TW201249945A - Cationic polymerizable adhesive and polarizing plate obtained by using the same - Google Patents

Abstract

The object of the present invention is to provide a cationic polymerizable adhesive which has excellent adhesiveness for kinds of protect films, especially for acrylic resin films, and a polarizing plate obtained by using the same. The present invention is related to the cationic polymerizable adhesive and the polarizing plate obtained by using the same to stick a polarizing plate and a protective film. The cationic polymerizable adhesive contains an aromatic glycidyl ether (A), an oxetane compound (B) having 2 or more oxetanyl groups, an alicyclic epoxy compound (C) presented by following general formula (7), and a cationic polymerization initiator (D). The cationic polymerizable adhesive is characterized by using 120 to 380 parts by mass of the oxetane compound (B) and 15 to 280 parts by mass of the alicyclic epoxy compound (C) relative to 100 parts by mass of the aromatic glycidyl ether (A).

Description

201249945 VI. [Technical Field] The present invention relates to a cationically polymerizable adhesive which can be used, for example, in the manufacture of a polarizing plate which is first used as a liquid crystal display or the like. A cationically polymerizable adhesive which is hard to cause hardening due to oxygen in the atmosphere and which can be cured after the supply of energy such as ultraviolet rays is stopped is attracting attention. Therefore, the development of cationic polymerizability is progressing significantly in the development of materials, and there are reports of adhesives suitable for various uses. In the case of the cationically polymerizable adhesive, for example, a cationically polymerizable adhesive is disclosed, which is a compound containing a glycidyl ether group obtained by distillation of a dimethyl ketone ether. a glycidyl ether group-containing compound obtained by distilling a bisphenol F type diglycidyl ether, a compound having an X solution of a sulfhydryl group and a chelating oxy group, and a cationic polymerization initiator, and having a chlorine content of 500 ppm ( For example, refer to the patent document 丨). In the protective film constituting the polarizing plate, among the cellulose triacetate (TAC) film and the cycloolefin polymer (c〇p) film which have been widely used, the above-mentioned cationically polymerizable adhesive has an indication to the tac film system. The continuation of the level of use. In addition, in recent years, in view of the cost reduction of the above-mentioned polarizing plate, the & ^ Λ ^ β - 』 replaces the TAC 溥 film, and the inexpensive acrylate film is being exhausted. In the above-mentioned cationically polymerizable adhesive, it is expected that the bonding strength is low due to the low bonding strength to the acrylic resin 201249945 acid resin film. Into the promotion of a cow. (Progress = In addition, since the above-mentioned cationically polymerizable adhesive has a high viscosity, when the above-mentioned adhesive is applied to the protective ruthenium film or the polarizer, it may cause unevenness in the adhesive layer, and may affect the optical characteristics of the polarizing plate. The problem of the problem is as follows: [Patent Document] [Patent Document] [Patent Document 2] Japanese Laid-Open Patent Publication No. JP-A No. Hei. [Patent Document 4] Japanese Patent Laid-Open Publication No. JP-A No. Hei. No. 2 〇 〇 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 126 阳离子 阳离子 阳离子 阳离子 阳离子 阳离子 阳离子 阳离子 阳离子 阳离子 阳离子 阳离子 阳离子 阳离子 阳离子 阳离子 阳离子The polarizing plate obtained by using the same, the cationically polymerizable adhesive has excellent adhesive strength not only for a wide variety of protective films, particularly for acrylic films. [Means for Solving the Problem] In order to solve the above problems, the inventors of the present invention have devoted themselves to researching a combination of various cationically polymerizable compounds. As a result, it was found that 'for the sulphate glycidyl bond, it is limited to the use of a special amount of an oxocyclobutane compound having two or more oxocyclobutenes (Xetanyl) and an alicyclic epoxy compound having a specific structure. The problem of the present invention can be solved. 201249945 That is, the present invention relates to the use of a straight squeezing earth ♦ s-type adhesive and the use of a splicer polarizer and a protective film cationically polymerizable adhesive containing aryl lanthanum:: partial slab,... ,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,, (, and cation polymerization parts of the range of 1 used:: 垸 compound (B) is used in the range of 28 Λ 返 alicyclic epoxy compound (6) is used in the range of 15 to 280 Å.

R2 (7) a hydrogen atom or a methyl group) (in the formula (7), 'R, I^R3 are each independently shown. [Effect of the invention]

The cationically polymerizable granules of the present invention ▲ 眭 眭 眭 不仅 不仅 不仅 不仅 不仅 不仅 不仅 不仅 不仅 不仅 不仅 不仅 不仅 不仅 不仅 不仅 不仅 不仅 不仅 , , 不仅 , 不仅 不仅 不仅 不仅 不仅 不仅 不仅 不仅 不仅 不仅 不仅 不仅 不仅 不仅 不仅 不仅 不仅The adhesive is provided with a thin film of the film, so that, for example, even when the protective agent is coated with the adhesive of the present invention, there is no unevenness in the bonding layer and adverse effects on the optical properties of the pure film. [Embodiment] 201249945 [Form of the Invention] First, the above aromatic glycidyl ether (A) will be described. The above aromatic glycidyl ether (A) is an essential component when it has a bonding strength. As the aromatic glycidyl ether (A), a good adhesion can be imparted by using a glycidyl group of 2 = or more, and therefore it is preferably 2 to 6 in terms of ruthenium. The aromatic glycidyl ether may be, for example, bisphenol A glycidyl ether, bisphenol F glycidyl ether, bisphenol s glycidyl ether or bisphenol AD glycidyl ether. These aromatic glycerol ethers may be used singly or in combination of two or more. From the viewpoint of the strength of the intermediate / Π», it is preferred to use a double-type A-type glycidyl bond or a bisphenol F-type glycidyl ether. As the bisphenol A type glycidyl ether, for example, bisphenol A diglycidyl ether can be used. Further, for the bisphenol F type glycidyl ether, for example, bisphenol F diglycidyl ether can be used. κ As the above aromatic glycidyl ether (A), the hardenability can be further improved by 4, and the hardness of the cured product can be moderately increased, and the butyl diglycidyl ether selected from the group consisting of bisphenol A diglycidyl ether can be used. It is preferred that the above-mentioned group of bisphenol F bisphosphonium glyceryl ether is more than the above. Further, in the present invention, the above-mentioned scented glycidyl ether (oxime) may be used in combination with other glycidol, as long as it does not impair the effects of the present invention. ^ The above other glycidyl ethers may have, for example, trihydromethane propane tris, monoterpene glyceryl ether, glycerol triglycidyl ether, polyglycerol triglycidyl linkage, glycerol diol, etc., having three glycidyl ether groups Greases 201249945

And trimethylolpropane diglycidyl ether, cyclohexane dimethanol diglycidyl ether, propylene glycol diethylene glycol diglycidyl ether, etc., having two shrinking glycidyl ethers, glyceryl compounds and the like. a glycidyl sulphate, a di-glycidyl ether group shrinkage, and the above-mentioned aromatics mentioned other glycidol - can also use a hydrogenated hydrogenated bisphenol A type glycidyl ether or a hydrogenated double-hop F type using glycidyl ether (A) Glycidol and the like. Next, the above oxygen cyclobutane compound will be described. The above oxycyclobutane compound (B) is particularly essential for imparting low viscosity. Further, the above-mentioned oxycyclobutane compound (B) is used in an amount of from 12 Å to 38 Å by mass in terms of 100 parts by mass of the above aromatic glycidol (A), which is necessary in solving the problems of the present invention. In the above, the aromatic glycidyl ether (A) is preferably in the range of from 1 40 to 375 parts by mass, and in the range of from 140 to 360 parts by mass, based on the 00 parts by mass of the aromatic glycidyl ether (A). The range is better. As the above oxycyclobutane compound (B), two or more oxocyclobutane groups which contribute to cation polymerization can be used, and it is preferred to have 2 to 4 members. A compound represented by the formula (1) or (2).

Specifically, the above-mentioned anthracene cyclobutane compound (B) can be used, for example, in the following general formulas 201249,945. In the above formulas (1) and (2), R1 each independently represents a hydrogen atom, a linear number of 1 to 6 carbon atoms, and a branched chain. Aromatic or cyclic alkyl, allyl, aryl, aralkyl, furyl or thiophene; R2 each independently represents a divalent organic residue 'Z each independently representing an oxygen atom or a sulfur atom. a branched or cyclic, or a di- or aryl group, for example, a phenyl aryl group, for example, a linear one having a carbon number of 1 to 6 as shown by the above R1, and a branching group, such as a fluorenyl group, and a A group, a n-butyl group, a pentyl group, a hexyl group, a cyclohexyl group, etc., and a phenyl fluorenyl group, a phenethyl group, and the like. In the above formula (1), R2 represents a divalent organic residue such as a linear, branched or cyclic alkyl group, and a poly(oxygen) having 4 to 3 carbon atoms. a structure represented by the following formulas (3) and (4). The linear number, the branched chain or the cyclic alkyl group constituting the above R2 is a carbon number such as a methylene group, an ethyl group, a 1,2- or 1> 3-propyl group, a butyl group and a cyclohexyl group. It is preferred that the alkyl group is up to 15. Further, a poly(oxyalkylene) group having 4 to 3 carbon atoms is preferred to have 4 to 8 carbon atoms, and for example, a poly(oxyethyl) group or a poly(oxygen) group is preferred. . -CHz /z^vCHa- 〇r3a\J> (3)

In the above formula (3), R3 represents an oxygen atom, a sulfur atom, CH2, NH, SO, so2, c(cf3)2 or c(ch3)2. ο ο —c — r* —ΰ — (4) Alkyl group of a carbon atom In the above formula (4), 'R4 represents a functional group having 1 to 6 extended aryl groups and the following general formula (5) 201249945 For example, 2 long ^> 士35 gas (5) In the above formula (5), a represents an integer from 1 to 6, and b represents an integer from 1 to 15. In the above formula (5), b is preferably an integer of from 1 to 3.

The above oxycyclobutane compound having 2 to 4 oxocyclobutane ring structures is, for example, commercially available ARONE OXETANE OXT-221 'ARONE OXETANE OXT-121, ARONE OXETANE OXT-223 (the above is manufactured by East Asia Synthetic Co., Ltd.) ); ETERNACOLL ΟΧΒΡ, ETERNACOLL OXTP, ETERNACOLL ΟΧΙΡΑ (the above is manufactured by Ube Industries Co., Ltd.). The molecular weight ' of the above-mentioned oxycyclobutane compound (Β) is preferably in the range of 100 to 800, and more preferably in the range of 1 Torr to 5 Torr, from the viewpoint of further improving the low viscosity. In the adhesive agent of the present invention, for example, when the polarizer and the protective film are subsequently adhered, in order to sufficiently cure the film, the film thickness of the adhesive layer is usually a film (a thickness of several μm), and the adhesive is uniformly applied to the above-mentioned degree. The film thickness and the adhesive are necessary for low viscosity. Further, the molecular weight of the above oxycyclobutane compound (Β) having two or more oxycyclobutane groups represents a molecular weight calculated from the structural formula. Further, the above-mentioned oxycyclobutane compound having two or more oxycyclobutane groups is preferably one represented by the above formula (1), and particularly, R1 in the formula is ethyl group. R2 is an anthracene group of bis [indenyl-(3-oxocyclobutane)] decyl ether, and since the film thickness of the adhesive after hardening can be made thinner, it can further improve hardenability and adhesiveness. Very good. Further, 'in the present invention', as in the case of non-destructive effects of the present invention, -10-201249945 (B) ^, with two or more oxocyclobutane oxocyclobutane compounds having an oxygen ring An alkylcyclobutane compound. A compound represented by the following formula (4) can be used. OR2 - (8) An oxocyclobutane compound having one oxycyclobutane group is, for example,

〇(Formula (6), R 1 Ben-*, a pyrophoric atom, a carbon number of 1 to 8, a carbon number of 1 to a decyl group or a carbon number! to a 6 ash alkyl group, R is not Atom, can be < and the number of mosquitoes i to i 烷 烷 知 知 知 % % % % % % % % % % % % % % % % % % % % % % % % % % % % % % % % % % % 2-ethyl and, for example, an alkyl group which may be listed. Further, an alkyl group having 1 to 8 carbon atoms which may constitute R1 in the formula (6), ethyl, n-propyl or isopropyl group may be mentioned. And 2-ethylhexyl group, etc. 'In the above formula (6), the alkoxy group having 1 to 5 carbon atoms which can constitute R1 can be exemplified by Xenon A | Milk T-based, Ethoxymethyl, Propoxymethyl, A Oxygen oxyethyl, propyl ethene, etc. 'In the above formula, the hydroxyalkyl group having 1 to 6 carbon atoms which may constitute R1 is exemplified by a hydroxymethyl group, a face 7# ethyl group, a hydroxypropyl group and the like. In (6), the branched carbon number 1 group which can constitute R2 may, for example, be a linear alkyl group such as a methyl group or a propyl group, or a branched alkyl group such as a hexyl group. In the middle of 'an aliphatic ring structure constituting R2 The cyclohexyl group or the like may have a substituted hydrogen atom, and in the above formula (6), the aromatic structure in which τ constitutes r2 may be, for example, an alkyl group which may have a substituted hydrogen atom, such as the above-mentioned stupid group, etc. -11- 201249945 Next, The alicyclic epoxy compound (c) component is described. The alicyclic epoxy compound (C) component is an alicyclic cyclic oxime compound represented by the following formula (7).

(In the formula (7), 'R, 尺 2 and R3 each independently represent a hydrogen atom or a methyl group). Further, the above alicyclic epoxy compound means a compound having an epoxy group-containing alicyclic epoxy group in the alicyclic structure. The above-mentioned aliphatic % cyclic oxime compound is particularly essential for imparting good adhesion strength to an acrylic resin film. Further, the above-mentioned alicyclic epoxy compound (C) is used in an amount of from 15 to 280 parts by mass per 100 parts by mass of the above aromatic glycidyl bond (A), which is necessary in order to solve the problem of the present invention. In the above, from the viewpoint of further questioning the strength, it is preferred to use the above aromatic glycidyl ether (A) in an amount of from 2 to 27 parts by mass, and from 3 to 5 parts by mass per part by mass. The range of 250 parts by mass is better. The above-mentioned g-ring epoxy compound (preferably, the j-based limonene is preferable from the viewpoint of the adhesive strength of the acrylic resin in the oxime. The commercially available product of the above-mentioned month may be manufactured by CELL XIDE). From the viewpoint of further improving the strength, the use of 12:8,9 bisepoxide as the applicable alicyclic epoxy compound can be applied to the above-mentioned alicyclic compound (〇3000 (Daicel Chemical Industry Co., Ltd.) -12- 201249945 In addition, in the present invention, within the σ range, the above-mentioned formula can also be used in the non-destructive and alicyclic epoxy compound of the present invention. "μ compound (C) is used in combination with the other Examples of the alicyclic emulsifiable compound include, for example, an epoxy compound having a thiol group of 2 to 4 months. The milk compound is a compound in which 3,4-epoxycyclohexenylmethyl-3,4-'oxy group is succinctly succinated (the compound of the formula (8), a is 0), a potted/incorporated product (a compound of the formula (8), & 1), a trimethylhexene 8 曰 modified shell (structural formula (9) and structural formula (1〇)), and Modified valerolactone, structural formula 、 1, "From this...............

(10) 201249945

<j«3 c> 〇"CM2.-CH— (11)

(12) q I c»3 C—〇 -αΐ2-€Η2-*αΐ-〇Η2~ C-0-CH2

Further, as the alicyclic epoxy group having two alicyclic epoxy groups, a compound represented by the following formula (14) can also be used. R1 R6 R5

R2 R3 R4 (R1 to R6 in the formula (14) each independently represent a hydrogen atom or a condensed group having a carbon number of 1 to 6). Specific examples of the compound represented by the above formula (14) include dicyclohexyl-3,3'-diepoxide. Further, as the alicyclic epoxy compound having three alicyclic epoxy groups, a compound represented by the following formula (15) can be used.

14-201249945 (in the formula (15), 'a and b each independently represent 〇 or 丨, and these may be the same or different). The alicyclic epoxy compound represented by the formula (15) is, for example, commercially available EPOLEAD GT301, EPOLEAD GT302 (the above is manufactured by Daicel Chemical Industry Co., Ltd.) and the like. Further, as the alicyclic epoxy compound having four alicyclic epoxy groups, for example, a compound represented by the following formula (16) can be used.

(In the above formula (16), a?d each independently represents 0 or 1, and these may be the same or different). The alicyclic epoxy compound of r is, for example, a commercially available EPOLEAD GT403 (the above is made of 〇31 €^EPOLEAD GT401, manufactured by the above-mentioned general formula (16), manufactured by Chemical Industry Co., Ltd.). Next, the cationic polymerization initiator (D) used in the present invention will be described. The cationic polymerization initiator (D) is a polymer which generates an acid capable of starting cationic polymerization, for example, by irradiation with an energy ray such as ultraviolet rays. The cationic polymerization initiator (D) is, for example, a cation.卩 is divided into -15- 201249945 aromatic oxime, aromatic hydrazine, aromatic diazo, aromatic ammonium, thiazide (thianthrenium). Thioxanthonium, (2,4-cyclopentadien-1-yl)[(1-methylethyl)benzene]-Fe cation; anion moiety BF, PF6_, SbF6_, [BX4 The sulfonium salt composed of (only X is a phenyl group substituted with at least two or more fluorine or a trifluoromethyl group) may be used alone or in combination of two or more. As the above aromatic sulfonium salt, for example, bis[4-(diphenyldihydrothio)phenyl]sulfide bishexafluorophosphate or bis[4-(diphenyldihydrothio)phenyl]sulfide double can be used. Hexafluoroantimonate, bis[4-(diphenyldihydrothio)phenyl]sulfide ditetrafluoropentate, bis[4-(diphenyldihydrothio)phenyl]sulfonium sulfide (five Fluorophenyl)borate, diphenyl-4-(phenylthio)phenylphosphonium hexafluorophosphate, diphenyl-4-(benzoyl)phenyl sulphate, diphenyl- 4-(phenylthio)phenylsulfonium tetrafluoroborate, diphenyl-4-(phenylthio)phenylphosphonium (pentafluorophenyl)borate, triphenylsulfonium hexafluorophosphate, triphenyl Hexafluoroantimonate, triphenylsulfonium tetrafluoroborate, triphenylsulfonium (pentafluorophenyl)borate, bis[4-(di(4-(2-hydroxyethoxy))benzene Dihydrothio)phenyl]sulfuric bishexafluorophosphate, bis[4-(bis(4-(2-hydroxyethoxy))phenyldihydrothio)phenyl]sulfide dihexafluoroantimonic acid Salt, bis[4-(bis(4-(2-hydroxyethoxy))phenyldihydrothio)phenyl]sulfide bistetrafluoroborate, bis[4-(di(4-(2-hydroxy)) Ethoxylate Dihydro phenyl) phenyl] sulfide tetrakis (pentafluorophenyl) shed acid salts. Further, as the above aromatic phosphonium salt, for example, diphenylphosphonium hexafluorophosphate, diphenylphosphonium hexafluoroantimonate, diphenylphosphonium tetrafluoroborate, diphenylphosphonium (pentafluorophenyl) can be used. Phytate, bis(dodecylphenyl)phosphonium hexafluorophosphate, bis(dodecylphenyl)phosphonium hexafluoroantimonate, bis(dodecyl-16- 201249945 phenyl) fluorene Fluoroborate, bis(dodecylphenyl)phosphonium (pentafluoro# borate, phenyl-4-U-methylethyl)phenyl t-based) _ ^ 虱 虱, 4-A Phenyl-4-yl-(1-methylethyl)phenylphosphonium hexafluoroantimonate, methyl 2-phenyl-4-(1-methylethyl)phenylphosphonium tetrafluoroborate, 4-methylbenzene Earth-4-(1-methylethyl)phenyl hydrazine (pentafluorophenyl) rotten acid salt, and the like. Further, as the above aromatic diazonium salt, for example, phenyldiazonium hexafluoride: phenyldiazonium hexafluoroantimonate 'phenyl diazotetrafluoroborate, phenyldiazonium pentoxide (pentafluorobenzene) can be used. Base) borate and the like. Further, as the above aromatic ammonium salt, for example, b benzyl·2·cyanamide hexahydrophosphate, 丨_ 基 _2 2 _ cyanopyridine hexafluoroantimonate, phenyl-2-cyano acridine can be used. Tetrafluoroborate, 丨_节基_2_cyanoacridinium phenyl) sphaplatinate, 1_(芡甲其,?一(不T基)_2_乱基pyridine hexafluorophosphate, nai Base)-2-cyano group. Bis-hexafluoroantimonate, b (naphthoquinone-based 2 octagonal bite tetrafluoroborate, extraction of it, 0 @ #

Ut, T-based)-2-cyano group. Than yttrium (pentafluorophenyl) borate. As the succinyl sulfonium salt, for example, S-biphenyl-2-isopropyl group, sulphur, sulphur, iron, hexahydrate, etc., and the above (2,4-cyclopentadienyl small group) [(1) As the methylethyl)benzene]A salt, for example, (2,4-cyclopentadienyl small)[(1-mercaptoethyl)benzene]-Fe (II) hexanoate, (2, 4) can be used. -cyclopentadienyl small)[(1-methylethyl)benzene]-Fe(n) hexafluoroantimonate, (2,4-cyclohexadimide) [(1_methylethyl) Phenylhydrazine (9) tetralithite salt, (2,4-cyclopentadienyl small) [(1 methylethyl) phenyl]-Fe(II) quinone (pentafluorophenyl) borate. The upper cationic polymerization initiator (D) is commercially available, for example, CPI_1〇lA, CPI-110P, CPI-200K, CPI-210S (above -17-201249945 SAN-APRO); CYRACURE light Hardening initiator UVI-6990, CYRACURE photohardening initiator UVI-6992, CYRACURE photohardening initiator UVI-6976 (above manufactured by Dow Chemical Japan); ADEKA OPTOMER SP-150, ADEKA OPTOMER SP-152 ' ADEKA OPTOMER SP-170, ADEKA OPTOMER SP-172, ADEKA OPTOMER SP-300 (above made by ADEKA); CI-5102, CI-2855 (above manufactured by 曹本曹达(股)); San-Aid SI-60L, San-Aid SI-80L, San-Aid SI-100L, San-Aid SI-110L, San-Aid SI-180L, San-Aid SI-ΠΟ, San-Aid SI-180 (above by Sanxin Chemical Industry Co., Ltd.; ESACURE 1 064, ESACURE 1 1 87 (manufactured by LAMBERTI); OMNICAT 550 (manufactured by IGM RESIN); IRGACURE 250 (manufactured by BASF JAP AN); RHODORSIL PHOTO INITIATOR 20 7 4 (RHODI A JAP AN (manufacturing)) and so on. The amount of the cationic polymerization initiator (D) to be used is preferably from 5 to 50 parts by mass based on 100 parts by mass of the above aromatic condensed glycidyl ether (A). The cationic polymerization initiator of the present invention may further contain an epoxy group-containing decane coupling agent (E), an epoxy group-containing decane coupling agent (E), in order to increase the strength of the adhesive strength or the adhesive layer coating film. Examples thereof include: 2-(3,4-epoxycyclohexyl)ethyltriethoxydecane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxydecane, 2-(3,4) -Epoxycyclohexyl)ethylmethyldioxanthene, 2_(3,4-epoxycyclohexyl)ethylmethyldiethoxydecane, 2-(34.epoxycyclohexyl)propyl Trioxantane, 2_(3,4·epoxycyclohexyl) • 18- 201249945 propyl decyl dioxa oxane, 2-(3,4-epoxycyclohexyl)propyl triethoxy decane, 2 a decane coupling agent containing a lipid oxime epoxy group such as (3,4-epoxycyclohexyl) propylmethyldiethoxy oxane; 3 glycidoxypropyltrioxoxane, 3-ring A money coupling such as oxypropoxypropyltriethoxysilane, 3-glycidoxypropylmethyldiethoxyoxane or 3-glycidoxypropylmethyldimethoxypyrene. The (four) sinter coupling agent may be used alone or in combination of two or more. The _, from the viewpoint of further improving the strength, is selected from the group consisting of ^=4-cyclod-cyclohexyl)ethyltriethoxy(tetra), 2(3,4 epoxy: and [I: bis/ Preferably, the above oxygenated decane is selected from the group consisting of Oxygen Oxide, 3_glycidoxypropyltrimethoxide, and Lactopropylpropyltriethoxysilane. Use of coupling agent (E) 10 〇 mass price μ μ · +. # I h Do not look at Lidan's scented aromatic glycidyl ether (A), in the range of 5 to 1 〇〇 It is preferably used internally. 'The cationically polymerizable adhesive (F) of the present invention. < / 3 is sensitized to the cationic polymerization of the present invention, followed by the use of the s' agent in the polarizer and the protective film. ^ The above-mentioned cationically polymerizable adhesive is applied to the above-mentioned protective film, and then, after the::..., the side of the ruthenium film is subjected to the case where the purple adhesive is cured as described later. When the cationic polymerization is difficult to pass light of 380 nm or more, as a protective film for adenine or π* transmission (for example, ΤΑC film), It is preferable that the sub-concentration U such as TAC/# has the above-mentioned first sensitizer (F) from the viewpoint of the curability of the α-carrier. -19- 201249945 The above-mentioned photosensitizer (F) can be used, for example. : hydrazine, hydrazine, thioxanthone, diphenyl ketone, benzoin isopropyl mystery, and derivatives of the specific compound. Among these, for the above reasons, the use of light having a wavelength of 380 nm or more exhibits a maximum absorption. Preferably, it is more preferable to use a lanthanoid compound. The above lanthanoid compound which exhibits a maximum absorption of light having a wavelength of more than 3 80 nm can be, for example, 9,10-dimethoxyanthracene, 9,10·diethoxyanthracene. , 9,10-dipropoxy fluorene, 9,1 fluorene diisopropoxy fluorene, 9,1 fluorene dibutoxy fluorene, 9,10-dipentoxy fluorene, 9,10-dihexyl Oxime, 9,10-bis(2-methoxyethoxy)anthracene, 9,10-bis(2-ethoxyethoxy)anthracene, 9,10-bis(2-butoxyB) Oxy) ruthenium, 9,10-bis(3-butoxypropoxy)fluorene, 2-methyl or 2-ethyl·9,10-dimethoxy oxime, 2-methyl or 2-ethyl Base-9,10-diethoxyanthracene, 2-methyl or 2-ethyl-9,10-dipropoxyfluorene, 2-indenyl or 2-ethyl-9,10-diisopropyl Base, 2-methyl or 2-ethyl-9,10-dibutoxyanthracene, 2-methyl or 2-ethyl-9,10-dipentyloxy oxime, 2-methyl or 2- Ethyl 9,10 - hexyl, sensation, etc. The above-mentioned enantiomers are, for example, commercially available "UVS-133 1" (manufactured by Kawasaki Chemical Industry Co., Ltd.), KAYACURE DETX-s (Sakamoto Chemical Co., Ltd.) The amount of the light sensitizer (F) used is desirably used in the range of 〇5 to 1 part by mass based on 1 part by mass of the above aromatic glycidyl ether (A). The sensitizing wavelength region of the sub-polymerization initiator (D) is further enhanced by the curing agent of the bonding agent (G). And 'when the above-mentioned photosensitizer (F) is used, in order to enlarge the above-mentioned cation 1', the cationic polymerization of the present invention may be combined with photo-sensitization to assist the above-mentioned photosensitizer (G). For example, nitronium may be used. And naphthalene compound -20- 201249945, etc., using hydrazine, 4-dimethoxynaphthalene, 1-ethoxy-4-methylmethoxy, 1,4-diethoxy 1, 1'4- - Propyl-based Qin, 1,4-dibutoxy-Cai, etc. are preferred. The amount of the photo-sensitizer (G) used is desirably used in an amount of from 0.5 to 1 part by mass based on 1 part by mass of the above aromatic glycidinium (A). Next, the cationically polymerizable adhesive of the present invention will be described. The cationically polymerizable adhesive of the present invention contains the above aromatic glycidyl ether (A), the above oxycyclobutane compound (B), and the above alicyclic epoxy. a compound (C), the above cationic polymerization initiator (D), and, if necessary, an epoxy group-containing decane coupling agent (E), a photosensitizer (F), and a photosensitizer (G), However, various additives may be contained within a range not impairing the effects of the present invention. The above additives can be used as a shake aid, a leveling agent, an antioxidant 7 sticky Wl (tackifier), 4 mice, a heat stabilizer, a light stabilizer, a glory increase, a guide package, a thermoplastic resin, and a thermosetting property. Resin, organic solvent, odor imparting agent, antistatic agent, moisture permeability improving agent, water repellent, Ning Ershi bubble, έ士曰> Children's day water compound, flame retardant, water absorption Agent, hygroscopic sheet, taste odorant, y, 士, *, ^★ 浥 稳定 stabilizer, defoamer, anti-mold agent 'preservative, anti-coating agent, sputum and so on. ...block, water-repellent, organic and inorganic water-soluble compound 2 2 , in addition to the above, in order to further reduce the rigidity of the cationic poly 4 of the present invention, it may also contain poly-polyol, etc. 201249945 Further, in addition to the above, the sclerosing property and the low viscosity of the cationic bismuth-based adhesive of the present invention are more than k, and the cation-polymerization is used as a target bond or a butyl epoxide. Dilute the above-mentioned ethyl ether ether system, for example, D-___ drunk monovinyl ether, hexanediol divinyl ether, diethylene glycol divinyl ether, triethylene glycol divinyl ether, neopentane Glycol divinyl ether, ketone, etc. k ^ 院 院 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二In addition, the viscosity of the cationically polymerizable adhesive is measured by a value of 25t. Degrees Next, a method for producing a cationically polymerizable adhesive of the present invention will be described. 4 σ 性 接接接剂系系能The cationically polymerizable adhesive agent of the present invention is, for example, a container having a stirrer or the like, and the above-mentioned aromatic shrinkage bond (4) and the above oxygen ring are preliminarily produced by mixing and stirring the i π 犴The butyl compound (Β), the alicyclic ring emulsion compound (C), the cationic polymerization initiator (D), and various additives described above may be produced. Δ曰 The cationically polymerizable adhesive of the present invention The cationically polymerizable adhesive of the present invention is cured by irradiation with energy rays such as ultraviolet rays. The irradiation of the energy rays such as ultraviolet rays is performed by irradiation with an energy ray such as ultraviolet rays. The range of 10 to 5000 mJ/cm 2 is preferably in the range of 20 to 2500 mJ/cm 2 , particularly preferably 3 〇 to %; the range of ^22-201249945 1 5 00 mJ/cm 2 is particularly good. The source of ultraviolet light can be used. For example: xenon lamps, mercury xenon lamps, metal halide lamps, high pressure mercury lamps, low pressure mercury lamps, etc., and 'UV irradiation is UV CHECKER; UV Power PucK (II) (Electronic Instrumentation And manufactured by the company, 'the value measured in the wavelength region of 300 to 390 nm is used as a reference. And 'may be necessary', after being irradiated by the above-mentioned energy ray, it is further accelerated by heating at about 40 to 80 C. Next, this is The polarizing plate of the present invention is an adhesive layer formed by the above-mentioned cationically polymerizable adhesive, which is followed by a protective film and a polarizer. For the protective film, for example, an acrylic resin or a lanthanum can be used. Resin, epoxy resin, gas resin, t-styrene resin, polyester resin, polyglycol resin, polyacrylate resin, polystyrene resin, polyvinylidene gas, norbornene, etc. Cycloolefin resin, amorphous polyolefin resin, polyimide resin, alicyclic poly phthalene resin, cellulose resin, PC (polycarbonate), ρΒτ (polyterephthalic acid) Films or flakes such as butyl vinegar), g^PPE (polyphenylene sulfide), ρΕΝ (polynaphthalene carboxylic acid vinegar), /ΕΤ (polyethylene terephthalate), etc.: or polylactic acid polymer, etc. Biodegradability Film. Further, the acrylic resin system L j uses an acrylic resin or a thermoplastic acrylic tree such as an acrylic resin or a thermoplastic acrylic tree having a number average particle diameter of 2, and the above-mentioned elastomer particles are excessively dispersed. Protect the film as a protective film. And the central portion of the direction of the -23-201249945 The thickness of the protective film used in the production of the polarizing plate of the present invention varies depending on the use, but is about 2 〇 μηη to 1 〇〇 μιη The range is good. Further, the thickness of the above polarizer is generally in the range of about 5 μm to 50 μm. For example, the grain of the saponification of the polyvinyl alcohol, the partially formaldehydeized polyvinyl alcohol, the polyethylene glycol, the partially saponified partial saponified product, etc. can be used. Polymer: The plastic substrate composed of the material is adsorbed by two materials such as bismuth or dichroic dye and stretched early; the surface of the plastic substrate is uniaxially stretched, and the above dichroic property is adsorbed. Materials; polyethylene dehydration treatment or hip preparation 7 咕 to the film generation. A polyene system such as a glycine hydrochloride treatment or the like. Among them, it is advisable to etch the film of the dichroic material of the field ear. The alcohol-based film and the adsorbed moth, etc. 4: The polarizing plate is, for example, a UV-compatible adhesive capable of emitting the above amount on the protective film. The polarizing plate is placed on the coated surface with an ionic polymerizable adhesive, and then the positive electrode is coated on the protective film, and then irradiated from the side of the protective film: a surface: a polarizer is placed, and the polarizing film of the present invention is further provided. The board system can be manufactured inside and outside the line. An ionic polymerizable adhesive, followed by applying the above-mentioned positive ultraviolet light to the light sheet, and irradiating the above-mentioned amount on the coated surface at 哕泠I $ , and manufacturing the film on the polarizing film; The film was placed on the side of the protective layer of the cationically polymerizable adhesive to illuminate the above-mentioned amount of purple:: cloth surface, and then manufactured from the above ', ". In the manufacture of the invention -24- 201249945

In the case of a polarizing plate, it is preferable that the thickness of the layer A and the binder of the binder are inferior to the optical properties, and it is preferably 5 or less, as much as possible. Divided into two: for example, irradiating the above-mentioned amount of ultraviolet rays on one surface of two protective films; then: in the coating, and then on the surface of the polarizer: 丄: respectively, the loading surface is loaded The product of the protective film/cationic concentrating sheet/cationic polymerizable adhesive/protective film is also coated on the single side of the two protective films:: splicing agent: The coated surface was placed on the double of the polarizer and then irradiated with the above-mentioned amount of ultraviolet rays to form the laminate. The method of applying the above-mentioned cationically polymerizable adhesive is not particularly limited, and a slit coating method such as a sapphire coating method, a roll coating method, a gravure coating method, a spray coating method, or the like can be used. Coating method. The polarizing plate of the present invention obtained by the above method can be used, for example, as a component of a mobile communication terminal device such as a mobile phone or a display such as a liquid crystal television, a personal computer, or a portable game machine. [Examples] Hereinafter, the present invention will be described in detail by way of examples. [Production Method of Polarizing Plate] A polyvinyl alcohol aqueous solution obtained by dissolving KURARAY POVAL PVA-117H (polyvinyl alcohol produced by KURARAY), having a polymerization degree of 17 〇〇, a completely saponified product, and a powdery form in water (not The volatile matter (8% by mass) was coated on the release film with a coating bar. Then, after drying for 5 minutes in an environment of 8 ° C, 25-201249945, the film was removed by a film thickness of 75 μm by removing the above-mentioned release film. The polyvinyl alcohol is then thinned, and the obtained polyvinyl alcohol., 'special film is fixed in a stretching machine, and the film is stretched to 3 times in the early axis direction in the warm water of 40 The size of the stretched film obtained by the above-mentioned stretching is immersed in the iodine containing 2 denier, 7 4 , and the water and 100 parts by mass are adjusted to 30. The 〇 置, the potassium iodide 2 parts by mass Next, in the aqueous solution of L. Next, the above-mentioned stretched thin amine;,, 3_, main, thick film β is stained with 12 parts by mass of potassium iodide, 5 parts by mass of boric acid, and water i 〇〇蜇 贝 贝 仂 仂 仂 仂 Λ Λ The injury is adjusted to 56.5. (: in the aqueous solution. The thinning after the above impregnation: filming is adjusted After washing in pure water at 8 ° C, drying is carried out at 65 ° C. _ ^ Drying to obtain a surface of the stretched film composed of polyethylene yeast and iodine and matching Polarizer (polarized ruthenium film) [Example 1] In a reaction vessel equipped with a scrambler, a reflux cooler, a w _ | benefits, a meter, a dropping funnel, and a nitrogen gas guide, mixed as a fragrance (10) parts by mass of EPICOL0 EXA_8 of the family glycidyl bond (4), Rp, 150 parts by mass of AR0NE 0XETANE OXT_221 as an oxygen ring-containing compound (B) having two or more oxygen-cyclobutanyl groups, as an alicyclic epoxy 250 parts by mass of CELL0XIDE of compound (6) and 40 parts by mass of diphenyl·4·(phenylthio)phenyl hexahydroperoxide as a cationic polymerization initiator (D), 50% by mass of carbonic acid The solution was mixed and mixed to prepare a cationically polymerizable adhesive having a viscosity of 23 mPa.s (25 ° C.) The surface of each of the acrylic resin film and the TAC film was coated with a wire -26-201249945. The yang is separated from the early date, and the ion-supporting agent is made to be about one thick: 雔: The cloth base material is attached to the above polarizer (polarizing film) and f, and after being pressurized with a blanket cylinder, a belt type I external line irradiation device (Fusion LH_6; output (10)%' belt speed 17.8 m/ Minutes) 'The ultraviolet light having a cumulative light amount of 13 〇〇 mJ/cm 2 from the side of the above-mentioned acrylic acid film to the 390 nm is obtained by having a protective film/cationic polymerizable adhesive layer/polarizer/cationic polymerization property. A polarizing plate composed of a coating layer/protective film. [Example 2] In a reaction vessel equipped with a blender, a reflux condenser, a thermometer, a dropping funnel, and a gas-conducting population, EPICL〇N EXA_83, which is a mass fraction of the aromatic glycidol mystery (Α) 〇CRp, AR〇NE ΟΧΕΤΑΝΕ _ _ _ _ _ _ _ _ 作为 作为 作为 具有 _ _ _ _ _ _ _ _ _ p p p p p p p p p p p p p p p p p p p p p p p p p p p p p p p p 40 parts by mass of a starting solution (D) of a 50-mass s % propylene carbonate solution of diphenyl ice (phenylthio)phenyl nickel hexahydrophosphate and stirred to thereby prepare a viscosity of 24 mPa.s ( A cationically polymerizable adhesive at 25 ° C). The surface of each of the acrylic resin film and the TAC film is coated with a cationically polymerizable adhesive obtained by wire coating to a thickness of about km, and the coated substrate is bonded to the polarizing film (polarizing film). Double sided. Then, after pressurizing with a blanket cylinder, a belt-type ultraviolet irradiation device (Fusion LH-6; output 1〇0%, conveyor speed 17.8 m/min) was used, and 3 to 3 90 nm was irradiated from the acrylic resin film side. The ultraviolet light having a cumulative light amount of i3 〇〇 mj/cm 2 was obtained as a polarizing plate having a protective film/cationic polymerizable adhesive layer/polarizer/cationic polymerizable adhesive layer/protective film of -27-201249945. [Example 3] EPICL〇N EXA_83〇CRp, which is #(10) parts by mass of the aromatic glycidyl ether (4), was mixed in a reaction vessel equipped with a stirrer, a reflux cooling H, a thermometer, a dropping funnel, and a nitrogen inlet, as (10) 237.5 parts by mass of ARONE OXETANE OXT-221 of the above oxygen cyclobutane oxycyclobutane compound (B), 162.5 parts of CELL0XIDE 3 作为 as an alicyclic epoxy compound (c), and as a cation 40 parts by mass of a polymerization initiator (9) of a 50% by mass of a propylene carbonate solution of diphenyl-4-(phenylthio)phenyl sulfonium phosphate and stirred to prepare a viscosity of 24 mPa.s (25 ° C) A cationically polymerizable adhesive. 3 In each of the acrylic resin film and the TAC film, each of the sheet 2 sheets is coated with a cationically polymerizable adhesive to obtain a thickness of about 砟 (7), and the cloth substrate is bonded to the polarizing film (polarized light). The film was then pressed, and then heated by a blanket cylinder, and irradiated from the side of the acrylic resin film by a belt type ultraviolet irradiation device (Fusion LH_6; output 1% by weight, belt speed: 8 m/knife). Ultraviolet rays having a cumulative light amount of 13 〇〇mJ/cm 2 to 390 ηηη were obtained as a polarizing plate having a protective film/cationic polymerizable adhesive layer/polarizer/cationic polymerizable adhesive layer/protective film thereon. [Example 4] In a reaction vessel equipped with a mixer, a reflux cooling $, a thermometer, a dropping funnel, and a nitrogen-conducting population, 100 parts by mass of EpiCL〇N EXA 83 was mixed as an aromatic glycidol mystery (8). CRp, 225 parts by mass of ARONE 0ΧΕΤΑΝΕ 〇χτ_22丨 having oxycyclobutane compound (B) having an oxycyclobutane group of 28-201249945 or more, and (2) parts by mass of CELL as an alicyclic epoxy compound (6) () XIDE 3_, as a cationic polymerization initiator (9), 40 parts of 4 parts of diphenyl_4_(phenylthio(tetra)(4) salt, 50% by mass of carbonic acid propylene vinegar solution, and as an epoxy group-containing oxime coupling agent (8) 50 parts by mass of 2_(3,4-epoxycyclohexylethyltrioxane) was added and mixed to prepare a cationically polymerizable adhesive having a viscosity of 24 mPa 3 (25 Å). Each of the surface of each of the film and the TAC film is coated with a cationically polymerizable adhesive obtained by wire ingot to have a thickness of about 祚, and then the σ海 coated substrate is attached to both sides of the polarizing film (polarizing film). Then 'use the blanket cylinder to pressurize and use A belt-type ultraviolet irradiation device (Fusion LH_6; output 1% by weight, conveyor speed: 17.8 m/min), and an ultraviolet light of 13 〇〇mJ/cm2 of 3 〇〇 to 39 〇mn is irradiated from the acrylic resin film side. A polarizing plate having a protective film/cationic polymerizable adhesive layer/polarizing plate/cationic polymerizable adhesive layer/protective film thereon is provided. [Example 5] A stirrer, a reflux condenser, a thermometer, a dropping funnel, and the like are provided. In the reaction container of the nitrogen gas inlet, 100 parts by mass of EPICL〇N EXA_83〇CRp as the aromatic glycidyl ether (A) and 35 parts of the oxygen cyclobutane compound (B) having (10) or more of the oxygen-cyclobutane group are mixed. 〇 mass parts of ARONE OXETANE OXT-221, 50 parts by mass of CELLOXIDE 3000 as the alicyclic epoxy compound (c), and 40 parts by mass of diphenyl _4_(phenyl sulphate as cationic polymerization initiator (D) Phenyl nickel hexafluorophosphorus-29- 201249945 50% by mass acid salt solution and a cationically polymerizable adhesive having a viscosity of 24 mPa.s (25 ° C) Resin film, TAC film表面μ φ The surface of each sheet of the film is coated with a cationically polymerizable splicer obtained by ingot coating to a thickness of about 2 μη1, and the coated substrate is attached to the front side (polarized film). Double-sided. Then 'use the blanket cylinder to pressurize and use the belt type UV irradiation device (Fusion LH-6; rim ΛΛ0/ σ, 100% out of the belt, conveyor speed 1 7.8 m / min)' A polarizing plate composed of a protective film/cationic polymerizable adhesive layer/polarizing sheet adhesive layer/protective film is irradiated with ultraviolet light having a cumulative light amount of I300 mj/cm2 of 300 to 390 nm from the side of the above-mentioned acrylic tree eucalyptus. [Example 6] A mixture of the above-mentioned/cationic polymerizable property in a reaction vessel having a stirrer, a reflux cooling@, a thermometer, a dropping funnel, and a nitrogen inlet was mixed as an aromatic glycidyl ether (in). EPICLONEXA_83〇CRp of a mass part, 375 parts by mass of ARONE OXETANE OXT_221 as an oxycyclobutane compound (B) having two or more oxycyclobutane groups, and 25 parts by mass of the alicyclic epoxy compound (c) CELL0XIDE 3000 and 40 parts by mass of a 50% by mass of a propylene carbonate solution of diphenyl-4-(phenylthio)phenylphosphonium hexaphosphate as a cationic polymerization initiator (D), and stirred thereby A cationically polymerizable adhesive having a viscosity of 25 mPa·s (25 t:) was prepared. On the surface of each of the acrylic resin film and the TAC film, the cationically polymerizable adhesive is applied by a wire bond to a thickness of about 2 μm, and the coated substrate is bonded to the polarizing film (polarized film). Double sided. Then, after pressurizing with a blanket cylinder, the ultraviolet ray irradiation apparatus (Fusion LH-6; output 〇〇〇 / /, belt speed: 17.8 m / min) of the belt type -30-201249945 was used to illuminate from the side of the above acrylic resin film. Ultraviolet rays having a cumulative light amount of i300 mJ/cm 2 from 3 Å to 390 nm were obtained as a polarizing plate having a protective film/cationic polymerizable adhesive layer/polarizer/cationic polymerizable adhesive layer/protective film thereon. [Comparative Example 1] In a reaction vessel equipped with a stirrer, a reflux condenser, a thermometer, a dropping funnel, and a nitrogen inlet, EPICL〇N EXA_83〇CRp, which is one part by mass of the aromatic glycidyl ether (VIII), was mixed. 4 parts by mass of ARONE OXETANE OXT-221 having 2 or more oxygen cyclobutane oxycyclobutane compounds (B), and 40 parts by mass of diphenyl _ as a cationic polymerization initiator (D) π mass ❶ / of 4_(phenylthio)phenylphosphonium hexafluorophosphate. The propylene carbonate solution was stirred and mixed, thereby preparing a cationically polymerizable adhesive having a viscosity of 24 mPa > s (25 ° C). On the surface of each of the acrylic resin film and the TAC film, the cationically polymerizable adhesive obtained by wire coating is brought into a thickness of about (10), and the cloth substrate is bonded to the polarizing film (the polarizing film is thin). Then, after pressurizing with a blanket cylinder, and using a conveyor belt type ^ external line device (Fusi () nLH seven output (10)%, conveyor speed of 7 "/ /), from the above acrylic resin film side irradiation (10) to A polarizing plate composed of an upper film/cationic polymerizable adhesive layer/polarizer/cationic splicer layer/protective film was obtained by an ultraviolet ray having a cumulative light amount of 39 〇〇mJ/cm2 at 39 〇 nm. 2) EPICOLN EXA_830CRP containing 1 part by mass of the aromatic glycidyl ether (A) in a reaction vessel equipped with a (4) machine, a reflux condenser, a thermometer, a dropping funnel, and a nitrogen inlet port of 31-201249945 395 parts by mass of ARONE OXETANE OXT_221 of two or more oxygen cyclobutane oxycyclobutane compounds (B), 50 parts by mass of CELLOXIDE 3000 as an alicyclic epoxy compound (6), and as a cationic polymerization initiator ( D) 40 mass * part of diphenyl, phenylthio) phenyl hydride;: 50% by mass of phosphate carbonated propylene vinegar solution and mixed, thereby modulating the viscosity of 25mPa.s (25 ° C) cation The polymerizable adhesive is applied to the surface of each of the surface of each of the acrylic resin film and the TAC film by wire coating, and the coated substrate is bonded to the polarizing film (polarizing film). Then, after the pressure is applied by a blanket cylinder, a belt type ultraviolet irradiation device (Fusion LH_6; output 1% by weight, conveyor speed minute) is used, and the acrylic resin film side is irradiated from 3 to 390 nm. Ultraviolet rays having a cumulative light amount of 1 300 mJ/cm 2 were obtained from a polarizing plate having a protective film/cationic polymerizable adhesive layer/polarizer/cationic polymerizable adhesive layer/protective film thereon. [Comparative Example 3] "With a blender In the reaction vessel of the reflux cooler, the temperature meter, the dropping funnel, and the nitrogen inlet, 'mixing in EPICL0N ΕχΑ8 as a wide mass part of the aromatic glycidyl ether (4), take Rp, as a (10), Oxygen %, butane-based oxygen 哀 丁 烷 化合物 化合物 化合物 AR AR AR AR AR AR AR AR AR AR AR AR 丨 丨 丨 丨 丨 丨 丨 丨 丨 丨 丨 丨 丨 丨 丨 丨 丨 丨 丨 丨 丨 丨 丨 丨 丨 丨 丨 丨 丨 丨 丨 丨 丨 作为40 parts by mass of diphenyl·4-(phenylthio)phenyl sulfaphos-32-201249945 acid salt as a cationic polymerization starting oxime (D), and the solution is stirred and borrowed. Thus, a cationically polymerizable adhesive having a viscosity of 23 mPa.s (25 t) was prepared. The cationically polymerizable adhesive obtained by coating the two sides of each of the acrylic resin film and the TAC film with a wire bond is formed to have a thickness of about >, and the coated substrate is attached to each of the working polarizers (polarized film). ) both sides. Then, after pressurizing with a blanket cylinder, and using a belt type ultraviolet irradiation device (Fusi () n LH seven output 1 Gg%, conveyor speed 1 7.8 m / min) 'from the above-mentioned 株 姑 + 戍 戍 戍 戍 烯 I I The ultraviolet light of the cumulative photometer m2 of 300 to 39 nm was irradiated on the film side to obtain a polarizing plate comprising a protective ruthenium film/cationic polymerizable adhesive layer/polarizer/cationic polymerizable adhesive layer/protective film. [Comparative Example 4] EPICL0N EXA_830CRp having 2 parts by mass of H as an aromatic glycidol hydride (4) in a reaction container having a mixing machine and a reflux condenser 'thermometer' dropping funnel and a nitrogen inlet, as having 2 50 parts by mass of ARONE®XETANE OXT_221 of the above oxycyclobutane oxycyclobutane compound (B), 400 parts by mass of CELL0XIDE 3_ as the alicyclic epoxy compound (6), and as a cationic polymerization initiator (9) 40 parts by mass of diphenyl·4_(phenylthio)phenyl hexafluorophosphate salt of 50 mass. The propyl carbonate solution was stirred and stirred to thereby modulate the cationically polymerizable adhesive of the viscosity UmPa.WMt:). On the surface of each of the acrylic resin film and the TAC film, the cationically polymerizable adhesive obtained by wire coating is used to have a thickness of about 3,000, and the coated substrate is bonded to the polarizing film (polarized film). Both sides. Then, after the pressure roller was pressurized, the ultraviolet irradiation device (Fusion LH_6; output 1%, conveyor speed 17.8 m/") of the conveyor type -33-201249945 was used, and the acrylic resin film side was irradiated 3 〇. Ultraviolet rays having a cumulative light amount of 13 〇〇mJ/cm 2 at 390 nm were obtained, and a polarizing plate having a protective film/cationic polymerizable adhesive layer/polarizer/cationic polymerizable adhesive layer/protective film thereon was obtained. [Comparative Example 5] In a reaction vessel equipped with a stirrer, a reflux condenser, a thermometer, a dropping funnel, and a nitrogen gas inlet, 100 parts by mass of EpiCL〇N EXA83〇CRp as an aromatic glycidol rough (A) was mixed as a fat. 400 parts by mass of CELL〇XIDE 3〇〇〇 of the cyclic epoxy compound (C), 曰=2 is a cationic polymerization initiator (D), 4 parts by mass of diphenyl-4 phenylthiophenyl)benzene A 5% by mass of a propylene carbonate solution of hexafluorophosphate is mixed and mixed, thereby preparing a cationic polymerizable agent having a viscosity of 22 mPa·s (25 (>c). 耆 in an acrylic resin film, a TAC film The surface of each sheet is coated with a cationically polymerizable adhesive obtained by ingot coating so as to be approximately "thickness", and then the coated substrate is bonded to both sides of the polarizing film (polarizing film). Adding money to the drum and using a belt-type ultraviolet-irradiated violet (FusiGn LH_6; output just %, conveyor speed 17.8 m/min)' ultraviolet light from the thin side of the acrylic resin to a cumulative light amount of 139 nm at 13 〇〇mJ/cm2 Get protected film / yang from top 1 A polarizing plate composed of a sub-polymerizable adhesive layer/polarizer/cationic adhesive layer/protective film. [Evaluation method of strength] The evaluation of the strength was evaluated by the following two items: -34- 201249945 ( 90-degree peel strength) The polarizing plates obtained in the examples and the comparative examples were cut into a test piece of a length of 80 nm and a width of 25 mm. The acrylic film of the test piece was placed on the aluminum plate of the adherend with an adhesive N〇. 56〇1 (made by Nitto Denko (manufacturing)). The laminated portion of the polarizer and the TAC film bonded to the end is peeled off from the side of the acrylic film, and the speed is 1 Omm/min based on JISz〇237. The 90-degree peel strength was measured under the conditions of 23 〇Γ and η tt m oyster L 50/gRH. In addition, the 90-degree peel strength: 3 N/25 mm or more was evaluated as "〇"; the evaluation was not performed on 3N/25 mm. "△"; those which did not reach 1.5 N/25 mm were evaluated as "X". (Fracture mode) The 90-degree peel strength was visually observed on the peeled surface after the test and was determined as follows. CF: Cationic polymerizable adhesive layer Agglomeration rupture, cation ♦ mouth The adhesive layer is peeled off from the acrylic resin film, and the CF-based cationically polymerizable adhesive layer is broken. Since the cationically polymerizable adhesive is followed by the acrylic resin film, it is judged that the adhesive strength to the acrylic resin film is good, and Further, the AF-based cationically polymerizable adhesive layer was judged to be "X,. -35-201249945 [Table 1] from the "acrylic resin: peeling".

[Table 2] Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Comparative Example 5 Aromatic glycidol_(A) EPICLON EXA-830CRP (part by mass) 100 100 100 100 100 Two or more oxygen cyclobutane groups Oxycyclobutane compound (B) '"ϊόο"""5〇"' ARONE OXETANE OXT-221 (parts by mass) 400 395 alicyclic epoxy compound (C) ""30〇" 400 CELLOXIDE 3000 (parts by mass) 5 Epoxy coupling agent containing epoxy group (E) 1.37 ~ 0.76 _ 0.10^ KBM-303 (parts by mass) 0.89 - 90 degree peel strength (N/25mm) 1.42 Evaluation of 90 degree peel strength XXXXX AF AF AF AF peeling mode AF peeling mode evaluation XXXXX

[Table 1] Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Aromatic glycidyl ether (A) EXA-830CRP (parts by mass) 100 100 100 100 100 100 2 or more oxygen ring Alkyloxycyclobutane compound (Β) λϋ〇ΝΕ ΟΧΕΤΑΝΕ ΟΧΤ-221 (parts by mass) 150 200 237.5 225 350 375 Month ring epoxy compound (C) 6ELLOXIDE 3000 (parts by mass) 250 200 162.5 125 50 25 Epoxy coupling agent containing epoxy group (E) iCBM-303 (parts by mass) __ 50 90 degree peel strength (N/25mm) 4.55 5.74 6.35 5.56 1.51 Evaluation of 90 degree peel strength 〇〇〇〇〇Δ Peeling mode CF CF Evaluation of CF CF CF CF Peeling Mode 〇〇〇〇〇〇 The abbreviations and the like in Tables 1 to 2 will be described. "EPICLON EXA-8 3 0CRP": bisphenol F diglycidol mystery "ARONE OXETANE OXT-221": double [Bu ethyl (3 _ _ 玉 衷 炫 ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) 9-Di-epoxy sulphate "KBM-303": 2-(3,4-epoxycyclohexyl)ethyltrioxoxazepine-36-201249945 It is known that the cationically polymerizable adhesive of the present invention Examples 1 to 6, in particular, have excellent adhesion strength to an acrylic resin film. On the other hand, it is understood that Comparative Example 1 is a state in which the alicyclic epoxy compound is not contained, and the strength is not good. Further, it is understood that the mass ratios of the oxygen butyl sulphonate compound and the alicyclic epoxy compound of Comparative Examples 2 to 4 are out of the range specified in the present invention, and the bonding strength of either of them is not good. Further, it is understood that Comparative Example 5 is a state in which no oxygen-cyclobutane compound is contained, and the strength is not good. [Simple description of the diagram] Benefits 〇 [Main component symbol description] None. -37-

Claims (1)

201249945 VII. Patent application scope: A cationically polymerizable adhesive comprising an aromatic glycidyl hydrazine (A), an oxocyclobutane compound (B) having two or more oxygen cycline groups (〇xetanyl), a cationically polymerizable adhesive of the alicyclic epoxy compound (C) represented by the following formula (7) and a cationic polymerization initiator (D), wherein the above aromatic glycidyl ether (A) is relative to 100 parts by mass of the above The above oxycyclobutane compound (B) is used in the range of 12 Å to parts by mass, and the alicyclic epoxy compound (c) is used in the range of 15 to 28 Å by mass. (In the formula (7), Ri, R2 and R3 each independently represent a hydrogen atom or a methyl group) 〇2. The cationically polymerizable adhesive according to the above item of the invention, wherein the above-mentioned scented glycidyl ether (A) It has two or more glycidyl ether bases. The cationically polymerizable adhesive according to claim 2, wherein the aromatic glycidyl ether (A) is selected from the group consisting of bisphenol A dimethyl condensate = oleyl ether and bisphenol F diglycidyl ether. More than one species. 4. The cationically polymerizable adhesive according to claim 1, wherein the molecular weight of the indole cyclobutane compound (B) is in the range of from 1 Torr to 8 Torr. 5. The cationically polymerizable adhesive of claim 4, wherein the oxycyclobutane compound (B) is a bis-ether. Iethyl (3-oxocyclobutane)] 6. The cationic poly-alicyclic epoxy compound (c)/bicyclic ring according to claim 1 of the patent scope is as follows: The cation concentration of one item: ^ #烯. - a step comprising a coupling with an epoxy group; a chelating agent, wherein the cation is a decane coupling agent having an epoxy group (E: an agent, wherein the cyclohexyl group) Triethoxy oxane, 2_(3,4_cyclo' from j.0,4-cyclooxymethoxyxane, 3-glycidoxypropyltriylhexyl)ethyltrioxypropene* The group consists of a group of yoghurt ceremonies and a group of 3 - epoxides and a polarizing plate, which are one or more types of cations. A polarizing plate for a film and a polarizer, wherein the above-mentioned cation-protecting agent is an ionic 4-bonding adhesive as disclosed in claims 1 to 8.阳离子 One cationic polymerization -39- 201249945 IV. Designated representative map: (1) The representative representative of the case is: None. (2) A brief description of the component symbols of this representative figure: None. 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: R2