WO2015194532A1 - 偏光子用粘着剤組成物及び偏光子用粘着シート - Google Patents

偏光子用粘着剤組成物及び偏光子用粘着シート Download PDF

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Publication number
WO2015194532A1
WO2015194532A1 PCT/JP2015/067257 JP2015067257W WO2015194532A1 WO 2015194532 A1 WO2015194532 A1 WO 2015194532A1 JP 2015067257 W JP2015067257 W JP 2015067257W WO 2015194532 A1 WO2015194532 A1 WO 2015194532A1
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Prior art keywords
group
sensitive adhesive
pressure
polarizer
adhesive composition
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PCT/JP2015/067257
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English (en)
French (fr)
Japanese (ja)
Inventor
山本　真之
国昭 武藤
俊 柴田
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王子ホールディングス株式会社
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Priority to KR1020177000346A priority Critical patent/KR101958680B1/ko
Priority to JP2016529355A priority patent/JP6508204B2/ja
Priority to CN201580032667.2A priority patent/CN106795416A/zh
Publication of WO2015194532A1 publication Critical patent/WO2015194532A1/ja

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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
    • C09J7/10—Adhesives in the form of films or foils without carriers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J201/00—Adhesives based on unspecified macromolecular compounds
    • C09J201/02—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C09J201/10—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing hydrolysable silane groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • 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
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • 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

Definitions

  • an adhesive is usually used.
  • the adhesive is preliminarily provided as an adhesive layer on one side of the polarizing plate because of the convenience that the polarizing plate can be fixed instantaneously and a drying step is not required to fix the polarizing plate.
  • the transparent protective film of the polarizer is eliminated and the pressure-sensitive adhesive layer is directly provided on the polarizer, if the pressure-sensitive adhesive layer having the conventional antistatic performance is used, the polyvinyl alcohol (PVA) which is a constituent element of the polarizer is used. It has been clarified by the present inventors that color loss (deterioration of the polarizer) of a dichroic dye such as iodine that is adsorbed and oriented occurs.
  • PVA polyvinyl alcohol
  • the cause of color loss of the polarizer is the antistatic agent for imparting antistatic performance contained in the pressure-sensitive adhesive layer.
  • the present inventors it was found that by using an antistatic agent having a specific composition in the pressure-sensitive adhesive composition, it is possible to suppress color loss of the polarizer without impairing the antistatic performance. It was.
  • the present inventors used an antistatic composition in which a salt having an anion having a fluoro group and a sulfonyl group dissolved in a plasticizer containing a polyether group in the main chain as an acrylic pressure-sensitive adhesive.
  • the color loss of the polarizer can be suppressed without impairing the antistatic performance by dispersing stably and uniformly and using this for bonding the polarizer and the optical member. Furthermore, the present inventors have found that the polarizing plate can be thinned by using such a pressure-sensitive adhesive composition for a polarizer, and have completed the present invention. Specifically, the present invention has the following configuration.
  • the antistatic composition is a composition in which a salt having an anion having a fluoro group and a sulfonyl group is dissolved in a polyether plasticizer containing a polyether group in the main chain [1].
  • An antistatic composition includes a composition in which a salt having an anion having a fluoro group and a sulfonyl group is dissolved in a polyether ester plasticizer containing a polyether group in the main chain;
  • the pressure-sensitive adhesive composition for polarizers according to any one of [1] to [6], wherein the pressure-sensitive adhesive composition for polarizers is a pressure-sensitive adhesive composition containing substantially no carboxyl group. .
  • a numerical range expressed using “to” means a range including numerical values described before and after “to” as a lower limit value and an upper limit value.
  • the pressure-sensitive adhesive composition for a polarizer of the present invention is a pressure-sensitive adhesive composition directly attached to at least one surface of a polarizer, and is a pressure-sensitive adhesive composition used for bonding a polarizer and an optical member. is there.
  • the pressure-sensitive adhesive composition for a polarizer of the present invention contains an antistatic composition.
  • the antistatic composition is a composition in which a salt having an anion having a fluoro group and a sulfonyl group is dissolved in a plasticizer containing a polyether group in the main chain.
  • the pressure-sensitive adhesive composition for a polarizer of the present invention has the above-described configuration, the polarizer and the pressure-sensitive adhesive layer are flexibly adhered to each other. Moreover, since the adhesive composition for polarizers of this invention can be directly affixed or laminated
  • the antistatic composition used in the pressure-sensitive adhesive composition for a polarizer of the present invention is selected from alkali metals, group 2 elements, transition metals and amphoteric metals in a plasticizer containing a polyether group in the main chain. It is also a composition in which a salt having at least one cation is dissolved.
  • the cation is preferably any cation selected from an alkali metal and a group 2 element, and more preferably an alkali metal cation. Especially, it is preferable that a cation is a lithium ion.
  • a cation which is a counter ion of an anion is coordinated to an oxygen atom of an ether in a plasticizer to form a complex. That is, a cation which is a counter ion of an anion having a fluoro group and a sulfonyl group forms a Lewis acid / base complex ion with a plasticizer containing a polyether group in the main chain.
  • a cation which is a counter ion of an anion having a fluoro group and a sulfonyl group is coordinated to an oxygen atom of an ether in a plasticizer containing a polyether group in the main chain. It is characterized in that it contains a complex.
  • the cation that forms a complex ion with the plasticizer is preferably at least one cation selected from alkali metals, Group 2 elements, transition metals and amphoteric metals, and more preferably lithium ions. That is, the complex formed is preferably a lithium polyether complex.
  • HPLC high performance liquid chromatography
  • a peak derived from the complex is detected. This peak is not detected only with a salt-only antistatic composition or a plasticizer containing a polyether group in the main chain, and is a peak derived from a complex.
  • the HPLC conditions are as follows. Column: XBridge C18, column diameter 4.6 ⁇ 250 mm (manufactured by Waters) Column temperature: 30 ° C Mobile phase; acetonitrile / water flow rate; 0.8 mL / min. Detection: 225 nm
  • an antistatic composition refers to a state where a salt having an anion having a fluoro group and a sulfonyl group is dispersed or dissolved in a plasticizer.
  • examples of such an antistatic composition include Sanconol AD2326 (manufactured by Sanko Chemical Industry Co., Ltd.), Sanconol AD2600 (manufactured by Sanko Chemical Industry Co., Ltd.), Sanconol TGR (manufactured by Sanko Chemical Industry Co., Ltd.), and the like.
  • a pressure-sensitive adhesive composition for a polarizer containing a conventional ionic compound When a pressure-sensitive adhesive composition for a polarizer containing a conventional ionic compound is directly applied to the polarizer, the cation may bleed out or bloom due to the poor fluidity of the ionic compound and the poor compatibility with the acrylic pressure-sensitive adhesive composition. As a result, a pseudo bond is formed with iodine ions (I 3 ⁇ , I 5 ⁇ ) of the polarizer, causing color loss of the polarizer.
  • the antistatic composition used in the present invention is dispersed in a plasticizer having a high affinity with the acrylic pressure-sensitive adhesive composition, it does not cause bleeding out or blooming. Furthermore, since the cation of the antistatic composition forms a complex acid of Lewis acid / base type with the plasticizer, it does not form a chemical bond with the iodine ion of the polarizer.
  • the content of the antistatic composition is preferably 0.01 to 30 parts by mass, preferably 0.1 to 30 parts by mass with respect to 100 parts by mass of the (meth) acrylic copolymer contained in the pressure-sensitive adhesive composition for polarizers. It is more preferable that it is 10 mass parts.
  • the antistatic composition is preferably a composition in which a salt having an anion having a fluoro group and a sulfonyl group is dissolved in a polyether ester plasticizer containing a polyether group in the main chain.
  • the polyether ester plasticizer contains a polyether group and an ester bond, and enters the gap between the resins, thereby preventing the resin from being regularly oriented.
  • the polyether ester plasticizer refers to one that maintains an amorphous state even below the glass transition point.
  • the polyether ester plasticizer is preferably a polyether ester compound represented by the following formula (1) or (2).
  • n and n are each an integer, and R represents an alkyl group.
  • Polyether ester plasticizer has low viscosity, good workability, low temperature flexibility, heat aging resistance, balance between flexibility and durability, non-volatility, non-migration, oil resistance, Excellent safety (PL conformance).
  • the antistatic composition may be a composition in which a salt containing an anion having a fluoro group and a sulfonyl group is dissolved in a polyether plasticizer containing a polyether group in the main chain. Further, the antistatic composition includes a composition in which a salt having an anion having a fluoro group and a sulfonyl group is dissolved in a polyether ester plasticizer containing a polyether group in the main chain; And a composition in which a salt containing an anion having a fluoro group and a sulfonyl group is dissolved in a polyether plasticizer containing in the main chain.
  • the polyether plasticizer is preferably a polyalkylene glycol (di or mono) alkyl ether compound represented by the following general formula (11).
  • the polyether plasticizer is particularly preferably a polyalkylene glycol alkyl ether compound.
  • the wettability of the pressure-sensitive adhesive layer to the adherend can be improved, and it is difficult to cause entrainment of bubbles at the time of sticking, and the plasticizer bleeds out from the pressure-sensitive adhesive layer. It becomes difficult to occur and adherend contamination can be suitably reduced.
  • Examples of the saturated or unsaturated acyclic hydrocarbon group in the mono- or dicarboxylic acid component constituting the ester include an alkyl group and an alkylene group, and among them, an alkyl group or alkylene group having 1 to 20 carbon atoms is preferable. Further, an alkyl group having 4 to 18 carbon atoms is more preferable, and an alkyl group having 4 to 14 carbon atoms is particularly preferable.
  • Such a mono- or dicarboxylic acid having a saturated or unsaturated acyclic hydrocarbon group has a carbon number close to the carbon number of the acrylic monomer constituting the acrylic pressure-sensitive adhesive composition used in the pressure-sensitive adhesive composition for polarizers. By having a number, the compatibility with the pressure-sensitive adhesive composition for polarizers is improved, and it is suitably retained in the pressure-sensitive adhesive composition for polarizers, so that bleeding out is suppressed.
  • Examples of monocarboxylic acids and dicarboxylic acids having a saturated or unsaturated acyclic hydrocarbon group include oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, and sebacic acid.
  • Mono- or polyester of linear aliphatic dicarboxylic acid such as dodecanedioic acid, acetic acid, propionic acid, butyric acid, chitosulic acid, capconic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, undecylic acid, lauric acid, tridecylic acid Saturated fatty acids such as myristic acid, pentadecylic acid, palmitic acid, margaric acid, stearic acid, nonadecyl acid, arachidic acid, crotonic acid, angelic acid, Linderic acid, myristoleic acid, palmitoleic acid, oleic acid, vaccenic acid, gadoleic acid , Eicosenoic acid, erucic acid, nervonic acid, linoleic acid Eicosadienoic acid, docosadienoic acid, linolenic acid, pinolenic acid,
  • the compatibility with the pressure-sensitive adhesive composition for polarizers is improved, and it is suitably retained in the pressure-sensitive adhesive composition for polarizers, so that bleeding out is suppressed.
  • the number of carbon atoms of the hydrocarbon group of the alcohol component is the number of carbon atoms of the acrylic monomer constituting the acrylic pressure-sensitive adhesive composition used in the pressure-sensitive adhesive composition for polarizers. In particular, it becomes easy to suppress adherend contamination.
  • Examples of the alcohol having such an acyclic hydrocarbon group include methyl alcohol, ethyl alcohol, propanol, butanol, pentanol, hexanol, heptanol, octyl alcohol, nonyl alcohol, decyl alcohol, undecyl alcohol, dodecyl alcohol, Examples include tridecyl alcohol, tetradecyl alcohol, pentadecyl alcohol, cetyl alcohol, heptadecyl alcohol, octadecyl alcohol, nonadecyl alcohol, and straight chain or branched alcohol of aralkyl alcohol. Of these, butanol, pentanol, hexanol, heptanol, octyl alcohol, nonyl alcohol, and decyl alcohol can be particularly preferably used.
  • an ester formed from the above mono- or dicarboxylic acid and an alcohol may be used as a plasticizer.
  • the ester may have a skeleton composed of a saturated or unsaturated hydrocarbon group, but is preferably an ester not having a skeleton composed of an unsaturated hydrocarbon group.
  • an epoxidized ester in which an unsaturated bond of an ester having a skeleton composed of the unsaturated hydrocarbon group is epoxidized can also be preferably used.
  • adipic acid monoester, sebacic acid monoester, and epoxidized fatty acid monoester can be particularly preferably used.
  • the ester used as the plasticizer may be either a monoester or a polyester, but it is easy to control the solubility parameter (SP value) within a suitable range and improves the compatibility with the pressure-sensitive adhesive composition for polarizers. Therefore, it is preferable that the ester has a weight average molecular weight in terms of PS of 1000 or less, particularly preferably an ester having a molecular weight of 300 to 800.
  • the plasticizer it is preferable to use a plasticizer having a solubility parameter (SP value) of 8.5 or less. Among these, 7.0 to 8.4 is preferable. If the SP value of the plasticizer is 8.5 or less, it is excellent in compatibility with the acrylic pressure-sensitive adhesive composition. Therefore, it is long in a high-temperature and high-humidity environment with the pressure-sensitive adhesive composition for the polarizer attached to the polarizer. Even when left for a period of time, fogging hardly occurs on the surface of the polarizer when it is peeled off from the surface of the polarizer. As the SP value of the plasticizer, a plasticizer having a value larger than 7.0 is generally used. The SP value is the value of J.P. The Small formula [P. A. J. et al. Small: J.M. Appl. Chem. , 3, 71 (1953)].
  • a salt having an anion having a fluoro group and a sulfonyl group is easily dissolved in a polyether ester plasticizer and a polyether plasticizer, and the salt concentration in the plasticizer can be increased.
  • a large amount of a salt having an anion having a fluoro group and a sulfonyl group can be incorporated into the pressure-sensitive adhesive composition for a polarizer in a large amount. .
  • a cation which is a counter ion of an anion is coordinated to an oxygen atom of an ether in a plasticizer to form a complex.
  • a solution of a plasticizer in which a salt having an anion having a fluoro group and a sulfonyl group is dissolved, in combination with the plasticity of the plasticizer, in the pressure-sensitive adhesive composition for polarizer, Gives plasticity.
  • the plasticizer which contains a polyether group in the main chain can be brought close to the solubility parameter (SP value) of the pressure-sensitive adhesive composition for polarizers, it has excellent affinity and does not bleed.
  • a solution of a plasticizer in which a salt having an anion having a fluoro group and a sulfonyl group is dissolved exhibits antistatic properties while maintaining adhesive physical properties in the pressure-sensitive adhesive composition for polarizers. Furthermore, since a plasticizer solution in which a salt having an anion having a fluoro group and a sulfonyl group is dissolved is highly compatible with the molecules constituting the pressure-sensitive adhesive composition for polarizers, bleeding, blooming, and migration contamination are prevented. It is possible to obtain a pressure-sensitive adhesive composition for a polarizer that does not occur and does not depend on humidity, has excellent rapidity, and maintains excellent antistatic properties.
  • the anion having a fluoro group and a sulfonyl group is preferably an anion selected from the group consisting of a bis (fluoroalkylsulfonyl) imide ion, a tris (fluoroalkylsulfonyl) methide ion and a fluoroalkylsulfonic acid ion.
  • the salt having an anion having a fluoro group and a sulfonyl group is composed of at least one cation selected from alkali metals, Group 2 elements, transition metals and amphoteric metals, and the anion having the fluoro group and the sulfonyl group.
  • the salt is preferably.
  • salts having an anion having a fluoro group and a sulfonyl group include alkali metal salts of bis (fluoroalkylsulfonyl) imide ions, alkali metal salts of tris (fluoroalkylsulfonyl) methide ions, and alkali metal salts of fluoroalkylsulfonic acid ions. It is preferable that Lithium salts are particularly preferred.
  • the salt is composed of bis (fluoroalkylsulfonyl) imide ion, tris (fluoroalkylsulfonyl) methide ion, and fluoroalkylsulfonic acid ion.
  • Alkylsulfonyl) imide alkali metal salts, tris (fluoroalkylsulfonyl) methide alkali metal salts and trifluoroalkylsulfonic acid alkali metal salts are preferred.
  • bis (trifluoromethanesulfonyl) imide lithium, tris (trifluoromethanesulfonyl) methide lithium, and lithium trifluoromethanesulfonate can be given.
  • bis (trifluoromethanesulfonyl) imidolithium and lithium trifluoromethanesulfonate are preferable, and the above-described effect can be further exerted only by adding a small amount thereof.
  • the state in which bis (fluoroalkylsulfonyl) imidolithium Li (CF 3 SO 2 ) 2 N is used and dissolved in tetraethylene glycol dimethyl ether means that the polar ether group is coordinated to the Li + ion. In this state, it is dispersed in the composition. That is, the composition contains a lithium polyether complex. Li + ions are surrounded by ether oxygen, are separated from (CF 3 SO 2 ) 2 N ⁇ ions, and are in a bare state, greatly contributing to antistatic properties.
  • a mixture of a plasticizer containing a lithium salt and a polyether group in the main chain forms a complex acid of Lewis acid / base type, and this complex behaves as a kind of ionic liquid, especially contributing greatly to antistatic properties.
  • the lithium salt forms a Lewis acid / base complex ion with a plasticizer containing a polyether group in the main chain, it cannot form a chemical bond with the iodine ion of the polarizer. Therefore, the color loss of the polarizer is not caused.
  • the antistatic composition may further contain a polymer type antistatic agent.
  • the polymer type antistatic agent can stabilize a salt provided with an anion.
  • this salt since the salt having an anion is dispersed in a state in which it is dissolved in a plasticizer containing a polyether group in the main chain, this salt has an affinity for a plasticizer containing a polyether group in the main chain. It is thought that the polymer type antistatic agent gathers in the presence and is stabilized by the affinity between them.
  • Examples of such a polymer type antistatic agent include a polyether block polyolefin copolymer, a polyoxyalkylene copolymer, and an ethylene oxide-propylene oxide-allyl glycidyl copolymer.
  • the plasticizer containing a polyether group in the main chain is preferably a polyether ester plasticizer and / or a polyether plasticizer, and the salt solution contains a fluoro group and a plasticizer. It can be obtained by adding a salt having an anion having a sulfonyl group and stirring.
  • the main component of the pressure-sensitive adhesive composition for a polarizer is an acrylic pressure-sensitive adhesive composition.
  • the acrylic pressure-sensitive adhesive composition includes a (meth) acrylic copolymer crosslinked by a crosslinking agent. Further, the “main component” means that 50% by mass or more is contained with respect to the whole pressure-sensitive adhesive.
  • the acrylic pressure-sensitive adhesive composition contains a (meth) acrylic copolymer (A) and a crosslinking agent (B).
  • the “acrylic pressure-sensitive adhesive composition” is a compound having a (meth) acryloyl group.
  • (Meth) acryloyl group” means an acryloyl group or a methacryloyl group.
  • (Meth) acrylic acid ester substituted with a hydrogen group is mentioned.
  • the hydrocarbon group preferably has 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms.
  • the hydrocarbon group may have a substituent.
  • the substituent is not particularly limited as long as it does not contain a crosslinkable group, and examples thereof include alkoxy groups such as methoxy group and ethoxy group.
  • the (meth) acrylic acid ester examples include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, Isobutyl (meth) acrylate, t-butyl (meth) acrylate, n-pentyl (meth) acrylate, n-hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n- (meth) acrylate Octyl, isooctyl (meth) acrylate, n-nonyl (meth) acrylate, isononyl (meth) acrylate, n-decyl (meth) acrylate, isodecyl (meth) acrylate, n-undecyl (meth) acrylate, N-do
  • (meth) acrylic acid means containing both “acrylic acid” and “methacrylic acid”.
  • n-butyl acrylate, 2-ethylhexyl acrylate, and methyl acrylate are preferable from the viewpoint of adhesiveness.
  • the amount of the non-crosslinkable acrylic monomer used for the polymerization of the (meth) acrylic copolymer (A) is preferably 60 to 99.99% by mass, and more preferably 65 to 99.9% by mass. If the amount of the non-crosslinkable acrylic monomer used for the polymerization is not less than the above lower limit value, sufficient adhesive force can be exhibited, and if it is not more than the above upper limit value, it can be sufficiently crosslinked.
  • hydroxy group-containing monomer examples include hydroxyalkyl (meth) acrylates such as 2-hydroxyethyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, (meth (Meth) acrylic acid [(mono, di or poly) alkylene glycol] such as mono (diethylene glycol) acrylic acid, and (meth) acrylic acid lactone such as (meth) acrylic acid monocaprolaclone.
  • amino group-containing monomers examples include (meth) acrylamide, allylamide, N, N-dimethyl (meth) acrylamide, N-butyl (meth) acrylamide and the like.
  • examples of the glycidyl group-containing monomer examples include glycidyl (meth) acrylate.
  • the amount of the crosslinkable monomer used for the polymerization of the (meth) acrylic copolymer (A) is preferably 0.01 to 20% by mass, more preferably 0.03 to 10% by mass, and More preferably, it is 05 to 10% by mass. If the amount of the crosslinkable monomer used for the polymerization is not less than the above lower limit value, it can be sufficiently crosslinked.
  • the crosslinking monomer is preferably a hydroxy group-containing monomer or an amino group-containing monomer from the viewpoints of adhesiveness, crosslinkability, polymerizability and durability, and reworkability that allows re-peeling and reuse of the glass.
  • a hydroxy group-containing monomer and an amino group-containing monomer may be used in combination.
  • As the hydroxy group-containing monomer hydroxyalkyl (meth) acrylate is more preferable, and 2-hydroxyethyl (meth) acrylate and 4-hydroxybutyl (meth) acrylate are particularly preferable.
  • As the amino group-containing monomer (meth) acrylamide, N, N-dimethyl (meth) acrylamide, and N-butyl (meth) acrylamide are preferable.
  • the amount of the carboxy group-containing monomer used for the polymerization of the (meth) acrylic copolymer (A) is preferably less than 0.5% by mass, and less than 0.05% by mass. More preferably. Furthermore, it is preferable that the monomer having a reactive functional group does not substantially contain a carboxy group-containing monomer.
  • the monomer having a reactive functional group substantially does not contain a carboxy group-containing monomer means that the acid value of the monomer having a reactive functional group used for the polymerization of the (meth) acrylic copolymer (A) is JIS. When measured according to K0070 (1992), the acid value is less than 0.1 mgKOH / g. If the acid value of the monomer having a reactive functional group is less than 0.1 mgKOH / g, it is considered that no intentionally added carboxy group-containing monomer is contained, and 0.1 to 1.0 mgKOH / g. For example, it is considered that a small amount of the carboxy group-containing monomer added intentionally is included.
  • the intentional addition means that a carboxy group-containing monomer is used as a crosslinkable monomer.
  • acrylic ester derivative from acrylic acid
  • a trace amount of unreacted acrylic acid may be contained as an impurity. I don't think.
  • Acid value (mgKOH / g) [B ⁇ f ⁇ 5.611] / S (1)
  • B is the amount (ml) of 0.1N potassium hydroxide-ethanol solution used
  • f is the factor of 0.1N potassium hydroxide-ethanol solution
  • S is the sample The amount collected (g).
  • the (meth) acrylic copolymer (A) may have other monomers other than the non-crosslinkable acrylic monomer and the crosslinkable monomer.
  • examples of other monomers include (meth) acrylonitrile, vinyl acetate, styrene, vinyl chloride, vinyl pyrrolidone, vinyl pyridine and the like.
  • the amount of the other monomer used for the polymerization of the (meth) acrylic copolymer (A) is preferably 0.1 to 20% by mass, and more preferably 0.5 to 10% by mass. If the amount of the other monomer used for the polymerization is not less than the above lower limit, the physical properties can be easily adjusted, and if it is not more than the above upper limit, yellowing due to deterioration with time can be prevented.
  • Crosslinking agent used for acrylic adhesive composition As the crosslinking agent (B) used in the acrylic pressure-sensitive adhesive composition, it is preferable to use a crosslinking agent capable of reacting with a crosslinking monomer which is a monomer having a reactive functional group. Examples thereof include an isocyanate-based crosslinking agent, an epoxy-based crosslinking agent, an oxazoline-based crosslinking agent, an aziridine-based crosslinking agent, a metal chelate-based crosslinking agent, and a butylated melamine-based crosslinking agent.
  • Examples of the isocyanate-based crosslinking agent include tolylene diisocyanate, xylylene diisocyanate, hexamethylene diisocyanate, and isophorone diisocyanate.
  • Examples of the epoxy crosslinking agent include ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, glycerin diglycidyl ether, neopentyl glycol diglycidyl ether, and 1,6-hexane.
  • the pressure-sensitive adhesive composition for polarizers of the present invention may contain components other than the acrylic pressure-sensitive adhesive composition and the antistatic composition.
  • a polyester resin, an amino resin, an epoxy resin, or a polyurethane resin may be used in combination.
  • the pressure-sensitive adhesive composition for a polarizer of the present invention includes a light stabilizer such as an antioxidant, a metal corrosion inhibitor, a tackifier, a silane coupling agent, an ultraviolet absorber, and a hindered amine compound, if necessary.
  • a light stabilizer such as an antioxidant, a metal corrosion inhibitor, a tackifier, a silane coupling agent, an ultraviolet absorber, and a hindered amine compound, if necessary.
  • Additives such as fillers may be included.
  • the antioxidant include phenolic antioxidants, amine-based antioxidants, lactone-based antioxidants, phosphorus-based antioxidants, sulfur-based antioxidants, and the like. These antioxidants may be used alone or in combination of two or more.
  • a benzotriazole-based resin is preferable because of the compatibility and high effect of the pressure-sensitive adhesive.
  • the pressure-sensitive adhesive composition for a polarizer is produced by dispersing a salt having an anion having a fluoro group and a sulfonyl group in a composition containing a pressure-sensitive adhesive resin such as an acrylic pressure-sensitive adhesive composition.
  • the production method comprises a step of preparing a salt solution obtained by dissolving a salt having an anion having a fluoro group and a sulfonyl group in a plasticizer containing a polyether group in the main chain, and a salt solution (first component).
  • the pressure-sensitive adhesive composition for a polarizer of the present invention can be formed into a sheet shape to obtain a pressure-sensitive adhesive sheet for a polarizer.
  • the pressure-sensitive adhesive sheet for a polarizer can be produced, for example, by dissolving a pressure-sensitive adhesive in a solvent, and coating and then removing the solvent.
  • the coating method can be appropriately selected from knife coaters, micro bar coaters, air knife coaters, reverse roll coaters, reverse gravure coaters, bario gravure coaters, die coaters, curtain coaters and the like.
  • the pressure-sensitive adhesive sheet of the present invention is used, there is no need for the application of a pressure-sensitive adhesive at the bonding stage and a drying step, and the pressure-sensitive adhesive sheet for pressure-sensitive adhesive is laminated and pressed between the optical film and the pressure-sensitive adhesive object. It is easy to do.
  • the thickness of the pressure-sensitive adhesive layer of the pressure-sensitive adhesive sheet for polarizers of the present invention is preferably 100 ⁇ m or less, and more preferably 5 to 50 ⁇ m. If it is below the said upper limit, the stress relaxation performance of an adhesive layer can fully be expressed.
  • the pressure-sensitive adhesive sheet with a release sheet for a polarizer preferably has a structure in which a release film provided with a release agent on a substrate is provided on one or both sides of the pressure-sensitive adhesive sheet.
  • a double-sided pressure-sensitive adhesive sheet with a release sheet provided with a release film on both sides of the pressure-sensitive adhesive layer was obtained by applying and drying the pressure-sensitive adhesive coating solution on the release layer surface of the first release film provided with the release agent layer on the polymer film.
  • the peel force of the release film on the heavy peel force side is preferably 0.05 N to 0.15 N, and the peel force of the peel film on the light peel force side is preferably 0.01 to 0.04 N.
  • the polarizer is sandwiched between protective films, and an adhesive sheet (adhesive layer) is attached to the protective film.
  • an adhesive sheet adheresive layer
  • the pressure-sensitive adhesive composition and the pressure-sensitive adhesive sheet for the polarizer of the present invention can be applied to such a configuration, the effect of the present invention is exhibited when directly sticking to the polarizer as shown in FIG. can do.
  • the polarizer adhesive composition and polarizer adhesive sheet of the present invention are for bonding a polarizer and a member having a thickness of 100 ⁇ m, preferably 1 mm or more.
  • the pressure-sensitive adhesive composition for a polarizer and the pressure-sensitive adhesive sheet for a polarizer of the present invention are for bonding a polarizer and an optical member.
  • an optical member a liquid crystal cell, a touch panel, etc. can be mentioned, and the image display apparatus provided with the adhesive sheet of this invention can be produced.
  • polarizer used in the polarizing plate for example, a polyvinyl alcohol resin film or a polyvinyl alcohol resin described in JP 2012-159778 is adsorbed and oriented.
  • the polyvinyl alcohol resin constituting the polarizer can be obtained by saponifying a polyvinyl acetate resin.
  • the polyvinyl acetate resin include polyvinyl acetate, which is a homopolymer of vinyl acetate, and copolymers of vinyl acetate and other monomers copolymerizable therewith.
  • Examples of other monomers copolymerized with vinyl acetate include unsaturated carboxylic acids, olefins, vinyl ethers, unsaturated sulfonic acids, and acrylamides having an ammonium group.
  • the degree of saponification of the polyvinyl alcohol resin is usually about 85 to 100 mol%, preferably 98 mol% or more.
  • This polyvinyl alcohol-based resin may be further modified, and for example, polyvinyl formal and polyvinyl acetal modified with aldehydes may be used.
  • the degree of polymerization of the polyvinyl alcohol resin is usually about 1,000 to 10,000, preferably about 1,500 to 5,000.
  • a film obtained by forming such a polyvinyl alcohol resin is used as an original film of a polarizer.
  • the method for forming a polyvinyl alcohol-based resin is not particularly limited, and can be formed by a known method.
  • the film thickness of the raw film made of polyvinyl alcohol resin is not particularly limited, but is, for example, about 1 to 150 ⁇ m. Considering easiness of stretching, the film thickness is preferably 3 ⁇ m or more.
  • the polarizer is a step of uniaxially stretching the polyvinyl alcohol resin film as described above or the polyvinyl alcohol resin described in JP2012-159778, and dyeing the polyvinyl alcohol resin or film with a dichroic dye.
  • the polarizing plate has a structure in which a transparent protective film is laminated on at least one of the polarizers produced as described above.
  • this transparent protective film what is formed from an appropriate transparent resin can be used.
  • transparent resin films include cellulose films such as triacetyl cellulose and diacetyl cellulose, polyester films such as polyethylene terephthalate, polyethylene isophthalate, and polybutylene terephthalate, polymethyl (meth) acrylate, and polyethyl (meth) acrylate.
  • Acrylic resin film, polycarbonate film, polyethersulfone film, polysulfone film, polyimide film, polyolefin film, polynorbornene film and the like can be used, but are not limited thereto.
  • the obtained (meth) acrylic copolymer (A-1) had a polystyrene equivalent weight average molecular weight Mw of 1,500,000 by GPC.
  • the weight average molecular weight Mw of the (meth) acrylic copolymer was measured by GPC (gel permeation chromatography) on a sample in which THF (tetrahydrafuran) was dissolved.
  • the obtained (meth) acrylic copolymer (A-2) had a polystyrene equivalent weight average molecular weight Mw of 1,800,000 by GPC.
  • carboxyl group-modified polyvinyl alcohol [trade name “KL-318” obtained from Kuraray Co., Ltd.] is dissolved in 100 parts of water on one side of the polarizer, and a water-soluble epoxy resin is dissolved in the aqueous solution.
  • An epoxy adhesive added with 1.5 parts of a polyamide epoxy additive [trade name “Smileise Resin 650 (30)” obtained from Taoka Chemical Co., Ltd., aqueous solution with a solid content of 30%] was applied.
  • TAC triacetyl cellulose film
  • the pressure-sensitive adhesive solution prepared as described above was used as a 38 ⁇ m-thick polyethylene terephthalate film (separator film) having a release agent layer treated with a silicone release agent (manufactured by Oji F-Tex: 38RL-07 (2)). On the surface of the film, uniformly apply with an applicator so that the coating amount after drying is 20 ⁇ m / m 2, and dry for 3 minutes in a 100 ° C. air circulation type constant temperature oven. Formed.
  • Example 2 ⁇ Preparation of acrylic adhesive solution> For 100 parts of the solid content of the (meth) acrylic copolymer (A-2) obtained in Production Example 2, 0.1 part of xylylene diisocyanate (manufactured by Mitsui Chemicals: Takenate 500) as a crosslinking agent and 3- 0.1 part of glycidoxypropylmethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd .: KBM-403) was added, and 50 parts of a polyether ester compound (Monocizer (registered trademark) W-262 and Polycizer ( (Registered trademark) W-230-H (1: 1 mixture)) and added 1.8 parts of a composition in which 50 parts of bis (trifluoromethanesulfonyl) imidolithium is dissolved.
  • xylylene diisocyanate manufactured by Mitsui Chemicals: Takenate 500
  • 3- glycidoxypropylmethoxysilane
  • the optical durability is excellent in addition to the polarizing plate durability. That is, in the examples, even when left in a high temperature / high humidity environment for a long time, there is little coloring and the light transmittance is high.
  • the comparative example is inferior in optical durability. Particularly, in Comparative Examples 1 and 2, the polarizing plate durability was not good and the function as a polarizing plate was inferior.
  • FIG. 3 shows from above the complex-containing antistatic composition, the extract of the antistatic composition-containing pressure-sensitive adhesive sheet obtained in the Examples, and the extract of the pressure-sensitive adhesive sheet containing no antistatic composition (Reference Example) It is a result of HPLC (high performance liquid chromatography) analysis of 1). As shown in the chromatogram of the extract of the adhesive sheet containing the antistatic composition in the middle stage, a complex peak was detected at a retention time of 15.0 minutes from the extract of the adhesive sheet containing the antistatic composition.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Polarising Elements (AREA)
  • Adhesive Tapes (AREA)
PCT/JP2015/067257 2014-06-18 2015-06-16 偏光子用粘着剤組成物及び偏光子用粘着シート WO2015194532A1 (ja)

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JP2016529355A JP6508204B2 (ja) 2014-06-18 2015-06-16 偏光子用粘着剤組成物及び偏光子用粘着シート
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JP2017171703A (ja) * 2016-03-18 2017-09-28 日本カーバイド工業株式会社 粘着剤組成物及び粘着剤層付偏光板
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TWI662099B (zh) 2019-06-11
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