Curable composition

Abstract

To provide a curable composition having improved adhesive strength.SOLUTION: A curable composition according to an embodiment of the invention comprises an isobutylene-based polymer (component A) having 1.2 or more (meth)acryloyl groups per one molecule on average, a vinyl monomer (component B) having one or more functional groups selected from a group consisting of a carboxyl group and an alkali metal salt thereof, a phosphate group and an alkali metal salt thereof, a hydroxyl group and an alkali metal salt thereof, an amino group, and an epoxy group, and a radical polymerization initiator (component C).SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a curable composition. [Background technology]

[0002] Conventionally, curable compositions containing isobutylene-based polymers having (meth)acryloyl groups have been used for applications such as sealing materials and adhesives. Examples of documents disclosing such curable compositions include Patent Documents 1 and 2. In addition, an example of a document disclosing a method for producing an isobutylene-based polymer having a (meth)acryloyl group is Patent Document 3. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] JP 2013-216782 A [Patent Document 2] International Publication No. 2013 / 047314 [Patent Document 3] International Publication No. 2017 / 047335 Summary of the Invention [Problem to be solved by the invention]

[0004] However, the above-mentioned conventional techniques leave room for further improvement in the adhesive strength between the substrate and the curable composition.

[0005] An object of one aspect of the present invention is to provide a curable composition having improved adhesive strength to a substrate. [Means for solving the problem]

[0006] In order to solve the above problems, a curable composition according to one embodiment of the present invention contains the following Components A to C: Component A: an isobutylene polymer having an average of 1.2 or more (meth)acryloyl groups per molecule; Component B: a vinyl monomer having one or more functional groups selected from the group consisting of a carboxyl group and its alkali metal salt, a phosphoric acid group and its alkali metal salt, a hydroxyl group and its alkali metal salt, an amino group, and an epoxy group; Component C: Radical polymerization initiator. Effect of the Invention

[0007] According to one aspect of the present invention, there is provided a curable composition having improved adhesive strength to a substrate. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0008] An example of an embodiment of the present invention will be described in detail below, but the present invention is not limited to the following embodiments and may be modified in various ways within the scope of the claims. An embodiment that combines technical means described in different embodiments is also included in the technical scope of the present invention.

[0009] Unless otherwise specified in this specification, "A to B" representing a numerical range means "A or more and B or less." In this specification, "(meth)acrylic" means "acrylic and / or methacrylic." In this specification, "(meth)acryloyl" means "acryloyl and / or methacryloyl."

[0010] 1. Components of the Curable Composition

[0011] The curable composition according to one embodiment of the present invention includes component A: an isobutylene-based polymer having an average of 1.2 or more (meth)acryloyl groups per molecule; component B: a vinyl-based monomer having one or more functional groups selected from the group consisting of a carboxyl group and its alkali metal salt, a phosphoric acid group and its alkali metal salt, a hydroxyl group and its alkali metal salt, an amino group, and an epoxy group; and component C: a radical polymerization initiator. The curable composition may include component D: a plasticizer and / or component E: a vinyl-based monomer other than component B as an optional component. The curable composition may include other components other than those described above. Each of these components may include only one type, or may include two or more types. Each component will be described in detail below.

[0012] [1.1. Component A: isobutylene polymer having an average of 1.2 or more (meth)acryloyl groups per molecule] Component A is an isobutylene polymer having (meth)acryloyl groups, the number of which is 1.2 or more on average per molecule.

[0013] The isobutylene polymer is a polymer mainly composed of units derived from isobutylene. The proportion of the units derived from isobutylene in the total weight of the isobutylene polymer is preferably 50% by weight or more, more preferably 70% by weight or more, and even more preferably 90% by weight or more.

[0014] Component A may have a unit derived from a monomer other than isobutylene. Examples of such monomers include aliphatic olefins (such as 1-butene); aromatic vinyls (styrene, methylstyrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, α-methylstyrene, etc.); dienes (1,3-butadiene, isoprene, etc.); vinyl ethers (such as butyl vinyl ether); silanes (vinyl trimethylsilane, allyl trimethylsilane, etc.); terpenes (α-pinene, β-pinene, limonene, etc.); vinyl carbazole; and acenaphthylene. In terms of ease of copolymerization with isobutylene and favorable physical properties of the resulting copolymer, the comonomer used is preferably one or more selected from the group consisting of 1-butene, styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, α-methylstyrene, 1,3-butadiene, isoprene, α-pinene, β-pinene, and limonene.

[0015] The lower limit of the number of (meth)acryloyl groups contained in component A is, on average, 1.2 or more, preferably 1.5 or more, and more preferably 1.7 or more per molecule. The upper limit of the number of (meth)acryloyl groups contained in component A can be, on average, 10.0 or less, 8.0 or less, 6.0 or less, 4.0 or less, or 2.0 or less per molecule. The average number of (meth)acryloyl groups contained in component A per molecule is 1 Calculated from HNMR spectrum.

[0016] In component A, the (meth)acryloyl group may be located at the end of the main chain, may be located in the middle of the main chain, or may be located at both of these. When located in the middle of the main chain, the (meth)acryloyl group is included in component A as a side chain. In one embodiment, the (meth)acryloyl group is located only at the end of the main chain of component A.

[0017] The (meth)acryloyl group contained in Component A is preferably represented by the following general formula (1). [ka]

[0018] R 1 R represents a hydrogen atom or a methyl group. 1 When R is a hydrogen atom, formula (1) is an acryloyl group. 1 is a methyl group, then formula (1) is a methacryloyl group.

[0019] R 2 R is a divalent saturated hydrocarbon group having 2 to 6 carbon atoms and containing no heteroatoms. 2 Examples of R include alkylene groups (methylene, propylene, butylene, pentylene, hexylene, etc.). From the standpoint of raw material availability and reactivity, R 2 is preferably a butylene group or a pentylene group.

[0020] R 3 ~R 6 are each independently a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, or an alkoxy group. Specific examples of the monovalent hydrocarbon group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a 2-ethylhexyl group, a nonyl group, and a decanyl group. Specific examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, and a butoxy group. From the viewpoint of reactivity, R 3 ~R 6 are preferably each independently selected from the group consisting of a hydrogen atom, a methyl group, and a methoxy group. 3 ~R 6 It is more preferable that each of the is a hydrogen atom.

[0021] The lower limit of the number average molecular weight (Mn) of component A is preferably 200 or more, more preferably 300 or more, and even more preferably 1,000 or more. The upper limit of the number average molecular weight (Mn) of component A is preferably 500,000 or less, more preferably 150,000 or less, and even more preferably 50,000 or less. The lower limit of the weight average molecular weight (Mw) of component A is preferably 200 or more, more preferably 300 or more, and even more preferably 1,000 or more. The upper limit of the weight average molecular weight (Mw) of component A is preferably 750,000 or less, more preferably 230,000 or less, and even more preferably 75,000 or less. If the molecular weight of component A is within the above range, it is easy to obtain a cured product with sufficient strength. The number average molecular weight and weight average molecular weight of component A are determined by a standard polystyrene conversion method using size exclusion chromatography (SEC).

[0022] The molecular weight distribution (Mw / Mn) of component A is preferably 1.8 or less, more preferably 1.5 or less, and even more preferably 1.3 or less. The lower limit of the molecular weight distribution of component A may be 1.0 or more. When the molecular weight distribution of component A is within the above range, a curable composition with high workability is easily obtained.

[0023] [1.1.1. Manufacturing method of component A] Component A can be produced by a known method, for example as follows (for a more specific example, see Production Example 1). 1. Isobutylene is subjected to living cationic polymerization in the presence of a polymerization initiator, a Lewis acid catalyst, and an electron donor component, thereby forming the main chain of an isobutylene-based polymer. 2. (Meth)acryloyl groups are introduced to the ends of the main chain using (meth)acrylate phenoxyalkyl compounds, etc. In this case, the number of (meth)acryloyl groups introduced to the main chain can be adjusted by the amount of (meth)acrylate phenoxyalkyl compound added to the polymerization system.

[0024] Examples of polymerization initiators include cumyl chloride, p-dicumyl chloride, tert-butyl chloride, and 2-chloro-2,4,4-trimethylpentane. Examples of Lewis acid catalysts include titanium tetrachloride. Examples of electron donor components include nitrogen-containing compounds (2-methylpyridine, 2,6-lutidine, triethylamine, etc.).

[0025] The polymerization solvent in the above-mentioned production method is preferably one or more selected from the group consisting of methyl chloride, butyl chloride, hexane, cyclohexane, methylcyclohexane, ethylcyclohexane and toluene. These solvents are easily available, dissolve the raw materials and the polymer well, and are inexpensive.

[0026] The reaction temperature in the above production method is preferably low (eg, −70° C.).

[0027] (Phenoxyalkyl (meth)acrylate compounds) The phenoxyalkyl (meth)acrylate compound may be a commercially available product as is, or may be synthesized by a known method.

[0028] One example of a method for synthesizing a phenoxyalkyl (meth)acrylate compound is to react a compound represented by the following general formula (2), which is an alcohol compound, with a compound represented by the following general formula (3). By using the phenoxyalkyl (meth)acrylate compound thus obtained, a (meth)acryloyl group represented by general formula (1) can be introduced. [ka]

[0029] In the general formulas (2) and (3), R 1 ~R 6 is as defined above. X is a chlorine atom, a bromine atom or an iodine atom.

[0030] When the compound represented by the general formula (2) is reacted with the compound represented by the general formula (3), a base may be added to the reaction system. This captures the generated HX (hydrogen chloride, hydrogen bromide, or hydrogen iodide) and promotes the reaction. Examples of the base include amine compounds and metal salts. Specific examples of the amine compounds include nitrogen-containing compounds such as ammonia, diethylamine, triethylamine, di-n-propylamine, tri-n-propylamine, di-i-propylamine, tri-i-propylamine, di-n-butylamine, tri-n-butylamine, di-i-butylamine, tri-i-butylamine, pyridine, α-picoline, β-picoline, aniline, methylaniline, dimethylaniline, and N,N-dimethylaniline. Examples of metal salts include lithium hydroxide, sodium hydroxide, potassium hydroxide, rubidium hydroxide, cesium hydroxide, lithium carbonate, sodium carbonate, potassium carbonate, rubidium carbonate, cesium carbonate, lithium bicarbonate, sodium bicarbonate, potassium bicarbonate, rubidium bicarbonate, cesium bicarbonate, lithium hydride, sodium hydride, potassium hydride, butyllithium, and lithium diisopropylamide.

[0031] The system in which the compound represented by the general formula (2) and the compound represented by the general formula (3) are reacted may be a solvent system or a solventless system. The solvent used in the solvent system is preferably a dehydrated solvent.

[0032] Examples of solvents include halogenated hydrocarbons (methylene chloride, chloroform, 1,1-dichloroethane, 1,2-dichloroethane, n-propyl chloride, n-butyl chloride, etc.); aromatic hydrocarbons (benzene, toluene, xylene, etc.); aliphatic hydrocarbons (pentane, n-hexane, cyclohexane, methylcyclohexane, ethylcyclohexane, etc.); ethers (diethyl ether, dibutyl ether, diisopropyl ether, tetrahydrofuran, dimethoxyethane, dioxane, etc.); esters (ethyl acetate, etc.); and other solvents (acetone, dimethylformamide, acetonitrile, pyridine, triethylamine, etc.).

[0033] The reaction temperature when reacting the compound represented by general formula (2) with the compound represented by general formula (3) is usually −70° C. to 200° C., and preferably 0° C. to 100° C. The reaction time is usually 1 minute to 24 hours.

[0034] Another example of a method for synthesizing a phenoxyalkyl (meth)acrylate compound includes reacting a compound represented by the following general formula (4) having a phenoxy group and a halogen group with a compound represented by the following general formula (5). [ka]

[0035] In the general formulas (4) and (5), R 1 ~R 6 is as defined above. X is a chlorine atom, a bromine atom or an iodine atom.

[0036] When the compound represented by the general formula (4) is reacted with the compound represented by the general formula (5), a base may be added to the reaction system. This captures the generated HX (hydrogen chloride, hydrogen bromide, or hydrogen iodide) and promotes the reaction. Examples of the base include amine compounds and metal salts. Specific examples of the amine compounds include nitrogen-containing compounds such as ammonia, diethylamine, triethylamine, di-n-propylamine, tri-n-propylamine, di-i-propylamine, tri-i-propylamine, di-n-butylamine, tri-n-butylamine, di-i-butylamine, tri-i-butylamine, pyridine, α-picoline, β-picoline, aniline, methylaniline, dimethylaniline, and N,N-dimethylaniline. Examples of metal salts include lithium hydroxide, sodium hydroxide, potassium hydroxide, rubidium hydroxide, cesium hydroxide, lithium carbonate, sodium carbonate, potassium carbonate, rubidium carbonate, cesium carbonate, lithium bicarbonate, sodium bicarbonate, potassium bicarbonate, rubidium bicarbonate, cesium bicarbonate, lithium hydride, sodium hydride, potassium hydride, butyllithium, and lithium diisopropylamide.

[0037] Prior to reacting the compound represented by the general formula (4) with the compound represented by the general formula (5), the compound represented by the general formula (5) may be reacted with the above-mentioned base. In this case, the resulting neutralized product is reacted with the compound represented by the general formula (4).

[0038] When the compound represented by the general formula (4) is reacted with the compound represented by the general formula (5), a phase transfer catalyst may be added to the reaction system to promote the reaction. Examples of the phase transfer catalyst include tetramethylammonium chloride, tetramethylammonium bromide, tetrabutylammonium chloride, and tetrabutylammonium bromide.

[0039] The system in which the compound represented by the general formula (4) and the compound represented by the general formula (5) are reacted may be a solvent system or a solventless system. The solvent used in the solvent system is preferably a dehydrated solvent.

[0040] Examples of solvents include halogenated hydrocarbons (methylene chloride, chloroform, 1,1-dichloroethane, 1,2-dichloroethane, n-propyl chloride, n-butyl chloride, etc.); aromatic hydrocarbons (benzene, toluene, xylene, etc.); aliphatic hydrocarbons (pentane, n-hexane, cyclohexane, methylcyclohexane, ethylcyclohexane, etc.); ethers (diethyl ether, dibutyl ether, diisopropyl ether, tetrahydrofuran, dimethoxyethane, dioxane, etc.); esters (ethyl acetate, etc.); and other solvents (acetone, dimethylformamide, acetonitrile, pyridine, triethylamine, etc.).

[0041] The reaction temperature when reacting the compound represented by the general formula (4) with the compound represented by the general formula (5) is usually −70° C. to 200° C., and preferably 0° C. to 100° C. The reaction time is usually 1 minute to 24 hours.

[0042] The compound represented by the general formula (4) may be a commercially available product and used as is, or the compound represented by the general formula (4) may be synthesized by a known method.

[0043] An example of a method for synthesizing a compound represented by general formula (4) is a method of reacting a compound represented by the following general formula (6) with a compound represented by the following general formula (7). [ka]

[0044] In the general formulas (6) and (7), R 2 ~R 6 The definition of is as described above. X and Y are chlorine atoms, bromine atoms, or iodine atoms. X and Y may be the same or different.

[0045] When the compound represented by the general formula (6) is reacted with the compound represented by the general formula (7), an alkali metal halide may be added to the reaction system to promote the reaction. Examples of the alkali metal halide include sodium iodide and potassium iodide.

[0046] When the compound represented by the general formula (6) is reacted with the compound represented by the general formula (7), a base may be added to the reaction system to promote the reaction. Examples of the base include metal salts. Specific examples of the metal salt include lithium hydroxide, sodium hydroxide, potassium hydroxide, rubidium hydroxide, cesium hydroxide, lithium carbonate, sodium carbonate, potassium carbonate, rubidium carbonate, cesium carbonate, lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, rubidium hydrogen carbonate, cesium hydrogen carbonate, lithium hydride, potassium hydride, sodium hydride, butyl lithium, and lithium diisopropylamide.

[0047] The system in which the compound represented by the general formula (6) and the compound represented by the general formula (7) are reacted may be a solvent system or a solventless system. The solvent used in the solvent system is preferably a dehydrated solvent.

[0048] Examples of solvents include halogenated hydrocarbons (methylene chloride, chloroform, 1,1-dichloroethane, 1,2-dichloroethane, n-propyl chloride, n-butyl chloride, etc.); aromatic hydrocarbons (benzene, toluene, xylene, etc.); aliphatic hydrocarbons (pentane, n-hexane, cyclohexane, methylcyclohexane, ethylcyclohexane, etc.); ethers (diethyl ether, dibutyl ether, diisopropyl ether, tetrahydrofuran, dimethoxyethane, dioxane, etc.); esters (ethyl acetate, etc.); and other solvents (acetone, dimethylformamide, acetonitrile, pyridine, triethylamine, etc.).

[0049] The reaction temperature when reacting the compound represented by the general formula (6) with the compound represented by the general formula (7) is usually −70° C. to 200° C., and preferably 0° C. to 100° C. The reaction time is usually 1 minute to 24 hours.

[0050] The phenoxyalkyl (meth)acrylate compound used in the synthesis of component A may be appropriately purified. The purification method is not particularly limited, and known methods can be used. Examples of the purification method include washing with water (water may be acidic, alkaline, or neutral) and using an adsorbent.

[0051] Other examples of methods for producing component A include the following. 1. A monomer having both a cationically polymerizable functional group and a (meth)acryloyl group is prepared. 2. The above monomer and isobutylene are copolymerized to obtain an isobutylene-based polymer having a (meth)acryloyl group as a side chain.

[0052] [1.2. Component B: a vinyl monomer having one or more functional groups selected from the group consisting of a carboxyl group and its alkali metal salt, a phosphoric acid group and its alkali metal salt, a hydroxyl group and its alkali metal salt, an amino group, and an epoxy group] Component B is a vinyl monomer. The vinyl monomer refers to a compound having a polymerizable vinyl group.

[0053] In one embodiment, component B is a (meth)acrylic monomer and / or an aromatic vinyl monomer. The (meth)acrylic monomer refers to a compound having a (meth)acryloyl group (the (meth)acryloyl group contains a polymerizable vinyl group). The aromatic vinyl monomer is a compound having an aromatic ring and a polymerizable vinyl group. In one embodiment, the aromatic vinyl monomer is a styrene monomer.

[0054] There is no particular limitation on the number of polymerizable vinyl groups contained in component B. For example, the number of polymerizable vinyl groups contained in component B is 5 or less, 4 or less, 3 or less, 2 or less, or 1.

[0055] In addition to the polymerizable vinyl group, component B further has one or more functional groups selected from the group consisting of a carboxyl group and its alkali metal salt, a phosphoric acid group and its alkali metal salt, a hydroxyl group and its alkali metal salt, an amino group and an epoxy group.

[0056] Alkali metals are elements in Group 1 of the periodic table excluding hydrogen. In one embodiment, the alkali metals are sodium and / or potassium.

[0057] When component B is an alkali metal salt, the number of alkali metal ions contained in component B may be one or more. When component B contains more than one alkali metal ion, the types of these alkali metal ions may be the same or different. When component B is an alkali metal salt, component B may contain a cation other than an alkali metal ion.

[0058] Examples of component B having a carboxyl group include (meth)acrylic acid, 2-carboxyethyl (meth)acrylate, and mono(2-(meth)acryloyloxyethyl) succinate (all (meth)acryloyl monomers); 4-vinylbenzoic acid, 2-vinylbenzoic acid, and cinnamic acid (all aromatic vinyl monomers). Examples of component B having a hydroxyl group include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxy-1-methylethyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, and 3-hydroxy-1-adamantyl (meth)acrylate (all (meth)acryloyl monomers); 4-vinylphenol, and 2-methoxy-4-vinylphenol (all aromatic vinyl monomers). An example of component B having a phosphoric acid group is 2-(meth)acryloyloxyethyl phosphoric acid ester (the above are (meth)acryloyl monomers). The above-mentioned alkali metal salts of component B are also included in the examples of component B. Examples of component B having an amino group are 2-dimethylaminoethyl (meth)acrylate, 2-diethylaminoethyl (meth)acrylate, and 2-dimethylaminoethyl quaternized (meth)acrylate (the above are (meth)acryloyl monomers); 4-aminostyrene, and 4-dimethylaminostyrene (the above are aromatic vinyl monomers). Examples of component B having an epoxy group are glycidyl (meth)acrylate, and 4-hydroxybutyl (meth)acrylate glycidyl ether (the above are (meth)acryloyl monomers).

[0059] The molecular weight of component B is preferably 5,000 or less, more preferably 1,500 or less, and even more preferably 500 or less. The number of carbon atoms in component B is preferably 400 or less, more preferably 120 or less, and even more preferably 40 or less.

[0060] [1.3. Component C: Radical polymerization initiator] Component C is a radical polymerization initiator. Examples of the radical polymerization initiator include a thermal radical polymerization initiator and a photoradical polymerization initiator.

[0061] In one embodiment, component C is a photoradical polymerization initiator. A photopolymerization initiator is a compound that generates an active species (radical species, etc.) that initiates polymerization of a monomer when irradiated with active energy rays. In this specification, the term "active energy rays" generally refers to light rays in a broad sense. Examples of active energy rays include radiation (α rays, β rays, etc.), electromagnetic waves (γ rays, X-rays, etc.), electron beams (EB), ultraviolet rays (wavelength: 100 to 400 nm), and visible light (wavelength: 400 to 800 nm). In one embodiment, the active energy rays are ultraviolet rays.

[0062] Examples of the photoradical polymerization initiator include those described in International Publication No. 2013 / 047314 and JP-A No. 2013-216782. Among these, compounds having a hydroxyl group and a phenyl ketone structure, compounds having a benzophenone structure, and compounds having an acylphosphine oxide structure are preferably used.

[0063] Examples of compounds having a hydroxyl group and a phenyl ketone structure include 2,2-dimethoxy-1,2-diphenylethan-1-one, 1-hydroxy-cyclohexyl-phenyl ketone, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanon-1-one, and 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one.

[0064] Examples of compounds having a benzophenone structure include benzophenone, 3-methoxybenzophenone, 4-methylbenzophenone, 4,4'-bis(diethylamino)benzophenone, 4-chlorobenzophenone, 4,4'-dimethoxybenzophenone, and 4-chloro-4'-benzylbenzophenone.

[0065] Examples of compounds having an acylphosphine oxide structure include bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide, and 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide.

[0066] The photoradical polymerization initiator may be used in combination with other compounds. Examples of such combinations include the following: Combination with amines (diethanolmethylamine, dimethylethanolamine, triethanolamine, etc.) Combination with amines and iodonium salts (e.g. phenyliodonium chloride) ·Combination with amines and dyes (e.g. methylene blue)

[0067] [1.4. Component D: Plasticizer] Component D is a plasticizer. Component D is an optional component, so it may or may not be included in the curable composition. Examples of component D include polybutene oil and process oil.

[0068] Polybutene oil is a polymer obtained by polymerizing n-butene (1-butene and 2-butene) and isobutene (2-methylpropene). Among these, a copolymer in which isobutene is the main monomer and n-butene is the comonomer can be preferably used. As the polybutene, a commercially available product may be used. Examples of commercially available products include Nippon Oil Polybutene (ENEOS Corporation); NOF Polybutene, EUMAT (all NOF Corporation); and Oppanol (BASF SE).

[0069] Examples of process oils include paraffin oil, naphthene oil, and aromatic oil. Among these, paraffin oil is preferred. Paraffin oil refers to an oil agent whose main component is paraffin (chain hydrocarbon). Examples of paraffin include n-paraffin and isoparaffin. Examples of n-paraffin include butane, pentane, hexane, heptane, octane, nonane, decane, undecane, dodecane, tetradecane, pentadecane, hexadecane, heptadecane, octadecane, nonadecane, and eicosane. Examples of isoparaffins include isobutane, isopentane, neopentane, isohexane, isopentane, neohexane, 2,3-dimethylbutane, methylhexanes, 3-ethylpentane, dimethylpentanes, 2,2,3-trimethylbutane, 3-methylheptane, dimethylhexanes, trimethylpentanes, isononane, 2-methylnonane, isodecane, isoundecane, isododecane, isotridecane, isotetradecane, isopentadecane, isooctadecane, isonadecane, isoeicosane, and 4-ethyl-5-methyloctane.

[0070] [1.5. Component E: Vinyl-based monomer other than component B] Component E is a vinyl monomer other than component B. Examples of component E include (meth)acrylic monomers, aromatic vinyl monomers, and other vinyl monomers. In one embodiment, component E is a (meth)acrylic monomer and / or an aromatic vinyl monomer.

[0071] Examples of (meth)acrylic monomers include (meth)acrylic acid esters, (meth)acryloyl group-containing alicyclic compounds, (meth)acrylamide, and (meth)acrylonitrile. Among these, (meth)acrylic acid esters are preferred. (Meth)acrylic acid esters are represented by the general formula "CH 2 =C(R 1 )COOR 2 " is a compound represented by the formula: 1 is a hydrogen atom or a methyl group. 2is, for example, a hydrocarbon group that may have a heteroatom (such as a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, a silicon atom, or a halogen atom). The number of carbon atoms contained in R2 may be 50 or less, 40 or less, 30 or less, 20 or less, or 15 or less. 2 The number of heteroatoms contained in R may be 10 or less, 8 or less, 5 or less, 4 or less, 3 or less, 2 or less, or 1 or less. 2 is composed only of carbon and hydrogen atoms.

[0072] Specific examples of (meth)acrylic acid esters include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, n-pentyl (meth)acrylate, isoamyl (meth)acrylate, n-hexyl (meth)acrylate, cyclohexyl (meth)acrylate, and n-hexyl (meth)acrylate. butyl, n-octyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isooctyl (meth)acrylate, nonyl (meth)acrylate, isononyl (meth)acrylate, decyl (meth)acrylate, isodecyl (meth)acrylate, undecyl (meth)acrylate, dodecyl (meth)acrylate, tridecyl (meth)acrylate, tetradecyl (meth)acrylate, pentadecyl (meth)acrylate, hexadecyl (meth)acrylate, Examples of the acrylate include heptadecyl acrylate, stearyl (meth)acrylate, isostearyl (meth)acrylate, oleyl (meth)acrylate, behenyl (meth)acrylate, 2-decyltetradecanyl (meth)acrylate, phenyl (meth)acrylate, toluyl (meth)acrylate, tolyl (meth)acrylate, 4-tert-butylcyclohexyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, 3,3,5-trimethylcyclohexyl (meth)acrylate, adamantyl (meth)acrylate, 3-hydroxy-1-adamantyl (meth)acrylate, 1-methyladamantyl (meth)acrylate, 1-ethyladamantyl (meth)acrylate, and benzyl (meth)acrylate.

[0073] Specific examples of aromatic vinyl monomers include styrene, vinyl ketone, α-methylstyrene, p-methylstyrene, and chlorostyrene.

[0074] Examples of other vinyl monomers include fluorine-containing vinyl monomers (perfluoroethylene, perfluoropropylene, vinylidene fluoride, etc.); silicon-containing vinyl monomers (vinyltrimethoxysilane, vinyltriethoxysilane, etc.); vinyl ester monomers (vinyl acetate, vinyl propionate, vinyl butyrate, vinyl pivalate, vinyl benzoate, vinyl cinnamate, etc.); vinyl chloride, vinylidene chloride, vinyl iodide, vinyl bromide, vinylidene bromide, allyl chloride, allyl alcohol, vinyl ether, and methyl vinyl ketone.

[0075] [1.6. Other ingredients] The curable composition may contain other components in addition to the above-mentioned components A to E. Examples of the other components include additives (fillers, plasticizers, antioxidants, UV absorbers, flame retardants, antistatic agents, pigments, etc.), elastomers ((meth)acryloyl group-containing oligomers, styrene-based block copolymers, etc.) that adjust the rubber properties of the cured product, thiol compounds, tertiary amine compounds, and adhesion promoters.

[0076] (Additives) Examples of additives include additives described in International Publication No. 2013 / 047314 and JP-A No. 2013-216782. The contents of the filler and plasticizer are preferably 0.1 to 500 parts by weight, and more preferably 1.0 to 300 parts by weight, relative to 100 parts by weight of Component A. The contents of the antioxidant, ultraviolet absorber, flame retardant, antistatic agent, and pigment are preferably 0.01 to 20.0 parts by weight, and more preferably 0.10 to 10.0 parts by weight, relative to 100 parts by weight of Component A. When the content of the additive is within the above range, the balance between the effect of adding the additive and the cost is appropriate.

[0077] ((Meth)acryloyl group-containing oligomer) Examples of the (meth)acryloyl group-containing oligomer include a compound having a main chain made of an oligomer and a (meth)acryloyl group. In one embodiment, the main chain of the (meth)acryloyl group-containing oligomer does not contain a unit derived from isobutylene. In one embodiment, the (meth)acryloyl group-containing oligomer has an average of one or more (meth)acryloyl groups per molecule.

[0078] Examples of the main chain structure of the (meth)acryloyl group-containing oligomer include polybutadiene, hydrogenated polybutadiene, polyisoprene, hydrogenated polyisoprene, polyether, polyester, polycarbonate, polyacrylate, polymer of epoxy compound, castor oil, and silicone polymer. Among these, polybutadiene, hydrogenated polybutadiene, polyisoprene, hydrogenated polyisoprene, polyacrylate, polymer of epoxy compound, and castor oil are preferred. These main chain structures have excellent compatibility with other components contained in the curable composition.

[0079] The number average molecular weight of the (meth)acryloyl group-containing oligomer is preferably 200 to 500,000, more preferably 1,000 to 100,000. The (meth)acryloyl group-containing oligomer having a number average molecular weight in the above range is easily available and has good compatibility with other components of the curable composition. In addition, the handleability of the obtained curable composition is also excellent.

[0080] The content of the (meth)acryloyl group-containing oligomer is preferably 0.1 to 1000 parts by weight, and more preferably 1.0 to 300 parts by weight, relative to 100 parts by weight of Component A. When the content is within the above range, the compatibility with other components of the curable composition is good, and the viscosity of the obtained curable composition is also appropriate.

[0081] (styrene block copolymer) Examples of styrene-based block copolymers include styrene-butadiene copolymer (SBS), styrene-isoprene copolymer (SIS), styrene-ethylene-butylene-styrene copolymer (SEBS), styrene-ethylene-propylene-styrene copolymer (SEPS), styrene-isobutylene-styrene copolymer (SIBS), acrylonitrile-styrene copolymer (AS), and styrene-butadiene-acrylonitrile copolymer (ABS). Among these, styrene-butadiene copolymer (SBS), styrene-isoprene copolymer (SIS), styrene-ethylene-butylene-styrene copolymer (SEBS), styrene-ethylene-propylene-styrene copolymer (SEPS), and styrene-isobutylene-styrene copolymer (SIBS) are preferred. These styrene-based block copolymers have excellent compatibility with other components contained in the curable composition, and impart suitable rubber properties to the resulting cured product.

[0082] The number average molecular weight of the styrene-based block copolymer is preferably 10,000 to 500,000, and more preferably 50,000 to 300,000. When the number average molecular weight is within the above range, the compatibility with other components of the curable composition is good, and the viscosity of the obtained curable composition is also appropriate.

[0083] The content of the styrene-based block copolymer is preferably 0.1 to 1000 parts by weight, and more preferably 1.0 to 300 parts by weight, relative to 100 parts by weight of component A. If the content is within the above range, a cured product having a good balance between adhesion and durability can be obtained.

[0084] (Thiol compounds) When a thiol compound is added to a curable composition, the crosslinking points are increased, improving the curability and the hardness and strength of the cured product. Alternatively, the crosslinking points are reduced by chain transfer, improving the flexibility and adhesion of the cured product.

[0085] Examples of thiol compounds include decanethiol, trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptopropionate), trimethylolpropane tris(3-mercaptobutyrate), trimethylolethane tris(3-mercaptobutyrate), trimethylolethane tris(3-mercaptobutyrate), ethylene glycol bis(3-mercaptoglycolate), butanediol bis(3-mercaptoglycolate), trimethylolpropane tris(3-mercaptoglycolate), pentaerythritol tetrakis(3 -mercaptoglycolate), tris-[(3-mercaptopropionyloxy)-ethyl]-isocyanurate, pentaerythritol tetrakis(3-mercaptopropionate), tetraethylene glycol bis(3-mercaptopropionate), dipentaerythritol hexakis(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptobutyrate), 1,4-bis(3-mercaptobutyryloxy)butane, 1,3,5-tris(3-mercaptobutyloxyethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione.

[0086] The content of the thiol compound is preferably 0.1 to 100 parts by weight, and more preferably 0.50 to 30 parts by weight, relative to 100 parts by weight of Component A. When the content is within the above range, the curable composition has good curability and handleability.

[0087] (Tertiary amine compounds) When the curable composition contains a tertiary amine compound, the photocurability is improved.

[0088] Examples of tertiary amine compounds include trimethylamine, triethylamine, tributylamine, N,N'-diethanolamine, N,N'-dimethyl-p-toluidine, N,N'-dimethyl-aniline, N-methyl-diethanolamine, N-methyl-dimethanolamine, N,N'-dimethylamino-acetophenone, N,N'-dimethylaminobenzophenone, N,N'-diethylamino-benzophenone, and triisopropanolamine.

[0089] The content of the tertiary amine compound is preferably 0.1 to 100 parts by weight, and more preferably 0.50 to 30 parts by weight, relative to 100 parts by weight of Component A. If the content is within the above range, the curable composition will have excellent curability.

[0090] (Adhesion promoter) When the curable composition contains an adhesion promoter, the adhesiveness of the cured product is improved.

[0091] Examples of adhesion promoters include 3-(meth)acryloxypropylmethyldimethoxysilane, 3-(meth)acryloxypropyltrimethoxysilane, 3-(meth)acryloxypropylmethyldiethoxysilane, 3-(meth)acryloxypropyltriethoxysilane, (meth)acryloxyoctyltrimethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltrichlorosilane, 3-glycidyloxypropylmethyldimethoxysilane, 3-glycidyloxypropyltrimethoxysilane, 3-glycidyloxypropylmethyldiethoxysilane, 3-glycidyloxypropyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, 3-chloropropyltrimethoxysilane, 3-aminopropylmethyldimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropylmethyldiethoxysilane, 3-aminopropyltriethoxysilane, silane, 3-mercaptopropyl methyl dimethoxy silane, 3-mercaptopropyl trimethoxy silane, 3-mercaptopropyl methyl diethoxy silane, 3-mercaptopropyl triethoxy silane, 3-(2-aminoethyl amino) propyl methyl dimethoxy silane, 3-(2-aminoethyl amino) propyl trimethoxy silane, 3-(2-aminoethyl amino) propyl methyl diethoxy silane, 3-(2-aminoethyl amino) propyl triethoxy silane, 2-(3,4-epoxycyclohexyl) ethyl trimethoxy silane, 3-ureidopropyl triethoxy silane, 2-hydroxyethyl (meth) acrylate phosphate ester, methacryloxyoxyethyl acid phosphate monoethylamine half salt, 2-hydroxyethyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate.Among these, 3-(meth)acryloxypropylmethyldimethoxysilane, 3-(meth)acryloxypropyltrimethoxysilane, 3-(meth)acryloxypropylmethyldiethoxysilane, 3-(meth)acryloxypropyltriethoxysilane, 3-glycidyloxypropylmethyldimethoxysilane, 3-glycidyloxypropyltrimethoxysilane, 3-glycidyloxypropylmethyldiethoxysilane, 3-glycidyloxypropyltriethoxysilane, 3-aminopropylmethyldimethoxysilane, 3-aminopropyltrimethoxysilane, Particularly preferred are silane, 3-aminopropylmethyldiethoxysilane, 3-aminopropyltriethoxysilane, 3-(2-aminoethylamino)propylmethyldimethoxysilane, 3-(2-aminoethylamino)propyltrimethoxysilane, 3-(2-aminoethylamino)propylmethyldiethoxysilane, 3-(2-aminoethylamino)propyltriethoxysilane, 2-hydroxyethyl(meth)acrylate phosphate ester, 2-hydroxyethyl(meth)acrylate, 3-hydroxypropyl(meth)acrylate, and 4-hydroxybutyl(meth)acrylate.

[0092] The content of the adhesion promoter is preferably 0.01 to 20.0 parts by weight, and more preferably 0.1 to 10.0 parts by weight, relative to 100 parts by weight of component A. If the content is within the above range, a good balance between curability and adhesion will be achieved.

[0093] 2. Composition of the Curable Composition The lower limit of the content of component B is preferably 1 part by weight or more, more preferably 3 parts by weight or more, and even more preferably 5 parts by weight or more, relative to 100 parts by weight of the content of component A. The upper limit of the content of component B is preferably 100 parts by weight or less, more preferably 80 parts by weight or less, even more preferably 50 parts by weight or less, and particularly preferably 30 parts by weight or less, relative to 100 parts by weight of the content of component A.

[0094] The lower limit of the content of component C is preferably 0.001 parts by weight or more, more preferably 0.005 parts by weight or more, even more preferably 0.01 parts by weight or more, and particularly preferably 0.05 parts by weight or more, relative to 100 parts by weight of the content of component A. The upper limit of the content of component C is preferably 10 parts by weight or less, more preferably 5 parts by weight or less, even more preferably 3 parts by weight or less, and particularly preferably 1 part by weight or less, relative to 100 parts by weight of the content of component A.

[0095] The lower limit of the content of component D is preferably more than 0 parts by weight, more preferably 3 parts by weight or more, and even more preferably 5 parts by weight or more, relative to 100 parts by weight of the content of component A. The upper limit of the content of component D is preferably 100 parts by weight or less, more preferably 80 parts by weight or less, even more preferably 50 parts by weight or less, and particularly preferably 30 parts by weight or less, relative to 100 parts by weight of the content of component A.

[0096] The lower limit of the content of component E is preferably 0.1 parts by weight or more, more preferably 1 part by weight or more, and even more preferably 5 parts by weight or more, based on 100 parts by weight of the content of component A. The upper limit of the content of component E is preferably 100 parts by weight or less, more preferably 80 parts by weight or less, and even more preferably 50 parts by weight or less, based on 100 parts by weight of the content of component A.

[0097] 3. Cured Products, Coatings, and Bonded Products The cured product according to one embodiment of the present invention is obtained by curing the above-mentioned curable composition. The curable composition can be cured, for example, by irradiation with UV light.

[0098] The cured product can be used for various applications. Examples of the products include sealing materials, adhesives, sealing materials, gasket materials, adhesives, coating materials, covering materials, resist materials, vibration-proofing materials, vibration-damping materials, shock-absorbing materials, buffer materials, electrical insulating materials, foams, paints, inks, casting agents, potting agents, molding materials, underfill materials, die-bonding materials, and fillers. Specific examples of parts in which the cured product is used include electric and electronic parts (LEDs, batteries, fuel cells, secondary batteries, sensors, semiconductors, circuit boards, displays, home appliances, optical communications and optical circuits, optical recording, magnetic recording, etc.), pharmaceuticals and medical products, automotive and marine parts, building parts, and acoustic parts. The shape of the cured product can be, for example, a sheet (film), a tape, or a molded product (packing, O-ring, belt, tube, valve, hose, etc.).

[0099] One aspect of the present invention is a coating obtained by coating the above-mentioned curable composition on an adhesive surface of a substrate. In the coating, the curable composition is uncured. Another aspect of the present invention is a bonded body in which a cured product obtained by curing the above-mentioned curable composition is bonded to an adhesive surface of a substrate. In the bonded body, the curable composition is cured to form a cured product. The bonded body is obtained by curing the curable composition contained in the coating. Therefore, if the bonded body is considered to be a product, the coating can be a semi-finished product.

[0100] When applying the curable composition to the substrate, known techniques can be used. The amount of the curable composition applied (weight per unit area, etc.) may be appropriately determined by those skilled in the art. The dimensions (thickness, etc.) of the cured product included in the bonded body may also be appropriately determined by those skilled in the art.

[0101] In one embodiment, at least a part of the adhesive surface is plasma-treated. The plasma-treated adhesive surface has fine scratches and generates many hydrophilic functional groups, improving the adhesive strength between the cured product and the substrate interface. Specific plasma treatment methods are well known in the art and can be appropriately determined by those skilled in the art.

[0102] In one embodiment, the material of at least a part of the adhesive surface is a metal. Examples of metals include iron, aluminum, iron-based alloys (steel, cast iron, stainless steel, etc.), and aluminum-based alloys. The above-mentioned curable composition has improved adhesion to stainless steel (particularly plasma-treated stainless steel). Therefore, it is preferable that the material of at least a part of the adhesive surface is stainless steel (particularly plasma-treated stainless steel).

[0103] [4. Summary] The present invention includes the following aspects. <1> A curable composition comprising the following components A to C: Component A: an isobutylene polymer having an average of 1.2 or more (meth)acryloyl groups per molecule; Component B: a vinyl monomer having one or more functional groups selected from the group consisting of a carboxyl group and its alkali metal salt, a phosphoric acid group and its alkali metal salt, a hydroxyl group and its alkali metal salt, an amino group, and an epoxy group; Component C: Radical polymerization initiator. <2> The component B is a (meth)acrylic monomer and / or an aromatic vinyl monomer. <1> The curable composition according to claim 1. <3> The component C is a photoradical polymerization initiator. <1> or <2> The curable composition according to claim 1. <4> The composition further contains the following component D: <1> ~ <3> The curable composition according to any one of the preceding claims, Component D: Plasticizer. <5> The component D is a polybutene oil and / or a paraffin oil. <4> The curable composition according to claim 1. <6> The following component E is further contained. <1> ~ <5> The curable composition according to any one of the preceding claims, Component E: A vinyl monomer other than Component B. <7> The component E is a (meth)acrylic monomer and / or an aromatic vinyl monomer. <6> The curable composition according to claim 1. <8> When the content of the component A is 100 parts by weight, the contents of the components B and C are as follows: <1> ~ <7> The curable composition according to any one of the preceding claims, Component B: 1~100 parts by weight; Ingredient C: 0.001~10 parts by weight. <9> When the content of the above component A is 100 parts by weight, the content of the above component D is as follows: <4> A curable composition according to claim 1, Component D: More than 0 parts by weight, less than 100 parts by weight. <10> <1> ~ <9> 2. A coated article obtained by coating the curable composition according to any one of claims 1 to 11 on an adhesive surface of a substrate. <11> At least a portion of the adhesive surface is plasma treated. <10> The coating material according to claim 1. <12> At least a part of the adhesive surface is made of stainless steel. <10> or <11> The coating material according to claim 1. <13> <1> ~ <9> 2. A bonded body, comprising a substrate and a cured product obtained by curing the curable composition according to claim 1, bonded to an adhesive surface of the substrate. <14> At least a portion of the adhesive surface is plasma treated. <13> The conjugate according to claim 1, <15> At least a part of the adhesive surface is made of stainless steel. <13> or <14> The conjugate according to claim 1, <16> <1> ~ <9> 2. A cured product obtained by curing the curable composition according to claim 1.

[0104] The present invention also includes the following aspects. <a1> A method for bonding a first substrate and a second substrate, comprising the steps of: <1> ~ <9> A method comprising the step of applying the curable composition according to any one of claims 1 to 5. <a2> At least a portion of the adhesive surface is plasma treated. <a1>The method described above. <a3> At least a part of the adhesive surface is made of stainless steel. <a1>or <a2>The method described above. <a4> The method further comprises a step of curing the curable composition. <a1> ~ <a3>2. The method according to claim 1 , EXAMPLES

[0105] [Measurement method] (1)Molecular weight The number average molecular weight (Mn) of the isobutylene polymer was measured by a standard polystyrene conversion method using size exclusion chromatography (SEC). The specifications of the SEC are as follows. SEC system: LC Module 1 (Waters) Stationary phase: Shodex GPCK-804 (polystyrene cross-linked gel packed column, Showa Denko K.K.) Mobile phase: Chloroform

[0106] (2) Number of (meth)acryloyl groups The average number of (meth)acryloyl groups introduced per molecule of the isobutylene polymer was determined by the following procedure. The number average molecular weight (Mn) of the isobutylene polymer was measured by the method described in 1.(1). 2. Isobutylene polymer 1 HNMR was measured. First, the area of ​​the peaks attributable to the two methyl groups in the isobutylene skeleton was used as the reference area. Specifically, the integral value of the peak near 1.3 ppm was set so as to satisfy the following formula. Integral value of the peak near 1.3 ppm = (Mn / 56.11) x 6 3. The peaks appearing in the vicinity of 5.8 to 5.9 ppm, 6.1 to 6.2 ppm, and 6.4 ppm were determined to be peaks derived from (meth)acryloyl groups. The integral value of each peak was calculated as a relative value to the reference area, and the average of the three integral values ​​was calculated. The obtained average value was determined to be the average number of (meth)acryloyl groups introduced per molecule of the isobutylene polymer.

[0107] (3) Peel test This was carried out according to the following procedure. 1. A first substrate, a second substrate, and a curable composition were prepared. The material of the first substrate was stainless steel (SUS304), an aluminum alloy (A2024), or polyethylene terephthalate. The dimensions of the first substrate were length: 25 mm x width: 100 mm x thickness: 2 mm (stainless steel), length: 25 mm x width: 100 mm x thickness: 1.6 mm (aluminum alloy), length: 25 mm x width: 100 mm x thickness: 3 mm (polyethylene terephthalate). The second substrate was glass. The dimensions of the second substrate were length: 25 mm x width: 100 mm x thickness: 5 mm. The curable composition was prepared in the examples or comparative examples. 2. If necessary, the surface of the first substrate was plasma-treated. For the plasma treatment, an atmospheric pressure plasma surface treatment device (Laboratory system with rotating nozzle RD1004 and 3-axis robot, Japan Plasmatreat Inc.) was used. The treatment conditions were as follows: (For stainless steels and aluminum-based alloys) Voltage: 280V Distance between nozzle and first substrate: 5mm Scanning speed: 100mm / sec (In the case of polyethylene terephthalate) Voltage: 280V Distance between nozzle and first substrate: 10mm Scanning speed: 300mm / sec 3. The first and second substrates were bonded together via their adhesive surfaces so that only the ends of the substrates overlapped. The dimensions of the adhesive surface were 25 mm long x 10 mm wide. The thickness of the curable composition applied to the adhesive surface was 1 mm. 4. The curable composition was cured by irradiating it with ultraviolet light. The irradiation conditions were: peak irradiance: 500 mW / cm 2 Ultra-accumulated light output of 5000mJ / cm 2 An electrodeless UV lamp bulb (LH6 (H-bulb), Heraeus) was used for UV irradiation. 5. The first substrate and the second substrate were pulled so that the directions of the forces applied to them were 180° different, and the stress at which the two substrates peeled off was measured. An AGS-J (Shimadzu Corporation) was used for the measurement. The peeled surface was also observed to determine whether it was interfacial failure (AF) or cohesive failure (CF).

[0108] 〔material〕 The materials used in the examples and comparative examples are as follows. Ingredient A (Meth)acryloyl group-containing isobutylene polymer: obtained in Production Example 1 ●Ingredient B Monomer B1: Acrylic acid Monomer B2: Ester of phosphoric acid and 2-hydroxyethyl methacrylate (Light Ester P-1M, Kyoeisha Chemical Co., Ltd.) Monomer B3: 4-hydroxybutyl acrylate Monomer B4: 2-Dimethylaminoethyl acrylate Monomer B5: Glycidyl methacrylate ●Component C Photoradical polymerization initiator: Obtained in Production Example 2 ●Component D Plasticizers (Nippon Oil Polybutene HV-100, ENEOS Corporation, Polybutene Oil) ●Ingredient E Vinyl monomers other than component B (lauryl acrylate) ●Other Antioxidants (hindered phenols, Adeka STAB AO-50, ADEKA Corporation)

[0109] [Production Example 1: Production of isobutylene polymer] An isobutylene polymer having an acryloyl group introduced at the molecular end was produced by the following procedure. 1. The atmosphere inside a 1L separable flask was replaced with nitrogen. 2. 44 mL of n-hexane and 395 mL of butyl chloride were charged and cooled to -70°C with stirring under a nitrogen atmosphere. n-Hexane and butyl chloride were dried over molecular sieves before use. 3. 159 mL of isobutylene (1.68 mol), 1.86 g of p-dicumyl chloride (0.0081 mol), and 0.302 g of 2,6-lutidine (0.00282 mol) were added to a vessel. 4. After the reaction mixture was cooled to -70°C, 0.88 mL of titanium tetrachloride (0.0080 mol) was added, which initiated the polymerization. 5. When the amount of isobutylene remaining was less than 0.5% of the amount charged, 4.08 g of 4-phenoxybutyl acrylate and 5.29 mL of titanium tetrachloride were added to the vessel. The amount of isobutylene remaining was measured by gas chromatography. 6. The mixture was stirred at -70°C for 1 hour. 7. 580g of pure water, 22g of 48% aqueous sodium hydroxide solution, 10mL of n-hexane and 87mL of butyl chloride were added to the vessel to stop the reaction. 8. The resulting polymerization solution was washed twice with 145 mL of pure water. 9. 8.3 g of powdered activated carbon (Taiko A, Futamura Chemical Co., Ltd.) was added to the washed polymerization solution, which was then stirred for 30 minutes and filtered through a filter with 1 μm mesh. 10. 0.17 g of 4-methoxyphenol was added to the obtained filtrate, and the solvent was distilled off under reduced pressure at 120° C. In this way, an isobutylene polymer having an acryloyl group introduced at the molecular end was obtained.

[0110] The isobutylene polymer had a number average molecular weight (Mn) of 15,200. The number of acryloyl groups introduced into the terminals of the isobutylene polymer was 1.88 on average per molecule.

[0111] [Production Example 2: Preparation of photopolymerization initiator] A photopolymerization initiator was prepared according to the following procedure. 1. 20 g of 2-hydroxy-2-methyl-1-phenyl-propan-1-one (DAROCUR1173, BASF Japan Ltd.) and 10 g of bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide (IRGACURE819, BASF Japan Ltd.) were weighed out. 2. Each component was mixed with a spatula for 5 minutes while being heated to 80°C. In this way, a photopolymerization initiator was obtained.

[0112] [Examples 1 to 26, Comparative Examples 1 to 5] A curable composition was obtained by the following procedure. 1. The components listed in Table 1 were prepared (unit: parts by weight). 2. All ingredients except for C were heated to 90°C and mixed by hand with a spatula for 5 minutes. 3. Component C was further added and mixed by hand for 2 minutes. 4. The curable composition was degassed in vacuum for 7 minutes using a rotation-revolution type mixer, Awatori Rentaro ARE-310 (Thinky Corporation).

[0113] 〔result〕 The results are shown in Table 1.

[0114] [Table 1]

[0115] JPEG2025081121000006.jpg230102

[0116] JPEG2025081121000007.jpg153136

[0117] As can be seen from Table 1, the curable compositions according to the Examples had higher peel strengths than the curable compositions according to the Comparative Examples. In particular, the peel strength was improved by subjecting the adhesive surface of the first substrate to plasma treatment (see comparison between Examples 1 to 12 and Examples 15 to 25). As for the material of the substrate 1, in addition to stainless steel, aluminum alloys and polyethylene terephthalate also showed high peel strengths (see Examples 13, 14, and 26). [Industrial Applicability]

[0118] The curable composition according to one embodiment of the present invention can be used in a variety of applications, including, for example, sealing materials, sealing materials for fuel cells and secondary batteries, sealing materials, coating agents, potting materials, fixed gaskets, on-site formed gaskets, adhesives, pressure sensitive adhesives, fillers, molded bodies, foams, films, casting materials, inks, and vibration-proofing, vibration damping, soundproofing, and seismic isolation materials. < / a1>

Claims

1. A curable composition comprising the following components A to C: Component A: An isobutylene-based polymer having an average of 1.2 or more (meth)acryloyl groups per molecule; Component B: A vinyl-based monomer having one or more functional groups selected from the group consisting of a carboxyl group and its alkali metal salt, a phosphate group and its alkali metal salt, a hydroxyl group and its alkali metal salt, an amino group, and an epoxy group; Component C: A radical polymerization initiator.

2. The curable composition according to claim 1, wherein the above-mentioned component B is a (meth)acrylic monomer and / or an aromatic vinyl monomer.

3. The curable composition according to claim 1, wherein the above-mentioned component C is a photo radical polymerization initiator.

4. The curable composition according to claim 1, further comprising the following component D: Component D: A plasticizer.

5. The curable composition according to claim 4, wherein the above-mentioned component D is polybutene oil and / or paraffin oil.

6. The curable composition according to claim 1, further comprising the following component E: Component E: A vinyl-based monomer other than component B.

7. The curable composition according to claim 6, wherein the above-mentioned component E is a (meth)acrylic monomer and / or an aromatic vinyl monomer.

8. The curable composition according to claim 1, wherein when the content of the above-mentioned component A is 100 parts by weight, the contents of the above-mentioned component B and the above-mentioned component C are as follows: Component B: 1 to 100 parts by weight; Component C: 0.001 to 10 parts by weight.

9. The curable composition according to claim 4, wherein when the content of the above-mentioned component A is 100 parts by weight, the content of the above-mentioned component D is as follows: Component D: More than 0 parts by weight and 100 parts by weight or less.

10. A coated article obtained by applying the curable composition according to any one of claims 1 to 9 to an adhesive surface of a substrate.

11. The coated article according to claim 10, wherein at least a part of the above-mentioned adhesive surface is plasma-treated.

12. The coated article according to claim 10, wherein at least a part of the material of the above-mentioned adhesive surface is stainless steel.

13. A bonded article in which a cured product obtained by curing the curable composition according to any one of claims 1 to 9 is bonded to an adhesive surface of a substrate.

14. The bonded article according to claim 13, wherein at least a part of the above-mentioned adhesive surface is plasma-treated.

15. The bonded body according to claim 13, wherein at least a part of the material of the bonding surface is stainless steel.

16. A cured product obtained by curing the curable composition according to any one of claims 1 to 9.

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