WO2012026456A1 - Composition d'agent adhésif - Google Patents

Composition d'agent adhésif Download PDF

Info

Publication number
WO2012026456A1
WO2012026456A1 PCT/JP2011/068949 JP2011068949W WO2012026456A1 WO 2012026456 A1 WO2012026456 A1 WO 2012026456A1 JP 2011068949 W JP2011068949 W JP 2011068949W WO 2012026456 A1 WO2012026456 A1 WO 2012026456A1
Authority
WO
WIPO (PCT)
Prior art keywords
meth
weight
pressure
sensitive adhesive
adhesive composition
Prior art date
Application number
PCT/JP2011/068949
Other languages
English (en)
Japanese (ja)
Inventor
庸佑 米田
慎也 服部
宏人 中野
雅仁 斉藤
Original Assignee
日本カーバイド工業株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 日本カーバイド工業株式会社 filed Critical 日本カーバイド工業株式会社
Priority to CN201180036207.9A priority Critical patent/CN103025837B/zh
Priority to JP2012530673A priority patent/JP5826179B2/ja
Priority to KR1020137007273A priority patent/KR101840072B1/ko
Publication of WO2012026456A1 publication Critical patent/WO2012026456A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • 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
    • 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
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen
    • C08G18/289—Compounds containing at least one heteroatom other than oxygen or nitrogen containing silicon
    • 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
    • C08G18/4081—Mixtures of compounds of group C08G18/64 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
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
    • C08G18/625—Polymers of alpha-beta ethylenically unsaturated carboxylic acids; hydrolyzed polymers of esters of these acids
    • C08G18/6254—Polymers of alpha-beta ethylenically unsaturated carboxylic acids and of esters of these acids containing hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • 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
    • C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
    • C08G18/6492—Lignin containing materials; Wood resins; Wood tars; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/062—Copolymers with monomers not covered by C08L33/06
    • C08L33/068—Copolymers with monomers not covered by C08L33/06 containing glycidyl groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
    • 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
    • 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
    • C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
    • C09J183/04—Polysiloxanes
    • 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
    • C09J7/10—Adhesives in the form of films or foils without carriers
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • 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
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5435—Silicon-containing compounds containing oxygen containing oxygen in a ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/10—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet
    • C09J2301/12—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet by the arrangement of layers
    • C09J2301/124—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet by the arrangement of layers the adhesive layer being present on both sides of the carrier, e.g. double-sided adhesive tape
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2433/00—Presence of (meth)acrylic polymer

Definitions

  • the present invention relates to an adhesive composition used when an optical film such as a polarizing film or a retardation film is attached to an adherend such as a liquid crystal cell. More specifically, the present invention relates to a pressure-sensitive adhesive composition that exhibits excellent durability even under high temperature and high humidity and is excellent in white spot suppression ability.
  • a liquid crystal display device usually includes a liquid crystal cell in which a liquid crystal component oriented in a predetermined direction is sandwiched between two supporting substrates such as glass and an optical film such as a polarizing film, a retardation film, and a brightness enhancement film. It is configured. Adhesives are often used when laminating these optical films or attaching optical films to liquid crystal cells.
  • Liquid crystal display devices are widely used as display devices for personal computers, televisions, car navigation systems, and the like. These may be used in harsh environments such as high temperature and high humidity. Accordingly, there is a demand for an adhesive that is excellent in durability and does not peel off or generate bubbles even after long-term use. In a severe environment such as high temperature and high humidity, the optical film undergoes large dimensional changes such as shrinkage and expansion. The conventional pressure-sensitive adhesive layer cannot relax the stress generated by such a dimensional change, and the residual stress of the optical film becomes non-uniform. As a result, there is a problem of so-called “white spots” in which light leaks from the periphery of the liquid crystal display device and becomes white.
  • Patent Document 1 Japanese Patent Laid-Open No. 10-279907
  • Patent Document 1 Japanese Patent Laid-Open No. 10-279907
  • Patent Document 1 Japanese Patent Laid-Open No. 10-279907
  • Patent Document 1 Japanese Patent Laid-Open No. 10-279907
  • Patent Document 1 Japanese Patent Laid-Open No. 10-279907
  • Patent Document 1 Japanese Patent Laid-Open No. 10-279907
  • Patent Document 1 Japanese Patent Laid-Open No. 10-279907
  • Patent Document 1 Japanese Patent Laid-Open No. 10-279907
  • Patent Document 1 Japanese Patent Laid-Open No. 10-279907
  • Patent Document 1 Japanese Patent Laid-Open No. 10-279907
  • Patent Document 1 Japanese Patent Laid-Open No. 10-279907
  • Patent Document 1 Japanese Patent Laid-Open No. 10-279907
  • Patent Document 1 Japanese Patent Laid-Open No. 10-279907
  • Patent Document 1 Japanese Patent Laid-Open No. 10-279907
  • a method for suppressing white spots a method for preventing white spots from occurring by relaxing the stress concentration following the dimensional change of the polarizing film, as in the pressure-sensitive adhesive composition described in Patent Document 1, is the opposite.
  • a method of suppressing the occurrence of white spots by using a pressure-sensitive adhesive composition having a high cohesive force and minimizing a region where stress is generated.
  • Patent Document 2 Japanese Patent Application Laid-Open No. 2007-112839
  • a peroxide 100 parts by weight of an acrylic copolymer
  • isocyanate A pressure-sensitive adhesive composition comprising 0.02 to 2 parts by weight of a system cross-linking agent and 1 to 40 parts by weight of a tackifying resin having a softening point of 80 ° C. or higher is disclosed.
  • Patent Document 2 has no description regarding white spots, and the ability to suppress white spots is insufficient only with the above configuration.
  • an object of the present invention is to provide a pressure-sensitive adhesive composition that is excellent in white spot suppression ability and durability.
  • the present invention provides a pressure-sensitive adhesive composition having the following constitution.
  • a (meth) acrylic copolymer (A) containing a carboxyl group, a (meth) acrylic copolymer (B) containing a carboxyl group and a hydroxyl group, and the (meth) acrylic copolymer A pressure-sensitive adhesive composition containing 5 to 20 parts by weight of a tolylene diisocyanate compound (C) and an epoxy group-containing silane coupling agent (D) with respect to a total of 100 parts by weight of (A) and (B) .
  • the above (6) or (6) comprising 1 to 20 parts by weight of the compound (F) having a hydroxyl group and a rosin skeleton with respect to a total of 100 parts by weight of the acrylic copolymers (A) and (B).
  • the epoxy group-containing silane coupling agent (D) is contained in an amount of 0.02 to 1 part by weight based on 100 parts by weight of the total of the (meth) acrylic copolymers (A) and (B) ( 1) The pressure-sensitive adhesive composition according to any one of (8).
  • the pressure-sensitive adhesive composition of the present invention has excellent durability even under high temperature and high humidity environments, and has excellent whiteout suppression ability.
  • the optical film using the pressure-sensitive adhesive composition of the present invention has excellent whiteout suppression ability and does not peel off or generate bubbles even under high temperature and high humidity conditions. Therefore, personal computers, televisions, car navigation systems, etc.
  • the display device can be suitably used.
  • the pressure-sensitive adhesive composition of the present invention has little change over time in adhesive strength and is excellent in reworkability.
  • reworkability means that when an optical film is stuck to an adherend using an adhesive, the optical film is peeled and removed from the adherend when a defect such as biting of a foreign matter occurs. This is the ease of re-applying the optical film.
  • the (meth) acrylic copolymer is mainly composed of an acrylate monomer or a methacrylic acid ester monomer, at least an acrylate monomer or a methacrylic acid ester monomer, and a reactive functional group. It is a copolymer obtained by copolymerizing a monomer having a group.
  • “(meth) acryl” is used to mean both “acryl” and “methacryl”.
  • the (meth) acrylic acid ester monomer is not particularly limited as long as it has a (meth) acrylic acid ester structure.
  • Examples of the monomer having a reactive functional group include a carboxyl group-containing monomer, a hydroxyl group-containing monomer, a glycidyl group-containing monomer, an amide group, an N-substituted amide group-containing monomer, and a tertiary amino acid.
  • 1 type (s) or 2 or more types, such as a group containing monomer, can be used.
  • carboxyl group-containing monomer examples include acrylic acid, methacrylic acid, maleic acid, maleic anhydride, fumaric acid, crotonic acid, itaconic acid, citraconic acid, cinnamic acid, monohydroxyethyl (meth) acrylate succinate, and maleic acid.
  • Acid monohydroxyethyl (meth) acrylate, fumarate monohydroxyethyl (meth) acrylate, phthalate monohydroxyethyl (meth) acrylate, 1,2-dicarboxycyclohexane monohydroxyethyl (meth) acrylate, (meth) acrylic acid dimer , ⁇ -carboxy-polycaprolactone mono (meth) acrylate, and the like can be used, but are not limited thereto.
  • hydroxyl group-containing monomer examples include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 3-methyl- 3-hydroxybutyl (meth) acrylate, 1,1-dimethyl-3-butyl (meth) acrylate, 1,3-dimethyl-3-hydroxybutyl (meth) acrylate, 2,2,4-trimethyl-3-hydroxypentyl (Meth) acrylate, 2-ethyl-3-hydroxyhexyl (meth) acrylate, glycerin mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, polyethylene glycol mono (meth) acrylate, poly (ethylene glycol-propylene Recall) mono (meth) acrylate, N- methylol acrylamide, allyl alcohol, can be used methallyl alcohol, but is not limited thereto.
  • Examples of the glycidyl group-containing monomer include glycidyl (meth) acrylate, 3,4-epoxycyclohexylmethyl (meth) acrylate, glycidyl vinyl ether, 3,4-epoxycyclohexyl vinyl ether, glycidyl (meth) allyl ether, 3,4 -Epoxycyclohexyl (meth) allyl ether or the like can be used, but is not limited thereto.
  • Examples of the amide group and N-substituted amide group-containing monomer include acrylamide, methacrylamide, N-methyl (meth) acrylamide, N-ethyl (meth) acrylamide, N-methoxymethyl (meth) acrylamide, and N-ethoxy.
  • Methyl (meth) acrylamide, N-propoxymethyl (meth) acrylamide, N-butoxymethyl (meth) acrylamide, N-tert-butyl acrylamide, N-octyl acrylamide, diacetone acrylamide and the like can be used, but are not limited thereto. Is not to be done.
  • dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, dimethylaminopropyl (meth) acrylamide, and the like can be used, but are not limited thereto.
  • the (meth) acrylic copolymer (A) used in the present invention contains a (meth) acrylic acid ester monomer and a carboxyl group-containing monomer as copolymer components.
  • the proportion of the (meth) acrylic acid ester monomer as a copolymer component is 80% by weight with respect to the (meth) acrylic copolymer (A). % Or more is preferable.
  • the proportion of the carboxyl group-containing monomer as a copolymer component is 0.5% relative to the (meth) acrylic copolymer (A). It is preferably ⁇ 5% by weight, more preferably 1 to 3% by weight. If the content of the carboxyl group-containing monomer is 0.5% by weight or more based on the (meth) acrylic copolymer (A), the cohesive force and durability of the pressure-sensitive adhesive composition may be increased. This is preferable because it is possible. On the other hand, if the content of the carboxyl group-containing monomer is 5% by weight or less with respect to the (meth) acrylic copolymer (A), it is preferable because reworkability is excellent.
  • the weight average molecular weight (Mw) of the (meth) acrylic copolymer (A) used in the present invention is preferably 500,000 to 2,500,000, and more preferably 1,000,000 to 2,500,000. If the weight average molecular weight (Mw) of the (meth) acrylic copolymer (A) is 500,000 or more, it is preferable because sufficient cohesive force can be obtained and generation of bubbles can be suppressed. Moreover, if the weight average molecular weight (Mw) of a (meth) acrylic-type copolymer (A) is 2.5 million or less, since an adhesive composition can be easily applied to an optical film etc., it is preferable.
  • the (meth) acrylic copolymer (B) used in the present invention contains a (meth) acrylic acid ester monomer, a carboxyl group-containing monomer, and a hydroxyl group-containing monomer as a copolymer component.
  • the proportion of the (meth) acrylic acid ester monomer as a copolymer component is 80% by weight with respect to the (meth) acrylic copolymer (B). % Or more is preferable.
  • the proportion of the carboxyl group-containing monomer as the copolymer component is 0.1% with respect to the (meth) acrylic copolymer (B). It is preferably ⁇ 5% by weight, more preferably 0.5-3% by weight. If the content of the carboxyl group-containing monomer is 0.1% by weight or more with respect to the (meth) acrylic copolymer (B), the durability of the pressure-sensitive adhesive composition can be increased, which is preferable. . On the other hand, if the content of the carboxyl group-containing monomer is 5% by weight or less based on the (meth) acrylic copolymer (B), it is preferable because reworkability is excellent.
  • the proportion of the hydroxyl group-containing monomer as a copolymer component is 0.01 to about (meth) acrylic copolymer (B).
  • the content is preferably 2% by weight, more preferably 0.1 to 1% by weight. If the content of the hydroxyl group-containing monomer is 0.01% by weight or more with respect to the (meth) acrylic copolymer (B), the white spot suppression ability is high and preferable. On the other hand, if the content of the hydroxyl group-containing monomer is 2% by weight or less with respect to the (meth) acrylic copolymer (B), it is preferable because peeling of the pressure-sensitive adhesive can be suppressed.
  • the weight average molecular weight (Mw) of the (meth) acrylic copolymer (B) used in the present invention is preferably 500,000 to 2,500,000, and more preferably 1,000,000 to 2,500,000.
  • a weight average molecular weight (Mw) of the (meth) acrylic copolymer (B) of 500,000 or more is preferable because sufficient cohesive force can be obtained and the generation of bubbles can be suppressed.
  • the weight average molecular weight (Mw) of a (meth) acrylic-type copolymer (B) is 2.5 million or less, since an adhesive composition can be easily applied to an optical film etc., it is preferable.
  • the weight average molecular weight (Mw) of the (meth) acrylic copolymer is a value measured by the following method.
  • GPC HLC-8220 GPC [manufactured by Tosoh Corporation] Column: 4 TSK-GEL GMHXL used Mobile phase solvent: Tetrahydrofuran Standard sample: Standard polystyrene Flow rate: 0.6 ml / min, Column temperature: 40 ° C
  • the polymerization method of the (meth) acrylic copolymers (A) and (B) used in the present invention is not particularly limited, and methods such as solution polymerization, emulsion polymerization, and suspension polymerization can be used. .
  • a process process is comparatively simple and can be performed in a short time, it is preferable to superpose
  • a predetermined organic solvent, a monomer, a polymerization initiator, and a chain transfer agent used as needed are generally charged in a polymerization tank, and stirred in a nitrogen stream or under reflux of the organic solvent.
  • a method such as heating reaction for several hours can be used.
  • the weight average molecular weights of the (meth) acrylic copolymers (A) and (B) used in the present invention are adjusted to the desired molecular weight by adjusting the reaction temperature, time, solvent amount, and type and amount of the catalyst. can do.
  • the pressure-sensitive adhesive composition of the present invention contains a tolylene diisocyanate compound (C).
  • tolylene diisocyanate compounds include 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, and dimers, trimers, and trimethylolpropane adducts thereof.
  • the content of the tolylene diisocyanate compound (C) in the pressure-sensitive adhesive composition of the present invention is 5 to 20 parts by weight with respect to a total of 100 parts by weight of the (meth) acrylic copolymers (A) and (B). It is preferable to do. If the content of the tolylene diisocyanate compound (C) is 5 parts by weight or more with respect to a total of 100 parts by weight of the (meth) acrylic copolymer (A) and (B), the white spot suppression ability is excellent. preferable.
  • the content of the tolylene diisocyanate compound (C) is 20 parts by weight or less with respect to a total of 100 parts by weight of the (meth) acrylic copolymer (A) and (B), the (meth) acrylic system
  • the compatibility with the copolymers (A) and (B) can be ensured, and a sufficient tack as an adhesive is obtained, which is preferable.
  • the pressure-sensitive adhesive composition of the present invention can be used in combination with a crosslinking agent other than the tolylene diisocyanate compound (C) as desired.
  • the pressure-sensitive adhesive composition of the present invention contains an epoxy group-containing silane coupling agent (D).
  • epoxy group-containing silane coupling agent (D) that can be used in the present invention include 3-glycidides such as 3-glycidoxypropyltrimethoxysilane and 3-glycidoxypropyltriethoxysilane.
  • 3-glycidoxypropylalkyldialkoxysilanes such as xylpropyltrialkoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, methyltri (glycidyl) silane, 2- (3 2- (3,4-epoxycyclohexyl) ethyltrialkoxysilane, such as 4-epoxycyclohexyl) ethyltrimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane And tetraethoxy Examples include, but are not limited to, a silicone alkoxy oligomer containing an epoxy group and a hydrolyzable alkoxy group in one molecule, such as a copolymer of orchid and a copolymer of 3-glycidoxypropyl
  • the epoxy group-containing silane coupling agent (D) in the present invention is one having at least one of a methoxy group or an ethoxy group in the molecule, the adhesive strength and reworkability can be easily adjusted. preferable.
  • an oligomer is used as the epoxy group-containing silane coupling agent (D) in the present invention, performance such as adhesive strength, durability, reworkability and the like can be stably obtained for a long period of time because of low volatility. preferable.
  • Examples of the epoxy group-containing silane coupling agent (D) that can be used in the present invention include product names KBM-303, KBM-403, KBE-402, KBE-403, X-41-1053 manufactured by Shin-Etsu Chemical Co., Ltd. Examples thereof include, but are not limited to, X-41-1056 and X-41-1095A.
  • the compounding amount of the epoxy group-containing silane coupling agent (D) in the pressure-sensitive adhesive composition of the present invention is 0.02 to the total of 100 parts by weight of the (meth) acrylic copolymers (A) and (B).
  • the amount is preferably 1 part by weight, more preferably 0.1 to 0.7 part by weight.
  • the amount of the epoxy group-containing silane coupling agent (D) is 0.02 parts by weight or more, the adhesive force and the reworkability can be sufficiently adjusted, which is preferable.
  • the compounding quantity of an epoxy-group-containing silane coupling agent (D) shall be 1 weight part or less, adhesive force will not become high too much or rework property will not worsen, and it is preferable.
  • the pressure-sensitive adhesive composition of the present invention may contain amino-modified silicone (E).
  • the pressure-sensitive adhesive composition of the present invention can easily control the adhesive strength and reworkability by adjusting the content of amino-modified silicone (E). Moreover, the time-dependent change of adhesive force can be suppressed by making the adhesive composition of this invention contain amino modified silicone (E).
  • amino-modified silicone (E) it is more preferable to use one having an amino group in the side chain.
  • Examples of the amino-modified silicone (E) that can be used in the present invention include the product names KF-868, KF-865, KF-864, KF-859, KF-393, KF-860, KF- manufactured by Shin-Etsu Chemical Co., Ltd. 880, KF-8004, KF-8002, KF-8005, KF-867, X-22-3820W, KF-869, KF-861, X-22-3939A, KF-877 and the like.
  • the amino-modified silicone (E) that can be used in the present invention is not limited to the above examples.
  • the compounding amount of the amino-modified silicone (E) in the pressure-sensitive adhesive composition of the present invention is 0.05 to 1 part by weight with respect to a total of 100 parts by weight of the (meth) acrylic copolymers (A) and (B).
  • the content is 0.1 to 0.7 parts by weight.
  • the compounding amount of the amino-modified silicone (E) is 0.05 parts by weight or more, the adhesive strength and the reworkability can be easily controlled, and the change with time of the adhesive strength can be suppressed.
  • the compounding amount of the amino-modified silicone (E) is 1 part by weight or less, it is preferable because the adhesive strength is not significantly reduced.
  • the pressure-sensitive adhesive composition of the present invention can optionally contain a compound (F) having a hydroxyl group and a rosin skeleton. It is preferable that the pressure-sensitive adhesive composition of the present invention contains a compound (F) having a hydroxyl group and a rosin skeleton because white spots can be further suppressed.
  • the compound (F) having a hydroxyl group and a rosin skeleton that can be used in the present invention, for example, a reaction product of rosin and a polyhydric alcohol, a reaction product of rosin and an epoxy compound, or rosin phenol can be used.
  • the rosin include wood rosin, gum rosin, hydrogenated rosin, disproportionated rosin, tall oil rosin and wood polymer rosin, gum polymer rosin, polymer oil rosin such as tall oil polymer rosin, and mixtures thereof. Can be used.
  • the polyhydric alcohol is not particularly limited as long as it is divalent or higher.
  • trihydric alcohols such as 1,5-triol and glycerin
  • tetrahydric alcohols such as diglycerin and pentaerythritol, but alcohols having a valence of 5 or more may also be used.
  • the reaction between the rosin and the polyhydric alcohol is not particularly limited, and various known means can be used. Specifically, rosin and polyhydric alcohol are charged into a reaction vessel (preferably under an inert gas stream such as nitrogen or a rare gas), and the system is usually heated to about 150 to 300 ° C. under atmospheric pressure. What is necessary is just to make it react, removing the water to do out of the system.
  • an esterification catalyst may be used.
  • acid catalysts such as acetic acid and p-toluenesulfonic acid
  • alkali metal hydroxides such as lithium hydroxide
  • alkaline earth metal hydroxides such as calcium hydroxide
  • calcium oxide, magnesium oxide and the like A metal oxide etc.
  • epoxy compound various known diepoxy compounds can be used. Specifically, ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, dipropylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, polypropylene Acyclic aliphatic diglycidyl ethers such as glycol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether; 2,2-bis (4-hydroxyphenyl) propane diglycidyl ether, bis ( 4-hydroxyphenyl) methanediglycidyl ether, 1,1-bis (4-hydroxyphenyl) ethanedigly Diethyl ether, 2,2-bis (4-hydroxycyclohexyl) propane diglycidyl
  • the reaction between the rosin and the epoxy compound is not particularly limited, and various known means can be used.
  • the ring-opening addition reaction may be continued in the presence of a catalyst of 1 mole of diepoxy compound and 2 moles of rosin at 120 to 200 ° C. until the acid value is 5 or less, preferably 3 or less.
  • the catalyst include amine catalysts such as trimethylamine, triethylamine, tributylamine, benzyldimethylamine, pyridine, 2-methylimidazole, quaternary ammonium salts such as benzyltrimethylammonium chloride, Lewis acids, boric acid esters, organometallic compounds.
  • Organic metal salts can be used.
  • the reaction product obtained by this method is a diol compound having a narrow molecular weight distribution having two rosin skeletons and two hydroxyl groups in the molecule.
  • polymers obtained by ring-opening polymerization of ethylene oxide, propylene oxide, or ⁇ -caprolactone using the diol compound as an initiator can be used in the same manner.
  • rosin phenol what is obtained by addition reaction of phenols with rosin, or so-called rosin phenol obtained by reacting rosin with a resol type phenol resin obtained by addition reaction of phenols and formaldehyde in the presence of an alkali catalyst.
  • rosin-modified phenol Any phenol can be used as long as it can be added to rosin. Specific examples include phenol, cresol, ⁇ -naphthol, para t-butylphenol, paraoctylphenol, paranonylphenol, and the like.
  • the compound (F) having a hydroxyl group and a rosin skeleton for example, “Pine Crystal D-6011”, “Pine Crystal KE-615-3”, “Pine Crystal D-6240”, “Pinecrytal KE-359” "Arakawa Chemical Industries, Ltd.”, “Neotor 125P”, “Neotor 150P” [Harima Kasei Co., Ltd.] and other commercial products can be suitably used.
  • a compound represented by the following formula (II) is particularly preferable.
  • the compounding amount of the compound (F) having a hydroxyl group and a rosin skeleton in the pressure-sensitive adhesive composition of the present invention is 1 to 20 weights with respect to a total of 100 parts by weight of the meth) acrylic copolymers (A) and (B). Part, preferably 5 to 15 parts by weight.
  • the amount of the compound (F) having a hydroxyl group and a rosin skeleton is 1 part by weight or more, white spots can be suppressed, which is preferable.
  • skeleton is 20 parts weight or less, since adhesive force does not become high too much and rework property does not fall, it is preferable.
  • the pressure-sensitive adhesive composition of the present invention can be appropriately blended with various additives, solvents, weathering stabilizers, plasticizers, softeners, dyes, pigments, inorganic fillers and the like as desired.
  • the range of blending amounts of weathering stabilizer, plasticizer, softener, dye, pigment, inorganic filler, etc. is 30 parts by weight or less with respect to 100 parts by weight of the total of the acrylic copolymers (A) and (B). More preferably, it is 20 parts by weight or less, and most preferably 10 parts by weight or less.
  • the pressure-sensitive adhesive composition can appropriately maintain the balance of the adhesive strength, wettability, heat resistance, and paste transferability of the pressure-sensitive adhesive composition, and exhibits a variety of good physical properties. can get.
  • a polarizing film was used as an example of the optical film, and a polarizing film having an adhesive layer was produced.
  • the pressure-sensitive adhesive composition was applied onto a release film surface-treated with a silicone release agent so that the coating amount after drying was 25 g / cm 2 .
  • it was dried with a hot air circulation dryer at 100 ° C. for 90 seconds to form an adhesive layer.
  • the pressure-sensitive adhesive layer surface is bonded to the back surface of a polarizing base film (a cellulose triacetate (TAC) film laminated on both sides of a polarizer mainly composed of a polyvinyl alcohol (PVA) film; about 190 ⁇ m), and then applied to a pressure nip roll. Crimped through.
  • the film was cured at 23 ° C. and 65% RH for 10 days to obtain a polarizing film having an adhesive layer.
  • the pressure-sensitive adhesive solution prepared in each of the following examples was applied to the release treatment surface of a polyethylene terephthalate (PET) film P (thickness: 10 ⁇ m) that had been subjected to release treatment on one side, and the thickness after drying was about
  • the pressure-sensitive adhesive layer was formed by casting to have a thickness of 25 ⁇ m and drying by heating at 100 ° C. for 1 minute.
  • a polyethylene terephthalate (PET) film Q (thickness: 50 ⁇ m) having a release treatment on one side is prepared, and the surface of the adhesive layer of the PET film P is prepared.
  • the PET film Q was overlapped so that the release treatment surface was in contact with each other and pressed through a pressure nip roll, and bonded together. Thereafter, curing was performed for 7 days under conditions of a temperature of 23 ° C. and a relative humidity of 50%, thereby obtaining a double-sided PSA sheet having a PET film on both sides of the PSA layer via a release treatment.
  • This double-sided pressure-sensitive adhesive sheet is a pressure-sensitive adhesive sheet made of a pressure-sensitive adhesive layer itself without a base material by peeling off two PET films provided through a release treatment.
  • the PET film Q with a thickness of 38 ⁇ m provided on one side of the obtained double-sided pressure-sensitive adhesive sheet is peeled off, and the PET film with a thickness of 100 ⁇ m that is not subjected to a release treatment so as to come into contact with the surface of the exposed pressure-sensitive adhesive layer
  • a test sheet was prepared by stacking R [trade name: A4100, manufactured by Toyobo Co., Ltd.], pressing through a pressure nip roll, and bonding.
  • test sheet described above was cut into 25 mm ⁇ 150 mm to obtain a sample piece, and the PET film P having a thickness of 100 ⁇ m was peeled off, and the surface of the exposed pressure-sensitive adhesive layer was formed on a 2 mm thick glass plate.
  • a test sample was prepared by pressure bonding using a table laminating machine. The obtained test sample was allowed to stand for 24 hours under the conditions of 23 ° C. and 50% RH, and then one end of the PET film R was oriented in the direction of 180 ° with a desktop material testing machine STA-1225 (Orientec Co., Ltd.). Tensile strength and adhesive strength at 180 ° peeling (peeling speed: 300 mm / min) were measured. Evaluation was performed according to the following evaluation criteria.
  • Example 1 506 parts by weight of the acrylic copolymer solution synthesized in Production Example 1 as the acrylic copolymer (A) (85 parts by weight as the acrylic copolymer (A)), and the production example as the acrylic copolymer (B) 76 parts by weight of the acrylic copolymer solution synthesized in 2 (15 parts by weight as the acrylic copolymer (B)), 17 parts by weight of coronate L as the tolylene diisocyanate compound (C) (manufactured by Nippon Polyurethane Co., Ltd., 13 parts by weight of active ingredient), 0.02 part by weight of TETRAD-X as an epoxy crosslinking agent (epoxy compound manufactured by Mitsubishi Gas Chemical Co., Ltd., 0.02 part by weight of active ingredient), a compound having a hydroxyl group and a rosin skeleton (F ) D-6011 as 5 parts by weight (rosin-containing diol manufactured by Arakawa Chemical Industries, active ingredient 5 parts by weight), and epoxy group-containing silane coupling agent (
  • a pressure-sensitive adhesive composition was obtained by sufficiently stirring and mixing the amino-modified silicone manufactured and 0.1 part by weight of the active ingredient. Using the obtained pressure-sensitive adhesive composition, a test optical film was prepared by the above-described test optical film preparation method, and the above-described various measurements were performed.
  • the optical film of Example 1 showed durability (80 ° C. DRY, 105 ° C. DRY, 60 ° C. ⁇ 90% RH), and the evaluation standard of the white-out item was “ ⁇ ”. That is, it was shown that the optical film of Example 1 was excellent in durability and white spot suppression ability even in a high temperature or high temperature and high humidity environment.
  • test optical films of Examples 2 to 17 and Comparative Examples 1 to 5 were prepared in the same manner as in Example 1, and the performance was improved. evaluated.
  • Coronate L Made by Nippon Polyurethane, 75% active ingredient X-41-1053: Shin-Etsu Chemical Co., Ltd., 100% active ingredient, alkoxy oligomer system, alkoxy group is methoxy / ethoxy X-41-1056: Shin-Etsu Chemical Co., Ltd., 100% active ingredient, alkoxy oligomer system, alkoxy group is methoxy KBM-403: Shin-Etsu Chemical Co., active ingredient 100%, alkoxy monomer system, alkoxy group is methoxy, chemical name is 3-glycidoxypropyltrimethoxysilane KBM-803: Shin-Etsu Chemical Co., Ltd., active ingredient 100%, alkoxy Monomer system, alkoxy group is methoxy, chemical name is 3-mercaptopropyltrimethoxysilane KF-859: manufactured by Shin-Etsu Chemical Co., Ltd., 100% active ingredient, amino-modified KF-353: manufactured by Shin-Ets

Abstract

L'invention a pour but de proposer une composition d'agent adhésif qui est utilisée dans l'adhésion d'un film optique, présente une durabilité supérieure même dans des milieux à haut degré d'humidité à haute température, et a une excellente capacité à empêcher des taches blanches de se produire. À cet effet, la composition d'agent adhésif selon l'invention contient : un copolymère (méth)acrylique (A) contenant un groupe carboxyle ; un copolymère (méth)acrylique (B) contenant un groupe carboxyle et un groupe hydroxyle ; 5-20 parties en poids d'un composé tolylène diisocyanate (C) pour chaque total de 100 parties en poids des copolymères (méth)acryliques (A et B) ; et un agent de couplage de type silane à teneur en groupe époxy (D).
PCT/JP2011/068949 2010-08-24 2011-08-23 Composition d'agent adhésif WO2012026456A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN201180036207.9A CN103025837B (zh) 2010-08-24 2011-08-23 粘合剂组合物
JP2012530673A JP5826179B2 (ja) 2010-08-24 2011-08-23 粘着剤組成物
KR1020137007273A KR101840072B1 (ko) 2010-08-24 2011-08-23 점착제 조성물

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2010-187558 2010-08-24
JP2010187557 2010-08-24
JP2010187558 2010-08-24
JP2010-187557 2010-08-24

Publications (1)

Publication Number Publication Date
WO2012026456A1 true WO2012026456A1 (fr) 2012-03-01

Family

ID=45723450

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2011/068949 WO2012026456A1 (fr) 2010-08-24 2011-08-23 Composition d'agent adhésif

Country Status (5)

Country Link
JP (1) JP5826179B2 (fr)
KR (1) KR101840072B1 (fr)
CN (1) CN103025837B (fr)
TW (1) TWI493001B (fr)
WO (1) WO2012026456A1 (fr)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014025000A (ja) * 2012-07-27 2014-02-06 Yokohama Rubber Co Ltd:The ウレタン接着剤組成物
WO2014156200A1 (fr) * 2013-03-29 2014-10-02 東洋インキＳｃホールディングス株式会社 Agent adhésif et feuille adhésive produite en l'utilisant
JP2014234419A (ja) * 2013-05-31 2014-12-15 日本カーバイド工業株式会社 光学部材用粘着剤組成物及び光学フィルム
WO2015008384A1 (fr) * 2013-07-19 2015-01-22 綜研化学株式会社 Composition adhésive sensible à la pression pour un élément optique, feuille adhésive sensible à la pression et stratifié
CN104379694A (zh) * 2012-06-05 2015-02-25 日本电石工业株式会社 偏振板用粘接剂组合物、带有粘接剂的偏振板和显示装置
KR20160024748A (ko) 2014-08-26 2016-03-07 삼성에스디아이 주식회사 점착제 조성물, 점착층, 이를 이용한 광학부재 및 화상표시장치
WO2016158609A1 (fr) * 2015-03-31 2016-10-06 日東電工株式会社 Composition d'adhésif, couche d'adhésif, film de polarisation avec couche d'adhésif, et dispositif d'affichage d'image
JP2016188309A (ja) * 2015-03-30 2016-11-04 日本カーバイド工業株式会社 粘着剤組成物及び粘着シート
JP2017066331A (ja) * 2015-10-02 2017-04-06 東洋インキＳｃホールディングス株式会社 粘着剤およびそれを用いた粘着シート
JP2017218594A (ja) * 2017-07-21 2017-12-14 日東電工株式会社 粘着剤組成物、粘着剤層、粘着剤層付偏光フィルム、及び画像表示装置
JP2018150536A (ja) * 2018-04-02 2018-09-27 東洋インキＳｃホールディングス株式会社 粘着剤およびそれを用いた粘着シート
JPWO2019031486A1 (ja) * 2017-08-07 2019-11-07 日東電工株式会社 粘着剤層、粘着剤層付光学フィルム、光学積層体、および画像表示装置

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104086774B (zh) * 2014-06-04 2017-01-04 河南卓立膜材料股份有限公司 一种合成树脂及利用该合成树脂制备的uv背涂液
WO2016032187A1 (fr) * 2014-08-26 2016-03-03 삼성에스디아이 주식회사 Composition adhésive, couche adhésive, élément optique l'utilisant et dispositif d'affichage d'image
MX2021015730A (es) * 2019-07-02 2022-01-24 Basf Coatings Gmbh Una composicion de barniz de 2k, su preparacion y uso de la misma.

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04117475A (ja) * 1990-09-07 1992-04-17 Toyo Ink Mfg Co Ltd 再剥離型粘着剤組成物
JPH10130612A (ja) * 1996-10-30 1998-05-19 Nippon Synthetic Chem Ind Co Ltd:The 粘着剤組成物
JPH10204399A (ja) * 1997-01-24 1998-08-04 Sekisui Chem Co Ltd アクリル系粘着剤組成物
JPH10298528A (ja) * 1997-04-30 1998-11-10 Arakawa Chem Ind Co Ltd ポリエステル系接着剤用粘着付与樹脂およびポリエステル系接着剤組成物
JP2006290994A (ja) * 2005-04-08 2006-10-26 Daio Paper Corp 粘着シート
WO2008090936A1 (fr) * 2007-01-22 2008-07-31 Sumitomo Chemical Company, Limited Film optique ayant un agent adhésif et laminé optique
WO2010024103A1 (fr) * 2008-09-01 2010-03-04 日本カーバイド工業株式会社 Composition d’adhésif autocollant, adhésif autocollant et film optique
WO2010110254A1 (fr) * 2009-03-24 2010-09-30 日本カーバイド工業株式会社 Composition d'agent adhésif

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5268137B2 (ja) * 2008-04-15 2013-08-21 日東電工株式会社 光学フィルム用粘着剤組成物、粘着型光学フィルムおよび画像表示装置
JP5923231B2 (ja) * 2008-09-01 2016-05-24 日本カーバイド工業株式会社 粘着剤組成物、光学フィルム、及び粘着剤組成物の製造方法

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04117475A (ja) * 1990-09-07 1992-04-17 Toyo Ink Mfg Co Ltd 再剥離型粘着剤組成物
JPH10130612A (ja) * 1996-10-30 1998-05-19 Nippon Synthetic Chem Ind Co Ltd:The 粘着剤組成物
JPH10204399A (ja) * 1997-01-24 1998-08-04 Sekisui Chem Co Ltd アクリル系粘着剤組成物
JPH10298528A (ja) * 1997-04-30 1998-11-10 Arakawa Chem Ind Co Ltd ポリエステル系接着剤用粘着付与樹脂およびポリエステル系接着剤組成物
JP2006290994A (ja) * 2005-04-08 2006-10-26 Daio Paper Corp 粘着シート
WO2008090936A1 (fr) * 2007-01-22 2008-07-31 Sumitomo Chemical Company, Limited Film optique ayant un agent adhésif et laminé optique
WO2010024103A1 (fr) * 2008-09-01 2010-03-04 日本カーバイド工業株式会社 Composition d’adhésif autocollant, adhésif autocollant et film optique
WO2010110254A1 (fr) * 2009-03-24 2010-09-30 日本カーバイド工業株式会社 Composition d'agent adhésif

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104379694A (zh) * 2012-06-05 2015-02-25 日本电石工业株式会社 偏振板用粘接剂组合物、带有粘接剂的偏振板和显示装置
CN104379694B (zh) * 2012-06-05 2016-07-06 日本电石工业株式会社 偏振板用粘接剂组合物、带有粘接剂的偏振板和显示装置
JP2014025000A (ja) * 2012-07-27 2014-02-06 Yokohama Rubber Co Ltd:The ウレタン接着剤組成物
WO2014156200A1 (fr) * 2013-03-29 2014-10-02 東洋インキＳｃホールディングス株式会社 Agent adhésif et feuille adhésive produite en l'utilisant
JP2014234419A (ja) * 2013-05-31 2014-12-15 日本カーバイド工業株式会社 光学部材用粘着剤組成物及び光学フィルム
WO2015008384A1 (fr) * 2013-07-19 2015-01-22 綜研化学株式会社 Composition adhésive sensible à la pression pour un élément optique, feuille adhésive sensible à la pression et stratifié
JPWO2015008384A1 (ja) * 2013-07-19 2017-03-02 綜研化学株式会社 光学部材用粘着剤組成物、粘着シートおよび積層体
KR20160024748A (ko) 2014-08-26 2016-03-07 삼성에스디아이 주식회사 점착제 조성물, 점착층, 이를 이용한 광학부재 및 화상표시장치
JP2016188309A (ja) * 2015-03-30 2016-11-04 日本カーバイド工業株式会社 粘着剤組成物及び粘着シート
JP2016190997A (ja) * 2015-03-31 2016-11-10 日東電工株式会社 粘着剤組成物、粘着剤層、粘着剤層付偏光フィルム、及び画像表示装置
WO2016158609A1 (fr) * 2015-03-31 2016-10-06 日東電工株式会社 Composition d'adhésif, couche d'adhésif, film de polarisation avec couche d'adhésif, et dispositif d'affichage d'image
US10768473B2 (en) 2015-03-31 2020-09-08 Nitto Denko Corporation Pressure-sensitive-adhesive composition, pressure-sensitive-adhesive layer, pressure-sensitive-adhesive-layer-attached polarizing film, and image display device
JP2017066331A (ja) * 2015-10-02 2017-04-06 東洋インキＳｃホールディングス株式会社 粘着剤およびそれを用いた粘着シート
JP2017218594A (ja) * 2017-07-21 2017-12-14 日東電工株式会社 粘着剤組成物、粘着剤層、粘着剤層付偏光フィルム、及び画像表示装置
JPWO2019031486A1 (ja) * 2017-08-07 2019-11-07 日東電工株式会社 粘着剤層、粘着剤層付光学フィルム、光学積層体、および画像表示装置
JP2020059280A (ja) * 2017-08-07 2020-04-16 日東電工株式会社 粘着剤層、粘着剤層付光学フィルム、光学積層体、および画像表示装置
JP2018150536A (ja) * 2018-04-02 2018-09-27 東洋インキＳｃホールディングス株式会社 粘着剤およびそれを用いた粘着シート

Also Published As

Publication number Publication date
KR20130096727A (ko) 2013-08-30
TW201229167A (en) 2012-07-16
CN103025837B (zh) 2016-05-04
JPWO2012026456A1 (ja) 2013-10-28
KR101840072B1 (ko) 2018-03-19
TWI493001B (zh) 2015-07-21
JP5826179B2 (ja) 2015-12-02
CN103025837A (zh) 2013-04-03

Similar Documents

Publication Publication Date Title
JP5826179B2 (ja) 粘着剤組成物
JP5484035B2 (ja) 粘着剤組成物及び光学フィルム
JP5746966B2 (ja) 粘着剤組成物
JP5611527B2 (ja) 粘着剤及び光学フィルム
TWI579357B (zh) Adhesive composition, adhesive polarizer and liquid crystal display device
KR101748873B1 (ko) 점착제 조성물, 광학필름 및 점착제 조성물의 제조방법
JPWO2010024103A1 (ja) 粘着剤組成物、粘着剤、及び光学フィルム
TW200902660A (en) Optically compensated acrylic pressure-sensitive adhesive composition, polarizing plate and liquid crystal display device containing the same
JP6870934B2 (ja) 偏光板用粘着フィルム、それを含む偏光板および光学表示装置
JP5557438B2 (ja) 粘着剤組成物及び光学フィルム
JP5465079B2 (ja) 偏光板用粘着剤組成物、並びにそれを用いた粘着剤付偏光板及び液晶表示装置
TWI470051B (zh) An adhesive composition for a polarizing plate, an adhesive-attached polarizing plate and a liquid crystal display device using the composition
JP5384423B2 (ja) 偏光板用粘着剤組成物、並びにそれを用いた粘着剤付偏光板及び液晶表示装置
TWI661018B (zh) 黏接劑組成物及黏接片
TW201245367A (en) Pressure-sensitive adhesive composition for optical members, adhesive optical member and image display device
JP6600914B2 (ja) 偏光板用粘着剤組成物
KR100947970B1 (ko) 아크릴계 점착제 조성물
TWI637973B (zh) 丙烯酸共聚物和包含丙烯酸共聚物的黏著劑組合物
JP2019014901A (ja) 粘着剤組成物及び粘着シート

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 201180036207.9

Country of ref document: CN

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 11819919

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 2012530673

Country of ref document: JP

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 20137007273

Country of ref document: KR

Kind code of ref document: A

122 Ep: pct application non-entry in european phase

Ref document number: 11819919

Country of ref document: EP

Kind code of ref document: A1