JPH10168299A - Curable composition excellent in adhesion of coating material - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a curable composition having a good adhesion of a coating material and used as a sealant which can form a cured product of improved stickiness by mixing an oxyalkylene polymer having reactive silicon groups with a modifier comprising an amino silicon compound and a limited silanol compound. SOLUTION: The oxyalkylene polymer is one having at least one reactive silicon group in the molecule and is desirably a polymer mainly consisting of propylene oxide. The reactive silicon group means a group which is hydrolyzed with atmospheric moisture and condenses with another silicon group to form a siloxane bond and is exemplified by -Si(OC3 )3 . The oxyalkylene polymer has desirably a number-average molecular weight of 1,000-30,000. The amino silicon compound used is exemplified by N-phenyl-γ- aminopropyltrimethoxysilane and is used in an amount of desirably 0.1-10 pts.wt. per 100 pts.wt, oxyalkylene polymer. The silanol compound is exemplified by trimethylsilanol or methyldiphenylsilanol and is used in an amount of desirably 0.1-10 pts.wt. per 100 pts.wt. oxyalkylene polymer.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a moisture-curable composition having excellent paint adhesion when a paint is applied.

[0002]

2. Description of the Related Art A reactive silicon group is a silicon atom-containing group which has a hydroxyl group or a hydrolyzable group bonded to a silicon atom and can be crosslinked by forming a siloxane bond. The polymer having a reactive silicon group cross-links and cures in the presence of moisture.In the polymer, for example, a curable composition using a polymer having a main chain skeleton of polyoxyalkylene such as polyoxypropylene,
At room temperature, it has the property of being liquid and becoming a rubber elastic body upon curing, and is widely used in architectural sealants and industrial sealants. However, when filling this into joints, etc., residual tack (stickiness) remains on the surface even after curing,
The contamination of the surface due to the adhesion of dust progressed, and there was an aesthetic problem.
Also, when applying paint to the surface, it can be easily applied to the surface, but the adhesion between the paint and the sealant surface is not always sufficient, especially when a solvent-based paint is used. there were.

[0003]

Means for Solving the Problems The present inventor has solved the above problems.
As a result of intensive investigations to determine
A silicon compound having at least one amino group in
Formula, R⁷ _ThreeUsing a silanol compound represented by SiOH
By doing so, we found that the above problems could be solved,
The present invention has been reached. That is, the present invention relates to (a)
Oxyalkyls containing at least one reactive silicon group
(B) at least one amino group in the molecule
A silicon compound having the formula (c):⁷ _ThreeSiOH,
(Where R ⁷Is an alkyl group having 1 to 20 carbon atoms, 6 carbon atoms
To 20 aryl groups, 7 to 20 aralkyl groups.
Or R^Three _ThreeSiO- (R^ThreeIs a monovalent carbon having 1 to 20 carbon atoms
A hydrogen group, and three R^ThreeMay be the same or different
Or a triorganosiloxy group represented by
Yes, three R⁷Can be the same or different
Curable containing a silanol compound represented by
Composition and a curable set containing the polymer of component (a)
In the method of applying paint to the cured product of the product, the above curability
A method of using the composition.

[0004]

DESCRIPTION OF THE PREFERRED EMBODIMENTS In the present invention, an oxyalkylene polymer having at least one reactive silicon group in a molecule is used as the component (A). The main chain of the oxyalkylene polymer has a repeating unit represented by the general formula (1). —R—O— (1) (wherein, R is a divalent alkylene group) In the above formula, R is a group having 1 to 14 carbon atoms, and more preferably 2 to 2 carbon atoms.
4, a linear or branched alkylene group is preferred.

[0005] Specific examples of the repeating unit represented by the above formula and
Is -CH_TwoO-, -CH_TwoCH_TwoO-, -CH_TwoCH
(CH_Three) O-, -CH_TwoCH (C _TwoH_Five) O-, -CH_Two
C (CH_Three)_TwoO-, -CH_TwoCH_TwoCH_TwoCH_TwoO- etc.
I can do it. Oxyalkylene polymer has only one main chain
May be composed of two or more repeating units.
It may consist of repeating units. Especially propylene oxide
It is preferred to be composed of a polymer containing as a main component. Also, heavy
The main chain of the union contains repeating units other than the alkylene group
It may be. In this case, the oxyalkylene in the polymer
50% by weight or more, preferably 80% by weight
The content is preferably 90% by weight or more.

The reactive silicon group is, for example, -Si (OCH
₃ ) The group represented by ₃ is hydrolyzed by moisture in the air or the like, and is subjected to a silanol condensation reaction with another reactive silicon group via silanol such as -Si (OH) ₃ to form a siloxane bond (Si
—O—Si). (CH ₃ O) ₃ Si ~ ~ ~ ~ ~ ~ ~ ~ Si (OCH ₃ ) ₃ → [(HO) ₃ Si ~ ~ ~ ~ ~ ~ ~ ~ Si (OH) ₃ ] → (~ ~ ~ ~ SiO) ₃ Si ~~~~~~~~ Si (OSi ~~~) ₃ Therefore, the polymer having a reactive silicon group crosslinks and cures even at room temperature in the presence of moisture. The reactive silicon group is a well-known functional group, and a typical example thereof is a group represented by the general formula (2).

[0007]

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Wherein R ¹ and R ² each have 1 carbon atom
20 alkyl group, an aryl group having 6 to 20 carbon atoms, an aralkyl group or R ³ of 7 to 20 carbon atoms ₃ SiO- (R ³
Is a monovalent hydrocarbon group having 1 to 20 carbon atoms, and three R
³ may be the same or different), and R ¹ or R ² is 2
When there are more than one, they may be the same or different. X is a hydroxyl group or a hydrolyzable group, and when two or more are present, they may be the same or different. a is an integer selected from 0 to 3, b is an integer selected from 0 to 2, and a + Σb ≧ 1
Is an integer. When m is 2 or more, each b does not need to be the same. m is an integer selected from 0 to 19. The hydrolyzable group in the general formula (2) is not particularly limited, and may be a conventionally known hydrolyzable group. For example, a hydrogen atom, a halogen atom, an alkoxy group,
Examples thereof include an acyloxy group, a ketoximate group, an amino group, an amide group, an aminooxy group, a mercapto group, and an alkenyloxy group. Among these, an alkoxy group such as a methyl group or an ethyl group is particularly preferred because of its mild hydrolyzability and easy handling. A reactive silicon group whose hydrolyzability is an alkoxy group is called an alkoxysilyl group.

The hydrolyzable group or hydroxyl group can be bonded to one silicon atom in the range of 1 to 3 and (a + Σ
b) preferably ranges from 1 to 5. When two or more hydrolyzable groups or hydroxyl groups are bonded to the reactive silicon group, they may be the same or different. The number of silicon atoms forming the reactive silicon group may be one,
The number may be more than 20, but in the case of silicon atoms linked by a siloxane bond or the like, the number is preferably up to 20. In particular, the reactive silicon group represented by the general formula (3) is preferable because a compound having a reactive silicon group used as a raw material is easily available.

[0010]

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(Wherein R ² , X and a are the same as described above). Also, R ¹ and R ² in the above general formulas (2) and (3)
Specific examples of the group include, for example, an alkyl group such as a methyl group and an ethyl group, a cycloalkyl group such as a cyclohexyl group, an aryl group such as a phenyl group, an aralkyl group such as a benzyl group, and a case where R ³ is a methyl group or a phenyl group. there triorganosiloxy group represented by R ³ ₃ SiO- and the like. As R ¹ and R ² , a methyl group is particularly preferred.

It is preferable that at least one, preferably 1.1 to 5 reactive silicon groups be present in the oxyalkylene polymer molecule. If the number of reactive silicon groups contained in the molecule is less than 1, the curability will be insufficient, and if it is too large, the network structure will be too dense to exhibit good mechanical properties such as rubber elastic behavior. The reactive silicon group may be present at the terminal of the molecular chain of the oxyalkylene polymer, may be present internally, or may be present at both.
In particular, when the reactive silicon group is present at the terminal of the molecular chain, it is preferable from the viewpoint that a rubbery cured product having high strength and high elongation can be easily obtained. These oxyalkylene polymers having a reactive silicon group may be used alone or in combination of two or more.

The polymer of the component (A) may be a linear polymer or a branched polymer, and has a number average molecular weight of 5
About 00-50,000, more preferably 1,000-
30,000. The introduction of the reactive silicon group into the polymer may be performed by a known method. That is, for example, the following method is used.

(A) An oxyalkylene polymer having a functional group such as a hydroxyl group in the molecule is reacted with an organic compound having an active group and an unsaturated group which are reactive with the functional group, thereby forming an unsaturated group. To obtain an oxyalkylene polymer. Alternatively, an unsaturated group-containing oxyalkylene polymer is obtained by copolymerization with an unsaturated group-containing epoxy compound.
Next, the obtained reaction product is reacted with a compound having a group capable of reacting with an unsaturated group and a reactive silicon group. Examples of the compound having a group capable of reacting with the unsaturated group and the reactive silicon group include a hydrosilane having a reactive silicon group and a mercapto compound having a reactive silicon group.

(B) an oxyalkylene polymer having a functional group such as a hydroxyl group, an acryloyl group, an amino group, a mercapto group, an epoxy group or an isocyanate group in a molecule;
A compound having a reactive functional group and a reactive silicon group is reacted with the functional group. Among the above methods, the method of (a) or the method of (b) is preferably a method of reacting a polymer having a hydroxyl group at a terminal with a compound having an isocyanate group and a reactive silicon group.

As a specific example of the component (A), Japanese Patent Publication No. Sho 45
JP-B-36319, JP-A-46-12154, JP-A-50-156599, JP-A-54-6096, JP-A-55-13767, JP-A-55-13468, JP-A-57-164123, Fairness 3-245
No. 0, U.S. Pat. No. 3,632,557, U.S. Pat. No. 4,345,053, U.S. Pat.
No. 6,307, U.S. Pat. No. 4,960,844, etc .;
No. 631, No. 61-215622, No. 61-
Nos. 215623 and 61-218632, and the number average molecular weight of 6,000 or more, Mw / M
An oxyalkylene polymer having a high molecular weight of n of 1.6 or less and a narrow molecular weight distribution can be exemplified, but is not particularly limited thereto.

The above oxyalkylene polymers having a reactive silicon group may be used alone or in combination of two or more. Further, a modified oxyalkylene polymer having a reactive silicon group may be used as the component (A). A typical modified product is a modified product obtained by polymerizing a monomer such as a vinyl monomer in the presence of an oxyalkylene polymer having a reactive silicon group.
A preferred specific example is an acrylate monomer having an alkyl group having 1 to 8 carbon atoms represented by the following general formula (4) and / or a methacrylate having an oxyalkylene polymer having a reactive silicon group. Polymerization of a mixture of an acrylate monomer, an acrylate monomer having an alkyl group having 10 or more carbon atoms and / or an alkyl methacrylate monomer represented by the following general formula (5) It is a modified product obtained. The use of this modified product improves the weather resistance of the cured product of the curable resin composition. CH ₂ ＣC (R ⁵ ) (COOR ⁴ ) (4) (wherein, R ⁴ represents an alkyl group having 1 to 8 carbon atoms, and R ⁵ represents a hydrogen atom or a methyl group). CH ₂ ＣC (R ⁵ ) (COOR ⁶ ) (5) (wherein, R ⁵ is the same as described above, and R ⁶ represents an alkyl group having 10 or more carbon atoms) As R ^{4 in the} general formula (4), for example, a methyl group,
Ethyl group, propyl group, n-butyl group, t-butyl group,
Examples thereof include an alkyl group having 1 to 8, preferably 1 to 4, and more preferably 1 to 2 carbon atoms such as a 2-ethylhexyl group. In addition, the monomer represented by the general formula (4) may be one kind, or two or more kinds.

As R ^{6 in the} general formula (5), for example, lauryl group, tridecyl group, cetyl group, stearyl group, alkyl group having 22 carbon atoms, behenyl group and the like have 10 or more carbon atoms, usually 10 to 30 carbon atoms. Preferably, a long-chain alkyl group of 10 to 20 is used. The monomer represented by the general formula (5) may be used alone or in combination of two or more.

The mixing ratio of the monomer of the formula (4) to the monomer of the formula (5) is preferably from 95: 5 to 40:60 by weight,
0:10 to 60:40 is more preferable. In this polymerization, a monomer other than the formulas (4) and (5) may be used in combination,
Examples of such a monomer include acrylic acid such as acrylic acid and methacrylic acid; amide groups such as acrylamide, methacrylamide, N-methylolacrylamide, and N-methylolmethacrylamide; epoxy groups such as glycidyl acrylate and glycidyl methacrylate; Monomers containing amino groups such as diethylaminoethyl acrylate, diethylaminoethyl methacrylate, aminoethyl vinyl ether; and other monomers such as acrylonitrile, styrene, α-methylstyrene, alkyl vinyl ether, vinyl chloride, vinyl acetate, vinyl propionate, and ethylene Is raised. In this case, the total of the polymerized monomers of the formulas (4) and (5) is preferably at least 50%, more preferably at least 70% by weight of the whole polymerized monomers.

Further, a polymer obtained by polymerizing a monomer containing a vinyl monomer having a reactive silicon group in the presence of an oxyalkylene polymer having no reactive silicon group may also be used in the present invention. Can be used as an ingredient. Such a modified polymer is disclosed in JP-A-59-78223 and JP-A-5-78223.
Specific disclosures in JP-A-9-168014, JP-A-60-228516, JP-A-60-228517 and the like are not intended to limit the scope of the present invention.

The curable composition of the present invention comprises (a) an oxyalkylene polymer having at least one reactive silicon group in a molecule and another polymer having a reactive silicon group, for example, polydimethylsiloxane. May be used in combination. Further, a polymer having no reactive silicon group may be used in combination. Among these polymers, preferred are vinyl polymers having a reactive silicon group, particularly those having a reactive silicon group and having a (meth) acrylate monoester represented by the general formula (4). It is a copolymer obtained by polymerizing a monomer and an alkyl (meth) acrylate monomer represented by the general formula (5). The use of this copolymer improves the weather resistance of a cured product of the curable resin composition. The abundance ratio of the unit derived from the monomer of the formula (4) and the unit derived from the monomer of the formula (5) in the polymer is 95: 5 to 40:60 by weight.
Is preferred, and 90:10 to 60:40 is more preferred.

The copolymer may be obtained by polymerizing a monomer other than the monomers of the formulas (4) and (5). Mers. In this case, the total of the monomer units of the formulas (4) and (5) in the copolymer is preferably 50% by weight, particularly preferably 70% by weight or more. The copolymer preferably has a number average molecular weight of 500 to 100,000 from the viewpoint of easy handling. As the reactive silicon group contained in the copolymer, the same reactive silicon group as the reactive silicon group in the oxyalkylene polymer of the component (a) used in the present invention can be used.
The number of reactive silicon groups during the copolymerization is preferably at least one, more preferably at least 1.1, particularly preferably at least 1.5 from the viewpoint of obtaining sufficient curability. It is preferable that the number is present so that the number average molecular weight per one becomes 300 to 4,000.

The vinyl polymer having a reactive silicon group is
JP-A-59-122541 and JP-A-63-11264.
No. 2, JP-A-6-172631, and the like. The silicon compound having at least one amino group in the molecule used as the component (b) in the present invention can be represented by the general formula (6).

[0024]

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(Wherein, Y is an alkyl group having an amino group, R ¹ is the same as described above. X is a hydroxyl group, a different or the same type of hydrolyzable group or —O—SiQ ₃ group, provided that Q is a hydroxyl group, a different group or Same type of hydrolysable group, 1-20 carbon atoms
Which is a group selected from a substituted or unsubstituted monovalent organic group or a triorganosiloxy group, which contains at least one hydroxyl group, a different or the same type of hydrolyzable group.
c is 1, 2 or 3, and d is 1 or 2. Examples of the silicon compound having at least one amino group and at least one hydrolyzable group in the molecule include γ-aminopropyltriethoxysilane (A-1100: manufactured by Nippon Unicar) and N- (β-aminoethyl) -γ- Aminopropyltrimethoxysilane (A-1120: Nippon Unicar Co., Ltd.), N- (β-aminoethyl) -γ-aminopropylmethyldimethoxysilane (KBM-602: Shin-Etsu Chemical Co., Ltd.), diethylenetriaminopropyltrimethoxysilane (A -1130: Nippon Unicar Co., Ltd.), N, N-dimethyl-γ-aminopropyltrimethoxysilane (D520
0: Chisso), N, N'-bis [γ-trimethoxysilylpropyl] ethylenediamine (XS1003: Chisso), N-benzyl-γ-aminopropyltrimethoxysilane (X-12-512: Shin-Etsu Chemical) ), N-phenyl-γ-aminopropyltrimethoxysilane (KB
M573: Shin-Etsu Chemical Co., Ltd.) and the like, but not limited thereto.

At least one amino acid in these molecules
The amount of the silicon compound having a group is based on the reactive silicon group.
Based on 100 parts by weight of oxyalkylene polymer having
About 0.01 to 20 parts by weight is preferable, and 0.1 to 10 parts by weight
More preferably, the amount is about parts. In the present invention, the component (c)
As the formula, R⁷ _ThreeTrialkylsila represented by SiOH
Knol compound is used. Where R⁷Has 1 to 20 carbon atoms
Alkyl group, aryl group having 6 to 20 carbon atoms, 7 to 7 carbon atoms
20 aralkyl groups or R^Three _ThreeSiO- (R^ThreeIs the carbon number
A monovalent hydrocarbon group of 1 to 20;^ThreeIs the same
Or may be different).
An organosiloxy group, three R ⁷Are the same
And may be different. R⁷Examples of
For example, alkyl groups such as methyl group and ethyl group, cyclohexyl
Ali groups such as cycloalkyl groups such as sil groups and phenyl groups
An aralkyl group such as a benzyl group or a benzyl group;^ThreeBut
R such as^Three _ThreeSiO-
And a liorganosiloxy group. R⁷As
A tyl group is particularly preferred.

Examples of the component (c) include, but are not limited to, trimethylsilanol, triethylsilanol, dimethylphenylsilanol, methyldiphenylsilanol, triphenylsilanol, and the like. The amount of the component (c) is 0.01 to 100 parts by weight of the oxyalkylene polymer having a reactive silicon group.
About 20 parts by weight, more preferably about 0.1 to 10 parts by weight.

Various plasticizers can be used in the composition of the present invention, if necessary. When these additives are used in such a manner that the total amount of the plasticizer is in the range of 0.1 to 150 parts by weight based on 100 parts by weight of the oxyalkylene polymer, preferable results can be obtained. If the amount exceeds 150 parts by weight, the liquid component increases and the improvement effect cannot be obtained. Examples of the plasticizer include phthalic esters such as dioctyl phthalate, diisodecyl phthalate, dibutyl phthalate, and butyl benzyl phthalate; epoxy plasticizers such as epoxidized soybean oil, epoxidized linseed oil, and benzyl epoxy stearate; dibasic acid Polyester-based plasticizers such as polyesters of styrene and dihydric alcohols; polyethers such as polypropylene glycol and derivatives thereof;
Polystyrenes such as poly-α-methylstyrene and polystyrene; plasticizers such as polybutadiene, butadiene-acrylonitrile copolymer, polychloroprene, polyisoprene, polybutene and chlorinated paraffins are used alone or in the form of a mixture of two or more. Can be used for

Further, the composition of the present invention may contain a silanol condensation catalyst for accelerating the reaction of the reactive silicon group. Examples of such silanol condensation catalysts include titanates such as tetrabutyl titanate and tetrapropyl titanate; dibutyl tin dilaurate, dibutyl tin maleate, dibutyl tin diacetate, octyl acid tin, naphthenate tin, dibutyl tin oxide and phthalic acid. Reaction products with esters, organic tin compounds such as dibutyltin diacetylacetonate; organic aluminum compounds such as aluminum trisacetylacetonate, aluminum trisethylacetoacetate, diisopropoxyaluminum ethylacetoacetate; bismuth-tris (2- Reaction products of bismuth salts such as ethylhexoate) and bismuth-tris (neodecanoate) with organic carboxylic acids; zirconium tetraacetylacetonate, titanium tetraa Chelate compounds such as chill acetonate; organic lead compounds such as lead octylate; organic vanadium compound; butylamine, octylamine,
Dibutylamine, monoethanolamine, diethanolamine, triethanolamine, diethylenetriamine, triethylenetetramine, oleylamine, cyclohexylamine, benzylamine, diethylaminopropylamine, xylylenediamine, triethylenediamine, guanidine, diphenylguanidine, 2,4,6-tris (Dimethylaminomethyl) phenol, morpholine, N-
Methylmorpholine, 2-ethyl-4-methylimidazole,
1,8-diazabicyclo (5,4,0) undecene-7 (DBU)
And the like; salts with amine compounds such as carboxylic acids and the like; low molecular weight polyamide resins obtained from excess polyamine and polybasic acid; reaction products of excess polyamine and epoxy compound; The condensation catalyst is not limited thereto, and a generally used condensation catalyst can be used. These silanol catalysts may be used alone or in combination of two or more. Among these silanol condensation catalysts, organometallic compounds or a combination of an organometallic compound and an amine compound are preferred from the viewpoint of curability.

The amount of these silanol condensation catalysts used is
Oxyalkylene polymer having reactive silicon group 10
The amount is preferably about 0.01 to 20 parts by weight, more preferably about 0.1 to 10 parts by weight, based on 0 parts by weight. If the amount of the silanol condensation catalyst used is too small relative to the oxyalkylene-based polymer, the curing rate becomes slow, and the curing reaction does not easily proceed sufficiently. On the other hand, if the amount of the silanol condensation catalyst used is too large relative to the oxyalkylene polymer, undesirably, local heat generation or foaming occurs during curing, making it difficult to obtain a good cured product.

The composition of the present invention may further contain, if necessary, a dehydrating agent, a compatibilizer, an adhesion improver, a physical property modifier, a storage stability improver, a filler, an antioxidant, an ultraviolet absorber, Various additives such as metal deactivators, ozone deterioration inhibitors, light stabilizers, amine radical chain inhibitors, phosphorus peroxide decomposers, lubricants, pigments, foaming agents, flame retardants, antistatic agents, silane compounds, etc. An agent can be appropriately added.

For example, when a filler is used as an additive,
Wood flour, walnut shell flour, rice hull flour, pulp, cotton chips, mica, graphite, diatomaceous earth, clay, kaolin, clay, talc, fumed silica, precipitated silica, silicic anhydride, quartz powder, glass beads, Calcium carbonate, magnesium carbonate, titanium oxide, aluminum powder, zinc powder, asbestos, glass fiber, carbon fiber and the like can be used. These fillers may be used alone or in combination of two or more.

(A) an oxyalkylene polymer and (b)
The method for preparing the composition of the present invention comprising the component and the component (c) is not particularly limited. As a specific example, the component (b) and the component (c) are added to the (a) oxyalkylene polymer, respectively. What is necessary is just to add, to adjust stirring conditions etc. suitably as needed, and to disperse uniformly. As the stirrer, for example, a method of mixing using a mixer, a three-roll mill, a kneader, or the like can be adopted.

The composition obtained as described above can be applied as a two-part or one-part type curable composition. In the latter case, it is obtained by preparing the composition of the present invention in a substantially water-free state, and when stored in a sealed state, can withstand long-term storage, and when exposed to the atmosphere, cures quickly from the surface. Start. The composition of the present invention can be used as an elastic sealing material in buildings, civil engineering works and the like. Further, it is useful in industrial fields such as automobiles, aircraft, vehicles, ships, containers and the like, and can also be used as paints, adhesives, fillers, and coating materials.

[0035]

The composition of the present invention will be described in more detail with reference to the following examples.

[0036]

EXAMPLE 1 A number average molecular weight of 17,000 containing an average of 2.1 methyldimethoxysilyl groups—Si (CH ₃ ) (OCH ₃ ) ₂ per molecule in a sealable kneader (planetary mixer). 100 parts by weight of propylene oxide polymer, 55 parts by weight of DIDP (diisodecyl phthalate) as a plasticizer, 120 parts by weight of surface-treated colloidal calcium carbonate as a filler, titanium oxide 20
Then, 2 parts by weight of an aliphatic amide wax as an anti-sagging agent, 1 part by weight of an ultraviolet absorber, and 1 part by weight of a light stabilizer were added, and the mixture was dehydrated by stirring under vacuum at 120 ° C. for 2 hours. After cooling to room temperature, 2 parts by weight of vinyltrimethoxysilane as a viscosity stabilizer, 2 parts by weight of U-220 (Nitto Kasei Co., Ltd.) as a curing catalyst, and N- (β-aminoethyl) -γ-aminopropyl as a surface modifier 5 parts by weight of trimethoxysilane and 1.2 parts by weight of trimethylsilanol were added and stirred at room temperature. This was filled in a closed container to obtain a one-part curable composition.

The composition obtained as described above is 3 mm
And cured at 23 ° C. and 55% RH. After one day, the surface of the cured product is coated with five commercially available industrial solvent-based acrylic paints (three acrylic urethane-based paints, one acrylic lacquer, one acrylic enamel 1). Seed) was coated with a brush, and after 7 days, a grid test (25 pieces) was performed at 2 mm intervals using cellophane tape made by Nichiban. The evaluation was shown as a percentage (%) of the number of grids remaining on the sealant surface with respect to the total number of grids.

A cured product of the composition obtained in the same manner was evaluated for tensile properties in accordance with JIS K6251. Table 1 shows the results.

[0039]

Examples 2-3 The same procedures as in Example 1 were carried out except that the amounts of N- (β-aminoethyl) -γ-aminopropyltrimethoxysilane and trimethylsilanol used in Example 1 were changed to the amounts shown in Table 1. Carried out. Table 1 shows the results.

[0040]

Comparative Examples 1 to 3 In Example 1, N- (β-aminoethyl) -γ-aminopropyltrimethoxysilane and / or
Or, it carried out similarly to Example 1 except not using trimethylsilanol. Table 1 shows the results.

[0041]

[Table 1]

[0042]

As described above, the present invention can provide a curable composition having excellent paint adhesion.

Claims (2)

[Claims] 1. A (a) oxyalkylene polymer containing at least one reactive silicon group in its molecule, a silicon compound having at least one amino group in (b) molecules, and (c) expression, R ⁷ ₃ SiOH, (wherein R ⁷ has 1 carbon atom
20 alkyl group, an aryl group having 6 to 20 carbon atoms, an aralkyl group or R ³ of 7 to 20 carbon atoms ₃ SiO- (R ³
Is a monovalent hydrocarbon group having 1 to 20 carbon atoms, and three R
³ may be the same, a triorganosiloxy group represented by different may be), the three R ⁷ may be the same, a silanol compound represented by the different may be) Curable composition containing. 2. A method for applying a paint to a cured product of a curable composition containing an oxyalkylene polymer containing at least one reactive silicon group in a molecule,
Silicon compound having at least one amino group in addition (b) in the molecule as the curable composition containing an oxyalkylene polymer containing at least one reactive silicon group in its molecule and (c) expression, R ⁷ ₃ SiOH, where R
⁷ is an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aralkyl group, or R ³ ₃ S 7 to 20 carbon atoms
a triorganosiloxy group represented by iO- (R ³ is a monovalent hydrocarbon group having 1 to 20 carbon atoms, and three R ^{3 s} may be the same or different); three R ⁷ may be the same, a method of using a curable composition containing a silanol compound represented by different may be).