JPH11279425A - Hardenable composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a hardenable composition capable of providing a hardened product having excellent mechanical strengths and an adhesive strength, and capable of maintaining the properties even after a long term preservation with water by including a specific organic polymer and a specified urea derivative. SOLUTION: This hardenable composition comprises (A) an organic polymer having at least one of silicon-containing group having a silicon atom bound to a hydroxy group or a hydrolyzable group, and (B) a urea derivative having the silicon-containing group containing the silicon atom bound to the hydroxy group or the hydrolyzable group [e.g. N-(3-trimethoxysilylpropyl)urea], regulated so that the weight ratio of the components A/B may be (100/0.1)-(100/40). A group of the formula; SiXa R<1> 3-a [R<1> is a 1-20C (substituted) monovalent hydrocarbon; X is OH or a monovalent hydrolyzable group; (a) is 1-3] is preferable as the silicon-containing group containing the silicon atom bound to the hydroxy group or the hydrolyzable group.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a modified curable composition, and more particularly to a curable composition which exhibits remarkably excellent mechanical properties and has particularly excellent adhesive strength.

[0002]

2. Description of the Related Art An organic polymer having at least one silicon-containing group containing a silicon atom to which a hydroxyl group or a hydrolyzable group is bonded (also referred to as a hydrolyzable silicon group) in a molecule has a cured product having rubber elasticity. It is used for applications such as coating compositions and sealing compositions, taking advantage of its characteristics.However, the strength of the cured product, especially the shear adhesive strength, is insufficient for applications such as adhesives, which is a practical problem. There is. For example, when this is used as an adhesive, there arises a problem that the shear adhesive strength is insufficient.

In order to solve these drawbacks, a hydrolyzable silicon-containing organic polymer is reacted with an amino-containing alkoxysilane or an epoxy-containing alkoxysilane or a methacryl-containing alkoxysilane. A composition comprising the obtained modified product has been proposed (JP-B-62-35421). However, in the case of addition of an amino group-containing alkoxysilane, problems such as thickening and changes in physical properties occur when stored for a long period of time while containing water. In addition, in the case of addition of the modified product, there were problems such as a large change in modulus of the cured product and brittleness of the cured product, and a problem that the destruction state of the test sample after the water resistance test shows a tendency of interfacial peeling.

[0004]

The object of the present invention is to solve the above-mentioned drawbacks, to provide a cured product having excellent mechanical properties and adhesive strength, and to maintain its properties even when stored for a long time with moisture. It is intended to provide a curable composition characterized by the following.

[0005]

The present invention provides an organic polymer (A) having at least one silicon-containing group containing a silicon atom to which a hydroxyl group or a hydrolyzable group is bonded in a molecule, and a hydroxyl group or a hydroxyl group. A curable composition comprising a urea derivative (B) having a silicon-containing group containing a silicon atom to which a hydrolyzable group is bonded.

[0006]

BEST MODE FOR CARRYING OUT THE INVENTION The organic polymer (A) having at least one silicon-containing group containing a silicon atom to which a hydroxyl group or a hydrolyzable group is bonded in the molecule according to the present invention includes:
An organic polymer derived from an organic polymer selected from polyether, polyester and polycarbonate is exemplified.

Also, acrylates, methacrylates, vinylalkyl ethers, dienes such as isobutylene, butadiene, chloroprene, polymerizable monomers such as chlorotrifluoroethylene, tetrafluoroethylene, ethylene or propylene, and hydrolyzable silicon groups are contained. Examples include a hydrolyzable silicon-containing vinyl polymer obtained by copolymerizing a polymerizable monomer.

[0008] Organic polymers derived from organic polymers selected from polyethers, polyesters and polycarbonates are particularly preferred, and among them, hydrolyzable silicon-containing polyethers derived from polyethers are particularly preferred.

The hydrolyzable silicon group-containing polyether is
It is particularly preferred that it is derived from a hydroxyl-containing polyether.

The hydroxyl group-containing polyether can be obtained by subjecting an initiator containing active hydrogen to a ring-opening polymerization reaction of a cyclic ether in the presence of a catalyst. As the cyclic ether, an alkylene oxide is preferable, and propylene oxide, ethylene oxide, butylene oxide, epichlorohydrin, styrene oxide, allyl glycidyl ether and the like are preferable. Propylene oxide is particularly preferred. Oxetane, tetrahydrofuran and the like can also be used.

Examples of the initiator include polyhydric active compounds such as polyhydric alcohols, polycarboxylic acids, and polyamines; monools containing terminal unsaturated groups; and unsaturated groups containing unsaturated phenols and unsaturated carboxylic acids. Active hydrogen compounds.

Examples of the catalyst include alkali metals such as sodium, potassium and cesium, alkali metal compounds such as hydroxides of these alkali metals, double metal cyanide complexes,
Metal porphyrin complexes can be used. It is particularly preferred to use double metal cyanide complexes.

In the present invention, a silicon-containing group containing a silicon atom to which a hydroxyl group or a hydrolyzable group is bonded, that is, a hydrolyzable silicon group, is defined by a moisture or a curing catalyst such as a silanol group or an alkoxysilyl group. It is capable of promoting a high molecular weight by causing a condensation reaction to crosslink the organic polymer, and is preferably represented by Formula 1.

[0014]

## STR2 ## -SiX _a R ¹ _3-a ··· Formula 1

In the formula 1, R ¹ is a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, X is a hydroxyl group or a monovalent hydrolyzable group, and a is an integer of 1 to 3.

The hydrolyzable silicon group-containing polyether is
When it is derived from a hydroxyl group-containing polyether, a hydrolyzable silicon group represented by Formula 1 is usually introduced via an organic group. Therefore, the organic polymer (A) in the present invention preferably has a group represented by Formula 2.

[0017]

[Formula 3] ^{_{-R 0 -SiX a R 1 3-}} a ··· Formula 2

In the formula 2, R ⁰ is a divalent organic group, R ¹ , X,
a is the same as above.

Here, R ^{0 in} Formula 2 is a divalent organic group, and is preferably a hydrocarbon group having 8 or less carbon atoms. Equation 1, Equation 2
Wherein R ¹ is a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, preferably an alkyl group having 8 or less carbon atoms, a phenyl group or a fluoroalkyl group. Particularly preferred are a methyl group, an ethyl group, a propyl group, a butyl group, a hexyl group, a cyclohexyl group and a phenyl group.

X in the formulas 1 and 2 is a hydroxyl group or a monovalent hydrolyzable group. Examples of the hydrolyzable group include a halogen atom, an alkoxy group, an acyloxy group, an amide group,
There is an amino group, an aminooxy group, a ketoximate group or a hydride group. Among these, the number of carbon atoms of the hydrolyzable group having a carbon atom is preferably 6 or less, particularly preferably 4 or less. Preferred X is an alkoxy group having 4 or less carbon atoms, particularly a methoxy group, an ethoxy group or a propoxy group. A in Formulas 1 and 2 is preferably 2 or 3.

Examples of the method for producing the organic polymer (A) in the present invention include, but are not limited to, the following (a) to (f). (A) to (d)
It is an example of a manufacturing method of a hydrolyzable silicon group-containing polyether, and (e) to (f) are examples of a manufacturing method of a hydrolyzable silicon group-containing vinyl polymer.

(A) A method in which an organosilicon compound having an isocyanate group and a hydrolyzable silicon group is reacted with a hydroxyl group-containing polyether.

Specific examples of the organosilicon compound include the following compounds.

[0024]

## STR4 ## (C ₂ H ₅ O) ₃ Si (CH ₂ ) ₃ NCO,
(CH ₃ O) ₃ Si (CH ₂ ) ₃ NCO, (CH ₃ O)
₂ (CH ₃ ) Si (CH ₂ ) ₃ NCO, (CH ₃ O) ₃
SiNCO, (CH ₃ O) ₂ Si (NCO) ₂ .

(B) Formula HSix _a R ¹³ _-a (wherein R ¹ ,
X and a are the same as described above), and a polyether having an unsaturated group introduced into a terminal thereof.

Here, as a method for introducing an unsaturated group,
A method in which OH of a hydroxyl group-containing polyether is converted to OM (M is an alkali metal) and then reacted with an unsaturated group-containing halogenated hydrocarbon such as allyl chloride, or a compound having a functional group capable of reacting with an unsaturated group and a hydroxyl group Is reacted with a hydroxyl group-containing polyether to form an ester bond, a urethane bond,
There is a method of introducing an unsaturated group through a carbonate bond or the like. Further, when producing an alkylene oxide in the production of a terminal hydroxyl group-containing polyether, a method of introducing an unsaturated group into a side chain by copolymerizing an unsaturated group-containing alkylene oxide such as allyl glycidyl ether, There is also a method of introducing an unsaturated group into a terminal by using a hydroxyl group-containing polyether produced using an unsaturated group-containing monol.

(C) A method in which a polyisocyanate such as tolylene diisocyanate is reacted with the terminal of the hydroxyl group-containing polyether to form an isocyanate group terminal, and the W group of the silicon compound represented by Formula 3 is reacted with the isocyanate group. .

[0028]

[Of 5] _{^{W-R 2 -SiX a R 1}} 3-a ··· Formula 3

In the formula 3, R ¹ , X and a are the same as described above, and R ² is a divalent hydrocarbon group having 1 to 20 carbon atoms;
W is an active hydrogen-containing group selected from a hydroxyl group, a carboxyl group, a mercapto group and an amino group (primary or secondary).

(D) A method of reacting an unsaturated group of a polyether having an unsaturated group introduced at a terminal thereof with a mercapto group of a silicon compound represented by the formula 3 wherein W is a mercapto group.

(E) A method of copolymerizing a polymerizable monomer having a hydrolyzable silicon group or an oligomer thereof and another polymerizable monomer or an oligomer thereof.

The polymerizable monomer is, for example, a single compound of the formula (4) or a mixture of two or more compounds.

[0033]

Embedded image CRR ³ = CR ⁴ R ⁵ Formula 4

In Formula 4, R and R ³ are a hydrogen atom, a halogen atom or a monovalent hydrocarbon group, preferably a hydrogen atom or a monovalent hydrocarbon group. R ⁴ and R ⁵ are a hydrogen atom, a halogen atom, or an organic group having 1 to 20 carbon atoms. As the organic group, an alkyl group, an alkenyl group,
C1-C20 substituted or unsubstituted 1 such as phenyl group
A group selected from a monovalent hydrocarbon group, an alkoxy group, a carboxyl group, an alkoxycarbonyl group, a glycidoxycarbonyl group, a cyano group, a cyano group-containing group, an alkenyl group, an acyloxy group, an amide group and a pyridyl group. .

Specific examples of the polymerizable monomer include styrene monomers such as styrene and α-methylstyrene, acrylic acid, methacrylic acid, esters thereof, and acrylic, methacrylic monomers such as acrylamide and methacrylamide, acrylonitrile, Group-containing monomers such as 1,4-dicyanobutene-1, vinyl ester monomers such as vinyl acetate, diene monomers such as isoprene and butadiene, olefins such as isobutylene and other unsaturated esters, halogenated olefins, vinyl ethers and the like. .

As the polymerizable monomer having a hydrolyzable silicon group, a compound represented by Formula 5 is used.

[0037]

Embedded image Y _3-b —SiR ⁶ _b R ⁷ Formula 5

In the formula 5, R ⁶ is a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, and Y is a hydroxyl group, a halogen atom, an alkoxy group, an acyloxy group, an amide group, an amino group, aminoxy group, a hydrolyzable group such as a ketoximate group, R ⁷ is an organic group having a polymerizable unsaturated group, b is an integer of 0-2.

Specific examples of the compound represented by the formula 5 include the following compounds.

[0040]

Embedded image CH ₂ CC (CH ₃ ) COO (CH ₂ ) ₃ Si (CH ₃ ) (OCH ₃ ) ₂ and CH ₂ CC (CH ₃ ) Si (CH ₃ ) (OCH ₃ ) ₂ .

(F) A method of polymerizing a polymerizable monomer in the presence of a chain transfer agent containing a hydrolyzable silicon group.

Specific examples of the chain transfer agent containing a hydrolyzable silicon group include the following compounds.

[0043]

Embedded image HS (CH ₂ ) ₃ Si (OCH ₃ ) ₃ , HS
_{(CH 2) 3 Si (CH} 3) (OCH 3) 2.

The molecular weight of the organic polymer (A) is preferably 1,000 or more. It is preferably 2,000 to 50,000, more preferably 3,000 to 50,000, particularly 5,000 to 30,000, and even more preferably 80 to 50,000.
00 to 30000 is preferred.

When a hydrolyzable silicon group-containing polyether is used as the organic polymer (A), its molecular weight is preferably calculated from the hydroxyl value of the starting hydroxyl group-containing polyether.

The total amount of the ionic impurities contained in the organic polymer (A) of the present invention is preferably 50 ppm or less. In particular, the total amount of metal ionic impurities is preferably 20 ppm or less. As a method for reducing ionic impurities, JP-A-6-323113 and JP-A-7-180336 are known.
And the like.

In the present invention, the urea derivative (B) having a silicon atom containing a silicon atom to which a hydroxyl group or a hydrolyzable group is bonded, ie, a urea derivative (B) having a hydrolyzable silicon group, has one hydrolyzable silicon group per molecule. Preferably, the compound has two or more compounds. The hydrolyzable silicon group in the urea derivative (B) is preferably a group represented by Formula 1, and particularly preferably an alkoxysilyl group having an alkoxy group having 4 or less carbon atoms. Examples of the alkoxysilyl group include a trialkoxysilyl group, a dialkoxysilyl group, and a monoalkoxysilyl group.

The urea derivative (B) having a hydrolyzable silicon group is a compound in which at least one of four hydrogen atoms in urea is substituted with a hydrolyzable silicon group or a group containing a hydrolyzable silicon group. A hydrogen atom that is not substituted with a hydrolyzable silicon group or a group containing a hydrolyzable silicon group may be substituted with another organic group. Examples of the organic group include a hydrocarbon group such as an alkyl group, an alkenyl group, and a phenyl group. Preferably, one or two hydrogen atoms in urea are substituted. It is particularly preferable that the compound has one ureido bond or one ureylene bond in one molecule.

The molecular weight of the urea derivative (B) is preferably less than 1,000.

As the urea derivative (B), specifically, N-
(3-trimethoxysilylpropyl) urea, N- (3
-Triethoxysilylpropyl) urea, N- (3-methyldimethoxysilylpropyl) urea, N- (3-dimethylmethoxysilylpropyl) urea, N-3-trimethoxysilylpropyl-N'-methylurea, N-3
-Triethoxysilylpropyl-N'-methylurea,
N-3-methyldimethoxysilylpropyl-N'-methylurea, N-3-dimethylmethoxysilylpropyl-
Examples include, but are not limited to, N'-methylurea. As the urea derivative (B) having a hydrolyzable silicon group, one type may be used alone, or a mixture of two or more types may be used.

The ratio of the urea derivative (B) having a hydrolyzable silicon group to the organic polymer (A) is (A) / (B) = 100 / 0.1 to 100/40 by weight.
Is preferable.

The curable composition of the present invention may further contain, if necessary, a filler, a plasticizer, a curing catalyst, and other additives.

Known fillers can be used as the filler. The amount of the filler to be used is preferably 0 to 1000 parts by weight, particularly preferably 50 to 250 parts by weight, based on 100 parts by weight of the organic polymer (A). Specific examples of the filler include the following. These fillers may be used alone or in combination of two or more.

Calcium carbonate, fumed silica, precipitated silica, silicic anhydride, hydrous silicic acid and carbon black, magnesium carbonate, diatomaceous earth, calcined clay, clay, talc, titanium oxide, bentonite, organic bentonite, ferric oxide, Powdered fillers such as zinc oxide, activated zinc flower, shirasu balloon, wood flour, pulp, cotton chips, mica, walnut flour, fir flour, graphite, aluminum fine powder, flint powder, asbestos, glass fiber, glass filament, Fibrous filler such as carbon fiber, Kevlar fiber and polyethylene fiber.

Known plasticizers can be used as the plasticizer. The use amount of the plasticizer is preferably 0 to 100 parts by weight based on 100 parts by weight of the organic polymer (A). The following are specific examples of the plasticizer.

Dioctyl phthalate, dibutyl phthalate,
Phthalate esters such as butylbenzyl phthalate. Aliphatic carboxylic acid esters such as dioctyl adipate, diisodecyl succinate, dibutyl sebacate and butyl oleate; Alcohol esters such as pentaerythritol ester. Phosphate esters such as trioctyl phosphate and tricresyl phosphate. Epoxy plasticizers such as epoxidized soybean oil, dioctyl 4,5-epoxyhexahydrophthalate, and benzyl epoxy stearate. Chlorinated paraffin. Hydrocarbon plasticizers such as alkylbenzene. Polyester-based plasticizers such as polyesters of dibasic acids and dihydric alcohols, polyethers such as polyoxypropylene glycol and derivatives thereof, poly-α-methylstyrene,
Polymer plasticizers such as oligomers of polystyrene such as polystyrene, oligomers such as polybutadiene, butadiene-acrylonitrile copolymer, polychloroprene, polyisoprene, polybutene, hydrogenated polybutene, and epoxidized polybutadiene.

In curing the curable composition of the present invention, a curing catalyst which promotes a curing reaction of a hydrolyzable silicon group may be used. Specific examples include the following compounds. One or more of them are used. The curing catalyst is preferably used in an amount of 0 to 10 parts by weight based on 100 parts by weight of the organic polymer (A).

Metal salts such as alkyl titanates, organosilicon titanates, bismuth tris (2-ethylhexanoate), acidic compounds such as phosphoric acid, p-toluenesulfonic acid and phthalic acid, ethylenediamine and hexanediamine Aliphatic diamines, aliphatic polyamines such as diethylenetriamine, triethylenetetramine and tetraethylenepentamine, heterocyclic amines such as piperidine and piperazine, aromatic amines such as m-phenylenediamine, alkanolamines, dibutylamine- Amine compounds such as amine salts such as 2-ethylhexoate and various modified amines used as curing agents for epoxy resins;

Tin dioctylate, dibutyltin dilaurate, dioctyltin dilaurate, carboxylic acid type organotin compounds of the formula (10), and mixtures of these carboxylic acid type organotin compounds with the above amines.

A sulfur-containing organotin compound of the formula

Organic tin oxides such as (nC ₄ H ₉ ) ₂ SnO and (nC ₈ H ₁₇ ) ₂ SnO, and these organic tin oxides, ethyl silicate, dimethyl maleate, diethyl maleate, dioctyl maleate, and phthalic acid Reaction products with ester compounds such as dimethyl, diethyl phthalate and dioctyl phthalate.

A chelate tin compound of the formula (12) and a reaction product of these tin compounds with alkoxysilane (acac is an acetylacetonato ligand, e-aca
c is an acetoacetate ligand).

A tin compound represented by the following formula:

[0064]

Embedded image (nC ₄ H ₉ ) ₂ Sn (OCOCH = CHCOOCH ₃ ) ₂ , (nC ₄ H ₉ ) ₂ S
n (OCOCH = CHCOOC ₄ H ₉ -n) ₂ , (nC ₈ H ₁₇ ) ₂ Sn (OCOCH = CHCOOCH
₃ ) ₂ , (nC ₈ H ₁₇ ) ₂ Sn (OCOCH = CHCOOC ₄ H ₉ -n) ₂ , (nC ₈ H ₁₇ ) ₂
Sn (OCOCH = CHCOOC ₈ H ₁₇ -iso) ₂ .

[0065]

Embedded image (nC ₄ H ₉ ) ₂ Sn (SCH ₂ COO), (nC ₈ H ₁₇ ) ₂ Sn (SCH ₂ C
OO), (nC ₈ H ₁₇ ) ₂ Sn (SCH ₂ CH ₂ COO), (nC ₈ H ₁₇ ) ₂ Sn (SCH ₂ C
OOCH ₂ CH ₂ OCOCH ₂ S), (nC ₄ H ₉ ) ₂ Sn (SCH ₂ COOC ₈ H ₁₇ -iso) ₂ ,
(nC ₈ H ₁₇ ) ₂ Sn (SCH ₂ COOC ₈ H ₁₇ -iso) ₂ , (nC ₈ H ₁₇ ) ₂ Sn (SCH
₂ COOC ₈ H ₁₇ -n) ₂ , (nC ₄ H ₉ ) ₂ SnS.

[0066]

Embedded image (nC ₄ H ₉ ) ₂ Sn (acac) ₂ , (nC ₈ H ₁₇ ) ₂ Sn (acac)
₂ , (nC ₄ H ₉ ) ₂ (C ₈ H ₁₇ O) Sn (acac), (nC ₄ H ₉ ) ₂ (C ₈ H ₁₇ O) S
n (e-acac).

[0067]

Embedded image (nC ₄ H ₉ ) ₂ (CH ₃ COO) SnOSn (OCOCH ₃ ) (nC ₄ H ₉ )
₂ , (nC ₄ H ₉ ) ₂ (CH ₃ O) SnOSn (OCH ₃ ) (nC ₄ H ₉ ) ₂ .

In the curable composition of the present invention, a compound containing an air oxidation-curable unsaturated group in the molecule (hereinafter referred to as an unsaturated group-containing compound) may be used as a surface modifier. Examples of the unsaturated group-containing compound include drying oils such as tung oil, linseed oil, and dehydrated castor oil, and modified and polymer forms thereof. Tung oil is particularly preferred.

These unsaturated group-containing compounds may be used alone or in combination of two or more.

The unsaturated group-containing compound is used in an amount of 0.1 to 20 parts, especially 1 to 100 parts by weight of the organic polymer (A).
10 parts are preferred.

Other dehydrating agents include alkyl orthoformates, hydrolyzable organic silicon compounds such as vinyltrimethoxysilane and tetraethylsilicate, and hydrolyzable organic titanium compounds. Adhesion-imparting agents include phenol resins and epoxy resins. Known silane coupling agents and denatured products thereof, various anti-aging agents, ultraviolet absorbers, light stabilizers and the like can be used.

The curable composition of the present invention cures at room temperature in the presence of moisture and can be used particularly for elastic sealants and adhesives. Since the curable composition of the present invention is excellent in adhesiveness and storage stability, it can be stored even in a state containing a certain amount of water under no catalyst. Therefore, it is particularly suitable as a two-part adhesive or a sealing material (for example, for building materials) in which a catalyst is added later.

[0073]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described with reference to embodiments. Example,
The compounds used in the comparative examples are as shown in Table 1.

Example 1 Polyoxypropylene triol was obtained by polymerization of propylene oxide with glycerin as an initiator using a zinc hexacyanocobaltate catalyst.
After converting the terminal hydroxyl group to an allyloxy group, methyldimethoxysilane was reacted in the presence of a platinum catalyst to convert the allyl group to a methyldimethoxysilylpropyl group, thereby obtaining polyether P1 having an average molecular weight of 17,000.

[0075]

[Table 1]

[Examples 2 to 3 (Examples) and Examples 4 to 7 (Comparative Examples)] 150 parts by weight of calcium carbonate and 50 parts by weight of a plasticizer were added to 100 parts by weight (hereinafter referred to as "parts") of the polyether P1.
Parts, 3 parts of a thixotropy imparting agent, compounds shown in the table among compounds B1, B2 and B3, the parts shown in the table and 5 parts of vinyltrimethoxysilane were added and mixed well. After measuring the viscosity of half of the obtained composition, 1 part of bisacetylacetonate tin catalyst was added, mixed well, cured and cured under moisture, and aluminum plate to aluminum plate (primer) according to JIS A5758. None) was evaluated as the initial value. Further, the other half of the composition was sealed and stored at 50 ° C. for one month, and this was similarly evaluated to obtain a value after one month. Table 2 shows the results.

In the table, M50 indicates a 50% modulus,
The unit is kg / cm ² , and the units of breaking strength, breaking elongation, and viscosity are kg / cm ² ,%, and 10,000 cP, respectively.

[0078]

[Table 2]

[Examples 8 to 9 (Examples) and Examples 10 to 13]
Comparative Example] Bisacetylacetonatotin catalyst 1 of Example 2
Parts instead of 1.5 parts of tin octylate and 0.1 part of laurylamine.
Except that 5 parts were used, the same evaluation as in Example 2 was performed. Table 3 shows the results.

[0080]

[Table 3]

[0081]

The curable composition of the present invention provides a curable composition characterized by exhibiting remarkably excellent mechanical properties and adhesive strength, and maintaining its properties even when stored for a long period of time with moisture. It has the effect of.

 ────────────────────────────────────────────────── ─── Continuing on the front page (72) Inventor Tatsuo Onoguchi 1150 Hazawacho, Kanagawa-ku, Yokohama-shi, Kanagawa Prefecture Inside Asahi Glass Co., Ltd.

Claims (3)

[Claims] 1. An organic polymer (A) having at least one silicon-containing group containing a silicon atom to which a hydroxyl group or a hydrolyzable group is bonded, and a silicon atom to which a hydroxyl group or a hydrolyzable group is bonded. A curable composition comprising a urea derivative (B) having a silicon-containing group containing: 2. The curable composition according to claim 1, wherein the urea derivative (B) is a compound having a ureido bond or a ureylene bond. 3. The curable composition according to claim 1, wherein the silicon-containing group containing a silicon atom to which a hydroxyl group or a hydrolyzable group is bonded is a group represented by the formula 1. ## STR1 ## Among -SiX _a R ¹ _3-a ··· Formula 1 Formula 1, R ¹ is 1 substituted or unsubstituted 1 to 20 carbon atoms
A monovalent hydrocarbon group, X is a hydroxyl group or a monovalent hydrolyzable group, and a is an integer of 1 to 3.