JPS62230822A - Production of polyether having terminal blocked with hydrolyzable silyl group - Google Patents

Abstract

PURPOSE:To obtain a polyester capable of forming a rubber-like elastomer, having good adhesive property and extension ratio and rich in flexibility, by reacting a specific polyoxyalkylene with a primary or secondary amine and organosilicon compound in the presence of a monohydric primary alcohol. CONSTITUTION:A polyether, obtained by reacting a polyoxyalkylene, expressed by formula I (R<1> and R<2> are bifunctional hydrocarbon; n is 10-250) and having molecular terminals blocked with epoxy groups with a monofunctional primary amine expressed by the formula R<3>-NH2 (R<3> is monofunctional hydrocarbon) or bifunctional secondary amine expressed by formula II (R<4> and R<6> are monofunctional hydrocarbon; R<5> is bifunctional organic group) and an organosilicon compound, expressed by formula III (R<7> and R<9> are monofunctional hydrocarbon; R<8> is bifunctional hydrocarbon; R<10> is 1-6C monofunctional hydrocarbon; a is 1-3) and having amino group and hydrolyzable group in the presence of a monofunctional primary alcohol expressed by the formula R<11>-OH (R<11> is same as R<10>) and expressed by formula IV or V (m is a value to give 1,000-50,000mol.wt.).

Description

Detailed Description of the Invention [Industrial Application Field] The present invention is useful as a base polymer for a room-temperature curable composition capable of forming a rubber-like elastic body that has adhesive properties and is highly elongated and highly flexible. The present invention relates to a method for producing a polyether end-capped with a hydrolyzable silyl group.

[Conventional technology and its problems]

A composition using a polymer having a hydrolyzable silicon functional group and whose main chain is essentially a polyether as a base polymer is disclosed in JP-A-52-7398, etc., and this type of composition is In recent years, it has begun to be used as a sealant for joints in buildings. However, since this type of polymer does not inherently have adhesive properties, it is necessary to pre-treat the surface to be coated with a primer or add a silane coupling agent to the composition to impart adhesive properties. It is necessary. However, the addition of a silane coupling agent causes a problem in that the elongation rate of the cured rubber-like elastic body decreases in exchange for adhesion, making it brittle and unusable as a sealing material.

The present invention was devised in view of such problems, and its purpose is to provide a base polymer suitable for a room-temperature curable composition capable of forming a rubber-like elastic body with adhesive properties and high elongation. , to provide a polyether end-capped with hydrolyzable silyl groups.

[Means for solving problems]

The present inventors first prepared the general formula (^); inside, p? , R8, R9 and a are as described above) A polyether (the following general formula [■]) having a hydrolyzable silyl group at the end of the molecular chain is obtained by reacting with an organosilicon compound represented by It has been found that it cures to give an elastic body and also has adhesive properties.

-R2-CIIC1lz-N-R'-St (OR”
) - (m) Furthermore, with the aim of obtaining a highly flexible elastic body with a high elongation rate, the present inventors developed a polyoxyalkylene compound in which the molecular chain terminals of (8) shown above are blocked with an epoxy group. and (B) -71 formula; R3-Ni1゜ and R
6 is as described above) and the organosilicon compound (C) shown above are reacted to form a compound at the end of the molecular chain represented by formula (1) or formula (n). An attempt was made to obtain a polyether having hydrolyzable silyl groups. However, the problem is that it is difficult to obtain a polymer with a high degree of polymerization that gives a rubber-like cured product with high elongation and high flexibility because unexpected viscosity upper limits and gelation occur during the reaction. was there.

As a result of further investigation into methods for solving these problems, the present inventors found that (A) the polyoxyalkylene whose molecular chain terminals are blocked with an epoxy group, and (B) a monovalent primary amine or a divalent primary amine. and (C) an organosilicon compound in the presence of (D) a monohydric primary alcohol represented by the general formula; R''-0)1 (wherein R1 is as described above). CI) and [hydrolyzable silyl compound represented by the formula The present invention was completed based on the discovery that it is possible to obtain a polyether end-capped with a group.

That is, the present invention provides the following: (8) General formula; (wherein, R1 and R2 are divalent hydrocarbon groups, and n is 10 to 2
50), in which the molecular chain bundle O:;; is blocked with an epoxy group, and (B) the general formula; 1? A monovalent primary amine or general formula represented by '-NH□ (wherein R' is a substituted or unsubstituted monovalent hydrocarbon group); (wherein n4. R6 is a monovalent hydrocarbon group, (R5 represents a divalent organic group) and (C) general formula; % formula %) (wherein, R7 is a monovalent hydrocarbon group, R8 is a divalent hydrocarbon group, R9 is a monovalent hydrocarbon group, RIG has 1 to 6 carbon atoms
(1) General formula: R''-011 (In the formula, R11 represents a monovalent hydrocarbon group having 1 to 6 carbon atoms) A general formula characterized in that the reaction is carried out in the presence of a monovalent primary alcohol; Medium, R1, Rg, R'+ R', R5, Rh,
R', p@.

R9, HIO, a and n are as described above, m is a number selected such that the molecular weight is in the range of t, ooo to 50,000), and the end is blocked with a hydrolyzable silyl group. This invention relates to a method for producing polyether.

(8), which is the first raw material component used in the present invention, is a polyoxyalkylene whose molecular chain terminals are blocked with an epoxy group, represented by the general formula (wherein R1, R2 and n are as described above). and the oxyalkylene unit R'0 of (A)
It is preferable to use an oxyethylene unit, an oxypropylene unit, or a combination of an oxyethylene unit at the 11'L position and an oxypropylene unit, and an oxypropylene unit is particularly preferable because it is easy to polymerize the raw materials manually and maintains a liquid state even at a high degree of polymerization. The degree of polymerization n of the R'0 unit in (A) is preferably 10 or more, since it is easy to obtain a polyether end-capped with a hydrolyzable silyl group, which gives a rubber-like cured product with high elongation. , is preferably 250 or less for the purpose of obtaining a composition with good adhesive properties. Also R2's 2
Examples of the valent hydrocarbon group include a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, a phenylene group, and a wrinkled group. Typical examples of these (A) include those obtained by adding epichlorohydrin to polyoxyethylene or polyoxypropylene, both ends of which are blocked with hydroxyl groups, in the presence of a basic catalyst.

The second raw material component (B) used in the present invention has the general formula; R''-Nil2 (wherein R3 is as described above)1
It is a divalent secondary amine represented by 1N-R'-Nil (wherein RJS and R6 are as described above), and (B
) as monovalent hydrocarbon groups for R3, R4 and R6; alkyl groups such as ethyl, propyl, butyl, hexyl; alkenyl groups such as vinyl and allyl; phenyl, tolyl, etc. Aryl groups such as benzyl groups and aralkyl groups such as β-phenylethyl groups are exemplified. In addition, as the substituted hydrocarbon group of the above R3, 2-hydroxyethyl group, 2-methoxyethyl group,
p-hydroxyphenyl group, p-chlorophenyl group, etc. can also be used. In addition, the divalent organic group of R5 is preferably a divalent hydrocarbon group from the viewpoint of ease of handling and synthesis of raw materials and precursors, and these divalent hydrocarbon groups include:
Examples include ethylene group, butylene group, hexamethylene group, phenylene group, and cyclohexylene group.

is Formula 10; HN-R"-5i (OR10),
(In the formula, RJII.

R9 and a are as described above), which is an organosilicon compound having an amine group and a hydrolyzable group;
) The monovalent hydrocarbon groups for R7 and R9 include alkyl groups such as methyl, ethyl, propyl, butyl, and hexyl; alkenyl groups such as vinyl and allyl; phenyl and tolyl groups; Aryl groups such as benzyl group, aralkyl group such as β-phenylethyl group, etc.
' is exemplified. Among these, as the monovalent hydrocarbon group for R9, a methyl group or a phenyl group is preferred from the viewpoint of ease of synthesis, and a methyl group is particularly preferred from the viewpoint of ease of obtaining raw material intermediates. As the divalent hydrocarbon group for R8, an alkylene group such as a methylene group, ethylene group, trimethylene group, or tetramethylene group is preferable from the viewpoint of ease of synthesis and availability of (C) itself or a precursor. (C) R
IG is selected from monovalent hydrocarbon groups having 1 to 6 carbon atoms such as methyl group, ethyl group, propyl group, and hexyl group, but methyl group and ethyl group are preferable from the viewpoint of high hydrolyzability, and methyl group is particularly preferred. preferable. The number a of hydrolyzable groups is 1 to
However, in order to obtain a composition that provides a rubber-like cured product with a high elongation rate, which is a feature of the present invention, a is preferably 2. On the other hand, when a is only 1, the curing speed is slow, and when a is only 3, it is difficult to obtain a rubber-like elastic body with high elongation and flexibility. It is desirable to use it.

Further, @m of the repeating unit of the polyether blocked with a hydrolyzable silyl group represented by the formula (1) and the formula rII) obtained in the present invention is represented by the formula ([) or (If). Polyether molecular weight is 1,000 to 50,0
Selected to be in the range 00. If the molecular weight is less than 1,000, a rubber-like cured product with a high elongation rate, which is a feature of the present invention, cannot be obtained.On the other hand, if it is larger than so or ooo, the viscosity becomes high and workability becomes poor.

(D) of the present invention is an essential component for obtaining a polyether terminal-capped with a hydrolyzable silyl group having a high degree of polymerization and giving a rubber-like cured product with a high elongation rate. Component (D) has the general formula; R''-011 (in the formula, 1-11 is carbon number 1-6
Among them, methanol and ethanol are preferred, and methanol is particularly preferred because they are effective in small amounts. The present invention is characterized in that (A), (B) and (C) are reacted in the presence of (D) to obtain a polyoxyalkylene end-capped with a hydrolyzable silyl group, (A), (B) and (
The amount of C) to be blended is theoretically such that the molar ratio is (A):(B
): (C) = (m+1) :m:2. However, in reality, it is acceptable to use (B) and (C) in amounts slightly exceeding the theoretical amounts. The reaction procedure is (8).

(B) and (C) may be added and reacted simultaneously in the presence of (D), but first, (A) and (B) are reacted in the presence of (D) to elongate the chain. After that, it is easier to control the degree of polymerization by adding (C) and carrying out the reaction in the presence of (D), and it is also possible to reliably introduce hydrolyzable groups to both ends of the molecular chain. Although this reaction may occur at ambient temperature, it is preferred to accelerate the reaction by using a temperature below the reflux temperature of (D), for example from 50<0>C to 150<0>C. The progress of these reactions can be confirmed by tracking the increase in viscosity or by direct titration of epoxy groups. If this reaction were to be carried out without the presence of component (0), an abnormal increase in viscosity or gelation would occur, and the elongation rate of the rubber-like cured product obtained by curing it would be low considering the viscosity of the obtained polymer. The problem arises that . On the other hand, if this reaction is carried out in the presence of component (D), which is a feature of the present invention, such problems will not occur and a hydrolyzable silyl with a high degree of polymerization will yield a rubber-like cured product with a high elongation rate. Polyethers end-capped with groups can be obtained.

Component (D) has the ability as an epoxy group ring-opening catalyst,
In addition, it has the effect of preventing addition of bonds due to the reaction between the alcoholic hydroxyl group and the hydrolyzable silicon group, which are generated when the epoxy ring opens.

In order to reliably exhibit these effects, it is preferable to use component (D) in an amount of 1% by weight or more, more preferably 3% by weight or more, based on component (^).

The upper limit of the amount of component (D) used is not particularly limited, but since using more component (D) than necessary will lead to a decrease in production efficiency, the upper limit is set at 100% by weight based on component (A). It is preferable to do so.

In addition, when carrying out this reaction, a hydrocarbon-based, ester-based, or ether-based solvent can also be used in combination.

Also, when the synthesis reaction is completed, that is, the (B) of the raw material
At the time when most of the components and the primary or secondary amine of component (C) are consumed, the equilibrium reaction described above hardly proceeds, so component (D) may be distilled off.

〔Effect of the invention〕

The polyether end-capped with hydrolyzable silyl groups obtained in the present invention contains tin carboxylates such as tin octylate; dibutyltin dilaurate and dibutyltin phthalate.
Organic tin carboxylates such as titanate and dibutyltin phthalate; Reactants with organic tin oxides and their esters; Organic titanate esters such as tetrabutyl titanate; Curing catalysts such as amines, amine salts, quaternary ammonium salts, and guanidine compounds. Fillers such as calcium carbonate, talc, clay, ground silica, fumed silica, precipitated silica, titanium oxide, etc. Other thixotrophic properties imparting agents, plasticizers, ultraviolet absorbers, etc. may be added as necessary for architectural use. It is possible to obtain a room-temperature-curable composition that can form a rubber-like elastic body that has adhesive properties, has a high elongation rate, and is rich in flexibility, and is suitable as a sealing material.

〔Example〕

Hereinafter, the present invention will be explained with reference to Examples. In addition, % in an example shows weight %.

Example 1 Polyoxypropylene with an average degree of polymerization of 15 and a molecular weight of about 1,000.25°C and a viscosity of 270 cSt. For 10 epoxy equivalents of glycidyl group-end-blocked polyoxypropylene, methanol in an amount of 10% of the polyoxypropylene and 4 mol of n-butylamine was added, and heating stirring was started at 60° C. under a nitrogen atmosphere. In addition, a small amount was taken out every hour after the start of heating and stirring and the viscosity at 25"C was measured.The viscosity was 90cSt before heating and stirring, but reached 200cSt 8 hours after heating and stirring started. ,
After that, the viscosity increase stopped C1hCII□NCII□CIl
Two moles of an organosilicon compound (silane compound) represented by □CIl□S i (OCII z) z was added, and heating and stirring was continued under the same conditions. A small amount was taken out every hour after the addition of the silane compound and the epoxy groups were titrated using the hydrochloric acid dimethylformamide method. As a result, the disappearance of the epoxy groups was observed 6 hours after the addition of the silane compound, so heating and stirring were stopped. , methanol is distilled off, 2
The viscosity at 5°C is 11,000 cSL, and the specific gravity at the same temperature is 1. A pale yellow viscous liquid (a polymer represented by the following formula) of Ol was obtained.

(CH30) zSi(CHz)r N-1l-CI
IzCHCHzMCHCHzO)=y011
08 CI+3- CIl zcHcll z
-N -h-CIl zcHcll zO(CIICI
I z discharge■■ CHzClhCIb -C11□ClICl1z-N(CHzhsi (OC
H3) z Example 2 Average degree of polymerization 32, molecular weight approximately 2,000, viscosity at 250°C 550 cSt 10 epoxy equivalents of glycidyl group-terminated polyoxypropylene, methanol in an amount of 10% of the polyoxypropylene Then, 4 mol of n-amylamine was added, and heating and stirring was started at 60° C. under a nitrogen atmosphere. Incidentally, every hour after the start of heating and stirring, a small amount was taken out and the viscosity at 25°C was measured. The viscosity, which was 210 cSt before heating and stirring, reached 3,700 cSt 8 hours after the start of heating and stirring, and after that, the viscosity increased by adding 2 moles of a stopper silicon compound (silane compound) and heating and stirring under the same conditions. Continued. A small amount was extracted every hour after the addition of the silane compound and the epoxy groups were titrated using the hydrochloric acid dimethylformamide method. As a result, the disappearance of the epoxy groups was observed 6 hours after the addition of the silane compound, so the methanol was distilled off. 25
A viscous liquid (polymer expressed by the following formula) having a viscosity of 24,000 cSt at ℃ and a specific gravity of 1.01 at the same temperature was obtained.

(CIl:30) zsi(Cllz juice N -(-Cl
2CHCH20(C1lCH2O stone-C)1zcHcH
z-N(C)Izmido-ysi(OCI,)2lh Example 3 For 6 epoxy equivalents of glycidyl group-end-blocked polyoxypropylene with an average degree of polymerization of 50 and a molecular weight of approximately 3.000.25°C and a viscosity of 970 cSt. , ethanol in an amount of 10% of polyoxypropylene and 2 moles of allylamine were added, and heating and stirring at 60° C. under nitrogen atmosphere was started. A small amount was taken out every hour from the start of heating and stirring, and the viscosity at 25°C was measured. 370 before heating and stirring
The viscosity, which was cSt, decreased to 3 after 8 hours from the start of heating and stirring.
, 900 cS t was reached, and the viscosity increase stopped after that, so heating C1h C11C11zNCHzCII□C
Two moles of an organosilicon compound (silane compound) represented by 1l□5i(OC11+)z were added, and heating and stirring was continued under the same conditions. After the addition of the silane compound, a small amount was taken out every hour and the epoxy group was titrated using the hydrochloric acid dimethylformamide method. As a result, the disappearance of the epoxy group was observed 6 hours after the addition of the silane compound, so heating and stirring was stopped. Ethanol was distilled off to obtain a pale yellow viscous liquid (polymer shown below) having a viscosity of 31.000 cSt at 25°C and a specific gravity of 1.01 at the same temperature.

-CII□CII CII□-N-(-CIl□-hS
i (OC113) 2 Example 4 For 10 epoxy equivalents of glycidyl group-end-blocked polyoxypropylene with an average weight of 15 and a molecular weight of about 1.000.25°C and a viscosity of 270 cSt as used in Example 1, Methanol in an amount of 10% of polyoxypropylene and 4 moles of n-hexylamine were added, and heating and stirring at 60° C. under a nitrogen atmosphere was started. Incidentally, every hour after the start of heating and stirring, a small amount was taken out and the viscosity at 25°C was measured. The viscosity was 90cSt before heating and stirring, but it decreased to 1,100cS 8 hours after heating and stirring started.
St, and the viscosity increase stopped thereafter, so 12 hours after the start of heating and stirring, CH, CIl□NCHzCHzCHzSi(OCI+*
) Organosilicon compound (silane compound) represented by 3
1 mol and Cl13CH2NCH2CII□CII
Heating and stirring was continued under the organic condition represented by zSi (CH3) z. After adding the silane compound, a small amount was withdrawn every hour and the epoxy group was titrated using the hydrochloric acid dimethylborumamide method. As a result, the disappearance of the epoxy method was observed 6 hours after the addition of the silane compound, so heating and stirring was stopped. Methanol was distilled off to obtain a pale yellow viscous liquid having a viscosity of 12,000 cSt at 25°C and a specific gravity of 1.01 at the same temperature.

Example 5 6 epoxy equivalents of glycidyl group-end-blocked polyoxypropylene having the same average polymerization degree of 50 and molecular weight of about 3.000 as used in Example 3 were heated at 90°C under pressure in a nitrogen atmosphere. Heating and stirring was started. When a small amount was taken out every 6 hours from the start of heating and stirring and the viscosity at 25°C was measured, the viscosity was 390 cSt before heating and stirring, but 2,900 cSt 24 hours after heating and stirring started.
The temperature reached 60°C in the viscosity, and the temperature was reduced to
2.4 mol of an organosilicon compound (silane compound) represented by HzClhCII□5i(OCH:+)z was added, and heating and stirring was continued under the same conditions. After the addition of the silane compound, a small amount was taken out every hour and the epoxy group was titrated using the hydrochloric acid dimethylformamide method. As a result, the disappearance of the epoxy group was observed 6 hours after the addition of the silane compound, so heating and stirring was terminated, and methanol was distilled off to obtain a pale yellow viscous liquid (polymer shown below) having a viscosity of 28.000 cSt at 25°C and a specific gravity of 1.01 at the same temperature.

-ClhCllCILz-N(C1l□hsiiOCH
+)z Application Example 1 For 100 parts by weight of the polymer obtained in Example 1, 30 parts by weight of fatty acid-treated colloidal calcium carbonate, 15 parts by weight of rutile titanium oxide, 65 parts by weight of fatty acid-treated light calcium carbonate, and 15 u of dioctyl phthalate. 3 parts by weight of hydrogenated castor oil, 22 parts by weight of antioxidant [2゜2'-methylenebis(4-methyl-5-t-butylphenol)], 22 parts by weight of ultraviolet absorber [2(2'-hydroxy-3゛), 5° -G-t
-butylphenyl)-5-chlorobenzotriazole 3
After adding 2 parts by weight and 0.5 parts by weight of carbon blank and mixing uniformly with three rolls, the mixture was heated to 60 to 70°C and the degree of vacuum was 5 mm.
Kneading was carried out for 2 hours using 11 g. After cooling, 1 part by weight of dibutyltin dilaurate was added and mixed under reduced pressure to obtain Sample 1.

Using sample 1 thus obtained, a specimen for a tensile test as shown in FIG. 1 was prepared. The prepared test specimen was heated at 25°C.
After curing and curing for 4 days, a tensile test was conducted to measure the rubber physical properties and adhesive strength.

The results are shown in Table 1.

Application Example 2 For 100 parts by weight of the polymer obtained in Example 2, 50 parts by weight of fatty acid-treated colloidal calcium carbonate, 50 parts by weight of ground calcium carbonate, 30 parts by weight of dioctyl phthalate, 4 parts by weight of hydrogenated castor oil, and rutile. 20 parts by weight of type titanium oxide, antioxidant [4,4''-butylidene bis(3-methyl-6-
t-butylphenol)] 2 parts by weight, ultraviolet absorber [2
Add 32 parts by weight of (2°-hydroxy-3''5+-di-t-butylphenyl)-5-chlorobenzotriazole and mix uniformly using three rolls, then heat at 60 to 70°C and vacuum at 5 mmHg for 2 hours. Kneading was performed. After cooling, 1 part by weight of dibutyltin dilaurate was added.
Sample 2 was obtained by mixing under reduced pressure. Using Sample 2, the same measurements as in Application Example 1 were performed. The results are also shown in Table 1.

Application Example 3 To 100 parts by weight of the polymer obtained in Example 3, 30 parts by weight of fatty acid-treated colloidal calcium carbonate, 30 parts by weight of light calcium carbonate, 15 parts by weight of rutile-type titanium helidene, 6 parts by weight of hydrogenated castor oil, Antioxidant [2,6-bis(2-hydroxy-5-methylbenzyl)-4-methylphenol) 2 ffiit parts, UV absorber (2(2'-hydroxy-5-methylphenyl)henzotriadur)] 2 parts After adding parts by weight and mixing uniformly with 3 rolls, 60~70°
Kneading was carried out for 2 hours at a C1 vacuum of 5 mn + 1 g. After cooling, 1 part by weight of dibutyltin oxide was added and mixed under reduced pressure to obtain Sample 3.

The same measurements as in Application Example 1 were performed using Sample 3.

The results are also shown in Table 1.

Application example 4 For 100 parts by weight of the polymer obtained in Example 4, 30 parts by weight of fatty acid-treated colloidal calcium, 1 part by weight of rutile titanium oxide
5 parts by weight, 65 parts by weight of fatty acid-treated light calcium carbonate,
15 parts by weight of dioctyl phthalate, 3 parts by weight of hydrogenated castor oil, antioxidant (L3,5-trimethyl-2,4,6-1
- Lis(3,5-di-butyl-4-hydroxybenzyl) Hensen] 5 parts by weight, UV absorber [2 (2°
-Hydroxy-5-methylphenyl)benzotriazole] 2 parts by weight, add 0.5 parts by weight of carbon blank and 3
After uniformly mixing with this roll, the temperature is 60-70℃ and the degree of vacuum is 5.
Kneading was carried out for 2 hours at mm11H. After cooling, 1 ffi part of dibutyltin dilaurate was added and mixed under reduced pressure to obtain Sample 4. Application example 1 using sample 4
The same measurements were carried out. The results are also shown in Table 1.

Application Example 5 To 100 parts by weight of the polymer obtained in Example 5, 30 parts by weight of fatty acid-treated colloidal calcium carbonate, 30 parts by weight of light calcium carbonate, 15 parts by weight of rutile titanium oxide, 6 MM parts of hydrogenated castor oil, and antioxidant. [2,6-bis(2-hydroxy-5-methylbenzyl)-4-methylphenol]
and ultraviolet absorber C2 (2''-hydroxy-5-methylphenyl)benzotriazole] were added, and after uniformly mixing with three rolls, the mixture was heated to 60 to 70°C.
The mixture was kneaded for 2 hours at a vacuum degree of 5 mmHg.

After cooling, 1 part by weight of dibutyltin oxide was added and mixed under reduced pressure to obtain Sample 5. The same measurements as in Application Example 1 were performed using Sample 5. The results are also shown in Table 1.

[Brief explanation of drawings]

FIG. 1 is a perspective view of a test specimen for a tensile test. Also,
Numerical values other than those listed below indicate dimensions, and the unit is mm. l: Sample 2: Adherent

Claims (1)

[Claims] 1(A) General formula; ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R^1 and R^2 are divalent hydrocarbon groups, and n is 10
~250), the molecular chain end is blocked with an epoxy group, and (B) general formula; R^3-NH_2 (wherein R^3 is a substituted or unsubstituted 1
Monovalent primary amine or general formula represented by a monovalent hydrocarbon group: ▲Mathematical formula, chemical formula, table, etc.▼ (In the formula, R^4 and R^6 are monovalent hydrocarbon groups, R^5 is 2
Divalent secondary amine represented by (representing a valent organic group) and (C) general formula; ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R^7 is a monovalent hydrocarbon group, R^ 8 is a divalent hydrocarbon group, R^9 is a monovalent hydrocarbon group, R^1^0 is a monovalent hydrocarbon group having 1 to 6 carbon atoms, and a represents a number from 1 to 3). An organosilicon compound having an amino group and a hydrolyzable group represented by (D) general formula; A general formula characterized by reacting in the presence of a monovalent primary alcohol represented by (representing a hydrocarbon group); ▲ There are mathematical formulas, chemical formulas, tables, etc. , there are tables, etc. ▼ [II] (R^1, R^2, R^3, R^4, R^5, R^6,
R^7, R^8, R^9, R^1^0, a and n are as mentioned above, m is a number selected so that the molecular weight is in the range of 1,000 to 50,000) A method for producing a polyether end-capped with a hydrolyzable silyl group. 2. The manufacturing method according to claim 1, wherein R^1 is an ethylene group and/or a propylene group. 3. The manufacturing method according to claim 1, wherein R^5 is a divalent hydrocarbon group. 4. The manufacturing method according to claim 1, wherein R^1^0 and R^1^1 are a methyl group or an ethyl group. 5. The manufacturing method according to claim 4, wherein R^1^0 and R^1^1 are methyl groups.