CN103403120A - Cationic polymerizable adhesive and polarizing plate obtained using same - Google Patents

Cationic polymerizable adhesive and polarizing plate obtained using same Download PDF

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Publication number
CN103403120A
CN103403120A CN2012800102042A CN201280010204A CN103403120A CN 103403120 A CN103403120 A CN 103403120A CN 2012800102042 A CN2012800102042 A CN 2012800102042A CN 201280010204 A CN201280010204 A CN 201280010204A CN 103403120 A CN103403120 A CN 103403120A
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cationically polymerizable
tackiness agent
mass parts
glycidyl ether
ing
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CN103403120B (en
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山本辰弥
田中浩二郎
小尾一树
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DIC Corp
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Dainippon Ink and Chemicals Co Ltd
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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
    • C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • C08G59/245—Di-epoxy compounds carbocyclic aromatic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/08—Saturated oxiranes
    • C08G65/10—Saturated oxiranes characterised by the catalysts used
    • C08G65/105—Onium compounds
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/16—Cyclic ethers having four or more ring atoms
    • C08G65/18—Oxetanes
    • 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
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • 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
    • C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
    • C09J171/02—Polyalkylene oxides
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • 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
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Nonlinear Science (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Mathematical Physics (AREA)
  • Polarising Elements (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

The present invention provides: a cationic polymerizable adhesive having water resistance and adhesion properties excellent enough that even when the polarizing plate or the like is bent, there is no peeling away from the protective film and/or polarizer, and cracks do not form in the adhesive layer; and a polarizing plate obtained using the same. The present invention pertains to: a cationic polymerizable adhesive containing an aromatic glycidyl ether (A), an oxetane compound (B) having at least two oxetanyl groups, a silane coupling agent (C) containing an alicyclic epoxy group, and a cationic polymerization initiator (D), the cationic polymerizable adhesive being characterized by using 100 parts by mass of the aromatic glycidyl ether (A), 300-395 parts by mass of the oxetane compound (B), and 5-100 parts by mass of the silane coupling agent (C).

Description

Cationically polymerizable tackiness agent and use the polarization plates that it obtains
Technical field
The present invention relates to a kind of can be for the cationically polymerizable tackiness agent of the various uses headed by the manufacture of the polarization plates such as to use at liquid-crystal display etc.
Background technology
As tackiness agent, be difficult to cause that the curing obstruction that is caused by the oxygen in atmosphere and the cationically polymerizable tackiness agent that also can be cured reaction after stopping ultraviolet homenergic supply receive publicity.Thus, the exploitation of cationically polymerizable tackiness agent has obvious progress in recent years, reports all-purpose tackiness agent.
As described cationically polymerizable tackiness agent, following cationically polymerizable tackiness agent was for example disclosed, namely, contain: by cyclohexanedimethanodiglycidyl diglycidyl ether distillablely contain the compound of glycidyl ether, by the distillable compound of glycidyl ether, the compound that contains water-disintegrable silyl and epoxy group(ing) and the cationic polymerization initiators of containing of Bisphenol F type diglycidylether, cl content is that 500ppm is (for example with reference to patent documentation 1.)。
Described cationically polymerizable tackiness agent is low because of cementability and the cl content of the level that can use in practical, and has excellent perviousness.But; described cationically polymerizable tackiness agent is because rigidity is high; therefore by described cationically polymerizable tackiness agent for example for the protection of the laminating of film and polaroid in and during the formation polarization plates; in the situation that this polarization plates is subject to warpage, has the cationically polymerizable adhesive layer and from described protective membrane and/or polaroid, peel off, adhesive layer, form the problems such as crackle.
In addition, because the viscosity ratio of described cationically polymerizable tackiness agent is higher, therefore in the situation that the described tackiness agent of coating on protective membrane, polaroid, can in adhesive layer, produce uneven, thereby also have the problems such as optical characteristics to polarization plates exerts an influence.
On the other hand, as the protective membrane that forms polarization plates, what extensively utilized is triacetyl cellulose (TAC) film in the past.
But the TAC film is because water-absorbent is strong, the water droplet of therefore bringing into etc. become bubble and be mixed in adhesive layer and TAC intermembranous, optical characteristics is caused to detrimentally affect, in addition, described water droplet etc. pass through adhesive layer and arrive polaroid, thereby have the problems such as iodine decolouring in polaroid.
So as tackiness agent, strong request can overcome the water tolerance of this kind problem.
According to more than, reality is that strong request has the cementability of following degree, the cationically polymerizable tackiness agent of water tolerance excellence; namely; even in the situation that polarization plates etc. are subject to warpage, can from protective membrane and/or polaroid, peeling off, crackle not appear in adhesive layer yet.
The prior art document
Patent documentation
Patent documentation 1: TOHKEMY 2010-32766 communique
Summary of the invention
The problem that invention will solve
Problem to be solved by this invention is, even provide in the situation that polarization plates etc. are subject to warpage also can not peel off from protective membrane and/or polaroid, can adhesive layer, not occur the cationically polymerizable tackiness agent of the cementability of the degree of crackle, water tolerance excellence and use the polarization plates that it obtains.
For the method for dealing with problems
The inventor etc., in solving the research that described problem carries out, have furtherd investigate the combination of various cationically polymerizable compounds.
Find therein, containing aromatic glycidyl ether, contain silane coupling agent, the cationic polymerization initiators of ester ring type epoxy group(ing), and in the situation that in composition, aromatic glycidyl ether is used, can obtain possessing the tackiness agent of the improvement of water tolerance and to a certain degree good bonding strength.But, still can't prevent from the crackle of the peeling off of protective membrane and/or polaroid, adhesive layer.
So, the inventor etc. for the rigidity that reduces adhesive layer, further improve the purpose of bonding strength, be conceived to make up oxetane compound in above-mentioned tackiness agent.
But in the situation that used and had oxetane compound 1 oxetanyl, so-called 1 official's energy as oxetane compound, the molecular weight of tackiness agent reduces, and can't obtain good bonding strength.
Based on above-mentioned viewpoint, the inventor etc. are studied being used in combination the oxetane compound with the oxetanyl more than 2.
Consequently find, only with respect to aromatic glycidyl ether, used the oxetane compound with the oxetanyl more than 2 of specified quantitative and contained in the situation of silane coupling agent of ester ring type epoxy group(ing), can solve problem of the present invention.
namely, the invention provides a kind of cationically polymerizable tackiness agent, it is to contain aromatic glycidyl ether (A), oxetane compound (B) with the oxetanyl more than 2, the silane coupling agent (C) that contains the ester ring type epoxy group(ing), and the cationically polymerizable tackiness agent of cationic polymerization initiators (D), it is characterized in that, with respect to described aromatic glycidyl ether (A) 100 mass parts, in the scope of 300～395 mass parts, use described oxetane compound (B), in the scope of 5～100 mass parts, use described silane coupling agent (C), provide in addition use this cationically polymerizable tackiness agent by polaroid and protective membrane bonding and must polarization plates.
The effect of invention
Because cationically polymerizable tackiness agent of the present invention is excellent in adhesion, even, therefore in the situation that the polarization plates that use tackiness agent of the present invention obtains etc. are subject to warpage, can not peel off from protective membrane and/or polaroid, crackle can not appear in adhesive layer yet.
Therefore in addition, due to the water tolerance excellence of cationically polymerizable tackiness agent of the present invention, in the situation that by the manufacture of tackiness agent of the present invention for polarization plates, can suppress to form bubble or foaming in the duplexer of polarization plates.
In addition; because cationically polymerizable tackiness agent of the present invention possesses low viscosity and good solidified nature; therefore for example in the situation that protective membrane or polaroid coating tackiness agent of the present invention can not produce inequality yet in adhesive layer, can not cause detrimentally affect to the optical characteristics of polarization plates.
Embodiment
At first, described aromatic glycidyl ether (A) is described.
Described aromatic glycidyl ether (A) is essential composition for possessing cementability.As described aromatic glycidyl ether (A), with regard to giving good cementability, the preferred material with the glycidyl ether more than 2 that uses, more preferably use and have 2～6.As described aromatic glycidyl ether (A), such as using bisphenol A-type glycidyl ether, Bisphenol F type glycidyl ether, bisphenol S type glycidyl ether, dihydroxyphenyl propane D type glycidyl ether etc., in the middle of them, preferably use bisphenol A-type glycidyl ether, Bisphenol F type glycidyl ether.
As described bisphenol A-type glycidyl ether, for example can use bisphenol A diglycidyl ether.
As described Bisphenol F type glycidyl ether, for example can use the Bisphenol F diglycidylether.
As described aromatic glycidyl ether (A), the viewpoint of moderately adjusting the hardness of cured article from can further improving solidified nature and can improving cementability considers, preferred use be selected from bisphenol A diglycidyl ether and Bisphenol F diglycidylether more than a kind.
In addition, in the present invention, so long as in the scope of not damaging effect of the present invention, also can be by glycidyl ether the use of described aromatic glycidyl ether (A) with other.
as described other glycidyl ether, for example can use trihydroxymethylpropanyltri diglycidyl ether, T 55, the Polyglycerine triglycidyl ether, two T 55s etc. have the aliphatic glycidyl based compound of 3 glycidyl ethers, the TriMethylolPropane(TMP) diglycidylether, 1, the 6-hexanediol diglycidyl ether, 1, the 4-butanediol diglycidyl ether, cyclohexanedimethanodiglycidyl diglycidyl ether, propylene glycol diglycidylether, glycol ether diglycidylether etc. has the glycidyl compound of 2 glycidyl ethers etc.
In addition, as described other glycidyl ether, also can use being hydrogenated of described aromatic glycidyl ether (A) Hydrogenated Bisphenol A type glycidyl ether, A Hydrogenated Bisphenol A F type glycidyl ether etc.
Below, described oxetane compound (B) is described.
Described oxetane compound (B) be especially prevent from protective membrane and/or polaroid the crackle of peeling off, prevent adhesive layer, give low viscosity aspect essential composition.
In addition, from the aspect that solves problem of the present invention, consider, described oxetane compound (B) must use with respect to described aromatic glycidyl ether (A) 100 mass parts in the scope of 300～395 mass parts.
As described oxetane compound (B), can use have more than 2, preferred 2～4 compounds that participate in the oxetanyl of cationoid polymerisations.
As described oxetane compound (B), specifically, such as using with the compound of following general formula (1), (2) expression etc.
Figure BDA0000371047170000041
Figure BDA0000371047170000051
In above-mentioned general formula (1), (2), R 1Represent independently of one another hydrogen atom, carbonatoms is the alkyl of 1～6 straight chain shape, a chain or ring-type, allyl group, aryl, aralkyl, furyl or thienyl, R 2Represent independently of one another organic residue of divalent, Z represents Sauerstoffatom or sulphur atom independently of one another.
As described R 1Represented carbonatoms is the alkyl of 1～6 straight chain shape, a chain or ring-type, is for example methyl, ethyl, just or sec.-propyl, just, the XOR tertiary butyl, amyl group, hexyl, cyclohexyl etc., in addition, as aryl, such as being phenyl, naphthyl, tolyl, xylyl etc., in addition, as aralkyl, such as being benzyl, styroyl etc.
In addition, in described general formula (1), as R 2Organic residue of represented divalent, for example have the straight chain shape, prop up the alkylidene group of chain or ring-type, has the polyoxyalkylenes of 4～30 carbon atoms, phenylene, and xylylene, with the structure of following general formula (3) and (4) expression.
Form described R 2The alkylidene group of straight chain shape, chain or ring-type be preferably methylene radical, ethylidene, 1, the carbonatomss such as 2-or trimethylene, butylidene, cyclohexylidene are 1～15 alkylidene group.In addition, polyoxyalkylenes with 4～30 carbon atoms preferably has 4～8 carbon atoms, for example is preferably polyoxyethylene groups, polyoxypropylene base.
Figure BDA0000371047170000052
In described general formula (3), R 3Expression Sauerstoffatom, sulphur atom, CH 2, NH, SO, SO 2, C (CF 3) 2Or C (CH 3) 2.
[changing 4]
Figure BDA0000371047170000061
In described general formula (4), R 4Expression has alkylidene group, the arylidene of 1～6 carbon atom and the functional group that represents with following general formula (5).
Figure BDA0000371047170000062
In described general formula (5), a represents 1～6 integer, and b represents 1～15 integer.
As described general formula (5), b is preferably 1～3 integer.
As described oxetane compound with 2～4 trimethylene oxide ring structures, such as ARONE OXETANE OXT-221, ARONE OXETANE OXT-121, ARONE OXETANE OXT-223 (above is East Asia synthetic (strain) system), ETERNACOLL OXBP, ETERNACOLL OXTP, ETERNACOLL OXIPA (above be that the emerging product of space section (strain) is made) etc. just commercially available.
As the molecular weight of described oxetane compound (B), from the viewpoint that can further improve low viscosity, consider, be preferably 100～800 scope, more preferably 100～500 scope.This be because; tackiness agent of the present invention is for example in the situation that bonding polaroid and protective membrane; in order to advance and to solidify fully; usually how the thickness of adhesive layer is carried out with film (number μ m is thick); for the uniform film thickness ground of tackiness agent with described degree is coated with, tackiness agent need to be low viscosity.And the molecular weight of described oxetane compound (B) represents the molecular weight that is calculated by structural formula.
In addition, as described oxetane compound (B), among above-mentioned, the preferred compound that uses with described general formula (1) expression, particularly use the R in this formula 1For ethyl R 2For two [1-ethyl (3-oxetanyl)] methyl ethers of methylene radical, the thickness of the tackiness agent after can making to solidify is thinner, can further improve solidified nature, cementability, therefore particularly preferably.
In addition, in the present invention, so long as in the scope of not damaging effect of the present invention, also can be by described oxetane compound (B) and the oxetane compound with 1 oxetanyl use.
As described trimethylene oxide based compound with 1 oxetanyl, for example can use the compound shown in following general formula (6).
Figure BDA0000371047170000071
(the R in general formula (6) 1Expression hydrogen atom, carbonatoms are that 1～8 alkyl, carbonatoms are that 1～5 alkoxyalkyl or carbonatoms are 1～6 hydroxyalkyl.
R 2Expression hydrogen atom, carbonatoms that also can branch are 1～10 alkyl, aliphatics ring type structure, aromatic structure.)
As the R that can form in described general formula (6) 1Carbonatoms be the example of 1～8 alkyl, can enumerate methyl, ethyl, n-propyl, sec.-propyl and 2-ethylhexyl etc.
In addition, as the R that can form in described general formula (6) 1Carbonatoms be the example of 1～5 alkoxyalkyl, can enumerate methoxymethyl, ethoxyl methyl, propoxy-methyl, methoxy ethyl, ethoxyethyl group, propoxy-ethyl etc.
In addition, as the R that can form in described general formula (6) 1Carbonatoms be the example of 1～6 hydroxyalkyl, can enumerate hydroxymethyl, hydroxyethyl and hydroxypropyl etc.
In addition, as the R that can form in described general formula (6) 2Also can branch carbonatoms be 1～10 alkyl, can enumerate the alkyl of the straight chain shapes such as methyl, ethyl, propyl group, or as 2-ethylhexyl etc. branch alkyl.
In addition, as the R that can form in described general formula (6) 2Aliphatics ring type structure, such as enumerating cyclohexyl etc.Described cyclohexyl etc. also can have alkyl etc. and replace hydrogen atom.
In addition, as the R that can form in described general formula (6) 2Aromatic structure, such as enumerating phenyl etc.Described phenyl etc. also can have alkyl etc. and replace hydrogen atom.
Below, described silane coupling agent (C) is described.
Described silane coupling agent (C) considers it is essential from the intensity aspect of giving cementability or water tolerance, adhesive layer and filming.
In addition, from the aspect that solves problem of the present invention, consider, described silane coupling agent (C) must use with respect to described aromatic glycidyl ether (A) 100 mass parts in the scope of 5～100 mass parts.
as described silane coupling agent (C), so long as have the ester ring type of epoxy group(ing) epoxy group(ing) is arranged in alicyclic structure silane coupling agent, just be not particularly limited, however (3, the 4-epoxy group(ing) cyclohexyl) ethyl trimethoxy silane that for example can use 2-, 2-(3,4-epoxy group(ing) cyclohexyl) ethyl triethoxysilane, 2-(3,4-epoxy group(ing) cyclohexyl) ethyl three positive propoxy silane, 2-(3,4-epoxy group(ing) cyclohexyl) ethyl three isopropoxy silane, 2-(3,4-epoxy group(ing) cyclohexyl) ethyl-methyl dimethoxy silane, 2-(3,4-epoxy group(ing) cyclohexyl) ethyl-methyl diethoxy silane, 2-(3,4-epoxy group(ing) cyclohexyl) ethyl-methyl two positive propoxy silane, 2-(3,4-epoxy group(ing) cyclohexyl) ethyl-methyl diisopropoxy silane, 2-(3,4-epoxy group(ing) cyclohexyl) ethyl dimethyl methyl TMOS, 2-(3,4-epoxy group(ing) cyclohexyl) ethyl dimethylethoxysilane, 2-(3,4-epoxy group(ing) cyclohexyl) ethyl dimethyl n propoxy-silane, 2-(3,4-epoxy group(ing) cyclohexyl) ethyl dimethyl isopropoxy silane, 2-(3,4-epoxy group(ing) cyclohexyl) ethyl diethyldithiocarbamate dimethoxy silane, 2-(3,4-epoxy group(ing) cyclohexyl) ethyl diethyldithiocarbamate diethoxy silane etc.In the middle of them, from the viewpoint of further raising solidified nature or cementability, water tolerance, consider, preferred use be selected from 2-(3,4-epoxy group(ing) cyclohexyl) ethyl trimethoxy silane and 2-(3,4-epoxy group(ing) cyclohexyl) ethyl triethoxysilane more than a kind.
In addition, in the present invention, so long as in the scope of not damaging effect of the present invention, also can be in described silane coupling agent (C) and with other silane coupling agent.
As described other silane coupling agent, such as using 3-glycidoxypropyltrime,hoxysilane, 3-glycidoxy propyl-triethoxysilicane, 3-glycidoxy propyl group methyldiethoxysilane, 3-glycidoxy propyl group methyl dimethoxysilane etc.
Below, described cationic polymerization initiators (D) is described.
The cationic polymerization initiators that uses in the present invention (D) refers to that the irradiation that for example utilizes ultraviolet homenergic ray produces the compound of the acid that can cause cationoid polymerisation.
As described cationic polymerization initiators (D), for example can use cationic moiety as aromatic matte, aromatic series iodine, aromatic series diazonium, aromatic series ammonium, thianthrene, thioxanthone, (2,4-cyclopentadiene-1-yl) [(1-methylethyl) benzene]-Fe positively charged ion, anionicsite by BF 4 -, PF 6 -, SbF 6 -, [BX 4] -The salt that (wherein, X is the phenyl that has been replaced by the fluorine more than at least 2 or trifluoromethyl) forms etc.
as described aromatic series sulfonium salt, for example can use the two hexafluorophosphates of two [4-(phenylbenzene sulfonium base) phenyl] thioethers, the two hexafluoro antimonates of two [4-(phenylbenzene sulfonium base) phenyl] thioether, the two a tetrafluoro borates of two [4-(phenylbenzene sulfonium base) phenyl] thioether, two [4-(phenylbenzene sulfonium base) phenyl] thioether four (pentafluorophenyl group) borate, phenylbenzene-4-(thiophenyl) phenyl sulfonium hexafluorophosphate, phenylbenzene-4-(thiophenyl) phenyl sulfonium hexafluoro antimonate, phenylbenzene-4-(thiophenyl) phenyl sulfonium a tetrafluoro borate, phenylbenzene-4-(thiophenyl) phenyl sulfonium four (pentafluorophenyl group) borate, the triphenylsulfonium hexafluorophosphate, the triphenylsulfonium hexafluoro antimonate, the triphenylsulfonium a tetrafluoro borate, triphenylsulfonium four (pentafluorophenyl group) borate, the two hexafluorophosphates of two [4-(two (4-(2-hydroxyl-oxethyl)) phenyl sulfonium base) phenyl] thioether, the two hexafluoro antimonates of two [4-(two (4-(2-hydroxyl-oxethyl)) phenyl sulfonium base) phenyl] thioether, the two a tetrafluoro borates of two [4-(two (4-(2-hydroxyl-oxethyl)) phenyl sulfonium base) phenyl] thioether, two [4-(two (4-(2-hydroxyl-oxethyl)) phenyl sulfonium base) phenyl] thioether four (pentafluorophenyl group) borate etc.
in addition, described aromatic series salt compounded of iodine, for example can use diphenyl iodine hexafluorophosphate, phenylbenzene iodine hexafluoro antimonate, phenylbenzene iodine a tetrafluoro borate, phenylbenzene iodine four (pentafluorophenyl group) borate, two (dodecylphenyl) iodine hexafluorophosphate, two (dodecylphenyl) iodine hexafluoro antimonate, two (dodecylphenyl) iodine a tetrafluoro borate, two (dodecylphenyl) iodine four (pentafluorophenyl group) borate, 4-aminomethyl phenyl-4-(1-methylethyl) phenyl-iodide hexafluorophosphate, 4-aminomethyl phenyl-4-(1-methylethyl) phenyl-iodide hexafluoro antimonate, 4-aminomethyl phenyl-4-(1-methylethyl) phenyl-iodide a tetrafluoro borate, 4-aminomethyl phenyl-4-(1-methylethyl) phenyl-iodide four (pentafluorophenyl group) borate etc.
In addition, as described aromatic series diazonium salt, such as using phenyl diazonium hexafluorophosphate, phenyl diazonium hexafluoro antimonate, phenyl diazonium a tetrafluoro borate, phenyl diazonium four (pentafluorophenyl group) borate etc.
In addition, as described aromatic series ammonium salt, can use 1-benzyl-2-cyanopyridine hexafluorophosphate, 1-benzyl-2-cyanopyridine hexafluoro antimonate, 1-benzyl-2-cyanopyridine a tetrafluoro borate, 1-benzyl-2-cyanopyridine four (pentafluorophenyl group) borate, 1-(naphthyl methyl)-2-cyanopyridine hexafluorophosphate, 1-(naphthyl methyl)-2-cyanopyridine hexafluoro antimonate, 1-(naphthyl methyl)-2-cyanopyridine a tetrafluoro borate, 1-(naphthyl methyl)-2-cyanopyridine four (pentafluorophenyl group) borate etc.
In addition, as described thioxanthone salt, can use S-xenyl ITX hexafluorophosphate etc.
In addition, described (2,4-cyclopentadiene-1-yl) [(1-methylethyl) benzene]-Fe salt, can use (2,4-cyclopentadiene-1-yl) [(1-methylethyl) benzene]-Fe (II) hexafluorophosphate, (2,4-cyclopentadiene-1-yl) [(1-methylethyl) benzene]-Fe (II) hexafluoro antimonate, 2,4-cyclopentadiene-1-yl) [(1-methylethyl) benzene]-Fe (II) a tetrafluoro borate, 2,4-cyclopentadiene-1-yl) [(1-methylethyl) benzene]-Fe (II) four (pentafluorophenyl group) borate etc.
described cationic polymerization initiators (D) is CPI-100P for example, CPI-101A, CPI-110P, CPI-200K, CPI-210S (above is SUN-APRO (strain) system), CYRACURE trigger for optical solidification UVI-6990, CYRACURE trigger for optical solidification UVI-6992, CYRACURE trigger for optical solidification UVI-6976 (above is DOW Chemical Japan (strain) system), Adekaoptomer SP-150, Adekaoptomer SP-152, Adekaoptomer SP-170, Adekaoptomer SP-172, Adekaoptomer SP-300 (above is (strain) ADEKA system), CI-5102, CI-2855 (above is Japanese Cao Da (strain) system), Sun-Aid SI-60L, Sun-Aid SI-80L, Sun-Aid SI-100L, Sun-Aid SI-110L, Sun-Aid SI-180L, Sun-Aid SI-110, Sun-Aid SI-180 (more than be three new chemical industry (strain) system), Esacure1064, Esacure1187 (above is Lamberti company system), Omnicat550 (IGM Resins company system), Irgacure250 (BASF Japan (strain) system), RHODORSIL PHOTOINITIATOR2074 (Rhodia Japan (strain) system) etc. are just commercially available.
For the usage quantity of described cationic polymerization initiators (D), with respect to described aromatic glycidyl ether (A) 100 mass parts, preferably as effective constituent, in the scope of 5～50 mass parts, use.
As cationically polymerizable tackiness agent of the present invention, also can also comprise photosensitizer (E).
By cationically polymerizable tackiness agent of the present invention during for polaroid and protective membrane bonding; following situation is arranged; namely; on described protective membrane, be coated with described cationically polymerizable tackiness agent; then, on this coated face, place polaroid, thereafter; from the protective membrane side, carry out uviolizing described later, make the cationically polymerizable adhesive solidification.In this situation; in the situation that use the protective membrane that is difficult to see through the light more than 380nm (such as the TAC film etc.) as described protective membrane; from the viewpoint of the solidified nature that can improve the cationically polymerizable tackiness agent, consider, preferably contain described photosensitizer (E).
Described photosensitizer (E) such as the derivative that can use anthracene, anthraquinone, thioxanthone, benzophenone, benzoin iso-propylether and these compounds etc.In the middle of them, based on above-mentioned reason, preferably use and wavelength is illustrated to the material of very big absorption as the light display more than 380nm, more preferably use the anthracene based compound.
as described to wavelength, be the anthracene based compound that light display more than 380nm illustrates very big absorption, can use 9,10-dimethoxy anthracene, 9,10-diethoxy anthracene, 9,10-dipropoxy anthracene, 9,10-diisopropoxy anthracene, 9,10-dibutoxy anthracene, 9,10-, bis-pentyloxy anthracenes, 9,10-, bis-hexyloxy anthracenes, two (2-methoxy ethoxy) anthracenes of 9,10-, two (2-ethoxy ethoxy) anthracenes of 9,10-, two (the 2-butoxy oxyethyl group) anthracenes of 9,10-, two (the 3-butoxy propoxy-) anthracenes of 9,10-, 2-methyl or EDMO, 2-methyl or 2-ethyl-9,10-diethoxy anthracene, 2-methyl or 2-ethyl-9,10-dipropoxy anthracene, 2-methyl or 2-ethyl-9,10-diisopropoxy anthracene, 2-methyl or 2-ethyl-9,10-dibutoxy anthracene, 2-methyl or 2-ethyl-9,10-bis-pentyloxy anthracenes, 2-methyl or 2-ethyl-9,10-bis-hexyloxy anthracenes etc., (" UVS-1331 " Kawasaki chemical industry (strain) system), Kayacure DETX-S (Japanese chemical drug (strain) system) etc. are just commercially available.
For the usage quantity of described photosensitizer (E), with respect to described aromatic glycidyl ether (A) 100 mass parts, be preferably in the scope of 0.5～10 mass parts and use.
In addition, in the situation that use described photosensitizer (E), due to meeting, widen the sensitization wavelength region of described cationic initiator (D), further improve the solidified nature of cationically polymerizable tackiness agent of the present invention, therefore also can make simultaneously photoactivation auxiliary agent (F).
As described photosensitization auxiliary agent (F), such as using nitrofluorene, naphthalene series compound etc., can preferably use Isosorbide-5-Nitrae-dimethoxy-naphthalene, 1-oxyethyl group-4-methoxynaphthalene, Isosorbide-5-Nitrae-diethoxy naphthalene, Isosorbide-5-Nitrae-dipropoxy naphthalene, Isosorbide-5-Nitrae-dibutoxy naphthalene etc.
For the usage quantity of described photosensitization auxiliary agent (F), with respect to described aromatic glycidyl ether (A) 100 mass parts, be preferably in the scope of 0.5～10 mass parts and use.
Below, cationically polymerizable tackiness agent of the present invention is described.
Cationically polymerizable tackiness agent of the present invention contains described aromatic glycidyl ether (A), have the oxetane compound (B) of the oxetanyl more than 2, contain the silane coupling agent (C) of ester ring type epoxy group(ing) and cationic polymerization initiators (D), use as required described photosensitizer (E), photosensitization auxiliary agent (F), yet, so long as do not damage the scope in effect of the present invention, also can contain various additives.
As described additive, such as can use thixotropic agent, leveling agent, antioxidant, thickening material, paraffin, thermo-stabilizer, fast light stablizer, white dyes, whipping agent, thermoplastic resin, heat-curing resin, organic solvent, electroconductibility imparting agent, anti-static electricity interference agent, water vapour permeability rising agent, hydrophobizing agent, hollow foam, contain the crystal water compound, fire retardant, water-retaining agent, moisture adsorbent, deodorant, surfactant, defoamer, mould inhibitor, sanitas, algaecide, antiblocking agent, anti hydrolysis agent, organic and inorganic water-soluble compound etc.
In addition, beyond above-mentioned, can also, for further reducing the purpose of the rigidity of cationically polymerizable tackiness agent of the present invention, contain the polyvalent alcohols such as polyether glycol.
In addition, beyond polyvalent alcohol, can also, for further improving the purpose of solidified nature, lowering viscousity in cationically polymerizable tackiness agent of the present invention, contain the cationically polymerizable compounds such as vinyl ether or tetrahydrofuran (THF), ester ring type epoxy compounds.
As described vinyl ether, such as using butyleneglycol divinyl ether, hexylene glycol divinyl ether, diethylene glycol divinyl ether, triethylene glycol divinyl ether, neopentyl glycol divinyl ether, cyclohexanedimethanol divinyl ether etc.
In addition, as described ester ring type epoxy compounds, for example can use the epoxy compounds of the ester ring type epoxy group(ing) with 1～4.
As described epoxy compounds with 1 ester ring type epoxy group(ing), for example can enumerate the ester ring type epoxy compounds with following general formula (7) expression.
Figure BDA0000371047170000121
(in formula (7), R 1, R 2And R 3Represent independently of one another hydrogen atom or methyl.)
In addition, as the epoxy compounds with 2 ester ring type epoxy group(ing), for example can use with 3 of following general formula (8) expression, 4-epoxy group(ing) cyclohexenyl methyl-3, (in general formula (8), a is 0 compound to 4-epoxy-cyclohexane carboxylicesters.), (in general formula (8), a is 1 compound to its caprolactone modification thing.), its trimethylammonium caprolactone modification thing (structural formula (9) and structural formula (10)), with and valerolactone modifier (structural formula (11) and structural formula (12)), with the compound of structural formula (13) expression.
Figure BDA0000371047170000131
(a in general formula (8) represents 0 or 1.)
Figure BDA0000371047170000141
In addition, as described epoxy compounds with 2 ester ring type epoxy group(ing), also can use the such compound shown in following general formula (14).
(R in general formula (14) 1～R 6Represent that independently of one another hydrogen atom or carbonatoms are 1～6 alkyl.)
Compound as shown in described general formula (14), specifically, can use dicyclohexyl-3,3 '-diepoxide.
In addition, as the epoxy compounds with 3 ester ring type epoxy group(ing), can use the compound with following general formula (15) expression.
Figure BDA0000371047170000151
(in general formula (15), a and b are 0 or 1 independently of one another, and they both can be the same or different.)
As the ester ring type epoxy compounds with general formula (15) expression, such as having bought EPOLEAD GT301, EPOLEAD GT302 (above is Daicel chemical industry (strain) system) etc.
In addition, as the epoxy compounds with 4 ester ring type epoxy group(ing), for example can use the compound with following general formula (16) expression.
Figure BDA0000371047170000152
(in described general formula (16), a～d represents 0 or 1 independently of one another, and they both can be the same or different.)
As the ester ring type epoxy compounds with described general formula (16) expression, such as EPOLEAD GT401, EPOLEAD GT403 (above be that Daicel chemical industry (strain) is made) etc. just commercially available.
Cationically polymerizable tackiness agent of the present invention possesses low viscosity, and the viscosity under normal temperature is the scope of 10～100mPas.And the viscosity table of described cationically polymerizable tackiness agent is shown in the value of measuring with Brookfield viscometer under 25 ℃.
Below, the manufacture method of cationically polymerizable tackiness agent of the present invention is described.Cationically polymerizable tackiness agent of the present invention for example can utilize following method to manufacture.
Cationically polymerizable tackiness agent of the present invention is such as possessing by use the container etc. of stirrer, and described aromatic glycidyl ether (A), described oxetane compound (B), described silane coupling agent (C), described cationic polymerization initiators (D) and the mixing such as described various additives of using as required of manufacturing in advance, stirring are manufactured.
It is curing that cationically polymerizable tackiness agent of the present invention can utilize the irradiation of ultraviolet homenergic ray to advance.And cationically polymerizable tackiness agent of the present invention is to utilize after the irradiation of energy-ray of ultraviolet ray etc. the material that just starts to show cementability.
The irradiation of described ultraviolet homenergic ray is preferably 10～5000mJ/cm 2Scope, 20～2500mJ/cm more preferably 2Scope, be particularly preferably 30～1500mJ/cm 2Scope.
As ultraviolet generating source, such as using the known lamps such as xenon lamp, xenon-mercuryvapour lamp, metal halide lamp, high pressure mercury vapour lamp, Cooper-Hewitt lamp.And ultraviolet irradiation amount is to use the UV meter: UV Power PucK (II) (Electronic Instrumentation and Technology company system) measures in the wavelength region of 300～390nm value is as benchmark.
In addition, as required, also can be after the irradiation of described energy-ray, by with about 40～80 ℃ heating, and further promote to solidify.
Below, polarization plates of the present invention is described.
Polarization plates of the present invention is by the bonding member that forms of the adhesive linkage that comprises described cationically polymerizable tackiness agent by protective membrane and polaroid.
described protective membrane for example can adopt and use acrylic resin, silicon is resin, epoxy is resin, fluorine resin, polystyrene resin, polyester based resin, polysulfones is resin, polyarylester is resin, polyvinyl chloride (PVC) RESINS, polyvinylidene chloride, the cyclic olefine resins such as norbornylene, the amorphism polyolefin-based resins, polyimide is resin, the ester ring type polyimide is resin, cellulose-based resin, PC (polycarbonate), PBT (polybutylene terephthalate), MODIFIED PP E (polyphenylene oxide), PEN (PEN), the film of PET (polyethylene terephthalate) etc. or the material of sheet, the biological degradability films such as polylactic acid polymer.
In addition; as described acrylic resin; can use second-order transition temperature (Tg) is acrylic resin, the thermoplastic acrylic resin more than 100 ℃; also can in them, contain number average bead diameter is the elastomerics particle below 2.0 μ m, forms the protective membrane that described elastomerics particle set is distributed in the thickness direction central part of protective membrane.
The thickness of the described protective membrane that uses while manufacturing polarization plates of the present invention is according to the purposes that is used and difference, yet is preferably the scope of about 20 μ m～100 μ m.In addition, the thickness of described polaroid is preferably the scope of about 5 μ m～50 μ m usually.
in addition, as described polaroid, be not particularly limited, can use various materials, yet for example can use by polyvinyl alcohol, part formalizing polyvinyl alcohol, the ethylene vinyl acetate copolymer pastern divide saponified wait on the plastic basis material that hydrophilic macromolecular compounds forms unilateral stretching after the dichroic material such as absorption iodine or dichroic dye and material, described plastic basis material is carried out to unilateral stretching oriented film the described dichroic material of surface adsorption and material, the polyenes such as the desalination acid treatment thing of the processed thing of polyvinyl alcohol or polyvinyl chloride are alignment films etc.Especially, preferably use polyvinyl alcohol mesentery and adsorbed the film of the dichroic substance such as iodine.
In addition; polarization plates of the present invention for example also can be manufactured by following operation; namely; on described protective membrane, be coated with described cationically polymerizable tackiness agent; then after this coated face is irradiated to the ultraviolet ray of described amount; by on this coated face, placing also bonding polaroid, manufacture; in addition; can also manufacture by following operation, that is, and the described cationically polymerizable tackiness agent of coating on described protective membrane; then; on this coated face, place polaroid, thereafter, from described protective membrane side, irradiate the ultraviolet ray of described amount and manufacture.In addition; polarization plates of the present invention also can be manufactured by following operation; namely; the described cationically polymerizable tackiness agent of coating on described polaroid; then; after this coated face being irradiated to the ultraviolet ray of described amount; on this coated face, place and bonding protective membrane and manufacturing, in addition, can also manufacture by following operation; namely; the described cationically polymerizable tackiness agent of coating, then, place protective membrane on this coated face on described polaroid; from described protective membrane side irradiate the ultraviolet ray of described amount and manufacture thereafter.When manufacturing polarization plates of the present invention, for the thickness of the adhesive linkage that consists of described cationically polymerizable tackiness agent, based on not damaging the reason such as optical characteristics, more Bao Yuehao, be preferably below 5 μ m specifically.
in addition, polarization plates of the present invention for example also can followingly be manufactured, namely, one side at 2 protective membranes, be coated with respectively described cationically polymerizable tackiness agent, then, after this coated face being irradiated to the ultraviolet ray of described amount, by this coated face is placed respectively, be bonded in the two sides of polaroid, and form, from above, play the duplexer into protective membrane/cationically polymerizable adhesive layer/polaroid/cationoid polymerisation adhesive layer/protective membrane, in addition, all right following manufacture, namely, one side at 2 protective membranes, be coated with respectively described cationically polymerizable tackiness agent, this coated face is placed on respectively to the two sides of polaroid, thereafter, irradiate the ultraviolet ray of described amount and manufacture described duplexer.
Method as the described cationically polymerizable tackiness agent of coating, be not particularly limited, such as the method that can use the coatings such as the slit coater methods such as showering curtain type plane coating method or mould Tu Fa, scraper for coating method, rolling method, intaglio plate coating method, utilization spraying.
Utilize polarization plates of the present invention that above method obtains such as can be for the member of the indicating meter that forms the mobile communication terminal such as mobile phone or LCD TV, PC, portable game etc.
Embodiment
Below, the present invention is described in detail to utilize embodiment.
[work of polaroid method processed]
Kuraray POVAL PVA-117H (polyvinyl alcohol of (strain) Kuraray system, the polymerization degree 1700, fully saponified thing, Powdered) is dissolved in the water, use excellent painting machine to be coated on mold release film the polyvinyl alcohol water solution of gained (nonvolatile component 8 quality %), then, after under the environment of 80 ℃ dry 5 minutes, by removing described mold release film, and produce the polyvinyl alcohol film of thick 75 μ m.
Then, the polyvinyl alcohol film of gained is fixed in drawing machine, in the warm water of 40 ℃ by the size of described film along unilateral stretching to 3 times.
After removing the water that is attached to the surface that utilizes the stretched film that aforesaid operations obtains, described stretched film is immersed in to being adjusted in the aqueous solution of 30 ℃ of water of the potassiumiodide of the iodine that contains 0.02 mass parts, 2 mass parts and 100 mass parts.
Then, described stretched film is immersed in to being adjusted in the aqueous solution of 56.5 ℃ of water of the boric acid of the potassiumiodide that contains 12 mass parts, 5 mass parts and 100 mass parts.
Stretched film after described dipping is cleaned in being adjusted into the pure water of 8 ℃ after, by dry under the environment at 65 ℃, and obtain the polaroid (polarizing coating) that surface adsorption in the stretched film that consists of polyvinyl alcohol has iodine and has been orientated.
[embodiment 1]
by possessing stirrer, reflux cooler, thermometer, in the reaction vessel of dropping funnel and nitrogen inlet, mix the EPICLON EXA-830CRP as aromatic glycidyl ether (A) of 100 mass parts, the conduct of 300 mass parts has the ARONE OXETANE OXT-221 of the oxetane compound (B) of the oxetanyl more than 2, the conduct of 100 mass parts contains the KBM-303 of the silane coupling agent (C) of ester ring type epoxy group(ing), the propylene glycol carbonate 50 quality % solution of the phenylbenzene-4-as cationic polymerization initiators (D) of 40 mass parts (thiophenyl) phenyl sulfonium hexafluorophosphate, 2.5 mass parts as 9 of photosensitizer (E), 10-dibutoxy anthracene, 2.5 mass parts as 1 of photosensitization auxiliary agent (F), 4-diethoxy naphtho-stirs, and prepare the cationically polymerizable tackiness agent that viscosity is 25mPas (25 ℃).
Usining separately the surface of polymethylmethacrylate as acrylic resin film and the TAC film of principal constituent, use the wire drawing rod to reach the about mode of the thickness of 2 μ m, to be coated with respectively the cationically polymerizable tackiness agent of gained, this coated substrate is fitted in respectively to the two sides of described polaroid (polarizing coating).Then, after using the rubber rollers pressurization, by using the UV irradiation equipment (Fusion LH-6 output rating 100%, line speed 17.8m/ minute) of conveyor-type, the accumulative total light quantity of irradiating 300～390nm from described acrylic resin film side is 1300mJ/cm 2Ultraviolet ray, and obtain having the polarization plates that rises from above as the structure of protective membrane/cationically polymerizable adhesive layer/polaroid/cationically polymerizable adhesive layer/protective membrane.
[embodiment 2]
by possessing stirrer, reflux cooler, thermometer, in the reaction vessel of dropping funnel and nitrogen inlet, mix the EPICLON EXA-830CRP as aromatic glycidyl ether (A) of 100 mass parts, the conduct of 350 mass parts has the ARONE OXETANE OXT-221 of the oxetane compound (B) of the oxetanyl more than 2, the conduct of 50 mass parts contains the KBM-303 of the silane coupling agent (C) of ester ring type epoxy group(ing), the propylene glycol carbonate 50 quality % solution of the phenylbenzene-4-as cationic polymerization initiators (D) of 40 mass parts (thiophenyl) phenyl sulfonium hexafluorophosphate, 2.5 mass parts as 9 of photosensitizer (E), 10-dibutoxy anthracene, 2.5 mass parts as 1 of photosensitization auxiliary agent (F), 4-diethoxy naphtho-stirs, and prepare the cationically polymerizable tackiness agent that viscosity is 26mPas (25 ℃).
Usining separately the surface of polymethylmethacrylate as acrylic resin film and the TAC film of principal constituent, use the wire drawing rod to reach the about mode of the thickness of 2 μ m, to be coated with respectively the cationically polymerizable tackiness agent of gained, this coated substrate is fitted in respectively to the two sides of described polaroid (polarizing coating).Then, after using the rubber rollers pressurization, by using the UV irradiation equipment (Fusion LH-6 output rating 100%, line speed 17.8m/ minute) of conveyor-type, the accumulative total light quantity of irradiating 300～390nm from described acrylic resin film side is 1300mJ/cm 2Ultraviolet ray, and obtain having from the polarization plates of top structure for protective membrane/cationically polymerizable adhesive layer/polaroid/cationically polymerizable adhesive layer/protective membrane.
[embodiment 3]
by possessing stirrer, reflux cooler, thermometer, in the reaction vessel of dropping funnel and nitrogen inlet, mix the EPICLON EXA-830CRP as aromatic glycidyl ether (A) of 100 mass parts, the conduct of 375 mass parts has the ARONE OXETANE OXT-221 of the oxetane compound (B) of the oxetanyl more than 2, the conduct of 25 mass parts contains the KBM-303 of the silane coupling agent (C) of ester ring type epoxy group(ing), the propylene glycol carbonate 50 quality % solution of the phenylbenzene-4-as cationic polymerization initiators (D) of 40 mass parts (thiophenyl) phenyl sulfonium hexafluorophosphate, 2.5 mass parts as 9 of photosensitizer (E), 10-dibutoxy anthracene, 2.5 mass parts as 1 of photosensitization auxiliary agent (F), 4-diethoxy naphtho-stirs, and prepare the cationically polymerizable tackiness agent that viscosity is 26mPas (25 ℃).
Using polymethylmethacrylate as the acrylic resin film of principal constituent and TAC film separately-individual surface, use the wire drawing rod to reach the about mode of the thickness of 2 μ m, to be coated with respectively the cationically polymerizable tackiness agent of gained, this coated substrate is fitted in respectively to the two sides of described polaroid (polarizing coating).Then, after using the rubber rollers pressurization, by using the UV irradiation equipment (Fusion LH-6 output rating 100%, line speed 17.8m/ minute) of conveyor-type, the accumulative total light quantity of irradiating 300～390nm from described acrylic resin film side is 1300mJ/cm 2Ultraviolet ray, and obtain having the polarization plates that rises from above as the structure of protective membrane/cationically polymerizable adhesive layer/polaroid/cationically polymerizable adhesive layer/protective membrane.
[embodiment 4]
by possessing stirrer, reflux cooler, thermometer, in the reaction vessel of dropping funnel and nitrogen inlet, mix the EPICLON EXA-830CRP as aromatic glycidyl ether (A) of 100 mass parts, the conduct of 390 mass parts has the ARONE OXETANE OXT-221 of the oxetane compound (B) of the oxetanyl more than 2, the conduct of 10 mass parts contains the KBM-303 of the silane coupling agent (C) of ester ring type epoxy group(ing), the propylene glycol carbonate 50 quality % solution of the phenylbenzene-4-as cationic polymerization initiators (D) of 40 mass parts (thiophenyl) phenyl sulfonium hexafluorophosphate, 2.5 mass parts as 9 of photosensitizer (E), 10-dibutoxy anthracene, 2.5 mass parts as 1 of photosensitization auxiliary agent (F), 4-diethoxy naphtho-stirs, and prepare the cationically polymerizable tackiness agent that viscosity is 26mPas (25 ℃).
Usining separately the surface of polymethylmethacrylate as acrylic resin film and the TAC film of principal constituent, use the wire drawing rod to reach the about mode of the thickness of 2 μ m, to be coated with respectively the cationically polymerizable tackiness agent of gained, this coated substrate is fitted in respectively to the two sides of described polaroid (polarizing coating).Then, after using the rubber rollers pressurization, by using the UV irradiation equipment (Fusion LH-6 output rating 100%, line speed 17.8m/ minute) of conveyor-type, the accumulative total light quantity of irradiating 300～390nm from described acrylic resin film side is 1300mJ/cm 2Ultraviolet ray, and obtain having the polarization plates that rises from above as the structure of protective membrane/cationically polymerizable adhesive layer/polaroid/cationically polymerizable adhesive layer/protective membrane.
[embodiment 5]
by possessing stirrer, reflux cooler, thermometer, in the reaction vessel of dropping funnel and nitrogen inlet, mix the EPICLONEXA-830CRP as aromatic glycidyl ether (A) of 100 mass parts, the conduct of 395 mass parts has the ARONE OXETANE OXT-221 of the oxetane compound (B) of the oxetanyl more than 2, the conduct of 5 mass parts contains the KBM-303 of the silane coupling agent (C) of ester ring type epoxy group(ing), the propylene glycol carbonate 50 quality % solution of the phenylbenzene-4-as cationic polymerization initiators (D) of 40 mass parts (thiophenyl) phenyl sulfonium hexafluorophosphate, 2.5 mass parts as 9 of photosensitizer (E), 10-dibutoxy anthracene, 2.5 mass parts as 1 of photosensitization auxiliary agent (F), 4-diethoxy naphtho-stirs, and prepare the cationically polymerizable tackiness agent that viscosity is 26mPas (25 ℃).
Usining separately the surface of polymethylmethacrylate as acrylic resin film and the TAC film of principal constituent, use the wire drawing rod to reach the about mode of the thickness of 2 μ m, to be coated with respectively the cationically polymerizable tackiness agent of gained, this coated substrate is fitted in respectively to the two sides of described polaroid (polarizing coating).Then, after using the rubber rollers pressurization, by using the UV irradiation equipment (Fusion LH-6 output rating 100%, line speed 17.8m/ minute) of conveyor-type, the accumulative total light quantity of irradiating 300～390nm from described acrylic resin film side is 1300mJ/cm 2Ultraviolet ray, and obtain having the polarization plates that rises from above as the structure of protective membrane/cationically polymerizable adhesive layer/polaroid/cationically polymerizable adhesive layer/protective membrane.
[comparative example 1]
by possessing stirrer, reflux cooler, thermometer, in the reaction vessel of dropping funnel and nitrogen inlet, mix the EPICLON EXA-830CRP as aromatic glycidyl ether (A) of 100 mass parts, the conduct of 400 mass parts has the ARONE OXETANE OXT-221 of the oxetane compound (B) of the oxetanyl more than 2, the propylene glycol carbonate 50 quality % solution of the phenylbenzene-4-as cationic polymerization initiators (D) of 40 mass parts (thiophenyl) phenyl sulfonium hexafluorophosphate, 2.5 mass parts as 9 of photosensitizer (E), 10-dibutoxy anthracene, 2.5 mass parts as 1 of photosensitization auxiliary agent (F), 4-diethoxy naphtho-stirs, and prepare the cationically polymerizable tackiness agent that viscosity is 26mPas (25 ℃).
Usining separately the surface of polymethylmethacrylate as acrylic resin film and the TAC film of principal constituent, use the wire drawing rod to reach the about mode of the thickness of 2 μ m, to be coated with respectively the cationically polymerizable tackiness agent of gained, this coated substrate is fitted in respectively to the two sides of described polaroid (polarizing coating).Then, after using the rubber rollers pressurization, by using the UV irradiation equipment (Fusion LH-6 output rating 100%, line speed 17.8m/ minute) of conveyor-type, the accumulative total light quantity of irradiating 300～390nm from described acrylic resin film side is 1300mJ/cm 2Ultraviolet ray, and obtain having the polarization plates that rises from above as the structure of protective membrane/cationically polymerizable adhesive layer/polaroid/cationically polymerizable adhesive layer/protective membrane.
[comparative example 2]
by possessing stirrer, reflux cooler, thermometer, in the reaction vessel of dropping funnel and nitrogen inlet, mix the EPICLONEXA-830CRP as aromatic glycidyl ether (A) of 100 mass parts, 397.5 the conduct of mass parts has the ARONE OXETANE OXT-221 of the oxetane compound (B) of the oxetanyl more than 2, 2.5 the conduct of mass parts contains the KBM-303 of the silane coupling agent (C) of ester ring type epoxy group(ing), the propylene glycol carbonate 50 quality % solution of the phenylbenzene-4-as cationic polymerization initiators (D) of 40 mass parts (thiophenyl) phenyl sulfonium hexafluorophosphate, 2.5 mass parts as 9 of photosensitizer (E), 10-dibutoxy anthracene, 2.5 mass parts as 1 of photosensitization auxiliary agent (F), 4-diethoxy naphtho-stirs, and prepare the cationically polymerizable tackiness agent that viscosity is 26mPas (25 ℃).
Usining separately the surface of polymethylmethacrylate as acrylic resin film and the TAC film of principal constituent, use the wire drawing rod to reach the about mode of the thickness of 2 μ m, to be coated with respectively the cationically polymerizable tackiness agent of gained, this coated substrate is fitted in respectively to the two sides of described polaroid (polarizing coating).Then, after using the rubber rollers pressurization, by using the UV irradiation equipment (Fusion LH-6 output rating 100%, line speed 17.8m/ minute) of conveyor-type, the accumulative total light quantity of irradiating 300～390nm from described acrylic resin film side is 1300mJ/cm 2Ultraviolet ray, and obtain having the polarization plates that rises from above as the structure of protective membrane/cationically polymerizable adhesive layer/polaroid/cationically polymerizable adhesive layer/protective membrane.
[comparative example 3]
by possessing stirrer, reflux cooler, thermometer, in the reaction vessel of dropping funnel and nitrogen inlet, mix the EPICLONEXA-830CRP as aromatic glycidyl ether (A) of 100 mass parts, the conduct of 250 mass parts has the ARONE OXETANE OXT-221 of the oxetane compound (B) of the oxetanyl more than 2, the conduct of 150 mass parts contains the KBM-303 of the silane coupling agent (C) of ester ring type epoxy group(ing), the propylene glycol carbonate 50 quality % solution of the phenylbenzene-4-as cationic polymerization initiators (D) of 40 mass parts (thiophenyl) phenyl sulfonium hexafluorophosphate, 2.5 mass parts as 9 of photosensitizer (E), 10-dibutoxy anthracene, 2.5 mass parts as 1 of photosensitization auxiliary agent (F), 4-diethoxy naphtho-stirs, and prepare the cationically polymerizable tackiness agent that viscosity is 24mPas (25 ℃).
Usining separately the surface of polymethylmethacrylate as acrylic resin film and the TAC film of principal constituent, use the wire drawing rod to reach the about mode of the thickness of 2 μ m, to be coated with respectively the cationically polymerizable tackiness agent of gained, this coated substrate is fitted in respectively to the two sides of described polaroid (polarizing coating).Then, after using the rubber rollers pressurization, by using the UV irradiation equipment (Fusion LH-6 output rating 100%, line speed 17.8m/ minute) of conveyor-type, the accumulative total light quantity of irradiating 300～390nm from described acrylic resin film side is 1300mJ/cm 2Ultraviolet ray, and obtain having the polarization plates that rises from above as the structure of protective membrane/cationically polymerizable adhesive layer/polaroid/cationically polymerizable adhesive layer/protective membrane.
[comparative example 4]
by possessing stirrer, reflux cooler, thermometer, in the reaction vessel of dropping funnel and nitrogen inlet, mix the EPICLONEXA-830CRP as aromatic glycidyl ether (A) of 100 mass parts, the conduct of 400 mass parts contains the KBM-303 of the silane coupling agent (C) of ester ring type epoxy group(ing), the propylene glycol carbonate 50 quality % solution of the phenylbenzene-4-as cationic polymerization initiators (D) of 40 mass parts (thiophenyl) phenyl sulfonium hexafluorophosphate, 2.5 mass parts as 9 of photosensitizer (E), 10-dibutoxy anthracene, 2.5 mass parts as 1 of photosensitization auxiliary agent (F), 4-diethoxy naphtho-stirs, and prepare the cationically polymerizable tackiness agent that viscosity is 24mPas (25 ℃).
Usining separately the surface of polymethylmethacrylate as acrylic resin film and the TAC film of principal constituent, use the wire drawing rod to reach the about mode of the thickness of 2 μ m, to be coated with respectively the cationically polymerizable tackiness agent of gained, this coated substrate is fitted in respectively to the two sides of described polaroid (polarizing coating).Then, after using the rubber rollers pressurization, by using the UV irradiation equipment (Fusion LH-6 output rating 100%, line speed 17.8m/ minute) of conveyor-type, the accumulative total light quantity of irradiating 300～390nm from described acrylic resin film side is 1300mJ/cm 2Ultraviolet ray, and obtain having the polarization plates that rises from above as the structure of protective membrane/cationically polymerizable adhesive layer/polaroid/cationically polymerizable adhesive layer/protective membrane.
[comparative example 5]
by possessing stirrer, reflux cooler, thermometer, the conduct that mixes 450 mass parts in the reaction vessel of dropping funnel and nitrogen inlet has the ARONE OXETANE OXT-221 of the oxetane compound (B) of the oxetanyl more than 2, the conduct of 50 mass parts contains the KBM-303 of the silane coupling agent (C) of ester ring type epoxy group(ing), the propylene glycol carbonate 50 quality % solution of the phenylbenzene-4-as cationic polymerization initiators (D) of 40 mass parts (thiophenyl) phenyl sulfonium hexafluorophosphate, 2.5 mass parts as 9 of photosensitizer (E), 10-dibutoxy anthracene, 2.5 mass parts as 1 of photosensitization auxiliary agent (F), 4-diethoxy naphtho-stirs, and prepare the cationically polymerizable tackiness agent that viscosity is 15mPas (25 ℃).
Usining separately the surface of polymethylmethacrylate as acrylic resin film and the TAC film of principal constituent, use the wire drawing rod to reach the about mode of the thickness of 2 μ m, to be coated with respectively the cationically polymerizable tackiness agent of gained, this coated substrate is fitted in respectively to the two sides of described polaroid (polarizing coating).Then, after using the rubber rollers pressurization, by using the UV irradiation equipment (Fusion LH-6 output rating 100%, line speed 17.8m/ minute) of conveyor-type, the accumulative total light quantity of irradiating 300～390nm from described acrylic resin film side is 1300mJ/cm 2Ultraviolet ray, and obtain having the polarization plates that rises from above as the structure of protective membrane/cationically polymerizable adhesive layer/polaroid/cationically polymerizable adhesive layer/protective membrane.
[evaluation method of cementability]
The polarization plates that obtains in embodiment and comparative example is cut out and cut the size into 3mm * 60mm, using the material of gained as test film, under 23 ℃, the condition of 50%RH, this test film is wound on the rod of diameter 3 Φ.Utilize the outward appearance of the moment on the Visual Confirmation volume, estimate as shown below.
Well " zero ": do not peel off, in adhesive layer, do not have crackle.
Bad " * ": peel off or in a part, crackle is arranged in adhesive layer.
[evaluation method of water tolerance]
The polarization plates that obtains in embodiment and comparative example is cut out and cut the size into 50mm * 50mm, using the material of gained as test film, this test film was flooded 24 hours in the warm water of 60 ℃, utilize Visual Confirmation outward appearance thereafter, estimate as shown below.
Well " zero ": in test film, do not have the iodine decolouring, peel off.
Bad " * ": in all or part of of test film, can confirm to have the iodine decolouring, maybe can confirm to peel off.
[table 1]
[table 1] Embodiment 1 Embodiment 2 Embodiment 3 Embodiment 4 Embodiment 5
Aromatic glycidyl ether (A) ? ? ? ? ?
EPICLON EXA-830CRP (mass parts) 100 100 100 100 100
Oxetane compound (B) with the oxetanyl more than 2 ? ? ? ? ?
ARONE OXETANE OXT-221 (mass parts) 300 350 375 390 395
The silane coupling agent (C) that contains the ester ring type epoxy group(ing) ? ? ? ? ?
KBM-303 (mass parts) 100 50 25 10 5
The evaluation of cementability ○ ○ ○ ○ ○
The evaluation of water tolerance ○ ○ ○ ○ ○
[table 2]
[table 2] Comparative example 1 Comparative example 2 Comparative example 3 Comparative example 4 Comparative example 5
Aromatic glycidyl ether (A) ? ? ? ? ?
EPICLON EXA-830CRP (mass parts) 100 100 100 100 0
Oxetane compound (B) with the oxetanyl more than 2 ? ? ? ? ?
ARONE OXETANE OXT-221 (mass parts) 400 3975 250 0 450
The silane coupling agent (C) that contains the ester ring type epoxy group(ing) ? ? ? ? ?
KBM-303 (mass parts) 0 25 150 400 50
The evaluation of cementability × × × × ×
The evaluation of water tolerance × ○ ○ × ×
Simple symbol in his-and-hers watches 1～2 etc. describes.
" EPICLON EXA-830CRP ": Bisphenol F diglycidylether
" ARONE OXETANE OXT-221 ": two [1-ethyl (3-oxetanyl)] methyl ether
" KBM-303 ": 2-(3,4-epoxy group(ing) cyclohexyl) the ethyl trimethoxy silane embodiment as cationically polymerizable tackiness agent of the present invention 1～5 as can be known has excellent cementability and water tolerance.
As can be known on the other hand, comparative example 1 is the mode that does not contain silane coupling agent (C), yet cementability and water tolerance are bad.
In addition we know, comparative example 2 and 3 is modes that the usage quantity of oxetane compound (B) and silane coupling agent (C) breaks away from the scope of stipulating in the present invention, yet cementability is all bad.
In addition we know, comparative example 4 is the modes that do not contain oxetane compound (B) and silane coupling agent (C), and comparative example 5 is the modes that do not contain aromatic glycidyl ether (A), yet cementability and water tolerance are bad.

Claims (9)

1. cationically polymerizable tackiness agent, it is characterized in that, contain aromatic glycidyl ether (A), have the oxetane compound (B) of the oxetanyl more than 2, the silane coupling agent (C) with ester ring type epoxy group(ing) and cationic polymerization initiators (D)
With respect to described aromatic glycidyl ether (A) 100 mass parts, in the scope of 300～395 mass parts, use described oxetane compound (B), in the scope of 5～100 mass parts, use described silane coupling agent (C).
2. cationically polymerizable tackiness agent according to claim 1, wherein,
Described aromatic glycidyl ether (A) has the glycidyl ether more than 2.
3. cationically polymerizable tackiness agent according to claim 2, wherein,
Described aromatic glycidyl ether (A) is the aromatic glycidyl ether more than a kind that selects in white bisphenol A diglycidyl ether and Bisphenol F diglycidylether.
4. cationically polymerizable tackiness agent according to claim 1, wherein,
The molecular weight of described oxetane compound (B) is 100～800 scope.
5. cationically polymerizable tackiness agent according to claim 4, wherein,
Described oxetane compound (B) is two [1-ethyl (3-oxetanyl)] methyl ethers.
6. cationically polymerizable tackiness agent according to claim 1, wherein,
Described silane coupling agent (C) be select in white 2-(3,4-epoxy group(ing) cyclohexyl) ethyl trimethoxy silane and 2-(3,4-epoxy group(ing) cyclohexyl) ethyl triethoxysilane more than a kind.
7. cationically polymerizable tackiness agent according to claim 1, wherein,
Also contain photosensitizer (E).
8. cationically polymerizable tackiness agent according to claim 7, wherein,
Described photosensitizer (E) is that light display more than 380nm illustrates very big absorption to wavelength.
9. a polarization plates, is characterized in that, its be by protective membrane and polaroid by the bonding polarization plates that forms of cationically polymerizable tackiness agent,
Described cationically polymerizable tackiness agent is the described cationically polymerizable tackiness agent of any one in claim 1～8.
CN201280010204.2A 2011-04-19 2012-02-20 Cationic polymerizable adhesive and polarizing plate obtained using same Expired - Fee Related CN103403120B (en)

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TWI821172B (en) 2017-02-13 2023-11-11 日商三菱化學股份有限公司 Adhesive composition for polarizing plates, adhesives for polarizing plates and polarizing plates utilizing the same
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