TW201249948A - Active-energy-ray-curable adhesive composition for plastic film or sheet - Google Patents

Abstract

To provide an active-energy-ray-curable adhesive composition that has low viscosity, excellent curability, and excellent adherability to various plastic films and the like, particularly to hydrophilic plastic films, and that exhibits sufficient performance even in applications that require extreme durability. The active-energy-ray-curable adhesive composition contains components (A) and (B) as curable components, and a component (C) as a polymerization initiator. The component (A) is a compound represented by formula (1) (in formula (1), R1 is a C1-6 alkyl group, m is an integer from 1 to 20, and R2 is an m-valent residue of a compound selected from the group consisting of aliphatic alcohols, polyalkylene oxides, polyester polyols, compounds including a phenolic hydroxyl group, and alkylene oxide-modified products thereof). The component (B) is an ethylenically unsaturated compound. The component (C) is a photo-cationic polymerization initiator.

Description

201249948 VI. Description of the Invention: [Technical Field of the Invention] [00 0 1] The present invention relates to an active energy line hardening type adhesive composition by an electron beam (electron beam, eH3eam) An active high-energy ray-curable adhesive composition in which various active plastic films or sheets are adhered by irradiation with active high-energy rays such as ultraviolet rays. The composition of the present invention is very suitable for application to a thin layer adherent of a plastic film or sheet; and is also suitable for use in a liquid crystal display (LCD) or the like. The manufacture of various optical films or sheets is a very practical material in this technical field. Further, in the present specification, an acrylate and/or a methacry ate is a (meta) acry acid salt ((meta) acry 1 ate ) ; acryloyl and / or methacryloyl as (meta) acryloyl; acrylic acid and / or methacrylic acid Table. In the following, the plastic film or sheet is generally referred to as a "plastic film or the like" unless otherwise specified. The film or sheet is collectively referred to as "film". [Prior Art] [000 2] A thin layer of a plastic film or the like has been adhered to, or a plastic film, etc.

10112053S 1013293844-0 201249948 A thin layer of adherend made of 4 layers of adherends and other materials, lamination of each other 'mainly by dry lamination method (iaminati〇n), this method A solvent-type adhesive lock containing a polymer of ethylene vinyi acetate copolymer (EVA) or polyurethane (p〇iyUrethane) is applied to a thin layer of adherend of S- After drying, the first thin layer of the adherend is adhered by a rubber roller or the like. The adhesive composition used in the method is generally a composition containing a large amount of solvent for uniform coating of the composition, but therefore, a large amount of/valve vapor is volatilized during drying to form toxicity and work. Safety and environmental pollution issues. Further, such an adhesive composition is used for adhering a heat seal of a laminate film, a scribing operation for engraving a groove, etc., just after adhering a thin layer of adherend. In the post-processing work, there is a problem that the thin layer is peeled off by the adherend. As a binder composition for solving these problems, a solvent-free adhesive composition has been studied. 〇 [0 0 0 3] As a non-solubilized rugged product, it has a two-component adhesive composition and an adhesive composition which is hardened by an active high-energy ray such as ultraviolet rays or electron beams. - Liquid type adhesive composition, mainly using a polyisocyanate compound having a tc» main component at the terminal hetero group (hyd dish yl) and an isocyanate group (is〇cy_te) as a hardener , the so-called polyurethane (p〇lyurethane) 1G1120538 5 1013293844-0 201249948 type of adhesive composition. However, this composition has a drawback in that it takes a long time to harden, and therefore, after the _ __ thing, it is impossible to carry out the post-processing operation of the group, which has such a problem. On the other hand, the active high-energy ray-curable adhesive composition has a high rate of hardening and is excellent in productivity, and has recently attracted attention. [0 0 0 4] On the other hand, liquid crystal display devices are characterized by thinness, light weight, and power saving, from the navigation system for automobiles, mobile phones, and personal digital assistants (PDAs). Small electronic machines to the word processor or personal computer (personai computer), and even television receivers, have universal applications. In recent years, the bonding of various optical films and the like used in such liquid crystal display elements,

Active high energy ray hardening type adhesive compositions are gradually being used. Q

[0005] As an optical film, there are a polarizing plate, a phase difference film, a viewing angie CCM pensati〇np〇iarizing film, a brightness enhancement film, and an anti-reflection film (anti- Reflection film), an anti-glare film, a lens sheet, a diffuser sheet, and the like can be cited, and 101120538 1013293844-0 201249948 These can be produced using various kinds of plastics. Among these plastics, as a eccentricity, polyethylene glycol and diacetin (QH) are particularly reused. These plastics contain a characteristic of having a very high hydrophilicity when compared with a general Na. 〇【00 0 7】 • As a composition of active high-energy ray-curable adhesive for polarizing plates, it is known that a radical integrated composition using radical photopolymerization, a cationic chelate pattern of enzymatic photopolymerization, And a hybrid composition which combines free radical recording and cationic photopolymerization. [0008] As a radical photopolymerizable composition, a radical polymerizable compound containing a polar group such as a carboxyl group or a polar group and a radical polymerization having no polar group are known. A compound which is prepared in a specific ratio, Patent Document 1 and the like. However, this composition 'has a large shrinkage at the time of hardening, and it is difficult to obtain sufficient peel strength with the stress generated at the parent interface depending on the kind of the adherend. Further, in order to solve this problem, a composition containing a large molecular weight of polyaminol 101120538 7 1013293844-0 201249948 s urethane (meta) acrylate has been studied (for example, Patent Document 2, etc.) . However, the 'this composition' has a problem in that the viscosity of the composition is increased and the coating of the enamel film cannot be performed by the painting device. Moreover, the shrinkage stress at the time of hardening may also be alleviated by the increase in the flexibility of the adhesive d composition, but such a method is due to the heat resistance of the adhesive (heating such as shirt (6) and water-based (finance). His fastness is reduced, and in applications requiring strict durability, peeling (peeling) or foaming (f〇aming), cracking (crad〇, etc.) may occur. [0009] As a cationic photopolymerization composition For example, a composition containing an aromatic ring-free epoxy resin as a main component (Patent Document 3), and an aliphatic-containing epoxy, a fat-free epoxy, and/or an oxygen-burning (Qxetane) 敝The patent "Patent Document 4" is well known. Such a composition 'relative to the radical photopolymerizable composition, because of the relatively small shrinkage of ◎ during hardening, can suppress the stress at the interface. Advantages. However, cationic photopolymerization generally causes polymerization inhibition caused by moisture or alkaline substances, and is well known in the environment of humidity, a substrate having a large moisture content, and a surface. In the case of a composition containing a multifunctional ruthenium oxide resin as a main component, the influence of the decrease in the hardenability due to polymerization inhibition may be changed. Smaller, but such a composition, viscosity increased, resulting in the problem of film coating can not be achieved by the coating device 101120538 1013293844-0 201249948. [0010] As a mixed composition, for example, contains: with isocyanuric acid ( Is〇cyanuric acid) a ring-structured (partial) acrylate, an alicyclic epoxy compound, a hydroxyl group-containing compound, and a composition containing a photoacid generator (PAG); Patent Document 5; An epoxy resin having two or more epoxy groups, at least one of which is a lipid oxime ring epoxy group, having two or more epoxy groups and having no alicyclic ring. Epoxy group epoxy group, cation A composition of a photopolymerization initiator and a polymerizable monomer (mo_er) "Patent Document 6"; comprising: a compound having two or more (meta) acrylic acid groups, having a hydroxyl group and a (Partial) C A compound of a olefinic acid group, a cationically polymerizable compound having a (partially) acrylic acid group, a composition of a radical photopolymerization initiator and a cationic photopolymerization initiator, is known as Patent Document 7. [0011] These compositions are mixed to solve the polymerization inhibition problem caused by shrinkage at the time of hardening, but according to the research of the team of the present invention, the following problems have been confirmed. [0012] Patent Document 5 discloses The composition contains a composition of a (partial) progestate compound having an isocyanic acid ring structure as an essential component 101120S38 9 1013293844-0 201249948, but according to the research of the team of the present invention, if the composition Including a plurality of (partial) acrylates having two or more (meta) acrylic acid groups, the shrinkage during hardening does not become considerably small, and thus stress generation cannot be suppressed at the interface. Therefore, it has been confirmed that it is difficult to obtain sufficient peel strength due to the relationship of New Zealand. [0013] Patent Document 6 relies on reading secrets, and the axis is made up of 域 Ο Ο Ο Ο Ο , , , , , , , , Ο Ο Ο , , , , , , , , , , , , , , , , , , , , , _Regularization is made into a shouting material 0 [0014] The composition disclosed in Patent Document 7 uses a cationically polymerizable compound having a specific ratio of (6) acetoacetate as a conversion component, but according to the remaining team It has been confirmed that the shrinkage at the time of hardening does not become small if the compound contains $ 匕 3 open in the composition, and it has been confirmed that it is required to obtain sufficient peel strength from ", ± material" (peel strength). [Prior Art Document] [Patent Document] 101120538 1013293844-0 10 201249948 [Patent Document 1] Fine 2__阙29# "*Request Patent Range" [Patent Document 2]_ [Patent Document 3] Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. 4-245925. 】Tekeli Ling _233279 Bulletin "Application for Patent Scope" [ [Patent Document 7] JP-A-2008-257199, "Application Patent Scope" [Patent Document 7] JP-A-2008-260879, "Application Patent Scope" [Disclosure] [Problems to be Solved by the Invention] [0 0 16] The present invention is In view of the foregoing problems, the object of the present invention is to provide excellent curability at low viscosity and excellent axial force for plastic enamel, especially hydrophilic plastic film, even when strict durability is required. The active high-energy ray-curable adhesive composition for a plastic film or a sheet which can exhibit sufficient performance in terms of the traits. [Method for Solving the Problem] [0017] The team of the present invention has found out the following results through various studies. Active high energy ray-curable adhesive composition, 101120538 11 1013293844-0 201249948 As a curable component, (A) molecule comprises: at least one of the following chemical formulas (1,) ^ [◦0 18] [Chemical 5]

〇—(η 〇 [0019] The compound represented by the functional group "linear or branched alkyl group having 1 to 6 carbon atoms", and (Β) ethylenically unsaturated compound (_咖) ^ ethylene compound); as a polymerization initiator "containing at least (C) cationic photopolymerization initiator; such an active energy ray-curable adhesive composition 'for various plastic films and the like, among them, polyethylene glycol (P 〇1yvinyl alcohol) Hydrophilic plastic film such as polarizing element film, such as postal bribery, low degree of addition, and high durability in the case of New Zealand's “Looking & Recording”. [0020] Further, according to the present invention, a laminate obtained by laminating a substrate, a hardened layer of the adhesive composition of the present invention, and a plastic film or sheet in this order can be obtained; 101120538 12 1013293844-0 201249948 and a polarizing plate made of a laminate of a polyethylene-based polarizing element film or sheet, a hardened layer of the adhesive composition of the present invention, and a plastic fine or material-based scale. The invention will be described in detail. OBJECT OF THE INVENTION [0021] The group of the present invention is a red compound and an ethylenically unsaturated compound of the above formula (1) as a hard recording, and the domain can be hardened at least in the presence of a photopolymerization initiator.彳 _ has excellent characteristics, for all kinds of plastic thin lining, the system is a polyethylene _ polarized components, such as the hydrophilicity of the thin film, etc., even in the high squatting Wei, it also has a very high ambiguity, in various The plastic film or the like is extremely effective in adhesion (four) adhesion, and can be suitably applied to the manufacture of an optical film by a liquid crystal display device or the like. [Embodiment] [0 0 2 2] The present invention has a _ active high lining line Wei __城物, the present invention is composed of at least a hard-dip component (tetra) __; the hard-aged age is at least composed of the following components (1) and (8); the polymerization initiator is composed of at least the following component (6); An active high-energy ray-curable adhesive composition of a plastic film or sheet. 101120538 1013293844-0 201249948 (A): The following chemical formula (1) [00 2 3] [Chem. 6] 〇

[0024] "Chemical Formula (1) ' is a direct bond or a branched alkyl group of a carbon atom; 6 is an integer of 1 to 20, which is a linear or branched chain of a number of carbon atoms. Aliphatic alcohol and its alkylene 〇xide degenerate, linear or branched chain polyethylene oxide, polyester polyol a m-valent residue of a compound selected from the group consisting of aromatic alcohol and its alkylene oxide denature, and a compound having a phen〇iic hydroxyl group and an alkylene oxide denature thereof ( Residue), if a unit containing 0CH2C(0H)(Ri)CH2〇—is also represented by the compound “hereinafter, referred to as (A) component”; [0025] (B) component: ethylenically unsaturated compound ( Unsaturated ethylene compound) "hereinafter, referred to as (B) component"; 101120538 101^293844-0 201249948 (C) Component: Cationic photo-polymerization initiator "The following" is called (c) component . Further, the adhesive composition of the present invention may contain a (D) radical photo-polymerization initiator (hereinafter referred to as (D) component) as needed. Hereinafter, each component is demonstrated. 〇【0 0 2 6】 4 1, _ (A) component (A), as shown in the above chemical formula (1), the alkyl group having more than one oxirane ring in the molecule has an alkyl group A glycidyl group of a substituent, a compound having an ether linkage as a medium. [0027] The formula (1) is an alkyl group having 1 to 6 carbon atoms, and the alkyl group may be a straight chain or a branched chain, and a mercapto group or an ethyl group may be considered for convenience of synthesis. It is more ideal than ideal, especially the base is ideal. The integer number of the m series 1 to 20 is better than ideal, and the 3 is more desirable. [0028] R2 is a linear or branched chain fatty alcohol having a molecular weight of 1 to 2 〇, a linear or branched chain of densely diluted oxygen (p〇iy_aik fine (4), 101120538) 1013293844-0 201249948 P〇1yester polyol, aromatic alcohol and, roasted oxygenated denatured, and compounds having a phenolic hydroxyl group and their naturalized oxygenated denatured substances The m-valent residue of the compound selected in the group 'supplement' contains a unit of CH£(OH)(R丨)CM). When a compound of the formula (1) is produced, a bad oxygen group of the obtained epoxy compound is reacted to form a multimer. In the case where a polymer is formed, R2 becomes -0CH2C (0H). (Ri) (10) - a unit of the compound. As R2, the m-valent residue of the compound selected from the group consisting of a compound having a phenolic hydroxyl group and a riding oxygenated denature is more desirable than the ideal 'in this case'--secret) (5) (10)—The unit can also be 0 [0029] (A) component, which can be easily manufactured by the following method. For example, the gas (2) is based on the base of the epoxy-based epoxy gas (Mkyl-indicated ichl〇r〇) Hydrin) Ο ", called compound (2)", and a compound such as an alcohol or a phenol in the molecule having more than one base group (such as a decoction) (3). The reaction can be easily carried out by a known method, for example, "Foreclosure, Unexamined-Japanese-Patent No. 08-283379". [00 3 0] [Chem. 7] 101120538 16 1013293844-0 (2) 201249948

[0031] In the chemical formula (2), the Ri is a linear or branched alkyl group having 1 to 6 carbon atoms. 〇 [0 0 3 2] [Chemical 8] R2--Ο-Η

Jm (3) [0 0 3 3] In the chemical formula (3), „! is an integer of 1 to 20; an aliphatic alcohol having a straight or branched chain of carbon atoms 丨 to 邡, a linear or branched chain of poly-alkylene oxide, a polyether polyol (p〇iyester polyo1), an aromatic alcohol and a thinned oxygen denature thereof, and a phenolic hydroxyl group (phen a m-valent residue of a compound selected from the group consisting of a compound of 〇iic hydroxyl group and an alkylene oxide denature thereof. [〇〇34] 101120538 17 1013293844-0 201249948 A compound of the formula (3) The reaction residue of the following compound (3) is R2 of the chemical formula (1). Specific examples of the compound (3) are as follows. [00 3 5] * A linear or branched carbon number of 1 to 20 Branched chain fatty alcohol (aHphaticalcohol) A linear or branched chain fatty alcohol having 1 to 20 carbon atoms, which may be used, for example, decyl alcohol, ethanol, propanol, isopropanol, butanol, hexanol, 2 -2-ethylhexanol, etc., having a carbon number of 1 to 20, even if there is a branched chain, it is also very good aliphatic 1 Alcohol; glycols such as ethylene glycol, propylene glycol, neopentyl glycol (ne〇pentyi giyC〇i); 1,3-propanediol , an aliphatic divalent alcohol such as 1,4-butanediol, 1,6-hexanediol, etc.; trimethylolpropane, trioxindole Trimethylolethane, glycerin, diglycerine, butanol (erythritol, erythrit〇l, pentaerythritol), sorbitol (s〇rbh)脂肪i) an aliphatic polyvalent alcohol; an alicyclic aliphatic aliphatic polyvalent alcohol such as n〇rb〇rnaneciimethanol; an alkylene oxide denature of these compounds, etc. [00 3 6] - ※ p〇ly_alkyiene oxide of a direct bond or a branched chain 101120538 18 1013293844-0 201249948 A linear or branched chain of p〇ly-alkylene oxide, which can be enumerated There are polyethylene glycol (p〇lyethyiene glycol), polypropylene glycol (polypropylene glycol), polybutylene glycol (polybutylene glycol), A linear or branched chain polyoxochemical compound such as polytetramethylene glycol. [0 0 3 7] ❹ Polyol Polyol As the polyether polyol, for example, a compound obtained by reacting a polyvalent alcohol with a polyvalent carboxylic acid can be used. [0 0 3 8] The aromatic alcohol is exemplified by the use of an alkylene oxide denatured product, which is exemplified by the use of the phthalocyanine (Xylene 〇 glyco1). [0039] * A compound having a phenolic hydroxyl group as a compound having a phenolic hydroxyl group, and examples thereof include: phenol, bisphenol Onsphenol, biphenol (bi(phen〇1)), and phenolic resin. Etc., among them, compounds selected from the group consisting of age, double and age resins are more desirable. 10112QS38 19 1013293844-0 201249948 As a categorization, it can be cited as a valence compound, a catechol compound, a divalent compound such as a catechol, and a divalent compound. (oimylpheriGl) a derivative such as a derivative of a hydrogen atom of a naphtha ring, or a hydrogen atom of an aromatic ring substituted by a linear or branched alkyl group of carbon number 6; A maternal oxygen degeneration of the compound, and the like. Examples of the two-aged ones include, for example, biguanide derivatives such as succinyl A and bispan F, and alkylene oxide denatured products of these compounds. 〇 酴 酴 酴 酴 酴 酴 酴 酴 酴 骑 骑 骑 骑 骑 骑 骑 骑 骑 骑 骑 骑 骑 骑 骑 骑 骑 骑 骑 。 。 。 。 。 。 。 。 。 。 。 。 Examples of the phenol resin include a phenol novolac resin, a cresol novolac resin, and a polyvinyl phenol. In the compound of the alkylene oxide denatured product, the alkylene oxide denatured product may be exemplified by an ethylene oxide denatured product or a propylene oxide denatured product. Wait. [0 04 1] A preferred example of the compound (3), an alkyl alcohol having a branched carbon number of 1 to 8, or an alkyl alcohol having a branched or branched carbon number of 1 to 8.

10112CI53S 1013293844-0 20 201249948 ethylene-alcohol denatured product, ethylene glycol diol, di-glycol diol, polyethylene glycol, polypropylene glycol, discretionary b-oxygen, catechin 12, tea Alkenyl oxide denatured, t-butyl catecol, alkylene oxide denatured poly(butyl catechol), pyroantimony bismuth, pyrolysis , biphenyl hope (5) fine phenol), biphenyl olefin alkylene oxide denature, bisphenol A, bisphenol A alkylene oxide denature, bisphenol F, bisphenol F olefination denatured, phenolic phenolic Resin, a phenolic age-based resin, and the like can be used. 〇 [004 2] m' of the chemical formula (3) is an integer of 1 to 2 ,, 1 to 5 is more desirable, and 1 to 3 is more desirable. The method for producing the component (A) from the compound (2) and the compound (3) can be carried out by a generally known method for producing an epoxy compound. For example, when the compound (2) and the polyvalent phenol are used as the compound (3) to produce the component (U), it can be obtained by reacting an alkaline compound. As the test compound, a hydroxide, a carbonate, a bicarbonate or the like of a metal or a metal-based metal can be used. Specifically, sodium hydroxide or hydroxide can be used. Calcium, Hydroxide Dehydration, Carbon 101120538 1013293844-0 21 201249948 Sodium, sodium bicarbonate, etc. 'A mixture of these compounds can also be used. The reaction temperature at this time is listed as 3〇~12〇. Hey. When the compound of the compound (3) is used as the compound (3), it may be obtained by the same method as the above method. When the compound (2) and the compound (3) having m or more are 2 or more, the component (A) represented by the chemical formula (1) is obtained. 'With the production method, a part of the polymerization becomes a high molecular weight, and two of the polymers are obtained. A compound having such a cationic polymerization promoter group as defined in the above formula (1) can be used as the component (A) of the present invention; examples of such a polymer obtained can be exemplified, for example. The chemical formula m is a compound of 2 or more, and examples of the actual compound include resorcin (resorcin; resorcin® 1), bisphenol A, biguanide F, and phenol novolac resin. ), cresyl phenolic resin (cres〇i nov〇iac resin) and norbornane dimethanol (norbornanedimethanol). [0044] The component (A) is a compound represented by the above chemical formula (1), 岐 1 or 2, and the R 2 is a compound having a phenolic hydroxyl group and an m-valent residue of the alkylene oxide denatured product. A unit containing an ocHzCCOHXRO CH2〇- is also a good compound, and a desirable example of such a compound is shown in the following chemical formulas (5) to (9). 101120538 1013293844-0 22 201249948 [0045] [Chemical 9]

(5) [0046] 化学 "Chemical formula (5) 'Rl is a linear or branched chain of 1 to 6 carbon atoms; η is 0 or a positive number" (5) towel 'chemical formula (2 The compound can be combined at the ◦-position, the inter-position (m_p〇siti〇n), or the position (p_p〇siti〇n), and the _ is the adjacent position or position. The linear or branched chain of a fluorene having 1 to 6 carbon atoms in the formula (5) is preferable because the methyl group or the ethyl group is preferable and the fluorenyl group is more preferable. The secret or positive number of the chemical formula (5), 〇~1〇 is more desirable ‘0~5 is ideal, and particularly ideal is 0~1. [0047] [10]

[0 04 8] 1013293844-0 10Γ12Ό538 201249948 "R! is a linear or branched alkyl group having a carbon number of 丨~6 in the chemical formula (6); n is 0 or a positive number" Chemical formula (6) The compound of (2) is bound at the o-position, the inter position (m-p0siti〇n), the position (p-p0Siti0n), the ί# position (〇-position), the position, the position (m,- Position), or right, position (p-position) can be any, ideally the adjacent position, the position, the adjacent 'position, or the pair, the position "again, the so-called adjacent position, the position, and For the position, the case where the compound of the formula (2) is bonded to the benzene ring at the end of the side of the chemical formula (8) is shown. The chemical formula (8) is preferably a straight or branched chain of carbon atoms, a methyl group or an ethyl group (tetra), and a methyl group is more desirable. The n of the formula (6) can be lightly colored with respect to the compound of the chemical formula such as bijection; the η or positive number of the chemical formula (8), 〇~1〇 is ideal, and 0~5 is ideal, special duty I think about it. Because: (differences in the case of a double _ knot one ^ ^ 〇 4 set (mouth, p position) "neighbor, "neighbor, no Η, (°, P PQSition)", 0, PP 〇 Sltl 〇 n) Or "neighbor, neighbor, position (〇, 〇, position)" is ideal. ,υ,υ 0049] 【化11】

24 101120538 1013293844-0 (7) 201249948 [0050] "Chemical formula (7) in the 'secret carbon atom number 6 straight or branched chain of the burning group; R3 is a linear or branched chain of 1 to 6 carbon atoms In the formula (7), R3 is bonded to either the adjacent position (〇_p〇siti〇n), the inter position (m position), or the position (p_p〇siti〇n). More than σ to the ideal neighbor position or position. The number of carbon atoms of the formula (7) is 60. The linear or branched chain filaments are preferably methyl or ethyl, and the methyl group is more desirable. The R3 group of the formula (7) is a linear or branched alkyl group having 1 to 6 carbon atoms, preferably a butyl group, a butyl group or a hexyl group, and a tert-butyl group is more preferable. [Chemical 12]

[0 0 5 2] In the chemical formula (8), R is a linear or branched alkyl group having a carbon number of 丨6 or less. A straight chain of a quinone carbon number of 1 to 6 of the formula (8) or The alkyl, sulfhydryl or ethyl group of the branched chain is preferred, and the fluorenyl group is more desirable. 101120538 25 1013293844-0 201249948 [Chem. 13]

[Chemical Formula (9), R! is a carbon atom; a straight or branched chain of ι~6; a system of 0 or a positive number"

In the chemical formula (9), the compound of the chemical formula (1) is bonded at an o-position, an inter-position (m-positi〇n), a p-positi〇n, a 位置-position, Between, position (m'-position), or right,

Any of the positions (p, -position) can be, ideally, the adjacent position, the position, the neighbor, the position, or the pair, the position "again, the so-called adjacent position, the position, and the position" The compound of the chemical formula (2) is bonded to the benzene ring at the end of one side of the chemical formula (9); the adjacent position, position, position, and pair, position, represent the stupid ring of the end of the chemical (8) _ opposite side The situation of the combination. The linear or branched alkyl group having a lanthanoid number of 1 to 6 in the formula (9) is preferably an alkyl group, and the fluorenyl group is more preferable. ^ The chemical formula (9) is adjusted from the amount of the compound relative to the compound of the chemical formula such as bisphenol A; the oxime system of the formula (9) or a positive number, 10 is ideal, and 〇~5 is ideal 'particularly 〇~〗. Therefore, the bonding position of bisphenol A when the chemical formula of π is a positive number can be used in any one,

1—J 101120538 1013293844-0 26 201249948 Ideal for 'location', "neighbor, pair" position, "neighbor, position" or "neighbor, neighbor, position". [00 5 5] As the component (A), among the compounds of the above chemical formulas (5) to (9), the compounds of the formula (5) (6) and (8) are preferred, and further,亲娜娜相麟# On the age, the compound of formula (8) is ideal from the viewpoints of solubility, kiosk and enthalpy. ‘, [0056] As the component (A), the above-mentioned compounds may be used singly or in combination of two or more. [0 0 5 7] () The proportion of the component (A) is 'hardening component' total weight ι〇〇% by weight ratio '20 to 70% by weight, more preferably 3 〇 to _ weight ratio . (1) When the ratio of the component is 20% by weight or more, the cured product is excellent in heat resistance and water resistance. When the ratio is 70% by weight or less, the composition becomes low in viscosity and is excellent in coatability. The adhesion is extremely excellent. Γ0 0 5 81 2, (B) component 101120538 1013293S44-0 27 201249948 (B) The component is an ethylenically unsaturated compound, and any compound having an ethylenically unsaturated group can be used. The ethylenically unsaturated group may, for example, be a (meta) acryloyl group, a vinyl group or a vinyl ether group. (B) Component 呻 blending ratio The total weight of the curable component is 1% by weight, and the ratio is 30 to 80% by weight, more preferably 40 to 70% by weight. When the proportion of the component (B) is 30% by weight or more, the hardenability can be improved and the viscosity can be lowered. When the ratio is 80% by weight or less, the adhesive strength and water resistance of the composition can be prevented from being lowered. [B] The (B) component 'is exemplified by (b), an ethylenically unsaturated compound having a trans group "hereinafter referred to as (M) component"; and two or more ethylenic unsaturation in the molecule. a compound of the group "hereinafter referred to as (b2) component"; and a compound having one ethylenically unsaturated group, (bl) and (b2) in the molecule, "hereinafter referred to as other monofunctional unsaturated compounds" 》. [00 6 0] The (bl) component is an ethylenically unsaturated compound having a hydroxyl group. It is preferable that the (bl) component 'is a (meta) acrylate having one radical and one ethylenic unsaturated group in the molecule. 101120538 1013293844-0 28 201249948 Related (partial) acrylates, specifically, exemplified by: 2-hydroxyethyl (meta) acrylate, 2-propyl propyl ( Bis) 2-hydroxypropyl (meta)acrylate, 2-butyl (meta) acrylate, 4-hydroxybutyl (meta) acrylate, cyclohexane dimethanol Monoacrylate), cyclohexene oxide (meta)acrylic acid adduct, polyethylene glycol O mono(meta)acrylate , polypropylene glycol mono (meta) acrylate, polytetramethylene glycol mono (meta) acrylate, polyethylene glycol polypropylene glycol mono (meta) acrylate (polyethylene) Glycol polypropylene glycol mono(meta)acrylate), polyethylene glycol polytetramethylene glycol mono (meta) acrylate, polypropylene glycol polytetramethylene glycol mono (meta) acrylate, 2-carbyl-3-benzene 2-hydroxy-3-phenoxy 〇propyl (2-hydroxy-3-phenoxy 〇propyl ( Meta)acrylate), 2-hydroxy-3-butooxy propyl (meta)acrylate, 2-(meta)propenyloxyethyl-2 2-(meta)acryl〇yl〇xyethyl-2-hydroxyethyl phthalate) 2-(P)acryloyloxyethyl-2-hydroxypropyl phthalate. [00 6 1] 101120538 1013293844-0 29 201249948 In the (bl) component, it is preferable that the compound having a very low viscosity and having a very good adhesion to the material of the material s of 3 GG or less is preferable. The compound which can be obtained in the molecule can be exemplified by, for example, 2_ethyl (6) acrylate, 2 propyl (meta) acrylate, 2-butyl (meta) acrylate, 4_ a (partial) acrylic acid addition product of butyl (meta) acrylate, cyclohexane dimethanol monopropionate, epoxy cyclohexane (cycl 〇he), 2-carbo-phenoxypropyl (Partial) propylene _ vinegar, etc.; from the point of view of water resistance, '4-nail base (partial) propylene is more desirable. The blending ratio of the (bl) component and the total weight of the curable component are 1 嶋 by weight, and 10 to 50% by weight is desirable, and more preferably 2 〇 to 4 〇% by weight. When the proportion of the component (M) is at least 1% by weight, the hardenability can be improved and the viscosity can be lowered. When the ratio is 5% by weight or less, the adhesion of the composition and the water resistance can be prevented from being lowered. [0063] In the component (A) of the present invention, after the completion of the irradiation of the active high-energy ray, the reaction is still carried out and hardened, and due to the so-called dark reaction phenomenon, there is a problem with the use of the diserepaney. Or an unsatisfactory situation; for example, 'Yi Xiao in the thin 峨 的 制造 制造 制造 制造 制造 , , , , , , , , , , , 活性 活性 活性 活性 活性 活性 活性 活性 活性 活性 活性 活性 活性 活性 活性 活性 活性 活性 活性 活性 活性 活性 活性 活性 活性 活性 活性-0 201249948 The shape of the song will be left behind. 'The film is easy to present such problems as undulati〇n or dent. In the case of preventing such a problem, it is desirable that the elastic modulus of the adhesive layer is increased after the irradiation of the active high-energy ray, and that the (b2) component is highly effective in the (β) component. Moreover, since the cross-linking density (cr〇ssiink density) is improved, heat resistance is also improved.化合物 [0064] The compound (b2) is preferably a compound having two or more (meta) acryloyl groups, hereinafter referred to as a multifunctional (polar) acrylate. Specific examples of the multifunctional (partial) acrylate include polyol (meta) acrylate, such as 1,4-butanediol di(di) acrylate (l , 4-butandiol di(meta)acrylate), neopentyl glycol di(meta)acrylate, 1,6-hexanediol di(meta)acrylic acid g (l,6-hexandiol) Di(meta)acrylate), 3-methyl-l, 5-pantadiol di(meta)acrylate, 2-butyl-2-ethyl 2-(2-butyl-2-ethyl-l, 3-nonanediol di(meta)acrylate) 2-mercapto-1,8-octanediol 2-methyl-l, 8-octanediol di(meta)acrylate, 2-amino-1,3-di(ex)propenyloxypropane (2-hydroxy-) l, 3-di(meta)acryloyloxy propane), 2-carbyl-3-(Partial) 101120538 1 1013293844-0 201249948 Propyleneoxypropyl (partial) acrylic acid vinegar (2-hydroxy-3-( Meta) acryloyl〇xypropyi (meta)aciTiate), glycerin di(meta)acrylate, trimethylolpropane tri Trimethylolpropane tri(meta)acrylate, pentaerythritol tri(meta)acrylate, pentaerythritol tetra(meta)acrylate, dipentaerythritol five (bias) ) pentaerythritol penta (meta) acrylate, dipentaerythritol hexa(di) acrylate, bis (trimethyl methacrylate) tetra (meta) acrylate g, etc. Diester acid ester; di(p-) acrylate of an indene phenol olefin alkylene oxide adduct; bismuth hexamethylene acrylate; Tri(p-)acrylic acid acrylate of olefinic oxyethylene adduct of glycerol, tri(pre) acrylate of trimethyl propylene oxide alkylene oxide adduct, tri(p-)acrylic acid of pentaerythritol alkylene oxide adduct Poly(p-)-pro-glycolic acid vinegar of an alkylene oxide adduct of a polyol such as vinegar; neopentyl glycol modified (m〇dified) trimethyl methacrylate (partial) acrylic acid vinegar, etc. Glycol-modified polyol poly(meta) acrylate; capr 〇lactone modified A caprolactone-based modified polyol poly(meta) acrylate such as pentaerythritol hexa-(acrylic acid) vinegar; ethylene giyC〇i di(meta)acrylate And propylene glycol di(pre) acrylate vinegar, and butane diol di(p-) acrylate vinegar, etc. aikylene gi_ di(meta)acrylate; 101120538 32 1013293844- 0 201249948 diethylene glycol di(meta)acrylate, triethylene glycol di(meta)acrylate, multiolefin diol di(meta) acrylate vinegar; An alicyclic diol such as tricyclodecane dimethylol di(meta)acrylate and dicyclopentanyl di(meta)acrylate (Partial) acrylic acid ester; bis(di) acrylate of bisphenol A alkylene oxide adduct, bis(meta) acrylate of bisphenol F alkylene oxide adduct, and bisphenol S olefination Bis(di)propionate of a dioxonated alkylene oxide adduct of a di-(p-) acrylate such as an oxygen adduct; hydrogenated bisp a hydrogenated bisphenol compound alkylene oxide adduct of a bis(meta) acrylate of an alkylene oxide adduct of henol A) and a di(meta) acrylate of an alkylene oxide adduct of hydrogenated bisphenol F Di(p-)acrylic acid acrylate; isocyanuric acid alkylene oxide adduct of di(p-)polyacrylic acid ester, isocyanuric acid alkylene oxide adduct of tris(di)acrylic acid ester , poly(meta) acrylate of isocyanuric acid such as tris(di)acrylate of isocyanurate caprolactone adduct; neopentyl glycol by nitrapentyl acid (ne〇pentylglyc〇i hydr〇xypivalate) Di- (meta) acrylate of ester diol such as (partial) acrylate, hydroxypivalic acid neopentyl glycol di(pre) acrylate; modified pentylene glycol hydroxypivalic acid a di(meta) acrylate of a dicaprolactone-modified ester diol of di(4)acrylic acid g|#;

10112053S 1013293844-0 33 201249948 The polyol is reacted with (meta)acrylic acid and a fatty acid having a carbon number of 2 to 4, and the obtained fatty acid is modified with dipentaerythritol penta (partial) propionate and Fatty acid modified dipentaerythritol tetra (partial) acrylate, etc.; hexahydro-1,3,5_tris(1-oxo-2-propenyl)_1,3, 5-triacyl (triacrylformal); Trimethylolpropane (me ta ) aery 1 ic ac id ) benzoic acid (benzo ic ac id ) ester, Oguso 1E A-0200, 0500, 1000 "fluorinated acrylate", Osaka C) Aromatic multifunctional (partial) acrylates manufactured by Gas Chemical Co., Ltd., etc. Further, examples of the oxidative oxygen addition product include an ethylene oxide adduct and a pr〇pyiene oxide adduct. Further, the oligomer (oligomer) which can be used as the component (b2) may, for example, be a polyester (meta) acrylate or a Q epoxy (epoxy) acrylate (ep0Xy). (meta) aCrylate), and polyether (meta) acrylate (polyether (meta) acrylate) and the like. Further, although these oligomers are compounds having two (partially) acrylonitrile groups, they are used in accordance with customary usage, and in particular, there is no prohibition of limitation. [0066] 101120538 34 1013293844-0 201249948 酉曰 (meta) acrylate (meta) acryiate), may be, from the dehydration of dehydration (dehydrau〇n condensation). Here, as the polyester polyol, a reaction product of a polyhydric alcohol with a carboxylic acid or an acid anhydride thereof may be mentioned. 0 As the polyol, there may be mentioned ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, polypropylene glycol, butanol, poly Butylene glycol, tetramethylene glycol, hexamettiylene glycol, neopentyl glycol, cyclohexane dimethanol, 3-methyl-1,5-pentanediol, 1 , a low molecular weight polyol such as 6-hexanediol, glycerin, pentaerythritol, and dipentaerythritol, and an alkylene oxide adduct thereof. As a carboxylic acid or an anhydride thereof, orthophthalic acid, isophthalic acid, terephthalic acid, and dimethoate may be mentioned. Acid (adipic acid), succinic acid (succinic acid), succinic acid (fumaric acid), fumaric acid (maleic acid), hexahydrophthalic acid A dibasic acid such as dicarboxylic acid (hexahydro-phthalic acid) or tetrahydro-phthalic acid or an acid needle thereof. 35 101120538 1013293S44-0 201249948 EB hard-poly (poly) acrylate, such as the foregoing

For the chemical materials, the compounds contained in the 74~76 hundred hearts I page 6 can be used. [0068] Epoxy (8) propylene salt (epGxy (meta) aGr fine) is a compound which reacts with a (acrylic) acrylic acid on an epoxy resin, for example, the above-mentioned document "υν·ΕΒ hardened material" 74 to 75 pages The compound which is described is exemplified and used.

The resin resin may be exemplified by an aromatic epoxy resin and an aliphatic epoxy resin. The aromatic epoxy resin, specifically, may be exemplified by resorcinol diglycidyl ether; double expectant A, double F, bisphenol S, bisphenol fluorene or its alkenyl a phenolic epoxy resin such as a phenol novolac type epoxy resin or a cresol novolac type epoxy resin; a glycidyl group adjacent to a oxyphenol adduct; Glycidyl phthaliinide; diglycidyl ο-phthalate. In addition to these compounds, it is also possible to use, for example, the second chapter of the literature "Epoxy resin one recent development one" [Zhao Shengtang's 1990 issue], or the literature "Polymer processing" book 9 · Volume 22 Supplement Various compounds described in 4 to 6 pages and 9 to 16 pages of epoxy resin [Molecular Publications, issued in 1988). 36 10112Q533 1013293844-0 201249948 [0070] As a fat bribe, the more you can

Diglycidyl diols of diols, "butanediol and heart diols (10); diethylene glycol diols of I gamma and diglycidyl diols of polypropylene glycol, etc. Ether; Ο Ο neopentyl alcohol - / odor neopentyl glycol (dibiO___yl (4) > n diglycidyl ether of alkylene oxide adduct; trimethyl hydrazine (trimethyl hydrazine), trimethoprim Soil, = alcohol and its dilute oxygen adducts, two or three water-reducing _, and including the second and third or tetraglycidyl poly-alcohols of the quaternary alcohol and its alkylene oxide adduct Glycerin shout; hydrogenated double A and its thinned oxygen adducts of one or more glycidol; four gasified phthalic acid (tet_dn)-phthalie acid) condensed water; benzodiazepine (hydroquinone) Glycidyl ether or the like. Other than the above-mentioned D product, for example, the compounds described in the above-mentioned document "Polymer Processing", Epoxy Resin, 3 to 6 pages can be cited. [007 1] These aromatic epoxy resins and aliphatic jobs In addition to Wei Shuzhen, an epoxy compound having a triazine core on a structural skeleton can also be cited, for example,

TEPIC(tit)>Denac〇1 EX-310(NagasechemteX 101120538 37 1013293844-0 201249948 (share) company made 箄.又符么寻” is also like a narration of the literature "gang molecular processing" album Epoxy tree moonlight The compound described in 289, page 296 can also be used. For example, the alkylene oxide of the alkylene oxide adduct in the month described above is a combination of ethylene oxime (Xeide) and propoxy propylene (Propylene oxide). [0072] As a P〇lyether (methacrylate) oligomer, there is: a poly(hydrocarbyl glycol) di(p-) acetoacetate (p〇lyalkylene glyc〇l 0 di ( Meta)acrylate) 'for example, polyethylene glycol di(poly) acrylate, polypropylene glycol di(di) acrylate, and polytetramethylene glycol di(meta) acrylate, etc. [0 0 7 3] Examples of the compound other than the (partial) acrylate of the component (b2) include a compound having two or more cations (aiiyi groUp); diallyl phthalate; , triallyl isocyanurate and triallyl isocyanurate The polymer (triallyl cyanurate) or the like can be used. The polymer which can be used as the component (b2) is a (partial) acrylic polymer having a (Part) acryloyloxy group, that is, A compound composed of a (meta) acryloyl group introduced into a side chain of a functional (partial) acrylic polymer, as described in the above-mentioned document "υν·ΕΒhardening material", pages 78 to 79 38101120538 1013293844-0 201249948 [0074] From the viewpoint of preventing unfavorable conditions due to dark reaction and improving heat resistance, as the component (b2), it is preferable to have a poly Olefinyl diol di(pre)acrylic acid self-deuterated, dicyclic decane dimethylol di (meta) acrylate, diphenyl decane dimethylol di (meta) acrylate Ester, olefinic oxygen denatured di(pre) acrylate of bisphenol F, di(trans)acrylate of isocyanuric acid alkylene oxide adduct, capable of maintaining adhesion to hydrophilic plastics Point of view Desirable are: trisuccinic acid esters of poly(nicotinoic acid) diisopropionate, isocyanuric acid, and oxygenated adducts. (b2) The proportion of the components to be blended, and the total weight of the curable component is 1% by weight. 'Comparatively, it is preferably 1 to 50% by weight, more preferably 1 to 継 by weight 0 O (b2) When the ratio of the component is 1% by weight or more, it is possible to prevent an unfavorable situation due to a dark reaction and to improve the heat-generating property; when the ratio is 50% by weight or less, the hardening shrinkage of the composition is suppressed, and it becomes an adhesive force. Excellent composition. Examples of the other monofunctional unsaturated compound include an ethylenic compound, an allyl compound, a (meta) acrylamide compound, and one ethylenic group in the molecule. Unsaturated aromatic ring skeleton structure or 39 101120538 1013293844-0 201249948 Compound of alicyclic skeleton structure, aliphatic (partial) propylene _, acid group-containing (meta) acrylate, containing phosphate group ) two women's acid salts. [0076] The substance having a low viscosity and excellent heat resistance and adhesion is provided with an aromatic ring skeleton structure or an alicyclic skeleton structure containing one ethylenically unsaturated group. Ideally; in terms of frequency, it can be used: alicyclic (partial) acrylate, aromatic (partial) propionate, imide (meta) acrylate (imide (meta) acrylate) . [0077]

The alicyclic (bias) acrylate may be exemplified by isobornyl (meta) acrylate, b〇rnyl (meta) acrylate, or tricyclic oxime. Tricycl〇decanyl di(meta)acrylate, dicycl〇pentanyl Q (meta)acrylate, 4-butylcyclohexyl (meta) acrylate ( 4-butyl cyclohexyl (meta)acrylate), tetrahydrofurfuryl (meta)acrylate, cyclohexyl (meta)acrylate, dicyclopentenyl ( Dicyclopentenyl (meta) acrylate, adamantyl (meta) acrylate, tricyclic terpine (bias) acrylate 40 10112 Ό 538 1013293844-0 201249948 (tricyclodecanedi (meta )acrylate), dicyclopentenyloxyethyl (meta)acrylate, and the like. [0 0 78] The aromatic (partial) acrylate may be exemplified by (p-) acrylate, phenol derivative (partial) acrylate, benzyl (benzyl) ( (Partic) acrylic acid, phenoxyethyl (meta) acrylic acid vinegar, (partial) acrylate of olefinic oxygenated denatured product, and (partial) acrylic acid of oxidized denatured product of cresol (pre) acrylates of esterified oxygenated denatured esters of p-Cumylphenol, (partially) acrylates of orthobenzenes of nonylphenol (Partic) acrylate of ozonized oxygenated denatured material of ο-phenylphenol, (partial) acrylate of dilute oxygenated denatured substance of p-phenylphenol, tribromobenzene ( Tribromophenol) (bias) acrylate, neopentyl glycol (meta) benzoic acid ester, and the like. [0079] An imide (meta) acrylate, which can be exemplified by: N-(meta) propylene methoxyethyl hexahydrophthalene imide (N-( Meta)acryloyloxy ethyl hexahydrophthal imide) 2-(1 2-cyclohex-1-enedimethylimine)ethyl (meta) acrylate (2-(l,2-cl〇hexa-i-en dicarboximide) Ethyl (meta)acrylate), FANCRYL FA-502A "曰101120538 1013293844-0 41 201249948 manufactured by Lihuacheng Industrial Co., Ltd." and the like. Among these compounds, for the reason that heat resistance or adhesion can be high, it is preferable to use iS〇b〇rnyl (meta)acrylate, DiCyCi〇perrtanyi (meta)acrylate, tetrahydrofurfuryl (meta)acrylate, dicyclopentenyl (meta) phthalate (dicyclopentenyl) (meta)acrylate), dicyclopentenyloxyethyl (meta)acrylate, benzyl (partial) acrylic acid, phenoxyethyl (phen0Xyethyl) (N-(meta)acryloyloxy ethyl) Hexahydrophthalimide), 2-(1,2-cyclohex-1-enedimethyleneimine)ethyl (partial) acrylate (2-(1,2-clohexa-l-en dicarboximide) ethyl ◎ (meta )acrylate) and so on. [0 0 8 1] Examples of the vinyl compound include styrene, vinyltoluene, N-vinyl-pyrrolidone, and N. -N-Vinyl-caprolactam, vinylimidazole, ethylene-beta beta ratio 42 101120538 1013293844-0 201249948 (vinyl-pyridin) and other monofunctional ethylene compounds Ethylene compounds such as divinylbenzene. [0 0 8 2] Examples of the allyl compound include a compound such as a propylene compound such as allyl alcohol. 〇【0 0 8 3】 As a (meta) acrylamide compound, diacetone (meta) acrylamide, isobutoxy (diacetone) Isobutoxy)methyl (partial) acrylamide, N,N-dimercapto (p-) acrylamide, t-Ctyl (meta) acrylamide, N, N- Diethyl (meta) acrylamide, N, N-dimethyl aminopropyl (meta) acrylamide, (p-) propylene ketone morpholine ( Meta)acryl〇ylmorpholine), (meta) acrylamide-2-me1:hylpropane sulfonic acid, N-isopropyl (p-) acrylamide, etc. . Specific examples of the aliphatic (partial) acrylate may be exemplified by using fluorenyl (partial) acrylic acid vinegar, ethyl (partial) acrylic acid vinegar, propyl (partial) propylene (four), and different Propyl (4) acrylic acid vinegar, butyl (partial) acrylic acid vinegar, sulfhydryl (partial) acrylic acid vinegar, isobutyl (4) 1011205 38 43 1013293B44-0 201249948 , 'acrylic acid| __, different collar bias (four) _ purpose, hexyl (8) acrylic vinegar, silk (partial) yttrium acrylate, octyl (〇 ctyi) (partial) acrylic acid vinegar, isooctyl (partial) acrylic acid vinegar, 2-ethyl Hexyl (partial) acrylic acid vinegar, mercapto (partial) acrylic acid S, decyl (partial) dienoic acid vinegar, isodecyl (partial) acrylic acid vinegar, undecyl (bias) acrylic acid , 12 烧 基 (d〇decyl) (partial) acrylic acid vinegar, lauryl (partial) acrylic acid vinegar, carbon number 12~13 dazzle (partial) propylene vinegar, cetyl (cetyl (Partially) acrylic acid, stearyl (partial) acrylic acid vinegar, isostearyl (p-) acrylic acid g, isomyristyl (partial) hydrazine acrylate, oxime Methoxyethyl (partial) propylene Ester, 3-methoxybutyl (meta) acrylate, ethyl carbitol (ethyicarbit〇l) (partial) acrylate, 2-ethylhexyl carbitol (partial) acrylate, B Ethoxyethoxyethyl (meta) acrylate, butoxyethyl (meta) acrylate, methoxyethylene glycol (col) acrylate, ethoxydiethylene Ethylene diethylene glycol (partial) acrylate, ethoxyethyl (meta) acrylate, decyloxytriethylene glycol (partial) hydrazine acrylate, methoxy polyethylene glycol ( Partial) acrylate, decyloxypolypropylene glycol (meta) acrylate, dimethylaminoethyl (meta) acrylate, diethylaminoethyl (meta) acrylate, 7-amino-3, 7- Dimethyloctyl (partial) acrylate and the like. [00 8 5] Specific examples of the (meta) acrylate having a carboxylic acid group include, for example, (partial) acrylic acid, (dimer) acrylic dimer (dimer), 2-(meta) propylene oxy group.乙44 101120538 1013293844-0 201249948 2-(meta)acryloyloxy ethyl succinic acid, 2-(meta)acryloyloxy ethyl phthalic acid ,2-(meta)acryloyl〇xy ethyl hexahydro-phthalic acid' ω-carboxypolycaprolactone (ω-carboxypolycaprolactone) (Polar) acrylate containing a carboxylic acid group such as a acrylate. 〇【0 0 8 6】 The (partial) acrylate containing a phosphoric acid group may be, for example, 2-(meta)acryloyloxy ethyl acid phosphate or the like. . [0087] In addition to these compounds, the component (B) which is another monofunctional unsaturated compound Ο can be used, for example, the literature "Latest UV Hardening Technology" (issued by the Printing Information Association of 1991), 53-56 pages The compounds described can be used. The ratio of the other monofunctional unsaturated compound is 100% by weight of the total weight of the curable component, and the ratio is preferably 〇 to weight ratio, more preferably 0 to 30% by weight. When the ratio is 40% by weight or less, the heat resistance of the cured product can be improved. [0 08 8] 1013293844-0 101120538 201249948 3 ' (C) The component (c) is a Cationic photo-polymerization initiator. The component (C) is a compound which initiates a polymerization reaction, and irradiates a cation or a Lewis acid with a reactive high-energy ray to start a polymerization reaction of the component (A) which is a cationic photopolymerizable compound. Specific examples of the component (C) include sulfonium salt, magnetic salt (i〇d〇niumsalt), and azozonium ion ◎. [0089] Examples of sulfonium salts, for example: triphenylsulfonium hexafluorophosophate triphenylsulfonium hexafluoroantimonate triphenyl Diphenylsulfonium tetraki s-(pentaf1uoropheny1)borate) diphenyl-4-(phenylthio)phenylphosphonium hexafluorophosphate (di pheny1-4-(pheny1th) i ο) pheny1su1fon i um hexafluorophosophate) diphenyl-4-(phenylthio)phenyl sulfonium hexafluoroantimonate 46 101120538 1013293844-0 201249948 (di pheny1-4-(pheny1th io) pheny1su1fon i um hexafluoroantimonate) 4,4'-bis[diphenylsulfonio] diphenyl sulfide bi s-hexafluorophosophate 4,4'-double [two (no-menstrual) (4,4*-bis[di-(^-hydroxyethoxy)phenylsulfonio] diphenyl O sulfide bis-hexafluoroantimonate) 4, 4'-double [ Di(p-hydroxyethoxy)phenylindenyl]phenyl sulfide dihexafluorophosphoric acid (4, ^ -b Is[di-(β-hydroxyethoxy)phenylsulfonio] diphenyl sulfide bi s-hexafluorophosophate) 7-[bis(p_曱benzylidene)indolyl]-2-isopropylthioxanthone hexafluoroantimonate (7 -[di(p-toluy1)su1f on i 〇]-2-i sopropy1 thioxanthone hexaf1uoroant imonate) 〇7-[bis(p-tolylmethyl) fluorenyl]-2-isopropyl thioxanthone four ( Hexafluorophenyl)boronic acid (7-[di(p-toluyl)sulfonio]-2-isopropyl thioxanthone tetraki s-(pentafluoropheny1)borate) 4-phenylcarbonyl-4'-diphenylmercaptophenyl sulfide hexafluoro 4-phenylcarbonyl-4'-diphenyl sulfonio diphenyl sulfide hexafluorophosophate 4-(p-tert-butylphenylcarbonyl)-4'-diphenylmercaptophenyl sulfide hexafluoroantimonate (4-( P-tert-butylphenylcarbonyl)-4*-diphenyl sulfonio 47 101120538 1013293844-0 201249948 diphenyl sulfide hexaf1uoroantimonate) 4-(p-tert-butylphenylcarbonyl)-4'-bis(p-tolylmethyl) fluorenyl Triarylsulfonium salt such as 4-(p-tert-butylphenylcarbonyl)-4'-(p-toluyl)sulfonio diphenyl sulfide tetrakis-(pentafluorophenyl)borate (Triaryl sulfonium salt) may include use. [0 0 9 0] Examples of iodonium salts, for example: diphenyl iodonium tetrakis-(pentafluoropheny1) borate diphenyl hydrazine Diphenyl iodonium hexafluorophosophate Diphenyl iodonium diphenyl iodonium

Hexaf1uoroantimonate) Q bis(4-tert-butylphenyl) mothyl hexafluoride (di(4-t-butylphenyl) iodoni um hexaf1uorophosophat) one (4-tert-butylphenyl) sulfonium salt Di(4-t-butylphenyl) i odonium hexaf1uoroant i monate 曱 曱 曱 曱 U U 埃 埃 埃 U U U U U U U U U U U U U U U U U U U U U U U U U U U U U U Borate) Equivalent salt (4-methylphenyl)[4-(2-methylpropyl)phenyl]-hexafluorophosphoric acid 101120538 48 1013293S44-0 201249948 (i odon i um(4-methy1pheny1)[4 -(2-methylpropy1)pheny1 -hexafluorophosophate) Di(4-nonylphenyl) iodonium hexafluorophosophate di(4-alkylphenyl) base salt A diaryl iodonium salt such as di(4-alkylphenyl) iodonium hexaf luorophosophate can be used. Examples of the azozonium ion, for example, benzene diazonium hexafluoroantimonate, benzene diazonium hexaf luorophosophate, and the like can be used. [0 0 9 2] Commercially available products of the component (C) include: ADEKA 0PT0MER SP-100, 150, 152, 170, 172 "Manufactured by ADEKA"; Photoinitiator 2074 "Manufactured by Rhodia"; KAYARAd PCI-220, 620 Nippon Chemical Co., Ltd. Manufacturing; Irgacure 250 "Manufactured by CIBA · JAPAN"; CPM00P, 101A, 200K, 210S "Manufactured by SAN-APRO"; WPI-113, 116 "Manufactured by Wako Pure Chemical Industries Co., Ltd."; BBI -102, 49 101120538 1O13293S44-0 :: 201249948 103 TPS 103 > DTS-102 'DTS-103 (manufactured by Midori Kagaku Co., Ltd.), etc. Among these compounds, excellent in active high energy ray hardenability The reason why the hardened film is excellent in water resistance and not colored, and the triaryl sulfonium salt and the diaryl base salt are preferable; in particular, from the viewpoint of excellent hardenability, the diaryl iodonium salt More desirable. Diaryl sulfonium salts ' Among the foregoing compounds, preferred is triphenyl sulfonium salt (tr i pheny 1 su 1 fon i um hexaf 1 uorophosophate ) Diphenyl-4-(phenylthio)phenyl sulfonium salt hexafluoro Phosphoric acid (di pheny1-4-(pheny1th io) pheny1su1fon i um hexafluorophosophate). Diaryl iodonyl salts, among the above compounds, preferably benzinyl cumyl ketone salts (pentafluoride) Phenyl) boryl iodonium tetrakis-(pentafluorophenyl)borate, diphenyl iodonium hexafluorophosophate 'iodoyl salt (4-mercaptophenyl)[4-(2 -Methylpropyl) phenylene]-(4-methylphenyl)[4-(2-methyl propyl)phenyl-hexafluorophosophate, bis(4-tert-butylphenyl) moth Di(4-t-butylphenyl) iodonium hexaf luorophosophat and WPI-113, manufactured by Wako Pure Chemical Industries, Ltd. [0 0 9 3] 50 101120538 1013293844-0 201249948 As component (c), These compounds may be used alone or in combination of two or more. The blending ratio of the component (C) is 1 20 20% by weight based on the total weight of the curable component. The ratio is preferably 0.1 to 20% by weight. ~ should be weight ratio. (c) When the ratio of the component is 〇. 1% by weight or more, the composition becomes an active high-energy ray-curable material, and it can be excellent in adhesion; on the other hand, 2 (10) by weight or less, the adhesive layer The internal hardenability is good, and it can be excellent in adhesion. Further, in the present invention, in order to improve the cationic photocurability, a sensitizer may be used. These are also included in the composition as the component (c). Examples of the sensitizer include: anthracene compound, 4-methoxy-l-naphthol, fluorene, pyrene, and stilbene. (stilbene) and so on. Q Anthracene compounds, such as onion, 9,10-dimethoxy anthracene, 9,10-diethoxy onion, 9,10-dipropoxy onion, 2-ethyl-9,10-dimethoxy onion, 2-ethyl-9,10-diethoxy onion, 2-ethyl-9,10-dipropoxy onion, 4'-nitro Benzyl-9,10-dimethoxy anthracene-2-sulphonate, 4'-stone-based base-9,10-diethoxy The onion _2-sulfonate, 4'-nitrobenzyl-9,1 fluorene-dipropoxy onion-2-acid salt and the like can be used. 10112Q538 1013293844-0 201249948 Among these compounds, 'from the viewpoint of solubility, photosensitivity, etc., 9,1 〇 dimethoxy onion, 9,10-diethoxy onion, 9,10-dipropoxy onion More ideal than ideal. Commercial products of these sensitizers, such as Antracure UVS-1331, 1221, and 1101, ET-2111, manufactured by Kawasaki Kasei Kogyo Co., Ltd., can be used. The compounding ratio of the sensitizer is preferably from 0.1 to 20% by weight, more preferably from 10 to 10% by weight, based on 100% by weight of the total weight of the curable component. When the plastic of the adherend has a large ultraviolet absorbing property and a dredged salt is used as the component (C), it is preferable to use a quinone compound as a sensitizer. [0 0 9 6] 4. Component (D) The component (D) is a radical photopolymerization initiator (radicai photo-polymerization initiator). The 〇)) component is a compound which generates a radical by irradiation with active high-energy ray and starts a polymerization reaction of the component (B) containing an ethylenic unsaturated compound. Further, depending on the type of the component (d), there is a compound which promotes photolysis of the component (C) and can be used as a photosensitizer. [00 9 7] 1013293844-0 10112Q538 201249948 Specific examples of (D) components are: benzyl dimethyl ketal, benzyl, benzoin, benzoin ethyl ether , benzoin isopropyl ether, benzoin isobutyl ether, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenyl 2-hydroxy-2-methyl-l-phenylpropan-l-one, 1-[4-(2-carbylethoxy)-phenyl]~2-yl-2-yl 1-[4-(2-hydroxyethoxy)-phenyl]-2hydroxy-2-methyl-l-propan-1-one), oligo[2-pyridyl-2 -Methyl-l,[4-l-(methylethlyl)phenyl]propanone](〇11舀〇[2-1^(1]:〇«7-2-11161:]1丫1-1 - [4-l-(methylvinyl)phenyl]propanone]), 2-yl-l-{4-[4-(2-yl-2-methyl-propionyl)-]]-phenyl]-phenyl }-2-methyl-1-(4-(4-hydroxy-2-methyl-propionyl)benzyl]-phenyl}-2-methyl Q propan-1-one , 2-mercapto-l-[4-(methylthio)phenyl]-2-oxalyl-l-one (2-methyl-l-[4-(methylthio)) -phenyl]-2-morpholino propan-l-one), 2-benzyl-2-didecylamino-1-(4-morphinylphenyl)butan-1-one (2-benzyl-2-dimethylamino) -l-(4-morpholino phenyl)butan-l-one), 2-dimethylamino-2-(4-mercaptobenzyl)-1-(4-morpholin-4-yl-phenyl)- 2-dimethy1amino-2-(4-methy1benzy1)-1-(4-morpholin -4-y 1 -pheny 1) -butan-1 -one ), ADEKA 0PT0MER N-1414 "旭电化53 101120538 1013293B44-0 201249948 Manufactured by the company, phenyl glyoxylic acid methyl ester, ethy 1 anthraqu i none and phenanthrene

Aromatic ketone compounds such as I quinones; benzophenone, 2-methylbenzophenone, 3-methylbenzophenone, 4-methyldibenzophenone, 2,4, 6-trimethyldiphenyl fluorenone, 4-phenylbenzophenone, 4-(methyl phenylthio) phenyl phenyl methane, thiol-2- bis Benzophenone, l-[4-(4-phenylhydrazinophenyl fluorenyl)phenyl]-2-methyl-2-(4-methylphenylsulfine) propyl hydrazine (1-[4 -(4-Benzoy1pheny1su1fany1) pheny1] -2-methyl-2-(4-methylphenyl sulfonyl)propan-l-one) '4, 4'-bis(dimercaptoamino)benzophenone (4,4' - Bis(dimethylamino) benzophenone), 4,4'-bis(diethylamino)benzophenone, N,N'-tetramethyl-4,4'-diaminodibenzophenone (N, N' - Tetramethyl-4,4'-diamino benzophenone), hydrazine, Ν'-tetraethyl-4,4'-diaminobiphenyl-, and 4-methoxy-4'-dimercaptoaminodiphenyl hydrazine_ Ethylene benzophenone | bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide ,4,6-tridecyldiphenylhydrazine Phenylphosphine oxide, ethyl (2,4,6-trimethylbenzoyl) phenyl phosphinate, and bis(2,6-dimethoxy) Diphenyl hydrazine)-2,4,4-trimethylphenylpentyl phosphine oxide (bis(2,6-dimethoxy benzoyl)-2,4,4-trimethyl 54 101120S38 1013293844-0 201249948 pentyl phenylphosphineoxide) Acyl phosphine oxide compound; thioxanthone, 2-aestheticone, 2,4-diethylserthione, isopropyl ketoxime, 1-chloro-4- Propyl ketone, 3-[3,4-dimercapto-9-oxo-9H-sultoxan-2-yl]oxy-2-hydroxypropyl-N,N,N-tridecyl chloride Ammonium (3-[3, 4dimethyl-9-oxo-9H-thioxanthone-2yl] oxy-2-hydroxy1 propyl- N, N, N- trimethyl ammonium O chloride), and sevotonone Acridine compounds such as acridone and 10-butyl-2-chloroacridone; 1,2-octanedione 1-[4-(phenylthio)-2-(0 -1,2-octandione l-[4-(phenylthio) -2-(0-benzoyl oxime)], ethyl ketone l-[9-ethyl-6-(2-A Dibenzoquinone)-9H-carbazol-3-yl]- 1-(0-ethinyl) (ethanone 〇1-[9-ethy1-6-(2-methy1benzoy1)-9H-carbazo1e-3-y1] -1-(0-&〇6171(^丨1 ^) Equivalent esters, 2-(o-chlorophenyl)-4, 5-diphenyl imidazole dimer, 2- (o-p-phenyl)-4,5-di(m-decyloxy)imidazole dimer, 2-(o-fluorophenyl)-4, 5-phenylimidazole dimer, 2- (o-nonyloxyphenyl)-4,5-diphenylimidazole dimer, 2-(p-methoxyphenyl)-4,5-diphenylimidazole dimer, 2, 4- Bis(p-methoxyphenyl)-5-phenylimidazole dimer, and 2-(2,4-dimethyl 101120538 1013293844-0 55 201249948 oxybenyl)_4, 5-diphenyl pm beta Sitting on a monomeric 2, 4, 5_ triaryl imidazole dimer; and 9-phenylacridine and 1,7-bis (9, 9,-τ) »Bite base) An anthracene derivative such as 1,7-bis (9,9'-acridinyl) heptane can be used. Among these compounds, the ketoxime compound is preferable in that it can improve the photosensitivity of the component (c). Among the ketoxime compounds, 2,4-diethyl ketoxime and isopropyl oxime are more desirable from the viewpoint that the active high energy ray hardenability is excellent and the hardened film discoloration is small. The compound (D) can be used singly or in combination of two or more kinds of <[0100]' relative to the total weight of the curable component.

Formulation ratio of component (D) 101120558 1013293844-0 201249948 Composition of sex. 5. Other components In the present invention, in addition to the components (A), (B), (C), and (D) described above, other components may be blended as needed.理想 [0102] The ideal component which can be used in the present invention is one which has one or more cationically polymerizable Wei groups in the molecule and a compound other than the component (A); and the compound which is a chemical formula (1) An epoxy compound which is a hydrogen atom "hereinafter, referred to as an unsubstituted epoxy compound", an alicyclic epoxy compound, an oxetane compound, or a vinyl ether compound. 〇 [0 10 3] Unsubstituted epoxy compounds, classified into aromatics and aliphatics. Examples of the aromatic group include Bisphenol A diglycidyl ether, diglycidyl ether of bisphenol f, diglycidyl ether of bisphenol S, and brominated bisphenol a. Diglycidyl ether

Bisphenol A diglycidyl ether), diglycidyl ether of brominated dip-f, glycerol bismuth bromide, rubber-modified Bisphenol A diglycidyl ether, double Phenolphthalein 101120538 1013293844-0 57 201249948 (Bisphenolfluorene) or a bisphenol type epoxy resin such as di- or poly-glycidyl ether of its alkylene oxide adduct; phenol novolac (phenol n 〇v〇lac) epoxy resin, o-cresol novolac epoxy resin, brominated phenol, varnish-type epoxy resin, desertification, a pair of varnish epoxy resin A varnish-type epoxy resin such as a dicyclopentadiene benzene age-old varnish-type epoxy resin; a naphthalene epoxy resin; an Alkyl phenol epoxy resin; a naphthol type (naphthol) Epoxy resin: biphenyl epoxy resin; ◎ Hydroquinone diglycidyl ether; resorcin diglycidyl. ether; terephthalic acid ( Terephtalic acid) - glycidol puzzle Phthalic acid diglycidyl ether, styrene-butadiene copolymer epoxy, styrene-isoprene copolymer epoxide, Addition reaction of terminal carboxylic acid polybutadiene with bis-A epoxy resin, N,N,N',N'-tetraglycidyl-m-diphenylene diamine 〇(Ν,Ν,Ν', Ν '-tetraglycidyl-m-Xylene diamine) and the like. In addition, in addition to these compounds, the literature "Epoxy resin - recent developments" [Zhao Shengtang, issued in 1990] Chapter 2, or the literature "Polymer Processing" Book 9 · Volume 22 Supplemental Epoxy Resin The various compounds described in pages 4 to 6, pages 9 to 16, and pages 29 to 55 of the [Molecular Publications Association, issued in 48th year of the Showa] can be used. Here, the term "epoxy resin" means a compound or a polymer having an average of two or more unsubstituted epoxy groups in the molecule and hardened by the reaction. According to the conventional art in the field, the invention is as follows. In the present invention, the term "in the present specification" is a compound having two or more hardening unsubstituted epoxy groups in the molecule, and even a monomer is called an epoxy resin. Examples of the aromatic unsubstituted epoxy compound other than these compounds include Epikote 5050, 505, 1031, 1032H60, 604, 630, 871, 872, 191P, YX310, 545, YL6810, Π8800, and YL980. Above, jappon O Epoxy Resin (share) company manufacturing. Specific examples of the aliphatic unsubstituted epoxy compound include ethylene glycol, propylene glycol, u-butanediol, and anthracene diols such as 6-hexanediol (alkylene gly C〇l). Diglycidyl ether; diglycidyl mystery of polyolefin-based diols such as polyethylene glycol and polypropylene glycol condensed 7JC glycerol (tetra); neopentyllglycol, dibromo neopentyl glycol (dibmn〇) Neopentylglycol), and diglycidyl ether of its diluted oxygen (sweet xide) adduct; trimethyl sulfonate, trimethyl propyl propyl alcohol and its alkylene oxide a di- or tri-glycidol test of a product, and a polycondensation of a polyvalent alcohol such as pentaerythritol (Pentaemhrit Ql) and (iv) an oxygen adduct of a di-, tri- or tetra-glycolate; gasification double_ and its thinning One or more glycidol test of oxygen adduct; four gas o-benzene-formic acid (9) Shi ahydrophtha Uc acid) diglycidyl hydrazine; hydroquinone 101120538 59 1013293844-0 201249948 (hydroquinone) diglycidyl ether, etc., can be enumerated β other compounds other than the aforementioned literature "polymer plus The compounds described in the pages 3 to 6 of the epoxy resin can also be used. Examples of the aliphatic unsubstituted epoxy compound other than these compounds include Denarex R-45EPT, manufactured by Nagase ChemteX Corporation,

Epoflend ΑΤ5 (Π, CT310, Epoleed PB3600, above, Daicel Ο

Manufactured by Corporation, KL-630 "Manufactured by KURARAY CO., LTD", TETRAD-C "Manufactured by Mitsubishi Gas Chemical Co., Ltd.", and TEPIC "Manufactured by Silicon Chemical Industry Co., Ltd.". Specific examples of the alicyclic epoxy compound include: dicyclopentadiene dioxide, limonene ◎ dioxide, and 4-ethylene cyclohexanide (4) -Vinylcyclohexene dioxide), 3,4-epoxy cyclohexyl methyl (3,4-epoxy) cyclohexane (^1 ^〇\13 士6), bis(3,4-epoxy cyclohexylmethyl) adipate, 3,4-epoxycyclohexyl Methyl (meta) acrylates and the like can be used. In addition to these compounds, the literature "Epoxy resin one recent development one" (Zhao 60 101120538 1013293844-0 201249948 sangtang, issued in 1990) Chapter 2, or literature The various compounds described in the pages of pages 18 to 20 of the "Polymer Processing", vol. 22, Vol. 22, Supplement No. j, Epoxy Resin (Southern Molecular Publications, Issued in Showa 48) can be used. An oxetane compound is a compound having more than one oxetane ring in the molecule. Specific example, JP-A-8-857 The various oxetane compounds described in, for example, JP-A No. 8-134405, etc., may be used, and among these compounds, j or a plurality of oxetanyl groups may be used. The compound is more desirable. Examples of monofunctional oxetane are: 3-ethyl-3-(hydroxyfyl)oxetane, 3-ethyl-3-[(phenoxy) 3-ethyl-3-[(phenoxy)methyl] oxetaqe), 3-ethyl-3-(hexyloxyindenyl)oxetane (3-ethyb 3- (hexyloxy methyl) oxetane), 3-ethyl-3-(2-ethylhexyloxymethyl)oxetane, 3-ethyl-3-(3-chloroindenyl)oxetane, etc. Illustrative use; examples of two functional oxetane are: 1,4-bis[(3-ethyl-3-oxetanylmethoxy)f-yl]benzene (l'4-bis[( 3-ethyl-3-oxetanylmethoxy)methyl]benzene), bis{[1-ethyl(3-oxetanyl)]methyl}ether (bis{[l-ethyl(3-oxetanyl))methyl}ether And the like may be exemplified. [0109] The vinyl ether compound has one or more of two molecules in the molecule of 101120538 1013293844-0 61 201 249948 A vinyl ether based compound. Specific examples include, for example, n-propyl divinyl ether, isopropyl-ethylene bromide, η-butyl-ethyl sulfonate, trans-ethylidene diethyl fluorene, and cyclohexane dimethanol monodiethylene. Ether (cycl〇hexane dimethan〇1 ether), monoethyl alcohol monodiethylene _, 4-butyl butyl diethylene _, cyclohexyl diethyl hydrazine bond, eleven alkyl group, dodecyl vinyl ether, Octadecyl vinyl ether, iauryl vinyl ether, cetyi vinyi ether, 2-ethylhexyl divinyl ether, 2-( Ubiquinone monofunctional divinyl ether, such as 2-vinyloxyethoxy)ethyl (meta) acrylate; 1,4-butadiol di-vinyl ether, ring A multifunctional dichotomy of hexane didecyl bis (divinyl ether), diethylene glycol di(diethyl ether), and diethylene glycol di(diethyl ether). A compound other than the component (A) having one or more cationically polymerizable functional groups in the molecule, since the adhesiveness is high and the viscosity is low, the compound having a low amount of scorpion is relatively Desirably, a specific example is a compound having a molecular weight of 2 or less. Particularly preferred examples include lim〇nene dioxide and 3,4-epoxycyclohexyldecyl (3,4-epoxy)cyclohexanecarboxylate (3, 4-epoxy cyclohexyl methyl (3,4-epoxy) cyclohexane carboxy late ), 3-ethyl-3-(hydroxyindenyl) oxetane, 3-ethyl_3_[(phenoxy)methyl] Oxygen J (buty 1~3~[(phenoxy) methyl] oxetane), bis(3-ethyl-3-oxetanyl) linkage 62 120538 1013293844-0 201249948 (bis(3- Ethyl-3-oxetanylmethyl) ether). The composition of the present invention may be blended with other components of the commonly used adhesive composition formulation in addition to the various compounds described above. [0 112] For example, 'can be formulated, for example, silane coupling agent, inorganic fiUer, softener, antioxidant (antioxidani:), anti-aging agent (age) Resistors, stabilizers, tackifiers (= tackifying agent) resins, ieveiing agents, antifoaming agents, plasticizers, organic solvents, dyes Inert ingredients such as (dye), colorants, processing agents, and ultraviolet light screening agents. Tackifier resin 'for example: rosin acid, rosin acid, rosin acid vinegar, rosin, terpeneresin, terpene-phenol resin, aromatic hydrocarbon resin ( Aromafic hydrocarbon resin, aliphatic saturated hydrocarbon resin, petroleum resin, and the like can be used. [0 113] _ _ 63 10X120538 1013293844-0 201249948 As a silane coupling agent, the use of: 2- (3,4-epoxycyclohexyl) ethyl trimethoxy decane. (2-(3,4-epoxycyclohexyl)ethyl trimethoxy sulane), 3-Glycidoxypropyl trimethoxy silane, 3-glycidoxypropylmethyldiethyl氡-based alkane, 3-glycidoxypropyl-diethoxy sulphate, 3-(meta)acryloxypropylmethyldimethoxysilane, 3 -T* 3-methacryloxypropyl 〇tr imethoxy sulane, 3-(partial) propylene methoxypropyl decyl diethoxy decane, 3-(meta) propylene Methoxypropyl decyl triethoxy decane, N 2 -(amino-2-ethylpropyl-3-methoxypropyl dimethoxy silane), N -2-(aminoethyl)-3-aminopropyltrioxane

Basestone, N-2-(aminoethyl)-3-aminopropyltriethoxycarbazide, 3-aminopropyldimethoxydecane, 3-aminopropyltriethoxydecane, 3- 3-ethoxy silyl-N-(J (1' 3-dimethyl-butylidene) propylamine), N-stupid N-pheny 1 -3-aminopropy 1 trimethoxy si lane, 3-mercapto propyl methyl dimethoxy silane And 3-hydrothiopropyltrimethoxy oxalate, etc. The above-mentioned compound may be used singly or in combination of two or more kinds. [0114] 10112Ό538 1013293844-0 :, : 64 201249948 The method for producing the composition of the invention can be produced by mixing and mixing the components (A) to (c) and the component (D) and other components as needed according to a general method. In this case, Heating as needed; the heating temperature is preferably set according to the composition, substrate and purpose used, to 3 〇 8 (r [0115] 黏 The viscosity of the composition is preferably from 10 to 1000 mPa·s (rnPa · S) from the viewpoint of excellent coatability to the substrate. [0116] The composition of the present invention can be applied. Bonding of similar materials such as plastic film, plastic film, etc., and other various substrates, hereinafter referred to as "other substrates". In the following description, when the "base material" is used alone, it means plastic. A general term for ruthenium film and the like and other substrates. Other substrates such as paper and metal can be used. The method of using the composition of the present invention can be used for the usual usage, and specific examples can be cited, such as coating on a substrate. After the above, it is bonded to the other substrate, and irradiated with active high-energy rays. [0117] 1013293844-0 101120538 65 201249948 Plastic film and other related materials, for example, polyvinyl chloride resin, polyethylene dioxide (polyvinylidene chloride), cellulose (resin) resin, polyethylene, polypropylene, polystyrene, ABS resin (ABS resins; aery l Onitri le butadiene j styrene resins), polyamide, polyester, polycarbonate (po 1 ycarbonat e ), poly-cut vinegar (mouth 1〇1^61:113116), polyethylene glycol (1 ) 17乂11171 alcohol), triacetyl cellulose, Cyclo olefin polymer, polymethyl 〇methacry 1 ate, acrylic-styrene resin (aery 1) An ic styrene res i η ), a styrene-cluster acid copolymer, and a chlorinated polypropylene may be used. The paper used 'is: simi 1 i paper, wood free paper, Kraft paper, coated paper,

Cast coated paper, machine glazed poster paper, parchment paper, waterproof paper, g 1 ass i ne paper, and corrugated paper O, etc. can be enumerated for use. Examples of the metal foil, such as aluminum foil, may be used. [0118] The coating of the substrate may be carried out in accordance with a known method, and the method of use may be mentioned: ": natural coater, blade type belt Knife belt coater, floating knife (floating illusion, roller scraper 101120538 66 1013293844-0 201249948 coating (knifeoverroll), with knife layer coating (knifeo/?blanke1:), spraying (Spray), dip Dip, wet-roll, squeeze rol 1 , reverse r〇l 1 , air_blade, curtain flow Coater), comma coater, gravure coater, micro gravure coater, die coater (Die Coater) and curtain coater ( The coating thickness of the composition of the present invention can be selected depending on the substrate to be used and the use, and is preferably 0.1 to 1 μm, more preferably 1 to 25 μm. Active high energy ray, which can be enumerated Visible light, ultraviolet rays, xenon rays, electron beams, etc. 'But in order to use a cheaper device, 'ultraviolet light is more desirable. 〇Using ultraviolet light as a hardening light source, various light sources can be used, for example, a mercury lamp or a mercury lamp. A metal halide lamp (metd_halide lamp), a xenon lamp, an eiectr〇deiess discharge iamp, a carbon arc lamp, and a light-emitting diode lamp (LE: D) can be cited. When electron beam hardening is used, an electron beam irradiation (electr〇nbeam irradiation; EB irradiation) device can be used, and various devices such as a C〇ckr〇ft-Walton's apparatus can be used. Van der ge 101120538 67 1013293844-0 201249948 Van de Graaff generat〇r and tunable suspension type (such as (4)) bribes, etc. The electron beam is more ideal than the energy with 5q~ surface electron volts w, More preferably, it is 1 〇〇 to 3 〇〇 eV. [0 12 0] The composition of the present invention can be suitably applied to a thin layer of adherend which she cooperates as a substrate. When bonding a thin layer of adherends, the method of use can be carried out in accordance with the method generally described for the manufacture of a laminate. For example, the composition is coated on the first thin layer of the adherend, and if necessary, the second thin layer is adhered to the adherend, and the active high-energy ray is irradiated. [0 12 1] As the thin layer of the adherend, a plastic film or the like, a paper or a metal foil, or the like can be used. Plastic films and the like must pass through active high-energy rays; the thickness of the film should be selected according to the thin layer of the adherend and the use. The ideal thickness is 0.2 mm or less. [0 12 2] 68 101120538 1013293844-0 201249948 The composition of the present invention, among these thin layer adherends, can be suitably applied to the naphthalene film equivalent _ _ _ _, * and more advanced, or (four) cut Articles of re-hydrophilic plastics such as polyvinyl alcohol or cellulose triacetate are used. [0 12 3] Further, in order to increase the adhesion between the layers before bonding the adherend, the surface may be activated on one or both sides. Surface activation treatment, plasma treatment, corona discharge treatment, chemical treatment, blast treatment, etching treatment, flame treatment, etc. It can be enumerated and used, and these methods can also be used together. [0124] The coating of the thin layer adherend can be carried out in accordance with a known method, and the method of 〇 is the same as described above. Further, the coating thickness of the composition of the present invention can be selected in accordance with the thin layer adherend and the use, and is preferably the same coating thickness as described above. Further, in this case, it is not limited to the planar state, and the bonding may be performed in the curved state. 101120538 1013293844 69 201249948 That is, for example, a method in which a substrate is bent into a concave state or a convex state, and the composition is coated in this state, and then the other substrate is bonded and irradiated with active high-energy rays can be used. Other methods, such as a method in which the substrate is in a planar state, coated with the composition of the present invention, bonded to the other substrate, bent into a concave state or a convex state, and irradiated with an active high-energy ray, may also be used. In this case, the method of coating the composition in a planar state may be carried out in accordance with the aforementioned method. The method of coating the composition in a curved state can be exemplified by spraying (spray), dip coating, curtain coating, curtain printing (screening) Screenprinting) and slit die coating (phantom Die Coater) and other methods. [0 12 6] By the above method, the hardening of the naphthalene film/the composition of the present invention can be produced.

A layered body composed of a material/return thief, a hardened Q material/other substrate. The laminate of a laminated film obtained from the composition of the present invention is excellent in adhesion under conditions of high temperature and high humidity, and can be suitably used for polarizing plates and protections used in liquid crystal display devices and the like. An optical film such as a film phase difference film. This month's composition 'special flaws' can be ideally applied to the production of polarized plates and biased films with phase difference films. The method for producing the polarizing plate will be described below. 101120538 70 1013233844-0 201249948 [0 12 7] Further, in the case of the book towel, the optical element and the film are shown as a film or film having a polarizing function to be described later, and the polarizing plate is a side or two of the polarizing element. The side is protected by a thin thief film and a polarizing element with a protective layer. Further, the polarizing plate affixed with the retardation film is shown as a polarizing element or a polarizing plate, and the film is bonded to the film, or a polarizing plate having a function of the difference is formed by coating. [0128] As described above, the composition of the present invention can be suitably applied to the bonding of a hydrophilic plastic in the production of a polarized yarn, and the polyethylene triacetate used as a polarizing element and the cellulose triacetate used as a polarizing element protective film are equivalent. A compound of hydrophilic plastic. 〇 [0129] The composition of the present invention can be applied to the bonding of a polarizing element and a protective film, or the bonding of a polarizing plate and a retardation film. [0130] The polarizing element is a substance having a function of selectively penetrating linearly polarized light in one direction of natural light. 71 10112053S 1013293844-0 201249948 Specific examples of the polarizing element include a moth element-based polarizing element that adsorbs and aligns iodine on a polyvinyl alcohol film, on a 1 ethyl alcohol film. Dichroism dye-adsorbed and arranged dye-based polarizing elements; liquid-liquid crystalline liquid crystals ([Ly〇1;r〇pic] liquid crystals) in the form of pigment coating, alignment, and immobilization Overlying polarizing elements, etc. These iodine-based polarizing elements, dye-based polarizing elements, and coated polarizing elements are also substances having a function of selectively transmitting linearly polarized light in one direction of natural light and absorbing linearly polarized light in the other direction. Absorptive polarizing element. In the above iodine element-based polarizing element and dye-based polarizing element, a protective layer is usually provided on one side or both sides, and the composition of the present invention can be applied to bonding of a polarizing element and a protective film. [0 13 2] A protective film used for the protective layer, for example, a cellulose acetate resin film such as cellulose triacetate or cellulose diacetate; Resin film, polymerized acid | p〇lyarylate resin film; polyethersulphone resin film; cyclic olefin such as norbornene (norb〇rnene) as a ring of monomers A polyolefin resin film etc. are used, for example. 101120538 1013293844-0 72 201249948 [0 13 3] Next, the composition of the present invention can be applied to adhesion of a polarizing plate and a retardation film. In this case, the polarizing plate may be a polarizing plate provided with a protective layer on one or both sides. In this case, the protective layer may be a protective film bonded as described above, or may be formed by coating. Protective film. Only the polarizing plate which is designed as a protective layer in the early stage, and the surface to which the retardation film is adhered may be a face having a protective layer or a face having no protective layer. [0134] Various retardation films can be used, and examples thereof include an optical (four) film which is applied by uniaxial or biaxial stretching, or a liquid crystal compound, a permeation, and an immobilization. The processed optical film or the like is a film that controls the three dimensional indices of refraction according to the use conditions, and the film "optical indicatrix (index llipsoid)"; mainly because of liquid crystal The color correction or compensation of the liquid crystal layer of the display is used due to changes in the phase difference caused by the viewing angle. [0135] In the case of a specific example of the retardation film, for example, a raw material for an optical film of a film which is subjected to processing such as stretching can be exemplified by polyethylene, polypropylene, and cyclic polyolefin. Polyalkylene, or polycarbonate, polystyrene 101120538 73 1013293844-0 201249948 (polystyrene), p〇lymethyi methacrylate, polyarylate (p〇iyary ia1) :e ) and polypamine (p〇lyamide) and the like. The above-mentioned cyclic polyolefin ' is a general term for a resin obtained from a cyclic olefin of norbornene, tetxacyc 1 ododecene or a derivative of these compounds, and for example, The compound disclosed in Japanese Laid-Open Patent Publication No. Hei 3-122137, and the like. Specifically, it can be exemplified by a ring-opening polymer of a cyclic olefin, an addition polymer of a cyclic hydrocarbon, an annular flue gas and ethylene, a random copolymer of an α-olefin such as acryl; and a graft modified product in which these compounds are denatured in the presence of an unsaturated carboxylic acid or a derivative thereof. Further, a hydride of these compounds can also be used. Commercially available products include:

ipp0ΝΕΧ, ZE0N0R manufactured by Nippon Zeon Co., Ltd.; ART0N manufactured by JSR Co., Ltd.; T0PAS manufactured by TIC0NA. ◎ [0136] In addition, 'WFilm』 (Fuji Film Co., Ltd.)] "LC Film", which is a liquid film which is coated with a liquid crystal compound and which is subjected to arranging and immobilization. 』, "NH Film" (all manufactured by JX Nippon Mining & Energy Co., Ltd.). 101120538 74 1013293844-0 201249948 [0 13 7] A method of manufacturing a polarizing plate or a phase difference film polarizing plate using the composition of the present invention will be described below. This manufacturing method includes the following methods <1> to <3>. <1> Coating operation: a coating operation of the composition of the present invention coated on any one of a polarizing element, a polarizing plate, a protective film, a protective film, a retardation film, and a retardation film as an adherend; 〇 <2> Adhesive work: Any one of a polarizing element, a polarizing plate, a protective film, a protective film, a retardation film, and a retardation film which is the other adherend on the film coated with the above-mentioned composition Adhesion work on the top; <3> Irradiation operation: After the film is adhered, the substrate coated with the composition of the present invention is penetrated and irradiated with active high-energy rays. In the case of a single-sided adhesive protective film or a retardation film, a polarizing plate or a retardation film with a retardation film may be manufactured in accordance with the above-described procedure; however, when the two sides are attached to each other, the operation can be repeated <1> and &lt;2&gt; After the operation <3> is performed twice, the operations <1>, <2>, and <3> may be repeated twice. The coating method in the above operation <1> and the irradiation method of the active high-energy ray in the above-mentioned operation <3> may be carried out in the same manner as described above. Further, as in the above, it is also possible to bond in the curved state. 101120538 75 1013293844-0 201249948 [0139] When a phase difference film polarizing plate is used as a circular polarizing plate, in order to form a pendulum | circular polarization (circular p〇larizati〇n) state in a wide band On the retardation film side of the retardation film polarizing plate, a retardation film having a different phase difference can be adhered. Specifically, for the polarizing element film, there is a method of pasting a retardation film having a 1/2 wavelength with respect to each wavelength and then pasting a retardation film having a quarter wavelength with respect to each wavelength. In this case, the operation <丨> and <2> may be repeated twice, and the operation <3> may be performed; the operations <丨>, <2>, and <3> may be repeated three times. [Examples] [0 14 0] Hereinafter, the present invention will be more specifically described by way of examples and comparative examples. Also, in the following examples, "partial" means "weight part". [Production Example 1] Methylepichlorohydrin (hereinafter referred to as "mech") is produced by the method described in Synthesis Example 1 of "Patent Document 8", which is hereinafter referred to as "Patent Document 8". . 1013293844-0 10112053^8 76 201249948 [0142] 〇Production Example 2 [Production of Component (A)] The MECH and bisphenol F obtained in Production Example 1 were used, and the method described in Example 10 of Patent Document 8 was used. 'Manufacture of bisphenol F dimethyl glycidyl ether derivative (in the chemical formula (6), a compound having a fluorenyl fluorenyl group and η is hydrazine; hereinafter, referred to as "BFMGE" . The obtained compound 'is a mixture of the following three compounds. 【0 14 3】 【化14】

[Production Example 3] Production of (A) component The MECH and resorcinol (resorcinol) obtained in Production Example 1 were used in accordance with the method described in Example 9 of Patent Document 8. , manufacturing between the two - dimercapto glycidol (resorcinol dimethyl glycidyl 101120538 1013293844-0 77 201249948 ether) derivative (derivative) in the chemical formula (5), R 甲基 methyl, n is 0 compound; Hereinafter, it is called "RMGE". 〇Production Example 4 [Production of Component (A)] The MECH and phenol obtained in Production Example 1 were used to produce a phenol-methyl group according to the method described in Example 1 of Patent Document 8. Pheno1 methyl glycidyl ether derivative "In the chemical formula (8), a Ri-based thiol compound; hereinafter, referred to as "PMGE". Example 1 to Example 6, Comparative Example 1 to Comparative Example 6 According to the formulation components shown in Tables 1 and 2 below, the components (A) to (D) and other components were 'in 6 (TC). The mixture was heated and stirred for 1 hour to dissolve to prepare an active high-energy ray-curable adhesive composition. [0 147] [Table 1] Example ____ Evaluation results of the composition (A) (B) (C) (D) Viscosity* Peel strength BFMGE RMGE PMGE HBA PEA Irg250 DETX Peel strength (N/25ram) Stripping state I 50 50 4 1 56 [Ο] 13.42 Aggregation damage 1 30 20 50 4 1 20 3.28 Agglutination damage 78 101120538 1013293844-0 201249948 [〇] ~ r—---- 3 30 20 50 4 1 —--- 14 [〇] 1.94 Pulling damage 4 50 30 20 4 1 80 [〇] 1.78 Slope interface damage 5 30 20 30 20 4 1 28 [〇] ------- 1.25 ---— _ Glass interface damage 6 30 20 30 20 4 1 20 [〇] 3.55 Set results glass interface damage 0 * Unit: mPa · s; L shown in brackets under viscosity ———--J meaning Ο 【0 148】 【Table 2】

Q Comparative Example Composition (A) (B) (C) (D) Other Viscosity % 253 [X] Price Prediction BFMGE PMGE PEA Irg250 DETX jER EX-201 CEL 2021 OXT 211 One Peel Strength Peel Strength ^/25mm) Peeling State 1 4 1 100 0.09 Glass boundary f Destruction 2 4 1 50 50 55 [〇] 0.06 Glass interface damage 3 50 4 1 50 34~ [〇] 0.50 PET interface damage 4 50 4 1 50 ----- 55 [〇 l 0.20 PETES' damage 5 50 4 1 50 —-31 t〇l 0.28 PET interface damage 6 50 50 4 1 ---- 153 ΓΛτ 0.41 —---- mmm flat proof .mra · s, 鄱 ι ι 孩Fox π corpse; τ no, 〇 〇 判定 determine 4 士果 [0149] 101120538 1013293844-0 79 201249948 In Table 1 and Table 2, the number of the components of the composition means the number of "parts". Further, the abbreviations in Tables 1 and 2 have the meanings indicated below except those defined above. 1) (B) component • HBA · 4-hydroxybutyl acrylate, Viscoat 4-HBA "trade name" manufactured by Osaka Organic Chemical Industry Co., Ltd. • PEA: phenoxy phenoXyethyl acrylate, Kyoeisha C) Chemical Acrylate Ρ0-Α "trade name" 2) (C) Ingredients • Irg 250: iodonium salt Cationic photopolymerization initiator, Irgacure 250 "trade name" manufactured by BASF Japan Co., Ltd. 3) (D) Ingredients DE DETX : 2,4-diethyl thioxanthone, Japanese chemical DETX-S "commodity name" manufactured by the company 4) Other components • j ER: diglycidyl bond of double age F, j ER807 "trade name" manufactured by Japan Epoxy Resin Co., Ltd. • EX-201: M-phenylene diglycidyl hydrazine (res〇rcinol diglycidyl 80 10112 Ό 538 1013293844-0 201249948 ether), Denacol EX-201 "trade name" manufactured by Nagase ChemteX Co., Ltd. • CEL2021: 3,4-epoxycyclohexane Alkenylmercapto-3',4'-epoxycyclohexyl ester (3, 4-epoxyc yclohexenyl methyl-3 , 4' -epoxy cyclohexene carboxy late) 'CEL0XIDE 2021 P "Product Name" manufactured by MI CEL Chemical Industry Co., Ltd. • 0XT 211: 3-ethyl-3-phenoxymethyloxetane (3 -ethy-3-phenoxymethyl oxetane) 'Aron Oxetane 0XT-211 "Product Name" manufactured by Toagosei Co., Ltd. [0 15 0] ※Evaluation of the obtained composition is evaluated according to the following test methods, and the results are displayed. In Table 1 and Table 2. [0 15 1] Fortunately, the viscosity of the composition was measured at 25 ° C using an E-type viscometer. At the time of film coating of the coating operation, due to 25. (: Viscosity is better than ideal with low viscosity, judged by the following criteria. 〇·Unsupplied 100 mPa·s (mpa · s); △: 100~200 mPa·s; 10112Q538 81 1013293844-0 201249948 X : More than 200 mPa·sec. [0152] The manufacture of the laminate was carried out on a polyethylene terephthalate (PET) film having a thickness of 50 μm using a bar coater. The composition was coated to a thickness of 2 microns and then pasted onto a glass plate. Next 'Use a 80 watt/millimeter (W/cm) concentration metal-halide lamp at 30 m/ The conveyance speed (Conveyor Speed) of one minute (111/1^11) is irradiated with ultraviolet light of one type from the glass side to harden it to produce a laminate. The strength of the outer line of the rabbit is 233 mW/cm2 (mW/cm2). The integral light counter is 114 mJ/cm 2 (mJ/cm 2 ) "Either at 365 nm (coffee) value". 〇 [0 15 3] * Peel strength is measured by the following conditions The peel strength of the obtained laminate (Tension testing machines) : Instron Japan Co Instr〇n 5564 manufactured by mpany Limited ♦ test piece: 25 mm xioo mm ♦ test method: 180 degree peeling 101120538 82 1013293844-0 201249948 ♦ peeling speed: mm / min «min) [0154] As clearly shown in Table 1, this The composition of the invention is a material having a low viscosity and a high peeling strength. In contrast, the composition of the component (A) of the present invention, "Comparative Example 15", and the composition of the component (8) of the present invention are not contained. Comparative Example 6, at least one of the viscosity and peel strength of any one is not touchable. Example 7 to Example 16, Comparative Example 7 to Comparative Example 15 According to the formulations shown in Tables 3 and 4 below, the components (A) to (D) and other components were heated and stirred at 60 ° C. After 1 hour, it was dissolved to prepare an active high energy ray-curable adhesive composition. 〇[0156] [Table 3] Example (A) Composition (B) (C) (D) Other (b 1) (b2) (b3) BFMGE HBA ΗΡΑ M313 M203 M270 PEA IBXA THFA Irg250 CPI DBA DETX OXT211 7 50 30 20 4 1 8 48 30 2 20 4 1 9 40 30 10 20 4 1 10 30 30 20 20 4 1 11 40 30 10 20 4 1 12 48 30 2 10 10 4 1 13 48 30 2 20 4 1 101120538 1013293844 -0 83 201249948

[Table 4]

[0158] In Tables 3 and 4, the numerical values of the respective components of the subtracted matter indicate the number of Qs of the "parts". Further, the abbreviations in Tables 3 and 4 have the meanings indicated below in addition to those defined above. 1) (B) Sparse • ΗΡΑ: 2-Hydroxypropyl acrylate - Light Ester 共0Ρ-Α "Product Name" 10112Ό538 1013293844-0 84 201249948 M313. Ethoxylated uric acid dihydrogen uric acid dihydrogen vinegar (e 〇 Xyiated isocyanuric acid di/triacrylate), Aronix M-313 "trade name" manufactured by East Asia Synthetic Co., Ltd. • M203. TriCyCi〇decane dimethaol diacrylate, Aronix m-203 "trade name" manufactured by East Asia Synthetic Co., Ltd. • M325: ε-caprolactone modified three (acryloyloxyethyl) (ε-caprolactone modified tris acryloyloxy ethyl O isocyanurate ), Aronix M_325 "trade name" manufactured by East Asia Synthetic Co., Ltd. • M-270. Polypropylene glycol diacrylic acid vinegar (p〇iypr〇pyiene giyC 〇i diacrylate) Aronix m-270 "trade name" manufactured by East Asia Synthetic Co., Ltd. • PEA. phenoxyethyl acrylate, Light manufactured by Kyoeisha Chemical Co., Ltd. Acrylate Ρ0-Α "Commodity 》 IBXA · isobornyl acrylate, light Acrylate IB-ΧΑ "trade name" 共 · THFA : tetrahydrofurfuryl acrylate , Viscoat #15〇 "trade name" manufactured by Osaka Organic Chemical Industry Co., Ltd. 2) (C) Ingredients • CPI: 5% by weight of suif〇nium sait cationic photopolymerization initiator A solution of pr〇pylene carb〇nate, CPM00P "trade name" manufactured by SAN-APR0 Company • DBA. 9,10-dibutoxy onion (9, l〇-dibutoxyanthracene) 'Kawasaki 85 101120538 1013293844-0 201249948 Anthracure* UVS-1331 "Product Name" manufactured by the company 3) Other Ingredients • YX: Hydrogenated bisphenol A diglycidyl ether ' Made by Japan Epoxy Resin Co., Ltd. ΥΧ-8000 "Product Name" • 100MF: Trimethylolpropane triglycidyl ether - Epolight 1〇〇Mp 〇 "Product Name" • CEL300 0 : Limonene dioxide, CEL0XIDE 3000 "trade name" manufactured by DAICEL Chemical Industry Co., Ltd. • 0XT 221 : 3-ethyl-3-{[(3-ethyloxetane- 3-yl)nonyloxy]fluorenyl}

Oxetane (3_ethyl-3-{[(3-ethyloxetan-3-yl) methpxy] methyl} oxetane), Aron Oxetane OXT-221 "trade name" manufactured by East Asia Synthetic Co., Ltd. Q • SM 100 : 3,4-ethoxycyclohexyl methyl metacry late, Syclomer-M-100 "trade name" manufactured by DAICEL Chemical Industry Co., Ltd. [0159] ※ Evaluation 101120538 1013293844-0 86 201249948 The composition of the service was evaluated according to the following test methods, and the results were not shown in Tables 5 and 6. [0 16 0] Wood 25 ° C viscosity The viscosity was measured using an E-type viscometer in the same manner as described above. Ο [0 16 1] Manufacturing Example 1 of 〇polarizing element 1 The mass fraction of 破·〇·05 and potassium hydride are dissolved. The 5 mass part is dissolved in 1 〇〇 mass of water to prepare a dyeing solution. The liquid is heated to 55. (:, after immersing the PVA film "Cnyray film VF-PS manufactured by Curaray Co., Ltd., 75 μm" for 1 minute, 'stretching the film 6 times in one direction. Then, washing after dyeing' A polarizing element having a film thickness of 30 μm is formed by a solution of 4 parts by mass of boric acid and 6 parts by mass of potassium iodide dissolved in 9 parts by mass of water. [0 16 2] 〇 Polarized light Production Example 1 A corona cellulose film (manufactured by FujiTack 'Fuji Film Co., Ltd., manufactured under the trade name FujiTack 'Fuji Film Co., Ltd.') having a thickness of 80 μm is hereinafter referred to as "UVA-TAC". Discharge treatment) "Navistar 87 120538 1013293S44-0 201249948 Polydyne manufactured 1, output: 〇. 丨仟 ;; processing speed: leap seconds / cm" as easy adhesion treatment. Then 'on the polarizing element obtained in the manufacturing example 1 'Applying a 5 micron thick active high energy ray-curable composition with a coating bar. Here, the UVA-TAC after the corona treatment is laminated, and then turned over to 'samely coat the active high energy ray hardening groupAnd carry out the UVA_TAC lamination after the corona treatment is carried out. Then, using a 8 watt/Amy concentrating metal i-lamp, at a conveying speed of 5 m/min, each surface is irradiated with ultraviolet rays of one wavelength. , harden it, and then cure it for 12 hours or more at room temperature. A TAC-type polarizing plate is produced as a test object. The ultraviolet intensity is 250 mW/m 2 (mW 八 m2), and the integrated light amount (integral light counter) is 1 〇〇mJ/cm 2 (mJ/cm) "Either at 365 nm (nm) value". [0 16 3] 制造 Polaroid plate manufacturing example 2 〇 use A polarizing plate was produced in the same manner as in Production Example 1 of the polarizing plate except that the UV-free Weigang m-dimensional film ("L0F0 manufactured" is hereinafter referred to as "TAC") having a thickness of 1 GG μm was used instead of WA_TAC. [0 164] 氺Peeling strength 101120538 88 1013293844-0 201249948 The test object obtained in the manufacturing example 1 of the polarizing plate was cut to a length of 100 mm x a width of 25 mm. The substrate-free double-sided tape 465 manufactured by Sumitomo 3M was attached to the glass. The layers of the body are constructed from top to bottom [UVA-TAC (l) / Adhesive / Polarizing element / Adhesive / UVA-TAC (2) / Double-sided tape / glass]. Peel strength between the obtained polarizing element of the laminate and UYA-TACC2) It was measured under the following conditions. Further, the test object of Production Example 2 in which the polarizing plate was produced in the same manner was also measured for peel strength. ♦ Tension testing machines: Instron 5564 manufactured by Instron Japan Company Limited ♦ Test piece: 25 mm X 100 mm ♦ Test method: 90 degree peeling ♦ Peeling speed: 200 mm/min (mm/min) [0165] 〇* wet and heat resistance The test object obtained in the manufacturing examples 1 and 2 of the polarizing plate was placed in a constant temperature and humidity device of 6 ° C / 90% relative humidity (HR) for 500 to 1000 hours. Observe the change in appearance. 〇: non-decolorization △: a part of fading can be seen X: almost completely fading 89 101120538 1013293844-0 201249948 [0166] *film curl (film curl) in the polarizing plate ray example 1 and 2 , _ hardened, insufficiently maintained hardened state of the laminate cut into 100 mm X _ 冕 5 〇耄 m, with Cell 〇 e tape (Cell〇phane tape) attached to a 3 inch paper tube. Then, the film was sufficiently cured at room temperature for more than 12 hours, and the appearance of the film on the horizontal surface was taken off. 〇: The height of the warpage at the edge of the film is less than j Ai ◎ x : The warpage height at the edge of the film is more than 1 cm [0167] [Table 5] 25. . Viscosity* Peeling fiber polarizing plate manufacturing example 1 Polarizing plate manufacturing example 2 Peeling strength (N/25 mm) Humidity resistance 60 ° C / 90% relative humidity Appearance Film curling resistance to moist heat 60 ° C / 90% relative humidity Appearance film curl 500 Hour face hour 500 hours 1000 hours Example 7 40 [〇] 8.57 〇〇X 〇〇X Example 8 41 [Ο] 7.97 〇〇〇〇〇〇Example 9 40 [Ο] Hard material 〇〇〇〇〇 〇Example 10 38 [〇] Hard material 〇〇〇〇〇〇 Example 11 37 [〇] 5.24 〇〇〇〇〇〇 Example 12 32 [Ο] 7.88 〇〇〇〇〇〇 Example 13 42 [ 〇] 9.21 〇△ 〇〇Δ 〇

90 101120538 1013293844-0 201249948 Example 14 51 [〇] 3.14 〇Δ ~~-- __ 〇〇△ 〇Example 15 38 [〇] 8.65 〇Δ 〇〇△ 〇Example 16 40 [〇] 9.17 〇〇〇 〇〇〇氺 unit: mPa · s; shown in parentheses under viscosity, meaning the result of the judgment. 〇

氺Unit: mPa · s; Handle under viscosity [0169] 91 101120538 1013293844-0 201249948 It is clearly shown from Table 5 that the composition of the present invention is low in viscosity, and the peel strength and the high temperature test are excellent after the test. The thin stalk of the dark reaction of the tilt is also suppressed. The composition "Comparative Example 8 to 15" which does not contain the component (A) of the present invention, and the composition "Comparative Example 7" which does not contain the component (8) of the present invention, "viscosity, peel strength," At least one of the appearances after the high temperature test is insufficient. [Industrial Applicable Applications] [0170] The composition of the present invention can be used as an adhesive for various thinner materials, and can also be used as an adhesive for hydrophilic plastic films, etc., especially for optical devices such as liquid crystal display devices. Manufacture of _ especially in the manufacture of polarizing plates. 101120538 92 1013293844-0

Claims (1)

201249948 VII. Patent application scope: 1. The active five-energy ray-curable adhesive composition is composed of at least a sclerosing κ δ initiator. The aforementioned hardening component is at least composed of the following (a) and (Β) components. The composition of the active high-energy ray-curable adhesive composed of the following components (6); (Α) component: the compound of the following chemical formula (1): 〇 [Chemical 1] In the chemical formula (1), a linear or branched alkyl group having a lanthanoid number of carbon atoms 丨~6; an integer of m to 1 to 20; R2 is a number of carbon atoms 丨~ other straight chain or fraction Branched alcoholic alcohol and its alkylene oxide degenerate, linear or branched polyalkylene oxide, polyfluorene polyol (p〇iyester polyol) ), an aromatic alcohol and its thinned oxygen denatured material, and a m-valent residue of a compound selected from a group of compounds having a phenolic hydroxyl group and an alkylene oxide denature thereof (residue) ), if the unit containing -OCMXOHXROCmO- can also be used; (B) component: unsaturated ethylene compound* 101120538 1013293844-0 93 201249948 (C) component. Ion photopolymerization initiator (cati〇njc photo-p〇lymeriZati〇n initiator). 2. The active high-energy ray-curable adhesive composition according to claim 1, wherein the 100% by weight of the curable component comprises 20 to 70% by weight of the component (A) and the above (8) The component has a weight ratio of 30 to 8 % by weight; and the component (c) contains 0.1 to 20 parts by weight based on the entire weight portion of the curable component. ζ) 3. The active high energy ray-curable adhesive composition according to claim 1 or 2, wherein the (Α) component is a compound represented by the above chemical formula (丨), and the number of private carbon atoms a linear or branched alkyl group of 1 to 6; m system 1 or 2; R2 contains a compound of phen〇iic hydroxyl gr0Up and a 111-valent residue of an alkylene oxide denatured product. (residue), a unit containing -OCH2C(OH)(Ri)CH2〇- may also be used. 4. The active high energy ray-curable adhesive composition according to claim 3, wherein the compound containing a lanthanide phenolic hydroxyl group in the above component (A) is selected from the group consisting of phenol and phenol. A compound of a group of benzene (biphenyl), bisphenol, and phenol resin. The active high energy ray-curable adhesive composition according to the above-mentioned application, wherein the component (A) is the following chemical formula (5), (6) or (8) Compounds listed: [Chemical 2] "In the chemical formula (5), "R" is a linear or branched alkyl group having 1 to 6 carbon atoms; η is 0 or a positive number; In the chemical formula (6), R! is a linear or branched alkyl group having 1 to 6 carbon atoms; η is 0 or a positive number; [Chemical 4] Ri 101120538 1013293844-0 95 (8 ) 201249948 In the chemical formula (8), R! is a linear or branched alkyl group having 1 to 6 carbon atoms. The active high-energy ray-curable adhesive composition according to any one of claims 1 to 5, wherein the component (B) comprises an ethylenically unsaturated compound having a hydroxyl group ( Bl). 7. The active high energy ray-curable adhesive composition according to claim 6, wherein the hardening component comprises 1% to 40% of the total (b) component of the (bl) component. weight ratio. 8. The active high energy ray-curable county composition according to any one of the items of the present invention, wherein the cap (8) age comprises a compound having one or more ethylenically unsaturated groups in the molecule. (Μ). The active high-energy ray-curable adhesive composition according to claim 8, wherein the hardening component comprises 1% to 50% by weight of the component (b2). . 1. The active high energy ray-curable adhesive composition as described in any one of claims 1 to 9 wherein the aforementioned polymeric contact further comprises (9) a radical photopolymerization initiator (radiealphGtQ_pGlymeri her The active high-energy ray-curable adhesive composition according to the first aspect of the invention, wherein the (100) part of the hardenable component is contained in the above (D) The composition is 0.1 to 20 parts by weight. 12. The active high energy ray-ray hardening adhesive composition according to any one of claims 6 to 2, which is applied to the adhesion of a hydrophilic plastic film or sheet. \13. The active high-energy ray-curable adhesive composition for producing a polarizing plate according to claim 12, wherein the hydrophilic valve film or sheet is a polyvinyl alcohol (PVA) type polarizing element film. Or flakes. 〇14. A laminate, a substrate, a cured layer of the composition according to any one of the above-mentioned items, and a layer or a sheet of a plastic film, which are laminated in this order. Integral. 15. The laminate according to claim 14, wherein the substrate is a plastic film or sheet. A polarizing plate, which is a polyvinyl alcohol-based polarizing element, or a thin layer of a composition, and a cured product layer of the composition according to any one of the items 1 to 11 and a plastic material. A film or sheet, a polarizing plate laminated in this order. 10112053S 1013293844-0 98 201249948 IV. Designated representative map: (1) The representative representative figure of this case is: the (none) map. (2) A brief description of the symbol of the representative figure: Ο 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: 【化1】 101120538 1013293844-0