CN1837314A - Pressure sensitive adhesive composition and optical materials - Google Patents
Pressure sensitive adhesive composition and optical materials Download PDFInfo
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- CN1837314A CN1837314A CNA2006100035523A CN200610003552A CN1837314A CN 1837314 A CN1837314 A CN 1837314A CN A2006100035523 A CNA2006100035523 A CN A2006100035523A CN 200610003552 A CN200610003552 A CN 200610003552A CN 1837314 A CN1837314 A CN 1837314A
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- adhesive composition
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- sensitive adhesive
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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
- 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
- C09J133/062—Copolymers with monomers not covered by C09J133/06
- C09J133/066—Copolymers with monomers not covered by C09J133/06 containing -OH groups
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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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C09J7/385—Acrylic polymers
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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
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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
- 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
Abstract
The pressure-sensitive adhesive composition comprises (A) an acrylic copolymer which is obtained by the copolymerization of an alkyl (meth)acrylate having a 1-18C alkyl group and a functional group-containing monomer and has a mass-average molecular weight (in terms of the GPC polystyrene value) of 500,000-2,500,000, (B) a crosslinking agent, and (C) a silane coupling agent having an acid anhydride group as an organic functional group. The present invention provides a pressure-sensitive adhesive composition for optically functional films which has excellent durability performance under the circumstances of high temperature and humidity, and particularly has excellent adhesion and adhesion durability even when a hydroxy group-based acrylic copolymer is used as the major component of the pressure-sensitive adhesive composition in order to inhibit the deterioration of optically functional films.
Description
Technical field
Used pressure sensitive adhesive composition and the optical material that in optically functional film, is provided with the layer that contains above-mentioned composition such as when the present invention relates to that optically functional films such as polarizing film and phase-contrast film are sticked on glass substrate (liquid crystal cell (cell) etc.), specifically, the optical material that the present invention relates to contain the pressure sensitive adhesive composition of organo silane coupling agent and in optically functional film, be provided with the layer that contains above-mentioned composition.Pressure sensitive adhesive composition provided by the invention has the excellent durability under hot and humid, even the host in pressure sensitive adhesive composition uses the hydroxy kind acrylic copolymer to suppress also have good tight joint and adhesive durability under the situation of deterioration of optically functional film.
Background technology
In opticinstrument or display unit, use polaroid usually for obtaining polarisation.For example, in liquid crystal indicator, use by the pressure sensitive adhesives layer polaroid is fixed on polaroid fixed sturcture thing on the liquid crystal cell face (mainly being made up of sheet glass).The pressure sensitive adhesives of forming above-mentioned pressure sensitive adhesives layer mainly uses the acrylic acid or the like pressure sensitive adhesives.
But, when general acrylic acid or the like pressure sensitive adhesives uses, can produce the phenomenon that the pressure sensitive adhesives layer bubbles, adhesive segment comes off under high temperature or high humidity, can not obtain good polaroid fixed sturcture thing.
For this reason, in the pressure sensitive adhesives, for improving the tight joint of pressure sensitive adhesives and glass substrate, existing optically functional film also proposed to mix the method (for example patent documentation 1) of the organo silane coupling agent that contains epoxy group(ing) and the method (for example patent documentation 2) of the organo silane coupling agent that mixing contains ketone ester (ketoester) structure etc. in addition with being added with organo silane coupling agent in the pressure sensitive adhesives in the acrylic polymer zoarium.
When adding above-mentioned organo silane coupling agent, because the kind of the functional group in the pressure sensitive adhesives, pressure sensitive adhesives can not obtain effect of sufficient.For example; high durable in order to prevent with the deterioration that water decomposition causes that adds of polaroid with the tri acetyl cellulose in the pressure sensitive adhesives (TAC) film; functional group in the acrylic acid or the like pressure sensitive adhesives is preferably hydroxyl, but does not have at present to find to make above-mentioned binding agent give full play to the organo silane coupling agent of effect.
[patent documentation 1] spy opens flat 7-20314 communique
No. 3533446 communiques of [patent documentation 2] special permission
Summary of the invention
The present invention is In view of the foregoing proposed.The purpose of this invention is to provide the optically functional film pressure sensitive adhesive composition, said composition has the excellent durability under hot and humid, even the host in pressure sensitive adhesive composition uses the hydroxy kind acrylic copolymer to suppress also have good tight joint and adhesive durability under the situation of deterioration of optically functional film.
For achieving the above object, the inventor furthers investigate to find to contain and specifies acrylic copolymer, linking agent and as the pressure sensitive adhesive composition of the organo silane coupling agent with anhydride group of organo-functional group, have the excellent durability under hot and humid, realize the object of the invention thus.The present invention is based on above-mentioned discovery and finishes.
Just, the invention provides following pressure sensitive adhesive composition and optical material.
A kind of pressure sensitive adhesive composition, it is characterized in that to contain (A) be (methyl) alkyl acrylate of 1-18 by the alkyl carbon atoms number and contain acrylic copolymer that weight-average molecular weight that the monomer copolymerization of functional group obtains is 500,000-2,500,000 (GPC polystyrene conversion values), (B) linking agent and (C) as the organo silane coupling agent with anhydride group of organo-functional group.
In the above-mentioned pressure sensitive adhesive composition, described (C) is the silane compound of being represented by following general formula (I) as the organo silane coupling agent with anhydride group of organo-functional group.
Wherein, R represents that carbonatoms is the alkyl of 1-6, and n is that 2-8, m are that 1-3, l are that 1-3, k are the integers of 0-2, and k+l+m=4.
In the above-mentioned pressure sensitive adhesive composition, with respect to 100 parts by weight of acrylic interpolymers, the content of organo silane coupling agent is the 0.005-5 weight part.
In the above-mentioned pressure sensitive adhesive composition, the described monomeric described functional group that contains functional group is a hydroxyl.
A kind of optical material is characterized in that, the two sides of optically functional film or single face are provided with the layer that contains pressure sensitive adhesive composition provided by the invention.
Pressure sensitive adhesive composition of the present invention and optical material, owing to mix organo silane coupling agent in the above-mentioned appointment acrylic copolymer with anhydride group, weather resistance with the excellence under hot and humid can be provided, even under the situation of the deterioration that the use of the host in pressure sensitive adhesive composition hydroxy kind acrylic copolymer is suppressed optically functional film, also have good tight joint and adhesive durability.
Embodiment
Pressure sensitive adhesive composition of the present invention (hereinafter to be referred as " adhesive composition ") contains: (A) be (methyl) alkyl acrylate of 1-18 by the alkyl carbon atoms number and contain acrylic copolymer that weight-average molecular weight that the monomer copolymerization of functional group obtains is 50-250 ten thousand (gel permeation chromatography (GPC) polystyrene conversion value), (B) linking agent and (C) as the organo silane coupling agent with anhydride group of organo-functional group.
(A) the alkyl carbon atoms number in the composition is that (methyl) alkyl acrylate of 1-1 8 for example can be (methyl) methyl acrylate, (methyl) ethyl propenoate, (methyl) propyl acrylate, (methyl) n-butyl acrylate, (methyl) isobutyl acrylate, (methyl) tert-butyl acrylate, (methyl) vinylformic acid pentyl ester, (methyl) Ethyl acrylate, (methyl) cyclohexyl acrylate, (methyl) ethyl acrylate, (methyl) Isooctyl acrylate monomer, (methyl) decyl acrylate, (methyl) dodecylacrylate, (methyl) vinylformic acid tetradecyl ester, (methyl) vinylformic acid palm ester, (methyl) stearyl acrylate ester etc.These (methyl) alkyl acrylates can use separately, also can two or more be used in combination.
In addition, (A) monomer that contains functional group in the composition for example can be (methyl) 2-Hydroxy ethyl acrylate, (methyl) vinylformic acid-2-hydroxy propyl ester, (methyl) vinylformic acid-3-hydroxy propyl ester, (methyl) vinylformic acid-2-hydroxyl butyl ester, (methyl) vinylformic acid-3-hydroxyl butyl ester, (methyl) vinylformic acid-(methyl) vinylformic acid hydroxyalkyl acrylates such as 4-hydroxyl butyl ester; Acrylic amides such as acrylamide, Methacrylamide, N methacrylamide, N-methyl acrylamide, N hydroxymethyl acrylamide, N-methylol methacrylamide; Methacrylic acid one alkylaminoalkyls such as (methyl) vinylformic acid monomethyl aminoethyl ester, (methyl) vinylformic acid one ethyl aminoethyl ester, (methyl) vinylformic acid monomethyl aminopropyl ester, (methyl) vinylformic acid one ethyl aminopropyl ester; Ethene unsaturated carboxylic acids such as vinylformic acid, methacrylic acid, butenoic acid, toxilic acid, methylene-succinic acid, citraconic acid etc.These monomers can use separately, also can two or more be used in combination.
Among the present invention, the described functional group in the above-mentioned monomer that contains functional group is preferably hydroxyl.In the existing adhesive composition that is added with machine silane coupling agent; functional group in the binding agent can not obtain sufficient binding agent effect during for hydroxyl; but in the present invention; even functional group is a hydroxyl; under stringent condition, still the binding agent effect can be kept, and the deterioration that highly durable polarization plate causes with the chance water decomposition of the tri acetyl cellulose in the pressure sensitive adhesives (TAC) film can be effectively prevented.
In addition, in the scope that does not influence the object of the invention, (A) also can contain other monomer in the acrylic copolymer of composition.Other monomer that uses in (A) composition for example can be vinyl esters such as vinyl-acetic ester, propionate as required; Olefines such as ethene, propylene, iso-butylene; Halogenated alkenes such as vinylchlorid, vinylidene chloride hydro carbons; Styrene monomer such as vinylbenzene, alpha-methyl styrene; Dienes monomers such as divinyl, isoprene, chloroprene; Nitrile monomer such as vinyl cyanide, methacrylonitrile; N,N-DMAA, N, N such as N-dimethylmethacryl amide, N-dialkyl group substituted acrylamide class etc.These can use separately by monomer, also can two or more be used in combination.
The general initiator that uses during copolymerization, initiator for example can be Diisopropyl azodicarboxylate, benzoyl peroxide, ditertiary butyl peroxide, cumene hydroperoxide etc.
With in the composition, the copolymerized form of acrylic copolymer is not particularly limited, and can be in random copolymerization, block copolymerization, the graft copolymerization any one at binding agent of the present invention.
In addition, the molecular weight of acrylic copolymer adopts weight-average molecular weight to represent, is 500,000-2,500,000, is preferably 800,000-1,800,000.Be decided to be as mentioned above by scope, can guarantee tight joint and the adhesive durability of binding agent, and can suppress to float or come off bonded bodies such as glass substrates with weight-average molecular weight.
Above-mentioned weight-average molecular weight is the polystyrene conversion value of measuring by gel permeation chromatography (GPC).
Consider and the tight joint and the adhesive durability of bonded body that (A) the monomeric content that contains functional group in the acrylic copolymer of composition is preferably 0.1-10 weight %, more preferably 0.5-5 weight %.
At least contain 2 above functional groups as the linking agent of (B) composition, the kind of functional group is not particularly limited, can use the linking agent in the cross-linking type binding agent commonly used in the prior art.About the linking agent of 2 above functional groups, the bridging property functional group kind according in the interpolymer of (A) composition can suitably be selected from for example linking agents such as polyisocyanate compounds, epoxy compounds, metallo-chelate, metal alkoxide, metal-salt.In addition, linking agent also can two or more and usefulness.
Polyisocyanate compounds for example can be alicyclic polymeric isocyanates such as aliphatic polymeric isocyanates such as aromatic poly-isocyanate, HDI, isophorone diisocyanate, hydrogenation diphenylmethanediisocyanate such as toluene support vulcabond, diphenylmethanediisocyanate, triphenylmethane triisocyanate, xylylene vulcabond, perhaps the addition compound of polyol such as the dimer of these polymeric polyisocyanates or tripolymer or these polymeric polyisocyanates and TriMethylolPropane(TMP) etc.
In addition, metallo-chelate for example can be aluminum chelates such as aluminum isopropoxide, aluminium-sec-butylate, aluminium acetylacetonate, or metallo-chelate such as four isobutyl-titanates, four (2-ethyl hexyl oxy) titanate.
The acrylic copolymer of above-mentioned (A) composition of relative 100 weight parts, the consumption of the linking agent of above-mentioned conduct (B) composition is generally the 0.05-10 weight part, preferably uses the 0.1-5 weight part.Be decided to be as mentioned above by scope, can obtain good tight joint and weather resistance linking agent.
Among the present invention, use organo silane coupling agent conduct (C) composition that contains as organo-functional group with anhydride group.
The above-mentioned organo silane coupling agent with anhydride group as organo-functional group is preferably the silane compound by following general formula (I) expression.
R in the general formula (I) represents that carbonatoms is the alkyl of 1-6, is preferably methyl or ethyl; N is that 2-8, m are that 1-3, l are that 1-3, k are the integers of 0-2, and k+l+m=4.
The specific examples of the organo silane coupling agent of general formula (I) expression can for the 2-Trimethoxy silane ethyl succinyl oxide of following formula (II) expression (SHIN-ETSU HANTOTAI's chemical industry (strain) system, X-12-967) etc.
Add in the adhesive composition by the organo silane coupling agent that will contain anhydride group, even the host in the adhesive composition is the hydroxy kind acrylic copolymer, under wet heat condition, also can improve cohesiveness, be not easy to produce the unsteady of polarizing film and come off liquid crystal cell (glass).The acrylic copolymer of above-mentioned (A) composition of relative 100 weight parts, the addition of organo silane coupling agent is preferably the 0.005-5 weight part, more preferably the 0.01-1 weight part.
In adhesive composition of the present invention, in the scope that does not influence the object of the invention, can add the known various additives that use in the conventional adhesive composition as required, for example plasticizer, tackifier, UV light absorber, antioxidant etc.
Adhesive layer can be by adhesive composition directly being coated in optically functional films such as polarizing film the two sides or single face on form, also can form by being bonded on the two sides of optically functional film or the single face on the lift-off processing face that adhesive composition is coated in the stripping film of implementing lift-off processing and with it.
The coating liquid that is used for adhesive composition of the present invention can be any one of organic solvent class, latex class, solvent-free class.
The organic solvent that is used for organic solvent class coating liquid for example can be toluene, dimethylbenzene, methyl alcohol, ethanol, isopropylcarbinol, propyl carbinol, acetone, butanone, hexone, ethyl acetate, tetrahydrofuran (THF) etc.These solvents can use separately, also can two or more be used in combination.
Consider convenient coating, use these organic solvents, it is 10-50 weight % that coating liquid preferably is mixed with the concentration that makes solids component.
The coating method of coating liquid can adopt and well known to a person skilled in the art coating method, and for example bar is coated with method (bar coat), rolling method (roll coat), spread coating (knife coat), roller cutter and is coated with method (roll knife coat), punch die and is coated with method (die coat), gravure formula and is coated with that method (gravure coat), air doctor blade are coated with method (air doctorcoat), scraper is coated with method (doctor blade coat) etc.
After the coating, under 70-120 ℃ temperature drying treatment 1-5 minute usually, obtain required adhesive layer thus.
The thickness of above-mentioned adhesive layer is preferably the 5-150 micron usually, more preferably the 10-100 micron.
As the optically functional film that sticks on the glass substrate (liquid crystal cell etc.); can use polarizing film; wherein above-mentioned polarizing film is to extend the transparent polymer film directed along a direction of principal axis; absorption such as iodine and/or dichroic dye are oriented in obtain film in the oriented molecule gap, and its film two sides is utilized protective film to cover to obtain.Above-mentioned transparent polymer film nearly all is PVA (PVOH) FILM at present, and protective film then uses the tri acetyl cellulose film mostly.
Polarizing film for example can use various films such as iodine class polarizing film, dye class polarizing film, colored polarizing film, polyvinylene polarizing film, infrared polarizing film, ultraviolet polarizing film, is not particularly limited.By above-mentioned adhesive layer is arranged on the two sides or single face of these optically functional films, can obtain optical material of the present invention.
[embodiment]
Describe the present invention more in detail below by embodiment, but the present invention is not limited to these embodiment.
The adhesive composition that obtains in each embodiment and comparative example is carried out evaluation as described below.
(1) weather resistance
Will (being of a size of 233mm * 309mm) utilizes laminater (Off ジ Network ラ (strain) system, ラ ミ パ Star カ one) to stick on after non-alkali glass (エ ヌ エ ス ジ one プ レ シ ジ ヨ Application (strain) system, コ one ニ Application グ #1 737) goes up with the polaroid of pressure sensitive adhesives, join in the autoclave (the former making of (strain) chestnut is made), under 50 ℃, 0.5MPa, handled 20 minutes, then after placing 500 hours under each condition of 80 ℃, 90 ℃, 60 ℃ and relative humidity (Rh) 90%, the appearance change of polaroid is carried out evaluation as described below.(using the magnifying glass visual valuation)
Zero: there are not bubble and striped, *: bubble and striped are arranged, * *: have to come off
(2) deterioration of polaroid
Identical with Evaluation of Durability, will be after placing 500 hours under 60 ℃, the condition of relative humidity (Rh) 90% with the polaroid of pressure sensitive adhesives, whether the visual observation polaroid is aging.
(3) cohesive force
During normality: will utilize laminater (Off ジ Network ラ (strain) system with the polaroid (25mm width) of pressure sensitive adhesives, ラ ミ パ Star カ one) sticks on non-alkali glass (エ ヌ エ ス ジ one プ レ シ ジ ヨ Application (strain) system, コ one ニ Application グ #1 737) after on, join in the autoclave (the former making of (strain) chestnut is made), at 50 ℃, 0.5MPa following processing 20 minutes, then at 23 ℃, place after 24 hours under the condition of relative humidity (Rh) 65%, utilize omnipotent tension tester ((strain) エ one ア Application De デ イ system) to measure cohesive force (stripping conditions is by JIS Z 0237 standard).
When damp and hot: after will being bonded on the non-alkali glass (エ ヌ エ ス ジ one プ レ シ ジ ヨ Application (strain) system, コ one ニ Application グ #1737) with the polaroid (25mm width) of pressure sensitive adhesives, identical autoclave is handled when carrying out with normality, then places 24 hours under 60 ℃, the condition of relative humidity (Rh) 90%.After the taking-up, further under 23 ℃, the condition of relative humidity (Rh) 65%, place damping in 2 hours after, utilize omnipotent tension tester ((strain) エ one ア Application De デ イ system) to measure cohesive force (stripping conditions is by JIS Z 0237 standard).
(4) peeling force
On the face that does not apply pressure sensitive adhesives of the polaroid (25mm * 150) of having pressure sensitive adhesives, paste double sticky tape (tape), and with its face and glass bonding.Then, with 0.3 meter/minute peeling rate and the 180 ° of peel angle peeling force when adhesive layer is peeled off, utilize omnipotent tension tester ((strain) エ one ア Application De デ イ system) to measure for stripping film.
In addition, the condition determination of the weight-average molecular weight of acrylic copolymer (polystyrene conversion value) is as follows.
Device: East ソ (strain) system, HLC-8020 (post (column): East ソ (strain) system, TSKgelGMHxL*TSKgel GMHxL*TSKgel G2000HxL)
Solvent: tetrahydrofuran (THF), temperature: 40 ℃, flow: 1 ml/min
Embodiment 1
The Diisopropyl azodicarboxylate as initiator of the positive butyl ester of 99 parts by weight of acrylic, 1 parts by weight of acrylic-4-hydroxyl butyl ester, 0.2 weight part is added in the ethyl acetate of 200 weight parts, stirred 17 hours down at 60 ℃, obtain weight-average molecular weight and be 1,500,000 acrylic acid copolymer liquid solution.In the solution that contains the above-mentioned interpolymer of 100 weight parts, add the linking agent (the military field chemistry of Mitsui (strain) system ケ ネ one ト D-110N) of the polyisocyanate compounds formation of 0.2 weight part (solids component) and 2-Trimethoxy silane ethyl succinyl oxide (SHIN-ETSU HANTOTAI's chemical industry (strain) system of 0.05 weight part (solids component), X-12-967) organo silane coupling agent, form adhesive composition, and utilize butanone dilution to form about 20 weight % solution it, as coating liquid.
Utilize spread coating to be coated in stripping film (リ Application テ Star Network (strain) system the coating liquid that obtains; SP-PET3811) on the lift-off processing face; 90 ℃ of dryings after 1 minute; with polaroid (3 layers of layered product of tri acetyl cellulose film/PVA (PVOH) FILM/tri acetyl cellulose film; 180 microns of total thickness) lamination is produced thickness and is 25 microns the polaroid that contains the pressure sensitive adhesives layer.
The polaroid that contains the pressure sensitive adhesives layer that utilization obtains is estimated adhesive composition, and its result is as shown in table 1.
Embodiment 2
Present embodiment is except the 2-Trimethoxy silane ethyl succinyl oxide that uses 0.1 weight part, and other all carries out similarly to Example 1.The polaroid that contains the pressure sensitive adhesives layer that utilization obtains is estimated adhesive composition, and its result is as shown in table 1.
Embodiment 3
Present embodiment is except the 2-Trimethoxy silane ethyl succinyl oxide that uses 0.2 weight part, and other all carries out similarly to Example 1.The polaroid that contains the pressure sensitive adhesives layer that utilization obtains is estimated adhesive composition, and its result is as shown in table 1.
Embodiment 4
The Diisopropyl azodicarboxylate as initiator of the positive butyl ester of 99 parts by weight of acrylic, 1 parts by weight of acrylic 4-hydroxyl butyl ester, 0.2 weight part is added in the ethyl acetate of 200 weight parts, 60 ℃ stir 17 hours after, the Diisopropyl azodicarboxylate as initiator of the positive butyl ester of 49.5 parts by weight of acrylic, 0.5 parts by weight of acrylic-4-hydroxyl butyl ester, 0.1 weight part is added to dissolving obtains solution in the toluene of 1 00 weight parts.Afterwards, further stirred 17 hours down, obtain weight-average molecular weight and be 1,100,000 acrylic acid copolymer liquid solution at 65 ℃.In the solution of the above-mentioned interpolymer that contains 100 weight parts, add the linking agent (the military field chemistry of Mitsui (strain) system ケ ネ one ト D-110N) of the polyisocyanate compounds formation of 0.2 weight part (solids component) and the 2-Trimethoxy silane ethyl succinyl oxide organo silane coupling agent of 0.05 weight part (solids component), form adhesive composition, and, be used as coating liquid with its solution that utilizes the about 20 weight % of butanone dilution formation.
The coating liquid that utilization obtains, method is made the polaroid with the pressure sensitive adhesives layer similarly to Example 1.And utilizing the polaroid that contains the pressure sensitive adhesives layer that obtains to estimate adhesive composition, its result is as shown in table 1.
Embodiment 5
Present embodiment is except the 2-Trimethoxy silane ethyl succinyl oxide that uses 0.1 weight part, and other all carries out similarly to Example 4.The polaroid that contains the pressure sensitive adhesives layer that utilization obtains is estimated adhesive composition, and its result is as shown in table 1.
Embodiment 6
Present embodiment is except the 2-Trimethoxy silane ethyl succinyl oxide that uses 0.2 weight part, and other all carries out similarly to Example 4.The polaroid that contains the pressure sensitive adhesives layer that utilization obtains is estimated adhesive composition, and its result is as shown in table 1.
Comparative example 1
This comparative example is not except being added with the machine silane coupling agent, and other all carries out similarly to Example 1.The polaroid that contains the pressure sensitive adhesives layer that utilization obtains is estimated adhesive composition, and its result is as shown in table 2.
Comparative example 2
3-glycidoxypropyltrime,hoxysilane (SHIN-ETSU HANTOTAI chemical industry (strain) system of this comparative example except adding 0.2 weight part, KBM-403) replace among the embodiment 1 2-Trimethoxy silane ethyl succinyl oxide as outside the organo silane coupling agent, other all carries out similarly to Example 1.The polaroid that contains the pressure sensitive adhesives layer that utilization obtains is estimated adhesive composition, and its result is as shown in table 2.
Comparative example 3
The 2-Trimethoxy silane ethyl succinyl oxide of this comparative example in the 3-glycidoxypropyltrime,hoxysilane replacement embodiment 1 that adds 2 weight parts, other all carries out similarly to Example 1.The polaroid that contains the pressure sensitive adhesives layer that utilization obtains is estimated adhesive composition, and its result is as shown in table 2.
Comparative example 4
This comparative example is except 3-methacryloxypropyl methoxy silane (SHIN-ETSU HANTOTAI's chemical industry (strain) system of the 3-glycidoxypropyltrime,hoxysilane of adding 0.1 weight part and 0.1 weight part, KBM-503) outside the 2-Trimethoxy silane ethyl succinyl oxide among the replacement embodiment 1, other all carries out similarly to Example 1.The polaroid that contains the pressure sensitive adhesives layer that utilization obtains is estimated adhesive composition, its result such as table 2 expression.
[table 1]
| Embodiment 1 | Embodiment 2 | Embodiment 3 | Embodiment 4 | Embodiment 5 | Embodiment 6 | |
| (evaluation of adhesive composition) | ||||||
| (1) weather resistance | ||||||
| 80℃ | ○ | ○ | ○ | ○ | ○ | ○ |
| 90℃ | ○ | ○ | ○ | ○ | ○ | ○ |
| 60℃、90％Rh | ○ | ○ | ○ | ○ | ○ | ○ |
| (2) deterioration of polaroid | No | No | No | No | No | No |
| (3) cohesive force (ox/25 millimeter) | ||||||
| During normality (23 ℃, 65%Rh place 24 hours) | 20.3 | 28.8 | 28.8 | 20.4 | 26.2 | 27.3 |
| When damp and hot (60 ℃, 90%Rh place 24 hours) | 27.2 | 27.5 | 31.8 | 27.0 | 27.8 | 32.4 |
| (4) peeling force (milli ox/25 millimeter) | 22 | 25 | 29 | 25 | 28 | 30 |
[table 2]
| Comparative example 1 | Comparative example 2 | Comparative example 3 | Comparative example 4 | |
| (evaluation of adhesive composition) | ||||
| (1) weather resistance | ||||
| 80℃ | × | × | ○ | × |
| 90℃ | ×× | × | × | × |
| 60℃、90％Rh | ×× | ×× | ○ | ×× |
| (2) deterioration of polaroid | No | No | No | No |
| (3) cohesive force (ox/25 millimeter) | ||||
| During normality (23 ℃, 65%Rh place 24 hours) | 3.9 | 5.2 | 5.7 | 5.6 |
| When damp and hot (60 ℃, 90%Rh place 24 hours) | 5.8 | 9.9 | 11.2 | 8.9 |
| (4) peeling force (milli ox/25 millimeter) | 19 | 24 | 48 | 22 |
Claims (5)
1, a kind of pressure sensitive adhesive composition, it is characterized in that said composition contains: be (methyl) alkyl acrylate of 1-18 and to contain weight-average molecular weight that the monomer copolymerization of functional group obtains be 500,000-2,500,000 acrylic copolymer, (B) linking agent and (C) as the organo silane coupling agent with anhydride group of organo-functional group (A) by the alkyl carbon atoms number.
2, pressure sensitive adhesive composition according to claim 1, wherein, described (C) is the silane compound of being represented by following general formula (I) as the organo silane coupling agent with anhydride group of organo-functional group:
Wherein, R represents that carbonatoms is the alkyl of 1-6, and n is that 2-8, m are 1-3, the 1st, and 1-3, k are the integers of 0-2, and k+l+m=4.
3, pressure sensitive adhesive composition according to claim 1 and 2, wherein, with respect to 100 parts by weight of acrylic interpolymers, the content of organo silane coupling agent is the 0.005-5 weight part.
4, according to any described pressure sensitive adhesive composition among the claim 1-3, wherein, the described monomeric described functional group that contains functional group is a hydroxyl.
5, a kind of optical material is characterized in that, the two sides of optically functional film or single face are provided with any described pressure sensitive adhesive composition layer among the claim 1-4.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2005084199 | 2005-03-23 | ||
| JP2005084199A JP2006265349A (en) | 2005-03-23 | 2005-03-23 | Pressure-sensitive adhesive composition and optical member |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1837314A true CN1837314A (en) | 2006-09-27 |
| CN100577763C CN100577763C (en) | 2010-01-06 |
Family
ID=37014827
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200610003552A Expired - Fee Related CN100577763C (en) | 2005-03-23 | 2006-02-13 | Pressure sensitive adhesive composition and optical materials |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP2006265349A (en) |
| KR (1) | KR20060102494A (en) |
| CN (1) | CN100577763C (en) |
| TW (1) | TW200636037A (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101724358A (en) * | 2008-10-29 | 2010-06-09 | 乐金华奥斯株式会社 | Pressure-sensitive bonding sheet |
| CN104946172A (en) * | 2014-03-31 | 2015-09-30 | 信越化学工业株式会社 | Pressure-sensitive adhesive composition, pressure-sensitive adhesive polarizing plate and liquid crystal display device |
| TWI512403B (en) * | 2011-08-29 | 2015-12-11 | Toray Industries | Colored resin composition and resin black matrix substrate |
| CN105273648A (en) * | 2014-05-30 | 2016-01-27 | 住友化学株式会社 | Optical film with adhesive and optical laminate |
| CN106978122A (en) * | 2011-08-17 | 2017-07-25 | 积水化学工业株式会社 | Sealing material for liquid crystal display device and liquid crystal display cells |
| CN107709369A (en) * | 2015-12-02 | 2018-02-16 | 积水化学工业株式会社 | Light wet-cured type resin combination, electronic component-use bonding agent and display element bonding agent |
| CN112513164A (en) * | 2018-07-30 | 2021-03-16 | 3M创新有限公司 | Transparent elastomeric nanocomposites |
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| JP5262672B2 (en) * | 2008-12-17 | 2013-08-14 | 信越化学工業株式会社 | Pressure-sensitive adhesive composition for liquid crystal elements |
| JP5346220B2 (en) * | 2009-02-03 | 2013-11-20 | リンテック株式会社 | Adhesive and adhesive sheet |
| JP5990847B2 (en) * | 2012-04-04 | 2016-09-14 | サイデン化学株式会社 | Optical pressure-sensitive adhesive composition and optical functional film using the same |
| KR102198346B1 (en) * | 2014-12-29 | 2021-01-04 | 동우 화인켐 주식회사 | Adhesive composition for polarizing plate |
| JP6708158B2 (en) * | 2017-04-14 | 2020-06-10 | 信越化学工業株式会社 | Adhesive composition and film using this composition |
| JP6891036B2 (en) * | 2017-04-28 | 2021-06-18 | 藤森工業株式会社 | Adhesive composition and adhesive film |
| KR102415718B1 (en) | 2017-08-07 | 2022-07-05 | 닛토덴코 가부시키가이샤 | Optical laminate, and image display device |
| JP6697637B2 (en) | 2017-08-07 | 2020-05-20 | 日東電工株式会社 | Adhesive layer, optical film with adhesive layer, optical laminate, and image display device |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3426410B2 (en) * | 1995-05-12 | 2003-07-14 | 日本合成化学工業株式会社 | Adhesive composition |
| JPH09269414A (en) * | 1996-03-29 | 1997-10-14 | Nippon Synthetic Chem Ind Co Ltd:The | Polarizing plate having tacky adhesive layer |
| JPH09269413A (en) * | 1996-03-29 | 1997-10-14 | Nippon Synthetic Chem Ind Co Ltd:The | Polarizing plate having tacky adhesive layer |
| JP2003193014A (en) * | 2001-06-27 | 2003-07-09 | Nippon Carbide Ind Co Inc | Pressure-sensitive adhesive composition for polarizing film |
-
2005
- 2005-03-23 JP JP2005084199A patent/JP2006265349A/en active Pending
-
2006
- 2006-02-13 CN CN200610003552A patent/CN100577763C/en not_active Expired - Fee Related
- 2006-03-03 KR KR1020060020471A patent/KR20060102494A/en not_active Application Discontinuation
- 2006-03-20 TW TW095109384A patent/TW200636037A/en unknown
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101724358A (en) * | 2008-10-29 | 2010-06-09 | 乐金华奥斯株式会社 | Pressure-sensitive bonding sheet |
| CN101724358B (en) * | 2008-10-29 | 2016-06-01 | 乐金华奥斯株式会社 | Pressure sensitive adhesion sheet |
| CN106978122A (en) * | 2011-08-17 | 2017-07-25 | 积水化学工业株式会社 | Sealing material for liquid crystal display device and liquid crystal display cells |
| TWI512403B (en) * | 2011-08-29 | 2015-12-11 | Toray Industries | Colored resin composition and resin black matrix substrate |
| CN104946172A (en) * | 2014-03-31 | 2015-09-30 | 信越化学工业株式会社 | Pressure-sensitive adhesive composition, pressure-sensitive adhesive polarizing plate and liquid crystal display device |
| CN104946172B (en) * | 2014-03-31 | 2018-12-07 | 信越化学工业株式会社 | Pressure-sensitive adhesive composition, pressure-sensitive adhesion polarizing film and liquid crystal display device |
| CN105273648A (en) * | 2014-05-30 | 2016-01-27 | 住友化学株式会社 | Optical film with adhesive and optical laminate |
| CN107709369A (en) * | 2015-12-02 | 2018-02-16 | 积水化学工业株式会社 | Light wet-cured type resin combination, electronic component-use bonding agent and display element bonding agent |
| CN107709369B (en) * | 2015-12-02 | 2021-04-23 | 积水化学工业株式会社 | Light-moisture-curable resin composition, adhesive for electronic component, and adhesive for display element |
| CN112513164A (en) * | 2018-07-30 | 2021-03-16 | 3M创新有限公司 | Transparent elastomeric nanocomposites |
| CN112513164B (en) * | 2018-07-30 | 2023-04-21 | 3M创新有限公司 | Transparent elastomer nanocomposite |
Also Published As
| Publication number | Publication date |
|---|---|
| CN100577763C (en) | 2010-01-06 |
| KR20060102494A (en) | 2006-09-27 |
| TW200636037A (en) | 2006-10-16 |
| JP2006265349A (en) | 2006-10-05 |
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