JPH06107941A - Curable composition - Google Patents

Abstract

PURPOSE:To obtain a curable composition, having great tack reducing effects and good in preservation stability. CONSTITUTION:The objective curable composition is obtained by copolymerizing alphaomega-bis(3-aminopropyl)-polydimethylsiloxane with propylene oxide-using a hexacyanocobaltzinc-glyme complex and adding the resultant compound to a polymer prepared by introducing methyldimethoxysilylpropyl group into 75% terminals of a polyoxypropylendiol obtained by using the hexacyanocobaltzinc-glyme complex.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a curable composition containing a hydrolyzable silicon group-containing polymer and a polyorganosiloxane-modified polyoxyalkylene polymer as active ingredients.

[0002]

2. Description of the Related Art Polyoxyalkylene having at least one hydrolyzable silicon group in the molecule is compounded with various compounding agents and used as a sealing agent for buildings and the like. However, depending on the composition of the composition and the conditions of use, tack (stickiness) remains on the surface of the cured product, and dust or the like adheres to the composition, which causes the appearance to be impaired.

JP-A-55-21453 discloses that a curable composition comprising a hydrolyzable silicon group-containing polymer and an organic silicon polymer is effective in reducing tack. However, this method has a problem in that the compatibility of the composition is poor and the storage stability of the blend is extremely poor.

Further, in JP-A-57-145147, a copolymer containing both a polysiloxane unit and an organic polymer unit, which is obtained by reacting an organopolysiloxane having a silanol group and a hydrolyzable silicon group-containing polyether, is disclosed. A curable composition prepared by mixing a polymer with a hydrolyzable silicon group-containing polymer is disclosed. However, in order to obtain the copolymer, it is necessary to introduce a hydrolyzable silicon group into the polyether and then react with the silanol group-containing polysiloxane, which is a complicated process.

[0005]

SUMMARY OF THE INVENTION It is an object of the present invention to provide a curable composition which satisfies tack reduction and storage stability.

[0006]

The present invention uses an organopolysiloxane compound having an active hydrogen-containing functional group capable of reacting with an alkylene oxide as an initiator to carry out ring-opening polymerization of the alkylene oxide in the presence of a catalyst. The resulting modified polyoxyalkylene polymer (A) 0.1 to 100
Curable composition characterized by containing 100 parts by weight of a silicon-containing polymer (B) having at least one hydrolyzable silicon group in the molecule and having a main chain consisting essentially of polyoxyalkylene. It is a thing.

Examples of the catalyst used in the present invention include catalysts such as alkali metal catalysts, complex metal cyanide complex catalysts, metal porphyrins and LiPF ₄ . Of these, the complex metal cyanide complex catalyst is particularly preferable.

The complex metal cyanide complex catalyst is a complex containing two or more kinds of metals and having a cyan ion as a part or all of the ligands, and has the ability to catalyze the ring-opening polymerization reaction of alkylene oxide. Refers to something with. Specifically, for example, hexacyanocobalt zinc complex such as hexacyanocobalt zinc-glyme complex described in JP-B-59-15336, and other U.S. Pat. Nos. 3,278,457 to 327.
There are complex metal cyanide complex catalysts such as those described in 8459.

This catalyst is known to exhibit high catalytic activity for ring-opening polymerization of alkylene oxide. It is known that this catalyst can be used as a catalyst for the polymerization of alkylene oxide using a highly hydrophobic initiator having an organopolysiloxane structure in the molecule.
No. 6 is described.

The complex metal cyanide complex in the present invention has the following chemical formula (4) as shown in the above-mentioned known examples.
It is considered to have the structure of M ¹ _a [M ² _x (CN) _y ] _b (H ₂ O) _c R _d (4)

However, M ¹ is Zn (II), Fe (II), Fe
(III), Co (II), Ni (II), Al (III), Sr (II),
Mn (II), Cr (III), Cu (II), Sn (II), Pb (I
I), Mo (IV), Mo (VI), W (IV), W (VI) and other metal ions, and M ² is Fe (II), Fe (III), Co (II),
Co (III), Cr (II), Cr (III), Mn (II), Mn (I
II), Ni (II), V (IV), V (V) and other metal ions, and R is an organic ligand. a, b, x and y are positive integers that change depending on the valence and coordination number of the metal, and c and d
Is a positive number that depends on the coordination number of the metal.

In the complex metal cyanide complex represented by the chemical formula (4), M ¹ is preferably Zn (II) and M ² is F.
e (II), Fe (III), Co (II), Co (III) and the like are preferable. Examples of organic ligands include ketones, ethers,
Examples include aldehydes, esters, alcohols, amides, nitriles, sulfides.

A particularly preferable complex metal cyanide complex is a hexacyanocobalt zinc complex. Further, a catalyst obtained by combining a hexacyanocobalt zinc complex with another complex metal cyanide complex can also be used. The combination may be a combination of metal components or a mixture of two or more catalysts.

The complex metal cyanide complex represented by the chemical formula (4) is a metal salt M ¹ Y _g (M ¹ is the same as above. Y is M
Anion that forms a salt with ¹ . g is a positive integer that changes depending on the valence of the metal. ) And polycyanometallate (salt) Z _e [M
² _x (CN) _y ] _f (M ² , x and y are the same as above. Z is hydrogen,
Alkali metals, alkaline earth metals, etc. e and f are Z and M
^A positive integer determined by the valence of ² and the coordination number. 2) each aqueous solution or a solution of a mixed solvent of water and an organic solvent is mixed, and the obtained complex metal cyanide is brought into contact with the organic ligand R, and then the excess solvent and the organic ligand R are removed. It is manufactured by

Polycyanometallate (salt) Z _e [M ² _x (C
N) _y ] _f may use various metals such as hydrogen and alkali metals for Z, but lithium salt, sodium salt,
Preference is given to potassium salts, magnesium salts and calcium salts. Particularly preferred are conventional alkali metal salts, that is, sodium salts and potassium salts. The metal salt is preferably a metal halide, such as zinc chloride.

The organopolysiloxane compound having an active hydrogen-containing functional group capable of reacting with an alkylene oxide used as an initiator in the present invention has at least one active hydrogen-containing functional group serving as a polymerization initiation point of the alkylene oxide in the molecule. It is an organopolysiloxane compound having. This active hydrogen-containing functional group is a functional group having 1 to 2 hydrogen atoms with which an alkylene oxide such as a hydroxyl group, a mercapto group, a primary amino group, a secondary amino group, and a carboxyl group can react.

The organopolysiloxane compound is a polymer of siloxane to which at least one organic group is bonded, and at least one of the organic groups is an organic group having an active hydrogen-containing functional group. The organic group having an active hydrogen-containing functional group may be present at at least one of both ends of the molecule, or may be present in the middle of the molecular chain. The organopolysiloxane compound may be a low polymer such as an organodisiloxane compound. The upper limit of the number of polymerized units is not particularly limited, but 500, particularly 200 is preferable.

It is preferable that two organic groups are bonded to the silicon atom excluding both terminals of the organopolysiloxane compound. A hydrocarbon group is preferable as the organic group except the organic group having an active hydrogen-containing functional group. The hydrocarbon group is preferably an alkyl group, an alkenyl group, an aryl group or the like. Particularly, an alkyl group having 4 or less carbon atoms (hereinafter also referred to as a lower alkyl group) and a phenyl group are preferable. It is preferable that three organic groups are bonded to the silicon atoms at both ends, and the above hydrocarbon group is preferable as this organic group except the organic group having an active hydrogen-containing functional group.
Further, at least one of the three organic groups may be a long chain hydrocarbon group.

[0019] Examples of the organic group having an active hydrogen-containing functional _{groups, -OH, -SH, -NH 2,} -NHR 10, -CO 2
A hydrocarbon group having 3 to 10 carbon atoms and containing one or more functional groups of one or more kinds selected from H is preferable. Further, it may further contain a linking group such as an ether bond, a thioether bond or an amino bond. In particular, the organic group preferably has 1 to 4 active hydrogen-containing functional groups. Further, the organopolysiloxane compound preferably has 1 to 10 active hydrogen-containing functional groups.

As the specific organopolysiloxane compound, compounds represented by the following chemical formulas (1) to (3) are preferable.

[0021]

[Chemical 4]

[0022]

[Chemical 5]

[0023]

[Chemical 6]

(In the formula, X is --OH, --SH, --NH ₂ ,
It is a hydrocarbon group having 3 to 10 carbon atoms and containing one or more functional groups of at least one selected from —NHR ¹⁰ and —CO ₂ H, and may contain an ether bond, a thioether bond or an amino bond. R ¹ , R ² , R ³ , R ⁴ , R ⁶ , R
⁷ , R ⁸ and R ¹⁰ are the same or different and each have 1 to 6 carbon atoms.
Is a hydrocarbon group. R ⁵ and R ⁹ are hydrocarbon groups having 1 to 18 carbon atoms. n is 0 or an integer of 1 to 200, m
Is an integer of 1 to 10. )

R ¹ and R ² are each preferably a lower alkyl group, particularly a methyl group. Each of R ^{3 to} R ¹⁰ is preferably a lower alkyl group. Preferred examples of X include a hydroxyalkyl group, a dihydroxyalkyl group, a hydroxyalkoxy-substituted alkyl group, a mercaptoalkyl group, an aminoalkyl group, an N-aminoalkyl-substituted aminoalkyl group, and a carboxyalkyl group.

The alkylene oxide which can be used in the ring-opening polymerization reaction in the present invention includes all those which can be polymerized by a double metal cyanide complex catalyst. In particular,
For example, ethylene oxide, propylene oxide, 1-butene oxide, 2-butene oxide, izobutene oxide, 1-hexene oxide, cyclohexene oxide,
Examples include phenyl glycidyl ether, allyl glycidyl ether, and styrene oxide.

Particularly preferred alkylene oxides are alkylene oxides having 2 to 4 carbon atoms such as ethylene oxide, propylene oxide, 1-butene oxide, 2-butene oxide and isobutene oxide. Two or more kinds of alkylene oxides can be used in combination, and in this case, two or more kinds of alkylene oxides can be mixed and reacted, or separately and sequentially.

In the actual polymerization reaction, the mixture of the initiator, the complex metal cyanide complex and the alkylene oxide may be heated under the nitrogen atmosphere to the polymerization reaction temperature condition. At this time,
The alkylene oxide may be added all at once, or may be added little by little while confirming the progress of the reaction. Also,
When two or more kinds of alkylene oxides are polymerized as described above, a block copolymer or a random copolymer can be freely produced by the addition method. That is, a random copolymer can be obtained by adding a mixture of two or more alkylene oxides, and another alkylene oxide can be added after each polymerization reaction of two or more alkylene oxides is completed. For example, a block copolymer can be produced.

The polymerization reaction temperature is suitably 20 to 180 ° C., preferably 60 to 130 ° C. This polymerization reaction can be performed with or without a solvent.
When a solvent is used, the solvent can be recovered by distilling from the reaction mixture after completion of the reaction.

Examples of the solvent usable in the present invention include ether type, hydrocarbon type, halogenated hydrocarbon type, ketone type, amide type and ester type solvents, and ether type and ketone type solvents are particularly preferable. Specifically, tetrahydrofuran, diethyl ether, 1,2-dimethoxyethane, 1,2-dimethoxypropane, diethylene glycol dimethyl ether, methyltetrahydrofuran,
Dioxane, acetone, methyl ethyl ketone, etc. may be mentioned.

The silicon-containing polymer (B) in the present invention whose main chain consists essentially of polyoxyalkylene and contains at least one hydrolyzable silicon group in the molecule is disclosed, for example, in JP-A-3-47820, Kaihei 3-72527,
JP-A-3-79627, JP-B-46-30711,
It is a polymer proposed in JP-B-45-36319 and JP-B-46-17553.

The silicon-containing polymer (B) is preferably produced by introducing a hydrolyzable silicon group into the terminal of a polyoxyalkylene compound having a functional group. The polyoxyalkylene compound is an alkali metal catalyst exemplified above, a complex metal cyanide complex catalyst, a metal porphyrin,
A hydroxyl-terminated one produced by reacting an initiator such as a hydroxy compound having at least one hydroxyl group in the presence of a catalyst such as LiPF ₄ with a monoepoxide such as alkylene oxide is preferable. The number of functional groups of the polyoxyalkylene compound is preferably 2 or more, and particularly preferably 2 or 3.

Specific examples of the polyoxyalkylene compound include polyoxyethylene compounds, polyoxypropylene compounds, polyoxybutylene compounds, polyoxyhexylene compounds, polyoxytetramethylene compounds and / or copolymers thereof. To be

Particularly preferred polyoxyalkylene compounds are polyoxypropylene compounds, specifically polyoxypropylene diol and polyoxypropylene triol. When used in the following methods (a) and (d), an olefin-terminated polyoxyalkylene compound such as an allyl-terminated polyoxypropylene monool can also be used.

The hydrolyzable silicon group in the present invention may be any silicon group which can undergo a hydrolysis and a crosslinking reaction in the presence of moisture to form a siloxane bond, and a generally known hydrolyzable silicon group is used. it can.

For example, a silyl group represented by the chemical formula (5) is preferable. -SiQ _a R ¹¹ _3-a (5)

In the formula, R ¹¹ is a monovalent hydrocarbon group or a halogenated hydrocarbon group, preferably having 1 to 20 carbon atoms,
Particularly, it is an alkyl group having 8 or less carbon atoms, a phenyl group, or a fluoroalkyl group. Particularly preferred are methyl group, ethyl group, propyl group, propenyl group, butyl group, hexyl group, cyclohexyl group, phenyl group and the like.

Q is a hydrolyzable group, and examples thereof include a halogen atom, an alkoxy group, an acyloxy group, an amide group, an amino group, an aminooxy group, a ketoximate group, an acid amide group and a hydride group.

Of these, the hydrolyzable group having a carbon atom preferably has 6 or less carbon atoms, and particularly preferably 4 or less carbon atoms. Preferred hydrolyzable groups are lower alkoxy groups having 4 or less carbon atoms, especially methoxy group, ethoxy group, propoxy group,
A propenyloxy group etc. can be illustrated. a is 1, 2 or 3, and particularly preferably 2 or 3.

The method of introducing the silyl group represented by the chemical formula (5) into the polyoxyalkylene compound is not particularly limited, but it can be introduced, for example, by the following method.

(A) A method of reacting a polyoxyalkylene compound having a functional group with an olefin group introduced at the terminal and a hydrosilyl compound represented by the chemical formula (6). HSiQ _a R ¹¹ _3-a (6) (wherein R ¹¹ , Q, and a are the same as above).

As a method for introducing an olefin group, a compound having an unsaturated group and a functional group is reacted with a terminal hydroxyl group of a polyoxyalkylene compound and bonded by an ether bond, an ester bond, a urethane bond, a carbonate bond or the like. Or a method of introducing an olefin group into the side chain by copolymerizing by adding an olefin group-containing epoxy compound such as allyl glycidyl ether when polymerizing the alkylene oxide.

(B) A method of reacting the terminal of a polyoxyalkylene compound having a functional group with the compound represented by the chemical formula (7). R ¹¹ _3-a SiQ _a —R ¹² NCO (7) (wherein R ¹¹ , Q, and a are the same as above. R ¹² has 1 to 1 carbon atoms.
A divalent hydrocarbon group of 7. )

(C) A polyoxyalkylene compound having a functional group is reacted with a polyisocyanate compound such as tolylene diisocyanate to form an isocyanate group terminal, and the isocyanate group is then converted to a silicon compound represented by the chemical formula (8). A method of reacting the W group.

R ¹¹ _3-a SiQ _a —R ¹² W (8) (wherein R ¹¹ , R ¹² , Q, and a are the same as above. W is a hydroxyl group,
An active hydrogen-containing group selected from a carboxyl group, a mercapto group and an amino group (primary or secondary). )

(D) An olefin group is introduced at the terminal of a polyoxyalkylene compound having a functional group, and the olefin group is reacted with the mercapto group of a silicon compound represented by the chemical formula (8)) in which W is a mercapto group. How to make.

The number of hydrolyzable silicon groups is preferably 50% or more, and more preferably 70% or more on average in all the terminal groups.

The molecular weight of the silicon-containing polymer (B) of the present invention is not particularly limited. For example, a compound having a molecular weight of 2000 or more can be used. Preferably molecular weight 8000-5000
0 organic polymers can be used. When the molecular weight of the organic polymer is lower than 8,000, the cured product becomes hard and has a low elongation. When the molecular weight exceeds 50,000, flexibility and elongation of the cured product are not a problem, but the viscosity of the polymer itself is remarkably high. It becomes larger and less practical. The molecular weight is particularly preferably 10,000 to 30,000.

The curable composition of the present invention comprises 0.1 to 100 parts by weight of the modified polyoxyalkylene polymer (A) and at least one hydrolyzed molecule in the molecule, the main chain of which is essentially polyoxyalkylene. 100 parts by weight of a silicon-containing polymer (B) containing a hydrophilic silicon group. In particular, it is preferable to contain 0.1 to 20 parts by weight of the modified polyoxyalkylene polymer, more preferably 0.5 to 10 parts by weight, and 100 parts by weight of the silicon-containing polymer (B).

The curable composition of the present invention can also use a curing catalyst. Specific examples of the curing catalyst include titanates such as tetrabutyl titanate and tetrapropyl titanate, dibutyltin dilaurate, dibutyltin maleate, dibutyltin diacetate, organotin compounds such as tin octylate, and other lead octylate and octylate. zinc,
Organometallic compounds such as cobalt naphthenate; butylamine, octylamine, dibutylamine, monoethanolamine, diethanolamine, triethanolamine,
Diethylenetriamine, triethylenetetramine, oleylamine, octylamine, cyclohexylamine,
Benzylamine, diethylaminopropylene, xylylenediamine, triethylenediamine, guanidine, diphenylguanidine, 2,4,6-tris (dimethylaminoethyl) phenol, morpholine, N-methylmorpholine 1,8-diazabicyclo [5.4.0]. Reaction products of amine compounds such as undecene-7 (DBU) or low molecular weight polyamide resins and epoxy compounds obtained by reacting them with other basic acids; γ-aminopropyltrimethoxysilane, N- (β-amino A known silanol condensation catalyst such as a silane coupling agent having an amino group such as ethyl) aminopropylmethyldimethoxysilane;
A radical initiator may be used.

These may be used alone or in combination of two or more. A photosensitizer may be added if necessary.

Various fillers, additives and the like can be added to the composition of the present invention as required. Examples of the filler include heavy and light calcium carbonate, kaolin, talc, titanium oxide, aluminum silicate, carbon black and the like commonly used.

Examples of plasticizers include dioctyl phthalate, dibutyl benzyl phthalate, chlorinated paraffin,
Epoxidized soybean oil and the like are commonly used. Examples of the anti-sagging agent include publicly known ones such as hydrogenated castor oil, silicic acid anhydride, and organic bentonite. As examples of the antiaging agent, various kinds classified into ultraviolet absorbers, radical chain inhibitors, peroxide decomposers and the like can be used alone or in combination.

[0054]

The present invention will be described in detail with reference to the following examples, but the present invention is not limited to these examples.

[Modified polyoxyalkylene polymer (A)] (A-1) 1- (3-mercaptopropyl) -1,1,
25 g of 3,3,3-pentamethyldisiloxane was dissolved in 25 g of tetrahydrofuran, 0.05 g of hexacyanocobalt zinc-glyme complex was added, and the mixture was placed in an autoclave. Further, when 50 g of propylene oxide was added and heated at 100 ° C. under a nitrogen atmosphere, an exothermic reaction occurred. After the exotherm was completed, the reaction mixture was heated at 100 ° C. for another 30 minutes, and then the unreacted monomer was degassed under reduced pressure to obtain 74.8 g of an oily product (the product showed a single peak by GPC analysis).

(A-2) α, ω-bis (3-aminopropyl) -polydimethylsiloxane (average molecular weight 800)
A mixture of 25 g and 5 g of propylene oxide was heated in an autoclave at 120 ° C for 2 hours. After degassing the unreacted monomer and cooling to room temperature, 0.01 g of hexacyanocobalt zinc-glyme complex and 50 g of tetrahydrofuran are added,
50 g of propylene oxide in a nitrogen atmosphere with an internal temperature of 120
It was introduced little by little so as not to exceed ℃. After heating for 1 hour after the completion of the introduction of the monomer, the solvent and the unreacted monomer were flown out under reduced pressure, and an oily product having hydroxy groups at both ends was prepared.
1 g was obtained.

(A-3) Organosilicon polymer: polydimethylsiloxane (polymerization degree: about 450)

[Silicon-Containing Polymer (B)] An average molecular weight of 17,000 in which methyldimethoxysilylpropyl group is introduced into the terminal 75% of polyoxypropylene diol obtained by using hexacyanocobalt zinc-glyme complex.
Polymer.

[Examples 1 to 6 and Comparative Examples 1 and 2] (A-1) and (A-2) based on 100 parts by weight of (B).
Alternatively, (A-3) is mixed with parts by weight shown in Table 1, and N ₂
A uniform polyol raw material was prepared by stirring at 40 ° C. with a lower three-one motor. In addition, a system in which the modified polyoxyalkylene polymer (A) was not added (Comparative Example 1) and a system in which the organosilicon polymer was added (Comparative Example 2) were used as Comparative Examples.

[0060]

[Table 1]

Immediately after mixing the polymer mixture and at 50 ° C. for 1
The compatibility results after storage for 4 days are shown in Table 2.

Next, 130 parts by weight of calcium carbonate, 16 parts by weight of dioctyl phthalate, 20 parts by weight of titanium oxide, 1 part by weight of hydrogenated castor oil, 0.5 part by weight of antioxidant with respect to 100 parts by weight of the obtained polymer raw material. Part, tin octylate (I
I) 2.25 parts by weight and laurylamine 0.75 parts by weight were added and mixed well with a three-paint roll to obtain a blend. This is made into a sheet with a thickness of about 3 mm, and the temperature is 6
Cured at 0% RH. After 1 day, 3 days, and 14 days after curing, the surface residual tacks were determined by touching with fingers. The results are shown in Table 2. However, the evaluation method is as follows. Compatibility: ○ Good, △ Not good. Surface residual tack: ◎ No tack at all when touched by fingers,
○ There is some tack, × there is tack.

[0063]

[Table 2]

As shown in Table 2, the surface residual tack was obviously reduced in the system to which the modified polyoxyarlequin polymer was added, as compared with Comparative Example 1 in which the modified polyoxyarlequin polymer was not added. In addition, the compatibility of Comparative Example 2 to which the organic silicon polymer was added was poor and the two phases were separated, while the compatibility of the polymer mixed solution was good in storage stability.

[0065]

INDUSTRIAL APPLICABILITY The present invention comprises as an essential component a compound containing a polyorganosiloxane-modified polyoxyalkylene polymer in a polymer having at least one hydrolyzable silicon main chain which is essentially polyoxyalkylene. It relates to a curable composition, and the cured product obtained from this composition has a particularly large tack reduction effect, and the storage stability of the compounded product is also good. In addition, the polyorganosiloxane-modified polyoxyalkylene polymer of the present invention can be obtained without complicated steps, and is economically advantageous.

 ─────────────────────────────────────────────────── ─── Continued Front Page (72) Inventor Shigeyuki Ozawa 1150 Hazawa-machi, Kanagawa-ku, Yokohama, Kanagawa Prefecture Asahi Glass Co., Ltd. Central Research Laboratory

Claims (7)

[Claims] 1. A modified polyoxyalkylene polymer obtained by ring-opening polymerization of an alkylene oxide in the presence of a catalyst using an organopolysiloxane compound having an active hydrogen-containing functional group capable of reacting with an alkylene oxide as an initiator. (A) 0.1 to 100 parts by weight and a silicon-containing polymer (B) whose main chain consists essentially of polyoxyalkylene and contains in the molecule at least one hydrolyzable silicon group.
A curable composition comprising 100 parts by weight. 2. The curable composition according to claim 1, wherein the active hydrogen-containing functional group is a functional group selected from a hydroxyl group, a mercapto group, a primary amino group, a secondary amino group, and a carboxyl group. 3. The curable composition according to claim 1, wherein the organopolysiloxane compound is at least one compound represented by the following chemical formulas (1) to (3). [Chemical 1] [Chemical 2] [Chemical 3] (Wherein X _{is, -OH, -SH, -NH 2,} -NHR 10,
It is a hydrocarbon group having 3 to 10 carbon atoms and containing one or more functional groups of at least one selected from —CO ₂ H, and may contain an ether bond, a thioether bond or an amino bond. R ¹ , R ² , R ³ , R ⁴ , R ⁶ , R ⁷ , R ⁸ , R ¹⁰
Are the same or different hydrocarbon groups having 1 to 6 carbon atoms. R ⁵ and R ⁹ are hydrocarbon groups having 1 to 18 carbon atoms. n is 0 or an integer of 1 to 200, and m is an integer of 1 to 10. ) 4. The organopolysiloxane compound is R ¹ ,
The curable composition according to claim 3, wherein R ² is a polydimethylsiloxane compound in which all R ² are methyl groups. 5. X is a hydroxyalkyl group, a dihydroxyalkyl group, a hydroxyalkoxy-substituted alkyl group,
The curable composition according to claim 3, which is a mercaptoalkyl group, an aminoalkyl group, an N-aminoalkyl-substituted alkyl group, or a carboxyalkyl group. 6. The curable composition according to claim 1, wherein the catalyst is a double metal cyanide complex catalyst. 7. The curable composition according to claim 1, wherein the alkylene oxide is an alkylene oxide having 2 to 4 carbon atoms.