JPH06212077A - Room temperature curing composition - Google Patents

Abstract

PURPOSE:To obtain the subject condensation curing composition having quick curability, deep curability and workability by using a silanol or alkoxysilyl- containing alkylene oxide as a base and compounding the base with 4 specific kinds of components. CONSTITUTION:The objective composition contains (A) an alkylene oxide polymer containing silanol or alkoxysilyl group, (B) an organic silicon compound having >=2 hydroxyl groups (e.g. dimethyldimethoxysilane), (C) a carbonyl- containing organic compound (preferably acetone or cyclohexane), (D) an organic compound containing primary amino group (preferably gamma- aminopropyltriethoxysilane) and (E) a curing catalyst (e.g. tin naphthenate). The component A is e.g. a polyoxyalkylene polyether containing terminal silanol group and produced by hydrolyzing an addition reaction product of a polyoxypropylene having allyloxy group at the terminal with methyldichlorosilane.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a room temperature curable composition using a silanol- or alkoxysilyl-modified alkylene oxide polymer as a base component.

[0002]

2. Description of the Related Art Condensation-curable room-temperature-curable alkylene oxide polymer compositions are widely used, for example, in the fields of electric / electronics, building materials, etc., as adhesives for parts requiring vibration-proof properties. . In such applications, it is required that the curing rate is high, the adhesive strength is strong, and the cured product is an elastic body.

The basic composition of this condensation-curable room-temperature-curable alkylene oxide polymer composition is that a polymer such as polyoxyalkylene polyether having a hydrolyzable group at the molecular end is mixed with a crosslinking agent and a curing catalyst. Conventionally, a one-pack type in which the amount of the crosslinking agent is reduced as much as possible to improve the speed of crosslinking (curing) by hydrolysis of the hydrolyzable group, or the crosslinking agent and the curing catalyst are packaged separately. A two-pack type is known.

[0004]

However, although the former one-pack type composition has a high curing rate from the surface, it requires a considerable amount of time for deep curing, and the latter two-pack type composition does not. Although it has excellent deep-part curability, it has the drawbacks that the workability of metering and mixing is poor and it is difficult to adapt to an automatic mixer because the volume ratio or the weight ratio for mixing the two liquids is not 1: 1. In addition, the two-part composition has a narrow appropriate range of the amounts of the crosslinking agent and the curing catalyst necessary to completely cure the deep portion, so that the addition amount is strictly controlled or water is used as the deep curing agent. It was necessary to add. Therefore,
An object of the present invention is to provide a condensation curing type room temperature curable alkylene oxide polymer composition which is excellent in fast curability, depth curability and workability.

[0005]

According to the present invention, (A)
A silanol group- or alkoxysilyl group-containing alkylene oxide polymer, (B) an organic silicon compound having at least two hydrolyzable groups in one molecule, (C) an organic compound having a carbonyl group, and (D) a primary amino group. Provided is a room temperature curable composition containing an organic compound and (E) a curing catalyst.

[0006]

According to the present invention, the water required for the crosslinking by the hydrolysis of the silanol or alkoxysilyl group introduced into the alkylene oxide polymer is adjusted to the carbonyl group in the component (C) and the moisture in the first component in the component (D). It has succeeded in solving the above-mentioned problem by generating in a composition by reaction with a primary amino group. That is, in the composition of the present invention, at the time of curing, the carbonyl group of the component (C) and the primary amino group of the component (D) have the following formula:> C = O + H ₂ N- →> C = N− + H ₂ O reacts to produce water. This water generated in the composition promotes curing as a deep-curing agent, and thus the rapid curability and the deep-curability of the composition are significantly improved. Moreover, when the composition of the present invention is packaged in two liquids and mixed at the time of use, the two liquids are mixed at a ratio of 1: 1.
It has the advantage of being easy to mix, and the component added to generate water, that is, the organic compound having a carboxyl group of component (C) and the primary amino group of component (D). It is easily available together with an organic compound having, and is extremely practical.

Component (A) The silanol group- or alkoxysilyl group-containing alkylene oxide polymer of component (A) is a base component, and is represented by the following general formula (1):

[0008]

[Chemical 1] [In the formula, R ¹ represents an unsubstituted or substituted monovalent hydrocarbon group,
Or a trimethylsiloxy group, R ² is a hydrogen atom or an alkyl group, R ³ is a divalent hydrocarbon group, a is 1 or 2, b is an integer of 10 to 400, and c is an integer of 1 to 5. The terminal-modified polyoxyalkylene polyether represented by [1] is typical. As is clear from the above general formula (1), this polymer has a main chain composed of a polyoxyalkylene chain, and has silanol groups or alkoxysilyl groups at both ends of the molecular chain. Reacts with and easily becomes a polymer (three-dimensional) to form a cured product. Further, it has an advantage that it is stable and easy to handle as compared with the above-mentioned polyoxyalkylene polyether having a hydrolyzable group.

In the general formula (1), R ¹ is a monovalent hydrocarbon group or a trimethylsiloxy group, and the monovalent hydrocarbon group is an alkyl group such as a methyl group, an ethyl group or a propyl group, A cycloalkyl group such as a cyclohexyl group, an aryl group such as a phenyl group and a tolyl group, an aralkyl group such as a benzyl group and a phenylethyl group, and a group in which some or all of the hydrogen atoms of these groups are substituted with halogen or the like (for example, Examples thereof include a chloromethyl group and a 3,3,3-trifluoropropyl group), and among these, a methyl group and a phenyl group are preferable. R ² is a hydrogen atom or an alkyl group. When R ² is a hydrogen atom, the molecular chain end is blocked with a silanol group, and when it is an alkyl group, it is blocked with an alkoxysilyl group. Examples of this alkyl group include a lower alkyl group such as a methyl group, an ethyl group, a propyl group and a butyl group, and a particularly preferable one is a methyl group.

Further, the divalent hydrocarbon group R ³ is preferably an alkylene group having 2 or 3 carbon atoms, and particularly preferably --CH ₂ CH _2- , --CH ₂ C (C
H ₃₎ H-, can be exemplified. Also in the main chain −
In the OR ³ − repeating structure, R ³ is not limited to one kind, and two or more kinds of R ³ may be combined to form a repeating structure. Examples of the repeating structure formed by combining two or more types of R ³ include a polyoxyethylene polyoxypropylene structure.

The terminal-modified polyoxyalkylene polyether represented by the above general formula can be synthesized by the following method, for example, in the case where the terminal is a silanol group. First, following general formula _{(2): CH 2 = CH} -CH 2 - (OR 3) b -O-CH 2 -CH = CH 2 (2) wherein, R ³ and b are the same, and the] in polyethers with a molecular chain terminal unsaturated group represented by the general formula ^{(3): HSi (R 1} ) a Cl 2-a (3) wherein, R ^1, a is the same, and the] in Si-H shown
The bond-containing silanes are subjected to an addition reaction in the presence of a catalyst such as chloroplatinic acid to give the following general formula (4):

[0012]

[Chemical 2] (In the formula, R ¹ , a and b have the same meanings as described above) A polyether having Si—Cl bonds at both ends of the molecular chain is synthesized.

Next, this polyether was added to -10 to 13
While maintaining at 0 ° C., preferably 110 to 60 ° C., water of equimolar amount or more with respect to chlorine atom in this polyether is added and hydrolyzed to obtain a target terminal silanol group-containing polyoxyalkylene polyether. Easily synthesized. In this case, a hydrochloric acid scavenger may be used if necessary. Examples of the hydrochloric acid scavenger include ammonia, triethylamine, diethylamine, pyridine, pyricon, amines such as urea, sodium hydrogen carbonate, sodium carbonate,
Examples thereof include alkali metal carbonates such as potassium carbonate.

In carrying out each of the above-mentioned reactions, the use of a solvent is not particularly required. However, for example, when a starting material or the like has a high viscosity and the operation such as stirring is difficult, it is not suitable. An active organic solvent may be used. Such organic solvents include benzene, toluene, aromatic hydrocarbon solvents such as xylene, hexane, aliphatic hydrocarbon solvents such as octane, ether solvents such as ethyl ether, ketone solvents such as methyl ethyl ketone, trichloroethylene and the like. Examples thereof include halogenated hydrocarbon solvents.

In the above reaction, the fact that the Si--Cl bond is changed to the corresponding Si--OH bond is easily caused by the appearance of the OH absorption band by infrared absorption spectrum analysis or the quantification of silanol group by the Grignard reagent. You can check. The polyether having an unsaturated group at both ends of the molecular chain represented by the formula (2) and the Si—H bond-containing silanes represented by the formula (3) are known compounds and are easily available. It is possible.

The modified polyoxyalkylene polyether having an alkoxysilyl group at the terminal is, for example, the modified polyoxyalkylene polyether having a silanol group at the terminal obtained above, and the corresponding alcohol or alcohol in the presence of an acid or an alkali. It can be easily synthesized by reacting the component (B) described below. Further, by utilizing the reaction of the compounds of the above general formulas (2) and (3), a compound in which the Cl group of the general formula (3) is substituted with an alkoxy group,
It can also be easily synthesized by reacting with the polyether of the general formula (2).

Component (B) Component (B) is a cross-linking agent, and an organosilicon compound having at least two hydrolyzable groups in one molecule is used.
That is, the organosilicon compound and the modified polyoxyalkylene polyether are condensed in the presence of water to form a three-dimensionally elastic cured product. Examples of the hydrolyzable group include an alkoxy group, an acyloxy group, a ketoxime group, an amide group, an unsubstituted or N-substituted amino group,
Examples thereof include an unsubstituted or N-substituted aminooxy group and an alkenyloxy group.

A typical example of such an organosilicon compound is the following average composition formula (5): R ⁴ _d Y _e SiO _{4-de / 2} (5) [wherein R ⁴ is a monovalent hydrocarbon group, Y Is a hydrolyzable group exemplified above, d is 0 ≦ d ≦ 2, e is 0 <e ≦ 4, where 0 <d + e ≦ 4], and one molecule of the hydrolyzable group Y is represented by It is a silane or siloxane having at least two of them. In the formula (5), examples of the monovalent hydrocarbon group R ⁴ include alkyl groups such as methyl group, ethyl group and propyl group, alkenyl groups such as vinyl group and allyl group, aryl groups such as phenyl group and naphthyl group. And aralkyl groups such as benzyl group.

Specific examples of the component (B) organosilicon compound that can be used in the present invention are given below.
It is not limited to this. Dimethyldimethoxysilane, diethyldimethoxysilane, diphenyldimethoxysilane, dimethyldiethoxysilane, diethyldiethoxysilane, diphenyldiethoxysilane, methylvinyldiethoxysilane, phenylvinyldiethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, methyl Di- or tri-, such as tripropoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, propyltrimethoxysilane, propyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, etc. Alkoxysilanes, partially hydrolyzed condensates thereof, and alkoxylans and tetraalkoxysilanes and / or monoalkoxysilas Partially hydrolyzed condensate of a mixture of.

Di- or triacyl compounds such as dimethyl diacetoxy silane, diethyl acetoxy silane, diphenyl diacetoxy silane, methyl vinyl diacetoxy silane, methyl triacetoxy silane, ethyl triacetoxy silane, phenyl triacetoxy silane and vinyl triacetoxy silane. Siloxysilanes, partially hydrolyzed condensates thereof, and partially hydrolyzed condensates of mixtures of these acyloxysilanes with tetraacyloxysilane and / or monoacyloxysilane.

Dimethyl-bis (methylethylketoxime) silane, methylvinyl-bis (methylethylketoxime) silane, methyl-tris (dimethyloxime)
Silane, methyl-tris (methyl ethyl ketoxime)
Silane, ethyl-tris (dimethylketoxime) silane, ethyl-tris (methylethylketoxime) silane, vinyl-tris (dimethylketoxime) silane,
Vinyl-tris (methylethylketoxime) silane,
Phenyl-tris (dimethylketoxime) silane, phenyl-tris (methylethylketoxime) silane,
Ketoxime silanes such as tetra (methylethylketoxime) silane, and partially hydrolyzed condensates of these ketoxime silanes.

Dimethyl-bis (N-methylformamide) silane, dimethyl-bis (N-methylacetamido) silane, diethyl-bis (N-methylformamide) silane, diethyl-bis (N-methylacetamido) silane, diphenyl-bis (N-methylformamide) silane, diphenyl-bis (N-methylacetamide) silane, methylvinyl-bis (N-methylformamide) silane, methylvinyl-bis (N-methylacetamide) silane, methyl-tris (formamide) silane , Methyl-tris (acetamido) silane, methyl-
Tris (N-methylformamide) silane, methyl-tris (N-methylacetamido) silane, phenyl-tris (formamide) silane, phenyl-tris (acetamido) silane, phenyl-tris (N-methylformamide) silane, phenyl-Tris (N-methylacetamido) silane, vinyl-tris (formamido) silane, vinyl-tris (acetamido) silane, vinyl-tris (N-methylformamide) silane, vinyl-
Amidosilanes such as tris (N-methylacetamido) silane, and partially hydrolyzed condensates of these amidosilanes.

Dimethyl-bis (N, N-dibutylamino) silane, diethyl-bis (N, N-dibutylamino) silane, diphenyl-bis (N, N-dibutylamino) silane, methyl-tris (N-butylamino) silane ) Aminosilanes such as silane, ethyl-tris (N-butylamino) silane, phenyl-tris (N-butylamino) silane, vinyl-tris (N-butylamino) silane, and partially hydrolyzed condensates of these aminosilanes.

Dimethyl-bis (N, N-diethylaminooxy) silane, diethyl-bis (N, N-diethylaminooxy) silane, diphenyl-bis (N, N-diethylaminooxy) silane, methylvinyl-bis (N,
N-diethylaminooxy) silane, dimethyl-bis (N, N-diphenylaminooxy) silane, methyl-
Tris (N, N-diphenylaminooxy) silane, tetra- (N, N-diphenylaminooxy) silane, methyl-tris (N, N-diethylaminooxy) silane, tetra- (N-methyl-N-ethylaminooxy) )
Silane, ethyl-tris (N, N-diethylaminooxy) silane, phenyl-tris (N, N-dipropylaminooxy) silane, 3-chloropropylmethyl-bis (N, N-dimethylaminooxy) silane, the following formula :

[0025]

[Chemical 3] And an aminooxysilane partially hydrolyzed condensate of these aminooxysilanes. The following formula

[0026]

[Chemical 4] Such as alkenyloxysilanes, and their partial hydrolysis-condensation products. The following formula

[0027]

[Chemical 5] Alkenyloxy group-containing disiloxane such as.

The above-mentioned organosilicon compounds can be used singly or in combination of two or more kinds. Among them, the partial hydrolyzed condensate has two or more hydrolyzable groups in one molecule. Any of linear polysiloxanes having 2 or more silicon atoms and cyclic polysiloxanes having 3 or more silicon atoms can be used as long as they are available.

The composition of the present invention is cured by the cross-linking reaction between the component (A) and the component (B). In order to make the curing reaction proceed better, the component (A) is silicon. In the case where one molecule has two hydroxyl groups directly bonded to each other, it is desirable to use an organosilicon compound having three or more hydrolyzable groups in one molecule as the component (B).

In the present invention, the above-mentioned component (B) is
1 to 30 parts by weight, especially 5 per 100 parts by weight of component (A)
It is preferred to use in an amount of -15 parts by weight. When this amount is small, a cured product excellent in elasticity and mechanical strength cannot be obtained, and when it is too large, the obtained cured product tends to be hard and brittle.

The organic compound having a carbonyl group (C═O) used as the component (C) (C) has the primary amino group (NH ₂ ) of the component (D) as described above. It reacts with an organic compound to produce water that acts as a deep curing agent. As such a carbonyl group-containing compound, any organic compound can be used as long as it has a carbonyl group reactive with the primary amino group of component (D). Specifically, acetone, cyclohexanone, methyl ethyl ketone, ketones such as acetophenone, ethyl acetate, butyl acetate, methyl propionate, ethyl acrylate, esters such as butyrolactone, dimethylformamide, diethylacetamide, amides such as butyrolactam, acetic acid. Carboxylic acids such as propionic acid and benzoic acid, and silane coupling agents having a carbonyl group as a functional group constituting the above-mentioned ketone, ester, amide, carboxylic acid, various polymers having a carbonyl group, oligomers, etc. They can be used alone or in combination of two or more. Among these, acetone and cyclohexanone are preferable.

The component (C) is preferably used in an amount of 0.001 to 1 mol, particularly 0.01 to 0.1 mol, per 100 g of the component (A). When this amount is less than 0.001 mol, the composition does not exhibit sufficient deep-curing property upon curing, and when it is more than 1 mol, the strength and hardness of the elastic body obtained by curing the composition are low. Tends to be unsatisfactory.

[0033] Component (D) Component (D) is an organic compound having a primary amino group, as described above, to generate water that acts by reacting with compounds of component (C) as a deep curing agent . Examples of the organic compound having a primary amino group include primary amines such as methylamine, ethylamine, butylamine, ethylenediamine, triethylenetetramine, aniline, 4,4′-diaminodiphenyl ether; aliphatic polyamines; Polymers or oligomers having primary amino groups such as alkylene oxide polymers containing primary amino groups;
Examples thereof include silane coupling agents having a primary amino group as a functional group and amino group-containing organosilicon compounds such as primary amino group-containing polysiloxane. Among these, the amino group-containing organosilicon compound is preferable because a cured product having particularly good rubber elasticity can be obtained.

The amino group-containing organosilicon compound is
For example, the basic molecular skeleton is represented by the following formula: —Si (R ⁵ ) ₂ —O
^{-, - Si (R 5)} 2 -, - Si (R 5) 2 -Si (R
⁵ ) ₂ −,> Si (R ⁵ ) —O−, ≡Si (R ⁵ ),
[In the formula, R ^{5 s} may be the same or different and may be an alkyl group such as a methyl group or an ethyl group, an alkenyl group such as a vinyl group or an allyl group, an aryl group such as a phenyl group, a trifluoropropyl group or a methoxy group. , An ethoxy group, an alkoxy group such as an isopropoxy group, an amino group, an aminoxy group, an acetoxy group, etc.]

A primary amino group having a structure represented by the formula (1) or a combination of two or more types, and having a silicon atom constituting the basic skeleton through a suitable linking group such as an alkylene group. Is a combination of. The molecular structure (linear, branched, cyclic or a combination thereof), molecular weight, etc. of the amino group-containing organosilicon compound are not particularly limited,
It is optional as long as the amino group has reactivity with the carbonyl group in the component (C). In the present invention,
As a typical example of this amino group-containing organosilicon compound,
γ-aminopropyltriethoxysilane, and the following formula,

[0036]

[Chemical 6]

[0037]

[Chemical 7]

[0038]

[Chemical 8] Can be mentioned. In the above formula,
Me is a methyl group, Et is an ethyl group, Ph is a phenyl group,
Vi represents a vinyl group and i-Bu represents an isobutyl group. Commercial products of such amino group-containing organosilicon compounds include KF393, KF859 and KF manufactured by Shin-Etsu Chemical Co., Ltd.
F86, KF861, KF867, KF869, KF8
80, KF8002, KF8004, KF8005, K
There are F864, KF865, KF868, KF8003 (trade name), etc.

The amount of the primary amino group in the above component (D) is 0.0 per mol of the carbonyl group in the component (C).
It is preferably used in an amount of 1 to 10 mol, particularly 0.8 to 1.2 mol from the viewpoint of the curing rate of the composition, long-term storage stability in an uncured state, economical efficiency, and the like.

Component (E) The component (E) is a curing catalyst, and is the above-mentioned (A) and (B).
Used to accelerate the condensation curing of components. As such a curing catalyst, a known catalyst conventionally used for condensation-curing type compositions, for example, a tin-based catalyst and a titanium-based catalyst can be used. Specifically, tin naphthenate,
Tin caprylate, tin oleate, dibutyltin diacetate, dibutyltin dioctate, dibutyltin dilaurate, dibutyltin dioleate, diphenyltin diacetate, dibutyltin oxide, dibutyltin dimethoxide, dibutylbis (triethoxysiloxy) tin, dibutyltin benzylma Tin compounds such as rates; titanic acid esters or titanium chelates such as tetraisopropoxy titanium, tetra-n-butoxy titanium, tetrabis (2-ethylhexoxy) titanium, dipropoxybis (acetylacetona) titanium, titanium isopropoxyoctylene glycol. Examples thereof include compounds.

This component (E) catalyst is composed of the component (A) 10
It is used in an amount of 0.1 to 10 parts by weight, particularly 0.5 to 5 parts by weight, based on 0 parts by weight, from the viewpoint of curing rate, long-term storability in an uncured state, and economical efficiency. Is preferred.

Other Components In addition to the components (A) to (E), various components can be added to the room temperature curable composition of the present invention, if necessary. For example, a basic compound can be used in combination in order to enhance the activity of the catalyst (component E). Examples of the basic compound include amines such as octylamine and laurylamine, imidazolines that are cyclic amidines, theorahydropyrimidines, and 1,8-diazabicyclo (5, 4,
0) Examples include guanidyl group-containing silane compounds such as undecene-7 and guanidinepropyltris (trimethylsiloxy) silane, partial hydrolysates thereof, and guanidyl group-containing siloxanes.

In addition to the above basic compounds, fumed silica, precipitated silica, aluminum oxide, quartz powder,
Carbon powder, reinforcing agents such as talc and pentonite, fibrous fillers such as asbestos, glass fibers and organic fibers, colorants such as pigments and dyes, heat resistance improvers such as red iron oxide and cerium oxide, cold resistance improvers, Dehydrating agent, rust inhibitor, adhesion improver such as γ-acryloxypropyltrimethoxysilane, triorganosiloxy unit and Si
A liquid reinforcing agent such as a reticulated polysiloxane composed of O ₂ units may be added, and these are used in an amount suitable for the purpose as long as the curability of the composition is not impaired. The composition of the present invention further comprises, as a polymer component, the following general formula (6):

[0044]

[Chemical 9] A dihydroxydiorganopolysiloxane represented by the formula [wherein R ⁶ and R ⁷ are unsubstituted or substituted monovalent hydrocarbon groups and p is a positive integer] can be blended. This diorganopolysiloxane has hydroxyl groups bonded to silicon atoms at both ends of the molecular chain, and reacts with the component (B), which is a crosslinking agent, as in the component (A) to cure. Therefore, by blending this diorganopolysiloxane, the cured product is provided with the excellent properties possessed by the polysiloxane such as heat resistance, cold resistance, light resistance, chemical resistance, and electrical characteristics. However, if the blending amount is too large, the purpose of the present invention of obtaining a cured product mainly composed of the component (A) will be impaired, and therefore, usually, the maximum amount is equal to that of the component (A).
In particular, it should be 50 parts by weight or less per 100 parts by weight of the component (A). Of course, depending on the purpose, more than this is allowed.

In the above general formula (6), the substituted or unsubstituted monovalent hydrocarbon groups R ⁶ and R ⁷ are alkyl groups such as methyl group, ethyl group, propyl group and butyl group,
Cycloalkyl group such as cyclohexyl group, alkenyl group such as vinyl group, allyl group and isopropenyl group, aryl group such as phenyl group, naphthyl group and tolyl group, aralkyl group such as benzyl group and phenylethyl group, and these groups A group in which at least a part of the hydrogen atoms of is substituted with a halogen atom, a cyano group or the like, for example, a chloromethyl group, a 3,3,3-trifluoropropyl group or the like is exemplified. Further, such a dihydroxydiorganopolysiloxane has a viscosity of 1 at 25 ° C.
It is desirable to be in the range of 00 to 500,000 cSt. Therefore, n in the general formula (6) is a positive integer, but it is particularly preferable that the number is such that the viscosity is in the above range. Further, the above-mentioned dihydroxydiorganopolysiloxane is a polysiloxane having a substantially linear structure, but may have a trifunctional or four-tube siloxane unit in the molecular structure within a small amount range.

Preparation of Composition The composition of the present invention is prepared by uniformly mixing a predetermined amount of each of the components (A) to (E) and optional components added as necessary in a dry atmosphere. Obtained as a liquid-type room-temperature fast-curing composition. In this case, the components (C) or (D) are preferably microencapsulated by a means known per se and mixed, whereby a one-pack type room temperature curable composition having improved storage stability is obtained. be able to. Further, it is also possible to adopt a method in which the two liquids are separately packaged and mixed at the time of use. In the case of the two-liquid type, it is easy to set the mixing ratio of the two liquids to 1: 1 and workability is good.

Uses This composition is, for example, a sealing material for construction, a coating material, a sealing material for electric and electronic parts, a potting material, a fiber treating agent, for automobiles, from the viewpoint of its rapid curing property and deep curing property. It is useful as an adhesive for construction and electrical / electronic use.
In particular, it can be effectively used as an oil seal material for automobiles, which is required to have high fast-curing property and deep-curing property in the manufacturing process, and a sealing material for electric and electronic materials and potting material, which is required to rationalize the process.

[0048]

EXAMPLES In the following examples, the viscosity is a measured value at 25 ° C.

Synthesis Example 1 Polyoxypropylene having allyloxy groups at both ends of the molecular chain (average molecular weight: about 6000, viscosity: about 2,200 cSt) 3
00g Dimethylchlorosilane 11.5g Chloroplatinic acid in isopropyl alcohol (platinum equivalent:
About 2% by weight) 0.3 g Toluene 200 g was charged into a reaction flask and reacted (addition reaction) at 40 ° C. for 1 hour and 110 ° C. for 3 hours while stirring.
To this reaction solution, 12 g of triethylamine was added, and water was added with stirring while keeping the internal temperature at 30 ° C.
5 g was added, and then the mixture was stirred at 40 ° C. for 2 hours to carry out hydrolysis reaction. Then, triethylamine hydrochloride as a by-product was filtered off, and toluene was distilled off under reduced pressure at 60 ° C. to obtain 305 g of a yellowish brown viscous liquid (viscosity: 2,520 cSt).
was gotten. As a result of analysis, the above product was confirmed to have an average molecular weight of about 6,200 and to be a terminal silanol group-containing polyoxyalkylene polyether corresponding to the following formula. Hereinafter this is referred to as POA-1.

[0050]

[Chemical 10]

Synthesis Example 2 The procedure of Synthesis Example 1 was repeated except that the hydrolysis reaction step (step of stirring at 40 ° C. for 2 hours) was carried out at 100 ° C. for 4 hours. The average molecular weight was about 1245.
A terminal silanol group-containing polyoxyalkylene polyether corresponding to the following formula having 0 (which is 2 of POA-1)
301 g) was obtained. Hereinafter this is referred to as POA-2.

[0052]

[Chemical 11]

Synthesis Example 3 Polyoxypropylene having an allyloxy group at the end of the molecular chain (average molecular weight: about 4,100, viscosity: about 790 cSt) 3
00 g, methyldichlorosilane 18.5 g, chloroplatinic acid in isopropyl alcohol (platinum equivalent:
About 2% by weight) 0.3 g Toluene 200 g was charged into a reaction flask and reacted (addition reaction) at 40 ° C. for 1 hour and 110 ° C. for 3 hours while stirring. The reaction solution was added dropwise to a mixed solution of 50 g of toluene, 50 g of triethylamine and 9 g of water while stirring at a temperature of 0 ° C. over 30 minutes, and then stirred at 30 ° C. for 2 hours to carry out a hydrolysis reaction. Then, by-produced triethylamine hydrochloride was filtered off, and toluene was distilled off at 60 ° C. under reduced pressure. As a result, a terminal silanol group-containing polyoxyalkylene polyether corresponding to the following formula (average molecular weight: about 4200) 3
06g was obtained. Hereinafter this is referred to as POA-3.

[0054]

[Chemical 12]

Examples 1 to 3, Comparative Examples 1 to 5 To 100 parts by weight of each of POA-1 to 3 obtained in Synthesis Example 1-3, 15 parts by weight of dioctyl phthalate and 80 parts by weight of precipitated calcium carbonate were added. The above blends were kneaded with three rolls to prepare three types of bases 1 to 3, respectively. A method in which these bases are blended with the composition shown in Table 1 below, molded into a sheet having a thickness of 2 mm, and then cured in an atmosphere of 20 ° C. and 55% RH, and after 1 day, conforms to JIS-K-6301. I checked the physical properties. The deep-curing property was evaluated by putting the above composition in a 10 mm thick plastic container and measuring the deep-curing thickness after 3 hours. The results are as shown in Table 1.

[0056]

[Table 1]

[0057]

EFFECTS OF THE INVENTION The room-temperature-curable alkylene oxide polymer composition of the present invention, when cured, produces water as a deep-curing agent in the system. Also, it is extremely excellent in deep-part curability.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Masatoshi Arai 1 Hitomi, Osamu Matsuida-cho, Usui-gun, Gunma 10 Shin-Etsu Chemical Co., Ltd. Silicone Electronic Materials Research Laboratory

Claims (3)

[Claims] 1. A silanol group- or alkoxysilyl group-containing alkylene oxide polymer (A), (B) an organosilicon compound having at least two hydrolyzable groups in one molecule, (C) a carbonyl group-containing organic compound, A room temperature curable composition comprising (D) an organic compound having a primary amino group, and (E) a curing catalyst. 2. The composition according to claim 1, wherein the carbonyl group of the component (C) and the primary amino group of the component (D) react with each other to produce water. 3. A cured product obtained by curing the composition according to claim 1.