JPH0912889A - Room temperature curing organopolysiloxane composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To prepare a room temp. curing compsn. having excellent waterproofing adhesion by incorporating a silane crosslinking agent, a polyadduct of an acrylic ester with an amino-contg. silane, an epoxy-contg. compd. and the like into a particular diorganopolysiloxane. SOLUTION: A hydrolyzable silane represented by formula II (R<2> represents a hydrocarbon; X represents a hydrolyzable group; and a is 0 to 1), a hydrolysis- condensation product of the silane, or a mixture thereof (B), a product of Michael addition (C) between a (meth)acrylic ester and an amino-contg. silane represented by formula III (R<3> represents a hydrocarbon; R<4> represents a hydrocarbon substituted with an alkyl-substd. amino; and m is 0 to 3), (meth) acrylonitrile or epoxy-contg. compd. (D), and curing catalyst and a filler are incorporated into a diorganopolysiloxane (A) represented by formula I (R<1> represents a hydrocarbon; and n is 15 or more) to prepare a room temp. curing flooring material. The component (B) functions as a crosslinking agent, and the component (C) functions as an agent for imparting adhesiveness. The component (D) functions to block active water in the compsn., keeping the adhesion to an area to be applied and exposed to water without using any primer.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a room-temperature-curable organopolysiloxane composition whose cured product has excellent water-resistant adhesiveness and which is particularly useful as a sealing material for construction.

[0002]

2. Description of the Related Art Room-temperature-curable organopolysiloxane compositions are used as architectural sealants because the cured products are excellent in heat resistance, ultraviolet resistance, weather resistance and the like. In particular, the organopolysiloxane composition used for this sealant for construction is required to have so-called water-resistant adhesiveness, which does not easily lower the adhesiveness to the construction portion even after being exposed to water after curing. Conventionally, when an organopolysiloxane composition having no self-adhesiveness is used as a sealing material, in order to improve the above-mentioned water-resistant adhesiveness, the surface of the application site is pre-treated with a primer and then applied. However, in the method using a primer, adjustment of the coating amount of the primer and control of the air-drying time after the coating are complicated, and after the primer is coated, the surface is prevented from being contaminated until it is dried. There is also the problem of requiring caution. In addition, there is a problem in application work such as the occurrence of a construction site where the primer is forgotten to be applied. An organopolysiloxane composition containing an amine-based adhesion-imparting agent is known as a sealing material that adheres to the surface of a construction site without such a primer treatment. However, this sealing material has a drawback that the water-resistant adhesiveness is insufficient.

[0003]

SUMMARY OF THE INVENTION An object of the present invention is to provide a room temperature curable organopolysiloxane composition having a cured product excellent in water-resistant adhesion.

[0004]

The present inventors have found that the amino groups of the above-mentioned amine-based adhesion promoter and active hydrogen atoms remaining in the composition after curing are the cause of lowering the water-resistant adhesion. Has reached the present invention. That is, the present invention
(A) General formula (1) below: HO (SiR ¹ ₂ O) _n H (1) (In the formula, R ¹ is independently an unsubstituted or substituted monovalent hydrocarbon group, and n is an integer of 15 or more. (B) the following general formula (2): R ² _a SiX _4-a (2) (wherein R ² is an unsubstituted or substituted monovalent hydrocarbon group). And X is a hydrolyzable group and a is 0 or 1), a hydrolyzable silane represented by the formula, a partial hydrolyzed condensate thereof or a mixture thereof, (C) (meth) acrylic acid ester, General formula (3) below: R ³ _m (R ³ O) _3-m Si—R ⁴ —NH ₂ (3) (In the formula, R ³ is independently an unsubstituted or substituted monovalent hydrocarbon group, R ⁴ is an unsubstituted or divalent hydrocarbon group in which at least a part of hydrogen atoms bonded to carbon atoms are substituted with an alkyl-substituted amino group, or an imino group is present. And is a divalent organic group in which two divalent hydrocarbon groups are bonded, and m is 0, 1, 2
Or 3), a Michael-type polyaddition reaction product with an amino group-containing silane, (D) a compound containing a (meth) acryloyl group or an epoxy group, (E) a curing catalyst, and (F) a filler. It is a room temperature curable organopolysiloxane composition containing. Hereinafter, the present invention will be described in detail.

(A) Diorganopolysiloxane The diorganopolysiloxane used in the present invention is represented by the above general formula (1). In the formula, examples of the unsubstituted or substituted monovalent hydrocarbon group for R ¹ include, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, neopentyl group,
Alkyl groups such as hexyl group, heptyl group, octyl group, nonyl group, decyl group, dodecyl group; cyclopentyl group,
Cycloalkyl groups such as cyclohexyl group and cycloheptyl group; vinyl group, allyl group, propenyl group, isopropenyl group, butenyl group, isobutenyl group, hexenyl group,
Alkenyl groups such as cyclohexenyl group; aryl groups such as phenyl group, tolyl group, xylyl group, naphthyl group, biphenylyl group; aralkyl groups such as benzyl group, phenylethyl group, phenylpropyl group, methylbenzyl group; and these groups A group in which some or all of the hydrogen atoms bonded to the carbon atom of are substituted with a halogen atom such as fluorine, chlorine or bromine, a cyano group or an amino group, for example, a chloromethyl group, a 2-bromoethyl group, 3 -Chloropropyl group,
3-aminopropyl group, 3,3,3-trifluoropropyl group, chlorophenyl group, fluorophenyl group, cyanoethyl group, 3,3,4,4,5,5,6,6,6-nonafluorohexyl group, etc. Are preferred, and a methyl group, a phenyl group, and a 3,3,3-trifluoropropyl group are preferred. In the general formula (1), n is an integer of 15 or more, and usually has a viscosity of 25 to 500,0 at 25 ° C.
00cP range, preferably 700-100,000c
It is an integer in the range of P.

(B) Hydrolyzable silane or its partial hydrolysis
Decomposition Condensate The component (B) used in the present invention is a hydrolyzable silane represented by the above general formula (2), a partial hydrolysis condensate thereof or a mixture thereof, and a crosslinking agent in the composition of the present invention. Acts as. In the formula, a is 0 or 1. Where R
The ^second non-substituted or substituted monovalent hydrocarbon group include the same groups as those exemplified as R ¹ in the general formula (1). In the formula, the hydrolysable groups X, for example, a methoxy group, an ethoxy group, an alkoxy group or a butoxy group; dimethyl ketoxime group, the following equation such as methyl ethyl ketoxime _{^{group: -O-N = CR 5 2}} ( where , R ⁵ are independently an alkyl group having 1 to 7 carbon atoms such as a methyl group, an ethyl group and a propyl group), a ketoxime group (hereinafter the same); an acyloxy group such as an acetoxy group; N- Amino group such as butylamino group, N, N-diethylamino group; Amido group such as N-methylacetamide group; Aminooxy group such as N, N-dimethylaminooxy group; Propenyloxy group, isopropenyloxy group, isobu Examples thereof include an alkenyloxy group such as a tenyloxy group and a cyclohexenyloxy group.

As the hydrolyzable silane represented by the general formula (2), the hydrolyzable silane usually used in the condensation-curing type silicone rubber composition of this kind is preferably used. Yes, as a concrete example,
Tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane, tetrabutoxysilane, methyltrimethoxysilane, methyltriethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane,
Alkoxysilanes such as 3-chloropropyltrimethoxysilane, 3-chloropropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane; methyltris (dimethylketoxime) silane, methyltris (diethylketoxime). Silane, methyltris (methylethylketoxime) silane, vinyltris (dimethylketoxime) silane, vinyltris (diethylketoxime) silane,
Ketooxime silanes such as vinyltris (methylethylketoxime) silane, tetra (dimethylketoxime) silane, tetra (diethylketoxime) silane, tetra (methylethylketoxime) silane; methyltriacetoxysilane, ethyltriacetoxysilane, vinyltriacetoxysilane, Acyloxysilanes such as phenyltriacetoxysilane; methyltris (N-methylacetamido) silane, ethyltris (N-methylacetamido) silane, vinyltris (N-methylacetamido) silane, phenyltris (N-methylacetamido) silane and other amidosilanes; methyltris (N-butylamino) silane, vinyl tris (N-butylamino)
Silane, phenyltris (N-butylamino) silane,
Aminosilanes such as methyltris (N, N-diethylamino) silane, vinyltris (N, N-diethylamino) silane and phenyltris (N, N-diethylamino) silane; methyltris (N, N-dimethylaminooxy)
Silane, methyltris (N, N-diethylaminooxy) silane, vinyltris (N, N-dimethylaminooxy) silane, vinyltris (N, N-diethylaminooxy) silane, phenyltris (N, N-dimethylaminooxy) silane, phenyl Aminooxysilanes such as tris (N, N-diethylaminooxy) silane; vinyltriisopropenyloxysilane; vinyltripropenyloxysilane; methyltriisobutenyloxysilane; alkenyloxysilanes such as phenyltricyclohexenyloxysilane. To be Such a silane compound having a hydrolyzable group or a partial hydrolysis-condensation product thereof can be used alone or in combination of two or more.

The amount of the component (B) used is the same as the amount of the above-mentioned component (A).
It is 0.2 to 10 parts by weight, preferably 0.5 to 8 parts by weight, per 100 parts by weight. If the amount used is too small, crosslinking may not proceed sufficiently and rubber properties suitable as a sealing material may not be obtained. On the other hand, if the amount is too large, the unreacted component (B) remaining in the cured composition may be hydrolyzed over time to generate active hydrogen atoms, and the water-resistant adhesion of the cured product may be reduced. In addition, the cured product may become brittle and the mechanical strength may decrease.

(C) Michael-type polyaddition reaction product Component (C) used in the present invention is a Michael-type polyaddition product of a (meth) acrylic acid ester and an amino group-containing silane represented by the general formula (3). It is an addition reaction product. (Meth) Acrylic Acid Ester The above-mentioned (meth) acrylic acid ester is a compound having a (meth) acryloyloxy group represented by the following general formula (4) or general formula (5). _{CH 2 = CHCOO-Y (4} ) CH 2 = C (CH 3) in COO-Y (5) wherein, as the group represented by Y include methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl Group, isobutyl group, tert-butyl group, pentyl group, neopentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, dodecyl group, and other alkyl groups; the following general formula: -R ⁶ -SiR ⁷ _L ( OR ⁷ ) _3-L (In the formula, R ⁶ is, for example, an alkylene group having 1 to 10 carbon atoms such as a methylene group, an ethylene group, and a propylene group, and R ⁷ is independently a methyl group, An alkyl group having 1 to 7 carbon atoms such as an ethyl group and a propyl group, L
Is an integer of 0 to 3), the following general formula:

[0010]

Embedded image (In the formula, R ⁸ is independently the same alkyl group or (meth) acryloyloxy group as the above R ^7, and p is an integer of 3 to 10), the following general formula: — (R ⁸ ₂ SiO) _M —R ⁹ (in the formula, R ⁸ is the same as defined above, R ⁹ is an alkyl group similar to the above R ⁷ , and M is an integer of 3 to 10) Etc. Specific examples of such (meth) acrylic acid ester include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, and 2- (meth) acrylate.
Ethylhexyl (meth) acrylate, γ- (meth) acryloyloxypropyltrimethoxysilane, 1,
Examples include 3,5,7-tetrakis [(meth) acryloyloxypropyl] -1,3,5,7-tetramethyltetracyclosiloxane and ring-opening polymerization of the cyclosiloxane. Such (meth) acrylic acid ester preferably has a molecular weight of 1,000 or less, particularly 600 or less. If the molecular weight is too large, it may be impossible to impart self-adhesiveness to the composition unless the compounding amount is increased. When siloxane is used as the (meth) acrylic acid ester, those not modified with a polyether group are preferable. Further, a (meth) acrylic acid ester having no hydrophilic functional group is preferable because it improves the water-resistant adhesiveness of the composition of the present invention.

Amino Group-Containing Silane The amino group-containing silane is represented by the above general formula (3). In the formula, m is 0, 1, 2 or 3. In the formula, R ³
Examples of the unsubstituted or substituted monovalent hydrocarbon group include the same as those exemplified as R ^{1 in} the above general formula (1). In the formula, examples of the divalent hydrocarbon group represented by R ⁴ include alkylene groups such as methylene group, ethylene group, trimethylene group, methylethylene group, tetramethylene group, hexamethylene group and methylpropylene group; phenylenemethylene group, phenylene group. an ethylene group, phenylene alkylene group such as phenylene propylene group; phenylene methylene group, represented by the following general formula, such as phenylenemethylene ethylene group ^{(I): -R 10 -Ph-} R 10 - (I) ( wherein, R ¹⁰ is, An alkylene group similar to the above, P
h is a phenylene group), a hydrogen atom bonded to a carbon atom of such a divalent hydrocarbon group such as a group represented by, for example, an N-aminomethyl group. , N-aminoethyl group, N-aminopropyl group and the like substituted with an alkyl-substituted amino group, for example, 2- (N
Examples include -aminoethyl) propylene group and 2- (N-aminoethyl) phenyleneethylene group. Also, R
The divalent hydrocarbon group of ⁴ is 2 via an imino group represented by the following general formula: —R ¹¹ —NH—R ¹¹ — (wherein R ¹¹ is independently a divalent hydrocarbon group). Two divalent hydrocarbon groups are bonded 2
Examples include valent organic groups. Examples of the divalent hydrocarbon group for R ¹¹ include the above-mentioned alkylene groups; phenylene alkylene groups; and the groups represented by the general formula (I).
Specific examples of such a divalent organic group include, for example, -C
_{H 2 NHCH 2 -, - CH} 2 NHC 2 H 4 -, - C 2 H
_{4 NHC 2 H 4 -, -} C 2 H 4 NHC 3 H 6 -, - C 3
_{H 6 NHC 3 H 6 -,} - C 2 H 4 NHCH 2 -Ph-C 2 H 4
-(However, Ph is a phenylene group) etc. are mentioned.

Specific examples of such amino group-containing silanes include γ-aminopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropylmethyldimethoxysilane, H ₂ NC ₂ H ₄ NH.
_{C 3 H 6 -Si (OMe)} 3 ( where, Me is a methyl _{group), H 2 NC 2 H 4} NHC 3 H 6 -Si (Me) (OMe) 2 ( where, Me is a methyl group) , H ₂ NC ₂ H ₄ NHCH ₂ −
Ph-C ₂ H ₄ Si (OMe) ₃ (However, Me is a methyl group, Ph
Is a phenylene group) and the like.

Michael-type polyaddition reaction product The above-mentioned Michael-type polyaddition reaction product is a Michael-type polyaddition product of the (meth) acrylic acid ester and the amino group-containing silane represented by the general formula (3). It is a reaction product.
The (meth) acrylic acid ester and the amino group-containing silane may be used in such amounts that the (meth) acryloyloxy group content in the ester and the amino group content in the silane are equimolar. The reaction temperature is 50 to 150 ° C.
The reaction time may be about 3 to 10 hours.

Examples of such Michael type polyaddition reaction products include those represented by the following general formulas (6) and (7). _{^{R 3 m (R 3 O)}} 3-m Si-R 4 -NHCH 2 -CH 2 COO-Y (6) R 3 m (R 3 O) 3-m Si-R 4 -NHCH 2 -CH (CH 3 ) COO-Y (7) (In the formula, R ³ , R ⁴ , Y and m are the same as above.) Such a Michael type polyaddition reaction product may be used alone or in combination of two or more. Can be used. The amount of component (C) used is 0.1 to 10 parts by weight, preferably 0.1 to 2 parts by weight, per 100 parts by weight of component (A). If the amount used is too small, it may not be possible to impart sufficient self-adhesiveness to the composition. On the other hand, if the amount is too large, the mechanical strength of the cured product may decrease.

(D) (meth) acryloyl group or epoxy
Compound Containing Si Group The component (D) used in the present invention is used to block active hydrogen atoms in the composition, particularly amino groups remaining in the composition. Examples of the compound containing a (meth) acryloyl group used in the present invention include the same compounds as the (meth) acrylic acid ester used to obtain the component (C).

The compound containing an epoxy group used in the present invention is not particularly limited, but a compound containing no hydrophilic group such as a polyether group is preferable. Specific examples of such epoxy group-containing compounds include, for example, allyl glycidyl ether, γ-glycidoxypropyltrimethoxysilane, β- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, and bisphenol A type compounds. An epoxy compound etc. are mentioned. The compound having an epoxy group preferably has a molecular weight of 1,000 or less, particularly 600 or less. These components (D) may be used alone or in combination of two or more.

The amount of the component (D) used is the same as that of the above-mentioned component (A).
It is 0.1 to 10 parts by weight, preferably 0.3 to 7 parts by weight, per 100 parts by weight. If the amount used is too small, it may not be possible to block amino groups remaining in the composition, and if it is too large, the components involved bleed out on the surface at the initial stage of curing of the composition, Adhesiveness to a body (for example, the surface of a construction part) may be deteriorated.

(E) Curing Catalyst Examples of the curing catalyst include tin carboxylates such as tin octenoate, tin naphthenate, stannous caprylate and tin oleate; dibutyltin diacetate, dibutyltin dioctoate, dibutyltin. Dilaurate, dibutyltindiolate,
Tin compounds such as diphenyltin diacetate, dibutyltin oxide, dibutyltin dimethoxide, dibutylbis (triethoxysiloxy) tin and dibutyltin benzylmalate; metal alkoxides such as tetraethyl titanate, tetrapropyl titanate, tetrabutyl titanate and tetraethoxy zirconate. Iron octenoate, iron naphthenate, lead naphthenate, zinc naphthenate, zinc stearate, zinc-2-ethylhexoate, lead-2-ethyloctoate, iron-2-ethylhexoate, cobalt-
Organometallic compounds such as 2-ethylhexoate, manganese-2-ethylhexoate, cobalt naphthenate, and alkoxyaluminum compounds; aminoalkyl such as 3-aminopropyltriethoxysilane and N- (trimethoxysilylpropyl) ethylenediamine Group-substituted alkoxysilanes; amine compounds such as hexylamine and dodecyldodecylamine phosphate and salts thereof; quaternary ammonium salts such as benzyltriethylammonium acetate; lower fatty acid salts of alkali metals such as potassium acetate, sodium acetate and lithium bromide. And dialkylhydroxylamine such as dimethylhydroxylamine and diethylhydroxylamine.

The amount of the component (E) used is the same as that of the above-mentioned component (A).
It is 0.01 to 5 parts by weight, preferably 0.01 to 2 parts by weight, per 100 parts by weight. If the amount used is too small, a sufficient catalytic function will not be exhibited, and conversely, if the amount is too large, the water-resistant adhesiveness to the adherend (for example, the construction part) may deteriorate.

(F) Filler The filler of the component (F) used in the present invention is not particularly limited and may be an inorganic filler usually added to a room temperature curable organopolysiloxane composition. Are, for example, fumed silica and the surface of which is hydrophobically treated with chlorosilane; ground silica, colloidal calcium carbonate and those whose surface is treated with fatty acid soap, rosin or rosin acid ester; heavy calcium carbonate;
Diatomaceous earth; iron oxide; titanium oxide; zinc oxide; magnesium carbonate; zinc carbonate; metal carbonates; carbon black; finely powdered mica. Filler alone or 2
A combination of more than one species may be used.

The amount of the component (F) used is the same as that of the component (A).
1 to 400 parts by weight, preferably 1 per 100 parts by weight
0 to 300 parts by weight. If the amount used is too small, rubber properties suitable as a sealing material may not be obtained. On the other hand, if the amount is too large, the composition of the present invention becomes hard and, for example, the workability during sealing may be deteriorated.

Other Components In addition to the components (A) to (F), the composition of the present invention comprises
If necessary, colorants such as pigments and dyes; heat resistance improvers such as red iron oxide and cerium oxide; dehydrating agents; anticorrosive agents;
A fungicide; a silicone resin or the like may be added. Uses of the composition The room temperature curable organopolysiloxane composition of the present invention comprises
For example, it is useful as a sealant for building materials where appearance is important.

[0023]

EXAMPLES Hereinafter, the present invention will be described more specifically with reference to Examples and Comparative Examples. In each Example, “part” means “part by weight”,
The viscosity is a measured value at 25 ° C. (Example 1) Synthesis of component (C) 1 mol (221 g) of γ-aminopropyltrimethoxysilane was charged into a 1000 ml four-necked flask equipped with a stirrer, a thermometer, a cooling trap, and a dropping funnel, and the dropping funnel was used. 1 mol (234 g) of γ-acryloyloxypropyltrimethoxysilane was added dropwise over 3 hours. Next, the flask contents were heated to 80 ° C. and aged for 5 hours. Then, after confirming that 95 mol% or more of the above-mentioned γ-aminopropyltrimethoxysilane has reacted by using gas chromatography, the reaction is terminated, and a component (C) is obtained as a pale yellowish transparent liquid. It was This (C) component was analyzed by IR and ¹ H-NMR, and the following formula: (MeO) ₃ SiC ₃ H ₆ OCOC ₂ H ₄ NHC ₃ H ₆ Si (OMe) ₃ (wherein Me is a methyl group). It was found that the main component is the addition reaction product represented by (1).

Preparation of Composition A main component was prepared by mixing 100 parts of dimethylpolysiloxane (viscosity: 20000 cP) in which both ends of the molecular chain were terminated with hydroxyl groups and 80 parts of colloidal calcium carbonate surface-treated with a rosin acid ester. 180 parts of the main agent, 1 part of tetrapropoxysilane, 1 part of the prepared (C) component,
0.1 parts of dibutyltin dilaurate and 1 part of butyl acrylate were mixed to obtain a room temperature curable organopolysiloxane composition.

Water Resistance Adhesion Test Using the obtained room temperature curable organopolysiloxane composition and float glass as an adherend, JIS A 5
An H-shaped block was prepared according to 758. After leaving the H-shaped block in an atmosphere of 20 ° C. and 55% RH for 7 days, the H-shaped block was further placed in a dryer at 50 ° C. for 7 days.
By heating for a day, the room temperature-curable organopolysiloxane composition portion of the H-type block was cured. Next, this H-shaped block was immersed in warm water at 80 ° C. And H after immersion
The maximum tensile strength (kg / cm ² ) when peeling the adherend from the cured composition of the mold block and the cohesive failure rate (%) described below were measured. Table 1 shows the results. In Table 1, the initial means the test results of the H-shaped block before immersion, and the 7 days, 14 days, 28 days and 56 days means the H-shaped block after immersion for each period. Represents the test results.

Cohesive failure rate (%) When the adherend is peeled off from the cured composition, the ratio of the area broken in the composition layer to the contact area between the composition and the adherend is expressed as a percentage. The cohesive failure rate was 100% when the composition layer was completely broken, and the cohesive failure rate was 0% when the composition layer was peeled from the adherend surface on all contact surfaces.

(Example 2) Synthesis of component (C) A 1000 ml four-necked flask equipped with a stirrer, a thermometer, a cooling trap and a dropping funnel was charged with the following formula (8): H ₂ NC ₂ H ₄ NHC ₃ H ₆ -Si (OMe) ₃ (8) (In the formula, Me is a methyl group) 1 mol of trimethoxysilane (222 g) was charged, and 1 mol of γ-methacryloyloxypropyltrimethoxysilane ( 248 g) was added dropwise over 3 hours. Then
The contents of the flask were heated to 120 ° C. and aged for 12 hours. Then, after confirming that 90 mol% or more of the trimethoxysilane represented by the above formula (8) has reacted by using gas chromatography, the reaction is terminated and a pale yellowish transparent liquid (C ) Component was obtained. This (C) component is analyzed by IR and ¹ H-NMR, and the following formula: (MeO) ₃ SiC ₃ H ₆ OCOCH (Me) CH ₂ NHC ₂ H ₄ NHC ₃ H
It was found that the main component is an addition reaction product represented by ₆ Si (OMe) ₃ (in the formula, Me is a methyl group).

Preparation of Composition 180 parts of the same main agent as in Example 1, 1 part of tetrapropoxysilane, 1 part of the prepared component (C), 0.1 part of dibutyltin dilaurate and the following formula (9):

Embedded image 4 parts of a compound containing an epoxy group represented by the formula (wherein Ph is a phenyl group) was mixed to obtain a room temperature curable organopolysiloxane composition. A water resistance adhesion test was conducted on the composition in the same manner as in Example 1. Table 1 shows the results.

(Example 3) Main agent 180 similar to that of Example 1
Parts, 1 part of tetrapropoxysilane, 1 part of the component (C) prepared in Example 1, 0.5 of the component (C) prepared in Example 2
Parts, 0.1 part of dibutyltin dilaurate and 1,3,5
7-tetrakis (acryloyloxypropyl) -1,
3 parts of 3,5,7-tetramethyltetracyclosiloxane were mixed to obtain a room temperature curable organopolysiloxane composition. A water resistance adhesion test was conducted on the composition in the same manner as in Example 1. Table 1 shows the results.

(Comparative Example 1) Main agent 180 similar to that of Example 1
Parts, tetrapropoxysilane 1 part, γ-aminopropyltrimethoxysilane 1 mol and dibutyltin dilaurate 0.1 part were mixed to obtain a room temperature curable organopolysiloxane composition. A water resistance adhesion test was conducted on the composition in the same manner as in Example 1. Table 1 shows the results.

Comparative Example 2 A room temperature curable organopolysiloxane composition was obtained in the same manner as in Example 1 except that butyl acrylate was not used. A water resistance adhesion test was conducted on the composition in the same manner as in Example 1. Table 1 shows the results.

(Comparative Example 3) Base material 180 similar to that of Example 1
Parts, tetrapropoxysilane 1 part, γ-aminopropyltrimethoxysilane 1 mol, dibutyltin dilaurate 0.1 part and the epoxy group-containing compound 5 parts represented by the above formula (9) are mixed and cured at room temperature. A hydrophilic organopolysiloxane composition was obtained. A water resistance adhesion test was conducted on the composition in the same manner as in Example 1. Table 1 shows the results.

[0033]

[Table 1]

[0034]

The room-temperature-curable organopolysiloxane composition of the present invention is useful as a sealant for building materials in which the cured product has excellent water-resistant adhesiveness and appearance is important.

Claims (1)

[Claims] (A) The following general formula (1): HO (SiR ¹ ₂ O) _n H (1) (wherein R ¹ is independently an unsubstituted or substituted monovalent hydrocarbon group, and n Is an integer of 15 or more), (B) the following general formula (2): R ² _a SiX _4-a (2) (wherein R ² is an unsubstituted or substituted 1 Which is a valent hydrocarbon group, X is a hydrolyzable group, and a is 0 or 1), a partially hydrolyzed condensate thereof or a mixture thereof, (C) (meth) Acrylic ester and the following general formula (3): R ³ _m (R ³ O) _3-m Si—R ⁴ —NH ₂ (3) (In the formula, R ³ is independently an unsubstituted or substituted monovalent carbon. hydrogen radical, R ⁴ is a divalent hydrocarbon group or at least some of the hydrogen atoms attached to an unsubstituted or carbon atom is substituted with an alkyl-substituted amino group Via the imino group is a divalent organic group in which two divalent hydrocarbon radical bonded, m is 0, 1, 2
Or 3), a Michael-type polyaddition reaction product with an amino group-containing silane, (D) a compound containing a (meth) acryloyl group or an epoxy group, (E) a curing catalyst, and (F) a filler. A room temperature curable organopolysiloxane composition containing: