WO2014097719A1 - Composition adhésive pour film optique et film de protection de surface - Google Patents

Composition adhésive pour film optique et film de protection de surface Download PDF

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Publication number
WO2014097719A1
WO2014097719A1 PCT/JP2013/077644 JP2013077644W WO2014097719A1 WO 2014097719 A1 WO2014097719 A1 WO 2014097719A1 JP 2013077644 W JP2013077644 W JP 2013077644W WO 2014097719 A1 WO2014097719 A1 WO 2014097719A1
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Prior art keywords
meth
sensitive adhesive
pressure
mass
adhesive composition
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PCT/JP2013/077644
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English (en)
Japanese (ja)
Inventor
中西　健一
一博 佐々木
雄太 竹内
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昭和電工株式会社
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Priority to CN201380065202.8A priority Critical patent/CN104870592B/zh
Priority to KR1020157018415A priority patent/KR101686761B1/ko
Priority to JP2014552972A priority patent/JP6251687B2/ja
Publication of WO2014097719A1 publication Critical patent/WO2014097719A1/fr

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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
    • 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
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
    • 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
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/24—Catalysts containing metal compounds of tin
    • 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
    • C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
    • C08G18/4063—Mixtures of compounds of group C08G18/62 with other macromolecular compounds
    • 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
    • C08G18/48—Polyethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/32—Compounds containing nitrogen bound to oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/02—Polyalkylene oxides
    • 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
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0025—Crosslinking or vulcanising agents; including accelerators
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
    • C08K5/57—Organo-tin compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
    • C09J2301/408—Additional features of adhesives in the form of films or foils characterized by the presence of essential components additives as essential feature of the adhesive layer
    • 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
    • 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
    • C09J2471/00—Presence of polyether

Definitions

  • the present invention relates to an adhesive composition for an optical film and a surface protective film.
  • Patent Documents 1 and 2 disclose pressure-sensitive adhesives obtained by adding a polyether polyol as an antistatic agent to an acrylic copolymer.
  • Patent Document 3 discloses an adhesive that achieves both antistatic properties and transparency by grafting a polyether polyol onto an acrylic polymer.
  • this pressure-sensitive adhesive has a high acid value, there is a problem that it is difficult to use it for an optical member that dislikes corrosion such as an ITO film.
  • the present invention provides an optical film pressure-sensitive adhesive composition and a surface protective film that are excellent in antistatic properties and transparency, and have low contamination and corrosion properties to adherends, in view of the problems of the above-described conventional techniques. Objective.
  • the present inventors have obtained (meth) acrylic resins having a specific weight average molecular weight, polyoxy having a specific number average molecular weight.
  • the pressure-sensitive adhesive composition for optical films containing alkylene polyol, polyisocyanate, ionic compound and tin-based catalyst in specific weight ratios exhibits good antistatic properties and transparency, low contamination and corrosion properties on the adherend.
  • the present invention was completed based on this finding.
  • the present invention is shown by the following (1) to (10).
  • (1) (A) (meth) acrylic resin 65 to 85% by mass, (B) polyoxyalkylene polyol 10 to 30% by mass, (C) polyisocyanate 1.0 to 5.0% by mass, D) A pressure-sensitive adhesive composition for an optical film comprising 0.2 to 1.0% by mass of an ionic compound and (E) a tin-based catalyst of 0.005 to 0.1% by mass, comprising (A) (meta (2) A pressure-sensitive adhesive composition for optical films, wherein the acrylic resin has a weight average molecular weight of 100,000 to 600,000 and (B) the polyoxyalkylene polyol has a number average molecular weight of 500 to 1500.
  • a pressure-sensitive adhesive layer obtained by curing the pressure-sensitive adhesive composition for an optical film according to any one of (1) to (7) is formed on one surface of a transparent substrate. A surface protective film.
  • the transparent base material is polyethylene terephthalate, polyethylene, polypropylene, polystyrene, polyimide, polyvinyl alcohol, polyvinyl chloride or cellulose having a thickness of 5 to 200 ⁇ m.
  • a pressure-sensitive adhesive composition for an optical film and a surface protective film that are excellent in antistatic properties and transparency, and have low contamination and corrosiveness to an adherend.
  • the pressure-sensitive adhesive composition for an optical film of the present invention comprises (A) (meth) acrylic resin, (B) polyoxyalkylene polyol, (C) polyisocyanate, (D) ionic compound, and (E).
  • a tin-based catalyst In the present invention, (meth) acrylic resin refers to acrylic resin or methacrylic resin, and (meth) acrylate refers to acrylate or methacrylate.
  • (meth) acrylate type resin refers to the polymer whose 80 mol% or more of all the structural monomers are (meth) acrylate type monomers.
  • (A) (Meth) acrylic resin The (meth) acrylic monomer used in the polymerization of the (A) (meth) acrylic resin in the present invention is not particularly limited, but a carboxyl group (chemical formula: -COOH) What does not contain is preferable.
  • (meth) acrylic monomers examples include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, tert-butyl (meth) ) Acrylate, isobutyl (meth) acrylate, n-hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isooctyl (meth) acrylate, lauryl (meth) acrylate, isodecyl (meth) acrylate, stearyl (meth) acrylate, tridecyl Alkyl (meth) acrylates such as (meth) acrylate and isostearyl (meth) acrylate, cyclohexyl (meth) acrylate, norbornyl (meth) acrylate, iso
  • (A) (meth) acrylic resin and (B) polyoxyalkylene polyol that is, transparency of the pressure-sensitive adhesive layer obtained by curing the pressure-sensitive adhesive composition for optical films
  • (A) ( The copolymer component of the (meth) acrylic resin preferably contains 15 to 50 mol%, more preferably 25 to 45 mol% of methyl acrylate or methyl methacrylate.
  • the (A) (meth) acrylic resin in the present invention can be integrated by reacting with a polyoxyalkylene polyol via a polyisocyanate (transparency is improved). It is preferable to contain a (meth) acrylic monomer.
  • hydroxyl-containing (meth) acrylic monomers examples include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, and 1,3-butanediol (meth) acrylate , Hydroxyl group-containing (meth) acrylates such as 1,4-butanediol (meth) acrylate, 1,6-hexanediol (meth) acrylate, and 3-methylpentanediol (meth) acrylate.
  • 2-hydroxyethyl (meth) acrylate is preferable in view of copolymerizability and reactivity.
  • the hydroxyl group-containing (meth) acrylic monomer is preferably contained in an amount of 0.5 to 10 mol%, more preferably 0.6 to 8.0 mol%, as a copolymer component of the (A) (meth) acrylic resin. .
  • polymerizable monomers can be used as a copolymerization component as long as the polymerizability is not impaired.
  • examples of such polymerizable monomers include acrylonitrile, methacrylonitrile, styrene, ⁇ -methylstyrene, vinyl acetate, vinyl propionate, vinyl stearate, vinyl chloride, vinylidene chloride, alkyl vinyl ether, vinyl toluene, vinyl pyridine, Examples thereof include vinylpyrrolidone, itaconic acid dialkyl ester, fumaric acid dialkyl ester, allyl alcohol, acrylic chloride, methyl vinyl ketone, N-acrylamidomethyltrimethylammonium chloride, allyltrimethylammonium chloride, and dimethylallyl vinylketone.
  • the (A) (meth) acrylic resin in the present invention needs to have a weight average molecular weight of 100,000 to 600,000, preferably 150,000 to 500,000, more preferably 200,000 to 400,000.
  • a weight average molecular weight 100,000 to 600,000, preferably 150,000 to 500,000, more preferably 200,000 to 400,000.
  • the weight average molecular weight is smaller than 100,000, the cohesive force becomes small, and an adhesive residue is generated.
  • the weight average molecular weight is larger than 600,000, the compatibility between the (A) (meth) acrylic resin and the (B) polyoxyalkylene polyol is deteriorated, and the transparency of the resulting pressure-sensitive adhesive layer is deteriorated.
  • the weight average molecular weight is measured at normal temperature using gel permeation chromatography (manufactured by Showa Denko KK, Shodex (registered trademark) GPC-101) under the following conditions, and is calculated in terms of polystyrene. Is. Column: Showa Denko KK, Shodex (registered trademark) LF-804 Column temperature: 40 ° C Sample: 0.2 mass% tetrahydrofuran solution of copolymer Flow rate: 1 ml / min Eluent: Tetrahydrofuran
  • the glass transition temperature (Tg) of the (A) (meth) acrylic resin in the present invention is preferably ⁇ 80 to 0 ° C., more preferably ⁇ 70 to ⁇ 10 ° C.
  • Tg is higher than 0 ° C.
  • Tg is lower than ⁇ 80 ° C.
  • the cohesive force becomes small, which may cause adhesive residue, which is not preferable.
  • Tg of (A) (meth) acrylic-type resin can be adjusted by changing suitably the monomer component and composition ratio to be used.
  • Tg refers to that obtained from the following method.
  • (A) A 10 mg sample was taken from the (meth) acrylic resin, and the temperature was changed from ⁇ 80 ° C. to 200 ° C. at a rate of temperature increase of 10 ° C./min using a differential scanning calorimeter (DSC). Differential scanning calorimetry is performed, and the endothermic start temperature due to glass transition is defined as Tg. When two Tg's are observed, the average value of the two Tg's is taken.
  • DSC differential scanning calorimeter
  • the polymerization method of the (A) (meth) acrylic resin in the present invention is not particularly limited, and it can be polymerized by a known method such as solution polymerization, emulsion polymerization, bulk polymerization, suspension polymerization, or alternating copolymerization. Among these, solution polymerization is particularly preferable. In addition, the obtained copolymer may be any of a random copolymer, a block copolymer, and the like.
  • the polymerization initiator used in the polymerization of the (meth) acrylic resin is not particularly limited, and can be appropriately selected from known ones.
  • 2,2′-azobis isobutyronitrile
  • 2,2′-azobis (4-methoxy-2,4-dimethylvaleronitrile)
  • 1,1′-azobis 1,1′-azobis (cyclohexane-1-carbonitrile)
  • dimethyl- Azo polymerization initiators such as 2,2′-azobis (2-methylpropionate); 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) cyclod
  • An oil-soluble polymerization initiator such as
  • polymerization initiators may be used alone or in combination of two or more.
  • the amount of the polymerization initiator used may be a normal amount, for example, can be selected from the range of about 0.01 to 5 parts by weight with respect to 100 parts by weight of the monomer, and 0.02 to 4 parts by weight The range is preferably 0.03 to 3 parts by mass.
  • solvents include esters such as ethyl acetate, n-propyl acetate and n-butyl acetate, aromatic hydrocarbons such as toluene and benzene, aliphatic hydrocarbons such as n-hexane and n-heptane, Examples thereof include organic solvents such as cycloaliphatic hydrocarbons such as cyclohexane and methylcyclohexane, and ketones such as methyl ethyl ketone and methyl isobutyl ketone. These solvents may be used alone or in combination of two or more.
  • the blending amount of the (A) (meth) acrylic resin in the present invention is required to be 65 to 85% by mass, and more preferably 70 to 85% by mass.
  • the blending amount is less than 65% by mass, the adherend is contaminated.
  • the blending amount exceeds 85% by mass, sufficient charging characteristics cannot be obtained.
  • (B) Polyoxyalkylene polyol The (B) polyoxyalkylene polyol in the present invention is not particularly limited as long as it is a polymer polyol having an ether group, and known polymer polyols can be used as appropriate.
  • Examples of (B) polyoxyalkylene polyols include polyethylene glycol, polypropylene glycol, polytetramethylene ether glycol, and derivatives or copolymers thereof.
  • polypropylene glycol is preferable because it is easy to adjust the compatibility with the (meth) acrylic resin. These may be used alone or in combination of two or more.
  • the (B) polyoxyalkylene polyol in the present invention needs to have a number average molecular weight of 500 to 1500, preferably 800 to 1200.
  • a number average molecular weight exceeds 1500, the transparency of the pressure-sensitive adhesive layer is deteriorated.
  • the number average molecular weight is smaller than 500, there is a possibility that adhesive residue may be generated, which is not preferable.
  • the number average molecular weight is obtained by measuring by GPC (gel permeation chromatography).
  • the blending amount of the (B) polyoxyalkylene polyol in the present invention is required to be 10 to 30% by mass, and more preferably 15 to 25% by mass.
  • the blending amount is less than 10% by mass, sufficient charging characteristics cannot be obtained.
  • the blending amount exceeds 30% by mass, the adherend is contaminated.
  • (C) Polyisocyanate Examples of (C) polyisocyanate in the present invention include aromatic, aliphatic and alicyclic polyisocyanates.
  • (C) Examples of polyisocyanates include 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate (HDI), 2-methyl-1,5-pentane diisocyanate, 3-methyl-1,5-pentane diisocyanate , Trimethylhexamethylene diisocyanate, isophorone diisocyanate, cyclohexyl diisocyanate, tolylene diisocyanate (TDI), hydrogenated tolylene diisocyanate, diphenylmethane diisocyanate, hydrogenated diphenylmethane diisocyanate, polyphenylmethane polyisocyanate, xylene diisocyanate, hydrogenated xylene diisocyanate, tetramethylxylylene Diisocyanate, norborn
  • the blending amount of the (C) polyisocyanate in the present invention is required to be 1.0 to 5.0% by mass, and more preferably 2.0 to 4.0% by mass.
  • the blending amount is less than 1.0% by mass, sufficient cohesive force cannot be obtained.
  • the blending amount exceeds 5.0% by mass, the adhesive layer becomes too hard and adheres to the adherend. The wettability becomes worse.
  • (D) Ionic Compound As the (D) ionic compound used in the present invention, a liquid or solid ionic compound composed of an anion and a cation at 25 ° C. may be mentioned. Specific examples include alkali metal salts, ionic liquids (liquid form at 25 ° C.), surfactants and the like. Of these, alkali metal salts are preferred because they are less likely to contaminate the adherend. Examples of the alkali metal salt include compounds comprising an alkali metal cation such as lithium, sodium and potassium and an anion.
  • These alkali metal salts may be used alone or in combination of two or more.
  • the blending amount of the (D) ionic compound in the present invention is required to be 0.2 to 1.0% by mass, and more preferably 0.3 to 0.8% by mass. When the blending amount is less than 0.2% by mass, sufficient charging characteristics cannot be obtained. On the other hand, when the blending amount exceeds 1.0% by mass, the adherend is contaminated.
  • (E) Tin-based catalyst examples include dibutyltin dilaurate, dibutyltin diethylhexoate, and dioctyltin dilaurate. Of these, dioctyltin dilaurate is preferred because (C) the polyisocyanate has good curability and high safety.
  • the amount of the (E) tin-based catalyst in the present invention is required to be 0.005 to 0.1% by mass, and more preferably 0.01 to 0.05% by mass.
  • the blending amount is less than 0.005% by mass, sufficient cohesive force cannot be obtained.
  • the blending amount exceeds 0.1% by mass, the stability of the (meth) acrylic resin is poor. The pot life will be shortened.
  • the pressure-sensitive adhesive composition for an optical film of the present invention preferably has an acid value of 0 to 5 mgKOH / g, more preferably 0 to 1 mgKOH / g, and further preferably 0 to 0.3 mgKOH / g. More preferably, it is 0 to 0.1 mgKOH / g. If the acid value is higher than 5 mgKOH / g, it is difficult to use it for materials that are susceptible to corrosion, such as ITO films.
  • the acid value of the composition is a value measured according to JIS K0070. For example, measurement is performed as follows.
  • B is the amount of 0.1N potassium hydroxide-ethanol solution used (ml)
  • f is the factor of 0.1N potassium hydroxide-ethanol solution
  • S is the amount of sample collected ( g).
  • additives may be added to the pressure-sensitive adhesive composition for optical films of the present invention as necessary within a range not impairing transparency.
  • Additives include plasticizers, surface lubricants, leveling agents, softeners, antioxidants, antioxidants, light stabilizers, UV absorbers, polymerization inhibitors, benzotriazole-based light stabilizers, phosphate esters System and other flame retardants, and antistatic agents such as surfactants.
  • the optical film pressure-sensitive adhesive composition of the present invention may be diluted with an organic solvent for the purpose of adjusting the viscosity during coating.
  • organic solvent examples include methyl ethyl ketone, acetone, ethyl acetate, tetrahydrofuran, dioxane, cyclohexanone, n-hexane, toluene, xylene, n-propanol, isopropanol, and n-propyl acetate.
  • These organic solvents may be used alone or in combination of two or more.
  • a pressure-sensitive adhesive layer obtained by curing the above-described pressure-sensitive adhesive composition for optical films is formed on one side of a transparent substrate.
  • the thickness of the pressure-sensitive adhesive layer is usually 3 to 100 ⁇ m, preferably 5 to 50 ⁇ m.
  • the transparent substrate include polyethylene terephthalate, polyethylene, polypropylene, polystyrene, polyimide, polyvinyl alcohol, polyvinyl chloride, and cellulose.
  • the thickness of the transparent substrate is usually about 5 to 200 ⁇ m, preferably about 10 to 100 ⁇ m.
  • easy adhesion treatment such as plasma treatment or ultraviolet treatment can be performed.
  • the transparent substrate those subjected to antistatic treatment are more preferably used.
  • the antistatic treatment applied to the transparent substrate is not particularly limited, but a method of providing an antistatic layer on at least one side of a commonly used transparent substrate or a method of kneading an antistatic agent on the transparent substrate is used. Can do.
  • a known coating method can be used.
  • Conventional coaters such as gravure roll coaters, reverse roll coaters, kiss roll coaters Coating can be performed using a dip roll coater, bar coater, knife coater, spray coater, comma coater, direct coater or the like.
  • a separator can be bonded to the surface of the pressure-sensitive adhesive layer for the purpose of protecting the pressure-sensitive adhesive surface as necessary.
  • a base material constituting the separator there are paper and plastic film, but a plastic film is preferably used from the viewpoint of excellent surface smoothness.
  • the film is not particularly limited as long as it can protect the above-mentioned pressure-sensitive adhesive layer, and examples thereof include a polyethylene film, a polypropylene film, a polyethylene terephthalate film, and a polybutene film.
  • the surface protective film of the present invention configured as described above has a surface specific resistance value of an adhesive surface of 1.0 ⁇ 10 10 ⁇ / ⁇ or less and a haze of 1.2 or less, it is a plastic that easily generates static electricity. Used for products. Among them, it can be suitably used as a surface protective film used for the purpose of protecting the surface of an optical member such as a polarizing plate, a wave plate, a retardation plate, an optical compensation film, a reflection sheet, and a brightness enhancement film used for a liquid crystal display. .
  • a (meth) acrylic resin (A-1) having a glass transition temperature of ⁇ 30 ° C. and a weight average molecular weight of 250,000.
  • the glass transition temperature and the weight average molecular weight of the (meth) acrylic resin were measured by the method described above.
  • the (meth) acrylic resin (A-2) and the (meth) acrylic resin (A-3) are the same as the (meth) acrylic resin (A-1) except that the monomers used are changed as shown in Table 1. ).
  • the glass transition temperature and the weight average molecular weight were also measured. The results are shown in Table 1.
  • Examples 1 and 2 and Comparative Examples 1 to 7 > (Meth) acrylic resin, polyoxyalkylene polyol, polyisocyanate, ionic compound and tin-based catalyst are blended with the composition shown in Table 2, and the solid content concentration is adjusted to 50% by mass with ethyl acetate. Then, a pressure-sensitive adhesive composition solution for an optical film was obtained by mixing using a disper. This solution was cast and applied on a release surface of a separator obtained by subjecting one side of a 38 ⁇ m-thick polyethylene terephthalate (PET) film to a release treatment so that the thickness after drying was 50 ⁇ m. For 5 minutes and at 110 ° C. for 3 minutes, and then a PET film having a thickness of 50 ⁇ m was bonded to prepare an adhesive sheet.
  • PET polyethylene terephthalate
  • ⁇ Transparency> The obtained pressure-sensitive adhesive sheet was cut into a size of 30 mm ⁇ 30 mm, the separator of the pressure-sensitive adhesive sheet was peeled off, and the sample was bonded to a glass plate was used as a measurement sample.
  • the haze was measured using Haze meter NM-150 (made by Murakami Color Research Laboratory Co., Ltd.) using “HR-100 type” manufactured by Murakami Color Research Laboratory Co., Ltd.
  • the haze (%) was calculated by dividing the diffuse transmittance by the total light transmittance and multiplying by 100.
  • n number was made into 3 times and the average value was employ
  • the results are shown in Table 2.
  • haze value means that transparency is so high that a value is small.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne une composition adhésive pour film optique, ladite composition contenant (A) 65 à 85 % en masse d'une résine (méth)acrylique ayant un poids moléculaire moyen en poids allant de 100 000 à 600 000, (B) 10 à 30 % en masse d'un polyol de polyoxyalkylène ayant un poids moléculaire moyen en nombre allant de 500 à 1 500, (C) 1,0 à 5,0 % en masse d'un polyisocyanate, (D) 0,2 à 1,0 % en masse d'un composé ionique et (E) 0,005 à 0,1 % en masse d'un catalyseur d'étain. La composition adhésive pour film optique présente l'avantage d'avoir d'excellentes propriétés antistatiques et une excellente transparence, une faible contamination et une faible corrosion de l'élément adhérent.
PCT/JP2013/077644 2012-12-19 2013-10-10 Composition adhésive pour film optique et film de protection de surface WO2014097719A1 (fr)

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CN201380065202.8A CN104870592B (zh) 2012-12-19 2013-10-10 光学膜用粘着剂组合物及表面保护膜
KR1020157018415A KR101686761B1 (ko) 2012-12-19 2013-10-10 광학 필름용 점착제 조성물 및 표면 보호 필름
JP2014552972A JP6251687B2 (ja) 2012-12-19 2013-10-10 光学フィルム用粘着剤組成物及び表面保護フィルム

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JP2012-276951 2012-12-19
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JP2019127526A (ja) * 2018-01-24 2019-08-01 日東電工株式会社 表面保護フィルムおよび保護フィルム付き光学部材
WO2024080146A1 (fr) * 2022-10-14 2024-04-18 日東電工株式会社 Composition adhésive, feuille adhésive et film de renfort

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JP6068403B2 (ja) * 2014-08-07 2017-01-25 藤森工業株式会社 透明導電性フィルム用表面保護フィルム及びそれを用いた透明導電性フィルム
WO2020066866A1 (fr) * 2018-09-26 2020-04-02 昭和電工株式会社 Composition adhésive de feuille de protection de surface sensible et film de protection de surface
CN111534248B (zh) * 2020-05-25 2023-04-21 中国乐凯集团有限公司 压敏胶粘剂及其制备方法、表面保护膜和元件
CN113583282B (zh) * 2021-09-10 2023-01-17 中国科学技术大学先进技术研究院 抗静电光学膜及其制备方法、以及显示面板

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JP2005325255A (ja) * 2004-05-14 2005-11-24 Nitto Denko Corp 粘着剤組成物、粘着シート類、および表面保護フィルム
JP2010037355A (ja) * 2008-07-31 2010-02-18 Big Technos Kk 電気剥離性粘着剤組成物、電気剥離性粘着製品及びその剥離方法
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WO2024080146A1 (fr) * 2022-10-14 2024-04-18 日東電工株式会社 Composition adhésive, feuille adhésive et film de renfort

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CN104870592B (zh) 2016-10-12
TW201425507A (zh) 2014-07-01
KR101686761B1 (ko) 2016-12-14
TWI510584B (zh) 2015-12-01
JPWO2014097719A1 (ja) 2017-01-12
KR20150095798A (ko) 2015-08-21
CN104870592A (zh) 2015-08-26
JP6251687B2 (ja) 2017-12-20

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