JPH07224168A - (meth)acrylic function organopolysiloxane and its production - Google Patents

Abstract

PURPOSE:To obtain the subject polysiloxane useful as a graft copolymer having excellent water repellency, mold release characteristics, etc., containing (meth) acrylic group at the end, a silicon atom bonded through an alkylene group to the (meth)acrylic group and a trimethylsiloxy group bonded to the silicon atom. CONSTITUTION:(A) A (meth)acrylic functional organosilicon compound of formula I [R<1> is H or methyl; R<2> is methyl or OSi(CH3)3 group; (m) is 1-14 integer; A is H or Li] is reacted with (B) hexamethylcyclotrisiloxane to give an intermediate of formula II ((n) is 3-200 integer). This intermediate is, directly or after conversion of A into H in the case where A is Li, reacted with an end hindering agent selected from oragnosilicon compounds of formula III to formula V (R<3> to R<5> are a monofunctional hydrocarbon; R<6> to R<8> each is H or alkyl) to give a (meth)acrylic functional organopolysiloxane of formula VI. In the reaction, the compound of formula I wherein A is H is preferably usedand the reaction is preferably carried out in the presence of a specific 5-coordination silicon catalyst.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention has one (meth) acryl group at the terminal represented by the following general formula (1), and the (meth) acryl group is a silicon atom through an alkylene group. A novel (meth) acryl-functional organopolysiloxane in which a trimethylsiloxy group is bonded to the silicon atom and a method for producing the same, and in particular, copolymerizable with a vinyl-based monomer and graft-copolymerized with the vinyl-based monomer The invention relates to a (meth) acryl-functional organopolysiloxane capable of producing a graft copolymer having excellent water repellency, releasability, slipperiness, weather resistance and gas permeability, and a method for producing the same.

[0002]

[Chemical 6] (In the formula, R ¹ is a hydrogen atom or a methyl group, R ² is a methyl group or —OSi (CH ₃ ) ₃ group, R ³ , R ⁴ and R ⁵ are each a substituted or unsubstituted monovalent hydrocarbon group, m Is an integer from 1 to 14,
n is an integer of 3 to 200. )

[0003]

2. Description of the Related Art It has been known to synthesize an organopolysiloxane having a (meth) acryl group at one end by ring-opening polymerization of hexamethylcyclotrisiloxane. There is.
For example, in JP-A-59-78236, hexamethylcyclotrisiloxane is subjected to ring-opening polymerization using lithium trimethylsilanolate as a polymerization initiator, and 3
A method for synthesizing an organopolysiloxane having a (meth) acryl group at one end by stopping the reaction with-(2-methacryloxyethoxy) propyldimethylchlorosilane has been proposed.

In Japanese Patent Laid-Open No. 2-92933, lithium (3-methacryloxy) propyldimethylsilanolate is used as a polymerization initiator, hexamethylcyclotrisiloxane is subjected to ring-opening polymerization, and the reaction is stopped with trimethylchlorosilane. Have proposed a method for synthesizing an organopolysiloxane having a (meth) acrylic group at one end.

Further, hexamethylcyclotrisiloxane is subjected to ring-opening polymerization in the presence of a pentacoordinated silicon catalyst, using trimethylsilanol or 3-methacryloxypropyldimethylsilanol as an initiator, and then 3-methacryloxypropyldimethylchlorosilane, respectively. Alternatively, a method of synthesizing an organopolysiloxane having a (meth) acryl group at one end by stopping the reaction with trimethylchlorosilane is also known.

However, since the hydroxyl group bonded to the trimethylsilyl group and the 3- (meth) acryloxypropyldimethylsilyl group is generally unstable, it is relatively easily dehydrated and condensed to form a dimer. That is, when performing the polymerization using trimethylsilanol as a polymerization initiator,
There is a problem that hexamethyldisiloxane and water are generated by the condensation, and di (meth) acryldisiloxane is generated by the reaction of this water and the chlorosilane having a (meth) acryl group as an end-capping agent. .

Further, a dimer is also easily produced from a lithium silanolate compound obtained by lithiating a silanol compound. In particular, when the polymerization was carried out using a silanol compound or a lithium silanolate compound having a (meth) acrylic group as an initiator, di (meth) acryldisiloxane was immediately produced and remained in the system as it was. It was difficult to remove the di (meth) acrylic disiloxane even if the (meth) acrylic functional organopolysiloxane was washed with methanol.

Therefore, when an attempt is made to obtain a copolymer by copolymerizing the (meth) acryl-functional organopolysiloxane obtained by the above synthesis method with a vinyl monomer, the above-mentioned residual di (meth) There was a problem that the copolymer was gelled by using acrylic disiloxane as a crosslinking agent.

The present invention has been made in view of the above circumstances.
An object of the present invention is to provide a (meth) acrylic functional organopolysiloxane having a low content of di (meth) acrylic compound and a method for producing the same.

[0010]

MEANS TO SOLVE THE PROBLEMS As a result of intensive studies to achieve the above object, the present inventor has found that a (meth) acryl-functional organosilicon compound represented by the following general formula (2) is used as a polymerization initiator. Was used as a reaction product and reacted with hexamethylcyclotrisiloxane to obtain an intermediate represented by the following general formula (3). If necessary, A in the formula (3) was a lithium atom, which was converted to a hydrogen atom. Then, by reacting an end-capping agent selected from the organosilicon compounds represented by the following general formulas (4) to (6), the following general formula (1)
It was found that a novel (meth) acrylic functional organopolysiloxane represented by

[0011]

[Chemical 7] (In the formula, R ¹ is a hydrogen atom or a methyl group, R ² is a methyl group or —OSi (CH ₃ ) ₃ group, R ³ , R ⁴ and R ⁵ are each a substituted or unsubstituted monovalent hydrocarbon group, m Is an integer from 1 to 14,
n is an integer of 3 to 200, A is a hydrogen atom or a lithium atom, and R ⁶ , R ⁷ , and R ⁸ are a hydrogen atom or an alkyl group. )

The (meth) acryl-functional organopolysiloxane of the formula (1) has a stable silanol group or lithium silanolate group as a polymerization initiator,
In addition, since it is synthesized using a silicon compound that also has a (meth) acrylic group, the content of di (meth) acrylic compound is small,
Therefore, even when this (meth) acrylic functional organopolysiloxane is copolymerized with a vinyl-based monomer, it does not gel and has excellent water repellency, releasability, slipperiness, weather resistance, gas permeability, etc. It has been found that a copolymer can be obtained. Further, although the conventional (meth) acryl-functional organopolysiloxane uses expensive 3-methacryloxypropyldimethylchlorosilane as a raw material, the formula (2) for obtaining the (meth) acryl-functional organopolysiloxane of the present invention is used. The organosilicon compound of 1) can be easily synthesized from inexpensive 3-methacryloxypropylmethyldichlorosilane or 3-methacryloxypropyltrichlorosilane, which can also be a raw material of a silane coupling agent, and is advantageous in terms of cost. Knowing that there is
The present invention has been completed.

The only known organic silicon compounds having a (meth) acrylic group and a silanol group in one molecule are those in which an alkyl group such as a methyl group is bonded to a silicon atom bonded to a hydroxyl group. Such silanol groups are generally unstable and easily dehydrate and condense to give di (meth) acryldisiloxane. Therefore, in the (meth) acrylic functional polysiloxane obtained using such an organosilicon compound as an initiator, di (meth)
Although the acrylic disiloxane remains, the silanol compound represented by the above general formula (2) has one or two trimethylsiloxy groups bonded to the silicon atom to which the hydroxyl group is bonded. It is difficult for the body to generate.
The reason is presumed to be steric hindrance to the silanol group of the reaction substrate due to the presence of the bulky trimethylsiloxy group around the silanol group.

Therefore, according to the present invention, the (meth) acryl-functional organopolysiloxane represented by the general formula (1) and the organosilicon compound represented by the general formula (2) are reacted with cyclotrisiloxane to produce the above-mentioned compound. When the intermediate of the general formula (3) is obtained and A of the intermediate of the general formula (3) is a lithium atom, if necessary, this is converted into a hydrogen atom, and then the organic compound of the general formulas (4) to (6) is obtained. Provided is a method for producing a (meth) acrylic functional organopolysiloxane of the formula (1), which comprises reacting with an end-capping agent selected from silicon compounds.

The present invention will be described in more detail below. The (meth) acrylic functional organopolysiloxane of the present invention is represented by the following formula (1).

[0016]

[Chemical 8] (In the formula, R ¹ is a hydrogen atom or a methyl group, R ² is a methyl group or —OSi (CH ₃ ) ₃ group, R ³ , R ⁴ and R ⁵ are each a substituted or unsubstituted monovalent hydrocarbon group, m Is an integer from 1 to 14,
n is an integer of 3 to 200. )

Here, the substituted or unsubstituted monovalent hydrocarbon group is preferably one having 1 to 10 carbon atoms, particularly 1 to 8 carbon atoms, and an alkyl group, an alkenyl group, an aryl group, an aralkyl group or a group thereof. In the above, some or all of the hydrogen atoms are substituted with halogen atoms, and the following are exemplified.

[0018]

[Chemical 9]

Specific examples of the (meth) acrylic functional organopolysiloxane represented by the above formula (1) include those shown below.

[0020]

[Chemical 10]

[0021]

[Chemical 11]

[0022]

[Chemical 12]

The (meth) acryl-functional organopolysiloxane of the above formula (1) is prepared by using an organosilicon compound represented by the following general formula (2) as a polymerization initiator, as shown in the following reaction formula. It can be obtained by polymerizing with methylcyclotrisiloxane and then reacting the obtained intermediate of the general formula (3) with an end capping agent of the general formulas (4) to (6).

[0024]

[Chemical 13] (In the formula, R ¹ is a hydrogen atom or a methyl group, R ² is a methyl group or —OSi (CH ₃ ) ₃ group, R ³ , R ⁴ and R ⁵ are each a substituted or unsubstituted monovalent hydrocarbon group, m Is an integer from 1 to 14,
n is an integer of 3 to 200, A is a lithium atom of a hydrogen atom, and R ⁶ , R ⁷ , and R ⁸ are hydrogen atoms or alkyl groups. In this case, the alkyl group preferably has 1 to 6 carbon atoms. )

Here, the organosilicon compound (polymerization initiator) of the formula (2) is one or two trimethylsiloxy groups [OSi (CH ₃ )] on the silicon atom to which the (meth) acryl group is bonded via the alkylene group. _[3 ] are bonded to each other, and specifically include the following.

[0026]

[Chemical 14]

[0027]

[Chemical 15]

In this case, the silanol group-containing organosilicon compound in which A is a hydrogen atom has been proposed by the present applicant in Japanese Patent Application No. 5-226438, and the corresponding (meth) acrymex Methyldichlorosilane or (meth) acryloxyalkyltrichlorosilane is reacted with 1 or 2 equivalents of trimethylsilanol to introduce a trimethylsiloxy group, and then the remaining chloro group is reacted with water to form silanol, which is then purified by distillation. Can be manufactured by.

The lithium silanolate group-containing organosilicon compound in which A is a lithium atom is easily synthesized by reacting the silanol group-containing organosilicon compound with an organolithium reagent such as n-butyllithium in a conventional manner. can do.

When the organosilicon compound (polymerization initiator) of the above formula (2) is reacted with hexamethylcyclotrisiloxane, the molar ratio is 1: 1 to 1:70, particularly 1: 1 to 1: 1.
It is preferably 1:50.

In this reaction, the following general formula (7)
A pentacoordinated silicon catalyst represented by the following formula can be used, and particularly when the above-mentioned lithium silanolate group-containing organosilicon compound is used as a polymerization initiator, such a catalyst is not necessarily required, but a silanol group-containing compound wherein A is a hydrogen atom When using an organosilicon compound, it is recommended to use the pentacoordinated silicon catalyst.

[0032]

[Chemical 16] (In the formula, R ⁹ is a substituted or unsubstituted monovalent hydrocarbon group, and M is Li, Na, K, NH ₄ or C ₆ H ₅ CH ₂ N (CH ₃ ) _3. )

The pentacoordinated silicon catalyst represented by the above formula (7) is described in JP-B-45-1070, and specific examples thereof include the following.

[0034]

[Chemical 17]

Of these, a pentacoordinated silicon catalyst having an alkali metal as a counter ion is preferable from the viewpoints of ease of synthesis, stability with time, and excellent polydispersity of the polysiloxane obtained by polymerization. Used.

The amount of the pentacoordinated silicon catalyst used is 100 to 1000 pp relative to hexamethylcyclotrisiloxane.
m, particularly preferably 200 to 500 ppm.

The above reaction is preferably carried out in a solvent. Examples of such a reaction solvent include polar solvents and non-polar solvents containing no active hydrogen, and specifically, acetonitrile, tetrahydrofuran, 1,4-dioxane, methyl ethyl ketone, methyl isobutyl ketone, dimethyl sulfoxide, dimethylformamide, hexane. , Toluene, xylene, and the like. Among them, acetonitrile is particularly preferably used when the silanol group-containing organosilicon compound is used, and tetrahydrofuran is preferably used when the lithium silanolate group-containing organosilicon compound is used. . These reaction solvents are preferably dehydrated using a desiccant such as molecular sieves.

Although the reaction conditions are appropriately selected, when the silanol group-containing organosilicon compound is used as a polymerization initiator, the reaction temperature is 50 to 100 ° C., particularly 60 to 80 ° C.
The reaction time can be 1 to 20 hours, and when the lithium silanolate group-containing organosilicon compound is used as a polymerization initiator, the reaction temperature is -30 to 20 ° C, particularly -15 to 5 ° C.
The reaction temperature may be 1 ° C. and the reaction time may be 1 to 10 hours.

Thus, a (meth) acryl group and one or two trimethylsiloxy groups at one end and a silanol group or a lithium silanolate group at the other end are obtained, and the above formula (3) The indicated organopolysiloxane intermediate can be obtained.

Next, the intermediate of the formula (3) is reacted with the organochlorosilane of the formula (4), the aminosilane of the formulas (5) and (6) or silazane as a terminal blocking agent,
Replacing the A of the formula (3) to -SiR ³ R ⁴ R ^5. In this case, when A is a lithium atom, if necessary, the lithium atom can be converted to a hydrogen atom and reacted with the above-mentioned terminal blocking agent.
When the aminosilane or silazane of (6) is used, it is preferable to convert the lithium atom into a hydrogen atom before the reaction. This conversion of lithium atoms into hydrogen atoms can be carried out by treating with water.

Here, examples of the organochlorosilane of the above formula (4) include the following.

[0042]

[Chemical 18]

The amount of the organochlorosilane of the formula (4) used is preferably 1.0 to 1.3 parts by mole per 1 mol of the organopolysiloxane intermediate of the formula (3).

When the reaction is carried out using the above-mentioned organochlorosilane, it is possible to employ a method in which the organochlorosilane is added dropwise to the reaction solution containing the organopolysiloxane intermediate (3) to carry out the termination reaction. In this case, the termination reaction is preferably carried out in the presence of a hydrochloric acid scavenger such as pyridine or triethylamine. In this case, the reaction conditions are as follows: in the formula (1), when A is a hydrogen atom, the reaction temperature is 20 to 100 ° C., particularly 50 to 80 ° C.
The reaction temperature is preferably -10 to 30 ° C, particularly 0 to 20 ° C when A is a lithium atom.
The reaction time is preferably 1 to 10 hours.

After the completion of the reaction, the amine hydrochloride or lithium chloride is removed by a treatment such as washing with water or filtration, and the solvent is removed by stripping to obtain the desired (meth) acryl-functional organopolysiloxane. be able to.

On the other hand, specific examples of the aminosilanes of the formulas (5) and (6) include the following compounds.

[0047]

[Chemical 19]

The amount of the organosilicon compound of the above formula (5) or (6) used is preferably 1.0 to 1.3 mol per 1 mol of the organopolysiloxane intermediate of the above formula (3). .

When the organosilicon compound is dropped into the reaction solvent in which the organopolysiloxane intermediate (3) is formed to carry out the termination reaction, the termination reaction is 50 to 80 ° C., particularly 60 to
It is preferable to carry out at 70 ° C. The reaction time is usually 1
~ 10 hours.

After completion of the reaction, the desired (meth) acryl-functional organopolysiloxane can be obtained by washing with water, separating the oil layer, and removing the reaction solvent by stripping.

The (meth) acryl-functional organopolysiloxane thus obtained is a by-product di (meth).
The amount of acrylics produced is small. In addition, since this (meth) acrylic functional organopolysiloxane has a (meth) acrylic group at one end, it is copolymerizable with vinyl monomers and does not gel when copolymerized with vinyl monomers. With water repellency, releasability,
A graft copolymer with excellent slipperiness, weather resistance and gas permeability can be obtained. Therefore, water repellent for concrete, anti-sticking paint, underwater antifouling paint, weather resistant paint, and sticking prevention for thermal transfer recording film. It is useful as a synthetic intermediate for graft copolymers used in applications such as agents, water repellants, anti-snow coatings, and cosmetics.

[0052]

The (meth) acryl-functional organopolysiloxane of the present invention has a (meth) acryl group at one end, and therefore can be copolymerized with a vinyl-based monomer. It is possible to obtain a graft copolymer having excellent properties, slipperiness, weather resistance and gas permeability. Further, according to the production method of the present invention, such a (meth) acrylic functional organopolysiloxane can be reliably synthesized.

[0053]

EXAMPLES The present invention will be specifically described below by showing Examples and Comparative Examples, but the present invention is not limited to the following Examples.

Example 1 In a glass reactor equipped with a stirrer, a thermometer, a reflux condenser, and a dropping funnel, the following formula (2)
The silanol compound represented by a) (70.0 g), hexamethylcyclotrisiloxane (355.2 g) and dehydrated acetonitrile (106.6 g) were charged, and the content was homogenized by heating the internal temperature to 70 ° C. in an oil bath. Various solutions.

[0055]

[Chemical 20]

To this solution was added 0.1 g of a pentacoordinated silicon catalyst represented by the following formula (7a), and the mixture was stirred at 80 ° C. for 11 hours to carry out a polymerization reaction. After completion of the polymerization, pyridine 19.
0 g and 47.8 g of toluene were added and mixed, and the reaction solution was ice-cooled and trimethylchlorosilane 23.9 was added at 10 ° C.
When g was added dropwise, pyridine hydrochloride was precipitated during the addition.

[0057]

[Chemical 21]

After completion of dropping, cooling was stopped, the reaction solution was heated, and stirred at 70 ° C. for 2 hours to carry out a terminal blocking reaction. The reaction solution was cooled to 30 ° C., washed with 1N hydrochloric acid water to remove excess pyridine, and then washed with water until the neutrality of the reaction solution was confirmed with a bromothymol blue indicator.

Subsequently, stripping was performed under the condition of 100 ° C./10 mmHg to remove toluene and a small amount of low volatile matter, and a colorless transparent oil was obtained. Yield is 3
The yield was 05.4 g, 85.7%.

The viscosity of this oil at 25 ° C., the specific gravity,
The refractive index and the weight average molecular weight (measured by gel permeation chromatography) were measured. As a result of a gelation test conducted by the following method, gelation did not occur even after 15 hours. The results of these measurements are shown in Table 1.

Method of gelation test 10 g of the obtained (meth) acrylic organopolysiloxane oil was placed in a glass reactor equipped with a cooling tube.
Methyl methacrylate 10g, Toluene 30g, AIB
Charge 0.2 g of N (azobisisobutyronitrile),
Bubbling was performed with nitrogen for 10 minutes to dissolve AIBN. Thereafter, the reactor was kept in an oil bath at 60 ° C., and the polymerization reaction was carried out for 15 hours without stirring.

Further, as a result of infrared absorption spectrum, nuclear magnetic resonance spectrum analysis and elemental analysis, it was found that the obtained oil had a structure represented by the following formula (1a). FIG. 1 shows the infrared absorption spectrum of this (meth) acrylic functional organopolysiloxane, and FIG. 2 shows the nuclear magnetic resonance spectrum of this (meth) acrylic functional organopolysiloxane.

[0063]

[Chemical formula 22] In addition, the methacryl equivalent calculated from the proton ratio from the internal standard was 2224 (theoretical value 2198).

[0064]

[Table 1]

[0065]

[Chemical formula 23]

Example 2 The following formula (2) was used as a polymerization initiator.
The same operation as in Example 1 was carried out except that 55.2 g of the organosilicon compound shown in b) was used and the polymerization conditions were changed to 70 ° C. for 4 hours to obtain a colorless and transparent oil. Was measured. The measurement results are also shown in Table 1.

[0067]

[Chemical formula 24]

Further, as a result of performing the following analysis in the same manner as in Example 1, it was found that the obtained oil had a structure represented by the following formula (1b).

[0069]

[Chemical 25]

[0070]

[Table 2]

[0071]

[Chemical formula 26]

[Example 3] 67.2 g of a polymerization initiator represented by the following formula (2c) and hexamethylcyclotrisiloxane 4
The same polymerization reaction as in Example 1 was carried out except that 4.4 g, 13.3 g of acetonitrile, and 0.01 g of the same pentacoordinated silicon catalyst as in Example 1 were used. The polymerization reaction is 70 ° C, 2
It was time.

[0073]

[Chemical 27]

After completion of the polymerization, 35.4 g of toluene was added and mixed, the reaction solution was heated to 60 ° C. in an oil bath, and 17.7 g of hexamethyldisilazane was added dropwise. Stirring was carried out at 60 ° C. for 2 hours to carry out an end-capping reaction. The obtained aqueous solution was dried with neutral anhydrous sodium sulfate and filtered. Then, to remove toluene and a small amount of low volatile matter, 100 ° C / 1
Stripping was performed under the condition of 0 mmHg to obtain a colorless transparent oil, and the physical properties were measured in the same manner as in Example 1. The measurement results are also shown in Table 1.

Further, as a result of conducting the following analysis in the same manner as in Example 1, it was found that the obtained oil had a structure represented by the following formula (1c).

[0076]

[Chemical 28]

[0077]

[Table 3]

[0078]

[Chemical 29]

Example 4 A glass reactor equipped with a stirrer, a thermometer, a reflux condenser and a dropping funnel was charged with 740.0 g of hexamethylcyclotrisiloxane and 1480 g of dehydrated tetrahydrofuran and stirred at room temperature. To give a uniform solution. Then, the internal temperature was cooled to 0 ° C. with a handy cooler. To this solution was added 46.8 g of a lithium silanolate polymerization initiator represented by the following formula (2d), the reaction solution was kept at 0 ° C., and a polymerization reaction was carried out for 5 hours while allowing a slight amount of dry nitrogen to flow into the reactor. It was

[0080]

[Chemical 30]

After completion of the polymerization, tributylchlorosilane 2
5.8 g was added dropwise. Then, cooling was stopped, and stirring was carried out for 2 hours to carry out an end-capping reaction. After removing lithium chloride by filtration, in order to remove tetrahydrofuran and a small amount of low volatile matter, stripping was performed under conditions of 100 ° C./10 mmHg to obtain a colorless transparent oil, and in the same manner as in Example 1. The physical properties were measured. The measurement results are also shown in Table 1.

Further, as a result of conducting the following analysis in the same manner as in Example 1, it was found that the obtained oil had a structure represented by the following formula (1d).

[0083]

[Chemical 31]

[0084]

[Table 4]

[0085]

[Chemical 32]

Example 5 As the polymerization initiator, the following formula (2)
The same polymerization reaction as in Example 4 was carried out except that 51.0 g of the lithium silanolate compound shown in e), 1480.0 g of hexamethylcyclotrisiloxane and 2960 g of tetrahydrofuran were used.

[0087]

[Chemical 33]

After completion of the polymerization, cooling was stopped, the reaction solution was washed with water and separated, and the terminal lithium silanolate group was replaced with a silanol group. Then diethylaminotrimethylsilane 1
The same end capping reaction as in Example 3 was performed using 59.5 g. The obtained solution was dried with neutral anhydrous Glauber's salt and filtered. Subsequently, in order to remove tetrahydrofuran and a small amount of low volatile matter, stripping was performed under conditions of 100 ° C./10 mmHg to obtain a colorless transparent oil, and physical properties were measured in the same manner as in Example 1. The results are also shown in Table 1.

Further, as a result of conducting the following analysis in the same manner as in Example 1, it was found that the obtained oil had a structure represented by the following formula (1e).

[0090]

[Chemical 34]

[0091]

[Table 5]

[0092]

[Chemical 35]

[Comparative Example 1] A colorless and transparent oil was obtained in the same manner as in Example 1 except that 40.0 g of the organosilicon compound represented by the following formula (i) was used as a polymerization initiator.
Physical properties were measured in the same manner as in Example 1. Table 1 shows the measurement results
Also described in.

[0094]

[Chemical 36]

Further, as a result of conducting the following analysis in the same manner as in Example 1, it was found that the obtained oil had a structure represented by the following formula (ii).

[0096]

[Chemical 37]

[0097]

[Table 6]

[0098]

[Chemical 38]

[0099]

[Table 7]

[Brief description of drawings]

1 is an infrared absorption spectrum of the (meth) acryl-functional organopolysiloxane obtained in Example 1. FIG.

2 is a nuclear magnetic resonance spectrum of the (meth) acrylic functional organopolysiloxane obtained in Example 1. FIG.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Toshio Yamazaki, Inventor Toshio Yamazaki, No. 1 Hitomi, Matsuida-cho, Usui-gun, Gunma Prefecture, Shin-Etsu Chemical Co., Ltd. Silicone Electronic Materials Research Laboratory (72) Shoji Ichinohe Matsui, Usui-gun, Gunma Prefecture Tamachi Daiji Hitomi 1-10 Shin-Etsu Chemical Co., Ltd. Silicone Electronic Materials Technology Laboratory

Claims (3)

[Claims] 1. A (meth) acrylic functional organopolysiloxane represented by the following general formula (1). [Chemical 1] (In the formula, R ¹ is a hydrogen atom or a methyl group, R ² is a methyl group or —OSi (CH ₃ ) ₃ group, R ³ , R ⁴ and R ⁵ are each a substituted or unsubstituted monovalent hydrocarbon group, m Is an integer from 1 to 14,
n is an integer of 3 to 200. ) 2. The following general formula (2): (In the formula, R ¹ is a hydrogen atom or a methyl group, R ² is a methyl group or —OSi (CH ₃ ) ₃ group, m is an integer of 1 to 14,
A is a hydrogen atom or a lithium atom. ) Is reacted with hexamethylcyclotrisiloxane to give a compound represented by the following general formula (3): (In the formula, R ¹ , R ² , A and m have the same meanings as described above,
n is an integer of 3 to 200. ), An intermediate represented by the formula (3) is directly or, if A of the intermediate is a lithium atom, optionally converted to a hydrogen atom, and then the following general formulas (4) to ( 6) [Chemical 4] (In the formula, R ^{3 to} R ⁵ are each a substituted or unsubstituted monovalent hydrocarbon group, and R ^{6 to} R ⁸ are each a hydrogen atom or an alkyl group.) The method for producing a (meth) acryl-functional organopolysiloxane according to claim 1, which comprises reacting with an agent. 3. An organosilicon compound of the formula (2) wherein A is a hydrogen atom is used, and the reaction of the organosilicon compound with hexamethylcyclotrisiloxane is represented by the following general formula (7): (In the formula, R ⁹ is a substituted or unsubstituted monovalent hydrocarbon group, and M is Li, Na, K, NH ₄ or C ₆ H ₅ CH ₂ N (CH ₃ ) ₃ ). 3. The production method according to claim 2, wherein the production is carried out in the presence of a silicon catalyst.