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WO2016099149A1 - Composition adhésive - Google Patents

Composition adhésive Download PDF

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Publication number
WO2016099149A1
WO2016099149A1 PCT/KR2015/013801 KR2015013801W WO2016099149A1 WO 2016099149 A1 WO2016099149 A1 WO 2016099149A1 KR 2015013801 W KR2015013801 W KR 2015013801W WO 2016099149 A1 WO2016099149 A1 WO 2016099149A1
Authority
WO
WIPO (PCT)
Prior art keywords
pressure
sensitive adhesive
compound
adhesive composition
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/KR2015/013801
Other languages
English (en)
Korean (ko)
Inventor
김기영
김일진
윤정애
윤성수
김수정
홍상현
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.)
LG Chem Ltd
Original Assignee
LG Chem 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
Priority claimed from KR1020150179554A external-priority patent/KR101815355B1/ko
Application filed by LG Chem Ltd filed Critical LG Chem Ltd
Priority to CN201580054942.0A priority Critical patent/CN106795410B/zh
Priority to US15/513,760 priority patent/US10851269B2/en
Priority to JP2017516066A priority patent/JP6384698B2/ja
Publication of WO2016099149A1 publication Critical patent/WO2016099149A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • 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
    • C09J201/00—Adhesives based on unspecified macromolecular compounds
    • C09J201/02—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C09J201/06—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • 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
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements

Definitions

  • the present application relates to an adhesive composition, an optical laminate, a polarizing plate, and a display device.
  • a so-called adhesive or adhesive is used.
  • a liquid crystal display (LCD) device includes a liquid crystal panel that is a display panel and an optical film, and an adhesive or an adhesive may be used when attaching the optical film to a liquid crystal panel or laminating optical films.
  • an optical film there exist a polarizing film, retardation film, a brightness improving film, etc.
  • the said adhesive or adhesive agent can be used in order to laminate
  • the main required physical properties of the pressure-sensitive adhesive or adhesive for optical films include cohesion, adhesion, reworkability, low light leakage characteristics, and stress relaxation.
  • the adhesive for achieving the said physical property is proposed.
  • the pressure-sensitive adhesive or adhesive for an optical film is basically required to ensure durability at high temperature and / or high humidity conditions, and in some cases it may also be required to ensure an appropriate antistatic performance.
  • adhesiveness with an optical film is calculated
  • the adhesive or the adhesive may come out during cutting of the film, which not only causes contamination of other optical films or display panels, but also the edges when the optical film is attached. There is a problem that sufficient adhesion is not secured at the portion.
  • the adhesive or the like may remain in the adherend when reworking, ie, peeling the optical film once attached again, may cause various problems.
  • Patent Document 1 Republic of Korea Patent No. 1023839
  • Patent Document 2 Republic of Korea Patent No. 1171976
  • Patent Document 3 Republic of Korea Patent No. 1171977
  • One object of the present application is to provide a pressure-sensitive adhesive composition capable of forming a pressure-sensitive adhesive optical member that is excellent in durability at high temperature or high humidity conditions, and has excellent adhesiveness with an optical film and is excellent in cutting properties and reworkability. .
  • the present application can also effectively suppress warpage even when applied to thin substrates such as glass substrates of very thin thickness, minimize the time required for stabilization of physical properties, and prevent the deterioration of the secured physical properties over time. It is also an object of the present invention to provide an adhesive composition capable of forming an adhesive.
  • Another object of the present application is to provide a pressure-sensitive adhesive optical member, an optical laminate, and a display device formed using the pressure-sensitive adhesive composition as described above.
  • Exemplary pressure-sensitive adhesive composition may include (A) block copolymer as one component.
  • block copolymer may refer to a copolymer comprising blocks of different polymerized monomers.
  • the block copolymer may include a first block having a glass transition temperature of 50 ° C. or more and a second block having a glass transition temperature of ⁇ 10 ° C. or less.
  • the "glass transition temperature of a predetermined block" of a block copolymer may mean a glass transition temperature calculated by monomers forming the block.
  • the glass transition temperature of the first block may be 60 ° C. or more, 65 ° C. or more, 70 ° C. or more, 75 ° C. or more, 80 ° C. or more, 85 ° C. or more, 90 ° C. or more, or 95 ° C. or more.
  • the upper limit of the glass transition temperature of the first block is not particularly limited, but for example, the glass transition temperature may be about 150 ° C. or less, 140 ° C. or less, 130 ° C. or less or 120 ° C. or less.
  • the glass transition temperature of the second block may be -20 ° C or less, -30 ° C or less, -35 ° C or less, or -40 ° C or less.
  • the lower limit of the glass transition temperature of the second block is not particularly limited, but for example, the glass transition temperature may be about -80 ° C or higher, -70 ° C or higher, -60 ° C or higher, or about -55 ° C or higher. .
  • the block copolymer including at least two kinds of the blocks may form, for example, a fine phase separation structure in the pressure-sensitive adhesive.
  • a block copolymer can form an adhesive which exhibits appropriate cohesive force and stress relaxation property according to temperature change and maintains excellent physical properties required for optical films, such as durability reliability, light leakage preventing property and reworkability.
  • the first block may have, for example, a number average molecular weight (Mn) in a range of 2,500 to 150,000.
  • the number average molecular weight of the first block means, for example, the number average molecular weight of a polymer prepared by polymerizing only the monomers forming the first block, or the block copolymer is prepared by the first block acting as a macro initiator. If so, it may mean the number average molecular weight of the macroinitiator.
  • the number average molecular weight referred to in the present specification can be measured by, for example, the method shown in the Examples by using GPC (Gel Permeation Chromatograph).
  • the number average molecular weight of the first block may be about 100,000 or less, about 90,000 or less, about 80,000 or less, about 70,000 or less, about 60,000 or less, about 50,000 or less, about 40,000 or less, or about 35,000 or less. Further, in another example, the number average molecular weight of the first block may be about 5,000 or more, about 10,000 or more, about 15,000 or more, about 20,000 or more, or about 25,000 or more.
  • the block copolymer may have a number average molecular weight in the range of 50,000 to 300,000.
  • the number average molecular weight of the block copolymer may in another example be at least 90,000, at least about 100,000, at least about 150,000 or at least about 200,000.
  • the number average molecular weight may be about 250,000 or less in another example.
  • the block copolymer has a molecular weight distribution (PDI; Mw / Mn), that is, a ratio (Mw / Mn) of weight average molecular weight (Mw) and number average molecular weight (Mn) in the range of 1.0 to 3.5 or in the range of about 1.4 to 2.0. There may be.
  • the molecular weight characteristics can be adjusted as described above to provide a pressure-sensitive adhesive composition or pressure-sensitive adhesive.
  • the block copolymer may be a crosslinkable copolymer having a crosslinkable functional group.
  • a crosslinkable functional group a hydroxyl group, a carboxyl group, an isocyanate group, a glycidyl group, etc. can be illustrated, For example, a hydroxyl group can be used.
  • the functional group When including a crosslinkable functional group, the functional group may be included in, for example, either one of the first or second blocks, or both the first and second blocks.
  • the crosslinkable functional group may be included in the second block having a low glass transition temperature.
  • the first block may not include a crosslinkable functional group, and only the second block may include a crosslinkable functional group.
  • the cross-linkable functional group When the cross-linkable functional group is included in the second block, it exhibits an appropriate cohesion force and stress relaxation property according to the temperature change, thereby forming an adhesive that maintains excellent physical properties required for optical films such as durability, light leakage prevention properties, and reworkability. can do.
  • the type of monomers forming the first block and the second block in the block copolymer is not particularly limited as long as the glass transition temperature is secured by the combination of the monomers.
  • the first block may comprise polymerized units derived from (meth) acrylic acid ester monomers.
  • that the monomer is included in the polymer or the block as a polymerized unit may mean that the monomer forms a backbone, for example, a main chain or a side chain of the polymer or block through a polymerization reaction.
  • an alkyl (meth) acrylate can be used, for example.
  • alkyl having an alkyl group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms ( Meta) acrylates can be used.
  • Examples of such monomers include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, t-butyl (meth ) Acrylate, sec-butyl (meth) acrylate, pentyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, 2-ethylbutyl (meth) acrylate, n-octyl (meth) acrylate, iso Bornyl (meth) acrylate, isooctyl (meth) acrylate, isononyl (meth) acrylate, and lauryl (meth) acrylate, and the like, and the glass transition temperature of one or more of the above is ensured.
  • the monomer forming the first block in consideration of the ease of glass transition temperature control and the like is a methacrylic acid ester monomer, for example, 1 to 20 carbon atoms, 1 to 16 carbon atoms Alkyl methacrylate having an alkyl group having 1 to 12, 1 to 8 carbon atoms or 1 to 4 carbon atoms can be used.
  • the second block of the block copolymer comprises, for example, polymerized units derived from 90 to 99.9 parts by weight of the (meth) acrylic acid ester monomer and 0.1 to 10 parts by weight of the copolymerizable monomer having a crosslinkable functional group. can do.
  • the unit weight part may mean a ratio of weights between components.
  • the second block may include polymerized units derived from 90 to 99.9 parts by weight of the (meth) acrylic acid ester monomer and 0.1 to 10 parts by weight of the copolymerizable monomer having a crosslinkable functional group.
  • the ratio (A: B) based on the weight of the (meth) acrylic acid ester monomer (A) and the copolymerizable monomer (B) having a crosslinkable functional group forming the polymerized unit of the second block is from 90 to 99.9: It may mean the case of 0.1 to 10.
  • the (meth) acrylic acid ester monomer forming the second block it is possible to secure the glass transition temperature in the above-described range through copolymerization with the copolymerizable monomer among the monomers that may be included in the first block.
  • kinds of monomers can be selected and used.
  • the (meth) acrylic acid ester monomer forming the second block in consideration of the ease of glass transition temperature control, etc. is an acrylic acid ester monomer, for example, 1 to 20 carbon atoms among the monomers described above.
  • Alkyl acrylates having an alkyl group having 1 to 16, 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms can be used.
  • copolymerizable monomer which has a crosslinkable functional group for example, it has a site
  • Copolymerizable monomers having such crosslinkable functional groups are variously known in the field of pressure-sensitive adhesives, and all of these monomers may be used in the polymer.
  • a copolymerizable monomer which has a hydroxyl group 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxy Hydroxyalkyl (meth) acrylates such as hexyl (meth) acrylate or 8-hydroxyoctyl (meth) acrylate, or 2-hydroxyethylene glycol (meth) acrylate or 2-hydroxypropylene glycol (meth) Hydroxyalkylene glycol (meth) acrylates such as acrylate may be used, but is not limited thereto.
  • hydroxyalkyl acrylate or hydroxyalkylene glycol acrylate may be used among the above monomers. no.
  • the first block and / or the second block may further comprise other optional comonomers, if necessary, for example, for the control of the glass transition temperature, and the monomers may be included as polymerized units. have.
  • said comonomer it is (meth) acrylonitrile, (meth) acrylamide, N-methyl (meth) acrylamide, N-butoxy methyl (meth) acrylamide, N-vinyl pyrrolidone, or N-vinyl capro Nitrogen-containing monomers such as lactams and the like; Alkoxy alkylene glycol (meth) acrylic acid ester, alkoxy dialkylene glycol (meth) acrylic acid ester, alkoxy trialkylene glycol (meth) acrylic acid ester, alkoxy tetraalkylene glycol (meth) acrylic acid ester, alkoxy polyethylene glycol (meth) acrylic acid Esters, phenoxy alkylene glycol (meth) acrylic acid esters, phenoxy dialkylene glycol
  • Such comonomers may be included in the polymer by selecting one or more kinds thereof as necessary.
  • Such comonomers may be included in the block copolymer, for example, in a ratio of 20 parts by weight or less, or 0.1 to 15 parts by weight, relative to the weight of other monomers in each block.
  • the block copolymer may include, for example, 5 parts by weight to 50 parts by weight of the first block and 50 parts by weight to 95 parts by weight of the second block. By adjusting the ratio of the weight between the first block and the second block as described above, it is possible to provide the pressure-sensitive adhesive composition and pressure-sensitive adhesive of excellent physical properties.
  • the block copolymer may include 5 parts by weight to 45 parts by weight of the first block and 55 parts by weight to 95 parts by weight of the second block, or 5 parts by weight to 45 parts by weight of the first block and 60 parts by weight of the second block. 95 parts by weight may be included.
  • the block copolymer may comprise at least about 50%, at least about 55%, at least about 60%, at least about 65%, at least about 70%, at least about 75% or at least about 80% of the second block by weight. It may include more.
  • the first block may be included in a proportion of about 99% or less and about 95% or more by weight.
  • the second block may be included in a ratio of about 5 to 100 parts by weight with respect to 100 parts by weight of the first block.
  • the second block is about 90 parts by weight, about 80 parts by weight, about 70 parts by weight, about 60 parts by weight, about 50 parts by weight, about 40 parts by weight or less, about 100 parts by weight of the first block. 30 parts by weight or less, about 20 parts by weight or less, or about 15 parts by weight or less.
  • the block copolymer may be a diblock copolymer including the first and second blocks, that is, a block copolymer including only two blocks of the first and second blocks. .
  • a diblock copolymer By using a diblock copolymer, the durability, stress relaxation property, and reworkability of an adhesive can be maintained more excellently.
  • the method for producing the block copolymer is not particularly limited and can be prepared in a conventional manner.
  • the block polymer may be polymerized by, for example, a Living Radical Polymerization (LRP) method, for example, an organic rare earth metal complex may be used as a polymerization initiator, or an organic alkali metal compound may be used as a polymerization initiator.
  • LRP Living Radical Polymerization
  • an inorganic acid salt such as a salt
  • the pressure-sensitive adhesive composition may further include a crosslinking agent (B) capable of crosslinking the block copolymer as an additional component.
  • a crosslinking agent the crosslinking agent which has at least two functional groups which can react with the crosslinkable functional group contained in the said block copolymer can be used.
  • an isocyanate crosslinking agent an epoxy crosslinking agent, an aziridine crosslinking agent or a metal chelate crosslinking agent can be exemplified.
  • a polyfunctional isocyanate compound can be used as a crosslinking agent normally.
  • the polyfunctional isocyanate compound includes two or more isocyanate groups, for example, 2 to 10, 2 to 9, 2 to 8, 2 to 7, 2 to 6, 2 It may mean a compound containing about 5 to 5 or about 2 to 4.
  • polyfunctional isocyanate compound which can be used as the crosslinking agent for example, tolylene diisocyanate, xylene diisocyanate, diphenylmethane diisocyanate, hexamethylene diisocyanate, isoborone diisocyanate, tetramethylxylene diisocyanate or naphthalene diisocyanate Diisocyanate compounds such as; Or a compound obtained by reacting one or more of the diisocyanate compounds with a polyol, but is not limited thereto.
  • a polyol which can be used above trimethylol propane etc. can be illustrated.
  • crosslinking agents may be used in the pressure-sensitive adhesive composition, but a crosslinking agent that may be used is not limited thereto.
  • the multifunctional crosslinking agent may be included in the pressure-sensitive adhesive composition in an amount of 0.01 to 10 parts by weight based on 100 parts by weight of the block copolymer.
  • the crosslinking agent may be included in a ratio of 0.03 parts by weight or more or 0.05 parts by weight or more.
  • the crosslinking agent may be included in another proportion of 8 parts by weight or less, 6 parts by weight or less, 4 parts by weight or less, 2 parts by weight or less, or 1 part by weight or less. It is possible to maintain excellent gel fraction, cohesion, adhesion and durability of the pressure-sensitive adhesive in the range as described above.
  • the pressure-sensitive adhesive composition may further include (C) a polyfunctional epoxy compound or a polyfunctional aziridine compound as an additional component.
  • a polyfunctional epoxy compound refers to two or more epoxy groups, for example, 2 to 10, 2 to 9, 2 to 8, 2 to 7, 2 to 6, 2 It can mean a compound containing from about 5 to about 5 or 2 to 4, the term multifunctional aziridine compound is at least two, for example, 2 to 10, 2 to 9, It may mean a compound containing 2 to 8, 2 to 7, 2 to 6, 2 to 5 or about 2 to 4.
  • epoxy group in the present application may refer to a cyclic ether having three ring constituent atoms or a monovalent moiety derived from a compound containing the cyclic ether, unless otherwise specified.
  • examples of the epoxy group include glycidyl group, epoxyalkyl group, glycidoxyalkyl group or alicyclic epoxy group.
  • the alicyclic epoxy group may mean a monovalent moiety derived from a compound containing an aliphatic hydrocarbon ring structure, wherein the two carbon atoms forming the aliphatic hydrocarbon ring also include an epoxy group.
  • an alicyclic epoxy group having 6 to 12 carbon atoms can be exemplified, for example, a 3,4-epoxycyclohexylethyl group or the like can be exemplified.
  • the term aziridine group is a heterocycle-type functional group including three ring-constituting atoms, and may mean a functional group including one amine group and two methylene bridges or a derivative derived from the functional group.
  • (C) component can contribute especially to improving adhesiveness between an adhesive and an optical film.
  • the pressure-sensitive adhesive is formed on an optical film into which a functional group such as a hydroxyl group or a carboxyl group is introduced, as described below
  • the optical film is formed by various chemical or physical interactions of the component (C) with the functional group on the optical film.
  • the adhesion between the adhesive and the adhesive may increase.
  • polyfunctional epoxy compound (C) examples include ethylene glycol diglycidyl ether, triglycidyl ether, trimethylolpropane triglycidyl ether, N, N, N ', N'-tetraglycidyl ethylenediamine and glycerin
  • diglycidyl ether examples include ethylene glycol diglycidyl ether, triglycidyl ether, trimethylolpropane triglycidyl ether, N, N, N ', N'-tetraglycidyl ethylenediamine and glycerin
  • diglycidyl ether examples include ethylene glycol diglycidyl ether, triglycidyl ether, trimethylolpropane triglycidyl ether, N, N, N ', N'-tetraglycidyl ethylenediamine and glycerin
  • the polyfunctional aziridine compound N, N'-toluene
  • Component (C) may be included in the pressure-sensitive adhesive composition in a ratio of 0.1 to 10 parts by weight based on 100 parts by weight of the block copolymer (A).
  • Component (C) may, in another example, be included at least 0.3 parts by weight relative to 100 parts by weight of component (A).
  • component (C) may be included in an amount of 8 parts by weight, 6 parts by weight or 4 parts by weight or less based on 100 parts by weight of component (A). Within such a range, while ensuring proper adhesion with the optical film, other physical properties required for the pressure-sensitive adhesive can also be stably maintained.
  • the pressure-sensitive adhesive composition may further include one or more compounds selected from the group consisting of (D) an imidazole compound, a phosphine compound, an amine compound, a phenol compound, and an acid anhydride. Such a compound may promote physical or chemical interaction of the pressure-sensitive adhesive composition or the pressure-sensitive adhesive on the optical film surface to further enhance the adhesion to the surface and shorten the time required for securing the adhesion.
  • an imidazole compound a phosphine compound, an amine compound, a phenol compound, etc. which can be applied as a component (D)
  • the following compounds can be used, for example.
  • the compound represented by following formula (1) can be used as an imidazole compound.
  • R 1 to R 4 in Formula 1 are each independently hydrogen, an alkyl group, or an aryl group.
  • an alkyl group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms may be exemplified, and the alkyl group may be linear, branched or cyclic. It may be optionally substituted with one or more substituents.
  • an aryl group having 6 to 30 carbon atoms, 6 to 24 carbon atoms, 6 to 18 carbon atoms, or 6 to 12 carbon atoms may be exemplified, and such an aryl group may be optionally substituted with one or more substituents.
  • R1 is hydrogen or an alkyl group
  • R2 to R4 are each independently hydrogen, an alkyl group or an aryl group
  • at least R4 and / or R3 is an alkyl group or an aryl group
  • Such compounds include 2-methylimidazole, 2-ethylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-ethyl-4-methylimidazole, and 2-phenyl. Midazole or 2-phenyl-4-methylimidazole and the like can be exemplified, but is not limited thereto.
  • the compound represented by following formula (2) can be used, for example.
  • R 5 to R 7 in Formula 2 are each independently hydrogen, an alkyl group, or an aryl group.
  • Examples of the compound represented by the formula (2) include triphenylphosphine, tributylphosphine, tri (p-methphenyl) phosphine or tri (nonylphenyl) phosphine, and the like.
  • the compound represented by following formula (3) or (4) can be used, for example.
  • L1 and L2 are alkylene groups.
  • R8 to R10 are each independently hydrogen, an alkyl group, an aryl group, an arylalkyl group, or a hydroxyalkyl group.
  • alkylene group an alkylene group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms may be exemplified. It may be chain or cyclic, and may be optionally substituted with one or more substituents.
  • 1,8-diazabicyclo [5.6.0] unde-7-ene, benzyl dimethylamine or triethanolamine and the like can be exemplified, but is not limited thereto.
  • phenolic compound for example, a compound represented by the following formula (5) may be used.
  • R11 to R15 are each independently hydrogen, an alkyl group, an aminoalkyl group, an alkylaminoalkyl group or a dialkylaminoalkyl group.
  • alkyl group or aryl group in the formula (5) is the same as in the case of formula (1).
  • R11 to R15 are each independently hydrogen, an alkyl group, an aminoalkyl group, an alkylaminoalkyl group or a dialkylaminoalkyl group, and at least one of R11 to R15 is an aminoalkyl group, an alkylaminoalkyl group or a di
  • R11 to R15 are each independently hydrogen, an alkyl group, an aminoalkyl group, an alkylaminoalkyl group or a dialkylaminoalkyl group, and at least one of R11 to R15 is an aminoalkyl group, an alkylaminoalkyl group or a di
  • Compounds that are alkylaminoalkyl groups can be exemplified.
  • Examples of such a compound include, but are not limited to, 2- (dimethylaminomethyl) phenol.
  • maleic anhydride or tetrahydrophthalic anhydride may be used as the acid anhydride-based compound, but is not limited thereto.
  • Component (D) may be included in the pressure-sensitive adhesive composition in a ratio of 0.001 to 5 parts by weight based on 100 parts by weight of the block copolymer (A).
  • Component (D) may be included in another example at least 0.005 parts by weight relative to 100 parts by weight of component (A), in another example at most 4 parts by weight, at most 3 parts by weight, at most 2 parts by weight or It may be included in a ratio of 1 part by weight or less. Within this range, the desired adhesion and the like can be secured, and other physical properties can be maintained stably.
  • the pressure-sensitive adhesive composition may include a tin compound as an additional component.
  • a tin-based compound may allow the crosslinked pressure-sensitive adhesive to exhibit excellent interfacial adhesion with the optical film while the pressure-sensitive adhesive effectively crosslinks through interaction with the component (D).
  • an organic tin compound may be used, for example, dialkyl tin oxide, a fatty acid salt of dialkyl tin or a fatty acid salt of stannous tin, and the like, and specifically, a dialkyl tin oxide or Dialkyl tin dilaurate and the like can be used.
  • alkyl may be linear, branched or cyclic alkyl having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms.
  • the tin-based compound may be included in the pressure-sensitive adhesive composition in a ratio of 0.001 to 5 parts by weight based on 100 parts by weight of the (A) block copolymer.
  • the tin compound may, in another example, be included in an amount of at least 0.005 parts by weight based on 100 parts by weight of component (A), and in another example, 4 parts by weight, 3 parts by weight, 2 parts by weight or less, based on 100 parts by weight of component (A) or It may be included in a ratio of 1 part by weight or less. Within this range, the desired crosslinking degree, adhesion, etc. can be secured, and other physical properties can be stably maintained.
  • the pressure-sensitive adhesive composition may include an ionic compound as an additional component.
  • an ionic compound an inorganic salt or an ionic liquid can be used. From the viewpoint of securing the above-described interfacial adhesion or the like and causing no curing retardation phenomenon, it was confirmed that the ionic liquid can bring a beneficial effect over the inorganic salt.
  • the term ionic liquid may mean an ionic compound present in a liquid state at room temperature.
  • the room temperature is a natural temperature that is not heated or reduced, and may mean a temperature of about 10 ° C to 30 ° C, about 15 ° C to 30 ° C, about 20 ° C to 30 ° C, about 25 ° C, or about 23 ° C. Can be.
  • the ionic compound may be included in the pressure-sensitive adhesive composition so that the pressure-sensitive adhesive may have appropriate antistatic properties.
  • the salt containing an alkali metal cation or alkaline earth metal cation can be used as said inorganic salt.
  • Such cations include lithium ions (Li + ), sodium ions (Na + ), potassium ions (K + ), rubidium ions (Rb + ), cesium ions (Cs + ), beryllium ions (Be 2 + ), magnesium ions (Mg 2 +), calcium ion (Ca 2+), strontium ion (Sr 2 +) and barium ion (Ba + 2) there is a iljong or different than, such as may be illustrated, for example, a lithium ion, a sodium ion Lithium ions may be used in consideration of one kind or two or more kinds of potassium ions, magnesium ions, calcium ions and barium ions, or ion stability and mobility.
  • the compound which has onium salt containing nitrogen, sulfur, or phosphorus as a cation component can be used as said ionic liquid.
  • Such cations include N-ethyl-N, N-dimethyl-N-propylammonium, N, N, N-trimethyl-N-propylammonium, N-methyl-N, N, N-tributylammonium and N-ethyl -N, N, N-tributylammonium, N-methyl-N, N, N-trihexylammonium, N-ethyl-N, N, N-trihexylammonium, N-methyl-N, N, N-tri Quaternary ammonium compounds such as octyl ammonium or N-ethyl-N, N, N-trioctyl ammonium, phosphonium or derivatives thereof, such as tetraalkyl phosphonium, pyridinium or derivatives thereof, t
  • a compound containing a cation in which the alkyl group included in the cation is substituted with an alkoxy group, a hydroxy group, an alkynyl group, an epoxy group, or the like among the aforementioned cations may be used.
  • a cation represented by Chemical Formula A may be applied as the cation of the ionic liquid.
  • R 1 to R 4 in formula (A) each independently represent hydrogen, alkyl, alkoxy, alkenyl or alkynyl.
  • Alkyl or alkoxy in formula (A) may be alkyl or alkoxy having 1 to 20 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms.
  • the alkyl or alkoxy may be linear, branched or cyclic alkyl or alkoxy, and may be optionally substituted with one or more substituents.
  • Alkenyl or alkynyl in Formula A may be alkenyl or alkynyl having 2 to 20 carbon atoms, 2 to 12 carbon atoms, 2 to 8 carbon atoms, or 2 to 4 carbon atoms.
  • the alkenyl or alkynyl may be linear, branched or cyclic alkenyl or alkynyl, and may be optionally substituted with one or more substituents.
  • substituents include hydroxy, alkyl, alkoxy, alkenyl, alkynyl, cyano, thiol, amino, aryl or Heteroaryl, and the like, but is not limited thereto.
  • R 1 to R 4 of Formula A may each independently be alkyl, for example, straight or branched alkyl of 1 to 12 carbon atoms.
  • R 1 to R 4 in Formula (A) each independently represent linear or branched alkyl having 1 to 12 carbon atoms, but R 1 to R 4 may not correspond to alkyl having the same carbon number at the same time. In such a case, the case where R1 to R4 are all alkyl groups having the same carbon number is excluded in the range of the formula (A). When R1 to R4 are all alkyl having the same carbon number, there is a high probability that the compound exists in the solid phase at room temperature.
  • R1 may be alkyl having 1 to 3 carbon atoms
  • R2 to R4 may be each independently alkyl having 4 to 20 carbon atoms, 4 to 15 carbon atoms, or 4 to 10 carbon atoms.
  • anion contained in the ionic compound is PF 6 -, AsF -, NO 2 -, fluoride (F -), chloride (Cl -), bromide (Br -), iodide (I -), perchlorate (ClO 4 -), hydroxide (OH -), carbonate (CO 3 2 -), nitrate (NO 3 -), trifluoromethane sulfonate (CF 3 SO 3 -), sulfonate (SO 4 -), hexafluorophosphate (PF 6 -), methyl benzene sulfonate (CH 3 (C 6 H 4 ) SO 3 -), p- toluenesulfonate (CH 3 C 6 H 4 SO 3 -), tetraborate (B 4 O 7 2- ), carboxybenzenesulfonate (COOH (C 6 H 4 ) SO 3 ⁇ ), trichloromethanesulfonate (CF
  • an anion represented by the following formula (B) or bisfluorosulfonylimide may be used as the anion.
  • X is a nitrogen atom or carbon atom
  • Y is a carbon atom or sulfur atom
  • R f is a perfluoroalkyl group
  • m is 1 or 2
  • n is 2 or 3.
  • Anions or bis (fluorosulfonyl) imides of formula B exhibit high electronegativity due to perfluoroalkyl groups (R f ) or fluorine groups, and also include unique resonance structures, forming weak bonds with cations At the same time, it has hydrophobicity. Therefore, while an ionic compound shows the outstanding compatibility with other components of compositions, such as a polymer, it can provide high antistatic property even with a small amount.
  • R f of Formula B may be a perfluoroalkyl group having 1 to 20 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms, in which case the perfluoroalkyl group is linear, branched, or cyclic. It may have a mold structure.
  • the anion of the formula (B) may be a sulfonyl metide, sulfonylimide, carbonyl metide, or carbonyl imide anion, and specifically, tristrifluoromethanesulfonylmethide and bistrifluoromethanesulphate Ponylimide, bisperfluorobutanesulfonylimide, bispentafluoroethanesulfonylimide, tristrifluoromethanecarbonylmide, bisperfluorobutanecarbonylimide or bispentafluoroethanecarbonyl It may be a kind of imide or the like or a mixture of two or more thereof.
  • the ionic compound is present in the pressure-sensitive adhesive composition in a ratio of 0.01 to 15 parts by weight, 0.01 to 10 parts by weight, 0.01 to 5 parts by weight, 0.1 to 5 parts by weight or 0.5 to 5 parts by weight with respect to 100 parts by weight of the block copolymer (A).
  • the pressure-sensitive adhesive composition may further include a silane coupling agent.
  • a silane coupling agent the silane coupling agent which has a beta-cyano group or an acetoacetyl group can be used, for example.
  • Such a silane coupling agent may, for example, allow the pressure-sensitive adhesive formed by a low molecular weight copolymer to exhibit excellent adhesion and adhesion stability, and also to maintain excellent durability and the like in heat and moisture resistant conditions. have.
  • silane coupling agent which has a beta-cyano group or an acetoacetyl group
  • the compound represented by following formula (5) or 6 can be used, for example.
  • R1 is a beta-cyanoacetyl group or a beta-cyanoacetylalkyl group
  • R3 is an acetoacetyl group or an acetoacetylalkyl group
  • R2 is an alkoxy group
  • n is a number from 1 to 3.
  • the alkyl group may be an alkyl group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms, and the alkyl group may be linear, branched or cyclic. have.
  • the alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms, and the alkoxy group may be linear, branched or cyclic. have.
  • N in Formula 5 or 6 may be, for example, 1 to 3, 1 to 2 or 1.
  • acetoacetylpropyl trimethoxy silane for example, acetoacetylpropyl trimethoxy silane, acetoacetylpropyl triethoxy silane, beta-cyanoacetylpropyl trimethoxy silane or beta-cyanoacetylpropyl triethoxy silane Etc. may be illustrated, but is not limited thereto.
  • the silane coupling agent may be included in an amount of 0.01 parts by weight to 5 parts by weight or 0.01 parts by weight to 1 parts by weight with respect to 100 parts by weight of the (A) block copolymer. Can be.
  • An adhesive composition may further contain a tackifier as needed.
  • a tackifier for example, a hydrocarbon resin or a hydrogenated substance thereof, a rosin resin or a hydrogenated substance thereof, a rosin ester resin or a hydrogenated substance thereof, a terpene resin or a hydrogenated substance thereof, a terpene phenol resin or a hydrogenated substance thereof, a polymerized rosin resin or One kind or a mixture of two or more kinds such as a polymerized rosin ester resin may be used, but is not limited thereto.
  • the tackifier may be included in the pressure-sensitive adhesive composition in an amount of 100 parts by weight or less based on 100 parts by weight of the block copolymer.
  • the pressure-sensitive adhesive composition may further further comprise one or more additives selected from the group consisting of epoxy resins, curing agents, ultraviolet stabilizers, antioxidants, colorants, reinforcing agents, fillers, defoamers, surfactants and plasticizers, if desired.
  • the pressure-sensitive adhesive composition may have a gel fraction of 80% by weight or less after implementing the crosslinked structure.
  • the gel fraction can be calculated by the following general formula (1).
  • A is the mass of the pressure-sensitive adhesive composition embodying a crosslinked structure
  • B is 72 hours in ethyl acetate at room temperature in a state that the pressure-sensitive adhesive composition of mass A in a mesh of 200 mesh size
  • the dry mass of the insoluble fraction collected after deposition is shown.
  • the lower limit of the gel fraction of the pressure-sensitive adhesive composition is not particularly limited, and may be, for example, 0 wt%.
  • the gel fraction of 0 wt% does not mean that the crosslinking did not proceed at all in the pressure-sensitive adhesive composition.
  • the pressure-sensitive adhesive composition having a gel fraction of 0% by weight the pressure-sensitive adhesive composition or crosslinking did not proceed at all, but the degree of crosslinking was low, so that the gel could not be maintained in the 200-mesh network. Leakage may also be included.
  • the pressure-sensitive adhesive composition may be a pressure-sensitive adhesive composition for an optical film.
  • the pressure-sensitive adhesive composition for an optical film may, for example, laminate optical films such as a polarizing film, a retardation film, an anti-glare film, a wide viewing angle compensation film, or a brightness enhancement film to each other, or the optical film or a laminate thereof such as a liquid crystal panel or the like. It can be used for attachment to adherends.
  • the pressure-sensitive adhesive composition as a pressure-sensitive adhesive composition for a polarizing plate, may be an pressure-sensitive adhesive composition used for attaching the polarizing film to the liquid crystal panel.
  • the present application also relates to an adhesive optical member, for example, an adhesive polarizing plate.
  • An exemplary optical member includes an optical film; And it may include a pressure-sensitive adhesive layer formed on one side or both sides of the optical film.
  • the pressure-sensitive adhesive layer may be, for example, a pressure-sensitive adhesive layer for attaching the optical film to a liquid crystal panel or the like of another LCD device or another optical film.
  • the pressure-sensitive adhesive layer may include the pressure-sensitive adhesive composition of the present application described above.
  • the pressure-sensitive adhesive composition may be included in the pressure-sensitive adhesive layer in a state of implementing a crosslinked structure.
  • a polarizer, a polarizing plate, a retardation film, a brightness enhancing film, or the like, or a laminate in which two or more kinds are stacked in the above may be exemplified.
  • the term polarizer and the polarizing plate is a concept that is distinguished from each other, for example, the polarizer means a layer itself exhibiting a polarizing function such as a polyvinyl alcohol film described later, and the polarizing plate includes such a polarizer together with other elements. It may mean a laminate.
  • a functional group capable of interacting with the pressure-sensitive adhesive layer as a functional group capable of interacting with the pressure-sensitive adhesive layer, such as a hydroxyl group, an amino group, a carboxyl group, a urethane bond or a urea bond, etc. This may be introduced.
  • Such functional groups may enhance the adhesion between the optical film and the pressure-sensitive adhesive layer through physical or chemical interactions with the polyfunctional isocyanate compound, the polyfunctional epoxy compound, or the polyfunctional aziridine compound present in the pressure-sensitive adhesive layer.
  • the functional group may be introduced by employing an optical film formed of a polymer having such a functional group in a molecule, or by an easy adhesion treatment such as corona discharge or plasma treatment.
  • an easy adhesion treatment such as corona discharge or plasma treatment.
  • the surface of the optical film into which the above functional groups are introduced or a portion of the optical film subjected to the corona discharge or the plasma treatment may be referred to as an easy adhesion layer.
  • corona or plasma treatment conditions performed to introduce such functional groups are not particularly limited, and methods known in the art may be appropriately employed and applied.
  • the present application also relates to a pressure-sensitive adhesive polarizing plate.
  • the polarizing plate may have, for example, a structure in which the optical film is a polarizer in the adhesive optical member.
  • the kind of polarizer contained in a polarizing plate is not specifically limited,
  • the polarizer is a functional film capable of extracting only light vibrating in one direction from incident light while vibrating in various directions.
  • a polarizer may be, for example, a form in which a dichroic dye is adsorbed in a polyvinyl alcohol-based resin film.
  • Polyvinyl alcohol-type resin which comprises a polarizer can be obtained by gelatinizing polyvinylacetate-type resin, for example.
  • the polyvinylacetate resin which can be used may include not only a homopolymer of vinyl acetate but also a copolymer of vinyl acetate and other monomers copolymerizable with the above.
  • Examples of the monomer copolymerizable with vinyl acetate include unsaturated carboxylic acids, olefins, vinyl ethers, unsaturated sulfonic acids, and a mixture of one or two or more kinds of acrylamides having an ammonium group, but are not limited thereto. no.
  • the degree of gelation of the polyvinyl alcohol-based resin may be about 85 mol% to 100 mol% or 98 mol% or more.
  • the polyvinyl alcohol-based resin may be further modified, for example, polyvinyl formal or polyvinyl acetal modified with aldehydes may be used.
  • the degree of polymerization of the polyvinyl alcohol-based resin may be about 1,000 to 10,000 or about 1,500 to 5,000.
  • the polarizer is a step of stretching (ex. Uniaxial stretching) the polyvinyl alcohol resin film as described above, a step of dyeing the polyvinyl alcohol resin film with a dichroic dye, adsorbing the dichroic dye, and a dichroic dye adsorbed.
  • the polyvinyl alcohol-based resin film can be produced through a process of treating with a boric acid aqueous solution and a process of washing with water after treating with a boric acid aqueous solution.
  • the dichroic dye iodine or a dichroic organic dye may be used.
  • the polarizing plate may further include a protective film attached to one side or both sides of the polarizer, in which case, the pressure-sensitive adhesive layer may be formed on one side of the protective film.
  • the type of protective film is not particularly limited, and includes, for example, a cellulose film such as triacetyl cellulose (TAC); Polyester film such as polycarbonate film or PET (poly (ethylene terephthalet)); Polyether sulfone-based film; Alternatively, a film having a laminated structure of one layer or two or more layers, such as a polyethylene film, a polypropylene film or a polyolefin-based film produced using a resin having a cyclo or norbornene structure, an ethylene-propylene copolymer, or the like can be used.
  • the polarizing plate may further include one or more functional layers selected from the group consisting of a protective layer, a reflective layer, an antiglare layer, a retardation plate, a wide viewing angle compensation film, and a brightness enhancing film.
  • the easy adhesion layer may be a layer formed by the hydroxy group, amino group, carboxyl group, urethane bond, urea bond, or the like present on the surface of the other functional layer such as the polarizer or a protective film formed on one surface of the polarizer, or the like. It may be a layer formed by performing corona discharge or plasma treatment on the surface of the polarizer or another functional layer.
  • the method of forming the pressure-sensitive adhesive layer on the polarizing plate or the optical film as described above is not particularly limited.
  • the pressure-sensitive adhesive composition may be directly coated on the polarizing plate or the optical film and cured to realize a crosslinked structure.
  • a method of transferring it to a polarizing plate or an optical film may be used.
  • the method of coating the pressure-sensitive adhesive composition in the above is not particularly limited, and for example, a method of applying the pressure-sensitive adhesive composition by a conventional means such as a bar coater may be used.
  • the multifunctional crosslinking agent included in the pressure-sensitive adhesive composition is preferably controlled from the crosslinking reaction of the functional group from the viewpoint of performing a uniform coating process, whereby the crosslinking agent crosslinks in the curing and aging process after the coating operation.
  • the cohesive force of the pressure-sensitive adhesive may be improved, and adhesive properties and cuttability may be improved.
  • the coating process is also preferably carried out after sufficiently removing the bubble-inducing components such as volatile components or reaction residues in the pressure-sensitive adhesive composition, so that the crosslinking density or molecular weight of the pressure-sensitive adhesive is too low to lower the elastic modulus, at a high temperature Bubbles existing between the glass plate and the adhesive layer may be increased to prevent a problem of forming scatterers therein.
  • the method of implementing the crosslinking structure by curing the pressure-sensitive adhesive composition subsequent to the coating is also not particularly limited.
  • the coating layer may have an appropriate temperature such that a crosslinking reaction between the block copolymer contained in the coating layer and the multifunctional crosslinking agent may be caused. This can be done in such a way as to maintain.
  • a process of forming an easy adhesion layer on the surface on which the pressure-sensitive adhesive layer is formed may be performed, for example, corona discharge or plasma treatment.
  • the present application also provides a thin glass substrate;
  • the polarizing plate or the optical member may be attached to the glass substrate by the adhesive described above.
  • the pressure-sensitive adhesive layer formed by the pressure-sensitive adhesive composition of the present application can exhibit excellent adhesion with the substrate as described above, and can also effectively suppress warpage even when applied to a thin substrate.
  • the glass substrate may have a thickness of, for example, about 1 mm or less, about 0.9 mm or less, or about 0.8 mm or less.
  • the lower limit of the thickness of the glass substrate is not particularly limited and may be, for example, about 0.1 mm or more, about 0.3 mm or more, or about 0.5 mm or more.
  • the present application also relates to a display device, for example an LCD device.
  • the display device may include the above-described adhesive optical member or polarizing plate.
  • the display device may include a liquid crystal panel and the polarizing plate or optical member attached to one side or both sides of the liquid crystal panel.
  • the polarizing plate or the optical member may be attached to the liquid crystal panel by the adhesive described above.
  • the liquid crystal panel in the apparatus may be, for example, a passive matrix panel such as twisted nematic (TN) type, super twisted nematic (STN) type, ferroelectic (F) type or polymer dispersed (PD) type; Active matrix panels such as two-terminal or three-terminal; All known panels, such as an In Plane Switching (IPS) panel and a Vertical Alignment (VA) panel, can be applied.
  • TN twisted nematic
  • STN super twisted nematic
  • F ferroelectic
  • PD polymer dispersed
  • Active matrix panels such as two-terminal or three-terminal
  • All known panels such as an In Plane Switching (IPS) panel and a Vertical Alignment (VA) panel, can be applied.
  • IPS In Plane Switching
  • VA Vertical Alignment
  • liquid crystal display device for example, upper and lower substrates such as a color filter substrate or an array substrate, are not particularly limited, and a configuration known in the art may be employed without limitation.
  • a pressure-sensitive adhesive composition which is excellent in durability at high temperature or high humidity conditions, and excellent in adhesion with an optical film, and capable of forming a pressure-sensitive adhesive excellent in cutting properties and reworkability.
  • even when applied to a thin substrate such as a very thin glass substrate it is possible to effectively suppress the warp, to minimize the time required for stabilization of physical properties, and to prevent the deterioration of the secured physical properties over time.
  • the adhesive composition which can form the adhesive which can be formed, the adhesive optical member formed using the above-mentioned adhesive composition, an optical laminated body, and a display apparatus can be provided.
  • Mn number average molecular weight
  • PDI molecular weight distribution
  • the adhesive polarizing plate of the Example or the comparative example was cut
  • a physical property analyzer texture analyzer, stable microsystem
  • the polarizing plates that have elapsed by the time described in the following evaluation criteria, respectively, was cut to have a width of 7 cm and a length of 10 cm, and a release sheet (release PET film)
  • the adhesive tape (measuring adhesive tape) for measuring adhesive peeling with a laminator is affixed with an adhesive area of 5 cm in width and 10 cm in length.
  • the resultant was maintained at constant temperature and humidity conditions (25 ° C., 50% relative humidity) for 5 minutes, and the residual amount of the adhesive remaining on the surface of the polarizing plate substrate was checked while removing the attached adhesive tape.
  • a grating is displayed in the longitudinal direction of the polarizing plate, and visually observed and confirmed based on the amount of the adhesive remaining in the grating.
  • the adhesive polarizing plate of Example or Comparative Example was cut to have a width of 50 mm and a length of 50 mm to prepare a specimen, and after removing the release PET adhered to the adhesive layer of the specimen, the surface resistance was measured. Surface resistance was measured according to the manufacturer's manual using an MCP-HT 450 instrument (manufactured by Mitsubishi Chemical, Japan). The specimens were maintained at 23 ° C. and 50% relative humidity for 24 hours before the release sheet (release PET film) was removed from the polarizer and measured after applying a voltage of 500 volts (V) for 1 minute.
  • EBiB ethyl 2-bromoisobutyrate
  • MMA methyl methacrylate
  • EAc ethyl acetate
  • the flask containing the mixture was sealed with a rubber membrane, purged with nitrogen at about 25 ° C. for about 30 minutes, and dissolved oxygen was removed by bubbling.
  • 0.002 g of CuBr2, 0.005 g of tris (2-pyridylmethyl) amine) and 0.017 g of V-65 (2,2'-azobis (2,4-dimethyl valeronitrile)) were added to the oxygen-free mixture.
  • the reaction was initiated by immersing in a reactor at about 67 ° C. (polymerization of the first block).
  • a mixture of 310 g of butyl acrylate (BA), 1.6 g of hydroxybutyl acrylate (HBA) and 500 g of ethyl acetate (EAc) previously bubbled with nitrogen at a time when the conversion rate of methyl methacrylate is about 75% was added in the presence of nitrogen.
  • 0.006 g of CuBr2, 0.012 g of TPMA, and 0.05 g of V-65 were added to the reaction flask, and a chain extension reaction was performed (polymerization of the second block).
  • Block copolymers were prepared by exposing the reaction mixture to oxygen and terminating the reaction by dilution in an appropriate solvent when the conversion of monomers (BA) reached 80% or more (in the process V-65 takes into account its half-life). Appropriately divided to the end of the reaction).
  • a block copolymer as shown in Table 1 was prepared in the same manner as in Preparation Example 1, except that the kind of the raw material (monomer, etc.) used in the polymerization of the block copolymer and the polymerization conditions were adjusted.
  • a crosslinking agent (Coronate LS, Nippon Polyurethane) with respect to 100 weight part of block copolymers (A1) in the manufacture example 1, a polyfunctional epoxy compound (N, N, N ', N'- tetraglycidyl ethylenediamine) 0.5 parts by weight, ionic liquid (FC-4400, 3M) 1.0 part by weight, 2-methylimidazole (Acros) 0.01 part by weight, DBTDL (Dibutyltin dilaurate, Alfa Aesar) 0.01 part by weight and beta-cyanoacetyl 0.4 parts by weight of a silane coupling agent having a group (AD M-812, LG Chem) was mixed, and ethyl acetate was mixed as a solvent to adjust the coating solid content to about 10 to 13 wt% to prepare a coating solution (adhesive composition).
  • a silane coupling agent having a group AD M-812, LG Chem
  • the prepared pressure-sensitive adhesive composition was coated on a release treated surface of a poly (ethylene terephthalate) PET (MRF-38, manufactured by Mitsubishi Corporation) having a thickness of about 38 ⁇ m after the release treatment as a release sheet, so as to have a thickness of about 25 ⁇ m,
  • the pressure-sensitive adhesive layer was formed by maintaining in an oven at 110 ° C. for about 3 minutes.
  • An adhesive composition (coating liquid) and a pressure-sensitive adhesive polarizing plate were manufactured in the same manner as in Example 1 except that the composition was changed as described in Table 2 or 3 in the process of preparing the pressure-sensitive adhesive composition.
  • Adhesive force (gf / 25mm) Interface adhesion Surface resistance ( ⁇ 10 11 ⁇ / ⁇ )
  • a pressure-sensitive adhesive composition which is excellent in durability at high temperature or high humidity conditions, and excellent in adhesion with an optical film, and capable of forming a pressure-sensitive adhesive excellent in cutting properties and reworkability.
  • even when applied to a thin substrate such as a very thin glass substrate it is possible to effectively suppress the warp, to minimize the time required for stabilization of physical properties, and to prevent the deterioration of the secured physical properties over time.
  • the adhesive composition which can form the adhesive which can be formed, the adhesive optical member formed using the above-mentioned adhesive composition, an optical laminated body, and a display apparatus can be provided.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
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  • General Physics & Mathematics (AREA)
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Abstract

La présente application concerne une composition adhésive, qui présente une excellente durabilité dans des conditions de température élevée ou d'humidité élevée, qui présente une excellente adhérence à un film optique, et qui permet ainsi de former un adhésif présentant une excellente propriété de coupe, aptitude au refaçonnage, etc.. En outre, la présente application concerne une composition adhésive qui peut former un adhésif, qui peut supprimer efficacement la flexion, même lorsqu'elle est appliquée à un substrat mince, tel qu'un substrat de verre présentant une très faible épaisseur, qui nécessite un temps réduit de stabilisation des propriétés physiques, et qui peut empêcher la dégradation des propriétés physiques sécurisées pendant que le temps s'écoule, un élément optique de type adhérant formé à l'aide de la composition adhésive, un stratifié optique, et un dispositif d'affichage.
PCT/KR2015/013801 2014-12-16 2015-12-16 Composition adhésive Ceased WO2016099149A1 (fr)

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CN201580054942.0A CN106795410B (zh) 2014-12-16 2015-12-16 压敏粘合剂组合物
US15/513,760 US10851269B2 (en) 2014-12-16 2015-12-16 Pressure-sensitive adhesive composition
JP2017516066A JP6384698B2 (ja) 2014-12-16 2015-12-16 粘着剤組成物

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KR10-2014-0181434 2014-12-16
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2021504510A (ja) * 2017-11-22 2021-02-15 ジーケイエヌ エアロスペース トランスパランシー システムズ インコーポレイテッド 耐久性を備えた導電性ポリウレタン組成物および同組成物を塗布する方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20000025443A (ko) * 1998-10-12 2000-05-06 이터널 케미칼 컴퍼니 리미티드 에폭시 수지 조성물
KR20050076706A (ko) * 2004-01-20 2005-07-26 주식회사 엘지화학 편광판용 아크릴계 점착제 조성물
KR20090039498A (ko) * 2007-10-18 2009-04-22 주식회사 엘지화학 접착제 조성물, 접착 필름, 다이싱 다이본딩 필름 및반도체 장치
KR20130135157A (ko) * 2012-05-31 2013-12-10 주식회사 엘지화학 점착제 조성물
KR20140128887A (ko) * 2013-04-29 2014-11-06 주식회사 엘지화학 점착제 조성물

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20000025443A (ko) * 1998-10-12 2000-05-06 이터널 케미칼 컴퍼니 리미티드 에폭시 수지 조성물
KR20050076706A (ko) * 2004-01-20 2005-07-26 주식회사 엘지화학 편광판용 아크릴계 점착제 조성물
KR20090039498A (ko) * 2007-10-18 2009-04-22 주식회사 엘지화학 접착제 조성물, 접착 필름, 다이싱 다이본딩 필름 및반도체 장치
KR20130135157A (ko) * 2012-05-31 2013-12-10 주식회사 엘지화학 점착제 조성물
KR20140128887A (ko) * 2013-04-29 2014-11-06 주식회사 엘지화학 점착제 조성물

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2021504510A (ja) * 2017-11-22 2021-02-15 ジーケイエヌ エアロスペース トランスパランシー システムズ インコーポレイテッド 耐久性を備えた導電性ポリウレタン組成物および同組成物を塗布する方法
JP7383612B2 (ja) 2017-11-22 2023-11-20 ジーケイエヌ エアロスペース トランスパランシー システムズ インコーポレイテッド 耐久性を備えた導電性ポリウレタン組成物および同組成物を塗布する方法
JP2023179430A (ja) * 2017-11-22 2023-12-19 ジーケイエヌ エアロスペース トランスパランシー システムズ インコーポレイテッド 耐久性を備えた導電性ポリウレタン組成物および同組成物を塗布する方法
JP7592132B2 (ja) 2017-11-22 2024-11-29 ジーケイエヌ エアロスペース トランスパランシー システムズ インコーポレイテッド 耐久性を備えた導電性ポリウレタン組成物および同組成物を塗布する方法

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