WO2014109490A1 - Composition pour agent adhésif - Google Patents

Composition pour agent adhésif Download PDF

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Publication number
WO2014109490A1
WO2014109490A1 PCT/KR2013/011778 KR2013011778W WO2014109490A1 WO 2014109490 A1 WO2014109490 A1 WO 2014109490A1 KR 2013011778 W KR2013011778 W KR 2013011778W WO 2014109490 A1 WO2014109490 A1 WO 2014109490A1
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WO
WIPO (PCT)
Prior art keywords
weight
parts
sensitive adhesive
pressure
meth
Prior art date
Application number
PCT/KR2013/011778
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English (en)
Korean (ko)
Inventor
최한영
유지희
Original Assignee
동우화인켐 주식회사
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.)
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Application filed by 동우화인켐 주식회사 filed Critical 동우화인켐 주식회사
Priority to CN201380069855.3A priority Critical patent/CN104919018B/zh
Priority to JP2015551597A priority patent/JP6236468B2/ja
Publication of WO2014109490A1 publication Critical patent/WO2014109490A1/fr

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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
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
    • C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
    • C08G18/6225—Polymers of esters of acrylic or methacrylic acid
    • C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • 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
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/671—Unsaturated compounds having only one group containing active hydrogen
    • C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • 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
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/062—Copolymers with monomers not covered by C09J133/06
    • C09J133/066—Copolymers with monomers not covered by C09J133/06 containing -OH groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks

Definitions

  • the present invention relates to a pressure-sensitive adhesive composition excellent in antistatic properties and durability and shortened curing period.
  • a liquid crystal display device In general, a liquid crystal display device (LCD) is provided with a liquid crystal cell and a polarizing plate containing a liquid crystal, and an appropriate pressure-sensitive adhesive layer for bonding them is used.
  • the pressure sensitive adhesive is often used an acrylic pressure sensitive adhesive based on an acrylic copolymer having excellent adhesiveness and transparency.
  • peeling the release film from the pressure-sensitive adhesive layer generates static electricity.
  • the generated static electricity affects the alignment of the liquid crystal and causes defects or flows between the liquid crystal cell and the adhesive due to electrostatic attraction. It causes contamination by foreign objects.
  • an ionic antistatic agent is mixed and used in the pressure-sensitive adhesive composition, but a bleed out phenomenon that precipitates due to the surface migration of the ionic antistatic agent may cause lifting, bubbles, and peeling. In particular, this problem may be exacerbated when exposed to a high temperature or high temperature and high humidity environment.
  • a pressure-sensitive adhesive composition containing an acrylic copolymer copolymerized using a monomer containing an alkylene oxide group has been proposed (Korean Patent Publication Nos. 2012-0073093 and 2009-0055576).
  • the acrylic copolymer may have a problem of viscosity increase due to change over time, so that storage after mass production is difficult.
  • the pressure-sensitive adhesive composition acts as an important factor in the curing period that affects productivity, warehouse capacity, inventory management, and emergency shipment response.
  • the present invention relates to a pressure-sensitive adhesive composition that can simultaneously improve the antistatic properties and durability without fear of viscosity increase due to changes over time, and can shorten the curing period without the use of a catalyst for crosslinking.
  • the present invention is an acrylic copolymer containing 4 to 30 parts by weight of (meth) acrylic acid and 0.1 to 2 parts by weight of 4-hydroxybutyl acrylate with respect to 100 parts by weight of the copolymer; Isocyanate crosslinking agents; And it provides a pressure-sensitive adhesive composition containing an ionic antistatic agent
  • the acrylic copolymer is 68 to 95.9 parts by weight of (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms, 4 to 30 parts by weight of acrylic acid, and 4-hydroxybutyl acrylate 0.1 based on 100 parts by weight of the copolymer. To 2 parts by weight.
  • the ionic antistatic agent is a cation salt selected from the group consisting of pyridinium, imidazonium and tetraalkylammonium;
  • An anion selected from the group consisting of PF 6 , BF 4 and I may be an ionic salt.
  • the ionic antistatic agent may be a solid ionic solid at room temperature (25 ° C.).
  • the ionic antistatic agent in the solid phase at room temperature may be 4-methyl-1-octylpyridinium hexafluorophosphate or FC4400 (3M company).
  • the crosslinking agent may contain 0.1 to 3 parts by weight and the ionic antistatic agent to 0.1 to 5 parts by weight based on 100 parts by weight of the acrylic copolymer.
  • the pressure-sensitive adhesive composition may further contain a silane coupling agent.
  • the pressure-sensitive adhesive composition of the present invention can improve the antistatic properties and durability at the same time, there is an advantage that there is no fear of deterioration of physical properties due to changes over time (high temperature or high temperature and high humidity environment changes).
  • the pressure-sensitive adhesive composition of the present invention is significantly shortened in the curing period 6 to 24 hours as compared to the conventional, so that the use of excess additives used to shorten the curing period is usually suppressed, thereby improving problems such as clogging of equipment. There is an advantage to this.
  • the present invention relates to a pressure-sensitive adhesive composition excellent in antistatic properties and durability.
  • the pressure-sensitive adhesive composition of the present invention is an acrylic copolymer containing 4 to 30 parts by weight of (meth) acrylic acid and 0.1 to 2 parts by weight of 4-hydroxybutyl acrylate based on 100 parts by weight of the copolymer; Isocyanate crosslinking agents; And ionic antistatic agents.
  • the (meth) acrylic acid inhibits the bleed out phenomenon, in which the ionic antistatic agent moves to the surface, thereby improving durability, and the 4-hydroxybutyl acrylate crosslinks with the crosslinking agent. It serves as an acid catalyst, the 4-hydroxybutyl acrylate has a high fluidity in the copolymer serves to shorten the curing of the pressure-sensitive adhesive composition by increasing the crosslinking reaction rate.
  • the present invention in order to simultaneously improve the antistatic properties, durability, curing period, etc., by selectively using an acrylic copolymer mixed with (meth) acrylic acid and 4-hydroxybutyl acrylate, and the mixing ratio of the components It is characterized by the optimization.
  • the acrylic copolymer of the present invention is 68 to 95.9 parts by weight of (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms, 4 to 30 parts by weight of (meth) acrylic acid, and 4-hydride, based on 100 parts by weight of the total copolymer. It is preferable to contain 0.1 to 2 parts by weight of oxybutyl acrylate.
  • Examples of the (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms include n-butyl (meth) acrylate, 2-butyl (meth) acrylate, t-butyl (meth) acrylate, and 2-ethylhexyl (meth).
  • the (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms may contain 68 to 95.9 parts by weight, preferably 75 to 90 parts by weight, based on 100 parts by weight of the total copolymer. If it is less than 68 parts by weight, the adhesive force may not be sufficient, and when it exceeds 95.9 parts by weight, cohesion may be lowered.
  • the (meth) acrylic acid may contain 4 to 30 parts by weight, preferably 5 to 20 parts by weight, based on 100 parts by weight of the total copolymer. If the content is less than 4 parts by weight, the effect of suppressing the bleed out phenomenon of the ionic antistatic agent is insignificant and durability may be lowered. When the content exceeds 30 parts by weight, the crude liquid stability of the pressure-sensitive adhesive composition is lowered due to excessive crosslinking reaction. Can be.
  • the 4-hydroxybutyl acrylate is preferably contained 0.1 to 2 parts by weight, preferably 0.5 to 1.5 parts by weight based on 100 parts by weight of the total copolymer. If the content is less than 0.1 parts by weight, the curing period may be shortened, and when it exceeds 2 parts by weight, the crude liquid stability may be lowered due to excessive crosslinking reaction.
  • the acrylic copolymer of the present invention may further contain a polymerizable monomer having a crosslinkable functional group in addition to the (meth) acrylic acid and 4-hydroxybutyl acrylate.
  • the polymerizable monomer having a crosslinkable functional group has a function of imparting cohesive force or adhesive strength by chemical bonding with the following crosslinking agent, and includes a monomer having a hydroxy group, a monomer having a carboxyl group, a monomer having an amide group, and a monomer having a tertiary amine group. Etc. can be mentioned. These can be used individually or in mixture of 2 or more types.
  • Examples of the monomer having a hydroxy group include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 2-hydroxyethylene glycol (meth) acrylate, 2-hydroxypropylene glycol (meth) acrylate, hydroxyalkylene glycol (meth) acrylate having 2-4 carbon atoms of an alkylene group, 4-hydroxybutyl vinyl Ether, 5-hydroxypentyl vinyl ether, 6-hydroxyhexyl vinyl ether, 7-hydroxyheptyl vinyl ether, 8-hydroxyoctyl vinyl ether, 9-hydroxynonyl vinyl ether and 10-hydroxydecyl vinyl ether Among these, 4-hydroxybutyl vinyl ether is preferable.
  • Monovalent acids such as (meth) acrylic acid, crotonic acid, carboxyethyl acrylic 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 to 3 carbon atoms of an alkyl group, among which carboxyethyl acrylic acid is preferred.
  • 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 ) Acrylates and the like.
  • the crosslinkable monomer is preferably contained in an amount of 0.05 to 10 parts by weight, and more preferably 0.1 to 8 parts by weight, based on 100 parts by weight of the total content of the acrylic copolymer. If the content is less than 0.05 parts by weight, the cohesive force of the pressure-sensitive adhesive may be reduced, the durability may be lowered. If the content is more than 10 parts by weight, the adhesive strength is lowered by a high gel fraction may cause problems in durability.
  • polymerizable monomers in addition to the monomers may be further included in an amount of 10 parts by weight or less based on 100 parts by weight of the total monomer used in the preparation of the acrylic copolymer, such as to reduce the adhesion.
  • 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 copolymer has a weight average molecular weight (polystyrene equivalent, Mw) measured by gel permeation chromatography (GPC) of 50,000 to 2 million, preferably 400,000 to 2 million.
  • Mw polystyrene equivalent
  • GPC gel permeation chromatography
  • a crosslinking agent can improve adhesiveness and durability, and can maintain the reliability and shape of an adhesive at high temperature.
  • the present invention is preferably an isocyanate type in consideration of the reactivity of the (meth) acrylic acid and 4-hydroxybutyl acrylate, adhesive strength, durability and light leakage resistance.
  • the isocyanate type is tolylene diisocyanate, xylene diisocyanate, 2,4-diphenylmethane diisocyanate, 4,4-diphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, tetramethyl xylene diisocyanate, naphthalenedi Diisocyanate compounds such as isocyanate; Diisocyanate obtained from 2 moles of an adduct obtained by reacting 3 moles of a diisocyanate compound with 1 mole of a polyhydric alcohol compound such as trimethylolpropane, an isocyanurate obtained by self-condensing 3 moles of the diisocyanate compound, and 3 moles of the diisocyanate compound And polyfunctional isocyanate compounds containing three functional groups such as biuret, triphenylmethanetriisocyanate, and methylenebistriisocyanate, in which the remaining 1 mo
  • Such a crosslinking agent may be contained in an amount of 0.1 to 3 parts by weight, preferably 0.3 to 2 parts by weight, based on 100 parts by weight of the acrylic copolymer. If the content is less than 0.1 part 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 3 parts by weight, problems may occur in reducing residual stress due to excessive crosslinking reaction.
  • the ionic antistatic agent is not particularly limited as long as it is an ionic salt composed of an anion and a cation and can impart ionic conductivity to the pressure-sensitive adhesive.
  • a cation selected from the group consisting of alkali metal salts, ammonium salts, sulfonium salts and phosphonium salts; It may be an ionic salt consisting of an anion selected from the group consisting of fluorine-containing inorganic salts, fluorine-containing organic salts and iodine ions.
  • Such ionic antistatic agents may be alkali metal salts, ionic liquids or ionic solids.
  • alkali metal salts may have insufficient durability due to low compatibility with the pressure-sensitive adhesive, and the ionic liquid may have a high fluidity in the pressure-sensitive adhesive composition, which may lower the antistatic performance due to changes over time. That is, in view of the stability of the durability and antistatic properties over time, an ionic solid which is a solid at room temperature (25?) Is preferable.
  • the ionic solid is a cation salt selected from the group consisting of pyridinium, imidazonium and tetraalkylammonium;
  • An anion selected from the group consisting of PF 6 , BF 4 and I may be at least one selected from ionic salts.
  • Such an ionic antistatic agent may contain 0.1 to 5 parts by weight, preferably 0.5 to 3 parts by weight, based on 100 parts by weight of the acrylic copolymer. If the content is less than 0.1 parts by weight may be insufficient antistatic properties and if it exceeds 10 parts by weight it may be difficult to secure durability.
  • the pressure-sensitive adhesive composition of the present invention may further contain a silane coupling agent.
  • the kind of the silane coupling agent is not particularly limited, and for example, vinylchlorosilane, vinyltrimethoxysilane, vinyltriethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-glycidoxy Propyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, p-styryltrimethoxysilane, 3-metha Krilloxypropyltriethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-acryloxypropyltrimethoxysilane , N-2- (aminoethyl) -3-aminopropylmethyld
  • the pressure-sensitive adhesive composition is a tackifying resin, antioxidant, leveling agent, surface lubricant, dye, pigment, antifoaming agent, in order to adjust the adhesion, cohesion, viscosity, elastic modulus, glass transition temperature, etc. It may further contain additives such as fillers and light stabilizers.
  • Such additives can be appropriately adjusted in a range not impairing the effects of the present invention.
  • the pressure-sensitive adhesive composition of the present invention can be used as a pressure-sensitive adhesive for polarizing plates and a surface protective film for bonding to liquid crystal cells.
  • it can be used as a general commercial adhesive sheet product as well as a protective film, a reflective sheet, a structural adhesive sheet, a photographic adhesive sheet, a lane marking adhesive sheet, an optical adhesive product, an adhesive for electronic parts, and the like.
  • Nitrogen gas was refluxed and the monomer mixture consisting of the composition of Table 1 was added to a 1 L reactor equipped with a cooling device to facilitate temperature control, and then 100 parts by weight of ethyl acetate was added as a solvent. Then, after purging nitrogen gas for 1 hour to remove oxygen, it was maintained at 78 °C. After homogenizing the mixture, 0.03 parts by weight of azobisisobutyronitrile (AIBN) was added as a reaction initiator, and reacted for 8 hours to prepare an acrylic copolymer having a weight average molecular weight of about 730,000.
  • AIBN azobisisobutyronitrile
  • an acrylic copolymer, an ionic antistatic agent, a crosslinking agent, and a silane coupling agent were mixed, and then diluted in ethyl acetate to prepare a pressure-sensitive adhesive composition having a solid content concentration of 15%.
  • the pressure-sensitive adhesive composition prepared above was applied on a release film coated with a silicone release agent to have a thickness of 25 ⁇ m, and dried at 100 ° C. for 1 minute to form an adhesive layer.
  • An adhesive sheet was prepared by laminating another release film thereon.
  • the pressure-sensitive adhesive layer was laminated on an iodine-based polarizing plate having a thickness of 185 ⁇ m by adhesive processing to prepare a polarizing plate with pressure-sensitive adhesive.
  • the prepared polarizing plate was stored for 20 days under conditions of 23 degreeC and 60% RH.
  • the gel fraction was measured by the following method on a daily basis, and the gel fraction was no longer increased, that is, the curing period was measured.
  • the adhesive layer of an adhesive sheet is affixed on the fixed 250 mesh wire mesh (100 mm x 100 mm), and it wraps so that a gel powder may not leak.
  • the wire mesh is immersed in ethyl acetate solution for 3 days.
  • the immersed wire mesh is taken out, washed with a small amount of ethyl acetate solution, dried at 120 ° C. for 24 hours, and weighed.
  • the gel fraction was calculated by the following equation 1 using the measured weight. Curing periods were determined based on the time when the value of the calculated gel fraction was in the range of 70 to 80% and there was no change over time.
  • A is the weight of the wire mesh (g)
  • B is the weight of the wire mesh with the adhesive layer (BA: adhesive weight, g)
  • C is the weight of the dried wire mesh after immersion (CA: weight of the gelled resin, g )being].
  • the prepared pressure-sensitive adhesive polarizing plate was cut to a size of 90 mm x 170 mm, the release film was peeled off, and the specimens were prepared by attaching the optical absorption axis perpendicular to both surfaces of the glass substrate (110 mm x 190 mm x 0.7 mm).
  • the applied pressure was 5kg / cm2 and the clean room work so as not to generate bubbles or foreign matter.
  • the heat resistance characteristics were observed whether bubbles or peeling occurred after 1000 hours at 80 °C temperature, and the heat-resistant characteristics were bubbles or peeling after 1000 hours at 60 °C temperature and 90% RH conditions Was observed. At this time, it was observed after leaving for 24 hours at room temperature immediately before evaluating the state of the specimen.
  • the surface non-constant term was used for the surface resistance measuring instrument (MCP-HT450 / MITSUBISHI CHEMICAL), Probe (URS, UR100), Probe Checker (for URS, UR 100).
  • Examples 1 to 18 containing an acrylic copolymer, an isocyanate-based crosslinking agent, and an ionic antistatic agent containing a certain amount of (meth) acrylic acid and 4-hydroxybutyl acrylate according to the present invention are Comparative Example 1 It was confirmed that the antistatic property, durability (heat and moisture resistance), and storage stability were superior at the same time, and the curing period was greatly reduced to 8 to 36 hours.

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

Abstract

L'invention concerne une composition pour agent adhésif, et plus spécifiquement, une composition pour agent adhésif comprenant : un copolymère acrylique contenant 4-30 parts en poids d'un acide (méta)acrylique et 0,1-2 parts en poids d'un acrylate de 4-hydroxybutyle par rapport au contenu total de 100 parts en poids du copolymère ; un agent de réticulation à base d'isocyanate ; et un agent antistatique ionique, ce qui permet d'améliorer à la fois les propriétés antistatiques et la durabilité, et de ne pas se préoccuper de l'affaiblissement de propriétés physiques à cause de changements environnementaux, tels qu'une élévation de la température, une élévation de la température et de l'humidité et une réduction de la durée de durcissement.
PCT/KR2013/011778 2013-01-08 2013-12-18 Composition pour agent adhésif WO2014109490A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN201380069855.3A CN104919018B (zh) 2013-01-08 2013-12-18 粘合剂组合物
JP2015551597A JP6236468B2 (ja) 2013-01-08 2013-12-18 粘着剤組成物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2013-0002029 2013-01-08
KR1020130002029A KR101314202B1 (ko) 2013-01-08 2013-01-08 점착제 조성물

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WO2014109490A1 true WO2014109490A1 (fr) 2014-07-17

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KR (1) KR101314202B1 (fr)
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Cited By (1)

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KR102094917B1 (ko) * 2018-07-31 2020-03-30 (주)이녹스첨단소재 디스플레이용 점착시트 및 이를 포함하는 디스플레이
WO2020050169A1 (fr) * 2018-09-03 2020-03-12 日東電工株式会社 Composition adhésive, feuille adhésive et corps lié
KR102152295B1 (ko) * 2018-09-04 2020-09-04 (주)이녹스첨단소재 디스플레이용 점착시트 및 이를 포함하는 디스플레이
KR20210098188A (ko) * 2020-01-31 2021-08-10 (주)이녹스첨단소재 디스플레이용 점착 시트
KR102274506B1 (ko) * 2020-03-06 2021-07-07 한국신발피혁연구원 상온 경화형 아크릴계 접착제 조성물

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