WO2013161826A1 - Radiation-curing composition, adhesive and polarizing plate - Google Patents
Radiation-curing composition, adhesive and polarizing plate Download PDFInfo
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- WO2013161826A1 WO2013161826A1 PCT/JP2013/061942 JP2013061942W WO2013161826A1 WO 2013161826 A1 WO2013161826 A1 WO 2013161826A1 JP 2013061942 W JP2013061942 W JP 2013061942W WO 2013161826 A1 WO2013161826 A1 WO 2013161826A1
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- curable composition
- adhesive
- radiation curable
- polarizing plate
- compound
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
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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
- 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
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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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
- G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
- G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
Definitions
- the present invention relates to a radiation curable composition, an adhesive, and a polarizing plate.
- the present invention relates to a radiation curable composition suitable as an adhesive for producing an optical member such as a polarizing plate, an adhesive, and a polarizing plate using them.
- liquid crystal display devices are widely used as display devices for displaying characters, images, and the like.
- a liquid crystal display device usually includes a liquid crystal cell composed of two polarizing plates and a glass substrate, a transparent electrode, a color filter, a light distribution film, a liquid crystal, and the like disposed therebetween.
- a polarizing plate used in a liquid crystal display device is obtained by bonding a protective film such as a triacetyl cellulose film on one or both surfaces of a polarizing film (polarizer) obtained by adsorbing iodine or the like on a stretched and oriented polyvinyl alcohol sheet. It is formed by bonding through an agent layer.
- the polarizing plate In recent years, from the viewpoint of power saving, there has been a movement to make the backlight of a liquid crystal display device into an LED, and for heat generation of the LED, the polarizing plate has been required to have heat and moisture resistance and thermal shock resistance.
- a polarizing plate using a triacetylcellulose-based film having a high moisture permeability as a protective film is not sufficiently resistant to the above, and therefore, an alternative to a film having a low moisture permeability is in progress.
- composition suitable for an adhesive used for manufacturing a polarizing plate those having various curing systems are known. Among them, it is known that a curing reaction proceeds by heating, ultraviolet irradiation, etc., and those capable of forming an adhesive layer or film having a high crosslinking density can exhibit good adhesive strength and coating film strength. .
- resin compositions that can be cured by heating, ultraviolet irradiation, or the like radically polymerizable and cationically polymerizable resins are known.
- the radical polymerization of the resin composition sometimes stopped before the curing sufficiently progressed, or caused curing shrinkage as the polymerization reaction proceeded.
- cationic polymerization is insufficient in terms of adhesive strength, it has the advantage that it does not cause radical termination reaction or deactivation, and the degree of curing shrinkage is small.
- an alicyclic epoxy compound as a cationic polymerizable compound, a compound having at least two hydroxyl groups in the molecule
- an adhesive composition containing a photoacid generator can be cured in a short time and is excellent in performance such as adhesive strength (for example, see Patent Document 1).
- the polarizing plate using the adhesive has a problem that the protective film is peeled off in the heat and humidity resistance test and the thermal shock test. This was considered to be because the adhesive film was not sufficiently cured because the polarizing film absorbed the radiation. Therefore, there is a need for a polarizing plate having high weather resistance that is excellent in moist heat resistance and thermal shock resistance, and a radiation curable composition and an adhesive that enable production of such a polarizing plate.
- an object of the present invention is to provide a radiation curable composition and an adhesive that enable the production of a polarizing plate having high weather resistance while maintaining high adhesiveness of a protective film, or polarized light having high weather resistance. It is to provide a plate and to provide such a polarizing plate.
- the total number of epoxy groups of a specific epoxy compound contained in the composition and the total number of hydroxyl groups of the trifunctional alcohol contained in the composition By keeping the ratio within a certain range, it was found that the protective film of the polarizing plate was not peeled off even after the moisture and heat resistance test and the thermal shock test while maintaining the adhesiveness, and the present invention was completed. It was.
- the present invention (A) a compound having two or more alicyclic epoxy groups in the molecule, A radiation curable composition comprising (B) a compound having three hydroxyl groups in the molecule, and (C) a photoacid generator, [The number of all alicyclic epoxy groups of (A) contained in the radiation curable composition / the total number of hydroxyl groups of (B) contained in the radiation curable composition] is less than 2.0. Radiation curable compositions are provided.
- the compound having two or more alicyclic epoxy groups in the molecule is preferably a compound represented by the following formula (I).
- X represents a single bond or a linking group.
- X is preferably a linking group containing an ester bond.
- the compound having three hydroxyl groups in the molecule is preferably a polyester triol.
- the present invention also provides: An adhesive containing the radiation curable composition is provided.
- the adhesive does not contain a photosensitizer.
- the present invention also provides: An adhesive for polarizing plate containing the radiation curable composition is provided.
- the polarizing plate adhesive does not contain a photosensitizer.
- the present invention also provides: Provided is a polarizing plate obtained by adhering a protective film to at least one surface of a polarizing film using the adhesive.
- the polarizing plate is preferably a polarizing plate obtained by curing the adhesive by irradiation with radiation with an irradiation light amount of 300 mJ / cm 2 or less.
- a polarizing plate obtained by adhering a protective film using these is polarized even after a moist heat resistance test and a thermal shock test while maintaining high adhesiveness of the protective film. Peeling of the protective film on the plate does not occur, and reliability can be ensured.
- the radiation curable composition of the present invention comprises: (A) a compound having two or more alicyclic epoxy groups in the molecule, A radiation curable composition comprising (B) a compound having three hydroxyl groups in the molecule, and (C) a photoacid generator, [A total number of alicyclic epoxy groups of (A) contained in the radiation curable composition / total number of hydroxyl groups of (B) contained in the radiation curable composition] may be less than 2.0. The point is not particularly limited.
- the number of all alicyclic epoxy groups in (A) contained in the radiation curable composition / the total number of hydroxyl groups in (B) contained in the radiation curable composition is 2.
- it is preferably 0.5 to 2.0, preferably 0.7 to 1. 9 is more preferable, and 1.0 to 1.8 is particularly preferable.
- the mixing ratio of (A) a compound having two or more alicyclic epoxy groups in the molecule and (B) a compound having three hydroxyl groups in the molecule is not particularly limited.
- the mass ratio is preferably 30:70 to 70:30 (the former: the latter), more preferably 40:60 to 60:40 (the former: the latter), and 45: Particularly preferred is 55 to 55:45 (the former: the latter).
- the viscosity of the radiation curable composition of the present invention is not particularly limited, but is preferably 40 to 800 mPa ⁇ s, more preferably 40 to 500 mPa ⁇ s from the viewpoint of coating workability.
- An alicyclic epoxy group means an epoxy group composed of two adjacent carbon atoms and oxygen atoms constituting the alicyclic ring.
- the compound having two or more alicyclic epoxy groups in the molecule is preferably a compound having a cyclohexene oxide group from the viewpoints of transparency and heat resistance, and in particular, a compound represented by the following formula (I) Is preferred.
- X represents a single bond or a linking group (a divalent group having one or more atoms).
- the linking group include a divalent hydrocarbon group, a carbonyl group, an ether bond, an ester bond, a carbonate group, an amide group, and a group in which a plurality of these are linked.
- Examples of the alicyclic epoxy compound in which X in the above formula (I) is a single bond include 3,4,3 ′, 4′-diepoxybicyclohexane and the like.
- Examples of the divalent hydrocarbon group include a linear or branched alkylene group having 1 to 18 carbon atoms and a divalent alicyclic hydrocarbon group.
- Examples of the linear or branched alkylene group having 1 to 18 carbon atoms include a methylene group, a methylmethylene group, a dimethylmethylene group, an ethylene group, a propylene group, and a trimethylene group.
- divalent alicyclic hydrocarbon group examples include 1,2-cyclopentylene group, 1,3-cyclopentylene group, cyclopentylidene group, 1,2-cyclohexylene group, 1,3-cyclopentylene group, And divalent cycloalkylene groups (including cycloalkylidene groups) such as cyclohexylene group, 1,4-cyclohexylene group, and cyclohexylidene group.
- the linking group X is particularly preferably a linking group containing an oxygen atom, specifically, —CO—, —O—CO—O—, —COO—, —O—, —CONH—; A group in which a plurality of groups are linked; a group in which one or more of these groups are linked to one or more of divalent hydrocarbon groups, and the like. From the viewpoint of adhesion to an adherend, an ester A linking group having a bond (—COO—) is particularly preferred. Examples of the divalent hydrocarbon group include those exemplified above.
- Typical examples of the alicyclic epoxy compound represented by the above formula (I) include compounds represented by the following formulas (I-1) to (I-10).
- l and m each represents an integer of 1 to 30.
- R in the following formula (I-5) is an alkylene group having 1 to 8 carbon atoms, and is a methylene group, ethylene group, propylene group, isopropylene group, butylene group, isobutylene group, s-butylene group, pentylene group, hexylene.
- linear or branched alkylene groups such as a group, a heptylene group, and an octylene group.
- N1 to n6 in the following formulas (I-9) and (I-10) each represents an integer of 1 to 30.
- the compound (I-1) such as seloxide 2021P
- the compound (I-1) such as seloxide 2021P
- other alicyclic epoxy compounds represented by the formula (I) are used. It is preferable to use together.
- (B) Compound having three hydroxyl groups in the molecule [(B) Compound having three hydroxyl groups in the molecule]
- (B) Examples of the compound having three hydroxyl groups in the molecule include polyester triol, glycerin, trimethylol ethane, trimethylol propane, adamantane triol, and the like, but are not particularly limited, but are esters from the viewpoint of compatibility with epoxy compounds. Polyester triols containing groups are preferred and polycaprolactone triols are particularly preferred.
- the polycaprolactone triol is not particularly limited, but a compound represented by the following formula (II) is preferable.
- a, b and c are all integers of 1 or more, and are each in the range of, for example, 1 to 30, preferably 1 to 10, and a + b + c is preferably in the range of 3 to 30,
- R 1 is a trivalent hydrocarbon group, preferably a trivalent aliphatic hydrocarbon group, and R 1 preferably has 3 to 20, more preferably 3 to 15, and still more preferably 3 to 10 carbon atoms.
- typical examples of R 1 include trivalent hydrocarbon groups represented by the following formulas (III-1) to (III-4).
- polycaprolactone triol examples include Plaxel 303, Plaxel 305, Plaxel 308, Plaxel 312, Plaxel L312AL, Plaxel 320, Plaxel 320ML, Plaxel L320AL, Plaxel L330AL; Among them, polycaprolactone triol, particularly Plaxel 305, which is liquid at room temperature is preferable from the viewpoint of easy mixing and no fear of precipitation.
- the photoacid generator examples include a sulfonium salt such as triarylsulfonium hexafluorophosphate (eg, p-phenylthiophenyldiphenylsulfonium hexafluorophosphate) and a triarylsulfonium hexafluoroantimonate (particularly, a triarylsulfonium salt).
- a sulfonium salt such as triarylsulfonium hexafluorophosphate (eg, p-phenylthiophenyldiphenylsulfonium hexafluorophosphate) and a triarylsulfonium hexafluoroantimonate (particularly, a triarylsulfonium salt).
- Iodonium salts of phosphonium salts such as tetrafluorophosphonium hexafluorophosphate; N-hexylpi
- pyridinium salts such as tetrafluoroborate or the like. These can be used alone or in combination of two or more.
- the total amount of (A) a compound having two or more alicyclic epoxy groups in the molecule and (B) a compound having three hydroxyl groups in the molecule is 100 parts by mass. For example, it is about 1 to 20 parts by mass, preferably 4 to 10 parts by mass.
- the usage-amount of a photo-acid generator is less than the said range, the problem of the adhesive force deficiency by a cure failure and the fall of a weather resistance may arise.
- the amount of the photoacid generator used exceeds the above range, the water resistance may deteriorate due to the high concentration of the ionic substance after curing.
- the radiation curable composition of the present invention is preferably an organic solvent for adjusting the viscosity if necessary (an organic solvent capable of cationic curing, specifically, 1,3-butanediol, Celoxide 2000, etc., all of which are manufactured by Daicel Corp.), inorganic fillers for improving adhesive strength and screen printability (for example, Spherical silica manufactured by Denki Kagaku Kogyo Co., Ltd., such as FB-5SDC, FB-3SDC, etc., and silane coupling agents that improve adhesion strength (eg, Evonik Degussa Japan Co., Ltd., Dynasylan AMEO, Dynasylan GLYMO, etc.) ), Leveling agents that improve coating performance (for example, BYK-307, BYK-333, etc., manufactured by BYK Japan, Inc.) and other additives are included within a range that does not interfere with the effects of the present invention.
- an organic solvent capable of cationic curing specifically, 1,3-
- the adhesive of this invention should just contain the said radiation-curable composition, and is not restrict
- the polarizing plate of this invention should just be a polarizing plate formed by adhere
- a method for producing a polarizing plate by adhering a protective film to at least one surface of the polarizing film using, for example, an adhesive between the polarizing film and the protective film by a conventionally known method, for example.
- light (radiation) including i-line (365 nm), h-line (405 nm), g-line (436 nm), etc. Is irradiated with an illuminance of 10 to 1200 mW / cm 2 and an irradiation light quantity of 20 to 2500 mJ / cm 2 to cure the photocurable adhesive composition, whereby a polarizing plate can be obtained.
- the irradiation light amount is preferably 20 to 600 mJ / cm 2 , more preferably 20 to 300 mJ / cm 2 .
- the irradiation light quantity is 300 mJ / cm 2 or less, there is a great advantage that the deterioration of the protective film and the polarizing film due to the radiation is dramatically reduced.
- an adhesive is applied to at least one surface of the polarizing film with a bar coater, a roll coater, a gravure roll, etc., and a protective film is attached.
- a polarizing plate can be obtained by irradiating and curing the photocurable adhesive composition in the same manner as in the above case. It is also possible to obtain a polarizing plate by applying an adhesive between the protective film and the polarizing film (upper and lower two layers), and irradiating and adhering radiation from one side in the same manner as described above. When viewed from the radiation side, the UV light reaches only about one-third of the light on the lower surface of the polarizing film. (B) Improved curability by compounding with a compound having three hydroxyl groups in the molecule.
- the adhesive of the present invention is particularly useful.
- the polarizing film is not particularly limited, and specific examples include a polyvinyl alcohol polarizing film produced by adsorbing a dichroic dye on a polyvinyl alcohol resin film and uniaxially stretching the dichroic dye.
- the polyvinyl alcohol resin used for the polarizing film is usually obtained by saponifying polyvinyl acetate obtained by polymerizing vinyl acetate.
- 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 copolymerizable with vinyl acetate include unsaturated carboxylic acids, unsaturated sulfonic acids, olefins, and vinyl ethers.
- the saponification degree of the polyvinyl alcohol resin is not particularly limited, but is preferably about 85 to 100 mol%.
- the polyvinyl alcohol resin may be further modified. For example, polyvinyl formal or polyvinyl acetal modified with aldehydes may be used.
- the polymerization degree of the polyvinyl alcohol resin is not particularly limited, but is preferably about 1,000 to 10,000.
- the polyvinyl alcohol resin is not limited to those obtained by saponifying polyvinyl acetate obtained by polymerizing vinyl acetate, and a small amount of unsaturated carboxylic acid (including salts, esters, amides, nitriles, etc.) , Modified polyvinyl alcohols containing components copolymerizable with vinyl acetate, such as olefins having 2 to 30 carbon atoms (including ethylene, propylene, n-butene, isobutene, etc.), vinyl ethers, unsaturated sulfonates, etc. Resin or the like may be used.
- the weight average molecular weight of the polyvinyl alcohol-based resin is not particularly limited, but is preferably 60000 to 300000.
- a film obtained by forming such a polyvinyl alcohol resin is used as an original film of a polarizing film.
- the method for forming a polyvinyl alcohol-based resin is not particularly limited, and can be formed by a known method.
- the method for producing the polarizing film is not particularly limited.
- a step of dyeing a polyvinyl alcohol resin film with a dichroic dye and adsorbing the dichroic dye, a polyvinyl alcohol type on which the dichroic dye is adsorbed It is manufactured by a manufacturing method including a step of treating a resin film with a boric acid aqueous solution, a step of uniaxially stretching a polyvinyl alcohol resin film, and the like.
- the step of dyeing a polyvinyl alcohol resin film with a dichroic dye and adsorbing the dichroic dye, and the step of treating the polyvinyl alcohol resin film adsorbed with the dichroic dye with an aqueous boric acid solution are simultaneously performed. You can go.
- Uniaxial stretching may be performed before dyeing with a dichroic dye, may be performed simultaneously with dyeing, or may be performed after dyeing. In uniaxial stretching, it may be uniaxially stretched between rolls having different peripheral speeds, or may be uniaxially stretched using a hot roll. Further, it may be dry stretching such as stretching in the air, or may be wet stretching in which stretching is performed in a state swollen with a solvent.
- the draw ratio is preferably about 1.5 to 10 times.
- the dyeing of the polyvinyl alcohol resin film with the dichroic dye is performed, for example, by immersing the polyvinyl alcohol resin film in an aqueous solution containing the dichroic dye.
- dye For example, an iodine, a dichroic organic dye, etc. are used.
- the dyeing method when iodine is used as the dichroic dye is not particularly limited.
- a method of immersing a polyvinyl alcohol-based resin film in an aqueous solution containing iodine and potassium iodide is employed.
- the iodine content in this aqueous solution is preferably about 0.01 to 0.5 parts by mass with respect to 100 parts by mass of water, and the potassium iodide content is preferably with respect to 100 parts by mass of water.
- the immersion time (dyeing time) in this aqueous solution is preferably about 30 to 300 seconds.
- the boric acid treatment after dyeing with the dichroic dye is performed by immersing the polyvinyl alcohol resin film in a boric acid-containing aqueous solution.
- the boric acid content in the boric acid-containing aqueous solution is usually about 2 to 15 parts by weight per 100 parts by weight of water.
- the boric acid-containing aqueous solution preferably contains potassium iodide.
- the content of potassium iodide in the boric acid-containing aqueous solution is usually about 1 to 20 parts by weight with respect to 100 parts by weight of water.
- the immersion time in the boric acid-containing aqueous solution is usually about 10 to 1200 seconds.
- a polarizing film in which a dichroic dye is adsorbed and oriented on a uniaxially stretched polyvinyl alcohol resin film.
- the thickness of the polarizing film can be about 10 to 40 ⁇ m.
- each component in Table 1 is as follows.
- PVA film A staining solution was prepared by dissolving 20 parts by mass of boric acid, 0.2 parts by mass of iodine, and 0.5 parts by mass of potassium iodide in 480 parts by mass of water.
- a PVA film (Vinylon film # 40, manufactured by Aicello) was immersed in this dyeing solution for 30 seconds, and then the film was stretched twice in one direction and dried to prepare a PVA film having a thickness of 30 ⁇ m.
- a protective film As a protective film, acryl viewer (PMMA film, manufactured by Nippon Shokubai Co., Ltd.) was used. The protective film was subjected to corona discharge treatment on the film surface with a discharge amount of 320 W ⁇ min / m 2 using a corona surface treatment device (“Corona Surface Modification Evaluation Device (TEC-4AX)” manufactured by Kasuga Electric Co., Ltd.). And adhesion was carried out within 1 hour after the surface treatment.
- TEC-4AX Corona Surface Modification Evaluation Device
- UVC-02516S1AA02 manufactured by Ushio Inc., illuminance 120 mW / cm 2, irradiation amount 199mJ / cm 2 was irradiated with light.
- the adhesiveness (peeling strength) of the produced polarizing plate was measured according to “JISK6854-4 Adhesive—Peeling Adhesive Strength Test Method Part 4: Floating Roller Method”.
- the produced polarizing temporary was fixed on a metal plate (stainless steel, dimensions: length 200 mm, width 25 mm, thickness 1.5 mm) with a double-sided adhesive tape (ST-416P, manufactured by Sumitomo 3M).
- ST-416P double-sided adhesive tape
- the sample is attached to a floating roller, the edge of the peeled film sample is fixed to the grip of the tensile tester, and the grip is lifted at a speed of 300 mm / min using the tensile tester to peel the film.
- the average peel force (N / 25 mm) was measured, and the adhesiveness (peel strength) was determined as follows. The results are shown in Table 1. ⁇ : The measured average peel force was 2 N / 25 mm or more. X: The measured average peel force was less than 2 N / 25 mm.
- the wet heat test was conducted under conditions of a temperature of 60 ° C., a relative humidity of 90%, and 500 hours.
- a polarizing plate obtained by adhering a protective film using these is polarized even after a moist heat resistance test and a thermal shock test while maintaining high adhesiveness of the protective film. Since the protective film of the plate does not peel off and reliability can be secured, it is particularly useful as a material applicable to optical members such as polarizing plates.
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Abstract
Description
(A)脂環式エポキシ基を分子内に2個以上有する化合物、
(B)水酸基を分子内に3個有する化合物、及び
(C)光酸発生剤、を含む放射線硬化性組成物であって、
[放射線硬化性組成物中に含まれる(A)の全脂環式エポキシ基数/放射線硬化性組成物中に含まれる(B)の全水酸基数]が2.0未満であることを特徴とする放射線硬化性組成物、を提供する。 That is, the present invention
(A) a compound having two or more alicyclic epoxy groups in the molecule,
A radiation curable composition comprising (B) a compound having three hydroxyl groups in the molecule, and (C) a photoacid generator,
[The number of all alicyclic epoxy groups of (A) contained in the radiation curable composition / the total number of hydroxyl groups of (B) contained in the radiation curable composition] is less than 2.0. Radiation curable compositions are provided.
(A)脂環式エポキシ基を分子内に2個以上有する化合物が、下記式(I)で表される化合物であることが好ましい。
(A) The compound having two or more alicyclic epoxy groups in the molecule is preferably a compound represented by the following formula (I).
Xが、エステル結合を含有する連結基であることが好ましい。 In the radiation curable composition,
X is preferably a linking group containing an ester bond.
(B)水酸基を分子内に3個有する化合物がポリエステルトリオールであることが好ましい。 In the radiation curable composition,
(B) The compound having three hydroxyl groups in the molecule is preferably a polyester triol.
前記放射線硬化性組成物を含有する接着剤、を提供する。 The present invention also provides:
An adhesive containing the radiation curable composition is provided.
前記放射線硬化性組成物を含有する偏光板用接着剤、を提供する。 The present invention also provides:
An adhesive for polarizing plate containing the radiation curable composition is provided.
偏光膜の少なくとも一方の面に、前記接着剤を用いて、保護フィルムを接着してなる偏光板、を提供する。 The present invention also provides:
Provided is a polarizing plate obtained by adhering a protective film to at least one surface of a polarizing film using the adhesive.
本発明の放射線硬化性組成物は、
(A)脂環式エポキシ基を分子内に2個以上有する化合物、
(B)水酸基を分子内に3個有する化合物、及び
(C)光酸発生剤、を含む放射線硬化性組成物であって、
[放射線硬化性組成物中に含まれる(A)の全脂環式エポキシ基数/放射線硬化性組成物中に含まれる(B)の全水酸基数]が2.0未満であれば良く、その他の点では特に制限されない。 [Radiation curable composition]
The radiation curable composition of the present invention comprises:
(A) a compound having two or more alicyclic epoxy groups in the molecule,
A radiation curable composition comprising (B) a compound having three hydroxyl groups in the molecule, and (C) a photoacid generator,
[A total number of alicyclic epoxy groups of (A) contained in the radiation curable composition / total number of hydroxyl groups of (B) contained in the radiation curable composition] may be less than 2.0. The point is not particularly limited.
脂環式エポキシ基とは、脂環を構成する隣接する2つの炭素原子と酸素原子とで構成されるエポキシ基を意味する。 [(A) Compound having two or more alicyclic epoxy groups in the molecule]
An alicyclic epoxy group means an epoxy group composed of two adjacent carbon atoms and oxygen atoms constituting the alicyclic ring.
(B)水酸基を分子内に3個有する化合物としては、ポリエステルトリオール、グリセリン、トリメチロールエタン、トリメチロールプロパン、アダマンタントリオール等が挙げられ、特に制限されないが、エポキシ化合物との相溶性の観点からエステル基を含むポリエステルトリオールが好ましく、ポリカプロラクトントリオールが特に好ましい。 [(B) Compound having three hydroxyl groups in the molecule]
(B) Examples of the compound having three hydroxyl groups in the molecule include polyester triol, glycerin, trimethylol ethane, trimethylol propane, adamantane triol, and the like, but are not particularly limited, but are esters from the viewpoint of compatibility with epoxy compounds. Polyester triols containing groups are preferred and polycaprolactone triols are particularly preferred.
a、b、cは、いずれも1以上の整数であり、それぞれ、例えば1~30、好ましくは1~10の範囲内であり、a+b+cは好ましくは3~30の範囲内であり、
R1は、3価の炭化水素基、好ましくは3価の脂肪族炭化水素基であり、R1の炭素数は好ましくは3~20、より好ましくは3~15、さらに好ましくは3~10の範囲内であり、R1の代表例としては、以下の式(III-1)~(III-4)で表される3価の炭化水素基等が挙げられる。
a, b and c are all integers of 1 or more, and are each in the range of, for example, 1 to 30, preferably 1 to 10, and a + b + c is preferably in the range of 3 to 30,
R 1 is a trivalent hydrocarbon group, preferably a trivalent aliphatic hydrocarbon group, and R 1 preferably has 3 to 20, more preferably 3 to 15, and still more preferably 3 to 10 carbon atoms. Within the range, typical examples of R 1 include trivalent hydrocarbon groups represented by the following formulas (III-1) to (III-4).
(C)光酸発生剤としては、特に制限されないが、紫外線照射により酸を発生し、発生した酸によりカチオン重合を開始させる作用を有するものが好ましい。 [(C) Photoacid generator]
(C) Although it does not restrict | limit especially as a photo-acid generator, The thing which generate | occur | produces an acid by ultraviolet irradiation and has an effect | action which starts cationic polymerization by the generated acid is preferable.
本発明の放射線硬化性組成物は、上記(A)~(C)成分の他、必要に応じて、粘度を調整するための有機溶剤(カチオン硬化しうる有機溶剤が好ましく、具体的には、1,3-ブタンジオール、セロキサイド2000等が挙げられる。いずれもダイセル社製のものが市販品の具体例として挙げられる。)、接着強度及びスクリーン印刷性を向上させるための無機質充填剤(例えば、電気化学工業社製の球状シリカである、FB-5SDC、FB-3SDC等)、さらに接着強度を向上させるシランカップリング剤(例えば、エボニック・デグサ・ジャパン社製である、Dynasylan AMEO、Dynasylan GLYMO等)、塗布性能を向上させるレベリング剤(例えば、ビックケミー・ジャパン社製である、BYK-307、BYK-333等)、その他添加剤を本発明の効果を妨げない範囲で含有していても良い。 [Other ingredients]
In addition to the components (A) to (C), the radiation curable composition of the present invention is preferably an organic solvent for adjusting the viscosity if necessary (an organic solvent capable of cationic curing, specifically, 1,3-butanediol, Celoxide 2000, etc., all of which are manufactured by Daicel Corp.), inorganic fillers for improving adhesive strength and screen printability (for example, Spherical silica manufactured by Denki Kagaku Kogyo Co., Ltd., such as FB-5SDC, FB-3SDC, etc., and silane coupling agents that improve adhesion strength (eg, Evonik Degussa Japan Co., Ltd., Dynasylan AMEO, Dynasylan GLYMO, etc.) ), Leveling agents that improve coating performance (for example, BYK-307, BYK-333, etc., manufactured by BYK Japan, Inc.) and other additives are included within a range that does not interfere with the effects of the present invention. It may be.
本発明の接着剤は、前記放射線硬化性組成物を含有していれば良く、その他の点では特に制限されない。 [adhesive]
The adhesive of this invention should just contain the said radiation-curable composition, and is not restrict | limited in particular at another point.
本発明の偏光板は、偏光膜の少なくとも一方の面に、前記接着剤を用いて、保護フィルムを接着してなる偏光板であれば良く、その他の点では特に制限されない。 [Polarizer]
The polarizing plate of this invention should just be a polarizing plate formed by adhere | attaching a protective film on the at least one surface of a polarizing film using the said adhesive agent, and is not restrict | limited in particular at another point.
偏光膜としては、特に制限されないが、具体的には、ポリビニルアルコール系樹脂フィルムに二色性染料を吸着させ、これを一軸延伸して製造されるポリビニルアルコール系偏光膜等が挙げられる。 [Polarizing film]
The polarizing film is not particularly limited, and specific examples include a polyvinyl alcohol polarizing film produced by adsorbing a dichroic dye on a polyvinyl alcohol resin film and uniaxially stretching the dichroic dye.
撹拌装置付きの容器に、表1に示す配合割合(質量比)で、成分(A)~(C)を投入し、4時間撹拌し均一に混合した。撹拌を停止し、24時間静置して、実施例1~3に用いる放射線硬化性組成物を得た。同様に、比較例1~7に用いる放射線硬化性組成物を得た。 [1. Preparation of radiation curable composition for adhesive]
Components (A) to (C) were added in a mixing ratio (mass ratio) shown in Table 1 in a container equipped with a stirrer, and stirred for 4 hours to mix uniformly. Stirring was stopped and the mixture was allowed to stand for 24 hours to obtain radiation curable compositions used in Examples 1 to 3. Similarly, radiation curable compositions used in Comparative Examples 1 to 7 were obtained.
(A)成分
セロキサイド2021P:3,4-エポキシシクロヘキセニルメチル(3’,4’-エポキシ)シクロヘキサンカルボキシレート[3,4-エポキシシクロヘキシルメチル(3,4-エポキシ)シクロヘキサンカルボキシレート、ダイセル社製]
セロキサイド3000:1,2:8,9-ジエポキシリモネン(ダイセル社製)
エポリードPB3600:エポキシ化ポリブタジエン(液状)(ダイセル社製)
(B)成分
プラクセル205:ポリカプロラクトンジオール(分子量530)(ダイセル社製)
プラクセル305:ポリカプロラクトントリオール(分子量550)(ダイセル社製)
(C)成分
CPI-100P:ジフェニル[4-(フェニルチオ)フェニル]スルホニウムヘキサフルオロホスファート(サンアプロ社製) In addition, the compound name of each component in Table 1 is as follows.
Component (A) Celoxide 2021P: 3,4-epoxycyclohexenylmethyl (3 ′, 4′-epoxy) cyclohexanecarboxylate [3,4-epoxycyclohexylmethyl (3,4-epoxy) cyclohexanecarboxylate, manufactured by Daicel Corporation]
Celoxide 3000: 1, 2: 8,9-diepoxy limonene (Daicel)
Epolide PB3600: Epoxidized polybutadiene (liquid) (Daicel)
Component (B) Placcel 205: Polycaprolactone diol (molecular weight 530) (manufactured by Daicel)
PLACCEL 305: polycaprolactone triol (molecular weight 550) (Daicel)
(C) Component CPI-100P: Diphenyl [4- (phenylthio) phenyl] sulfonium hexafluorophosphate (manufactured by San Apro)
[偏光膜(PVAフィルム)]
ホウ酸20質量部、ヨウ素0.2質量部、ヨウ化カリウム0.5質量部を水480質量部に溶解させて染色液を調製した。この染色液にPVAフィルム(ビニロンフィルム#40、アイセロ社製)を、30秒浸漬した後、フィルムを一方向に2倍に延伸し、乾燥させて、膜厚30μmのPVAフィルムを作製した。 [2. Production or preparation of adhesive substrate]
[Polarizing film (PVA film)]
A staining solution was prepared by dissolving 20 parts by mass of boric acid, 0.2 parts by mass of iodine, and 0.5 parts by mass of potassium iodide in 480 parts by mass of water. A PVA film (Vinylon film # 40, manufactured by Aicello) was immersed in this dyeing solution for 30 seconds, and then the film was stretched twice in one direction and dried to prepare a PVA film having a thickness of 30 μm.
保護フィルムとして、アクリビュア(PMMAフィルム、日本触媒社製)を使用した。なお、保護フィルムは、コロナ表面処理装置(春日電機社製の「コロナ表面改質評価装置(TEC-4AX)」)を用い、320W・分/m2の放電量でフィルム表面にコロナ放電処理を行い、表面処理後1時間以内に接着を実施した。 [Protective film]
As a protective film, acryl viewer (PMMA film, manufactured by Nippon Shokubai Co., Ltd.) was used. The protective film was subjected to corona discharge treatment on the film surface with a discharge amount of 320 W · min / m 2 using a corona surface treatment device (“Corona Surface Modification Evaluation Device (TEC-4AX)” manufactured by Kasuga Electric Co., Ltd.). And adhesion was carried out within 1 hour after the surface treatment.
[実施例1~3、比較例1~7]
得られた放射線硬化性組成物を、ワイヤーバーコーター#3を用いてアクリビュア(保護フィルム)上に塗工し、その上にPVAフィルムを気泡等の欠陥が入らないように金属ローラーを用いて貼合した。次にアクリビュア(保護フィルム)上に、上記放射線硬化性組成物を、ワイヤーバーコーター#3を用いて塗工し、上記貼合したPVAフィルム上に、気泡等の欠陥が入らないように貼合した。ガラス板上に、張り合わせたものの四方をテープで固定し、高圧水銀ランプ(UVC-02516S1AA02:ウシオ電機社製、照度120mW/cm2、照射光量199mJ/cm2)で光照射した。 [3. Production of polarizing plate]
[Examples 1 to 3, Comparative Examples 1 to 7]
The obtained radiation curable composition is coated on an acrylic (protective film) using a wire bar coater # 3, and a PVA film is pasted thereon using a metal roller so that bubbles and other defects do not enter. Combined. Next, the radiation curable composition is applied onto an acrylic viewer (protective film) using a wire bar coater # 3, and bonded to the bonded PVA film so that defects such as bubbles do not enter. did. On a glass plate, a four-way despite bonded taped, high pressure mercury lamp (UVC-02516S1AA02: manufactured by Ushio Inc., illuminance 120 mW / cm 2, irradiation amount 199mJ / cm 2) was irradiated with light.
得られた偏光板の接着性(剥離強度)、湿熱試験後における偏光板の外観(耐湿熱性)、温度衝撃試験後における偏光板の外観(耐熱衝撃性)を下記の方法により評価した。結果を表1に示す。なお、得られた放射線硬化性組成物の、[放射線硬化性組成物中に含まれる(A)の全脂環式エポキシ基数/放射線硬化性組成物中に含まれる(B)の全水酸基数]もあわせて表1に[全エポキシ基数]/[全水酸基数]として示す。 [4. Evaluation]
The adhesion (peeling strength) of the obtained polarizing plate, the appearance of the polarizing plate after the wet heat test (wet heat resistance), and the appearance of the polarizing plate after the temperature shock test (thermal shock resistance) were evaluated by the following methods. The results are shown in Table 1. In addition, [the number of all the alicyclic epoxy groups of (A) contained in the radiation curable composition / the total number of hydroxyl groups of (B) contained in the radiation curable composition] of the obtained radiation curable composition] These are also shown in Table 1 as [total number of epoxy groups] / [total number of hydroxyl groups].
作製した偏光板の接着性(剥離強度)は「JISK6854-4接着剤-剥離接着強さ試験法第4部:浮動ローラ法」に準じて測定した。作製した偏光仮を金属板(ステンレス製、寸法:長さ200mm、幅25mm、厚み1.5mm)上に両面粘着テープ(ST-416P、住友スリーエム社製)で固定した。偏光板中、PVAフィルムと保護フィルムの間において、カッターナイフを用いて長手方向の端を剥離した。JIS法に従い、浮動ローラにサンプルを取り付け、剥離したフィルムサンプルの端を引っ張り試験機のつかみ具に固定し、引っ張り試験機を用いて300mm/分の速度でつかみ具を上昇させ、フィルムが剥離するときの平均剥離力(N/25mm)を測定し、接着性(剥離強度)を以下のように判定した。結果を表1に示す。
○:測定された平均剥離力が2N/25mm以上であった
×:測定された平均剥離力が2N/25mm未満であった (Adhesive evaluation)
The adhesiveness (peeling strength) of the produced polarizing plate was measured according to “JISK6854-4 Adhesive—Peeling Adhesive Strength Test Method Part 4: Floating Roller Method”. The produced polarizing temporary was fixed on a metal plate (stainless steel, dimensions: length 200 mm, width 25 mm, thickness 1.5 mm) with a double-sided adhesive tape (ST-416P, manufactured by Sumitomo 3M). In the polarizing plate, the end in the longitudinal direction was peeled between the PVA film and the protective film using a cutter knife. According to the JIS method, the sample is attached to a floating roller, the edge of the peeled film sample is fixed to the grip of the tensile tester, and the grip is lifted at a speed of 300 mm / min using the tensile tester to peel the film. The average peel force (N / 25 mm) was measured, and the adhesiveness (peel strength) was determined as follows. The results are shown in Table 1.
○: The measured average peel force was 2 N / 25 mm or more. X: The measured average peel force was less than 2 N / 25 mm.
以下のように、湿熱試験、又は温度衝撃試験を行い、試験前後の偏光板を目視により観察することで、偏光板の耐湿熱性、耐熱衝撃性を評価した。耐湿熱性、耐熱衝撃性の評価基準として、湿熱試験後における偏光板の外観、及び温度衝撃試験後における偏光板の外観を以下のように判定した。結果を表1に示す。
○:試験前後の偏光板に変化が無かった
×:試験後の偏光板には、偏光板の色抜けや保護フィルムの剥離があった (Evaluation of wet heat resistance and thermal shock resistance)
A wet heat test or a temperature impact test was performed as follows, and the wet and heat resistance and thermal shock resistance of the polarizing plate were evaluated by visually observing the polarizing plate before and after the test. As evaluation criteria for heat and humidity resistance and thermal shock resistance, the appearance of the polarizing plate after the wet heat test and the appearance of the polarizing plate after the temperature shock test were determined as follows. The results are shown in Table 1.
○: There was no change in the polarizing plate before and after the test. ×: The polarizing plate after the test had color loss of the polarizing plate and peeling of the protective film.
湿熱試験は、温度60℃、相対湿度90%、500時間の条件で行った。 (Moist heat test)
The wet heat test was conducted under conditions of a temperature of 60 ° C., a relative humidity of 90%, and 500 hours.
湿熱試験は、温度-40℃~80℃、1サイクル30分、100サイクルの条件で行った。 (Temperature shock test)
The wet heat test was performed under the conditions of a temperature of −40 ° C. to 80 ° C., one cycle of 30 minutes, and 100 cycles.
Claims (10)
- (A)脂環式エポキシ基を分子内に2個以上有する化合物、
(B)水酸基を分子内に3個有する化合物、及び
(C)光酸発生剤、を含む放射線硬化性組成物であって、
[放射線硬化性組成物中に含まれる(A)の全脂環式エポキシ基数/放射線硬化性組成物中に含まれる(B)の全水酸基数]が2.0未満であることを特徴とする放射線硬化性組成物。 (A) a compound having two or more alicyclic epoxy groups in the molecule,
A radiation curable composition comprising (B) a compound having three hydroxyl groups in the molecule, and (C) a photoacid generator,
[The number of all alicyclic epoxy groups of (A) contained in the radiation curable composition / the total number of hydroxyl groups of (B) contained in the radiation curable composition] is less than 2.0. Radiation curable composition. - (A)脂環式エポキシ基を分子内に2個以上有する化合物が、下記式(I)で表される化合物である、請求項1記載の放射線硬化性組成物。
- Xが、エステル結合を含有する連結基である、請求項2記載の放射線硬化性組成物。 The radiation curable composition according to claim 2, wherein X is a linking group containing an ester bond.
- (B)水酸基を分子内に3個有する化合物がポリエステルトリオールである、請求項1~3の何れか1項に記載の放射線硬化性組成物。 (B) The radiation curable composition according to any one of claims 1 to 3, wherein the compound having three hydroxyl groups in the molecule is a polyester triol.
- 請求項1~4の何れか1項に記載の放射線硬化性組成物を含有する接着剤。 An adhesive containing the radiation curable composition according to any one of claims 1 to 4.
- 光増感剤を含まないことを特徴とする、請求項5に記載の接着剤。 The adhesive according to claim 5, which does not contain a photosensitizer.
- 請求項1~4の何れか1項に記載の放射線硬化性組成物を含有する偏光板用接着剤。 An adhesive for a polarizing plate comprising the radiation curable composition according to any one of claims 1 to 4.
- 光増感剤を含まないことを特徴とする、請求項7に記載の偏光板用接着剤。 The adhesive for polarizing plates according to claim 7, which does not contain a photosensitizer.
- 偏光膜の少なくとも一方の面に、請求項5又は6に記載の接着剤を用いて、保護フィルムを接着してなる偏光板。 A polarizing plate obtained by adhering a protective film to at least one surface of the polarizing film using the adhesive according to claim 5 or 6.
- 照射光量が300mJ/cm2以下の放射線照射によって、前記接着剤が硬化してなる、請求項9記載の偏光板。 The polarizing plate according to claim 9, wherein the adhesive is cured by irradiation with an irradiation light amount of 300 mJ / cm 2 or less.
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JPH10130611A (en) * | 1996-10-30 | 1998-05-19 | Nippon Synthetic Chem Ind Co Ltd:The | Self-adhesive composition |
JPH10330717A (en) * | 1997-05-27 | 1998-12-15 | Nippon Kayaku Co Ltd | Adhesive composition, substrate and liquid crystal panel |
JP2011242582A (en) * | 2010-05-18 | 2011-12-01 | Sumitomo Chemical Co Ltd | Polarizing plate set, liquid crystal panel using polarizing plate set and liquid crystal display device using polarizing plate set |
JP2012001690A (en) * | 2010-06-21 | 2012-01-05 | Adeka Corp | Photocurable resin composition |
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CN101235257A (en) * | 2007-02-02 | 2008-08-06 | Jsr株式会社 | Composition for radiation solidifying adhesive, composite body and preparation method for the composite body |
-
2013
- 2013-04-23 CN CN201380020692.XA patent/CN104245777A/en active Pending
- 2013-04-23 KR KR1020147032843A patent/KR20150015475A/en not_active Application Discontinuation
- 2013-04-23 WO PCT/JP2013/061942 patent/WO2013161826A1/en active Application Filing
- 2013-04-23 JP JP2014512617A patent/JPWO2013161826A1/en active Pending
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Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH10130611A (en) * | 1996-10-30 | 1998-05-19 | Nippon Synthetic Chem Ind Co Ltd:The | Self-adhesive composition |
JPH10330717A (en) * | 1997-05-27 | 1998-12-15 | Nippon Kayaku Co Ltd | Adhesive composition, substrate and liquid crystal panel |
JP2011242582A (en) * | 2010-05-18 | 2011-12-01 | Sumitomo Chemical Co Ltd | Polarizing plate set, liquid crystal panel using polarizing plate set and liquid crystal display device using polarizing plate set |
JP2012001690A (en) * | 2010-06-21 | 2012-01-05 | Adeka Corp | Photocurable resin composition |
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