JPS6333425A - Copolymer having molecular chain terminal blocked with hydrolyzable silyl group and production thereof - Google Patents

Abstract

PURPOSE:To obtain the titled copolymer forming a rubbery elastomer with moisture, by reacting a polyxyalkylene having epoxy group at molecular terminal with a siloxane, an amine compound and an organic Si compound having epoxy group and hydrolyzable group. CONSTITUTION:The objective copolymer of formula V or formula VI can be produced by reacting (A) a polyoxyalkylene of formula I (R<1> and R<2> are bivalent hydrocarbon group; m is 10-500) having epoxy group at molecular chain terminals, (B) a siloxane of formula II (R<3> is unhydrolyzable bivalent hydrocarbon group having a main chain composed solely of C, N, S and O atoms and free from adjacent hetero-atom; R<4> is hydrocarbon group; n is 6-500) having epoxy group at molecular chain terminals, (C) an amine compound of formula R<5>NH2 (R<5> is hydrocarbon group) or a diamine compound of formula III (R<6> and R<8> are H or hydrocarbon group; R<7> is bivalent organic group) and (D) an organic Si compound of formula IV (R<9> is same as R<3>; R<10> is hydocarbon group; X is hydrolyzable group; a is 1-3) having epoxy group and hydrolyzable group.

Description

Detailed Description of the Invention [Technical Field of the Invention] The present invention relates to copolymers whose molecular chain ends are blocked with hydrolyzable silyl groups and which can be cured into a rubber-like elastic body at room temperature when exposed to moisture. In particular, the present invention relates to a copolymer useful as a base polymer for a room-temperature curable composition that provides a rubber-like cured product with excellent adhesiveness and high elongation, and a method for molding the copolymer.

[Technical background of the invention and its problems]

Polymers having hydrolyzable silicon functional groups and having a polyether main chain are known (Japanese Patent Laid-Open No. 50-156599).
Publications, etc.). In recent years, room-temperature-curable compositions based on this polymer have begun to be used as sealants for joints in buildings and joints in transportation machinery (Japanese Patent Laid-Open No. 52-7399
Publication No. 8, etc.).

However, since this type of polymer does not inherently have adhesive properties, it is necessary to pre-treat the surface to which it is applied by applying a brimer, or add a silane coupling agent to the composition to improve its adhesive properties. It is necessary to grant. However, the addition of a silane coupling agent poses a problem in that the elongation rate of the rubber-like elastic body after curing decreases, making it brittle, in exchange for the acquisition of adhesive properties.

[Purpose of the invention]

The present invention is intended to solve these problems, and provides a copolymer useful as a base polymer for a room-temperature curable composition that provides a rubber-like cured product with excellent adhesion and high elongation, and its production. The purpose is to provide a method.

[Means for solving problems]

That is, the present invention is based on the general formula % (wherein R1 and R2 are divalent hydrocarbon groups, R3 and R9 have main chains consisting only of C, N, S and O atoms,
A non-hydrolyzable divalent hydrocarbon group having no adjacent heteroatoms, R4 and R16 are monovalent hydrocarbon groups, R5 is a substituted or unsubstituted monovalent hydrocarbon group, R6
and R8 is a hydrogen atom or a monovalent hydrocarbon group, R7 is a divalent organic group, X is a hydrolyzable group, a is a number from 1 to 3, m
is a number from 10 to 500, n is a number from 6 to 500, k and j
is a number from 1 to 10 and the molecular weight of the copolymer is 1.000 to 50.
,000. ) A copolymer whose molecular chain ends are blocked with a hydrolyzable silyl group, and (8) -formula (wherein R1 and R2 are divalent hydrocarbon groups, Akebono is a 10
Indicates a number of ~500. ) Polyoxyalkylene whose molecular chain end is blocked with an epoxy group, (B)-formula (wherein R3 is a main chain consisting only of C, N, S and O atoms, and the adjacent hetero atoms are a non-hydrolyzable divalent hydrocarbon group, R4 is a monovalent hydrocarbon group,
n represents a number from 6 to 500. ) A siloxane whose molecular chain end is blocked with an epoxy group, (C)-format R'-NH, (wherein R5 represents a substituted or unsubstituted monovalent hydrocarbon group) An amine compound or a diamine compound represented by the general formula % (wherein P and R11 are a hydrogen atom or a monovalent hydrocarbon group, and R7 is a divalent organic group) and a (D)-form RIG3- (In the formula, R9 is a non-hydrolyzable divalent hydrocarbon group whose main chain consists only of C, N, S, and O atoms and has no adjacent heteroatoms, and RIO is a monovalent hydrocarbon group. base,
X represents a hydrolyzable group, and a represents a number from 1 to 3. ) is reacted with an organosilicon compound having an epoxy group and a hydrolyzable group. , k and j are numbers from 1 to 10, and the molecular weight of the copolymer is 1.
, 6oo to 50,000. ) The present invention relates to a method for producing a copolymer whose molecular chain terminals are blocked with a hydrolyzable silyl group represented by the following formula.

General formula of the present invention % formula % (wherein R'""R" , X , a + II +
n, and j are as described above. ) In the copolymer represented by R'0, the oxyalkylene unit represented by R'0 is preferably an oxyethylene unit, an oxypropylene unit, or a combination system of an oxyethylene unit and an oxypropylene unit, since raw materials are easy to obtain and polymerize, and high polymerization is possible. Oxypropylene units are particularly preferred because they can easily maintain their liquid state even at low temperatures.

Examples of the divalent hydrocarbon group for R2 include a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, a phenylene group, and a cyclohexylene group. Among these groups,
A methylene group is preferred from the viewpoint of easy availability of raw materials.

R3 and R9 are non-hydrolyzable divalent hydrocarbon groups whose main chain consists only of C, N, S and O atoms and no adjacent heteroatoms, and -CHz-0(C
Hz)r, -CHzCHzOCHzCHz-.

-(C1bCHzO)-rCRzGHz-, -0CHz
An example is Hz-. After these, due to the availability of raw materials, -CHz-0+CHz)y (however,
A trimethylene group is bonded to the silicon atom. ) is preferable.

R4 and RIG are monovalent hydrocarbon groups, including alkyl groups such as methyl, ethyl, propyl, butyl, and hexyl; alkenyl groups such as vinyl and allyl;
Examples include aryl groups such as phenyl group and tolyl group; aralkyl groups such as β-phenylethyl group and β-phenylpropyl group; however, methyl group and phenyl group are preferred from the viewpoint of ease of synthesis of raw materials, and are easily available. A methyl group is particularly preferred.

R3 is a substituted or unsubstituted monovalent hydrocarbon group;
In addition to those exemplified by 4 and RIG, examples thereof include hydroxyethyl group, 2-methoxyethyl group, p-hydroxyphenyl group, p-chlorophenyl group, and the like. Among these, because it has excellent heat resistance and weather resistance,
Aromatic groups such as phenyl and p-hydroxyphenyl are preferred.

R6 and R8 are hydrogen atoms or monovalent hydrocarbon groups, and examples of the monovalent hydrocarbon groups include those exemplified for R4 and RIo.

Further, the divalent organic group of R7 is preferably a divalent hydrocarbon group from the viewpoint of ease of obtaining raw materials and precursors and synthesis, and examples thereof include an ethylene group, a trimethylene group, a hexamethylene group, a cyclohexylene group, and a phenylene group. Ru. On the other hand, phenylene groups, which have excellent heat resistance and weather resistance,
A divalent aromatic group such as divalent is preferred.

The hydrolyzable group of X is an alkoxy group, an alkoxyalkoxy group, an acyloxy group, an N,N-dialkylamino group,
Examples include N-alkylamide group, N,N-dialkylaminoxy group, ketoxime group, and alkenoxy group,
Because of their ease of availability, reactivity, and non-corrosion of hydrolyzed products to metals, alkoxy groups having 1 to 6 carbon atoms, such as methoxy, ethoxy, propoxy, isopropoxy, and hexyloxy groups, and A 2-methoxyethoxy group is suitable, a methoxy group and an ethoxy group are preferred from the viewpoint of high hydrolyzability, and a methoxy group is particularly preferred. The number a of hydrolyzable groups is selected within the range of 1 to 3, but it is preferable that a is 2 in order to obtain a base polymer of a composition that provides a rubber-like cured product with a high elongation rate.

The polymerization degree layer of oxyalkylene units is selected in the range of 10 to 500, and when m is less than 10, a copolymer that provides a rubber-like cured product with a sufficient elongation rate at a viscosity below that which provides practical workability. becomes difficult to obtain. On the other hand, m is 500
If it is larger, the adhesiveness, which is a feature of the present invention, will be reduced.

The degree of polymerization n of the siloxane unit is selected in the range of 6 to 500. If n is smaller than 6, it becomes difficult to obtain a copolymer that provides a rubber-like cured product with a high elongation rate. Also, n is 5
If it is larger than 00, the non-staining property and post-paintability of the rubber-like cured product using this as a base polymer will deteriorate.

k and j are numbers from 1 to 10, and the molecular weight of the copolymer is i
, ooo to 50,000. If the molecular weight is less than i, ooo, it will not be possible to obtain a copolymer that provides a rubber-like cured product with a high elongation rate, which is a feature of the present invention, and if it exceeds 50,000, the viscosity will increase and workability will decrease.

The copolymer of the present invention has, for example, the (A)-formula (wherein R1 and R2 are divalent hydrocarbon groups, m is 10
Indicates a number of ~500. ) Polyoxyalkylene whose molecular chain end is blocked with an epoxy group, (B)-Formula % (In the formula, R3 is a main chain consisting only of C, N, S and 0 atoms, which are adjacent to each other. A non-hydrolyzable divalent hydrocarbon group that does not have a heteroatom, R4 is a monovalent hydrocarbon group,
n represents a number from 6 to 500. ) A siloxane whose molecular chain end is blocked with an epoxy group, (C)-format R'-NH, (wherein R5 represents a substituted or unsubstituted monovalent hydrocarbon group) Amine compounds or diamine compounds represented by the general formula % formula % (wherein R6 and R8 represent a hydrogen atom or a monovalent hydrocarbon group, and R7 represents a divalent organic group) and (D)-formula % formula % (wherein, R9 is a non-hydrolyzable divalent hydrocarbon group whose main chain consists only of C, N, S and 0 atoms and has no adjacent heteroatoms, R1 (1 is monovalent can be synthesized by reacting an epoxy group represented by a hydrocarbon group, X is a hydrolyzable group, and a is a number from 1 to 3 with an organosilicon compound having a hydrolyzable group. can.

A typical example of (A) is one obtained by adding epichlorohydrin to polyoxyethylene or polyoxypropylene, both ends of which are blocked with hydroxyl groups, in the presence of a basic catalyst or the like.

A typical example of (B) is obtained by adding allyl glycidyl ether to polydimethylsiloxane or polymethylphenylsiloxane in which both ends are blocked with hydrogen atoms bonded to silicon atoms in the presence of a platinum catalyst. Things can be mentioned.

A typical example of (C) is C as RS-NH2.
H3 (CHz) 3NH2, C1t3 (eHz) aN
Hz, CHz=CiIC)lzN)lz.

H Examples include.

Specific examples of component (D) include γ-glycidoxypropyltrimethoxysilane, γ-glycidoxybutyltrimethoxysilane, T-glycidoxypropyltriethoxysilane, γ-glycidoxybutyl Triethoxysilane, Methyl (T-glycidoxypropyl) dimethoxysilane, Methyl (T-glycidoxybutyl) dimethoxysilane, Methyl (T-glycidoxypropyl) jetoxysilane, Methyl (γ-glycidoxybutyl) Jetoxysilane, phenyl (T-glycidoxypropyl) dimethoxysilane, phenyl (T-glycidoxybutyl) dimethoxysilane, dimethyl (T-glycidoxypropyl)
Methoxysilane, dimethyl (γ-glycidoxybutyl)
Methoxysilane and compounds in which these alkoxy groups are replaced with alkoxyalkoxy groups, acyloxy groups, N,N-dialkylamino groups, N-alkylamido groups, N,N-dialkylaminoxy groups, ketoxime groups, alkenoxy groups, etc. can give.

The copolymer of the present invention comprises (A), CB) and (D)
It is obtained by the reaction between the epoxy group of (C) and the amino group of (C).

The reactions of (^), (B), (C) and (D) are preferably carried out at a temperature higher than the ambient temperature, e.g. 50-150°C. Preferably, compounds such as (dimethylaminomethyl)phenol are used as reaction accelerators. Methanol is one of the preferred ones. Note that hydrocarbon-based, ether-based, and ester-based solvents can be used when carrying out this reaction, but if the liquid is relatively small, the compatibility of each component is good, so it is necessary to use a solvent. There is no.

The amounts of (A), (B), (C) and (D) to be blended are theoretically such that the molar ratio is (A):(B):(C):(D
) = k : j : (k+j+1):2. However, in reality, there is no problem even if (C) and (D) are used in amounts slightly exceeding the theoretical amounts.

The reaction procedure is (A), (B), (
C) and (D) may be added and reacted at the same time,
First, (A), (B) and an amount exceeding their equivalents,
and i; React an amount of (C) suitable for obtaining a copolymer having a molecular weight in the range indicated in I in the presence of an alcohol or phenol, and after copolymerization, a necessary amount or a slightly larger amount. It is easier to control the degree of polymerization by adding (D) to the reaction, and it is also possible to reliably introduce a hydrolyzable group to the end of the molecular chain.

〔Effect of the invention〕

The copolymer of the present invention has excellent adhesive properties and is useful as a base polymer for room-temperature curable compositions that yield rubber-like cured products with high elongation. By using the copolymer of the present invention as a base polymer, adhesiveness can be developed without brimer treatment on the adherend or without adding an adhesion improver such as a silane coupling agent to the composition. Furthermore, it is possible to obtain a sealing material that is free from staining due to adhesion of dust.

6 Examples] EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples.

In the Examples, Applied Examples, and Applied Comparative Examples, all parts are by weight, and % is by weight.

Example 1 Average degree of polymerization] 51 3 moles of glycidyl group-end-blocked polyoxypropylene having a molecular weight of about 1,000.25°C and a viscosity of 270 eSt, 2 moles of siloxane represented by CH3C11ff, and the total weight of oxypropylene and siloxane. Add methanol in an amount equivalent to 10% and heat at 80°C under nitrogen atmosphere.
Heating and stirring was started. A portion of the sample was taken out at 4-hour intervals from the start of heating and stirring, and the total amount of epoxy groups and primary amines in the sample was determined using potentiometric titration, and the viscosity at 25° C. was also measured. 16 hours after the start of heating and stirring, the titration of epoxy groups and primary amines decreased by almost the theoretical amount, and the viscosity, which was 150 cSt before heating, decreased to □3.
Since the temperature reached 600 cSt, the temperature was changed to C11 and heating and stirring was continued under the same conditions. After adding the silane, a portion was taken out at 4 hour intervals and the total amount of epoxy groups and primary amines in the sample was determined using potentiometric titration, and it was found that they almost disappeared 12 hours after the addition of the silane. However, since no peak due to protons of epoxide methylene was observed by NMR, heating and stirring was stopped, methanol was distilled off, and the viscosity at 25°C was 1.
A pale yellow viscous liquid (polymer represented by the following formula) having a specific gravity of 1.01 at the same temperature was obtained. This polymer is hereinafter referred to as P-1.

Cll3 0H)I
tlOHCH3CL
OH1l 1
1,000 GHz CII-CIlz (l(C11zChichoH3i-0)rrSi-(CIlrhrO-CH2-C
ICI (2-CH, CH3 Example 2 2 moles of glycidyl group-end-blocked polyoxypropylene having an average degree of polymerization of 50 and a molecular weight of about 3,000.25°C viscosity of 970 cSt, used in Example 1, C) Is 1 mole of siloxane represented by Cll3, 4 moles of n-butyl 7mine, and phenol equivalent to 5% by weight based on the total weight of polyoxypropylene and siloxane were added, and the mixture was heated and stirred at a temperature of 60°C under a nitrogen atmosphere. It started. A portion of the sample was extracted every 4 hours from the start of heating and stirring, and the total amount of epoxy groups and amines in the sample was determined using potentiometric titration. As a result, the titration amount of epoxy groups and amines increased within 16 hours from the start of heating and stirring. The viscosity decreased by almost the theoretical amount, and when the viscosity was measured at 25°C, it reached 33.000 cSt. To this was added 2 moles of CH3 organosilicon compound, and heating and stirring was continued under the same conditions. After adding the above silane, a portion was taken out every 4 hours and the total amount of epoxy groups and amines in the sample was determined using potentiometric titration, and it was found that they had almost disappeared 8 hours after the addition of the silane. In addition, since the peak due to protons of epoxide methylene was no longer observed by NMR, heating and stirring was stopped, and the viscosity at 25°C was 38.000 cSt, and the specific gravity at the same temperature was 1.01.
A pale yellow viscous liquid (polymer represented by the following formula) was obtained. Hereinafter, this polymer will be referred to as P-2.

(CIIIiO)zsiffclhh-0-CHz-CH
-CHz N-HCHzCH-CHz-0-II3 -CHzCH-CHz-0-(CHg)r-St(OC
H3)z Example 3 2 moles of glycidyl group-end-capped polyoxypropylene with an average degree of polymerization of 50 and a molecular weight of about 3.000.25°C viscosity of 97QcSt, 2 moles of siloxane represented by the following, 5 moles of n-butylamine, and Phenol corresponding to 3% by weight based on the total weight of polyoxypropylene and siloxane was added, and using tetrahydrofuran as a solvent, heating and stirring was started at the solvent reflux temperature under a nitrogen atmosphere. After starting heating and stirring, 4
When a portion was taken out every hour and the total amount of epoxy groups and amine was measured using potentiometric titration, it was found that the titration of epoxy groups and amine decreased by approximately the theoretical amount 20 hours after the start of heating and stirring.

After distilling off the solvent tetrahydrofuran, the viscosity at 25°C was measured and found to be 42.000 cSt. To this was added 2 moles of CH3 organosilicon compound, and heating and stirring was continued under the same conditions. After adding the above silane, a portion was taken out every 4 hours and the total amount of epoxy groups and amines in the sample was determined using potentiometric titration, and it was found that they almost disappeared 12 hours after the addition of the silane. Since the peak due to protons of epoxide methylene was no longer observed by NMR, the viscosity at 25°C after heating and stirring was ended and the solvent tetrahydrofuran was distilled off was 45.000.
A pale yellow viscous liquid (polymer represented by the following formula) having a specific gravity of 1.01 at the same temperature as cSt was obtained. This polymer is hereinafter referred to as P-3.

CH30H (CHz) 5cHs OHI
II 1(C)1
30) zsi-(C1l□h-0-CHz CHC
)It N--HCHzCH-CHz-0--(CH
CHzO)vicHz -CI-CHz -N -hH
CHzclI -Cl t -0--(C1lz)y-
(Si-0)nrsi(CHzh-0-CHz CH
CHz-N-ShoI C'As CH3 -CHzCH-CHg-0-(CHz)r Si (Q
C) I: +) z Example 4 Same as used in Example 1, average degree of polymerization 15, molecular weight approximately 1,000.25°C viscosity 270 cS
3 moles of polyoxypropylene with glycidyl groups blocked at both ends of t, the mountain used in Example 3? II.

Added 3 moles of siloxane represented by 3 moles of ethylenediamine, 3% by weight of phenol based on the total weight of oxypropylene and siloxane, used tetrahydrofuran as a solvent, and started heating and stirring at the solvent reflux temperature under a nitrogen atmosphere. . After the start of heating and stirring, a portion was taken out every 4 hours and added to the epoxy groups using potentiometric titration.
1. When quantifying &S i of primary amine,
After 16 hours, the total amount of epoxy groups and primary amines decreased by almost the same amount as the theoretical value. After distilling off the solvent tetrahydrofuran, the viscosity at 25°C was 38. o
It had reached ooC5t. Add 2 organic silicon compounds to this
mol was added, and heating and stirring was continued under the same conditions. After adding the above silane, a portion was taken out every 4 hours and the total amount of epoxy groups and primary amines was determined using potentiometric titration method, and it was found that they almost disappeared after 12 hours. Since the peak due to protons of epoxide methylene was no longer observed, heating and stirring was stopped, and a pale yellow viscous liquid with a viscosity of 41,000 cst at a temperature of 25°C and a specific gravity of 1.01 at the same temperature (expressed by the following formula) Polymer) was obtained. This polymer is hereinafter referred to as P-4.

CH30HHtl Kano', CII 30) ZS i day CH2 agency 0-CIl□
-CII -C11□-N-(C1l□斤N (Ctl
zCII-C1l□-CH30HHtl OH 11+ 1 1-0-(cl
lcHzzohicHz-(j(C1lz-N 4C1l
□hN hill-(c++ zclI -co□-〇-CH3
CHi OHII Itl
1 II 1-(CH
2) T→5i-0)-1 Si→CH, 0-CL
CIICtLz-N (CH□斤N]gol CH3CH3 -CHzCH-CHz-0beCHJySi (OCH:
+)! Application Examples 1 to 4 100 parts of the copolymer obtained in Examples 1 to 4, in which the molecular chain ends were blocked with hydrolyzable silyl groups, were given the fillers, inorganic pigments, and thixotrovisotic properties shown in Table 1. After adding the agent and uniformly dispersing it with a Miki roll, the first
The organic tin compounds shown in the table were added and mixed to obtain samples 1 to 4. These samples were cured into sheets with a thickness of about 2 mm+, cured for 14 days at room temperature, and then punched into JIS No. 2 Danhers, and the surface condition was observed by finger touch and a tensile test was performed. Then, in the same manner, the obtained dumbbell-shaped test piece was placed in a 150°C dryer and a weather meter, and after being subjected to the deterioration conditions (heating and ultraviolet irradiation) for the period shown in Table 1, the sample piece was Condition observation and tensile test were conducted.

These results are also shown in Table 1.

Application Comparative Example 1 About 8,000 molecules, (C1130) as the terminal group zSi-CI□CI, CH□-〇-
For 100 parts of polyoxypropylene having
After adding the filler, a-free pigment, and thixotropy imparting agent shown in the table and uniformly dispersing them with a triple roll, the organic tin compound shown in Table 1 was added and mixed to obtain sample 5. . Tests similar to Application Examples 1 to 4 were conducted using this sample 5. The results are also shown in Table 1.

Application Examples 5 to 8 Using the same samples 1 to 4 as those prepared in Application Examples 1 to 4, shear adhesion test specimens shown in FIG. 1 were created. After curing the prepared test specimens at room temperature for 28 days, a tensile test was conducted.

The results are shown in Table 2.

Application Comparative Example 2 Using the same sample 5 as that prepared in Application Comparative Example 1, a shear adhesion test specimen shown in FIG. 1 was prepared. Tests similar to those in Application Examples 5 to 8 were conducted using this test specimen. The results are also shown in Table 2.

[Brief explanation of the drawing]

FIG. 1 shows a perspective view of a specimen subjected to a shear adhesion test. Note that the unit in the figure is mm. 1... Sample

Claims (1)

[Claims] 1 General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R^1 and R^2 are divalent hydrocarbon groups, R ^
3 and R^9 are non-hydrolyzable divalent hydrocarbon groups whose main chain consists only of C, N, S, and O atoms and have no adjacent heteroatoms, R^4 and R^1 ^0 is a monovalent hydrocarbon group, R^5 is a substituted or unsubstituted monovalent hydrocarbon group, R^6 and R^8 are hydrogen atoms or monovalent hydrocarbon groups, R^7 is a divalent hydrocarbon group organic group, X is a hydrolyzable group, a is a number from 1 to 3, m is a number from 10 to 500, n is a number from 6 to
The number 500, k and j are numbers from 1 to 10 and are selected so that the molecular weight of the copolymer is in the range from 1,000 to 50,000. ) is a copolymer whose molecular chain ends are blocked with hydrolyzable silyl groups. 2. The copolymer according to claim 1, wherein R^1 is an ethylene group and/or a propylene group. 3 Claim 2, in which R^1 is a propylene group
Copolymer described in section. 4. The copolymer according to claim 1, wherein R^2 is a methylene group. 5 R^3 and R^9 are -CH_2O-(CH_2)
-_3 (However, the trimethylene group is bonded to the silicon atom.) Claim 1
Copolymer described in section. 6. The copolymer according to claim 1, wherein R^4 and R^1^0 are methyl groups. 7. The copolymer according to claim 1, wherein R^7 is a divalent hydrocarbon group. 8. The copolymer according to claim 1, wherein R^7 is a divalent aromatic group. 9. The copolymer according to claim 1, wherein X is an alkoxy group having 1 to 6 carbon atoms. 10. The copolymer according to claim 8, wherein X is a methoxy group. 11. The copolymer according to claim 1, wherein a is 2. 12 (A) Molecules represented by the general formula ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (In the formula, R^1 and R^2 are divalent hydrocarbon groups, and m represents a number from 10 to 500.) Polyoxyalkylene whose chain end is blocked with an epoxy group, (B) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R^3 is a main chain consisting only of C, N, S, and O atoms. , a non-hydrolyzable divalent hydrocarbon group having no adjacent heteroatoms, R^4 is a monovalent hydrocarbon group, n is 6 to 500
Indicates the number of ) A siloxane whose molecular chain end is blocked with an epoxy group, (C) with the general formula R^5-NH_2 (wherein R^5 represents a substituted or unsubstituted monovalent hydrocarbon group). Amine compounds or general formulas represented by ▲ Numerical formulas, chemical formulas, tables, etc.▼ (In the formula, R^6 and R^8 are hydrogen atoms or monovalent hydrocarbon groups, and R^7 is a divalent organic group. ) and (D) general formula ▲ mathematical formula, chemical formula, table, etc. A non-hydrolyzable divalent hydrocarbon group having no atoms, R^1^0 is a monovalent hydrocarbon group, X is a hydrolyzable group, and a represents a number from 1 to 3.) A general formula characterized by reacting the expressed epoxy group with an organosilicon compound having a hydrolyzable group ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula , R^1 to R^1^0, X, a, m and n are as described above, k and j are numbers from 1 to 10, and the molecular weight of the copolymer is in the range of 1,000 to 50,000. A method for producing a copolymer whose molecular chain ends are blocked with a hydrolyzable silyl group, represented by the number selected as follows.