Resin composition, curable composition, and cured product

Abstract

To provide a resin composition having high transparency.SOLUTION: A resin composition comprises: a component A that is a (meth)acrylic polymer having a silyl group; a component B that is a hydrocarbon having a carbon-carbon double bond in its molecule; and a component C that is a radical generator. When the content of the component A is defined as 100 pts.wt., the content of the component B is more than 0 pt.wt. and 0.5 pt.wt. or less. The component A is a polymer that satisfies specific conditions.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a resin composition, a curable composition, and a cured product. [Background technology]

[0002] Polymer molecules having silyl groups form siloxane bonds with other polymer molecules as a result of hydrolysis of the silyl groups. This crosslinking reaction produces a rubber-like cured product. Curable compositions containing such polymer molecules are used in sealants, adhesives, paints, etc. (see, for example, Patent Document 1). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication No. 2023 / 048155 Summary of the Invention [Problem to be solved by the invention]

[0004] The curable compositions disclosed in the prior art such as Patent Document 1 sometimes had low transparency due to the resin components, and therefore the transparency of the cured product also sometimes was low.

[0005] An object of one aspect of the present invention is to provide a resin composition having high transparency. [Means for solving the problem]

[0006] In order to solve the above problems, a resin composition according to one embodiment of the present invention contains the following components A to C: Component A: a (meth)acrylic polymer having a silyl group; Component B: Hydrocarbons having a carbon-carbon double bond in the molecule; Component C: Radical generator; When the content of the above component A is 100 parts by weight, the content of the above component B is more than 0 parts by weight and 0.5 parts by weight or less: Here, the component A is The molecule has an XY diblock structure having an X block and a Y block, or an XYX triblock structure, The number of repeating units derived from the silyl group-containing (meth)acrylic acid ester monomer contained in the X block is more than 2.0 on average, the content of repeating units derived from silyl group-containing (meth)acrylic acid ester monomers contained in the Y block is 0% by weight or more and less than 5% by weight based on the weight of all repeating units contained in the Y block, The molecular weight distribution (Mw / Mn) is 1.8 or less. Effect of the Invention

[0007] According to one aspect of the present invention, a highly transparent resin composition is provided. 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." Unless otherwise specified in this specification, "silyl group" means "hydrolyzable silyl group." In one embodiment, the silyl group is an alkoxysilyl group.

[0010] 1. Components of the Resin Composition and the Curable Composition A resin composition according to one embodiment of the present invention includes component A: a (meth)acrylic polymer having a silyl group, component B: a hydrocarbon having a carbon-carbon double bond in the molecule, and component C: a radical generator. The resin composition may include, as an optional component, component D: a reducing agent and / or component E: one or more plasticizers selected from the group consisting of ether-based plasticizers, ester-based plasticizers, and ether ester-based plasticizers. A resin composition further containing a curing catalyst can be a curable composition.

[0011] [1.1. Component A: (meth)acrylic polymer having silyl group] Component A is a (meth)acrylic polymer having a silyl group. Component A has a silyl group derived from a silyl group-containing (meth)acrylic ester monomer. Component A has an X block having a high frequency of silyl groups and a Y block having a low frequency of silyl groups. Component A can be polymerized, for example, by changing the monomer composition during polymerization.

[0012] Component A has an X block and a Y block, and contains an XY diblock structure or an XYX triblock structure in the molecule. The structure of the entire molecule of component A is not particularly limited as long as it contains an XY diblock structure or an XYX triblock structure, and may be, for example, an XYXY tetrablock structure.

[0013] Here, the term "XYX triblock structure" means the "ABA triblock structure" generally known among those skilled in the art. The ratio of X / Y in component A is preferably from (5 / 95) to (60 / 40), more preferably from (15 / 85) to (40 / 60).

[0014] In one embodiment, the molecule of component A has an XY diblock structure. In the molecule of the XY diblock structure, the X block can be a region of 40% or less, 30% or less, or 25% or less from one end of the molecule (all repeating units contained in the molecule are taken as 100%). Here, the X block is the block on the side where silyl groups are distributed in a relatively large amount.

[0015] In one embodiment, the molecule of component A has an XYX triblock structure. In the molecule of the XYX triblock structure, the X blocks can be 40% or less, 30% or less, or 25% or less of the region from the ends of the molecule (all repeat units contained in the molecule are taken as 100%). Here, the X blocks are blocks located at both ends of the molecule.

[0016] Component A has a repeating unit derived from a silyl group-containing (meth)acrylic acid ester monomer. The repeating unit derived from the silyl group-containing (meth)acrylic acid ester monomer is contained relatively more in the X block. The repeating units derived from the silyl group-containing (meth)acrylic acid ester monomer contained in the X block are more than 2.0 on average. When component A has two or more X blocks in one molecule, the total number of repeating units derived from the silyl group-containing (meth)acrylic acid ester monomer contained in the multiple X blocks is more than 2.0 on average. On the other hand, the repeating units derived from the silyl group-containing (meth)acrylic acid ester monomer contained in the Y block are 0% by weight or more and less than 5% by weight based on the weight of all repeating units contained in the Y block.

[0017] The repeating units derived from the silyl group-containing (meth)acrylic acid ester monomer contained in the X block are more than 2.0 on average, preferably 2.1 or more, more preferably 2.2 or more, even more preferably 2.3 or more, and particularly preferably 2.5 or more. Similarly, the repeating units derived from the silyl group-containing (meth)acrylic acid ester monomer contained in the X block are preferably 0.5% by weight or more, more preferably 2.0% by weight or more, and even more preferably 3.0% by weight or more, based on the weight of all repeating units contained in the X block. The upper limit of the repeating units derived from the silyl group-containing (meth)acrylic acid ester monomer contained in the X block is preferably 90% by weight or less, more preferably 60% by weight or less, and even more preferably 30% by weight or less.

[0018] The upper limit of the repeating units derived from the silyl group-containing (meth)acrylic acid ester monomer contained in the Y block is less than 5% by weight, preferably 4% by weight or less, more preferably 3% by weight or less, even more preferably 2% by weight or less, and particularly preferably 1% by weight or less, based on the weight of all repeating units contained in the Y block. The lower limit of the repeating units derived from the silyl group-containing (meth)acrylic acid ester monomer contained in the Y block is preferably 0% by weight or more, more preferably more than 0% by weight, based on the weight of all repeating units contained in the Y block.

[0019] The number of silyl groups introduced into component A is, on average, more than 2.0, preferably 2.2 or more, more preferably 2.6 or more, even more preferably 3.0 or more, and particularly preferably 3.4 or more, in the whole molecule. The upper limit of the number of silyl groups introduced into the (meth)acrylic polymer is preferably 10.0 or less, more preferably 8.0 or less, even more preferably 6.0 or less, and particularly preferably 5.0 or less. If the number of silyl groups is within the above range, a resin composition and a cured product with good physical properties can be obtained.

[0020] Specific examples of silyl group-containing (meth)acrylic acid ester monomers include 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, and 3-acryloxypropyltrimethoxysilane.

[0021] Component A may contain a repeating unit derived from a (meth)acrylic monomer having a long side chain. In this specification, the term "(meth)acrylic monomer having a long side chain" refers to a repeating unit derived from a (meth)acrylic monomer having a long side chain, represented by the formula: CH2=C(R 1 )COOR 2 In the formula, R 1 R is a hydrogen atom or a methyl group. 2 is a group having 9 or more carbon atoms.

[0022] The content of the repeating unit derived from the (meth)acrylic monomer having a long side chain is preferably 1% by weight or more of all the constitutional units contained in Component A. Component A containing such a repeating unit may improve the compatibility with the polyoxyalkylene polymer and improve the physical properties of the obtained cured product. The upper limit of the content of the repeating unit derived from the (meth)acrylic monomer having a long side chain is preferably 5% by weight or less, more preferably 3% by weight or less. If the content is within the above range, the production cost of Component A does not increase excessively.

[0023] Examples of (meth)acrylic monomers having a long side chain include nonyl (meth)acrylate, decyl (meth)acrylate, undecyl (meth)acrylate, dodecyl (meth)acrylate, tridecyl (meth)acrylate, tetradecyl (meth)acrylate, pentadecyl (meth)acrylate, hexadecyl (meth)acrylate, heptadecyl (meth)acrylate, octadecyl (meth)acrylate, icosyl (meth)acrylate, docosyl (meth)acrylate, oleyl (meth)acrylate, linoleyl (meth)acrylate, and isobornyl (meth)acrylate.

[0024] Among the above-mentioned monomers, one or more selected from octadecyl (meth)acrylate, oleyl (meth)acrylate, and linoleyl (meth)acrylate are preferred. These monomers have the advantage of being liquid at room temperature and having high polymerization stability. In addition, by blending these monomers, a (meth)acrylic acid-based polymer having high compatibility with a polyoxyalkylene-based polymer can be obtained.

[0025] In this specification, the term "(meth)acrylic monomer having a non-long side chain" refers to a (meth)acrylic monomer having a non-long side chain in the above formula, R 2represents a monomer having 8 or less carbon atoms. Examples of such monomers include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, pentyl (meth)acrylate, n-hexyl (meth)acrylate, cyclohexyl (meth)acrylate, heptyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, octyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, 2-ethoxyethyl (meth)acrylate, 2-butoxyethyl (meth)acrylate, isopropoxyethyl (meth)acrylate, benzyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2,2,2-trifluoroethyl (meth)acrylate, glycidyl (meth)acrylate, 1-ethylcyclopentyl ether (meth)acrylate, and dimethylaminoethyl (meth)acrylate.

[0026] Among the above-mentioned monomers, one or more selected from methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, and 2-ethylhexyl (meth)acrylate are preferred. These monomers have low procurement costs and are suitable for the purpose of reducing the production cost of component A.

[0027] Furthermore, from the viewpoint of glass transition point, one or more types selected from n-butyl acrylate and 2-ethylhexyl acrylate are preferred. Component A obtained from these monomers has a low glass transition point and a low polymer viscosity. Therefore, a resin composition that is easy to use in a low temperature environment is obtained.

[0028] Component A may have a repeating unit derived from a monomer other than a (meth)acrylic acid ester monomer. The proportion of the repeating unit derived from a (meth)acrylic acid ester monomer in Component A is preferably 50% by weight or more, more preferably 70% by weight or more, and even more preferably 90% by weight or more of the total weight of Component A.

[0029] [1.1.2. Silyl groups possessed by (meth)acrylic copolymers] The silyl group contained in Component A may be derived from a silyl group-containing (meth)acrylic acid ester monomer. In one embodiment, the silyl group is represented by the following general formula: [Si(R 3 ) 2-b (Y) b O] m -Si(R 4 ) 3-a (Y) a

[0030] In the formula, R 3 and R 4 are independently an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, a methoxymethyl group, or a triorganosiloxy group represented by (R')3SiO-. R' is a monovalent hydrocarbon group having 1 to 20 carbon atoms. The three R's may be the same or different. R 3 or R 4 When two or more are present, they may be the same or different. Y represents a hydroxyl group or a hydrolyzable group. Examples of the hydrolyzable group include an alkoxy group, an acetoxy group, and an oxime group. In one embodiment, Y is a hydroxyl group, a methoxy group, an ethoxy group, or an isopropoxy group. When a single silyl group contains a plurality of X's, they may be the same or different. When a single molecule of component A contains a plurality of silyl groups, Y may be different for each silyl group. a is 0, 1, 2, or 3. b is 0, 1, or 2. m is an integer of 0 to 19. However, the relationship a+mb≧1 is satisfied.

[0031] The specific structure of the silyl group-containing (meth)acrylic acid ester monomer is not particularly limited. An example is a monomer represented by the following general formula: H2C=C(R 5 )C(=O)-O-(CH2) m -SiR 6 n(OR 7 ) 3-n

[0032] In the formula, R 5 is hydrogen or a methyl group. 6 and R 7 R is at least one selected from the group consisting of hydrogen, a methyl group, and an ethyl group. 6 and / or R 7 When a plurality of are present, they may be the same or different. m is an integer of 0 to 10. n is an integer of 0 to 2.

[0033] Specific examples of silyl group-containing (meth)acrylic acid ester monomers include 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, and 3-acryloxypropyltrimethoxysilane.

[0034] [1.1.3. Physical properties of component A] In one embodiment, the lower limit of the number average molecular weight of component A is preferably 2,000 or more, more preferably 10,000 or more, and even more preferably 15,000 or more. The upper limit of the number average molecular weight of component A is preferably 50,000 or less, more preferably 30,000 or less, and even more preferably 20,000 or less. If the number average molecular weight of component A is within the above range, the viscosity of the resin composition does not become too high, and sufficient workability can be ensured.

[0035] In one embodiment, the molecular weight distribution of component A is 1.8 or less, preferably 1.5 or less, 1.4 or less, 1.3 or less, or 1.2 or less. If the molecular weight distribution is within the above range, the viscosity of the polymer tends to decrease and the workability tends to improve. The molecular weight distribution is a value given by "weight average molecular weight ÷ number average molecular weight".

[0036] The weight average molecular weight and number average molecular weight are measured by gel permeation chromatography (GPC). For GPC measurement, chloroform is used as the mobile phase and a polystyrene gel column is used as the stationary phase. The molecular weight obtained by the measurement is the molecular weight converted into standard polystyrene.

[0037] [1.1.4. Manufacturing method of component A] The polymerization method of component A is not particularly limited, and known polymerization methods can be used (radical polymerization method, cationic polymerization method, anionic polymerization method, etc.). The polymerization method called SGO (Solid Grade Oligomer; high temperature continuous bulk polymerization) is preferred because it is a method that can obtain component A without using a polymerization solvent, a polymerization initiator, a chain transfer agent, etc. A living polymerization method is preferred because it can introduce a functional group near the end of the polymer molecule and can synthesize component A with a small molecular weight distribution. Examples of living polymerization methods include living radical polymerization method, living cationic polymerization method, and living anionic polymerization method, and among them, living radical polymerization method is suitable for polymerization of (meth)acrylic monomers. Examples of living radical polymerization methods include the following. Atom Transfer Radical Polymerization (ATRP) (see J. Am. Chem. Soc. 1995, 117, 5614; Macromolecules. 1995, 28, 1721) Single Electron Transfer Polymerization (SET-LRP (see J. Am. Chem. Soc. 2006, 128, 14156; JPSChem 2007, 45, 1607)) Reversible Chain Transfer Catalyzed Polymerization (RTCP) (see "Living Radical Polymerization Controlled by Organic Catalysts" Polymer Journal Vol. 68, 223-231 (2011); JP Patent Publication No. 2014-111798) Reversible addition-fragmentation chain transfer polymerization (RAFT polymerization) Nitroxy radical method (NMP method) Polymerization using organotellurium compounds (TERP method) · Polymerization method using organoantimony compounds (SBRP method) Polymerization method using organobismuth compounds (BIRP method) -Iodine transfer polymerization method

[0038] An example of a method for introducing a silyl group into component A is the method described in JP 2018-162394 A. The method disclosed in the document introduces a silyl group into component A by copolymerizing a (meth)acrylic acid ester monomer and a silyl group-containing (meth)acrylic acid ester monomer. More specifically, a silyl group is introduced near the terminal of the component A molecule by controlling the input amount of the silyl group-containing (meth)acrylic acid ester monomer according to the progress stage of the living polymerization. Component A obtained by these methods may have a silyl group locally at the terminal or near the terminal of the molecule.

[0039] [1.2. Component B: Hydrocarbons having a carbon-carbon double bond in the molecule] Component B is a hydrocarbon having a carbon-carbon double bond in the molecule. A "hydrocarbon" is a compound mainly composed of carbon and hydrogen. The lower limit of the number of carbon atoms contained in component B can be 2 or more, 3 or more, 4 or more, 5 or more, 6 or more, or 7 or more. The upper limit of the number of carbon atoms contained in component B can be 30 or less, 25 or less, 20 or less, or 15 or less.

[0040] Component B may have a small number of heteroatoms (such as oxygen, nitrogen, sulfur, phosphorus, and silicon atoms). The number of heteroatoms contained in component B may be 5 or less, 4 or less, 3 or less, 2 or less, or 1 or less. In one embodiment, component B is composed of only carbon and hydrogen atoms.

[0041] The number of carbon-carbon double bonds that component B has is not particularly limited. The number of carbon-carbon double bonds that component B has may be 5 or less, 4 or less, 3 or less, 2 or less, or 1. In one embodiment, component B has only one carbon-carbon double bond.

[0042] It is believed that the transparency of the resin composition is increased by blending component B. The presumed mechanism of action is as follows (however, the following is an explanation for the purpose of facilitating understanding of the present invention and is not intended to restrict the scope of the claims). Component A may contain unreacted (meth)acrylic monomer as an impurity. When the unreacted (meth)acrylic monomer reacts with component B, the amount of unreacted (meth)acrylic monomer present is reduced. This improves transparency. - At the end of component A synthesized by living polymerization, there is a halogen atom (such as a bromine atom) derived from the initiator. When the halogen atom at the end of component A is eliminated, the carbon-carbon double bond of component B is cleaved, and a carbon-carbon single bond is formed between component A and component B. This improves transparency.

[0043] Component B is preferably an α-olefin. Examples of α-olefins include ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 1-octene, 4-methyl-1-pentene, 4,4-dimethyl-1-pentene, 1-octene, 1-nonene, 1-decene, 1-undecene, 1-dodecene, 1-tridecene, 1-tetradecene, 1-pentadecene, 1-hexadecene, 1-heptadecene, 1-octadecene, 1-nonadecene, and 1-icosene.

[0044] The number of carbon atoms in the α-olefin is preferably 4 or more, more preferably 6 or more, and even more preferably 7 or more. Examples of such α-olefins include 1-butene, 1-pentene, 1-hexene, 3,3-dimethyl-1-butene, 4-methyl-1-pentene, 4,4-dimethyl-1-pentene, 1-octene, 1-nonene, 1-decene, 1-undecene, 1-dodecene, 1-tridecene, 1-tetradecene, 1-pentadecene, 1-hexadecene, 1-heptadecene, 1-octadecene, 1-nonadecene, and 1-icosene.

[0045] [1.3. Component C: Radical generator] Component C is a radical generator. A radical generator is a compound that generates radicals by applying light energy and / or heat energy. Examples of component C include photoradical generators and thermal radical generators. Component C generates a reaction with the mechanism of action described in Section [1.2.].

[0046] Examples of photoradical generators include carbonyl compounds, sulfur compounds, and acylphosphine oxides. Examples of carbonyl compounds include benzoin, benzoin monomethyl ether, benzoin isopropyl ether, acetoin, benzil, benzophenone, p-methoxybenzophenone, diethoxyacetophenone, benzil dimethyl ketal, 2,2-diethoxyacetophenone, 1-hydroxycyclohexyl phenyl ketone, methylphenyl glyoxylate, ethylphenyl glyoxylate, and 2-hydroxy-2-methyl-1-phenylpropane-1-one. Examples of sulfur compounds include tetramethylthiuram monosulfide and tetramethylthiuram disulfide. Examples of acylphosphine oxides include 2,4,6-trimethylbenzoyldiphenylphosphine oxide.

[0047] Examples of thermal radical generators include peroxides. Among peroxides, organic peroxides are preferred. Examples of organic peroxides include t-butyl peroxy octate, t-butyl peroxy isobutyrate, t-butyl peroxy laurate, t-butyl peroxy 3,5,5-trimethylhexanoate, t-butyl peroxy isopropyl monocarbonate, t-butyl peroxy-2-ethylhexanoate, 2,5-dimethyl-2,5-di(benzoylperoxy)hexane, t-butyl peroxy acetate, t-butyl peroxy benzoate, di-t-butyl peroxy isophthalate, benzoyl peroxide, diisopropyl peroxy dicarbonate, di-sec-butyl peroxy dicarbonate, azobisisobutyronitrile, and peroxy dicarbonate.

[0048] [1.4. Component D: Reducing agent] Component D is a reducing agent. Component D is an optional component, so it may or may not be included in the resin composition. By combining Component C, which is an oxidizing agent, with Component D, a redox initiator system can be formed. This allows radicals to be generated even at room temperature, improving the transparency of the resin composition in a room temperature environment. Examples of Component D include sulfinic acid, amines, and transition metal salts. Among these, amines are preferred, and organic amines are more preferred.

[0049] Examples of organic amines include primary amines (such as para-toluidine, octylamine, and laurylamine), secondary amines (such as dipropylamine, diethanolamine, and morpholine), tertiary amines (such as diisopropyl-p-toluidine, dimethylaniline, dimethyl-p-toluidine, trimethylamine, and tris-(dimethylaminomethyl)phenol), α-aminosulfones (such as bis-(tolylsulfonemethyl)amine, bis-(tolylsulfonemethyl)ethylamine, and bis-(tolylsulfonemethyl)-benzylamine), amine-aldehyde condensation products (such as condensation products of primary amines such as aniline or butylamine with aliphatic aldehydes such as butyraldehyde), and thiourea derivatives (such as 2-mercaptobenzimidazole, methylthiourea, dibutylthiourea, tetramethylthiourea, and ethylenethiourea).

[0050] [1.5. Component E: One or more plasticizers selected from the group consisting of ether-based plasticizers, ester-based plasticizers, and ether-ester-based plasticizers] Component E is one or more plasticizers selected from the group consisting of ether-based plasticizers, ester-based plasticizers, and ether ester-based plasticizers. By blending component E, the transparency of the resin composition can be further improved.

[0051] Examples of ether-based plasticizers include triethylene glycol 2-ethyl butyrate, diethylene glycol dibutyl ether, and tetraethylene glycol dimethyl ether. Examples of ester-based plasticizers include phthalates (dibutyl phthalate, diheptyl phthalate, di(2-ethylhexyl) phthalate, diisodecyl phthalate, butyl benzyl phthalate, etc.), non-aromatic dibasic acid esters (dioctyl adipate, dioctyl sebacate, dibutyl sebacate, isodecyl succinate, etc.), aliphatic esters (butyl oleate, methyl acetyl ricinoleate, etc.), esters of polyalkylene glycols (diethylene glycol dibenzoate, triethylene glycol dibenzoate, pentaerythritol esters, etc.), phosphate esters (tricresyl phosphate, tributyl phosphate, etc.), trimellitic acid esters, dipentaerythritol esters, and pyromellitic acid esters. Examples of the ether ester plasticizer include polyether ester plasticizers, polyvalent carboxylic acid ether ester plasticizers, and alkyl ether phosphate plasticizers.

[0052] [1.6.Curing catalyst] The resin composition may contain a curing catalyst. The resin composition containing the curing catalyst can function as a curable composition.

[0053] Examples of the curing catalyst include tin-based curing catalysts. Specific examples of the tin-based curing catalyst include dialkyltin carboxylates (dibutyltin dilaurate, dibutyltin diacetate, dibutyltin diethylhexanolate, dibutyltin dioctate, dibutyltin dimethyl maleate, dibutyltin diethyl maleate, dibutyltin dibutyl maleate, dibutyltin diisooctyl maleate, dibutyltin ditridecyl maleate, dibutyltin dibenzyl maleate, dibutyltin maleate, dioctyltin diacetate, dioctyltin distearate, dioctyltin dilaurate, dioctyltin diethyl maleate, dioctyltin diisooctyl maleate, etc.); dialkyltin oxides (dibutyltin oxide, dioctyltin oxide, a mixture of dibutyltin oxide and phthalic acid ester, etc.); tetravalent tin compounds (dialkyltin oxide, dialkyltin diacetate, etc.) and silyl group-containing low molecular weight silicon divalent tin compounds (such as tin octoate, tin naphthenate, and tin stearate); monoalkyltin compounds (such as monobutyltin compounds (such as monobutyltin tris-octoate and monobutyltin triisopropoxide), and monooctyltin compounds); reaction products or mixtures of amine compounds and organic tin compounds (such as reaction products or mixtures of laurylamine and tin octoate); chelate compounds (such as dibutyltin bisacetylacetonate, dioctyltin bisacetylcetonate, dibutyltin bisethylacetonate, and dioctyltin bisethylacetonate); and tin alcoholates (such as dibutyltin dimethylate, dibutyltin diethylate, dioctyltin dimethylate, and dioctyltin diethylate).

[0054] Among these, chelate compounds (such as dibutyltin bisacetylacetonate) and tin alcoholates are preferred because they have high activity as silanol condensation catalysts, and dibutyltin dilaurate is preferred because it causes little coloring when added to a curable composition, is inexpensive, and is easily available.

[0055] [1.7. Other ingredients] The resin composition may contain various additives in addition to the above-mentioned components. By adding these additives, various physical properties of the resin composition and the cured product can be adjusted. Examples of additives include the following. These additives may be used alone or in combination of two or more.

[0056] (Adhesion promoter) The resin composition may contain an adhesion promoter. By adding an adhesion promoter, the risk of the sealant peeling off from the adherend such as a siding board can be reduced (this peeling occurs when the joint width changes due to an external force). In addition, there may be cases where the need to use a primer to improve adhesion is eliminated. In this case, simplification of the construction work is expected.

[0057] An example of an adhesion promoter is a silane coupling agent. Specific examples of silane coupling agents include isocyanate group-containing silanes (γ-isocyanate propyl trimethoxysilane, γ-isocyanate propyl triethoxysilane, γ-isocyanate propyl methyl diethoxysilane, γ-isocyanate propyl methyl dimethoxysilane, etc.); amino group-containing silanes (γ-aminopropyl trimethoxysilane, γ-aminopropyl triethoxysilane, γ-aminopropyl methyl dimethoxysilane, γ-aminopropyl methyl diethoxysilane, N-(β-aminoethyl)-γ-aminopropyl trimethoxysilane, N-(β-aminoethyl)-γ-aminopropyl methyl dimethoxysilane, N-(β-aminoethyl)-γ-aminopropyl triethoxysilane, N-(β-aminoethyl)-γ-aminopropyl methyl diethoxysilane, γ-ureidopropyl trimethoxysilane, N-phenyl-γ-aminopropyl trimethoxysilane, N-benzyl-γ-aminopropyl trimethoxysilane, silane, N-vinylbenzyl-γ-aminopropyltriethoxysilane, etc.); mercapto group-containing silanes (γ-mercaptopropyltrimethoxysilane, γ-mercaptopropyltriethoxysilane, γ-mercaptopropylmethyldimethoxysilane, γ-mercaptopropylmethyldiethoxysilane, etc.); carboxysilanes (β-carboxyethyltriethoxysilane, β-carboxyethylphenylbis(2-methoxyethoxy)silane, N-(β-carboxymethyl)aminoethyl-γ-aminopropyltrimethoxysilane, etc.); vinyl-type unsaturated group-containing silanes (vinyltrimethoxysilane, vinyltriethoxysilane, γ-methacryloyloxypropylmethyldimethoxysilane, γ-acroyloxypropylmethyltriethoxysilane, etc.); halogen-containing silanes (γ-chloropropyltrimethoxysilane, etc.); isocyanurate silanes (tris(trimethoxysilyl)isocyanurate, etc.).In addition, derivatives obtained by modifying silane coupling agents, such as amino-modified silyl polymers, silylated amino polymers, unsaturated aminosilane complexes, phenylamino long-chain alkylsilanes, aminosilylated silicones, and silylated polyesters, can also be used as silane coupling agents.

[0058] The content of the adhesion promoter is preferably 0.1 to 20 parts by weight, and more preferably 0.5 to 10 parts by weight, based on 100 parts by weight of the content of component A.

[0059] (filling material) The resin composition may contain a filler. Examples of the filler include wood flour, reinforcing fillers (pulp, cotton chips, asbestos, mica, walnut shell powder, rice husk powder, graphite, white clay, silica (fumed silica, precipitated silica, crystalline silica, fused silica, dolomite, silicic anhydride, hydrated silicic acid, etc.), carbon black, etc.), fillers (heavy calcium carbonate, colloidal calcium carbonate, magnesium carbonate, diatomaceous earth, calcined clay, clay, talc, titanium oxide, bentonite, organic bentonite, ferric oxide, red iron oxide, fine aluminum powder, flint powder, zinc oxide, activated zinc oxide, zinc powder, zinc carbonate, shirasu balloon, etc.), and fibrous fillers (asbestos, glass fiber and glass filament, carbon fiber, Kevlar fiber, polyethylene fiber, etc.).

[0060] The content of the filler is preferably from 5 to 5,000 parts by weight, more preferably from 10 to 2,500 parts by weight, and particularly preferably from 15 to 1,500 parts by weight, relative to 100 parts by weight of the total content of component A.

[0061] (Physical property adjuster) The resin composition may contain a physical property modifier that adjusts the tensile properties of the cured product. By using the physical property modifier, it is possible to increase the hardness of the cured product, or conversely, to decrease the hardness of the cured product and increase the elongation.

[0062] Examples of physical property adjusters include alkylalkoxysilanes (methyltrimethoxysilane, dimethyldimethoxysilane, trimethylmethoxysilane, n-propyltrimethoxysilane, etc.); alkylisopropenoxysilanes (dimethyldiisopropenoxysilane, methyltriisopropenoxysilane, etc.); alkoxysilanes having functional groups (vinyldimethylmethoxysilane, γ-aminopropyltrimethoxysilane, N-(β-aminoethyl)aminopropylmethyldimethoxysilane, γ-mercaptopropyltrimethoxysilane, γ-mercaptopropylmethyldimethoxysilane, etc.); silicone varnishes; and polysiloxanes.

[0063] The content of the physical property adjusting agent is preferably 0.1 to 80 parts by weight, and more preferably 0.1 to 50 parts by weight, relative to 100 parts by weight of the total content of component A.

[0064] (Thixotropic agent (anti-sagging agent)) The resin composition may contain a thixotropy imparting agent (anti-sagging agent) in order to prevent sagging and improve workability.

[0065] Examples of the thixotropic agent include polyamide waxes; hydrogenated castor oil derivatives; and metal soaps (calcium stearate, aluminum stearate, barium stearate, etc.).

[0066] The content of the thixotropy-imparting agent is preferably 0.1 to 50 parts by weight, and more preferably 0.2 to 25 parts by weight, relative to 100 parts by weight of the total content of component A.

[0067] (light curing substance) The resin composition may contain a photocurable substance. A photocurable substance is a substance that undergoes a chemical change in a short time by the action of light, resulting in a change in physical properties (such as curing). By including a photocurable substance, the tackiness (residual tack) of the surface of the cured product can be reduced. A typical photocurable substance can be cured by leaving it at room temperature for one day in a sunny position indoors (such as near a window). Many photocurable substances are known, such as organic monomers, oligomers, resins, and compositions containing these, and the types are not particularly limited. Examples of photocurable substances include unsaturated acrylic compounds, polyvinyl cinnamates, and azido resins.

[0068] Specific examples of unsaturated acrylic compounds include (meth)acrylic acid esters of low molecular weight alcohols (ethylene glycol, glycerin, trimethylolpropane, pentaerythritol, neopentyl alcohol, etc.); (meth)acrylic acid esters of alcohols obtained by modifying acids (bisphenol A, isocyanuric acid) or low molecular weight alcohols with ethylene oxide, propylene oxide, etc.; (meth)acrylic acid esters (polyether polyols whose main chain is polyether and has hydroxyl groups at the terminals, and vinyl monomers radically polymerized in polyols whose main chain is polyether). polymer polyols obtained by reacting an epoxy resin (such as bisphenol A type or novolak type) with (meth)acrylic acid, polyester polyols having a polyester main chain and hydroxyl groups at the terminals, and polyols having a vinyl or (meth)acrylic copolymer main chain and hydroxyl groups in the main chain; epoxy acrylate oligomers obtained by reacting an epoxy resin (such as bisphenol A type or novolak type) with (meth)acrylic acid; and urethane acrylate oligomers having urethane bonds and (meth)acrylic groups in the molecular chain obtained by reacting a polyol, a polyisocyanate, a hydroxyl group-containing (meth)acrylate, etc.

[0069] The content of the photocurable substance is preferably 0.01 to 30 parts by weight, assuming the total content of component A to be 100 parts by weight.

[0070] (Antioxidants and Light Stabilizers) The resin composition may contain an antioxidant and / or a light stabilizer. Various antioxidants and light stabilizers are known. For example, the substances described in [Kenichi Saruwatari et al., "Antioxidant Handbook," Taiseisha, 1976] and [Zenjiro Osawa, editor, "Deterioration and Stabilization of Polymer Materials," CMC, 1990, pp. 235-242] can be mentioned.

[0071] Examples of the antioxidant include thioether-based antioxidants such as ADK STAB PEP-36 and ADK STAB AO-23 (all manufactured by ADEKA Corporation); phosphorus-based antioxidants such as Irgafos38, Irgafos168, and IrgafosP-EPQ (all manufactured by Ciba Specialty Chemicals); and hindered phenol-based antioxidants. Among the above, hindered phenol-based antioxidants are preferred.

[0072] Specific examples of hindered phenol-based antioxidants include 2,6-di-t-butyl-4-methylphenol, 2,6-di-t-butyl-4-ethylphenol, mono (or di or tri) (α-methylbenzyl)phenol, 2,2'-methylenebis(4-ethyl-6-t-butylphenol), 2,2'-methylenebis(4-methyl-6-t-butylphenol), 4,4'-butylidenebis(3-methyl-6-t-butylphenol), 4,4'-thiobis(3-methyl-6-t-butylphenol), and 2,5-di-t-butylhydroquinone. , 2,5-di-t-amylhydroquinone, triethylene glycol-bis-[3-(3-t-butyl-5-methyl-4-hydroxyphenyl)propionate], 1,6-hexanediol-bis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], 2,4-bis-(n-octylthio)-6-(4-hydroxy-3,5-di-t-butylanilino)-1,3,5-triazine, pentaerythrityl-tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], 2,2-thio-diethylene 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxybenzyl)benzene, bis(3,5-di-t-butyl-4-hydroxybenzyl)propionate, octadecyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, N,N'-hexamethylenebis(3,5-di-t-butyl-4-hydroxy-hydrocinnamamide), 3,5-di-t-butyl-4-hydroxy-benzylphosphonate-diethyl ester, 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxybenzyl)benzene, bis(3,5-di-t-butyl-4-hydroxybenzyl)propionate ethyl benzylphosphonate) calcium, tris-(3,5-di-t-butyl-4-hydroxybenzyl) isocyanurate, 2,4-bis[(octylthio)methyl]o-cresol, N,N'-bis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionyl]hydrazine, tris(2,4-di-t-butylphenyl)phosphite, 2-(5-methyl-2-hydroxyphenyl)benzotriazole, 2-[2-hydroxy-3,5-bis(α,α-dimethylbenzyl)phenyl]-2H-benzotriazole, 2-(3,5-di-t-butyl-2-hydroxyphenyl)benzotriazole, 2-(3-t-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole, 2-(3,5-di-t-butyl-2-hydroxyphenyl)-5-chlorobenzotriazole, 2-(3,5-di-t-amyl-2-hydroxyphenyl)benzotriazole, 2-(2'-hydroxy-5'-t-octylphenyl)-benzotriazole, methyl-3-[3-t-bu ethyl-5-(2H-benzotriazol-2-yl)-4-hydroxyphenyl]propionate-polyethylene glycol (molecular weight about 300) condensate, hydroxyphenylbenzotriazole derivatives, 2-(3,5-di-t-butyl-4-hydroxybenzyl)-2-n-butylmalonic acid bis(1,2,2,6,6-pentamethyl-4-piperidyl), 2,4-di-t-butylphenyl-3,5-di-t-butyl-4-hydroxybenzoate.

[0073] Examples of commercially available antioxidants include Nocrac 200, Nocrac M-17, Nocrac SP, Nocrac SP-N, Nocrac NS-5, Nocrac NS-6, Nocrac NS-30, Nocrac 300, Nocrac NS-7, and Nocrac DAH (all manufactured by Ouchi Shinko Chemical Industry Co., Ltd.); ADK STAB AO-30, ADK STAB AO-40, ADK STAB AO-50, ADK STAB AO-60, ADK STAB AO-616, ADK STAB AO-635, ADK STAB AO-658, ADK STAB AO-80, ADK STAB AO-15, ADK STAB AO-18, ADK STAB 328, and ADK STAB AO-37 (all manufactured by ADEKA Corporation); IRGANOX-245, IRGANOX-259, IRGANOX-565, IRGANOX-1010, IRGANOX-1024, IRGANOX-1035, IRGANOX-1076, IRGANOX-1081, IRGANOX-1098, IRGANOX-1222, IRGANOX-1330, IRGANOX-1425WL (all manufactured by Chiba Specialty Chemicals); Sumilizer GM, Sumilizer GA-80, Sumilizer GS (all manufactured by Sumitomo Chemical Co., Ltd.).

[0074] Examples of light stabilizers include ultraviolet absorbers (benzotriazole compounds such as Tinuvin P, Tinuvin 234, Tinuvin 320, Tinuvin 326, Tinuvin 327, Tinuvin 329, and Tinuvin 213 (all manufactured by Ciba Specialty Chemicals); triazine light stabilizers such as Tinuvin 1577; benzophenone compounds such as CHIMASSORB81; benzoate compounds such as Tinuvin 120 (manufactured by Ciba Specialty Chemicals); and hindered amine compounds). Of the above, hindered amine compounds are preferred.

[0075] Specific examples of the hindered amine compound include dimethyl succinate-1-(2-hydroxyethyl)-4-hydroxy-2,2,6,6-tetramethylpiperidine polycondensate, poly[{6-(1,1,3,3-tetramethylbutyl)amino-1,3,5-triazine-2,4-diyl}{(2,2,6,6-tetramethyl-4-piperidyl)imino}], N,N'-bis(3aminopropyl)ethylenediamine-2,4-bis[N-butyl-N-(1,2,2,6,6-pentamethyl-4-piperidyl)amino]-6-chloro-1,3,5-triazine condensate, bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate, and bis(2,2,6,6-tetramethyl-4-piperidinyl)succinate.

[0076] Examples of commercially available light stabilizers include Tinuvin 622LD, Tinuvin 144, CHIMASSORB944LD, and CHIMASSORB119FL (all manufactured by Chiba Specialty Chemicals), Adeka STAB LA-52, Adeka STAB LA-57, Adeka STAB LA-62, Adeka STAB LA-67, Adeka STAB LA-63, Adeka STAB LA-68, Adeka STAB LA-82, and Adeka STAB LA-87 (manufactured by ADEKA Corporation); Sanol LS-770, Sanol LS-765, Sanol LS-292, Sanol LS-2626, Sanol LS-1114, Sanol LS-744, and Sanol LS-440 (manufactured by Chiba Specialty Chemicals).

[0077] An antioxidant and a light stabilizer may be used in combination. By using them in combination, the effect of each agent may be further improved, and the heat resistance, weather resistance, etc. of the cured product may be improved. For example, in order to improve weather resistance, an ultraviolet absorber and a hindered amine compound (HALS) may be combined. This combination is preferable because it can further improve the effect of each agent.

[0078] The content of the antioxidant and / or the light stabilizer is preferably 0.1 to 20 parts by weight, respectively, when the total content of component A is 100 parts by weight.

[0079] 2. Composition of Resin Composition and Curable Composition The lower limit of the content of component B is more than 0 part by weight, preferably 0.01 part by weight or more, more preferably 0.03 part by weight or more, and even more preferably 0.05 part 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 0.5 parts by weight or less, preferably 0.3 parts by weight or less, and more preferably 0.1 parts by weight or less, relative to 100 parts by weight of the content of component A.

[0080] 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, and even more preferably 0.01 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 C is preferably 0.1 parts by weight or less, and more preferably 0.08 parts by weight or less, based on 100 parts by weight of the content of component A.

[0081] The lower limit of the content of component D is preferably 0.001 parts by weight or more, and more preferably 0.005 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 D is preferably 0.1 parts by weight or less, more preferably 0.08 parts by weight or less, and even more preferably 0.05 parts by weight or less, based on 100 parts by weight of the content of component A.

[0082] The lower limit of the content of component D is preferably 0.001 parts by weight or more, and more preferably 0.005 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 D is preferably 0.1 parts by weight or less, more preferably 0.08 parts by weight or less, and even more preferably 0.05 parts by weight or less, based on 100 parts by weight of the content of component A.

[0083] In the curable composition, the lower limit of the content of the curing catalyst is preferably 0.1 parts by weight or more, and more preferably 0.5 parts by weight or more, based on 100 parts by weight of the content of component A. The upper limit of the content of the curing catalyst is preferably 5 parts by weight or less, and more preferably 3 parts by weight or less, based on 100 parts by weight of the content of component A.

[0084] 3. Form of the curable composition The curable composition containing components A to C and a curing catalyst may be a one-component type or a multi-component type. A one-component type curable composition is one in which all the components are mixed in advance and then sealed and stored. A one-component type curable composition is cured by moisture in the environment after use. In a multi-component type curable composition, the curing catalyst and the other components are prepared separately, and the two are mixed at the time of use. A multi-component type curable composition may contain other optional agents (such as a colorant) in addition to the above components.

[0085] When the curable composition is prepared as a multi-component type, a colorant can be further added when mixing the respective components. The colorant is preferably a paste obtained by mixing, for example, a pigment, a plasticizer, and, if necessary, a filler, from the viewpoint of workability.

[0086] In addition, for multi-component curable compositions, a retarder can be added when mixing the base agent and the curing agent, allowing fine adjustment of the curing speed at the work site.

[0087] [4. Cured product] A cured product can be obtained from the above-mentioned curable composition by a known method. For example, the above-mentioned curable composition can absorb moisture in the surroundings and spontaneously change into a cured product. The use of the cured product is not particularly limited. Examples include architectural and industrial sealants, electrical and electronic component materials (such as solar cell back sealants), electrical insulating materials (such as insulating coating materials for electric wires and cables), pressure sensitive adhesives, adhesives, elastic adhesives, contact adhesives, tile adhesives, paints, coating materials, sealing materials for can lids, etc., potting agents for electrical and electronic use, films, gaskets, casting materials, various molding materials, artificial marble, rust-proofing and waterproofing sealants for cut parts of wire-reinforced glass or laminated glass, and waterproofing agents.

[0088] In one embodiment, the cured product is in the form of a film. The lower limit of the thickness of the film produced may be 0.1 mm or more, 0.5 mm or more, 1 mm or more, 5 mm or more, or 10 mm or more. The upper limit of the thickness of the film produced may be 100 mm or less, 90 mm or less, 80 mm or less, 70 mm or less, 60 mm or less, or 50 mm or less.

[0089] The film-like cured product can be produced, for example, by applying the curable composition to a substrate and then curing it. The film may be used in a state where it is peeled off from the substrate, or in a state where the substrate and the film are integrated. Examples of applications of the film-like cured product include sealing materials, coating agents, and adhesives.

[0090] [5. Summary] <1> A resin composition comprising the following components A to C: Component A: a (meth)acrylic polymer having a silyl group; Component B: Hydrocarbons having a carbon-carbon double bond in the molecule; Component C: Radical generator; A resin composition, wherein the content of the component B is more than 0 part by weight and 0.5 part by weight or less when the content of the component A is 100 parts by weight: Here, the component A is The molecule has an XY diblock structure having an X block and a Y block, or an XYX triblock structure, The number of repeating units derived from the silyl group-containing (meth)acrylic acid ester monomer contained in the X block is more than 2.0 on average, the content of repeating units derived from silyl group-containing (meth)acrylic acid ester monomers contained in the Y block is 0% by weight or more and less than 5% by weight based on the weight of all repeating units contained in the Y block, The molecular weight distribution (Mw / Mn) is 1.8 or less. <2> The above component A is CH2=C(R 1 )COOR 2 (In the formula, R 1 is a hydrogen atom or a methyl group, and R 2 is a group having 9 or more carbon atoms), <1> The resin composition according to claim 1. <3> The number average molecular weight of the component A is 2,000 to 50,000. <1> or <2> The resin composition according to claim 1. <4> The component B is an α-olefin. <1> ~ <3> The resin composition according to any one of the preceding claims. <5> The α-olefin has 4 or more carbon atoms. <4> The resin composition according to claim 1. <6> The component C is an organic peroxide. <1> ~ <5> The resin composition according to any one of the preceding claims. <7> The composition further contains the following component D: <1> ~ <6> The resin composition according to any one of the preceding claims: Component D: Reducing agent. <8> The component D is an amine. <7> The resin composition according to claim 1. <9> The following component E is further contained. <1> ~ <8> The resin composition according to any one of the preceding claims: Component E: One or more plasticizers selected from the group consisting of ether-based plasticizers, ester-based plasticizers, and ether ester-based plasticizers. <10> <1> ~ <9> 2. A curable composition comprising the resin composition according to claim 1 and a curing catalyst. <11> <10> A cured product obtained by curing the curable composition described in 1. EXAMPLES

[0091] [Measurement method] [Number average molecular weight] The following device was used to measure the number average molecular weight. The measured value is a polystyrene-equivalent molecular weight. Liquid delivery system: HLC-8120GPC (Tosoh Corporation) Column: TSK-GEL H type (Tosoh Corporation) Solvent: THF

[0092] [Terminal silyl group introduction rate] 1 The introduction rate of terminal silyl groups was calculated from the results of H-NMR measurement. 1 The following equipment was used for H-NMR measurements. Measuring instrument: JNM-LA400 (manufactured by JEOL Ltd.) Solvent: CDCl3

[0093] [Measurement of optical properties of resin composition] The prepared resin composition was poured into a glass cell (width: 45 mm × height: 45 mm, optical path length: 10 mm) as a measurement container, while being careful not to introduce bubbles. The haze was measured using a haze meter (HZ-V3, Suga Test Instruments Co., Ltd.). A D65 light source was used as the light source. In addition, the hue in the L*a*b* color space was measured using a spectrometer (SC-P, Suga Test Instruments Co., Ltd.).

[0094] [Viscosity of resin composition] The viscosity of the prepared resin composition was measured using an E-type viscometer (VICOMETER TV-25 type H, Toki Sangyo Co., Ltd.) at a temperature of 23°C.

[0095] 〔material〕 The materials used in the examples and comparative examples are as follows. Ingredient A (Meth)acrylic polymer (A) having a silyl group obtained in the production example ●Ingredient B Hydrocarbons with carbon-carbon double bonds in the molecule (1-decene, Tokyo Chemical Industry Co., Ltd.) ●Component C Radical generator (Perbutyl O, NOF Corporation, t-butylperoxy-2-ethylhexanoate) ●Component D Reducing agent (toluidine, Tokyo Chemical Industry Co., Ltd.) ●Ingredient E Plasticizer (P-0803N, NOF Corporation, ether-based plasticizer)

[0096] [Production Example: Synthesis of (Meth)acrylic Polymer (A)] A (meth)acrylic polymer (A) having a silyl group was synthesized according to the following procedure. (preparation) 1. A 2000 mL three-neck flask was prepared. 108 g of ethyl acrylate, 707 g of n-butyl acrylate, and 186 g of octadecyl acrylate were charged into the flask and mixed. This mixture is referred to as "(meth)acrylic acid ester monomer mixture." 2. Another stirring vessel was prepared. 52.7 mg of cupric bromide (CuBr2), 54.4 mg of hexamethyltris(2-aminoethyl)amine (Me6TREN) and 1.82 g of methanol were charged into the stirring vessel and stirred under a nitrogen stream until a homogeneous solution was obtained. This homogeneous solution is referred to as the "copper solution." The amount of copper contained in the copper solution was equivalent to 15 ppm relative to the total amount of the (meth)acrylic acid ester monomer mixture. 3. Another stirring vessel was prepared. 30.8 mL of methanol, 1.0 g of ascorbic acid, and 1.6 mL of triethylamine were charged into the stirring vessel and stirred under a nitrogen stream to obtain a homogeneous solution. This homogeneous solution is called "ascorbic acid solution." (1st step) 4. 5.60g of ethyl α-bromobutyrate (initiator; 0.029 mol), 20% by weight of the total amount of (meth)acrylic acid ester monomer mixture, 10g of 3-methacryloxypropylmethyldimethoxysilane (0.045 mol; 1.5 molar equivalent to the initiator), 107.68g of methanol, and the total amount of copper solution were added to the stirrer, and stirred for 30 minutes under a nitrogen stream to obtain a homogeneous solution. The stirrer used at this time was a stirrer with a jacket temperature control, and the jacket temperature was set to 45°C. 5. When the temperature in the polymerization system reached 40°C or higher, the ascorbic acid solution was continuously dripped to start the polymerization reaction. The dripping rate of the ascorbic acid solution was set to a rate at which 144 mg of ascorbic acid was added to the polymerization system per hour. 6. The temperature in the polymerization system was monitored and it rose as soon as the dropping of ascorbic acid started, reached a maximum temperature, and then gradually decreased. When the temperature difference between the temperature in the polymerization system and the jacket temperature reached 1°C, a small amount of the reaction solution in the polymerization system was sampled and analyzed by gas chromatography. As a result, 90% by weight of the (meth)acrylic acid ester monomer mixture initially charged had been consumed. (2nd process) 7. The remaining (meth)acrylic acid ester monomer mixture that was not added in the first step (80% by weight of the total amount) was continuously added dropwise to the polymerization system over a period of 90 minutes. The ascorbic acid solution was added dropwise at a rate of 48 mg of ascorbic acid per hour to the polymerization system. Sampling was also carried out sequentially and analyzed by gas chromatography. The polymerization was continued until 88% by weight of the total (meth)acrylic acid ester monomer mixture added to the polymerization system was consumed. (3rd step) 8. 11 g of 3-methacryloxypropylmethyldimethoxysilane (0.049 mol; 1.6 molar equivalents relative to the initiator) was added to the polymerization system. The ascorbic acid solution was continuously added dropwise until 98% by weight of the total amount of the (meth)acrylic acid ester monomer mixture added to the polymerization system was consumed. Thereafter, the addition of the ascorbic acid solution was stopped to terminate the polymerization. 9. The jacket temperature was changed to 80°C, and the solvent was then volatilized. A diaphragm pump was used first, and then a vacuum pump was used. After volatilization was completed, the jacket temperature was cooled to 60°C or less. (purification) 10. 1000g of butyl acetate was added to a jacket temperature-controlled stirring device and mixed with the polymer after devolatilization until a homogeneous solution was obtained. An adsorbent was added to this homogeneous solution and stirred for 1 hour. As the adsorbent, 10g of Kyoward 500SH (Kyowa Chemical Industry Co., Ltd.) and 10g of Kyoward 700SEN-S (Kyowa Chemical Industry Co., Ltd.) were used. 11. After the stirring was completed, the mixture was filtered through a filter equipped with a bag filter cloth. This resulted in a clear polymer solution. 1.5 g of an antioxidant (Sumilizer GS; Sumitomo Chemical Co., Ltd.) was added to the solution and mixed until homogenous. Thereafter, the solvent was removed from the solution using a diaphragm pump first and then a vacuum pump. In this manner, a (meth)acrylic copolymer (A) was obtained.

[0097] The (meth)acrylic copolymer (A) was an XYX type block copolymer, with a number average molecular weight of 5,5000, a molecular weight distribution of 1.11, and a number of silyl groups introduced per molecule of 2.1. The X block of the (meth)acrylic copolymer (A) had an average of 2.1 repeating units derived from silyl group-containing (meth)acrylic acid ester monomers per copolymer molecule. The Y block of the (meth)acrylic copolymer (A) had 1.1% by weight of repeating units derived from silyl group-containing (meth)acrylic acid ester monomers (based on the weight of all repeating units contained in the Y block). The repeating units derived from silyl group-containing (meth)acrylic acid ester monomers contained in the Y block were extremely small. Therefore, when calculated with two significant digits, the repeating units derived from silyl group-containing (meth)acrylic acid ester monomers contained in the entire molecule and the repeating units derived from silyl group-containing (meth)acrylic acid ester monomers contained in the entire X block were both 2.1.

[0098] [Examples 1 to 5, Comparative Example] A sample for evaluating physical properties was prepared according to the following procedure. 1. Prepare each ingredient in the amount (unit: g) shown in Table 1. 2. Components A, B, C, D, and E were placed in a 150cc plastic cup in this order and stirred with a spoon. 3. Using a planetary stirring / defoaming device (ARE-310, Thinky Corporation), the mixture was stirred (1600 rpm×90 seconds) and degassed (2200 rpm×300 seconds) to obtain a resin composition. 5. The obtained resin composition was left to stand and cured under one of the following standing conditions. In this way, a resin composition was obtained (this resin composition was not cured but was in a liquid state). Condition A: Leave at 80℃ for 1 hour Condition B: Leave at room temperature for 24 hours

[0099] 〔result〕 The results are shown in Table 1. [Table 1]

[0100] As can be seen from Table 1, the resin composition according to the embodiment containing component B and component C has a lower haze than the resin composition according to the comparative example not containing these components. In fact, even when visually confirmed, the resin composition according to the embodiment had reduced cloudiness. Furthermore, the inclusion of component B and component C did not cause a significant change in the viscosity of the resin composition, and the viscosity was equivalent to that of the prior art. This result suggests that the resin composition according to one embodiment of the present invention can be used as a highly transparent curable composition.

[0101] As can be seen from the results of Example 4, the transparency of the resin composition is further improved by including Component E. As can be seen from the results of Example 5, if a redox initiator system is formed by including both Component C and Component D, the haze can be reduced even when aged at room temperature. [Industrial Applicability]

[0102] The resin composition according to one embodiment of the present invention has excellent transparency. Therefore, when applied to a curable composition, the resin composition can be suitably used as a clear coating film or a sealing material with excellent appearance.

Claims

1. A resin composition comprising the following components A to C: Component A: a (meth)acrylic polymer having a silyl group; Component B: a hydrocarbon having a carbon-carbon double bond in the molecule; Component C: radical generator; A resin composition, in which the content of the component B is more than 0 part by weight and 0.5 part by weight or less when the content of the component A is 100 parts by weight: Here, the component A is The molecule has an XY diblock structure having an X block and a Y block or an XYX triblock structure, the number of repeating units derived from the silyl group-containing (meth)acrylic acid ester monomer contained in the X block is more than 2.0 on average, a repeating unit derived from a silyl group-containing (meth)acrylic acid ester monomer contained in the Y block is 0% by weight or more and less than 5% by weight based on the weight of all repeating units contained in the Y block, The molecular weight distribution (Mw / Mn) is 1.8 or less.

2. The above component A is CH ２ = C(R １ ) COOR ２ (In the formula, R １ is a hydrogen atom or a methyl group, R ２ The resin composition according to claim 1 , comprising 1% by weight or more of repeating units derived from

3. The resin composition according to claim 1, wherein the number average molecular weight of the component A is 2,000 to 50,000.

4. The resin composition according to claim 1, wherein the component B is an α-olefin.

5. The resin composition according to claim 4, wherein the α-olefin has 4 or more carbon atoms.

6. The resin composition according to claim 1 , wherein the component C is an organic peroxide.

7. The resin composition according to claim 1, further comprising the following component D: Component D: Reducing agent.

8. The resin composition according to claim 7 , wherein component D is an amine.

9. The resin composition according to claim 1, further comprising the following component E: Component E: one or more plasticizers selected from the group consisting of ether-based plasticizers, ester-based plasticizers, and ether ester-based plasticizers.

10. A curable composition comprising the resin composition according to any one of claims 1 to 9 and a curing catalyst.

11. A cured product obtained by curing the curable composition according to claim 10.

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