Organopolysiloxane compounds and methods for producing the same

Abstract

Branched organopolysiloxanes synthesized by conventional methods have a broad molecular weight distribution and contain many low molecular weight components, making it difficult to reduce outgassing. From the viewpoint of preventing problems such as bubble generation and contamination of heating furnaces, there is still room for further investigation. The present invention provides a branched organopolysiloxane compound with a narrow molecular weight distribution and low outgassing, and a method for producing the same. [Solution] An organopolysiloxane compound represented by formula (1), having a molecular weight distribution (Mw / Mn) of 2.0 or less. TIFF2026059089000026.tif21102 (R 1 ~R 4 (where represents a given base, n is an integer greater than or equal to 3, and p is 3 or 4.)

Description

[Technical Field]

[0001] The present invention relates to an organopolysiloxane compound characterized by having a narrow molecular weight distribution and a method for producing the same. [Background technology]

[0002] Organopolysiloxane compounds are not only useful as raw materials for silicone rubber compositions widely used in building materials, daily necessities, medical devices, and electronic materials, but they also have high utility value because, when used as additives to organic resins, they can impart properties such as flexibility, water repellency, mold release properties, weather resistance, heat resistance, and electrical insulation, which are due to the structure of the organopolysiloxane compounds, to the organic resins.

[0003] In general, organopolysiloxane compounds are known not only in linear forms but also in branched forms. For example, Patent Document 1 discloses a branched organopolysiloxane for the purpose of producing an adhesive sheet with easy peelability and little change in peel strength over time for solvent-free release agents, and Patent Document 2 discloses a branched organopolysiloxane for the purpose of improving the processability, peel strength, and flatness of a solvent-free pressure-sensitive adhesive.

[0004] However, the molecular weight distribution of these branched organopolysiloxanes has not been studied. Generally, a broad molecular weight distribution tends to result in a higher proportion of low molecular weight components. When organopolysiloxanes with a high proportion of such low molecular weight components are used as a product, these components volatilize as outgassing, causing various problems such as bubble formation and contamination of heating furnaces.

[0005] On the other hand, Reference 3 discloses a linear organopolysiloxane compound having a narrow molecular weight distribution, one unsaturated group end, and one hydride end, which is expected to exhibit reduced viscosity, improved low-temperature curability, and enhanced mechanical properties by using a living anion ring-opening polymerization method, and a method for producing the same compound.

[0006] However, in Reference Document 3, branched organopolysiloxanes have not been studied, and the evaluation of the remaining low molecular weight components has not been carried out either.

Prior Art Documents

Patent Documents

[0007]

Patent Document 1

Patent Document 2

Patent Document 3

Summary of the Invention

Problems to be Solved by the Invention

[0008] Branched organopolysiloxanes synthesized by conventional methods have a wide molecular weight distribution and contain many low molecular weight components. Therefore, it is difficult to reduce outgassing, and there is room for consideration from the perspective of preventing problems such as the generation of bubbles and the contamination of heating furnaces. An object of the present invention is to provide a branched organopolysiloxane compound with less outgassing and a narrow molecular weight distribution, and a method for producing the same. [[ID=—]]

Means for Solving the Problems

[0009] The present inventors conducted diligent research to solve these problems. As a result, they discovered that a branched organopolysiloxane compound having a narrow molecular weight distribution can be produced by reacting an organometallic compound with a cyclic siloxane to produce a metal silanolate, followed by a step of reacting it with cyclotrisiloxane or cyclotetrasiloxane, stopping polymerization by adding water or acid as needed, and then reacting it with trichlorosilane, tetrachlorosilane, trialkoxysilane, or tetrakoxysilane. Furthermore, they found that the branched organopolysiloxane compound with a controlled narrow molecular weight distribution obtained by the above production method exhibits low outgassing, thus completing the present invention.

[0010] This invention includes the following configuration.

[0011] [1] An organopolysiloxane compound represented by formula (1), having a molecular weight distribution (Mw / Mn) of 2.0 or less. TIFF2026059089000001.tif21102 In formula (1), R 1 is hydrogen, an alkyl group in which at least one hydrogen may be replaced by a halogen, an alkenyl group in which at least one hydrogen may be replaced by a halogen, an alkynyl group in which at least one hydrogen may be replaced by a halogen, a cycloalkyl group in which at least one hydrogen may be replaced by a halogen, an aryl group in which at least one hydrogen may be replaced by a halogen, a functional group, or a group having a functional group; R 2 is alkyl or aryl; R 3is each independently hydrogen, alkyl in which at least one hydrogen may be replaced by halogen, alkenyl in which at least one hydrogen may be replaced by halogen, alkynyl in which at least one hydrogen may be replaced by halogen, cycloalkyl in which at least one hydrogen may be replaced by halogen or aryl in which at least one hydrogen may be replaced by halogen; R 4 is hydrogen, alkyl in which at least one hydrogen may be replaced by halogen, alkenyl in which at least one hydrogen may be replaced by halogen, alkynyl in which at least one hydrogen may be replaced by halogen, cycloalkyl in which at least one hydrogen may be replaced by halogen, aryl in which at least one hydrogen may be replaced by halogen, a functional group or a group having a functional group; n is an integer of 3 or more; p is 3 or 4.

[0012] [2] In formula (1), R 1 is hydrogen or alkenyl having 2 to 6 carbon atoms; R 2 is alkyl having 1 to 4 carbon atoms or phenyl; R 3 is each independently hydrogen, methyl, vinyl, 3,3,3-trifluoropropyl or phenyl, the organopolysiloxane compound according to [1].

[0013] [3] In formula (1), R 1 is hydrogen or vinyl; R 2 is alkyl having 1 to 4 carbon atoms or phenyl; R 3 is each independently hydrogen, methyl, vinyl, 3,3,3-trifluoropropyl or phenyl, the organopolysiloxane compound according to [1] or [2].

[0014] [4] In formula (1), R 1 is hydrogen or vinyl; R 2 is butyl; R 3 is methyl; R4 An organopolysiloxane compound according to any one of items [1] to [3], wherein is hydrogen or methyl.

[0015] [5] A process of reacting an organometallic compound with a cyclic siloxane to produce a metal silanolate, The following steps involve reacting cyclotrisiloxane or cyclotetrasiloxane with a metal silanolate to produce the compound shown in formula (2), A method for producing an organopolysiloxane compound according to any one of items [1] to [4], further comprising the step of reacting a compound represented by formula (3) with a compound represented by formula (2). TIFF2026059089000002.tif2185 TIFF2026059089000003.tif885 In formula (2), R 1 is hydrogen, an alkyl group in which at least one hydrogen may be replaced by a halogen, an alkenyl group in which at least one hydrogen may be replaced by a halogen, an alkynyl group in which at least one hydrogen may be replaced by a halogen, a cycloalkyl group in which at least one hydrogen may be replaced by a halogen, an aryl group in which at least one hydrogen may be replaced by a halogen, a functional group, or a group having a functional group; R 2 is alkyl or aryl; R 3 Each is independently a hydrogen atom, an alkyl atom in which at least one hydrogen atom may be replaced by a halogen, an alkenyl atom in which at least one hydrogen atom may be replaced by a halogen, an alkynyl atom in which at least one hydrogen atom may be replaced by a halogen, a cycloalkyl atom in which at least one hydrogen atom may be replaced by a halogen, or an aryl atom in which at least one hydrogen atom may be replaced by a halogen; M is a monovalent metal; n is an integer greater than or equal to 3; In formula (3), R 4is hydrogen, an alkyl group in which at least one hydrogen may be replaced by a halogen, an alkenyl group in which at least one hydrogen may be replaced by a halogen, an alkynyl group in which at least one hydrogen may be replaced by a halogen, a cycloalkyl group in which at least one hydrogen may be replaced by a halogen, an aryl group in which at least one hydrogen may be replaced by a halogen, a functional group, or a group having a functional group; X is a halogen or alkoxy; p is either 3 or 4.

[0016] [6] A method for producing an organopolysiloxane compound according to item [5], wherein the organometallic compound is an alkyllithium compound, the cyclic siloxane is a compound represented by formula (4), and the metal silanolate is a lithium silanolate. TIFF2026059089000004.tif2682 (The symbol "Me" above represents methyl.) In formula (4), R 5 is hydrogen or vinyl, and m is 3 or 4.

[0017] [7] A process of reacting an organometallic compound with a cyclic siloxane to produce a metal silanolate, The following steps involve reacting cyclotrisiloxane or cyclotetrasiloxane with a metal silanolate to produce the compound shown in formula (2), The following steps involve stopping the polymerization of the compound represented by formula (2) by adding water or acid to produce the compound represented by formula (2'), A method for producing an organopolysiloxane compound according to any one of items [1] to [4], further comprising the step of reacting a compound represented by formula (3) with a compound represented by formula (2'). TIFF2026059089000005.tif2185 TIFF2026059089000006.tif2186 TIFF2026059089000007.tif885 In formula (2), R 1 is hydrogen, an alkyl group in which at least one hydrogen may be replaced by a halogen, an alkenyl group in which at least one hydrogen may be replaced by a halogen, an alkynyl group in which at least one hydrogen may be replaced by a halogen, a cycloalkyl group in which at least one hydrogen may be replaced by a halogen, an aryl group in which at least one hydrogen may be replaced by a halogen, a functional group, or a group having a functional group; R 2 is alkyl or aryl; R 3 Each is independently a hydrogen, an alkyl whose at least one hydrogen may be replaced by a halogen, an alkenyl whose at least one hydrogen may be replaced by a halogen, an alkynyl whose at least one hydrogen may be replaced by a halogen, a cycloalkyl whose at least one hydrogen may be replaced by a halogen, or an aryl whose at least one hydrogen may be replaced by a halogen; M is a monovalent metal; n is an integer greater than or equal to 3; In formula (2'), R 1 , R 2 and R 3 R in equation (2) 1 , R 2 and R 3 It is the same basis of definition as; n has the same definition as n in equation (2); In formula (3), R 4 is hydrogen, an alkyl group in which at least one hydrogen may be replaced by a halogen, an alkenyl group in which at least one hydrogen may be replaced by a halogen, an alkynyl group in which at least one hydrogen may be replaced by a halogen, a cycloalkyl group in which at least one hydrogen may be replaced by a halogen, an aryl group in which at least one hydrogen may be replaced by a halogen, a functional group, or a group having a functional group; X is a halogen or alkoxy; p is either 3 or 4.

[0018] [8] A method for producing an organopolysiloxane compound according to item [7], wherein the organometallic compound is an alkyllithium compound, the cyclic siloxane is a compound represented by formula (4) as described in item [6], and the metal silanolate is a lithium silanolate. [Effects of the Invention]

[0019] According to the present invention, a branched organopolysiloxane compound can be obtained that reduces outgassing by creating a narrow molecular weight distribution through living anionic ring-opening polymerization. [Modes for carrying out the invention]

[0020] The embodiments of the present invention will be described in detail below, but the following description is merely an example (representative example) of the embodiments of the present invention, and the present invention is not limited in any way to these. Furthermore, the embodiments of the present invention can be combined as appropriate. In this specification, the symbol "Me" represents methyl, n The symbol "Bu" represents normal butyl.

[0021] <Organopolysiloxane compounds> The organopolysiloxane compound of the present invention is represented by formula (1), has a molecular weight distribution (Mw / Mn) of 2.0 or less, and is characterized by being branched. TIFF2026059089000008.tif21102

[0022] In equation (1), R 1 R is a hydrogen atom, an alkyl group in which at least one hydrogen atom may be replaced by a halogen atom, an alkenyl group in which at least one hydrogen atom may be replaced by a halogen atom, an alkynyl group in which at least one hydrogen atom may be replaced by a halogen atom, a cycloalkyl group in which at least one hydrogen atom may be replaced by a halogen atom, an aryl group in which at least one hydrogen atom may be replaced by a halogen atom, a functional group, or a group having a functional group; R 1At least one -CH2- contained in may be replaced with alkenylene, alkylylene, cycloalkylene, cycloalkenylene, phenylene, ether, carbonyl, ester, amide, imide, urethane, urea, sulfide, disulfide, sulfonyl, 1-oxo-2-oxapropane-1,3-diyl, 2-oxapropane-1,3-diyl (1,3-dioxo-2-oxapropane-1,3-diyl), or polyalkylene oxy.

[0023] Specific examples of alkyl groups in which at least one hydrogen may be replaced by a halogen include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, hexadecyl, octadecyl, icosyl, docosyl, or triacontyl.

[0024] Specific examples of alkenyls in which at least one hydrogen atom may be replaced by a halogen include vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tetradecenyl, hexadecenyl, octadecenyl, icocenyl, or dococenyl.

[0025] Specific examples of alkynyls in which at least one hydrogen atom may be replaced by a halogen include acetylenyl, propynyl, butynyl, or hexynyl.

[0026] Specific examples of cycloalkyls in which at least one hydrogen may be replaced by a halogen include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bornyl, isobornyl, norbornyl, norbornenyl, norbornadienyl, cyclopentadienyl, dicyclopentadienyl, dihydrodicyclopentadienyl, tetrahydrodicyclopentadienyl, decalyl, or adamantyl.

[0027] Specific examples of aryls in which at least one hydrogen may be replaced by a halogen include phenyl, tolyl, benzyl, phenylethyl, naphthyl, vinylphenyl, styryl, metastyryl, phenylpropyl, or vinylphenylethyl.

[0028] Specific examples of functional groups include hydroxy, amino, nitro, mercapto, phosphino, cyano, isocyanate, alkoxy, carboxy, sulfone, oxyranyl, oxetanyl, epoxycyclohexyl, acryloyl, or methacryloyl.

[0029] A functional group is a group composed of a divalent group and a functional group that is bonded to the Si atom via the divalent group. Specific examples of divalent groups include alkylene, cycloalkylene, alkylcycloalkylene, alkylenephenylene, alkylphenylene, or alkylphenylalkylene, and these functional groups are bonded to the Si atom via these divalent groups. Specific examples of functional groups that are bonded via a divalent group include hydroxy, amino, nitro, mercapto, phosphinone, cyano, isocyanate, alkoxy, carboxy, sulfone, oxyranyl, oxetanyl, epoxycyclohexyl, or (meth)acryloyl.

[0030] From the viewpoint of introducing reactive groups to the polysiloxane chain terminus and raw material availability, R 1 It is preferably hydrogen or an alkenyl having 2 to 6 carbon atoms, and more preferably hydrogen or vinyl.

[0031] In equation (1), R 2 It is alkyl or aryl.

[0032] Specific examples of alkyl groups include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, hexadecyl, octadecyl, icosyl, docosyl, or triacontyl.

[0033] Specific examples of aryls include phenyl, tolyl, benzyl, phenylethyl, naphthyl, vinylphenyl, (meth)styryl, phenylpropyl, or vinylphenylethyl.

[0034] From the perspective of raw material availability, R 2 The element is preferably an alkyl or phenyl compound having 1 to 4 carbon atoms, and butyl is more preferred from the viewpoint of handling properties.

[0035] In equation (1), R 3 Each is independently a hydrogen atom, an alkyl atom in which at least one hydrogen atom may be replaced by a halogen atom, an alkenyl atom in which at least one hydrogen atom may be replaced by a halogen atom, an alkynyl atom in which at least one hydrogen atom may be replaced by a halogen atom, a cycloalkyl atom in which at least one hydrogen atom may be replaced by a halogen atom, or an aryl atom in which at least one hydrogen atom may be replaced by a halogen atom; R 3 At least one -CH2- contained in may be replaced with alkenylene, alkylylene, cycloalkylene, cycloalkenylene, phenylene, ether, carbonyl, ester, amide, imide, urethane, urea, sulfide, disulfide, sulfonyl, 1-oxo-2-oxapropane-1,3-diyl, 2-oxapropane-1,3-diyl (1,3-dioxo-2-oxapropane-1,3-diyl), or polyalkylene oxy.

[0036] Specific examples of alkyl groups in which at least one hydrogen may be replaced by a halogen include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, hexadecyl, octadecyl, icosyl, docosyl, or triacontyl.

[0037] Specific examples of alkenyls in which at least one hydrogen atom may be replaced by a halogen include vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tetradecenyl, hexadecenyl, octadecenyl, icocenyl, or dococenyl.

[0038] Specific examples of alkynyls in which at least one hydrogen atom may be replaced by a halogen include acetylenyl, propynyl, butynyl, or hexynyl.

[0039] Specific examples of cycloalkyls in which at least one hydrogen may be replaced by a halogen include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bornyl, isobornyl, norbornyl, norbornenyl, norbornadienyl, cyclopentadienyl, tetrahydrodicyclopentadienyl, dihydrodicyclopentadienyl, dicyclopentadienyl, decalyl, or adamantyl.

[0040] Specific examples of aryls in which at least one hydrogen may be replaced by a halogen include phenyl, tolyl, benzyl, phenylethyl, naphthyl, vinylphenyl, (meth)styryl, phenylpropyl, or vinylphenylethyl.

[0041] From the perspective of raw material availability, R 3 The compound is preferably hydrogen, methyl, vinyl, 3,3,3-trifluoropropyl, or phenyl, and more preferably methyl from the viewpoint of polymerizability.

[0042] In equation (1), R 4R is a hydrogen atom, an alkyl group in which at least one hydrogen atom may be replaced by a halogen atom, an alkenyl group in which at least one hydrogen atom may be replaced by a halogen atom, an alkynyl group in which at least one hydrogen atom may be replaced by a halogen atom, a cycloalkyl group in which at least one hydrogen atom may be replaced by a halogen atom, an aryl group in which at least one hydrogen atom may be replaced by a halogen atom, a functional group, or a group having a functional group; R 4 At least one -CH2- contained in may be replaced with alkenylene, alkylylene, cycloalkylene, cycloalkenylene, phenylene, ether, carbonyl, ester, amide, imide, urethane, urea, sulfide, disulfide, sulfonyl, 1-oxo-2-oxapropane-1,3-diyl, 2-oxapropane-1,3-diyl (1,3-dioxo-2-oxapropane-1,3-diyl), or polyalkylene oxy.

[0043] Specific examples of alkyl groups in which at least one hydrogen may be replaced by a halogen include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, hexadecyl, octadecyl, icosyl, docosyl, or triacontyl.

[0044] Specific examples of alkenyls in which at least one hydrogen atom may be replaced by a halogen include vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tetradecenyl, hexadecenyl, octadecenyl, icocenyl, or dococenyl.

[0045] Specific examples of alkynyls in which at least one hydrogen atom may be replaced by a halogen include acetylenyl, propynyl, butynyl, or hexynyl.

[0046] Specific examples of cycloalkyls in which at least one hydrogen may be replaced by a halogen include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bornyl, isobornyl, norbornyl, norbornenyl, norbornadienyl, cyclopentadienyl, dicyclopentadienyl, dihydrodicyclopentadienyl, tetrahydrodicyclopentadienyl, decalyl, or adamantyl.

[0047] Specific examples of aryls in which at least one hydrogen may be replaced by a halogen include phenyl, tolyl, benzyl, phenylethyl, naphthyl, vinylphenyl, (meth)styryl, phenylpropyl, or vinylphenylethyl.

[0048] Specific examples of functional groups include hydroxy, amino, nitro, mercapto, phosphino, cyano, isocyanate, alkoxy, carboxy, sulfone, oxyranyl, oxetanyl, epoxycyclohexyl, or (meth)acryloyl.

[0049] A functional group is a group composed of a divalent group and a functional group that is bonded to the Si atom via the divalent group. Specific examples of divalent groups include alkylene, cycloalkylene, alkylcycloalkylene, alkylenephenylene, alkylphenylene, or alkylphenylalkylene, and these functional groups are bonded to the Si atom via these divalent groups. Specific examples of functional groups that are bonded via a divalent group include hydroxy, amino, nitro, mercapto, phosphinone, cyano, isocyanate, alkoxy, carboxy, sulfone, oxyranyl, oxetanyl, epoxycyclohexyl, or (meth)acryloyl.

[0050] From the viewpoint of reliably introducing organopolysiloxane chains to obtain branched organopolysiloxane compounds, 4 Hydrogen or methyl is preferred.

[0051] From the viewpoint of reliably introducing organopolysiloxane chains and obtaining branched organopolysiloxane compounds, in formula (1), n ​​is preferably an integer between 3 and 300, and more preferably an integer between 6 and 200.

[0052] In equation (1), p is an integer of 3 or 4.

[0053] The organopolysiloxane compounds obtained by the production method of the present invention have a narrow molecular weight distribution, resulting in fewer low molecular weight components, which reduces outgassing during heating. The molecular weight distribution (Mw / Mn) of the organopolysiloxane compounds obtained by the production method of the present invention is 2.0 or less, and more preferably 1.5 or less.

[0054] <Method for producing organopolysiloxane compounds> The present invention provides a method for producing an organopolysiloxane compound, comprising the steps of: reacting an organometallic compound with a cyclic siloxane to produce a metal silanolate; subsequently, reacting a cyclotrisiloxane or cyclotetrasiloxane with the metal silanolate to produce a compound represented by formula (2); optionally, stopping the polymerization of the compound represented by formula (2) by adding water or acid to produce a compound represented by formula (2'); and further, reacting a compound represented by formula (3) with a compound represented by formula (2) or (2'). Furthermore, when the polymerization of the compound shown in formula (2) is stopped by adding water or acid, the polymerization is stopped because the growing end is neutralized by the water or acid. TIFF2026059089000009.tif2185 TIFF2026059089000010.tif2186 TIFF2026059089000011.tif885

[0055] Specific examples of organometallic compounds include methyllithium, ethyllithium, propyllithium, butyllithium, phenyllithium, or phenylsodium. Of these, methyllithium, n-butyllithium, s-butyllithium, t-butyllithium, or phenyllithium are preferred, with n-butyllithium being particularly preferred.

[0056] Specific examples of cyclic siloxanes include trimethylcyclotrisiloxane, hexamethylcyclotrisiloxane, hexaethylcyclotrisiloxane, pentamethylvinylcyclotrisiloxane, trimethyltrivinylcyclotrisiloxane, trimethyltriphenylcyclotrisiloxane, hexaphenylcyclotrisiloxane, tris(trifluoropropyl)trimethylcyclotrisiloxane, tetramethylcyclotetrasiloxane, octamethylcyclotetrasiloxane, heptamethylcyclotetrasiloxane, tetramethyltetravinylcyclotetrasiloxane, tetramethyltetraphenylcyclotetrasiloxane, octaphenylcyclotetrasiloxane, or tetrakis(trifluoropropyl)tetramethylcyclotetrasiloxane. Of these, trimethylcyclotrisiloxane, trimethyltrivinylcyclotrisiloxane, tetramethylcyclotetrasiloxane, or tetramethyltetravinylcyclotetrasiloxane are preferred.

[0057] Specific examples of cyclotrisiloxanes or cyclotetrasiloxanes to be reacted with the generated metal silanolate include trimethylcyclotrisiloxane, hexamethylcyclotrisiloxane, pentamethylvinylcyclotrisiloxane, hexaethylcyclotrisiloxane, trimethyltrivinylcyclotrisiloxane, trimethyltriphenylcyclotrisiloxane, hexaphenylcyclotrisiloxane, tris(trifluoropropyl)trimethylcyclotrisiloxane, tetramethylcyclotetrasiloxane, heptamethylcyclotetrasiloxane, octamethylcyclotetrasiloxane, tetramethyltetravinylcyclotetrasiloxane, tetramethyltetraphenylcyclotetrasiloxane, octaphenylcyclotetrasiloxane, or tetrakis(trifluoropropyl)tetramethylcyclotetrasiloxane. Of these, trimethylcyclotrisiloxane, hexamethylcyclotrisiloxane, trimethyltriphenylcyclotrisiloxane, hexaphenylcyclotrisiloxane, tris(trifluoropropyl)trimethylcyclotrisiloxane, tetramethylcyclotetrasiloxane, octamethylcyclotetrasiloxane, tetramethyltetraphenylcyclotetrasiloxane, octaphenylcyclotetrasiloxane, or tetrakis(trifluoropropyl)tetramethylcyclotetrasiloxane are preferred, with hexamethylcyclotrisiloxane or octamethylcyclotetrasiloxane being particularly preferred.

[0058] In the compound represented by formula (2), M is not particularly limited as long as it is a monovalent metal, but specifically, lithium or sodium are examples, of which lithium is preferred.

[0059] When an acid is used to stop the polymerization of the compound represented by formula (2) by adding water or an acid as needed, the acid used is not particularly limited as long as it is a Brønsted acid or an aqueous solution thereof, but specific examples of the acid include formic acid, acetic acid, nitric acid, sulfuric acid, or hydrochloric acid, of which acetic acid is preferred.

[0060] Specific examples of compounds represented by formula (3) include, when X is a halogen, allyltrichlorosilane, chloropropyltrichlorosilane, trichloroethylsilane, trichlorooctadecylsilane, trichlorooctylsilane, trichlorochloromethylsilane, trichlorocyanoethylsilane, trichlorocyanopropylsilane, trichlorocyclohexylsilane, trichlorosilane, trichlorodecylsilane, trichlorododecylsilane, trichlorotridecafluorooctylsilane, trichlorotrifluoropropylsilane, trichlorotolylsilane, and trichlorovinylsilane. Examples include lan, trichlorophenylethylsilane, trichlorophenylsilane, trichlorophenylpropylsilane, trichlorophenylhexylsilane, trichloropropylsilane, trichlorohexylsilane, trichloropentafluorophenylpropylsilane, trichloromethylsilane, butyltrichlorosilane, bromoundecyltrichlorosilane, bromopropyltrichlorosilane, 3-(2-bromo-2-methylpropanoyloxy)propylchlorosilane, 3-(meth)acryloyloxypropyltrichlorosilane, or tetrachlorosilane. Of these, trichlorosilane, trichloromethylsilane, trichlorophenylsilane, or tetrachlorosilane are preferred, and trichlorosilane, trichloromethylsilane, or tetrachlorosilane are more preferred.

[0061] If X is an alkoxy, then 3-[2-(2-aminoethylamino)ethylamino]propyltrimethoxysilane, 3-(2-aminoethylamino)propyltrimethoxysilane, aminopropyltrimethoxysilane, allyltrimethoxysilane, ureidopropyltrimethoxysilane, epoxycyclohexylethyltrimethoxysilane, chloropropyltrimethoxysilane, glycidyloxypropyltrimethoxysilane, N,N-diethylaminopropyltrimethoxysilane, N,N-dimethylaminopropyltrimethoxysilane, trifluoropropyltrimethoxysilane, trimethoxyoctadecylsilane, trimethoxyoctylsilane, trimethoxyvinylsilane, trimethoxyphenylethylsilane, trimethoxyphenylsilane, trimethoxymethylaminopropylsilane, trimethoxymethylsilane, N-phenylaminopropyltrimethoxysilane, butyltrimethoxysilane, bromopropyltrimethoxysilane, hexadecyl Trimethoxysilane, (meth)acryloyloxypropyltrimethoxysilane, mercaptopropyltrimethoxysilane, iodopropyltrimethoxysilane, aminopropyltriethoxysilane, isocyanatopropyltriethoxysilane, chloropropyltriethoxysilane, chlorophenyltriethoxysilane, cyanoethyltriethoxysilane, cyanopropyltriethoxysilane, dodecyltriethoxysilane, triethoxyethylsilane, triethoxyocta Examples include decylsilane, triethoxyoctylsilane, triethoxyglycidyloxypropylsilane, triethoxysilane, triethoxythienylsilane, triethoxyvinylsilane, triethoxyphenylsilane, triethoxymethylsilane, triethoxymercaptopropylsilane, tridecafluorooctyltriethoxysilane, butyltriethoxysilane, tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane, or tetrabutoxysilane. Of these, trimethoxysilane, trimethoxymethylsilane, trimethoxyphenylsilane, triethoxysilane, triethoxymethylsilane, triethoxyphenylsilane, tetramethoxysilane, or tetraethoxysilane are preferred, and trimethoxysilane, trimethoxymethylsilane, triethoxysilane, triethoxymethylsilane, tetramethoxysilane, or tetraethoxysilane are more preferred.

[0062] The step of producing the metal silanolate has a reaction temperature of preferably 0 to 50°C, more preferably 20 to 40°C, and a reaction time of preferably 0.1 to 6 hours, more preferably 0.1 to 2 hours. The step of reacting with the cyclic siloxane has a reaction temperature of preferably 0 to 20°C, and a reaction time of preferably 1 to 6 hours. If polymerization is to be stopped by adding water or acid to the compound represented by formula (2) as needed, the reaction temperature when reacting with water or acid while stirring is preferably 0 to 30°C, and the reaction time is preferably 0.1 to 20 hours. The step of reacting the generated compound represented by formula (1) with the compound represented by formula (2) has a reaction temperature of preferably 0 to 20°C, more preferably 0 to 10°C, and a reaction time of preferably 0.1 to 20 hours. [Examples]

[0063] The present invention will be described in more detail below with reference to synthesis examples and examples of the organopolysiloxane compounds of the present invention, but the present invention is not limited in any way by these examples.

[0064] <Measuring molecular weight> The molecular weight of organopolysiloxane compounds was measured by gel permeation chromatography (GPC), and the ratio of weight-average molecular weight (Mw) to number-average molecular weight (Mn) was defined as the molecular weight distribution (Mw / Mn). Polystyrene was used as a standard sample, and the polystyrene-equivalent molecular weight was measured. Furthermore, the polystyrene-equivalent molecular weight measurement by the GPC method was performed under the following measurement conditions. a) Measuring instrument: JASCO Corporation Manufactured by HPLC LC-2000Plus series b) Column: Shodex KF-804L manufactured by Resonac Co., Ltd. (formerly Showa Denko K.K.) (two connected in series) c) Oven temperature: 40 °C d) Eluent: Toluene 0.7 mL / min e) Detector: RI-2031 f) Standard sample: TSK standard polystyrene manufactured by Tosoh Corporation g) Injection volume: 20 μL h) Concentration: 0.025 g / 10 mL i) Sample preparation: Using toluene as a solvent, it was stirred and dissolved at room temperature.

[0065] <NMR (Nuclear Magnetic Resonance Spectrum)> Using a 500 MHz NMR measuring device manufactured by JEOL Ltd., 1 1H-NMR and 29 For 29Si-NMR, the measurement sample was dissolved in deuterated chloroform (manufactured by Fujifilm Wako Pure Chemical Corporation) and measured at room temperature.

[0066] <TG (Thermogravimetric Analysis)> Using a TG measuring device manufactured by Rigaku Corporation, the weight loss amount from the initial sample weight when heating from room temperature to 250 °C at a heating rate of 10 °C / min was measured, and the reduction rate was calculated as TG to use as an index for the amount of outgas generated by heating. That is, a higher TG value means a larger amount of outgas, and a lower TG value means a smaller amount of outgas. Note that TG was performed under the following measurement conditions. a) Measuring instrument: Thermo plus EVO2 TG-DTA8120 / S manufactured by Rigaku Corporation b) Pan: Made of aluminum c) Heating rate: 10 °C / min d) Measurement atmosphere: Air 200 mL / min e) Standard sample: Al2O3 f) Sample amount: 10 mg

[0067] <Example 1> (Synthesis of silanol compound (2'-1) with n=27) In a 500 mL four-necked flask equipped with a stirring bar, thermometer, and reflux condenser, 2,4,6-trimethyl-2,4,6-trivinylcyclotrisiloxane (3.9 g) and toluene (35.4 g) were added at room temperature and the mixture was purged with nitrogen. Then, n-butyllithium (11.8 g; 2.6 mol / L) was added and the mixture was stirred for 1 hour. Hexamethylcyclotrisiloxane (51.8 g) and toluene (65.9 g) were added to the flask, and N,N-dimethylformamide (9.1 g) was added at 10°C and the mixture was reacted for 3.5 hours. Acetic acid (5.5 g) was added at 10°C to stop polymerization, and the mixture was stirred for another hour. At room temperature, 150g of water was added to a flask and stirred for 15 minutes. The mixture was then transferred to a separatory funnel and allowed to stand. After confirming that it had separated into two layers, the lower aqueous layer was removed from the separatory funnel. The upper layer was then washed with 200g of water, and this process was repeated eight times. The organic layer remaining in the separatory funnel was transferred to a 300 mL round-bottom flask and heated stepwise to 100°C under reduced pressure using a vacuum pump. A pale yellow, transparent liquid (50.5 g) was obtained by distilling off any volatile substances remaining in the product. 1 H-NMR and 29 The chemical shift obtained from the Si-NMR measurement is shown below. 1 H-NMR: δ(ppm); 6.13~5.69(3H), 2.27(1H), 1.34~1.26(6H), 0.90~0.84(5H), 0.62~0.56(2H), 0.20~-0.07(163H). 29 Si-NMR: δ(ppm): -1.92, -8.3, -18.7, -19.0~-20.5. These NMR measurement results confirmed that the obtained compounds, on average, have the structure of equation (2'-1). TIFF2026059089000012.tif2092

[0068] GPC analysis of the obtained compound revealed a number-average molecular weight (Mn) of 2400, a weight-average molecular weight (Mw) of 2800, and a molecular weight distribution (Mw / Mn) of 1.16. These average molecular weight values ​​are reference values ​​for structural identification using the above formula (2'-1).

[0069] (Synthesis and evaluation of a four-branched vinyl organopolysiloxane compound (1-1)) In a 100 mL three-necked flask equipped with a stirring bar, thermometer, and dropping funnel, N,N-dimethylformamide (1.8 g) and toluene (15.8 g) were added at room temperature and purged with nitrogen. Tetrachlorosilane (77.0 mg) was then added, the mixture was cooled to 0°C, and stirred for 10 minutes. N,N-dimethylformamide (0.4 g), toluene (4.0 g), the compound (2'-1) obtained in Example 1 (4.0 g), and triethylamine (0.3 g) were charged into the dropping funnel and added dropwise into the flask over 30 minutes, and the mixture was allowed to react for 1 hour. Polymerization was stopped by adding 3% aqueous acetic acid solution (20 g) at 20°C. The solution was then transferred to a separatory funnel and allowed to stand. After confirming that it had separated into two layers, the lower aqueous layer was removed from the separatory funnel. The upper layer was then neutralized with 5% sodium bicarbonate solution (20g), the lower layer was removed from the separatory funnel, and the subsequent washing with water (20g) was repeated three times. The organic layer remaining in the separatory funnel was transferred to a 100 mL round-bottom flask and heated stepwise to 100°C under reduced pressure using a vacuum pump to remove residual volatile substances from the product, yielding a pale yellow transparent liquid (3.9 g). 1 H-NMR and 29 The chemical shift obtained from the Si-NMR measurement is shown below. 1 H-NMR: δ(ppm); 6.13~5.69(12H), 1.36~1.24(24H), 0.91~0.83(18H), 0.62~0.56(8H), 0.20~-0.08(619H). 29 Si-NMR: δ(ppm): -0.78, -16.2~-19.5, -91.5, -95.9. From these NMR measurement results, it was confirmed that the obtained compounds, on average, had the structure shown in formula (1-1). TIFF2026059089000013.tif20108

[0070] GPC analysis of the obtained compound revealed a number-average molecular weight (Mn) of 5800, a weight-average molecular weight (Mw) of 6700, and a molecular weight distribution (Mw / Mn) of 1.17. These average molecular weight values ​​are reference values ​​for structural identification using the above formula (1-1).

[0071] When the TG content of the obtained compound was measured, it was found to be 0.23%.

[0072] <Example 2> (Synthesis of the silanol compound (2'-2) with n=44) In a 1 L four-necked flask equipped with a stirring bar, thermometer, and reflux condenser, 2,4,6-trimethyl-2,4,6-trivinylcyclotrisiloxane (9.6 g) and toluene (86.8 g) were added at room temperature and purged with nitrogen. Then, n-butyllithium (28.6 g; 2.6 mol / L) was added and the mixture was stirred for 1 hour. Hexamethylcyclotrisiloxane (270.9 g) and toluene (344.4 g) were added to the flask, and N,N-dimethylformamide (36.4 g) was added at 10°C and the mixture was reacted for 3.5 hours. Acetic acid (13.3 g) was added at 10°C to stop polymerization, and the mixture was stirred for a further 14 hours. At room temperature, 150g of water was added to a flask and stirred for 15 minutes. The mixture was then transferred to a separatory funnel and allowed to stand. After confirming that it had separated into two layers, the lower aqueous layer was removed from the separatory funnel. The upper layer was then washed with 200g of water, and this process was repeated eight times. The organic layer remaining in the separatory funnel was transferred to a 500 mL four-necked flask equipped with a stirring bar, thermometer, collection flask, and distillation head. The mixture was then heated in stages to 100°C under reduced pressure using a vacuum pump, and residual volatile substances were removed by distillation to obtain a pale yellow, transparent liquid (248.8 g). 1 H-NMR and 29The chemical shift obtained from the Si-NMR measurement is shown below. 1 H-NMR: δ(ppm); 6.11~5.69(3H), 2.22(1H), 1.33~1.26(6H), 0.87(4H), 0.58(2H), 0.19~-0.07(264H). 29 Si-NMR: δ(ppm): -1.9, -12.7, -19.3, -19.6~-20.3. These NMR measurement results confirmed that the obtained compounds, on average, have the structure of equation (2'-2). TIFF2026059089000014.tif2092

[0073] GPC analysis of the obtained compound revealed a number-average molecular weight (Mn) of 4100, a weight-average molecular weight (Mw) of 4500, and a molecular weight distribution (Mw / Mn) of 1.10. These average molecular weight values ​​are reference values ​​for structural identification using the above formula (2'-2).

[0074] (Synthesis and evaluation of four-branched vinyl organopolysiloxane compounds (1-2)) In a 100 mL three-necked flask equipped with a stirring bar, thermometer, and dropping funnel, N,N-dimethylformamide (1.8 g) and toluene (15.8 g) were added at room temperature and purged with nitrogen. Tetrachlorosilane (45.0 mg) was then added, the mixture was cooled to 0°C, and stirred for 10 minutes. N,N-dimethylformamide (0.4 g), toluene (4.0 g), the compound (2'-2) obtained in Example 2 (4.0 g), and triethylamine (0.3 g) were charged into the dropping funnel and added dropwise into the flask over 30 minutes, and the mixture was allowed to react for 1 hour. Polymerization was stopped by adding 3% aqueous acetic acid solution (20 g) at 20°C. The solution was then transferred to a separatory funnel and allowed to stand. After confirming that it had separated into two layers, the lower aqueous layer was removed from the separatory funnel. The upper layer was then neutralized with 5% sodium bicarbonate solution (20g), the lower layer was removed from the separatory funnel, and the subsequent washing with water (20g) was repeated three times. The organic layer remaining in the separatory funnel was transferred to a 100 mL round-bottom flask and heated stepwise to 100°C under reduced pressure using a vacuum pump to remove residual volatile substances from the product, yielding a pale yellow transparent liquid (3.9 g). 1 H-NMR and 29 The chemical shift obtained from the Si-NMR measurement is shown below. 1 H-NMR: δ(ppm); 6.13~5.69(12H), 1.36~1.24(24H), 0.91~0.83(17H), 0.62~0.56(8H), 0.20~-0.08(1034H). 29 Si-NMR: δ(ppm): -0.78, -16.2~-19.5, -91.5, -95.9. From these NMR measurement results, it was confirmed that the obtained compounds, on average, had the structure shown in equation (1-2). TIFF2026059089000015.tif20108

[0075] GPC analysis of the obtained compound revealed a number-average molecular weight (Mn) of 11,200, a weight-average molecular weight (Mw) of 13,300, and a molecular weight distribution (Mw / Mn) of 1.19. These average molecular weight values ​​are reference values ​​for structural identification using the above formula (1-2).

[0076] When the TG content of the obtained compound was measured, it was found to be 0.19%.

[0077] <Example 3: Synthesis and evaluation of tri-branched vinyl organopolysiloxane compounds (1-3)> In a 100 mL three-necked flask equipped with a stirring bar, thermometer, and dropping funnel, N,N-dimethylformamide (1.8 g) and toluene (15.8 g) were added at room temperature and purged with nitrogen. Trichloromethylsilane (90.0 mg) was then added, the mixture was cooled to 0°C, and stirred for 10 minutes. N,N-dimethylformamide (0.4 g), toluene (4.0 g), the compound (2'-1) obtained in Example 1 (4.0 g), and triethylamine (0.2 g) were charged into the dropping funnel and added dropwise into the flask over 30 minutes, and the mixture was allowed to react for 1 hour. Polymerization was stopped by adding 3% aqueous acetic acid solution (20 g) at 20°C. The solution was then transferred to a separatory funnel and allowed to stand. After confirming that it had separated into two layers, the lower aqueous layer was removed from the separatory funnel. The upper layer was then neutralized with 5% sodium bicarbonate solution (20g), the lower layer was removed from the separatory funnel, and the subsequent washing with water (20g) was repeated three times. The organic layer remaining in the separatory funnel was transferred to a 100 mL round-bottom flask and heated stepwise to 100°C under reduced pressure using a vacuum pump to remove residual volatile substances from the product, yielding a pale yellow transparent liquid (3.9 g). 1 H-NMR and 29 The chemical shift obtained from the Si-NMR measurement is shown below. 1 H-NMR: δ(ppm); 6.13~5.69(9H), 1.39~1.22(19H), 0.92~0.82(16H), 0.64~0.48(7H), 0.25~-0.10(548H). 29 Si-NMR: δ(ppm): -1.69, -18.3~-20.5, -53.5. From these NMR measurement results, it was confirmed that the obtained compounds, on average, had the structure shown in equation (1-3). TIFF2026059089000016.tif20108

[0078] GPC analysis of the obtained compound revealed a number-average molecular weight (Mn) of 4800, a weight-average molecular weight (Mw) of 5700, and a molecular weight distribution (Mw / Mn) of 1.21. These average molecular weight values ​​are reference values ​​for structural identification using the above formula (1-3).

[0079] When the TG content of the obtained compound was measured, it was found to be 0.18%.

[0080] <Example 4: Synthesis and evaluation of tri-branched vinyl organopolysiloxane compounds (1-4)> In a 100 mL three-necked flask equipped with a stirring bar, thermometer, and dropping funnel, N,N-dimethylformamide (1.8 g) and toluene (15.8 g) were added at room temperature and purged with nitrogen. Trichloromethylsilane (53.0 mg) was then added, the mixture was cooled to 0°C, and stirred for 10 minutes. N,N-dimethylformamide (0.4 g), toluene (4.0 g), the compound (2'-2) obtained in Example 2 (4.0 g), and triethylamine (0.2 g) were charged into the dropping funnel and added dropwise into the flask over 30 minutes, and the mixture was allowed to react for 1 hour. Polymerization was stopped by adding 3% aqueous acetic acid solution (20 g) at 20°C. The solution was then transferred to a separatory funnel and allowed to stand. After confirming that it had separated into two layers, the lower aqueous layer was removed from the separatory funnel. The upper layer was then neutralized with 5% sodium bicarbonate solution (20g), the lower layer was removed from the separatory funnel, and the subsequent washing with water (20g) was repeated three times. The organic layer remaining in the separatory funnel was transferred to a 100 mL round-bottom flask and heated stepwise to 100°C under reduced pressure using a vacuum pump to remove residual volatile substances from the product, yielding a pale yellow transparent liquid (3.8 g). 1 H-NMR: δ(ppm); 6.13~5.69(9H), 1.39~1.22(18H), 0.92~0.82(16H), 0.64~0.48(7H), 0.25~-0.10(779H). 29 Si-NMR: δ(ppm): -1.69, -18.3~-20.5, -53.5. From these NMR measurement results, it was confirmed that the obtained compounds, on average, had the structure shown in formulas (1-4). TIFF2026059089000017.tif20108

[0081] GPC analysis of the obtained compound revealed a number-average molecular weight (Mn) of 9300, a weight-average molecular weight (Mw) of 11000, and a molecular weight distribution (Mw / Mn) of 1.18. These average molecular weight values ​​are reference values ​​for structural identification using the above formula (1-4).

[0082] When the TG content of the obtained compound was measured, it was found to be 0.15%.

[0083] <Comparative Example 1: Synthesis and Evaluation of 4-Branched Vinyl Organopolysiloxane Compounds (1-5)> In this comparative example, compounds (1-5) were synthesized using the same method as described in Japanese Patent No. 5039250. Specifically, in a 100 mL three-necked flask equipped with a stirring bar, thermometer, dropping funnel, and reflux condenser, tetrakis[dimethyl(vinyl)silyloxy]silane (2.16 g), octamethylcyclotetrasiloxane (37.0 g), and trifluoromethanesulfonic acid (1.7 g) were added at room temperature, the flask was purged with nitrogen, and the temperature was raised to 90°C for 5 hours. After cooling to room temperature, water (5 g) was added and the mixture was stirred for 15 minutes. The mixture was then transferred to a separatory funnel and allowed to stand. After confirming that it had separated into two layers, the lower aqueous layer was removed from the separatory funnel. The upper layer was then neutralized with 5% sodium bicarbonate solution (10 g), the lower layer was removed from the separatory funnel, and the process of washing with water (20 g) was repeated three times. The organic layer remaining in the separatory funnel was transferred to a 500 mL round-bottom flask and heated stepwise to 100°C under reduced pressure using a vacuum pump. A pale yellow transparent liquid (37.9 g) was obtained by distilling off any volatile substances remaining in the product. 1 H-NMR: δ(ppm); 6.13~5.70(12H), 0.28~-0.08(553H). 29Si-NMR: δ(ppm): -0.78, -16.2~-19.5, -91.5, -95.9. From these NMR measurement results, it was confirmed that the obtained compounds, on average, had the structure shown in equations (1-5). TIFF2026059089000018.tif20108

[0084] GPC analysis of the obtained compound revealed a number-average molecular weight (Mn) of 3700, a weight-average molecular weight (Mw) of 8500, and a molecular weight distribution (Mw / Mn) of 2.30. These average molecular weight values ​​are reference values ​​for structural identification using the above formulas (1-5).

[0085] When the TG of the obtained compound was measured, the TG was found to be 0.89%.

[0086] Examples 1-4 and Comparative Example 1 show that organopolysiloxane compounds with a molecular weight distribution (Mw / Mn) of 2.0 or less exhibit less weight loss at 250°C compared to organopolysiloxane compounds with a molecular weight distribution (Mw / Mn) greater than 2.0, indicating less outgassing due to heating. [Industrial applicability]

[0087] The organopolysiloxane compound of the present invention is a material that can be used as a raw material for silicone rubber compositions in building materials, daily necessities, medical devices, electronic materials, etc. By using it as a raw material for silicone rubber compositions or as an additive to organic resins, it can be used to impart properties such as flexibility, water repellency, mold release, weather resistance, heat resistance, and electrical insulation to organic resins, which are due to the structure of the organopolysiloxane compound. In particular, by using it for electronic materials such as semiconductors that are undesirable due to outgassing, it is expected to have the effect of preventing contact failures, adhesion failures, and contamination of heating furnaces.

Claims

1. An organopolysiloxane compound represented by formula (1), having a molecular weight distribution (Mw / Mn) of 2.0 or less. In formula (1), R １ is hydrogen, an alkyl group in which at least one hydrogen may be replaced by a halogen, an alkenyl group in which at least one hydrogen may be replaced by a halogen, an alkynyl group in which at least one hydrogen may be replaced by a halogen, a cycloalkyl group in which at least one hydrogen may be replaced by a halogen, an aryl group in which at least one hydrogen may be replaced by a halogen, a functional group, or a group having a functional group; R ２ is alkyl or aryl; R ３ Each is independently a hydrogen, an alkyl whose at least one hydrogen may be replaced by a halogen, an alkenyl whose at least one hydrogen may be replaced by a halogen, an alkynyl whose at least one hydrogen may be replaced by a halogen, a cycloalkyl whose at least one hydrogen may be replaced by a halogen, or an aryl whose at least one hydrogen may be replaced by a halogen; R ４ is hydrogen, an alkyl group in which at least one hydrogen may be replaced by a halogen, an alkenyl group in which at least one hydrogen may be replaced by a halogen, an alkynyl group in which at least one hydrogen may be replaced by a halogen, a cycloalkyl group in which at least one hydrogen may be replaced by a halogen, an aryl group in which at least one hydrogen may be replaced by a halogen, a functional group, or a group having a functional group; n is an integer greater than or equal to 3; p is either 3 or 4.

2. In formula (1), R １ is hydrogen or an alkenyl with 2 to 6 carbon atoms; R ２ R is an alkyl or phenyl molecule having 1 to 4 carbon atoms; ３ The organopolysiloxane compound according to claim 1, wherein each of them is independently hydrogen, methyl, vinyl, 3,3,3-trifluoropropyl, or phenyl.

3. In formula (1), R １ is hydrogen or vinyl; R ２ is alkyl having 1 to 4 carbon atoms or phenyl; R ３ is each independently hydrogen, methyl, vinyl, 3,3,3-trifluoropropyl or phenyl, the organopolysiloxane compound according to claim 1.

4. In formula (1), R １ is hydrogen or vinyl; R ２ is butyl; R ３ is methyl; R ４ The organopolysiloxane compound according to claim 1, wherein is hydrogen or methyl.

5. A process of reacting an organometallic compound with a cyclic siloxane to produce a metal silanolate, The following steps involve reacting cyclotrisiloxane or cyclotetrasiloxane with a metal silanolate to produce the compound shown in formula (2), A method for producing an organopolysiloxane compound according to any one of claims 1 to 4, further comprising the step of reacting a compound represented by formula (3) with a compound represented by formula (2). In formula (2), R １ is hydrogen, an alkyl group in which at least one hydrogen may be replaced by a halogen, an alkenyl group in which at least one hydrogen may be replaced by a halogen, an alkynyl group in which at least one hydrogen may be replaced by a halogen, a cycloalkyl group in which at least one hydrogen may be replaced by a halogen, an aryl group in which at least one hydrogen may be replaced by a halogen, a functional group, or a group having a functional group; R ２ is alkyl or aryl; R ３ Each is independently a hydrogen, an alkyl whose at least one hydrogen may be replaced by a halogen, an alkenyl whose at least one hydrogen may be replaced by a halogen, an alkynyl whose at least one hydrogen may be replaced by a halogen, a cycloalkyl whose at least one hydrogen may be replaced by a halogen, or an aryl whose at least one hydrogen may be replaced by a halogen; M is a monovalent metal; n is an integer greater than or equal to 3; In formula (3), R ４ is hydrogen, an alkyl group in which at least one hydrogen may be replaced by a halogen, an alkenyl group in which at least one hydrogen may be replaced by a halogen, an alkynyl group in which at least one hydrogen may be replaced by a halogen, a cycloalkyl group in which at least one hydrogen may be replaced by a halogen, an aryl group in which at least one hydrogen may be replaced by a halogen, a functional group, or a group having a functional group; X is a halogen or alkoxy; p is either 3 or 4.

6. A method for producing an organopolysiloxane compound according to claim 5, wherein the organometallic compound is an alkyllithium compound, the cyclic siloxane is a compound represented by formula (4), and the metal silanolate is a lithium silanolate. (The symbol "Me" above represents methyl.) In formula (4), R ５ is hydrogen or vinyl, and m is 3 or 4.

7. A process of reacting an organometallic compound with a cyclic siloxane to produce a metal silanolate, The following steps involve reacting cyclotrisiloxane or cyclotetrasiloxane with a metal silanolate to produce the compound shown in formula (2), The following steps involve stopping the polymerization of the compound represented by formula (2) by adding water or acid to produce the compound represented by formula (2'), A method for producing an organopolysiloxane compound according to any one of claims 1 to 4, further comprising the step of reacting a compound represented by formula (3) with a compound represented by formula (2'). In formula (2), R １ is hydrogen, an alkyl group in which at least one hydrogen may be replaced by a halogen, an alkenyl group in which at least one hydrogen may be replaced by a halogen, an alkynyl group in which at least one hydrogen may be replaced by a halogen, a cycloalkyl group in which at least one hydrogen may be replaced by a halogen, an aryl group in which at least one hydrogen may be replaced by a halogen, a functional group, or a group having a functional group; R ２ is alkyl or aryl; R ３ Each is independently a hydrogen, an alkyl whose at least one hydrogen may be replaced by a halogen, an alkenyl whose at least one hydrogen may be replaced by a halogen, an alkynyl whose at least one hydrogen may be replaced by a halogen, a cycloalkyl whose at least one hydrogen may be replaced by a halogen, or an aryl whose at least one hydrogen may be replaced by a halogen; M is a monovalent metal; n is an integer greater than or equal to 3; In formula (2'), R １ , R ２ and R ３ R in equation (2) １ , R ２ and R ３ It is the same basis of definition as; n has the same definition as n in equation (2); In formula (3), R ４ is hydrogen, an alkyl group in which at least one hydrogen may be replaced by a halogen, an alkenyl group in which at least one hydrogen may be replaced by a halogen, an alkynyl group in which at least one hydrogen may be replaced by a halogen, a cycloalkyl group in which at least one hydrogen may be replaced by a halogen, an aryl group in which at least one hydrogen may be replaced by a halogen, a functional group, or a group having a functional group; X is a halogen or alkoxy; p is either 3 or 4.

8. A method for producing an organopolysiloxane compound according to claim 7, wherein the organometallic compound is an alkyllithium compound, the cyclic siloxane is a compound represented by formula (4) as described in claim 6, and the metal silanolate is a lithium silanolate.

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