[go: up one dir, main page]

WO2015099279A1 - Composition adhésive contenant un agent anti-statique ionique - Google Patents

Composition adhésive contenant un agent anti-statique ionique Download PDF

Info

Publication number
WO2015099279A1
WO2015099279A1 PCT/KR2014/010270 KR2014010270W WO2015099279A1 WO 2015099279 A1 WO2015099279 A1 WO 2015099279A1 KR 2014010270 W KR2014010270 W KR 2014010270W WO 2015099279 A1 WO2015099279 A1 WO 2015099279A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
adhesive composition
sensitive adhesive
pressure
group
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/KR2014/010270
Other languages
English (en)
Korean (ko)
Inventor
최한영
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dongwoo Fine Chem Co Ltd
Original Assignee
Dongwoo Fine Chem Co Ltd
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 Dongwoo Fine Chem Co Ltd filed Critical Dongwoo Fine Chem Co Ltd
Publication of WO2015099279A1 publication Critical patent/WO2015099279A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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
    • 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
    • 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
    • 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
    • C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • 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
    • C08K2201/00—Specific properties of additives
    • C08K2201/017—Additives being an antistatic agent
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0075—Antistatics
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
    • C08K5/3445—Five-membered rings
    • 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
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays
    • 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
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F2202/00—Materials and properties
    • G02F2202/28—Adhesive materials or arrangements

Definitions

  • the present invention relates to an adhesive composition comprising an ionic antistatic agent.
  • the image display device is composed of a liquid crystal cell containing a liquid crystal and a polarizing plate, which is mainly bonded by forming an adhesive layer on one surface of the polarizing plate.
  • a surface protection film such as a retardation plate, a wide viewing angle compensation plate, and brightness enhancement is additionally attached to the polarizing plate through an adhesive or the like.
  • the optical members such as the surface protection film and the polarizing plate are made of a plastic material, static electricity is generated during friction and peeling, and when voltage is applied to the liquid crystal while the static electricity remains, the orientation of the liquid crystal molecules is lost or the panel is defective. This can happen. Therefore, various antistatic treatments are performed to prevent such defects.
  • Korean Patent Publication No. 2011-0112263 discloses a method of introducing a functional group having excellent compatibility with an antistatic agent in a monomer of the pressure-sensitive adhesive composition to suppress bleeding of the antistatic agent. However, durability is deteriorated under high temperature and high humidity conditions. Did not solve.
  • Patent Document 1 Korean Patent Publication No. 2011-0112263
  • An object of the present invention is to provide an adhesive composition with remarkably improved antistatic properties and durability.
  • a pressure-sensitive adhesive composition comprising an acrylic copolymer, a crosslinking agent and an ionic antistatic agent represented by the following general formula (1):
  • R 1 is a hydrogen atom, a straight or branched chain alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 12 carbon atoms
  • X is a halogen atom, a cyano group, -OR 2 , -OCOR 3 , or- NR 4 R 5
  • R 2 , R 3 , R 4 and R 5 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, or an aryl group having 6 to 12 carbon atoms
  • Y ⁇ is an anion.
  • Acid compound, n is an integer from 1 to 30).
  • the pressure-sensitive adhesive sheet comprising an adhesive layer formed of the pressure-sensitive adhesive composition of any one of the above 1 to 4.
  • a polarizing plate having a pressure-sensitive adhesive layer formed of the pressure-sensitive adhesive composition of any one of the above 1 to 4 on at least one side.
  • Image display device including the polarizing plate of the above six.
  • the pressure-sensitive adhesive composition of the present invention exhibits markedly improved antistatic properties and durability, and thus can maintain excellent adhesion even in harsh conditions such as high temperature and high humidity.
  • the present invention relates to a pressure-sensitive adhesive composition
  • a pressure-sensitive adhesive composition comprising an acrylic copolymer, a crosslinking agent, and an ionic antistatic agent, and exhibits not only excellent antistatic performance, but also markedly improved durability, and can maintain excellent adhesion even in harsh conditions such as high temperature and high humidity.
  • Pressure-sensitive adhesive composition comprising an acrylic copolymer, a crosslinking agent, and an ionic antistatic agent.
  • the pressure-sensitive adhesive composition of the present invention includes an acrylic copolymer, a crosslinking agent and an ionic antistatic agent.
  • the ionic antistatic agent of the present invention is represented by the following general formula (1), and contains a polyethylene glycol derivative in the molecule, stabilizes the cation in the molecule and at the same time improves the freedom of movement of the anion, it shows only excellent antistatic performance In addition, it is excellent in compatibility with the pressure-sensitive adhesive composition, it is possible to prevent the bleed out of the ionic compound to provide a pressure-sensitive adhesive composition excellent in durability.
  • R 1 is a cycloalkyl group and a hydrogen atom, an alkyl group of straight or branched chain of 1 to 12 carbon atoms, or having from 3 to 12
  • X is a halogen atom, a cyano group, -OR 2, -OCOR 3, -NR 4 R 5 , R 2 , R 3 , R 4, and R 5 are each independently a hydrogen atom, a straight or branched chain alkyl group having 1 to 12 carbon atoms, or an aryl group having 6 to 12 carbon atoms, and n is 1 to 30 Is an integer.
  • Y - is an anionic compound Cl -, Br -, I - , AlCl 4 -, Al 2 Cl 7 -, BF 4 -, PF 6 -, ClO 4 -, NO 3 -, CH 3 COO -, CF 3 COO -, CH 3 SO 3 -, CF 3 SO 3 -, (CF 3 SO 2) 2 N - (CF 3 SO 2) 3 C -, AsF 6 -, SbF 6 -, NbF 6 -, TaF 6 -, ( CN) 2 N -, C 4 F 9 SO 3 -, (C 2 F 5 SO 2) 2 N -, C 3 F 7 COO -, (CF 3 SO 2) (CF 3 CO) N - and N (SO 2 F) an anionic compound consisting of 2 ⁇ .
  • ionic antistatic agent may be at least one compound selected from the group consisting of the following Chemical Formulas 2 to 9.
  • the content of the ionic antistatic agent is not particularly limited.
  • the ionic antistatic agent may be included in an amount of 0.1 to 10 parts by weight, preferably 0.5 to 5 parts by weight, based on 100 parts by weight of the acrylic copolymer. If the content is less than 0.1 parts by weight, the antistatic function may be insufficient. If the content is more than 10 parts by weight, the content of the anionic compound in the composition is excessive, easily bleed out may occur peeling failure under heat conditions.
  • the acrylic copolymer of this invention can suppress the bleed out of an ionic compound with the outstanding compatibility with the ionic compound of an antistatic agent, and can further improve durability of an adhesive composition.
  • the acrylic copolymer may be polymerized including a (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms and a polymerizable monomer having a crosslinkable functional group, wherein the (meth) acrylate is an acrylate and a methacrylate. Means all.
  • n-butyl (meth) acrylate As a (meth) acrylate monomer which has a C1-C12 alkyl group, n-butyl (meth) acrylate, 2-butyl (meth) acrylate, t-butyl (meth) acrylate, 2-ethylhexyl (meth) Acrylate, ethyl (meth) acrylate, methyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, pentyl (meth) acrylate, n-octyl (meth) acrylate, Isooctyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, lauryl (meth) acrylate, and the like, among which n-butyl acrylate, 2-ethylhexyl acrylate or Mix
  • the content and mixing ratio of the (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms is not particularly limited.
  • the content may be 85 to 99.9 parts by weight based on 100 parts by weight of the total monomers, based on solid content. Preferably it is 90 to 95 parts by weight. If the content is less than 85 parts by weight, sufficient adhesion cannot be exerted, and if it exceeds 99.9 parts by weight, the cohesion may be lowered.
  • the polymerizable monomer having a crosslinkable functional group is a component for reinforcing the cohesive force or adhesive strength of the pressure-sensitive adhesive composition by chemical bonding and imparting durability and cutting property, such as a monomer having a carboxyl group, a monomer having a hydroxy group, a monomer having an amide group, The monomer etc. which have a tertiary amine group are mentioned, These can be used individually or in mixture of 2 or more types, It is preferable not to contain acrylic acid from the viewpoint of corrosion prevention improvement.
  • Monovalent acids such as (meth) acrylic acid and a crotonic acid; Diacids such as maleic acid, itaconic acid and fumaric acid, and monoalkyl esters thereof; 3- (meth) acryloylpropionic acid; Succinic anhydride ring-opening adduct of 2-hydroxyalkyl (meth) acrylate with 2-3 carbon atoms of an alkyl group, Succinic anhydride ring opening adduct of hydroxyalkylene glycol (meth) acrylate with 2-4 carbon atoms of an alkylene group And a compound obtained by ring-opening addition of succinic anhydride to a caprolactone adduct of 2-hydroxyalkyl (meth) acrylate having 2 or 3 carbon atoms of an alkyl group, and among these, (meth) acrylic acid is preferable.
  • (meth) acrylic acid is preferable.
  • Examples of the monomer having an amide group include (meth) acrylamide, N-isopropylacrylamide, N-tert-butylacrylamide, 3-hydroxypropyl (meth) acrylamide, 4-hydroxybutyl (meth) acrylamide, 6 -Hydroxyhexyl (meth) acrylamide, 8-hydroxyoctyl (meth) acrylamide, 2-hydroxyethylhexyl (meth) acrylamide, etc. are mentioned, Among these, (meth) acrylamide is preferable.
  • Monomers having a tertiary amine group include N, N- (dimethylamino) ethyl (meth) acrylate, N, N- (diethylamino) ethyl (meth) acrylate, and N, N- (dimethylamino) propyl ( Meth) acrylate, etc. are mentioned.
  • the content and mixing ratio of the polymerizable monomer having a crosslinkable functional group are not particularly limited.
  • the polymerizable monomer may be included in an amount of 0.1 to 15 parts by weight, preferably 0.5 to 8 parts by weight, based on 100 parts by weight of the total monomers. Madam is good. If the content is less than 0.1 parts by weight, the cohesive force of the pressure-sensitive adhesive may be lowered, the durability may be lowered. If the content is more than 15 parts by weight, the adhesive strength is lowered and durability may be lowered by a high gel fraction.
  • the acrylic copolymer may further include a polymerizable monomer known in the art in addition to the above monomers in a range that does not lower the adhesive strength, such as 10 wt% or less of the total weight of the monomers.
  • the production method of the copolymer is not particularly limited, and may be prepared using a method such as bulk polymerization, solution polymerization, emulsion polymerization or suspension polymerization, which are commonly used in the art, and solution polymerization is preferable.
  • a solvent, a polymerization initiator, a chain transfer agent for molecular weight control, and the like, which are usually used in the polymerization may be used.
  • the acrylic copolymer preferably has a weight average molecular weight (polystyrene equivalent, Mw) measured by gel permeation chromatography (GPC) of 50,000 to 2 million, more preferably 400,000 to 2 million. If the weight average molecular weight is less than 50,000, there is a lack of cohesion between the copolymers may cause problems in adhesion durability, if the weight average molecular weight is more than 2 million may require a large amount of dilution solvent to ensure fairness during coating.
  • Mw polystyrene equivalent
  • the crosslinking agent is a component for appropriately crosslinking the copolymer to improve cohesion, and the kind thereof is not particularly limited.
  • an isocyanate type, an epoxy type, or the like may be used, and these may be used alone or in combination of two or more thereof. have.
  • Isocyanate type crosslinking agent specifically, tolylene diisocyanate, xylene diisocyanate, 2, 4- diphenylmethane diisocyanate, 4, 4- diphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, tetramethylene xylene diisocyanate, Diisocyanate compounds such as naphthalene diisocyanate, adducts of polyhydric alcohol-based compounds such as diisocyanate and trimethanol propane, isocyanurates obtained by self-condensing diisocyanates, biuret bodies condensed with diisocyanates in diisocyanate urea, and tri The polyfunctional isocyanate compound containing three functional groups, such as phenylmethane triisocyanate and methylene bistriisocyanate, etc. are mentioned.
  • Epoxy type crosslinking agent specifically, ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, polypropylene Glycol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, polytetramethylene glycol diglycidyl ether, glycerol diglycidyl ether, glycerol triglycidyl ether , Diglycerol polyglycidyl ether, polyglycerol polyglycidyl ether, resorcin diglycidyl ether, 2,2-dibromoneopentyl glycol diglycidyl ether, trimethylol propane triglycidyl ether, pentaerythrate Lithol poly
  • At least one crosslinking agent selected from the group consisting of melamine derivatives such as hexamethyrolmelamine, hexamethoxymethylmelamine, hexabutoxymethylmelamine and the like may be further added.
  • melamine derivatives such as hexamethyrolmelamine, hexamethoxymethylmelamine, hexabutoxymethylmelamine and the like
  • crosslinking agent examples include Cor-L (Japan Polyurethane Industry Co., Ltd.).
  • the content of the crosslinking agent is not particularly limited within the range capable of performing its function, for example, 0.1 to 15 parts by weight, preferably 0.1 to 5 parts by weight, based on 100 parts by weight of the acrylic copolymer. Can be. If the content is less than 0.1 parts by weight, the cohesive force may be reduced due to insufficient crosslinking degree, thereby impairing the adhesive durability and the cutting property. If the content is more than 15 parts by weight, problems may occur in relieving residual stress due to an excessive crosslinking reaction.
  • the pressure-sensitive adhesive composition of the present invention may further include a silane coupling agent.
  • the silane coupling agent covalently bonds to the adherend surface polar group, thereby improving adhesion.
  • a silane coupling agent will not be specifically limited if it contains functional groups, such as an amino group, an epoxy group, an acetoacetyl group, a polyalkylene glycol group, an acryl group, and an alkyl group,
  • functional groups such as an amino group, an epoxy group, an acetoacetyl group, a polyalkylene glycol group, an acryl group, and an alkyl group
  • silane coupling agents include KBM-403 (Shin-Etsu Co., Ltd.).
  • the content of the silane coupling agent is not particularly limited.
  • the silane coupling agent may be included in an amount of 0.1 to 2 parts by weight, preferably 0.1 to 0.5 parts by weight, based on 100 parts by weight of the acrylic copolymer.
  • the content is less than 0.1 parts by weight, the adhesion to the substrate may be insufficient, so that peeling may occur under moisture-resistant heat conditions.
  • the content is more than 2 parts by weight, the cohesion may be excessively increased, and thus the durability may be lowered as the adhesive properties such as adhesive strength are lowered. have.
  • the pressure-sensitive adhesive composition of the present invention may further include additives such as antioxidants, corrosion inhibitors, antifoaming agents, fillers, antistatic agents, and the like, which are commonly used in the art, without departing from the object of the present invention.
  • additives such as antioxidants, corrosion inhibitors, antifoaming agents, fillers, antistatic agents, and the like, which are commonly used in the art, without departing from the object of the present invention.
  • the present invention provides a pressure-sensitive adhesive sheet comprising a pressure-sensitive adhesive layer formed of the pressure-sensitive adhesive composition.
  • the thickness of the adhesive layer is not particularly limited, and may be, for example, 3 to 100 ⁇ m, preferably 10 to 100 ⁇ m.
  • the adhesive sheet of the present invention includes an adhesive layer formed on at least one surface of the release film.
  • the pressure-sensitive adhesive layer can be formed by coating the pressure-sensitive adhesive composition on at least one surface of the release film.
  • the coating method is not particularly limited, and methods known in the art may be used. For example, methods such as a bar coater, air knife, gravure, reverse roll, kiss roll, spray, blade, die coater, casting, and spin coating may be used. It is available.
  • the release film is not particularly limited, and a release film commonly used in an adhesive sheet may be used, for example, polyester resins such as polyethylene terephthalate, polybutyrene terephthalate, polyethylene naphthalate, and polybutylene naphthalate; Polyimide resins; Acrylic resins; Styrene resins such as polystyrene and acrylonitrile-styrene; Polycarbonate resins; Polylactic acid resins; Polyurethane resins; Polyolefin resins such as polyethylene, polypropylene, ethylene-propylene copolymers; Vinyl resins such as polyvinyl chloride and polyvinylidene chloride; Polyamide resins; Sulfone resins; Polyether ether ketone resins; Allyl resins; Or it may be formed of a mixture of the resin.
  • polyester resins such as polyethylene terephthalate, polybutyrene terephthalate, polyethylene naphthalate, and polybutylene
  • the thickness of the release film is not particularly limited, and may be, for example, 5 to 500 ⁇ m, and preferably 10 to 100 ⁇ m.
  • the present invention provides a polarizing plate including a pressure-sensitive adhesive layer formed on at least one surface of the pressure-sensitive adhesive composition.
  • the polarizing plate of the present invention includes a polarizer, a protective film bonded to at least one surface of the polarizer, and an adhesive layer formed of the pressure-sensitive adhesive composition on the protective film.
  • the polarizer may be a polarizer known in the art, and for example, may be manufactured by swelling, dyeing, crosslinking, stretching, washing, drying, and the like of a polyvinyl alcohol-based film.
  • the protective film is not particularly limited as long as the film is excellent in transparency, mechanical strength, thermal stability, moisture shielding, and isotropy.
  • polyester film such as polyethylene terephthalate, polyethylene isophthalate, polybutylene terephthalate; Cellulose films such as diacetyl cellulose and triacetyl cellulose; Polycarbonate film; Acrylic films such as polymethyl (meth) acrylate and polyethyl (meth) acrylate; Styrene films such as polystyrene and acrylonitrile-styrene copolymers; Polyolefin-based film; Vinyl chloride film; Polyamide films such as nylon and aromatic polyamides; Imide film; Sulfone film; Polyether ketone film; Sulfided polyphenylene-based films; Vinyl alcohol film; Vinylidene chloride-based film; Vinyl butyral film; Allylate film; Polyoxymethylene film; Urethane film; Epoxy film; Silicone film etc. are mentioned.
  • the adhesive layer may be directly coated on the protective film, or may be formed by attaching the adhesive sheet to the protective film.
  • the present invention provides an image display device including the polarizing plate.
  • the image display apparatus of the present invention may further include a configuration known in the art in addition to the polarizing plate.
  • Nitrogen gas is refluxed, 90 parts by weight of n-butyl acrylate, 7 parts by weight of methacrylate, 2 parts by weight of 2-hydroxyethyl acrylate, 1 weight of acrylic acid in a 1 L reactor equipped with a cooling device for easy temperature control After adding a monomer mixture consisting of parts, 100 parts by weight of ethyl acetate was added as a solvent. Nitrogen gas was then purged for 1 hour to remove oxygen and then held at 62 ° C. After the mixture was uniformly mixed, 0.07 parts by weight of azobisisobutyronitrile (AIBN) was added as a reaction initiator, and reacted for 8 hours to prepare an acrylic copolymer (a weight average molecular weight of about 1 million).
  • AIBN azobisisobutyronitrile
  • N-methylimidazole (82g, 1mol) and 1-Chloro-2- (2-methoxy-ethoxy) -ethane (139g, 1mol) were dissolved in 300g of toluene, heated to 80 ° C, stirred for 12 hours, and then distilled water Slowly add a solution of NaPF6 (168g, 1mol) in (300g), stir for an additional 6 hours at the same temperature, cool the reaction solution to room temperature, separate the toluene layer using a separatory funnel, and add Washing was repeated three times using 300 g of distilled water to remove metal salts, and the obtained organic layer was distilled under reduced pressure to remove the solvent and the remaining reactants to obtain Chemical Formula A-1.
  • N-methylimidazole (82 g, 1 mol)
  • N-ethylimidazole (96 g, 1 mol)
  • a pressure-sensitive adhesive composition having the composition and content shown in Table 1.
  • the silicone release agent was coated on the film, and dried at 100 ° C. for 1 minute to form a pressure-sensitive adhesive layer having a thickness of 25 ⁇ m.
  • a release film was laminated on the pressure-sensitive adhesive layer to prepare a pressure-sensitive adhesive sheet.
  • a pressure-sensitive adhesive layer was laminated on an iodine polarizing plate containing a TAC protective film of 185 ⁇ m thickness to prepare a polarizing plate with pressure-sensitive adhesive.
  • the pressure-sensitive adhesive compositions of Examples and Comparative Examples were applied on a release film coated with a silicone release agent so as to have a thickness of 25 ⁇ m, and dried at 100 ° C. for 1 minute to form an adhesive layer.
  • the adhesive layer prepared above was laminated on the iodine-based polarizing film (total thickness 185 ⁇ m) to which a triacetyl cellulose protective film was bonded on both sides, to prepare a polarizing plate.
  • the prepared polarizing plate was stored for 7 days under the condition of 23 ° C., 60% RH.
  • the release film of the polarizing plate prepared above was removed, bonded to the corning glass, subjected to autoclave treatment, and allowed to stand for 500 hours at a temperature of 80 ° C., followed by evaluation of the occurrence of bubbles or peeling. Evaluation was performed after standing for 24 hours at room temperature immediately before the evaluation after the heat treatment.
  • the release film of the polarizing plate prepared above was removed, bonded to a corning glass, and subjected to autoclave treatment, and then left for 500 hours at a temperature and humidity of 60 ° C. 90%, followed by evaluation of the occurrence of bubbles or peeling. Evaluation was performed after standing for 24 hours at room temperature immediately before the evaluation after the heat treatment.
  • the surface resistivity of the prepared polarizing plate was measured.
  • X surface resistivity value of 1.0X10 12 or more
  • Example 5 in which the amount of the antistatic agent was included in a small amount, the antistatic function was slightly lowered, and in Example 7 included in the scope of the present invention but included slightly in excess of the preferred range, the heat resistance was lowered. It could be confirmed.
  • Example 8 contained slightly in excess of the scope of the present invention, the antistatic function was excellent, but the content of the anionic compound in the pressure-sensitive adhesive composition is excessive, easily bleed out occurs, the heat resistance and moisture heat resistance slightly decreased I could confirm it.
  • Comparative Example 2 using the chemical formula A-10 instead of the antistatic agent of the present invention is slightly reduced antistatic performance, do not contain a polyethylene glycol derivative in the molecule, the compatibility with the pressure-sensitive adhesive composition is lowered, the adhesive strength is slightly reduced at high temperature conditions It could be confirmed. However, the heat-and-moisture resistance showed the same excellent effect as that of the Example.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Nonlinear Science (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

La présente invention concerne une composition adhésive contenant un agent antistatique ionique, et plus spécifiquement, une composition adhésive comprenant un copolymère acrylique, un agent de réticulation, et l'agent antistatique ionique représenté par la formule chimique (1), ladite composition présentant ainsi une excellente performance anti-statique, une durabilité considérablement améliorée, et conservant une excellente force adhésive dans des conditions extrêmes, telles qu'une température élevée et une humidité élevée.
PCT/KR2014/010270 2013-12-27 2014-10-30 Composition adhésive contenant un agent anti-statique ionique Ceased WO2015099279A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2013-0164919 2013-12-27
KR1020130164919A KR102084644B1 (ko) 2013-12-27 2013-12-27 이온성 대전 방지제를 포함하는 점착제 조성물

Publications (1)

Publication Number Publication Date
WO2015099279A1 true WO2015099279A1 (fr) 2015-07-02

Family

ID=53479095

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2014/010270 Ceased WO2015099279A1 (fr) 2013-12-27 2014-10-30 Composition adhésive contenant un agent anti-statique ionique

Country Status (2)

Country Link
KR (1) KR102084644B1 (fr)
WO (1) WO2015099279A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112639553A (zh) * 2018-09-12 2021-04-09 富士胶片株式会社 液晶膜、偏振片、圆偏振片及图像显示装置
CN113278377A (zh) * 2020-01-31 2021-08-20 利诺士尖端材料有限公司 用于显示器的粘结片

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7036880B2 (ja) * 2020-10-07 2022-03-15 住友化学株式会社 粘着剤層付き偏光板及びその製造方法、その製造に用いる活性エネルギー線硬化性高分子組成物並びに液晶表示装置

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20080024215A (ko) * 2005-06-24 2008-03-17 도요 잉키 세이조 가부시끼가이샤 대전방지 아크릴 점착제
KR20080047436A (ko) * 2005-09-20 2008-05-28 소켄 케미칼 앤드 엔지니어링 캄파니, 리미티드 편광판용 점착제 조성물 및 점착제층을 구비한 편광판
KR20080078205A (ko) * 2007-02-22 2008-08-27 동우 화인켐 주식회사 반응성 관능기를 갖는 이온성 액체 화합물을 포함하는대전방지성 점착제 조성물, 이의 제조 방법, 및 이를이용한 편광판
KR20110036720A (ko) * 2004-03-08 2011-04-08 닛토덴코 가부시키가이샤 점착제 조성물, 점착 시트류 및 표면 보호 필름
WO2013058182A1 (fr) * 2011-10-19 2013-04-25 日東電工株式会社 Composition d'adhésif acrylique repositionnable de type dispersion aqueuse et feuille adhésive

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20110096985A (ko) * 2010-02-24 2011-08-31 동우 화인켐 주식회사 점착제 조성물 및 이를 포함하는 편광판
KR20110112263A (ko) 2011-09-02 2011-10-12 임광식 약용식물에서 추출한 성분을 이용한 발모제 피부 투여제 제조방법
KR20130092355A (ko) * 2012-02-09 2013-08-20 동우 화인켐 주식회사 아크릴계 공중합체 및 이를 함유하는 점착제 조성물

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20110036720A (ko) * 2004-03-08 2011-04-08 닛토덴코 가부시키가이샤 점착제 조성물, 점착 시트류 및 표면 보호 필름
KR20080024215A (ko) * 2005-06-24 2008-03-17 도요 잉키 세이조 가부시끼가이샤 대전방지 아크릴 점착제
KR20080047436A (ko) * 2005-09-20 2008-05-28 소켄 케미칼 앤드 엔지니어링 캄파니, 리미티드 편광판용 점착제 조성물 및 점착제층을 구비한 편광판
KR20080078205A (ko) * 2007-02-22 2008-08-27 동우 화인켐 주식회사 반응성 관능기를 갖는 이온성 액체 화합물을 포함하는대전방지성 점착제 조성물, 이의 제조 방법, 및 이를이용한 편광판
WO2013058182A1 (fr) * 2011-10-19 2013-04-25 日東電工株式会社 Composition d'adhésif acrylique repositionnable de type dispersion aqueuse et feuille adhésive

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112639553A (zh) * 2018-09-12 2021-04-09 富士胶片株式会社 液晶膜、偏振片、圆偏振片及图像显示装置
CN112639553B (zh) * 2018-09-12 2022-09-13 富士胶片株式会社 液晶膜、偏振片、圆偏振片及图像显示装置
CN113278377A (zh) * 2020-01-31 2021-08-20 利诺士尖端材料有限公司 用于显示器的粘结片
CN113278377B (zh) * 2020-01-31 2023-02-28 利诺士尖端材料有限公司 用于显示器的粘结片

Also Published As

Publication number Publication date
KR20150076562A (ko) 2015-07-07
KR102084644B1 (ko) 2020-03-04

Similar Documents

Publication Publication Date Title
WO2010120105A2 (fr) Composition adhésive
WO2014204250A1 (fr) Composition d'adhésif
WO2009131393A2 (fr) Composition adhésive et plaques polarisantes et écrans à cristaux liquides utilisant une telle composition
WO2014204253A1 (fr) Composition adhésive
WO2017010765A1 (fr) Composé
WO2018159923A1 (fr) Film de fenêtre, stratifié de film de fenêtre le comprenant et dispositif d'affichage d'image
WO2019093803A1 (fr) Stratifié optique
WO2018159918A1 (fr) Substrat de fenêtre de couverture et dispositif d'affichage d'image comprenant celui-ci
WO2015099279A1 (fr) Composition adhésive contenant un agent anti-statique ionique
WO2019054751A1 (fr) Stratifié optique
WO2015099289A1 (fr) Composition adhésive contenant un agent anti-statique ionique
WO2014038810A1 (fr) Composition adhésive
WO2014027766A1 (fr) Composition adhésive à base d'acryle
WO2015152540A1 (fr) Composition adhésive contenant un agent antistatique ionique
WO2015190748A1 (fr) Composition adhésive et plaque polarisante la comportant
WO2021194071A1 (fr) Composition adhésive pour film protecteur, adhésif la comprenant et feuille adhésive l'utilisant
WO2016006875A1 (fr) Plaque de polarisation ultramince, et dispositif d'affichage à cristaux liquides muni de cette plaque
WO2015190826A1 (fr) Composition adhésive présentant des propriétés antistatiques et plaque de polarisation fabriquée à l'aide de celle-ci
WO2015167132A1 (fr) Composition adhésive antistatique et plaque polarisante fabriquée au moyen de celle-ci
WO2022220498A1 (fr) Composition adhésive sensible à la pression
WO2015099283A1 (fr) Nouveau composé à base de pyridinium, procédé pour le fabriquer, et agent anti-statique et composition adhésive contenant le nouveau composé pyridinium
WO2015156517A1 (fr) Composition adhésive antistatique et plaque de polarisation fabriquée à l'aide de celle-ci
WO2019107951A1 (fr) Stratifié optique
WO2014038815A1 (fr) Composition adhésive
WO2019132455A1 (fr) Composition adhésive et film protecteur l'utilisant

Legal Events

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

Ref document number: 14875160

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 14875160

Country of ref document: EP

Kind code of ref document: A1