Hardening components

A curable composition with (meth)acrylic polymer, polyfunctional unsaturated compound, and metal soap addresses adhesion issues with mortar and aluminum, offering odor-free adhesion.

JP2026096099APending Publication Date: 2026-06-12KANEKA CORP

Patent Information

Authority / Receiving Office
JP · JP
Patent Type
Applications
Current Assignee / Owner
KANEKA CORP
Filing Date
2024-12-02
Publication Date
2026-06-12

AI Technical Summary

Technical Problem

Existing sealants do not adhere well to mortar and aluminum, and traditional primer compositions used to improve adhesion contain organic solvents that cause odor issues.

Method used

A curable composition comprising a (meth)acrylic polymer with reactive silicon groups, a polyfunctional unsaturated compound, a metal soap, and a curing catalyst, which adheres well to various substrates like mortar and aluminum while minimizing solvent odors.

🎯Benefits of technology

The composition effectively adheres to mortar and aluminum while suppressing solvent odors, providing a suitable primer solution.

✦ Generated by Eureka AI based on patent content.

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Abstract

To provide a curable composition that adheres well to various substrates, particularly mortar and aluminum, while suppressing odors derived from organic solvents, making it suitable for use as a primer. [Solution] A curable composition comprising a (meth)acrylic polymer (A) having reactive silicon groups, a polyfunctional unsaturated compound (B), a metal soap (C), and a curing catalyst (D), wherein the (meth)acrylic polymer contains constituent units derived from (meth)acrylic acid ester, the polyfunctional unsaturated compound (B) is a compound having two or more allyl groups, and the metal soap (C) is a metal carboxylate salt and / or a metal sulfonic acid salt.
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Description

[Technical Field] 【0001】 The present invention relates to a curable composition comprising a (meth)acrylic polymer (A) having reactive silicon groups, a polyfunctional unsaturated compound (B), a metal soap (C), and a curing catalyst (D). [Background technology] 【0002】 Traditionally, sealants have been frequently applied to joints and other areas in various buildings. Mortar and aluminum are widely used as building materials, but when the material of the area where the sealant is applied is mortar or aluminum, the sealant often does not adhere well to the mortar or aluminum. Therefore, when applying sealant to mortar or aluminum, a primer composition may be applied to the mortar or aluminum before applying the sealant. 【0003】 As such a primer composition, for example, a primer composition comprising an alkoxysilane and / or a partial hydrolysate thereof, a compound obtained by adding an organosilicon compound of a specific structure to an unsaturated hydrocarbon compound having two or more unsaturated groups, a titanate ester, and an organic solvent has been proposed (see Patent Document 1). [Prior art documents] [Patent Documents] 【0004】 [Patent Document 1] Japanese Patent Application Publication No. 04-300961 [Overview of the Initiative] [Problems that the invention aims to solve] 【0005】 However, while the primer composition described in Patent Document 1 adheres well to mortar and the like, it has problems such as odor due to the inclusion of organic solvents. 【0006】 The present invention has been made in view of the above problems, and aims to provide a curable composition that can be suitably used as a primer, which adheres well to various substrates, particularly mortar and aluminum, while suppressing odors derived from organic solvents. [Means for solving the problem] 【0007】 The present inventors have found that the above problems can be solved by using a curable composition comprising a (meth)acrylic polymer (A) having a reactive silicon group, a polyfunctional unsaturated compound (B), a metal soap (C), and a curing catalyst (D), by using a (meth)acrylic polymer containing constituent units derived from (meth)acrylic acid ester, a compound having two or more allyl groups as the polyfunctional unsaturated compound (B), and a metal carboxylate salt and / or a metal sulfonic acid salt as the metal soap (C), and have completed the present invention. 【0008】 More specifically, the present invention provides the following (1) to (7). (1) comprising a (meth)acrylic polymer having reactive silicon groups (A), a polyfunctional unsaturated compound (B), a metal soap (C), and a curing catalyst (D), The reactive silicon group is represented by the following formula (1): -SiR 1 a X 3-a (1) (In formula (1), R 1 is a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, or R 0 It is a triorganosiloxy group represented as 3SiO-, and R 0 (where is a hydrocarbon group having 1 to 20 carbon atoms, X is a hydroxyl group or a hydrolyzable group, and a is 0, 1, or 2.) It is a base represented by, The molecular chain of the (meth)acrylic polymer (A) contains constituent units derived from (meth)acrylic acid ester. The polyfunctional unsaturated compound (B) is a compound having two or more allyl groups, A curable composition in which the metal soap (C) is a metal carboxylate and / or a metal sulfonate. (2) The number average molecular weight of the (meth)acrylic polymer (A) is from 3,000 to 60,000, The curable composition according to (1), wherein the weight average molecular weight of the (meth)acrylic polymer (A) is from 6,000 to 180,000. (3) In formula (1), a is 0, the curable composition according to (1) or (2). (4) The curable composition according to any one of (1) to (3), wherein the metal soap (C) is a metal carboxylate. (5) The curable composition according to any one of (1) to (4), wherein the amount of the (meth)acrylic polymer (A) in 100 parts by weight of the curable composition is from 1 to 30 parts by weight. (6) The curable composition according to any one of (1) to (5), which is used as a primer. (7) The curable composition according to (6), which is used as a primer for mortar or aluminum. 【Advantages of the Invention】 【0009】 According to the present invention, it is possible to provide a curable composition that can be suitably used as a primer, which adheres well to various substrates, particularly mortar and aluminum, while suppressing the odor derived from organic solvents. 【Embodiments for Carrying Out the Invention】 【0010】 Hereinafter, the present invention will be described in detail. 【0011】 ≪Curable Composition≫ The curable composition contains a (meth)acrylic polymer (A) having a reactive silicon group, a polyfunctional unsaturated compound (B), a metal soap (C), and a curing catalyst (D). The molecular chain of the (meth)acrylic polymer (A) contains a structural unit derived from an alkyl (meth)acrylate. The polyfunctional unsaturated compound (B) is a compound having two or more allyl groups. The metal soap (C) is a metal carboxylate and / or a metal sulfonate. The curable composition may contain various other additives as necessary. 【0012】 The above curable composition adheres well to various substrates, particularly mortar and aluminum, while suppressing the odor derived from organic solvents. 【0013】 Hereinafter, the essential or optional components that the curable composition may contain will be described. 【0014】 <(Meth)acrylic polymer (A)> (The (meth)acrylic polymer (A) (hereinafter, may be simply referred to as "polymer (A)") has a reactive silicon group at the end of the molecular chain. The polymer (A) has a polymer skeleton and polymer chain ends bonded to the polymer skeleton. The polymer skeleton is a structure in which a plurality of structural units derived from monomers are continuously bonded. The monomers may be of one type or multiple types. 【0015】 The polymer chain end is a site located at the end of the polymer (B). The number of polymer chain ends of the polymer (A) is 2 when the main chain structure is linear, and 3 or more when the polymer skeleton is branched. When the polymer (A) is a mixture of a polymer having a linear main chain structure and a polymer having a branched main chain structure, the number of polymer chain ends is a numerical value between 2 and 3 as an average value. 【0016】 (Reactive silicon group) The reactive silicon group is a group capable of generating a silanol group by hydrolysis. When the reactive silicon group generates a silanol group, the polymer (A) is crosslinked by the condensation reaction between silanol groups. 【0017】 The reactive silicon group is a group represented by the following formula (1). -SiR 1 a X 3-a (1) In formula (1), R1 is a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, or R 0 It is a triorganosiloxy group represented as 3SiO-. In the triorganosiloxy group, there are three R 0 These are hydrocarbon groups with 1 to 20 carbon atoms. 0 They may be the same or they may be different. X is a hydroxyl group or a hydrolyzable group. a is 0, 1, or 2. R 1 For each of , and X, if there are multiple of them, then multiple R 1 , and multiple X's, may be the same or different. 【0018】 R in equation (1) 1 Specific examples include alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-hexyl, 2-ethylhexyl, and n-dodecyl; unsaturated hydrocarbon groups such as vinyl, isopropenyl, and allyl; alkoxymethyl groups such as methoxymethyl; halogenated methyl groups such as chloromethyl; cycloalkyl groups such as cyclohexyl; aryl groups such as phenyl, toluyl, and 1-naphthyl; and aralkyl groups such as benzyl. Among these groups, alkyl groups and aryl groups are preferred, methyl, ethyl, and phenyl groups are more preferred, methyl and ethyl groups are even more preferred, and methyl groups are particularly preferred. 1 If multiple R 1 These may be the same group, or a combination of two or more different groups. 【0019】 In formula (1), X is a hydroxyl group or a hydrolyzable group. The hydrolyzable group is not particularly limited and may be any known hydrolyzable group. Specific examples of hydrolyzable groups include hydrogen atoms, halogen atoms, alkoxy groups, acyloxy groups, ketoximate groups, amino groups, amide groups, acid amide groups, aminooxy groups, mercapto groups, and alkenyloxy groups. Among these, alkoxy groups, acyloxy groups, ketoximate groups, and alkenyloxy groups are preferred, and alkoxy groups such as methoxy groups and ethoxy groups are more preferred because they are mildly hydrolyzable and easy to handle. Methoxy groups are preferred because they allow for easy adjustment of the curability of the curable composition. 【0020】 The reactive silicon group represented by formula (1) is not particularly limited. Specific examples of the reactive silicon group represented by formula (1) include dimethoxymethylsilyl group, diethoxymethylsilyl group, trimethoxysilyl group, triethoxysilyl group, dimethoxyphenylsilyl group, methoxymethyldimethoxysilyl group, methoxymethyldiethoxysilyl group, triisopropenyloxysilyl group, and triacetoxysilyl group. Among these, the dimethoxymethylsilyl group and the trimethoxysilyl group are preferred because they facilitate the synthesis of polymer (A). The trimethoxysilyl group and the methoxymethyldimethoxysilyl group are preferred because they exhibit excellent curability. The dimethoxymethylsilyl group is particularly preferred because of its excellent stability. 【0021】 Reactive silicon groups can be present in the polymer backbone and at the polymer chain ends. Furthermore, two or more reactive silicon groups may be present at the polymer chain ends. When using a curable composition in adhesives, sealants, elastic coatings, or other adhesives, it is preferable that the reactive silicon groups in polymer (A) are present at the polymer chain ends. 【0022】 (Regarding the main chain structure of polymer (A)) Polymer (A) contains constituent units derived from alkyl (meth)acrylate. Polymer (A) may also contain constituent units derived from two or more alkyl (meth)acrylates. (Meth)acrylate alkyl ester means alkyl acrylate and / or alkyl methacrylate. Specific examples of alkyl acrylates include methyl acrylate, ethyl acrylate, n-propyl acrylate, n-butyl acrylate, isobutyl acrylate, tert-butyl acrylate, n-hexyl acrylate, 2-ethylhexyl acrylate, n-decyl acrylate, n-undecyl acrylate, lauryl acrylate, n-tridecyl acrylate, myristyl acrylate, cetyl acrylate, and stearyl acrylate, behenyl acrylate, and others. 【0023】 Specific examples of alkyl methacrylates include methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, tert-butyl methacrylate, n-hexyl methacrylate, 2-ethylhexyl methacrylate, n-decyl methacrylate, n-undecyl methacrylate, lauryl methacrylate, n-tridecyl methacrylate, myristyl methacrylate, cetyl methacrylate, stearyl methacrylate, and behenyl methacrylate. 【0024】 The ratio of the weight of constituent units derived from alkyl (meth)acrylate to the weight of polymer (A) is preferably 50% by weight or more, more preferably 70% by weight or more, and even more preferably 90% by weight or more. 【0025】 From the viewpoint of the stability of polymer (A), alkyl (meth)acrylate esters having an alkyl group with 1 to 30 carbon atoms are preferred as monomers for preparing polymer (A). 【0026】 Alkyl (meth)acrylate esters having an alkyl group with 1 to 30 carbon atoms are defined by the following formula (A1): CH2=CR a1 COOR a2 (A1) (In formula (A1), R a1 R is a hydrogen atom or a methyl group. ba(These are alkyl groups with 1 to 30 carbon atoms.) It is represented as follows. 【0027】 In equation (A1), R a2 Examples include alkyl groups having 1 to 30 carbon atoms, such as methyl group, ethyl group, n-propyl group, n-butyl group, tert-butyl group, 2-ethylhexyl group, lauryl group, n-tridecyl group, cetyl group, and stearyl group. R a2 The number of carbon atoms in the alkyl group is more preferably 1 to 20. 【0028】 The monomers used to produce polymer (A) may include monomers other than alkyl (meth)acrylate. Other monomers include acrylic acid and methacrylic acid; (meth)acrylamides such as acrylamide, methacrylamide, N-methylolacrylamide, and N-methylolmethacrylamide; epoxy group-containing (meth)acrylic acid esters such as glycidyl acrylate and glycidyl methacrylate; amino group-containing unsaturated compounds such as 2-(N,N-diethylamino)ethyl methacrylate and 2-aminoethyl vinyl ether; acrylonitrile and methacrylonitrile; styrenes such as styrene and α-methylstyrene; alkyl vinyl ethers; vinyl chloride; fatty acid vinyl esters such as vinyl acetate and vinyl propionate. 【0029】 The number-average molecular weight (Mn) of polymer (A) is not particularly limited. The number-average molecular weight of polymer (B), as polystyrene-equivalent molecular weight in GPC, is preferably 3,000 to 60,000, and more preferably 3,500 to 50,000. The weight-average molecular weight (Mw) of polymer (A), expressed as polystyrene-based molecular weight in GPC, is preferably 6,000 to 180,000, and more preferably 7,000 to 160,000. With respect to polymer (A), it is particularly preferable that the number-average molecular weight is 3,000 to 60,000 and the weight-average molecular weight is 6,000 to 180,000. 【0030】 The molecular weight distribution (Mw / Mn) of polymer (A) is not particularly limited. A narrow molecular weight distribution of polymer (A) is preferred. Specifically, the molecular weight distribution is preferably 3.0 or less, more preferably 1.4 or less, even more preferably 2.7 or less, and particularly preferably 2.3 or less. The molecular weight distribution of polymer (A) can be determined from the number-average molecular weight and weight-average molecular weight obtained by GPC measurement. 【0031】 Polymer (A) can be produced by conventional vinyl polymerization methods. Examples of vinyl polymerization methods include solution polymerization by radical reaction and bulk polymerization. However, vinyl polymerization methods are not limited to these methods. The polymerization reaction described above is typically carried out at 50-150°C in the presence of monomers, radical initiators, chain transfer agents, and solvents. The conditions for the polymerization reaction are not limited to those described above. 【0032】 Specific examples of radical initiators include azobisisobutyronitrile, 2,2'-azobis(2-methylbutyronitrile), and benzoyl peroxide. Specific examples of chain transfer agents include mercaptans such as n-dodecyl mercaptan, tert-dodecyl mercaptan, and lauryl mercaptan, as well as halogen-containing compounds. As solvents, solvents that are inert to polymerization reactions, such as ethers, hydrocarbons, and esters, can preferably be used. 【0033】 Various methods are known for introducing reactive silicon groups into (meth)acrylic polymers. For example, I) A method for copolymerizing a compound having an ethylenically unsaturated double bond and a reactive silicon group with an alkyl (meth)acrylate represented by formula (A1); II) A copolymer obtained by copolymerizing a compound having an ethylenically unsaturated double bond and a reactive functional group (e.g., acrylic acid) with an alkyl (meth)acrylate represented by formula (A1), wherein the reactive functional group is reacted with reactive silicon and a compound capable of reacting with the reactive group (e.g., a reactive silicon group-containing isocyanate compound); III) A method for polymerizing an alkyl (meth)acrylate represented by formula (A1) in the presence of a mercaptan having a reactive silicon group as a chain transfer agent; VI) A method for polymerizing an alkyl (meth)acrylate represented by formula (A1) using an azobisnitrile compound having a reactive silicon group or a disulfide compound having a reactive silicon group as an initiator; and V) A method is used in which a reactive silicon group is introduced at the end of the molecular chain in a polymer obtained by polymerizing an alkyl (meth)acrylate represented by formula (A1) using a living radical polymerization method. The method for introducing reactive silicon groups into (meth)acrylic polymers is not limited to the method described above. 【0034】 The compound having an ethylenically unsaturated double bond and a reactive silicon group used in the method described in I) above is the following formula (A2): CH2=CR a5 COOR a6 -SiR 1 3-a X a (A2) (In formula (A2), R 1 , X, and a are R in equation (1) 1 , X, and a are the same. R a5 R is a hydrogen atom or a methyl group. a6 (This refers to an alkylene group with 1 to 6 carbon atoms.) Compounds represented by are preferred. 【0035】 In equation (A2), R a6The alkylene group is an alkylene group having 1 to 6 carbon atoms, such as a methylene group, an ethane-1,2-diyl group (ethylene group), and a propane-1,3-diyl group (trimethylene group), and preferably an alkylene group having 1 to 4 carbon atoms. 【0036】 Specific examples of compounds having an ethylenically unsaturated double bond and a reactive silicon group include γ-methacryloxypropyl alkoxysilanes such as γ-methacryloxypropyltrimethoxysilane, γ-methacryloxypropylmethyldimethoxysilane, and γ-methacryloxypropyltriethoxysilane; γ-acryloxypropyl alkoxysilanes such as γ-acryloxypropyltrimethoxysilane, γ-acryloxypropylmethyldimethoxysilane, and γ-acryloxypropyltriethoxysilane; and vinyl alkoxysilanes such as vinyltrimethoxysilane, vinylmethyldimethoxysilane, and vinyltriethoxysilane. 【0037】 Examples of reactive functional groups in compounds having an ethylenically unsaturated double bond and a reactive functional group used in method II) above include amino groups, hydroxyl groups, and carboxyl groups. Examples of groups that can react with these reactive functional groups include isocyanate groups. Furthermore, as described in other publications such as Japanese Patent Publication No. 54-36395, Japanese Patent Publication No. 01-272654, and Japanese Patent Publication No. 02-214759, allyl groups can be used as reactive functional groups. Silicon hydride (H-Si) groups can react with allyl groups. 【0038】 Examples of mercaptans containing reactive silicon groups as chain transfer agents used in method III) above include γ-mercaptopropyltrimethoxysilane, γ-mercaptopropylmethyldimethoxysilane, and γ-mercaptopropyltriethoxysilane. 【0039】 Examples of azobisnitrile compounds and disulfide compounds having a reactive silicon group used in the method described in IV) above include azobisnitrile compounds having an alkoxysilyl group and disulfide compounds having an alkoxysilyl group as described in Japanese Patent Publication No. 60-23405 and Japanese Patent Publication No. 62-70405, etc. 【0040】 An example of the method described in (V) above is the method described in Japanese Patent Publication No. 09-272714, etc. 【0041】 Other methods include those described in Japanese Patent Publication No. 59-168014 and Japanese Patent Publication No. 60-228516, which involve the combined use of a mercaptan having a reactive silicon group and a radical polymerization initiator having a reactive silicon group. 【0042】 The number of reactive silicon groups in polymer (A) is not particularly limited. Preferably, polymer (A) has an average of 0.1 to 5.0 reactive silicon groups per molecule, and more preferably 0.5 to 4.0 reactive silicon groups. 【0043】 The amount of polymer (A) used in the curable composition is not particularly limited, as long as the desired effect is not impaired. The amount of polymer (A) used is preferably 1 to 30 parts by weight, more preferably 5 to 27 parts by weight, and even more preferably 10 to 25 parts by weight, as the amount of polymer (A) per 100g by weight of the curable composition. 【0044】 It is common practice among those skilled in the art to select the monomer composition of polymer (A) according to the application and purpose of the curable composition. In terms of the superior strength of the cured product of the curable composition, it is preferable that the glass transition temperature (Tg) of polymer (A) is relatively high. Specifically, the Tg of (meth)acrylic acid ester polymer (A) is preferably 0 to 200°C, and more preferably 20 to 100°C. The Tg can be determined from the following Fox formula. 【0045】 Fox's formula: 1 / (Tg(K))=Σ(Mi / Tgi) (In the formula, Mi is the weight fraction of monomer i that constitutes the polymer, and Tgi is the glass transition temperature (K) of the homopolymer of monomer i.) 【0046】 For example, polymethyl methacrylate is known as a (meth)acrylic polymer with a relatively high glass transition temperature (Tg). Therefore, in the monomer used to produce polymer (A), the larger the ratio of methyl methacrylate to the weight of the monomer, the higher the glass transition temperature (Tg) of polymer (B) tends to be. Conversely, the smaller the ratio of methyl methacrylate to the weight of the monomer, the lower the glass transition temperature (Tg) of polymer (A) tends to be. It is preferable that the weight ratio of methyl methacrylate to the weight of the monomer used in the production of polymer (A) is 50% or more, as this facilitates the formation of a high-strength cured product. On the other hand, it is preferable that the weight ratio of methyl methacrylate to the weight of the monomer used in the production of polymer (A) is less than 50%, as this results in a curable composition with low viscosity and good workability. 【0047】 <Polyfunctional unsaturated compound (B)> The polyfunctional unsaturated compound (B) is a compound having two or more allyl groups. The polyfunctional unsaturated compound (B) acts as a reactive plasticizer in the curable composition. Furthermore, alkenyl groups having an unsaturated bond at the terminal end with four or more carbon atoms, such as the 3-butenyl group, are considered to be groups containing an allyl group. 【0048】 Examples of polyfunctional unsaturated compounds (B) include allyl ester compounds in which two or more carboxyl groups are substituted with allyloxycarboxyl groups in a polycarboxylic acid having two or more carboxyl groups, allyl ether compounds in which two or more hydroxyl groups are substituted with allyloxy groups in a polyol having two or more hydroxyl groups, and allylthio compounds in which two or more thiol groups are substituted with allylthio groups in a polythiol having two or more thiol groups. Among the above compounds, allyl ester compounds and allyl thio compounds are preferred. 【0049】 Suitable examples of allyl ester compounds include diallyl esters of aromatic dicarboxylic acids such as diallyl phthalate, diallyl isophthalate, and diallyl terephthalate; diallyl esters of linear aliphatic dicarboxylic acids such as diallyl oxalate, diallyl malonate, diallyl succinate, diallyl maleate, diallyl fumarate, diallyl glutarate, and diallyl adipicate; and triallyl 1,2,3-propanetricarboxylic acid, triallyl 1,2,3-butanetricarboxylic acid, triallyl 1,2,4-butanetricarboxylic acid, triallyl 1,2,3-pentanetricarboxylic acid, triallyl 1,2,4-pentanetricarboxylic acid, triallyl 1,2,5-pentanetricarboxylic acid, triallyl 1,3,4-pentanetricarboxylic acid, triallyl 1,3,5-pentanetricarboxylic acid, and triallyl 2,3,4-pentanetricarboxylic acid. Triaryl esters of linear aliphatic tricarboxylic acids such as allyl esters, 1,2,5-hexanetricarboxylic acid trialyl ester, 1,1,6-hexanetricarboxylic acid trialyl ester, 1,3,5-hexanetricarboxylic acid trialyl ester, 1,2,6-hexanetricarboxylic acid trialyl ester, 1,3,3-hexanetricarboxylic acid trialyl ester, 1,2,4-hexanetricarboxylic acid trialyl ester, 2,4,4-hexanetricarboxylic acid trialyl ester, 1,4,5-hexanetricarboxylic acid trialyl ester, 1,3,4-hexanetricarboxylic acid trialyl ester, 1,3,6-hexanetricarboxylic acid trialyl ester, 2,3,5-hexanetricarboxylic acid trialyl ester, 2-carboxymethyl-1,3-propanedicarboxylic acid trialyl ester, 3-carboxymethyl-1,5-pentanedicarboxylic acid trialyl ester, and 3-carboxyethyl-1,5-pentanedicarboxylic acid trialyl ester;Examples include tetraallyls of linear aliphatic tetracarboxylic acids such as 1,2,3,4-butanetetracarboxylic acid tetraallyl ester, 1,2,2,3-butanetetracarboxylic acid tetraallyl ester, 1,2,3,5-pentanetetracarboxylic acid tetraallyl ester, 1,2,4,5-pentanetetracarboxylic acid tetraallyl ester, and 1,2,5,6-hexanetetracarboxylic acid tetraallyl ester; and diallyls of alicyclic dicarboxylic acids such as 1,4-cyclohexanedicarboxylic acid diallyl ester, 1,3-cyclohexanedicarboxylic acid diallyl ester, and 1,2-cyclohexanedicarboxylic acid diallyl ester. 【0050】 Specific examples of allyl ether compounds include ethylene glycol diallyl ether, diethylene glycol diallyl ether, triethylene glycol diallyl ether, propylene glycol diallyl ether (CH2=CHCH2-O-CH2CH2CH2-O-CH2CH=CH2), dipropylene glycol diallyl ether (CH2=CHCH2-O-(CH2CH2CH2-O)2-CH2CH=CH2), and tripropylene glycol diallyl ether (C H2=CHCH2-O-(CH2CH2CH2-O)3-CH2CH=CH2), Propylene glycol diallyl ether (CH2=CHCH2-O-CH(CH3)CH2-O-CH2CH=CH2), Dipropylene glycol diallyl ether (CH2=CHCH2-O-(CH(CH3)CH2-O)2-CH2CH=CH2), Tripropylene glycol diallyl ether (CH2=CHCH2-O-(CH(CH3)CH2-O)3-CH2CH=CH2) Examples include diallyl ethers of linear aliphatic diols such as 1,4-butanediol diallyl ether, 1,5-pentanediol diallyl ether, and 1,6-hexanediol diallyl ether; triallyl ethers of linear aliphatic triols such as glycerin triallyl ether and trimethylolpropane triallyl ether; tetraallyl ethers of linear aliphatic tetraols such as diglycerin tetraallyl ether, di(trimethylolpropane)tetraallyl ether, and pentaerythritol tetraallyl ether; pentaallyl ethers of linear aliphatic pentaols such as triglycerin pentaallyl ether; hexaallyl ethers of linear aliphatic hexaols such as dipentaerythritol hexaallyl ether; and diallyl ethers of alicyclic diols such as 1,4-cyclohexanediol diallyl ether, 1,3-cyclohexanediol diallyl ether, and 1,2-cyclohexanediol diallyl ether. 【0051】 The curable composition may contain two or more compounds as polyfunctional unsaturated compound (B). 【0052】 The amount of polyfunctional unsaturated compound (B) used in the curable composition is not particularly limited, as long as the desired effect is not impaired. The amount of polyfunctional unsaturated compound (B) used is preferably 2 to 50 times the weight of polymer (A), more preferably 2.5 to 30 times, and even more preferably 3 to 5 times. 【0053】 The ratio of the total weight of polymer (A) to the weight of polyfunctional unsaturated compound (B) to the weight of the curable composition is preferably 50% by weight or more, more preferably 70% by weight or more, even more preferably 80% by weight or more, and particularly preferably 90% by weight or more. 【0054】 <Metallic soap (C)> The curable composition contains a metal soap (C). The metal soap (C) is a metal carboxylate salt and / or a metal sulfonic acid salt, with the metal carboxylate salt being preferred. 【0055】 The type of metal soap (C) is not particularly limited, as long as metal soap (C) is a carboxylic acid metal salt or a sulfonic acid metal salt. Typically, metal soaps are compounds in which a long-chain aliphatic carboxylic acid or long-chain aliphatic sulfonic acid is bonded to a metal ion. Examples of long-chain aliphatic carboxylic acids or long-chain aliphatic sulfonic acids include saturated aliphatic carboxylic acids having 1 to 18 carbon atoms, unsaturated aliphatic carboxylic acids having 3 to 18 carbon atoms, aliphatic dicarboxylic acids, saturated aliphatic sulfonic acids having 1 to 18 carbon atoms, and unsaturated aliphatic sulfonic acids having 3 to 18 carbon atoms. Among these, saturated aliphatic carboxylic acids having 1 to 18 carbon atoms are preferred, and saturated aliphatic carboxylic acids having 6 to 18 carbon atoms are more preferred. Examples of metal ions include alkali metal ions, alkaline earth metal ions, zinc ions, cobalt ions, and aluminum ions. 【0056】 Suitable specific examples of metal soap (C) include lithium stearate, lithium 12-hydroxystearate, lithium laurate, lithium oleate, lithium 2-ethylhexanoate, sodium stearate, sodium 12-hydroxystearate, sodium laurate, sodium oleate, sodium 2-ethylhexanoate, potassium stearate, potassium 12-hydroxystearate, potassium laurate, potassium oleate, potassium 2-ethylhexanoate, magnesium stearate, magnesium 12-hydroxystearate, magnesium laurate, and oleate. Examples include magnesium stearate, magnesium 2-ethylhexanoate, calcium stearate, calcium 12-hydroxystearate, calcium laurate, calcium oleate, calcium 2-ethylhexanoate, barium stearate, barium 12-hydroxystearate, barium laurate, zinc stearate, zinc 12-hydroxystearate, zinc laurate, zinc oleate, zinc 2-ethylhexanoate, lead stearate, lead 12-hydroxystearate, cobalt stearate, aluminum stearate, manganese oleate, and barium ricinoleate. 【0057】 The amount of metal soap (C) used is preferably 0.01 to 20 parts by weight, more preferably 0.05 to 10 parts by weight, and particularly preferably 0.1 to 5 parts by weight, per 100 parts by weight of polyfunctional unsaturated compound (B). 【0058】 <Curing catalyst (D)> The curable composition contains a curing catalyst (D) for the purpose of promoting the hydrolysis condensation reaction between reactive silicon groups in polymer (A) and extending or crosslinking the polymer chain. Examples of curing catalysts (D) include organotin compounds, metal carboxylate salts, amine compounds, carboxylic acids, and alkoxy metals. 【0059】 Specific examples of organotin compounds include dibutyltin dilaurate, dibutyltin dioctanoate, dibutyltin bis(butylmaleate), dibutyltin diacetate, dibutyltin oxide, dibutyltin diacetylacetonate, dioctyltin diacetylacetonate, dioctyltin dilaurate, dioctyltin distearate, dioctyltin diacetate, dioctyltin oxide, reaction products of dibutyltin oxide and silicate compounds, reaction products of dioctyltin oxide and silicate compounds, and reaction products of dibutyltin oxide and phthalate esters. 【0060】 Specific examples of metal carboxylate salts include tin carboxylate, bismuth carboxylate, titanium carboxylate, zirconium carboxylate, and iron carboxylate. Furthermore, salts combining the following carboxylic acids with various metals can be used as metal carboxylate salts. 【0061】 Specific examples of amine compounds include amines such as octylamine, 2-ethylhexylamine, laurylamine, and stearylamine; nitrogen-containing heterocyclic compounds such as pyridine, 1,8-diazabicyclo[5,4,0]undecene-7 (DBU), and 1,5-diazabicyclo[4,3,0]nonene-5 (DBN); guanidines such as guanidine, phenylguanidine, and diphenylguanidine; biguanides such as butyl biguanide, 1-o-tolylbiguanide, and 1-phenylbiguanide; amino group-containing silane coupling agents; and ketimine compounds. 【0062】 Specific examples of carboxylic acids include acetic acid, propionic acid, butyric acid, 2-ethylhexanoic acid, lauric acid, stearic acid, oleic acid, linoleic acid, neodecanoic acid, and versatic acid. 【0063】 Specific examples of alkoxy metals include titanium compounds such as tetrabutyl titanate, titanium tetrakis (acetylacetonate), and diisopropoxytitanium bis (ethylacetoacetate), as well as aluminum compounds such as aluminum tris (acetylacetonate) and diisopropoxyaluminum ethylacetoacetate, and zirconium compounds such as zirconium tetrakis (acetylacetonate). Other silanol condensation catalysts that can be used include fluorine anion-containing compounds, photoacid generators, and photobase generators. 【0064】 The curing catalyst (D) may be used in combination with two or more different catalysts. The amount of curing catalyst (D) used is preferably 0.01 to 20 parts by weight, more preferably 0.05 to 10 parts by weight, and particularly preferably 0.1 to 5 parts by weight, per 100 parts by weight of polymer (A). 【0065】 <Highly polar liquid (E)> The curable composition preferably contains a highly polar liquid (E) with a dissolution parameter SP value of 8 or higher. 【0066】 As the highly polar liquid (E), at least one selected from the group consisting of alcohols, amine compounds, amide compounds, and (meth)acrylic acid monomers is preferred. Examples of alcohols include methanol, ethanol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, n-pentyl alcohol, n-hexyl alcohol, n-heptyl alcohol, n-octyl alcohol, 2-ethylhexyl alcohol, n-nonyl alcohol, and n-decyl alcohol. Examples of amine compounds include liquid compounds among the amine compounds mentioned above for the curing catalyst (D) whose solubility parameter, SP value, is 8 or higher. Examples of amide compounds include N,N-dimethylacrylamide, dimethylformamide, dimethylacetamide, and N,N-dimethylacrylamide. Examples of (meth)acrylic acid monomers include 4-hydroxybutyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, and isobornyl (meth)acrylate. 【0067】 The amount of highly polar liquid (E) used is preferably 0.01 to 20 parts by weight, and more preferably 0.1 to 10 parts by weight, based on 100 parts by weight of the total weight of polymer (A) and polyfunctional unsaturated compound (B). 【0068】 <Other additives> The curable composition may contain other additives besides the polymer (A), polyfunctional unsaturated compound (B), metal soap (C), and curing catalyst (D), to the extent that the desired effect is not impaired. Examples of other additives include curing catalysts, fillers, adhesion promoters, plasticizers, solvents, diluents, light stabilizers, UV absorbers, property modifiers, epoxy group-containing compounds, photocurable substances, epoxy resins, other resins, surface modifiers, foaming agents, curing modifiers, flame retardants, silicates, radical inhibitors, metal deactivators, phosphorus-based peroxide decomposers, lubricants, pigments, and antifungal agents. Furthermore, some of the other additives include compounds that fall under the category of highly polar liquids (E) mentioned above. 【0069】 (Filler) Various fillers may be added to the curable composition. Examples of fillers include reinforcing fillers such as fumed silica, precipitated silica, crystalline silica, fused silica, dolomite, anhydrous silicic acid, hydrated silicic acid, and carbon black; fillers such as heavy calcium carbonate, colloidal calcium carbonate, magnesium carbonate, diatomaceous earth, calcined clay, clay, talc, titanium dioxide, bentonite, organic bentonite, ferric oxide, aluminum powder, flint powder, zinc oxide, activated zinc oxide, and resin powder; and fibrous fillers such as asbestos, glass fibers, and filaments. Examples of resin powders include PVC powder and PMMA powder. When using a filler, the amount of filler used is preferably 1 to 100 parts by weight, and more preferably 5 to 50 parts by weight, per 100 parts by weight of the total weight of polymer (A) and polyfunctional unsaturated compound (B). 【0070】 When a hardened product with high strength is desired using these fillers, fillers selected from fumed silica, precipitated silica, crystalline silica, fused silica, dolomite, anhydrous silicic acid, hydrated silicic acid, carbon black, surface-treated fine calcium carbonate, calcined clay, clay, and activated zinc oxide are preferably used. In terms of the strength of the cured product, the preferred amount of these fillers to use is 1 to 100 parts by weight per 100 parts by weight of the polymer (A) and the polyfunctional unsaturated compound (B). Furthermore, if it is desired to obtain a cured product with low strength and high elongation at break, fillers selected mainly from titanium dioxide, calcium carbonate, magnesium carbonate, talc, ferric oxide, zinc oxide, and shirasu balloons can be preferably used. In terms of the elongation at break of the cured product, the preferred amount of these fillers to use is 1 to 100 parts by weight per 100 parts by weight of the polymer (A) and the polyfunctional unsaturated compound (B). 【0071】 Generally, the larger the specific surface area of ​​calcium carbonate, the greater the improvement in the fracture strength, elongation at fracture, and adhesion of the cured product. These fillers may be used individually or in mixtures of two or more types. Fatty acid surface-treated colloidal calcium carbonate and untreated heavy calcium carbonate or other calcium carbonate with a particle size of 1 μm or larger can be used in combination. 【0072】 The curable composition may contain spherical hollow bodies, such as balloons, for the purpose of reducing the weight (specific gravity) of the cured product. A balloon is a hollow, spherical filler. Examples of balloon materials include inorganic materials such as glass, shirasu (volcanic ash), and silica, and organic materials such as phenolic resin, urea resin, polystyrene, saran, and acrylonitrile. However, the balloon material is not limited to these materials. The balloon material may be a composite material consisting of inorganic and organic materials. Furthermore, the balloon material may consist of multiple layers laminated together. In addition, a single type of balloon may be used, or two or more types may be used in combination. The surface of the balloon may be surface-treated, coated, or treated with various surface treatment agents. For example, organic balloons coated with calcium carbonate, talc, titanium dioxide, etc., or inorganic balloons surface-treated with silane coupling agents can be used. 【0073】 The balloon particle size is preferably 3 μm to 200 μm, and particularly preferably 10 μm to 110 μm. When the balloon particle size is within the above range, the cured product can be made lighter to the desired extent by using an appropriate amount of balloons, and the cured product can be formed while suppressing the occurrence of surface irregularities and a decrease in elongation. 【0074】 When using balloons, slip-preventing agents such as those described in Japanese Patent Publication No. 2000-154368 and amine compounds that create an uneven and matte surface on the cured product, as described in Japanese Patent Publication No. 2001-164237, can be added to the curable composition. Among the aforementioned amine compounds, primary and / or secondary amines with a melting point of 35°C or higher are particularly preferred. 【0075】 Specific examples of balloons are described in Japanese Patent Publication Nos. Hei 2-129262, Hei 4-8788, Hei 4-173867, Hei 5-1225, Hei 7-113073, Hei 9-53063, Hei 10-251618, Hei 2000-154368, Hei 2001-164237, WO97 / 05201, and others. 【0076】 The amount of spherical hollow bodies (balloons) used is preferably 0.01 to 30 parts by weight per 100 parts by weight of the total weight of polymer (A) and polyfunctional unsaturated compound (B). The lower limit is more preferably 0.1 parts by weight, and the upper limit is more preferably 20 parts by weight. Using an amount of spherical hollow bodies within the above range results in a good curable composition and makes it easy to form a cured product with excellent elongation and tensile strength. 【0077】 (Adhesion-enhancing agent) The curable composition may contain an adhesion promoter. An example of an adhesion promoter is a silane coupling agent. Silane coupling agents are compounds having a hydrolyzable silicon group and a functional group other than a hydrolyzable silicon group in their molecule. When a curable composition is applied to various substrates, such as inorganic substrates like glass, aluminum, stainless steel, zinc, copper, and mortar, and organic substrates like vinyl chloride, acrylic, polyester, polyethylene, polypropylene, and polycarbonate, a significant improvement in adhesion is observed under non-primer conditions or primer-treated conditions. The effect of improving adhesion to various substrates is particularly pronounced when the curable composition is used under non-primer conditions. In addition to the above functions, silane coupling agents can also function as dehydrating agents, property modifiers, and dispersibility modifiers for inorganic fillers. 【0078】 The hydrolyzable groups in the hydrolyzable silicon groups of the silane coupling agent are not particularly limited. Examples of hydrolyzable groups include hydrogen atoms, halogen atoms, alkoxy groups, aryloxy groups, alkenyloxy groups, acyloxy groups, ketoximate groups, amino groups, amide groups, acid amide groups, aminooxy groups, and mercapto groups. Among these, halogen atoms, alkoxy groups, alkenyloxy groups, and aryloxy groups are preferred due to their high activity. Chlorine atoms and alkoxy groups are preferred because they are easily introduced into the silane coupling agent. Alkoxy groups such as methoxy groups and ethoxy groups are more preferred, with methoxy groups and ethoxy groups being particularly preferred, due to their mild hydrolysis and ease of handling. Furthermore, ethoxy groups and isopropenyloxy groups are preferred in terms of safety because the compounds eliminated by the reaction are ethanol and acetone, respectively. The number of hydrolyzable groups bonded to the silicon atoms in the silane coupling agent may be preferably three to ensure good adhesion. Alternatively, two may be preferable to ensure the storage stability of the curable composition. 【0079】 When using a silane coupling agent as an adhesion promoter, an aminosilane coupling agent having a hydrolyzable silicon group and a substituted or unsubstituted amino group is preferred because it has a greater adhesion-improving effect. The substituent on the substituted amino group is not particularly limited. Examples of such substituents include alkyl groups, aralkyl groups, and aryl groups. 【0080】 Specific examples of aminosilane coupling agents include 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropyltriisopropoxysilane, 3-aminopropylmethyldimethoxysilane, 3-aminopropylmethyldiethoxysilane, 3-(2-aminoethylamino)propyltrimethoxysilane, 3-(2-aminoethylamino)propylmethyldimethoxysilane, 3-(2-aminoethylamino)propyltriethoxysilane, 3-(2-aminoethylamino)propylmethyldiethoxysilane, 3-(2-aminoethylamino)propyltriisopropoxysilane, 3-(2-(2-aminoethylamino)ethylamino)propyltrimethoxysilane, 3-(6-aminohexylamino)propyltrimethoxysilane, and 3-ethylamino-2-methylpropyltrimethoxysilane. Examples of amino group-containing silanes include 3-ureidopropyltrimethoxysilane, 3-ureidopropyltriethoxysilane, 3-phenylaminopropyltrimethoxysilane, 3-benzylaminopropyltrimethoxysilane, 3-(vinylbenzylamino)propyltriethoxysilane, N-cyclohexylaminomethyltriethoxysilane, N-cyclohexylaminomethyldiethoxymethylsilane, N-phenylaminomethyltrimethoxysilane, N-butylaminopropyltrimethoxysilane, (2-aminoethylamino)methyltrimethoxysilane, N,N'-bis[3-(trimethoxysilyl)propyl]ethylenediamine, and bis(trimethoxysilylpropyl)amine; and ketimine-type silanes such as N-(1,3-dimethylbutylidene)-3-(triethoxysilyl)-1-propanamine. 【0081】 Of these, 3-aminopropyltrimethoxysilane, 3-(2-aminoethylamino)propyltrimethoxysilane, and 3-(2-aminoethylamino)propylmethyldimethoxysilane are preferred in terms of good adhesion of the cured product. One aminosilane coupling agent may be used, or two or more may be used in combination. It has been noted that 3-(2-aminoethylamino)propyltrimethoxysilane is more irritating than other aminosilanes. Irritation can be mitigated by reducing the amount of 3-(2-aminoethylamino)propyltrimethoxysilane and using 3-aminopropyltrimethoxysilane in combination. Furthermore, silane coupling agents oligomerized by partially condensing hydrolyzable silicon groups can also be suitably used in terms of safety and stability. The silane coupling agents to be condensed may be a single agent or multiple agents. Examples of oligomerized silane coupling agents include Dynasylan 1146 from Evonik. In terms of good storage stability of the curable composition, 3-aminopropyltrimethoxysilane and 3-(2-aminoethylamino)propylmethyldimethoxysilane are preferred. 【0082】 Specific examples of silane coupling agents other than aminosilane coupling agents include epoxy group-containing silane coupling agents such as 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, and 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane; isocyanate group-containing silane coupling agents such as 3-isocyanatetopropyltrimethoxysilane, 3-isocyanatetopropyltriethoxysilane, 3-isocyanatetopropylmethyldiethoxysilane, 3-isocyanatetopropylmethyldimethoxysilane, (isocyanatemethyl)trimethoxysilane, and (isocyanatemethyl)dimethoxymethylsilane; and 3-mercaptopropyltrimethoxysilane, 3-mercaptopropyltriethoxysilane. Examples include mercapto group-containing silane coupling agents such as 3-mercaptopropylmethyldimethoxysilane, 3-mercaptopropylmethyldiethoxysilane, and mercaptomethyltriethoxysilane; carboxysilane coupling agents such as 2-carboxyethyltriethoxysilane, 2-carboxyethylphenylbis(2-methoxyethoxy)silane, and N-2-(carboxymethylamino)ethyl-3-aminopropyltrimethoxysilane; vinyl-type unsaturated group-containing silane coupling agents such as vinyltrimethoxysilane, vinyltriethoxysilane, 3-methacryloyloxypropylmethyldimethoxysilane, and 3-acryloyloxypropylmethyltriethoxysilane; halogen-containing silane coupling agents such as 3-chloropropyltrimethoxysilane; and isocyanurate silane coupling agents such as tris(trimethoxysilyl)isocyanurate. In addition, condensates obtained by partially condensing the above silane coupling agents can also be used. Examples of such condensates include Dynasylan6490 and Dynasylan6498 from Evonik.Furthermore, modified derivatives of these, 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. 【0083】 Of these, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, and 3-glycidoxypropylmethyldimethoxysilane are preferred in terms of good adhesion of the cured product. 【0084】 The above silane coupling agents may be used individually or in combination of two or more types. The amount of silane coupling agent used is preferably 0.1 to 20 parts by weight, and more preferably 0.5 to 10 parts by weight, per 100 parts by weight of the total weight of polymer (A) and polyfunctional unsaturated compound (B). 【0085】 In addition to the adhesion promoters mentioned above, compounds with a surface tension of 20 to 110 mN / m, calculated at 23°C according to the parachol method, are also preferred as adhesion promoters. Examples of adhesion-imparting agents exhibiting the above-mentioned surface tension include silane coupling agents, silicone oils with reactive groups, polyethyleneimines, organic amines other than polyethyleneimines, nitrogen-containing aromatic heterocyclic compounds, organic carboxylic acids, dicarboxylic acid anhydrides, drying oils, carboxylic acid amides, and phosphate esters. 【0086】 These compounds can form covalent or hydrogen bonds with components contained in the curable composition, or with the surfaces of various articles to which the curable composition is applied. Therefore, these compounds can improve the adhesion of the curable composition and its cured products. 【0087】 For example, when dropping a liquid onto a glass substrate, liquids with lower surface tension spread more easily on the glass substrate. In other words, because the surface of a liquid with low surface tension is energetically stable, there is less of a force that would cause it to spheroidize in order to minimize the surface area, and as a result, it has good affinity with other materials. For this reason, adhesion promoters having a surface tension that is not excessively high, as described above, disperse uniformly in the curable composition and also have good wettability to the surface of the article to which the curable composition is applied. For these reasons, it is considered that adhesion promoters exhibiting the above-mentioned predetermined surface tension improve the adhesion of the curable composition. While a lower surface tension is preferable, a surface tension of 20 mN / m or higher is preferable due to the practical availability of adhesion promoters. 【0088】 Among the adhesion-imparting agents mentioned above, silane coupling agents, silicone oils having reactive groups, and polyethyleneimines are preferred. The silane coupling agents are as described above. 【0089】 The following describes silicone oils and polyethyleneimines that have reactive groups. 【0090】 • Silicone oil containing reactive groups The main chain structure of silicone oil consists of polysiloxane. Silicone oil having reactive groups is a silicone oil in which reactive groups are introduced into the side chains or the main chain. Here, the reactive group is a functional group that can react with functional groups of essential or optional components contained in the cured composition. This reaction includes not only chemical reactions that form covalent bonds, but also intermolecular reactions that form hydrogen bonds. As a silicone oil having a reactive group, a silicone oil having a reactive group at both ends of the main chain of the silicone oil is preferred. The reactive group of the silicone oil is preferably one or more selected from the group consisting of an amino group, a dicarboxylic acid anhydride group, an epoxy group, a reactive silicon group, a hydroxyl group, a mercapto group, a carboxyl group, and a (meth)acrylic group, with an amino group being more preferred. 【0091】 • Polyethyleneimine The polyethyleneimine is not particularly limited as long as its surface tension, measured under specified conditions, is between 20 and 110 mN / m. The polyethyleneimine can be appropriately selected from commercially available liquid polyethyleneimines available at room temperature. 【0092】 The adhesion-imparting agents exhibiting the specific surface tension described above may be used individually or in combination of two or more types. 【0093】 The amount of adhesion-imparting agent exhibiting the specific surface tension described above is preferably 0.01 to 5 parts by weight, and more preferably 0.05 to 3 parts by weight, per 100 parts by weight of the total weight of polymer (A) and polyfunctional unsaturated compound (B). 【0094】 (Plasticizer) The curable composition may contain a plasticizer. By adding a plasticizer, the viscosity and slump of the curable composition, as well as the mechanical properties of the cured product, such as tensile strength and elongation, can be adjusted. 【0095】 Specific examples of plasticizers include phthalate ester compounds such as dibutyl phthalate, diisononyl phthalate (DINP), diheptyl phthalate, di(2-ethylhexyl) phthalate, diisodecyl phthalate (DIDP), and butyl benzyl phthalate; terephthalate ester compounds such as bis(2-ethylhexyl)-1,4-benzenedicarboxylate; hydrogenated phthalate compounds such as 1,2-cyclohexanedicarboxylic acid diisononyl ester; dioctyl adipate, dioctyl sebacate, dibutyl sebacate, and disuccinate. Examples include aliphatic polycarboxylic acid ester compounds such as isodecyl and tributyl acetylcitrate; unsaturated fatty acid ester compounds such as butyl oleate and methyl acetylricinoleate; alkyl sulfonate phenyl esters; phosphate ester compounds such as tricresyl phosphate and tributyl phosphate; trimellitic acid ester compounds; chlorinated paraffin; hydrocarbon oils such as alkyldiphenyl and partially hydrogenated terphenyl; process oils; epoxy plasticizers such as epoxidized soybean oil and benzyl epoxy stearate. A specific example of a terephthalate ester compound is EASTMAN 168 (trade name, manufactured by EASTMAN CHEMICAL). A specific example of a non-phthalate ester compound is Hexamoll DINCH (trade name, manufactured by BASF). A specific example of an alkylsulfonate phenyl ester is Mesamoll (trade name, manufactured by LANXESS). 【0096】 High molecular weight plasticizers can also be used. Using high molecular weight plasticizers allows the initial properties of the cured product to be maintained over a longer period compared to using low molecular weight plasticizers. Furthermore, the drying properties (coatability) when alkyd paint is applied to the cured product are improved. 【0097】 Specific examples of polymeric plasticizers include vinyl polymers, which are polymers of vinyl monomers; esters of polyalkylene glycols and polyols such as diethylene glycol dibenzoate, triethylene glycol dibenzoate, and pentaerythritol ester; polyester plasticizers obtained from dibasic acids such as sebacic acid, adipic acid, azelaic acid, and phthalic acid, and dihydric alcohols such as ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, and dipropylene glycol; polyether polyols (polyoxyalkylene compounds) such as polyethylene glycol, polypropylene glycol, and polytetramethylene glycol with a number average molecular weight of 500 or more, and even 1,000 or more; derivatives of these polyether polyols obtained by converting the hydroxyl groups to ester groups, ether groups, etc.; polystyrenes such as polystyrene and poly-α-methylstyrene; and polybutadiene, polybutene, polyisobutylene, butadiene-acrylonitrile, and polychloroprene. Polymeric plasticizers are not limited to these. 【0098】 The polymeric plasticizer is preferably compatible with polymer (A) and / or polyfunctional unsaturated compound (B). From this point of view, polyethers and vinyl polymers are preferred. When polyethers are used as plasticizers, surface curability and deep curability are improved, and curing delay after storage does not occur. Among polyethers, polypropylene glycol is more preferred. Vinyl polymers are also preferred from the viewpoint of compatibility with polymer (A) and / or polyfunctional unsaturated compound (B), as well as the weather resistance and heat resistance of the cured product. Among vinyl polymers, acrylic polymers and / or methacrylic polymers are preferred, and acrylic polymers such as alkyl polyacrylates are even more preferred. As for the synthesis method of vinyl polymers, living radical polymerization is preferred, and atom transfer radical polymerization is even more preferred, because it yields polymers with a narrow molecular weight distribution and low viscosity. Furthermore, the so-called SGO process, described in Japanese Patent Publication No. 2001-207157, which involves continuous bulk polymerization of alkyl acrylate monomers at high temperature and high pressure, is also a preferred method for producing vinyl polymers. 【0099】 The number-average molecular weight of the polymeric plasticizer is preferably 500 to 15,000, more preferably 800 to 10,000, even more preferably 1,000 to 8,000, particularly preferably 1,000 to 5,000, and most preferably 1,000 to 3,000. When the number-average molecular weight of the polymeric plasticizer is within the above range, the leaching of the plasticizer from the cured product over time due to heat, rainfall, etc., can be suppressed, the initial physical properties of the cured product can be maintained for a long period of time, the curable composition has an appropriate viscosity, and the curable composition has good workability. The molecular weight distribution of the polymeric plasticizer is not particularly limited, but a narrow distribution is preferred. Specifically, the molecular weight distribution is preferably less than 1.80, more preferably 1.70 or less, even more preferably 1.60 or less, still more preferably 1.50 or less, particularly preferably 1.40 or less, and most preferably 1.30 or less. 【0100】 The number-average molecular weight of vinyl polymers is measured by GPC (Geomorphic Spectroscopy). The number-average molecular weight of polyether polymers is measured by end-group analysis. Furthermore, the molecular weight distribution (Mw / Mn) is measured by GPC (polystyrene equivalent). 【0101】 The polymeric plasticizer may or may not have reactive silicon groups. If the polymeric plasticizer has reactive silicon groups, it acts as a reactive plasticizer, preventing the migration of the plasticizer from the cured product. When the polymeric plasticizer has reactive silicon groups, the number of reactive silicon groups is preferably one or less on average per molecule, and more preferably 0.8 or less. When using a plasticizer having reactive silicon groups, particularly a polyether polymer having reactive silicon groups, its number-average molecular weight must be lower than the number-average molecular weight of the polyoxyalkylene polymer (A) and / or the (meth)acrylic polymer (B). 【0102】 Among the plasticizers described above, at least one selected from the group consisting of phthalate esters, hydrogenated phthalate esters, and polyoxyalkylene compounds is preferred. 【0103】 The amount of plasticizer used is preferably 5 to 150 parts by weight, more preferably 10 to 120 parts by weight, and even more preferably 20 to 100 parts by weight, based on 100 parts by weight of the total weight of polymer (A) and polyfunctional unsaturated compound (B). When the amount of plasticizer used is within the above range, it is possible to form a cured product with excellent mechanical strength while fully obtaining the desired effect of using the plasticizer. The plasticizer may be used alone or in combination of two or more types. A low molecular weight plasticizer and a high molecular weight plasticizer may be used in combination. These plasticizers may be blended into polymer (A) when producing polymer (A). 【0104】 (Solvents, diluents) The curable composition may contain a small amount of a solvent or diluent that does not fall under the category of highly polar liquids (E), provided that odor problems do not occur. The solvent and diluent are not particularly limited. Examples of solvents and diluents include aliphatic hydrocarbons, aromatic hydrocarbons, alicyclic hydrocarbons, halogenated hydrocarbons, alcohols, esters, ketones, and ethers. When using a solvent or diluent, the boiling point of the solvent is preferably 150°C or higher, more preferably 200°C or higher, and particularly preferably 250°C or higher, due to concerns about air pollution when the curable composition is used indoors. The solvent or diluent may be used alone or in combination of two or more. The content of the solvent or diluent is preferably 2 parts by weight or less, and more preferably 1 part by weight or less, per 100 parts by weight of the curable composition. 【0105】 (Light stabilizer) The curable composition may contain a light stabilizer. Using a light stabilizer can prevent photo-oxidative degradation of the cured product. Examples of light stabilizers include benzotriazole compounds, hindered amine compounds, and benzoate compounds. The amount of light stabilizer used is preferably 0.1 to 10 parts by weight, and more preferably 0.2 to 5 parts by weight, per 100 parts by weight of the total weight of polymer (A) and polyfunctional unsaturated compound (B). Specific examples of light stabilizers are described, for example, in Japanese Patent Publication No. 9-194731. 【0106】 (UV absorber) The curable composition may contain an ultraviolet absorber. Using an ultraviolet absorber can improve the surface weather resistance of the cured product. Examples of ultraviolet absorbers include benzophenone compounds, benzotriazole compounds, salicylate compounds, triazine compounds, substituted tolyl compounds, and metal chelate compounds. Among these, benzotriazole compounds are particularly preferred. Specific examples of benzotriazole compounds include tinubine 234, tinubine 326, tinubine 327, tinubine 328, tinubine 329, tinubine 350, tinubine 571, tinubine 900, tinubine 928, tinubine 1130, tinubine 1600 (all manufactured by BASF); and SONGSORB 3290 (manufactured by SONGWON). Specific examples of triazine compounds include Tinuvin 400, Tinuvin 405, Tinuvin 477, and Tinuvin 1577ED (all manufactured by BASF); and SONGSORB CS400 and SONGSORB 1577 (manufactured by SONGWON). Specific examples of benzophenone compounds include SONGSORB 8100 (manufactured by SONGWON). The amount of UV absorber used is preferably 0.1 to 10 parts by weight, and more preferably 0.2 to 5 parts by weight, per 100 parts by weight of the total weight of polymer (A) and polyfunctional unsaturated compound (B). It is preferable to use a combination of a phenolic antioxidant or a hindered phenolic antioxidant, a hindered amine light stabilizer, and a benzotriazole UV absorber. AddworksIBC760 (manufactured by Clariant) can be used as a product containing antioxidants, light stabilizers, and UV absorbers. 【0107】 (Property modifier) The curable composition may optionally contain a property modifier to adjust the tensile properties of the cured product. The property modifier is not particularly limited. Examples of property modifiers include alkylalkoxysilanes such as methyltrimethoxysilane, dimethyldimethoxysilane, trimethylmethoxysilane, and n-propyltrimethoxysilane; alkylisopropenoxysilanes such as dimethyldiisopropenoxysilane, methyltriisopropenoxysilane, and 3-glycidoxypropylmethyldiisopropenoxysilane; alkoxysilanes having functional groups such as 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, vinyltrimethoxysilane, vinyldimethylmethoxysilane, 3-aminopropyltrimethoxysilane, N-2-aminoethyl-3-aminopropylmethyldimethoxysilane, 3-mercaptopropyltrimethoxysilane, and 3-mercaptopropylmethyldimethoxysilane; silicone varnishes; and polysiloxanes. By using property modifiers, it is possible to increase the hardness of the cured material or, conversely, decrease its hardness and increase its elongation at break. These property modifiers may be used alone or in combination of two or more types. 【0108】 In particular, compounds that produce a compound having a monovalent silanol group in the molecule upon hydrolysis have the effect of lowering the modulus of the cured product without worsening the stickiness of the surface of the cured product. Among the compounds that produce a compound having a monovalent silanol group in the molecule upon hydrolysis, compounds that produce trimethylsilanol are particularly preferred. Examples of compounds that produce a compound having a monovalent silanol group in the molecule upon hydrolysis include the compounds described in Japanese Patent Publication No. 5-117521. In addition, examples of compounds that produce trialkylsilanols such as trimethylsilanol upon hydrolysis include derivatives of alkyl alcohols such as hexanol, octanol, and decanol, and derivatives of polyhydric alcohols having 3 or more hydroxyl groups such as trimethylolpropane, glycerin, pentaerythritol, or sorbitol, which produce trialkylsilanols such as trimethylsilanol upon hydrolysis, as described in Japanese Patent Publication No. 11-241029. Examples include derivatives of oxyalkylene polymers that produce silicon compounds that generate trialkylsilanols such as trimethylsilanol upon hydrolysis, as described in Japanese Patent Publication No. 7-258534. Furthermore, polymers having a crosslinkable hydrolyzable silicon-containing group and a silicon-containing group that can become a monosilanol-containing compound upon hydrolysis, as described in Japanese Patent Publication No. 6-279693, can also be used. The property modifier is used in an amount of 0.1 to 20 parts by weight, preferably 0.5 to 10 parts by weight, per 100 parts by weight of the total weight of polymer (A) and polyfunctional unsaturated compound (B). 【0109】 (Compounds containing epoxy groups) The curable composition may contain compounds containing epoxy groups. Using compounds with epoxy groups can improve the resilience of the cured product. Examples of compounds with epoxy groups include epoxidized unsaturated oils and fats, epoxidized unsaturated fatty acid esters, alicyclic epoxy compounds, epichlorohydrin derivatives, and mixtures thereof. Specific examples of compounds with epoxy groups include epoxidized soybean oil, epoxidized linseed oil, bis(2-ethylhexyl)-4,5-epoxycyclohexane-1,2-dicarbonoxylate (E-PS), epoxyoctyl stearate, and epoxybutyl stearate. The amount of epoxy group-containing compound used is preferably 0.5 to 50 parts by weight per 100 parts by weight of the total weight of polymer (A) and polyfunctional unsaturated compound (B). 【0110】 (Epoxy resin) The curable composition may contain an epoxy resin. Curable compositions containing an epoxy resin are preferred as adhesives, particularly as adhesives for exterior wall tiles. Examples of epoxy resins include bisphenol A type epoxy resins and novolac type epoxy resins. The ratio of the total weight of polymer (A) and polyfunctional unsaturated compound (B) to the weight of epoxy resin is preferably in the range of 100 / 1 to 1 / 100, expressed as (weight of polymer (A) and polyfunctional unsaturated compound (B)) / (weight of epoxy resin). When polymer (A) and polymer (B) and epoxy resin are used in the above ratio, it is easy to form a high-strength cured product with excellent impact strength and toughness. When using epoxy resin, the curing composition may contain a curing agent along with the epoxy resin. The type of curing agent is not particularly limited, and commonly used curing agents can be used. The amount of hardener used is preferably 0.1 to 300 parts by weight per 100 parts by weight of epoxy resin. 【0111】 (light curing substance) The curable composition may contain a photocurable substance. Using a photocurable substance forms a film of the photocurable substance on the surface of the cured product, improving the stickiness and weather resistance of the cured product. Various compounds such as organic monomers, oligomers, and resins are known as photocurable substances. Numerous compositions containing photocurable substances are also known. Representative photocurable substances include unsaturated acrylic compounds, polyvinyl polycinnamates, and azidized resins. Examples of unsaturated acrylic compounds include monomers, oligomers, or mixtures thereof having one or more acrylic or methacrylic unsaturated groups. The amount of photocurable substance used is preferably 0.1 to 20 parts by weight, and more preferably 0.5 to 10 parts by weight, per 100 parts by weight of the total weight of polymer (A) and polyfunctional unsaturated compound (B). When an amount of photocurable substance within this range is used, it is easy to form a flexible cured product with excellent weather resistance and suppressed cracking. 【0112】 Preparation of curable compositions The curable composition can be prepared as a one-component type, where all components are pre-mixed and sealed for storage, and then cured by moisture in the air after application. Alternatively, a curing agent containing a curing catalyst (D), filler, plasticizer, water, etc., can be added separately, and the mixture can be mixed with the polymer composition containing polymer (A) before use to prepare a two-component type. From the viewpoint of workability, a one-component type is preferred. 【0113】 When the curable composition is a one-component type, all components are mixed in advance. Therefore, it is preferable that components containing water be dehydrated and dried before use, or that they be dehydrated during mixing by reduced pressure or the like. In addition to the dehydration drying method, the storage stability of the curable composition is further improved by adding alkoxysilane compounds such as methyltrimethoxysilane, phenyltrimethoxysilane, n-propyltrimethoxysilane, vinyltrimethoxysilane, vinylmethyldimethoxysilane, γ-mercaptopropylmethyldimethoxysilane, γ-mercaptopropylmethyldiethoxysilane, and γ-glycidoxypropyltrimethoxysilane to the curable composition. 【0114】 Uses of curable compositions The curable composition is suitably used as a primer applied to a substrate before applying a sealant to the substrate of a building or the like. The type of substrate is not particularly limited, but mortar or aluminum is preferred. [Examples] 【0115】 The present invention will be described in more detail below with reference to examples. However, the present invention is not limited to the following examples. 【0116】 The number-average molecular weight in the examples is the GPC molecular weight measured under the following conditions. Liquid delivery system: Tosoh HLC-8220GPC Column: Tosoh TSKgel SuperH series Solvent: THF Molecular weight: Polystyrene equivalent Measurement temperature: 40℃ 【0117】 (Method for calculating the average number of reactive silyl groups bonded to the terminal or internal structure of the polymer skeleton in one molecule of a (meth)acrylic polymer) Based on the amount of reactive silyl group-containing monomer and reactive silyl group-containing chain transfer agent used, the average number of reactive silyl groups bonded to the terminals or interior of the polymer backbone in one molecule of (meth)acrylic polymer was calculated. 【0118】 Specifically, the average number of reactive silyl groups was calculated according to the following formula. In the following, the "average number of reactive silyl groups bonded to the ends of the polymer skeleton in one (meth)acrylic polymer molecule" and the "average number of reactive silyl groups bonded to the interior of the polymer skeleton in one (meth)acrylic polymer molecule" will be referred to as the "number of internally bonded silyl groups." 【0119】 Number of internally bonded silyl groups = (Number-average molecular weight of polymer / Total number of solid parts during polymer synthesis) × [(Sum of (Number of each reactive silyl group-containing monomer / Molecular weight of the monomer)] 【0120】 (Preparation Example 1-1) 55 parts of butyl acetate were charged into a reaction vessel equipped with a stirrer, thermometer, reflux condenser, nitrogen gas inlet tube, and dropping funnel, and the temperature was raised to 110°C while introducing nitrogen gas. Then, a mixture consisting of 14 parts by weight of styrene, 13.6 parts by weight of γ-methacryloxypropyltrimethoxysilane, 52 parts by weight of methyl methacrylate, 19.4 parts by weight of n-butyl acrylate, 1 part by weight of N-methylolacrylamide, 1 part by weight of n-dodecyl mercaptan, 12 parts by weight of toluene, 1 part by weight of methanol, and 6 parts by weight of 2,2'-azobisisobutyronitrile was added dropwise at a constant rate over 5 hours using a dropping funnel. After the dropwise addition was complete, 0.8 parts by weight of 2,2'-azobisisobutyronitrile and 15 parts by weight of butyl acetate were added dropwise at a constant rate over 1 hour. The reaction solution was then held at 110°C for 2 hours and then cooled to room temperature. Butyl acetate was added to the cooled resin solution to obtain a polymer solution containing vinyl polymer (A-1) at a resin solids content of 40% by weight. The number-average molecular weight of the obtained vinyl polymer (A-1) was 3500. 【0121】 (Preparation Example 2-1) A mixture containing 10 parts by weight of polymer (A-1) obtained in Synthesis Example 1-1, 25 parts by weight of polymer solution, and 90 parts by weight of diallyl phthalate (B-1) (manufactured by Tokyo Chemical Industry Co., Ltd.) was added and stirred. The resulting mixture was heated to 110°C, and the butyl acetate solvent was removed by distillation under reduced pressure using a rotary evaporator. As a result, a polymer mixture (M-1) was obtained with a solid content concentration of 99% by weight or more and a weight ratio of polymer (A-1) / diallyl phthalate (B-1) of 10 / 90. 【0122】 (Preparation Examples 2-2 to 2-4) Polymer mixtures (M-2) to (M-4) were obtained in the same manner as in Preparation Example 2-1, except that the weight ratio of polymer (A-1) / diallyl phthalate (B-1) was changed to the ratio shown in Table 1. 【0123】 (Preparation Examples 2-5) A polymer mixture (M-5) was obtained in the same manner as in Synthesis Example 2-1, except that diallyl phthalate (B-1) was replaced with pentaerythritol tetraallyl ether (manufactured by Osaka Soda Co., Ltd.). 【0124】 (Preparation Example 3) A linear polyoxypropylene polymer (a-1) having methyldimethoxysilyl groups at its termini and an isobutyl alcohol solution (60% solids by weight) of an acrylic polymer (b-1) obtained by polymerizing 14.5 parts by weight of methyl methacrylate, 68.2 parts by weight of butyl acrylate, 14.9 parts by weight of stearyl methacrylate, and 2.4 parts by weight of (3-methacryloylpropyl)methyldimethoxysilane in isobutyl alcohol using 2,2'-azobis(2-methylbutyronitrile) as an initiator, were mixed to obtain a mixed solution. The ratio of silyl groups to terminal groups in polymer (a-1) was 0.7. The number-average molecular weight of polymer (a-1) was 28,500. The number-average molecular weight of polymer (b-1) was 20,600, and the weight-average molecular weight was 39,100. The resulting mixture was heated to 110°C, and the solvent, isobutyl alcohol, was removed by distillation under reduced pressure using a rotary evaporator. As a result, polymer mixture (c-1) was obtained with a solid content of 99% by weight or more and a weight ratio of polymer (a-1) / polymer (b-1) of 70 / 30. The viscosity of polymer mixture (c-1) at 23°C was 55 Pa·s. 【0125】 [Examples 1-5] To each of the polymer mixtures (M-1) to (M-5) containing the polymer (A-1) and polyfunctional unsaturated compound (B) in the amounts listed in Table 1, a solution of potassium 2-ethylhexanoate as the metal soap (C) in the amount listed in Table 1 and N,N-dimethylacrylamide as the highly polar liquid (E) was added. Polymer mixtures (M-1) to (M-5), to which metal soap (C) and a highly polar liquid (E) were added, were each mixed with a spatula. Then, to polymer mixtures (M-1) to (M-5), the amounts listed in Table 1 for γ-glycidoxypropyltrimethoxysilane (manufactured by Momentive Performance Materials Japan LLC, trade name: SILQUEST A-187 SILAN) and the amounts listed in Table 1 for polyeneimine with a number average molecular weight of 600 (manufactured by Tokyo Chemical Industry Co., Ltd.) were added, respectively. Next, to polymer mixtures (M-1) to (M-5), the amounts listed in Table 1 for dibutyltin diacetylacetonate (manufactured by Nitto Chemical Co., Ltd., trade name: Neostan U220H) were each added, and the mixtures were mixed with a spatula to obtain the curable compositions of Examples 1 to 5. 【0126】 [Comparative Example 1] To 75 parts by weight of a polymer solution containing 30 parts by weight of polymer (A-1) obtained in Synthesis Example 1-1, 18.85 parts by weight of ethyl acetate and 0.9 parts by weight of methyl orthoacetate were added, and the resulting mixture was stirred. The mixture was then held at 23°C for 2 hours to dehydrate it, and then 0.15 parts by weight of BT453Z (manufactured by Kaneka Corporation) was added to the mixture as a curing agent and stirred and mixed. Furthermore, 4.5 parts by weight of γ-glycidoxypropyltrimethoxysilane (SIQUESTA187, manufactured by Momentive Japan Co., Ltd.) and γ-mercaptopropyltrimethoxysilane (trade name SIQUESTA189, manufactured by Momentive Japan Co., Ltd.) were added to the mixture to obtain the solvent-based primer composition of Comparative Example 1. 【0127】 The curable composition of the example and the curable composition of the comparative example were used to evaluate odor and hot water adhesion according to the following method. 【0128】 <Odor Evaluation> Experienced panelists confirmed the presence or absence of odors from organic solvents derived from the curable composition. As a result, no odor of organic solvents was detected in the curable compositions of Examples 1 to 5. On the other hand, an odor of organic solvents was detected in the curable composition of Comparative Example 1. 【0129】 <Evaluation of hot water adhesion resistance> The curable compositions of Examples 1-5 and Comparative Example 1 were applied at a rate of 1 g each to a mortar substrate measuring 8.0 mm × 25 mm × 30 mm (manufactured by Engineering Test Service Co., Ltd.) and an aluminum substrate measuring 1.5 mm × 25 mm × 100 mm (compliant with JIS H4000, manufactured by Engineering Test Service Co., Ltd.). The coating film on the substrate was dried and cured for 24 hours in an environment of 23°C and 55% relative humidity to form a primer film. 【0130】 To 100 parts by weight of the polymer mixture (c-1) obtained in Preparation Example 3, 3 parts by weight of vinyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name: KBM-1003) and 3 parts by weight of N-2-(aminoethyl)-3-aminopropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name: KBM-603) as dehydrating agents, and 2 parts by weight of dibutyltin diacetylacetonate (manufactured by Nitto Chemical Co., Ltd., trade name: Neostan U220H) as a curing catalyst were added and thoroughly mixed to obtain a sealant curable composition. 【0131】 The obtained sealant-curing composition was applied to a mortar substrate and a primer film formed on an aluminum substrate to a thickness of 2 mm. The coating film made of the sealant-curing composition was cured for 7 days at 23°C and 55% relative humidity to form a cured sealant film. 【0132】 Test specimens of each substrate coated with a sealing material were immersed in 50°C hot water for 28 days. The adhesion of the sealant film to the primer-coated substrate was evaluated by hand peel (180° peel) after 7 days of curing, 14 days of hot water immersion, and 28 days of hot water immersion. The evaluation results showed that, under all of the above conditions, the sealant film adhered well to the primer film formed using the curable compositions of Examples 1 to 5 and the curable composition of Comparative Example 1. 【0133】 [Table 1]

Claims

[Claim 1] The material comprises a (meth)acrylic polymer having a reactive silicon group (A), a polyfunctional unsaturated compound (B), a metal soap (C), and a curing catalyst (D). The reactive silicon group is represented by the following formula (1): -SiR 1 a X 3-a (1) (In formula (1), R 1 is a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, or R 0 3 It is a triorganosiloxy group represented by SiO-, and R 0 (where is a hydrocarbon group having 1 to 20 carbon atoms, X is a hydroxyl group or a hydrolyzable group, and a is 0, 1, or 2.) It is a base represented by, The molecular chain of the (meth)acrylic polymer (A) contains constituent units derived from (meth)acrylic acid ester, The polyfunctional unsaturated compound (B) is a compound having two or more allyl groups, A curable composition in which the metal soap (C) is a metal carboxylate salt and / or a metal sulfonic acid salt. [Claim 2] The number average molecular weight of the (meth)acrylic polymer (A) is 3,000 to 60,000. The curable composition according to claim 1, wherein the weight-average molecular weight of the (meth)acrylic polymer (A) is 6,000 to 180,000. [Claim 3] The curable composition according to claim 1, wherein a is 0 in formula (1). [Claim 4] The curable composition according to claim 1, wherein the metal soap (C) is a metal carboxylate salt. [Claim 5] The curable composition according to claim 1, wherein the amount of the (meth)acrylic polymer (A) in 100 parts by weight of the curable composition is 1 to 30 parts by weight. [Claim 6] A curable composition according to claim 1, used as a primer. [Claim 7] The curable composition according to claim 6, which is used as a primer for mortar or aluminum.