CN102686689B - Polarizer binder composition and make use of the Polarizer of said composition - Google Patents
Polarizer binder composition and make use of the Polarizer of said composition Download PDFInfo
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- CN102686689B CN102686689B CN201080046723.5A CN201080046723A CN102686689B CN 102686689 B CN102686689 B CN 102686689B CN 201080046723 A CN201080046723 A CN 201080046723A CN 102686689 B CN102686689 B CN 102686689B
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- 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
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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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- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/625—Polymers of alpha-beta ethylenically unsaturated carboxylic acids; hydrolyzed polymers of esters of these acids
- C08G18/6254—Polymers of alpha-beta ethylenically unsaturated carboxylic acids and of esters of these acids containing hydroxy groups
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/794—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aromatic isocyanates or isothiocyanates
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- 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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- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/08—Homopolymers or copolymers of acrylic acid esters
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- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
- C09J7/22—Plastics; Metallised plastics
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- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C09J7/385—Acrylic polymers
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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
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
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- 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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- 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
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
- C08K5/34924—Triazines containing cyanurate groups; Tautomers thereof
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- 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
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- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays
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- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/302—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
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- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
- C09J2301/408—Additional features of adhesives in the form of films or foils characterized by the presence of essential components additives as essential feature of the adhesive layer
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- Chemical & Material Sciences (AREA)
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- Polymers & Plastics (AREA)
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- Polarising Elements (AREA)
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Abstract
The present invention relates to a kind of Polarizer binder composition and make use of the Polarizer of said composition, described Polarizer binder composition can be formed by the slaking between short-term has excellent weather resistance and the binder layer of leakproof photosensitiveness.The feature of this Polarizer binder composition is, containing following composition (A) and composition (B), that is, (A) is (methyl) acrylic polymers 100 mass parts of 300,000 ~ 1,500,000 to the obtaining containing the monomer copolymerization of carboxyl of major general's mass percent 1 ~ 10%, weight-average molecular weight; (B) there is tolylene diisocyanate compounds 4 ~ 20 mass parts of isocyanurate structure.
Description
Technical field
The present invention relates to a kind of Polarizer binder composition, more specifically, relate to a kind of can be formed by the slaking between short-term have the excellent adaptive binder layer of optics, Polarizer binder composition and utilize the Polarizer of said composition.
Background technology
Liquid crystal cell has liquid crystal material and is held in structure between two substrates, and is bonded with Polarizer by binder layer on a surface of the substrate.In recent years, liquid crystal cell is expanded, and measuring instrument to vehicle boarded use, room is used, the purposes such as indicating meter, TV of computer, and accompany therewith, environment for use also becomes very harsh.
Polarizer has the multilayered structure of differing materials, therefore from the characteristic shortage dimensional stability of constituent material.Especially under high temperature, high damp and hot environment for use, stress concentration is made due to the contraction because of Polarizer, thus cause the double refraction of Polarizer, and tackiness agent itself also carries out orientation due to stress concentration thus produces double refraction, therefore produce color spot (light leak) in the end of stress concentration, and reduce display quality.In addition, in such a case, the bad phenomenon in the foaming of interface of Polarizer and glass or the stripping of Polarizer etc. is easily produced.Therefore, require that the tackiness agent of Polarizer has excellent leakproof photosensitiveness and weather resistance.
On the other hand, when Polarizer is formed binder layer, manifest to make above-mentioned leakproof photosensitiveness and weather resistance, and need under the state being coated with binder composition on Polarizer, the curing step of about one week is such as at room temperature set and binder composition is solidified, but due between this long-term maturation period, and create the problem that productivity reduces or tank farm stock increases.
Be directed to this problem, and propose following method, that is, in the mixture of the acrylate copolymer containing hydroxyl and isocyanates linking agent, by making further containing carboxyl in the acrylate copolymer containing hydroxyl, thus promote the method (patent documentation 1) of solidification.But in the art, the addition of isocyanates linking agent is less, thus sufficient leakproof photosensitiveness and weather resistance cannot be obtained by the slaking of short period of time.In addition a kind of surface protective film binder composition is disclosed; described surface protective film binder composition contains: containing hydroxyl and the acrylic polymers of carboxyl and polyfunctional isocyanate's class of aliphatic category or the alicyclic ring same clan or isocyanuric acid ester compound, thus shorten setting up period (patent documentation 2).But the amount of the carboxyl of the acrylic polymers used in this binder composition is defined, thus be not suitable for the purposes of the bonding between Polarizer and glass.Suppose to the addition of above-mentioned aliphatic category or alicyclic ring in the tackiness agent that carboxyl of the present invention is a above when belonging to polyfunctional isocyanate's class or the isocyanuric acid ester compound of class, will there is the tendency in shortening heat life-span, therefore cannot actual use.
In addition, a kind of binder composition (patent documentation 3 and patent documentation 4) that with the addition of the optical thin film of isocyanate ester compound in the acrylic polymers with carboxyl is disclosed.But these technology, to improve re-workability, leakproof photosensitiveness for target, do not carry out any consideration to the shortening between the maturation period.Therefore, disclosed binder composition all cannot obtain sufficient optics adaptability by the slaking between short-term in those references.
At first technical literature
Patent documentation
Patent documentation 1: Japanese Unexamined Patent Publication 2008-156513 publication
Patent documentation 2: Japanese Unexamined Patent Publication 2005-247909 publication
Patent documentation 3: Japanese Patent No. 4136524 publication
Patent documentation 4: Japanese Unexamined Patent Publication 2008-144126 publication
Summary of the invention
Invent problem to be solved
Therefore, expect a kind of can by the slaking between short-term, and form the Polarizer binder composition of the binder layer possessing excellent weather resistance and leakproof photosensitiveness, problem of the present invention is, provides this Polarizer binder composition.
For solving the method for problem
The present inventor carries out found that of wholwe-hearted research repeatedly in order to solve above-mentioned problem, by using the tolylene diisocyanate compounds with isocyanurate structure using as linking agent, and relative to have specified range molecular weight containing the acrylic polymers of carboxyl, and mix this tolylene diisocyanate compounds relatively largely, even if thus by the slaking between short-term, also can be formed and there is excellent weather resistance and the binder layer of leakproof photosensitiveness, this completes the present invention.
Namely, the present invention is a kind of Polarizer binder composition, it is characterized in that, containing following composition (A) and composition (B), that is, (A) is (methyl) acrylic polymers 100 mass parts of 300,000 ~ 1,500,000 to the obtaining containing the monomer copolymerization of carboxyl of major general's mass percent 1 ~ 10%, weight-average molecular weight; (B) there is tolylene diisocyanate compounds 4 ~ 20 mass parts of isocyanurate structure.
In addition, the present invention is a kind of Polarizer, and it forms by arranging the binder layer formed by above-mentioned Polarizer binder composition on the face of at least side of polarizing film.
The effect of invention
Binder composition of the present invention by by this binder composition for Polarizer, even if thus under hot and humid condition, also effectively can prevent the generation of light leak, in addition there is excellent weather resistance, the generation of the foaming of binder layer or stripping etc. can be suppressed.And, because curing speed is very fast, and the significantly shortening between the maturation period can be realized, therefore, it is possible to boost productivity significantly, and reduce tank farm stock.
Embodiment
Acrylic polymers for the composition (A) of Polarizer binder composition of the present invention is, contains the monomer copolymerization of carboxyl and the polymkeric substance obtained to major general.
As the above-mentioned monomer containing carboxyl, can list: (methyl) vinylformic acid, 2-carboxy ethyl (methyl) acrylate, 3-carboxypropyl (methyl) acrylate, 4-carboxybutyl (methyl) acrylate, methylene-succinic acid, β-crotonic acid, toxilic acid, fumaric acid and maleic anhydride etc.
Monomer containing carboxyl is mass percent 1 ~ 10% (following, to be represented by " % ") relative to the content of the formation monomer entirety of composition (A) acrylic polymers, is preferably 2 ~ 8%, is more preferably 2 ~ 6%.To be not easy when being less than 1% to obtain cohesive force, and more than 10% time cohesive force too high or bounding force is risen, be not therefore preferred.
As other formation monomer of the acrylic polymers of composition (A), can list: (methyl) alkyl acrylate, the monomer containing hydroxyl, the monomer containing phenyl ring, (methyl) vinylformic acid alkoxy ester, the monomer containing amino, the monomer etc. containing amide group.
As above-mentioned (methyl) vinylformic acid alkoxy ester, preferably have carbonatoms be 1 ~ 12 can with the material of the alkyl of side chain, specifically, can list: (methyl) methyl acrylate, (methyl) ethyl propenoate, (methyl) propyl acrylate, (methyl) isopropyl ester, (methyl) butyl acrylate, (methyl) isobutyl acrylate, (methyl) amyl acrylate, (methyl) Ethyl acrylate, 2-ethylhexyl (methyl) acrylate, (methyl) vinylformic acid octyl group ester, (methyl) nonylphenol acrylate ester, (methyl) vinylformic acid certain herbaceous plants with big flowers ester, (methyl) dodecylacrylate, (methyl) lauryl acrylate.In these materials, because the balance of the bounding force of butyl acrylate, methyl acrylate and weather resistance is good, therefore preferably use.
(methyl) alkyl acrylate is 10 ~ 99% relative to the content of the formation monomer entirety of composition (A) acrylic polymers, is preferably 50 ~ 98.5%.The balance of bounding force and weather resistance cannot be obtained sometimes when being less than 10%, and more than 99% time weather resistance be deteriorated sometimes.
As the above-mentioned monomer containing hydroxyl, can illustrate: 2-hydroxyethyl (methyl) acrylate, 4-hydroxybutyl (methyl) acrylate, 2-hydroxypropyl (methyl) acrylate, 2-hydroxybutyl (methyl) acrylate, 6-hydroxyl hexyl (methyl) acrylate, 1,4-cyclohexanedimethanol list (methyl) acrylate, chloro-2-acrylate, Diethylene Glycol list (methyl) acrylate, vinyl carbinol etc., by making this monomer copolymerization containing hydroxyl, thus gel ratio can be improved further.In these materials, because the copolymerizable of 2-hydroxyethylmethacry,ate, 4-hydroxybutyl acrylate and (methyl) alkyl acrylate is good, therefore preferably use.
Monomer containing hydroxyl is 0 ~ 1% relative to the content of the formation monomer entirety of composition (A) acrylic polymers, is preferably 0.05 ~ 1%.When more than 1% time gel ratio will become too high, thus cementability will reduce, thus the possibility occurring under being present in high temperature, high damp and hot condition to peel off etc.
The above-mentioned monomer containing phenyl ring has positive intrinsic double refraction, by the monomer copolymerization making this contain phenyl ring, thus can reduce the double refraction of (methyl) acrylic polymers.Specifically, can list: phenyl acrylate, Phenoxyethyl (methyl) acrylate, (methyl) benzyl acrylate, phenoxy group Diethylene Glycol (methyl) acrylate, ethylene-oxide-modified nonylphenol (methyl) acrylate, hydroxyethylated 2-Naphthol acrylate, (methyl) biphenyl acrylate, vinylbenzene, Vinyl toluene, alpha-methyl styrene etc.In these materials, because the consistency of benzyl acrylate, phenoxyethyl acrylate and (methyl) alkyl acrylate, copolymerizable are better, and can not the transparency be reduced, therefore preferably use.
Monomer containing phenyl ring is 0 ~ 40% relative to the content of the formation monomer entirety of composition (A) acrylic polymers, is preferably 0 ~ 30%.When more than 40% time cannot obtain suitable bounding force sometimes.
As above-mentioned (methyl) vinylformic acid alkoxy ester, can illustrate: (methyl) vinylformic acid 2-methoxy acrylate, (methyl) vinylformic acid 2-ethoxy ethyl ester, (methyl) vinylformic acid 2-methoxyl group propyl ester, (methyl) vinylformic acid 3-methoxyl group propyl ester, (methyl) vinylformic acid 2-methoxybutyl, (methyl) vinylformic acid 4-methoxybutyl etc.(methyl) vinylformic acid alkoxy ester is 0 ~ 90% relative to the content of the formation monomer entirety of composition (A) acrylic polymers, is preferably 0 ~ 80%.
As above-mentioned containing amino monomer, can illustrate: (methyl) acrylate, (methyl) vinylformic acid diethylamino ethyl ester etc.
As the above-mentioned monomer containing amide group, can illustrate: (methyl) acrylamide, (methyl) N hydroxymethyl acrylamide etc.All relative to the formation monomer of (A) acrylic polymers, these contain the monomer of amino, the usage quantity of the monomer containing amide group is about 0 ~ 1%.
Composition of the present invention (A) by utilizing the existing known polymerizations such as solution polymerization process, mass polymerization, emulsion polymerization method, suspension polymerization, can make the polymerization of mixtures of above-mentioned monomer component, thus preparing.In these compositions (A), be more preferably the composition (A) prepared by the solution polymerization process not containing the polymerization stabilizer such as emulsifying agent or suspension agent or mass polymerization.
The weight-average molecular weight (Mw) of the composition (A) obtained in the above described manner is 300,000 ~ 1,500,000, is preferably 400,000 ~ 1,200,000.When weight-average molecular weight is less than 300,000, weather resistance will be deteriorated, and viscosity will increase when weight-average molecular weight is greater than 1,500,000, thus have problems in process.In addition, in this manual, weight-average molecular weight refers to, the value obtained by measuring method described in an embodiment.
In addition, the second-order transition temperature of the acrylic polymers of composition (A) is preferably less than 0 DEG C, is more preferably less than-20 DEG C, is especially preferably-80 DEG C ~-30 DEG C.When second-order transition temperature is higher than 0 DEG C, the tackiness agent obtained will reduce to the binding property of base material or the pliability of binder layer, thus the stripping occurred sometimes from base material or tilting.In addition, in this manual, glass transition temperature is the value calculated by following FOX formula.
(FOX formula)
1/Tg＝Wa/Tga+Wb/Tgb+…
Tg: the second-order transition temperature of multipolymer
Tga, Tgb ...: monomer a, monomer b ... the second-order transition temperature of homopolymer
Wa, Wb ...: monomer a, monomer b ... weight ratio
The composition (B) used in the present invention, the tolylene diisocyanate compounds with isocyanurate structure is, in its structure, comprise the compound of the isocyanurate ring formed by tolylene diisocyanate trimerizing, and also comprise various modification body.The compound of composition (B) can be obtained by the method recorded in Japanese Unexamined Patent Publication 8-193114 publication, No. 2006/137307th, International Publication etc., as the compound being equivalent to composition (B), can that (CORONATE) 342 of Lip river, can Lip river that 2030 (being Japanese Polyurethane industrial system) etc. go on the market.
The allotment amount of the composition (B) in Polarizer binder composition of the present invention, relative to composition (A) 100 mass parts (following, to be expressed as " part "), be 4 ~ 20 parts, be preferably 6 ~ 15 parts.Be less than 4 parts of hourglass optical properties by bad owing to working as, and when becoming too high more than cohesive force when 20 parts, be not therefore preferred.
In addition, in Polarizer binder composition of the present invention, can be used together the linking agent (composition (C)) outside mentioned component (B).As this linking agent, can list: tolylene diisocyanate class linking agent (except the material with isocyanurate structure), epoxies linking agent, ethylenimine class linking agent, can use in these materials one or more.
As above-mentioned tolylene diisocyanate class linking agent (except the material with isocyanurate structure), can list: tolylene diisocyanate; Make isocyanate compound, biuret form compound that described tolylene diisocyanate and the polyvalent alcohol such as TriMethylolPropane(TMP), tetramethylolmethane carry out addition reaction and obtain; Described tolylene diisocyanate and known polyether glycol, polyester polyol, acrylic polyol, polybutadiene polyol, polyisoprene polyol etc. is made to carry out addition reaction and the derivative such as isocyanate compound of the carbamate prepolymer type obtained.By and with this tolylene diisocyanate class linking agent (except the material with isocyanurate structure), thus the binding property relative to base material can be improved, suppress thus to peel off.In these materials, be preferably tolylene diisocyanate, trimethylolpropane toluene vulcabond etc.
In Polarizer binder composition of the present invention, tolylene diisocyanate class linking agent (except the material with isocyanurate structure) is preferably, and allocates in the mode becoming 1: 3 ~ 3: 1 relative to the allotment ratio of composition (B).When allotment ratio is outside this scope, slaking will need between longer-term, and occur sometimes to peel off under high temperature, high wet heat condition.
As above-mentioned epoxy crosslinking agent, the compound containing plural epoxy group(ing) in the molecule of following material can be listed, described material comprises: the redix of bisphenol A/epichlorohydrin type, ethylene glycidyl ether, polyethyleneglycol diglycidylether, glycerin diglycidyl ether, T 55, 1, 6-hexanediol diglycidyl ether, trihydroxymethylpropanyltri diglycidyl ether, diglycidylaniline, diamines glycidyl group amine, N, N, N ', N '-four glycidyl group m-xylene diamine, 1, two (the N of 3-, N '-diamines glycidyl-amino methyl) hexanaphthene etc.By and with these epoxies linking agents, thus gel ratio can be improved further.In these materials, preferably use N, N, N ', N '-four glycidyl group m-xylene diamine, 1,3-two (N, N '-diamines glycidyl-amino methyl) hexanaphthene.
The allotment amount of the epoxy crosslinking agent in Polarizer binder composition of the present invention is 0 ~ 1% relative to composition (B), is preferably 0.05 ~ 0.5%.When allotment amount is outside this scope, slaking will need between longer-term, and occur sometimes to peel off under high temperature, high wet heat condition.
As above-mentioned ethylenimine class linking agent, can list: 1,1 '-(methylene radical-two pairs of phenylenes) two-3, two-3, the 3-aziridinyl ureas of 3-aziridinyl urea, 1,1 '-(hexa-methylene), 2,4,6-tri-aziridinyls-1,3,5-triazines, TriMethylolPropane(TMP)-three-(2-aziridinyl propionic ester) etc.By and with these ethylenimine class linking agents, thus gel ratio can be improved further.
The allotment amount of the ethylenimine class linking agent in Polarizer binder composition of the present invention is 0 ~ 1% relative to composition (B), is preferably 0.05 ~ 0.5%.When allotment amount is outside this scope, slaking will need between longer-term, and occur sometimes to peel off under high temperature, high wet heat condition.
Be preferably, in Polarizer binder composition of the present invention, also allotment has silane coupling agent (D), and described allotment silane coupling agent (D) carries out containing with contained carboxyl in composition (A) acrylic polymers the group that reacts.By using described silane coupling agent (D), thus tackiness agent can be made to be bonded in securely on glass, can prevent from thus peeling off under hygrothermal environment.Specifically, described silane coupling agent (D) can list: the silane coupling agent containing epoxy group(ing) such as 3-glycidylpropyl Trimethoxy silane, 3-glycidylpropyl triethoxyl silane, 3-glycidylpropyl methyldiethoxysilane, 2-(3,4-expoxycyclohexyl) ethyl trimethoxy silane; And 3-TSL 8330, N-2 (amino-ethyl) 3-TSL 8330 etc. are containing amino silane coupling agent etc.
The allotment amount of the silane coupling agent (D) in Polarizer binder composition of the present invention is 0.05 ~ 1 part relative to composition (A) 100 parts, is preferably 0.1 ~ 0.5 part.Owing to will easily peel off under hygrothermal environment when being less than 0.05 part, and when being greater than 1 part in high temperature environments silane coupling agent by imbibition, easily peel off on the contrary, be not therefore preferred.
The mode that is prepared as follows of Polarizer binder composition of the present invention is carried out, namely, mentioned component (A), composition (B) are allocated with composition (C), composition (D) or other any composition as required, and they mixed by ordinary method.As operable any composition, can list: oxidation inhibitor, UV light absorber, plasticizer, antistatic agent etc., these materials can be allocated in the scope not affecting effect of the present invention.
In order to obtain Polarizer adhesive sheet of the present invention by Polarizer binder composition obtained thus, the face of at least side by ordinary method on supporting mass is coated with this binder composition, and carries out drying, slaking and form binder layer after coating.Drying carries out about 2 ~ 10 minutes usually at 80 ~ 110 DEG C.On the other hand, binder composition of the present invention can significantly shorten between the maturation period compared with existing material, such as, 23 DEG C, the condition of 50%RH is cured fully by the slaking of about 1 ~ 3 day, thus can obtains possessing good bounding force and the adaptive binder layer of optics.The gel ratio of the binder layer after slaking is preferably 60 ~ 90%, is more preferably 65 ~ 85%.When outside this scope, weather resistance can be deteriorated thus easily peel off sometimes.In addition, in this manual, gel ratio refers to, the value obtained by measuring method described in embodiment.As supporting mass, effects on surface can have been used the to carry out polyester film of lift-off processing.The thickness of binder layer is generally 10 ~ 30 μm, is preferably about 15 ~ 25 μm.
In addition, by being arranged on the face of at least side of polarizing film by the binder layer formed by above-mentioned Polarizer binder composition, thus Polarizer of the present invention can be obtained.The thickness being arranged on the binder layer on polarizing film is generally 10 ~ 30 μm, is preferably about 15 ~ 25 μm.
When polarizing film arranges binder layer, binder layer can be formed in the following way, that is, binder composition is coated on polarizing film, and make its drying, slaking; Or will to be coated on supporting mass and dried film is attached on polarizing film, and to make its slaking.Drying, the condition of slaking and the scope etc. of gel ratio, same as above.
In addition, as polarizing film used in the present invention, also stackedly can have the layer of other functions, specifically, also comprise elliptical polarized light film, phase-contrast film etc.
By being arranged on the substrate surface of liquid crystal cells by the Polarizer of the present invention obtained by aforesaid way, thus produce liquid crystal cell.As the type of the liquid crystal cell of use Polarizer of the present invention, be not particularly limited, TN type, VA type, IPS type, OCB type etc.By suitably installing the component parts of backlight etc. on this liquid crystal cell, thus produce the liquid crystal indicator reducing light leak.
Polarizer binder composition of the present invention, can be formed by the slaking between short-term and possess excellent leakproof photosensitiveness and the binder layer of weather resistance, think that its reason is as follows.
That is, can say when during excessive interpolation isocyanate ester compound, will the polyureas in isocyanate ester compound source being generated in tackiness agent.Although this polyureas tangles with the host polymer of tackiness agent and physical property occurs and is combined, thus there is the reticulated structure identical with general tackiness agent, but when having the tolylene diisocyanate compounds of isocyanurate structure, think that also there is the identical reticulated structure produced by tangling.Snappiness is become due to the polyureas in the tolylene diisocyanate compounds source because having isocyanurate structure, and also can control double refraction, therefore leakproof photosensitiveness becomes good, and, owing to there is the tolylene diisocyanate compounds of isocyanurate structure compared with other isocyanate ester compound, reactivity is higher, thus the formation reaction of crosslinking reaction or polyureas is very fast, therefore, it is possible to significantly shorten between the maturation period.
Embodiment
Next, enumerate embodiment and the present invention is described in more detail, but the present invention is not limited to these embodiments.
Preparation example 1
The preparation of acrylic polymers:
In the flask possessing agitator, nitrogen ingress pipe, thermometer and reflux condensing tube, add butyl acrylate 97 mass parts, vinylformic acid 3 mass parts, ethyl acetate 100 mass parts, NSC 62789 base mercaptan (NDM) 0.04 mass parts, and while import nitrogen in flask, the content in flask is heated to 60 DEG C.Then, under agitation polymerization starter Diisopropyl azodicarboxylate (AIBN) 0.1 mass parts fully replaced by nitrogen is added in flask.Carry out heating and the cooling of 10 hours, to make the temperature of the content in flask can maintain 60 DEG C, finally add ethyl acetate 100 parts and obtain acrylic polymers A1 solution.For this acrylic polymers A1, according to following GPC condition determination, weight-average molecular weight (Mw), number molecular-weight average (Mn) are measured, thus obtain dispersity (Mw/Mn).In addition, by following method, nonvolatile component (nV) and viscosity are also measured.Measurement result and monomer are formed and is shown in table 1 in the lump.
<GPC condition determination >
Determinator: HLC-8120GPC (Tosoh Inc.)
GPC chromatographic column is formed: following five pedestals (being all Tosoh Inc.)
(1) TSK-GELHXL-H (guard column)
(2)TSK-GELG7000HXL
(3)TSK-GELGMHXL
(4)TSK-GELGMHXL
(5)TSK-GELG2500HXL
Sample concentration: with tetrahydrofuran (THF) dilution to become 1.0mg/cm
3
Mobile phase solvent: tetrahydrofuran (THF)
Flow: 1ml/ minute
Column temperature: 40 DEG C
The measuring method > of < nonvolatile component
Put into the acrylic copolymer solution of about 1g in tin ware (n1) after accurate weighing, and at accurate weighing after total weight (n2), heat 3 hours at 105 DEG C.Afterwards, this tin ware is placed 1 hour in the moisture eliminator of room temperature, and then accurate weighing, thus determine the total weight (n3) after heating.Utilize the weight measurement (n1 ~ n3) that obtains and calculate nonvolatile component by following formula.
Nonvolatile component (%)=100 × [weight (n2-n1) before the weight (n3-n1) after heating/heating]
The measuring method > of < viscosity
Use Brookfield viscometer and at room temperature measure.
Preparation example 2 ~ 6
Except replacing with the monomer composition shown in table 1, obtain acrylic polymers A2 ~ A6 solution in the mode identical with preparation example 1.By the mode identical with preparation example 1, Mw, the Mn of this polymkeric substance, nonvolatile component, viscosity are measured.Show the result in table 1.
Relatively preparation example 1 ~ 4
Except replacing with the monomer composition shown in table 1, obtain acrylic polymers B1 ~ B4 solution in the mode identical with preparation example 1.By the mode identical with preparation example 1, Mw, the Mn of this polymkeric substance, nonvolatile component, viscosity are measured.Show the result in table 1.
[table 1]
Abbreviation in table is as follows.
BA: butyl acrylate
AA: vinylformic acid
HEA:2-carboxyethyl acrylate
BzA: benzyl acrylate
POA: phenoxyethyl acrylate
MEA: methoxyethyl acrylate
Embodiment 1
There is the making of the Polarizer of binder layer:
(preparation of binder composition)
Acrylic polymers A1 (solids component) 100 mass parts of the acrylic polymers A1 solution obtained with respect to preparation example 1, and the isocyanurate-modified body adding tolylene diisocyanate (TDI) class can those 342 (Japanese Polyurethane Inc.) 5 mass parts of Lip river, KBM-403 (Shin-Etsu Chemial Co., Ltd's system) 0.2 mass parts as silane coupling agent, and they are fully obtained by mixing binder composition.
(making of Polarizer)
After removing bubble, utilize scraper and obtained binder composition is coated on the polyester film of lift-off processing, and at 90 DEG C dry 3 minutes immediately.After the drying, be attached on Polarizer, and leave standstill and slaking under the condition of room temperature 23 DEG C, humidity 50%, thus obtain the Polarizer with binder layer.Make to be 1,3,7 between the maturation period.
Embodiment 2 ~ 12
Except acrylic polymers and linking agent being replaced by as described in Table 2, obtain binder composition in the same manner as example 1.In addition, utilize the binder composition obtained, and produce the Polarizer with binder layer in the same manner as example 1.
Comparative example 1 ~ 11
Except acrylic polymers and linking agent being replaced by as described in Table 3, obtain binder composition in the same manner as example 1.In addition, utilize the binder composition obtained, and produce the Polarizer with binder layer in the same manner as example 1.
Test example 1
In the Polarizer obtained by embodiment 1 ~ 12 and comparative example 1 ~ 11, by following method to be the weather resistance of Polarizer of 1 day and 7 days between the maturation period, leakproof photosensitiveness evaluates.These results are gathered and is shown in table 2 and table 3.
The evaluation method > of < weather resistance
The Polarizer with binder layer is cut into the size of 150mm × 250mm, and the side utilizing roll squeezer and be attached to sheet glass on the surface, then, being adjusted to 50 DEG C, keeping 20 minutes in the autoclave of 5 air pressure, thus make test board.Make two identical test boards, and under the condition of temperature 60 C, humidity 95%RH (humidity resistance) and temperature 85 DEG C condition under (thermotolerance) place 500 hours, and according to following standard, observe generation of stripping etc. by visual and evaluate.
(standard)
Zero: do not occur foaming, stripping, crackle
△: occur foaming, stripping, crackle a little
×: comprehensive appearance foaming, stripping, crackle
The evaluation method > of < leakproof photosensitiveness
Utilize laminating roll and in the mode becoming mutually crossed Nicol position, and the Polarizer two with binder layer is attached at surface and the back side of 19 inches of widescreen TN watch-dogs (model: BenQFP93VW), then, being adjusted to 50 DEG C, keeping 20 minutes in the autoclave of 5 air pressure, thus make test board.The test board made is placed 500 hours under 70 DEG C of conditions, and by visual, light leak is observed, and evaluate according to following standard.
(standard)
Zero: do not occur light leak
△: light leak appears in part
×: comprehensively there is light leak
[table 2]
Abbreviation in table is as follows.
L-45:TDI kind isocyanate (Soken Chemical Company system)
Can the isocyanurate-modified body of that 342:TDI class of Lip river (Japanese Polyurethane Inc.)
Can that 2030:TDI kind isocyanate of Lip river (Japanese Polyurethane Inc.)
Can Lip river that 2041: polymeric MDI (polymethylene multi-phenenyl isocyanate, Japanese Polyurethane Inc.)
TD-75:XDI class (Soken Chemical Company system)
E-5XM: epoxies linking agent
How resistance to moral (DURANATE) TPA-100:HDI class isocyanuric acid ester (Asahi Kasei Corporation's system)
KBM-403: silane coupling agent (chemical industrial company of SHIN-ETSU HANTOTAI system)
[table 3]
※ 1 cannot be coated with due to gelation
Test example 2
About the Polarizer with the slaking binder layer of 1,3,7 days obtained by embodiment 1 ~ 12 and comparative example 1 ~ 11, by the following method bounding force is evaluated.In addition, the binder layer formed about the binder composition by being obtained by embodiment 1 ~ 12 and comparative example 1 ~ 11, is evaluated the slaking gel ratio of 1,3,7 days by following method.These results are shown in table 4.
The measuring method > of < bounding force
The Polarizer with binder layer is cut into the size of 70mm × 25mm and makes test film.Peel off polyester film from test film, and the side being attached to sheet glass utilizing roll squeezer on the surface after, being adjusted to 50 DEG C, keeping 20 minutes in the autoclave of 5 air pressure.Then, 23 DEG C, place 1 hour under 50%RH environment after, to stretch to 90 ° of directions with the speed of 300mm/ minute, thus mensuration stripping strength.
The measuring method > of < gel ratio
The mode of 20 μm is being become with dried thickness, obtained binder composition is coated on the surface of the polyester of lift-off processing, and after its drying, the polyester film through lift-off processing is attached on the surface at opposite side, and 23 DEG C, slaking 1,3,7 days under the condition of 50%RH, thus make test film.Be about 0.1g from test film collection tackiness agent and put into sample bottle, and add ethyl acetate 30cc and vibration 24 hours after, with the content in stainless this sample bottle of steel metal mesh filter of 200 object, and by the residue on wire netting at 100 DEG C dry 2 hours, and dry weight is measured, thus obtained gel ratio by following formula.
Gel ratio (%)=(binder wt of dry weight/collection) × 100
[table 4]
※ 2 cannot be coated with due to gelation and measure
Show following situation, namely, Polarizer in comparative example 1 ~ 11, when normal temperature slaking 1 day, cannot obtain leakproof photosensitiveness and weather resistance Polarizer comparatively fully, on the other hand, in embodiment 1 ~ 12, become leakproof photosensitiveness and the good Polarizer of weather resistance when slaking 1 day, in addition, bounding force and gel ratio are also more stable when slaking 1 day, thus Absorbable organic halogens ground maintains these performances.
Utilizability in industry
Binder composition of the present invention, following binder layer can be formed by the slaking between short-term, that is, effectively prevent light leak, and there is excellent weather resistance, even and if also can the binder layer of generation of control foaming, stripping etc. under hot and humid condition.Therefore, this binder composition can utilize ideally as the binder composition of Polarizer.
Claims (6)
1. a Polarizer binder composition, is characterized in that,
Containing following composition (A) and composition (B), that is,
(methyl) acrylic polymers 100 mass parts that (A) is to the monomer containing carboxyl of major general's mass percent 1 ~ 10% and (methyl) acrylic monomer copolymerization containing hydroxyl of mass percent 0.05 ~ 1% obtains, weight-average molecular weight is 300,000 ~ 1,500,000;
(B) there is tolylene diisocyanate compounds 8 ~ 20 mass parts of isocyanurate structure.
2. Polarizer binder composition as claimed in claim 1, wherein,
Also containing composition (C), described composition (C) for be selected from not there is isocyanurate structure tolylene diisocyanate class linking agent, epoxies linking agent and ethylenimine class linking agent in one or more linking agent.
3. Polarizer binder composition as claimed in claim 1 or 2, wherein,
Also containing composition (D), described composition (D) is silane coupling agent.
4. a Polarizer adhesive sheet, it forms by arranging the binder layer formed by Polarizer binder composition according to claim 1 on the face of at least side of supporting mass.
5. a Polarizer, it forms by arranging the binder layer formed by Polarizer binder composition according to claim 1 on the face of at least side of polarizing film.
6. a manufacture method for liquid crystal cell, is characterized in that,
Polarizer is arranged on the substrate surface of liquid crystal cells, described Polarizer is provided with the binder layer formed by binder composition on the face of at least side of polarizing film, described binder composition contains following composition (A) and composition (B), namely
(methyl) acrylic polymers 100 mass parts that (A) is to the monomer containing carboxyl of major general's mass percent 1 ~ 10% and (methyl) acrylic monomer copolymerization containing hydroxyl of mass percent 0.05 ~ 1% obtains, weight-average molecular weight is 300,000 ~ 1,500,000;
(B) there is tolylene diisocyanate compounds 8 ~ 20 mass parts of isocyanurate structure.
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| JP2009261506 | 2009-11-17 | ||
| JP2009-261506 | 2009-11-17 | ||
| PCT/JP2010/070260 WO2011062127A1 (en) | 2009-11-17 | 2010-11-15 | Adhesive composition for polarizing plate and polarizing plate using the same |
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| CN102686689A CN102686689A (en) | 2012-09-19 |
| CN102686689B true CN102686689B (en) | 2015-12-16 |
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| JP (1) | JP5764496B2 (en) |
| KR (1) | KR101587804B1 (en) |
| CN (1) | CN102686689B (en) |
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| JP5777416B2 (en) * | 2011-06-13 | 2015-09-09 | 日本カーバイド工業株式会社 | Adhesive composition, optical film using the same, and liquid crystal display device |
| JP5949014B2 (en) * | 2012-03-21 | 2016-07-06 | 住友化学株式会社 | Adhesive sheet, optical film with adhesive, and optical laminate |
| JP5949013B2 (en) * | 2012-03-21 | 2016-07-06 | 住友化学株式会社 | Adhesive sheet, optical film with adhesive, and optical laminate |
| JP6024382B2 (en) * | 2012-10-23 | 2016-11-16 | 大日本印刷株式会社 | Adhesive composition, adhesive sheet and image display device |
| JP6013898B2 (en) * | 2012-12-17 | 2016-10-25 | 藤森工業株式会社 | Adhesive layer and adhesive film |
| KR102135645B1 (en) * | 2014-11-04 | 2020-07-20 | 소켄 케미칼 앤드 엔지니어링 캄파니, 리미티드 | Adhesive composition for polarizing plates and polarizing plate having adhesive layer |
| JP6390661B2 (en) * | 2016-04-19 | 2018-09-19 | 東洋インキＳｃホールディングス株式会社 | Adhesive and adhesive sheet |
| JP6160743B2 (en) * | 2016-06-08 | 2017-07-12 | 住友化学株式会社 | Adhesive sheet, optical film with adhesive, and optical laminate |
| JP6197919B2 (en) * | 2016-06-08 | 2017-09-20 | 住友化学株式会社 | Adhesive sheet, optical film with adhesive, and optical laminate |
| KR102294142B1 (en) * | 2018-06-22 | 2021-08-26 | 산진 옵토일렉트로닉스 (쑤저우) 컴퍼니 리미티드 | Quantitative method for polarizer adhesive leakage |
| CN111548761B (en) * | 2019-02-08 | 2023-08-18 | 日本电石工业株式会社 | Adhesive composition for polarizing plate, polarizing plate with adhesive layer, and vehicle-mounted display device |
| CN113755101A (en) * | 2021-09-07 | 2021-12-07 | 常州都铂高分子有限公司 | Glue composition with good re-peeling property |
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| CN1490372A (en) * | 2002-08-29 | 2004-04-21 | 综研化学株式会社 | Adhesive for optical member and optical member therewith |
| JP2007119667A (en) * | 2005-10-31 | 2007-05-17 | Sumitomo Chemical Co Ltd | Adhesive |
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| JPH04136524A (en) | 1990-09-27 | 1992-05-11 | Nissan Motor Co Ltd | Wet type frictional engagement plate |
| JP3830375B2 (en) * | 2001-11-07 | 2006-10-04 | リンテック株式会社 | Adhesive sheet primer, adhesive sheet affixed product and method for producing the same |
| JP2003154797A (en) * | 2001-11-26 | 2003-05-27 | Toppan Printing Co Ltd | Transfer sheet |
| JP4623485B2 (en) | 2004-03-02 | 2011-02-02 | サイデン化学株式会社 | Adhesive composition and surface protective film |
| JP4976075B2 (en) * | 2005-12-26 | 2012-07-18 | リンテック株式会社 | Adhesive for polarizing plate, polarizing plate with adhesive and method for producing the same |
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| JP2009132751A (en) * | 2007-11-28 | 2009-06-18 | Cheil Industries Inc | Adhesive composition and optical member |
| JP4963485B2 (en) * | 2008-04-07 | 2012-06-27 | 綜研化学株式会社 | Adhesive composition for polarizing plate and method for producing the same |
| JP5304339B2 (en) * | 2009-03-11 | 2013-10-02 | 東洋インキＳｃホールディングス株式会社 | Adhesive composition and adhesive laminate comprising the same |
| JP5526645B2 (en) * | 2009-08-07 | 2014-06-18 | 東洋インキＳｃホールディングス株式会社 | Optical pressure-sensitive adhesive and optical pressure-sensitive adhesive sheet using the optical pressure-sensitive adhesive |
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- 2010-11-12 TW TW099139043A patent/TWI486417B/en not_active IP Right Cessation
- 2010-11-15 CN CN201080046723.5A patent/CN102686689B/en not_active Expired - Fee Related
- 2010-11-15 WO PCT/JP2010/070260 patent/WO2011062127A1/en active Application Filing
- 2010-11-15 JP JP2011541907A patent/JP5764496B2/en not_active Expired - Fee Related
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1490372A (en) * | 2002-08-29 | 2004-04-21 | 综研化学株式会社 | Adhesive for optical member and optical member therewith |
| JP2007119667A (en) * | 2005-10-31 | 2007-05-17 | Sumitomo Chemical Co Ltd | Adhesive |
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| CN102686689A (en) | 2012-09-19 |
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| TW201132723A (en) | 2011-10-01 |
| KR20120115203A (en) | 2012-10-17 |
| WO2011062127A1 (en) | 2011-05-26 |
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| KR101587804B1 (en) | 2016-01-22 |
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