TW201249946A - 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 and water resistance, and a polarizing plate obtained by using the same. The adhesiveness of the cationic polymerizable adhesive is on the order that the cationic polymerizable adhesive does not peel from a protective layer and/or a polarizing plate, and the protective layer does not crack even when the polarizing plate and others are bending. 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 having 2 or more oxetanyl groups (B), a silane coupling agent containing an alicyclic epoxy group (C), and a cationic polymerization initiator (D). The cationic polymerizable adhesive is characterized by using 300 to 395 parts by mass of the oxetane compound (B) and 5 to 100 parts by mass of the silane coupling agent (C) relative to 100 parts by mass of the aromatic glycidyl ether (A).

Description

201249946 VI. Description of the Invention: [Technical Field to Be Invented by the Invention] This invention relates to a cationically-added α1 cationically polymerizable adhesive, for example, firstly used as a liquid crystal display. [Previous technique of polarizing plate used] In the case of the subsequent agent, cationic polymerization is also performed for the energy supply which is not easily caused by atmospheric neutralization, and stops in the ultraviolet junction hole & the external line 4 Sexual succulent adhesives are being reported in recent years, and the use of adhesives for the development of the use of cations and sputums has been significantly improved in recent years. For example, _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ A compound having a glycidyl ether group containing a hydrolyzable mercapto group and a cationic agent, and having a chlorine content of 4,500 ppm (for example, referring to a cationically polymerizable adhesive agent described in the patent document) Contactability and excellent permeability due to low chlorine content θ is high in rigidity due to the upper cationically polymerizable adhesive, and the cationic adhesive is used, for example, on the protective film. When the polarizing plate is formed, when the polarizing plate is bent, a problem occurs in that the sub-polymerizable adhesive is cracked from the protective film and/or the adhesive layer on the polarizing film. The hardening of the cation can be hardened by using each of the manufactured oxygen. It is suitable for all kinds of cations of glycerin, and the degree of polymerization initiation. However, the above-mentioned polarizing sheet has a positive separation, or 201249946, and because of the above cationic polymerization property, it is in the protective film and The polarizer is coated with: := degree is relatively, the problem point. The protective film that constitutes the polarizing plate affects the optical characteristics of the polarizing plate, and the ancient system widely utilizes cellulose triacetate (TAC) thin: film aspect'- However, the TAC film has adverse effects due to the water droplets in the adhesive layer and the TAC film, and bubbles are given to the optical characteristic film, so that the adhesive layer in the polarizer reaches the eclipse polarizer. The problem of iodine discoloration, etc., this 'strongly pursues the water resistance of the adhesive layer. u, ask the more than the distortion point, in fact, is a strong agent, its Even when the polarizing plate is peeled off, the polarizing plate is not excellent in the adhesive agent and the water resistance. The continuation of the prior art document patent which seeks a cationic polymerization property and does not cause cracks from the protective film and/or the partial layer is sought. [Problem to be Solved by the Invention] In order to solve the problem of the present invention, a cationically polymerizable adhesive and a polarizing plate obtained using the same are provided. This cationically polymerizable adhesive is excellent in the degree of adhesion and the like which is peeled off from the protective film and/or the polarizer even if it is bent, and the degree of cracking of the adhesive layer does not occur. 201249946 [ MEANS FOR SOLVING THE PROBLEMS The inventors of the present invention have conducted research to solve the above problems and have studied a combination of various cationically polymerizable compounds. Among them, in the composition containing an aromatic glycidyl ether, an alicyclic fluorenyl group, a hospital coupling agent, and a cationic polymerization initiator, when the second = fragrant galacyl ether is used as a main component, it is found that An adhesive with improved adhesion to a certain degree of strength is obtained. However, it is still impossible to prevent (4) the self-protecting film and/or the polarizer: the crack of the coating layer. And the inventors of the present invention and the like, based on the reduction of the rigidity of the adhesive layer, the one-step improvement followed by the strong sound of the adhesive layer, the oxygen-inducing ring, and the combination of the butane in the above-mentioned adhesive (. as a %% decane compound' When a monofunctional oxycyclobutane compound having an oxygen ring: earth or XeUnyl is used, the knives are lowered in the knives, and good adhesion strength cannot be obtained. In the present inventors, the inventors of the present invention reviewed a compound having two or more oxygen cyclobutane 1 gas cyclobutanes in combination. Quantitative 'discovered with respect to aromatic glycidol _, only the special: an oxygen ring butyl compound having a ring r group and a problem. In the case of the earth-alkali coupling agent, the polarizing plate obtained by the present invention, which is obtained by following the cationic polymerization, having two cationically polymerizable adhesives of the present invention, and a polarizing plate and a protective film, can be solved. , ,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,, , the above-mentioned gas-based Ding Bu, human scented scented glycidyl ether (A) i 〇〇 is used within the range:: = = (8) is in the range of 300 to 395 parts by mass, the squirting coupler (C) is 5 to use within the scope of the scenery. [1] The effect of the invention is that the cationically polymerizable adhesive of the present invention is excellent in adhesion, and the polarizing plate or the like obtained by using the adhesive is not caused by bending. The 讅 4 Μ and/or the polarizer is peeled off, and the adhesive layer is free of cracks. Further, the cationically polymerizable adhesive of the invention has excellent water resistance. Therefore, when the adhesive of the present invention is used in the production of a polarizing plate, bubbles or foaming in the laminated body constituting the polarizing plate can be suppressed. Further, since the cationically polymerizable adhesive of the present invention has low puncture properties and good curability, for example, even when the adhesive of the present invention is applied onto the protective film and the polarizer, no problem occurs on the adhesive layer. The sentence ' does not adversely affect the optical properties of the polarizer. [Embodiment] First, the above aromatic glycidyl ether (Α) will be described. The above aromatic glycidyl ether (Α) is an essential component when it has an adhesive property. When the above-mentioned aromatic glycidyl ether (Α) is used, two or more glycidyl ether groups are used, and it is preferable to provide good adhesion, and it is more preferable to use two to six. As the aromatic glycidyl ether, for example, bisphenol hydrazine glycidyl ether, bisphenol F glycidyl ether, bisphenol § glycidyl ether, and bisphenol AD glycidyl ether can be used, among which a double wheel type A is used. Glycidol scale, bisphenol p-type glycidyl ether is preferred. 201249946 The soul of the double-seeking type A glycidylation mystery can be used, for example: double singular a succinyl ether. For example, the F-type glycidyl ether can be used as the F-type glycidyl ether. The aromatic glycidyl ether (A) can improve the hardenability and moderately adjust the hardness of the cured product, and it is known from the viewpoint of the use of bisphenol A diglycidyl ether and bisphenol. It is preferred that one or more of F diglycidyl ether is in the group. Further, in the present invention, the above aromatic glycidyl ether (VIII) and other glycidyl hydrazine may be used in combination as long as it does not impair the effects of the present invention. Other glycidyl ethers can be used, for example, three thioglycolate, glycidol mystery, glycerol triglycidide, polyglycerol triacetin, ether, diglycerin, triglycidoxime, etc., with 3 glycidol Shouted: aliphatic glycidyl compound; and trimethylolpropane diglycidyl ether 'I1,6' hexanediol diglycidil test, μ-butan: alcohol diglycidyl dihexane hexane dimethanol diglycidyl Ether, propylene glycol diglycidyl ether: glycidyl-based compound having two glycidyl groups, such as glycerol = water glycerol.

The other glycidyl bond may be used for the condensation of the above-mentioned aromatic glycidyl ether (hydroquinone), hydrogenated bisphenol A, bisphenol F glycidyl ether or the like. "Hybrid glyceryl ether or gas oxime: Oxygen oxime on the oxirane compound (Β) is described. And / or polarizer (4) from ^ D 'especially in order to prevent the viscosity of the protective film from becoming necessary Then, the agent layer is cracked and is low 201249946 and 'the above-mentioned oxycyclobutane compound (B) is in the range of 300 to 395 with respect to the above-mentioned aromatic glycidol compound. The above-mentioned oxycyclobutane is necessary in solving the problem of the present invention. In the case of the compound (B), two or more oxocyclobutane groups may be used, and the oxocyclobutane compound (Β) may be specifically represented by the formula (1) or (2). A) It is preferable that Q is in the range of 100 parts by mass of the mass, and it is preferable to use a cation to be aggregated to four.

The above alkyl group or the third group is, for example, the above formula (1), (2), and R is independently

a linear, branched or cyclic aryl group, an aralkyl group, a furyl group or a thienyl group having a carbon number of 1 C to 6; an organic residue of R 2 2^; Z each independently represents an oxygen knife R1 The straight chain of carbon number 1 to 6 is, for example, methyl, ethyl, n- or yl, pentyl, hexyl and cyclohexyl, etc., naphthyl, anthracenylphenyl and diphenylphenyl, etc. Ethyl and the like. And in the above formula (1), R 2 represents a 2 ^ : linear, branched or cyclic alkyl group of a carbon atom (oxyalkylene), a phenyl group, and a benzene group (3) And the structure shown in (4). The ground represents a hydrogen atom, a burnt group, and a fluorenyl group each independently represents a [sub or sulfur atom. , branched or cyclic isopropyl, Ortho or iso, and aryl, 'and aralkyl valent organic residues, having 4 to 30 fluorenyl groups and the following composition 201249946 Linear, branched or cyclic alkyl group

It is preferred that the atom is broken, for example, a poly(oxyethylene) group or a poly(oxygen) group.

In the above formula (3), R3 represents an oxygen atom 'sulfur atom, CH2, nh, SO, S02, C(CF3)2 or C(CH3)2. C-R^-d:- (4) In the above formula (4), 'R4' represents a stretching group having from 1 to 6 carbon atoms, an extended aryl group, and a functional group represented by the following formula (5).

In the above formula (5), a represents an integer of 1 to 6, and b represents an integer of 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 oxygen cyclobutane structures is, for example, commercially available ARONE OXETANE OXT-221 'AR0NE OXETANE 0XT-121, ARONE OXETANE OXT-223 (the above is manufactured by East Asia Synthetic Co., Ltd.) ETERNACOLL 0ΧΒΡ, ETERNACOLL 0ΧΤΡ, ETERNACOLL 0ΧΙΡΑ (the above is manufactured by Ube Industries Co., Ltd.). -10- 201249946 Degree 2 molecular weight, the range is better. h GG is in the range of 1 fm 0* 接着 之 之 系 系 系 系 系 系 系 系 系 系 系 系 例如 例如 例如 接着 为了 为了 为了 为了 为了 为了 为了 为了 为了 为了 为了 为了 为了 为了 为了 为了 为了 为了 为了 为了 为了 为了 为了 为了 为了 为了 为了The molecular weight of the above-mentioned oxygen ring butyl group is the same as that of the amine compound (8) having a low degree of molecular weight, and the molecular weight of the compound (8) is represented by the formula m. R2 Ding is better, especially in the formula! Petrochemical, methylene double π_ethyl (3_oxycyclobutene hardened 蛀芏10, ; J τ ^ clock film thickness is thinner, due to Further, it is particularly preferable for the adhesiveness. 'And' the towel of the present invention, if not damaged, may be used in combination with the above-mentioned oxygen, the butyl compound (8) and the butyl compound. ##κ^ One of the oxygen-cyclobutane groups is oxocyclobutane, and a compound represented by the following formula (6) is used. R1?r〇R2 (8) Ο (In the formula (6), Ri represents a hydrogen atom and a carbon number!妷1 to 5 夕&amp; A hydrogen atom, a branchable oxygen hospital or a carbon number, a burnt, a carbon number of 1 to 10, a fat square Family structure). It is more suitable for coating the film thickness of the low-viscosity <100 to 500 polarizer and the protective layer. In addition, the configuration can be used to improve the hardenability by using the above-mentioned ethyl group as the ethyl ether. The range of the effect is an oxocyclobutane compound such as a group of 8 or a group; and R2 represents a group ring structure 201249946. In the above formula (6), for example, a compound having a carbon number of 1 to 8 which can constitute R1 can be cited. a group having a carbon number of 1 to 5, wherein R1 has a carbon number of 1 to 5, in the formula (6),曱氡 exemplified by: 曱 甲基 甲基 、, ethoxy methoxy, propyl methoxy, propyl ethoxy, etc. Further, in the above 诵 烷 烷 式 式 k formula (6), can constitute R Examples of the carbon number of the crucible of 1 to 6 may include hydroxymethyl, hydroxyethyl, hydroxypropyl, etc. 5 ! Λ AA 1^ In the above formula (6), R2 may be formed. The calcination group having a carbon number of 1 to 10 which may be branched may be, for example, a linear alkyl group such as a methyl group or an ethyl group or a propyl group: a branched alkyl group such as a hexyl group or the like. Medium, which can constitute R2 fat The ring-type structure may, for example, be a ruthenium group or a hexyl group. The cyclohexyl group or the like may have an alkyl group substituted for 11 atoms. In the above formula (6), an aromatic group of R2 may be formed. Examples of the structure include, for example, abbreviated formulas. The above-mentioned phenyl group may have an alkyl group substituted with a hydrogen atom. The above description of the above decane coupling agent (c). The above decane coupling agent (c) It is necessary to impart adhesiveness, water resistance, and strength of the adhesive layer coating film. Further, the above-mentioned breaking coupler (c) is 5 to 1 with respect to 100 parts by mass of the above-mentioned aromatic shrinkage KA). The use of the test within the scope of the mass part is necessary to solve the problem of the present invention. = Shi Xi siu coupling agent (C), such as a decane coupling agent having an epoxy group containing an epoxy group, a cyclic oxime-type epoxy group is not particularly limited, and can be used -12-201249946 For example: 2-(3 , 4_epoxycyclohexyl)ethyltrimethoxine, 2 (3,4-epoxy-hydroxyhexyl)ethyltriethoxylate, 2_(34 epoxycyclohexyl)ethane Propionate, 2·(3,4-epoxycyclohexyl)ethyltriisopropoxy octa 2 (3,4'epoxycyclohexyl)ethylmethyldimethoxydecane, I '4 ethoxylated hexyl}ethylmethyldiethoxy decane, 2_(3,4-epoxyhexyl)ethylmethyldi-n-propoxy calcination, 2_(3,4 epoxy ring Hexyl)-ethylmethyldiisopropoxy sylvestre, 2_(3,4-epoxycyclohexyl)ethyl-methylmethoxy; oxime, 2-(3,4-epoxy ring Hexyl)ethyldimethyl ethoxylate 2 (3,4-epoxycyclohexyl)ethyldiindenylpropane, 2 (3,4ro ring-based cyclohexyl)ethyldimethyliso Propoxy oxane, 2-(3,4·epoxy%hexyl)ethylethyldimethoxydecane, 2(3,4-epoxycyclohexyl)ethylethyl-ethoxypropane, and the like. Among these, from the viewpoint of further improving curability, adhesion, and water resistance, it is selected from 2 (3,4 epoxycyclohexyl)ethyltrimethoxydecane and 2·(34-epoxy ring). It is preferred that one or more of hexyl)ethyltriethoxylate is formed into a group. Further, in the present invention, as in the range of the effects of the present invention, the above-mentioned decane coupling agent (C) may be used in combination with another decane coupling agent, and the above other decane coupling agent may be used, for example, a 3-ring. Oxypropoxypropyltrimethoxydecane, 3_glycidoxypropyltriethoxydecane, glycidoxypropylsulfonyldiethoxydecane, 3_glycidoxypropylmethyldi a decane coupling agent such as a decane or the like. Next, the above cationic polymerization initiator will be described. The cationic polymerization initiator (D) used in the present invention is, for example, a compound which can generate an acid which starts cationic polymerization by irradiation with an energy ray such as ultraviolet rays. Further, the cationic polymerization initiator (D) may be, for example, an aromatic oxime, an aromatic oxime, an aromatic diazonium, an aromatic ammonium or a thianthrenium. Thiotonantium (Thioxanthonium), (2,4-cyclopentadiene-buyl)!^-mercaptoethyl)benzene]_Fe cation; anion moiety is BF4., PF6-, SbF6-, [BX4 a rust salt composed of - (except for a phenyl group in which X is substituted with at least two or more fluorine or trifluoromethyl groups). 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 Fluorine based) 叾 S S salt, monophenyl 4-(phenylthio)phenyl hexahydrofluoride, dipyridyl-4 -(phenylthio)phenyl hexafluoroantimonate, Diphenyl _ 4 _ (phenylthio) phenyl fluorene tetrafluoroborate, diphenyl-4-(phenylthio)phenyl hydrazine (pentafluorophenyl) decanoate, triphenyl sulfonium hexafluoride Phosphate, triphenylsulfonium hexafluoroantimonate, triphenylsulfonium tetrafluoroborate, triphenylsulfonium (pentafluorophenyl)borate, bis[4-(di(4-(2-hydroxy)) Oxy))phenyldihydrothio)phenyl]sulfuric bishexafluorophosphate, bis[4-(bis(4-(2-hydroxyethoxy))phenyldihydrothio)phenyl]sulfide Bis(hexafluoroantimonate), bis[4-(bis(4-(2-hydroxyethoxy))phenyldihydrothio)phenyl]sulfide ditetrafluoroborate, bis[4_(bis(4_( 2_经基乙Yl)) phenyl-dihydro-thio) phenyl] sulfide tetrakis (pentafluorophenyl) borate. As the above aromatic phosphonium salt, for example, diphenylphosphonium hexafluorophosphate, diphenylphosphonium hexafluoroantimonate, diphenylphosphonium tetrafluoroborate, diphenylphosphonium (pentafluorophenyl) borate can be used. , bis(dodecylphenyl)phosphonium hexafluorophosphate, bis(dodecylphenyl)phosphonium hexafluoroantimonate, bis(dodecylbenzene) -14- 201249946 鍈tetrafluoroborate , bis(dodecylphenyl)phosphonium (penta-phenyl)borate, 4-methylphenyl-4-(1-methylethyl)phenylphosphonium hexafluorophosphate, 4-fluorenyl Phenyl-4-(1-mercaptoethyl) stilbene hexafluoroantimonate, 4-mercaptophenyl-4-(1-indolylethyl) stupyl fluorene tetrafluoroborate, indomethacin Phenyl_4_(1_mercaptoethyl)benyl quinone (pentafluorophenyl)-decarboxylate or the like. And 'the above aromatic diazonium salt can be used, for example, phenyldiazonium hexahydrochloride, phenyldiazonium hexafluoroantimonate, phenyldiazonium tetrafluoroborate, phenyldiazonium hydride (pentafluorobenzene) Base) borate and the like. Further, 'the above aromatic ammonium salt can be used, for example, a benzyl-2-cyano group, a hexafluoroate, a 1-benzyl-2-cyanopyridine hexafluoroantimonate, a 1-benzyl-2- Cyano acridine tetrafluoroborate, 丨_节基-2-cyanoβpyridinium (pentafluorophenyl) succinate, 1-(naphthylquinone)_2-cyanoacridine hexafluorophosphate, 1_(naphthyl)-2-cyano. Pyridinium hexafluoroantimonate, naphthoquinone) 2 - cyano acridine tetrafluoroborate, 1-(naphthylmethyl) 2-cyanoacridinium (pentafluorophenyl) borate. Further, as the above thioxanthone rust salt, for example, S-biphenyl-2-isopropyl thioxanthone hexafluorophosphate or the like can be used. Further, as the above (2,4-cyclodecadien-1-yl)[(1-methylethyl)benzene]-Fe salt, for example, (2,4-cyclopentadien-1-yl) can be used. (1-mercaptoethyl)benzene]-Fe(II) hexafluorophosphate, (2,4-cyclopentadien-1-yl)[(1-methylethyl)benzene]-Fe(II) Hexafluoroantimonate, (2,4-cyclopentadien-1-yl)[(1-methylethyl)benzene]-Fe(II) tetrafluoroborate, (2,4-cyclopentadiene) -1-yl)[(1-methylethyl)benzene]-Fe(II) quinone (pentafluorophenyl) shed acid salt. The above cationic polymerization initiator (D) is, for example, commercially available CPI-1 OOP, CPI-101A, CPI-110P, CPI-200K, CPI-210S (above -15-201249946 SAN-APRO (manufactured by the company); CYRACURE Photohardening Starter UVI-6990, CYRACURE Photohardening Starter UVI-6992, CYRACURE Photohardening Starter 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 manufactured by ADEKA); CI-5102, CI-2855 (above manufactured by Sakamoto Soda (share)); San -Aid SI-60L, San-Aid SI-80L, San-Aid SI-100L &gt; San-Aid SI-110L 'San-Aid SI-180L &gt; San-Aid SI-110, San-Aid SI-180 ( The above is manufactured by Sanshin Chemical Industry Co., Ltd.; ESACURE 1064, ESACURE 1187 (manufactured by LAMBERTI); OMNICAT 550 (manufactured by IGM RESIN); IRGACURE 250 (manufactured by BASF JAPAN); RHODORSIL PHOTOINITIATOR 2074 (RHODIA) JAPAN (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 cationically polymerizable adhesive of the present invention may further contain a photosensitizer (E). When the cationically polymerizable adhesive of the present invention is used in the subsequent step of the polarizer and the protective film, the cationic polymerization may be applied to the protective film. After the polarizer is placed on the coated surface, the ultraviolet ray irradiation described later is performed from the side of the protective film to cure the cationically polymerizable adhesive. In this case, when the protective film is made of a protective film (for example, a taC film or the like) which is difficult to penetrate light of 380 nm or more, the protective film is improved from the viewpoint of improving the hardenability of the cationically polymerizable adhesive. It is preferred to contain the above-mentioned photosensitizer (E). As the photo sensitizer (E), for example, hydrazine, hydrazine, D-zegitone, succinyl ketone, benzoin isopropyl ether, and derivatives of the compounds can be used. Among these, it is preferable to use a light having a wavelength of 38 〇 nm or more for maximum absorption, and it is more preferable to use a lanthanoid compound. The above lanthanoid compound which exhibits maximum absorption at a wavelength of 3 80 nm or more can be, for example, 9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 9,1 fluorene-dipropoxy fluorene, 9,10-diisopropoxy oxime, 91 〇-dibutoxy fluorene, 9,10-dipentoxy fluorene, 9,10-dihexyloxy fluorene, 9,10-bis(2-oxime Ethyloxy)anthracene, 9,10-bis(2-ethoxyethoxy)anthracene, 9,10-bis(2-butoxyethoxy)anthracene, 9,10-bis(3-butenyl) Propyloxy) hydrazine, 2-hydrazino or 2-ethyl-9,10-dimethoxyanthracene, 2-methyl or 2-ethyl-9,10-diethoxyanthracene, 2-methyl Or 2-ethyl-9,10-dipropoxyfluorene, 2-methyl or 2-ethyl-9,10-diisopropoxy fluorene, 2-mercapto or 2-ethyl-9,10 - Dibutyloxy hydrazine, 2-mercapto or 2-ethyl-9,10-dipentyloxy fluorene, 2-mercapto or 2-ethyl-9,10-dihexyloxy hydrazine, etc., commercially available The amount of the above-mentioned photosensitizer (E), such as "UVS-1331" (manufactured by Kawasaki Chemical Industry Co., Ltd.) and KAYACURE DETX-S (manufactured by Sakamoto Chemical Co., Ltd.), relative to the above aromatic glycidol Ether (A) 100 parts by mass, desirably in the range of 0.5 to 10 parts by mass . Further, in the case of using the above-mentioned photosensitizer (E), in order to enlarge the sensitization wavelength region of the above cationic polymerization initiator (D), the cationic poly-17-201249946 of the present invention is combined with photo-sensitization aid. The hardenability of the bonding agent is more enhancer (F). Etc., etc., so that ... dimethoxy-Cai, 彳:: Xiao Di and Cai line compound one-oxy-Cai, Di-propoxy-Cai, 2-base Cai, Jia.丨, 4--butylene naphthalene or the like is 100 parts by mass of the glycidyl ether (A), and it is desirable to use it within the aromatic condensation. Expectations are 〇·5 to 1. Scope of parts by mass Next, for the cationic poly argon of the present invention. The cationically polymerizable adhesive of the present invention contains: an upper glycidyl ether (A), a gas ring butyl compound having two or more oxygen oxime bases, and a valence compound (B). Alicyclic epoxy/conditional coupling agent (C), "Meson polymerization initiator (D), and % escaping <Upper glare breaker fish light sensitizer (F)' In the range 2 which does not affect the effects of the present invention, various additives may be contained. The above additives may be used as a shake aid, a leveling agent, an antioxidant, a urethane, a enamel, a heat stabilizer, a light stabilizer, a lacquer brightener, a foaming agent, a thermoplastic resin, and a thermosetting property. Resin, organic solvent', conductivity imparting agent, antistatic agent, moisture permeability improving agent, water repellent, zhonggongxuan body, crystal water compound, flame retardant, water absorbing agent, moisture absorbent, deodorizer , foam stabilizer, defoamer, anti-mold agent, preservative: anti-algae agent, anti-caking agent, water-repellent agent, organic and inorganic water-soluble compounds. In addition, in addition to the above, in order to further reduce the rigidity of the cationically polymerizable adhesive of the present invention, a polyol such as a polyether polyol may be contained. Further, in addition to the polyol, the curing property and the low-strength property of the cationically polymerizable adhesive of the present invention are further improved to (4), and may contain ethylene ether or oxolane or alicyclic epoxy. A cationically polymerizable compound such as a compound. As the vinyl ether, hexanediol diethylene sulfonium, diethylenedivinyl ether, neopentyl glycol divinyl ketone 1, or the like can be used. For example: butanediol divinyl ether, alcohol divinyl ether, triethylene glycol diether ether, cyclohexane dimethanol diethylene, and up to 4 alicyclic epoxy groups of epoxy compounds described above The alicyclic ring 4 is an alicyclic epoxy compound represented by the following formula (7).

Further, an epoxy compound having two alicyclic gas-based bases can be, for example, a compound represented by the following formula (8): ?^ 2 2 3,4·epoxy ring Alkenylmethyl-3,4-%oxycyclohexanecarboxylate (in the formula (8), a is a humanized 4 2 , a caprolactone modified product thereof (in the formula (8) ° ^ 3 J τ 'a is a compound of 1), 201249946 methyl caprolactone modification (structural formula (9) and structural formula (ι)) and its internal reforming (structural formula (11) and structure a compound of the formula (12)) or the formula U3).

〇 (8) (general + 0

a represents 0 or 1) (9) CII3 -aia-c-CHy-CH-aij-c-o-aijs ο ο Μ CII3 CH3ci &lt;k lo

(10)

ο ο (11) (12)

(13) Further, the above epoxy compound having two alicyclic epoxy groups may also give a compound represented by the following formula (14): $4. -20- (14) 201249946 R1 R6 R5

(R1 to R0 in the formula (14) each independently represent a hydrogen atom or a breaking group of 1 to 6). As the compound represented by the above formula (14), specifically, a dicyclohexyl-3,3'-diepoxide can be used. Further, as the epoxy compound having three alicyclic epoxy groups, a compound represented by the following formula (15) can be used.

0

(15)

Or 1, these may be, for example, commercially available from Daicel (in the formula (15), a and b are each independently represented as the same or different). An alicyclic epoxy compound represented by the formula (15), EPOLEAD GT301, EPOLEAD GT302 (manufactured by the above-mentioned industry). Further, as the alicyclic gas oxy-compound having four alicyclic epoxy groups, for example, a compound represented by the following formula (16) can be used. (16)201249946

CM jj*Cw[ O -^Cll C - o o 『*~~~C-|&lt;J -(Cll2^-C |〇~CHf

Each of d to d represents independently or 1, and these may be the same or different in the formula (16). The alicyclic epoxy compound represented by the above formula (16) is, for example, commercially available EPOLEAD GT4〇1, Ep〇LEAD 〇τ4〇3 (the above is manufactured by Chemical Industry Co., Ltd.). The cationically polymerizable graft of the present invention also has a low viscosity, and has a viscosity at a temperature of 10 to 1 ΛΛ 00 mPa.s. Further, the viscosity of the above cationically polymerizable adhesive is determined. Measurement of m W at 25 C Next, the cation method of the present invention will be described. The method for producing a cationically polymerizable::agent of the present invention is produced by the following method. For example, in the case of the cation-type k UJ丨-xs-based adhesive of the present invention, for example, a container of the 曰 曰 machine, the J*.+. 4 water which has been previously prepared by stirring and stirring is used. Glyceryl ether (A), the above-mentioned 襄 迷 香 香 乂 % % % % % % % % % % % % % % % % % % % % % % % % % % % % % % % % ψ ψ ψ ψ ψ ψ ψ ψ ψ ψ ψ ψ It can be manufactured as necessary. -22-201249946 The cationically polymerizable adhesive of the present invention can be cured by irradiation with an energy ray such as ultraviolet rays. Further, the cationically polymerizable adhesive of the present invention first exhibits a susceptibility by irradiation with an energy ray such as ultraviolet rays. The irradiation of the energy rays of the ultraviolet rays or the like is preferably in the range of 1 〇 to 5000 mJ/cm 2 , more preferably in the range of 2 〇 to 25 〇〇 mJ/cm 2 , particularly preferably in the range of 30 to 1,500 mJ/cm 2 . . A source of ultraviolet light can be, for example, a conventional lamp such as a xenon lamp, a mercury xenon lamp, a metal halogen lamp, a pressurized mercury lamp, or a low pressure mercury lamp. And 'UV exposure is UV CHECKER; UV Power

PucK (II) (available from Electronic Instrumentation and Technology, Inc.) uses a value measured in a wavelength region of 300 to 39 〇 nm as a reference ' and 'may also be necessary to pass the above energy ray after irradiation with 40 to 8 〇C is heated to the left to further promote hardening. Next, the polarizing plate of the present invention will be described. The polarizing plate of the present invention is a protective film and a polarizer which are formed by an adhesive layer composed of the above cationically polymerizable adhesive. As the protective film, for example, an acrylic resin, a fluorene resin, an epoxy resin, a fluorine resin, a polystyrene resin, a polyester resin, a polysulfone resin, a polyacrylate resin, or a polyvinyl chloride resin can be used.曰 曰 — 氯 氯 氯 ' 降 降 降 降 降 降 降 降 降 降 降 降 降 烯 降 降 降 降 降 降 降 烯 烯 烯 烯 烯 烯 烯 烯 烯 烯 烯 烯 烯 烯 烯 烯 烯 烯 烯 烯 烯PC (polycarbonate), PBT (polybutylene terephthalate), modified PPE (polyphenylene ether), PEN (polyethylene naphthalate; 23-201249946 ester), ΡΕΤ (poly pairs A biodegradable film of a biofilm such as a dibasic acid or a polylactic acid polymer, such as a vinegar or a film or a flaky material. Further, the acrylic resin may be (Tg) 1 〇 (rC or more of the acrylic resin glass transition temperature, such that the content may be averaged, and, 'raw (F-based) acrylic resin, as the above-mentioned elastomer The protective film of the elastic body of the seven-week elastic body is located in the protective thin film. The waist and the direction of the polarizing plate of the present invention are made in the thickness of the protective film according to the use of the protective film: Preferably, the polarizer is preferably in the range of 50 ym. U is 5 # m and the polarizer can be used without, for example, the flat 7 咕 π A column can be used in various places, and the acetic acid can be used. The dilute copolymer is a partial compound such as: a wide material, a vinyl material composed of a material, a 7-sex molecular combination, / a soil material and a moth or a dichroic material. The material is uniaxial. Add 妯土. + L 丨 丨 Wangmu 4 dichroic stretch film # t ' soil material, 冱 early axis stretching derived from the alcohol to the monument ~ color material; polyethylene treatment or poly The gas of ethylene goes to sleep and the acid is weak to the film. The polyene system such as Ganmufeng s夂 treatment, temple It is preferable to use a polyvinyl alcohol to thin the M &amp; n &gt; singularly squeezing and squeezing/adhesive film and a film adsorbing an existing substance such as iodine. In addition, the polarizing plate of the present invention is, for example, coated. The above-mentioned protective film can be shot by the above-mentioned protective film, and the coated surface is irradiated with ultraviolet rays in the sputum, and then manufactured on the coated surface, and then... Applying the above-mentioned engraved adhesive to the cation-preserving film on the cation-preserving film, and then placing the polarizer on the surface of the slab--24-201249946, and then, from the above protection And the polarizing plate of the present invention may be applied to the cationically polymerizable adhesive porphyrit polarizer by applying the above-mentioned ultraviolet rays to the polarizing plate of the present invention, and then irradiating the coated surface on the coated surface to irradiate the above amount. And the above-mentioned polarizing light is applied to the above-mentioned positive film (four) film, and then the protective film is cut on the coating polymerizable adhesive, and the protective film is irradiated with the above-mentioned amount of ultraviolet rays 'then' from the above polarizing plate By the above yang The sub-polymerization is preferably used to form the thickness of the layer of the present invention, and is based on an optical property of an adhesive composed of a sputum agent, and is specifically as thin as possible for the reason of 5 to the following. In the polarizing plate of the invention, for example, the above-mentioned cationic 綮A is applied to the surface of the soap, and the above-mentioned amount of the D-type adhesive is applied to the coated surface of the two protective films, and then placed on the coated surface, followed by the polarizer. Surface: by coating the coated surface with a polymerizable adhesive layer/polarizing sheet/, a laminate of a protective film/anyang film, and a polymerizable adhesive layer/protective coating of the above cationic polymerizability One side of the second protective film of the agent 2 is placed on both sides of the polarizer, and then the above laminated body is respectively carried on the upper:::垓 coated surface.制成 Ή 紫外线 紫外线 紫外线 紫外线 : : 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 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 阳离子 阳离子 阳离子 阳离子 阳离子. ', cloth method, spray method, etc. = the above method, the invention becomes a mobile communication such as a mobile phone: the board can be used, for example, in a display of a brain-building, a portable game machine, etc.: LCD TV, personal electric -25-201249946 [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 P〇VAl PVA-117H [K-ray alcohol, polymerization degree 丨7 〇〇, complete saponification, powder form] manufactured by KURARAY Co., Ltd. in water] (non-volatile content of 8 mass%) was coated on the release film with a coating bar 'then' 纟 8 〇. . After drying for 5 minutes in the environment, the above-mentioned release film was removed to prepare a polyethylene film having a thickness. . Next, the obtained polyvinyl alcohol film was fixed to a stretching machine, and the film was stretched to a doubling direction in a uniaxial direction in warm water of 4 ° C. After removing the water adhering to the surface of the obtained stretched film, the stretched film is immersed in an aqueous solution containing 2 parts by mass of iodine, 2 parts by mass of potassium iodide, and 100 parts by mass of water adjusted to 3 〇〇c. . Knife /, the above-mentioned stretched film was immersed in a solution containing 2 parts by mass of moth detoxification and 5 parts by mass of water adjusted to %. 〃 The above-mentioned impregnated stretched film is washed in pure water adjusted to 8 and dried in an environment of 65 ° C, thereby obtaining iodine and aligning the surface of the stretched film composed of polyalcohol. Polarized film). [Numerical Example 1] In a reaction vessel equipped with a stirrer, a reflux condenser, a thermometer, a dropping funnel, and a nitrogen inlet, 100 parts by mass of epiclinz〇 EXA83〇cRp as an aromatic glycosaminoglycan (A) was mixed. 300 parts by mass of ARONE OXETANE OXT-221 as an oxocyclobutane compound (B) having 2-26 to 201249946 or more of an oxocyclobutane group, and a decane coupling agent (C) containing an alicyclic epoxy group 100 parts by mass of KBM-3 03, as a cationic polymerization initiator (D), 40 parts by mass of di- phenyl-4-phenylsulfonyl hexafluorophosphate, 50% by mass of propylene carbonate a solution, 2 to 5 parts by mass of 9,10-dibutoxyanthracene as the photosensitizer (E), and 2.5 parts by mass of 1,4 -diethoxynaphthalene as a photosensitizer (F) By stirring, a cationically polymerizable adhesive having a viscosity of 25 mPa.s (25 ° C) was prepared. The cationically polymerizable adhesive obtained by coating the surface of each of the acrylic resin film and the TAC film, which are mainly composed of polymethyl methacrylate, is made to have a thickness of about 2 #m. Then, the ruthenium-coated substrate is bonded to both sides of the polarizer (polarizing film). Then, after pressurizing with a blanket cylinder, a belt type ultraviolet irradiation device (Fusion LH-6; output 100 〇/〇, belt speed 17 8 m/min) was used, and the acrylic resin film side was irradiated from 3 〇〇 to 390 nm. The ultraviolet light having a light amount of UOOmJ/cm2 was accumulated to obtain a polarizing plate comprising a protective film/cationic polymerizable adhesive layer/polarizer/cationic polymerizable adhesive layer. [Example 2] EPICLON EXA-830CRP containing 100 parts by mass of the aromatic glycidyl ether (A) was mixed in a reaction container equipped with a stirrer, a reflux condenser, a thermometer, a dropping funnel, and a nitrogen inlet. 35 parts by mass of ARONE OXETANE OXT-221 of the above-mentioned oxycyclobutane oxycyclobutane compound (B), and 50 parts by mass of KBM-303 as a decane-containing oxane coupling agent (C) As a cationic poly-27- 201249946 -4-(stupylthio)phenyl fluorene

The surface of each sheet of the binder film is prepared by coating the obtained cationically-initiating agent (D) with 40 parts by mass of diphenyl-4 quinone fluorophosphonate 2 (F), respectively. The thickness of the coating substrate was about 2 μm, and the coated substrate was bonded to both surfaces of the polarizing film (polarizing film). Then, after pressurizing with a blanket cylinder, a belt-type ultraviolet irradiation device (Fusion LH-6; output 100%, belt speed 17 8 m/min) was used, and the cumulative amount of light of 300 to 39 〇 nm was irradiated from the acrylic resin film side. Ultraviolet rays of 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. [Example 3] In a reaction vessel equipped with a mixer, a reflux condenser, a thermometer, a dropping funnel, and a nitrogen gas inlet, 100 parts by mass of EPICLON EXA-830CRP as an aromatic glycidol bond (A) was mixed therein. 375 parts by mass of ARONE OXETANE OXT-221 of two or more oxycyclobutane oxycyclobutane compounds (B), and 25 parts by mass of KBM as a decane coupling agent (C) containing an alicyclic epoxy group. 303. As a cationic sensitizer (D), 40 parts by mass of diphenyl-4-(phenylthio)phenyl sulphate, 50% by mass of a propylene carbonate solution, as a photosensitizer ( E) 2.5 parts by mass of 9,10-dibutoxyanthracene and 2.5 parts by mass of a photo-sensitizer -28-201249946 (F), and a mixture of ethylene and zinc Thus, a cationically polymerizable adhesive having a viscosity of 26 mPa.s (25 〇c) was prepared. In the acrylic resin film containing water methacrylate as a main component, the main π of the TAC film, and the surface of the sheet, the cation-based adhesive agent obtained by the wire coating is used as a cation-bonding agent. The thickness of #m is further attached to the both sides of the polarizing plate (polarizing film). Next, the rubber roller was used to pressurize t, and a belt type ultraviolet irradiation device (Fusion LH-6; output 100% 'conveyor speed 17 8 m/min) was used to irradiate the acrylic resin film side from 3 〇〇 to 39 〇 nm. Ultraviolet rays having a light amount of 13 〇〇mJ^cm 2 were obtained as a polarizing plate having a protective film/cationic polymerizable adhesive layer/polarizing plate/cationic polymerizable adhesive layer/protective film thereon. [Example 4] EPICLON EXA-830CRP containing 1 part by mass of the aromatic glycidyl ether (A) was mixed in a reaction vessel equipped with a stirrer, a reflux condenser 'thermometer, a dropping funnel, and a nitrogen gas inlet port. 39 parts by mass of ARONE OXETANE OXT-221 of two or more oxycyclobutane oxycyclobutane compounds (B), and 10 parts by mass of the Shixiayuan coupling agent (C) containing an alicyclic epoxy group KBM-303, as a cationic polymerization initiator (D), 40 parts by mass of diphenyl·4-(phenylthio) stupyl hexafluorophosphate, 50% by mass of propylene carbonate solution, as a light increase 2.5 parts by mass of 9,10-dibutoxy onion of the sensitizer (E) and 2.5 parts by mass of 1,4-diethoxynaphthalene as a photosensitizer (F), and stirred thereby A cationically polymerizable adhesive having a viscosity of 2 6 mPa a · s (25 ° C) was prepared. -29- 201249946 The surface of each sheet of the acrylic resin film and the TAC film which are mainly composed of polymethyl methacrylate as the main component, and the cationically polymerizable adhesive obtained by ingot coating are made into about .2 / The coated substrate is bonded to both sides of the polarizing film (polarizing film), respectively. Then, after pressurizing with a blanket cylinder, a cumulative amount of light of 300 to 390 nm was irradiated from the acrylic resin film side using a belt type ultraviolet irradiation device (Fusion LH-6; output of 1% by weight, belt speed of 17 8 m/min). The ultraviolet ray of 1300 mJ/cm 2 was obtained as a polarizing plate composed of a protective film/cationic polymerizable adhesive layer/polarizer/cationic polymerizable adhesive layer/protective film. [Example 5] 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 (A), was mixed. 395 parts by mass of ARONE 0XETANE OXT_221 having two or more oxocyclobutane oxycyclobutane compounds (B), and 5 parts by mass of hydrazine as an alicyclic epoxy: decane coupling agent (C) 303. A 50 mass% dipropyl carbonate solution of diphenyl-4-(phenylthio)phenylphosphonium hexaphosphate as a cationic polymerization initiator (D), 2.5 as a photosensitizer Parts by mass of 9,10-dibutoxyanthracene and 2.5 parts by mass of ruthenium, 4-diethoxynaphthalene as a photosensitizer (F) and stirred to thereby prepare a viscosity of 26 mPa.s (25°) C) A cationically polymerizable adhesive. On the surface of each of the acrylic resin film and the TAC film which are mainly composed of polyacrylic acid ruthenium, the cationically polymerizable adhesive obtained by wire coating is applied to a thickness of about 2/zm, and the coating is applied. Substrate -30- 201249946 is attached to both sides of the above polarizer (polarizing film). Then, after pressurizing with a blanket cylinder, a belt-type ultraviolet irradiation device (FUSi0nLH-6; output of 1% by weight, conveyor speed of 17 8 m/min) was used, and a cumulative light amount of 1300 mJ was irradiated from the acrylic resin film side at 300 to 390 nm. Ultraviolet light of /cm2 gives a polarizing plate composed of a protective film/cationic poly-amp; f developer layer/polarizer/cationic polymerizable adhesive layer/protective film. [Comparative Example 1] In a reaction vessel equipped with a stirrer, a reflux condenser, a thermometer, a dropping funnel, and a nitrogen gas inlet, the EPICOLN EXA-830CRP was mixed with 100 parts by mass of the aromatic glycidol (A). 4 parts by mass of ARONE OXETANE OXT-221 of the above oxycyclobutane oxycyclobutane compound (B), and 40 parts by mass of diphenyl _4_ (phenyl sulphate) as cationic polymerization initiator (D) 50% by mass of a propylene carbonate solution of phenylphosphonium hexafluorophosphate, 2.5 parts by mass of 9,10-dibutoxyfluorene as a photosensitizer (E), and as a photosensitizer (? 25 parts by mass of 1,4-diethoxynaphthalene was stirred and stirred to prepare a cationically polymerizable adhesive having a viscosity of 26 mPa.s (25 ° C). On the surface of each of the acrylic resin film and the TAC film which are mainly composed of decyl methacrylate, the cationically polymerizable adhesive is applied by wire coating to a thickness of about 2 /zm, and the coated substrate is further coated. They are bonded to both sides of the above polarizer (polarizing film). Then, after pressurizing with a blanket cylinder, a belt-type ultraviolet irradiation device (Fusion LH-6·' output 100%, conveyor speed 17 8 m/min) was used, and the acrylic resin film side was irradiated from 3 〇 to 39 〇 nm. The amount of light of -31 - 201249946 13 00 mJ/cm2 was obtained, and a polarizing plate having a protective film/cationic polymerizable adhesive layer/polarizer/cationic polymerizable adhesive layer/protective film was obtained. [Comparative Example 2] EPICLON EXA-830CRP containing 100 parts by mass of the aromatic glycidyl ether (A) was mixed in a reaction vessel equipped with a stirrer, a reflux condenser, a thermometer, a dropping funnel, and a nitrogen inlet. 397 parts by mass of ARONE OXETANE OXT-221 of oxycyclobutane oxycyclobutane compound (B), and 2,5 parts by mass of KBM_3 as decane coupling agent (C) containing an alicyclic epoxy group 〇3, a 50% by mass of a propylene carbonate solution of 40 parts by mass of diphenyl(phenylthio)phenanthryl hexafluorophosphate as a cationic polymerization initiator (D), and 2.5 lbs as a photosensitizer 9,10-dibutoxyanthracene and 2.5 parts by mass of 1,4-diethoxynaphthalene as a photosensitizer (F) were stirred and stirred to prepare a viscosity of 26 mPa.s (25t: a cationically polymerizable adhesive. On the surface of each of the acrylic resin film and the TAC film which are mainly composed of polymethyl methacrylate as a main component, the obtained cationically polymerizable adhesive is applied to a thickness of about 2 #m, and the coated substrate is further coated. They are bonded to both sides of the above polarizer (polarizing film). Next, after pressurizing with a blanket cylinder, and using a belt type ultraviolet irradiation device (Fusion LH-6; 100% rotation, conveyor speed 178111/minute, the cumulative amount of light is irradiated from the acrylic resin film side to 300 to 39 〇 nm. The ultraviolet ray of 13 〇〇mJtm2 was obtained as a polarizing plate composed of a protective film/cation = σ 丨 刎 刎 layer/polarizer/cationic polymerizable adhesive layer/protective film. -32- 201249946 [Comparative Example 3] In a reaction vessel equipped with a stirrer, a reflux condenser, a thermometer, a dropping funnel, and a nitrogen inlet, 100 parts by mass of EPICLON EXA-830CRP as an aromatic glycidyl ether (A) is mixed as a mixture of two or more oxygen. 250 parts by mass of ARONE OXETANE OXT-221 of the oxidized base-oxygenated compound (B), and 150 parts by mass of KBM_3〇3 as an alicyclic epoxy group-containing ceramide coupling agent (C) 40 parts by mass of diphenyl(phenylthio)phenylphosphonium hexafluorophosphate of 50% by mass of a propylene carbonate solution of the polymerization initiator (D), and 2.5 parts by mass as a photosensitizer , 10-dibutoxy onion and as light 2.5 mass (4) of M-diethoxynaphthalene with a sensitizer (F) and stirred to prepare a viscosity of 24 〇 1 卩 3.8 (25. cation cationically polymerizable adhesive. In the case of polymethyl methacrylate Each of the acrylic resin film and the TAC film of each of the TAC films has a thickness of about 2 &quot; m by a cationically polymerizable adhesive obtained by wire coating, and the coating is applied to the polarizing film (polarizing film). On both sides of the soil blanket press I, and use the belt type UV (FusionLH·6; output _, belt speed clock) f the above acrylic film side is irradiated with ultraviolet light of 300 to 39 〇nm ,, which is obtained from A polarizing plate having a light-quantity adhesive layer/polarizer/cationic polymerizable structure. ',° only 4 film [Comparative Example 4] In a reaction vessel equipped with a stirrer, a reflux condenser, and a temperature nitrogen inlet , mixed as aroma:: funnel and glycine glycidyl ether-33- 201249946 (eight) of 1 part by mass of £1 (: two (^ ugly eight-83001^, as an alicyclic epoxy group) KB of 4 parts by mass of the decane coupling agent (c) M-30, as a cationic polymerization initiator (D), 40 parts by mass of diphenyl-4-(phenylthio)phenylphosphonium hexafluorophosphate, 5 〇 mass% propylene carbonate solution, as a light increase 2.5 parts by mass of 9,10-dibutoxyanthracene of the sensitizer (E) and 2.5 parts by mass of 1,4-diethoxynaphthalene as a photosensitizer (F), and A cationically polymerizable adhesive having a viscosity of 24 mPa·s (25 ° C) was prepared. The surface of each of the acrylic resin film and the TAC film which are mainly composed of poly-f-acrylic acid-based acrylic acid is coated with a cationically polymerizable adhesive having a thickness of about 2 Å m, and the coating base is applied. The materials are bonded to both sides of the above polarizer (polarizing film). Then, after pressurizing with a rubber roller, a belt type ultraviolet irradiation device (Fusion LH_6; output of 1% by weight, a belt speed of m/min, and a total of 3 〇〇 to 39 〇 nm from the side of the acrylic resin film are used. A polarizing plate having a light amount of 130 〇mj/cm 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]

A: A_E: T_221 containing 450 parts of a mixture of two or more oxocyclobutane compounds (8) in a reaction vessel equipped with a recirculating cooler of a blender, a thermometer, a dropping funnel, and a disordered population. Ring-type epoxy decane coupling oxime (C) 50 parts by mass of κβμ_3〇3 _ θ F horse (five) ion polymerization initiator () 40 parts of diphenyl _4 IL Lane ·) base 铳Hexafluorophosphate-34- 201249946 5 〇 quality 伸 酷 酷 酷 solution, as a photosensitizer (8) 2.5 parts by mass of 9,1 〇-dibutoxy fluorene and as a photosensitizer (7) 25 quality A cation-polymerizable adhesive having a viscosity of 15 mPa·s (25 ° C) was prepared by mixing &amp; 1,4-di:oxynaphthalene. On the surface of each sheet of the acrylic acid resin film and the TAC film which are mainly composed of polymethyl methacrylate and the TAC film, the cationically polymerizable adhesive obtained by the wire coating is approximately 2 m libraries. From the thickness of m, the coated substrate is attached to both sides of the polarizer 丨值水# field September (pre-bonded film). Then, after using the blanket cylinder to pressurize and use the value w, F .... use the belt-type ultraviolet irradiation device (Fusion LH-6, turn out 1〇〇%, suspicion, ...^ The τ speed is 17.8 m/min), and the cumulative light amount from the UV 33 〇〇 to 39 〇 of the above-mentioned acrylic resin film side UOOmJW &lt;external line is obtained by μ g 士 mg ^ compositive adhesive layer / hemipare MM The upper eight has a polarizing plate composed of a protective film/cationic poly-first film/a ionic polymerizable adhesive layer/with a 嘈m晅. The demon has a W layer/protection 4 溥 film [Evaluation method of adhesion] The size of the actual example & comparative example is taken as the test #. The partial 7^ reverse cut into 3mmx60mm specimens are rolled into a straight 栌 3 φ C, 50 〇 / 0RH conditions, and the evaluation and evaluation such as; The stick. At the moment of winding, it is visually observed that there is no peeling or cracking of the adhesive layer in the house. [Water resistance evaluation X price side:: peeling or adhesive layer crack. Will implement the example and

A polarizing plate known as a 50 mm object was cut into 50 mm X warm water t 24 H test piece 'The test piece was immersed at 6 (TC, and then visually confirmed the appearance, and evaluated as follows. -35 - 201249946 Good "〇": There is no iodine discoloration or peeling of the test piece. Poor "X": It is confirmed that all or part of the test piece has iodine discoloration and peeling. Table 1 [Table 1] Example 1 Example 2 Example 3 Example 4 Example 5 Aromatic glycidyl ether (A) EPICLONEXA-830CRP (parts by mass) 100 100 100 100 100 Oxycyclobutane compound (B) having two or more oxycyclobutane groups (B) ARONEOXETANEOXT-221 (Quality 300 350 375 390 395 Decane coupling agent with alicyclic epoxy group (C) ΚΒΜ·303 (parts by mass) 100 50 25 10 5 Evaluation of the subsequent evaluation of water resistance〇〇〇〇 Table 2

[Table 2] Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Comparative Example 5 Aromatic glycidol Si (A) EPICLONEXA-830 CRP (part by mass) 100 100 100 100 0 Oxygen having 2 or more oxygen cyclobutane groups Cyclobutane compound (B) ARONEOXETANEOXT-221 (parts by mass) 400 397.5 250 0 450 decane coupling agent with alicyclic epoxy group (C) KBM-303 (parts by mass) 0 2.5 150 0 50 Evaluation of follow-up XXXXX Evaluation of water resistance X 〇〇 XX The abbreviations in Tables 1 to 2 and the like will be described. "EPICLON EXA-8 3 0CRP": bisphenol F diglycidyl ether "ARONE OXETANE OXT-221": bis [1-ethyl (3-oxocyclobutane)] decyl ether "KBM-303": 2 - (3,4-Epoxycyclohexyl)ethyltrimethoxysulfonate It is understood that Examples 1 to 5 of the cationically polymerizable adhesive of the present invention have excellent adhesion and water repellency. On the other hand, it is understood that Comparative Example 1 is a state in which the decane coupling agent (C) is not contained, and the adhesion and water resistance are not good. Further, it can be seen that the comparative examples 2 and 3 oxycyclobutane compounds (B) and the decane coupling agent (C) are used in an amount exceeding the range specified in the present invention, and the respective strengths are not good. Further, Comparative Example 4 is a state in which the oxygen-cyclobutane compound (B) and the decane coupling agent (C) are not contained, and Comparative Example 5 is a state in which the aromatic glycidyl ether (A) is not contained, and the adhesion and water resistance are maintained. Sex is not good. [Simple description of the diagram] None. [Main component symbol description] None. -37-

Claims (1)

201249946 VII. Patent application scope: A cationically polymerizable adhesive, an oxocyclobutane compound (B) of L-oxocyclobutane (.xetanyi), and an ancient tower T ^ ether compound (Β), and Oxycyclobutane () of nI) has a 矽%-type ketone-based decane coupling agent (cationic polymerization of ionic polymerization initiator (D), followed by = for 10 parts by mass of the above aromatic The above-mentioned oxygen-based butane compound (B) is used in the range of 3 〇〇 你 ) ) ) ) ) , , , , , , , , , , , , 贝 贝 贝 贝 贝 贝 贝 贝 贝 贝 贝 贝 贝 贝 贝 贝 贝 贝 贝4 巳2. 2. For the patented range of &quot; cationic polymerization adhesive, 苴中j aromatic glycidyl ether (4) has more than 2 glycidyl screamers. 3. If the scope of patent application is 2 The cationically polymerizable adhesive, wherein the aromatic glycidyl ether (A) is one or more aromatic selected from the group consisting of bisphenol A condensed water: oleyl ether and bisphenol F diglycidyl ether. Glycidyl ether. 4. If the scope of patent application is 帛, the cationic polymerization of the member The agent wherein the oxycyclobutane compound (B) has a molecular weight of from 1 Å to 8 Å, such as the cationically polymerizable adhesive of claim 4, and the above oxycyclobutane compound (B) A bis(1-ethyl(3-oxocyclobutane))methyl group. The cationically polymerizable adhesive according to claim </RTI> wherein the decane coupling agent (c) is selected from the group consisting of 2-(3, One or more selected from the group consisting of 4-epoxycyclohexyl)ethyltrimethoxine and 2-(3,4-epoxycyclohexyl^ethyltri-) ethoxylate. -38- 9. 201249946 7· The cationic polymerizability as in the first paragraph of the patent application is further contained with a photosensitizer (Ε). &gt; • Cationic polymerizability as in claim 7 of the patent application, followed by the above photosensitizer (Ε) is a polarizing plate having a wavelength of 38 〇 nm or more, which is a polarizing plate agent of a film and a polarizer, and is a conjugated adhesive as claimed in the patent application. A cationically polymerizable adhesive, wherein the above cationic polymerization 1 to 8 of the ingredients of the item, the 1 7 7 agent, which shows the maximum absorption and protection Then the cationic poly-39- 201249946 IV. Designation of the representative figure: (1) The representative figure of the case is: No. (2) The symbol of the symbol of the representative figure is simple: No. 5. If there is a chemical formula in this case, please reveal the best Chemical formula showing the characteristics of the invention: