JPWO2019187701A1 - Curable resin composition - Google Patents

Abstract

An object of the present invention is to provide a curable resin composition having excellent weather resistance, cured physical properties and workability. The present invention has a reactive silyl group at the end and side chain of a molecular chain, the molecular chain has a repeating unit of a polymerizable vinyl monomer, and the average number of reactive silyl groups per molecule is 1 The number of reactive silyl groups at the terminal or side chain exceeds 0.5, the weight average molecular weight is 30,000 to 110,000, and the number average molecular weight is 9,000 to 40,000, With a vinyl polymer (A) having a glass transition temperature of −100 to −10° C., and having no reactive silyl group, a molecular chain having a repeating unit of a polymerizable vinyl monomer, and a weight average molecular weight of A vinyl polymer (B) containing a vinyl polymer (B) of 20,000 or less and a curing catalyst (C), the molecular chain of the vinyl polymer (A) having a repeating unit of a polymerizable vinyl monomer. A vinyl polymer (a) having a group represented by *-S-L1-X1 (S: sulfur atom, L1: divalent linking group, X1: reactive silyl group, *: bonding position) at the terminal of It is a curable resin composition containing.

Description

The present invention relates to a curable resin composition.

Conventionally, a composition containing a polyoxyalkylene polymer having a reactive silicon group and a (meth)acrylic polymer having a reactive silicon group is known as a sealing material.

For example, Patent Document 1 discloses a crosslinkable silyl group-containing organic polymer (A) for the purpose of providing a sealant composition having paint adhesion and paint non-staining properties and excellent workability, and A curable sealing material containing a specific crosslinkable silyl group terminal-containing (meth)acrylic acid ester polymer (B) having a glass transition temperature of -100°C to -10°C is described.

Japanese Patent No. 5138186

Under these circumstances, the present inventors prepared a composition containing a vinyl polymer having a reactive silyl group and a polyoxyalkylene polymer having a reactive silyl group with reference to Patent Document 1 and evaluated it. As a result, it was revealed that such a composition may have low weather resistance, low physical properties such as elongation of the cured product, or low composition viscosity and poor workability (Comparative Example 7). ).
When a vinyl polymer having no reactive silyl group is used with respect to a vinyl polymer having a reactive silyl group, the weight average molecular weight of the vinyl polymer having no reactive silyl group is too high. It was revealed that the composition may have high viscosity and poor workability (Comparative Example 8).
Therefore, an object of the present invention is to provide a curable resin composition having excellent weather resistance, cured physical properties, and workability. Examples of the cured physical properties include elongation of the cured product. Examples of the workability include that the viscosity of the composition can be set in an appropriate range.

As a result of intensive studies to solve the above problems, the inventors of the present invention have a vinyl polymer (a) in which a molecular chain has a repeating unit of a polymerizable vinyl monomer and a specific group is bonded to the terminal, Having reactive silyl groups at the ends and side chains of the molecular chain, the molecular chain having repeating units of polymerizable vinyl monomers, the total number of reactive silyl groups, the number of reactive silyl groups at the ends and side chains , A vinyl polymer (A) having a weight average molecular weight, a number average molecular weight, and a glass transition temperature within specific ranges, respectively, and having no reactive silyl group and a molecular chain having a repeating unit of a polymerizable vinyl monomer. It was found that the desired effect can be obtained by containing the vinyl polymer (B) having a weight average molecular weight of 20,000 or less and the curing catalyst (C), and has reached the present invention.
The present invention is based on the above findings and the like, and specifically solves the above problems by the following configurations.

[1] Having a reactive silyl group at the end and side chain of the molecular chain, the molecular chain having a repeating unit of a polymerizable vinyl monomer,
On average per molecule, the total number of reactive silyl groups exceeds 1, the number of reactive silyl groups at the terminals exceeds 0.5, and the number of reactive silyl groups in the side chains is 0. More than 5
A vinyl polymer (A) having a weight average molecular weight of 30,000 to 110,000, a number average molecular weight of 9,000 to 40,000, and a glass transition temperature of -100 to -10°C;
A vinyl polymer (B) having no reactive silyl group, a molecular chain having a repeating unit of a polymerizable vinyl monomer, and a weight average molecular weight of 20,000 or less;
Containing a curing catalyst (C),
The vinyl polymer (A) has a repeating unit of a polymerizable vinyl monomer in the molecular chain, and a vinyl polymer (a) having a group represented by the following formula (I) at the end of the molecular chain. Curable resin composition containing.
^{* -S-L 1 -X 1 (} I)
In formula (I), S is a sulfur atom, L ¹ represents a divalent linking group, X ¹ represents a reactive silyl group, and * represents a bonding position.
[2] The curable resin composition according to [1], wherein the content of the vinyl polymer (B) is 1 to 100 parts by mass with respect to 100 parts by mass of the vinyl polymer (A).
[3] The curing catalyst (C) is at least one selected from the group consisting of tin compounds, titanium compounds, acidic compounds and amine compounds,
The curable resin composition according to [1] or [2], wherein the content of the curing catalyst (C) is 0.1 to 20 parts by mass with respect to 100 parts by mass of the vinyl polymer (A).
[4] The curable resin composition according to any one of [1] to [3], which further contains a hollow resin body.
[5] The curable resin composition according to any one of [1] to [4], further containing an antioxidant.
[6] The curable resin composition according to any one of [1] to [5], wherein the vinyl polymer (A) has a weight average molecular weight of 45,000 to 90,000.
[7] The curable resin composition according to any one of [1] to [6], wherein the vinyl polymer (A) has a number average molecular weight of more than 10,000 and less than 20,000.
[8] The curable resin composition according to any one of [1] to [7], wherein the vinyl polymer (A) further has a hydrocarbon group in a side chain. However, the above hydrocarbon group does not have a reactive silyl group.
[9] The curable resin composition according to [8], wherein the hydrocarbon group has 1 to 12 carbon atoms.
[10] The curable resin composition according to any one of [1] to [9], wherein the vinyl polymer (A) has a linear molecular chain.
[11] The curable resin composition according to any one of [1] to [10], wherein in formula (I), the reactive silyl group as X ₁ is a dialkoxysilyl group.
[12] Any one of [1] to [11], wherein the molecular chain of the vinyl polymer (A) has a repeating unit represented by the following formula (II) and a repeating unit represented by the formula (III). The curable resin composition according to.
In formula (II), R ^2-1 represents a hydrogen atom or a monovalent hydrocarbon group, L ² represents a divalent linking group, and R ^2-2 represents a monovalent hydrocarbon group.
In formula (III), R ^3-1 represents a hydrogen atom or a monovalent hydrocarbon group, L ³ represents a divalent linking group, and R ^3-2 and R ^3-3 each independently represent a monovalent hydrocarbon group. It represents a hydrocarbon group, m3 is 1-3, n3 is 0-2, and m3+n3 is 3.
[13] The curable resin composition according to [12], wherein in the formula (III), m3 is 2 and n3 is 1.
[14] The curable resin composition according to any one of [1] to [13], wherein the group represented by the formula (I) is a group represented by the following formula (I-1).
In formula (I-1), R ^1-1 represents a divalent hydrocarbon group, R ^1-2 and R ^1-3 each independently represent a monovalent hydrocarbon group, and m1 is 1 to 3 Yes, n1 is 0 to 2, m1+n1 is 3, and * represents a bonding position.
[15] The curable resin composition according to [14], wherein in the formula (I-1), m1 is 2 and n1 is 1.
[16] The curable resin composition according to any one of [1] to [15], wherein the vinyl polymer (a) has one terminal having a group represented by the formula (I).
[17] The curable resin composition according to any one of [1] to [16], wherein the vinyl polymer (a) further has a reactive silyl group on a side chain of the molecular chain.
[18] In the vinyl polymer (A), the reactive silyl group at the terminal of the molecular chain is a group represented by the following formula (V), [1] to [17]. Curable resin composition.
^{* -S-L 1 -X 1 (} V)
In formula (V), S is a sulfur atom, L ¹ represents a divalent linking group, X ¹ represents a reactive silyl group, and * represents a bonding position.
[19] In any one of [1] to [18], the total number of the reactive silyl groups in the vinyl polymer (A) is more than 1 and less than 1.80 per molecule on average. The curable resin composition described.
[20] Further, containing a plasticizer,
The plasticizer contains at least a polyoxyalkylene polyol having a number average molecular weight of 1,500 to 15,000,
The curable resin composition according to any one of [1] to [19], wherein the mass ratio of the plasticizer to the vinyl polymer (B) is 0.1 or more and less than 1.0.
[21] The curable resin composition according to any one of [1] to [20], which is used as an adhesive.
[22] A sealing material containing the curable resin composition according to any one of [1] to [20], which is used as a sealing material.

The curable resin composition of the present invention has excellent weather resistance, cured physical properties, and workability.

The present invention will be described in detail below.
In addition, in this specification, (meth)acrylate represents acrylate or methacrylate, (meth)acryloyl represents acryloyl or methacryloyl, and (meth)acryl represents acryl or methacryl. Poly(meth)acrylate represents polyacrylate, polymethacrylate, or a copolymer of acrylate and methacrylate.
Further, in the present specification, the numerical range represented by using "to" means a range including the numerical values before and after "to" as the lower limit value and the upper limit value.
In the present specification, the method for producing each component is not particularly limited. For example, conventionally known ones can be mentioned.
In the present specification, unless otherwise specified, each component may be a single substance corresponding to the component or a combination of two or more types. When a component contains two or more substances, the content of the component means the total content of the two or more substances.

[Curable resin composition]
The curable resin composition of the present invention (the composition of the present invention) is
Having a reactive silyl group at the end and side chain of the molecular chain, the molecular chain has a repeating unit of a polymerizable vinyl monomer,
On average per molecule, the total number of reactive silyl groups exceeds 1, the number of reactive silyl groups at the terminals exceeds 0.5, and the number of reactive silyl groups in the side chains is 0. More than 5
A vinyl polymer (A) having a weight average molecular weight of 30,000 to 110,000, a number average molecular weight of 9,000 to 40,000, and a glass transition temperature of -100 to -10°C;
A vinyl polymer (B) having no reactive silyl group, a molecular chain having a repeating unit of a polymerizable vinyl monomer, and a weight average molecular weight of 20,000 or less;
Containing a curing catalyst (C),
The vinyl polymer (A) has a repeating unit of a polymerizable vinyl monomer in the molecular chain, and a vinyl polymer (a) having a group represented by the following formula (I) at the end of the molecular chain. It is a curable resin composition containing.
^{* -S-L 1 -X 1 (} I)
In formula (I), S is a sulfur atom, L ¹ represents a divalent linking group, X ¹ represents a reactive silyl group, and * represents a bonding position.

Since the composition of the present invention has such a constitution, it is considered that a desired effect can be obtained. The reason for this is not clear, but it is estimated to be approximately as follows.
Generally, when a polyoxyalkylene polymer having a reactive silyl group is exposed to an outdoor environment, the bond between carbon and oxygen in the polyoxyalkylene, which is the molecular chain (main chain), is affected by the external environment. And easy to cut. Therefore, the sealing material containing the polyoxyalkylene polymer usually has low weather resistance.

On the other hand, the vinyl polymer (A), the vinyl polymer (a) and the vinyl polymer (B) contained in the present invention are chemically stable as compared with polyoxyalkylene.
Further, since the vinyl polymer (A) has a large weight average molecular weight and/or number average molecular weight, even if the polyoxyalkylene polymer is cleaved in the molecular chain, it is obtained by the presence of the vinyl polymer (A). The elongation of the sealing material can be maintained within an appropriate range.
For the above reasons, it is assumed that the sealing material obtained by using the composition of the present invention has excellent weather resistance.

Further, the present invention is excellent in weather resistance, cured physical properties, and workability by containing the predetermined vinyl polymer (B).
The reason why the composition of the present invention is excellent in weather resistance and cured property by containing the vinyl polymer (B) is that the vinyl polymer (B) does not have a reactive silyl group (therefore, the vinyl polymer The polymer (B) does not undergo, for example, a hydrolysis condensation reaction or a hydrosilylation reaction with the reactive silyl group contained in the vinyl polymer (A).), and the molecular chain has a repeating unit of a polymerizable vinyl monomer. The present inventors presume that this is because when the weight average molecular weight is 20,000 or less, flexibility is imparted to the cured product.
In addition, the reason why the composition of the present invention is excellent in workability by containing the vinyl polymer (B) is that the vinyl polymer (B) does not have a reactive silyl group and the vinyl polymer (A And the vinyl polymer (B) have a high affinity because the main chain is a vinyl polymer, and the weight average molecular weight of the vinyl polymer (B) is 20,000 or less. The present inventors presume that this is because the viscosity of the composition is within an appropriate range.
Hereinafter, each component contained in the composition of the present invention will be described in detail.

<< vinyl polymer (A) >>
The vinyl polymer (A) contained in the composition of the present invention has a reactive silyl group at the terminal and side chain of the molecular chain, and the molecular chain has a repeating unit of a polymerizable vinyl monomer,
On average per molecule, the total number of reactive silyl groups exceeds 1, the number of reactive silyl groups at the terminals exceeds 0.5, and the number of reactive silyl groups in the side chains is 0. More than 5
It is a polymer having a weight average molecular weight of 30,000 to 110,000, a number average molecular weight of 9,000 to 40,000, and a glass transition temperature of -100 to -10°C.
The composition of the present invention is excellent in weather resistance because it contains the vinyl polymer (A).

<Molecular chain>
In the present invention, the vinyl polymer (A) has a molecular chain, and the molecular chain has a repeating unit of a polymerizable vinyl monomer.
Since the molecular chain has a repeating unit of a polymerizable vinyl monomer, the molecular chain (main chain or skeleton) can be substantially hydrocarbon.
In the present invention, the term “substantially” means that the molecular chain of the vinyl polymer (A) may further include a repeating unit other than —[C—C]—, but the above —[C—C ]- means that the content of the repeating unit of the vinyl polymer (A) is 50% by mass or more. The content of -[C-C]- is preferably 80% by mass or more based on the above total.

Examples of the molecular chain of the vinyl polymer (A) include poly(meth)acrylate-based polymers. The same applies to the molecular chain of the vinyl polymer (a).

The repeating unit of the polymerizable vinyl monomer that constitutes (the skeleton of) the molecular chain is not particularly limited as long as it is a repeating unit of a compound having a carbon-carbon double bond. For example, an olefin monomer such as ethylene; a (meth)acrylic monomer such as (meth)acrylate, (meth)acrylamide, or (meth)acrylic acid; a repeat with an aromatic vinyl monomer such as styrene The unit is mentioned.

In addition, at least a part of the repeating units constituting the molecular chain of the vinyl polymer (A) may have a reactive silyl group. When the repeating unit has a reactive silyl group, the vinyl polymer (A) can have the reactive silyl group in, for example, a side chain. Examples of the repeating unit having a reactive silyl group include a repeating unit of (meth)acrylate having a reactive silyl group.

(Repeating unit composed of (meth)acrylate monomer)
Among them, the repeating unit constituting the molecular chain (skeleton) of the vinyl polymer (A) is a repeating unit of a (meth)acrylate monomer from the viewpoint of being more excellent in weather resistance, cured physical properties or workability. It is preferable. The (meth)acrylate monomer (the repeating unit thereof) may have a reactive silyl group. The repeating unit (or (meth)acrylate monomer) composed of a (meth)acrylate monomer described later may have a reactive silyl group.

The (meth)acrylate monomer is not particularly limited as long as it is a (meth)acrylic acid ester. Examples of the hydrocarbon group constituting the ester portion of the (meth)acrylic acid ester include an aliphatic hydrocarbon group (linear, branched or cyclic), an aromatic hydrocarbon group, or a combination thereof. To be
When the (meth)acrylate monomer has a reactive silyl group, the reactive silyl group can be bonded to, for example, an ester residue in the (meth)acrylate monomer.

The ester residue (hydrocarbon group constituting the ester) in the (meth)acrylate monomer may have a hydrocarbon group having 1 to 12 carbon atoms from the viewpoint of being more excellent in weather resistance, cured physical properties or workability. preferable. However, when the (meth)acrylate monomer has a reactive silyl group in the ester residue, the ester residue in the (meth)acrylate monomer has a reactive silyl group The carbon number of the ester residue after removal is assumed.

Examples of the hydrocarbon group having 1 to 12 carbon atoms include aliphatic hydrocarbon groups such as propyl group, butyl group, pentyl group, hexyl group, octyl group, 2-ethylhexyl group, isononyl group and lauryl group; To a divalent or higher valent aliphatic hydrocarbon group.

(Molecular chain is linear)
The shape of the molecular chain of the vinyl polymer (A) is not particularly limited. The shape of the above-mentioned molecular chain is preferably a linear one from the viewpoint that it is more excellent in weather resistance, cured properties or workability.

<Reactive silyl group>
The reactive silyl group contained in the vinyl polymer (A) is not particularly limited as long as it has a silicon atom and is a reactive group. For example, a silyl group in which 1 to 3 hydrolyzable groups are bonded to a silicon atom may be mentioned.
The reactive silyl group contained in the vinyl polymer (A) is preferably a silyl group in which two hydrolyzable groups are bonded to one silicon atom from the viewpoint of being more excellent in weather resistance, cured physical properties or workability. The same applies to the reactive silyl group having a side chain or a terminal. The same applies to the reactive silyl group contained in the vinyl polymer (a).
Examples of the hydrolyzable group include hydrogen, a halogen atom, an alkoxy group, an acyloxide group, a ketoximate group, an amino group, an amide group, an acid amide group, an aminooxy group, a mercapto group, and an alkenyloxide group. Of these, an alkoxy group is preferable.

The reactive silyl group is preferably a dialkoxysilyl group, more preferably an alkyldialkoxysilyl group or a dimethoxysilyl group, from the viewpoint of being more excellent in weather resistance, cured physical properties or workability.

When one or two hydrolyzable groups are bonded to one silicon atom, the groups other than the hydrolyzable groups that can be bonded to the silicon atom are not particularly limited. For example, an aliphatic hydrocarbon group (linear, branched or cyclic), an aromatic hydrocarbon group, or a combination thereof can be mentioned. Of these, an aliphatic hydrocarbon group having 1 to 6 carbon atoms is preferable. Specific examples include a methyl group and an ethyl group.

(Reactive silyl group and molecular chain)
In the present invention, the vinyl polymer (A) has the reactive silyl group at the end and side chain of the molecular chain.
The reactive silyl group can be bonded to the end of the molecular chain directly or through an organic group. The organic group is not particularly limited.
The reactive silyl group can be bonded to the side chain of the molecular chain directly or through an organic group. The organic group is not particularly limited.
In the above vinyl polymer (A), from the viewpoint of excellent weather resistance and/or workability and excellent elongation of a cured product to be obtained, a reactive silyl group at a terminal and a reactive silyl group at a side chain are At least one of them is preferably a dialkoxysilyl group, and more preferably a dimethoxysilyl group.
In the dialkoxysilyl group (or the dimethoxysilyl group), another hydrocarbon group that can be bonded to a silicon atom is not particularly limited. For example, an alkyl group is mentioned. When the dialkoxysilyl group (or the dimethoxysilyl group) has an alkyl group as another hydrocarbon group that can be bonded to the silicon atom, it becomes an alkyldialkoxysilyl group (or an alkyldimethoxysilyl group).
In the above vinyl polymer (A), from the viewpoint of excellent weather resistance and/or workability and excellent elongation of a cured product to be obtained, a reactive silyl group at the terminal and a reactive silyl group at the side chain are It is preferred that all are dialkoxysilyl groups.

The vinyl polymer (A) is, for example, a mixture of vinyl polymers having the reactive silyl group at the terminal or side chain of the molecular chain; vinyl polymer having the reactive silyl group at the terminal or side chain of the molecular chain. A vinyl polymer having the reactive silyl group at the terminal or side chain of the molecular chain, or a mixture of vinyl polymers having the reactive silyl group at the terminal or side chain of the molecular chain.

<Total number of reactive silyl groups>
In the present invention, the total number of the reactive silyl groups that the vinyl polymer (A) has per molecule on average exceeds one.
The total number of the reactive silyl groups is the average number of the reactive silyl groups per molecule of the vinyl polymer (A) in the entire vinyl polymer (A).

From the viewpoint of being more excellent in weather resistance, cured physical properties or workability, the above total number is preferably more than 1 and 3 or less on average, more preferably more than 1 and 2 or less on average. And more than 1.80 are more preferable.
The total number of the reactive silyl groups can be the total number of the number of reactive silyl groups at the terminal and the number of reactive silyl groups at the side chain, which will be described later.

In the present invention, the number (total number) of reactive silyl groups is theoretically determined from the composition ratio of the monomers and the chain transfer agent used in the production of the vinyl polymer (A) and the number average molecular weight (Mn). It can be calculated by calculating the number of reactive silyl groups and the group represented by the formula (I) per molecule of the polymer. Regarding the vinyl polymer (A) described later, the number of the reactive silyl groups at the terminal or side chain, the number of the group represented by the formula (V) at the terminal; the vinyl polymer (a) described below is The number of reactive silyl groups and the number of groups represented by formula (I) at the terminal are also the same.

<Reactive silyl group at terminal>
The vinyl polymer (A) has a reactive silyl group at the terminal from the viewpoint of excellent weather resistance, cured physical properties or workability.

When the reactive silyl group is bonded to the terminal of the molecular chain of the vinyl polymer (A) through an organic group, the group having the reactive silyl group is represented by the following formula (V). Groups.

^{* -S-L 1 -X 1 (} V)
In formula (V), S is a sulfur atom, L ¹ represents a divalent linking group, X ¹ represents a reactive silyl group, and * represents a bonding position.

The above formula (V) is the same as the group represented by the formula (I) which the vinyl polymer (a) described later has at the end of the molecular chain.

<Number of reactive silyl groups at the end>
In the present invention, the number of the above-mentioned reactive silyl groups that the vinyl polymer (A) has at the end on average per molecule exceeds 0.5.
The number of the above-mentioned reactive silyl groups is the number of the above-mentioned reactive silyl groups that the vinyl polymer (A) has at the end on average per molecule in the whole vinyl polymer (A).
From the viewpoint of being more excellent in weather resistance, cured physical properties or workability, the above number is preferably more than 0.5 and not more than 2 on average, and more preferably 0.6 to 1.0. , 0.6 or more and less than 0.9 are more preferable.

<Reactive silyl group in side chain>
The vinyl polymer (A) has a reactive silyl group in its side chain from the viewpoint of excellent weather resistance, cured physical properties, and workability.

When the reactive silyl group is bonded to the side chain of the molecular chain of the vinyl polymer (A) through an organic group, the group having the reactive silyl group is, for example, represented by the following formula (IV). Group.

* -L ⁴ -X ⁴ (IV)
In formula (IV), L ⁴ represents a divalent linking group, X ⁴ represents a reactive silyl group, and * represents a bonding position.
L ⁴ of formula (IV) is the same as L ^{3 of} formula (III) described later.
X ^{4 in} formula (IV) is the same as X ^{1 in} formula (I), which represents a group at the end of the molecular chain of the vinyl polymer (a) described later.

<Number of reactive silyl groups in the side chain>
In the present invention, the number of the reactive silyl groups in the side chain of the vinyl polymer (A) is more than 0.5 per molecule on average.
The number of the reactive silyl groups is the number of the reactive silyl groups that the vinyl polymer (A) has in the side chain on average per molecule in the entire vinyl polymer (A).
From the viewpoint of being more excellent in weather resistance, cured physical properties or workability, the above number is preferably more than 0.5 and not more than 2 on average, and more preferably 0.6 to 1.0. , 0.6 or more and less than 0.9 are more preferable.

(Another side chain)
The vinyl polymer (A) preferably further has a hydrocarbon group in its side chain from the viewpoint of being more excellent in weather resistance, cured physical properties or workability. The above hydrocarbon group does not have a reactive silyl group.
Examples of the hydrocarbon group include an aliphatic hydrocarbon group (linear, branched or cyclic), an aromatic hydrocarbon group, or a combination thereof. Specific examples thereof include a hydrocarbon group having 1 to 8 carbon atoms. The hydrocarbon group is preferably an aliphatic hydrocarbon group having 1 to 8 carbon atoms.

The hydrocarbon group can be bonded to the molecular chain directly or via an organic group.
The organic group is not particularly limited. Examples thereof include ester bond, amide bond, ether bond and carbonyl group.

(Repeating unit constituting vinyl polymer (A))
-Repeating Unit Represented by Formula (III) The molecular chain of the vinyl polymer (A) has a repeating unit represented by formula (III) from the viewpoint of being more excellent in weather resistance, cured physical properties or workability. Is preferred.

In formula (III), R ^3-1 represents a hydrogen atom or a monovalent hydrocarbon group, L ³ represents a divalent linking group, and R ^3-2 and R ^3-3 each independently represent a monovalent hydrocarbon group. It represents a hydrocarbon group, m3 is 1-3, n3 is 0-2, and m3+n3 is 3.

・R ^3-1
In formula (III), R ^3-1 represents a hydrogen atom or a monovalent hydrocarbon group.
Examples of the monovalent hydrocarbon group include an aliphatic hydrocarbon group such as a methyl group.

・L ³
In formula (III), L ³ represents a divalent linking group.
Examples of the divalent linking group as L ³ include a divalent hydrocarbon group L ^3-1 ; a substituent L ^3-2 such as an ester bond, an amide bond, an ether bond and a carbonyl group.
Examples of the divalent hydrocarbon group L ^3-1 include an aliphatic hydrocarbon group (linear, branched or cyclic), an aromatic hydrocarbon group, or a combination thereof. Specific examples thereof include an aliphatic hydrocarbon group having 1 to 8 carbon atoms.

Examples of L ³ include a combination of a divalent hydrocarbon group L ^3-1 and a substituent L ^3-2 .
Of these, a combination of a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms and an ester bond is preferable.

・R ^3-2 , R ^3-3
In formula (III), R ^3-2 and R ^3-3 each independently represent a monovalent hydrocarbon group.
Examples of the monovalent hydrocarbon group include an aliphatic hydrocarbon group (linear, branched or cyclic), an aromatic hydrocarbon group, or a combination thereof.
Of these, aliphatic hydrocarbon groups such as methyl group and ethyl group are preferable.

・M3
In the formula (III), m3 is 1 to 3.
m3 is preferably 2 from the viewpoint that it is more excellent in weather resistance, cured physical properties or workability, and that the pot life can be secured with an appropriate length.

・N3
In the formula (III), n3 is 0 to 2.
n3 is preferably 1 from the viewpoint that it is more excellent in weather resistance, cured physical properties or workability, and that the pot life can be secured with an appropriate length.

Examples of the group represented by the above formula (III) include groups represented by the following formula (III-1).

In formula (III-1), R ^3-1 represents a hydrogen atom or a monovalent hydrocarbon group, R ^3-2 and R ^3-3 each independently represent a monovalent hydrocarbon group, and R ^{3- 4} represents a divalent hydrocarbon group, m3 is 1 to 3, n3 is 0 to 2, and m3+n3 is 3.
R ^3-1 of formula ^{(III-1), R 3-2} , R 3-3, m3, n3 are the same as the formula (III).
R ^{3-4 in} formula (III-1) is the same as the above divalent hydrocarbon group L ^3-1 . Of these, a propylene group is preferred.

-Repeating Unit Represented by Formula (II) The molecular chain of the vinyl polymer (A) further includes a repeating unit represented by the following formula (II) as a repeating unit of the (meth)acrylate monomer. Can have units.

In formula (II), R ^2-1 represents a hydrogen atom or a monovalent hydrocarbon group, L ² represents a divalent linking group, and R ^2-2 represents a monovalent hydrocarbon group.

・R ^2-1
In the formula (II), R ^2-1 represents a hydrogen atom or a monovalent hydrocarbon group.
Examples of the monovalent hydrocarbon group include an aliphatic hydrocarbon group such as a methyl group.

・L ²
In formula (II), L ² represents a divalent linking group.
Examples of the divalent linking group include an ester bond, an amide bond, an ether bond and a carbonyl group.
Of these, an ester bond is preferable.

・R ^2-2
In the formula (II), R ^2-2 represents a monovalent hydrocarbon group.
Examples of the monovalent hydrocarbon group include an aliphatic hydrocarbon group (linear, branched or cyclic), an aromatic hydrocarbon group, or a combination thereof.
R ^2-2 is preferably a hydrocarbon group having 1 to 12 carbon atoms, and more preferably a hydrocarbon group having 4 to 8 carbon atoms, from the viewpoint of being more excellent in weather resistance, cured physical properties or workability.
Specific examples of R ^2-2 include an aliphatic hydrocarbon group such as a butyl group, a pentyl group, a hexyl group, an octyl group, a 2-ethylhexyl group, an isononyl group, and a lauryl group. Of these, a butyl group, a pentyl group, a hexyl group, an octyl group and a 2-ethylhexyl group are preferable.

<Weight average molecular weight>
In the present invention, the weight average molecular weight of the vinyl polymer (A) is 30,000 to 110,000.
When the weight average molecular weight is within the above range, the composition of the present invention has excellent weather resistance, cured physical properties and workability.

The weight average molecular weight of the vinyl polymer (A) is preferably 45,000 to 100,000, from the viewpoint that weather resistance, cured physical properties or workability are excellent, and the initial elongation of the cured product can be maintained for a long period of time. More preferably, it is 50,000 to 90,000.
Further, the weight average molecular weight of the vinyl polymer (A) is preferably 45,000 to 100,000, and more preferably 60,000 to 90,000, from the viewpoint of being more excellent in weather resistance, cured product properties or workability.

<Number average molecular weight>
In the present invention, the vinyl polymer (A) has a number average molecular weight of 9,000 to 40,000.

The number average molecular weight of the vinyl polymer (A) is more excellent in weather resistance (particularly longer-term weather resistance), cured physical properties or workability, and the initial elongation of the cured product can be maintained for a long period of time. It is preferably more than 1,000 and less than 20,000, more preferably 16,000 or more and less than 20,000.

In the present invention, the vinyl polymer (A) was analyzed by the gel permeation chromatography (GPC) method, and the weight average molecular weight or the number average molecular weight of the vinyl polymer (A) was calculated by polystyrene conversion under the following conditions.

-Device: GPC-8220 (manufactured by Tosoh Corporation)
-Column: One G7000HXL/7.8mmID, two GMHXL/7.8mmID and one G2500HXL/7.8mmID were used.
・Medium: Tetrahydrofuran ・Flow rate: 1.0 mL/min
・Concentration: 1.5 mg/ml
・Injection volume: 300 μL
・Column temperature: 40℃

In the present invention, the glass transition temperature (Tg) of the vinyl polymer (A) is -100 to -10°C.
When the glass transition temperature is within the above range, the composition of the present invention has excellent weather resistance, cured physical properties and workability.

The glass transition temperature is preferably −60 to −10° C. from the viewpoint of being more excellent in weather resistance, cured physical properties or workability.

In the present invention, for the glass transition temperature (Tg) of the vinyl polymer (A), a differential thermal analysis (DTA) or a differential scanning calorimeter (DSC) is used, and the sample (vinyl polymer (A)) is kept at a constant rate. It is possible to derive the Tg of the sample by raising the temperature at, and measuring the intersection of the tangent line of the baseline in the DTA curve or the DSC curve and the tangent line of the steep descending position of the endothermic region due to glass transition.

<<vinyl polymer (a)>>
In the present invention, the vinyl polymer (A) includes the vinyl polymer (a).
In the present invention, the vinyl polymer (a) is a polymer whose molecular chain has a repeating unit of a polymerizable vinyl monomer and which has a group represented by the following formula (I) at the terminal of the molecular chain. ..
^{* -S-L 1 -X 1 (} I)
In formula (I), S is a sulfur atom, L ¹ represents a divalent linking group, X ¹ represents a reactive silyl group, and * represents a bonding position.

<Molecular chain>
In the present invention, the molecular chain of the vinyl polymer (a) has a repeating unit of a polymerizable vinyl monomer.
The molecular chain of the vinyl polymer (a) can be the same as the molecular chain of the vinyl polymer (A).
The repeating unit of the polymerizable vinyl monomer contained in the molecular chain of the vinyl polymer (a) can be the same as the repeating unit of the polymerizable vinyl monomer contained in the molecular chain of the vinyl polymer (A). ..

-Side chain The vinyl polymer (a) preferably has a reactive silyl group in its side chain from the viewpoint of being more excellent in weather resistance, cured physical properties or workability.

-Number of reactive silyl groups in the side chain The number of reactive silyl groups in the side chain of the vinyl polymer (a) can be 0 to 2 per molecule of the vinyl polymer (a).
The number of reactive silyl groups in the side chain of the vinyl polymer (a) is preferably 1 to 2 per molecule of the vinyl polymer (a) from the viewpoint of being more excellent in weather resistance, cured physical properties or workability. ..

The reactive silyl group that the vinyl polymer (a) can have in the side chain can be the same as the reactive silyl group that the vinyl polymer (A) has in the side chain.

<End>
In the present invention, the vinyl polymer (a) has a group represented by the following formula (I) at the terminal of the molecular chain.
^{* -S-L 1 -X 1 (} I)
In formula (I), S is a sulfur atom, L ¹ represents a divalent linking group, X ¹ represents a reactive silyl group, and * represents a bonding position.

・L ¹
In formula (I), L ¹ represents a divalent linking group.
Examples of the divalent linking group include those similar to the above divalent hydrocarbon group L ^3-1 .
Of these, a propylene group is preferred.

・X ¹
In the formula (I), X ¹ represents a reactive silyl group.
The reactive silyl group is not particularly limited. For example, the same thing as the above is mentioned.

The reactive silyl group as X ¹ is preferably a dialkoxysilyl group, more preferably an alkyldialkoxysilyl group, and even more preferably a methyldimethoxysilyl group, from the viewpoint of being excellent in weather resistance, cured physical properties or workability.

*
In formula (I), * represents a bonding position.
In the present invention, the vinyl polymer (a) has a group represented by the above formula (I) at the terminal of the molecular chain. The group represented by the above formula (I) can be bonded to the terminal of the molecular chain of the above vinyl polymer (a) in the above *.

The group represented by the above formula (I) can be bonded to the terminal of the molecular chain of the above vinyl polymer (a) directly or through an organic group. The organic group is not particularly limited.

The vinyl polymer (a) preferably has one or more reactive silyl groups per molecule (on average). The reactive silyl group is the same as above.
The number of reactive silyl groups per molecule (on average) in the vinyl polymer (a) is preferably 1 to 6 from the viewpoint of being more excellent in weather resistance, cured physical properties or workability.

The vinyl polymer (a) preferably has one terminal having a group represented by the formula (I) from the viewpoint of being more excellent in weather resistance, cured physical properties or workability.
The residue due to the polymerization initiator used when producing the vinyl polymer (A) may be bonded to the other end of the vinyl polymer (a).
In addition, in the vinyl polymer (A), for example, a residue due to the polymerization initiator used when producing the vinyl polymer (A) may be bonded to the terminal.

-Formula (I-1)
The group represented by the formula (I) is preferably a group represented by the following formula (I-1) from the viewpoint of being more excellent in weather resistance, cured physical properties or workability.
In formula (I-1), R ^1-1 represents a divalent hydrocarbon group, R ^1-2 and R ^1-3 each independently represent a monovalent hydrocarbon group, and m1 is 1 to 3 Yes, n1 is 0 to 2, m1+n1 is 3, and * represents a bonding position.

・R ^1-1
In formula (I-1), R ^1-1 represents a divalent hydrocarbon group.
Examples of the divalent hydrocarbon group include an aliphatic hydrocarbon group (linear, branched or cyclic), an aromatic hydrocarbon group, or a combination thereof. Especially, a C1-C6 aliphatic hydrocarbon group is preferable and a propylene group is more preferable.

・R ^1-2 , R ^1-3
In formula (I-1), R ^1-2 and R ^1-3 each independently represent a monovalent hydrocarbon group.
Examples of the monovalent hydrocarbon group include an aliphatic hydrocarbon group (linear, branched or cyclic), an aromatic hydrocarbon group, or a combination thereof.
Of these, aliphatic hydrocarbon groups such as methyl group and ethyl group are preferable.

・M1
In the formula (I-1), m1 is 1 to 3.
m1 is preferably 2 from the viewpoint that it is more excellent in weather resistance, cured properties or workability, and that the pot life can be secured with an appropriate length.

・N1
In the formula (I-1), n1 is 0 to 2.
n1 is preferably 1 from the viewpoint that it is more excellent in weather resistance, cured physical properties or workability, and that the pot life can be secured with an appropriate length.

*
In formula (I-1), * represents a bonding position. * In formula (I-1) is the same as * in formula (I).

The weight average molecular weight, number average molecular weight or glass transition temperature of the vinyl polymer (a) can be the same as those of the vinyl polymer (A).

In the present invention, all or part of the vinyl polymer (A) may be the vinyl polymer (a).
When a part of the vinyl polymer (A) is the vinyl polymer (a), the vinyl polymer (A) has a polymerizable vinyl monomer whose molecular chain is in addition to the vinyl polymer (a). It may further include a vinyl polymer (a′) having a repeating silyl group according to the above and having a reactive silyl group at the terminal and/or side chain (excluding the above vinyl polymer (a)).
The vinyl polymer (a') may be a by-product in producing the vinyl polymer (A).

-Content of vinyl polymer (a) The content of the vinyl polymer (a) can be 0.1 to 100 mass% with respect to the entire vinyl polymer (A).

(Method for producing vinyl polymer (A))
The method for producing the vinyl polymer (A) is not particularly limited. For example, the vinyl polymer (A) can be produced by polymerizing the polymerizable vinyl monomer in the presence of a polymerization initiator and a chain transfer agent.

-Polymerizable vinyl monomer The polymerizable vinyl monomer is not particularly limited as long as it is a compound having a carbon-carbon double bond.
Examples of the polymerizable vinyl monomer include compounds represented by the following formula (III′). As the polymerizable vinyl monomer, for example, a compound represented by the following formula (II′) can be used. As a preferred embodiment, the compound represented by the following formula (III′) and the compound represented by the following formula (II′) are used in combination as the polymerizable vinyl monomer.

The repeating unit represented by the above formula (II) can be formed by the compound represented by the above formula (II′).
The repeating unit represented by the above formula (III) can be formed by the compound represented by the above formula (III′).

- The chain transfer agent The chain transfer agent, for example, formula (I '): a compound represented by HS-L ¹ -X ¹ can be mentioned.
The group represented by the above formula (I) can be formed at the terminal of the vinyl polymer (a) by the compound represented by the above formula (I′). The same applies to the vinyl polymer (A).

-Amount of the compound represented by the formula (III') used When the compound represented by the formula (II') and the compound represented by the formula (III') are used in combination as the polymerizable vinyl monomer, The amount of the compound represented by the formula (III′) to be used is 0. 0 with respect to 100 parts by mass of the compound represented by the formula (II′) from the viewpoint of being more excellent in weather resistance, cured product properties or workability. The amount is preferably 1 to 100 parts by mass, more preferably 0.4 to 2.0 parts by mass, and even more preferably 0.5 to 1.5 parts by mass.

When the molecular chain (main chain) of the vinyl polymer (A) has a repeating unit represented by the formula (II) and a repeating unit represented by the formula (III), the vinyl polymer ( The molar ratio of the compound represented by the above formula (II′) to the compound represented by the above formula (III′), which is used in the production of A), is determined by the molecular chain of the above vinyl polymer (A). It can be reflected in the number of repeating units represented by the above formula (II) and the repeating unit represented by the formula (III), which constitutes the (main chain).

-Amount of chain transfer agent used The amount of the chain transfer agent used is 0.2 to 100 parts by mass of the total amount of the polymerizable vinyl monomer, from the viewpoint of being more excellent in weather resistance, cured physical properties or workability. The amount is preferably 5 parts by mass, more preferably 0.8 to 3.6 parts by mass.
By reducing the amount of the chain transfer agent used, the weight average molecular weight and/or the number average molecular weight of the vinyl polymer (A) can be increased.

-Polymerization initiator The above-mentioned polymerization initiator is not particularly limited. Examples thereof include azo compounds such as azobisisobutyronitrile, organic peroxides, and metallocene catalysts.
The amount of the polymerization initiator used is not particularly limited.
The amount of the polymerization initiator used is preferably 0.05 to 5.0 parts by mass, and 0.1 to 3.0 parts by mass, based on 100 parts by mass of the total amount of the polymerizable vinyl monomer. Is more preferable.

In the above production method, a solvent can be used if necessary.

The vinyl polymer (A) may be mentioned as one of preferred embodiments having no urethane bond or urea bond. The same applies to the vinyl polymer (a).

<< vinyl polymer (B) >>
The vinyl polymer (B) contained in the composition of the present invention does not have a reactive silyl group, has a repeating unit of a polymerizable vinyl monomer in its molecular chain, and has a weight average molecular weight of 20,000. The polymer is
By containing the vinyl polymer (B), the composition of the present invention is excellent in weather resistance, cured physical properties, workability, and heat resistance.

<Molecular chain>
In the present invention, the vinyl polymer (B) has a molecular chain, and the molecular chain has a repeating unit of a polymerizable vinyl monomer.
Since the molecular chain has a repeating unit of a polymerizable vinyl monomer, the molecular chain (main chain or skeleton) can be substantially hydrocarbon.
In the present invention, the term “substantially” means that the molecular chain of the vinyl polymer (B) may further include a repeating unit other than —[C—C]—. ]- means that the content of the repeating unit of the vinyl polymer (A) is 50% by mass or more. The content of -[C-C]- is preferably 80% by mass or more based on the above total.

The repeating unit of the polymerizable vinyl monomer that constitutes (the skeleton of) the molecular chain is not particularly limited as long as it is a repeating unit of a compound having a carbon-carbon double bond.
Specifically, for example, an olefin monomer such as ethylene;
(Meth) acrylates, (meth) acrylamide, (meth) such as acrylic _{acid, CH 2 = CR-CO- (} R is a hydrogen atom or a methyl group) having a (meth) acrylic monomer;
The repeating unit may be an aromatic vinyl monomer such as styrene.

Examples of the molecular chain of the vinyl polymer (B) include (meth)acrylic polymers.
The repeating unit constituting the (meth)acrylic polymer is not particularly limited as long as it is a repeating unit of the (meth)acrylic monomer.

(Molecular chain is linear)
The shape of the molecular chain of the vinyl polymer (B) is not particularly limited. The shape of the above-mentioned molecular chain is preferably a linear one from the viewpoint that it is more excellent in weather resistance, cured properties or workability.

<No reactive silyl group>
In the present invention, the vinyl polymer (B) does not have a reactive silyl group.
Therefore, the vinyl polymer (B) does not undergo, for example, a hydrolysis condensation reaction or a hydrosilylation reaction with the reactive silyl group contained in the vinyl polymer (A).
Since the vinyl polymer (B) does not have a reactive silyl group, the composition of the present invention has excellent weather resistance, cured physical properties (e.g., elongation of cured product), and workability.

Further, the vinyl polymer (B) is preferably a non-functional group-type (meth)acrylic polymer from the viewpoint of being excellent in weather resistance, cured physical properties or workability.
The non-functional group-type (meth)acrylic polymer means a (meth)acrylic polymer having no functional group.
Examples of the functional group include, in addition to the reactive silyl group, a hydroxy group, a carboxy group, an epoxy group, and a vinyl group.
In addition, the vinyl polymer (B) can be mentioned as one of preferred embodiments in which it does not have a silicon atom.

<Weight average molecular weight>
In the present invention, the weight average molecular weight of the vinyl polymer (B) is 20,000 or less.
When the weight average molecular weight is within the above range, the composition of the present invention has excellent weather resistance, cured physical properties, workability, and heat resistance.

The weight average molecular weight of the vinyl polymer (B) is excellent in weather resistance, cured product properties or workability, is excellent in heat resistance, and can maintain the initial elongation of the cured product for a long period of time. From the viewpoint that B) is less likely to bleed out and has excellent stain resistance, 1,000 to 10,000 is preferable, and 1,500 to 8,000 is more preferable.
The weight average molecular weight of the vinyl polymer (B) is excellent in cured physical properties or workability, is excellent in heat resistance, and can maintain the initial elongation of the cured product for a long period of time. From the viewpoint of being less likely to bleed out and being excellent in stain resistance, it is preferably 4,000 to 10,000.

In the present invention, the weight average molecular weight of the vinyl polymer (B) is a standard polystyrene conversion value based on the value measured by gel permeation chromatography (GPC) using tetrahydrofuran (THF) as a solvent.

(Content of vinyl polymer (B))
The content of the vinyl polymer (B) is excellent in weather resistance, cured physical properties or workability, is excellent in heat resistance, and can maintain the initial elongation of the cured product for a long period of time. ) Is less likely to bleed out and has excellent stain resistance, is preferably 1 to 100 parts by mass, and more preferably 2 to 90 parts by mass, relative to 100 parts by mass of the vinyl polymer (A). The amount is preferably 5 to 80 parts by mass, more preferably 40 to 70 parts by mass.
Further, the content of the vinyl polymer (B) is 45 to 58 parts by mass with respect to 100 parts by mass of the vinyl polymer (A) from the viewpoint of excellent balance between cured physical properties and workability in addition to the above viewpoints. Is preferred.

<<Curing catalyst (C)>>
The curing catalyst (C) contained in the composition of the present invention is not particularly limited as long as it is a catalyst capable of acting on the reactive silyl group or the group represented by the formula (I).

As the curing catalyst (C), for example, a catalyst which hydrolyzes and/or condenses a hydrolyzable silyl group, or a conventionally known catalyst generally used as a silanol condensation catalyst can be used. For example, a tin compound, a titanium compound, an acidic compound, and an amine compound may be mentioned.

Among them, tin compounds are preferable from the viewpoint of excellent curing speed and/or storage stability.
Examples of the tin compound include a tetravalent dialkyltin compound (eg, dimethyltin compound, dibutyltin compound, dioctyltin compound),
Reaction product of dibutyltin oxide and phthalic acid ester,
Dialkylstanoxane dicarboxylate,
Dialkyltin alcoholates, such as dibutyltin dimethoxide,
(Dialkylstannoxane) disilicate compound,
Tetravalent dialkyltin compounds such as dialkyltin chelates such as dibutyltin diacetylacetonate;
Tetravalent monoalkyltin compounds such as monobutyltin tris octoate, monobutyltin triisopropoxide, monooctyltin compounds, etc.;
Examples include divalent tin compounds such as tin octylate, tin naphthenate, tin stearate and the like.

-Content of the curing catalyst (C) The content of the curing catalyst (C) is from 0. 0 to 100 parts by mass of the vinyl polymer (A) from the viewpoint of being more excellent in weather resistance, cured physical properties or workability. The amount is preferably 1 to 20 parts by mass, more preferably 0.1 to 5.0 parts by mass.

(Resin hollow body)
The composition of the present invention preferably further contains a resin hollow body (resin balloon) from the viewpoint of being more excellent in workability.

The hollow resin body has an outer shell made of resin and a hollow interior.
The hollow resin body can function as a filler.
Examples of the material for the outer shell of the resin hollow body include phenol resin; urea resin; polystyrene resin; polyvinylidene chloride; acrylonitrile copolymer (for example, acrylonitrile-methacrylonitrile copolymer, acrylonitrile and acrylonitrile). Copolymerizable butadiene, copolymers with vinyl monomers such as styrene, etc.), and thermoplastic resins such as vinylidene chloride polymers.
The material of the outer shell of the resin-based hollow body is preferably an acrylonitrile copolymer from the viewpoint of being more excellent in weather resistance and/or workability.
The average particle diameter of the resin-based hollow body may be 20 μm or more, and is preferably 20 to 70 μm.
The average particle size of the resin hollow body can be measured by a laser diffraction method.
The true specific gravity of the resin-based hollow body is preferably 0.05 to 0.35 from the viewpoint of being more excellent in workability.

The hollow resin body may be expanded by heating. The temperature (heat resistant temperature) at which the hollow resin body can start expanding can be, for example, 100 to 190°C.

The hollow resin body may be coated with a filler such as calcium carbonate, talc, or titanium oxide.
The hollow resin body is preferably coated with the filler from the viewpoint of being more excellent in weather resistance and/or workability.

The method for producing the resin-based hollow body is not particularly limited, and can be produced by a conventionally known method.
Examples of commercially available products of the hollow resin body include MFL-60CAS manufactured by Matsumoto Yushi-Seiyaku Co., Ltd.

The content of the resin hollow body is preferably 1 to 30 parts by mass and preferably 1 to 10 parts by mass with respect to 100 parts by mass of the vinyl polymer (A) from the viewpoint of being more excellent in workability. Is more preferable, and 1 to 5 parts by mass is further preferable.

(Anti-aging agent)
The composition of the present invention preferably further contains an antioxidant from the viewpoint of being more excellent in weather resistance, cured physical properties or workability.

Examples of the antiaging agent include hindered amines (HALS) such as amino and amino ether derivatives of 2,2,6,6-tetramethylpiperidine;
A hindered phenol such as 2,4,6-tris-(N-1,4-dimethylpentyl-p-phenylenediamino)-1,3,5-triazine;
Butyl hydroxytoluene (BHT), butyl hydroxytoluene anisole (BHA), benzotriazole, 2-(5-chloro-2H-benzotriazol-2-yl)-4-methyl-6-tert-butylphenol and the like can be mentioned.

The content of the anti-aging agent is preferably 0.1 to 20 parts by mass with respect to 100 parts by mass of the vinyl polymer (A), from the viewpoint of excellent prevention of cracks on the surface of the sealing material, and is preferably 0. The amount is more preferably 1 to 10 parts by mass, further preferably 0.1 to 5 parts by mass.

-Plasticizer The composition of the present invention may further contain a plasticizer from the viewpoint of being more excellent in weather resistance, cured properties or workability. From the same viewpoint as above, the composition of the present invention preferably further contains a plasticizer.
It is mentioned as one of the preferred embodiments that the plasticizer does not have a reactive silyl group.
The vinyl polymer (A) or the vinyl polymer (B) does not correspond to the plasticizer.
The plasticizer is not particularly limited. For example, an oxyalkylene polymer may be mentioned.

Examples of the oxyalkylene polymer include polyoxyalkylene polyols such as polyethylene glycol and polypropylene glycol.

The number average molecular weight of the plasticizer is preferably 1,500 to 15,000 from the viewpoint of being more excellent in weather resistance, cured physical properties or workability.
The weight average molecular weight of the plasticizer is preferably 1,500 to 15,000 from the viewpoint of being more excellent in weather resistance, cured physical properties or workability.
The number average molecular weight or the weight average molecular weight of the plasticizer is a standard polystyrene conversion value based on the value measured by gel permeation chromatography (GPC) using tetrahydrofuran (THF) as a solvent.

.. Content of plasticizer The content of the plasticizer is 1 to 100 parts by mass with respect to 100 parts by mass of the vinyl polymer (A) from the viewpoint of being more excellent in weather resistance, cured product properties or workability. It is preferable that the amount is 10 to 30 parts by mass.
..Mass ratio of plasticizer to vinyl polymer (B) (plasticizer/vinyl polymer (B))
When the composition of the present invention further contains a plasticizer, the mass ratio of the plasticizer to the vinyl polymer (B) (plasticizer/vinyl polymer (B)) depends on weather resistance, cured physical properties or workability. From the viewpoint of being excellent, 0.1 or more and less than 1.0 is preferable, 0.10 to 0.50 is more preferable, and 0.10 to 0.30 is further preferable.

-Additive The composition of the present invention may further contain an additive. Examples of the above-mentioned additives include fillers such as calcium carbonate and carbon black (excluding the above resin hollow bodies); viscosity reducing agents such as solvents; titanium oxide, silane coupling agents, adhesion imparting agents, sagging agents. Examples include antioxidants, ultraviolet absorbers, antioxidants, and pigments.
The content of the filler (excluding the resin hollow body) is 10 to 300 parts by mass with respect to 100 parts by mass of the total amount of the vinyl polymer (A) and the vinyl polymer (B). Is preferred.

-Silane coupling agent The composition of the present invention preferably further contains a silane coupling agent from the viewpoint of excellent curability, adhesiveness or storage stability.
Examples of the silane coupling agent include vinyl group-containing silane coupling agents, amino group- and/or imino group-containing silane coupling agents, (meth)acryloyl group-containing silane coupling agents, and mercapto group-containing silane coupling agents. , And an isocyanate group-containing silane coupling agent.

The content of the silane coupling agent is 0.1 to 10 parts by mass with respect to 100 parts by mass of the vinyl polymer (A) from the viewpoint of excellent curability, adhesiveness, and storage stability. It is more preferably 0.1 to 5 parts by mass.

The composition of the present invention has, as one of preferred embodiments, having a reactive silyl group and containing substantially no polyoxyalkylene polymer having a molecular chain of polyoxyalkylene.
That the composition of the present invention does not substantially contain the polyoxyalkylene polymer means that the content of the polyoxyalkylene polymer is 0 to 0.1% by mass with respect to the total amount of the composition of the present invention. Means there is.

Further, the composition of the present invention has a reactive silyl group, a urethane bond and/or a urea bond, and has at least one selected from the group consisting of polyoxyalkylene, polyester, polycarbonate and polyvinyl as a molecular chain. It is mentioned as one of the preferred embodiments that substantially no organic polymer is contained.
The fact that the composition of the present invention does not substantially contain the organic polymer means that the content of the organic polymer is 0 to 0.1% by mass with respect to the total amount of the composition of the present invention. To do.

(Production method)
The method for producing the composition of the present invention is not particularly limited.
For example, the composition of the present invention can be produced by mixing the vinyl polymer (A), the vinyl polymer (B), and the curing catalyst (C). The above optional components (components other than the above vinyl polymer (A), the above vinyl polymer (B) and the above curing catalyst (C)) can be further used if necessary.
About the said manufacturing method, the said vinyl polymer (B) can be added to the said vinyl polymer (A), or the said vinyl polymer (A) can be added to the said vinyl polymer (B). The timing of adding the curing catalyst (C) or the optional component in the production method is not particularly limited.

(Applicable substrate)
The substrate to which the composition of the present invention can be applied is not particularly limited. For example, metal, plastic, rubber, glass, concrete, tile, stone material, etc. may be mentioned.
The method of applying the composition of the present invention to the substrate is not particularly limited.

(Curing)
The composition of the present invention is curable when used in the presence of moisture. The water content is not particularly limited. For example, the humidity in the air may be mentioned.
The temperature condition when using or curing the composition of the present invention can be, for example, room temperature condition.

(Use)
Applications of the composition of the present invention include, for example, sealing materials (for example, for construction), adhesives, coating agents.

The present invention will be specifically described below with reference to examples. However, the present invention is not limited to these.
<Production of vinyl polymer (A)>
Each vinyl polymer (A) was manufactured as follows. The unit "parts" of the amounts of components used in the following production means "parts by mass".

・Vinyl polymer (A-1)
50 parts of methyl ethyl ketone was charged into the reaction vessel, and the temperature was raised to 60° C. with stirring. 100 parts of n-butyl acrylate and 1.86 parts of γ-methacryloxypropylmethyldimethoxysilane (trade name KBM-502, manufactured by Shin-Etsu Chemical Co., Ltd.; the same applies below) were added dropwise thereto, and the inside of the reaction vessel was stirred. The atmosphere was replaced with nitrogen. Next, 1.40 parts of γ-mercaptopropylmethyldimethoxysilane (trade name KBM-802, manufactured by Shin-Etsu Chemical Co., Ltd.; the same applies hereinafter) was added, and after stirring for 30 minutes, 2,2′-azobisisobutyronitrile ( (Tokyo Chemical Industry Co., Ltd., the same applies hereinafter), 0.05 part was added. After that, 0.5 parts of 2,2′-azobisisobutyronitrile was added every 30 minutes and added four times. Further, the reaction was carried out for 4 hours while maintaining the temperature in the reaction container to obtain a vinyl polymer solution. The solvent was removed from the vinyl polymer solution with an evaporator to obtain a vinyl polymer (A-1).

・Vinyl polymer (A-2)
50 parts of methyl ethyl ketone was charged into the reaction vessel, and the temperature was raised to 60° C. with stirring. 100 parts of n-butyl acrylate and 1.24 parts of γ-methacryloxypropylmethyldimethoxysilane were added dropwise thereto, and the inside of the reaction vessel was replaced with nitrogen while stirring. Next, 0.90 part of γ-mercaptopropylmethyldimethoxysilane was added, and after stirring for 30 minutes, 0.05 part of 2,2′-azobisisobutyronitrile was added. After that, 0.5 parts of 2,2′-azobisisobutyronitrile was added every 30 minutes and added four times. Further, the reaction was carried out for 4 hours while maintaining the temperature in the reaction container to obtain a vinyl polymer solution. The solvent was removed from the vinyl polymer solution with an evaporator to obtain a vinyl polymer (A-2).

・Vinyl polymer (A-3)
50 parts of methyl ethyl ketone was charged into the reaction vessel, and the temperature was raised to 60° C. with stirring. 100 parts of n-butyl acrylate and 0.74 part of γ-methacryloxypropylmethyldimethoxysilane were added dropwise thereto, and the inside of the reaction vessel was replaced with nitrogen while stirring. Next, 0.80 part of γ-mercaptopropylmethyldimethoxysilane was added, and after stirring for 30 minutes, 0.05 part of 2,2′-azobisisobutyronitrile was added. After that, 0.5 parts of 2,2′-azobisisobutyronitrile was added every 30 minutes and added four times. Further, the reaction was carried out for 4 hours while maintaining the temperature in the reaction container to obtain a vinyl polymer solution. The solvent was removed from the vinyl polymer solution with an evaporator to obtain a vinyl polymer (A-3).

-(Comparative) vinyl polymer (A-4)
50 parts of methyl ethyl ketone was charged into a reaction vessel, and the temperature was raised to 80° C. with stirring. 100 parts of n-butyl acrylate and 2.40 parts of γ-methacryloxypropylmethyldimethoxysilane were added dropwise thereto, and the inside of the reaction vessel was refluxed while stirring. Next, 0.05 part of 2,2'-azobisisobutyronitrile was added. After that, 0.5 parts of 2,2′-azobisisobutyronitrile was added every 30 minutes and added four times. Further, the reaction was carried out for 4 hours while maintaining the temperature in the reaction container to obtain a vinyl polymer solution. The solvent was removed from the vinyl polymer solution with an evaporator to obtain a (comparative) vinyl polymer (A-4).

-(Comparative) vinyl polymer (A-5)
50 parts of methyl ethyl ketone was charged into a reaction vessel, and the temperature was raised to 80° C. with stirring. 100 parts of n-butyl acrylate and 3.60 parts of γ-methacryloxypropylmethyldimethoxysilane were added dropwise thereto, and the inside of the reaction vessel was refluxed while stirring. Next, 0.10 parts of 2,2'-azobisisobutyronitrile was added. Then, 0.1 part of 2,2'-azobisisobutyronitrile was added every 30 minutes and added four times. Further, the reaction was carried out for 4 hours while maintaining the temperature in the reaction container to obtain a vinyl polymer solution. The solvent was removed from the vinyl polymer solution with an evaporator to obtain a (comparative) vinyl polymer (A-5).

-(Comparative) vinyl polymer (A-6)
50 parts of methyl ethyl ketone was charged into the reaction vessel, and the temperature was raised to 60° C. with stirring. 100 parts of n-butyl acrylate and 5 parts of γ-methacryloxypropylmethyldimethoxysilane were added dropwise thereto, and the inside of the reaction vessel was replaced with nitrogen while stirring. Next, 4 parts of γ-mercaptopropylmethyldimethoxysilane was added, and after stirring for 30 minutes, 0.05 part of 2,2′-azobisisobutyronitrile was added. After that, 0.5 parts of 2,2′-azobisisobutyronitrile was added every 30 minutes and added four times. Further, the reaction was carried out for 4 hours while maintaining the temperature in the reaction container to obtain a vinyl polymer solution. The solvent was removed from the vinyl polymer solution with an evaporator to obtain a (comparative) vinyl polymer (A-6).

-(Comparative) vinyl polymer (A-7)
50 parts of methyl ethyl ketone was charged into the reaction vessel, and the temperature was raised to 60° C. with stirring. 100 parts of n-butyl acrylate and 0.15 part of γ-methacryloxypropylmethyldimethoxysilane were added dropwise thereto, and the inside of the reaction vessel was replaced with nitrogen while stirring. Next, 0.89 part of γ-mercaptopropylmethyldimethoxysilane was added, and after stirring for 30 minutes, 0.05 part of 2,2′-azobisisobutyronitrile was added. After that, 0.5 parts of 2,2′-azobisisobutyronitrile was added every 30 minutes and added four times. Further, the reaction was carried out for 4 hours while maintaining the temperature in the reaction container to obtain a vinyl polymer solution. The solvent was removed from the vinyl polymer solution with an evaporator to obtain a (comparative) vinyl polymer (A-7).

-Table 1 shows the details of the vinyl polymers (A-1) to (A-7).
Referring to the column "Number of reactive silyl groups at the end of vinyl polymer (A)" in Table 1, vinyl polymers (A-1) to (A-3) and (A-6) to (A-6). The above number in -7) is greater than zero. Therefore, in the vinyl polymers (A-1) to (A-3) and (A-6) to (A-7), the molecular chain has a repeating unit of a polymerizable vinyl monomer, It is considered to contain at least the vinyl polymer (a) having a group represented by the above formula (I) at one end (one end).

(Production of vinyl polymer (B-3))
The following (comparative) vinyl polymer (B-3) was produced. The unit "parts" of the amounts of components used in the following production means "parts by mass".
100 parts of methyl ethyl ketone, 100 parts of n-butyl acrylate, and 0.5 parts of 2,2′-azobisisobutyronitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) were charged into a reaction vessel, and the temperature was raised to 80° C. with stirring. After refluxing for an hour, a vinyl polymer solution was obtained. The solvent and the residual monomer were removed from the vinyl polymer solution with an evaporator to obtain a (comparative) vinyl polymer (B-3).
(Comparative) The weight average molecular weight of the vinyl polymer (B-3) was 21,000. The weight average molecular weight of the (comparative) vinyl polymer (B-3) is a standard polystyrene conversion value based on the value measured by gel permeation chromatography (GPC) using tetrahydrofuran (THF) as a solvent.

<Production of polyoxyalkylene polymer (D)>
-Polyoxyalkylene polymer (D-1)
Using polyoxypropylene diol having a number average molecular weight of about 2,000 as an initiator, propylene oxide was polymerized with a zinc hexacyanocobaltate glyme complex catalyst to obtain polyoxypropylene diol having a number average molecular weight of 29,000. A 1.2 times equivalent of a solution of NaOMe in methanol was added to the hydroxyl group of the obtained polyoxypropylene diol to distill off methanol, and 1.6 times equivalent of 3-chloro-2-methyl-1-propene was added. Was added to convert the terminal hydroxyl group into a methallyl group. Next, the inside of the container was replaced with 6% O ₂ /N ₂ , and 100 parts by weight of the obtained methallyl group-terminated polyoxypropylene polymer was added with 100 ppm of sulfur (0.25% by weight of hexane solution), platinum divinyldiene 2.30 parts by weight of dimethoxymethylsilane was slowly added dropwise with stirring while adding 100 ppm of a siloxane complex (3% by weight of isopropanol solution in terms of platinum). By reacting the mixed solution at 100° C. for 5 hours, a linear reaction in which the terminal is a dimethoxymethylsilyl group, the average number of silicon groups per molecule is 1.9, and the number average molecular weight is 29,000. Thus, a polyoxypropylene polymer having a hydrophilic silicon group (polyoxyalkylene polymer (D-1)) was obtained.

<Production of composition>
The components shown in Table 2 below were used in the composition (parts by mass) shown in the same table, and these were mixed with a stirrer to produce a composition.

<Evaluation>
The following evaluation was performed using the composition manufactured as described above. The results are shown in Table 2.
-Viscosity Using a B-type viscometer (Toki Sangyo Co., Ltd., No. 7 rotor), the initial viscosity of the composition produced as described above was measured under the conditions of a rotation speed of 1 rpm and 23°C (unit: Pa.・S).
In the present invention, the workability is excellent when the viscosity of the composition is 2,000 to 4,000 Pa·s.
Moreover, when the viscosity of the composition is 3,000 to 3,900 Pa·s, the workability is evaluated to be superior, and when it is 3,500 to 3,800 Pa·s, the workability is evaluated to be further excellent. did.

-Initial elongation at break-Preparation of sample The composition produced as described above was aged for 72 hours at 23°C and 50% RH (relative humidity). Then, a JIS No. 3 dumbbell-shaped sample (initial sample) having a thickness of 2 mm was punched out from the obtained cured product.

.. Tensile test Using each of the initial samples prepared as described above, according to JIS K6251:2010 (vulcanized rubber and thermoplastic rubber-method for determining tensile properties), a tensile speed of 500 mm/min and room temperature conditions The tensile test was conducted in order to measure the initial elongation at break (%).

-Evaluation criteria for initial breaking elongation In the present invention, when the initial breaking elongation is 200% or more, the breaking elongation is excellent.

-Weather resistance---Preparation of sample The composition produced as described above was aged for 72 hours at 23°C and 50% RH (relative humidity). Then, a sample having a thickness of 5 mm was prepared from the obtained cured product.

.. Weather resistance test Using each sample prepared as described above, with a metal halide weather meter (conditions: 63° C., 50% RH, light energy 75 mW/cm ² , shower with water for 120 seconds every 2 hours). A weather resistance test was conducted in which the treatment was carried out for 500 hours or 750 hours.

-Evaluation criteria After the weather resistance test, each sample was visually observed to confirm the presence or absence of cracks.
When the sample had no cracks, it was evaluated as having excellent weather resistance, and this was designated as "A".
When the sample had cracks that were barely visible to the naked eye, the weather resistance was evaluated to be slightly excellent, and this was indicated as “B”.
When there was a clearly visible crack in the sample visually, it was evaluated that the weather resistance was a little poor, and this was indicated as "C".
When the sample had a large crack (the width of the crack was 0.5 mm to 1.0 mm), the weather resistance was evaluated to be extremely poor, and this was indicated as "D".

Details of each component shown in Table 2 are as follows.
-Vinyl polymers (A-1) to (A-7): Vinyl polymers (A-1) to (A-7) produced as described above.

-Vinyl polymer (B-1): A non-functional group type acrylic polymer. UP1000, manufactured by Toagosei. Weight average molecular weight 3,000.
-Vinyl polymer (B-2): A non-functional group type acrylic polymer. UP1080, manufactured by Toagosei. Weight average molecular weight 6,000.
-(Comparative) vinyl polymer (B-3): (Comparative) vinyl polymer (B-3) produced as described above.

-Polyoxyalkylene polymer (D-1): Polyoxyalkylene polymer (D-1) produced as described above

-Colloidal calcium carbonate: Calfine 200M, manufactured by Maruo Calcium-Heavy calcium carbonate: Ryton A-4, manufactured by Bihoku Powder Co., Ltd.-Titanium oxide: R820, manufactured by Ishihara Sangyo Co., Ltd.

-Plasticizer: polypropylene glycol, Preminol 4002, manufactured by Asahi Glass Co., Ltd. Number average molecular weight 4,000

-Silane 1: Vinyltriethoxysilane, KBM-1003, manufactured by Shin-Etsu Chemical Co., Ltd.-Silane 2: N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, KBM-603, manufactured by Shin-Etsu Chemical Co., Ltd.

Curing catalyst (C): dibutyltin diacetylacetonate (trade name: Neostan U-220, manufactured by Nitto Kasei Co., Ltd.)

-Antiaging agent: 2-(5-chloro-2H-benzotriazol-2-yl)-4-methyl-6-tert-butylphenol, trade name Tinuvin 326, manufactured by BASF.

Resin hollow body: A plastic microballoon whose shell composition is an acrylonitrile-based copolymer and which is coated with calcium carbonate. Product name MFL-60CAS, Matsumoto Yushi-Seiyaku Co., Ltd. Average particle size 60 μm. Heat resistance temperature 140-150°C.

As is clear from the results shown in Table 2, the predetermined vinyl polymer (A) was not contained, and instead, a reactive silicon group-containing polyoxypropylene polymer (polyoxyalkylene polymer (D-1)) was used. In Comparative Example 1 containing C, the weather resistance (particularly after 500 hours) was very poor and deteriorated immediately after the start of the weather resistance test.
Comparative Example 2 which did not contain the predetermined vinyl polymer (B) had poor weather resistance.
Comparative Examples 3 and 4, which did not contain the predetermined vinyl polymer (A) but instead contained the vinyl polymer not containing the vinyl polymer (a), had poor weather resistance and cured physical properties.
Comparative Example 5, which does not contain the predetermined vinyl polymer (A), but instead contains the vinyl polymer having a weight average molecular weight and/or a number average molecular weight outside the predetermined range, has a weather resistance, a cured physical property, and a workability. Was bad.
Comparative Example 6 which does not contain the predetermined vinyl polymer (A), but instead contains the vinyl polymer in which the total number of reactive silyl groups and/or the number of reactive silyl groups in the side chain is out of the predetermined range. Had poor weather resistance.
A vinyl polymer which does not contain a predetermined vinyl polymer (A) and a predetermined vinyl polymer (B), and instead has a weight average molecular weight and/or a number average molecular weight out of a predetermined range, and a reactive silicon group. Comparative Example 7 containing the contained polyoxypropylene polymer (polyoxyalkylene polymer (D-1)) had poor weather resistance, cured physical properties, and workability.
Comparative Example 8 which does not contain the predetermined vinyl polymer (B) but instead contains the vinyl polymer having a weight average molecular weight outside the predetermined range has poor workability.

On the other hand, the composition of the present invention was excellent in weather resistance, cured property and workability.

Claims (22)

Having a reactive silyl group at the end and side chain of the molecular chain, the molecular chain has a repeating unit of a polymerizable vinyl monomer,
On average per molecule, the total number of the reactive silyl groups exceeds 1, the number of reactive silyl groups at the terminal exceeds 0.5, and the number of reactive silyl groups in the side chain is 0. More than 5
A vinyl polymer (A) having a weight average molecular weight of 30,000 to 110,000, a number average molecular weight of 9,000 to 40,000, and a glass transition temperature of -100 to -10°C;
A vinyl polymer (B) having no reactive silyl group, a molecular chain having a repeating unit of a polymerizable vinyl monomer, and a weight average molecular weight of 20,000 or less;
Containing a curing catalyst (C),
The vinyl polymer (A) is a vinyl polymer (a) having a repeating unit of a polymerizable vinyl monomer in the molecular chain and a group represented by the following formula (I) at the terminal of the molecular chain. Curable resin composition containing.
^{* -S-L 1 -X 1 (} I)
In formula (I), S is a sulfur atom, L ¹ represents a divalent linking group, X ¹ represents a reactive silyl group, and * represents a bonding position. The curable resin composition according to claim 1, wherein the content of the vinyl polymer (B) is 1 to 100 parts by mass with respect to 100 parts by mass of the vinyl polymer (A). The curing catalyst (C) is at least one selected from the group consisting of tin compounds, titanium compounds, acidic compounds and amine compounds,
The curable resin composition according to claim 1 or 2, wherein the content of the curing catalyst (C) is 0.1 to 20 parts by mass with respect to 100 parts by mass of the vinyl polymer (A). The curable resin composition according to claim 1, further comprising a hollow resin body. Further, the curable resin composition according to any one of claims 1 to 4, further comprising an antioxidant. The curable resin composition according to any one of claims 1 to 5, wherein the vinyl polymer (A) has a weight average molecular weight of 45,000 to 90,000. The curable resin composition according to any one of claims 1 to 6, wherein the vinyl polymer (A) has a number average molecular weight of more than 10,000 and less than 20,000. The curable resin composition according to claim 1, wherein the vinyl polymer (A) further has a hydrocarbon group in a side chain. However, the hydrocarbon group does not have a reactive silyl group. The curable resin composition according to claim 8, wherein the hydrocarbon group has 1 to 12 carbon atoms. The curable resin composition according to any one of claims 1 to 9, wherein the vinyl polymer (A) has a linear molecular chain. The curable resin composition according to any one of claims 1 to 10, wherein in formula (I), the reactive silyl group as X ₁ is a dialkoxysilyl group. The molecular chain of the vinyl polymer (A) has a repeating unit represented by the following formula (II) and a repeating unit represented by the formula (III), and the polymer chain according to any one of claims 1 to 11. Curable resin composition.
In formula (II), R ^2-1 represents a hydrogen atom or a monovalent hydrocarbon group, L ² represents a divalent linking group, and R ^2-2 represents a monovalent hydrocarbon group.
In formula (III), R ^3-1 represents a hydrogen atom or a monovalent hydrocarbon group, L ³ represents a divalent linking group, and R ^3-2 and R ^3-3 each independently represent a monovalent hydrocarbon group. It represents a hydrocarbon group, m3 is 1-3, n3 is 0-2, and m3+n3 is 3. The curable resin composition according to claim 12, wherein m3 is 2 and n3 is 1 in the formula (III). The curable resin composition according to any one of claims 1 to 13, wherein the group represented by the formula (I) is a group represented by the following formula (I-1).
In formula (I-1), R ^1-1 represents a divalent hydrocarbon group, R ^1-2 and R ^1-3 each independently represent a monovalent hydrocarbon group, and m1 is 1 to 3 Yes, n1 is 0 to 2, m1+n1 is 3, and * represents a bonding position. In the formula (I-1), the curable resin composition according to claim 14, wherein m1 is 2 and n1 is 1. The curable resin composition according to any one of claims 1 to 15, wherein the vinyl polymer (a) has one terminal having a group represented by the formula (I). The curable resin composition according to any one of claims 1 to 16, wherein the vinyl polymer (a) further has a reactive silyl group on a side chain of the molecular chain. The curability according to any one of claims 1 to 17, wherein in the vinyl polymer (A), the reactive silyl group at the terminal of the molecular chain is a group represented by the following formula (V). Resin composition.
^{* -S-L 1 -X 1 (} V)
In formula (V), S is a sulfur atom, L ¹ represents a divalent linking group, X ¹ represents a reactive silyl group, and * represents a bonding position. The curing according to any one of claims 1 to 18, wherein in the vinyl polymer (A), the total number of the reactive silyl groups is more than 1 and less than 1.80 per molecule on average. Resin composition. Furthermore, containing a plasticizer,
The plasticizer contains at least a polyoxyalkylene polyol having a number average molecular weight of 1,500 to 15,000,
The curable resin composition according to any one of claims 1 to 19, wherein a mass ratio of the plasticizer to the vinyl polymer (B) is 0.1 or more and less than 1.0. The curable resin composition according to any one of claims 1 to 20, which is used as an adhesive. The curable resin composition according to any one of claims 1 to 20, which is used as a sealing material.