CN101824296A - Cation-polymerizable adhesive and polarizing plate using the same - Google Patents

Cation-polymerizable adhesive and polarizing plate using the same Download PDF

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Publication number
CN101824296A
CN101824296A CN201010127540A CN201010127540A CN101824296A CN 101824296 A CN101824296 A CN 101824296A CN 201010127540 A CN201010127540 A CN 201010127540A CN 201010127540 A CN201010127540 A CN 201010127540A CN 101824296 A CN101824296 A CN 101824296A
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Prior art keywords
tackiness agent
cationically polymerizable
compound
ethyl
cyclobutyl
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坂本高章
田中浩二郎
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DIC Corp
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Dainippon Ink and Chemicals Co Ltd
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Publication of CN101824296A publication Critical patent/CN101824296A/en
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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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • 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
    • 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
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
    • G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
    • G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
    • G02B5/3041—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid comprising multiple thin layers, e.g. multilayer stacks
    • G02B5/305—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid comprising multiple thin layers, e.g. multilayer stacks including organic materials, e.g. polymeric layers
    • 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
    • G02F1/133528—Polarisers

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Organic Chemistry (AREA)
  • Nonlinear Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Mathematical Physics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Polarising Elements (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Polyethers (AREA)

Abstract

The object of the present invention is to provide a cation-polymerizable adhesive which can maintain the excellent normal state adhesion strength and can not be affected by the heat and light, and to provide a polaroid sheet formed via adhering a polarizer and a protection film by the adhesive. The invention relates to the cation-polymerizable adhesive, charaterized in that, the adhesive contains heterocyclic butane compound (A) which has more than two oxygen heterocyclic butyls and molecular weights of 100 - 800, aromatic glycidyl ether (B) and cation-polymerizabl initiator (C), the chlorine remained in the total amount of the adhesive is below 1500 ppm. The invention also relates to the polaroid sheet formed via adhering the polarizer and the protection film by the adhesive.

Description

Cationically polymerizable tackiness agent and use the polaroid of its acquisition
Technical field
The present invention relates to a kind of cationically polymerizable tackiness agent, it can be used in for example with the various uses headed by the manufacturing of opticses such as polaroid.
Background technology
As the polaroid that is used for liquid-crystal display etc.; usually be known that following polaroid: on the polarizer that is made of the polyvinyl alcohol mesentery that is impregnated with dichroism materials such as iodine, lamination is the transparent protective membrane that resin etc. constitutes by triacetyl cellulose, thermoplasticity saturated norbornene.For the tackiness agent that is used for bonding described polarizer and described protective membrane; what industrial community required is; has the excellent normal state bond strength for described polarizer and these two adherends of protective membrane; and be not subjected to the light from Backlight For Liquid Crystal Display Panels etc., the influence of heat, can keep excellent normal state bond strength for a long time for polarizer and protective membrane.
On the other hand; as tackiness agent; in recent years; suppress and stop to supply with the cationically polymerizable tackiness agent that also can be cured reaction behind the ultraviolet homenergic to get most of the attention even curing that the oxygen in the atmosphere causes be difficult for to take place, also beginning one's study is applied to the bonding purposes of described polarizer and protective membrane.
For example; as the tackiness agent that is used for bonding described polarizer and protective membrane; be known that by being the tackiness agent that composition was constituted of main component with the Resins, epoxy that does not contain aromatic nucleus; particularly, be known that contain hydrogenated epoxy resin, alicyclic epoxy resin or aliphatic epoxy resin and light cationic polymerization initiators tackiness agent (for example with reference to patent documentation 1.)。
But; described tackiness agent does not reach the desired level of industrial community as yet for the normality bond strength of the polarizer that is formed by polyvinyl alcohol etc.; in addition; since from the normality bond strength that influence caused of the light of backlight etc., heat through the time reduce, exist in the situation that polarizer and protective membrane are peeled off took place in relatively shorter period.
Like this; along with showing the more competitively exploitation of the liquid-crystal display of image; also require very high-caliber various characteristics for the optics that constitutes it; wherein; can keep to be used for the cationically polymerizable tackiness agent of excellent normal state bond strength of the bonding purposes level of polarizer and protective membrane for a long time, in practical situation, also find.
The prior art document
Patent documentation
Patent documentation 1: TOHKEMY 2004-245925 communique
Summary of the invention
The problem that invention will solve
The problem to be solved in the present invention is; provide a kind of and be not heated, the influence of light etc. and can keep the cationically polymerizable tackiness agent of excellent normal state bond strength for a long time, and provide the polaroid that uses bonding polarizer of this tackiness agent and protective membrane to form.
The scheme that is used to deal with problems
The inventor etc. study known various cationically polymerizable combination of compounds such as hydroxy-containing compounds, oxygen heterocyclic ring butyl (oxetanyl) compound, alicyclic epoxy compounds in order to address the above problem.
Particularly, the tackiness agent that is combined by molecular weight ratio lower oxygen heterocyclic ring butylation compound, aromatic glycidyl ether and light cationic polymerization initiators is studied, described tackiness agent be difficult to fully to prevent the normality bond strength through the time reduce.
Therefore, the inventor etc. to the specific combination of above-mentioned cationically polymerizable compound and with the tackiness agent that is obtained in the various combinations of contained residual chlorine dose study, found that, in the tackiness agent that contains low-molecular-weight oxetane compound, aromatic glycidyl ether and cationic polymerization initiators, remaining chlorine is that the following tackiness agent of 1500ppm can solve problem of the present invention in the total amount of described tackiness agent.
Promptly; the present invention relates to a kind of cationically polymerizable tackiness agent and use its bonding polarizer and protective membrane and the polaroid that obtains; described cationically polymerizable tackiness agent is characterised in that; this tackiness agent contains oxetane compound (A), aromatic glycidyl ether (B) and the cationic polymerization initiators (C) with 2 above oxa-cyclobutyl and molecular weight 100～800, and remaining chlorine is below the 1500ppm in the total amount of described tackiness agent.
The effect of invention
Cationically polymerizable tackiness agent of the present invention because be not heated, the influence of light etc., and can long-term performance excellent normal state bond strength, therefore be suitable for towards the tackiness agent of optical materials such as polaroid, building materials, automobile internal and external ornamental part.In addition; cationically polymerizable tackiness agent of the present invention; because the polyvinyl alcohol film that uses in the material for common polarizer has good normality bond strength; therefore can be specifically designed to the manufacturing of polaroid; particularly, can perform well in constituting the bonding of the polarizer of polaroid and protective membrane.
Embodiment
Cationically polymerizable tackiness agent of the present invention is the tackiness agent that contains oxetane compound (A), aromatic glycidyl ether (B), cationic polymerization initiators (C) and other additive as required with 2 above oxa-cyclobutyl and molecular weight 100～800; remaining chlorine is below the 1500ppm in the total amount of described tackiness agent, can be specifically designed to the bonding of the polarizer that constitutes polaroid and protective membrane well.In addition, described molecular weight is represented to calculate and the value of trying to achieve based on formula weight.
As the oxetane compound that uses among the present invention (A), it is very important using the compound with molecular weight of 100～800.In order to be cured fully, the thickness with binder layer carries out the bonding of polarizer and protective membrane in the mode of film (a few μ m are thick) usually, and for the uniform film thickness ground of tackiness agent with described degree is coated with, tackiness agent is necessary for low viscosity.And,, must use the lower oxetane compound of described molecular weight ratio in order to obtain described low viscous tackiness agent.Using molecular weight for example is the tackiness agent that about 1500 oxetane compound replaces described oxetane compound (A) to obtain, because its viscosity ratio is higher, therefore be difficult to filming, may cause the reduction of the solidified nature of this binder layer, the reduction of bond strength.
From the coating operability of further raising cationically polymerizable tackiness agent of the present invention, the viewpoint of solidified nature, as described oxetane compound (A), more preferably use the compound of molecular weight, the preferred especially compound that uses molecular weight with 150～400 scopes with 100～500 scopes.
In addition, can give good solidified nature and normality bond strength aspect, as described oxetane compound (A), the preferred use has more than 2, is preferably 2～4 compounds that help the trimethylene oxide ring structure of cationoid polymerisation.
As the oxetane compound that uses among the present invention (A), particularly, may be used singly or in combination of two or more kinds the compound shown in for example following general formula (1), (2) etc.
[Chemical formula 1]
Figure GSA00000037401400041
[Chemical formula 2]
Figure GSA00000037401400042
R in above-mentioned general formula (1) and (2) 1Straight chain shape, chain or cyclic alkyl, allyl group, aryl, aralkyl, furyl or the thienyl of representing hydrogen atom, carbonatoms 1～6 respectively independently, R 2Organic residue of representing divalent respectively independently, Z are represented Sauerstoffatom or sulphur atom respectively independently.
As the R in described general formula (1) and (2) 1The straight chain shape of shown carbonatoms 1～6, chain or cyclic alkyl, for example be methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, the tertiary butyl, amyl group, hexyl, cyclohexyl etc., in addition, as aryl, for example be phenyl, naphthyl, tolyl, xylyl etc., in addition, as aralkyl, for example be benzyl, styroyl etc.
In addition, as the R in the described general formula (1) 2The organic residue of represented divalent for example has: straight chain shape, chain or cyclic alkylidene group have poly-(oxyalkylene) bases of 4～30 carbon atoms, the structure shown in phenylene, xylylene, following general formula (3) and (4).
Constitute the R in the described general formula (1) 2Straight chain shape, chain or cyclic alkylidene group, be preferably methylene radical, ethylidene, 1, the alkylidene group of carbonatomss 1～15 such as 2-or trimethylene, butylidene, cyclohexylidene.In addition, poly-(oxyalkylene) base with 4～30 carbon atoms preferably has 4～8 carbon atoms, for example is preferably poly-(oxygen ethene) base, poly-(oxypropylene) base.
[chemical formula 3]
Figure GSA00000037401400051
R in the described general formula (3) 3Expression Sauerstoffatom, sulphur atom, CH 2, NH, SO, SO 2, C (CF 3) 2Or C (CH 3) 2
[chemical formula 4]
Figure GSA00000037401400052
R in the described general formula (4) 4Expression have 1～6 carbon atom alkylidene group, arylidene, and following general formula (5) shown in functional group.
[chemical formula 5]
Figure GSA00000037401400061
A in the described general formula (5) 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, commercially available have for example ARON OXETANE OXT-221, ARON OXETANEOXT-121, ARON OXETANE OXT-223 (above Toagosei Co., Ltd system), an ETERNACOLL OXBP (above Ube Industries, Ltd system) etc.
As described oxetane compound (A), preferably use the compound shown in the described general formula (1), particularly use the R in the general formula (1) 1Be ethyl, R 2For two [1-ethyl (3-oxa-cyclobutyl)] methyl ethers of methylene radical can make the thickness attenuation of the tackiness agent after the curing, therefore solidified nature can be further improved, and the reduction of the bond strength that heat, light etc. cause can be prevented for a long time, therefore preferred.
In addition; among the present invention; except that described oxetane compound (A) with 2 above oxa-cyclobutyl; be used in combination oxetane compound (D) as required with 1 oxa-cyclobutyl; from guaranteeing that sufficient open assembly time is to paste polarizer and protective membrane and can prevent for a long time that it is preferred by pasting the viewpoint of peeling off that polaroid that they obtain causes owing to heat, light etc.The equivalent ratio of the oxa-cyclobutyl that oxa-cyclobutyl that preferred especially described oxetane compound (A) is had and described oxetane compound (D) are had [the oxa-cyclobutyl that (A) is had/(D) had oxa-cyclobutyl] is preferably 1～5 scope especially 0.1～35.0, more preferably use in the scope 0.2～10.0.
In addition, as described oxetane compound (D), can use the compound shown in for example following general formula (6) with 1 oxa-cyclobutyl.
[chemical formula 6]
Figure GSA00000037401400071
(the R in the general formula (6) 1Expression hydrogen atom, the alkyl of carbonatoms 1～8, the alkoxyalkyl of carbonatoms 1～5 or the hydroxyalkyl of carbonatoms 1～6.R 2Expression hydrogen atom, alkyl, aliphatics ring type structure, aromatic structure that can ramose carbonatoms 1～10.)
As the R that can constitute in the described general formula (6) 1The example of alkyl of carbonatoms 1～8, can enumerate methyl, ethyl, n-propyl, sec.-propyl and 2-ethylhexyl etc.
In addition, as the R that can constitute in the described general formula (6) 1The example of alkoxyalkyl of carbonatoms 1～5, can enumerate methoxymethyl, ethoxyl methyl, propoxy-methyl, methoxy ethyl, ethoxyethyl group, propoxy-ethyl etc.
In addition, as the R that can constitute in the described general formula (6) 1The example of hydroxyalkyl of carbonatoms 1～6, can enumerate methylol, hydroxyethyl and hydroxypropyl etc.
In addition, as the R that can constitute in the described general formula (6) 2Can ramose carbonatoms 1～10 alkyl, can enumerate ramose alkyl like that such as straight catenate alkyl such as methyl, ethyl, propyl group or 2-ethylhexyl.
In addition, as the R that can constitute in the described general formula (6) 2Aliphatics ring type structure, can enumerate for example cyclohexyl etc.Described cyclohexyl etc. also can have alkyl to be waited and replaces hydrogen atom.
In addition, as the R that can constitute in the described general formula (6) 2Aromatic structure, can enumerate for example phenyl etc.Described phenyl etc. also can have alkyl to be waited and replaces hydrogen atom.
As described oxetane compound (D), the preferred compound that uses, the preferred compound that uses with molecular weight of 150～500 with molecular weight of 100～500.
In addition, as described oxetane compound (D), more preferably use be selected from the group that 3-methylol-3-ethyl trimethylene oxide, 3-ethyl-3-(phenoxymethyl) trimethylene oxide, 3-ethyl-3-(2-ethyl hexyl oxy methyl) trimethylene oxide and 3-ethyl-3-(cyclohexyloxy) methyl trimethylene oxide formed more than a kind.
Among the present invention, with respect to the total amount of cationically polymerizable tackiness agent, described oxetane compound (A) reaches and (D) preferably uses in the scope of 20～70 quality %.In addition, owing to can improve solidified nature and prevent the reduction of the bond strength that heat, light etc. cause for a long time, therefore as described oxetane compound (A), with respect to described oxetane compound (A) and total metering (D), preferably use two [1-ethyl (3-oxa-cyclobutyl)] methyl ethers with 20～70 quality %; And,,, preferably be used in combination 3-methylol-3-ethyl trimethylene oxide with 20～70 quality % with respect to described oxetane compound (A) and total metering (D) as described oxetane compound (D).
Next, the aromatic glycidyl ether (B) that uses among the present invention is described.
Among the present invention, as can be by cationic polymerization initiators described later (C) open loop and form the compound of crosslinking structure, use aromatic glycidyl ether (B).
As described aromatic glycidyl ether (B), bisphenol A-type glycidyl ether, Bisphenol F type glycidyl ether, bisphenol S type glycidyl ether, dihydroxyphenyl propane D type glycidyl ether be can use, bisphenol A-type glycidyl ether, Bisphenol F type glycidyl ether wherein preferably used.
From the solidified nature of further raising cationically polymerizable tackiness agent of the present invention and prevent the viewpoint of the reduction of the bond strength that heat, light etc. cause for a long time, as described aromatic glycidyl ether (B), preferred bisphenol A-type glycidyl ether, the Bisphenol F type glycidyl ether of using wherein especially preferably uses bisphenol A diglycidyl ether, Bisphenol F diglycidylether.
From giving good normality bond strength viewpoint, as described aromatic glycidyl ether (B), the preferred compound with 2 above glycidyl ethers that uses more preferably uses the compound with 2～6 glycidyl ethers.
In addition, described aromatic glycidyl ether (B) can be made by making dihydroxyphenyl propane or reactions such as Bisphenol F and Epicholorohydrin, but may remnant in the aromatic glycidyl ether that is obtained comes from the chlorine of described Epicholorohydrin etc.In addition, in the commercially available usually compound that contains glycidyl ether, the chlorine about several %～tens % can residually be arranged also usually.
Therefore, from giving excellent normal state bond strength further and prevent the viewpoints such as variable color of polarizer, when making described aromatic glycidyl ether (B), preferably implement to remove the processing of dechlorination etc. by rectifying etc.Described rectifying is for example preferably being carried out about 1～200 hour under the temperature about 50～200 ℃.In addition, the amount of remaining chlorine in the above-mentioned aromatic glycidyl ether (B) can be measured according to JI SK 1200-3-2:00.
Described aromatic glycidyl ether (B) preferably contains 5～50 quality % in the total amount of cationically polymerizable tackiness agent of the present invention, keep for a long time the excellent normal state bond strength aspect, more preferably the scope at 10～40 quality % contains.
In addition, among the present invention, except that described aromatic glycidyl ether (B), can use other glycidyl ether as required.
As described other glycidyl ether, for example can use trihydroxymethylpropanyltri diglycidyl ether, T 55, the polyglycerol triglycidyl ether, two glycerol triglycidyl ether etc. have the aliphatic glycidyl based compound (a1) of 3 glycidyl ethers, or TriMethylolPropane(TMP) diglycidylether, 1, the 6-hexanediol diglycidyl ether, 1, the 4-butanediol diglycidyl ether, cyclohexanedimethanodiglycidyl diglycidyl ether, propylene glycol diglycidylether, Diethylene Glycol diglycidylether etc. has the glycidyl compound of 2 glycidyl ethers.
In addition, as described other glycidyl ether, also can use Hydrogenated Bisphenol A type glycidyl ether after described aromatic glycidyl ether (B) hydrogenation, A Hydrogenated Bisphenol A F type glycidyl ether, other aromatic glycidyl ether.
Next, the cationic polymerization initiators (C) that uses among the present invention is described.
The cationic polymerization initiators that uses among the present invention (C), for example be: can cause smooth cationic polymerization initiators cationoid polymerisation, acidic by irradiation ultraviolet radiation homenergic ray, can wait and acidic hot cationic polymerization initiators by heating.Wherein, with polarizer with protective membrane is bonding when making polaroid or when making other optical material, the viewpoint from the distortion of the base material that prevents to cause because of heat, variable color etc. preferably makes and uses the light cationic polymerization initiators.
As described smooth cationic polymerization initiators, for example may be used singly or in combination of two or more kinds cationic moiety is aromatic matte, aromatic series iodine, aromatic series diazonium, aromatic series ammonium, thianthrene (thianthrenium), thioxanthone (thioxanthonium), (2,4-cyclopentadiene-1-yl) [(1-methylethyl) benzene]-Fe positively charged ion, anionicsite is by BF 4 -, PF 6 -, SbF 6 -, [BX 4] -The salt that (wherein, X is by the phenyl of at least 2 above fluorine or trifluoromethyl replacement) constitutes.
As described aromatic series sulfonium salt, for example can use the two hexafluorophosphates of two [4-(phenylbenzene sulfonium) phenyl] thioethers, the two hexafluoro antimonates of two [4-(phenylbenzene sulfonium) phenyl] thioether, the two a tetrafluoro borates of two [4-(phenylbenzene sulfonium) phenyl] thioether, two [4-(phenylbenzene sulfonium) phenyl] thioether four (pentafluorophenyl group) borate, phenylbenzene-4-(phenyl sulphur) phenyl sulfonium hexafluorophosphate, phenylbenzene-4-(phenyl sulphur) phenyl sulfonium hexafluoro antimonate, phenylbenzene-4-(phenyl sulphur) phenyl sulfonium a tetrafluoro borate, phenylbenzene-4-(phenyl sulphur) 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) phenyl] thioether, the two hexafluoro antimonates of two [4-(two (4-(2-hydroxyl-oxethyl)) phenyl sulfonium) phenyl] thioether, the two a tetrafluoro borates of two [4-(two (4-(2-hydroxyl-oxethyl)) phenyl sulfonium) phenyl] thioether, two [4-(two (4-(2-hydroxyl-oxethyl)) phenyl sulfonium) phenyl] thioether four (pentafluorophenyl group) borate etc.
In addition, as 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, for example can use 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-cyanogen pyridine hexafluorophosphate, 1-benzyl-2-cyanogen pyridine hexafluoro antimonate, 1-benzyl-2-cyanogen pyridinium tetrafluoroborate salt, 1-benzyl-2-cyanogen pyridine four (pentafluorophenyl group) borate, 1-(naphthyl methyl)-2-cyanogen pyridine hexafluorophosphate, 1-(naphthyl methyl)-2-cyanogen pyridine hexafluoro antimonate, 1-(naphthyl methyl)-2-cyanogen pyridinium tetrafluoroborate salt, 1-(naphthyl methyl)-2-cyanogen pyridine four (pentafluorophenyl group) borate etc.
In addition, as described thioxanthone salt, can use S-xenyl 2-isopropyl thioxanthone hexafluorophosphate etc.
In addition, as 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.
As described smooth cationic polymerization initiators, commercially available have a for example CPI-100P, CPI-101A, CPI-200K (above San-Apro Ltd. system), Cyracure trigger for optical solidification UVI-6990, Cyracure trigger for optical solidification UVI-6992, Cyracure trigger for optical solidification UVI-6976 (above Dow Chemical Japan Ltd. system), Adeka Optomer SP-150, Adeka Optomer SP-152, Adeka OptomerSP-170, Adeka Optomer SP-172, Adeka Optomer SP-300 (above Asahi Denka Co., Ltd. system), CI-5102, CI-2855 (above Tso Tat Co., Ltd., Japan system), Sunaid SI-60L, Sunaid SI-80L, Sunaid SI-100L, SunaidSI-110L, Sunaid SI-180L, Sunaid SI-110, Sunaid SI-180 (above three new chemical industry Co., Ltd. systems), Esacure 1064, Esacure 1187 (above LAMBERTI corporate system), Omnicat 550 (IGM RESINS system), Irgacure250 (the different chemical of western Bart company limited system), RHODORSILPHOTOINITIATOR 2074 (Rhodia Japan Ltd. system) etc.
In addition, as described hot cationic polymerization initiators, for example can use benzyl sulfonium salt, thiophene salt, tetramethylene sulfide salt, benzyl ammonium salt, pyridinium salt, season hydrazonium salt, carboxylicesters, sulphonate, amine imide etc.
As described hot cationic polymerization initiators, can also use " AdekaoptonCP77 ", " Adekaopton CP66 " (above Asahi Denka Co., Ltd. system), " CI-2639 ", " CI-2624 " (above Tso Tat Co., Ltd., Japan system), " SunaidSI-60L ", " Sunaid SI-80L ", " Sunaid SI-100L " commercially available products such as (above three new chemical industry Co., Ltd. systems).
The consumption of described cationic polymerization initiators (C) is not particularly limited, but with respect to the total amount of described cationically polymerizable tackiness agent, expectation is preferably the scope of 0.1～20 quality %, the more preferably scope of 1～15 quality %.
In addition, in the cationically polymerizable tackiness agent of the present invention, except described oxetane compound (A), described aromatic glycidyl ether (B) and described cationic polymerization initiators (C), can be as required and with alicyclic epoxy compound (E), contain epoxy radicals silicone hydride compound (F) etc.
Aspect improving the bond strength at stickup initial stage, preventing the skew of base material, the preferred described alicyclic epoxy compound (E) that uses in the tackiness agent of the present invention.
As described alicyclic epoxy compound (E), can use compound with a plurality of, preferred 2～4 ester ring type epoxy group(ing).
In the described alicyclic epoxy compound (E), as alicyclic epoxy compound with 2 ester ring type epoxy group(ing), for example can use 3 shown in the following general formula (7), 4-oxirane ring hexenyl methyl-3, (a is 0 compound to the 4-epoxycyclohexane carboxylate in the general formula (7).), (a is 1 compound to its caprolactone modification thing in the general formula (7).), the compound shown in its trimethylammonium caprolactone modification thing (structural formula (8) and structural formula (9)) and valerolactone modifier (structural formula (10) and structural formula (11)) and the structural formula (12).
[chemical formula 7]
Figure GSA00000037401400131
(a in the general formula (7) represents 0 or 1.)
[chemical formula 8]
[chemical formula 9]
Figure GSA00000037401400133
[Chemical formula 1 0]
Figure GSA00000037401400141
[Chemical formula 1 1]
Figure GSA00000037401400142
[Chemical formula 1 2]
Figure GSA00000037401400143
In addition, as the alicyclic epoxy compound of the adipic acid ester shown in the described general formula (12) system, commercially available for example have a Cyracure UVR-6128 (above DowChemical Japan Ltd. system) etc.
In addition, in the described alicyclic epoxy compound (E),, also can use the compound shown in the following general formula (13) as alicyclic epoxy compound with 2 ester ring type epoxy group(ing).
[Chemical formula 1 3]
Figure GSA00000037401400144
(in the general formula (13), R 1～R 6The alkyl of representing hydrogen atom or carbonatoms 1～6 respectively independently.)
Compound as shown in the described general formula (13) particularly, can use dicyclohexyl-3,3 '-diepoxide.
As alicyclic epoxy compound, can use the compound shown in the following general formula (14) with 3 ester ring type epoxy group(ing).
[Chemical formula 1 4]
Figure GSA00000037401400151
In the general formula (14), a and b are 0 or 1 respectively independently, and they can be the same or different.
As the alicyclic epoxy compound shown in the general formula (14), commercially available have for example Epolead GT301, an Epolead GT302 (above Daicel Chemical Industries, Ltd. system) etc.
As alicyclic epoxy compound, for example can use the compound shown in the following general formula (15) with 4 ester ring type epoxy group(ing).
[Chemical formula 1 5]
Figure GSA00000037401400152
In the described general formula (15), a～d represents 0 or 1 respectively independently, and they can be the same or different.
As the alicyclic epoxy compound shown in the described general formula (15), for example commercially available have Epolead GT401, an Epolead GT403 (above Daicel ChemicalIndustries, Ltd. system) etc.
Described alicyclic epoxy compound (E), total amount with respect to cationically polymerizable tackiness agent of the present invention, preferably in the scope of 1～20 quality %, use, aspect improving the bond strength at stickup initial stage, preventing the skew of base material, preferably in the scope of 2～10 quality %, use.
In addition, the described epoxy radicals silicone hydride compound (F) that contains owing to can further improve the normality bond strength of gained tackiness agent, and especially can prevent the variable color etc. of polarizer, therefore preferably uses in the tackiness agent of the present invention.Vinyl silanes such as aminosilane, vinyltriacetoxy silane such as use 3-aminopropyltriethoxywerene werene wait when replacing described compound (F), compare with the situation of using described compound (F), prevent that from there is the tendency that reduces slightly in the effect of polarizer variable color.
As the described epoxy radicals silicone hydride compound (F) that contains, for example preferably use the 3-glycidoxypropyltrimewasxysilane, 3-glycidoxypropyl triethoxyl silane, 3-glycidoxypropyl methyldiethoxysilane, 3-glycidoxypropyl methyl dimethoxysilane, 2-(3, the 4-epoxycyclohexyl) ethyl trimethoxy silane, 2-(3, the 4-epoxycyclohexyl) ethyl triethoxysilane etc., wherein can give more excellent normal state bond strength, and prevent aspects such as fading of polarizer, the preferred use is selected from by 3-glycidoxypropyl triethoxyl silane, the 3-glycidoxypropyltrimewasxysilane, 2-(3, the 4-epoxycyclohexyl) in the group formed of ethyl trimethoxy silane and 2-(3, the 4-epoxycyclohexyl) ethyl triethoxysilane more than a kind.
In addition, as the described epoxy radicals silicone hydride compound (F) that contains, can use the silicone oil shown in following general formula (16) and (17).
[Chemical formula 1 6]
(n in the above-mentioned general formula (16) represents the integer more than 1.)
[Chemical formula 1 7]
Figure GSA00000037401400172
(R in the above-mentioned general formula (16) represents organic group, and n represents the integer more than 1.)
In the reduction of the bond strength that can not take place to cause and prevent aspects such as fading of polarizer because of influences such as heat, with respect to the total amount of cationically polymerizable tackiness agent of the present invention, described to contain that epoxy radicals silicone hydride compound (F) uses in the scope of 0.1～1.5 quality % be preferred.
From giving more excellent heat-resisting bond strength and preventing the viewpoints such as variable color of polarizer etc., for the cationically polymerizable tackiness agent that uses among the present invention, the amount that makes chlorine remaining in the total amount of this cationically polymerizable tackiness agent is to be very preferred below the 1500ppm.When described chlorine dose surpasses 1500ppm, may cause the variable color of binder layer and gained polarizer, the reduction of bond strength.
Wherein, said chlorine is meant among the present invention, derive from chlorine, the muriate of the raw materials such as Epicholorohydrin that use in the manufacturing of described aromatic glycidyl ether (B) and derive from can with the butters such as for example sodium-chlor of the various additives of tackiness agent of the present invention and usefulness.
With respect to the total amount of cationically polymerizable tackiness agent, the amount of described chlorine is below the 1500ppm, is preferably below the 1000ppm, more preferably below the 800ppm, can take into account fading of polarizer etc. etc. and secular normality bond strength thus.In addition, the amount of remaining chlorine can be measured according to JISK 1200-3-2:00 in the total amount of cationically polymerizable tackiness agent of the present invention.
Particularly for the variable color that further prevents described polarizer etc., preferably use described contain epoxy radicals silicone hydride compound (F) in, chlorine dose remaining in the cationically polymerizable tackiness agent is adjusted to below the 1500ppm.
As the method that remaining chlorine dose in the cationically polymerizable tackiness agent of the present invention is adjusted to below the 1500ppm, for example can enumerate by and the method for chlorine being removed with rectifying and the trapping agent that can catch described chlorine etc.Described rectifying is for example preferably being carried out about 1～200 hour under the temperature about 50～200 ℃.
Cationically polymerizable tackiness agent of the present invention can be made by for example following method.
Cationically polymerizable tackiness agent of the present invention for example can be as the manufacturing of getting off: use hermetic type planetary stirring machine etc., with the described oxetane compound (A) that makes in advance, described aromatic glycidyl ether (B), described cationic polymerization initiators (C) and as required described have the oxetane compound (D), described alicyclic epoxy compound (E) of 1 oxa-cyclobutyl, the described epoxy radicals silicone hydride compound (F) that contains mixes and stirs.When using described oxetane compound (D), also can be in advance with described oxetane compound (A) and (D) mixing back use.
Cationically polymerizable tackiness agent by described method obtains from reducing the viewpoint of the thickness of formed bonding coat as far as possible, is preferably the following viscosity of 25 ℃ of following 100mPas.This viscosity is mainly by using thinner such as oxetane compound, alicyclic ring epoxy compound or using lower molecular weight and adjust for aqueous described aromatic glycidyl ether (B) waits.
Cationically polymerizable tackiness agent of the present invention can contain various additives in the scope of not damaging effect of the present invention as required.
As described additive, for example can and use thixotropic agent, sensitizing agent, described various polyvalent alcohol and other polyvalent alcohol in addition thereof, flow agent, antioxidant, tackifier, wax, thermo-stabilizer, fast light stablizer, white dyes, whipping agent, thermoplastic resin, heat-curing resin, organic solvent, the electroconductibility imparting agent, static inhibitor, the water vapour permeability rising agent, water-resisting agent, the hollow foam, contain the crystal water compound, fire retardant, water-retaining agent, moisture adsorbent, reodorant, suds-stabilizing agent, defoamer, mould inhibitor, sanitas, anti-algae agent, caking inhibiter, hydrolysis-resisting agent, organic and inorganic water-soluble compound etc.
As described thixotropic agent, can use for example surface treatment lime carbonate, micropowder silica, wilkinite, zeolite etc.
When using described various additive, for example using hermetic type planetary stirring machine etc. that described oxetane compound (A), described aromatic glycidyl ether (B), described cationic polymerization initiators (C) and described alicyclic epoxy compound (E) as required, the described epoxy radicals silicone hydride compound (F) that contains are mixed, when stirring, can in the lump described additive be mixed.
Cationically polymerizable tackiness agent of the present invention can be cured by irradiation ultraviolet radiation homenergic ray.
The irradiation of described ultraviolet homenergic ray is preferably 50～5000mJ/cm 2, 100～3000mJ/cm more preferably 2, be preferably 300～1500mJ/cm especially 2Scope.
As ultraviolet generation source, for example can use known lamps such as xenon lamp, xenon-mercury lamp, metal halide lamp, high voltage mercury lamp, low pressure mercury lamp.In addition, ultraviolet irradiation amount is benchmark with the value of using UV detector UVR-N1 (Nippon Storage Battery Co., Ltd's system) to record under the wavelength region may of 300～390nm.
In addition, shine described energy-ray after, as required, can further promote to solidify by heating under about 40～80 ℃.
Then, polaroid of the present invention is described.
Polaroid of the present invention forms by bonding protective membrane of bonding coat and the polarizer that is formed by described cationically polymerizable tackiness agent.
As the protective membrane that can use in the manufacturing of described polaroid; from improving viewpoints such as polarized light property, weather resistance; can use the film or the flap that form by cellulose-based resins such as triacetyl cellulose, resin, norbornene resin etc., wherein preferably use cellulose-based resins such as triacetyl cellulose with cycloolefin structure.
As described celluosic resin, for example can use rhodia, cellulose acetate propionate, cellulose acetate butyrate, acetate propionic acid cellulose butyrate, Cellacefate and nitrocellulose etc., they may be used singly or in combination of two or more kinds, wherein, therefore preferably use rhodia owing to using rhodia can obtain mechanical properties and the excellent film of the transparency.
In addition, be not particularly limited as described polarizer, can use various polarizers, for example can use: the polarizer that dichroism materials such as being divided plastic basis material absorption iodine that hydrophilic macromolecular compounds such as saponified forms or dichroic dye by polyvinyl alcohol, part formalizing polyvinyl alcohol, ethylene/vinyl acetate multipolymer pastern and uniaxial extension are formed, polyenoid such as the desalination acid treatment thing of the processed thing of polyvinyl alcohol, polychlorostyrene ethene are alignment films etc.Wherein, preferably use polyvinyl alcohol mesentery and be adsorbed with the film of dichroism material such as iodine.
The thickness of the described protective membrane that uses when making polaroid of the present invention is according to the purposes of its use and difference probably is the scope of 20 μ m～100 μ m preferably.In addition, the thickness of described polarizer usually, probably is the scope of 5 μ m～50 μ m preferably.
In addition; polaroid of the present invention can be as the manufacturing of getting off: as described in cationically polymerizable tackiness agent as described in the coating on the protective membrane, then, this coated face is shone the ultraviolet ray of described amount after; on this coated face, place polarizer and bonding, thereby make polaroid of the present invention.At this moment, the thickness of the bonding coat that constitutes by described cationically polymerizable tackiness agent, preferably thin as much as possible for not damaging reason such as optical characteristics, particularly be preferably below the 5 μ m.
By the polaroid of the present invention that above method obtains, for example can be used to constitute the parts of the indicating meter of mobile communication terminal, LCD TV, computer, portable game machine etc. such as mobile telephone.
[embodiment]
Below, by embodiment and comparative example the present invention is carried out more specific description.
[modulation example 1]
The cl content that to try to achieve according to JISK 1200-3-2:00 is that the isomer mixture (B '-6) of 3.5% Bisphenol F type 2-glycidyl ether compound distills under the condition of 1.3kPa and 185 ℃, then carry out rectifying under the condition of 0.02MPa and 70 ℃, obtaining cl content thus is the compound that contains glycidyl ether (B-1) of 600ppm.In addition, as contained cl content in the described compound (B-1) that contains glycidyl ether, for the compound of counting with sodium-chlor more than 0.05%, use the value of trying to achieve by Fu Erhade (Volhard) improved method, for in sodium-chlor less than 0.05% compound, use the value of trying to achieve by the ion chromatography method.In addition, the cl content of the compound that contains glycidyl ether (B-2) of record, (B '-3) and (B '-4) in the following modulation example 2～3 is also by measuring with above-mentioned same method.
[modulation example 2]
The cl content that to try to achieve according to JISK 1200-3-2 is that the isomer mixture of 3.5% bisphenol A-type diglycidylether distills under the condition of 1.3kPa and 185 ℃, then carry out rectifying under the condition of 0.02MPa and 70 ℃, obtaining cl content thus is the compound that contains glycidyl ether (B-2) of 600ppm.
[modulation example 3]
To be 6.5% cyclohexanedimethanodiglycidyl diglycidyl ether distill under the condition of 1.3kPa and 185 ℃ the cl content that will try to achieve according to JISK 1200-3-2, then carry out rectifying one by one under the condition of 0.02MPa and 70 ℃, obtaining cl content thus is the compound that contains glycidyl ether (B '-3) of 500ppm, the compound that contains glycidyl ether (B '-4) that cl content is 1000ppm, the compound that contains glycidyl ether (B '-5) that cl content is 10000ppm.
[embodiment 1]
In the hermetic type planetary stirring machine, 20.0 mass parts are contained the compound (B-1) of glycidyl ether and the compound that 20.0 mass parts contain glycidyl ether (B '-4), 35.0 mass parts ARON OXETANE OXT-221 (two [1-ethyl (3-oxa-cyclobutyl)] methyl ethers of Toagosei Co., Ltd's system) and 25.0 mass parts ARONOXETANE OXT-101 (the 3-methylol of Toagosei Co., Ltd's system-3-ethyl trimethylene oxide) and 4 mass parts are mixed and stirring as the CPI-100P (50 quality % carbonic allyl ester solutions of the phenylbenzene-4-of San-Apro Ltd. system (phenyl sulphur) phenyl sulfonium hexafluorophosphate) of light cationic polymerization initiators (C), modulate cationically polymerizable tackiness agent (1) thus.Obtain contained cl content in the total amount of resulting cationically polymerizable tackiness agent (1) by the aftermentioned method, it is 247ppm.
[embodiment 2]
In the hermetic type planetary stirring machine, 20.0 mass parts are contained the compound (B-1) of glycidyl ether and the compound that 20.0 mass parts contain glycidyl ether (B '-3), 35.0 mass parts ARON OXETANE OXT-221 (two [1-ethyl (3-oxa-cyclobutyl)] methyl ethers of Toagosei Co., Ltd's system) and 25.0 mass parts ARONOXETANE OXT-101 (the 3-methylol of Toagosei Co., Ltd's system-3-ethyl trimethylene oxide) and 4 mass parts are mixed and stirring as the CPI-100P (50 quality % carbonic allyl ester solutions of the phenylbenzene-4-of San-Apro Ltd. system (phenyl sulphur) phenyl sulfonium hexafluorophosphate) of light cationic polymerization initiators (C), modulate cationically polymerizable tackiness agent (2) thus.Obtain contained cl content in the total amount of resulting cationically polymerizable tackiness agent (2) according to the aftermentioned method, it is 219ppm.
[embodiment 3]
In the hermetic type planetary stirring machine, 20.0 mass parts are contained the compound (B-2) of glycidyl ether and the compound that 20.0 mass parts contain glycidyl ether (B '-3), 35.0 mass parts ARON OXETANE OXT-221 (two [1-ethyl (3-oxa-cyclobutyl)] methyl ethers of Toagosei Co., Ltd's system) and 25.0 mass parts ARONOXETANE OXT-101 (the 3-methylol of Toagosei Co., Ltd's system-3-ethyl trimethylene oxide) and 4 mass parts are mixed and stirring as the CPI-100P (50 quality % carbonic allyl ester solutions of the phenylbenzene-4-of San-Apro Ltd. system (phenyl sulphur) phenyl sulfonium hexafluorophosphate) of light cationic polymerization initiators (C), modulate cationically polymerizable tackiness agent (3) thus.Obtain contained cl content in the total amount of resulting cationically polymerizable tackiness agent (3) by the aftermentioned method, it is 211ppm.
[embodiment 4]
In the hermetic type planetary stirring machine, 20.0 mass parts are contained the compound (B-1) of glycidyl ether and the compound that 20.0 mass parts contain glycidyl ether (B '-3), 35.0 mass parts ARON OXETANE OXT-221 (two [1-ethyl (3-oxa-cyclobutyl)] methyl ethers of Toagosei Co., Ltd's system) and 25.0 mass parts ARONOXETANE OXT-101 (the 3-methylol of Toagosei Co., Ltd's system-3-ethyl trimethylene oxide), 0.5 mass parts is mixed and is stirred as containing the KBE-403 (the 3-glycidoxypropyl triethoxyl silane of Shin-Etsu Chemial Co., Ltd's system) of epoxy radicals silicone hydride compound (F) and the 4 mass parts CPI-100P (50 quality % carbonic allyl ester solutions of the phenylbenzene-4-of San-Apro Ltd. system (phenyl sulphur) phenyl sulfonium hexafluorophosphate) as light cationic polymerization initiators (C), modulates cationically polymerizable tackiness agent (4) thus.Obtain contained cl content in the total amount of resulting cationically polymerizable tackiness agent (4) by the aftermentioned method, it is 218ppm.
[embodiment 5]
In the hermetic type planetary stirring machine, 20.0 mass parts are contained the compound (B-1) of glycidyl ether and the compound that 20.0 mass parts contain glycidyl ether (B '-3), 25.0 mass parts ARON OXETANE OXT-221 (two [1-ethyl (3-oxa-cyclobutyl)] methyl ethers of Toagosei Co., Ltd's system) and 30.0 mass parts ARONOXETANE OXT-101 (the 3-methylol of Toagosei Co., Ltd's system-3-ethyl trimethylene oxide), 5.0 mass parts is as CELLOXIDE 2021P (the Daicel Chemical Industries of alicyclic epoxy compound (E), Ltd. the system 3,4-oxirane ring hexenyl methyl-3 ', 4 '-oxirane ring hexene carboxylicesters) and 4 mass parts mix as the CPI-100P (50 quality % carbonic allyl ester solutions of the phenylbenzene-4-of San-Apro Ltd. system (phenyl sulphur) phenyl sulfonium hexafluorophosphate) of light cationic polymerization initiators (C) and stir, modulate cationically polymerizable tackiness agent (5) thus.Obtain contained cl content in the total amount of resulting cationically polymerizable tackiness agent (5) by the aftermentioned method, it is 209ppm.
[embodiment 6]
In the hermetic type planetary stirring machine, 20.0 mass parts are contained the compound (B-1) of glycidyl ether and the compound that 20.0 mass parts contain glycidyl ether (B '-3), 45.0 mass parts ARON OXETANE OXT-221 (two [1-ethyl (3-oxa-cyclobutyl)] methyl ethers of Toagosei Co., Ltd's system) and 15.0 mass parts ARONOXETANE OXT-211 (3-ethyl-3-(phenoxymethyl) trimethylene oxide of Toagosei Co., Ltd's system) and 4 mass parts are mixed and stirring as the CPI-100P (50 quality % carbonic allyl ester solutions of the phenylbenzene-4-of San-Apro Ltd. system (phenyl sulphur) phenyl sulfonium hexafluorophosphate) of light cationic polymerization initiators (C), modulate cationically polymerizable tackiness agent (6) thus.Obtain contained cl content in the total amount of resulting cationically polymerizable tackiness agent (6) by the aftermentioned method, it is 212ppm.
[embodiment 7]
In the hermetic type planetary stirring machine, 20.0 mass parts are contained the compound (B-1) of glycidyl ether and the compound that 20.0 mass parts contain glycidyl ether (B '-3), 35.0 mass parts ARON OXETANE OXT-221 (two [1-ethyl (3-oxa-cyclobutyl)] methyl ethers of Toagosei Co., Ltd's system) and 25.0 mass parts ARONOXETANE OXT-211 (3-ethyl-3-(phenoxymethyl) trimethylene oxide of Toagosei Co., Ltd's system) and 4 mass parts are mixed and stirring as the CPI-100P (50 quality % carbonic allyl ester solutions of the phenylbenzene-4-of San-Apro Ltd. system (phenyl sulphur) phenyl sulfonium hexafluorophosphate) of light cationic polymerization initiators (C), modulate cationically polymerizable tackiness agent (7) thus.Obtain contained cl content in the total amount of resulting cationically polymerizable tackiness agent (7) by the aftermentioned method, it is 214ppm.
[embodiment 8]
In the hermetic type planetary stirring machine, 20.0 mass parts are contained the compound (B-1) of glycidyl ether and the compound that 20.0 mass parts contain glycidyl ether (B '-3), 35.0 mass parts ARON OXETANE OXT-221 (two [1-ethyl (3-oxa-cyclobutyl)] methyl ethers of Toagosei Co., Ltd's system) and 25.0 mass parts ARONOXETANE OXT-212 (the 3-ethyl-3-of Toagosei Co., Ltd's system (2-ethyl hexyl oxy methyl) trimethylene oxide) and 4 mass parts are mixed and stirring as the CPI-100P (50 quality % carbonic allyl ester solutions of the phenylbenzene-4-of San-Apro Ltd. system (phenyl sulphur) phenyl sulfonium hexafluorophosphate) of light cationic polymerization initiators (C), modulate cationically polymerizable tackiness agent (8) thus.Obtain contained cl content in the total amount of resulting cationically polymerizable tackiness agent (8) by the aftermentioned method, it is 208ppm.
[embodiment 9]
In the hermetic type planetary stirring machine, 20.0 mass parts are contained the compound (B-1) of glycidyl ether and the compound that 20.0 mass parts contain glycidyl ether (B '-3), 35.0 mass parts ARON OXETANE OXT-221 (two [1-ethyl (3-oxa-cyclobutyl)] methyl ethers of Toagosei Co., Ltd's system) and 25.0 mass parts ARONOXETANE OXT-213 (3-ethyl-3-(cyclohexyloxy) methyl trimethylene oxide of Toagosei Co., Ltd's system) and 4 mass parts are mixed and stirring as the CPI-100P (50 quality % carbonic allyl ester solutions of the phenylbenzene-4-of San-Apro Ltd. system (phenyl sulphur) phenyl sulfonium hexafluorophosphate) of light cationic polymerization initiators (C), modulate cationically polymerizable tackiness agent (9) thus.Obtain contained cl content in the total amount of resulting cationically polymerizable tackiness agent (9) by the aftermentioned method, it is 215ppm.
[embodiment 10]
In the hermetic type planetary stirring machine, 20.0 mass parts are contained the compound (B-1) of glycidyl ether and the compound that 20.0 mass parts contain glycidyl ether (B '-3), 25.0 mass parts ARON OXETANE OXT-221 (two [1-ethyl (3-oxa-cyclobutyl)] methyl ethers of Toagosei Co., Ltd's system) and 30.0 mass parts ARONOXETANE OXT-211 (3-ethyl-3-(phenoxymethyl) trimethylene oxide of Toagosei Co., Ltd's system), 5.0 mass parts is as CELLOXIDE 2021P (the Daicel Chemical Industries of alicyclic epoxy compound (E), Ltd. the system 3,4-oxirane ring hexenyl methyl-3 ', 4 '-oxirane ring hexene carboxylicesters), 0.5 mass parts is mixed and is stirred as containing the KBE-403 (the 3-glycidoxypropyl triethoxyl silane of Shin-Etsu Chemial Co., Ltd's system) of epoxy radicals silicone hydride compound (F) and the 4 mass parts CPI-100P (50 quality % carbonic allyl ester solutions of the phenylbenzene-4-of San-Apro Ltd. system (phenyl sulphur) phenyl sulfonium hexafluorophosphate) as light cationic polymerization initiators (C), modulates cationically polymerizable tackiness agent (10) thus.Obtain contained cl content in the total amount of resulting cationically polymerizable tackiness agent (10) by the aftermentioned method, it is 216ppm.
[embodiment 11]
In the hermetic type planetary stirring machine, 20.0 mass parts are contained the compound (B-1) of glycidyl ether and the compound that 20.0 mass parts contain glycidyl ether (B '-3), 35.0 mass parts ARON OXETANE OXT-221 (two [1-ethyl (3-oxa-cyclobutyl)] methyl ethers of Toagosei Co., Ltd's system) and 25.0 mass parts ARONOXETANE OXT-211 (3-ethyl-3-(phenoxymethyl) trimethylene oxide of Toagosei Co., Ltd's system), 5.0 mass parts is as CELLOXIDE 2021P (the Daicel Chemical Industries of alicyclic epoxy compound (E), Ltd. the system 3,4-oxirane ring hexenyl methyl-3 ', 4 '-oxirane ring hexene carboxylicesters), 0.5 mass parts is mixed and is stirred as containing the KBE-403 (the 3-glycidoxypropyl triethoxyl silane of Shin-Etsu Chemial Co., Ltd's system) of epoxy radicals silicone hydride compound (F) and the 4 mass parts CPI-100P (50 quality % carbonic allyl ester solutions of the phenylbenzene-4-of San-Apro Ltd. system (phenyl sulphur) phenyl sulfonium hexafluorophosphate) as light cationic polymerization initiators (C), modulates cationically polymerizable tackiness agent (11) thus.Obtain contained cl content in the total amount of resulting cationically polymerizable tackiness agent (11) by the aftermentioned method, it is 216ppm.
[comparative example 1]
In the hermetic type planetary stirring machine, the compound (B '-3) that 40.0 mass parts is contained glycidyl ether, 35.0 mass parts ARON OXETANE OXT-221 (two [1-ethyl (3-oxa-cyclobutyl)] methyl ethers of Toagosei Co., Ltd's system) and 25.0 mass parts ARON OXETANE OXT-101 (the 3-methylol of Toagosei Co., Ltd's system-3-ethyl trimethylene oxide) and 4 mass parts are mixed and stirring as the CPI-100P (50 quality % carbonic allyl ester solutions of the phenylbenzene-4-of San-Apro Ltd. system (phenyl sulphur) phenyl sulfonium hexafluorophosphate) of light cationic polymerization initiators (C), modulate cationically polymerizable tackiness agent (1 ') thus.Obtain cl content contained in the total amount of resulting cationically polymerizable tackiness agent (1 ') by the aftermentioned method, it is 194ppm.
[comparative example 2]
In the hermetic type planetary stirring machine, the compound (B '-4) that 40.0 mass parts is contained glycidyl ether, 35.0 mass parts ARON OXETANE OXT-221 (two [1-ethyl (3-oxa-cyclobutyl)] methyl ethers of Toagosei Co., Ltd's system) and 25.0 mass parts ARON OXETANE OXT-101 (the 3-methylol of Toagosei Co., Ltd's system-3-ethyl trimethylene oxide) and 4 mass parts are mixed and stirring as the CPI-100P (50 quality % carbonic allyl ester solutions of the phenylbenzene-4-of San-Apro Ltd. system (phenyl sulphur) phenyl sulfonium hexafluorophosphate) of light cationic polymerization initiators (C), modulate cationically polymerizable tackiness agent (2 ') thus.Obtain cl content contained in the total amount of resulting cationically polymerizable tackiness agent (2 ') by the aftermentioned method, it is 383ppm.
[comparative example 3]
In the hermetic type planetary stirring machine, 20.0 mass parts are contained the compound (B '-3) of glycidyl ether and the compound (B-1) that 20.0 mass parts contain glycidyl ether, 35.0 mass parts ARON OXETANE OXT-191 (the oxa-cyclobutyl silicate of Toagosei Co., Ltd's system) and 25.0 mass parts ARON OXETANE OXT-101 (the 3-methylol of Toagosei Co., Ltd's system-3-ethyl trimethylene oxide) and 4 mass parts are mixed and stirring as the CPI-100P (50 quality % carbonic allyl ester solutions of the phenylbenzene-4-of San-Apro Ltd. system (phenyl sulphur) phenyl sulfonium hexafluorophosphate) of light cationic polymerization initiators (C), modulate cationically polymerizable tackiness agent (3 ') thus.Obtain cl content contained in the total amount of resulting cationically polymerizable tackiness agent (3 ') by the aftermentioned method, it is 211ppm.
[comparative example 4]
In the hermetic type planetary stirring machine, 20.0 mass parts are contained the compound (B '-3) of glycidyl ether and the compound (B-2) that 20.0 mass parts contain glycidyl ether, 35.0 mass parts ARON OXETANE OXT-191 (the oxa-cyclobutyl silicate of Toagosei Co., Ltd's system), 25.0 mass parts ARON OXETANE OXT-101 (the 3-methylol of Toagosei Co., Ltd's system-3-ethyl trimethylene oxide) and 4 mass parts are mixed and stirring as the CPI-100P (50 quality % carbonic allyl ester solutions of the phenylbenzene-4-of San-Apro Ltd. system (phenyl sulphur) phenyl sulfonium hexafluorophosphate) of light cationic polymerization initiators (C), modulate cationically polymerizable tackiness agent (4 ') thus.Obtain cl content contained in the total amount of resulting cationically polymerizable tackiness agent (4 ') by the aftermentioned method, it is 213ppm.
[comparative example 5]
In the hermetic type planetary stirring machine, 20.0 mass parts are contained the compound (B-1) of glycidyl ether and the compound that 20.0 mass parts contain glycidyl ether (B '-5), 35.0 mass parts ARON OXETANE OXT-221 (two [1-ethyl (3-oxa-cyclobutyl)] methyl ethers of Toagosei Co., Ltd's system) and 25.0 mass parts ARONOXETANE OXT-101 (the 3-methylol of Toagosei Co., Ltd's system-3-ethyl trimethylene oxide) and 4 mass parts are mixed and stirring as the CPI-100P (50 quality % carbonic allyl ester solutions of the phenylbenzene-4-of San-Apro Ltd. system (phenyl sulphur) phenyl sulfonium hexafluorophosphate) of light cationic polymerization initiators (C), modulate cationically polymerizable tackiness agent (5 ') thus.Obtain cl content contained in the total amount of resulting cationically polymerizable tackiness agent (5 ') by the aftermentioned method, it is 2019ppm.
[comparative example 6]
In the hermetic type planetary stirring machine, the compound (B '-6) that 40.0 mass parts is contained glycidyl ether, 35.0 mass parts ARON OXETANE OXT-221 (two [1-ethyl (3-oxa-cyclobutyl)] methyl ethers of Toagosei Co., Ltd's system) and 25.0 mass parts ARON OXETANE OXT-101 (the 3-methylol of Toagosei Co., Ltd's system-3-ethyl trimethylene oxide) and 4 mass parts are mixed and stirring as the CPI-100P (50 quality % carbonic allyl ester solutions of the phenylbenzene-4-of San-Apro Ltd. system (phenyl sulphur) phenyl sulfonium hexafluorophosphate) of light cationic polymerization initiators (C), modulate cationically polymerizable tackiness agent (6 ') thus.Obtain cl content contained in the total amount of resulting cationically polymerizable tackiness agent (6 ') by the aftermentioned method, it is 13462ppm.
[measuring method of chlorine total content]
Contained cl content in the cationically polymerizable tackiness agent of the present invention is measured according to JIS K1200-3-2:00.Particularly, amount about the said chlorine of the present invention, for the tackiness agent of counting with sodium-chlor more than 0.05%, with the value of trying to achieve cl content as this tackiness agent by the Fu Erhade improved method, for in sodium-chlor less than 0.05% tackiness agent, with the value of trying to achieve cl content as this tackiness agent by the ion chromatography method.
[making method of polarizer]
With Kuraray Poval PVA-117H (KURARAY CO., LTD. Zhi polyvinyl alcohol, the polymerization degree 1700, fully saponified thing, Powdered) be dissolved into resulting polyvinyl alcohol water solution in the water (nonvolatile component 8 quality %) and be coated with machine with rod and be applied on the stripping film, after under 80 ℃ the environment dry 5 minutes, remove described stripping film, make the polyvinyl alcohol film of thickness 75 μ m.
Then, resulting polyvinyl alcohol film is fixed in the drawing machine, in 40 ℃ warm water, described film is stretched to 3 times size on the single shaft direction.
After the water that the adhering on surface of the oriented film that obtains in above-mentioned is removed, described oriented film is impregnated into contains being adjusted in 30 ℃ the aqueous solution of 0.02 mass parts iodine, 2 mass parts potassiumiodides and 100 mass parts water.
Then, described oriented film is impregnated into contains being adjusted in 56.5 ℃ the aqueous solution of 12 mass parts potassiumiodides, 5 mass parts boric acid and 100 mass parts water.
Oriented film behind the described dipping is in being adjusted to 8 ℃ pure water after the washing, dry under 65 ℃ environment, obtain the polarizer (polarizing coating) that surface adsorption at the oriented film that is made of polyvinyl alcohol has iodine and has been orientated thus.
[making method of polaroid]
2 pieces of tri acetyl cellulose membranes (the thickness 80 μ m that the cationically polymerizable tackiness agent separate application that obtains in embodiment and the comparative example crossed to corona treatment with spreader, long 297mm, wide 210mm) on single surface, reach the thickness of about 2 μ m, UV irradiation equipment CSOT-40 (high voltage mercury lamp of Nippon Storage Battery Co., Ltd's system, intensity 120W/cm) with conveyer belt type shines 30～100mJ/cm to this coated face 2Ultraviolet ray.
Then, at the polarizer that obtains by described method (thickness 42 μ m, long 297mm, wide 210mm) described 2 pieces of tri acetyl cellulose membranes are pasted on two sides respectively, with rubber rollers pressurization and with them bonding after, heating is 1 minute in 60 ℃ drying machine, makes polaroid thus.
[evaluation method of normality bond strength]
The polaroid that will be obtained by described method is placed 1500 hours in being set at 85 ℃ drying machine after, (the modern field of Co., Ltd. makes made with tensile testing machine, draw speed=50mm/ minute, the T type is peeled off), the stripping strength at the triacetyl cellulose of each polaroid of mensuration formation and the interface of polyvinyl alcohol.Described stripping strength is more than the 10N/25mm or causes the fracture (MB) of tri acetyl cellulose membrane, be evaluated as " well ", stripping strength less than 10N/25mm, is evaluated as " bad ".
[evaluation of fading etc. of the variation of transmissivity, polarizer]
About fading and the degree of variable color of the polarizer that influence caused of cationically polymerizable tackiness agent, according to estimating at the velocity of variation of placing transmissivity about 1500 hours, polaroid under the condition of 65 ℃ of temperature and humidity 90% by the polaroid that described method is made.
The transmissivity of polaroid is measured with visible spectrophotometer (the JASCO V-570 of Japanese beam split Co., Ltd. system measures wavelength 200～900nm, sweep velocity 400nm/min).To the transmissivity (%) of the transmissivity (%) of the polaroid after the described placement polaroid before with respect to described placement changed ± more than 5%, be evaluated as " * ", the variation of the transmissivity of the polaroid after the described placement less than ± 5%, is evaluated as " zero ".
Figure GSA00000037401400311
Figure GSA00000037401400321
Figure GSA00000037401400322

Claims (15)

1. cationically polymerizable tackiness agent, it is characterized in that, this tackiness agent contains oxetane compound (A), aromatic glycidyl ether (B) and the cationic polymerization initiators (C) with 2 above oxa-cyclobutyl and molecular weight 100～800, and remaining chlorine is below the 1500ppm in the total amount of described tackiness agent.
2. cationically polymerizable tackiness agent according to claim 1, described oxetane compound (A) are two [1-ethyl (3-oxa-cyclobutyl)] methyl ethers.
3. cationically polymerizable tackiness agent according to claim 1, described aromatic glycidyl ether (B) for be selected from the group of forming by bisphenol A diglycidyl ether and Bisphenol F diglycidylether more than a kind.
4. cationically polymerizable tackiness agent according to claim 1, it further contains the oxetane compound (D) with 1 oxa-cyclobutyl, and the equivalent ratio of the oxa-cyclobutyl that oxa-cyclobutyl that described oxetane compound (A) is had and described oxetane compound (D) are had [the oxa-cyclobutyl that (A) is had/(D) had oxa-cyclobutyl] is 0.1～35.0.
5. cationically polymerizable tackiness agent according to claim 4, described oxetane compound (D) has 100～500 molecular weight.
6. cationically polymerizable tackiness agent according to claim 4, described oxetane compound (D) for be selected from the group of forming by 3-methylol-3-ethyl trimethylene oxide, 3-ethyl-3-(phenoxymethyl) trimethylene oxide, 3-ethyl-3-(2-ethyl hexyl oxy methyl) trimethylene oxide and 3-ethyl-3-(cyclohexyloxy) methyl trimethylene oxide more than a kind.
7. cationically polymerizable tackiness agent according to claim 4, overall with respect to described cationically polymerizable tackiness agent, contain two [1-ethyl (3-oxa-cyclobutyl)] methyl ethers of the described oxetane compound of conduct (A) of 20～70 quality %, and contain being selected from of the described oxetane compound of conduct (D) of 20～70 quality % by 3-methylol-3-ethyl trimethylene oxide, 3-ethyl-3-(phenoxymethyl) trimethylene oxide, in the group that 3-ethyl-3-(2-ethyl hexyl oxy methyl) trimethylene oxide and 3-ethyl-3-(cyclohexyloxy) methyl trimethylene oxide are formed more than a kind.
8. cationically polymerizable tackiness agent according to claim 1, it further contains alicyclic epoxy compound (E).
9. cationically polymerizable tackiness agent according to claim 8, the compound of described alicyclic epoxy compound (E) for having structure shown in the following general formula (7),
Figure FSA00000037401300021
A in the general formula (7) represents 0 or 1.
10. cationically polymerizable tackiness agent according to claim 8, described alicyclic epoxy compound (E) is 3,4-oxirane ring hexenyl methyl-3 ', 4 '-oxirane ring hexene carboxylicesters.
11. according to claim 1 or 8 described cationically polymerizable tackiness agents, it further contains epoxy radicals silicone hydride compound (F).
12. cationically polymerizable tackiness agent according to claim 11 with respect to the total amount of described cationically polymerizable tackiness agent, contains the described epoxy radicals silicone hydride compound (F) that contains of 0.1～1.5 quality %.
13. cationically polymerizable tackiness agent according to claim 11, the described epoxy radicals silicone hydride compound (F) that contains is for being selected from by 3-glycidoxypropyl triethoxyl silane, 3-glycidoxypropyltrimewasxysilane, 3-glycidoxypropyl methyldiethoxysilane, 3-glycidoxypropyl methyl dimethoxysilane, 2-(3, the 4-epoxycyclohexyl) in the group formed of ethyl triethoxysilane and 2-(3, the 4-epoxycyclohexyl) ethyl trimethoxy silane more than a kind.
14. according to each described cationically polymerizable tackiness agent of claim 1～13, its use in the polarizer that constitutes polaroid and protective membrane bonding.
15. polaroid; it is characterized in that; this polaroid is protective membrane that is made of triacetyl cellulose or the protective membrane that is made of cycloolefin, is bonded by the cationically polymerizable tackiness agent with the polarizer that is made of polyvinyl alcohol, and described cationically polymerizable tackiness agent is the described cationically polymerizable tackiness agent of claim 14.
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