Resin composition, curable composition, and cured product

Abstract

To provide a resin composition having high transparency.SOLUTION: A resin composition according to one embodiment of the present invention comprises: component A, a (meth)acrylic polymer having a silyl group; component B, an acid anhydride; and component C, an ether-based plasticizer. Component A is a polymer meeting specific requirements.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: acid anhydride; Component C: Ether plasticizer; 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: an acid anhydride, and component C: an ether-based plasticizer. The resin composition may include, as an optional component, component D: one or more selected from the group consisting of an ester-based plasticizer, an alcohol, and an acid. A composition in which a curing catalyst is further added to the resin composition can be a curable composition. Each of these components may include only one type, or may include two or more types.

[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 the formula: CH 2 =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:

[0030] [Si(R 3 ) 2-b (Y) b O] m -Si(R 4 ) 3-a (Y) a 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 (R') 3 R' is a triorganosiloxy group represented by SiO-. 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: H 2 C=C(R 5 )C(=O)-O-(CH 2 )m -SiR 6 n (OR 7 ) 3-n 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.

[0032] Specific examples of silyl group-containing (meth)acrylic acid ester monomers include 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, and 3-acryloxypropyltrimethoxysilane.

[0033] [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.

[0034] 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".

[0035] 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 measurement is the molecular weight converted into standard polystyrene.

[0036] [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) ·Organoantimony Polymerization Method (SBRP Method) Polymerization method using organobismuth compounds (BIRP method) -Iodine transfer polymerization method

[0037] 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.

[0038] [1.2.Component B: Acid anhydride] Component B is an acid anhydride. An acid anhydride is a compound formed by dehydration condensation of two carboxylic acids. In one embodiment, the acid anhydride is a compound formed by dehydration condensation of two oxo acids contained in the same molecule.

[0039] Examples of component B include acetic anhydride, propionic anhydride, benzoic anhydride, oxalic anhydride, succinic anhydride, maleic anhydride, phthalic anhydride, and itaconic anhydride. Component B may be a compound in which one or more substituents are added to the above-mentioned compounds. The substituent may have, for example, 40 or less, 30 or less, 20 or less, or 10 or less carbon atoms. The substituent may have 5 or less, 4 or less, 3 or less, 2 or less, or 1 or less heteroatoms (oxygen atom, nitrogen atom, sulfur atom, phosphorus atom, silicon atom, halogen atom, etc.). In one embodiment, the substituent consists of only carbon atoms and hydrogen atoms. Examples of component B having a substituent include octenylsuccinic anhydride and 2,3-dimethylmaleic anhydride.

[0040] [1.3. Component C: Ether-based plasticizers] Component C is an ether-based plasticizer. Examples of Component C include triethylene glycol 2-ethyl butyrate, diethylene glycol dibutyl ether, and tetraethylene glycol dimethyl ether.

[0041] [1.4. Component D: one or more selected from the group consisting of ester-based plasticizers, alcohols, and acids] Component D is one or more selected from the group consisting of ester-based plasticizers, alcohols, and acids. Component D can replace a part of component C. Component C tends to be relatively expensive, with only a few varieties of products available on the market. Therefore, by reducing the amount of component C and substituting it with component D, the raw material cost of the resin composition can be reduced.

[0042] Examples of ester-based plasticizers include phthalate esters (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 acetylricinoleate, 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.

[0043] The alcohol may be a monohydric alcohol or a polyhydric alcohol having dihydric or higher hydricity. In one embodiment, the alcohol is a dihydric or trihydric alcohol. In one embodiment, the number of carbon atoms in the alcohol is 4 to 10. Examples of preferred alcohols include 1,3-butanediol, ethylene glycol, propylene glycol, and glycerin.

[0044] The acid may be a monovalent acid or a divalent or higher polyvalent acid. In one embodiment, the acid is a carboxylic acid. In one embodiment, the acid is a liquid acid (particularly, a liquid carboxylic acid). In one embodiment, the acid has 2 to 10 carbon atoms. Examples of preferred acids include neodecanoic acid, 2-ethylhexanoic acid, caproic acid, and linolenic acid.

[0045] [1.5.Curing catalyst] The resin composition may contain a curing catalyst. The resin composition containing the curing catalyst can function as a curable composition.

[0046] 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).

[0047] 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.

[0048] [1.6. 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.

[0049] (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.

[0050] 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.

[0051] 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.

[0052] (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.).

[0053] 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.

[0054] (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.

[0055] 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.

[0056] 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.

[0057] (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.

[0058] Examples of the thixotropic agent include polyamide waxes; hydrogenated castor oil derivatives; and metal soaps (calcium stearate, aluminum stearate, barium stearate, etc.).

[0059] 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.

[0060] (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.

[0061] 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.

[0062] 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.

[0063] (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.

[0064] 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.

[0065] 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.

[0066] 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.).

[0067] 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.

[0068] 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.

[0069] 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).

[0070] 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.

[0071] 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.

[0072] 2. Composition of Resin Composition and Curable Composition The lower limit of the content of component B is preferably 0.01 parts by weight or more, more preferably 0.03 parts by weight or more, and even more preferably 0.05 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 B is preferably 1 part by weight or less, more preferably 0.8 parts by weight or less, and even more preferably 0.5 parts by weight or less, based on 100 parts by weight of the content of component A.

[0073] The lower limit of the content of component C is preferably 0.1 parts by weight or more, more preferably 0.3 parts by weight or more, and even 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 component C is preferably 10 parts by weight or less, more preferably 8 parts by weight or less, even more preferably 5 parts by weight or less, particularly preferably 3 parts by weight or less, and even more preferably 2 parts by weight or less, based on 100 parts by weight of the content of component A.

[0074] The lower limit of the content of component D is preferably 0.1 parts by weight or more, more preferably 0.3 parts by weight or more, and even 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 component D is preferably 10 parts by weight or less, more preferably 8 parts by weight or less, even more preferably 5 parts by weight or less, and particularly preferably 3 parts by weight or less, based on 100 parts by weight of the content of component A.

[0075] The lower limit of the total content of component C and component D is preferably 0.1 parts by weight or more, more preferably 0.5 parts by weight or more, and even more preferably 1 part by weight or more, when the content of component A is 100 parts by weight. The upper limit of the total content of component C and component D is preferably 20 parts by weight or less, more preferably 10 parts by weight or less, even more preferably 8 parts by weight or less, particularly preferably 5 parts by weight or less, and even more preferably 3 parts by weight or less. If the total content of component C and component D is within the above range, the same degree of transparency as that of a resin composition containing only component C can be achieved.

[0076] When the resin composition contains component D, the lower limit of the proportion of component D in the total content of components C and D is preferably 20% by weight or more, and more preferably 30% by weight or more. When the resin composition contains component D, the upper limit of the proportion of component D in the total content of components C and D is preferably 80% by weight or less, and more preferably 70% by weight or less. If the proportion of component D is within the above range, transparency equivalent to that of a resin composition containing only component C can be achieved.

[0077] 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.

[0078] 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.

[0079] 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.

[0080] 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.

[0081] [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.

[0082] 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.

[0083] 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.

[0084] [5. Summary] The present invention includes the following aspects. <1> A resin composition comprising the following components A to C: Component A: a (meth)acrylic polymer having a silyl group; Component B: acid anhydride; Component C: Ether plasticizer; 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 CH 2 =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 tree described in <4> The composition further contains the following component D: <1> ~ <3> The resin composition according to any one of the preceding claims: Component D: one or more selected from the group consisting of ester-based plasticizers, alcohols, and acids. <5> The contents of the above-mentioned components B and C are as follows, assuming that the content of the above-mentioned component A is 100 parts by weight: <1> ~ <4> The resin composition according to any one of the preceding claims: Component B: 1 part by weight or less; Component C: 10 parts by weight or less. <6> The contents of the above-mentioned components C and D are as follows, assuming that the content of the above-mentioned component A is 100 parts by weight: <4> A resin composition according to claim 1, Component C: less than 3 parts by weight; Component D: 10 parts by weight or less. <7> <1> ~ <6> 2. A curable composition comprising the resin composition according to claim 1 and a curing catalyst. <8> <7> A cured product obtained by curing the curable composition described in 1. EXAMPLES

[0085] [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

[0086] [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 (JEOL Ltd.) Solvent: CDCl 3

[0087] [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, taking care not to introduce bubbles. 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, hue in the L*a*b* color space was measured using a spectrometer (SC-P, Suga Test Instruments Co., Ltd.).

[0088] [Tensile properties of cured product] Cured products were produced from the resin compositions prepared in the Examples and Comparative Examples according to the following procedures. 1. A curing catalyst (Neostan U-220H, Nitto Kasei Co., Ltd., dibutyltin), a dehydrating agent (Silquest A-171, Momentive Performance Materials, vinyltrimethoxysilane), and an adhesion promoter (KBM-603, Shin-Etsu Chemical Co., Ltd., N-2-(aminoethyl)-3-aminopropyltrimethoxysilane) were added to the resin composition and stirred with a spoon. 2. 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 curable composition. 3. The obtained curable composition was cured under conditions of 23°C and 50% RH to obtain a cured product. 4. In accordance with JIS K 6251, No. 3 dumbbell-shaped test pieces were obtained from the cured product and the tensile properties were measured. The tensile properties were measured at 23°C and 55% RH using an autograph. The evaluation items were the stress at 100% elongation, the stress at break, and the elongation at break.

[0089] [Tear strength of cured product] A crescent-shaped test piece was obtained from the cured product prepared as described above, and the tear strength was measured in accordance with JIS K 6252. The tear strength was measured using an autograph at 23°C and 55% RH.

[0090] [Transparency of the cured product] The transparency of the cured product (thickness: 2 mm) prepared as described above was visually confirmed. The evaluation criteria were as follows: +: No visible cloudiness. -: There is cloudiness that can be seen with the naked eye.

[0091] 〔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 · Acid anhydride (Octenylsuccinic anhydride) ●Component C Ether plasticizer (P-0803N, NOF Corporation) ●Component D Ester plasticizer (dioctyl adipate) Alcohol (1,3-butanediol) Acid (neodecanoic acid)

[0092] [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. Prepare another stirring vessel. Add 52.7 mg of copper(II) bromide (CuBr 2 ), 54.4 mg of hexamethyltris(2-aminoethyl)amine (Me 6 TREN) and 1.82 g of methanol were charged in a stirring vessel and stirred under a nitrogen gas flow until a homogeneous solution was obtained. This homogeneous solution is referred to as the "copper solution." The 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 (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 jacket temperature-adjustable stirrer, 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 stirrer 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 way, a (meth)acrylic copolymer (A) was obtained.

[0093] 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.

[0094] [Examples 1 to 3] 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. Each ingredient was placed in a 150cc plastic cup 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. 4. The obtained resin composition was left to stand for 1 hour at 50° C. to cure. In this way, a resin composition was obtained (this resin composition was not cured but was in a liquid state).

[0095] Comparative Example A resin composition consisting of component A alone was used.

[0096] 〔result〕 The results are shown in Table 1. [Table 1]

[0097] As can be seen from Table 1, the resin compositions according to the examples had lower haze than the resin compositions according to the comparative examples that did not contain these components. In fact, no turbidity was observed with the naked eye in the resin compositions according to the examples. This result was the same for the cured products made from the resin compositions. On the other hand, turbidity was observed in the resin compositions according to the comparative examples, and the turbidity remained even in the cured products.

[0098] The inclusion of components B and C did not result in any significant changes in the tensile properties and tear strength of the cured product, and the values ​​were equivalent to those of the prior art.

[0099] As can be seen from the results of Examples 2 to 4, even when a part of Component C was replaced with Component D, the transparency of the resin composition was maintained (generally, if the haze is less than about 5%, it appears transparent to the naked eye). Therefore, there was a possibility of reducing the raw material cost by replacing a part of Component C with Component D. [Industrial Applicability]

[0100] 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: acid anhydride; Component C: ether-based plasticizer; 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, further comprising the following component D: Component D: one or more selected from the group consisting of ester-based plasticizers, alcohols, and acids.

5. The resin composition according to claim 1, wherein the contents of the components B and C are as follows, assuming that the content of the component A is 100 parts by weight: Component B: 1 part by weight or less; Component C: 10 parts by weight or less.

6. The resin composition according to claim 4, wherein the contents of the components C and D are as follows, assuming that the content of the component A is 100 parts by weight: Component C: less than 3 parts by weight; Component D: 10 parts by weight or less.

7. A curable composition comprising the resin composition according to any one of claims 1 to 6 and a curing catalyst.

8. A cured product obtained by curing the curable composition according to claim 7.

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