JPH0567647B2 - - Google Patents

Description

[Detailed description of the invention]

INDUSTRIAL APPLICATION FIELD The present invention relates to a novel curable composition and curing method. BACKGROUND TECHNOLOGY AND PROBLEMS Conventionally, compositions prepared by adding acids, bases, organometallic catalysts, etc. to alkoxysilane-containing vinyl polymers have been known as compositions that can be crosslinked and cured at relatively low temperatures of room temperature to 100°C. For example, JP-A-60-
No. 67553 discloses a composition in which an aluminum chelate compound is blended with a vinyl polymer containing an alkoxysilane such as methacryloxypropyltrimethoxysilane. However, in the above-mentioned conventional composition, since the only crosslinking functional group is the acylanol group produced by hydrolysis of alkoxysilane, a large amount of water is required for curing, and by-products such as alcohol are produced during this hydrolysis. The physical properties of the cured product deteriorate because of the large amount produced, and when curing with only moisture in the air, only the surface that comes into contact with the air is cured, and the inside is hardly cured, resulting in the difference in hardening between the surface and the inside. There were drawbacks such as the tendency for stiffness to occur in the cured product. Means for Solving the Problems An object of the present invention is to provide a novel curable composition and curing method that can be sufficiently cured with a small amount of water. Another object of the present invention is to provide a novel curable composition and a curing method with excellent physical properties of the cured product. Another object of the present invention is to provide a new curable composition and a curing method that have a small difference in curing between the surface and the inside and do not cause sagging when cured using only moisture in the air. These and further objects of the invention will become clear from the description below. The present invention is based on the general formula

[ka] [In the formula, A is

[Formula] or

[Formula] is shown. R ₁ is a hydrogen atom or a methyl group, R ₂ is a divalent aliphatic saturated hydrocarbon group having 1 to 6 carbon atoms, R ₃ and R ₄ are the same or different, and are a phenyl group, a carbon number 1
-6 alkyl group or an alkoxy group having 1 to 6 carbon atoms, and R ⁵ represents an alkyl group having 1 to 6 carbon atoms, respectively. n represents an integer from 1 to 100. ] A copolymer containing as monomer components an alkoxysilane group-containing vinyl monomer and an oxirane group-containing vinyl monomer, which is a compound represented by
The present invention relates to a curable composition characterized by containing an aluminum chelate compound as a crosslinking reaction curing agent, and a curing method characterized by crosslinking the composition at 100° C. or lower in the presence of moisture. The inventor of the present invention conducted extensive research to eliminate the various drawbacks of the conventional curable compositions described in the above-mentioned publication, and as a result, discovered the following new facts. (1) By further incorporating an oxirane group into a vinyl polymer containing an alkoxysilane group, not only the silanol group but also the oxirane group becomes a crosslinking functional group, so that it is sufficiently cured in the presence of a small amount of water. (2) Therefore, since the amount of byproducts such as alcohol during curing is extremely small, there is almost no deterioration in the physical properties of the cured product, and the physical properties of the resulting cured product are excellent. (3) When curing with only moisture in the air, crosslinking and curing by silanol groups on the surface in contact with the air and crosslinking and curing by oxirane groups occurs in a chain reaction to the inside, so there is a difference in hardening between the surface and the inside. It does not cause stiffness. The present invention has been completed based on these new findings. In the general formula (), n is preferably 1 to 10
is an integer. In the general formula (), the divalent aliphatic saturated hydrocarbon group having 1 to 6 carbon atoms represented by R ₂ is a linear or branched alkylene group such as methylene, ethylene, propylene, tetramethylene,
Ethyl ethylene, pentamethylene, hexamethylene groups, etc. can be mentioned. Examples of the alkyl group having 1 to 6 carbon atoms represented by R ₃ , R ₄ and R ₅ include linear or branched alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl,
isobutyl, sec-butyl, tert-butyl, n-
Examples include pentyl, isopentyl, neopentyl, n-hexyl, and isohexyl groups. Examples of the alkoxy group having 1 to 6 carbon atoms represented by R ₃ and R ₄ include linear or branched alkoxy groups such as methoxy, ethoxy, n-propoxy,
Isopropoxy, n-butoxy, isobutoxy,
Examples include sec-butoxy, tert-butoxy, n-pentoxy, isopentoxy, n-hexyloxy, and isohexyloxy groups. Furthermore, in the general formula (), when n is 2 or more,
R ₃ comrades and R ₄ comrades may be the same or different. Of the compounds of general formula () used as monomers in the present invention, A is

[Formula] Examples include β-(meth)acryloxyethyltriethoxysilane, γ-(meth)acryloxypropyltrimethoxysilane, γ-(meth)acryloxypropyltriethoxysilane, γ-
(meth)acryloxypropyltripropoxysilane, γ-(meth)acryloxypropylmethyldimethoxysilane, γ-(meth)acryloxypropylmethyldiethoxysilane, γ-(meth)acryloxypropylmethyldipropoxysilane,
γ-(meth)acryloxybutylphenyldimethoxysilane, γ-(meth)acryloxybutylphenyldiethoxysilane, γ-(meth)acryloxybutylphenyldipropoxysilane, γ-
(meth)acryloxypropyldimethylmethoxysilane, γ-(meth)acryloxypropyldimethylethoxysilane, γ-(meth)acryloxypropyl phenylmethylmethoxysilane, γ-
(meth)acryloxypropylphenylmethylethoxysilane,

[ka]

[ka]

[ka]

【formula】

[ka]

[C] etc. can be mentioned. Furthermore, in the compound of general formula (), A is

[Formula] is, for example,

【formula】

【formula】

[ka]

[ka]

[ka]

[Formula] etc. can be mentioned. Moreover, as the oxirane group-containing vinyl monomer, various vinyl monomers containing an oxirane group in the molecule can be used. In particular, it is preferable to use a vinyl monomer containing an alicyclic oxirane group from the viewpoint of curability and the like. That is, when using a vinyl monomer containing an alicyclic oxirane group, the reactivity of the ring-opening polymerization reaction of the oxirane group is high, so that the effect of quick curing and further improvement of the physical properties of the cured coating film can be obtained. . Particularly preferred are acrylic acid or methacrylic esters containing an alicyclic oxirane group, specifically, for example, each of the following general formulas () to
Examples include those represented by parentheses.

[ka]

[ka]

[ka]

[ka]

[ka]

[ka]

[ka]

[ka]

[ka]

[ka]

[ka]

[In each general formula, R ₆ represents a hydrogen atom or a methyl group. R ₇ represents a divalent aliphatic saturated hydrocarbon group having 1 to 6 carbon atoms. R ₈ represents a divalent hydrocarbon group having 1 to 10 carbon atoms. m represents an integer of 1 to 10. In the above, the number of carbon atoms represented by R ₇ is 1
-6 divalent aliphatic saturated hydrocarbon groups include linear or branched alkylene groups such as methylene, ethylene, propylene, tetramethylene, ethylethylene, pentamethylene, and hexamethylene groups. Further, examples of the divalent hydrocarbon group having 1 to 10 carbon atoms represented by R ₈ include methylene, ethylene, propylene, tetramethylene, ethylethylene, pentamethylene, hexamethylene, polymethylene, phenylene,

【formula】

[Formula] groups, etc. can be mentioned. Furthermore, typical examples of vinyl monomers containing non-alicyclic oxirane groups include those represented by the following general formula ().

[In the formula, R ₆ and R ₇ are the same as above. ] The copolymer used as the resin component in the curable composition of the present invention is composed of an alkoxysilane group-containing vinyl monomer (hereinafter referred to as monomer A), which is a compound represented by the general formula (), and an oxirane group-containing vinyl monomer. It is a copolymer containing a monomer (hereinafter referred to as monomer B) as a monomer component. That is, it is a copolymer obtained using monomer A and monomer B as essential monomer components. Here, the ratio of monomer A and monomer B to be used is preferably approximately A:B=1:0.02 to 10,000 in terms of weight ratio.
If the B content exceeds this range, the curability tends to decrease, and if the B content decreases below this range, the physical properties of the cured product tend to deteriorate and sagging tends to occur, which is not preferable. The preferred amount used is A:B=1:0.1 to about 1000 in weight ratio. A particularly preferable usage amount is A:B=1:0.25 to 1:0.25 by weight.
It is about 100. In addition to monomers A and B, which are essential monomers, other α,β-ethylenically unsaturated monomers may be used in the copolymer, if necessary. In this case, the amount of the α,β-ethylenically unsaturated monomer used is usually about 99% by weight or less of the total monomers, in order not to impair the intended effects of the present invention.
The content is preferably about 97% by weight or less. The above copolymer can be produced using standard methods and conditions, and its number average molecular weight is approximately 3,000 to 3,000.
A range of about 100,000 is preferable. The α,β-ethylenically unsaturated monomer that can be used as an arbitrary monomer component in the above copolymer can be selected from a wide range depending on the desired performance. Representative examples of such unsaturated monomers are as follows. (a) Esters of acrylic acid or methacrylic acid, such as methyl acrylate, ethyl acrylate,
Propyl acrylate, isopropyl acrylate, butyl acrylate, hexyl acrylate,
Acrylic acid or methacrylic acid with 1 carbon number such as octyl acrylate, lauryl acrylate, methyl methacrylate, ethyl methacrylate, propyl methacrylate, isopropyl methacrylate, butyl methacrylate, hexyl methacrylate, octyl methacrylate, lauryl methacrylate, etc. -18 alkyl ester; alkoxy of acrylic acid or methacrylic acid having 2 to 18 carbon atoms, such as methoxybutyl acrylate, methoxybutyl methacrylate, methoxyethyl acrylate, methoxyethyl methacrylate, ethoxybutyl acrylate, ethoxybutyl methacrylate, etc. Alkyl ester; Alkenyl ester of acrylic acid or methacrylic acid having 2 to 8 carbon atoms, such as allyl acrylate, allyl methacrylate; Carbon number of acrylic acid or methacrylic acid, such as hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, etc. 2 to 8 hydroxyalkyl esters, and adducts of the hydroxyalkyl esters with lactones such as ε-caprolactone (e.g. "Plaxel FA-1",
"Plaxel FA-2", "Plaxel FA-3",
"Plaxel FM-1", "Plaxel FM-2",
"Plaxel FM-3" (manufactured by Daicel Chemical Co., Ltd., trade name); alkenyloxyalkyl ester of acrylic acid or methacrylic acid having 3 to 18 carbon atoms, such as allyloxyethyl acrylate and allyloxymethacrylate. (b) Vinyl aromatic compounds: e.g. styrene, α
-Methylstyrene, vinyltoluene, p-chlorostyrene. (c) Polyolefin compounds: for example, butadiene, isoprene, chloroprene. (d) Others: acrylonitrile, methacrylonitrile, methyl isopropenyl ketone, vinyl acetate, beoba monomer (Siel Chemicals), vinyl propionate, vinyl pivalate, etc. The curable composition of the present invention is a copolymer containing monomer A and monomer B as monomer components, and an aluminum chelate compound as a crosslinking reaction curing agent. The aluminum chelate compound used as a crosslinking reaction curing agent in the present invention is a well-known compound, but among them, one obtained by treating an organoaluminum with a chelating agent is preferable, and as the organoaluminum, In particular, the following general formula

[Formula] [In the formula, at least one of R ₉ , R ₁₀ and R ₁₁
One is an alkoxy group having 1 to 13 carbon atoms (e.g. methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, isoamyloxy, n-hexyloxy , n-heptyloxy, n-octyloxy, etc.) or carbon number 3-
10 alkoxyalkoxy groups (e.g., methoxymethoxy, methoxyethoxy, ethoxybutoxy, butoxypentoxy groups, etc.), and the remaining are alkyl groups having 1 to 6 carbon atoms (e.g., methyl, ethyl,
n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, amyl group, etc.), aryl group (especially phenyl, tolyl group), alkenyl group (e.g. vinyl, allyl group, etc.)
or represents an alkyl group having 1 to 6 carbon atoms substituted with a mercapto group or an amino group (e.g. γ-mercaptopropyl, aminoethyl, aminopropyl, aminobutyl group, etc.)] Compounds represented by the following are preferred, and specifically Examples include aluminum isoproporate, aluminum sec-butyrate, and aluminum tert-butyrate. Examples of the chelating agent that can be reacted with the organoaluminum include lower alkanolamines (e.g., triethanolamine, diethanolamine, dimethylaminoethanol, etc.), acetoacetate (e.g., methyl acetoacetate, ethyl acetoacetate, etc.), Diketone alcohols (e.g.
diacetone alcohol, etc.), diketones (e.g.
acetylacetone, etc.), glycols (e.g., ethylene glycol, octylene glycol, etc.),
Oxycarboxylic acids (e.g. lactic acid, tartaric acid, etc.), dicarboxylic acids or their esters (e.g. maleic acid,
ethyl malonate, etc.), salicylic acid, catechol, pyrogallol, etc. Among them, lower alkanolamines, oxycarboxylic acids, and diketones are preferred. Specifically, examples of aluminum chelate compounds advantageously used in the present invention include the following. Namely, ethyl acetoacetate aluminum diisoproporate, aluminum tris(ethylacetoacetate), tris(trifluoroacetylacetonato)aluminum, tris(hexafluoroacetylacetonato)aluminum, tris(ethylacetoacetate)aluminum, tris(n
-propylacetoacetate)aluminum, tris(iso-propylacetoacetate)aluminum, tris(n-butylacetoacetate)
Aluminum, Tris (salicylaldehydate)
Aluminum, isopropoxy bis(ethyl acetoacetate) aluminum, 2,2,6,6-
Tetramethyl-3,5-heptadionatoaluminum, tris(2-ethoxycarbonylphenolate)aluminum, diisopropoxyethylacetoacetate, acetylacetonatobis(ethylacetoacetate)aluminum, etc.
These may be partially condensed. In the present invention, any one type of aluminum chelate compound may be used as the crosslinking reaction curing agent, or two or more types may be used in combination as appropriate. The amount of the crosslinking reaction curing agent is suitably about 0.01 to 30 parts by weight based on 100 parts by weight of the copolymer. If the amount is less than this range, crosslinking curability tends to decrease, and if it is more than this range, it tends to remain in the cured product and reduce water resistance, which is not preferable. The preferred amount is 0.1 to 10 parts by weight, and the more preferred amount is 1 to 5 parts by weight. Extender pigments, coloring pigments, dyes, etc. can be added to the curable composition of the present invention, if necessary. In addition, if necessary, monofunctional or polyfunctional epoxy compounds, low molecular weight silane compounds such as triphenylmethoxysilane and diphenyldimethoxysilane, and other silicone resins having general alkoxysilane groups may be used. It is also possible to add a resin. Moreover, the above-mentioned chelating agent can be added for the purpose of improving storage stability. The curable composition of the present invention can be suitably used, for example, in paints, adhesives, inks, and the like. The curable composition of the present invention can be cured at 100% in the presence of moisture.
It can be easily crosslinked and cured at low temperatures below ℃. That is, according to the present invention, the composition can be sufficiently cured in about 8 hours to 7 days by simply adding water to the composition or exposing the composition to the air after application, and without any heating. can be done.
For example, when heated to 40 to 100°C, it can be sufficiently cured in about 5 minutes to 3 hours.
Furthermore, a small amount of moisture, comparable to that in the air, is sufficient for curing. When water is added before coating, an amount of about 0.1 to 1% by weight is usually sufficient. The reason why the curable composition of the present invention is easily crosslinked and cured at low temperature in the presence of a small amount of water is considered to be as follows. That is, as a first-stage reaction, an alkoxy group derived from monomer A is hydrolyzed in the presence of moisture using an aluminum chelate compound as a catalyst to generate a silanol group. Next, as a second reaction, cross-linking by dehydration condensation of silanol groups and reaction with an aluminum chelate compound are performed.

Crosslinking occurs by forming bonds. Furthermore, as a third reaction

[Formula] The bond coordinates to another silanol group to polarize the silanol group, and the polarized silanol group causes ring-opening polymerization of the oxirane group derived from monomer B, thereby causing crosslinking. Compared to the conventional case, in the conventional curable composition of this type, crosslinking and curing was performed only by the second reaction, whereas in the curable composition of the present invention, monomer B is particularly When used, the second-stage reaction and the third-stage reaction occur in parallel in a chain, resulting in crosslinking and curing, so it is thought that it can be cured suitably at low temperatures with a small amount of moisture. Effects of the Invention According to the curable composition of the present invention, since the copolymer used as the resin component contains both monomer A and monomer B as monomer components, the following effects can be achieved. This produces particularly remarkable effects. (1) It can be easily crosslinked and cured at a low temperature of 100°C or less in the presence of a small amount of moisture, such as moisture in the air. (2) Since the crosslinking by the condensation reaction etc. and the crosslinking by the ring-opening polymerization reaction occur simultaneously, there is little difference in hardenability between the surface and the inside, and no stiffness occurs. (3) Since there are few by-products such as alcohol, a cured product with excellent physical properties can be obtained. In particular, it has excellent physical properties such as water resistance, weather resistance, impact resistance, suitability for overcoating, flexibility, and stain resistance. (4) It has excellent storage stability and is stable for more than one year without moisture. Examples Hereinafter, the present invention will be explained in more detail with reference to Examples and Comparative Examples. Example 1 A vinyl copolymer having the following monomer composition was synthesized.

[Formula] 50.2% by weight n-butyl methacrylate 30.5% by weight

[Formula] 19.3% by weight The obtained 50% by weight toluene solution of the vinyl copolymer showed a viscosity of H on a Gardner viscometer. Furthermore, the GPC molecular weight showed a peak molecular weight at 15,000. 2g to 100g of this 50% by weight toluene resin liquid
of tris(n-propylacetoacetate)aluminum was added to obtain a curable composition of the present invention. Example 2 A vinyl copolymer having the following monomer composition was synthesized.

[Formula] 90% by weight

[Chemical formula] 10% by weight A 70% by weight solution of the obtained copolymer in isobutyl acetate showed a viscosity of Z on a Gardner viscometer. Furthermore, the GPC molecular weight showed a peak molecular weight at 5000. 20g of Tris (salicylaldehydate) in 100g of this 70% by weight isobutyl acetate resin solution
A curable composition of the present invention was obtained by adding aluminum. Example 3 A vinyl copolymer having the following monomer composition was synthesized.

[Formula] 40% by weight γ-acryloxypropylphenylmethylmethoxysilane 5% by weight Styrene 55% by weight The Gardner viscosity of a 50% by weight toluene solution of this copolymer was W. Furthermore, the peak molecular weight of GPC was 25,000. 1 g of tris(ethyl acetoacetate) aluminum was added to 100 g of this 50% by weight toluene resin solution to obtain a composition of the present invention. Example 4 A vinyl copolymer having the following monomer composition was synthesized.

[Formula] 15% by weight γ-methacryloxypropyltrimethoxysilane
50% by weight Methyl acrylate 35% by weight The Gardner viscosity of a 50% by weight toluene solution of this copolymer was X. Moreover, the GPC peak molecular weight was 40,000. To 100 g of this 50% by weight toluene resin liquid was added 10 g of tris(acetylacetonato)aluminum to obtain a composition of the present invention. Example 5 A vinyl copolymer having the following monomer composition was synthesized.

[ka] 5% by weight

[Formula] 1% by weight Methyl methacrylate 94% by weight The Gardner viscosity of a 50% by weight solution of this copolymer in toluene-butanol (1:1) was S.
Furthermore, the GPC molecular weight showed a peak at 28,000.
100g of this 50% by weight toluene-butanol resin liquid
After adding 50 g of rutile titanium white and thoroughly dispersing it, 1 g of tris(acetylacetonato)aluminum was added to obtain a composition of the present invention. Example 6 A vinyl copolymer having the following monomer composition was synthesized. Oxydicyclopentenyl acrylate
20.5% by weight Styrene 40.5% by weight n-butyl acrylate 29.0% by weight γ-methacryloxypropylmethyldimethoxysilane 10.0% by weight A 50% by weight toluene solution of this copolymer showed a viscosity of X on a Gardner viscometer. Also, GPC
The peak molecular weight was 35,000. A composition of the present invention was obtained by adding 10 g of tris(ethyl acetoacetate) aluminum to 100 g of this 50% by weight toluene resin liquid. Example 7 A vinyl copolymer having the following monomer composition was synthesized.

[Chemical formula] 50% by weight Methyl methacrylate 40% by weight γ-methacryloxypropyldimethylmethoxysilane 10% by weight A 50% by weight toluene solution of this copolymer showed a viscosity of Z ₂ on a Gardner viscometer. Also, GPC
The peak molecular weight was 8800. This 50
Add 0.5g of tris(salicylaldehydato)aluminum to 100g of weight% toluene resin liquid,
A composition of the present invention was obtained. Example 8 A vinyl copolymer having the following monomer composition was synthesized.

[Formula] 30% by weight Methyl methacrylate 20% by weight Ethyl acrylate 20% by weight

[Chemical formula] 30% by weight A 50% by weight toluene solution of this copolymer exhibited a viscosity of TU on a Gardner viscometer. Also, GPC
The peak molecular weight was 12,000. this
A composition of the present invention was obtained by adding 1 g of tris(ethyl acetoacetate) aluminum to 100 g of a 50% by weight toluene resin solution. Example 9 A vinyl copolymer having the following monomer composition was synthesized.

[ka] 90% by weight

[Chemical formula] 10% by weight A 50% by weight toluene solution of this copolymer showed a viscosity of Z ₂ on a Gardner viscometer. Also, GPC
The peak molecular weight was 20,000. this
Add 10g of tris(acetylacetonato)aluminum to 100g of 50% by weight toluene resin liquid,
A composition of the present invention was obtained. Example 10 A vinyl copolymer having the following monomer composition was synthesized.

[ka] 50% by weight Methyl methacrylate 40% by weight

[Chemical formula] 10% by weight A 50% by weight toluene solution of this copolymer exhibited a viscosity of W on a Gardner viscometer. Also, GPC
The molecular weight showed a peak molecular weight at 10,000. this
Add 1g of tris(acetylacetonato)aluminum to 100g of 50% by weight toluene resin liquid,
A composition of the present invention was obtained. Comparative Example 1 A vinyl copolymer having the following monomer composition was synthesized. n-Butyl methacrylate 95.0% by weight γ-methacryloxypropyltrimethoxysilane
5.0% by weight A 50% by weight toluene solution of this copolymer had a Gardner viscosity of N. In addition, the GPC molecular weight is
It showed a peak at 28,000. A comparative curable composition was obtained by adding 3 g of tris(acetylacetonato)aluminum to 100 g of this 50% by weight toluene resin liquid. Comparative Example 2 In Example 1

A comparative composition was obtained in the same manner as in Example 1, except that [Chemical formula] was not used. Next, the following tests were conducted. [Coating film performance test] After coating each composition of Examples 1 to 10 and Comparative Examples 1 and 2 to a dry film thickness of 100μ (however, water resistance and weather resistance were tested at 50μ), It was dried under the drying conditions listed in Table 1 and used for testing. Gel fraction: After the dried coating film was peeled off from the glass plate and extracted using a Soxhlet extractor at reflux temperature with acetone for 6 hours, the remaining content of the coating film was expressed in %. Impact resistance: The material used is mild steel plate. Using a Dupont impact tester, a 500g weight was dropped onto the painted surface, and the maximum fall distance (cm) without cracking or peeling of the paint film was determined. Water resistance: The material used is mild steel plate. The test piece was immersed in warm water (40°C) for 60 days, and then the condition of the painted surface was examined. Weather resistance: The material used is aluminum plate. QUV weather meter manufactured by The Q Panel (ultraviolet fluorescent lamp "No.QFS-40, UV-B", wavelength range 320
irradiation (~280 nm) at a temperature of 40-70 °C (15
The degree of paint film deterioration was observed after repeating the cycle of 2000 hours of dew condensation (15 minutes) and condensation (15 minutes). Suitability for overcoat: 40μ of "Vinide Lux" (manufactured by Kansai Paint Co., Ltd., acrylic resin emulsion paint) was applied on the paint film, and after drying at 20℃ for 2 hours, a cross cut was made on the painted surface and a cellophane tape peeling test was performed. After that, the degree of peeling was examined.The test results are shown in Table 1.

【table】

Claims (1)

[Claims] 1 General formula: [In the formula, A represents [Formula] or [Formula]. R ₁ is a hydrogen atom or a methyl group, R ₂ is a divalent aliphatic saturated hydrocarbon group having 1 to 6 carbon atoms, R ₃ and R ₄ are the same or different, and are a phenyl group, a carbon number 1
-6 alkyl group or an alkoxy group having 1 to 6 carbon atoms, and R ⁵ represents an alkyl group having 1 to 6 carbon atoms, respectively. n represents an integer from 1 to 100. ] A copolymer containing as monomer components an alkoxysilane group-containing vinyl monomer and an oxirane group-containing vinyl monomer, which is a compound represented by
A curable composition comprising an aluminum chelate compound as a crosslinking reaction curing agent. 2. The composition according to claim 1, wherein the oxirane group-containing vinyl monomer is an alicyclic oxirane group-containing vinyl monomer. 3 General formula [formula] [wherein A represents [formula] or [formula]]. R ₁ is a hydrogen atom or a methyl group, R ₂ is a divalent aliphatic saturated hydrocarbon group having 1 to 6 carbon atoms, R ₃ and R ₄ are the same or different, and are a phenyl group, a carbon number 1
-6 alkyl group or an alkoxy group having 1 to 6 carbon atoms, and R ⁵ represents an alkyl group having 1 to 6 carbon atoms, respectively. n represents an integer from 1 to 100. ] A copolymer containing as monomer components an alkoxysilane group-containing vinyl monomer and an oxirane group-containing vinyl monomer, which is a compound represented by
A curing method characterized by crosslinking a curable composition containing an aluminum chelate compound as a crosslinking reaction curing agent at 100°C or lower in the presence of moisture.