JP3224632B2 - Room temperature curable composition - Google Patents

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 cures to a rubbery state by reacting with atmospheric moisture, and particularly has excellent adhesiveness to various adherends and is 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) acrylate polymer which cures into a rubbery state by reacting with moisture in the atmosphere, for example, as described in JP-A-54-36395, an allyl group is disclosed. Acrylate polymer having
It is 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. (Wherein, 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 an atom selected from a halogen atom, an alkoxy group, an acyloxy group and a ketoxmate group. )

[0003] The (meth) acrylate polymer obtained in this way has excellent weather resistance and is useful as a base resin for adhesives, sealing materials, coating materials, etc., but is generally used as a (meth) acrylate ester polymer. There was a problem that the polymer alone had low adhesiveness.

[0004] Therefore, for the purpose of improving the adhesiveness, for example, Japanese Patent Publication No. 42868/1990 and Japanese Patent Application Laid-Open No. 57-105 / 1982.
No. 446 discloses that a hydrolyzable silyl group is contained in one molecule.
It is disclosed that an amine compound having at least one compound is added. However, there is a problem that sufficient adhesion to a poorly adherent such as a polyvinyl chloride steel sheet cannot be obtained only by adding the amine compound to the (meth) acrylate polymer.

[0005]

SUMMARY OF THE INVENTION The present invention solves the above-mentioned conventional problems and provides a room-temperature-curable composition having sufficient adhesiveness to difficult-to-adhere materials such as PVC steel sheets. It is intended to be.

[0006]

The room-temperature-curable composition of the first invention has a main chain essentially composed of a (meth) acrylate polymer and has a crosslinkable hydrolyzable silyl group. 100 parts by weight of the union (A) and two or more amino groups per molecule in the (meth) acrylate compound (a) having a hydrolyzable silyl group, selected from primary amino groups and secondary amino groups. Reaction product (B) of compound (b)
0.1 to 40 parts by weight, further containing a plasticizer, wet
It is characterized by comprising a composition which reacts with air and cures into a rubber-like state .

[0007] room temperature curable composition of the second invention, the main chain is essentially (meth) acrylic acid ester polymer, a polymer having a crosslinkable hydrolyzable silyl group (A) 1
00 parts by weight and two (meth) acryloyl groups in one molecule.
Compounds having more than five to (c), the first amine compound and an amine compound selected from the second amine compound having a hydrolyzable silyl group addition reaction product of (D) (C) 0.1 to
Contains 40 parts by weight, further contains a plasticizer, reacts with moisture
And a rubber-curable composition .

Hereinafter, the present invention will be described in detail. The polymer (A) used in the present invention is essentially a (meth) acrylate polymer having a main chain, and has a crosslinkable hydrolyzable silyl group in the molecule.

Such a polymer (A) can be synthesized, for example, by the method described in JP-A-54-36395, or as described in JP-A-57-179210. , (Meth) acrylic acid alkyl ester monomer and alkoxysilyl group-containing (meth) acrylic acid alkyl ethesyl 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. Can also be obtained by copolymerization in the presence of

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

Further, when the molecular weight of the polymer (A) is small, the elongation of the cured product is insufficient, and when the molecular weight is large, the viscosity becomes high and the workability when the compound is formed is reduced.
3,000-100,000 is preferred.

The addition reactant (B) used in the present invention is:
Compound (b) having two or more amino groups per molecule selected from a primary amino group and a secondary amino group to a (meth) acrylate compound (a) having a hydrolyzable silyl group
Is an addition reactant. That is, it is an addition reaction product in which the NH 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
orisson and Boyd Organic
Chemistry Sixth Edition
p977).

Generally, the above-mentioned 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 ＣＲCR ³ —COOY → Z- (NR ² —CH ₂ —CHR ³ —COOY) _m (1) In the formula (1), Z represents a primary amino group and R ² represents a hydrogen atom or a secondary amino group selected from secondary amino groups;
R ³ represents a hydrogen atom or a methyl group, and Y represents a (meth) acrylate residue having a hydrolyzable silyl group. M represents an integer of 2 or more.

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

As the above (meth) acrylate compound (a), a (meth) acrylate compound having an alkoxysilyl group as a hydrolyzable silyl group is preferable. For example, 3- (meth) acryloxypropyltrimethoxysilane, {(Meth) acryloxypropylmethyldimethoxysilane, 3} (meth) acryloxypropyltriethoxysilane, (meth) acryloxymethyltrimethoxysilane and the like.

Silanes having a functional group capable of reacting with an isocyanate group such as 3-mercaptopropyltrimethoxysilane and 3-aminopropyltrimethoxysilane; hexamethylene diisocyanate, isophorone diisocyanate, and diphenylmethanediamine; A reaction product obtained by reacting isocyanate, diisocyanate such as tolylene {2,6} diisocyanate at a ratio of 1: 1;
An isocyanate compound having a hydrolyzable silyl group such as 3-isocyanatopropyltrimethoxysilane,
Urethane (meth) acrylates having a hydrolyzable silyl group obtained by reacting with a (meth) acrylate compound having a hydroxy group are exemplified.

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 primary amino group and secondary amino group in one molecule include ethylenediamine, butylenediamine, hexamethylenediamine, 1,8-octane. Diamines, 1,9 ジ ア ミ ン nonanediamine, 1,10─decanediamine, alkylenediamines such as 1,12─dodecanediamine,

Polyethylenepolyamines such as diethylenetriamine, triethylenetetramine and tetraethylenepentamine;

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

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

In the room temperature curable composition of the first invention, the addition amount of the addition reactant (B) is 0.1 to 40 parts by weight, preferably 100 to 100 parts by weight of the polymer (A). 0.5
３５35 parts by weight. When the added amount is less than 0.1 part by weight, the effect of improving the adhesion 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 polymer as used in the first invention.

The addition reaction product (C) used in the second invention
Is a compound (c) having two or more (meth) acryloyl groups in one molecule, a first compound having a hydrolyzable silyl group.
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 the NH 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.

In general, the addition reaction product (C) is synthesized by, for example, 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 ＣＲCR ² -COO─) _n Z → (X ¹ ─NH─CH ₂ ─CHR ² -COO─) _n Z (2)

[0027] ^{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 (which 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 represents an integer of 2 or more.

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

In the above addition reaction of the compound (c) and the amine compound (d), both compounds (c) and (d) are reacted at room temperature to
This is performed by mixing and stirring at a temperature of 130 ° C. for several hours. Further, in order to prevent a remarkable thickening or gelling during the reaction, the ratio of the compound (c) to the compound (d) is such that the compound (d) is added to 1 mole of the (meth) acryloyl group of the compound (c) The reaction is preferably carried out so that the amount of active hydrogen derived from the amine is 1 mol or more.

The compound (c) contains (meth) in one molecule.
A compound having two or more acryloyl groups, for example, ethylene glycol di (meth) acrylate,
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, modified ethylene oxide 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, dicyclopentanyldi (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 modified Bisphenol A di (meth) acrylate, ethylene oxide modified bisphenol F di (meth) acrylate, ethylene oxide modified bisphenol S ) And acrylate, and the like,

Epoxy (meth) acrylates obtained by reacting an epoxy group of an 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) acrylate having a hydroxyl group;
A method of reacting a (meth) acrylate having a hydroxyl group with a polyisocyanate, a method of reacting a (meth) acrylate having a hydroxyl group with a polyisocyanate so that the isocyanate group remains, and reacting a polyol with the isocyanate group. Urethane (meth) acrylates obtained by

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

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

The 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. 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 screws
[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 reactant (C) is 0.1 to 40 parts by weight based on 100 parts by weight of the polymer (A). 0.5
３５35 parts by weight. When the added amount is less than 0.1 part 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 further can be expected. Can not.

Various kinds of fillers may be added to the room temperature-curable composition of the present invention, if necessary. Such fillers include, for example, calcium carbonate, magnesium carbonate, hydrous silicic acid, anhydrous silicic acid, calcium silicate, silica, titanium oxide, clay, talc, carbon black, and the like. Or two or more of them may be used in combination.

In addition, the above-mentioned composition includes a cured product of the composition.
In order to improve elongation performance and reduce modulus, plasticization
Add the agent. Examples of such a plasticizer include phosphates such as tributyl phosphate and tricresyl phosphate; phthalic esters such as dioctyl phthalate; aliphatic monobasic esters such as glycerin monooleate; dibutyl adipate; and dioctyl adipate. And the like. These plasticizers may be used alone or in combination of two or more.

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

In addition, the above composition contains
An anti-sagging agent such as hydrogenated castor oil and aliphatic bisamide may be added. Further, a pigment, an ultraviolet absorber, an antioxidant, and the like may be added to the composition as needed.

[0042]

Embodiments of the present invention will be described below. [Synthesis of silyl group-containing (meth) acrylate polymer (A)] In a 5-liter separable flask equipped with a thermometer and a cooling tube, 820 g of n-butyl acrylate was added.
160 g of ethyl acrylate, 15.2 g of 3-methacryloxypropyltrimethoxysilane, 11.8 g of 3-mercaptopropyltrimethoxysilane and 90 parts of ethyl acetate
While charging 0 g, the mixture was heated 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.

3 hours after the start of the polymerization, a solution prepared by dissolving 0.6 g of azobiscyclohexanecarbonitrile in 20 g of ethyl acetate was additionally added. After 3 hours, a solution obtained by dissolving 0.6 g of azobisisobutyronitrile in 20 g of ethyl acetate was added. Was added and heating and stirring were continued for 2 hours to complete the polymerization reaction. The resulting reaction solution has a solid content of 50.2% by weight,
The polymer (A) had a number average molecular weight of 14,100 and a weight average molecular weight of 39,500 in terms of styrene by GPC.
Met.

Reference Example 1 In a 100 ml three-necked flask, 11.6 g of hexamethylenediamine and 3
-Methacryloxypropyltrimethoxysilane 49.7
g and stirring the reactor under a stream of nitrogen.
C. 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 the shift to m ^-1 was observed, and the disappearance of the conjugation between the carbonyl group and the carbon-carbon double bond was estimated, the formation of an addition reaction product (B) of both was confirmed.

Reference Examples 2 to 7 In the same manner as in Reference Example 1,
A compound having two or more amino groups selected from a primary amino group and a secondary amino group in one molecule (b), dibutylamine having one secondary amino group, a predetermined amount shown in Table 1,
A (meth) acrylate compound having a hydrolyzable silyl group (a) and n-butyl acrylate, which is an acrylate having no hydrolyzable silyl group, are charged into a reactor, and the reactor is 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, Comparative Examples 1 to 8) Dioctyl phthalate (20 parts by weight) was added to and mixed with 100 parts by weight of the polymer (A) (in terms of solid content).
The pressure was reduced under heating to remove ethyl acetate and the remaining monomer.
Mixture 12 of the above polymer (A) and dioctyl phthalate
0 parts by weight, 100 parts by weight of calcium carbonate and 20 parts by weight of titanium oxide predried at 120 ° C. for 2 hours,
After uniformly kneading with a sealed mixing stirrer, 3 parts by weight of a moisture curing catalyst, dibutyltin dilaurate, a predetermined amount of an addition reactant (B) shown in Table 2 and other additives are uniformly mixed and stirred, and the mixture is cured at room temperature. A composition was prepared.

[Measurement of Physical Properties] Tensile adhesion was measured for the room temperature curable compositions obtained in the above Examples and Comparative Examples, and the results are shown in Table 2. (Tensile Adhesion) Regarding the obtained room temperature curable composition,
Prepare an H-type test piece based on IS A5758,
After curing at 60% RH for 2 weeks and at 30 ° C for 2 weeks, 50mm
A tensile test was performed at a rate of / min to measure tensile strength and elongation. Further, the mode of destruction of the test piece was visually observed. Incidentally, a PVC steel sheet was used as the adherend.

[0048]

[Table 1]

[0049]

[Table 2]

Reference Example 8 200 g of 3- [N- (2-aminoethyl) amino] propylmethyldimethoxysilane was placed in a 500 ml three-necked flask equipped with a thermometer.
Was charged, and 110 g of 1,6-hexanediol diacrylate was gradually added dropwise while stirring with ice and under a nitrogen stream. The reaction temperature rises and the system thickens with the addition,
The progress of the reaction was confirmed. After completion of the dropwise addition, the reactor was heated to 70 ° C. and reacted for further 8 hours. The obtained reaction product is a pale yellow viscous liquid, and its IR spectrum shows that it is derived from the vinyl group of 1,6-hexanediol diacrylate.
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 It was confirmed that the addition reaction product (C) was produced.

Reference Examples 9 to 17 Similarly to Reference Example 8,
An amine compound (d) or a hydrolyzable silyl group selected from a predetermined amount of a primary amine compound having a hydrolyzable silyl group and a secondary amine compound having a hydrolyzable silyl group shown in Tables 3 and 4 is used. A morpholine, which is an amine having no compound, is charged into a reactor, and a compound (c) having a predetermined amount of two or more (meth) acryloyl groups in one molecule shown in Tables 3 and 4 or 2-ethylhexyl acrylate which is a monoacrylate is used. Was gradually added dropwise. After the completion of the dropwise addition, the reactor was set at the temperature shown in Tables 3 and 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, Comparative Examples 9 to 14) To 100 parts by weight of the polymer (A) (in terms of solid content), 20 parts by weight of dioctyl phthalate were added and mixed, and then the mixture was heated at 120 ° C.
The pressure was reduced under heating to remove ethyl acetate and the remaining monomer.
Mixture 12 of the above polymer (A) and dioctyl phthalate
0 parts by weight, 100 parts by weight of calcium carbonate and 20 parts by weight of titanium oxide predried at 120 ° C. for 2 hours,
After uniformly kneading with a sealed mixing stirrer, 3 parts by weight of dibutyltin dilaurate, a predetermined amount of addition reactant (C) shown in Table 5, and other additives are uniformly mixed and stirred, and the mixture is stirred at room temperature. A composition was prepared.

With respect to the room temperature curable compositions obtained in the above Examples and Comparative Examples, the tensile adhesiveness was measured 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: "Light ester 1.6HX" manufactured by Kyoeisha Yushi Kagaku Co., Ltd.-Trimethylolpropane triacrylate: "Light acrylate TMP-A" manufactured by Kyoeisha Yushi Kagaku Co., Ltd.-Tetradecanediol diacrylate: Sartomer "Chemlink2000" manufactured by Toagosei 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. Polypro 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 has a main chain consisting essentially of a (meth) acrylate polymer,
Polymer (A) having a crosslinkable hydrolyzable silyl group
And addition of a compound (b) having two or more amino groups per molecule selected from a primary amino group and a secondary amino group to a (meth) acrylate compound (a) having a hydrolyzable silyl group Blend with reactant (B) and further add plasticizer
Composition that cures into a rubbery state by reacting with moisture.
By that, since the adhesiveness to various adherends is excellent, it can be used particularly suitably as a sealing material or an adhesive. The room-temperature-curable composition of the second invention is a polymer (A) whose main chain is essentially a (meth) acrylate polymer and has a crosslinkable hydrolyzable silyl group.
And an amine compound (d) selected from a primary amine compound and a secondary amine compound having a hydrolyzable silyl group to a compound (c) having two or more (meth) acryloyl groups in one molecule. Addition reactant (C) is blended,
A group that contains a plasticizer and reacts with moisture to harden into a rubber
Since the composition is excellent in adhesiveness to various adherends, it can be suitably used particularly 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 selected from a primary amine compound having a hydrolyzable silyl group and a secondary amine compound having a hydrolyzable silyl group to a compound (c) having two or more acryloyl groups in one molecule (d) Is excellent in adhesiveness to various adherends, and thus can be suitably used particularly as a sealing material or an adhesive.

Claims (2)

(57) [Claims] (A) 100 parts by weight of a polymer having a crosslinkable hydrolyzable silyl group whose main chain is essentially a (meth) acrylate polymer, and (B) a hydrolyzable polymer. (Meth) acrylate compounds having a silyl group (A)
Containing 0.1 to 40 parts by weight of 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 , and further comprising a plasticizer. Including
A room temperature curable composition comprising a composition which reacts with moisture and cures into a rubbery state . 2. (A) 100 parts by weight of a polymer having a crosslinkable hydrolyzable silyl group whose main chain is essentially a (meth) acrylate polymer, and (C) (meth)
Addition product of an amine compound (d) selected from a primary amine compound and a secondary amine compound having a hydrolyzable silyl group to a compound (c) having two or more acryloyl groups in one molecule. 1 to 40 parts by weight
Composition that contains a plasticizer and reacts with moisture to cure into rubber
A curable composition at room temperature, comprising a product.