JP3449991B2 - 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 workability, an adhesive property, a workability, an adhesive property, which is cured by moisture in the atmosphere to form a rubber-like elastic body.
The present invention also relates to a curable composition having excellent durability such as heat resistance and water resistance.

[0002]

2. Description of the Related Art Conventionally, as a moisture-curing resin component used for waterproof sealing materials for buildings, civil engineering, automobiles, adhesives, paints, etc. Resins such as chain polyethers containing a crosslinkable silyl group in the molecule and polyurethane resins are widely used because of their excellent workability and adhesiveness.

[0003]

However, in recent years,
In the fields of buildings, civil engineering, automobiles, etc., there is a growing need for so-called ultra-long life, which maintains performance over a long period of time, and the adhesiveness to sealants, adhesives, paints, etc. Further, further improvement in durability such as heat resistance, water resistance and weather resistance is required. Sealing materials containing modified silicone resin, adhesives, paints, etc., although workability is good, but the weather resistance is still insufficient, it has the drawback of poor durability such as water resistance and heat resistance, Furthermore, there is a problem that a special device is required for synthesizing the modified silicone resin, and the manufacturing is difficult and expensive. On the other hand, a polyurethane resin has the advantages that it has excellent adhesiveness and water resistance, is easy to manufacture, and is relatively inexpensive, but it has the drawback of poor weather resistance. Here, there is known a crosslinkable silyl group-containing polyurethane resin obtained by reacting an isocyanate group-containing polyurethane resin with a compound containing active hydrogen and a crosslinkable silyl group in the molecule (see, for example, Japanese Patent Publication No. 46-30711). ). However, while this resin has the characteristics that it is easy to synthesize and has excellent adhesiveness, it has a high viscosity,
It has a problem of poor durability such as water resistance, heat resistance, and weather resistance. Further, a resin having a crosslinkable silyl group and a urethane bond, which is obtained by reacting a compound having an isocyanate group and a crosslinkable silyl group with a polyol such as a polyether polyol, is also known (for example, JP-A-03-
47825). However, although this resin has a low viscosity, it has a problem of poor durability such as water resistance, heat resistance, and weather resistance.

An object of the present invention is to solve the above-mentioned problems of the known art and to produce a rubber-like elastic body which is easy to manufacture and has good workability, and which is cured by moisture in the atmosphere and has excellent physical properties. A low-viscosity one-component moisture-curable curable composition having excellent adhesiveness, weather resistance, heat resistance, and particularly water resistance.

[0005]

To achieve the above object, the present invention is obtained by reacting a hydroxyl group-containing polyoxyalkylene polymer, a crosslinkable silyl group-containing isocyanate compound and an organic monoisocyanate sequentially or simultaneously. A curable composition comprising a crosslinkable silyl group-containing resin as a curing component.

The present invention comprises a crosslinkable silyl group-containing resin obtained by reacting a hydroxyl group-containing polyoxyalkylene polymer, a crosslinkable silyl group-containing isocyanate compound and an organic monoisocyanate sequentially or simultaneously, and an additive. The curable composition is characterized by:

The present invention is the curable composition, wherein the additive is an antioxidant and / or a crosslinking catalyst.

The present invention is the curable composition, wherein the additive is an antioxidant, a crosslinking catalyst, a filler, a coupling agent, a thixotropic agent, and / or a storage stability improver.

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION First, the crosslinkable silyl group-containing resin in the present invention will be described. The crosslinkable silyl group-containing resin in the present invention is a resin containing in the molecule one or more silyl groups which are crosslinked to form a rubber-like cured product by reacting with moisture (water) to form a siloxane bond. The hydroxyl group-containing polyoxyalkylene polymer for producing the crosslinkable silyl group-containing resin is a polymer obtained by ring-opening addition polymerization of alkylene oxide, or a polymer obtained by ring-opening addition polymerization of alkylene oxide as an initiator. is there. As the initiator, ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, neopentyl glycol, 1,4-butanediol, 1,6-
Hexanediol, glycerin, trimethylolpropane, pentaerythritol, low molecular weight alcohols such as sucrose, polyhydric phenols such as bisphenol A, low molecular weight polyamines such as ethylenediamine, low molecular weight amino alcohols such as diethanolamine, or these Examples thereof include a mixture of two or more kinds. Examples of the alkylene oxide include ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, and a mixture of two or more thereof. That is, the hydroxyl group-containing polyoxyalkylene polymer has 2
A polyoxyalkylene polymer having one or more hydroxyl groups, specifically, for example, polyoxyethylene glycol, polyoxypropylene glycol, polytetramethylene ether glycol, poly (oxyethylene) -poly (oxypropylene) -Glycol and poly (oxyethylene) -poly (oxybutylene) -glycol can be mentioned, of which polyoxypropylene glycol is particularly preferred. As the hydroxyl group-containing polyoxyalkylene polymer, various polyols listed above and conventionally known polyisocyanates such as toluene diisocyanate, diphenylmethane diisocyanate (MDI), hexamethylene diisocyanate, and isophorone diisocyanate are used for isocyanate groups. A polymer having a hydroxyl group at the molecular end by reacting with excess hydroxyl groups is also included. These may be used alone or in combination of two or more. In the present invention, the hydroxyl group-containing polyoxyalkylene polymer has a number average molecular weight of 500 to 4 from the viewpoint of lowering the viscosity of the curable composition and increasing the elongation of the cured product.
50,000, more preferably 2,000 to 30,000, especially 1
30,000 to 30,000 are preferable, and 1
The average number of hydroxyl groups per molecule is preferably from 2 to 8, particularly preferably from 2 to 4, and further, the total unsaturation degree is 0.07 (meq / g) or less, particularly 0.04 (meq / g) or less. A narrow one is preferable.

The crosslinkable silyl group-containing isocyanate compound for producing the crosslinkable silyl group-containing resin in the present invention may contain at least one isocyanate group and at least one crosslinkable silyl group in the molecule. The crosslinkable silyl group is preferably one represented by the following general formula, which is easy to produce and easy to crosslink.

[0011]

[Chemical 1]

(In the formula, R is a hydrocarbon group and has 1 carbon atom.
~ 20 alkyl groups, C6-20 aryl groups or C7-20 aralkyl groups are preferred, and methyl groups are most preferred. The reactive group represented by X is a halogen atom,
A group selected from a hydrogen atom, a hydroxyl group, an alkoxy group, an acyloxy group, a ketoximate group, an amide group, an acid amide group, a mercapto group, an alkenyloxy group and an aminooxy group, and when X is plural, X are the same group. Or different groups may be used. Of these, X is preferably an alkoxy group, and more preferably a methoxy group, an ethoxy group or an isopropoxy group. a is an integer of 0, 1 or 2, and 0 or 1 is preferable. )

Specific examples of the crosslinkable silyl group-containing isocyanate compound include 3-isocyanatepropyltrimethoxysilane, 3-isocyanatepropyltriethoxysilane, 3-isocyanatepropylmethyldiethoxysilane, and 3-isocyanatepropylmethyldimethoxysilane. , 3-isocyanate propyl isopropoxy silane, isocyanate trimethoxy silane, diisocyanate dimethoxy silane, etc., and these can be used alone or in combination of two or more.

The organic monoisocyanate for producing the crosslinkable silyl group-containing resin in the present invention has 1 in the molecule.
Although it is sufficient to contain at least one isocyanate group,
It does not contain a crosslinkable silyl group. That is, the organic group other than the isocyanate group of the organic monoisocyanate is preferably a hydrophobic organic group containing no moisture (moisture) curable functional group. Specifically, n-butyl monoisocyanate, n-hexyl monoisocyanate, n-
Tetradecyl monoisocyanate, n-hexadecyl monoisocyanate, octadecyl monoisocyanate,
aliphatic monoisocyanate such as n-chloroethyl monoisocyanate, chlorophenyl monoisocyanate,
3,5-dichlorophenyl monoisocyanate, p-fluorophenyl monoisocyanate, 2,4-difluorophenyl monoisocyanate, o-trifluoromethylphenyl monoisocyanate, p-nitrophenyl monoisocyanate, p-isopropylphenyl monoisocyanate, 2,6 -Diisopropyl monoisocyanate, p-toluenesulfonyl monoisocyanate, p-
Examples thereof include aromatic monoisocyanates such as benzyloxyphenyl monoisocyanate, and 2-methacryloyloxyethyl isocyanate. Of these, aliphatic monoisocyanates are preferable because they improve water resistance. These can be used alone or in combination of two or more.

The crosslinkable silyl group-containing resin in the present invention has a crosslinkable silyl group-containing isocyanate compound and an organic monoisocyanate isocyanate group for the hydroxyl group of the hydroxyl group-containing polyoxyalkylene polymer.
It can be obtained by reacting sequentially or simultaneously. When sequentially reacting, the hydroxyl group-containing polyoxyalkylene polymer, the crosslinkable silyl group-containing isocyanate compound and the organic monoisocyanate may be reacted first, but first the crosslinkable silyl group-containing isocyanate compound is reacted Preferably followed by reaction with an organic monoisocyanate. The crosslinkable silyl group-containing resin of the present invention is crosslinked into the resin by reacting the isocyanate group of the crosslinkable silyl group-containing isocyanate compound with the hydroxyl group of the hydroxyl group-containing polyoxyalkylene polymer at an equivalence ratio that leaves some hydroxyl groups. A silyl group is introduced, and the isocyanate group of the organic monoisocyanate is reacted with a part or all of the remaining hydroxyl group to form a structure in which a hydrophobic organic group having no water-curing property is introduced. It is possible to obtain a curable resin in which rubber elasticity such as modulus and elongation can be freely adjusted, and water resistance after curing is remarkably improved. The hydroxyl group-containing polyoxyalkylene polymer, the crosslinkable silyl group-containing isocyanate compound, and the organic monoisocyanate have an isocyanate group / hydroxyl group equivalent ratio of 0.1 or more / 1.0, more preferably 0.5 to 1.
The reaction is preferably carried out within the range of 5 / 1.0, particularly 0.7 to 1.0 / 1.0. When the equivalent ratio of isocyanate group / hydroxyl group is less than 0.1 / 1.0, the crosslinkable silyl group-containing resin has few crosslinking groups and many hydroxyl groups, so that the physical properties of the cured product are not expressed and the water resistance is improved. do not do. When the hydroxyl group-containing polyoxyalkylene polymer and the crosslinkable silyl group-containing isocyanate compound and the organic monoisocyanate are sequentially reacted, the hydroxyl group-containing polyoxyalkylene polymer and the crosslinkable silyl group-containing isocyanate compound are isocyanate groups. / Hydroxyl group equivalent ratio is 0.05 ~
The reaction product and the organic monoisocyanate are added together with a crosslinkable silyl group-containing isocyanate compound in the range of 0.9 / 1.0, and further in the range of 0.3 to 0.9 / 1.0. And the equivalent ratio of isocyanate group / hydroxyl group is 0.1 or more / 1.0, more preferably 0.5 to 1.5 / 1.0,
It is particularly preferable to react in the range of 0.7 to 1.0 / 1.0. In this reaction, known urethanization catalysts such as organic metal compounds such as dibutyltin dilaurate and dioctyltin dilaurate, organic amines such as triethylenediamine, triethylamine, tri-n-butylamine and salts thereof, and the like can be used, Further, a known organic solvent can also be used.

It is preferable that the crosslinkable silyl group-containing resin molecule contains an average of 1 to 5 crosslinkable silyl groups from the viewpoint of curability and physical properties after curing.

Next, the additives in the curable composition of the present invention will be described. As the additive in the present invention,
Examples include antioxidants, ultraviolet absorbers, crosslinking catalysts, fillers, coupling agents, thixotropic agents, storage stability improvers (dehydrating agents), and colorants.

Antioxidants and ultraviolet absorbers are used for preventing oxidation, photodegradation and thermal deterioration of the cured resin, and further improving not only weather resistance but also heat resistance. Specific examples of the antioxidant include hindered amine-based and hindered phenol-based antioxidants.

As the hindered amine type antioxidant,
For example, [decanedioic acid bis (2,2,6,6-tetramethyl-1 (octyloxy) -4-piperidyl) ester, bis (1,2,2,6,6-pentamethyl-4-piperidyl) [ [3,5-bis (1,1-dimethylethyl) -4-hydroxyphenyl] methyl] butyl malonate, methyl 1,2,2,6,6-pentamethyl-4-
Piperidyl sebacate, bis (1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, 1- [2-
[3- (3,5-Di-tert-butyl-4-hydroxyphenyl) propionyloxy] ethyl] -4- [3
-(3,5-Di-tert-butyl-4-hydroxyphenyl) propionyloxy] -2,2,6,6-tetramethylpiperidine, 4-benzoyloxy-2,2
6,6-tetramethylpiperidine may be mentioned. Also,
Each compound of the ADEKA STAB series manufactured by Asahi Denka Co., Ltd. is also included.

Examples of the hindered phenol-based antioxidant include pentaerythritol-tetrakis [3-
(3,5-Di-tert-butyl-4-hydroxyphenyl) propionate], octadecyl-3- (3,5
-Di-tert-butyl-4-hydroxyphenyl) propionate], N, N'-hexane-1,6-diylbis [3- (3,5-di-tert-butyl-4-hydroxyphenylpropioamide], benzene Examples include propanoic acid 3,5-bis (1,1-dimethylethyl) -4-hydroxy C7-C9 side chain alkyl ester and 2,4-dimethyl-6- (1-methylpentadecyl) phenol.

Examples of the ultraviolet absorber include 2-
Benzotriazole-based UV absorbers such as (3,5-di-tert-butyl-2-hydroxyphenyl) benzotriazole, 2- (4,6-diphenyl-1,3,5-
Triazin-2-yl) -5-[(hexyl) oxy]
-Triazine-based UV absorbers such as phenol, benzophenone-based UV absorbers such as octabenzone, 2,4-di-tert-butylphenyl-3,5-di-tert-
Examples thereof include benzoate-based UV absorbers such as butyl-4-hydroxybenzoate.

Each of the antioxidant and the ultraviolet absorber is 0.1 to 100 parts by weight of the crosslinkable silyl group-containing resin.
It is preferable to add 10 parts by weight, particularly 0.5 to 5 parts by weight.

The cross-linking catalyst is a catalyst for cross-linking (curing) the cross-linkable silyl group-containing resin, and specific examples thereof include organic metal compounds and amines. Tin compounds are preferred. This organotin compound is specifically stannas octoate, dibutyltin dioctoate, dibutyltin dilaurate, dibutyltin diacetate, dibutyltin diacetylacetonate, dibutyltin oxide, dibutyltin bistriethoxysilicate, dibutyltin distearate, dioctyltin. Among them, dilaurate and dioctyltin diversate are preferred, and among them, dibutyltin diacetylacetonate is most preferable because it is a liquid having a high crosslinking rate and relatively low toxicity and brilliance. The crosslinking catalyst is preferably added in an amount of 0.1 to 10 parts by weight, particularly 0.3 to 5 parts by weight, based on 100 parts by weight of the crosslinkable silyl group-containing resin, from the viewpoints of the crosslinking rate, the physical properties of the cured product, and the like. .

A filler, a coupling agent, a thixotropic agent, a storage stability improving agent (dehydrating agent), a coloring agent and the like are used in the curing of the present invention for the purpose of improving adhesiveness, reinforcing, preventing sagging and the like. It can be used by being blended with a sexual composition.

Examples of the filler include calcium carbonate, clay, talc, slate powder, mica, kaolin, zeolite, diatomaceous earth, fatty acid-treated calcium carbonate, and the like.
Those having a particle size of 1 to 100 μm are preferable, and of these, fatty acid-treated calcium carbonate is more preferable.

Examples of the coupling agent include silane-based, aluminum-based, and zircoaluminate-based ones. Of these, silane-based coupling agents are preferable because of their excellent adhesiveness. As the silane coupling agent, specifically, N- (β-aminoethyl) -γ-
Aminopropylmethyldimethoxysilane, N- (β-aminoethyl) -γ-aminopropyltrimethoxysilane, N- (β-aminoethyl) -γ-aminopropylmethyldimethoxysilane, γ-glycidoxypropyltrimethoxysilane, Examples thereof include low molecular weight compounds having an alkoxysilyl group such as γ-glycidoxypropylmethyldiethoxysilane and having a molecular weight of 500 or less, preferably 400 or less.

Examples of the thixotropic agent include inorganic thixotropic agents such as colloidal silica and asbestos powder, and organic thixotropic agents such as organic bentonite, modified polyester polyols and fatty acid amides.

Examples of the storage stability improver include low molecular weight crosslinkable silyl group-containing compounds such as vinyltrimethoxysilane, calcium oxide, etc., which react with water present in the composition.

Examples of the colorant include inorganic pigments such as titanium oxide and iron oxide, organic pigments such as copper phthalocyanine, and carbon black.

The total amount of the filler, the coupling agent, the thixotropic agent, the storage stability improver, and the colorant is 0 to 500 parts by weight based on 100 parts by weight of the crosslinkable silyl group-containing resin.
Particularly, the range of 50 to 300 parts by weight is preferable.

In the curable composition of the present invention, each of the above components may be used alone or in combination of two or more.

In the curable composition of the present invention, if necessary, an ester solvent such as ethyl acetate, a ketone solvent such as methyl ethyl ketone, an aliphatic solvent such as n-hexane, or an alicyclic solvent such as cyclohexane. Any conventionally known organic solvent such as an aromatic solvent such as toluene or xylene that does not react with the crosslinkable silyl group may be used alone or in combination of two or more. The type and the amount used may be appropriately determined according to the application of the curable composition.

[0033]

EXAMPLES The present invention will now be described in more detail by way of examples. Here, the sealing material composition is shown as an example of the curable composition, but the invention is not limited thereto.

Synthesis Example 1 Polyoxypropylene glycol (number average molecular weight 16,000, total satiety 0.02 meq / g, Asahi glass (in a warm reaction vessel equipped with a stirrer, a thermometer, a nitrogen seal tube and a condenser) 800 ml (OH equivalent: 0.1) of PML-4016 manufactured by Shin-Etsu Chemical Co., Ltd. (K manufactured by Shin-Etsu Chemical Co., Ltd.)
BE-9007, measured isocyanate group content by titration 16.4% by weight) 15.4 g (NCO equivalent: 0.0
6) (R value (NCO equivalent / OH equivalent) = 0.6) and 0.82 g of dibutyltin dilaurate were added, and the mixture was heated and stirred at 80 ° C. for 10 minutes, and the isocyanate group content measured by titration was 0. It was cooled after confirming disappearance of the peak of the isocyanate group by FTIR. Then, in this, octadecyl monoisocyanate 11.
8 g (NCO equivalent: 0.04) (R value (NCO equivalent / O
H equiv.
After stirring for a minute, the disappearance of the peak of the isocyanate group was confirmed by FTIR, and the reaction was terminated by cooling to room temperature. The obtained triethoxysilyl group-containing polyoxypropylene-urethane resin is a liquid having a theory of translucency at room temperature, an isocyanate group content of 0.00 wt% measured by titration, and a viscosity of 14,800 mPa · s / 25 ° C. It was This resin is called NU-1.

Synthesis Example 2 In Synthesis Example 1, 3-isocyanatopropyltriethoxysilane (KBE-900 manufactured by Shin-Etsu Chemical Co., Ltd.)
7) 20.5 g (NCO equivalent: 0.08) (R value (N
CO equivalent / OH equivalent) = 0.8), and 5.9 g of octadecyl monoisocyanate (NCO equivalent: 0.0
2) (R value (NCO equivalent / OH equivalent) = 0.2) The reaction was performed in the same manner except that it was used. The obtained triethoxysilyl group-containing polyoxypropylene-urethane resin was translucent at room temperature, had a theoretical isocyanate group content of 0.00 wt% by titration, and a viscosity of 16,000 mPas.
-It was a liquid at s / 25 ° C. This resin is called NU-2.

Synthesis Example 3 A polyoxypropylene glycol (number average molecular weight 16,000, total satiety 0.02 meq / g, PML-401 manufactured by Asahi Glass Co., Ltd.) was placed in the same heating reaction vessel as in Synthesis Example 1.
6) 800 g (OH equivalent: 0.1) was charged, and while stirring, 3-isocyanatepropyltriethoxysilane (KBE-9007 manufactured by Shin-Etsu Chemical Co., Ltd.) 15.4 g
(NCO equivalent: 0.06) (R value (NCO equivalent / OH equivalent) = 0.6) and 0.82 g of dibutyltin dilaurate were added, followed by heating and stirring at 80 ° C. for 10 minutes, followed by titration. Measured isocyanate group content 0.00% by weight,
The disappearance of the isocyanate group peak was confirmed by FTIR, and the reaction was terminated by cooling to room temperature. The obtained triethoxysilyl group-containing polyoxypropylene-urethane resin has a theory of translucency at room temperature, an isocyanate group content measured by titration of 0.00% by weight, and a viscosity of 14.0.
It was a liquid of 0 mPa · s / 25 ° C. This resin is NU
-3.

Synthetic Example 4 In Synthetic Example 3, 3-isocyanatopropyltriethoxysilane (KBE-900 manufactured by Shin-Etsu Chemical Co., Ltd.)
7) 20.5 g (NCO equivalent: 0.08) (R value (N
The reaction was carried out in the same manner except that CO equivalent / OH equivalent) = 0.8) was used. The obtained triethoxysilyl group-containing polyoxypropylene-urethane resin has a theory of translucency at room temperature, an isocyanate group content measured by titration of 0.00% by weight, and a viscosity of 15,800 mPa · s / 25 ° C.
It was a liquid. This resin is called NU-4.

Synthetic Example 5 In Synthetic Example 3, 3-isocyanatopropyltriethoxysilane (KBE-900 manufactured by Shin-Etsu Chemical Co., Ltd.)
7) 25.6 g (NCO equivalent: 0.1) (R value (NC
The reaction was performed in the same manner except that O equivalent / OH equivalent) = 1.0) was used. The obtained triethoxysilyl group-containing polyoxypropylene-urethane resin was semi-transparent at room temperature, and the measured isocyanate group content by titration was 0.
The liquid was 00% by weight and had a viscosity of 18,000 mPa · s / 25 ° C. This resin is called NU-5.

Example 1 A trioxysilyl group-containing polyoxypropylene-urethane resin NU-1400 was placed in a kneading vessel equipped with a heating device.
g, hindered phenolic antioxidant: pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate] (Ciba Specialty Chemicals KK Irganox 1010) 4 g , Fatty acid (surface) treated calcium carbonate (Calfine 200M manufactured by Maruo Calcium Co., Ltd.) 35
0 g, fatty acid amide (fatty acid amide S manufactured by Kao Co., Ltd.) 4.5 g, and vinyltrimethoxysilane (Sila Ace S210 manufactured by Chisso Co., Ltd.) 6 g were charged, and the contents were stirred and mixed until uniform. Then 1 at 110 ℃
Dibutyltin diacetylacetonate (Neostan U-220 manufactured by Nitto Kasei Co., Ltd.)
2 g and 2 g of N- (β-aminoethyl) -γ-aminopropylmethyldimethoxysilane (Sila Ace S310 manufactured by Chisso Corporation) were charged, stirred and mixed to prepare a sealant composition.

Example 2, Comparative Examples 1 to 3 In Example 1, NU was used in place of the triethoxysilyl group-containing polyoxypropylene-urethane resin NU-1.
Sealing material compositions were prepared in the same manner except that each of −2 to 5 was used.

[Performance Test] Examples 1 and 2 and Comparative Example 1
The following tests were performed using the sealing material composition prepared in any one of Examples 1 to 3. (1) Extrudability Measured in accordance with "4.14 Extrusion Test with Test Cartridge" of JIS A1439: 1997 "Testing Method for Building Sealing Materials" (measurement temperature 23 ° C). (2) Slump (longitudinal) was measured in accordance with "4.1 Slump test" of JIS A1439: 1997 "Testing method for building sealing material" (measurement temperature 23 ° C). (3) Tensile Adhesion Property According to “4.21 Tensile Adhesion Test” of JIS A1439: 1997 “Testing Method for Building Sealants”, after curing, each test after hot water immersion treatment at 50 ° C. for 7 days A tensile test was conducted on the body. The test body was prepared by treating the slate with a primer (OP2531, manufactured by Auto Kagaku Kogyo Co., Ltd.), casting and curing the sealant composition. Modulus is 50% tensile stress (M50)
Values were evaluated as × ones of less than 30N / cm ² ○, less than 5N / cm ² or 30 N / cm ² or more at 5N / cm ² or more. Regarding the elongation, in the tensile test, those having Emax of 400% or more were evaluated as ◯, and those of less than 400% were evaluated as x. The results and the composition of the sealant composition are summarized in Table 1. In addition, in Table 1, the ratio of those values after 7 days of immersion in 50 ° C. warm water with respect to M50, Tmax, and Emax after curing is also shown as the tensile adhesiveness retention rate.

[0042]

[Table 1]

[0043]

As described above, the crosslinkable silyl group-containing resin of the present invention has a low viscosity, and has a modulus and elongation in an appropriate range and a high strength after curing. Therefore, a curable composition containing the same Has excellent workability and further has excellent adhesiveness after curing. Further, the curable composition of the present invention is excellent in weather resistance, heat resistance and particularly water resistance in addition to the above-mentioned properties, and therefore, it is suitable for ultralong life and high performance of recent buildings, civil engineering, automobiles, etc. Can be fully adapted. In particular, the curable composition of the present invention has an extremely long life such as joints of outer walls of buildings, a high performance sealing material or a building member,
Suitable for adhesives such as automobile parts.

─────────────────────────────────────────────────── --Continued from the front page (58) Fields surveyed (Int.Cl. ⁷ , DB name) C08L 71/00-71/08 C08G 18/00-18/87 C08G 65/00-65/48 C08L 75 / 04-75/16

Claims (4)

(57) [Claims] 1. A crosslinkable silyl group-containing resin obtained by reacting a hydroxyl group-containing polyoxyalkylene polymer, a crosslinkable silyl group-containing isocyanate compound, and an organic monoisocyanate sequentially or simultaneously is contained as a curing component. Curable composition characterized. 2. A crosslinkable silyl group-containing resin obtained by sequentially or simultaneously reacting a hydroxyl group-containing polyoxyalkylene polymer, a crosslinkable silyl group-containing isocyanate compound and an organic monoisocyanate, and an additive. A curable composition comprising: 3. The curable composition according to claim 2, wherein the additive is an antioxidant and / or a crosslinking catalyst. 4. The additive is an antioxidant, a crosslinking catalyst,
The curable composition according to claim 2, which is a filler, a coupling agent, a thixotropic agent, and / or a storage stability improver.