JPH0912862A - Room-temperature-curable composition - Google Patents

Abstract

PURPOSE: To obtain a room-temp.-curable compsn. which is satisfactory both in long-term storage stability and in depth curability in curing by compounding a polymer produced by a specific process and having hydrolyzable silicon groups with a specific compd. CONSTITUTION: This compsn. contains as the effective ingredients an org. polymer which is derived from a hydroxylated polyoxyalkylene polymer obtd. by polymerizing an alkylene oxide using an initiator in the presence of a composite metal cyanide complex as the catalyst and has hydrolyzable silicon groups represented the formula: -R<2> -SiXa R<1> 3-a (R<1> is an optionally substd. 1-20C hydrocarbon group; R<2> is an org. group; X is a hydroxyl or hydrolyzable group; and a is 1-3) and a total content of ionic impurities of 50ppm or lower, at least one compd. selected from among alkyl alcohols and keto-enol tautomers (pref. a 10C or lower alkyl mono- or polyhydric alcohol, a 1,3-diketone compd., or a β-keto ester), and a cure catalyst.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a room temperature curable composition which is cured in the presence of moisture and has excellent storage stability.

[0002]

2. Description of the Related Art Conventionally, a sealing material has been used by utilizing a curing reaction of various compounds having a hydrolyzable silicon group at a terminal, which is known as a modified silicone resin.
The method used for adhesives and the like is well known and industrially useful.

[0003]

Known polymers having such terminal hydrolyzable silicon groups are disclosed in Japanese Patent Publication No. 45-3.
6319, JP-B-46-17553, JP-B-61-18
582 and the like, and a composition obtained by adding an active hydrogen compound to the polymer is disclosed in JP-B-4-49593.
It is known to improve storage stability as described in.

However, when an active hydrogen compound is added to these polymers in which a hydrolyzable silicon group is introduced after a relatively low molecular weight polyether compound is linked with a polyfunctional halogen compound to increase the molecular weight, a composition is obtained. There is a drawback that the curability is lowered when the product is cured, and the curing speed in the deep portion of the cured product is remarkably slowed.

In order to solve such a drawback, Japanese Patent Application Laid-Open No. 7-62217 proposes a method of using a polyoxyalkylene polymer having a narrow molecular weight distribution, which is produced using a complex metal cyanide complex. The room temperature curable composition produced from this polymer shows good curability even when an active hydrogen compound is added.

However, in the conventional room temperature curable composition using such a polyoxyalkylene polymer having a narrow molecular weight distribution, even if an active hydrogen compound is used, it is known as a one-pack type room temperature curable composition. In the case of a composition of the type in which a curing catalyst is added and stored, the viscosity may increase during storage in some cases, and the extrudability after storage for a long time may deteriorate. Therefore,
There has been a demand for a composition which does not deteriorate the curability of deep parts more than before and has good long-term storage stability.

[0007]

DISCLOSURE OF THE INVENTION The inventors of the present invention conducted a study for the purpose of achieving both the curability in the deep portion and the storage stability for a long time as described above, and as a result, they were produced using a complex metal cyanide complex. In the case of using a polyoxyalkylene polymer having a narrow molecular weight distribution obtained in the case, a polymer with reduced impurities containing a hydrolyzable silicon group in the molecule, long-term storage when an active hydrogen compound is added The inventors have found that both stability and deep-part curability at the time of curing are compatible, leading to the present invention.

[0008]

DISCLOSURE OF THE INVENTION The present invention is the following invention intended to solve such a drawback. An organic polymer (A), an alkyl alcohol, and one or more compounds (B) selected from the group consisting of keto-enol tautomeric compounds and a curing catalyst (C) are contained as active ingredients. Room temperature curable composition.

(Organic Polymer) Derived from a hydroxyl group-containing polyoxyalkylene polymer (E) obtained by polymerizing an alkylene oxide with an initiator using a complex metal cyanide complex (D) as a catalyst, and represented by the formula (1). Has a hydrolyzable silicon group and the total amount of ionic impurities is 50 ppm
The following organic polymers (A).

-R ² -SiX _a R ¹ _3-a (1)

In the formula, R ¹ is a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, R ² is a divalent organic group, X is a hydroxyl group or a hydrolyzable group, and a is 1 to 3 Is an integer.

"Organic Polymer" The organic polymer (A) is derived from a hydroxyl group-containing polyoxyalkylene polymer (E) obtained by polymerizing an alkylene oxide with an initiator using a complex metal cyanide complex (D) as a catalyst. To be done.

By using the complex metal cyanide complex (D), M can be obtained rather than using a conventional alkali metal catalyst.
A hydroxyl group-containing polyoxyalkylene polymer (E) having a smaller _w / _Mn , a higher molecular weight and a lower viscosity can be obtained.

As the complex metal cyanide complex (D), a complex containing zinc hexacyanocobaltate as a main component is preferable, and its ether and / or alcohol complex is particularly preferable. Its composition is essentially Japanese Patent Publication No. 46-2725.
The values described in 0 can be used. As the ether, ethylene glycol dimethyl ether (glyme), diethylene glycol dimethyl ether (diglyme) and the like are preferable, and glyme is particularly preferable from the viewpoint of handling during the production of the complex.
The alcohol is preferably t-butanol.

As the initiator, a compound having 2 to 10 active hydrogens is preferable, a polyhydroxy compound is preferable, and a polyhydroxy compound having 2 to 8, especially 2 to 4 hydroxyl groups is preferable. Specifically, ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, neopentyl glycol, 1,
There are 4-butanediol, 1,6-hexanediol, glycerin, trimethylolpropane, pentaerythritol, diglycerin, sucrose and polyols having a lower molecular weight than the target product obtained by reacting these with alkylene oxide. These may be used alone or in combination of two or more. Further, an unsaturated group-containing monohydroxy compound such as allyl alcohol can also be used.

The organic polymer (A) of the present invention has a total amount of ionic impurities of 50 ppm or less. The present invention is particularly suitable when the ionic impurities are ionic impurities containing a metal compound and / or an alkali metal compound derived from the complex metal cyanide complex (D). The ionic impurities are preferably 30 ppm or less, more preferably 20 ppm or less.

By reducing the amount of these metal impurities, the storage stability of the organic polymer (A) and the curable composition of the present invention is further improved, and since the action of the curing catalyst is not hindered, excellent curing is achieved. Sex is obtained.

As the reducing method, the following (I) to
The method (III) can be mentioned. In particular, there is (III) as a method that can be used for removing the metal compound caused by the complex metal cyanide complex (D). The method (I) is particularly preferable because it can reduce ionic impurities effectively and economically.

(I) A method in which an ionic impurity contained in a polymer is converted into a salt which is essentially insoluble in the polymer, and then the salt is removed from the polymer. Specifically, after adding a compound capable of reacting with an ionic impurity to form a salt essentially insoluble in the polymer, water and, if necessary, a nonionic surfactant,
There is a method of precipitating a salt by dehydration and then removing the salt. As the compound capable of forming a salt, hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, pyrophosphoric acid, acidic sodium pyrophosphate and the like are preferable. The precipitated salt can be removed by filtration or adsorption.

(II) A method of removing a ionic impurity by adding a solvent to a polymer and then bringing the polymer into contact with an anion exchange resin and / or a cation exchange resin.

(III) A method of removing a metal compound derived from the complex metal cyanide complex (D) after treatment with a pH buffer and optionally ammonia and a chelating agent, after adding an aliphatic alcohol and a chelating agent, A method of removing a metal compound derived from the composite metal cyanide complex (D), a method of removing a metal compound derived from the composite metal cyanide complex (D) after treatment with an oxidizing agent.

The ionic impurities referred to in the present invention are
Cations and anions such as zinc ion, cobalt ion, cyan ion, and chlorine ion resulting from the complex metal cyanide complex (D); sodium ion and potassium ion mixed as impurities in the step of producing the organic polymer (A). Such as an alkali metal ion, a halogen ion; a carboxylate ion produced by polyoxyalkylene being oxidized in the step of producing the organic polymer (A); an ester bond in the step of producing the organic polymer (A),
Includes all anions and cations such as catalytic metal salts added when forming carbonate bonds and the like.

The organic polymer (A) has a hydrogen atom in the hydroxyl group of the hydroxyl group-containing polyoxyalkylene polymer (E),
Those substituted with formula (1) are preferred.

The number of hydroxyl groups per molecule of the polyoxyalkylene polymer (E) used in the present invention is preferably 2-10. From the balance of physical properties such as viscosity, strength and elongation, it is particularly preferable that the number is 2 to 8, especially 2 to 4.

Preferred polymers (E) are polyoxypropylene diols, polyoxypropylene triols and polyoxypropylene tetraols. When used in the following methods (a) and (d), an unsaturated group-terminated polyoxyalkylene monool such as polyoxypropylene glycol monoallyl ether can also be used.

The polyoxyalkylene polymer (E) preferably has a hydroxyl value-converted molecular weight of 5,000 to 30,000, more preferably 8,000 to 30,000.

In the present invention, the molecular weight converted to a hydroxyl value is the polyoxyalkylene polymer (E) containing a terminal hydroxyl group.
The molecular weight calculated by the product of the number of functional groups of the initiator used for the production of and the molecular weight per hydroxyl group of the polyoxyalkylene of the polymer.

The organic polymer (A) has a hydrolyzable silicon group represented by the formula (1).

--R ² --SiX _a R ¹ _3-a (1)

In the formula, R ¹ is a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, R ² is a divalent organic group, X is a hydroxyl group or a hydrolyzable group, and a is 1 to 3 Is an integer.

R in the formula (1) is a divalent organic group. 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, a phenyl group and the like.

X is a hydroxyl group or a hydrolyzable group, and the hydrolyzable group is, for example, a halogen atom, an alkoxy group, an acyloxy group, an amide group, an amino group, an aminooxy group, a ketoximate group or 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. Examples of preferable X include a lower alkoxy group having 4 or less carbon atoms, particularly a methoxy group, an ethoxy group and a propoxy group. a is an integer of 1 to 3, preferably 2 or 3.

Next, the method for producing the organic polymer (A) will be described. In the organic polymer (A) in the present invention, a hydrolyzable silicon group can be introduced into the terminal of the hydroxyl group-containing polyoxyalkylene polymer (E) by the methods described in (A) to (D) below. Such a compound is liquid at room temperature, and the cured product retains flexibility even at a relatively low temperature,
When used as a sealing material or an adhesive, it has desirable characteristics.

(A) A method of reacting the terminal unsaturated group-introduced product (F) of the polymer (E) with the silicon hydride compound represented by the formula (2).

HSiX _a R ¹ _3-a (2)

However, in the formula, R ¹ , X and a are the same as described above.

Terminal unsaturated group-introduced product (F) of polymer (E)
As a method for obtaining the above, after the terminal hydroxyl group OH of the polymer (E) is OM (M is an alkali metal), it is reacted with an unsaturated group-containing halogenated hydrocarbon such as allyl chloride, or with an unsaturated group and a hydroxyl group. There is a method in which a compound having a reactive functional group is reacted with the polymer (E) to bond it with an ester bond, a urethane bond, a carbonate bond or the like. Furthermore, when polymerizing an alkylene oxide in the production of the polymer (E), a method of introducing an unsaturated group into a side chain by copolymerizing an unsaturated group-containing alkylene oxide such as allyl glycidyl ether or a terminal as an initiator It can also be obtained by using an unsaturated group-containing monohydroxy compound.

(B) A compound having an isocyanate group and a hydrolyzable silicon group represented by the formula (1), and a polymer (E)
How to react.

(C) After reacting the polymer (E) with a polyisocyanate compound such as tolylene diisocyanate to form an isocyanate group terminal, the isocyanate group is reacted with the W group of the silicon compound represented by the formula (3). How to make.

R ¹ _3-a -SiX _a -R ⁵ W (3)

However, in the formula, R ¹ , X and a are the same as described above,
R ⁵ is a divalent organic group, 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) Formula (3) in which the unsaturated group of the terminal unsaturated group-introduced product (F) of the polymer (E) and W is a mercapto group.
The method of reacting the mercapto group of the silicon compound represented by.

The removal of ionic impurities is carried out from the above (a) to.
In each step (d), it is preferably carried out at an appropriate stage such as before reacting each silicon compound, and the total amount thereof is set to 50 ppm or less. That is, the following method can be exemplified.

The ionic impurities contained in the polymer (E) are converted into salts essentially insoluble in the polymer (E), and the salts are removed from the polymer (E) to remove the polymer (E). After adjusting the ionic impurities contained in () to 50 ppm or less, a hydrolyzable silicon group is introduced into the polymer (E) to obtain an organic polymer (A).

Terminal unsaturated group-introduced product (F) of polymer (E)
The ionic impurities contained in the salt are essentially insoluble in the terminal unsaturated group-introduced product (F), and the salt is removed from the terminal unsaturated group-introduced product (F) to remove the terminal unsaturated group. After adjusting the ionic impurities contained in the introduction product (F) to 50 ppm or less, the reaction product with the terminal unsaturated group introduction product (F) is reacted with the silicon hydride compound represented by the formula (2) to give an organic polymer (A ).

The molecular weight of the organic polymer (A) in the present invention is calculated based on the hydroxyl value-equivalent molecular weight of the polymer (E) as a raw material. The molecular weight is 5,000 to 30,000
Is preferred. When it is lower than 5,000, the cured product becomes hard and has low elongation. When it exceeds 30,000, the flexibility and elongation of the cured product are not problematic, but the viscosity of the polymer itself is remarkably increased and the practicality is lowered. Especially 8000-30
000 is preferred.

"Compound (B)" In the present invention, one or more compounds (B) selected from the group consisting of alkyl alcohols and keto-enol tautomeric compounds are used. The compound (B) is a compound selected from an alkyl monoalcohol having 10 or less carbon atoms, an alkyl polyalcohol having 10 or less carbon atoms, a 1,3-diketone compound having 10 or less carbon atoms, and a β-ketoester compound having 10 or less carbon atoms. Is preferred.

Examples of the alkyl monoalcohol having 10 or less carbon atoms and the alkyl polyalcohol having 10 or less carbon atoms include methanol, ethanol, 1-propanol and 2-
Propanol, 1-butanol, isobutyl alcohol, 2-butanol, t-butyl alcohol, n-amyl alcohol, isoamyl alcohol, 1-hexanol, octyl alcohol, 2-ethylhexanol, cellosolve, ethylene glycol, propylene glycol, glycerin and the like can be mentioned. To be Diethylene glycol, dipropylene glycol, etc. can also be used.

Examples of keto-enol tautomeric compounds are:
Any compound having a methylene group and carbonyl groups on both sides thereof in the molecule may be used, and a 1,3-diketone compound having 10 or less carbon atoms or a β-ketoester compound having 10 or less carbon atoms is preferable.

Specific examples include acetoacetic acid ester compounds such as acetylacetone, methyl acetoacetate, ethyl acetoacetate and butyl acetoacetate, and malonate ester compounds such as dimethyl malonate and diethyl malonate.

The compound (B) not only improves the storage stability, but also functions as a solvent to lower the viscosity of the composition and improve workability. The amount of the compound (B) used is 0.1 to 20 with respect to 100 parts by weight of the organic polymer (A).
Weight part is preferable, and if less than 0.1 part by weight, the effect is difficult to be exhibited. From the gist of the present invention, it is preferable that the compound (B) is added before or at least simultaneously with the addition of the curing catalyst (C).

In the present invention, the curing catalyst (C) is essential for curing the organic polymer. When the curing catalyst (C) is not used, the crosslinking reaction of the hydrolyzable silicon group does not have a significant reaction rate.

As the curing catalyst (C), compounds known as catalysts for the hydrolysis and condensation reaction of hydrolyzable silicon groups can be used. That is, metal titanates, organosilicon titanates, metal salts of carboxylic acids such as tin octylate and dibutyltin dilaurate, amine salts such as dibutylamine-2-ethylhexoate, and other acidic salts. Catalysts and basic catalysts can be used. The curing catalyst is preferably used in an amount of 0.001 to 10 parts by weight, and particularly preferably 0.01 to 5 parts by weight, based on 100 parts by weight of the organic polymer (A).

Fillers may be used in the present invention. The amount of the filler used is 0 to 1 with respect to the organic polymer (A).
000% by weight, especially 50 to 250% by weight is preferred. The following are specific examples of the filler. 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 white, shirasu balloon, wood flour, pulp, cotton chips, mica, walnut flour, rice flour, graphite, aluminum fine powder, flint powder, asbestos, glass fiber, glass filament, Fibrous fillers such as carbon fiber, Kevlar fiber and polyethylene fiber.

In the present invention, a plasticizer can be optionally used. Examples of the plasticizer include dioctyl phthalate, dibutyl phthalate, diisononyl phthalate, butylbenzyl phthalate, and other phthalates; 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, tricresyl phosphate; epoxy plasticizers such as epoxidized soybean oil, dioctyl 4,5-epoxyhexahydrophthalate, benzyl epoxystearate; Chlorinated paraffins may be used alone or as a mixture of two or more.

The composition of the present invention may further contain various known additives. As the additive, an adhesiveness imparting agent such as phenol resin or epoxy resin, a thixotropic agent such as hydrogenated castor oil, a pigment, various antiaging agents, an ultraviolet absorber or the like can be used.

The room-temperature-curable composition of the present invention cures at room temperature in the presence of moisture and can be used especially for elastic sealants and adhesives.

[0059]

EXAMPLES The present invention will be described below with reference to Examples (Examples 1 to 6, 15 to 2).
0) and comparative examples (Examples 7 to 14, 21 to 31), but the present invention is not limited thereto. First, Production Examples of organic polymers P1 to P7, which are raw materials of the organic polymer (A), will be shown by Synthesis Examples 1 to 7 (where P7 is an organic polymer for comparison). Compounds (T1 to T3), tin compounds (Q1 to Q3), and silicon compounds (K1 to K)
3) is shown in Table 6. Parts are parts by weight.

[Synthesis Example 1] Polymerization of propylene oxide was carried out using a zinc hexacyanocobaltate glyme complex with a glycerin-propylene oxide adduct having a molecular weight of 1000 as an initiator, and a hydroxyl value of 11.2 mgKOH /
A polyoxypropylene triol having a viscosity of 7,000 cP at 25 ° C. was obtained. Subsequently, 1.1 times equivalent of sodium methoxide to the hydroxyl group of polyoxypropylene triol was added, then methanol was distilled off, and allyl chloride was added to convert the terminal hydroxyl group to an allyloxy group to convert metal salt as an impurity. The contained organic polymer (P1) was obtained.

[Synthesis Example 2] Propylene oxide was polymerized using a zinc hexacyanocobaltate glyme complex with ethylene glycol as an initiator to give a hydroxyl value of 9.3.
A polyoxypropylene diol having mgKOH / g and a viscosity at 25 ° C. of 8000 cP was obtained. The terminal hydroxyl group was converted to an allyloxy group by the method described in Synthesis Example 1 to obtain an organic polymer (P2) containing a metal salt as an impurity.

[Synthesis Example 3] Polymerization of propylene oxide was carried out using a zinc hexacyanocobaltate glyme complex with ethylene glycol as an initiator to give a hydroxyl value of 5.6.
A polyoxypropylene diol having mgKOH / g and a viscosity at 25 ° C. of 17,000 cP was obtained. Subsequently, the terminal hydroxyl group was converted to an allyloxy group by the method described in Synthesis Example 1 to obtain an organic polymer (P3) containing a metal salt as an impurity.

[Synthesis Example 4] Propylene oxide was polymerized using a zinc hexacyanocobaltate glyme complex with a pentaerythritol-propylene oxide adduct having a molecular weight of 1000 as an initiator to give a hydroxyl value of 13.2 mg.
Polyoxypropylene tetraol having a KOH / g and a viscosity at 25 ° C. of 6000 cP was obtained. Subsequently, the terminal hydroxyl group was converted to an allyloxy group by the method described in Synthesis Example 1 to obtain an organic polymer (P4) containing a metal salt as an impurity.

[Synthesis Example 5] The polyoxypropylene diol obtained in Synthesis Example 3 and the polyoxypropylene triol obtained in Synthesis Example 1 were mixed in a weight ratio of 2: 1 and then Synthesis Example 1 was performed.
The terminal hydroxyl group was converted to an allyloxy group by the method described to obtain an organic polymer (P5) containing a metal salt as an impurity.

[Synthesis Example 6] The polyoxypropylene diol obtained in Synthesis Example 3 and the polyoxypropylene tetraol obtained in Synthesis Example 4 were mixed at a weight ratio of 4: 1, and then the terminal hydroxyl group was prepared by the method described in Synthesis Example 1. Was converted to an allyloxy group to obtain an organic polymer (P6) containing a metal salt as an impurity.

[Synthesis Example 7] Polyoxypropylene diol having a hydroxyl value-converted molecular weight of 3000 and chlorobromomethane were used in a molar ratio of 4: in accordance with the method described in JP-B-59-25808.
After reacting in the presence of alkali at a ratio of 3, allyl chloride was added to convert the terminal hydroxyl groups to allyloxy groups to obtain an organic polymer (P7) containing a metal salt.

[Examples 1 to 14] Organic polymers P1 to P7 were purified by the purification method A or the purification method B, and the amount of residual metal ions (unit: ppm) was measured. Purified organic polymer P1
Tables 1 and 2 also show the viscosities (unit: cP) of to P7.

Then, a methyldimethoxysilylpropyl group was introduced at the end of the organic polymer by a known method using a platinum catalyst to obtain organic polymers S1 to S14. The viscosity of the organic polymers S1 to S14 after production is also shown in the table. The content of the methyldimethoxysilylpropyl group as the terminal group is 0.11 mmol to 0.17 mmol per 1 g of the organic polymer.
Range. The residual metal ion amounts of the obtained organic polymers S1 to S14 were the same as those before the introduction of the methyldimethoxysilylpropyl group.

[Examples 15 to 31] Organic polymers (S1 to S1)
4) To 100 parts, add 160 parts of calcium carbonate, 20 parts of titanium oxide, 60 parts of dioctyl phthalate, 5 parts of hydrogenated castor oil, 1 part of phenolic antioxidant and heat dehydration while kneading, vinyltrimethoxy 1 part of silane, Table 3-
2 parts of the silicon compounds (K1 to K3) shown in Table 5 were added and kneaded in a nitrogen atmosphere, and then 1 part of the compounds (T1 to T3) shown in Tables 3 to 5 were added and kneaded. 5
2 parts of the tin compound (Q1 to Q3) shown in was added and further kneaded to obtain a curable composition.

The viscosity immediately after production of the curable composition (viscosity after production) (unit: cP) and the viscosity after storage at 50 ° C. for 14 days (viscosity after storage) (unit: cP) were measured. The results are shown in Tables 3 to 5.

Next, 3c was placed in a cylindrical cup having a diameter of 4cm.
Pour the curable composition to a thickness of 20
And left in an atmosphere of 65% humidity for 6 hours. Then J
Using a penetrometer compliant with IS-K2530, the state of curing from the surface to the depth direction was observed. The results are shown in Tables 3 to 5. The higher the penetration, the less the hardening from the surface.

(Purification method a) 5 g of a polyoxypropylene polymer having a molecular weight of 10,000, which is obtained by block-polymerizing ethylene oxide at the terminal 10% by weight, with respect to 1 kg of an organic polymer containing a metal salt as an impurity, 50 g of water, and sodium acid pyrophosphate. 10 g was added, and the mixture was stirred at 90 ° C. for 1 hour. Then, after distilling off the water at 90 ° C. under reduced pressure, 10 g of Kyoward 600 (synthetic magnesia silicate, manufactured by Kyowa Chemical Co., Ltd.) was added, dehydrated under reduced pressure at 90 ° C. for 1 hour, and then 2 liters of hexane was added to the organic substance. The polymer was dissolved, and insoluble materials were removed by filtration using a filter paper. Then, hexane was distilled off under reduced pressure to obtain a purified product.

(Purification method a) 1 kg of an organic polymer containing a metal salt as an impurity was dissolved in 3 kg of hexane to obtain 3% by weight.
1 kg of sulfuric acid water was added and stirred for 1 hour, but the whole became cloudy. Although the mixture was left standing at room temperature for 3 days, a slightly transparent hexane layer was separated in the uppermost layer by about 1/5 of the whole, so the hexane layer was separated by decantation, and hexane was distilled off under reduced pressure to obtain a purified product.

[0074]

[Table 1]

[0075]

[Table 2]

[0076]

[Table 3]

[0077]

[Table 4]

[0078]

[Table 5]

[0079]

[Table 6]

[0080]

EFFECTS OF THE INVENTION The curable composition of the present invention has remarkably improved storage stability and good curability in deep areas.

Claims (6)

[Claims] 1. An organic polymer (A), an alkyl alcohol, one or more compounds (B) selected from the group consisting of keto-enol tautomeric compounds, and a curing catalyst (C). A room temperature curable composition containing as an active ingredient. (Organic Polymer) Hydrolyzate derived from a hydroxyl group-containing polyoxyalkylene polymer (E) obtained by polymerizing alkylene oxide with an initiator using the composite metal cyanide complex (D) as a catalyst, and represented by the formula (1). Having a degradable silicon group,
An organic polymer having a total amount of ionic impurities of 50 ppm or less. —R ² —SiX _a R ¹ _3-a (1) In the formula, R ¹ is a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, R ² is a divalent organic group, X is a hydroxyl group or a hydrolyzable group, and a is an integer of 1 to 3. 2. The compound (B) comprises an alkyl monoalcohol having 10 or less carbon atoms, an alkyl polyalcohol having 10 or less carbon atoms, a 1,3-diketone compound having 10 or less carbon atoms, and a β-ketoester compound having 10 or less carbon atoms. The room temperature curable composition according to claim 1, which is a selected compound. 3. The room temperature curable composition according to claim 1, wherein the ionic impurities are ionic impurities containing a metal compound and / or an alkali metal compound derived from the double metal cyanide complex (D). 4. An organic polymer (A), wherein the ionic impurities contained in the polymer (E) are converted into salts essentially insoluble in the polymer (E), and then the salt is added to the polymer (E). ), The ionic impurities contained in the polymer (E) are reduced to 50 p
The room temperature curable composition according to any one of claims 1 to 3, which is an organic polymer obtained by introducing a hydrolyzable silicon group into the polymer (E) after adjusting it to pm or less. 5. The organic polymer (A) contains an ionic impurity contained in the terminal unsaturated group-introduced product (F) of the polymer (E),
After the salt is essentially insoluble in the terminal unsaturated group-introduced product (F), the salt is removed from the terminal unsaturated group-introduced product (F) to be contained in the terminal unsaturated group-introduced product (F). The organic polymer obtained by reacting the terminal unsaturated group-introduced product (F) with the silicon hydride compound represented by the formula (2) after adjusting the ionic impurities to 50 ppm or less.
Room temperature curable composition according to any one of 3 to 3. HSiX _a R ¹ _3-a (2) In the formula, R ¹ is a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, X is a hydroxyl group or a hydrolyzable group, and a is 1
-3. 6. A polymer (E) having a hydroxyl value-converted molecular weight of 50.
The room temperature curable composition according to any one of claims 1 to 5, which is from 00 to 30000.