WO2017065259A1 - 樹脂組成物およびこれを用いた光学フィルム - Google Patents
樹脂組成物およびこれを用いた光学フィルム Download PDFInfo
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- WO2017065259A1 WO2017065259A1 PCT/JP2016/080498 JP2016080498W WO2017065259A1 WO 2017065259 A1 WO2017065259 A1 WO 2017065259A1 JP 2016080498 W JP2016080498 W JP 2016080498W WO 2017065259 A1 WO2017065259 A1 WO 2017065259A1
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- polyvinyl alcohol
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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
- C08L29/00—Compositions of 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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical; Compositions of hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Compositions of derivatives of such polymers
- C08L29/02—Homopolymers or copolymers of unsaturated alcohols
- C08L29/04—Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
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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
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D129/00—Coating compositions 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 an alcohol, ether, aldehydo, ketonic, acetal, or ketal radical; Coating compositions based on hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Coating compositions based on derivatives of such polymers
- C09D129/02—Homopolymers or copolymers of unsaturated alcohols
- C09D129/04—Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids
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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
- 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
- G02B1/041—Lenses
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/133305—Flexible substrates, e.g. plastics, organic film
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
- G03C1/835—Macromolecular substances therefor, e.g. mordants
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring
- C08K5/353—Five-membered rings
Definitions
- the present invention relates to a resin composition and an optical film using the same, and more particularly, to a resin composition having excellent transparency and coating properties and low liquid crystal contamination, and an optical film using the same.
- Patent Documents 1 and 2 propose a composite film having a layer containing polyvinyl alcohol and a water-dispersible copolyester having a sulfonyloxy residue
- Patent Document 3 includes polyvinyl alcohol and a water-dispersible polyester. Coated film products having an aqueous tie layer have been proposed.
- a resin composition containing polyvinyl alcohol for an optical film for a flat panel display, a coating material for an optical film, a sealing agent for a liquid crystal dropping method, etc., in addition to high transparency and coatability, low liquid crystal contamination is present. Desired. However, in the resin composition containing polyvinyl alcohol, such physical properties are not necessarily sufficient, and the present situation is that further improvement is required.
- an object of the present invention is to provide a resin composition excellent in transparency and coating property and having low liquid crystal contamination, and an optical film using the same.
- a resin composition containing polyvinyl alcohol and polyester having a predetermined structure is excellent in transparency and applicability, has low liquid crystal contamination, and is a flat panel display.
- the present invention was completed by finding that it can be suitably used for optical films, optical film coating materials, sealing agents for liquid crystal dropping methods, and the like.
- the resin composition of the present invention is a resin composition containing polyvinyl alcohol and polyester,
- the polyester has a carboxyl group and / or a salt of a carboxyl group as a substituent.
- the polyvinyl alcohol may be a homopolymer or a copolymer having vinyl alcohol as an essential monomer.
- the polyvinyl alcohol preferably has an acetoacetate group.
- the saponification degree of the polyvinyl alcohol is preferably 85 or more.
- the content of the polyester is preferably 0.5 to 50% by mass in the solid content.
- the resin composition of the present invention preferably further contains a crosslinking agent.
- the said crosslinking agent is an oxazoline compound or a carbodiimide compound.
- the optical film of the present invention is characterized by comprising the resin composition of the present invention.
- the resin composition of the present invention is a resin composition containing polyvinyl alcohol and polyester, and the polyester has a carboxyl group and / or a salt of the carboxyl group as a substituent.
- the polyvinyl alcohol and polyester according to the resin composition of the present invention will be described in detail.
- the polyvinyl alcohol may be a homopolymer or a copolymer having vinyl alcohol as an essential monomer.
- Examples of the copolymerizable monomer include unsaturated carboxylic acids such as maleic acid, maleic anhydride, fumaric acid, crotonic acid, itaconic acid, acrylic acid, methacrylic acid, and esters thereof, ethylene, propylene, and the like.
- unsaturated carboxylic acids such as maleic acid, maleic anhydride, fumaric acid, crotonic acid, itaconic acid, acrylic acid, methacrylic acid, and esters thereof, ethylene, propylene, and the like.
- allyl sulfonic acid methallyl sulfonic acid, allyl sulfonic acid soda, methallyl sulfonic acid soda, sulfonic acid soda, sulfonic acid soda monoalkyl malate, disulfonic acid soda alkyl malate, N-methylol acrylamide, acrylamide alkyl
- examples include sulfonic acid alkali salts, N-vinylpyrrolidone, and N-vinylpyrrolidone derivatives.
- polyvinyl alcohol may be used alone or in combination of two or more.
- the weight average molecular weight (Mw) in terms of polystyrene by gel permeation chromatography (GPC) of polyvinyl alcohol is 10,000 to 200,000, and the saponification degree (hydrolysis rate) is 85 or more, particularly 85 to 100. It is preferable because water resistance is improved and durability of the film is improved.
- polyvinyl alcohol commercially available products can be used.
- Gohsenol NL-05, NH-18, NH-20, NH-26, NM-14, AH-17, A-300, GM-14L, GL- 05, KL-05, GH-23, KH-17 manufactured by Nippon Synthetic Chemical Industry
- Gosenx Z-100, Z-200, Z-300, Z-410, T-330H manufactured by Nippon Synthetic Chemical Industry
- Nichigo G-polymer OKS-1081, OKS-1083 manufactured by Nippon Synthetic Chemical Industry Co., Ltd.
- VF-17, V-S20 manufactured by Nippon Vinegar Poval
- Kuraray Poval PVA-103, PVA-105, PVA- 117, PVA-205, PVA-217, PVA-405, PVA-420 manufactured by Kuraray
- the polyester according to the resin composition of the present invention has at least one of a carboxyl group and a carboxyl group salt as a substituent. Such a polyester is dissolved in water, emulsified by dispersing in water, or dissolved in alkaline water.
- a carboxyl group salt an alkali metal salt, an ammonium salt or an amine salt is preferable because the effects of the present invention can be obtained satisfactorily.
- the carboxyl group in the polyester preferably has an acid value of 15 to 250 KOHmg / g of the produced polyester.
- the acid value is less than 15 KOHmg / g, it is difficult to disperse the polyester in water, and the uniformity is lowered, and the film forming property may be lowered. Further, when the acid value exceeds 250 KOHmg / g, the water resistance may be poor. The higher the acid value, the less the scattering in the visible region, the finer the dispersed particles and the better the affinity for water, and the better the compatibility with polyvinyl alcohol.
- polyesters according to the resin composition of the present invention those having a carboxyl group salt as a substituent are obtained, for example, by polycondensation of a trifunctional or higher polyvalent carboxylic acid and a compound having one or two hydroxyl groups. are preferred.
- trifunctional or higher polyvalent carboxylic acid examples include trimellitic acid, trimellitic anhydride, pyromellitic acid, pyromellitic anhydride, 4-methylcyclohexene-1,2,3 tricarboxylic acid anhydride, trimesic acid, etc. Is mentioned. These may be used alone or in combination of two or more.
- Examples of the compound having one or two hydroxyl groups include aliphatic polyols, polyhydroxy aromatic compounds, polyether diols, polyester diols, polyester polycarbonate diols, polycarbonate diols, polyolefin diols, and hydroxyl groups at one end of these compounds. Examples thereof include those alkoxylated with an alkyl group of 1 to 25. These may be used alone or in combination of two or more.
- Examples of the aliphatic polyol include ethylene glycol, 1,2-propanediol, 1,3-propanediol, 2-methyl-1,3-propanediol, and 2-butyl-2-ethyl-1,3-propane.
- polyether diol examples include ethylene oxide adducts such as diethylene glycol and triethylene glycol; propylene oxide adducts such as dipropylene glycol and tripropylene glycol; ethylene oxide and / or propylene oxide adducts of low molecular polyols, poly Examples include tetramethylene glycol.
- polyester diol examples include low molecular weight diols, dicarboxylic acids in an amount less than the stoichiometric amount, ester forming derivatives thereof such as esters, anhydrides, halides, and / or lactones or hydrolytic ring opening thereof. And those obtained by a direct esterification reaction and / or transesterification reaction with the hydroxycarboxylic acid thus obtained.
- dicarboxylic acid examples include oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, azelaic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, fumaric acid, maleic acid, dodecanedioic acid, 2- Methylsuccinic acid, 2-methyladipic acid, 3-methyladipic acid, 3-methylpentanedioic acid, 2-methyloctanedioic acid, 3,8-dimethyldecanedioic acid, 3,7-dimethyldecanedioic acid, hydrogenated dimer Aliphatic dicarboxylic acids such as acids and dimer acids; phthalic acid, terephthalic acid, isophthalic acid, dimethylmalonic acid, glutaric acid, trimethyladipic acid, 2,2-dimethylglutaric acid, itaconic acid, 1,3-cyclopentanedicarboxylic acid Acid, 1,
- Polycarbonate diols include poly (1,6-hexylene) carbonate and poly (3-methyl-1,5-pentylene) carbonate.
- Polyolefin diols include polybutadiene glycol, hydrogenated polybutadiene glycol, and hydrogenated polyisoprene glycol. Etc.
- polyether diol and / or polyester diol are particularly preferable.
- the molecular weight of the compound having one or two hydroxyl groups in the same molecule is 300 to 3,000, preferably 500 to 2,000.
- polyhydroxy aromatic compound examples include 4,4-biphenol, 1,1-bis (4-hydroxyphenyl) ethane, 2,2-bis (4-hydroxyphenyl) propane, and 2,2-bis (4 -Hydroxyphenyl) butane, bis (4-hydroxyphenyl) ether, bis (4-hydroxyphenyl) sulfide, bis (4-hydroxyphenyl) sulfone, 4,4 '-(1- ⁇ -methylbenzylidene) bisphenol, 4, 4 '-(1- ⁇ -ethylbenzylidene) bisphenol, 1,1-bis (4-hydroxyphenyl) cyclohexane, 9,9-bis (4-hydroxyphenyl) fluorene, ⁇ , ⁇ '-bis (4-hydroxyphenyl) ) -1,4-diisopropylbenzene, hydrogenated bisphenol compound, resorcinol, Loquinone, 2,5-di-tert-butylhydroquinone, 1,4-dihydroxy
- polyester polycarbonate diol examples include a reaction product of polyester glycol such as polycaprolactone polyol and alkylene carbonate, a reaction product obtained by reacting a reaction product of ethylene carbonate and glycol with an organic dicarboxylic acid, and the like. Can be mentioned.
- polystyrene diols examples include polybutadiene glycol, hydrogenated polybutadiene glycol, and hydrogenated polyisoprene glycol.
- the polyester according to the resin composition of the present invention may be prepared by graft polymerization of a polymerizable unsaturated carboxylic acid to the polyester, or as shown in JP-A-62-240318, a polyester or a polyester glycol having a hydroxyl group at the end and a tetra It can also be obtained by a method in which a carboxylic dianhydride is chain extended by a selective monoesterification reaction.
- polyester commercially available products can be used.
- Nichigo Polyester WR-961, WR-1031 manufactured by Nippon Synthetic Chemical Industry Co., Ltd.
- Pesresin A-680, A-690 A-210, A-230, A-695GE manufactured by Takamatsu Yushi Co., Ltd.
- Pluscoat Z-730, Z-760 manufactured by Kyoyo Chemical Co., Ltd.
- -1335, MD-1480, MD-1500, MD-1930, MD-1985, MD-2000 manufactured by Toyobo
- the weight average molecular weight (Mw) in terms of polystyrene by gel permeation chromatography (GPC) of the polyester is preferably 500 to 30,000 from the viewpoint of water resistance, and 1,000. More preferably, it is ⁇ 10,000.
- the blending ratio of polyvinyl alcohol and polyester is preferably 99.5: 0.5 to 50:50 in terms of solid content from the viewpoint of compatibility, and transparency and water resistance of the coating film. In view of the above, 95: 5 to 60:40 is more preferable.
- the water resistance and heat resistance can be improved by further adding a crosslinking agent and reacting with the carboxylate.
- Crosslinking agents include oxazoline compounds, carbodiimide compounds, epoxy compounds, oxetane compounds, vinyl ether compounds, polyamines, polyols, polyphenols, polyfunctional thiols, dicyandiamide derivatives, hydrazine compounds, polyhydrazide compounds (dihydrazide, trihydrazide), aldehydes , Methylol compounds, activated vinyl compounds, polyisocyanate compounds, alkylene carbonate compounds of phenolic compounds, polyvalent metal salts, silane coupling agents, organic titanium, organic zirconium, etc., among which oxazoline compounds and carbodiimide compounds
- the reaction is preferably performed at a heat drying temperature of 100 to 120 ° C.
- a commercially available product can be used as the crosslinking agent.
- Epocross WS-300, WS-500, WS-700 manufactured by Nippon Shokubai Co., Ltd.
- Carbodilite V-02, V- 02-L2, SV-02, V-04, V-10, SW-12G, E-02, E-03A, E-05 (Nisshinbo Chemical Co., Ltd.);
- SR-4GL, SR-6GL Sakamoto Yakuhin Kogyo Co., Ltd.
- Manufactured by ORGATICS ZC-126 and TC-315 manufactured by Matsumoto Fine Chemical Co., Ltd.
- the resin composition of the present invention can be obtained by mixing an aqueous solution or aqueous dispersion of polyvinyl alcohol and an aqueous solution, aqueous dispersion or water-dispersible emulsion of polyester, and if necessary, a coupling agent or a surfactant. Etc. can also be added.
- Examples of the coupling agent include alkyl functionalities such as dimethyldimethoxysilane, dimethyldiethoxysilane, methylethyldimethoxysilane, methylethyldiethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, and ethyltrimethoxysilane.
- Alkenyl functional alkoxysilanes such as functional alkoxysilane, vinyltrichlorosilane, vinyltrimethoxysilane, vinyltriethoxysilane, allyltrimethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3- Methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 2-methacryloxypropyltrimethoxysilane, ⁇ -glycy Epoxy-functional alkoxysilanes such as xylpropyltrimethoxysilane, ⁇ -glycidoxypropylmethyldiethoxysilane, ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxysilane, N- ⁇ (aminoethyl) - ⁇ -amino Aminofunctional alkoxysilanes
- the surfactant examples include fluorine surfactants such as perfluoroalkyl phosphates and perfluoroalkyl carboxylates, anionic surfactants such as higher fatty acid alkali salts, alkyl sulfonates, and alkyl sulfates, and higher amines. Cationic surfactants such as halogenates and quaternary ammonium salts, nonionic surfactants such as polyethylene glycol alkyl ethers, polyethylene glycol fatty acid esters, sorbitan fatty acid esters and fatty acid monoglycerides, amphoteric surfactants, silicone surfactants Surfactants such as agents can be used, and these may be used in combination.
- fluorine surfactants such as perfluoroalkyl phosphates and perfluoroalkyl carboxylates
- anionic surfactants such as higher fatty acid alkali salts, alkyl sulfonates, and alkyl sulfates,
- the resin composition of the present invention can be used as a photo / thermosetting resin composition by further adding a radical polymerizable compound, a polymerization initiator, and a sensitizer as necessary.
- the obtained photo / thermosetting resin composition is expected to have high water resistance and heat resistance.
- the radical polymerizable compound is not particularly limited, and those conventionally used can be used.
- unsaturated aliphatic hydrocarbons unsaturated polybasic acids, unsaturated monobasic acids and esters of polyhydric alcohols or polyhydric phenols, unsaturated polybasic acid anhydrides, unsaturated monobasic acids and polyamines Amides, unsaturated aldehydes, unsaturated aromatic compounds, unsaturated ketones, vinyl ethers, unsaturated imides, indenes, aliphatic conjugated dienes, macromonomers having a mono (meth) acryloyl group at the end of the polymer molecular chain , Vinyl chloride, vinylidene chloride, divinyl succinate, diallyl phthalate, triallyl phosphate, triallyl isocyanurate, vinyl thioether, vinyl imidazole, vinyl oxazoline, vinyl carbazole, vinyl pyrrolidone, vinyl pyridine, hydroxyl group-containing vinyl monomers
- the polymerization initiator may be any compound capable of initiating radical polymerization by receiving light / heat irradiation.
- Examples thereof include ketones such as acetophenone compounds, benzyl compounds, benzophenone compounds, and thioxanthone compounds.
- Photo-radical polymerization initiators such as 2,3′-azobisisobutyronitrile, 2,2′-azobis (methylisobutyrate), 2,2′-azobis-2,4- Azo initiators such as dimethylvaleronitrile, 1,1′-azobis (1-acetoxy-1-phenylethane); benzoyl peroxide, di-t-butylbenzoyl peroxide, t-butylperoxypivalate, di ( 4-t-butylcyclohexyl) peroxydicarbonate and other peroxide initiators, persulfate Moniumu, sodium persulfate, thermal radical polymerization initiator such as persulfate salts such as potassium sulfate. These can be used alone or in combination of two or more.
- the sensitizer is a compound capable of expanding the wavelength range in which light can be adapted when cured by light irradiation.
- the resin composition of the present invention can be applied on a supporting substrate such as glass, metal, paper, plastic, etc. by a known means such as a spin coater, bar coater, roll coater, curtain coater, various types of printing and dipping. .
- a support substrate such as a film
- it can be transferred onto another support substrate, and the application method is not limited.
- the resin composition of the present invention may be added to a colorant such as an acid generator, a base initiator, an inorganic filler, an organic filler, a pigment, and a dye, Sticky agent, leveling agent, thixotropic agent, carbon compound, metal fine particle, metal oxide, flame retardant, plasticizer, light stabilizer, heat stabilizer, anti-aging agent, elastomer particle, chain transfer agent, polymerization inhibitor, UV absorption
- a colorant such as an acid generator, a base initiator, an inorganic filler, an organic filler, a pigment, and a dye, Sticky agent, leveling agent, thixotropic agent, carbon compound, metal fine particle, metal oxide, flame retardant, plasticizer, light stabilizer, heat stabilizer, anti-aging agent, elastomer particle, chain transfer agent, polymerization inhibitor, UV absorption
- a colorant such as an acid generator, a base initiator, an inorganic filler, an organic filler, a pigment, and a dye,
- Specific applications of the resin composition of the present invention include glasses, optical materials represented by imaging lenses, paints, coating agents, lining agents, inks, resists, liquid resists, adhesives, and sealing agents for liquid crystal dropping methods. , Printing plates, insulating varnishes, insulating sheets, laminates, printed boards, for semiconductor devices, for LED packages, for liquid crystal injection ports, for organic EL, for optical elements, for electrical insulation, for electronic components, for separation membranes, etc.
- Sealing agent molding material, putty, glass fiber impregnating agent, sealing agent, passivation film for semiconductors and solar cells, interlayer insulating film, protective film, prism lens sheet used for backlight of liquid crystal display device, Lens parts of lens sheets such as Fresnel lens sheets and lenticular lens sheets used for projection television screens, or such sheets Liquid crystal color filter protective films and spacers, DNA separation chips, microreactors, nanobiodevices, recording materials for hard disks, solid-state imaging devices, solar cell panels, light emitting diodes, organic light emitting devices, luminescent films, etc.
- Examples include fluorescent films, MEMS elements, actuators, holograms, plasmon devices, polarizing plates, polarizing films, microlenses and other optical lenses, optical elements, optical connectors, optical waveguides, optical molding casting agents, and the like.
- Examples of the substrate that can be applied as the coating agent include metals, wood, rubber, plastic, glass, ceramic products and the like.
- the optical film of the present invention is composed of the resin composition of the present invention.
- the optical film of the present invention may be produced by forming a film or a sheet by a conventional method and without stretching (or orientation treatment) the obtained film or sheet, or by stretching (or orientation treatment). May be.
- a melt molding method such as extrusion molding or blow molding
- a casting method such as cast film forming method, solution casting method
- examples of the material for the transparent support include inorganic materials such as glass; diacetyl cellulose, triacetyl cellulose (TAC). ), Cellulose esters such as propionylcellulose, butyrylcellulose, acetylpropionylcellulose, nitrocellulose; polyamide; polycarbonate; polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate, poly-1,4-cyclohexanedimethylene terephthalate, polyethylene-1, Polyesters such as 2-diphenoxyethane-4,4′-dicarboxylate and polybutylene terephthalate; polystyrene; polyolefins such as polyethylene, polypropylene and polymethylpentene Emissions; acrylic resins such as polymethyl methacrylate, polycarbonate, polysulfone, polyether sulfone, polyether ketone; polyether
- the irradiation conditions such as the wavelength, intensity and irradiation time of the irradiated light depend on the activity of the photoinitiator and the photopolymerizable resin used.
- the light wavelength is usually preferably a wavelength peak of 350 to 400 nm, more preferably a wavelength peak of 360 to 380 nm in order to allow light to sufficiently enter the inside.
- the light intensity is preferably 10 to 300 mW / cm 2 , more preferably 25 to 100 mW / cm 2
- the irradiation time is preferably 5 to 500 seconds, more preferably 10 to 300 seconds.
- the heating conditions such as the heating temperature and the heating time may be appropriately adjusted depending on the activity of the radical polymerizable compound or the polymerization initiator. Is preferably 80 to 200 ° C., and the heating time is preferably 30 seconds to 60 minutes.
- the optical film of the present invention is not particularly limited in terms of shape, but is usually a film having an optical film on a transparent support and used for optical purposes, and for polarizing plates used in liquid crystal display devices and the like.
- the optical film of the present invention includes an optical recording layer of a write-once optical disc (CD ⁇ R, DVD ⁇ R, next-generation high-density disc, etc.) in which the optical film is applied to a support; various lenses; an optical filter for an image display device; Various filters typified by color filters and color conversion filters; or can be used as protective sealing films for organic EL light-emitting elements, inorganic EL light-emitting elements, electronic paper displays, and the like.
- a write-once optical disc CD ⁇ R, DVD ⁇ R, next-generation high-density disc, etc.
- Examples 1 to 36 and Comparative Examples 1 to 14 ⁇ Preparation of aqueous polyvinyl alcohol solution> First, 100.0 g of the following polyvinyl alcohols A-1 to A-7 were gradually added to 900.0 g of ion-exchanged water stirred at room temperature. The solution was stirred at room temperature for 10 minutes and then heated until the internal temperature reached 85 to 90 ° C., and stirring was continued at that temperature for 1 hour. After confirming the dissolution of the polyvinyl alcohol, the aqueous polyvinyl alcohol solution was cooled to room temperature. Thereafter, the prepared aqueous polyvinyl alcohol solution was filtered through a 1 ⁇ m filter.
- the blending amounts of PV-1 to PV-7, B-1 to B-6, B′-1, and B′-3 in Tables 1 to 8 below are ratios (mass%) in terms of solid content. Yes, and B'-2 is in a liquid form, so it is the total amount.
- A-1 GOHSENOL NL-05 (Saponification degree 99) manufactured by Nippon Synthetic Chemical Industry A-2 Gohsenol GL-05 (degree of saponification 87) manufactured by Nippon Synthetic Chemical Industry A-3 Nichigo G-polymer OKS-1083 (saponification degree 99) manufactured by Nippon Synthetic Chemical Industry A-4 Goseinex Z-300 (Saponification degree 98) manufactured by Nippon Synthetic Chemical Industry A-5 Goseinex Z-200 (degree of saponification 98) manufactured by Nippon Synthetic Chemical Industry A-6 GOHSENOL KL-05 (Saponification degree 80) manufactured by Nippon Synthetic Chemical Industry A-7 Goseinex T-330H manufactured by Nippon Synthetic Chemical Industry (degree of saponification 99, anionic modified product having a carboxyl group in the molecule)
- PV-7 A-7 aqueous solution B-6 Made by Takamatsu Yushi, Pesresin A-230 (Substituent: COOH, solid content 30%, acid value 80 mgKOH / g)
- C-1 Nippon Shokubai Epocross WS-700 (oxazoline compound; cross-linking agent, solid content 25%)
- VHR On the coating film obtained in the applicability test, the following liquid crystal compound no. 1-No.
- the liquid crystal composition consisting of 11 was contacted, and after 60 hours at 60 ° C., the liquid crystal composition was taken out to conduct a resin dissolution test.
- the VHR before and after the resin dissolution test was compared for the extracted liquid crystal composition, the reduction rate of VHR was determined, and evaluation was performed according to the following criteria.
- the liquid crystal composition was injected into a TN cell for liquid crystal evaluation (cell thickness 5 ⁇ m, electrode area 8 mm ⁇ 8 mm alignment film JALS2096), and VHR was measured using VHR-1A (manufactured by Toyo Technica).
- the measurement conditions were pulse voltage width: 60 ⁇ s, frame period: 16.7 ms, wave height: ⁇ 5 V, measurement temperature: 25 ° C.
- ⁇ : VHR is over 99% ⁇ : VHR is 97 to 99% X: VHR is less than 97%
- the resin composition of the present invention is excellent in transparency and coating properties and low in liquid crystal contamination. Therefore, the resin composition of the present invention can be suitably used for an optical film or a sealing agent for liquid crystal dropping method.
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Abstract
Description
前記ポリエステルが、カルボキシル基および/またはカルボキシル基の塩を置換基として有することを特徴とするものである。
本発明の樹脂組成物は、ポリビニルアルコールおよびポリエステルを含有する樹脂組成物であり、ポリエステルは、カルボキシル基および/またはカルボキシル基の塩を置換基として有する。以下、本発明の樹脂組成物に係るポリビニルアルコールおよびポリエステルについて、詳細に説明する。
本発明の樹脂組成物においては、ポリビニルアルコールは、ビニルアルコールを必須の単量体とするホモポリマーであってもよく、コポリマーであってもよい。一般的にポバールと呼ばれるビニルアルコールを重合させたポリビニルアルコール、部分けん化ポリビニルアルコール、完全けん化ポリビニルアルコールの他、カルボキシル基変性ポリビニルアルコール、アセト酢酸エステル基変性ポリビニルアルコール、メチロール基変性ポリビニルアルコール、アミノ基変性ポリビニルアルコール、エステル基変性ポリビニルアルコール、カルボキシル基変性ポリビニルアルコール、アミド基変性ポリビニルアルコール、スチリルピリジニウム基変性ポリビニルアルコール、四級アンモニウム塩基変性ポリビニルアルコール、アリル基変性ポリビニルアルコール、オキシプロピレン基変性ポリビニルアルコール、ウレタン基変性ポリビニルアルコール、エーテル基変性ポリビニルアルコール、リン酸エステル基変性ポリビニルアルコール、アセタール基変性ポリビニルアルコール、ブチラール基変性ポリビニルアルコール、シラノール基変性ポリビニルアルコール、側鎖に1,2-ジオール構造を有するポリビニルアルコールのような、変性されたポリビニルアルコール;酢酸ビニルと共重合性を有する単量体との共重合体のけん化物等が挙げられる。これらの中でも、アセト酢酸エステル基変性ポリビニルアルコールは熱処理によって架橋するため、好適に用いることができる。
本発明の樹脂組成物に係るポリエステルは、カルボキシル基およびカルボキシル基の塩の少なくともいずれか一方を置換基として有する。このようなポリエステルは、水に溶解、水分散して乳化、あるいはアルカリ水に溶解する。本発明の樹脂組成物に係るポリエステルにおいては、カルボキシル基の塩としては、アルカリ金属塩、アンモニウム塩またはアミン塩が、本発明の効果を良好に得られるので好ましい。
<ポリビニルアルコール水溶液の調製>
まず、イオン交換水900.0gを室温で撹拌しているところに、下記のA-1~A-7のポリビニルアルコール100.0gを徐々に添加した。この溶液を室温で10分撹拌した後に、内温が85から90℃になるまで加熱し、その温度で1時間撹拌を継続した。ポリビニルアルコールの溶解を確認した後、ポリビニルアルコール水溶液を室温まで冷却した。その後、調製したポリビニルアルコール水溶液を1μmフィルターでろ過した。ただし、下記表1~表8中のPV-1~PV-7、B-1~B-6およびB’-1、B’-3の配合量は、固形分換算の比率(質量%)であり、B’-2は液状であるため全量である。
A-2 日本合成化学工業製 ゴーセノールGL-05(けん化度87)
A-3 日本合成化学工業製 Nichigo G-polymer OKS-1083(けん化度99)
A-4 日本合成化学工業製 ゴーセネックス Z-300(けん化度98)
A-5 日本合成化学工業製 ゴーセネックス Z-200(けん化度98)
A-6 日本合成化学工業製 ゴーセノール KL-05(けん化度80)
A-7 日本合成化学工業製 ゴーセネックス T-330H(けん化度99、分子内にカルボキシル基を有するアニオン性変性品)
先に調製したポリビニルアルコール水溶液と、下記表1~表8に示すB-1~B-6およびB’-1~B’-3のポリエステル水溶液と、下記表6~表8に示すC-1~C-6の架橋剤とを、同表の配合に従って混合して、室温で1時間撹拌後、1μmフィルターでろ過し、各実施例および比較例の樹脂組成物を得た。
PV-2 A-2の水溶液
PV-3 A-3の水溶液
PV-4 A-4の水溶液
PV-5 A-5の水溶液
PV-6 A-6の水溶液
B-1 高松油脂製、ペスレジンA-690(置換基:COOH、固形分20%、酸価50mgKOH/g)
B-2 日本合成化学工業製、ポリエスターWR-961(置換基:COOH、固形分30%、酸価60mgKOH/g)
B-3 日本合成化学工業製、ポリエスターWR-1031(置換基:COOH、固形分30%、酸価80mgKOH/g)
B-4 互応化学工業製、プラスコートZ-730(置換基:COOH、固形分25%、酸価50mgKOH/g)
B-5 高松油脂製、ペスレジンA-210(置換基:COOH、固形分30%、酸価70mgKOH/g)
B’-1 高松油脂製、ペスレジンA-640(置換基:SO3Na、固形分25%)
B’-2 ADEKA製、アデカサイザーPN-77(フタル酸エステル系)
B’-3 互応化学製、プラスコートZ-446(置換基:SO3Na、固形分25%)
B-6 高松油脂製、ペスレジンA-230(置換基:COOH、固形分30%、酸価80mgKOH/g)
C-1 日本触媒製、エポクロスWS-700(オキサゾリン化合物;架橋剤、固形分25%)
C-2 日清紡ケミカル製、カルボジライトV-02-L2(カルボジイミド化合物;架橋剤、固形分40%)
C-3 阪本薬品工業製、SR-4GL(エポキシ化合物;架橋剤、有効成分100%)
C-4 阪本薬品工業製、SR-6GL(エポキシ化合物;架橋剤、有効成分100%)
C-5 マツモトファインケミカル製、オルガチックスZC-126(塩化ジルコニル化合物;架橋剤、固形分30%)
C-6 マツモトファインケミカル製、オルガチックスTC-315(チタンラクテート;架橋剤、固形分44%)
各樹脂組成物の状態を目視で確認した。判定基準は下記の通りである。
○:透明均一
△:白濁
×:相溶せず(相分離)
各樹脂組成物を、ガラス基板上にスピンコーターを用いて塗布した後、70℃のホットプレートで5分間、90℃のホットプレートで5分間の順にプリベークを行なった後、140℃で15分加熱を行なうことで評価用基板を作製した。膜厚は触針法で5.0~5.5μmとなるようスピンコートの条件を調整した。
得られた評価用基板について、目視で表面の状態を確認すると同時に、ヘイズ測定によって評価を行なった。測定には日本電色製ヘイズメーターNDH5000を使用し、判定基準は下記の通りとした。
○:膜が均一、ヘイズ1未満
△:膜が均一、ヘイズ1以上3未満
×:膜は全面に残存、ヘイズ3以上
××:膜の一部が剥離あるいは溶出
得られた評価用基板を85℃,85%RHの条件で100時間放置した後の基板の表面状態を、a)と同様にして評価した。判定基準は上記と同様である。
塗布性試験において得られた塗膜上に、下記液晶化合物No.1~No.11よりなる液晶組成物を接し、60℃で60時間後、液晶組成物を取り出すことにより樹脂溶出性試験を行った。取り出した液晶組成物について樹脂溶出性試験前後でのVHRを比較し、VHRの低下率を求め、下記基準により評価を行った。
○:VHRが99%超
△:VHRが97~99%
×:VHRが97%未満
Claims (8)
- ポリビニルアルコールおよびポリエステルを含有する樹脂組成物において、
前記ポリエステルが、カルボキシル基および/またはカルボキシル基の塩を置換基として有することを特徴とする樹脂組成物。 - 前記ポリビニルアルコールが、ビニルアルコールを必須の単量体とするホモポリマーまたはコポリマーである請求項1記載の樹脂組成物。
- 前記ポリビニルアルコールが、アセト酢酸エステル基を有する請求項1記載の樹脂組成物。
- 前記ポリビニルアルコールのけん化度が、85以上である請求項1記載の樹脂組成物。
- 前記ポリエステルの含有量が、固形分中0.5~50質量%である請求項1記載の樹脂組成物。
- さらに、架橋剤を含有する請求項1記載の樹脂組成物。
- 前記架橋剤が、オキサゾリン化合物またはカルボジイミド化合物である請求項6記載の樹脂組成物。
- 請求項1記載の樹脂組成物からなることを特徴とする光学フィルム。
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