WO2015076548A1 - 점착제 조성물 - Google Patents
점착제 조성물 Download PDFInfo
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- WO2015076548A1 WO2015076548A1 PCT/KR2014/011108 KR2014011108W WO2015076548A1 WO 2015076548 A1 WO2015076548 A1 WO 2015076548A1 KR 2014011108 W KR2014011108 W KR 2014011108W WO 2015076548 A1 WO2015076548 A1 WO 2015076548A1
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- WIPO (PCT)
- Prior art keywords
- sensitive adhesive
- pressure
- adhesive composition
- block
- weight
- Prior art date
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Classifications
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- 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
- C09J133/10—Homopolymers or copolymers of methacrylic acid esters
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- 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
- C09J153/00—Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
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- 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
- C09J7/22—Plastics; Metallised plastics
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- 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
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
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- 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
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C09J7/387—Block-copolymers
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
- G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
- G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
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- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays
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- 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
- C09J2453/00—Presence of block copolymer
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- 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
- C09J2453/00—Presence of block copolymer
- C09J2453/003—Presence of block copolymer in the primer coating
Definitions
- the present application relates to an adhesive composition, an optical laminate, a polarizing plate, and a display device.
- the adhesive can be used for various applications.
- the adhesive may be used for attaching an optical film such as a polarizing plate or a retardation film to a display device such as a liquid crystal display device (hereinafter referred to as "LCD device"), or an optical film such as the polarizing plate or retardation film. It can be used for the purpose of laminating each other.
- the adhesive used for an optical film etc. may require cohesion force, adhesive force, reworkability, or low light leakage property with excellent transparency.
- the adhesive composition for optics as mentioned above is proposed.
- 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
- the present application provides an adhesive composition, an optical laminate, a polarizing plate, and a display device.
- Exemplary pressure-sensitive adhesive composition may include a block copolymer.
- 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 measured from a polymer formed only of monomers included in the block.
- the glass transition temperature of the first block may be 60 ° C. or higher, 65 ° C. or higher, or 70 ° C. or higher.
- the upper limit of the glass transition temperature of the first block is not particularly limited, but may be, for example, about 150 ° C, 140 ° C, 130 ° C, or about 120 ° C.
- the glass transition temperature of the second block may be -20 ° C or less, -30 ° C or less, -35 ° C or less, -40 ° C or less, or -45 ° 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. Such 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 block copolymer may have a number average molecular weight within the range of 200,000 to 500,000.
- the term number average molecular weight, weight average molecular weight, or molecular weight distribution (PDI) may refer to a conversion value for standard polystyrene measured by gel permeation chromatography (GPC) as described in Examples below.
- the number average molecular weight of the block copolymer may be 220,000 or more, 250,000 or more, or 300,000 or more.
- the block copolymer may be about 450,000 or less or about 400,000 or less.
- the number average molecular weight of the block copolymer When the number average molecular weight of the block copolymer is maintained in the above range, it exhibits excellent durability even under severe conditions such as high temperature, high humidity, and room temperature and low humidity, as well as the harsh conditions, especially the harsh conditions such as high temperature or high temperature and high humidity. It is possible to provide an adhesive that exhibits excellent light leakage prevention and reworkability.
- the block copolymer may have a molecular weight distribution (PDI; Mw / Mn), that is, a ratio (Mw / Mn) of the weight average molecular weight (Mw) and the number average molecular weight (Mn) in the range of 2.0 to 5.0.
- PDI molecular weight distribution
- Mw / Mn a ratio of the weight average molecular weight (Mw) and the number average molecular weight (Mn) in the range of 2.0 to 5.0.
- the ratio Mw / Mn may be 2.5 or more or 3.0 or more.
- the ratio Mw / Mn may be about 4.5 or less. Within this range, it is possible to further improve the durability, light leakage prevention ability and reworkability of the pressure-sensitive adhesive.
- the first block included in the block copolymer may have a number average molecular weight within the range of 10,000 to 250,000.
- the number average molecular weight of the first block may mean, for example, the number average molecular weight of a polymer prepared by polymerizing only the monomers forming the first block. In one example, the number average molecular weight of the first block may be 15,000 or more or 20,000 or more. In another example, the number average molecular weight of the first block may be 200,000 or less or 180,000 or less.
- the block copolymer may be formulated to have a viscosity in a predetermined range.
- the block copolymer may have a room temperature viscosity of at least 3,000 cP or about 3,000 cP to 8,000 cP, measured in dilution with an organic solvent such as ethyl acetate such that its solid content is 30% by weight.
- room temperature is a natural temperature that is not heated or cooled, and may mean a temperature of about 10 ° C to 30 ° C, 15 ° C to 30 ° C, 20 ° C to 30 ° C, 25 ° C, or 22 ° C.
- 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, a second block having a low glass transition temperature.
- the first block having a high glass transition temperature 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 monomer forming the first or second block is such that the crosslinkable functional groups are introduced at appropriate positions by the combination of the monomers, and the glass transition temperature of each block and the number average molecular weight of the copolymer are appropriately controlled. As long as it is not restrict
- 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.
- the pressure-sensitive adhesive can exhibit an appropriate cohesion force and stress relaxation property with temperature change, thereby forming an pressure-sensitive adhesive having excellent durability reliability, light leakage preventing property, workability and the like.
- a hydroxy group or the like may be used as the crosslinkable functional group.
- the antistatic performance of the adhesive is such that the antistatic agent in which the functional group such as the hydroxy group is included in the adhesive has a uniform distribution. The change over time can be minimized.
- 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, but is not limited thereto.
- 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.
- the comonomer include (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 (meth)
- 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, 10 parts by weight to 50 parts by weight of the first block and 50 parts by weight to 90 parts by weight of the second block.
- the block copolymer may be, in another example, 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; 5 parts by weight to 45 parts by weight of the first block and 60 parts by weight to 95 parts by weight of the second block; Or 5 parts by weight to 40 parts by weight of the first block and 60 parts by weight to 95 parts by weight of the second block.
- 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 capable of crosslinking the block copolymer.
- a crosslinking agent capable of crosslinking the block copolymer.
- 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 and the like can be exemplified.
- an isocyanate crosslinking agent can be used.
- isocyanate crosslinking agent For example, diisocyanate compounds, such as tolylene diisocyanate, xylene diisocyanate, diphenylmethane diisocyanate, hexamethylene diisocyanate, isoborone diisocyanate, tetramethyl xylene diisocyanate, or naphthalene diisocyanate, Alternatively, a compound obtained by reacting the diisocyanate compound with a polyol may be used. As the polyol, for example, trimethylol propane may be used.
- 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, for example, in an amount of 0.01 to 10 parts by weight or 0.01 to 5 parts by weight with respect to 100 parts by weight of the block copolymer, and in this range, the gel fraction, cohesion, adhesive strength and Durability etc. can be kept excellent.
- 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 (1) or (2) can be used, for example.
- R 1 is a beta-cyanoacetyl group or a beta-cyanoacetylalkyl group
- R 3 is an acetoacetyl group or acetoacetylalkyl group
- R 2 is an alkoxy group
- n is 1 to 3 Is the number of.
- 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 is linear, branched or cyclic. It may be a phase.
- n in Formula 1 or 2 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 based on 100 parts by weight of the block copolymer, and may effectively impart desired properties to the pressure-sensitive adhesive within this range.
- 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 a pressure-sensitive adhesive optical laminate.
- Exemplary optical laminates include optical films; 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 polarizing film, a retardation film, a brightness enhancing film, or the like, or a laminate in which two or more kinds thereof are laminated may be exemplified.
- 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 polarizing film in the adhesive optical laminate.
- the kind of polarizing film included in the polarizing plate is not particularly limited, and for example, a general kind known in the art such as polyvinyl alcohol-based polarizing film can be used without limitation.
- the polarizing film is a functional film capable of extracting only light vibrating in one direction from incident light while vibrating in various directions.
- a polarizing film may be a form in which a dichroic dye is adsorbed and oriented in a polyvinyl alcohol-based resin film, for example.
- Polyvinyl alcohol-type resin which comprises a polarizing film 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 is usually 85 mol% to 100 mol%, preferably 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 polarizing film is a step of stretching (ex. Uniaxially stretching) the above-mentioned polyvinyl alcohol-based resin film, dyeing the polyvinyl alcohol-based resin film with a dichroic dye, adsorbing the dichroic dye, and dichroic dye.
- the adsorbed polyvinyl alcohol-based resin film can be produced through a process of treating with boric acid aqueous solution, and a process of washing with water after treating with 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 polarizing film, and in this 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 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.
- the present application also relates to a display device, for example an LCD device.
- An exemplary display device may include a liquid crystal panel and the polarizing plate or the optical laminate attached to one side or both sides of the liquid crystal panel.
- the polarizing plate or the optical laminate may be attached to the liquid crystal panel by the pressure-sensitive 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
- the upper and lower substrates such as a color filter substrate or an array substrate
- the upper and lower substrates are not particularly limited, and configurations known in the art may be employed without limitation.
- an adhesive composition capable of forming an adhesive excellent in cohesive force or stress relaxation property and excellent in durability reliability, light leakage preventing ability, and the like may be provided.
- the pressure-sensitive adhesive composition of the present application can be used, for example, for an optical film such as a polarizing plate.
- Mn number average molecular weight
- PDI molecular weight distribution
- Coating solid content was evaluated by the following method.
- Example 2 The pressure-sensitive adhesive composition of Example or Comparative Example is taken in an amount of about 0.3 g to 0.5 g (sample before drying) and placed in the aluminum dish.
- the coating solid content is evaluated by the following formula according to the measurement result.
- the viscosity of the pressure-sensitive adhesive composition was evaluated in the following manner using a Brookfield digital viscometer (DV-I +, DV-II + Pro).
- the pressure-sensitive adhesive composition prepared in Examples and Comparative Examples was coated, and the coating layer was visually observed to evaluate the following criteria.
- the polarizing plates prepared in Examples and Comparative Examples were cut to have a width of about 180 mm and a length of about 320 mm, to prepare a specimen, and attach it to a 19 inch commercial panel.
- the panel is then stored in an autoclave (50 ° C., 5 atmospheres) for about 20 minutes to prepare a sample.
- the heat resistance and moisture resistance of the prepared samples were evaluated according to the following criteria by observing the occurrence of bubbles and peeling at the adhesive interface after leaving the sample at 60 ° C. and 90% relative humidity for 500 hours, and the heat resistance of the samples at 80 ° C. After maintaining for 500 hours at and also observed the occurrence of bubbles and peeling evaluated by the following criteria.
- the room temperature low humidity durability after the heat-resistant heat was evaluated according to the following criteria by maintaining the sample subjected to the heat-resistant heat resistance evaluation for 30 days at 25 °C and 25% relative humidity conditions and again observed the occurrence of bubbles and peeling at the adhesive interface. .
- the glass transition temperature (Tg) of each block of the block copolymer was calculated according to the following formula.
- Wn is a weight fraction of the monomer used in each block and the like, and Tn represents a glass transition temperature that appears when the monomer used forms a homopolymer.
- the right side of the above formula is the sum of the calculated values after calculating all the monomers (Wn / Tn) divided by the glass transition temperature when the monomer forms the homopolymer (Wn / Tn). to be.
- MMA Conversion Rate (%) 100 ⁇ B / (A + B)
- A is the area of the peak derived from the methyl group derived from MMA contained in the polymer in the 1 H-NMR spectrum (approximately 3.4 ppm to 3.7 ppm)
- B is the peak derived from the methyl group of the unpolymerized MMA (3.7 per ppm). That is, the conversion rate of the monomer was calculated in consideration of the shift position of the methyl group peak in the structure of the MMA.
- the ratio of the 1st and 2nd block of a block copolymer is a following formula based on the ratio of methyl methacrylate (MMA) and butyl acrylate (BA) which are the main monomers used in forming a 1st block and a 2nd block. Calculated based on
- % Content of MMA in block copolymer 100 x MMA peak area / BA peak area
- the MMA peak area is the area value per 1 H proton of the 3.4 to 3.7 ppm vicinity peak in 1 H-NMR (peak observed by -CH 3 derived from MMA), and the BA peak area is 3.8 to 4.2 in 1 H-NMR. Area value per 1 H proton of the ppm vicinity peak (the peak observed by -OCH 2 -present in the polymer formed by BA).
- the weight ratio of the first and second blocks was calculated by calculating the relative values of the -CH 3 peak of the MMA structure and the -OCH 2 -peak of the polymer formed from BA.
- EBiB ethyl 2-bromoisobutyrate
- MMA methyl methacrylate
- EAc ethyl acetate
- the flask containing the mixture was sealed with a rubber membrane, purged with nitrogen for about 30 minutes at about 25 ° C., and dissolved to remove dissolved oxygen through bubbling.
- 0.002 g of CuBr 2 , 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 started 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 CuBr 2 , 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).
- Each 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) used in the polymerization of the block copolymer, the polymerization conditions, and the like were adjusted.
- MMA methyl methacrylate
- n-butyl acrylate n-butyl acrylate
- 4-hydroxybutyl acrylate 10 parts by weight of methyl methacrylate (MMA), 87.3 parts by weight of n-butyl acrylate and 2.7 parts by weight of 4-hydroxybutyl acrylate were added to a 1L reactor equipped with a refrigeration system for nitrogen gas reflux and for easy temperature control. 120 parts by weight of ethyl acetate was added as a solvent. Subsequently, the nitrogen gas is purged for about 60 minutes to remove oxygen, and 0.05 parts by weight of AIBN (azobisisobutyronitrile), which is a reaction initiator, is maintained at a temperature of 60 ° C., and the molecular weight and molecular weight distribution as mentioned below can be ensured.
- AIBN azobisisobutyronitrile
- the copolymer was reacted for about 8 hours while adjusting the polymerization conditions to prepare a random copolymer.
- the number average molecular weight (Mn) of the prepared random copolymer (C1) was about 232,000, and the molecular weight distribution (PDI) was about 4.9.
- the coating solution was prepared by mixing parts by weight, adjusting ethyl acetate as a solvent to adjust the coating solid content to about 30% by weight.
- the prepared coating solution was coated on a release treated surface of release PET (poly (ethylene terephthalate)) (MRF-38, manufactured by Mitsubishi) having a thickness of 38 ⁇ m, which was release-treated so that the thickness after drying was about 23 ⁇ m. And held for about 3 minutes.
- release PET poly (ethylene terephthalate)
- MRF-38 poly (ethylene terephthalate)
- TAC triacetyl cellulose
- PVA polyvinyl alcohol-based polarizing film
- the pressure-sensitive adhesive composition (coating liquid) and the pressure-sensitive adhesive polarizing plate were prepared in the same manner as in Example 1 except that each component and the ratio were adjusted as shown in Table 2 in the preparation of the pressure-sensitive adhesive composition (coating liquid).
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Abstract
Description
제조예 | ||||||||
1 | 2 | 3 | 4 | 5 | 6 | 7 | ||
A1 | A2 | A3 | A4 | B1 | B2 | B3 | ||
제1블록 | MMA 비율 | 100 | 80 | 60 | 70 | 80 | 60 | 81 |
BMA 비율 | 0 | 20 | 40 | 30 | 20 | 40 | 16 | |
HPMA 비율 | 0 | 0 | 0 | 0 | 0 | 0 | 3 | |
Tg(℃) | 110 | 90 | 72 | 80 | 90 | 72 | 90 | |
Mn(×10000) | 2.9 | 3.2 | 4.1 | 4.3 | 0.4 | 1.7 | 2.3 | |
PDI | 1.37 | 1.44 | 1.38 | 1.41 | 1.21 | 1.32 | 1.36 | |
제2블록 | BA비율 | 99.5 | 97.0 | 94.0 | 95.0 | 97.0 | 95.0 | 100 |
HBA 비율 | 0.5 | 3.0 | 6.0 | 5.0 | 3.0 | 5.0 | 0 | |
Tg(℃) | -47 | -46.2 | -47.5 | -47 | -46.2 | -47 | -45 | |
블록공중합체 | Mn(×10000) | 23.7 | 27.3 | 33.5 | 37.4 | 2.3 | 10.4 | 12.2 |
PDI | 2.8 | 3.1 | 3.3 | 4.1 | 1.4 | 2.2 | 1.8 | |
비율 단위: 중량부Tg: 유리전이온도Mn: 수평균분자량PDI: 분자량 분포BA: butyl acrylate (단독 중합체 Tg: 약 -45℃)HBA: 4-hydroxybutyl acrylate (단독 중합체 Tg: 약 -80℃)MMA: methyl methacrylate (단독 중합체 Tg: 약 110℃)BMA: butyl methacrylate (단독 중합체 Tg: 약 27℃)HPMA: 3-hydroxypropyl methacrylate (단독 중합체 Tg: 약 26℃) |
실시예 | 비교예 | |||||||||
1 | 2 | 3 | 4 | 1 | 2 | 3 | 4 | 5 | ||
블록공중합체 | 종류 | A1 | A2 | A3 | A4 | B1 | B2 | B2 | C1 | B3 |
함량 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | |
가교제 함량 | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 | 0.2 | 0.2 | 0.1 | |
DBTDL 함량 | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 | 0.2 | 0.2 | 0.1 | |
SCA 함량 | 0.2 | 0.2 | 0.2 | 0.2 | 0.2 | 0.2 | 0.2 | 0.2 | 0.2 | |
함량 단위: 중량부가교제: Coronate L, 일본 NPU제DBTDL: dibutyltin dilaurateSCA: β 시아노아세틸기를 가지는 실란 커플링제(M812, LG화학제) |
실시예 | 비교예 | ||||||||
1 | 2 | 3 | 4 | 1 | 2 | 3 | 4 | 5 | |
코팅성 | A | A | A | A | A | A | A | A | A |
내열내구성 | A | A | A | A | C | B | A | A | A |
내습열내구성 | A | A | A | A | B | A | A | B | C |
상온저습내구성 | A | A | A | A | C | C | C | C | C |
Claims (14)
- 유리전이온도가 50℃ 이상인 제 1 블록과 유리전이온도가 -10℃ 이하이며, 가교성 관능기를 포함하는 제 2 블록을 가지고, 수평균분자량이 20만 내지 50만의 범위 내에 있는 블록 공중합체를 포함하는 점착제 조성물.
- 제 1 항에 있어서, 제 1 블록의 수평균분자량이 1만 내지 25만의 범위 내에 있는 점착제 조성물.
- 제 1 항에 있어서, 블록 공중합체의 분자량 분포가 2.0 내지 5.0인 점착제 조성물.
- 제 1 항에 있어서, 블록 공중합체는 그 고형분 함량이 30 중량%가 되도록 에틸 아세테이트로 희석된 상태에서의 상온 점도가 3,000 cP 이상인 점착제 조성물.
- 제 1 항에 있어서, 가교성 관능기는 제 1 블록에는 포함되어 있지 않고, 제 2 블록에만 포함되어 있는 점착제 조성물.
- 제 1 항에 있어서, 가교성 관능기가 히드록시기인 점착제 조성물.
- 제 1 항에 있어서, 제 1 블록은 메타크릴산 에스테르 단량체로부터 유도된 중합 단위를 포함하는 점착제 조성물.
- 제 1 항에 있어서, 제 2 블록은 아크릴산 에스테르 단량체 90 내지 99.9 중량부 및 가교성 관능기를 가지는 공중합성 단량체 0.1 내지 10 중량부로부터 유도된 중합된 단위를 포함하는 점착제 조성물.
- 제 1 항에 있어서, 블록 공중합체는, 제 1 블록 및 제 2 블록을 가지는 디블록 공중합체인 점착제 조성물.
- 제 1 항에 있어서, 가교성 관능기와 반응할 수 있는 관능기를 2개 이상 가지는 가교제를 추가로 포함하는 점착제 조성물.
- 제 10 항에 있어서, 가교제는 블록 공중합체 100 중량부 대비 0.01 중량부 내지 10 중량부로 포함되는 점착제 조성물.
- 광학 필름; 및 상기 광학 필름의 일면 또는 양면에 존재하며, 가교 구조가 구현된 제 1 항의 점착제 조성물을 포함하는 점착제층을 가지는 점착형 광학 적층체.
- 편광 필름; 및 상기 편광 필름의 일면 또는 양면에 존재하며, 가교 구조가 구현된 제 1 항의 점착제 조성물을 포함하는 점착제층을 가지는 점착형 편광판.
- 제 12 항의 점착형 광학 적층체 또는 제 13 항의 점착형 편광판을 포함하는 디스플레이 장치.
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US14/765,696 US9976062B2 (en) | 2013-11-19 | 2014-11-19 | Pressure sensitive adhesive composition |
JP2015559210A JP6089287B2 (ja) | 2013-11-19 | 2014-11-19 | 粘着剤組成物 |
EP14863100.5A EP2947129B1 (en) | 2013-11-19 | 2014-11-19 | Adhesive composition |
CN201480005821.2A CN104937064B (zh) | 2013-11-19 | 2014-11-19 | 压敏粘合剂组合物 |
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KR1020140161373A KR101701569B1 (ko) | 2013-11-19 | 2014-11-19 | 점착제 조성물 |
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JP6253069B2 (ja) | 2013-11-26 | 2017-12-27 | エルジー・ケム・リミテッド | 粘着剤組成物 |
JP6943671B2 (ja) * | 2016-08-03 | 2021-10-06 | リンテック株式会社 | 表示用粘着ラベルの製造方法 |
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EP2947129A4 (en) | 2016-08-10 |
EP2947129B1 (en) | 2017-10-04 |
CN104937064A (zh) | 2015-09-23 |
TWI548712B (zh) | 2016-09-11 |
US9976062B2 (en) | 2018-05-22 |
KR20150058069A (ko) | 2015-05-28 |
JP6089287B2 (ja) | 2017-03-08 |
JP2016510359A (ja) | 2016-04-07 |
US20150376474A1 (en) | 2015-12-31 |
CN104937064B (zh) | 2018-05-11 |
TW201533193A (zh) | 2015-09-01 |
KR101701569B1 (ko) | 2017-02-01 |
EP2947129A1 (en) | 2015-11-25 |
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