JPS63241012A - Organosilicon group-containing copolymer and its preparation - Google Patents

Abstract

PURPOSE:To prepare the title copolymer which is excellent in heat resistance and vulcanization characteristics and small in permanent compression set, by polymerizing a monomer containing a double bond capable of addition polymn. and a specified organosilicon compound. CONSTITUTION:70-99.99mol.% monomer containing a double bond capable of addition polymn A (e.g. ethyl acrylate) and 30-0.01mol.% organosilicon compound B of formula I [where V is an organic group containing a double bond capable of addition polymn.; n is 0-10; m is 1-2; Y is a vinylsilyl-containing organosilicon group of formula II or III {where R is H or a monovalent hydrocarbon group; the end group of the respective groups constituting an organosilicon unit is SiR3; the siloxy units containing vinylsilyl are in an optional configuration; a is 0-30; b is 1-10; one or more of R on the side chain can be substituted by a group of formula IV; x is a; y is b; g is 0-1; d and e are a; f is 1-2, and g+f=2}], are polymerized, with the double bond in V of formula I in priority, allowing the vinylsilyl of ingredient B to remain, to give the title copolymer containing recurring units derived from ingredient A and recurring units of formula V derived from ingredient B and having an MW of 1,000-2,000,000.

Description

DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to a novel organosilicon foil-containing copolymer, and more specifically, it has excellent heat resistance, low compression set,
This invention relates to an organosilicon foil-containing copolymer with extremely excellent vulcanization properties and a method for producing the same.

BACKGROUND OF THE INVENTION It is a common practice to crosslink organic polymer materials with peroxide, sulfur, etc. to improve their physical properties. In particular, in the manufacturing process of rubber products, with some exceptions, the crosslinking reaction (generally called vulcanization) step is essential, and the performance of rubber products is often highly dependent on this vulcanization step. Therefore, vulcanizing agents and vulcanization accelerators have been used since ancient times.

Many studies have been conducted on accelerators, vulcanization conditions, etc.

On the other hand, in rubbers with low crosslinking efficiency such as ethylene-propylene rubber and acrylic rubber, a method of introducing reactive groups as crosslinking points has been conventionally used. The performance of the resulting rubber product is often greatly influenced by the type of reactive group introduced as a crosslinking point. Up to now, a series of studies have been made to introduce carbon-carbon double bonds into polymers as crosslinking points (crosslinking reactive groups). By the way, generally, in order to introduce a carbon-carbon double bond into a polymer as a crosslinking group, a conjugated diene or a non-conjugated diene compound is copolymerized, but ordinary organic diene compounds have two unsaturated bonds. Among them, the difference in reactivity between the unsaturated bonds that cause a polymerization reaction during addition polymerization and the unsaturated bonds that should be left as crosslinking points is not very large, so the unsaturated bonds that should be left as crosslinking points under the polymerization reaction conditions are also They tend to react and form branched or cross-linked structures in the polymer during the polymerization process, making it difficult to control the molecular weight and molecular weight distribution, resulting in a decline in product processability and physical properties. On the other hand, to overcome such drawbacks.

By lowering the reactivity of unsaturated bonds that should remain as crosslinking points,
The vulcanization properties deteriorate, and the heat resistance of the obtained rubber product also deteriorates and the compression set increases.

Therefore, a method has recently been proposed in which a vinylsilyl group with low polymerization reactivity is introduced into a polymer as a crosslinking reactive group using a vinylsilyl group-containing monomer (Japanese Patent Application Laid-Open No. 1989-1993).
-88015, JP-A-60-90205, JP-A-61-
127711, JP-A-6L-127764).

However, since the vinylsilyl group-containing monomers used in these known methods all have a vinylsilyl group at the end of the monomer, the polymerization reactivity of the vinylsilyl group is insufficiently low, and branching occurs in the polymer under single polymerization reaction conditions. It is not possible to prevent the formation of a cross-linked structure, and the resulting polymer cannot be said to have sufficient thermal properties, compression set, and vulcanization properties.

Problems to be Solved by the Invention The inventors have conducted intensive research with the aim of providing a polymer with even better heat resistance and compression set, and extremely excellent vulcanization properties. As a compound (monomer) having a vinylsilyl group-containing organosilicon group, a monomer in which a vinylsilyl group is present in the side chain or a monomer in which the vinylsilyl group has reduced polymerization reactivity due to steric hindrance is used, and this is subjected to addition polymerization. The inventors discovered that a copolymer with excellent heat resistance, compression set, and extremely excellent vulcanization properties could be obtained by copolymerizing with a monomer having a possible double bond, leading to the completion of the present invention. Ta.

Means for solving the problems, that is, the gist of the present invention is as follows: (1) General formula (I) monomer M±-(I) (M represents a monomer unit having a double bond capable of addition polymerization) 70 to 99.99 mol% of repeating units represented by
and General formula (11) (V represents a unit of an organic group having a double bond capable of addition polymerization.

n is 0 to 10. m is an integer of 1-2.

Y represents an organosilicon group containing a vinylsilyl group represented by the following general formula (m) or (IV), and has a repeating unit of 0.01 to 30 mol% and a molecular weight of 1.0
00-2,000,000 organosilicon group-containing copolymer.

(III) (Here, R is a hydrogen atom or a same or different unsubstituted or substituted monovalent hydrocarbon group excluding an alkenyl group, which may be the same or different, and which constitute the organosilicon unit. Among the various trees, the terminal group is S I R3.

Furthermore, siloxy units having a vinylsilyl group are optionally numbered. a is 0-30, and b is 1-10. Also, at least one of the R's in the side chain may be substituted with RCH=CH2R, where R is the same as above, X is O~30, and y is O~10. ) (Left below) ■ CH=CH2 (Here, R is a hydrogen atom, the same or different unsubstituted or substituted monovalent hydrocarbon groups excluding alkenyl groups, and each may be the same or different. is 0~
1. d is O~30, e is O~30, f is 1~2, g+f
=2, and if f is 2, then each d and each e in the two repeating units within the brackets may be different, )(2)
A monomer having a double bond capable of addition polymerization, and a general formula (V) Ve-e-(CH2)rl-Y), (
V) (V represents an organic group having a double bond capable of addition polymerization, n is 0Nio, m is an integer of 1 to 2; Y is a vinylsilyl group represented by the above general formula (m) or (IV) The organic silicon group-containing compound represented by ), which represents an organosilicon foil containing A method for producing an organosilicon group-containing copolymer, characterized in that the polymerization reaction is carried out under conditions that allow the polymerization to occur.

Hereinafter, the constituent elements of the present invention will be explained.

(Monomer having a vinylsilyl group-containing organic silicon foil) The monomer having a vinylsilyl group-containing organic silicon foil used in the present invention is a compound represented by the following general formula (V).

V-(-(CH2)n-Y), (V)
Here, ■ represents an organic group having a double bond capable of addition polymerization, and n is 0 to 10. m is an integer of 1-2. Y represents a vinylsilyl group-containing organosilicon foil.

Next, the vinylsilyl group-containing organosilicon foil will be explained.

The vinylsilyl group-containing organosilicon foil has the following general formula (m)
or (IV).

(m) In this formula, R is a hydrogen atom, a monovalent substituted or unsubstituted hydrocarbon of the same or different type excluding an alkenyl group, a methyl group, an alkyl group such as an ethyl group, a propyl group, a butyl group, and a phenyl group. aryl groups such as tolyl groups, cycloalkyl groups such as cyclohexyl groups, or groups in which some or all of the hydrogen atoms bonded to the carbon atoms of these groups are substituted with halogen atoms such as fluorine or chlorine, cyano groups, etc. An alkyl group having 1 to 4 carbon atoms or a phenyl group is preferable from the viewpoint of ease of obtaining an organosilicon compound, and a methyl group is more preferable. Among them, the terminal is -3iR3M, and the vinylsilyl group is only in the side chain.

When at least one of the terminal groups is a vinylsilyl group, branching and crosslinking structures are likely to be formed during the addition polymerization reaction, making it difficult to control the molecular weight and molecular weight distribution. However, if the terminal group is a group other than a vinylsilyl group, the polymerization reactivity will be lowered due to the effect of steric hindrance, and the heat resistance, compression set resistance, and vulcanization properties will be extremely good.

a is 0-30. Preferably it is 0 to 1o.

b is 1-10, preferably 1-5.

Further, it may be an organosilicon foil in which the polymerization reactivity of vinylsilyl groups is suppressed to a low level due to the effect of steric hindrance, Cf, or an organosilicon foil represented by the following general formula (IV).

(Left space below) -3i - CH=CH2 (IV) Here, R is a hydrogen atom or a non-concave or substituted monovalent hydrocarbon group of the same or different type excluding an alkenyl group, as in R in formula (III) above. 0g is O~1, and d is O~30. e
is 0 to 10, f is 1 to 2, g+f=2, and if f is 2, each d and each e in the two repeating units in brackets
may be different) The vinylsilyl group in this organosilicon group is present in the side chain, and even when d and e are zero, there is steric hindrance due to the presence of the 10 S t R3 group bonded to the silicon atom. As a result, polymerization reactivity is reduced.

(Organosilicon group-containing monomer) Specific examples of the organosilicon group-containing monomer used in the present invention include the following formula.

(Left below) Such vinyl group-containing organosilicon compounds can be obtained by applying well-known methods using these compounds. A method of cohydrolysis or condensation reaction with chlorosilane and a furkylchlorosilane such as trimethylchlorosilane or dimethyldichlorosilane, or a desalination reaction between the above-mentioned chlorosilane and (hereinafter referred to as the margin) (R, d, and e are as described above), etc. can get. Further, the ethylenic double bond or epoxy group-containing alkoxysilane can be obtained by known organic synthesis reactions such as Grignard reaction and hydrosilylation reaction.

(Septumer having an addition-polymerizable double bond) Monomer (M) having an addition-polymerizable double bond used in the present invention
Examples of such monomers include the following monomers, and these monomers may be used not only alone, but also in combination of 28 or more.

Olefins such as ethylene, propylene, isobutylene, dienes such as phtadiene, isoprene, chloroprene, ethylidenenorbornene, dicyclopentadiene, unsaturated carboxylic acids such as ethyl acrylate, butyl acrylate, methyl (meth)acrylate, methoxyethyl acrylate Examples include addition-polymerizable monomers such as vinyl compounds such as esters, vinyl chloride, vinyl acetate, styrene, acrylonitrile, methacrylonitrile, vinylidene chloride, vinylidene fluoride, tetrafluoroethylene, hexafluoropropylene, and vinylidene cyanide. However, the present invention is not limited to these.

(Polymerization method) The polymerization mode when polymerizing the monomer (M) having a double bond capable of addition polymerization and the vinyl group-containing organosilicon foil-containing compound includes solution polymerization, bulk polymerization, emulsion polymerization, and suspended fi polymerization. The zero-polymerization active species used may be an anion, a cation, or a radical. A vinyl group bonded to a silicon atom (
Vinylsilyl groups) hardly undergo a polymerization reaction under normal polymerization conditions due to steric hindrance by other organic groups. In particular, in the present invention, vinylsilyl groups do not have a terminal vinylsilyl group, or their silicon atom Because we use organosilicon group-containing monomers with other organic groups that have a strong steric hindrance effect.

Under normal polymerization conditions, vinyl silyl groups remain.

Does not create branching or bridging structures.

(Copolymer) The copolymer of the present invention has 70 to 99.99 repeating units represented by the general formula (I) +Mt (1) (M represents a monomer unit having a double bond capable of addition polymerization). With mole%.

General formula (■,) (V represents a unit of an organic group having an addition-polymerizable double bond.

n is 0-10. m is an integer of 1-2.

Y represents an organosilicon group containing a vinylsilyl group)
It is an organosilicon group-containing copolymer having a repeating unit of 0.01 to 30 mol % and a molecular weight t of ooo to 2,000,000.

The repeating unit of general formula (I) is 70 to 99.99 mol%, preferably 90 to 99.9 mol%. Also,
The repeating unit of general formula (II) is 0.01 to 30 mol%, preferably 0.1 to 10 mol%. If the repeating unit of general formula (n) is less than 0.01 mol 5, the crosslinking density will be low even if crosslinked, and the effect of improving physical properties by crosslinking will not be seen. If it becomes too high, it will have an adverse effect on physical properties.

(The number average molecular weight of the polymer of the present invention is 1,000 to 2.000.
,000, but preferably 10°000~i,
, o o o, o o o; particularly preferably 50
．． 000~aoo, ooo.

When t is smaller than ooo, effective crosslinking is difficult to be carried out even if the vinylsilyl group content is increased, so a good crosslinked product cannot be obtained.When it is larger than 2,000,000, the viscosity becomes too large and processability It worsens and is undesirable.

(Iodine value) The iodine value of the polymer of the present invention is 0.01 to 20, preferably 0.1 to 15, more preferably 0.5 to 10.
It is.

If it is less than 0.01, the crosslinking density will be too low and no effect will be seen even if it is crosslinked, and if it is more than 20, the crosslinking density will be too high and will affect the physical properties, which is also not preferable.

(Processing and Additives) The polymer of the present invention thus obtained can be processed by conventional methods using rolls, internal mixers, routers, etc. If necessary, black filling such as carbon black or Kettin black may be added. white fillers such as silica gel, clay, mica, charcoal, and talc, various plasticizers, R colorants, processing aids, extenders, oils, anti-aging agents, vulcanizing agents,
Vulcanization accelerators, vulcanization acceleration aids, etc. can be added.

Examples of the vulcanizing agent include peroxides, silicon compounds having two or more hydrosilyl groups, sulfur and sulfur compounds, and crosslinkable resins.

When the copolymer of the present invention is vulcanized with a silicon compound having two or more hydrosilyl groups, it is rapidly vulcanized in the presence of a catalyst such as a platinum compound.

EXAMPLES Next, the present invention will be specifically explained with reference to Examples, but the present invention is not limited to these Examples.

Synthesis example of a monomer having a vinylsilyl group-containing organosilicon group Synthesis example-1 A flask equipped with a dropping funnel was charged with 200 parts of γ-methacryloxypropyltrichlorosilane and 350 parts of tetrahydrofuran, mixed to homogenize, and then added to a flask equipped with a dropping funnel. 400 m of a 2N tetrahydrofuran solution of vinylmagnesium bromide was heated to a temperature of 10°C in a nitrogen stream.
The solution was added dropwise over a period of 2 hours while maintaining the temperature. After stirring for another hour to react, filter and distill.
196 parts of reaction product were obtained. When this reaction product was analyzed by gas chromatography, the purity of γ-methacryloxypropylvinyldichlorosilane was 82%.

Next, 600 parts of water was added to a flask equipped with a dropping funnel.
450 parts of hexane and 380 parts of methanol were charged and mixed uniformly. On the other hand, 196 parts of the above reaction product and 332 parts of trimethylchlorosilane were collected in another flask and made into a homogeneous mixture, and then added to an aqueous solution of n-hexane and methanol through a dropping funnel while maintaining the liquid temperature at 5°C. The mixture was added dropwise over a period of time and reacted by stirring for 15 minutes, followed by washing, drying and distillation under reduced pressure to obtain 115 parts of a vinyl group-containing polyorganosiloxane compound represented by the general formula %. .

Synthesis Example-2 207 parts of dimethyldichlorosilane and 570 parts of tetrahydrofuran were charged into a flask equipped with a dropping funnel, mixed and homogenized, and then 1000 parts of a tetrahydrofuran solution containing P-vinylphenylmagnesium chloride was poured into a nitrogen stream from the dropping funnel. The solution was added dropwise over 2 hours while keeping the temperature of the solution at 10°C. After stirring for another hour,
Passage and distillation were carried out in the same manner as in the example process to obtain 220 parts of P-vinylphenyldimethylquery silane.

Next, add 1000 parts of water to a flask equipped with a dropping funnel.
- 700 parts of hexane and 600 parts of methanol were charged and mixed uniformly. On the other hand, 197 parts of the aforementioned reaction product (p-vinylphenyldimethylchlorosilane), 212 parts of methylvinyldichlorosilane, and 183 parts of trimethylchlorosilane were collected in another flask and mixed to form a homogeneous mixture, and then n- It was dropped into an aqueous solution of hexane and methanol from a dropping funnel over 1 hour while keeping the liquid temperature at 5°C. After stirring for 15 minutes to react, the solution was washed in the same manner as in Example 1. By drying and distilling under reduced pressure, 61 parts of a vinyl group-containing polyorganosiloxane compound represented by the general formula: % formula % was obtained.

Synthesis Example-3 A flask equipped with a dropping funnel was charged with 128 parts of 2-(5-norbornenyl)ethyltrichlorosilane and 230 parts of tetrahydrofuran, mixed to homogenize, and 250 parts of a tetrahydrofuran solution of 0 and 2N vinylmagnesium bromide was prepared. ml at a temperature of 10°C in a nitrogen stream.
The solution was added dropwise over a period of 2 hours while maintaining the temperature. After stirring and reacting for an additional hour, filtration and vacuum distillation were performed in the same manner as in Example 1 to obtain 82 parts of 2-(5-norbornenyl)ethylvinyldichlorosilane.

Next, the above-mentioned 2-(5-
50 parts of (norbornenyl)ethylvinyl dichlorosilane and 120 parts of tetrahydrofuran were charged, mixed and homogenized, and then 130 parts of a polyorganosiloxane compound represented by the general formula: 2
It was added dropwise at 0°C over 2 hours, stirred for another 1 hour to react, and then washed, dried and distilled under reduced pressure in the same manner as in Example 1 to obtain a compound with the general formula: % formula %) 142 parts of the vinyl group-containing polyorganosiloxane compound shown was obtained.

Synthesis Example 4 In a flask, 200 parts of allyl itaconate, 130 parts of dimethylchlorosilane, and a 296 isopropyl alcohol solution of chloroplatinic acid with a platinum content of 10 ppm relative to dimethylchlorosilane were charged.

While stirring uniformly, the mixture was heated to 70 to 80°C and kept for 1 hour to react. Thereafter, washing, drying and dehydration were performed in the same manner as in Example 1 to obtain 360 parts of (hereinafter referred to as margin) X.

Next, 60 parts of this compound and 400 parts of tetrahydrofuran were charged into a flask equipped with a dropping funnel, and 300 parts of a polyorganosiloxane compound represented by the general formula:
The mixture was added dropwise over a period of time, stirred at 25° C. for 1 hour, and then washed, dried, and distilled under reduced pressure in the same manner as in Example 1.

(The following is a blank space) General formula: (Compound 4) 200 parts of a vinyl group-containing polyorganosiloxane compound represented by the following was obtained.

Synthesis Example-5 98.8 parts of methylvinyldichlorosilane and 350 parts of tetrahydrofuran were charged into a flask equipped with a dropping funnel and mixed uniformly, and then 450 parts of a tetrahydrofuran solution containing p-vinylphenylmagnesium chloride was poured from the dropping funnel into a nitrogen stream. The solution was added dropwise over 2 hours while keeping the temperature of the solution at 10°C. After stirring for another hour,
The mixture was passed through the mouth to remove the produced magnesium salt.

The filtered liquid was distilled to obtain 140 parts of a reaction product. When this reaction product was analyzed by gas chromatography, the purity of the target product, p-vinylphenylvinylmethylchlorosilane, was 91%.

Next, in a flask equipped with a dropping funnel, 500 parts of water, n
- 380 parts of hexane and 320 parts of methanol were charged and mixed uniformly. On the other hand, 140 parts of the above reaction product and 300 parts of trimethylchlorosilane were collected in another flask, thoroughly mixed to form a homogeneous mixture, and then poured into an aqueous solution of n-hexane and methanol through a dropping funnel. Warmth 5
The mixture was added dropwise for 1 hour while being kept at ℃. After that, add 1 part of the liquid
After reacting by stirring for 5 minutes, the mixture was washed, dried, and distilled under reduced pressure in the same manner as in Example 1.

(Margin below) General formula: %formula%) 84 parts of a reaction product represented by was obtained.

(Left below) Example 1 According to the polymerization recipe shown in Table 1, an autoclave with an internal volume of 6 liters was used, and the monomer conversion rate was 9 at a reaction temperature of 5°C.
After the reaction was completed, 0.5 part of sodium dimethylthiocarbamate was added to stop the polymerization.Next, 1 part of alkylated diphenylamine was added as a stabilizer to the reaction solution, and the mixture was heated by steam distillation. After removing the uncoupled monomer, aluminum sulfate was added to solidify the resulting polymer. This coagulated polymer was washed with water and then dried using a vacuum dryer.

(The following is a blank space) Examples 2 to 4 Polymers were obtained in the same manner as in Example 1 except that the seven-mer composition was changed as shown in Table 2.

(Leaving space below) Table 2 Example 5 2M of dehydrated n-hexane was charged into a 3-way separable flask that had been purged with nitrogen in advance, and then ethylene/
A mixed gas of propylene/hydrogen = 515/a (molar ratio) was introduced into the flask, and then 1.25 mmol of Compound-3, which had been dissolved at room temperature for about 10 minutes, was charged and stirred with a cuff. Zarani AMEt Cf1 mmol, vOC13
The polymerization reaction was started by charging 1,51,50.5 mmol.

After continuing the reaction for 30 minutes while maintaining the polymerization temperature at 20°C, 1mM of inpropyl alcohol was added to the polymerization solution to stop the polymerization reaction.The polymerization reaction solution was poured into a large amount of methanol to solidify and then vacuum-dried.

Comparative Example 1 A copolymer was obtained according to Example 1 of JP-A-61-127711.

Comparative Example 2 A copolymer was obtained according to Example 4 of JP-A-61-127711.

Examples 1 to 5, Comparative Examples 1 to 2, Comparative Example 3 (acrylic rubber ARI O1 manufactured by Japan Synthetic Rubber Co., Ltd.), Comparative Example 4 (
Ethylene propylene rubber EP4 manufactured by Japan Synthetic Rubber Co., Ltd.
Table 3 shows the molecular weight, molecular weight distribution, iodine value, Mooney viscosity, gel amount, and organic silicon group-containing monomer repeating unit (mol %) of the copolymer obtained in 3).

Examples 6-10, Comparative Examples 5-8 Examples 1-5. The polymers of Comparative Examples 1 to 4 were kneaded and blended in a conventional manner using an internal mixer, and evaluated.

The formulation and physical property values at that time are shown in Table 4.

Further, the vulcanization curves of Example 6 and Comparative Examples 5 and 7 are shown in FIG.
The physical property test of the vulcanized rubber was conducted according to JIS K6301. The vulcanization curve was measured using JSR Curastometer m (manufactured by Japan Synthetic Rubber Co., Ltd.).

(Hereinafter referred to as blank spaces) Effects of the Invention According to the present invention, a copolymer having excellent heat resistance, low compression set, and excellent vulcanization properties can be obtained.

[Brief explanation of drawings]

FIG. 1 shows the vulcanization curves of Example 6 and Comparative Examples 5 and 7 measured by JSR Curastmeter (manufactured by Japan Synthetic Rubber Co., Ltd.).

Claims (1)

[Claims] (1) 70 to 99.99 repeating units represented by the general formula (I) -[M]-(I) (M represents a monomer unit having a double bond capable of addition polymerization) mole%
and General formula (II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) (V indicates a unit of an organic group having a double bond capable of addition polymerization. n is 0 to 10, m is 1 to 2 is an integer of Y represents an organosilicon group containing a vinylsilyl group represented by the following general formula (III) or (IV). 0
00 to 2,000,000 organosilicon group-containing copolymers. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (III) (Here, R is a hydrogen atom, or the same or different unsubstituted or substituted monovalent hydrocarbon groups excluding alkenyl groups, which may be the same or different. , and among the various groups constituting the organosilicon unit, the terminal group is SiR_3. Also, the siloxy units having a vinylsilyl group are arranged arbitrarily, a is 0 to 30, and b is 1 to 10. .And also, at least one of the R's in the side chain may be substituted with ▲There are mathematical formulas, chemical formulas, tables, etc.▼ Here, R is the same as above, x is 0 to 30, and y is 0 to 10) ▲Mathematical formulas, chemical formulas, tables, etc.▼(IV) (Here, R is a hydrogen atom, an unsubstituted or substituted monovalent hydrocarbon group of the same or different type excluding an alkenyl group, and each They may be the same or different.g is 0 to
1, d is 0-30, e is 0-30, f is 1-2, g+f
=2, and when f is 2, each d and each e in the two repeating units within the brackets may be different. )(2)
Claim No. 1 having an iodine value of 0.01 to 20
) The copolymer described in item 1. (3) The monomer unit having an addition-polymerizable double bond represented by the general formula (I) is a monomer unit selected from olefins, dienes, unsaturated carboxylic acid esters, and vinyl compounds. ) The copolymer described in item 1. (4) The organosilicon group-containing monomer unit represented by general formula (II) is CH_2=CR-X-Y, ▲ mathematical formula, chemical formula,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, and ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (However, R is a hydrogen atom or a methyl group, and X is (CH_
2)_n, COO(CH_2)_n, CH_2-O-(
CH_2)_n, CH=CH(CH_2)_n, COO(CH_2)_n, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and n is an integer from 0 to 10. be. Y represents the organosilicon group. ) The copolymer according to claim 1, which is a compound selected from the following. (5) A monomer having a double bond capable of addition polymerization, and a general formula (V) V-(CH_2)_n-Y)_m(V) (V represents an organic group having a double bond capable of addition polymerization. n is an integer of 0 to 10, m is an integer of 1 to 2, and Y represents an organosilicon group containing a vinylsilyl group represented by the following general formula (III) or (IV). A group-containing compound is subjected to a polymerization reaction under conditions that leave the vinylsilyl group in the organosilicon group and preferentially polymerize the addition-polymerizable double bond in the organic group V. A method for producing a basic group-containing copolymer. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (III) (Here, R is a hydrogen atom, or the same or different unsubstituted or substituted monovalent hydrocarbon groups excluding alkenyl groups, which may be the same or different. , and among the various groups constituting the organosilicon unit, the terminal group is SiR_3. Also, the siloxy units having a vinylsilyl group are arranged arbitrarily. a is 0 to 30, and b is 1 to 10. , and also, at least one of the R's in the side chain may be substituted with ▲a mathematical formula, a chemical formula, a table, etc.▼, where R is the same as above, x is 0 to 30, and y is 0 to 30.) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (IV) (Here, R is a hydrogen atom, an unsubstituted or substituted monovalent hydrocarbon group of the same or different type excluding an alkenyl group, and each They may be the same or different.g is 0 to
1, d is 0-30, e is 0-30, f is 1-2, g+f
=2, and when f is 2, each d and each e in the two repeating units within the brackets may be different. ) (6) The method for producing a copolymer according to claim (5), which has an iodine value of 0.01 to 20. (7) The monomer having a double bond capable of addition polymerization is a monomer selected from olefins, dienes, unsaturated carboxylic acid esters, and vinyl compounds.
5) A method for producing a copolymer according to item 5). (8) The organosilicon group-containing compound represented by the general formula (IV) is CH_2=CR-X-Y, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and ▲There are mathematical formulas, chemical formulas, tables, etc.▼ ( However, R is a hydrogen atom or a methyl group, and X is (CH_
2)_n, COO(CH_2)_n, OH_2-O-,
(CH_2)_n, CH=CH(CH_2)_n, COO(CH_2)_n, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, where n is an integer from 0 to 10 It is. Y represents the organosilicon group. ) A method for producing a copolymer according to claim (5), wherein the copolymer is a compound selected from the following.