WO2013161812A1 - Composition adhésive à durcissement par uv et couche adhésive - Google Patents

Composition adhésive à durcissement par uv et couche adhésive Download PDF

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Publication number
WO2013161812A1
WO2013161812A1 PCT/JP2013/061915 JP2013061915W WO2013161812A1 WO 2013161812 A1 WO2013161812 A1 WO 2013161812A1 JP 2013061915 W JP2013061915 W JP 2013061915W WO 2013161812 A1 WO2013161812 A1 WO 2013161812A1
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Prior art keywords
meth
acrylate
adhesive composition
pressure
sensitive adhesive
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PCT/JP2013/061915
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English (en)
Japanese (ja)
Inventor
聖 渡邊
和毅 木村
澤田　浩
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荒川化学工業株式会社
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Priority to JP2014512610A priority Critical patent/JP6024748B2/ja
Priority to CN201380022223.1A priority patent/CN104302720B/zh
Priority to KR1020147029431A priority patent/KR102062177B1/ko
Publication of WO2013161812A1 publication Critical patent/WO2013161812A1/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
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/24—Catalysts containing metal compounds of tin
    • C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
    • 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
    • C08G18/4825—Polyethers containing two hydroxy groups
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
    • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/81—Unsaturated isocyanates or isothiocyanates
    • C08G18/8108—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group
    • C08G18/8116—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/81—Unsaturated isocyanates or isothiocyanates
    • C08G18/8141—Unsaturated isocyanates or isothiocyanates masked
    • C08G18/815—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen
    • C08G18/8158—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen
    • C08G18/8175—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen with esters of acrylic or alkylacrylic acid having only one group containing active hydrogen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • 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
    • C09J133/062—Copolymers with monomers not covered by C09J133/06
    • C09J133/066—Copolymers with monomers not covered by C09J133/06 containing -OH groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C09J175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
    • 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
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16

Definitions

  • the present invention relates to an ultraviolet curable adhesive composition and an adhesive layer.
  • liquid crystal display devices have been widely used for display devices such as on-vehicle devices, outdoor instruments, displays such as personal computers, and televisions, and the demand for them has been increasing. It is increasing. Recently, in particular, there are ATMs of financial institutions such as banks, vending machines, mobile phones, personal digital assistants, digital audio players, portable game machines, electronic dictionaries, photocopiers, fax machines, car navigation systems and other digital information equipment. A touch panel using a liquid crystal display device is often used.
  • the touch panel is an electronic component that combines a display device and a position input device, displays image information received from the outside on a liquid crystal display, senses touched screen position information, and outputs the information to the outside as an information signal. It has a function.
  • the touch panel position input device mainly has a control method such as a resistance film method, a capacitance method, an electromagnetic induction method, an optical method, and an acoustic method, and in particular, a resistance film method and a capacitance method are generally controlled. It has become a method.
  • the above resistive film type and capacitive type touch panel is a display device such as a front-surface protective film, a film provided with a transparent conductive layer such as glass and indium oxide (hereinafter referred to as “ITO”) film, glass, liquid crystal, etc. And other functional sheets.
  • a film, glass, and a functional sheet are usually bonded together with an optical pressure-sensitive adhesive.
  • the optical pressure-sensitive adhesive used for touch panel applications is a laminate of the frontmost protective film or glass and a film or glass provided with a transparent conductive layer, a film or glass provided with a transparent conductive layer, and liquid crystal. Since it is used for bonding with a display device, optical performance such as transparency and weather resistance is required.
  • an optical pressure-sensitive adhesive As such an optical pressure-sensitive adhesive, an optical pressure-sensitive adhesive composition composed of various high molecular weight acrylic polymers and various crosslinking agents has been proposed (see Patent Documents 1 and 2).
  • a thick adhesive layer having a thickness of 100 ⁇ m or more has been demanded in order to improve the impact resistance of the touch panel, absorb the printing step of the frontmost protective film or glass.
  • Such a thick film (having a thickness of 100 ⁇ m or more) can be obtained by forming a pressure-sensitive adhesive layer having a thickness of 25 ⁇ m or 50 ⁇ m from the optical pressure-sensitive adhesive composition and laminating them.
  • this method has problems such as high cost due to the large number of steps and low transparency due to bonding.
  • an adhesive layer having a thickness of 100 ⁇ m or more is formed by a single coating, foaming occurs when the coating solvent dries, and bubbles are generated in the coating film, thus satisfying optical performance. There was no problem.
  • a solventless adhesive composition As a method for obtaining an adhesive layer having a thickness of 100 ⁇ m or more by one coating without foaming, use of a solventless adhesive composition is considered.
  • a solventless pressure-sensitive adhesive composition an ultraviolet curable solventless pressure-sensitive adhesive composition containing various (meth) acrylate oligomers or (meth) acrylate monomers has been proposed (see Patent Document 3).
  • the present invention is a solvent-free optical pressure-sensitive adhesive composition used for touch panels and the like, and can form a thick-film pressure-sensitive adhesive layer by a single coating, and has transparency, adhesive strength, heating and humidification.
  • the main object is to provide an ultraviolet curable optical pressure-sensitive adhesive composition that is excellent in durability under conditions and that can be peeled off after bonding without adhesive residue.
  • the inventors of the present invention have adjusted the solvent content to less than 1% by weight, the viscosity at 25 ° C. to 100 to 10,000 mPa ⁇ s, and the color tone to Gardner color 1 or less in the ultraviolet curable pressure-sensitive adhesive composition.
  • A a polyfunctional urethane (meth) acrylate oligomer having a weight average molecular weight (polystyrene conversion value by gel permeation chromatography, hereinafter the same) of 10,000 to 100,000
  • B a tackifier
  • an adhesive layer that can solve the above problems can be provided by using the above-mentioned adhesive composition.
  • the present invention relates to the following ultraviolet curable pressure-sensitive adhesive composition and pressure-sensitive adhesive layer.
  • UV curable type having a solvent content of less than 1% by weight, a viscosity at 25 ° C. of 100 to 10,000 mPa ⁇ s, a color tone of Gardner color 1 or less, and the following (A) to (D): Adhesive composition.
  • C Monofunctional epoxy ester (meth) acrylate
  • D photopolymerization initiator having a weight average molecular weight of 10,000 to 100,000 Item 2.
  • the component (A) is a polyfunctional urethane (meth) acrylate oligomer obtained by reacting a polyether polyol, polyisocyanate, and a hydroxyl group-containing (meth) acrylate or isocyanato group-containing (meth) acrylate.
  • UV curable adhesive composition 3.
  • Item 3 The ultraviolet curable pressure-sensitive adhesive composition according to Item 1 or 2, wherein the component (B) is a tackifier having a color tone of Gardner color 1 or less. 4).
  • the pressure-sensitive adhesive composition of the present invention can be used for touch panels, plasma display panels and the like, and since it is solvent-free, it is not necessary to dry the solvent, and it is possible to form a thick-film pressure-sensitive adhesive layer by a single coating. . Moreover, the pressure-sensitive adhesive composition of the present invention is excellent in transparency, adhesive strength, durability under heating and humidification conditions, and can be peeled off without any adhesive residue after being bonded together. Therefore, the pressure-sensitive adhesive layer of the present invention formed from the pressure-sensitive adhesive composition is excellent in pressure-sensitive adhesiveness, transparency and durability, and is suitable as a pressure-sensitive adhesive layer used for touch panels, plasma display panels and the like.
  • the present invention has a solvent content of less than 1% by weight, a viscosity at 25 ° C. of 100 to 10,000 mPa ⁇ s, a color tone of Gardner color 1 or less, and (A) a weight average molecular weight of 10,000 to 100,000.
  • component (A) Polyfunctional urethane (meth) acrylate oligomer
  • component (B) tackifier
  • component (C) monofunctional epoxy ester
  • the solvent content is 1% by weight or more
  • a thick film (thickness of 100 ⁇ m or more) adhesive layer is formed, the coating solvent is dried and foamed when cured, and bubbles are generated in the coating film. There is a problem.
  • the color tone of the pressure-sensitive adhesive composition By setting the color tone of the pressure-sensitive adhesive composition to 1 or less in Gardner color, an adhesive layer having excellent transparency and color tone can be formed.
  • the adhesive strength of the adhesive layer can be improved.
  • the viscosity of a polyfunctional urethane (meth) acrylate oligomer can be made low because the weight average molecular weight of (A) component shall be 100,000 or less, and the handleability of an adhesive improves.
  • the component (A) is obtained by a reaction of polyol, polyisocyanate, and hydroxyl group-containing (meth) acrylate or isocyanato group-containing (meth) acrylate.
  • Polyether polyols such as polyethylene glycol, polypropylene glycol, polytetramethylene glycol, and these copolymers
  • Polyester polyols such as polycondensates of alcohols, polycondensates of phthalic acid and polyhydric alcohols, polyaddition products obtained by ring-opening reaction of lactones and polyhydric alcohols
  • Polycarbonate polyols obtained by reacting diols such as 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, cyclohexanedimethanol and phosgene
  • polyolefin polyols such as polybutadienediol and hydrogenated polybutadienepolyol Etc. It is.
  • polyisocyanate examples include 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 1,3-xylene diisocyanate, diphenylmethane-4,4-diisocyanate, 3-methyl-diphenylmethane diisocyanate, 1,5-naphthalene diisocyanate Aromatic diisocyanate compounds such as dicyclohexylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate and the like; and dimer to hexamers thereof. These may be used alone or in combination. Among these, the use of aliphatic diisocyanates is preferable from the viewpoints of lowering the viscosity of the pressure-sensitive adhesive, high adhesive strength of the pressure-sensitive adhesive layer, and durability.
  • a terminal hydroxyl group-containing urethane prepolymer obtained by reacting a hydroxyl group-containing (meth) acrylate with a terminal isocyanato group-containing urethane prepolymer obtained by reacting the polyol and polyisocyanate, or by reacting the polyol and polyisocyanate.
  • a polyfunctional urethane (meth) acrylate oligomer is obtained by reacting an isocyanato group-containing (meth) acrylate with the polymer.
  • hydroxyl group-containing (meth) acrylate examples include monofunctional compounds such as 2-hydroxy (meth) acrylate, hydroxypropyl (meth) acrylate, 4-hydroxy (meth) acrylate, and 2-hydroxy-2-methylpropyl (meth) acrylate ( (Meth) acrylates; polyfunctional (meth) acrylates such as pentaerythritol triacrylate and dipentaerythritol pentaacrylate; and epoxy ester (meth) acrylates obtained by reacting an epoxy compound with (meth) acrylic acid. These may be used alone or in combination.
  • isocyanato group-containing (meth) acrylate examples include 2-isocyanatoethyl (meth) acrylate and 1,1- (bisacryloyloxymethyl) ethyl isocyanate. These may be used alone or in combination.
  • the average functional group number of the polyfunctional urethane (meth) acrylate oligomer is at least 1.5, preferably 1.8 or more.
  • the average number of functional groups of the urethane (meth) acrylate oligomer is a number indicating how many acryloyl groups exist on average in one molecule of the urethane (meth) acrylate oligomer.
  • the average functional group number of the urethane (meth) acrylate oligomer is controlled by controlling the reaction equivalent of the hydroxyl group-containing (meth) acrylate compound or the isocyanato group-containing (meth) acrylate compound. be able to.
  • the component (B) is a tackifier.
  • Specific examples of the component (B) include petroleum resins, phenol resins, xylene resins, coumarone resins, rosin resins, terpene resins, hydrogenated petroleum resins, hydrogenated rosin resins, hydrogenated terpene resins, and the like. It is done. Among them, a color tone having a Gardner color of 1 or less is preferable. Examples of the color tone having a Gardner color of 1 or less include hydrogenated petroleum resins and hydrogenated rosin resins. These hydrogenated resins are usually tackifiers having excellent transparency because the color tone is Gardner color 1 or less, and improve the transparency of the optical pressure-sensitive adhesive and the pressure-sensitive adhesive layer. Furthermore, since these hydrogenated resins have little polymerization inhibition during polymerization due to ultraviolet irradiation, the use of these hydrogenated resins provides an optical pressure-sensitive adhesive having excellent curability.
  • the hydrogenated rosin resin is not particularly limited as long as it is a hydrogenated rosin resin, and known resins can be used.
  • the rosin resin for example, natural rosins such as gum rosin, tall oil rosin, and wood rosin, as well as natural rosins are processed by at least one method selected from polymerization, modification, disproportionation, and esterification.
  • rosin metal salts obtained by reacting natural rosins or processed rosins with metals such as calcium, magnesium, zinc, and the like.
  • a method for producing rosins processed by the polymerization method (hereinafter also referred to as “polymerized rosin”) is not particularly limited, and a known method can be employed.
  • a method in which the natural rosins or rosins obtained by processing natural rosins by at least one method selected from modification, disproportionation, and esterification is heated using a polymerization catalyst.
  • the polymerization catalyst include acids such as sulfuric acid, phosphoric acid, and hydrofluoric acid; and metal halides such as boron fluoride, aluminum chloride, and zinc chloride.
  • modified rosin The production method of rosins processed by the above modification method (hereinafter also referred to as “modified rosin”) is not particularly limited, and a known method may be employed. Usually, a method in which natural rosins and phenols or unsaturated acids are mixed and heated is used.
  • the phenols are not particularly limited, and specific examples include phenol and alkylphenol.
  • the unsaturated acid is not particularly limited, and specific examples include fumaric acid, maleic acid, (meth) acrylic acid and the like.
  • the production method of rosins processed by the above disproportionation method (hereinafter also referred to as “disproportionation rosin”) is not particularly limited, and a known method may be adopted.
  • natural rosins or processed rosins are saponified by reacting them at 220 to 250 ° C. for 2 to 6 hours without adding hydrogen in the presence of a reduction catalyst such as nickel, platinum or palladium or a carbon catalyst. It is done.
  • rosin ester The method for producing rosins processed by the above esterification method (hereinafter also referred to as “rosin ester”) is not particularly limited, and a known method can be adopted.
  • natural rosins or processed rosins and alcohol are mixed and heated in the presence of an esterification catalyst as necessary.
  • esterification catalysts include acid catalysts such as acetic acid and paratoluenesulfonic acid, alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkaline earth such as calcium hydroxide and magnesium hydroxide.
  • Metal oxides such as calcium oxide, magnesium oxide, zinc oxide, lead oxide and tin oxide can be used.
  • Examples of the alcohol include aliphatic monovalent or polyhydric alcohols having 1 to 20 carbon atoms.
  • examples of such alcohols include monohydric alcohols such as methanol, ethanol, isopropyl alcohol, isoamyl alcohol, n-hexyl alcohol, 2-ethylhexyl alcohol, n-octyl alcohol, dodecyl alcohol, lauryl alcohol, stearyl alcohol, and dihydroabiethyl alcohol.
  • Divalent alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and neopentyl glycol; trivalent alcohols such as glycerin, trimethylolethane, and trimethylolpropane; and tetrahydric alcohols such as pentaerythritol and diglycerin.
  • the above rosin resins may be used alone or in combination of two or more.
  • natural rosins and the like can be processed using two or more methods among polymerization, modification, disproportionation, and esterification.
  • the order of the methods is not particularly limited and can be a known method. For example, it may be polymerized after modifying natural rosins or processed rosins, or esterified after polymerization.
  • the hydrogenated petroleum resin as the component (B) is not particularly limited as long as it is a hydrogenated petroleum resin, and a known one can be used. Petroleum resins are roughly classified into aliphatic petroleum resins, aromatic petroleum resins, and dicyclopentadiene petroleum resins, for example, depending on the type of raw material monomer (fraction). Examples of the aliphatic petroleum resin include C5 petroleum resin and C5-C9 petroleum resin. Aromatic petroleum resins include C9 petroleum resins. The C5 petroleum resin is obtained by cationic polymerization of a C5 petroleum fraction (for example, pentene, methylbutene, isoprene, cyclopentene, etc.).
  • the C9 petroleum resin is not particularly limited, but is generally obtained by cationic polymerization of a C9 petroleum fraction (eg, styrene, vinyltoluene, ⁇ -methylstyrene, indene) obtained by naphtha cracking. Things can be used.
  • the C5-C9 petroleum resin is obtained by copolymerizing the C5 petroleum fraction and the C9 petroleum fraction in the same manner as in the production of the C5 petroleum resin.
  • the dicyclopentadiene-based petroleum resin is obtained by thermal polymerization or cationic polymerization of dicyclopentadiene.
  • These petroleum resins may be modified with polar groups such as hydroxyl groups and ester groups by a generally known method.
  • the color tone of petroleum resin is usually about 5 to 15 Gardner.
  • the component (C) is a monofunctional epoxy ester (meth) acrylate obtained by reacting a monofunctional epoxy compound with (meth) acrylic acid, and various known ones can be used without particular limitation.
  • monofunctional epoxy ester (meth) acrylate obtained by reacting phenylglycidyl ether and (meth) acrylic acid (methylphenyl) glycidyl ether and (meth) acrylic acid. It has an aromatic structure such as monofunctional epoxy ester (meth) acrylate obtained by reaction, monofunctional epoxy ester (meth) acrylate obtained by reacting (t-butylphenyl) glycidyl ether and (meth) acrylic acid.
  • (Meth) acrylate (ethylhexyl) glycidyl ether having an alkyl group having 1 to 30 carbon atoms such as monofunctional epoxy ester (meth) acrylate obtained by reacting methyl (meth) acrylate and (meth) acrylic acid ( And (meth) acrylate.
  • monofunctional epoxy ester (meth) acrylate having an aromatic structure is preferable from the viewpoint of compatibility with the urethane (meth) acrylate oligomer and the tackifier.
  • the component (D) various known ones can be used without particular limitation as long as they are photopolymerization initiators that decompose upon irradiation with ultraviolet rays to generate radicals.
  • examples of the component (D) include photopolymerization initiators such as benzoin compounds, acetophenone compounds, acylphosphine oxide compounds, titanocene compounds, thioxanthone compounds, and oxime ester compounds; photosensitizers such as amines and quinones.
  • Specific compounds include 2,2-dimethoxy-1,2-diphenylethane-1-one, 1-hydroxy-cyclohexyl-phenyl-ketone, 2-hydroxy-2-methyl-1-phenyl-propan-1-one 1- [4- (2-hydroxyethoxy) -phenyl] -2-hydroxy-2-methyl-1-propan-1-one, 2-hydroxy-1- [4- [4- (2-hydroxy-2 -Methyl-propionyl) -benzyl] phenyl] -2-methyl-propan-1-one, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one, 2- (dimethylamino) -2-[(4-Methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] -1-butanone, 2,4,6-trimethylbenzoyl-diphenyl Phosphine oxide, bis (2,4,6-trimethylbenzoyl) -phenylphosphin
  • 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide and bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide are preferable because the curability of the pressure-sensitive adhesive composition is improved. It is.
  • the blending ratio of the component (A) within the above range, the adhesive strength of the adhesive layer can be improved and the handling property of the adhesive can be improved.
  • the adhesive strength of the adhesive layer can be improved and the adhesive residue of the adhesive layer can be eliminated.
  • the handling property of the pressure-sensitive adhesive can be improved, and an appropriate viscosity can be obtained.
  • a thick-film pressure-sensitive adhesive layer can be applied once. Can be formed.
  • the ultraviolet curable pressure-sensitive adhesive composition of the present invention can be produced by mixing the components (A) to (D).
  • the mixing method is not particularly limited, and the addition order of the components (A) to (D) is not limited.
  • the pressure-sensitive adhesive composition of the present invention can contain various monofunctional or polyfunctional monomers as dilution monomers as long as the effects of the present invention are not impaired.
  • the monofunctional monomer examples include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, n-pentyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, nonyl (meth) acrylate, isononyl (meth) acrylate, Decyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, cetyl (meth) acrylate, stearyl (meth) acrylate, isostearyl (meth)
  • polyfunctional monomer examples include 1,4-butanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1.6-hexanediol (meth) acrylate, 1,9-nonanediol di ( Di (meth) acrylate having an aliphatic structure such as (meth) acrylate; Di (meth) acrylate having an alicyclic structure such as cyclohexanedimethanol di (meth) acrylate and tricyclodecane di (meth) acrylate; Bisphenol A ethylene Di (meth) acrylates having an aromatic structure such as oxide-modified di (meth) acrylate and bisphenol F ethylene oxide-modified di (meth) acrylate; trimethylolpropane tri (meth) acrylate, isocyanuric acid ethylene oxide-modified tri (meth) acrylate Relate, pentaerythritol triacrylate
  • the pressure-sensitive adhesive composition of the present invention can contain various additives, as necessary, within a range not impairing the effects of the present invention.
  • additives such as a surface conditioner, a surfactant, an ultraviolet absorber, an inorganic filler, a silane coupling agent, colloidal silica, an antifoaming agent, a wetting agent, a rust inhibitor, and a stabilizer can be contained.
  • the adhesive composition of the present invention into a pressure-sensitive adhesive layer
  • a technique called casting film formation Specifically, the adhesive composition was cast into a thin film on a protective film such as a polyethylene terephthalate film (PET film) coated with a release agent such as a silicone resin, and then the coating film was irradiated with ultraviolet rays.
  • the pressure-sensitive adhesive layer is obtained by polymerization and curing. According to such a manufacturing method, the stress applied to the pressure-sensitive adhesive composition during film formation is small, and the formation of defects is small. Moreover, the uniformity of the film thickness of the obtained coating film becomes high.
  • the ultraviolet light source examples include an ultraviolet irradiation device having a xenon lamp, a high-pressure mercury lamp, a metal halide lamp and the like.
  • conditions such as the amount of light, the light source, and the conveyance speed may be adjusted as appropriate.
  • the amount of light is usually about 80 to 160 W / cm, and the conveyance speed is usually about 5 to 50 m / min.
  • the thickness of the pressure-sensitive adhesive layer of the present invention is not particularly limited, but is usually about 10 to 1000 ⁇ m, preferably about 25 to 500 ⁇ m. By making the film thickness within this range, the impact resistance of the touch panel can be improved and the printing step on the surface can be absorbed, so it can be used as the frontmost protective film, etc. It can be.
  • Synthesis example 1 Synthesis of component (A-1) To a reactor equipped with a stirrer and a condenser, 955 parts of polypropylene glycol having a weight average molecular weight of 4,000, 34 parts of hexamethylene diisocyanate and 0.2 part of tin octylate were added, and The reaction was completed by NCO measurement and it was confirmed that a urethane oligomer was formed. Then, 11 parts of 2-isocyanatoethyl methacrylate was added, and the mixture was heated at 80 ° C. for 2 hours. Keep warm.
  • component (A-1) a urethane methacrylate oligomer having a weight average molecular weight of 30,000 and an average functional group number of 2.0 was obtained.
  • the weight average molecular weight is determined using a commercially available molecular weight measuring instrument (main product name “HLC-8220GPC”, manufactured by Tosoh Corporation; column product names “TSKGel G1000H”, “TSKGel G2000H”, manufactured by Tosoh Corporation; developing solvent. Tetrahydrofuran) (hereinafter the same)
  • Synthesis example 2 Synthesis of component (A-2)
  • component (A-2) a urethane acrylate oligomer having a weight average molecular weight of 25,000 and an average functional group number of 2.0 was obtained.
  • the disproportionated rosin was purified by distillation under a nitrogen seal under reduced pressure of 3 mmHg to obtain a purified disproportionated rosin having an acid value of 178, a softening point of 78 ° C., and a color tone Gardner 2.
  • 500 parts of this purified disproportionated rosin is placed in a 1 L four-necked flask, heated to 180 ° C. under a nitrogen seal, added with 60 parts of glycerin at 200 ° C. with melting and stirring, then heated to 280 ° C.
  • the esterification reaction was carried out at a temperature for 12 hours to obtain a purified disproportionated rosin ester having an acid value of 3.4, a softening point of 99 ° C., and a color tone Gardner 3.
  • 200 parts of this purified disproportionated rosin ester and 2 parts of 5% palladium carbon (water content 50%) were charged into a 2 L shaking autoclave to remove oxygen in the system, and then the system was filled with hydrogen at 100 kg / cm.
  • the mixture was heated to 255 ° C. while being pressurized to 2 , and subjected to a hydrogenation reaction at the same temperature for 3.5 hours.
  • a hydrogenated rosin ester having an acid value of 12.5, a softening point of 89.5 ° C. and a color tone Gardner of 1 or less Agent (B-1)) (hereinafter referred to as “component (B-1)”) was obtained.
  • Synthesis example 4 Synthesis of Component (B-2) 100 parts of dicyclopentadiene, 100 parts of allyl alcohol and 80 parts of xylene were charged into an autoclave and reacted at 270 ° C. for 2 hours in a nitrogen atmosphere to obtain a polymer oil.
  • the polymer oil was distilled under reduced pressure at 200 ° C. and 2.7 kPa for 15 minutes to remove unreacted monomer solvent and low polymer, thereby obtaining a softening point of 97.5 ° C., a color tone Gardner 8, a hydroxyl value of 210 mg KOH / g and a weight.
  • a hydroxyl group-containing petroleum resin having an average molecular weight of 540 (polystyrene equivalent value in GPC) was obtained. 100 parts of this hydroxyl group-containing petroleum resin, 100 parts of cyclohexane, and 2.0 parts of a stabilized nickel catalyst (trade name “N-113” manufactured by JGC Chemical Co., Ltd.) were charged into an autoclave and placed in a high-pressure hydrogen atmosphere at a hydrogen pressure of 18 MPa. And reacted at 240 ° C. for 5 hours. After the catalyst was filtered off, it was distilled at 220 ° C.
  • a hydride of a hydroxyl group-containing petroleum resin (tackifier (B-2)) (hereinafter referred to as “component (B-2)”) was obtained.
  • Synthesis example 5 Synthesis of Component (E-1)
  • 955 parts of polypropylene glycol having a weight average molecular weight of 4,000, 34 parts of hexamethylene diisocyanate and 0.2 part of tin octylate were added, and the temperature was raised to 80 ° C. After heating and holding for 2 hours, the reaction was completed by NCO measurement and it was confirmed that a urethane oligomer was formed. Then, 6 parts of 2-isocyanatoethyl methacrylate was added, and the temperature was kept at 80 ° C. for 2 hours. .
  • component (E-1) urethane methacrylate oligomer having a weight average molecular weight of 30,000 and an average functional group number of 1.0 was obtained.
  • Example 1 3-hydroxypropyl, a monofunctional epoxy ester acrylate obtained by reacting 25 parts of component (A-1), 5 parts of component (B-1) and reacting phenylglycidyl ether and acrylic acid as component (C) 45 parts of phenyl acrylate (HPPA) (trade name “Epoxy ester M-600A” manufactured by Kyoeisha Chemical Co., Ltd.), 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide (TPO) as component (D) ( 1 part of BASF Japan Co., Ltd., trade name “Lucirin TPO”), 25 parts of isostearyl acrylate (ISTA) (ISTA, manufactured by Osaka Organic Chemical Industry Co., Ltd.) as a dilution monomer, Prepared (Table 1). In addition, all compounding quantities are the ratios of solid content. The color tone Gardner color, viscosity, solvent content and compatibility of the obtained composition were evaluated,
  • Comparative Example 1 3-hydroxy, which is a monofunctional epoxy ester acrylate obtained by reacting 5 parts of component (B-1) without using component (A-1) and reacting phenylglycidyl ether and acrylic acid as component (C) 45 parts of propylphenyl acrylate (HPPA) (trade name “epoxy ester M-600A” manufactured by Kyoeisha Chemical Co., Ltd.), 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide (TPO) as component (D) 1 part of BASF Japan (trade name “Lucirin TPO”) and 50 parts of isostearyl acrylate (ISTA) (ISTA, manufactured by Osaka Organic Chemical Industry Co., Ltd.) as a diluting monomer Was prepared.
  • HPPA propylphenyl acrylate
  • TPO 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide
  • ISA isostearyl acrylate
  • Comparative Example 2 3-hydroxy, which is a monofunctional epoxy ester acrylate obtained by reacting 25 parts of component (A-1), no component (B-1), and reacting phenylglycidyl ether and acrylic acid as component (C) 45 parts of propylphenyl acrylate (HPPA) (trade name “epoxy ester M-600A” manufactured by Kyoeisha Chemical Co., Ltd.), 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide (TPO) as component (D) 1 part of BASF Japan (trade name “Lucirin TPO”) and 30 parts of isostearyl acrylate (ISTA) (ISTA, manufactured by Osaka Organic Chemical Industry Co., Ltd.) as a dilution monomer Was prepared.
  • HPPA propylphenyl acrylate
  • TPO 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide
  • ISA isostearyl acrylate
  • all compounding quantities are the
  • Comparative Example 3 Component (A-1) is 95 parts, Component (B-1) is 5 parts, Component (C) is not used, Component (D) is 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide (TPO) ) (BASF Japan Co., Ltd., trade name “Lucirin TPO”) was blended in an amount to prepare an adhesive composition. In addition, all compounding quantities are the ratios of solid content. As in Example 1, the color tone Gardner color, viscosity, solvent content and compatibility of the obtained composition were evaluated. The results are shown in Table 2.
  • Comparative Example 4 A monofunctional epoxy ester acrylate obtained by reacting phenylglycidyl ether and acrylic acid with 25 parts of urethane methacrylate oligomer comprising component (A-1), 5 parts of component (B-1), and component (C). 45 parts of 3-hydroxypropylphenyl acrylate (HPPA) (trade name “epoxy ester M-600A” manufactured by Kyoeisha Chemical Co., Ltd.), isostearyl acrylate (ISTA) as a diluent monomer without using component (D) 25 parts of Osaka Organic Chemical Industry Co., Ltd. (ISTA) was blended to prepare an adhesive composition. In addition, all compounding quantities are the ratios of solid content. As in Example 1, the color tone Gardner color, viscosity, solvent content and compatibility of the obtained composition were evaluated. The results are shown in Table 2.
  • Comparative Example 5 A pressure-sensitive adhesive composition was prepared in the same manner as in Example 1 except that the component (B-1) was changed to Nippon Zeon's trade name Quintone 1700 (softening point 100 ° C., color tone Gardner 4) (B-3). . As in Example 1, the color tone Gardner color, viscosity, solvent content and compatibility of the obtained composition were evaluated. The results are shown in Table 2.
  • Comparative Example 6 A pressure-sensitive adhesive composition in the same manner as in Example 1 except that the component was changed to Arakawa Chemical Co., Ltd., trade name Superester A100 (softening point 95 to 105 ° C., color tone Gardner 7) (B-4) was prepared. As in Example 1, the color tone Gardner color, viscosity, solvent content and compatibility of the obtained composition were evaluated. The results are shown in Table 2.
  • Comparative Example 7 A pressure-sensitive adhesive composition was prepared in the same manner as in Example 1 except that the component (A-1) was replaced with the component (E-1). As in Example 1, the color tone Gardner color, viscosity, solvent content and compatibility of the obtained composition were evaluated. The results are shown in Table 2.
  • Comparative Example 8 A pressure-sensitive adhesive composition was prepared in the same manner as in Example 1 except that the component (A-1) was replaced with the component (E-2). As in Example 1, the color tone Gardner color, viscosity, solvent content and compatibility of the obtained composition were evaluated. The results are shown in Table 2.
  • the viscosity (mPa ⁇ s) of the pressure-sensitive adhesive composition was measured with an E-type viscometer (TVE-10, Toki Sangyo Co., Ltd.) at 25 ° C. for 5 minutes.
  • solvent content The solvent content of the coating liquid was measured using a gas chromatograph apparatus.
  • GC Agilent, 6850 ⁇ GC measurement conditions>
  • GC column HP-1
  • Example 6 ⁇ Preparation of adhesive layer> Examples 6 to 10 and Comparative Examples 9 to 14
  • the composition of Example 1 was applied on a 38 ⁇ m-thick release-treated polyester film (trade name “SP-PET-01-38BU” manufactured by Panac Co., Ltd.) so as to have a film thickness of 150 ⁇ m.
  • Pre-curing was performed by passing once under a high-pressure mercury lamp (35 mJ / cm 2 ).
  • the cured product coated surface and a 38 ⁇ m thick release-treated polyester film were bonded together so that the release-treated surface was in contact, and cured by passing 4 times under high pressure mercury lamp (300 mJ / cm 2 ) in the air.
  • Example 6 An adhesive layer was obtained.
  • each haze value is a numerical value including the haze value of the polyester film which is a base material, and glass.
  • ⁇ Durability test> For the adhesive layers of Examples 6 to 10 and Comparative Examples 9 to 14, 50 ⁇ m PET / adhesive layer (150 ⁇ m) / glass test pieces were prepared in the same manner as the adhesive strength test, and the durability test was performed.
  • the durability test was a heat and humidity resistance test that was stored in a constant temperature and humidity chamber at 85 ° C. and 85% relative humidity for 500 hours.
  • the haze value after the wet heat resistance test was measured according to JIS K 5400 using a color haze meter manufactured by Murakami Color Research Laboratory.
  • each haze value is a numerical value including the haze value of the polyester film which is a base material, and glass.
  • the evaluation criteria of durability are as follows. ⁇ : No peeling, no adhesion layer leaching, no coating whitening ⁇ : Either peeling, adhesion layer leaching, or coating whitening

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Abstract

La présente invention concerne une composition adhésive à durcissement par UV qui est une composition adhésive optique sans solvant destinée à être utilisée dans des écrans tactiles et similaires, une couche adhésive épaisse pouvant être formée par une seule opération d'enduction ; la couche présente une transparence, une force d'adhérence et une durabilité excellentes dans des conditions de chaleur et d'humidité ; après recouvrement, le pelage est possible sans reste de colle. La présente invention concerne une composition adhésive à durcissement par UV comprenant (A) un oligomère de (méth)acrylate d'uréthane multifonctionnel ayant une masse moléculaire moyenne en poids de 10 000 à 100 000, (B) un promoteur d'adhérence, (C) un (méth)acrylate d'ester époxy monofonctionnel et (D) un initiateur de photopolymérisation ; la teneur en solvant étant inférieure à 1 % en poids, la viscosité à 25 °C étant de 100 à 10 000 mPa•s et la tonalité chromatique étant égale à 1 ou moins sur l'échelle des couleurs de Gardner.
PCT/JP2013/061915 2012-04-27 2013-04-23 Composition adhésive à durcissement par uv et couche adhésive WO2013161812A1 (fr)

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