JPH06322220A - Room-temperature-curable composition - Google Patents

Abstract

PURPOSE:To obtain a room-temperature-curable composition having sufficient adhesion even to a difficultly coatable substrate such as a PVC-covered steel sheet by mixing a silyl-containing acrylic ester polymer with a specified amino compound. CONSTITUTION:The composition comprises 100 pts.wt. polymer whose main chain is a (meth)acrylic ester polymer and which has cross-linkable and hydrolyzable silyl groups and 0.1-40 pts.wt. adduct of a (meth)acrylate compound having a hydrolyzable silyl group with a compound having at least two amino groups selected from among primary amino groups and secondary amino groups in the molecule. This composition has excellent adhesion to various substrates, and therefore it can desirably be used as especially a sealing material or an adhesive.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a room temperature curable composition which reacts with atmospheric moisture to cure into a rubber, and is particularly excellent in adhesiveness to various adherends and useful as a sealing material or an adhesive. It relates to a room temperature curable composition.

[0002]

2. Description of the Related Art As a (meth) acrylic acid ester-based polymer which is cured into a rubber-like substance by reacting with moisture in the atmosphere, an allyl group is disclosed, for example, in JP-A-54-36395. An acrylic ester polymer having
It can be obtained by reacting with a hydrosilicon compound represented by the general formula X _3-a SiR _a H in the presence of a Group III transition metal. (In the formula, R is a group selected from a monovalent hydrocarbon group and a halogenated monovalent hydrocarbon group, a is 0, 1 or 2,
X represents a group or atom selected from a halogen atom, an alkoxy group, an acyloxy group and a ketoximate group. )

The (meth) acrylic acid ester-based polymer thus obtained has excellent weather resistance and is useful as a base resin for adhesives, sealing materials, coating materials, etc., but it is generally (meth) acrylic acid ester-based polymer. The polymer alone has a problem of low adhesion.

Therefore, for the purpose of improving the adhesiveness, for example, Japanese Examined Patent Publication No. 42868/1990 and JP-A-57-105.
In Japanese Patent No. 446, a hydrolyzable silyl group is contained in one molecule in one molecule.
It is disclosed to add amine compounds having more than one. However, there is a problem in that sufficient adhesion cannot be obtained for difficult adherends such as a vinyl chloride steel plate simply by adding the amine compound to the (meth) acrylic acid ester-based polymer.

[0005]

DISCLOSURE OF THE INVENTION The present invention solves the above conventional problems and provides a room temperature curable composition having sufficient adhesiveness even to difficult-to-be-adhered materials such as vinyl chloride steel plates. Is intended.

[0006]

The room temperature curable composition of the first invention is a polymer whose main chain is essentially a (meth) acrylic acid ester-based polymer and which has a crosslinkable hydrolyzable silyl group. (A) and having a hydrolyzable silyl group (meth)
Primary amino group and secondary group to acrylate compound (a)
It is characterized by comprising an addition reaction product (B) of a compound (b) having two or more amino groups selected from amino groups in one molecule.

The room temperature curable composition of the second invention comprises a polymer (A) whose main chain is essentially a (meth) acrylic acid ester-based polymer and which has a crosslinkable hydrolyzable silyl group.
A compound (ha) having two or more (meth) acryloyl groups in one molecule is selected from a primary amine compound having a hydrolyzable silyl group and a secondary amine compound having a hydrolyzable silyl group. It is characterized by comprising an addition reaction product (C) of an amine compound (d).

The present invention will be described in detail below. The polymer (A) used in the present invention is essentially a (meth) acrylic acid ester-based polymer having a main chain and having a crosslinkable hydrolyzable silyl group in the molecule.

Such a polymer (A) is synthesized, for example, by the method described in JP-A-54-36395, and as disclosed in JP-A-57-179210. It can also be obtained by copolymerizing a (meth) acrylic acid alkyl ester monomer with an alkoxysilyl group-containing (meth) acrylic acid alkylethesul monomer in the presence of a mercapto group-containing chain transfer agent.

Further, as described in JP-A-59-78222, a (meth) acrylic acid alkyl ester monomer and a bifunctional radically polymerizable compound are used, and a mercaptan containing an alkoxysilyl group as a chain transfer agent. It can also be obtained by copolymerizing in the presence of

As the above-mentioned polymer (A), a polymer mainly composed of a monomer selected from C2-12 alkyl ester monomers whose main chain is acrylic acid or C6-14 alkyl ester monomers of methacrylic acid is a cured product. It is preferable from the viewpoint of flexibility, and above all, a polymer containing a C2-8 alkyl ester monomer of acrylic acid as a main component is more preferable.
As the hydrolyzable silyl group, an alkoxysilyl group is particularly preferable from the viewpoint of storage stability.

When the molecular weight of the polymer (A) is small, the elongation of the cured product is insufficient, and when it is large, the viscosity is high and the workability of the compounded product is deteriorated.
3,000 to 100,000 is preferable.

The addition reaction product (B) used in the present invention is
A compound (b) having two or more amino groups selected from a primary amino group and a secondary amino group in one molecule to the (meth) acrylate compound (a) having a hydrolyzable silyl group.
Is an addition reaction product of. That is, it is an addition reaction product in which N—H of the compound (b) is added to the C═C double bond in the α, β-unsaturated carbonyl group of the compound (a). It is already known that such an addition reaction easily occurs (for example, M
orison and Boyd Organic
Chemistry Six Edition
p977).

Generally, the addition reaction product (B) is synthesized by the following reaction formula (1) and has two or more hydrolyzable silyl groups and two or more nitrogen atoms in one molecule. . _{^{Z- (NR 2 H) m +}} mCH 2 = CR 3 -COOY → Z- (NR 2 -CH 2 -CHR 3 -COOY) m ··· (1) Equation (1), Z is and primary amino groups Represents a residue of an amino group selected from a secondary amino group, R ² is a hydrogen atom or a secondary
A residue of an amino group is shown, R ³ is a hydrogen atom or a methyl group, and Y is a (meth) acrylate residue having a hydrolyzable silyl group. Further, m represents an integer of 2 or more.

In the addition reaction of the compound (ii) to the (meth) acrylate compound (ii), both compounds (ii) and (ii) are mixed and stirred at a temperature of room temperature to 130 ° C. for several hours to tens of hours. It is obtained by doing. Further, in order to prevent remarkable thickening or gelation during the reaction, the ratio of both is preferably 2 mol or more of compound (a) with respect to 1 mol of compound (b).

The above-mentioned (meth) acrylate compound (a) is preferably a (meth) acrylate compound having an alkoxysilyl group as a hydrolyzable silyl group, such as 3- (meth) acryloxypropyltrimethoxysilane, 3 — (Meth) acryloxypropylmethyldimethoxysilane, 3- (meth) acryloxypropyltriethoxysilane, (meth) acryloxymethyltrimethoxysilane, and the like.

Further, silanes having a functional group capable of reacting with an isocyanate group such as 3-mercaptopropyltrimethoxysilane and 3-aminopropyltrimethoxysilane, hexamethylene diisocyanate, isophorone diisocyanate and diphenylmethane diamine. Reaction products obtained by reacting diisocyanates such as isocyanate and tolylene-2,6-diisocyanate at a ratio of 1: 1;
3-isocyanatopropyltrimethoxysilane and other isocyanate compounds having a hydrolyzable silyl group,
Examples include urethane (meth) acrylates having a hydrolyzable silyl group obtained by reacting with a (meth) acrylate compound having a hydroxy group.

Of these, 3- (meth) acryloxypropyltrimethoxysilane and 3- (meth) acryloxypropylmethyldimethoxysilane are preferably used.

Examples of the compound (b) having two or more amino groups selected from the primary amino group and the secondary amino group in one molecule include ethylenediamine, butylenediamine, hexamethylenediamine and 1,8-octane. Alkylenediamines such as diamine, 1,9-nonanediamine, 1,10-decanediamine and 1,12-dodecanediamine,

Polyethylenepolyamines such as diethylenetriamine, triethylenetetramine, tetraethylenepentamine,

Polyoxypropylenediamine, piperazine, metaxylenediamine, isophoronediamine, 1,
3-bis (aminomethyl) cyclohexane, 4,4'-
Examples thereof include diaminodicyclohexylmethane, polyamide polyamine synthesized by condensing dimer acid and polyethylene polyamine, and the like.

Among these, alkylenediamines, polyethylene polyamines and piperazine are preferably used.

In the room temperature curable composition of the first invention, the addition amount of the addition reaction product (B) is 0.1 to 40 parts by weight, preferably 100 parts by weight of the polymer (A). 0.5
~ 35 parts by weight. When the addition amount is less than 0.1 parts by weight, the effect of improving the adhesiveness of the cured product is small, and when it exceeds 40 parts by weight, the effect of improving the adhesiveness of the cured product cannot be expected any more. .

Next, the second invention will be described. The polymer (A) used in the second invention is the same as that used in the first invention.

Addition reaction product (C) used in the second invention
Is a first compound having a hydrolyzable silyl group to a compound (C) having two or more (meth) acryloyl groups in one molecule.
It is an addition reaction product of an amine compound (d) selected from an amine compound and a secondary amine compound having a hydrolyzable silyl group. That is, it is an addition reaction product in which N—H of the compound (d) is added to the C═C double bond in the α, β-unsaturated carbonyl group of the compound (c). It is already known that such an addition reaction easily occurs, as described above.

Generally, the addition reaction product (C) is, for example, synthesized by the following reaction formula (2) or (3) and has two or more hydrolyzable silyl groups and two or more nitrogen atoms in one molecule. is there. n (X ¹ --NH ₂ ) + (CH ₂ = CR ² --COO--) _n Z → (X ¹ --NH--CH ₂ --CHR ² --COO--) _n Z (2)

N (X ² --NY ² H) + (CH ₂ = CR ² --COO--) _n Z → (X ² --NY ² --CH ₂ --CHR ² --COO--) _n Z (3)

In the formulas (2) and (3), X ¹ represents a primary amine residue having a hydrolyzable silyl group, and X ² represents a secondary amine residue having a hydrolyzable silyl group. Show, Y
² represents a secondary amine residue (may or may not contain a hydrolyzable silyl group), R ² represents a hydrogen atom or a methyl group, and Z represents an n-valent organic group. And n is an integer of 2 or more.

The addition reaction product (C) obtained by the formula (2)
Has a secondary amino group, and therefore, when a compound having an excess of (meth) acryloyl group is present in the system, an addition reaction is further caused to carry out a polyaddition reaction.

In the addition reaction of the compound (C) with the amine compound (D), both compounds (C) and (D) are reacted at room temperature to
It is carried out by mixing and stirring at a temperature of 130 ° C. for several hours. Further, in order to prevent a remarkable thickening or gelation during the reaction, the ratio of the compound (ha) to the compound (d) is such that the compound (d) is based on 1 mol of the (meth) acryloyl group of the compound (c). It is preferable that the reaction is carried out such that the active hydrogen derived from the amine is 1 mol or more.

The above compound (C) contains (meta) in one molecule.
A compound having two or more acryloyl groups, for example, ethylene glycol di (meth) acrylate, 1,
4-Butanediol di (meth) acrylate, 1,6-
Hexanediol di (meth) acrylate, 1,3-butylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, 1,14-tetradecanediol di (meth) ) Acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, glycerol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, ethylene oxide modified trimethylolpropane Tri (meth) acrylate, propylene oxide modified trimethylolpropane tri (meth) acrylate,
Ditrimethylolpropane tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, dipentaerythritol monohydroxypenta (meth) acrylate, dicyclopentanyl di (meth) acrylate, tris [( (Meth) acryloxyethyl] isocyanurate, bis [(meth) acryloxyethyl] hydroxyethyl isocyanurate, bisphenol A di (meth) acrylate, bisphenol F di (meth) acrylate, bisphenol S di (meth) acrylate, ethylene oxide modification Bisphenol A di (meth) acrylate, ethylene oxide modified bisphenol F di (meth) acrylate, ethylene oxide modified bisphenol S di (meth) ) And acrylate, and the like,

Epoxy (meth) acrylates obtained by reacting the epoxy group of the epoxy resin with (meth) acrylic acid,

A method of reacting a polyol with a polyisocyanate to introduce an isocyanate group and then reacting a (meth) acrylic acid ester having a hydroxyl group,
Method of reacting (meth) acrylic acid ester having a hydroxyl group with polyisocyanate, method of reacting (meth) acrylic acid ester having a hydroxyl group with polyisocyanate so that an isocyanate group remains, and reacting the isocyanate group with a polyol Urethane (meth) acrylates obtained by

Polyester (meth) obtained by subjecting a hydroxyl group remaining in a polyester synthesized from a polyol and a polybasic acid to a (meth) acrylic acid condensation reaction or a (meth) acrylic acid ester to transesterification reaction. Examples thereof include acrylates and polyether (meth) acrylates obtained by transesterifying a polyether polyol with a (meth) acrylic acid ester.

Among these, 1,6-hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, tetradecanediol di (meth) acrylate, polyester (meth) acrylates, polyether ( (Meth) acrylates are preferably used.

The above-mentioned amine compound (b) is an amine compound selected from a primary amine compound having a hydrolyzable silyl group and a secondary amine compound having a hydrolyzable silyl group, which is a hydrolyzable silyl group. An amine compound selected from a primary amine compound and a secondary amine compound having an alkoxysilyl group as a group is preferable.
Aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) -3-aminopropyltriethoxysilane, N- (2-aminoethyl) -3- Aminopropyltriethoxysilane, N-
(2-Aminoethyl) -3-aminopropylmethyldimethoxysilane, N, N-bis- [3- (trimethoxysilyl) propyl] amine, N, N-bis- [3- (triethoxysilyl) propyl] amine , N, N-Bis-
[3- (methyldimethoxysilyl) propyl] amine,
3- [N-allyl-N- (2-aminoethyl)] aminopropyltrimethoxysilane, p- [N- (2-aminoethyl) aminomethyl] phenethyltrimethoxysilane, N, N-bis- [3- (Trimethoxysilyl) propyl] ethylenediamine, N, N-bis- [3- (methyldimethoxysilyl) propyl] ethylenediamine, N
-[3- (trimethoxysilyl) propyl] diethylenetriamine, N- [3- (methyldimethoxysilyl) propyl] diethylenetriamine, N- [3- (trimethoxysilyl) propyl] ethylenediamine, N- [3-
(Methyldimethoxysilyl) propyl] ethylenediamine and the like.

In the room temperature curable composition of the second invention, the addition amount of the addition reaction product (C) is 0.1 to 40 parts by weight, preferably 100 parts by weight of the polymer (A). 0.5
~ 35 parts by weight. When the addition amount is less than 0.1 parts by weight, the effect of improving the adhesiveness of the cured product is small, and when it exceeds 40 parts by weight, a further effect of improving the adhesiveness of the cured product may be expected. Can not.

If desired, various fillers may be added to the room temperature curable composition of the present invention. Examples of such fillers include calcium carbonate, magnesium carbonate, hydrous silicic acid, anhydrous silicic acid, calcium silicate, silica, titanium oxide, clay, talc, carbon black, and the like. And may be used in combination of two or more.

If necessary, a plasticizer may be added to the above composition in order to enhance the elongation performance of the cured product of the composition or to reduce the modulus. Examples of such a plasticizer include tributyl phosphate, tricresyl phosphate and other phosphate esters, phthalate ester such as dioctyl phthalate, aliphatic monobasic acid ester such as glycerin monooleate ester, dibutyl adipate and dioctyl adipate. And the like, and such plasticizers may be used alone or in combination of two or more kinds.

Further, a known silanol condensation catalyst may be added to the above composition in order to accelerate the moisture curing reaction. As the silanol condensation catalyst, for example, dibutyltin dilaurate, dibutyltin oxide, dibutyltin diacetate, dibutyltin phthalate, dibutyltin bisacetylacetonate, dibutyltin bis (monoester maleate), octyltin acid, dibutyltin dioctoate,
Tin compounds such as dioctyltin oxide, tetra-n-
Examples thereof include titanate compounds such as butyl titanate and tetraisopropyl titanate, amine salts such as dibutylamine-2-ethylhexoate, and amine compounds.

Further, in order to prevent sagging, the above composition contains
An anti-sagging agent such as hydrogenated castor oil or aliphatic bisamide may be added. Furthermore, a pigment, an ultraviolet absorber, an antioxidant and the like may be added to the above composition, if necessary.

[0042]

EXAMPLES Examples of the present invention will be described below. [Synthesis of silyl group-containing (meth) acrylic acid ester polymer (A)] A thermometer, a 5-liter separable flask equipped with a cooling tube, 820 g of n-butyl acrylate,
160 g of ethyl acrylate, 15.2 g of 3-methacryloxypropyltrimethoxysilane, 11.8 g of 3-mercaptopropyltrimethoxysilane and 90 of ethyl acetate.
0 g was charged, the temperature was raised to 80 ° C. in an oil bath while stirring and purging with nitrogen, and a solution of 0.6 g of azobiscyclohexanecarbonitrile dissolved in 20 g of ethyl acetate was added to initiate a polymerization reaction.

A solution of 0.6 g of azobiscyclohexanecarbonitrile dissolved in 20 g of ethyl acetate was added 3 hours after the initiation of the polymerization, and a solution of 0.6 g of azobisisobutyronitrile dissolved in 20 g of ethyl acetate was added 3 hours later. Was added and heating and stirring were continued for 2 hours to complete the polymerization reaction. The obtained reaction solution had a solid content of 50.2% by weight,
The styrene-equivalent molecular weight of the polymer (A) measured by GPC is: number average molecular weight 14,100, weight average molecular weight 39,500.
Met.

Reference Example 1 11.6 g of hexamethylenediamine and 3 in a 100 ml three-necked flask.
-Methacryloxypropyltrimethoxysilane 49.7
The reactor was charged with 120 g while stirring under a nitrogen stream.
The mixture was heated to ℃ and reacted for 10 hours. The obtained reaction product was a yellow liquid, and the peak at 1638 cm ⁻¹ derived from the isopropenyl group of 3-methacryloxypropyltrimethoxysilane disappeared in the IR spectrum, and the peak at 1720 cm ⁻¹ derived from the carbonyl group disappeared. 1729c on the high wave number side
Since it was shifted to m ⁻¹ , and the disappearance of the conjugation between the carbonyl group and the carbon-carbon double bond was estimated, the formation of the addition reaction product (B) of both was confirmed.

Reference Examples 2 to 7 In the same manner as in Reference Example 1,
A compound (b) having a predetermined amount of two or more amino groups selected from a primary amino group and a secondary amino group in one molecule shown in Table 1, a dibutylamine having one secondary amino group,
A (meth) acrylate compound (a) having a hydrolyzable silyl group and n-butyl acrylate, which is an acrylate having no hydrolyzable silyl group, were charged into a reactor, and the reactor was heated to a predetermined temperature shown in Table 1. Let react for 10 hours,
An addition reaction product (B) of the compound (b) and the compound (a) was obtained.

(Examples 1 to 5 and Comparative Examples 1 to 8) 20 parts by weight of dioctyl phthalate was added and mixed with 100 parts by weight of the polymer (A) (calculated as solid content), and then 120 ° C.
The mixture was heated under reduced pressure to distill off ethyl acetate and residual monomers.
Mixture 12 of the polymer (A) and dioctyl phthalate
To 0 parts by weight, 100 parts by weight of calcium carbonate preliminarily dried at 120 ° C. for 2 hours and 20 parts by weight of titanium oxide were added,
After uniformly kneading with a sealed mixing stirrer, 3 parts by weight of a moisture curing catalyst dibutyltin dilaurate, a predetermined amount of the addition reaction product (B) shown in Table 2 and other additives are uniformly mixed and stirred to cure at room temperature. A composition was prepared.

[Measurement of Physical Properties] The room temperature-curable compositions obtained in the above Examples and Comparative Examples were measured for tensile adhesion, and the results are shown in Table 2. (Tensile Adhesion) Regarding the obtained room temperature curable composition, J
An H-type test piece was prepared in accordance with IS A5758 and the temperature was 23 ° C.
50mm after curing at 60% RH for 2 weeks and at 30 ℃ for 2 weeks
A tensile test was performed at a speed of 1 / min to measure tensile strength and elongation. Further, the fractured form of the test piece was visually observed. A vinyl chloride steel plate was used as the adherend.

[0048]

[Table 1]

[0049]

[Table 2]

Reference Example 8 In a 500 ml three-necked flask equipped with a thermometer, 200 g of 3- [N- (2-aminoethyl) amino] propylmethyldimethoxysilane was added.
Then, 110 g of 1,6-hexanediol diacrylate was gradually added dropwise under a nitrogen stream while stirring with ice cooling. As the temperature dropped, the reaction temperature increased and the system thickened,
The progress of the reaction could be confirmed. After completion of dropping, the reactor was heated to 70 ° C. and further reacted for 8 hours. The obtained reaction product was a pale yellow viscous liquid and was derived from the vinyl group of 1,6-hexanediol diacrylate in the IR spectrum.
37cm ^-1, 1618cm ^-1 and 1409cm ^-1 disappeared, a peak of 1724 cm ^-1 derived from the carbonyl group is shifted to 1732 cm ^-1 of the high frequency side, conjugated with the carbonyl group and the carbon-carbon double bond Since it is estimated that the addition reaction product (C) has disappeared, the formation of both addition reaction products (C) was confirmed.

Reference Examples 9 to 17 In the same manner as in Reference Example 8,
The amine compound (d) or the hydrolyzable silyl group selected from the first amine compound having a predetermined amount of hydrolyzable silyl group and the second amine compound having a hydrolyzable silyl group shown in Tables 3 and 4 A compound (ha) or monoacrylate 2-ethylhexyl acrylate having two or more (meth) acryloyl groups in a predetermined amount shown in Tables 3 and 4 was prepared by charging a reactor with an amine having no morpholine. Was gradually added dropwise. After completion of the dropping, the reactor was set to the temperature shown in Table 3 and Table 4 and further reacted for 8 hours to obtain an addition reaction product (C) of the amine compound (d) and the compound (c).

(Examples 6 to 13 and Comparative Examples 9 to 14) 20 parts by weight of dioctyl phthalate was added and mixed with 100 parts by weight of the polymer (A) (calculated as solid content), and then 120 ° C.
The mixture was heated under reduced pressure to distill off ethyl acetate and residual monomers.
Mixture 12 of the polymer (A) and dioctyl phthalate
To 0 parts by weight, 100 parts by weight of calcium carbonate preliminarily dried at 120 ° C. for 2 hours and 20 parts by weight of titanium oxide were added,
After uniformly kneading with a sealed mixing stirrer, 3 parts by weight of moisture curing catalyst dibutyltin dilaurate, a predetermined amount of addition reaction product (C) shown in Table 5 and other additives are uniformly mixed and stirred to cure at room temperature. A composition was prepared.

The room temperature-curable compositions obtained in the above Examples and Comparative Examples were measured for tensile adhesion in the same manner as in Example 1, and the results are shown in Table 5.

[0054]

[Table 3]

[0055]

[Table 4]

[0056]

[Table 5]

The compounds used in Examples and Comparative Examples are as follows. -Aminosilane (1): N- (2-aminoethyl) -3
-Aminopropylmethyldimethoxysilane-Aminosilane (2): 3- [N- (2-aminoethyl) amino] propyltrimethoxysilane- 1,6-hexanediol diacrylate: "NK Ester A-HD" manufactured by Shin-Nakamura Chemical Co., Ltd. -1,6-hexanediol dimethacrylate: Kyoeisha Yushi Kagaku Co., Ltd. "light ester 1.6HX" -Trimethylol propane triacrylate: Kyoeisha Yushi Kagaku Co., Ltd. "light acrylate TMP-A" -Tetradecanediol diacrylate: Sartomer "Chemlink 2000" manufactured by Toa Gosei Co., Ltd. "Aronix M-6200" (having an average of two acryloyl groups in one molecule) Polyether acrylate: "NK Ester APG-400" manufactured by Shin Nakamura Chemical Co., Ltd. ( Poly Pro Pyrene glycol diacrylate) -Aminosilane (3): 3-aminopropyltrimethoxysilane-Aminosilane (4): N, N-bis- [3- (trimethoxysilyl) propyl] amine

[0058]

The room temperature curable composition of the first invention comprises a polymer (A) having a crosslinkable hydrolyzable silyl group, the main chain of which is essentially an acrylate polymer. An addition reaction product of a compound (b) having two or more amino groups selected from a primary amino group and a secondary amino group in one molecule to a (meth) acrylate compound (a) having a degradable silyl group ( By blending with A), the adhesiveness to various adherends is excellent, so that it can be particularly preferably used as a sealing material or an adhesive.

The room-temperature curable composition of the second invention comprises a polymer (A) whose main chain is essentially an acrylate polymer and has a crosslinkable hydrolyzable silyl group, and (meth) An amino compound (d) selected from a primary amine compound having a hydrolyzable silyl group and a secondary amine compound having a hydrolyzable silyl group to a compound (ha) having two or more acryloyl groups in one molecule Since the adhesiveness to various adherends is excellent by blending with the addition reaction product (C), it can be preferably used as a sealing material or an adhesive.

Claims (2)

[Claims] 1. (A) 100 parts by weight of a polymer whose main chain is essentially a (meth) acrylic acid ester-based polymer having a crosslinkable hydrolyzable silyl group, and (B) a hydrolyzable polymer. Addition reaction product of a compound (b) having two or more amino groups selected from a primary amino group and a secondary amino group in one molecule to a (meth) acrylate compound (a) having a silyl group. A room temperature curable composition comprising 40 parts by weight. 2. (A) 100 parts by weight of a polymer whose main chain is essentially a (meth) acrylic acid ester polymer and having a crosslinkable hydrolyzable silyl group, and (C) (meth) A compound having two or more acryloyl groups in one molecule (C)
Reaction product of an amine compound (d) selected from a primary amine compound having a hydrolyzable silyl group and a secondary amine compound having a hydrolyzable silyl group with 0.1 to 4
A room temperature curable composition comprising 0 parts by weight.