WO2022244557A1 - 粘着剤組成物、粘着シート、光学積層体及び画像表示装置 - Google Patents
粘着剤組成物、粘着シート、光学積層体及び画像表示装置 Download PDFInfo
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- WO2022244557A1 WO2022244557A1 PCT/JP2022/017652 JP2022017652W WO2022244557A1 WO 2022244557 A1 WO2022244557 A1 WO 2022244557A1 JP 2022017652 W JP2022017652 W JP 2022017652W WO 2022244557 A1 WO2022244557 A1 WO 2022244557A1
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- meth
- weight
- sensitive adhesive
- pressure
- acrylate
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- OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
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- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 238000007717 redox polymerization reaction Methods 0.000 description 1
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
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- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
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- 235000007586 terpenes Nutrition 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
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- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
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- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—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
- C09J133/08—Homopolymers or copolymers of acrylic acid esters
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- 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]
-
- 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
- C09J7/385—Acrylic polymers
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
Definitions
- the present invention relates to an adhesive composition, an adhesive sheet, an optical laminate, and an image display device.
- image display devices typified by liquid crystal display devices and electroluminescence (EL) display devices (eg, organic EL display devices and inorganic EL display devices) have rapidly spread.
- These various image display devices usually have a laminated structure of an image forming layer such as a liquid crystal layer and an EL light emitting layer, and an optical laminate including an optical film and an adhesive sheet.
- the pressure-sensitive adhesive sheet is mainly used for bonding between films included in the optical layered body and bonding between the image forming layer and the optical layered body.
- the optical film are a polarizing plate, a retardation film, and a polarizing plate with a retardation film in which the polarizing plate and the retardation film are integrated.
- Patent Documents 1 and 2 disclose an example of an optical layered body.
- An object of the present invention is to provide a pressure-sensitive adhesive composition suitable for forming a pressure-sensitive adhesive sheet that can suppress changes in the dimensions of the optical film contained in the optical laminate and also ensures durability.
- the present invention (Meth) acrylic polymer (A) as a main component, further comprising a cross-linking agent (B),
- the amount of the cross-linking agent (B) is 5 parts by weight or more with respect to 100 parts by weight of the (meth)acrylic polymer (A),
- the invention provides a A pressure-sensitive adhesive sheet formed from the pressure-sensitive adhesive composition of the present invention, I will provide a.
- the invention provides a An optical laminate comprising the adhesive sheet of the present invention and an optical film, I will provide a.
- the invention provides a an image display device comprising the optical layered body of the present invention; I will provide a.
- the pressure-sensitive adhesive composition according to the present invention is suitable for forming a pressure-sensitive adhesive sheet that can suppress changes in the dimensions of the optical film contained in the optical layered body and also ensures durability.
- FIG. 1 is a cross-sectional view schematically showing an example of the pressure-sensitive adhesive sheet of the present invention.
- FIG. 2 is a cross-sectional view schematically showing an example of the optical layered body of the present invention.
- FIG. 3 is a cross-sectional view schematically showing an example of the optical layered body of the present invention.
- FIG. 4 is a cross-sectional view schematically showing an example of the optical layered body of the present invention.
- FIG. 5 is a cross-sectional view schematically showing an example of the optical layered body of the present invention.
- FIG. 6 is a cross-sectional view schematically showing an example of the image display device of the present invention.
- (Meth)acrylic as used herein means acrylic and methacrylic. Moreover, “(meth)acrylate” means acrylate and methacrylate.
- the pressure-sensitive adhesive composition (I) of the present embodiment contains a (meth)acrylic polymer (A) and a cross-linking agent (B).
- the (meth)acrylic polymer (A) is contained in the pressure-sensitive adhesive composition (I) as a main component.
- the pressure-sensitive adhesive composition (I) is an acrylic pressure-sensitive adhesive composition.
- a main component means the component with the largest content rate also in a composition.
- the content of the main component is, for example, 50% by weight or more, and may be 60% by weight or more, 70% by weight or more, 73% by weight or more, or even 75% by weight or more.
- the blending amount of the cross-linking agent (B) is 5 parts by weight or more with respect to 100 parts by weight of the (meth)acrylic polymer (A).
- the pressure-sensitive adhesive composition (I) having a blending amount within the above range is suitable for forming a pressure-sensitive adhesive sheet having an increased elastic modulus.
- the cross-linking agent (B) reacts with each other during the formation of the pressure-sensitive adhesive sheet, facilitating the formation of a self-polymer of the cross-linking agent (B).
- the formation of the self-polymer increases the cohesive force of the adhesive sheet, thereby contributing to the formation of the adhesive sheet that can suppress the dimensional change of the optical film.
- the compatibility between the (meth)acrylic polymer (A) and the self-polymer is low, the durability of the pressure-sensitive adhesive sheet tends to decrease. A possible reason for the decrease is that an independent region rich in self-polymer tends to occur inside the pressure-sensitive adhesive sheet.
- the formation of the above areas can cause voids and the like due to progress of peeling at the interfaces of the areas when the pressure-sensitive adhesive sheet is deformed by an external force.
- the adhesive composition of the present embodiment assuming the self-polymer (C) of the cross-linking agent (B), the Hansen solubility between the (meth)acrylic polymer (A) and the self-polymer (C) The parameter (HSP) distance Ra is 12.3 or less. The smaller the distance Ra, the higher the compatibility between the polymers. Therefore, the pressure-sensitive adhesive composition of the present embodiment is suitable for forming a pressure-sensitive adhesive sheet in which durability is ensured.
- the Hansen Solubility Parameter is the solubility parameter introduced by Hildebrand divided into three components: the dispersion term ⁇ D, the polarization term ⁇ P and the hydrogen bonding term ⁇ H.
- ⁇ D indicates the energy derived from the intermolecular dispersion force.
- ⁇ P indicates the energy derived from intermolecular polar forces.
- ⁇ H indicates energy derived from intermolecular hydrogen bonding force.
- the unit of each component is usually MPa 1/2 .
- the three components define a point (vector) in a three-dimensional space known as Hansen's space.
- the distance Ra is defined by points (D A , P A , H A ) corresponding to the (meth)acrylic polymer (A) and points (D C , P C , H C ) and can be calculated by the formula: ⁇ 4 ⁇ ( ⁇ D A ⁇ D B ) 2 +( ⁇ P A ⁇ P B ) 2 +( ⁇ H A ⁇ H B ) 2 ⁇ 1/2 . Details of the Hansen Solubility Parameters are disclosed in "Hansen Solubility Parameters; A Users Handbook" (CRC Press, 2007).
- ⁇ D, ⁇ P and ⁇ H of the polymer can be determined by calculation using known software such as HSPiP (version 5) based on the constituent units possessed by the polymer and the content of such units in the polymer. More specifically, ⁇ D, ⁇ P and ⁇ H of each structural unit are individually calculated, and the weighted average value obtained by weighting the calculated ⁇ D, ⁇ P and ⁇ H by the content of the unit is used as the ⁇ D, ⁇ H of the polymer. ⁇ P and ⁇ H. However, the calculation is performed at a temperature of 23°C. Note that the calculated values of .delta.D, .delta.P and .delta.H may differ slightly depending on the software used. However, the difference is usually negligible in determining Ra. Hansen Solubility Parameters for crosslinkers are calculated only for those that form self-polymers.
- the distance Ra is 12.25 or less, 12.2 or less, 12.15 or less, 12.1 or less, 12.05 or less, 12.0 or less, 11.95 or less, 11.9 or less, 11.85 or less, 11 0.8 or less, 11.75 or less, or even 11.7 or less.
- the lower limit of the distance Ra is, for example, 6 or more.
- the (meth)acrylic polymer (A) preferably has, as a main unit, a structural unit derived from the (meth)acrylic monomer (A1) having an alkyl group having 1 to 30 carbon atoms in the side chain.
- the alkyl group may be linear or branched.
- the (meth)acrylic polymer (A) may have one or more structural units derived from the (meth)acrylic monomer (A1).
- Examples of (meth) acrylic monomers (A1) include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, s-butyl (meth) acrylate, t-butyl (meth) acrylate.
- the term "main unit" refers to the total structural units of the poly
- the (meth)acrylic polymer (A) may have structural units derived from the (meth)acrylic monomer (A1) having a long-chain alkyl group in its side chain.
- An example of said monomer (A1) is n-dodecyl (meth)acrylate (lauryl (meth)acrylate).
- the term "long-chain alkyl group” means an alkyl group having 6 to 30 carbon atoms.
- the (meth)acrylic polymer (A) is a structural unit derived from the (meth)acrylic monomer (A1) having a glass transition temperature (Tg) in the range of ⁇ 70 to ⁇ 20° C. when homopolymerized. may have An example of said monomer (A1) is n-butyl acrylate.
- the (meth)acrylic polymer (A) may have structural units other than the structural units derived from the (meth)acrylic monomer (A1).
- the structural unit is derived from the monomer (A2) copolymerizable with the (meth)acrylic monomer (A1).
- the (meth)acrylic polymer (A) may have one or more of these structural units.
- the monomer (A2) is an aromatic ring-containing monomer.
- the aromatic ring-containing monomer may be an aromatic ring-containing (meth)acrylic monomer.
- aromatic ring-containing monomers include phenyl (meth) acrylate, phenoxyethyl (meth) acrylate, benzyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, ethylene oxide-modified nonylphenol (meth) acrylate, hydroxyethylated ⁇ - naphthol (meth)acrylate and biphenyl (meth)acrylate.
- the content of structural units derived from aromatic ring-containing monomers in the (meth)acrylic polymer (A) is, for example, 0 to 50% by weight, 1 to 30% by weight, 5 to 25% by weight, 8 to 20% by weight. % by weight, 10-18% by weight, 12-16% by weight, or even 12-16% by weight.
- Having a structural unit derived from an aromatic ring-containing monomer in the (meth)acrylic polymer (A) is a phase between the (meth)acrylic polymer (A), the cross-linking agent (B), and its self-polymer. It can contribute to the improvement of solubility.
- the hydroxyl group-containing monomer may be a hydroxyl group-containing (meth)acrylic monomer.
- hydroxyl-containing monomers are 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, 8-hydroxyoctyl ( hydroxyalkyl (meth)acrylates such as meth)acrylates, 10-hydroxydecyl (meth)acrylate and 12-hydroxylauryl (meth)acrylate, and (4-hydroxymethylcyclohexyl)-methylacrylate.
- the hydroxyl group can react with various cross-linking agents.
- the content of structural units derived from hydroxyl group-containing monomers in the (meth)acrylic polymer (A) may be 1% by weight or less. It may be 5% by weight or less, further 0.1% by weight or less, or 0% by weight (without including the structural unit).
- the monomer (A2) may be a carboxyl group-containing monomer, an amino group-containing monomer, or an amide group-containing monomer.
- carboxyl group-containing monomers are (meth)acrylic acid, carboxyethyl (meth)acrylate, carboxypentyl (meth)acrylate, itaconic acid, maleic acid, fumaric acid and crotonic acid.
- amino group-containing monomers are N,N-dimethylaminoethyl (meth)acrylate and N,N-dimethylaminopropyl (meth)acrylate.
- amide group-containing monomers are (meth)acrylamide, N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N-isopropylacrylamide, N-methyl(meth)acrylamide, N- Butyl (meth)acrylamide, N-hexyl (meth)acrylamide, N-methylol (meth)acrylamide, N-methylol-N-propane (meth)acrylamide, aminomethyl (meth)acrylamide, aminoethyl (meth)acrylamide, mercaptomethyl (Meth) acrylamide-based monomers such as mercaptoethyl (meth) acrylamide; and N-vinyl group-containing lactam monomers such as N-vinylpyrrolidone and N-vinyl- ⁇ -caprolactam.
- the monomer (A2) may be a polyfunctional monomer.
- multifunctional monomers are hexanediol di(meth)acrylate (1,6-hexanediol di(meth)acrylate), butanediol di(meth)acrylate, (poly)ethylene glycol di(meth)acrylate, (Poly)propylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol hexa(meth)acrylate, trimethylolpropane tri( polyfunctional acrylates such as meth)acrylates, tetramethylolmethane tri(meth)acrylates, allyl (meth)acrylates, vinyl (meth)acrylates, epoxy acrylates, polyester acrylates and urethane acrylates; and divin
- the total content of structural units derived from the carboxyl group-containing monomer, amino group-containing monomer, amide group-containing monomer and polyfunctional monomer in the (meth)acrylic polymer (A) is preferably is 20% by weight or less, more preferably 10% by weight or less, and still more preferably 8% by weight or less.
- the total content is, for example, 0.01% by weight or more, and may be 0.05% by weight or more.
- the (meth)acrylic polymer (A) may not contain structural units derived from polyfunctional monomers.
- cross-linking Self-polymerization of the agent (B) can be enhanced. Improvement of the self-polymerization of the cross-linking agent (B) can contribute to suppression of peeling of the pressure-sensitive adhesive sheet in a humidified environment, and stabilization of physical properties of the pressure-sensitive adhesive sheet in a system having a high content of the cross-linking agent (B). .
- Examples of other monomers (A2) include 2-methoxyethyl (meth)acrylate, 2-ethoxyethyl (meth)acrylate, methoxytriethylene glycol (meth)acrylate, and 3-methoxy (meth)acrylate.
- Alkoxyalkyl (meth)acrylates such as propyl, 3-ethoxypropyl (meth)acrylate, 4-methoxybutyl (meth)acrylate and 4-ethoxybutyl (meth)acrylate; glycidyl (meth)acrylate and ( Epoxy group-containing monomers such as methyl glycidyl acrylate; sulfonic acid group-containing monomers such as sodium vinyl sulfonate; phosphoric acid group-containing monomers; cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate and (meth)acrylic acid esters having an alicyclic hydrocarbon group such as isobornyl (meth)acrylate; vinyl esters such as vinyl acetate and vinyl propionate; aromatic vinyl compounds such as styrene and vinyltoluene; ethylene, propylene olefins, such as butadiene, isoprene and isobutylene, or die
- the total content of structural units derived from the other monomer (A2) in the (meth)acrylic polymer (A) is, for example, 30% by weight or less, and may be 10% by weight or less, or 0 % by weight (not including the structural unit).
- the (meth)acrylic polymer (A) can be formed by polymerizing one or more of the above monomers by a known method.
- a monomer and a partial polymer of the monomer may be polymerized.
- Polymerization can be carried out, for example, by solution polymerization, emulsion polymerization, bulk polymerization, thermal polymerization, or active energy ray polymerization. Solution polymerization and active energy ray polymerization are preferred because they can form a pressure-sensitive adhesive sheet with excellent optical transparency.
- Polymerization is preferably carried out while avoiding contact of the monomer and/or partial polymer with oxygen. Polymerization in shutdown can be employed.
- the (meth)acrylic polymer (A) to be formed may be in any form such as a random copolymer, a block copolymer, or a graft copolymer.
- the polymerization system forming the (meth)acrylic polymer (A) may contain one or more polymerization initiators.
- the type of polymerization initiator can be selected depending on the polymerization reaction, and may be, for example, a thermal polymerization initiator or a photopolymerization initiator.
- Solvents used for solution polymerization include esters such as ethyl acetate and n-butyl acetate; aromatic hydrocarbons such as toluene and benzene; aliphatic hydrocarbons such as n-hexane and n-heptane; alicyclic hydrocarbons such as methylcyclohexane; and ketones such as methyl ethyl ketone and methyl isobutyl ketone.
- the solvent is not limited to the above examples.
- the solvent may be a mixed solvent of two or more solvents.
- Polymerization initiators used for solution polymerization are, for example, azo polymerization initiators, peroxide polymerization initiators, and redox polymerization initiators.
- Peroxide polymerization initiators are, for example, dibenzoyl peroxide and t-butyl permaleate.
- the azo polymerization initiator disclosed in JP-A-2002-69411 is preferable.
- the azo polymerization initiator for example, 2,2'-azobisisobutyronitrile (AIBN), 2,2'-azobis-2-methylbutyronitrile, 2,2'-azobis (2-methylpropion acid) dimethyl, 4,4'-azobis-4-cyanovaleric acid.
- AIBN 2,2'-azobisisobutyronitrile
- 2,2'-azobis-2-methylbutyronitrile 2,2'-azobis (2-methylpropion acid) dimethyl
- 4,4'-azobis-4-cyanovaleric acid is not limited to the above examples.
- the active energy rays used for active energy ray polymerization are, for example, ionizing radiation such as ⁇ -rays, ⁇ -rays, ⁇ -rays, neutron beams and electron beams, and ultraviolet rays.
- the active energy rays are preferably ultraviolet rays.
- Polymerization by irradiation with ultraviolet rays is also called photopolymerization.
- a polymerization system for active energy ray polymerization typically contains a photopolymerization initiator. Polymerization conditions for active energy polymerization are not limited as long as the (meth)acrylic polymer (A) is formed.
- Photopolymerization initiators include, for example, benzoin ether-based photopolymerization initiators, acetophenone-based photopolymerization initiators, ⁇ -ketol-based photopolymerization initiators, aromatic sulfonyl chloride-based photopolymerization initiators, and photoactive oxime-based photopolymerization initiators. , a benzoin-based photopolymerization initiator, a benzyl-based photopolymerization initiator, a benzophenone-based photopolymerization initiator, a ketal-based photopolymerization initiator, and a thioxanthone-based photopolymerization initiator.
- the photopolymerization initiator is not limited to the above examples.
- Benzoin ether-based photopolymerization initiators include, for example, benzoin methyl ether, benzoin ethyl ether, benzoin propyl ether, benzoin isopropyl ether, benzoin isobutyl ether, 2,2-dimethoxy-1,2-diphenylethan-1-one, anisolemethyl is ether.
- Acetophenone-based photopolymerization initiators include, for example, 2,2-diethoxyacetophenone, 2,2-dimethoxy-2-phenylacetophenone, 1-hydroxycyclohexylphenylketone, 4-phenoxydichloroacetophenone, 4-(t-butyl)dichloro Acetophenone.
- Examples of ⁇ -ketol photopolymerization initiators are 2-methyl-2-hydroxypropiophenone and 1-[4-(2-hydroxyethyl)phenyl]-2-methylpropan-1-one.
- the aromatic sulfonyl chloride photopolymerization initiator is, for example, 2-naphthalenesulfonyl chloride.
- a photoactive oxime-based photopolymerization initiator is, for example, 1-phenyl-1,1-propanedione-2-(o-ethoxycarbonyl)-oxime.
- a benzoin-based photopolymerization initiator is, for example, benzoin.
- a benzylic photopolymerization initiator is, for example, benzyl.
- benzophenone-based photopolymerization initiators examples include benzophenone, benzoylbenzoic acid, 3,3'-dimethyl-4-methoxybenzophenone, polyvinylbenzophenone, and ⁇ -hydroxycyclohexylphenyl ketone.
- a ketal photopolymerization initiator is, for example, benzyl dimethyl ketal.
- Thioxanthone-based photopolymerization initiators are, for example, thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2,4-dimethylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone, and dodecylthioxanthone.
- the amount of the photopolymerization initiator used is, for example, 0.01 to 1 part by weight, and may be 0.05 to 0.5 part by weight, based on 100 parts by weight of the total amount of the monomers.
- the weight average molecular weight (Mw) of the (meth)acrylic polymer (A) is, for example, 1,000,000 to 2,800,000, and from the viewpoint of the durability and heat resistance of the pressure-sensitive adhesive sheet, it is 1,200,000 or more, further 1,400,000 or more. may be
- the weight average molecular weight (Mw) of polymers and oligomers in this specification is a value (converted to polystyrene) based on GPC (gel permeation chromatography) measurement.
- the content of the (meth)acrylic polymer (A) in the pressure-sensitive adhesive composition (I) is, for example, 50% by weight or more, 60% by weight or more, 70% by weight or more, and further 80% by weight in terms of solid content. or more.
- the upper limit of the content is, for example, 99% by weight or less, and may be 97% by weight or less, 95% by weight or less, 93% by weight or less, or even 90% by weight or less.
- Cross-linking agent (B) is typically a polyfunctional cross-linking agent having two or more cross-linking reactive groups per molecule.
- the cross-linking agent (B) may be a tri- or higher functional cross-linking agent having 3 or more cross-linking reactive groups per molecule.
- the tri- or higher functional cross-linking agent (B) tends to form a self-polymer.
- the upper limit of the number of cross-linking reactive groups per molecule is 5, for example.
- the cross-linking agent (B) is, for example, an isocyanate-based cross-linking agent.
- the isocyanate-based cross-linking agent contains an isocyanate group as a cross-linking reactive group.
- the isocyanate-based cross-linking agent (B) may be an aromatic isocyanate compound, an alicyclic isocyanate compound, or an aliphatic isocyanate compound.
- aromatic isocyanate compounds that can be used for the cross-linking agent (B) include phenylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 2,2′-diphenylmethane diisocyanate, and 4,4′-diphenylmethane. diisocyanate, 4,4'-toluidine diisocyanate, 4,4'-diphenyl ether diisocyanate, 4,4'-diphenyl diisocyanate and 1,5-naphthalene diisocyanate, xylylene diisocyanate.
- alicyclic isocyanate compounds that can be used as the cross-linking agent (B) include 1,3-cyclopentene diisocyanate, 1,3-cyclohexane diisocyanate, 1,4-cyclohexane diisocyanate, isophorone diisocyanate, hydrogenated diphenylmethane diisocyanate, hydrogenated xyloxy diisocyanate, hydrogenated tolylene diisocyanate and hydrogenated tetramethylxylylene diisocyanate.
- aliphatic isocyanate compounds that can be used as the cross-linking agent (B) include trimethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, pentamethylene diisocyanate, 1,2-propylene diisocyanate, 1,3-butylene diisocyanate, and dodecamethylene diisocyanate. and 2,4,4-trimethylhexamethylene diisocyanate.
- the cross-linking agent (B) may be a derivative of the above isocyanate compound.
- derivatives include multimers (dimers, trimers, pentamers, etc.), adducts (adducts) obtained by adding polyhydric alcohols such as trimethylolpropane, urea modified products, and biuret modified products. , allophanate-modified, isocyanurate-modified, carbodiimide-modified, and urethane prepolymers obtained by addition to polyether polyol, polyester polyol, acrylic polyol, polybutadiene polyol, polyisoprene polyol, and the like.
- the cross-linking agent (B) is preferably an aromatic isocyanate compound and its derivatives, more preferably tolylene diisocyanate and its derivatives (in other words, tolylene diisocyanate-based (TDI-based) cross-linking agent).
- TDI-based cross-linking agents are superior to xylylene diisocyanate and its derivatives (in other words, xylylene diisocyanate-based (XDI-based) cross-linking agents) in terms of reaction uniformity.
- TDI-based cross-linking agent is an adduct of tolylene diisocyanate and a polyfunctional alcohol, and a more specific example is a trimethylolpropane/tolylene diisocyanate trimer adduct.
- a commercially available product can be used for the cross-linking agent (B).
- Examples of commercially available products include Millionate MT, Millionate MTL, Millionate MR-200, Millionate MR-400, Coronate L, Coronate HL and Coronate HX (manufactured by Tosoh; all trade names), Takenate D-102 and Takenate D. -103, Takenate D-110N, Takenate D-120N, Takenate D-140N, Takenate D-160N, Takenate D-165N, Takenate D-170HN, Takenate D-178N, Takenate 500 and Takenate 600 (manufactured by Mitsui Chemicals; Both are trade names).
- Coronate L Takenate D-102 and Takenate D-103 (all of which are trimethylolpropane/tolylene diisocyanate trimer adducts) can be preferably used.
- the amount of the cross-linking agent (B) in the adhesive composition (I) is 5 parts by weight or more, 6 parts by weight or more, and 7 parts by weight or more with respect to 100 parts by weight of the (meth)acrylic polymer (A). , 8 parts by weight or more, 9 parts by weight or more, 10 parts by weight or more, more than 10 parts by weight, or even 11 parts by weight or more.
- the upper limit of the compounding amount is, for example, 30 parts by weight or less, 28 parts by weight or less, 25 parts by weight or less, 23 parts by weight or less, 20 parts by weight or less, 19 parts by weight or less, 18 parts by weight or less, and further 15 parts by weight or less. may be
- the adhesive composition (I) may contain one or more cross-linking agents (B).
- cross-linking agents (B) When two or more cross-linking agents (B) are included, at least one cross-linking agent (B), for example, the self-polymer (C) of the cross-linking agent (B) with the largest blending amount, the distance Ra as long as it satisfies the range.
- the distance Ra may satisfy the above range for all self-polymers (C) of cross-linking agents (B) contained.
- the self-polymer (C) assumed in the calculation of the distance Ra is a single polymer composed of structural units derived from the cross-linking agent (B).
- the self-polymer of the cross-linking agent (B) actually contained in the pressure-sensitive adhesive sheet formed from the pressure-sensitive adhesive composition (I) contains structural units other than the structural units derived from the cross-linking agent (B).
- the pressure-sensitive adhesive sheet formed from the pressure-sensitive adhesive composition (I) has an interpenetrating network (IPN) structure of a cross-linked product of the (meth)acrylic polymer (A) and a self-polymer of the cross-linking agent (B).
- IPN interpenetrating network
- the IPN structure is suitable for improving the durability of the adhesive sheet.
- cross-linking agents (B) are peroxide-based cross-linking agents, epoxy-based cross-linking agents, imine-based cross-linking agents and polyfunctional metal chelates.
- the cross-linking agent (B) is preferably isocyanate-based.
- the total amount is 0.1 to 5 parts by weight with respect to 100 parts by weight of the (meth)acrylic polymer (A). parts are preferred, and 0.1 to 3 parts by weight, 0.1 to 2 parts by weight and 0.1 to 1 part by weight, in that order, are more preferred.
- the pressure-sensitive adhesive composition (I) may not contain a cross-linking agent (B) other than an isocyanate-based cross-linking agent, such as an epoxy-based cross-linking agent.
- the pressure-sensitive adhesive composition (I) may further contain a (meth)acrylic oligomer (D).
- the (meth)acrylic oligomer (D) can have the same composition as the (meth)acrylic polymer (A) described above, except that the weight average molecular weight (Mw) is different.
- the weight average molecular weight (Mw) of the (meth)acrylic oligomer (D) is, for example, 1000 or more, and may be 2000 or more, 3000 or more, or even 4000 or more.
- the upper limit of the weight average molecular weight (Mw) of the (meth)acrylic oligomer is, for example, 30,000 or less, and may be 15,000 or less, 10,000 or less, or even 7,000 or less.
- the (meth)acrylic oligomer (D) has, for example, one or more structural units derived from the following monomers: methyl (meth)acrylate, ethyl (meth)acrylate, propyl ( meth) acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, s-butyl (meth) acrylate, t-butyl (meth) acrylate, pentyl (meth) acrylate, isopentyl (meth) acrylate, hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, heptyl (meth)acrylate, octyl (meth)acrylate, isooctyl (meth)acrylate, nonyl (meth)acrylate, isononyl (meth)acrylate, decyl (meth)acrylate,
- the (meth)acrylic oligomer (D) preferably has structural units derived from a (meth)acrylic monomer having a relatively bulky structure.
- the adhesiveness of the adhesive sheet can be further enhanced.
- the acrylic monomer include alkyl (meth)acrylates having a branched alkyl group such as isobutyl (meth)acrylate and t-butyl (meth)acrylate; cyclohexyl (meth)acrylate and isobornyl (meth)acrylate.
- the monomer preferably has a cyclic structure, more preferably two or more cyclic structures.
- the (meth)acrylic oligomer (D) is polymerized and/or the pressure-sensitive adhesive sheet is formed when UV irradiation is performed, the progress of polymerization and/or formation is hardly inhibited. It preferably does not have an unsaturated bond, and for example, an alkyl (meth)acrylate having an alkyl group with a branched structure, or an ester of (meth)acrylic acid and an alicyclic alcohol can be used.
- the (meth)acrylic oligomer (D) include a copolymer of butyl acrylate, methyl acrylate and acrylic acid, a copolymer of cyclohexyl methacrylate and isobutyl methacrylate, and a copolymer of cyclohexyl methacrylate and isobornyl methacrylate.
- Copolymers of cyclohexyl methacrylate and acryloylmorpholine Copolymers of cyclohexyl methacrylate and diethylacrylamide, copolymers of 1-adamantyl acrylate and methyl methacrylate, copolymers of dicyclopentanyl methacrylate and isobornyl methacrylate.
- Polymer copolymer of methyl methacrylate and at least one selected from dicyclopentanyl methacrylate, cyclohexyl methacrylate, isobornyl methacrylate, isobornyl acrylate and cyclopentanyl methacrylate, homopolymer of dicyclopentanyl acrylate , a homopolymer of 1-adamantyl methacrylate and a homopolymer of 1-adamantyl acrylate.
- the polymerization method for the (meth)acrylic polymer (A) described above can be employed for the polymerization of the (meth)acrylic oligomer (D).
- the amount thereof is, for example, 70 parts by weight or less with respect to 100 parts by weight of the (meth)acrylic polymer (A), It may be 50 parts by weight or less, or even 40 parts by weight or less.
- the lower limit of the amount to be blended is, for example, 1 part by weight or more, 2 parts by weight or more, and may be 3 parts by weight or more with respect to 100 parts by weight of the (meth)acrylic polymer (A).
- the pressure-sensitive adhesive composition (I) may not contain the (meth)acrylic oligomer (D).
- the pressure-sensitive adhesive composition (I) may contain other additives.
- additives include silane coupling agents, colorants such as pigments and dyes, surfactants, plasticizers, tackifiers, surface lubricants, leveling agents, rework improvers, softeners, antioxidants, aging Inhibitors, light stabilizers, ultraviolet absorbers, polymerization inhibitors, antistatic agents (ionic compounds such as alkali metal salts, ionic liquids, ionic solids, etc.), inorganic fillers, organic fillers, powders such as metal powders , particles, and foils.
- the additive can be blended in an amount of, for example, 10 parts by weight or less, preferably 5 parts by weight or less, and more preferably 1 part by weight or less per 100 parts by weight of the (meth)acrylic polymer (A).
- silane coupling agents are 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldiethoxysilane and 2-(3,4-epoxycyclohexyl)ethyl Epoxy group-containing silane coupling agents such as trimethoxysilane; 3-aminopropyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, 3-triethoxysilyl-N-(1,3 -dimethylbutylidene)propylamine and amino group-containing silane coupling agents such as N-phenyl- ⁇ -aminopropyltrimethoxysilane; ) acrylic group-containing silane coupling agents; and isocyanate group-containing silane coupling agents such as 3-isocyanatopropyltriethoxysilane.
- the amount is, for example, 5 parts by weight or less, 3 parts by weight or less, relative to 100 parts by weight of the (meth)acrylic polymer (A), It may be 1 part by weight or less, 0.5 parts by weight or less, 0.2 parts by weight or less, 0.1 parts by weight or less, or even 0.05 parts by weight or less.
- the adhesive composition (I) may not contain a silane coupling agent.
- Types of the pressure-sensitive adhesive composition (I) are, for example, emulsion type, solvent type (solution type), active energy ray-curable type (light-curing type), and heat-melting type (hot-melt type).
- the pressure-sensitive adhesive composition (I) may be solvent-based from the viewpoint of forming a pressure-sensitive adhesive sheet with superior durability.
- the solvent-based pressure-sensitive adhesive composition (I) may not contain a photocuring agent such as an ultraviolet curing agent.
- the pressure-sensitive adhesive sheet 1 in FIG. 1 is formed from the pressure-sensitive adhesive composition (I).
- the adhesive sheet 1 contains, for example, a crosslinked product of (meth)acrylic polymer (A).
- the adhesive sheet 1 can be formed from the adhesive composition (I) as follows.
- the pressure-sensitive adhesive composition (I) or a mixture of the pressure-sensitive adhesive composition (I) and a solvent is applied to the base film, and the formed coating film is dried to form the pressure-sensitive adhesive sheet 1. .
- the pressure-sensitive adhesive composition (I) is thermally cured by heat during drying.
- the active energy ray-curable type for example, a monomer (group) that becomes a (meth)acrylic polymer (A) by polymerization, a cross-linking agent (B), and, if necessary, a monomer A mixture of the partial polymer of (group), polymerization initiator, oligomer (D), other cross-linking agent, additive, solvent, etc.
- the base film may be a film (release film) whose coating surface has been subjected to release treatment.
- the adhesive sheet 1 formed on the base film can be transferred to any layer.
- the base film may be an optical film, and in this case, an optical laminate including the adhesive sheet 1 and the optical film is obtained.
- Coating is, for example, roll coating, kiss roll coating, gravure coating, reverse coating, roll brushing, spray coating, dip roll coating, bar coating, knife coating, air knife coating, curtain coating, lip coating, extrusion coating using a die coater, or the like. can be implemented by
- the drying temperature after coating is, for example, 40 to 200°C.
- the drying temperature may be 160° C. or lower, 150° C. or lower, 130° C. or lower, 120° C. or lower, or even 100° C. or lower.
- the adhesive sheet 1 having excellent durability can be obtained.
- the adhesive sheet 1 may be obtained by drying the coating film of the adhesive composition (I) at a temperature of 130° C. or lower, 120° C. or lower, or further 100° C. or lower.
- the drying time is, for example, 5 seconds to 20 minutes, and may be 5 seconds to 10 minutes, or even 10 seconds to 5 minutes.
- the drying temperature and drying time when drying after coating may be within the above ranges.
- composition and mixture to be applied to the base film preferably have a viscosity suitable for handling and coating. Therefore, for the active energy ray-curable type, the mixture to be applied preferably contains a partial polymer of the monomer (group).
- the coated surface is subjected to release treatment with a silicone compound.
- the thickness of the adhesive sheet 1 is, for example, 1 to 200 ⁇ m, 5 to 150 ⁇ m, and may be 10 to 100 ⁇ m.
- the storage elastic modulus G′ (25° C.) of the adhesive sheet 1 is, for example, 0.15 MPa or higher, 0.2 MPa or higher, 0.25 MPa or higher, 0.3 MPa or higher, 0.4 MPa or higher, 0.5 MPa or higher, 0.5 MPa or higher, and 0.2 MPa or higher. It may be 6 MPa or more, 0.7 MPa or more, 0.8 MPa or more, 0.9 MPa or more, 1.0 MPa or more, 1.1 MPa or more, or even 1.2 MPa or more.
- the upper limit of the storage modulus G' (25°C) is, for example, 5 MPa or less, and may be 3.0 MPa or less, 2.5 MPa or less, or even 2.0 MPa or less.
- the pressure-sensitive adhesive sheet 1 having a storage elastic modulus G' within the above range is more suitable for suppressing changes in the dimensions of the optical film.
- the storage elastic modulus (25° C.) of PSA Sheet 1 can be evaluated by the following method. First, a sample for measurement made of the material constituting the adhesive sheet 1 is prepared. The shape of the measurement sample is disc-shaped. The measurement sample has a bottom diameter of 8 mm and a thickness of 2 mm. A sample for measurement may be obtained by punching a disc-shaped laminate from a laminate in which a plurality of pressure-sensitive adhesive sheets 1 are laminated. Next, a dynamic viscoelasticity measurement is performed on the measurement sample. For dynamic viscoelasticity measurement, for example, ARES-G2 manufactured by TA Instruments can be used. From the results of the dynamic viscoelasticity measurement, the storage elastic modulus G' of the pressure-sensitive adhesive sheet 1 at 25°C can be specified. The conditions for the dynamic viscoelasticity measurement are as follows. ⁇ Measurement conditions Frequency: 1Hz Deformation mode: Torsion Measurement temperature: -70°C to 150°C Heating rate: 5°C/min
- the gel fraction of the adhesive sheet 1 is, for example, 60% or more, and may be 65% or more, or even 70% or more.
- the upper limit of the gel fraction is, for example, 99% or less, and may be 98% or less, or even 95% or less.
- the adhesive sheet 1 having a gel fraction within the above range is more suitable for suppressing dimensional change of the optical film.
- the gel fraction of the adhesive sheet 1 can be evaluated by the following method. First, about 0.2 g is scraped from Adhesive Sheet 1 to obtain a small piece. Next, the obtained small piece is wrapped with an expanded porous membrane of polytetrafluoroethylene (NTF1122 manufactured by Nitto Denko, average pore size 0.2 ⁇ m) and tied with a kite string to obtain a test piece. Next, the weight A of the obtained test piece is measured. Weight A is the sum of the weights of the adhesive sheet piece, the stretched porous membrane and the kite string. The total weight B of the stretched porous membrane and the kite string used is measured in advance.
- NTF1122 polytetrafluoroethylene
- the haze of the adhesive sheet 1 when the thickness is 15 ⁇ m is, for example, 1.1% or less, 1% or less, 0.9% or less, 0.8% or less, 0.7% or less, and further 0.6%. % or less.
- the lower limit of haze is, for example, 0.1% or more.
- the adhesive sheet 1 can be used for optical applications, for example.
- the pressure-sensitive adhesive sheet 1 may be used for optical laminates and/or image display devices.
- the pressure-sensitive adhesive sheet 1 is suitable for use in image display devices, such as an image display device with a narrow frame and an image display device with a relatively large screen size, for which suppression of dimensional change in the optical film is particularly required. .
- image display devices such as an image display device with a narrow frame and an image display device with a relatively large screen size, for which suppression of dimensional change in the optical film is particularly required.
- optical laminate An example of the optical laminate of this embodiment is shown in FIG.
- the optical layered body 10A of FIG. 2 includes an adhesive sheet 1 and an optical film 2. As shown in FIG. The adhesive sheet 1 and the optical film 2 are laminated together. 10 A of optical laminated bodies can be used as an optical film with an adhesive sheet.
- optical film 2 examples are a polarizing plate, a retardation film, and a laminated film containing a polarizing plate and/or a retardation film.
- the optical film 2 is not limited to the above examples.
- the optical film 2 may contain a film made of glass.
- a polarizing plate includes a polarizer.
- a polarizer protective film may be bonded to at least one surface of the polarizer. Any pressure-sensitive adhesive or adhesive can be used for joining the polarizer and the polarizer protective film.
- the adhesive sheet 1 may be used for bonding.
- a polarizer is typically a polyvinyl alcohol (PVA) film in which iodine is oriented by stretching such as stretching in air (dry stretching) or stretching in boric acid solution.
- PVA polyvinyl alcohol
- a retardation film is a film that has birefringence in the in-plane direction and/or the thickness direction.
- a retardation film is, for example, a stretched resin film or a film in which a liquid crystal material is oriented and fixed.
- the retardation film includes a ⁇ / 4 plate, a ⁇ / 2 plate, an antireflection retardation film (see, for example, paragraphs 0221, 0222, 0228 of JP-A-2012-133303), a viewing angle compensation retardation film (for example, JP-A-2012-133303, paragraphs 0225 and 0226), obliquely oriented retardation film for viewing angle compensation (eg, JP-A-2012-13303, paragraph 0227).
- the retardation film is not limited to the above examples as long as it has birefringence in the in-plane direction and/or the thickness direction.
- the retardation value of the retardation film, the arrangement angle, the three-dimensional birefringence, whether it is a single layer or a multilayer, and the like are not limited.
- a known film can be used as the retardation film.
- the thickness of the optical film 2 is, for example, 1 to 200 ⁇ m.
- the thickness of the optical film 2, which is a polarizing plate, is, for example, 1 to 150 ⁇ m, and may be 100 ⁇ m or less, 75 ⁇ m or less, 50 ⁇ m or less, 20 ⁇ m or less, or even 15 ⁇ m or less.
- the lower limit of the thickness may be 10 ⁇ m or more, 20 ⁇ m or more, 50 ⁇ m or more, 75 ⁇ m or more, or even 100 ⁇ m or more.
- the optical film 2 may be a single layer or a laminated film composed of two or more layers.
- the adhesive sheet 1 may be used for joining the layers.
- FIG. 3 Another example of the optical laminate of this embodiment is shown in FIG.
- the optical layered body 10B of FIG. 3 has a layered structure in which a release liner 3, an adhesive sheet 1 and an optical film 2 are layered in this order. By peeling off the release liner 3, the optical laminate 10B can be used as an optical film with an adhesive sheet.
- the release liner 3 is typically a resin film.
- resins that make up the release liner 3 are polyesters such as polyethylene terephthalate (PET), polyolefins such as polyethylene and polypropylene, polycarbonates, acrylics, polystyrenes, polyamides, and polyimides.
- PET polyethylene terephthalate
- the surface of the release liner 3 that contacts the adhesive sheet 1 may be subjected to a release treatment.
- the release treatment is, for example, treatment with a silicone compound.
- the release liner 3 is not limited to the above example.
- the release liner 3 is peeled off when the optical layered body 10B is used, for example, when attached to the image forming layer.
- the optical laminate 10C of FIG. 4 has a laminate structure in which a release liner 3, an adhesive sheet 1, a retardation film 2A, an interlayer adhesive 4 and a polarizing plate 2B are laminated in this order. After peeling off the release liner 3, the optical layered body 10C can be used by attaching it to, for example, an image forming layer.
- a known adhesive can be used for the interlayer adhesive 4 .
- the adhesive sheet 1 may be used as the interlayer adhesive 4 .
- the optical laminate 10D of FIG. 5 has a laminate structure in which a release liner 3, an adhesive sheet 1, a retardation film 2A, an interlayer adhesive 4, a polarizing plate 2B and a protective film 5 are laminated in this order. After peeling off the release liner 3, the optical layered body 10D can be used by attaching it to, for example, an image forming layer.
- the protective film 5 has a function of protecting the outermost optical film 2 (polarizing plate 2B) during distribution and storage of the optical layered body 10D and when the optical layered body 10D is incorporated in an image display device. Moreover, it may be the protective film 5 that functions as a window to an external space when incorporated in the image display device.
- Protective film 5 is typically a resin film.
- the resin constituting the protective film 5 is, for example, polyester such as PET, polyolefin such as polyethylene and polypropylene, acrylic, cycloolefin, polyimide, and polyamide, preferably polyester.
- the protective film 5 is not limited to the above examples.
- the protective film 5 may be a glass film or a laminated film containing a glass film.
- the protective film 5 may be subjected to surface treatments such as antiglare, antireflection, and antistatic.
- the protective film 5 may be bonded to the optical film 2 with any adhesive. Bonding with the adhesive sheet 1 is also possible.
- the optical layered body of the present embodiment can be distributed and stored, for example, as a wound body in which a strip-shaped optical layered body is wound, or as a sheet-shaped optical layered body.
- the optical laminate of this embodiment is typically used in an image display device.
- the image display device is, for example, an EL display such as a liquid crystal display, an organic EL display and an inorganic EL display.
- the image display device 11 in FIG. 6 includes a substrate 7, an image forming layer (for example, an organic EL layer or a liquid crystal layer) 6, an adhesive sheet 1, a retardation film 2A, an interlayer adhesive 4, a polarizing plate 2B and a protective film 5 in this order. It has a laminated structure.
- the image display device 11 has the optical laminates 10A, 10B, 10C, and 10D of FIGS. 2 to 5 (excluding the release liner 3).
- the substrate 7 and the image forming layer 6 may have the same configurations as those of the substrate and the image forming layer provided in a known image display device.
- the image display device 11 in FIG. 6 may be an organic EL display or a liquid crystal display. However, the image display device 11 is not limited to this example.
- the image display device 11 may be an electroluminescence (EL) display, a plasma display (PD), a field emission display (FED: Field Emission Display), or the like.
- EL electroluminescence
- PD plasma display
- FED Field Emission Display
- the image display device 11 may be used for home appliance use, vehicle use, public information display (PID) use, and the like.
- the image display device of this embodiment can have any configuration as long as it includes the optical layered body of this embodiment.
- Storage elastic modulus G' (25°C) The storage elastic modulus G' (25°C) of the pressure-sensitive adhesive sheet was evaluated by the method described above. However, a sample for measurement was prepared by punching out a laminate obtained by stacking the produced pressure-sensitive adhesive sheets into a disc shape. ARES-G2 manufactured by TA Instruments was used for the dynamic viscoelasticity measurement of the measurement sample.
- Humidification durability (corresponding to an accelerated durability test) of the PSA sheet was evaluated by the following method. First, a pressure-sensitive adhesive sheet-attached circularly polarizing plate having the pressure-sensitive adhesive sheets prepared in Examples and Comparative Examples on one exposed surface was formed. Next, a circularly polarizing plate was fixed to the surface of a glass plate (Eagle XG manufactured by Corning) via the adhesive sheet. Fixing of the circularly polarizing plate was performed in an atmosphere of 23° C. and 50% RH. Next, after treatment in an autoclave at 50 ° C.
- polarizing plate P1> (Production of polarizer) A long polyvinyl alcohol (PVA) resin film (manufactured by Kuraray, product name “PE3000”, thickness 30 ⁇ m) is uniaxially stretched in the longitudinal direction using a roll stretching machine (total stretching ratio 5.9 times) at the same time. , swelling, dyeing, cross-linking, washing and drying were sequentially performed on the resin film to prepare a polarizer having a thickness of 12 ⁇ m. In the swelling treatment, the resin film was stretched 2.2 times while being treated with pure water at 20°C.
- PVA polyvinyl alcohol
- the resin film was stretched 1.4 times while being treated with an aqueous solution containing iodine and potassium iodide at a weight ratio of 1:7 at 30°C.
- the iodine concentration in the aqueous solution was adjusted so that the single transmittance of the polarizer to be produced was 45.0%.
- a two-step process was employed for the cross-linking treatment.
- the resin film was stretched 1.2 times while being treated with an aqueous solution of boric acid and potassium iodide at 40°C.
- the content of boric acid in the aqueous solution used for the first-stage cross-linking treatment was 5.0% by weight, and the content of potassium iodide was 3.0% by weight.
- the resin film was stretched 1.6 times while being treated with an aqueous solution of boric acid and potassium iodide at 65°C.
- the content of boric acid in the aqueous solution used in the second-stage cross-linking treatment was 4.3% by weight, and the content of potassium iodide was 5.0% by weight.
- a potassium iodide aqueous solution at 20° C. was used for the cleaning treatment.
- the content of potassium iodide in the aqueous solution used for the cleaning treatment was 2.6% by weight.
- the drying treatment was performed under drying conditions of 70° C. and 5 minutes.
- polarizing plate P1 Preparation of polarizing plate P1
- TAC triacetyl cellulose
- KC2UA product name “KC2UA”, thickness 25 ⁇ m
- a hard coat 7 ⁇ m thick
- ⁇ Preparation of retardation film R1> (Preparation of first retardation film) Isosorbide (ISB) 26.2 parts by weight, 9,9-[4-(2-hydroxyethoxy)phenyl]fluorene (BHEPF) 100.5 parts by weight, 1,4-cyclohexanedimethanol (1,4-CHDM) 10 .7 parts by weight, 105.1 parts by weight of diphenyl carbonate (DPC), and 0.591 parts by weight of cesium carbonate (0.2% by weight aqueous solution) as a catalyst were charged into a reaction vessel and dissolved under a nitrogen atmosphere ( about 15 minutes). At this time, the temperature of the heat medium in the reaction vessel was set at 150° C., and stirring was carried out as necessary.
- the pressure inside the reaction vessel was reduced to 13.3 kPa, and the temperature of the heat medium was raised to 190° C. in 1 hour. Phenol generated as the temperature of the heat medium increased was discharged out of the reaction vessel (the same applies hereinafter).
- the pressure in the reaction vessel was changed to 6.67 kPa, and the temperature of the heat medium was raised to 230° C. in 15 minutes.
- the stirring torque of the stirrer provided in the reaction vessel increased, the temperature of the heat medium was raised to 250° C. in 8 minutes, and the pressure in the reaction vessel was reduced to 0.200 kPa or less.
- a single screw extruder manufactured by Isuzu Kakoki, screw diameter 25 mm, cylinder set temperature 220 ° C.), T die (width 200 mm, set temperature 220 ° C.), chill roll A long resin film having a thickness of 120 ⁇ m was obtained using a film forming apparatus equipped with a set temperature of 120 to 130° C. and a winder. Next, the obtained resin film was stretched in the width direction with a tenter stretching machine at a stretching temperature of 137 to 139° C. and a stretching ratio of 2.5 to obtain a first retardation film.
- a side chain type liquid crystal polymer (weight average molecular weight 5000) represented by the following chemical formula (I) (where 65 and 35 are mol% of each structural unit), a polymerizable liquid crystal exhibiting a nematic liquid crystal phase (manufactured by BASF) , trade name “Paliocolor LC242”) 80 parts by weight, and a photopolymerization initiator (manufactured by Ciba Specialty Chemicals, trade name “Irgacure 907”) 5 parts by weight are dissolved in 200 parts by weight of cyclopentanone to form a liquid crystal coating liquid.
- a side chain type liquid crystal polymer (weight average molecular weight 5000) represented by the following chemical formula (I) (where 65 and 35 are mol% of each structural unit)
- a polymerizable liquid crystal exhibiting a nematic liquid crystal phase manufactured by BASF
- Paliocolor LC242 trade name “Paliocolor LC242”
- a norbornene-based resin film manufactured by Nippon Zeon, trade name “Zeonex”
- Zeonex which is a base film
- the coating film was cured by irradiation with ultraviolet rays to form a liquid crystal solidified layer (thickness: 0.58 ⁇ m) as a second retardation film on the substrate film.
- the polymerization reaction was allowed to proceed for 7 hours while maintaining the liquid temperature in the flask around 55°C.
- ethyl acetate was added to the resulting reaction solution to adjust the solid content concentration to 30% by weight to obtain a solution of a (meth)acrylic polymer used as an interlaminar pressure-sensitive adhesive.
- the weight average molecular weight of the obtained polymer was 2,200,000.
- trimethylolpropane/tolylene diisocyanate trimer adduct manufactured by Tosoh, trade name "Coronate L" is added to 100 parts by weight of the solid content of the solution.
- the pressure-sensitive adhesive composition PSA1 prepared above is applied to the release surface of a polyethylene terephthalate (PET) film (manufactured by Mitsubishi Chemical Polyester Film Co., Ltd., MRF38) having a thickness of 38 ⁇ m, which is a release film having a silicone-treated release surface. It was coated so that the thickness of the layer after drying was 12 ⁇ m, and dried at 155° C. for 1 minute to form an interlayer pressure-sensitive adhesive layer. Next, the formed interlayer pressure-sensitive adhesive layer was transferred to the protective layer (no hard coat) side of the polarizing plate P1 to obtain a polarizing plate with an interlayer pressure-sensitive adhesive layer.
- PET polyethylene terephthalate
- MRF38 silicone-treated release surface
- each pressure-sensitive adhesive sheet prepared in Examples and Comparative Examples was transferred from the release film and pasted.
- the polarizing plate with an interlayer pressure-sensitive adhesive layer prepared above was attached to the first retardation film side of the retardation film R1 via the interlayer pressure-sensitive adhesive layer to obtain a circularly polarizing plate with an pressure-sensitive adhesive sheet.
- the attachment of the retardation film R1 and the polarizing plate with an interlayer pressure-sensitive adhesive layer is performed by adjusting the angle formed by the slow axis of the first retardation film and the absorption axis of the polarizer when viewed from the side of the first retardation film. was 45 degrees counterclockwise.
- the (meth)acrylic polymer (A-1) had a weight average molecular weight (Mw) of 2,200,000.
- (Synthesis example 2) A (meth)acrylic polymer (meth)acrylic polymer ( A-2) solution was obtained.
- the (meth)acrylic polymer (A-2) had a weight average molecular weight (Mw) of 2,200,000.
- (Synthesis Example 6) A solution of (meth)acrylic polymer (A-6) was prepared in the same manner as in Synthesis Example 1, except that the monomers used were changed to 89.9 parts by weight of BA, 10.0 parts by weight of AA and 0.1 parts by weight of HBA. got The (meth)acrylic polymer (A-6) had a weight average molecular weight (Mw) of 2,600,000.
- Table 1 summarizes the types and charged amounts of the monomers and polymerization initiators used in Synthesis Examples 1 to 6, and the weight average molecular weight (Mw) of the resulting polymer.
- the pressure-sensitive adhesive sheets of Examples in which the amount of the cross-linking agent (B) was 5 parts by weight or more and the distance Ra was 12.3 or less had a larger dimension than the pressure-sensitive adhesive sheets of Comparative Examples. It is suitable for suppressing changes in the temperature and exhibits high durability.
- an adhesive sheet for use in image display devices can be formed.
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Abstract
Description
(メタ)アクリル系ポリマー(A)を主成分として含み、
架橋剤(B)を更に含み、
前記架橋剤(B)の配合量は、前記(メタ)アクリル系ポリマー(A)100重量部に対して5重量部以上であり、
前記架橋剤(B)の自己重合体(C)を想定したときに、前記(メタ)アクリル系ポリマー(A)と前記自己重合体(C)との間のハンセン溶解度パラメータ(HSP)の距離Raが12.3以下である、粘着剤組成物、
を提供する。
上記本発明の粘着剤組成物から形成された粘着シート、
を提供する。
上記本発明の粘着シートと、光学フィルムと、を含む、光学積層体、
を提供する。
上記本発明の光学積層体を備える画像表示装置、
を提供する。
本実施形態の粘着剤組成物(I)は、(メタ)アクリル系ポリマー(A)及び架橋剤(B)を含む。(メタ)アクリル系ポリマー(A)は、主成分として粘着剤組成物(I)に含まれる。換言すれば、粘着剤組成物(I)は、アクリル系粘着剤組成物である。主成分とは、組成物においても最も含有率の大きな成分を意味する。主成分の含有率は、例えば50重量%以上であり、60重量%以上、70重量%以上、73重量%以上、更には75重量%以上であってもよい。
(メタ)アクリル系ポリマー(A)は、炭素数1~30のアルキル基を側鎖に有する(メタ)アクリル系単量体(A1)に由来する構成単位を主たる単位として有することが好ましい。アルキル基は、直鎖状であっても分岐を有していてもよい。(メタ)アクリル系ポリマー(A)は、(メタ)アクリル系単量体(A1)に由来する構成単位を1種又は2種以上有していてもよい。(メタ)アクリル系単量体(A1)の例は、メチル(メタ)アクリレート、エチル(メタ)アクリレート、n-ブチル(メタ)アクリレート、s-ブチル(メタ)アクリレート、t-ブチル(メタ)アクリレート、イソブチル(メタ)アクリレート、n-ペンチル(メタ)アクリレート、イソペンチル(メタ)アクリレート、n-へキシル(メタ)アクリレート、イソヘキシル(メタ)アクリレート、イソヘプチル(メタ)アクリレート、2-エチルヘキシル(メタ)アクリレート、n-オクチル(メタ)アクリレート、イソオクチル(メタ)アクリレート、n-ノニル(メタ)アクリレート、イソノニル(メタ)アクリレート、n-デシル(メタ)アクリレート、イソデシル(メタ)アクリレート、n-ドデシル(メタ)アクリレート(ラウリル(メタ)アクリレート)、n-トリデシル(メタ)アクリレート及びn-テトラデシル(メタ)アクリレートである。本明細書において「主たる単位」とは、ポリマーが有する全構成単位のうち、例えば50重量%以上、好ましくは60重量%以上、より好ましくは70重量%以上、更に好ましくは80重量%以上を占める単位を意味する。
架橋剤(B)は、典型的には、1分子あたり2以上の架橋反応基を有する多官能性架橋剤である。架橋剤(B)は、1分子あたり3以上の架橋反応基を有する3官能以上の架橋剤であってもよい。3官能以上の架橋剤(B)は、自己重合体を形成しやすい。1分子あたりの架橋反応基の数の上限は、例えば5である。
粘着剤組成物(I)は、(メタ)アクリル系オリゴマー(D)を更に含んでいてもよい。
粘着剤組成物(I)は、その他の添加剤を含んでいてもよい。添加剤の例は、シランカップリング剤、顔料及び染料等の着色剤、界面活性剤、可塑剤、粘着性付与剤、表面潤滑剤、レベリング剤、リワーク向上剤、軟化剤、酸化防止剤、老化防止剤、光安定剤、紫外線吸収剤、重合禁止剤、帯電防止剤(イオン性化合物であるアルカリ金属塩、イオン液体、イオン固体等)、無機充填材、有機充填材、金属粉等の粉体、粒子、箔状物である。添加剤は、(メタ)アクリル系ポリマー(A)100重量部に対して、例えば10重量部以下、好ましくは5重量部以下、より好ましくは1重量部以下の範囲で配合できる。
本実施形態の粘着シートの一例を図1に示す。図1の粘着シート1は、粘着剤組成物(I)から形成されたものである。粘着シート1は、例えば、(メタ)アクリル系ポリマー(A)の架橋物を含む。粘着シート1は、粘着剤組成物(I)から、以下のように形成できる。
・測定条件
周波数:1Hz
変形モード:ねじり
測定温度:-70℃~150℃
昇温速度:5℃/分
本実施形態の光学積層体の一例を図2に示す。図2の光学積層体10Aは、粘着シート1と光学フィルム2とを含む。粘着シート1と光学フィルム2とは互いに積層されている。光学積層体10Aは、粘着シート付き光学フィルムとして使用できる。
本実施形態の画像表示装置の一例を図6に示す。図6の画像表示装置11は、基板7、画像形成層(例えば有機EL層又は液晶層)6、粘着シート1、位相差フィルム2A、層間粘着剤4、偏光板2B及び保護フィルム5がこの順に積層された積層構造を有している。画像表示装置11は、図2~5の光学積層体10A,10B,10C,10Dを有している(ただし、はく離ライナー3を除く)。基板7及び画像形成層6は、公知の画像表示装置が備える基板及び画像形成層と、それぞれ同様の構成を有していればよい。
(メタ)アクリル系ポリマーの重量平均分子量(Mw)は、GPCにより、以下の条件にて評価した。
・分析装置:Waters製、Acquity APC
・カラム:東ソー製、G7000HXL+GMHXL+GMHXL
・カラム温度:40℃
・溶離液:テトラヒドロフラン(酸添加)
・流速:0.8mL/分
・注入量:100μL
・検出器:示差屈折計(RI)
・標準試料:Agilent製、ポリスチレン(PS)
距離Raは、上述の方法により算出した。ソフトウェアには、HSPiP(version 5)を用いた。
粘着シートの貯蔵弾性率G’(25℃)は、上述の方法により評価した。ただし、測定用サンプルは、作製した粘着シートを重ねて得た積層体を円盤状に打ち抜いて準備した。測定用サンプルに対する動的粘弾性測定には、TA Instruments製、ARES-G2を用いた。
粘着シート(厚さ15μm)のヘイズは、JIS K7136:1981に準拠し、スガ試験機製のヘイズメーターHZ-V3を用いて、25℃の雰囲気で測定した。なお、測定は、松浪硝子工業製スライドグラスS012140(厚さ1.3mm)上に、評価対象の粘着シート(厚さ15μm)を貼り合わせた状態で実施した。
粘着シートの加湿耐久性(耐久性の加速試験に相当)は、以下の方法により評価した。最初に、実施例及び比較例で作製した各粘着シートを一方の露出面に備える粘着シート付き円偏光板を形成した。次に、上記粘着シートを介して、ガラス板(コーニング製、イーグルXG)の表面に円偏光板を固定した。円偏光板の固定は、23℃及び50%RHの雰囲気で実施した。次に、50℃及び5気圧(絶対圧)のオートクレーブにて15分処理した後、23℃に冷えるまで放置して、ガラス板への円偏光板の接合を安定させた後、60℃及び95%RHの加熱加湿雰囲気に500時間放置した。放置後、23℃及び50%RHの雰囲気に戻し、ガラス板からの円偏光板の剥がれや、ガラス板と円偏光板との間に発泡が生じていないかを目視により確認して、以下のように、加湿耐久性を評価した。
A:発泡や剥がれ等の外観上の変化がみられない。
B:端部において、単独の剥がれ又は発泡がわずかにみられるが、実用上、問題ない範囲にある。
C:端部において、連続した剥がれ又は発泡がわずかにみられるが、実用上、問題ない範囲にある。
D:端部に著しい剥がれ又は発泡がみられ、実用上、問題がある。
(偏光子の作製)
長尺状のポリビニルアルコール(PVA)系樹脂フィルム(クラレ製、製品名「PE3000」、厚さ30μm)を、ロール延伸機を用いて長手方向に一軸延伸(総延伸倍率5.9倍)すると同時に、上記樹脂フィルムに対して膨潤、染色、架橋、洗浄及び乾燥の各処理を順に施して、厚さ12μmの偏光子を作製した。膨潤処理では、上記樹脂フィルムを20℃の純水で処理しながら2.2倍延伸した。染色処理では、ヨウ素及びヨウ化カリウムを重量比1:7で含有する30℃の水溶液で処理しながら、上記樹脂フィルムを1.4倍延伸した。水溶液中のヨウ素濃度は、作製する偏光子の単体透過率が45.0%となるように調整された。架橋処理には、2段階処理を採用した。1段階目の架橋処理では、ホウ酸及びヨウ化カリウムを溶解させた40℃の水溶液で処理しながら、上記樹脂フィルムを1.2倍延伸した。1段階目の架橋処理に用いた水溶液におけるホウ酸の含有率は5.0重量%、ヨウ化カリウムの含有率は3.0重量%とした。2段階目の架橋処理では、ホウ酸及びヨウ化カリウムを溶解させた65℃の水溶液で処理しながら、上記樹脂フィルムを1.6倍延伸した。2段階目の架橋処理に用いた水溶液におけるホウ酸の含有率は4.3重量%、ヨウ化カリウムの含有率は5.0重量%とした。洗浄処理には、20℃のヨウ化カリウム水溶液を用いた。洗浄処理に用いた水溶液におけるヨウ化カリウムの含有率は2.6重量%とした。乾燥処理は、70℃及び5分間の乾燥条件で実施した。
上記作製した偏光子の各主面に、それぞれ、トリアセチルセルロース(TAC)フィルム(コニカミノルタ製、製品名「KC2UA」、厚さ25μm)をポリビニルアルコール系接着剤により貼り合わせた。ただし、一方の主面に貼り合わせたTACフィルムには、偏光子側とは反対側の主面にハードコート(厚さ7μm)が形成されていた。このようにして、ハードコート付き保護層/偏光子/保護層(ハードコートなし)の構成を有する偏光板P1を得た。
(第1の位相差フィルムの作製)
イソソルビド(ISB)26.2重量部、9,9-[4-(2-ヒドロキシエトキシ)フェニル]フルオレン(BHEPF)100.5重量部、1,4-シクロヘキサンジメタノール(1,4-CHDM)10.7重量部、ジフェニルカーボネート(DPC)105.1重量部、及び触媒として炭酸セシウム(0.2重量%水溶液)0.591重量部を反応容器に投入し、窒素雰囲気下にて溶解させた(約15分)。このとき、反応容器の熱媒温度は150℃とし、必要に応じて撹拌を実施した。次に、反応容器内の圧力を13.3kPaに減圧すると共に、熱媒温度を190℃まで1時間で上昇させた。熱媒温度の上昇に伴って発生するフェノールは、反応容器外へ抜き出した(以下、同じ)。次に、反応容器内の温度を190℃で15分保持した後、反応容器内の圧力を6.67kPaに変更すると共に、熱媒温度を230℃まで15分で上昇させた。反応容器が備える撹拌機の撹拌トルクが上昇してきた時点で、熱媒温度を250℃まで8分で上昇させ、更に、反応容器内の圧力を0.200kPa以下とした。所定の撹拌トルクに到達後、反応を終了させ、生成した反応物を水中に押し出してペレット化した。このようにして、BHEPF/ISB/1,4-CHDM=47.4モル%/37.1モル%/15.5モル%の組成を有するポリカーボネート樹脂を得た。得られたポリカーボネート樹脂のガラス転移温度は136.6℃であり、還元粘度は0.395dL/gであった。
下記化学式(I)(式中、65及び35は、各構成単位のモル%)により示される側鎖型液晶ポリマー(重量平均分子量5000)20重量部、ネマチック液晶相を示す重合性液晶(BASF製、商品名「PaliocolorLC242」)80重量部、及び光重合開始剤(チバスペシャリティーケミカルズ製、商品名「イルガキュア907」)5重量部をシクロペンタノン200重量部に溶解して、液晶塗工液を調製した。次に、基材フィルムであるノルボルネン系樹脂フィルム(日本ゼオン製、商品名「ゼオネックス」)の表面に、調製した液晶塗工液をバーコーターにより塗工した後、80℃で4分間、加熱及び乾燥させて、塗布膜に含まれる液晶を配向させた。次に、紫外線の照射により塗布膜を硬化させて、第2の位相差フィルムである液晶固化層(厚さ0.58μm)を基材フィルム上に形成した。波長550nmの光に対する液晶固化層の面内位相差Reは0nm、厚さ方向の位相差Rthは-71nmであり(nx=1.5326、ny=1.5326、nz=1.6550)、液晶固化層は、nz>nx=nyの屈折率特性を示した。
上記作製した第1の位相差フィルムの一方の面と、第2の位相差フィルムの液晶固化層とを接着剤を介して貼合せて、位相差フィルムR1を作製した。
(層間粘着剤の作製)
撹拌羽根、温度計、窒素ガス導入管、及び冷却器を備えた4つ口フラスコに、ブチルアクリレート79.9重量部、ベンジルアクリレート15重量部、アクリル酸5重量部及び4-ヒドロキシブチルアクリレート0.1重量部を含有する単量体混合物を仕込んだ。次に、単量体混合物100重量部に対して、重合開始剤として2,2’-アゾイソブチロニトリル0.1重量部を酢酸エチルと共に加え、緩やかに撹拌しながら窒素ガスを導入してフラスコ内を窒素置換した後、フラスコ内の液温を55℃付近に保って重合反応を7時間進行させた。次に、得られた反応液に酢酸エチルを加えて固形分濃度30重量%に調整して、層間粘着剤に使用する(メタ)アクリル系ポリマーの溶液を得た。得られたポリマーの重量平均分子量は、220万であった。
上記作製した粘着剤組成物PSA1を、剥離面にシリコーン処理が施された剥離フィルムである、厚さ38μmのポリエチレンテレフタレート(PET)フィルム(三菱化学ポリエステルフィルム製、MRF38)の剥離面に対して、乾燥後の層の厚さが12μmとなるように塗布し、155℃で1分間乾燥処理して、層間粘着剤層を形成した。次に、形成した層間粘着剤層を偏光板P1における保護層(ハードコートなし)側に転写して、層間粘着剤層付き偏光板を得た。
位相差フィルムR1における第2の位相差フィルム側(第2の位相差フィルムを作製する際に基材フィルムとして用いたノルボルネン系樹脂フィルムは剥離)に、実施例及び比較例で作製した各粘着シートを剥離フィルムから転写して貼りつけた。次に、位相差フィルムR1における第1の位相差フィルム側に、上記作製した層間粘着剤層付き偏光板を、層間粘着剤層を介して貼りつけて、粘着シート付き円偏光板を得た。位相差フィルムR1と層間粘着剤層付き偏光板との貼りつけは、第1の位相差フィルムの側から見て、第1の位相差フィルムの遅相軸と偏光子の吸収軸との成す角度が反時計回りに45度となるように実施した。
BA:n-ブチルアクリルレート
BzA:ベンジルアクリレート
AA:アクリル酸
HBA:4-ヒドロキシブチルアクリレート
NVP:N-ビニルピロリドン
AIBN:2,2’-アゾビスイソブチロニトリル
C/L:トリメチロールプロパン/トリレンジイソシアネート3量体付加物(イソシアネート系架橋剤;東ソー製、コロネートL)
TetradC:1,3-ビス(N,N-ジグリシジルアミノメチル)シクロヘキサン(多官能エポキシ系架橋剤;三菱ガス化学製、テトラッドC)
KBM403:3-グリシドキシプロピルトリエトキシシラン(シランカップリング剤;信越化学工業製、KBM403)
(合成例1)
撹拌羽根、温度計、窒素ガス導入管、及び冷却器を備えた4つ口フラスコに、BA94.9重量部、AA5.0重量部及びHBA0.1重量部を仕込んだ。次に、BA、AA及びHBAの混合物100重量部に対して、重合開始剤としてAIBN0.1重量部を加え、緩やかに撹拌しながら窒素ガスを導入してフラスコ内を窒素置換した後、フラスコ内の液温を55℃付近に保って重合反応を7時間進行させた。次に、得られた反応液に酢酸エチルを加えて固形分濃度12重量%に調整して、(メタ)アクリル系ポリマー(A-1)の溶液を得た。(メタ)アクリル系ポリマー(A-1)の重量平均分子量(Mw)は220万であった。
使用する単量体をBA79.9重量部、BzA15.0重量部、AA5.0重量部及びHBA0.1重量部に変更した以外は、合成例1と同様にして、(メタ)アクリル系ポリマー(A-2)の溶液を得た。(メタ)アクリル系ポリマー(A-2)の重量平均分子量(Mw)は220万であった。
使用する単量体をBA74.9重量部、BzA20.0重量部、AA5.0重量部及びHBA0.1重量部に変更した以外は、合成例1と同様にして、(メタ)アクリル系ポリマー(A-3)の溶液を得た。(メタ)アクリル系ポリマー(A-3)の重量平均分子量(Mw)は230万であった。
使用する単量体をBA92.9重量部、AA5.0重量部、HBA0.1重量部及びNVP2重量部に変更した以外は、合成例1と同様にして、(メタ)アクリル系ポリマー(A-4)の溶液を得た。(メタ)アクリル系ポリマー(A-4)の重量平均分子量(Mw)は250万であった。
使用する単量体をBA90.9重量部、AA5.0重量部、HBA0.1重量部及びNVP4重量部に変更した以外は、合成例1と同様にして、(メタ)アクリル系ポリマー(A-5)の溶液を得た。(メタ)アクリル系ポリマー(A-5)の重量平均分子量(Mw)は260万であった。
使用する単量体をBA89.9重量部、AA10.0重量部及びHBA0.1重量部に変更した以外は、合成例1と同様にして、(メタ)アクリル系ポリマー(A-6)の溶液を得た。(メタ)アクリル系ポリマー(A-6)の重量平均分子量(Mw)は260万であった。
(実施例1~7、比較例1~3)
以下の表2に示すように(メタ)アクリル系ポリマー(A)の固形分100重量部に対して架橋剤等を混合して、溶剤型の粘着剤組成物を得た。
Claims (11)
- (メタ)アクリル系ポリマー(A)を主成分として含み、
架橋剤(B)を更に含み、
前記架橋剤(B)の配合量は、前記(メタ)アクリル系ポリマー(A)100重量部に対して5重量部以上であり、
前記架橋剤(B)の自己重合体(C)を想定したときに、前記(メタ)アクリル系ポリマー(A)と前記自己重合体(C)との間のハンセン溶解度パラメータ(HSP)の距離Raが12.3以下である、粘着剤組成物。 - 前記架橋剤(B)がイソシアネート系である、請求項1に記載の粘着剤組成物。
- 前記架橋剤(B)がトリレンジイソシアネート系である、請求項1又は2に記載の粘着剤組成物。
- 前記架橋剤(B)が3官能以上である、請求項1~3のいずれか1項に記載の粘着剤組成物。
- 前記(メタ)アクリル系ポリマー(A)が、芳香環含有単量体に由来する構成単位を含む、請求項1~4のいずれか1項に記載の粘着剤組成物。
- 前記(メタ)アクリル系ポリマー(A)が、水酸基含有単量体に由来する構成単位を1重量%以下の含有率で含む、請求項1~5のいずれか1項に記載の粘着剤組成物。
- 溶剤型である、請求項1~6のいずれか1項に記載の粘着剤組成物。
- 請求項1~7のいずれか1項に記載の粘着剤組成物から形成された粘着シート。
- 25℃の貯蔵弾性率G’が0.5MPa以上である、請求項8に記載の粘着シート。
- 請求項8又は9に記載の粘着シートと、光学フィルムと、を含む、光学積層体。
- 請求項10に記載の光学積層体を備える画像表示装置。
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