Adhesive composition and adhesive

Abstract

To provide an adhesive composition containing a (meth)acrylate compound, an epoxy compound, and a photoacid generator that can produce a cured product with sufficient adhesive strength and further has a sufficiently low refractive index. [Solution] An adhesive composition is provided containing a (meth)acrylate compound, an epoxy compound, a crosslinking agent, and a photoacid generator. The crosslinking agent includes a (meth)acrylic resin having a first structural unit derived from (meth)acrylate having a fluorine-containing organic group, and a second structural unit derived from (meth)acrylate having a cyclic ether group.

Description

[Technical Field]

[0001] This disclosure relates to adhesive compositions and adhesives. [Background technology]

[0002] As an adhesive composition, a composition containing a (meth)acrylate compound, an epoxy compound, and a photoacid generator is known (see, for example, Patent Document 1). [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] Japanese Patent Publication No. 2018-141137 [Overview of the Initiative] [Problems that the invention aims to solve]

[0004] The primary objective of this disclosure is to provide an adhesive composition containing a (meth)acrylate compound, an epoxy compound, and a photoacid generator that can produce a cured product with sufficient adhesive strength and also has a sufficiently low refractive index. [Means for solving the problem]

[0005] The present inventors conducted diligent research to solve the above problems and discovered that by applying a predetermined crosslinking agent to the adhesive composition, the adhesive strength of the cured product is improved, and furthermore, the refractive index tends to become sufficiently low, thus completing the invention disclosed hereto.

[0006] This disclosure includes the following [1] to [7]. [1] Contains a (meth)acrylate compound, an epoxy compound, a crosslinking agent, and a photoacid generator, The crosslinking agent comprises a (meth)acrylic resin having a first structural unit derived from a (meth)acrylate having a fluorine-containing organic group, and a second structural unit derived from a (meth)acrylate having a cyclic ether group. Adhesive composition. [2] The content of the first structural unit is 10 to 90 mol%, based on the total structural units of the (meth)acrylic resin. The content of the second structural unit is 10 to 90 mol%, based on the total structural units of the (meth)acrylic resin. The adhesive composition described in [1]. [3] The (meth)acrylate compound includes a (meth)acrylate having a hydroxyl group and a (meth)acrylate having an alkoxy group, The adhesive composition described in [1] or [2]. [4] The (meth)acrylate compound may include a (meth)acrylate having a fluorine-containing organic group, The content of the (meth)acrylate having the fluorine-containing organic group is 0 to 30% by mass, based on the total amount of the (meth)acrylate compound. The adhesive composition described in [3]. [5] The epoxy compound includes an aliphatic epoxy compound. An adhesive composition according to any one of [1] to [4]. [6] The epoxy compound further comprises an alicyclic epoxy compound. The adhesive composition described in [5]. [7] comprising a first adherend, a second adherend, and an adhesive portion for adhering the first adherend and the second adherend to each other, The adhesive portion contains a cured product of the adhesive composition described in any of [1] to [6]. Adhesive body. [Effects of the Invention]

[0007] According to this disclosure, an adhesive composition containing a (meth)acrylate compound, an epoxy compound, and a photoacid generator is provided that can yield a cured product having sufficient adhesive strength and further having a low refractive index. Several forms of the adhesive composition can yield a cured product having sufficient curing speed and high infrared transmittance. Furthermore, according to this disclosure, an adhesive using such an adhesive composition is provided. [Modes for carrying out the invention]

[0008] The embodiments of this disclosure are described below. However, this disclosure is not limited to the embodiments described below.

[0009] In this specification, numerical ranges indicated using "~" represent a range that includes the numbers before and after "~" as the minimum and maximum values, respectively. In numerical ranges described in stages in this specification, the upper or lower limit of one stage of the numerical range may be replaced with the upper or lower limit of another stage of the numerical range. Also, in numerical ranges described in this specification, the upper or lower limit of that numerical range may be replaced with the values ​​shown in the examples. Furthermore, the upper and lower limits described individually can be combined in any way. In the notation "A~B" for a numerical range, the numbers A and B at both ends are included in the numerical range as the lower and upper limits, respectively. In this specification, for example, the description "10 or more" means "10" and "numbers greater than 10," and this applies even if the numbers are different. Also, for example, the description "10 or less" means "10" and "numbers less than 10," and this applies even if the numbers are different.

[0010] In this specification, the (meth)acrylate compound means a compound having one or more (meth)acryloyl groups, and the (meth)acrylic resin means a (co)polymer having at least a structural unit derived from the (meth)acrylate compound. The (meth)acrylate compound may be a compound having no epoxy group and no oxetanyl group. The (meth)acryloyl group means an acryloyl group or a corresponding methacryloyl group. The same applies to other similar expressions such as (meth)acrylate. Also, "A or B" means that either A or B may be included, or both may be included.

[0011] In this specification, the cyclic ether group means a group obtained by removing one hydrogen atom directly bonded to a carbon atom from a compound having a cyclic ether such as oxirane or oxetane. The cyclic ether group may be a group obtained by removing one hydrogen atom directly bonded to a carbon atom from a compound having a three-membered or four-membered cyclic ether. Examples of such a cyclic ether group include an epoxy group (oxiranyl group), an oxetanyl group, and the like. The cyclic ether group includes an alicyclic epoxy group such as an epoxycyclohexyl group (an epoxy group formed together with two carbon atoms constituting an alicyclic ring).

[0012] Unless otherwise specified, the materials exemplified below may be used alone or in combination of two or more. The amount of use or content of each component means the total amount of the plurality of substances corresponding to each component present in the composition when there are a plurality of substances corresponding to each component in the composition.

[0013] [Adhesive Composition] The adhesive composition of one embodiment contains a (meth)acrylate compound (hereinafter sometimes referred to as “component (A)”), an epoxy compound (hereinafter sometimes referred to as “component (B)”), a crosslinking agent (hereinafter sometimes referred to as “component (C)”), and a photoacid generator (hereinafter sometimes referred to as “component (D)”). The adhesive composition may further contain, for example, a photo radical generator (hereinafter sometimes referred to as “component (E)”) and an oxetane compound (hereinafter sometimes referred to as “component (F)”). The adhesive composition can be an adhesive composition exhibiting photocurability.

[0014] (A) component: (meth)acrylate compound The (A) component is not particularly limited as long as it is a compound having one or more (meth)acryloyl groups. The (A) component may include, for example, a (meth)acrylate having a hydroxy group (hereinafter sometimes referred to as “component (A1)”) and a (meth)acrylate having an alkoxy group (hereinafter sometimes referred to as “component (A2)”).

[0015] By including the (A) component as the (A1) component, the curability and adhesion of the adhesive composition can be further improved. The (A1) component may be, for example, a (meth)acrylate having a hydroxyalkyl group. Examples of the (meth)acrylate having a hydroxyalkyl group include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and the like.

[0016] From the viewpoints of the curability and adhesion of the adhesive composition, the content of the (A1) component may be 2% by mass or more, 4% by mass or more, 6% by mass or more, 8% by mass or more, or 10% by mass or more based on the total amount of the (A) component, and may be 40% by mass or less, 35% by mass or less, 30% by mass or less, 25% by mass or less, 20% by mass or less, or 15% by mass or less.

[0017] By including component (A2) in component (A), the solubility of component (C) described later can be improved, and furthermore, the permeability of the cured product of the adhesive composition can be further improved. Component (A2) may be, for example, a (meth)acrylate having an alkoxyalkyl group. Examples of component (A2) include 2-methoxyethyl acrylate and 2-ethoxyethyl (meth)acrylate.

[0018] The content of component (A2) may be 40% by mass or more, 45% by mass or more, 50% by mass or more, 55% by mass or more, 60% by mass or more, or 65% by mass or more, based on the total amount of component (A), and may be 95% by mass or less, 90% by mass or less, 85% by mass or less, 80% by mass or less, or 75% by mass or less, based on the solubility of component (C).

[0019] In one embodiment, component (A) may further contain a (meth)acrylate having a fluorine-containing organic group (hereinafter sometimes referred to as "component (A3)"). In one embodiment, component (A) may not contain component (A3).

[0020] The inclusion of component (A3) in component (A) tends to further enable lower refractive index in the cured product of the adhesive composition. Component (A3) may be, for example, a (meth)acrylate having a fluoroalkyl group. Examples of (meth)acrylates having a fluoroalkyl group include trifluoromethyl (meth)acrylate, 2,2,2-trifluoroethyl (meth)acrylate, 1,1,1,3,3,3-hexafluoro-2-propyl (meth)acrylate, perfluoroethylmethyl (meth)acrylate, perfluoropropylmethyl (meth)acrylate, perfluorobutylmethyl (meth)acrylate, perfluoropentylmethyl (meth)acrylate, perfluorohexylmethyl (meth)acrylate, perfluoroheptylmethyl (meth)acrylate, perfluorooctylmethyl (meth)acrylate, perfluorononylmethyl (meth)acrylate, perfluorodecylmethyl (meth)acrylate, perfluoroundecylmethyl (meth)acrylate, perfluorododecylmethyl (meth)acrylate, and perfluorotridecyl Examples include methyl(meth)acrylate, perfluorotetradecylmethyl(meth)acrylate, 2-(trifluoromethyl)ethyl(meth)acrylate, 2-(perfluoroethyl)ethyl(meth)acrylate, 2-(perfluoropropyl)ethyl(meth)acrylate, 2-(perfluorobutyl)ethyl(meth)acrylate, 2-(perfluoropentyl)ethyl(meth)acrylate, 2-(perfluorohexyl)ethyl(meth)acrylate, 2-(perfluoroheptyl)ethyl(meth)acrylate, 2-(perfluorooctyl)ethyl(meth)acrylate, 2-(perfluorononyl)ethyl(meth)acrylate, 2-(perfluorotridecyl)ethyl(meth)acrylate, 2-(perfluorotetradecyl)ethyl(meth)acrylate, and 1H,1H,5H-octafluoropentyl(meth)acrylate.

[0021] (A3) In a (meth)acrylate having a fluoroalkyl group as a component, the number of carbon atoms of the fluoroalkyl group may be, for example, 1 to 20, 2 or more, 3 or more, 4 or more, or 6 or more, or 18 or less, 16 or less, 14 or less, or 12 or less, from the viewpoint of lowering the refractive index of the cured product.

[0022] (A3) In a (meth)acrylate having a fluoroalkyl group as a component, the proportion of fluorine atoms in the fluoroalkyl group is calculated based on the total amount of hydrogen and fluorine atoms directly bonded to the carbon atoms constituting the fluoroalkyl group. For example, in the trifluoromethyl group of trifluoromethyl (meth)acrylate, there are 3 fluorine atoms and 0 hydrogen atoms, so the proportion of fluorine atoms is 100%. For example, in the 2,2,2-trifluoroethyl group of 2,2,2-trifluoroethyl (meth)acrylate, there are 3 fluorine atoms and 2 hydrogen atoms, so the proportion of fluorine atoms is 60%. From the viewpoint of lowering the refractive index of the cured product, the proportion of fluorine atoms may be, for example, 100% or less, 90% or less, or 80% or less, and may be 30% or more, 40% or more, or 50% or more.

[0023] The content of component (A3) may be 0 to 30% by mass, based on the total amount of component (A), from the viewpoint of lowering the refractive index of the cured product, and may be 0 to 25% by mass, 0 to 20% by mass, 0 to 15% by mass, 0 to 10% by mass, 0 to 5% by mass, 0 to 3% by mass, or 0 to 1% by mass. The content of component (A3) may be 0% by mass, based on the total amount of component (A). The content of component (A3) may be 25% by mass or less, 20% by mass or less, 15% by mass or less, 10% by mass or less, 5% by mass or less, 3% by mass or less, or 1% by mass or less, based on the total amount of component (A), and may be 1% by mass or more, 3% by mass or more, 5% by mass or more, 10% by mass or more, 15% by mass or more, or 20% by mass or more.

[0024] Component (A) may contain other (meth)acrylates (hereinafter sometimes referred to as "component (A4)") to the extent that they do not impair the effects of the present disclosure. Examples of component (A4) include monofunctional (meth)acrylates having one (meth)acryloyl group other than components (A1), (A2), and (A3), and polyfunctional (meth)acrylates having two or more (meth)acryloyl groups other than components (A1), (A2), and (A3). Component (A4) may contain polyfunctional (meth)acrylates.

[0025] Examples of monofunctional (meth)acrylates include alkyl (meth)acrylates having alkyl groups such as methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, n-hexyl (meth)acrylate, n-octyl (meth)acrylate, isooctyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isodecyl (meth)acrylate, and dodecyl (meth)acrylate; alkenyl (meth)acrylates having alkenyl groups such as 3-butenyl (meth)acrylate; (meth)acrylates having aromatic groups such as benzyl (meth)acrylate and phenoxyethyl (meth)acrylate; cyclohexyl (meth)acrylate, isobornyl (meth)acrylate. Examples include (meth)acrylates having alicyclic groups such as acrylate and dicyclopentanyl (meth)acrylate; (meth)acrylates having heterocyclic groups such as 4-(meth)acryloylmorpholine; alkoxy polyalkylene glycol (meth)acrylates such as methoxyethylene glycol (meth)acrylate, methoxytetraethylene glycol (meth)acrylate, methoxyhexaethylene glycol (meth)acrylate, and methoxyoctaethylene glycol (meth)acrylate; polyalkylene glycol mono(meth)acrylates such as tetraethylene glycol mono(meth)acrylate, hexaethylene glycol mono(meth)acrylate, and octapropylene glycol mono(meth)acrylate; and (meth)acrylates having a siloxane skeleton.

[0026] Examples of polyfunctional (meth)acrylates include difunctional (meth)acrylates such as ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, polyethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,3-bis((meth)acryloyloxy)-2-propanol, dioxane glycol di(meth)acrylate, isocyanuric acid EO-modified di(meth)acrylate, dimethylol tricyclodecane di(meth)acrylate, 1,3-adamantanediol di(meth)acrylate; trimethylolpropane tri(meth)acrylate; and other difunctional (meth)acrylates. )Acrylates, pentaerythritol tri(meth)acrylate, trimethylolpropane EO-modified tri(meth)acrylate, trimethylolpropane PO-modified tri(meth)acrylate, glycerin PO-modified tri(meth)acrylate, isocyanuric acid EO-modified tri(meth)acrylate, and other trifunctional (meth)acrylates; pentaerythritol tetra(meth)acrylate, sorbitol tetra(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate Examples include tetrafunctional (meth)acrylates such as dipentaerythritol tetra(meth)acrylate propionate; pentafunctional (meth)acrylates such as sorbitol penta(meth)acrylate; and hexafunctional (meth)acrylates such as dipentaerythritol hexa(meth)acrylate, sorbitol hexa(meth)acrylate, alkylene oxide-modified phosphazene hexa(meth)acrylate, and caprolactone-modified dipentaerythritol hexa(meth)acrylate.

[0027] The content of component (A4) may be 2% by mass or more, 4% by mass or more, 6% by mass or more, 8% by mass or more, or 10% by mass or more, based on the total amount of component (A), and may be 40% by mass or less, 35% by mass or less, 30% by mass or less, 25% by mass or less, 20% by mass or less, or 15% by mass or less.

[0028] The content of component (A) (the total amount of components (A1), (A2), (A3), and (A4)) may be 5% by mass or more, 10% by mass or more, or 12% by mass or more, and may be 35% by mass or less, 30% by mass or less, 25% by mass or less, or 20% by mass or less, based on the total amount of the adhesive composition.

[0029] (B) Component: Epoxy compound Component (B) is a compound having one or more epoxy groups. Component (B) may be a compound that does not have a (meth)acryloyl group and an oxetanyl group. Component (B) may be a compound having two or more epoxy groups. Component (B) may contain an aliphatic epoxy compound (hereinafter sometimes referred to as "component (B1)"). Component (B1) is a compound having epoxy groups other than alicyclic epoxy groups. Component (B) may contain an alicyclic epoxy compound (hereinafter sometimes referred to as "component (B2)"). Component (B2) is a compound having an alicyclic epoxy group. Component (B) may contain both component (B1) and component (B2).

[0030] The inclusion of component (B1) in component (B) tends to improve the compatibility and crosslinkability of the adhesive composition. Component (B1) may be, for example, an aliphatic diglycidyl ether having at least one aliphatic group (linking group) selected from the group consisting of alkylene groups, oxyalkylene groups, and cycloalkylene groups. Alternatively, component (B1) may be an epoxy compound that does not have an aromatic ring.

[0031] Examples of aliphatic diglycidyl ethers include diglycidyl ethers having alkylene groups such as ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, and 1,6-hexanediol diglycidyl ether; diglycidyl ethers having oxyalkylene groups such as diethylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, and polyethylene glycol diglycidyl ether; and diglycidyl ethers having cycloalkylene groups such as hydrogenated bisphenol A diglycidyl ether, 1,4-cyclohexanedimethanol diglycidyl ether, and diglycidyl-1,2-cyclohexanedicarboxylate.

[0032] Examples of components other than aliphatic diglycidyl ethers for (B1) include EHPE3150 (1,2-epoxy-4-(2-oxyranyl)cyclohexane adduct of 2,2-bis(hydroxymethyl)-1-butanol, manufactured by Daicel Corporation).

[0033] The content of component (B1) may be 30% by mass or more, 40% by mass or more, 50% by mass or more, 60% by mass or more, 70% by mass or more, or 80% by mass or more, based on the total amount of component (B), and may be 100% by mass or less, 95% by mass or less, 90% by mass or less, or 85% by mass or less.

[0034] Component (B2) is a compound having an epoxy group (e.g., an epoxycyclohexyl group) formed together with the two carbon atoms constituting the alicyclic ring. The inclusion of component (B2) in component (B) tends to improve the heat resistance and crosslinkability of the adhesive composition. Examples of commercially available components (B2) include Celoxide® 8010, 2021P, and 2081 (trade names, all manufactured by Daicel Corporation). Component (B2) may also be an epoxy compound that does not have an aromatic ring.

[0035] The content of component (B2) may be 0% by mass or more, 5% by mass or more, 10% by mass or more, or 15% by mass or more, based on the total amount of component (B), and may be 70% by mass or less, 60% by mass or less, 50% by mass or less, 40% by mass or less, 30% by mass or less, or 20% by mass or less.

[0036] Component (B) may include, in addition to components (B1) and (B2), other epoxy compounds (hereinafter sometimes referred to as "component (B3)"), to the extent that they do not impair the effects of the present disclosure. Examples of other epoxy compounds include epoxy compounds having aromatic rings.

[0037] Examples of component (B3) include diglycidyl phthalate, bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol AD ​​type epoxy resin, bisphenol S type epoxy resin, phenol novolac type epoxy resin, cresol novolac type epoxy resin, biphenyl type epoxy resin, and biphenyl aralkyl type epoxy resin.

[0038] The content of component (B3) may be 0-40% by mass, 0-30% by mass, 0-20% by mass, or 0-10% by mass, based on the total amount of component (B).

[0039] The content of component (B) (total amount of components (B1), (B2), and (B3)) may be 20% by mass or more, 25% by mass or more, 30% by mass or more, or 35% by mass or more, and may be 60% by mass or less, 55% by mass or less, or 50% by mass or less, based on the total amount of the adhesive composition.

[0040] (C) Ingredients: Crosslinking agent Component (C) comprises a (meth)acrylic resin having a first structural unit derived from a (meth)acrylate having a fluorine-containing organic group, and a second structural unit derived from a (meth)acrylate having a cyclic ether group. Component (C) may consist of the (meth)acrylic resin. The inclusion of component (C) in the adhesive composition tends to result in a cured product having sufficient adhesive strength and high infrared transmittance. Furthermore, the inclusion of component (C) in the adhesive composition tends to result in an adhesive composition having a low refractive index.

[0041] The (meth)acrylate having a fluorine organic group that gives the first structural unit may be, for example, a (meth)acrylate having a fluoroalkyl group. Examples of (meth)acrylates having a fluoroalkyl group include those exemplified in component (A3).

[0042] In a (meth)acrylate having a fluoroalkyl group, the number of carbon atoms of the fluoroalkyl group may be, for example, 1 to 10, 2 or more, 8 or less, 6 or less, 4 or less, or 3 or less, from the viewpoint of compatibility with component (A) or its polymer.

[0043] In a (meth)acrylate having a fluoroalkyl group, the proportion of fluorine atoms in the fluoroalkyl group may be, for example, 100% or less, 80% or less, or 70% or less, and may be 30% or more, 40% or more, or 50% or more, from the viewpoint of compatibility with component (A) or its polymer.

[0044] The content of the first structural unit may be 10-90 mol%, 20-90 mol%, 30-90 mol%, or 40-90 mol%, based on the total structural units of the (meth)acrylic resin, and from the viewpoint of compatibility with component (A) or its polymer.

[0045] The (meth)acrylate having a cyclic ether group that gives the second structural unit may be, for example, at least one selected from the group consisting of (meth)acrylates having an epoxy group and (meth)acrylates having an oxetanyl group. Examples of (meth)acrylates having an epoxy group include (meth)acrylates having alicyclic epoxy groups such as 3,4-epoxycyclohexylmethyl(meth)acrylate and (meth)acrylates having epoxy groups other than alicyclic epoxy groups such as glycidyl(meth)acrylate. Examples of (meth)acrylates having an oxetanyl group include (3-ethyloxetan-3-yl)methyl(meth)acrylate. The (meth)acrylate having a cyclic ether group may be, for example, a (meth)acrylate having an alicyclic epoxy group.

[0046] In (meth)acrylic resin, the content of the second structural unit may be 10-90 mol%, 10-80 mol%, 10-70 mol%, or 10-60 mol%, based on the total structural units of the (meth)acrylic resin, from the viewpoint of crosslinking with component (B), etc.

[0047] The (meth)acrylic resin may have other structural units other than the first and second structural units, to the extent that they do not impede the effects of the invention of this disclosure. Examples of compounds that provide other structural units include monofunctional (meth)acrylates having one (meth)acryloyl group, such as alkyl (meth)acrylates having an alkyl group, (meth)acrylates having an aromatic group, (meth)acrylates having an alicyclic group, (meth)acrylates having a nitrogen-containing oxygen heterocyclic group, alkoxy polyalkylene glycol (meth)acrylate, polyalkylene glycol mono(meth)acrylate, and (meth)acrylates having a siloxane skeleton; polyfunctional (meth)acrylates having two or more (meth)acryloyl groups, such as aliphatic poly(meth)acrylate and aromatic poly(meth)acrylate; and compounds having radical polymerizable groups other than (meth)acryloyl groups, such as styrene, 4-methylstyrene, vinylpyridine, vinylpyrrolidone, vinyl acetate, cyclohexylmaleimide, and phenylmaleimide.

[0048] The content of other structural units may be 0-40 mol%, 0-30 mol%, 0-20 mol%, or 0-10 mol%, based on the total structural units of the (meth)acrylic resin.

[0049] The weight-average molecular weight (Mw) of the (meth)acrylic resin may be, for example, 1,000 to 200,000, 3,000 or more, 5,000 or more, or 10,000 or more, and may be 150,000 or less, 100,000 or less, 60,000 or less, or 50,000 or less. The weight-average molecular weight (Mw) is a polystyrene equivalent value using a calibration curve with standard polystyrene by gel permeation chromatography (GPC). The weight-average molecular weight (Mw) can be measured, for example, by the method described in the examples.

[0050] (Meth)acrylic resins can be obtained, for example, by radical polymerization using a solution polymerization method. More specifically, they can be obtained by polymerizing monomers containing a (meth)acrylate having a cyclic ether group and a (meth)acrylate having a fluorine-containing organic group in a solvent.

[0051] The solvent can be any organic solvent commonly used in the field of radical polymerization. The solvent can be any solvent having a cyclic ether group (epoxy group or oxetanyl group) and not having a radical polymerizable group, since it allows the crosslinking agent ((meth)acrylic resin) to be directly incorporated into the polymerization reaction of curable resins such as compounds having a cyclic ether group (epoxy resin) without the need for isolation of the crosslinking agent ((meth)acrylic resin) (without the need for solvent removal and substitution). Examples of solvents include those commonly used in the field of epoxy resin diluents. Another example of a solvent is an epoxy resin that is liquid at 25°C. From the viewpoint of being usable as component (B1), the solvent can be, for example, an aliphatic diglycidyl ether. Examples of aliphatic diglycidyl ethers include those exemplified in component (B1).

[0052] In this specification, a radical polymerizable group means a group having a carbon-carbon double bond. Examples of radical polymerizable groups include (meth)acryloyl groups, vinyl groups, allyl groups, styryl groups, alkenyl groups, alkenylene groups, and maleimide groups.

[0053] The amount of solvent used can be appropriately determined depending on the type of monomer, reaction conditions, and the solid content concentration of the (meth)acrylic resin solution.

[0054] When polymerizing monomers, thermal radical generators, additives, etc., may be added as needed.

[0055] Examples of thermal radical generators include organic peroxides such as cumene hydroperoxide, diisopropylbenzene hydroperoxide, di-t-butyl peroxide, lauroyl peroxide, benzoyl peroxide, t-butyl peroxyisopropyl carbonate, t-amyl peroxy-2-ethylhexanoate, and t-butyl peroxy-2-ethylhexanoate; and azo compounds such as 2,2'-azobis(isobutyronitrile), 1,1'-azobis(cyclohexanecarbonile), 2,2'-azobis(2,4-dimethylvaleronitrile), and dimethyl-2,2'-azobis(2-methylpropionate).

[0056] The amount of thermal radical generator added can be set appropriately according to the type of monomer, reaction conditions, etc., and is not particularly limited, but may be 100 to 200,000 ppm by mass, 100 to 100,000 ppm by mass, 1,000 to 100,000 ppm by mass, 1,000 to 50,000 ppm by mass, 3,000 to 30,000 ppm by mass, or 10,000 to 80,000 ppm by mass, based on the total amount of monomers.

[0057] Examples of additives include chain transfer agents, antioxidants, light stabilizers, weather stabilizers, UV absorbers, and radical scavengers. The amount of additives added is not particularly limited, but may be 0.001 to 2% by mass or 0.005 to 1% by mass based on the total amount of monomers.

[0058] The polymerization temperature may be 40-120°C, 50-100°C, or 60-90°C. The polymerization time may be 0.1-24 hours, 0.5-20 hours, or 1-12 hours.

[0059] The content of component (C) may be 10% by mass or more, 15% by mass or more, 20% by mass or more, 25% by mass or more, or 30% by mass or more, based on the total amount of the adhesive composition, and may be 50% by mass or less, 45% by mass or less, or 40% by mass or less.

[0060] (D) Ingredients: Photoacid generator Component (D) is a component that generates an acid that initiates polymerization upon irradiation with light. Component (D) may be a component that generates an acid that initiates polymerization upon irradiation with light containing wavelengths in the range of 150 to 750 nm or light containing wavelengths in the range of 254 to 405 nm. Component (D) may also be a component that generates radicals that initiate radical polymerization upon irradiation with light. Component (D) may be a component that generates radicals and acid upon irradiation with light, and may be a component that generates radicals and acid upon irradiation with ultraviolet light.

[0061] (D) Examples of components include sulfonium salts, phosphonium salts, ammonium salts, diazonium salts, iodonium salts, anilinium salts, and other onium salts. An example of an anion for an onium salt is BF4. - , BR4 - (R represents a phenyl group substituted with two or more fluorine atoms or two or more trifluoromethyl groups.) PF6 - SbF6 - AsF6 - SO4R - Examples include (where R represents an alkyl group).

[0062] Examples of commercially available products containing component (D) include CPI-100P, CPI-110P, CPI-101A, CPI-200K, CPI-210S (all manufactured by Sunapro Co., Ltd.), UVI-6990, UVI-6992, UVI-6976 (all manufactured by Dow Chemical Japan Ltd.), SP-150, SP-152, SP-170, SP-172, SP-300 (all manufactured by ADEKA Corporation).

[0063] The content of component (D) may be, for example, 0.1 parts by mass or more, 0.5 parts by mass or more, or 1 part by mass or more, and may be 15 parts by mass, 10 parts by mass or less, or 5 parts by mass or less, based on 100 parts by mass of the total amount of components (B) and (C).

[0064] (E) Ingredient: Photoradical generator Component (E) may be a component that generates radicals upon irradiation with light containing wavelengths in the range of 150 to 750 nm or light containing wavelengths in the range of 254 to 405 nm. Component (E) may be a component that generates radicals upon irradiation with ultraviolet light. Component (E) may be a component that primarily acts on component (A).

[0065] Component (E) generates free radicals upon exposure to light. In other words, component (E) is a compound that generates radicals upon application of external light energy. Component (E) may be a compound having structures such as an oxime ester structure, a bisimidazole structure, an acridine structure, an α-aminoalkylphenone structure, an aminobenzophenone structure, an N-phenylglycine structure, an acylphosphine oxide structure, a benzyldimethyl ketal structure, or an α-hydroxyalkylphenone structure. Component (E) may be a compound having a structure selected from the group consisting of, for example, an oxime ester structure, an α-aminoalkylphenone structure, and an acylphosphine oxide structure, and may also be a compound having an acylphosphine oxide structure.

[0066] Specific examples of compounds having an oxime ester structure include 1-phenyl-1,2-butanedione-2-(o-methoxycarbonyl)oxime, 1-phenyl-1,2-propanedione-2-(o-methoxycarbonyl)oxime, 1-phenyl-1,2-propanedione-2-(o-ethoxycarbonyl)oxime, 1-phenyl-1,2-propanedione-2-o-benzoyloxime, 1,3-diphenylpropanetrione-2-(o-ethoxycarbonyl)oxime, and 1-phenyl-3-ethoxypropanetrione-2-(o-benzoyl)oxime.

[0067] Specific examples of compounds having an α-aminoalkylphenone structure include 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one and 2-benzyl-2-dimethylamino-1-morpholinophenyl)-butanone-1.

[0068] Specific examples of compounds having an acylphosphine oxide structure include bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, and diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide.

[0069] The content of component (E) may be 0.1 to 15 parts by mass, 0.5 to 10 parts by mass, or 1 to 8 parts by mass per 100 parts by mass of the total amount of component (A).

[0070] (F) Component: Oxetane compound Component (F) is a compound having one or more oxetanyl groups. Component (F) may be a compound that does not have (meth)acryloyl groups or epoxy groups. Component (F) may be a compound having two or more oxetanyl groups. Further inclusion of component (F) in the adhesive composition tends to further enable lower refractive index in the cured product of the adhesive composition.

[0071] Examples of commercially available products containing component (F) include Aronoxetane® OXT-101, OXT-211, OXT-213, OXT-212, OXT-121, and OXT-221 (product names, all manufactured by Toagosei Co., Ltd.).

[0072] The content of component (F) may be 1% by mass or more, 3% by mass or more, or 5% by mass or more, and may be 30% by mass or less, 20% by mass or less, or 10% by mass or less, based on the total amount of the adhesive composition.

[0073] The adhesive composition may contain other components. Examples of other components include coupling agents, antioxidants, and photosensitizers.

[0074] The coupling agent may be, for example, a silane coupling agent. The silane coupling agent may be, for example, a compound having a hydrolyzable silyl group and a functional group that can react with either a (meth)acrylate compound or an epoxy compound. The hydrolyzable silyl group is, for example, a group having a silicon atom and 1 to 3 alkoxy groups bonded to the silicon atom. The number of carbon atoms in the alkoxy group bonded to the silicon atom may be, for example, 1 to 4. Examples of functional groups include amino groups such as primary amino groups and secondary amino groups, epoxy groups, mercapto groups, (meth)acryloyl groups, and isocyanate groups. The functional group may be an isocyanate group because the effects of this disclosure are more easily obtained. That is, component (F) may contain a silane coupling agent having an isocyanate group. In this specification, compounds having a hydrolyzable silyl group and a (meth)acryloyl group, and compounds having a hydrolyzable silyl group and an epoxy group are classified as silane coupling agents.

[0075] Examples of commercially available silane coupling agents include KBM-303, KBM-402, KBM-403, KBE-402, KBE-403, KBM-4803, KBM-502, KBM-503, KBE-502, KBE-503, KBM-5103, KBM-5803, KBM-602, KBM-603, KBM-903, KBE-903, KBE-9103P, KBM-573, KBM-575, KBM-802, KBM-803, and KBE-9007N (product names, all manufactured by Shin-Etsu Chemical Co., Ltd.).

[0076] The silane coupling agent content may be 0.1% by mass or more, 0.2% by mass or more, or 0.5% by mass or more, based on the total amount of the adhesive composition, and may be 10% by mass or less, 8% by mass or less, 5% by mass or less, 3% by mass or less, or 2% by mass or less.

[0077] Examples of antioxidants include quinone derivatives such as benzoquinone and hydroquinone, phenol derivatives (hindered phenol derivatives) such as 4-methoxyphenol and 4-t-butylcatechol, aminooxyl derivatives such as 2,2,6,6-tetramethylpiperidine-1-oxyl and 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl, and hindered amine derivatives such as tetramethylpiperidyl methacrylate.

[0078] The antioxidant content may be 0.1 to 10% by mass, based on the total amount of the adhesive composition.

[0079] Examples of photosensitizers include benzoflavin, anthracene, pyrene, thioxanthone, benzophenone, anthraquinone, camphorquinone, coumarin dyes, and oxazole compounds.

[0080] The amount of photosensitizer may be 0.01 to 10% by mass, or 0.01 to 1% by mass, based on the total amount of the adhesive composition.

[0081] The adhesive composition can be prepared by mixing (or kneading) components (A), (B), (C), and (D), as well as components (E), (F), and other components. Mixing can be carried out using a combination of conventional agitators, rotary mixers, and other dispersers as appropriate. In addition, degassing treatment by vacuum degassing or the like may be applied as appropriate during mixing.

[0082] The adhesive composition can form an adhesive layer with excellent adhesion to various substrates. The adhesive layer can be obtained by placing the adhesive composition in a predetermined position to form an adhesive layer precursor, and then irradiating the placed adhesive layer precursor with light. Light irradiation may be performed while heating. The adhesive layer contains a cured product of the adhesive composition. Light irradiation may be performed directly on the adhesive composition or through a transparent resin, glass, or the like.

[0083] The light for light irradiation may be light including wavelengths within the range of 150 to 750 nm or light including wavelengths within the range of 254 to 405 nm, and may be ultraviolet light.

[0084] Examples of the light source for light irradiation include low-pressure mercury lamps, medium-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, xenon lamps, metal halide lamps, LED light sources, etc. The integrated light quantity of light irradiation can be set as appropriate, for example, it may be 100 to 5000 mJ / cm 2 and may be.

[0085] The atmosphere for light irradiation is not particularly limited, and for example, it may be an air atmosphere or an inert gas atmosphere such as nitrogen or argon.

[0086] When performing light irradiation while heating, the heating conditions may be, for example, 60 to 150 °C.

[0087] After performing light irradiation on the adhesive part precursor, heat treatment may further be performed on the adhesive part precursor. The heat treatment can be carried out, for example, under the conditions of a heating temperature of 60 to 180 °C and a holding time of 5 to 60 minutes.

[0088] The infrared transmittance of the cured product of the adhesive composition may be 70% or more, and may be 75% or more, 80% or more, 85% or more, 90% or more, 95% or more, or 97% or more. In this specification, the infrared transmittance of the cured product of the adhesive composition can be determined by measuring the transmittance of infrared rays with a wavelength of 1310 nm for the measurement sample using a spectrophotometer. The measurement sample can be prepared by the following procedure. First, a spacer film with a thickness of 500 μm is arranged on a glass plate so that the dimensions are 2 cm in length × 2 cm in width × 500 μm in thickness, and the adhesive composition is applied and formed on the glass plate. Next, for the formed adhesive composition, using an ultraviolet light irradiation device (wavelength: 365 nm), an illuminance of 30 mW / cm 2 and a time of 30 seconds, that is, an integrated light quantity of 900 mJ / cm 2Under these conditions, ultraviolet light is irradiated, and 600 seconds after the ultraviolet light irradiation ends, the spacer film is peeled off and used as the measurement sample. In addition, glass is used as the base material for the baseline.

[0089] [Adhesive body] An adhesive body according to one embodiment comprises a first adherend, a second adherend, and an adhesive portion that adheres the first adherend and the second adherend to each other. The adhesive portion contains a cured product of the adhesive composition described above.

[0090] Examples of the first and second adherends include organic materials such as polyolefin resin, polyamide resin, ABS (acrylonitrile butadiene styrene) resin, PC (polycarbonate) resin, PET (polyethylene terephthalate) resin, PPS (polyphenylene sulfide) resin, acrylic resin, and transparent resin; inorganic materials such as steel, stainless steel, metals (aluminum, copper, nickel, chromium, etc.) or alloys of these metals, glass, and silicon wafers; wood; and rubber. Furthermore, the first adherend 1 and the second adherend 2 may also be composite materials of the above-mentioned plastics and inorganic materials. Either the first adherend 1 or the second adherend 2 may be a transparent resin or glass from the viewpoint of light irradiation.

[0091] The thicknesses of the first adherend and the second adherend may be, for example, 0.1 to 2.0 mm, 0.1 to 1.0 mm, or 0.1 to 0.5 mm.

[0092] The adhesive can be obtained, for example, by a method that includes the steps of: applying an adhesive composition onto a first adherend to form an adhesive precursor containing the adhesive composition; placing a second adherend on the adhesive precursor to create a laminate; and irradiating the adhesive precursor of the laminate with light to form an adhesive portion containing a cured product of the adhesive composition.

[0093] The adhesive composition can be applied using a knife coater, roll coater, applicator, comma coater, die coater, dispenser, etc.

[0094] The light irradiation conditions (wavelength of light, light source, integrated light intensity, etc.) for the adhesive precursor of the laminate may be the same as those described above.

[0095] Light irradiation of the adhesive precursor of the laminate may be performed while heating. The heating conditions (heating temperature, etc.) may be the same as those described above.

[0096] After irradiating the adhesive precursor of the laminate with light, the adhesive precursor may be further subjected to heat treatment. The heat treatment conditions (heating temperature, holding time, etc.) may be the same as those described above.

[0097] The thickness of the bonded portion containing the cured product of the adhesive composition may be, for example, 0.01 to 1.0 mm, 0.01 to 0.5 mm, or 0.01 to 0.2 mm.

[0098] The adhesive composition of this embodiment has high infrared transmittance of the cured product and excellent adhesive strength, making it suitable for use as an adhesive for optical devices such as optical fibers used in communications, sensing, and medical applications (adhesive for optical devices). [Examples]

[0099] The present disclosure will be specifically described below with reference to examples, but the present disclosure is not limited to these examples.

[0100] [Synthesis of (meth)acrylic resin (crosslinking agent)] The following ingredients were prepared. • (meth)acrylate compounds M-3F: 2,2,2-trifluoroethyl methacrylate (light ester M-3F, Kyoeisha Chemical Co., Ltd.) TTA-15: 3,4-Epoxycyclohexylmethyl methacrylate (manufactured by Sun Chemical Co., Ltd.) MMA: Methyl methacrylate • Thermal radical generator V-601: Dimethyl-2,2'-azobis(2-methylpropionate) (Fujifilm Wako Pure Chemical Corporation) ·solvent NPG(D): Neopentyl glycol diglycidyl ether (Epogosei NPG(D)) (Yokkaichi Synthetic Co., Ltd.)

[0101] <Manufacturing Example 1> Mixture (a1) was prepared by mixing 144.38 g of M-3F and 42.13 g of TTA-15 (molar ratio of M-3F / TTA-15 = 80% / 20%) with 5.78 g of V-601 and 20.00 g of NPG(D). Separately, solution (b) was prepared by dissolving 1.87 g of V-601 in 106 g of NPG(D).

[0102] 156.51 g of NPG(D) was placed in a flask equipped with a stirrer, dropping funnel, condenser, thermometer, and gas inlet tube. The flask was stirred under a nitrogen atmosphere while gas substitution was performed, and the temperature was raised to 85°C. Next, mixture (a1) was added dropwise to the flask over 2 hours. After the addition was complete, the flask was stirred at 85°C for 20 minutes, then solution (b) was added, and the flask was stirred for a further 7 hours. Then, while continuing to stir, the flask was cooled to room temperature (25°C) to obtain the solution containing (meth)acrylic resin (crosslinking agent A) of Production Example 1. The solid content concentration was 50% by mass.

[0103] <Comparative Manufacturing Example 1> Mixture (a2) was prepared by mixing 88.00 g of MMA and 22.00 g of TTA-15 (molar ratio of MMA / TTA-15 = 80% / 20%) with 5.78 g of V-601 and 15.00 g of NPG(D). A solution containing (meth)acrylic resin (crosslinking agent a) of Comparative Production Example 1 was obtained in the same manner as in Production Example 1, except that mixture (a1) was replaced with mixture (a2). The solid content concentration was 50% by mass.

[0104] [Evaluation of (meth)acrylic resin (crosslinking agent)] (Measurement of viscosity (at 25°C)) The viscosity of solutions containing (meth)acrylic resin at 25°C was measured using an E-type viscometer (manufactured by Toki Sangyo Co., Ltd., product name: VISCOMETER-TV22, applicable cone-plate rotor: 3°×R17.65) with a sample volume of 0.5 to 1.0 mL, at a rotation speed of 10 rpm. The results are shown in Table 1.

[0105] (Measurement of weight-average molecular weight (Mw)) For Mw measurement, a solution containing (meth)acrylic resin was dissolved in tetrahydrofuran (THF) to prepare a 0.2% by mass THF solution. Mw was measured by gel permeation chromatography (GPC) and derived by conversion using a calibration curve for standard polystyrene. The GPC conditions are shown below. The results are shown in Table 1. Measuring device: SHODEX® GPC-101 (manufactured by Resonac Corporation) Detector: Differential refractometer SHODEX RI-71S (manufactured by RAZONAC Corporation) Column: Showdex LF-804 + LF-804 (manufactured by Resonac Co., Ltd.) Column temperature: 40℃ Eluent: Tetrahydrofuran (THF) Flow rate: 1mL / min

[0106] [Table 1]

[0107] [Preparation of adhesive composition] <Examples 1 and 2 and Comparative Examples 1-3> The adhesive compositions of Examples 1, 2 and Comparative Examples 1-3 were prepared by mixing each component in the amounts (unit: parts by mass) shown in Table 2 using a rotary mixer (5 min / 1500 rpm), and containing component (A), component (B), component (C), component (D), and a coupling agent.

[0108] Details of each ingredient are as follows: (A) Component: (meth)acrylate compound (A1) component 4-HBA: 4-Hydroxybutyl acrylate (manufactured by Osaka Organic Chemical Industry Co., Ltd.) ·(A2) Component 2-MTA: 2-Methoxyethyl acrylate (manufactured by Osaka Organic Chemical Industry Co., Ltd.) ·(A3) Component M-3F: 2,2,2-trifluoroethyl acrylate (light ester M-3F, manufactured by Kyoeisha Chemical Co., Ltd.) ·(A4) Component A-9300S: Tris(2-acryloxyethyl) isocyanurate (trifunctional, isocyanurate EO modified tri(meth)acrylate, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.) (B) Component: Epoxy compound ·(B1) component NPG(D): Neopentyl glycol diglycidyl ether (EPOGOSÉ® NPG(D)) (manufactured by Yokkaichi Synthetic Co., Ltd.) ·(B2) component 2021P: 3',4'-Epoxycyclohexylmethyl-3,4-Epoxycyclohexanecarboxylate (Celoxide® 2021P, manufactured by Daicel Corporation) (C) Ingredients: Crosslinking agent Manufacturing Example 1: (Meth)acrylic resin (crosslinking agent A) (c) Components: Crosslinking agents other than component (C) Comparative manufacturing example 1: (meth)acrylic resin (crosslinking agent a) (D) Ingredients: Photoacid generator CPI-110P: Sulfonium salt (manufactured by Sunapro Co., Ltd.) Coupling agent KBE-9007N: 3-Isocyanate-propyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.)

[0109] The amounts of (meth)acrylic resin (crosslinking agent A) of Production Example 1, which is component (C), and NPG(D), which is component (B), were adjusted using the solution containing (meth)acrylic resin (crosslinking agent A) of Production Example 1 obtained above. Similarly, the amounts of (meth)acrylic resin (crosslinking agent a) of Comparative Production Example 1, which is component (c), and NPG(D), which is component (B), were adjusted using the solution containing (meth)acrylic resin (crosslinking agent a) of Comparative Production Example 1 obtained above.

[0110] [Evaluation of adhesive compositions] (Measurement of refractive index) The refractive index of the adhesive composition at room temperature (25°C) was measured using an Abbemat300 (Anton Paar, wavelength: 589 nm) with a sample volume of 0.1-0.2 mL. The results are shown in Table 2.

[0111] (Measurement of shear strength) A 50 μm thick spacer film was placed on a glass slide so that its dimensions were 5 mm in length, 5 mm in width, and 50 μm in thickness, and an adhesive composition was applied to the glass slide. A glass chip measuring 7 mm in length, 7 mm in width, and 1.0 mm in thickness was placed on top of the applied adhesive composition, and an illuminance of 30 mW / cm² was applied using an LED lamp (manufactured by Ushio Inc., wavelength: 365 nm). 2 And for a time of 30 seconds, i.e., an integrated light intensity of 900 mJ / cm². 2 The adhesive composition was irradiated with ultraviolet light under the specified conditions. Shear strength was measured using a bond tester (Nordson, product name: DAGE4000) at a shear rate of 180 mm / min, with the sample being measured 270 seconds after the end of ultraviolet light irradiation. The results are shown in Table 2.

[0112] (Measurement of infrared transmittance) The infrared transmittance of the cured adhesive composition was measured using a spectrophotometer (Agilent Technologies, product name: Cary7000) at a wavelength of 1310 nm. The measurement samples were prepared using the following procedure: First, a 500 μm thick spacer film was placed on a glass plate to the dimensions of 20 mm (length) x 20 mm (width) x 500 μm (thickness), and the adhesive composition was applied to the glass plate and molded. Next, an LED lamp (Ushio Inc., wavelength: 365 nm) was used to irradiate the molded adhesive composition at an intensity of 30 mW / cm². 2 And for a time of 30 seconds, i.e., an integrated light intensity of 900 mJ / cm². 2 Under these conditions, ultraviolet light was irradiated, and 600 seconds after the termination of ultraviolet light irradiation, the spacer film was peeled off and used as the measurement sample. Glass was used as the base material for the baseline. The results are shown in Table 2.

[0113] [Table 2]

[0114] As shown in Table 2, the adhesive compositions of Examples 1 and 2 exhibited good refractive index and shear strength, whereas the adhesive compositions of Comparative Examples 1 to 3 lacked sufficient refractive index or shear strength. Furthermore, the adhesive compositions of Examples 1 and 2 were found to have a sufficient curing speed and sufficiently high infrared transmittance. From these results, it was confirmed that the adhesive composition of this disclosure, which contains a (meth)acrylate compound, an epoxy compound, and a photoacid generator, can provide a cured product with sufficient adhesive strength and also exhibits a sufficiently low refractive index.

Claims

1. It contains a (meth)acrylate compound, an epoxy compound, a crosslinking agent, and a photoacid generator. The crosslinking agent comprises a (meth)acrylic resin having a first structural unit derived from a (meth)acrylate having a fluorine-containing organic group, and a second structural unit derived from a (meth)acrylate having a cyclic ether group. Adhesive composition.

2. The content of the first structural unit is 10 to 90 mol%, based on the total structural units of the (meth)acrylic resin. The content of the second structural unit is 10 to 90 mol%, based on the total structural units of the (meth)acrylic resin. The adhesive composition according to claim 1.

3. The (meth)acrylate compound includes a (meth)acrylate having a hydroxyl group and a (meth)acrylate having an alkoxy group. The adhesive composition according to claim 1.

4. The (meth)acrylate compound may further contain a (meth)acrylate having a fluorine-containing organic group. The content of the (meth)acrylate having the fluorine-containing organic group is 0 to 30% by mass, based on the total amount of the (meth)acrylate compound. The adhesive composition according to claim 3.

5. The epoxy compound includes an aliphatic epoxy compound. The adhesive composition according to claim 1.

6. The epoxy compound further comprises an alicyclic epoxy compound. The adhesive composition according to claim 5.

7. It comprises a first adherend, a second adherend, and an adhesive portion that adheres the first adherend and the second adherend to each other. The adhesive portion contains a cured product of the adhesive composition described in any one of claims 1 to 6. Adhesive body.

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