkyl sulfate ester salt, alkyl ethoxy sulfate ester salt, alkyl phosphate ester salt, and sulfonate group-containing styrene copolymer. These compounds may be used alone or in combination of two or more.
  • zwitterionic antistatic agent examples include alkylbetaines, alkylimidazolium betaines, and carbobetaine graft copolymers. These compounds may be used alone or in combination of two or more.
  • Examples of the conductive material include tin oxide, antimony oxide, indium oxide, cadmium oxide, titanium oxide, zinc oxide, indium, tin, antimony, gold, silver, copper, aluminum, nickel, chromium, titanium, iron, cobalt, Examples include copper iodide, and alloys or mixtures thereof.
  • organic solvent used for forming the antistatic layer examples include methyl ethyl ketone, acetone, ethyl acetate, tetrahydrofuran, dioxane, cyclohexanone, n-hexane, toluene, xylene, methanol, ethanol, n-propanol, and isopropanol. Can be mentioned. These solvents may be used alone or in combination of two or more.
  • the blending amount of the antistatic agent is 20% by mass or less, preferably 0.05 to 10% by mass with respect to the total weight of the base film (plastic film).
  • the kneading method is not particularly limited as long as the antistatic agent can be uniformly mixed with the resin used for the base film (plastic film).
  • a heating roll, a Banbury mixer, a pressure kneader, A biaxial kneader or the like is used.
  • the (meth) acrylic polymer having as a main component the (meth) acrylic acid alkyl ester having an alkyl group having 1 to 20 carbon atoms includes the (meth) acrylic acid alkyl ester having an alkyl group having 1 to 20 carbon atoms.
  • the monomer unit (component) is within the above range, it is preferable from the viewpoint of obtaining appropriate wettability and cohesive strength in the pressure-sensitive adhesive composition.
  • specific examples of the (meth) acrylic acid alkyl ester having an alkyl group having 1 to 20 carbon atoms include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, s-butyl (meth) acrylate, t-butyl (meth) acrylate, isobutyl (meth) acrylate, hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate , N-nonyl (meth) acrylate, isononyl (meth) acrylate, n-decyl (meth) acrylate, isodecyl (meth) acrylate, n-dodecyl (meth) acrylate, n-
  • the glass transition temperature (Tg) is set to 0 ° C. or lower (usually ⁇ 100 ° C. or higher) for the purpose of easily balancing the adhesion performance. )
  • a polymerizable monomer for adjusting the glass transition temperature (Tg) and peelability of the acrylic polymer can be used as long as the effects of the present invention are not impaired.
  • a (meth) acrylate having a hydroxyl group (a hydroxyl group-containing (meth) acrylic monomer) is preferably used because crosslinking can be easily controlled. It is done.
  • a hydroxyl group-containing (meth) acrylic monomer that can be copolymerized with the (meth) acrylic acid alkyl ester, if necessary, for the purpose of modifying cohesion, heat resistance, crosslinkability, etc.
  • other monomer components may be included. These monomer compounds may be used alone or in admixture of two or more.
  • hydroxyl group-containing (meth) acrylic monomer By using the hydroxyl group-containing (meth) acrylic monomer, it becomes easy to control the crosslinking of the pressure-sensitive adhesive composition, and thus it becomes easy to control the balance between improvement of wettability by flow and reduction of adhesive strength in peeling. . Furthermore, unlike the above-mentioned carboxyl groups and sulfonate groups, which can generally act as crosslinking sites, hydroxyl groups can be added (blended) as antistatic agents (alkali metal salts, ionic liquids, etc.) Therefore, it can be suitably used also in terms of antistatic properties.
  • the hydroxyl group-containing (meth) acrylic monomer is included, the hydroxyl group-containing (meth) acrylic polymer with respect to all the structural units of the (meth) acrylic polymer (total monomer units (components): 100% by mass).
  • the monomer content is preferably 0.1 to 15% by mass, more preferably 0.5 to 12% by mass, and most preferably 1 to 10% by mass. Within the above range, it is easy to control the balance between wettability and cohesive force of the pressure-sensitive adhesive composition, which is preferable.
  • Carboxyl group-containing monomers such as acrylic acid, methacrylic acid, carboxyethyl acrylate, carboxypentyl acrylate, itaconic acid, maleic acid, fumaric acid, crotonic acid, and isocrotonic acid; Acid anhydride group-containing monomers such as maleic anhydride and itaconic anhydride; Sulphonic acid groups such as styrene sulfonic acid, allyl sulfonic acid, 2- (meth) acrylamide-2-methylpropane sulfonic acid, (meth) acrylamide propane sulfonic acid, sulfopropyl (meth) acrylate, (meth) acryloyloxynaphthalene sulfonic acid Containing monomers; Phosphoric acid group-containing monomers such as 2-hydroxyethylacryloyl phosphate; (Meth) acrylamide, N, N
  • the pressure-sensitive adhesive layer in the present invention is preferably formed by crosslinking a pressure-sensitive adhesive composition containing the (meth) acrylic polymer or the like. Obtaining a pressure-sensitive adhesive layer (antistatic pressure-sensitive adhesive sheet) with better heat resistance by appropriately adjusting the structural unit, the structural ratio, the selection and addition ratio of the crosslinking agent, etc. of the (meth) acrylic polymer. Can do.
  • isocyanate compound examples include lower aliphatic polyisocyanates such as butylene diisocyanate and hexamethylene diisocyanate, cyclopentylene diisocyanate, and cyclohexyl.
  • polyfunctional monomer examples include, for example, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, and 1,6 hexanediol.
  • examples thereof include di (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol hexa (meth) acrylate, divinylbenzene, and N, N′-methylenebisacrylamide.
  • photo radical polymerization initiator examples include benzoins such as benzoin, benzoin methyl ether, benzoin ethyl ether, methyl o-benzoylbenzoate-p-benzoin ethyl ether, benzoin isopropyl ether, ⁇ -methylbenzoin, benzyl dimethyl ketal, Acetophenones such as trichloroacetophenone, 2,2-diethoxyacetophenone, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methylpropiophenone, 2-hydroxy-4'-isopropyl-2-methylpropiophenone, etc.
  • benzoins such as benzoin, benzoin methyl ether, benzoin ethyl ether, methyl o-benzoylbenzoate-p-benzoin ethyl ether, benzoin isopropyl ether, ⁇ -methylbenzoin, benzyl dimethyl ketal,
  • the photopolymerization initiator is usually blended in an amount of 0.1 to 10 parts by weight and preferably in a range of 0.2 to 7 parts by weight with respect to 100 parts by weight of the (meth) acrylic polymer. Within the above range, it is preferable from the viewpoint of easily controlling the polymerization reaction and obtaining an appropriate molecular weight.
  • a photoinitiated polymerization aid such as amines in combination.
  • the photoinitiator aid include 2-dimethylaminoethyl benzoate, dimethylaminoacetophenone, p-dimethylaminobenzoic acid ethyl ester, p-dimethylaminobenzoic acid isoamyl ester, and the like. These compounds may be used alone or in combination of two or more.
  • the polymerization initiation assistant is preferably added in an amount of 0.05 to 10 parts by weight, more preferably 0.1 to 7 parts by weight, based on 100 parts by weight of the (meth) acrylic polymer. Within the above range, it is preferable from the viewpoint of easily controlling the polymerization reaction and obtaining an appropriate molecular weight.
  • the pressure-sensitive adhesive sheet of the present invention is formed by forming the pressure-sensitive adhesive layer on an antistatic layer, and in this case, the pressure-sensitive adhesive composition is generally crosslinked after application of the pressure-sensitive adhesive composition. However, it is also possible to transfer the pressure-sensitive adhesive layer comprising the crosslinked pressure-sensitive adhesive composition onto the antistatic layer.
  • the method for forming the pressure-sensitive adhesive layer on the antistatic layer is not particularly limited.
  • the pressure-sensitive adhesive composition (solution) is applied onto the antistatic layer, and the polymerization solvent is removed by drying. It is produced by forming an adhesive layer on the antistatic layer. Thereafter, curing may be performed for the purpose of adjusting the component transfer of the pressure-sensitive adhesive layer or adjusting the crosslinking reaction.
  • the pressure sensitive adhesive composition (solution) when preparing the antistatic layer by applying the pressure sensitive adhesive composition (solution) on the antistatic layer, it is a kind other than the polymerization solvent in the pressure sensitive adhesive composition so that it can be uniformly applied on the antistatic layer. The above solvent may be newly added.
  • the antistatic pressure-sensitive adhesive sheet having an antistatic layer of the present invention has an antistatic layer having excellent antistatic properties, and therefore can be used in surface protection applications and electronic component manufacturing / shipping process applications.
  • adhesion of dust and dust due to static electricity and destruction of electronic parts due to static electricity may occur, which can be suppressed and useful.
  • the antistatic pressure-sensitive adhesive sheet having the antistatic layer of the present invention can be attached to an optical film and used as an optical film with an antistatic pressure-sensitive adhesive sheet.
  • the surface of the optical film can be protected by sticking the antistatic pressure-sensitive adhesive sheet to the optical film, which is useful.
  • the antistatic pressure-sensitive adhesive sheet can be used for plastic products and the like that are prone to generate static electricity. Therefore, in the technical fields related to optical and electronic parts where charging becomes a particularly serious problem, Useful.
  • Example 1 Preparation of antistatic agent solution
  • a solution obtained by diluting the above (meth) acrylic polymer (A) solution (20% by weight) to 4.2% by weight with methyl ethyl ketone Coronate L (trimethylolpropane / tolylene diisocyanate) was used as a crosslinking agent.
  • Coronate L trimethylolpropane / tolylene diisocyanate
  • Example 2 (Preparation of antistatic agent solution) An antistatic agent solution (2) was prepared in the same manner as in Example 1 except that 10.0 parts of DMAEA-TFSI was used instead of 5.0 parts of DMAEA-TFSI.
  • An antistatic treatment film (2) was produced in the same manner as in Example 1 except that the antistatic agent solution (2) was used in place of the antistatic agent solution (1).
  • Example 3 (Preparation of antistatic agent solution) An antistatic agent solution (3) was prepared in the same manner as in Example 1 except that 20.0 parts of DMAEA-TFSI was used instead of 5.0 parts of DMAEA-TFSI.
  • An antistatic treatment film (5) was produced in the same manner as in Example 1 except that the antistatic agent solution (5) was used in place of the antistatic agent solution (1).
  • a pressure-sensitive adhesive sheet was produced in the same manner as in Example 1 except that the antistatic treatment film (5) was used instead of the antistatic treatment film (1).
  • Example 6 (Preparation of antistatic agent solution) Example 1 was used except that the (meth) acrylic polymer (C) was used in place of the (meth) acrylic polymer (A) and 5.0 parts of DMAEA-TFSI was not used as the conductive agent. Thus, an antistatic agent solution (6) was prepared.
  • An antistatic treatment film (6) was produced in the same manner as in Example 1 except that the antistatic agent solution (6) was used instead of the antistatic agent solution (1).
  • Example 7 (Preparation of antistatic agent solution) Instead of the (meth) acrylic polymer (A), the (meth) acrylic polymer (C) is used, and as a conductive agent, instead of 5.0 parts of DMAEA-TFSI, N-butyl-3-methylpyridinium.
  • An antistatic agent solution (7) was prepared in the same manner as in Example 1 except that 20.0 parts of bis (trifluoromethanesulfonyl) imide (BMP-TFSI in Table 1) was used.
  • An antistatic treatment film (7) was produced in the same manner as in Example 1 except that the antistatic agent solution (7) was used in place of the antistatic agent solution (1).
  • Example 8 (Preparation of antistatic agent solution)
  • the (meth) acrylic polymer (C) was used in place of the (meth) acrylic polymer (A), and DMAPAA-TFSI 20.0 parts was used in place of 5.0 parts of DMAEA-TFSI as a conductive agent. Except for this, an antistatic agent solution (8) was prepared in the same manner as in Example 1.
  • An antistatic treatment film (8) was produced in the same manner as in Example 1 except that the antistatic agent solution (8) was used in place of the antistatic agent solution (1).
  • a pressure-sensitive adhesive sheet was produced in the same manner as in Example 1 except that the antistatic treatment film (8) was used instead of the antistatic treatment film (1).
  • Example 9 (Preparation of antistatic agent solution) The same as Example 1 except that the (meth) acrylic polymer (D) was used instead of the (meth) acrylic polymer (A) and that 5.0 parts of DMAEA-TFSI was not used as the conductive agent. Thus, an antistatic agent solution (9) was prepared.
  • the antistatic agent solution (9) is used and applied onto a polyethylene terephthalate (PET) film (thickness 38 ⁇ m, Lumirror S10 manufactured by Toray Industries, Inc.) using a Meyer bar. The solvent was removed by drying at 130 ° C. for 1 minute to form an antistatic layer (thickness 0.1 ⁇ m), and an antistatic treatment film (9) was produced.
  • PET polyethylene terephthalate
  • a pressure-sensitive adhesive sheet was produced in the same manner as in Example 1 except that the antistatic treatment film (9) was used instead of the antistatic treatment film (1).
  • Example 10 (Preparation of antistatic agent solution)
  • Example 1 was used except that the (meth) acrylic polymer (E) was used instead of the (meth) acrylic polymer (A), and 5.0 parts of DMAEA-TFSI was not used as the conductive agent.
  • an antistatic agent solution (10) was prepared.
  • Example 11 (Preparation of antistatic film)
  • the antistatic agent solution (10) is used and applied onto a polyethylene terephthalate (PET) film (thickness 38 ⁇ m, Lumirror S10 manufactured by Toray Industries, Inc.) using a Mayer bar, The solvent was removed by drying at 130 ° C. for 1 minute to form an antistatic layer (thickness 0.1 ⁇ m), and an antistatic treatment film (11) was produced.
  • PET polyethylene terephthalate
  • a pressure-sensitive adhesive sheet was produced in the same manner as in Example 1 except that the antistatic treatment film (11) was used instead of the antistatic treatment film (1).
  • the antistatic agent solution (11) is used, and instead of a polyethylene terephthalate (PET) film (thickness 38 ⁇ m, Lumirror S10 manufactured by Toray Industries, Inc.), corona-treated polyethylene terephthalate
  • PET polyethylene terephthalate
  • An antistatic film (12) was produced in the same manner as in Example 1 except that a (PET) film (thickness 38 ⁇ m, manufactured by Mitsubishi Plastics, Diafoil T100C) was used.
  • a pressure-sensitive adhesive sheet was produced in the same manner as in Example 1 except that the antistatic treatment film (12) was used instead of the antistatic treatment film (1).
  • the weight average molecular weight (Mw) of the (meth) acrylic polymer (E) for the antistatic layer was measured using a GPC apparatus (HLC-8220GPC) manufactured by Tosoh Corporation. The measurement conditions are as follows. In addition, the weight average molecular weight was calculated
  • the opposite surface of the triacetyl cellulose polarizing plate was fixed to an acrylic plate with a double-sided adhesive tape, and the adhesive sheet was The adhesive strength when one end was peeled at a tensile speed of 0.3 m / min (low speed peeling) and a peeling angle of 180 ° was measured. The measurement was performed in an environment of 23 ° C. ⁇ 50% RH.
  • the opposite surface of the triacetyl cellulose polarizing plate is fixed to an acrylic plate with a double-sided adhesive tape as shown in FIG.
  • the adhesive strength was measured when one end of the sheet was peeled at a tensile speed of 30 m / min (high speed peeling) and a peeling angle of 180 °.
  • the measurement was performed in an environment of 23 ° C. ⁇ 50% RH. Those having an adhesive strength of less than 6.0 N / 25 mm during high-speed peeling were considered good, and those having an adhesive strength of 6.0 N / 25 mm or more were considered defective.
  • the measurement results are shown in Table 2.
  • the pressure-sensitive adhesive sheet 2 according to each example and comparative example was cut into a size of 70 mm in width and 130 mm in length, the separator was peeled off, and then the acrylic plate 4 (Mitsubishi Rayon Co., Ltd.) was previously neutralized.
  • the acrylic plate 4 Mitsubishi Rayon Co., Ltd.
  • polarizing plate 3 manufactured by Nitto Denko Corporation, SEG1425DU, width: 70 mm, length: 100 mm
  • one end on the surface is 30 mm It crimped
  • an absolute value is 1.0 kV or less, and it is more preferable that it is 0.5 kV or less. Within this range, dust collection due to static electricity and static electricity failure of electronic components can be prevented, which is useful.
  • the pressure-sensitive adhesive sheet was peeled off from the adherend by hand, and the state of contamination of the adherend surface at that time was visually observed.
  • the evaluation criteria are as follows. ⁇ If no contamination was found: ⁇ ⁇ If contamination is found: ⁇
  • the separator of the pressure-sensitive adhesive sheet according to each example and comparative example was peeled off and allowed to stand at 170 ° C. for 30 minutes and then left in an environment of 23 ° C. ⁇ 50% RH for 2 hours to determine the surface resistivity of the pressure-sensitive adhesive surface. It was measured with a rate measuring device (manufactured by Mitsubishi Chemical Corporation, Hiresta UP MCP-HT450 type). The applied voltage was 100 V, and the application time was 30 seconds.
  • the surface resistivity is preferably 10 13 or less, and more preferably 10 12 or less.
  • the pressure-sensitive adhesive sheet according to each Example and Comparative Example was cut to a size of 25 mm in width and 100 mm in length, and after peeling the release liner, a triacetyl cellulose polarizing plate (manufactured by Nitto Denko Corporation, SEG1425DU, width: 70 mm, length: 100 mm) was pressure-bonded with a hand roller and then laminated under pressure-bonding conditions of 0.25 MPa and 0.3 m / min to prepare an evaluation sample (an optical film with an antistatic pressure-sensitive adhesive sheet). After the above lamination, after leaving for 30 minutes in an environment of 23 ° C.
  • the opposite surface of the triacetyl cellulose polarizing plate was fixed to an acrylic plate with a double-sided adhesive tape, and the adhesive sheet was When one end is peeled off at a tensile speed of 30 m / min (high-speed peeling) and a peeling angle of 180 °, whether or not the adhesive remains on the surface of the triacetyl cellulose polarizing plate (adhesive residue) is visually observed. It was judged. When there is no adhesive residue: ⁇ When adhesive residue occurs: ⁇
  • Comparative Example 1 an antistatic pressure-sensitive adhesive sheet formed on a corona-treated base film with an antistatic layer using an antistatic agent made of an acrylic resin copolymerized with quaternary ammonium chloride. was produced, peeling electrification voltage exceeds ⁇ 1.0 kV, the surface resistivity after heating (above the detection limit) of greater than 10 13 resulted. Moreover, in Comparative Example 2, when the corona treatment was not performed on the base film as compared with Comparative Example 1, it was confirmed that the anchoring property was insufficient, and an adhesive sheet that can be evaluated was obtained. could not. Therefore, neither of Comparative Examples 1 and 2 can be obtained that satisfies all of antistatic properties (peeling voltage, surface resistivity), adhesive properties, low contamination, anchoring properties, and transparency. It was confirmed.

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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)
  • Laminated Bodies (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)

Abstract

La présente invention concerne une couche antistatique qui présente des propriétés antistatiques, une résistance à la chaleur, une transparence et des propriétés de faible contamination excellentes et qui est apte, en particulier, à supprimer une rupture d'un composant électronique due à l'électricité statique ou l'adhérence d'impuretés, de poussières ou analogues ; une feuille adhésive antistatique qui comprend la couche antistatique ; et un film optique. Une couche antistatique est caractérisée en ce qu'elle est formée à partir d'une composition d'agent antistatique qui contient un agent de réticulation et un polymère (méth)acrylique qui contient un liquide ionique réactif en tant qu'unité monomère.
PCT/JP2013/084359 2012-12-27 2013-12-20 Couche antistatique, feuille adhésive antistatique et film optique Ceased WO2014103964A1 (fr)

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CN201380060856.1A CN104812866B (zh) 2012-12-27 2013-12-20 防静电层、防静电性粘合片和光学薄膜
KR1020157011475A KR102132619B1 (ko) 2012-12-27 2013-12-20 대전 방지층, 대전 방지성 점착 시트 및 광학 필름

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JP2013262747A JP6263379B2 (ja) 2012-12-27 2013-12-19 帯電防止層、帯電防止性粘着シート、及び光学フィルム
JP2013-262747 2013-12-19

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EP3816227A4 (fr) * 2018-05-15 2021-07-07 Showa Denko Materials Co., Ltd. Composition de résine, matériau de stockage de chaleur et article
WO2022208317A1 (fr) 2021-04-02 2022-10-06 3M Innovative Properties Company Ruban adhésif transparent, résistant à la chaleur, doté de performances antistatiques et procédé d'utilisation associé
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TWI692895B (zh) 2017-10-23 2020-05-01 南韓商Ｌｇ化學股份有限公司 光學膜、光學膜的製造方法、及有機發光電子裝置的製造方法
JP6740489B2 (ja) * 2018-06-13 2020-08-12 リンテック株式会社 粘着シート
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JP7546244B2 (ja) * 2019-05-13 2024-09-06 株式会社ニコン・エシロール 眼鏡レンズ、組成物
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JP2023136273A (ja) 2022-03-16 2023-09-29 日東電工株式会社 粘着剤組成物、粘着剤層、及び粘着シート
JP2023177507A (ja) * 2022-06-02 2023-12-14 大成ファインケミカル株式会社 親水性塗料組成物
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KR102132619B1 (ko) 2020-07-10
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JP6263379B2 (ja) 2018-01-17
TWI624504B (zh) 2018-05-21
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JP2014141649A (ja) 2014-08-07

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