Method for producing aminoalkylalkoxydisiloxane compounds

Abstract

To provide a method capable of effectively producing a disiloxane compound having an alkoxysilyl group using an oligosiloxane compound discarded heretofore.SOLUTION: A method of producing an amino alkylalkoxy disiloxane compound represented by formula (4) includes a neutralization process of adding a metal hydroxide or a metal alkoxide to a mixture of an amino alkylalkoxy oligosiloxane compound and an amino alkylalkoxy silane compound for a reaction, and neutralizing the metal hydroxide or metal alkoxide in the resulting reaction mixture with Broensted acid. R1 is each independently an unsubstituted bivalent 1-8C hydrocarbon group. R2 and R3 are respectively independently an unsubstituted univalent 1-6C hydrocarbon group. A is an amino group.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a method for producing an aminoalkylalkoxydisiloxane compound. [Background technology]

[0002] Aminoalkylalkoxysilane compounds (hereinafter also referred to as "monomer compounds"), which are useful as silane coupling agents, surface treatment agents, resin additives, resin modifiers, or paint additives, can be hydrolyzed and condensed to produce the corresponding aminoalkylalkoxydisiloxane compounds (hereinafter also referred to as "disiloxane compounds"), aminoalkylalkoxytrisiloxane compounds (hereinafter also referred to as "trisiloxane compounds"), and further hydrolyzed and condensed compounds (hereinafter, the hydrolyzed and condensed products from trisiloxane compounds to octasiloxanes are collectively referred to as "oligosiloxane compounds"). These hydrolyzed and condensed products have a higher molecular weight than monomer compounds, making them less volatile and easier to handle. Furthermore, they emit fewer volatile organic compounds (VOCs) per unit mass than monomer compounds, resulting in less impact on the environment and human health. Disiloxane compounds, in particular, have a lower boiling point than larger oligosiloxane compounds, allowing for isolation by distillation and often being obtained without the coloration inherent to the amino group.

[0003] Examples of methods for producing such aminoalkylalkoxydisiloxane compounds include a method in which an aminoalkylalkoxysilane compound, which is a monomer compound, is hydrolyzed and condensed using 0.5 to 5 equivalent moles of water, followed by purification by distillation (Patent Document 1).

[0004] Furthermore, a method for producing a disiloxane compound that does not have an aminoalkyl group has been reported in which a linear oligosiloxane compound modified at both ends with alkoxy groups is reacted in the presence of an alkoxysilane compound using trifluoromethanesulfonic acid as a catalyst, and then the disiloxane compound is obtained by distillation purification without treating with trifluoromethanesulfonic acid (Patent Document 2). [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Laid-Open No. 2002-193976 [Patent Document 2] Japanese Patent Application Publication No. 8-319294 Summary of the Invention [Problem to be solved by the invention]

[0006] In the method described in Patent Document 1, the alkoxysilyl group in the monomer compound is a trialkylmonoalkoxy group, and therefore, when a hydrolysis condensation reaction is carried out, in principle, only a disiloxane compound having no alkoxysilyl group can be obtained. On the other hand, when the alkoxysilyl group in the monomer compound is a dialkyldialkoxysilyl group or a monoalkyltrialkoxysilyl group, the hydrolysis and condensation reaction proceeds non-selectively. In other words, since the target disiloxane compound also has an alkoxysilyl group capable of hydrolysis and condensation, an oligosiloxane compound may also be produced through further hydrolysis and condensation. For this reason, it is impossible to efficiently produce only a disiloxane compound through the hydrolysis and condensation reaction of an aminoalkylalkoxysilane compound whose alkoxysilyl group is a dialkyldialkoxysilyl group or an alkyltrialkoxysilyl group.

[0007] When producing an aminoalkylalkoxydisiloxane compound by the hydrolysis and condensation reaction of an aminoalkylalkoxysilane compound, it is important to add less than 0.5 moles of water per mole of the aminoalkylalkoxysilane compound to minimize the formation of oligosiloxane compounds. By doing so, the aminoalkylalkoxysilane compound, which is a monomer compound, remains, and can be recovered and reused by distillation purification. However, even in this case, the formation of oligosiloxane compounds cannot be completely suppressed. Therefore, the resulting oligosiloxane compounds cannot be reused and become waste.

[0008] On the other hand, when the method of Patent Document 2 is applied to the production of aminoalkylalkoxydisiloxane compounds, the high temperature conditions encountered during distillation result in the recovery of only the compound with the smallest molecular weight, i.e., the monomer compound, and no alkoxydisiloxane compound is obtained. This is because the acid catalyst is too strong, and the target aminoalkylalkoxydisiloxane compound itself is subject to cracking. Therefore, in the presence of a strong acid or strong base, the alkoxydisiloxane compound is also cracked, making it impossible to isolate.

[0009] The present invention has been made in view of the above circumstances, and has as its object to provide a method for producing a disiloxane compound having an alkoxysilyl group, which can efficiently produce a disiloxane compound having an alkoxysilyl group while reducing waste by producing the disiloxane compound using an oligosiloxane compound that would conventionally be discarded. [Means for solving the problem]

[0010]

[0003] The present inventors conducted extensive research to solve the above problems and discovered that adding an aminoalkylalkoxysilane compound and a metal hydroxide or metal alkoxide to a composition containing an oligosiloxane compound causes rearrangement of the aminoalkylalkoxysilane compound and the oligosiloxane compound, resulting in the production of an aminoalkylalkoxydisiloxane compound. Furthermore, they discovered that neutralizing the metal hydroxide or metal alkoxide with a Bronsted acid and purifying the reaction solution by distillation allows the aminoalkylalkoxydisiloxane compound to be stably isolated by distillation even under high-temperature conditions, thereby completing the present invention.

[0011] That is, the present invention is 1. The following general formula (1) [ka] [In the formula, R 1 each independently represents an unsubstituted divalent hydrocarbon group having 1 to 8 carbon atoms, and R 2 and R 3 each independently represents an unsubstituted monovalent hydrocarbon group having 1 to 6 carbon atoms, and X represents R 2 OR 3 Each A independently represents the following general formula (2): [ka] (In the formula, R 4 and R 5 each independently represents a hydrogen atom or an unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms which may contain an oxygen atom or a nitrogen atom, and may be bonded to each other to form a ring structure, but R 4 and R 5 and (a) are water atoms, and (b) are water atoms. n is 0 or 1, and m is an integer from 1 to 6. and an aminoalkylalkoxyoligosiloxane compound represented by the following general formula (3): [ka] (In the formula, R1 ~R 3 , A and n have the same meanings as above. and a neutralization step of neutralizing the metal hydroxide or metal alkoxide in the resulting reaction solution with a Bronsted acid. [ka] (In the formula, R 1 ~R 3 , A and n have the same meanings as above. A method for producing an aminoalkylalkoxydisiloxane compound represented by the formula: 2. The method for producing an aminoalkylalkoxydisiloxane compound according to claim 1, further comprising a distillation step after the neutralization step. to provide. [Effects of the Invention]

[0012] In the production method of the present invention, when an aminoalkylalkoxydisiloxane compound is produced by the hydrolysis and condensation reaction of an aminoalkylalkoxysilane compound, the aminoalkylalkoxydisiloxane compound can be produced using an aminoalkylalkoxyoligosiloxane compound that would previously have been discarded, thereby enabling the efficient production of an aminoalkylalkoxydisiloxane compound while reducing the amount of waste. DETAILED DESCRIPTION OF THE INVENTION

[0013] The present invention will be specifically described below. The production method of the present invention comprises the steps of adding a metal hydroxide or metal alkoxide to a mixture of an aminoalkylalkoxyoligosiloxane compound represented by the following general formula (1) (hereinafter also referred to as compound (1)) and an aminoalkylalkoxysilane compound represented by the following general formula (3) (hereinafter also referred to as compound (3)) to react them, and neutralizing the metal hydroxide or metal alkoxide in the resulting reaction solution with a Bronsted acid.

[0014] [ka]

[0015] In the above general formulas (1) and (3), R 1 each independently represents an unsubstituted divalent hydrocarbon group having 1 to 8 carbon atoms, preferably 1 to 5 carbon atoms, and more preferably 1 to 3 carbon atoms. R 1 The divalent hydrocarbon group may be linear, branched, or cyclic, and specific examples thereof include linear alkylene groups such as methylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, and octamethylene; branched alkylene groups such as methylethylene (propylene) and methyltrimethylene; cyclic alkylene groups such as cyclohexylene and methylenecyclohexylenemethylene; linear alkenylene groups such as propenylene, butenylene, hexenylene, and octenylene; branched alkenylene groups such as isopropenylene and isobutenylene; arylene groups such as phenylene; and aralkylene groups such as methylenephenylene and methylenephenylenemethylene. Among these, from the viewpoint of ease of procurement of raw materials, a linear alkylene group is preferred, and a linear alkylene group having 1 to 3 carbon atoms is more preferred.

[0016] In the above general formulas (1) and (3), R 2 and R 3 each independently represents an unsubstituted monovalent hydrocarbon group having 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms. R 2 and R 3The monovalent hydrocarbon group may be linear, branched, or cyclic, and specific examples thereof include linear alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, and n-hexyl; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, neopentyl, and thexyl; cyclic alkyl groups such as cyclopentyl and cyclohexyl; alkenyl groups such as vinyl, allyl, propenyl, butenyl, and pentenyl; and aryl groups such as phenyl. Among these, from the viewpoint of ease of procurement of raw materials, a linear alkyl group is preferred, and a linear alkyl group having 1 to 3 carbon atoms is more preferred.

[0017] In the above general formulas (1) and (3), each A independently represents a group represented by the following general formula (2).

[0018] [ka]

[0019] In the above general formula (2), R 4 and R 5 is a hydrogen atom or an unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, preferably 1 to 5 carbon atoms, and more preferably 1 to 3 carbon atoms, which may contain an oxygen atom or a nitrogen atom, and R 4 and R 5 cannot both be hydrogen atoms. R 4 and R 5The monovalent hydrocarbon group may be linear, branched, or cyclic, and specific examples thereof include linear alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, and decyl; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, neopentyl, thexyl, and 2-ethylhexyl; cyclic alkyl groups such as cyclopentyl and cyclohexyl; alkenyl groups such as vinyl, allyl (2-propenyl), 1-propenyl, butenyl, pentenyl, and octenyl; aryl groups such as phenyl and tolyl; and aralkyl groups such as benzyl and phenethyl.

[0020] Also, R 4 and R 5 may be bonded to each other to form a ring structure represented by the following general formula (7) together with the nitrogen atom.

[0021] [ka]

[0022] In general formula (7), R 4 and R 5 When R forms a ring, the number of carbon atoms contained in the ring is preferably 3 to 6. 4 and R 5 and preferably form a linear alkylene group having 3 to 6 carbon atoms. In addition, this alkylene chain may contain -O-, -NR- (where R represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms), etc. Examples of the linear alkylene group having 3 to 6 carbon atoms and the alkyl group having 1 to 6 carbon atoms include the above-mentioned R 1 and R 2 Examples of the groups include the same as those exemplified in the above. Examples of such a ring structure include a piperidine ring, a pyrrolidine ring, a piperazine ring, a methylpiperazine ring, and a morpholine ring.

[0023] In the general formula (1), X is R 2 OR 3 and R2 and R 3 As for the above R 2 and R 3 The same substituents as those mentioned above can be mentioned. Furthermore, m is an integer of 1 to 6, preferably an integer of 1 to 4, more preferably 1 or 2, and even more preferably 1. If m exceeds 6, the viscosity increases, making handling difficult.

[0024] In the general formulae (1) and (3), each n is independently 0 or 1.

[0025] Specific examples of compound (1) include 1,3,5-tris(diethylaminopropyl)-1,1,3,5,5-pentamethoxytrisiloxane, 1,3,5-tris(dimethylaminopropyl)-1,1,3,5,5-pentamethoxytrisiloxane, 1,3,5-tris(dibutylaminopropyl)-1,1,3,5,5-pentamethoxytrisiloxane, 1,3,5-tris(butylaminopropyl)-1,1,3,5,5-pentamethoxytrisiloxane, and 1,3,5-tris(phenylaminopropyl)-1,1,3,5,5-pentamethoxytrisiloxane. 1,3,5-tris(morpholinopropyl)-1,1,3,5,5-pentamethoxytrisiloxane, 1,3,5-tris(piperazinopropyl)-1,1,3,5,5-pentamethoxytrisiloxane, 1,3,5-tris(methylpiperazinopropyl)-1,1,3,5,5-pentamethoxytrisiloxane, 1,3,5-tris(diethylaminopropyl)-1,5-dimethoxy-1,3,5-trimethyltrisiloxane, 1,3,5-tris(dimethylaminopropyl)-1,5-dimethoxy-1,3,5-trimethyltrisiloxane, 1 ,3,5-Tris(dibutylaminopropyl)-1,5-dimethoxy-1,3,5-trimethyltrisiloxane, 1,3,5-tris(butylaminopropyl)-1,5-dimethoxy-1,3,5-trimethyltrisiloxane, 1,3,5-tris(phenylaminopropyl)-1,5-dimethoxy-1,3,5-trimethyltrisiloxane, 1,3,5-tris(morpholinopropyl)-1,5-dimethoxy-1,3,5-trimethyltrisiloxane, 1,3,5-tris(piperazinopropyl)-1,5-dimethoxy-1,3,5-trimethyltrisiloxane xane, 1,3,5-tris(methylpiperazinopropyl)-1,5-dimethoxy-1,3,5-trimethyltrisiloxane, 1,3,5-tris(diethylaminopropyl)-1,1,3,5,5-pentaethoxytrisiloxane, 1,3,5-tris(dimethylaminopropyl)-1,1,3,5,5-pentaethoxytrisiloxane, 1,3,5-tris(dibutylaminopropyl)-1,1,3,5,5-pentaethoxytrisiloxane, 1,3,5-tris(butylaminopropyl)-1,1,3,5,5-pentaethoxytrisiloxane, 1,3,5-tris(phenylaminopropyl)-1,1,3,5,5-pentaethoxytrisiloxane, 1,3,5-tris(morpholinopropyl)-1,1,3,5,5-pentaethoxytrisiloxane, 1,3,5-tris(piperazinopropyl)-1,1,3,5,5-pentaethoxytrisiloxane, 1,3,5-tris(methylpiperazinopropyl)-1,1,3,5,5-pentaethoxytrisiloxane, 1,3,5-tris(diethylaminopropyl)-1,5-diethoxy-1,3,5-trimethyltrisiloxane, 1,3,5-tris (dimethylaminopropyl)-1,5-diethoxy-1,3,5-trimethyltrisiloxane, 1,3,5-tris(dibutylaminopropyl)-1,5-diethoxy-1,3,5-trimethyltrisiloxane, 1,3,5-tris(butylaminopropyl)-1,5-diethoxy-1,3,5-trimethyltrisiloxane, 1,3,5-tris(phenylaminopropyl)-1,5-diethoxy-1,3,5-trimethyltrisiloxane, 1,3,5-tris(morpholinopropyl)-1,5-diethoxy-1,3,5-trimethyltrisiloxane, 1,3, Trisiloxane compounds such as 5-tris(piperazinopropyl)-1,5-diethoxy-1,3,5-trimethyltrisiloxane, 1,3,5-tris(methylpiperazinopropyl)-1,5-diethoxy-1,3,5-trimethyltrisiloxane; 1,3,5,7-tetrakis(diethylaminopropyl)-1,1,3,5,7,7-hexamethoxytetrasiloxane, 1,3,5,7-tetrakis(dimethylaminopropyl)-1,1,3,5,7,7-hexamethoxytetrasiloxane, 1,3,5,7-tetrakis(dibutylaminopropyl)-1 ,1,3,5,7,7-hexamethoxytetrasiloxane, 1,3,5,7-tetrakis(butylaminopropyl)-1,1,3,5,7,7-hexamethoxytetrasiloxane, 1,3,5,7-tetrakis(phenylaminopropyl)-1,1,3,5,7,7-hexamethoxytetrasiloxane, 1,3,5,7-tetrakis(morpholinopropyl)-1,1,3,5,7,7-hexamethoxytetrasiloxane, 1,3,5,7-tetrakis(piperazinopropyl)-1,1,3,5,7,7-hexamethoxytetrasiloxane, 1,3,5,7-Tetrakis(methylpiperazinopropyl)-1,1,3,5,7,7-hexamethoxytetrasiloxane, 1,3,5,7-tetrakis(diethylaminopropyl)-1,7-dimethoxy-1,3,5,7-tetramethyltetrasiloxane, 1,3,5,7-tetrakis(dimethylaminopropyl)-1,7-dimethoxy-1,3,5,7-tetramethyltetrasiloxane, 1,3,5,7-tetrakis(dibutylaminopropyl)-1,7-dimethoxy-1,3,5,7-tetramethyltetrasiloxane, 1,3,5,7-tetrakis(butylaminopropyl)-1,7-dimethoxy-1,3,5,7-tetramethyltetrasiloxane 1,3,5,7-tetrakis(methylpiperazinopropyl)-1,7-dimethoxy-1,3,5,7-tetramethyltetrasiloxane, 1,3,5,7-tetrakis(phenylaminopropyl)-1,7-dimethoxy-1,3,5,7-tetramethyltetrasiloxane, 1,3,5,7-tetrakis(morpholinopropyl)-1,7-dimethoxy-1,3,5,7-tetramethyltetrasiloxane, 1,3,5,7-tetrakis(piperazinopropyl)-1,7-dimethoxy-1,3,5,7-tetramethyltetrasiloxane, 1,3,5,7-tetrakis(methylpiperazinopropyl)-1,7-dimeth 1,3,5,7-tetrakis(diethylaminopropyl)-1,1,3,5,7,7-hexaethoxytetrasiloxane, 1,3,5,7-tetrakis(dimethylaminopropyl)-1,1,3,5,7,7-hexaethoxytetrasiloxane, 1,3,5,7-tetrakis(dibutylaminopropyl)-1,1,3,5,7,7-hexaethoxytetrasiloxane, 1,3,5,7-tetrakis(butylaminopropyl)-1,1,3,5,7,7-hexaethoxytetrasiloxane, 1,3,5 ,7-Tetrakis(phenylaminopropyl)-1,1,3,5,7,7-hexaethoxytetrasiloxane, 1,3,5,7-tetrakis(morpholinopropyl)-1,1,3,5,7,7-hexaethoxytetrasiloxane, 1,3,5,7-tetrakis(piperazinopropyl)-1,1,3,5,7,7-hexaethoxytetrasiloxane, 1,3,5,7-tetrakis(methylpiperazinopropyl)-1,1,3,5,7,7-hexaethoxytetrasiloxane, 1,3,5,7-tetrakis(diethylaminopropyl)-1,7-diethoxy-1,3,5,7-tetramethyltetrasiloxane, 1,3,5,7-tetrakis(dimethylaminopropyl)-1,7-diethoxy1,3,5,7-tetramethyltetrasiloxane, 1,3,5,7-tetrakis(dibutylaminopropyl)-1,7-diethoxy1,3,5,7-tetramethyltetrasiloxane, 1,3,5,7-tetrakis(butylaminopropyl)-1,7-diethoxy1,3,5,7-tetramethyltetrasiloxane, 1,3,5,7-tetrakis(phenylaminopropyl)-1,7-diethoxy1,3,5,7-tetramethyl Tetrasiloxane compounds such as 1,3,5,7-tetrakis(morpholinopropyl)-1,7-diethoxy-1,3,5,7-tetramethyltetrasiloxane, 1,3,5,7-tetrakis(piperazinopropyl)-1,7-diethoxy-1,3,5,7-tetramethyltetrasiloxane, and 1,3,5,7-tetrakis(methylpiperazinopropyl)-1,7-diethoxy-1,3,5,7-tetramethyltetrasiloxane; 1,3,5,7,9-pentakis(diethylaminopropyl)-1,1,3,5,7,9,9-heptamethoxy 1,3,5,7,9-pentakis(dimethylaminopropyl)-1,1,3,5,7,9,9-heptamethoxypentasiloxane, 1,3,5,7,9-pentakis(dibutylaminopropyl)-1,1,3,5,7,9,9-heptamethoxypentasiloxane, 1,3,5,7,9-pentakis(butylaminopropyl)-1,1,3,5,7,9,9-heptamethoxypentasiloxane, 1,3,5,7,9-pentakis(phenylaminopropyl)-1,1,3,5,7,9,9-heptamethoxypentasiloxane, 1,3,5,7,9-Pentakis(morpholinopropyl)-1,1,3,5,7,9,9-heptamethoxypentasiloxane, 1,3,5,7,9-Pentakis(piperazinopropyl)-1,1,3,5,7,9,9-heptamethoxypentasiloxane, 1,3,5,7,9-Pentakis(methylpiperazinopropyl)-1,1,3,5,7,9,9-heptamethoxypentasiloxane, 1,3,5,7,9-Pentakis(diethylaminopropyl)-1,9-dimethoxy-1,3,5,7,9-pentamethylpentasiloxane, 1,3,5,7,9-Pentakis(dimethylaminopropyl)-1,9-dimethoxy-1,3,5,7,9-pentamethylpentasiloxane, 1,3,5,7,9-Pentakis(dibutylaminopropyl)-1,9-dimethoxy-1,3,5,7,9-pentamethylpentasiloxane, 1,3,5,7,9-Pentakis(butylaminopropyl)-1,9-dimethoxy-1,3,5,7,9-pentamethylpentasiloxane, 1,3,5,7,9-Pentakis 1,3,5,7,9-pentakis(phenylaminopropyl)-1,9-dimethoxy-1,3,5,7,9-pentamethylpentasiloxane, 1,3,5,7,9-pentakis(morpholinopropyl)-1,9-dimethoxy-1,3,5,7,9-pentamethylpentasiloxane, 1,3,5,7,9-pentakis(piperazinopropyl)-1,9-dimethoxy-1,3,5,7,9-pentamethylpentasiloxane, 1,3,5,7,9-pentakis(methylpiperazinopropyl) 1,3,5,7,9-pentakis(diethylaminopropyl)-1,1,3,5,7,9,9-heptaethoxypentasiloxane, 1,3,5,7,9-pentakis(dimethylaminopropyl)-1,1,3,5,7,9,9-heptaethoxypentasiloxane, 1,3,5,7,9-pentakis(dibutylaminopropyl)-1,1,3,5, 7,9,9-heptaethoxypentasiloxane, 1,3,5,7,9-pentakis(butylaminopropyl)-1,1,3,5,7,9,9-heptaethoxypentasiloxane, 1,3,5,7,9-pentakis(phenylaminopropyl)-1,1,3,5,7,9,9-heptaethoxypentasiloxane, 1,3,5,7,9-pentakis(morpholinopropyl)-1,1,3,5,7,9,9-heptaethoxypentasiloxane, 1,3,5,7,9-Pentakis(piperazinopropyl)-1,1,3,5,7,9,9-heptaethoxypentasiloxane, 1,3,5,7,9-Pentakis(methylpiperazinopropyl)-1,1,3,5,7,9,9-heptaethoxypentasiloxane, 1,3,5,7,9-Pentakis(diethylaminopropyl)-1,9-diethoxy-1, 3,5,7,9-Pentamethylpentasiloxane, 1,3,5,7,9-Pentakis(dimethylaminopropyl)-1,9-diethoxy 1,3,5,7,9-pentamethylpentasiloxane, 1,3,5,7,9-Pentakis(dibutylaminopropyl)-1,9-diethoxy 1,3,5,7,9-pentamethylpentasiloxane, 1,3,5,7,9 - pentasiloxane compounds such as pentakis(butylaminopropyl)-1,9-diethoxy-1,3,5,7,9-pentamethylpentasiloxane, 1,3,5,7,9-pentakis(phenylaminopropyl)-1,9-diethoxy-1,3,5,7,9-pentamethylpentasiloxane, 1,3,5,7,9-pentakis(morpholinopropyl)-1,9-diethoxy-1,3,5,7,9-pentamethylpentasiloxane, 1,3,5,7,9-pentakis(piperazinopropyl)-1,9-diethoxy-1,3,5,7,9-pentamethylpentasiloxane, and 1,3,5,7,9-pentakis(methylpiperazinopropyl)-1,9-diethoxy-1,3,5,7,9-pentamethylpentasiloxane;1,3,5,7,9,11-Hexakis(diethylaminopropyl)-1,1,3,5,7,9,11,11-octamethoxyhexasiloxane, 1,3,5,7,9,11-Hexakis(phenylaminopropyl)-1,1,3,5,7,9,11,11-octamethoxyhexasiloxane, 1,3,5,7,9,11-Hexakis(morpholinopropyl)-1,1,3,5,7,9,11,11-octamethoxyhexasiloxane, 1,3,5,7,9, 11-Hexakis(diethylaminopropyl)-1,11-dimethoxy-1,3,5,7,9,11-hexamethylhexasiloxane, 1,3,5,7,9,11-Hexakis(phenylaminopropyl)-1,11-dimethoxy-1,3,5,7,9,11-hexamethylhexasiloxane, 1,3,5,7,9,11-Hexakis(morpholinopropyl)-1,11-dimethoxy-1,3,5,7,9,11-hexamethylhexasiloxane, 1,3,5 ,7,9,11-Hexakis(diethylaminopropyl)-1,1,3,5,7,9,11,11-octaethoxyhexasiloxane, 1,3,5,7,9,11-Hexakis(phenylaminopropyl)-1,1,3,5,7,9,11,11-octaethoxyhexasiloxane, 1,3,5,7,9,11-Hexakis(morpholinopropyl)-1,1,3,5,7,9,11,11-octaethoxyhexasiloxane, 1,3,5,7,9,11-Hexakis Hexasiloxane compounds such as sakis(diethylaminopropyl)-1,11-diethoxy-1,3,5,7,9,11-hexamethylhexasiloxane, 1,3,5,7,9,11-hexakis(phenylaminopropyl)-1,11-diethoxy-1,3,5,7,9,11-hexamethylhexasiloxane, and 1,3,5,7,9,11-hexakis(morpholinopropyl)-1,11-diethoxy-1,3,5,7,9,11-hexamethylhexasiloxane;1,3,5,7,9,11,13-heptakis(diethylaminopropyl)-1,1,3,5,7,9,11,13,13-nonamethoxyheptasiloxane, 1,3,5,7,9,11,13-heptakis(phenylaminopropyl)-1,1,3,5,7,9,11,13,13-nonamethoxyheptasiloxane, 1,3,5,7,9,11,13-heptakis(morpholinopropyl)-1,1,3,5,7,9,11,13,13-nonamethoxyheptasiloxane, 1,3,5,7,9,1 1,13-heptakis(diethylaminopropyl)-1,13-dimethoxy-1,3,5,7,9,11,13-heptamethylheptasiloxane, 1,3,5,7,9,11,13-heptakis(phenylaminopropyl)-1,13-dimethoxy-1,3,5,7,9,11,13-heptamethylheptasiloxane, 1,3,5,7,9,11,13-heptakis(morpholinopropyl)-1,13-dimethoxy-1,3,5,7,9,11,13-heptamethylheptasiloxane, 1,3,5 ,7,9,11,13-heptakis(diethylaminopropyl)-1,1,3,5,7,9,11,13,13-nonaethoxyheptasiloxane, 1,3,5,7,9,11,13-heptakis(phenylaminopropyl)-1,1,3,5,7,9,11,13,13-nonaethoxyheptasiloxane, 1,3,5,7,9,11,13-heptakis(morpholinopropyl)-1,1,3,5,7,9,11,13,13-nonaethoxyheptasiloxane, 1,3,5,7,9,11,13- Heptasiloxane compounds such as heptakis(diethylaminopropyl)-1,13-diethoxy-1,3,5,7,9,11,13-heptamethylheptasiloxane, 1,3,5,7,9,11,13-heptakis(phenylaminopropyl)-1,13-diethoxy-1,3,5,7,9,11,13-heptamethylheptasiloxane, and 1,3,5,7,9,11,13-heptakis(morpholinopropyl)-1,13-diethoxy-1,3,5,7,9,11,13-heptamethylheptasiloxane;1,3,5,7,9,11,13,15-Octakis(diethylaminopropyl)-1,1,3,5,7,9,11,13,15,15-decamethoxyoctasiloxane, 1,3,5,7,9,11,13,15-Octakis(phenylaminopropyl)-1,1,3,5,7,9,11,13,15,15-decamethoxyoctasiloxane, 1,3,5,7,9,11,13,15-Octakis(morpholinopropyl)-1,1,3,5,7,9,11,13,15,15-decamethoxyoctasiloxane, 1,3,5,7,9,11,13,15- Octakis(diethylaminopropyl)-1,15-dimethoxy-1,3,5,7,9,11,13,15-octamethyloctasiloxane, 1,3,5,7,9,111,3,5,7,9,11,13,15-octakis(phenylaminopropyl)-1,15-dimethoxy-1,3,5,7,9,11,13,15-octamethyloctasiloxane, 1,3,5,7,9,11,13,15-octakis(morpholinopropyl)-1,15-dimethoxy-1,3,5,7,9,11,13,15-octamethyloctasiloxane, 1,3,5,7, 9,11,13,15-Octakis(diethylaminopropyl)-1,1,3,5,7,9,11,13,15,15-decaethoxyoctasiloxane, 1,3,5,7,9,11,13,15-Octakis(phenylaminopropyl)-1,1,3,5,7,9,11,13,15,15-decaethoxyoctasiloxane, 1,3,5,7,9,11,13,15-Octakis(morpholinopropyl)-1,1,3,5,7,9,11,13,15,15-decaethoxyoctasiloxane, 1,3,5,7,9,11,13,15-Octakis(diethylaminopropyl)-1,1,3,5,7,9,11,13,15,15-decaethoxyoctasiloxane Examples of the octasiloxane compounds include 1,3,5,7,9,11,13,15-octakis(phenylaminopropyl)-1,15-diethoxy-1,3,5,7,9,11,13,15-octamethyloctasiloxane, 1,3,5,7,9,111,3,5,7,9,11,13,15-octakis(morpholinopropyl)-1,15-diethoxy-1,3,5,7,9,11,13,15-octamethyloctasiloxane, and the like.

[0026] The oligosiloxane compound of formula (1) can be obtained by hydrolyzing and condensing compound (3) and then removing compounds with boiling points lower than that of the trisiloxane compound by distillation.

[0027] These oligosiloxane compounds are R 1 ~R 3 As long as A and A are the same, that is, only the value of m is different, they may be used alone or as a mixture of two or more kinds.

[0028] Specific examples of compound (3) include trialkoxysilane compounds such as dimethylaminopropyltrimethoxysilane, diethylaminopropyltrimethoxysilane, dibutylaminopropyltrimethoxysilane, 1, butylaminopropyltrimethoxysilane, octylaminopropyltrimethoxysilane, phenylaminopropyltrimethoxysilane, morpholinopropyltrimethoxysilane, piperazinopropyltrimethoxysilane, methylpiperazinopropyltrimethoxysilane, diethylaminopropyltriethoxysilane, dimethylaminopropyltriethoxysilane, dibutylaminopropyltriethoxysilane, butylaminopropyltriethoxysilane, octylaminopropyltriethoxysilane, phenylaminopropyltriethoxysilane, morpholinopropyltriethoxysilane, piperazinopropyltriethoxysilane, and methylpiperazinopropyltriethoxysilane; diethylaminopropylmethyltriethoxysilane; Examples of alkyl dialkoxysilane compounds include alkyldimethoxysilane, dimethylaminopropylmethyldimethoxysilane, dibutylaminopropylmethyldimethoxysilane, butylaminopropylmethyldimethoxysilane, octylaminopropylmethyldimethoxysilane, phenylaminopropylmethyldimethoxysilane, morpholinopropylmethyldimethoxysilane, piperazinopropylmethyldimethoxysilane, methylpiperazinopropyltrimethoxysilane, diethylaminopropylmethyldiethoxysilane, dimethylaminopropylmethyldiethoxysilane, dibutylaminopropylmethyldiethoxysilane, butylaminopropylmethyldiethoxysilane, octylaminopropylmethyldiethoxysilane, phenylaminopropylmethyldiethoxysilane, morpholinopropylmethyldiethoxysilane, piperazinopropylmethyldiethoxysilane, and methylpiperazinopropylmethyldiethoxysilane.

[0029] Compound (3) is used to facilitate handling of the reaction solution obtained by the production method of the present invention and to increase the yield of compound (1). Specifically, adding a metal hydroxide or metal alkoxide can also cause rearrangement of siloxanes, but this is particularly effective in preventing an increase in the viscosity of the reaction solution obtained after recovering the target compound (4).

[0030] In the production method of the present invention, the compounding ratio of compound (1) to compound (3) is not particularly limited, but the amount of compound (3) relative to the number of moles of silicon contained in compound (1) is preferably 1 to 10 moles, more preferably 2 to 8 moles, and even more preferably 2 to 6 moles.

[0031] Adding a metal hydroxide or metal alkoxide to a mixture of compound (1) and compound (3) causes rearrangement of the siloxanes, resulting in an aminoalkylalkoxydisiloxane compound represented by general formula (4) (hereinafter also referred to as compound (4)).

[0032] The metal hydroxide or metal alkoxide is not particularly limited, and examples thereof include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkaline earth metal hydroxides such as barium hydroxide and calcium hydroxide; and alkali metal alkoxides such as lithium methoxide, lithium ethoxide, lithium tert-butoxide, sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium methoxide, potassium ethoxide, and potassium tert-butoxide, and two or more of these may be used in combination. In particular, from the viewpoint of reaction selectivity, it is preferable to use an alkali metal alkoxide.

[0033] The amount of metal hydroxide or metal alkoxide used is not particularly limited, but from the viewpoint of the amount of salt generated by neutralization, it is preferably 0.01 to 10 mass %, more preferably 0.03 to 5 mass %, and even more preferably 0.05 to 1 mass %, based on the total mass of compound (1) and compound (3).

[0034] The reaction temperature is not particularly limited, but is preferably 0 to 200°C, more preferably 0 to 150°C, and even more preferably 20 to 100°C. The reaction time is not particularly limited, but is preferably 0.5 to 10 hours, more preferably 0.5 to 4 hours.

[0035] The metal hydroxide or alkali metal alkoxide in the resulting reaction mixture is neutralized with a Bronsted acid. The Bronsted acid is not particularly limited, and examples thereof include oxo acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, nitric acid, and sulfuric acid; carboxylic acids such as acetic acid, propionic acid, butyric acid, lactic acid, 2-ethylhexanoic acid, linoleic acid, linolenic acid, oleic acid, palmitoleic acid, oxalic acid, malonic acid, and succinic acid; and sulfonic acids such as methanesulfonic acid and dodecylbenzenesulfonic acid. Carboxylic acids with low acidity are particularly preferred. The amount of Bronsted acid added is not particularly limited, but from the viewpoint of suppressing decomposition of the target product during distillation, it is preferably 1.0 to 2.0 mol, more preferably 1.0 to 1.5 mol per mol of metal hydroxide or metal alkoxide.

[0036] The reaction proceeds without a solvent, but can also be carried out in the presence of a solvent. Examples of the solvent include (iso)paraffin compounds such as hexane, octane, isooctane, decane, dodecane, and isododecane; aromatic hydrocarbon compounds such as toluene and xylene; alcohol compounds such as methanol and ethanol; ether compounds such as tetrahydrofuran, 2-methyltetrahydrofuran, 4-methyltetrahydropyran, cyclopentyl methyl ether, dioxane, ethylene glycol dimethyl ether, and propylene glycol dimethyl ether; and nitrile compounds such as acetonitrile, propionitrile, and butyronitrile. These may be used alone or in combination of two or more.

[0037] The above series of reactions yields a mixture of compounds (1), (3), (4) and a salt formed by the reaction of a metal hydroxide or metal alkoxide with a Bronsted acid. To isolate and purify the target compound (4) from this mixture, an appropriate purification method can be selected from those commonly used in organic synthesis, such as filtration, distillation, vacuum stripping, various types of chromatography, and treatment with an adsorbent. Among these, purification by distillation is preferred from the viewpoint of achieving high purity of the target product. When distilling, the salt generated by the reaction of the metal hydroxide or metal alkoxide with the Brønsted acid may be filtered before distillation.

[0038] Specific examples of compound (4) obtainable by the production method of the present invention include 1,3-bis(diethylaminopropyl)-1,1,3,3-tetramethoxydisiloxane, 1,3-bis(dimethylaminopropyl)-1,1,3,3-tetramethoxydisiloxane, 1,3-bis(dibutylaminopropyl)-1,1,3,3-tetramethoxydisiloxane, 1,3-bis(butylaminopropyl)-1,1,3,3-tetramethoxydisiloxane, 1,3-bis(octylaminopropyl)-1,1,3,3-tetramethoxydisiloxane, 1,3-bis(phenylaminopropyl)-1,1,3,3-tetramethoxydisiloxane, 1,3-bis(morpholinopropyl)-1,1,3,3-tetramethoxydisiloxane, 1,3-bis(piperazinopropyl)-1,1,3,3-tetramethoxydisiloxane, 1,3-bis(piperazinopropyl)-1,1,3,3-tetramethoxydisiloxane, 1,3-bis(methylpiperazinopropyl)-1,1,3,3-tetramethoxydisiloxane, 1,3-bis(diethylaminopropyl)-1,1,3,3-tetraethoxydisiloxane, 1,3-bis(dimethylaminopropyl)-1,1,3,3-tetraethoxydisiloxane, 1,3-bis(dibutylaminopropyl)-1,1,3,3-tetraethoxydisiloxane 1,3-bis(propyl)-1,1,3,3-tetraethoxydisiloxane, 1,3-bis(butylaminopropyl)-1,1,3,3-tetraethoxydisiloxane, 1,3-bis(octylaminopropyl)-1,1,3,3-tetraethoxydisiloxane, 1,3-bis(phenylaminopropyl)-1,1,3,3-tetraethoxydisiloxane, 1,3-bis(morpholinopropyl)-1,1,3,3-tetraethoxydisiloxane, 1,3-bis(piperazinopropyl)-1,1,3,3-tetraethoxydisiloxane, 1,3-bis(methylpiperazinopropyl) 1,3-bis(butylaminomethyl)-1,1,3,3-tetraethoxydisiloxane, 1,3-bis(diethylaminomethyl)-1,1,3,3-tetramethoxydisiloxane, 1,3-bis(dimethylaminomethyl)-1,1,3,3-tetramethoxydisiloxane, 1,3-bis(dibutylaminomethyl)-1,1,3,3-tetramethoxydisiloxane, 1,3-bis(butylaminomethyl)-1,1,3,3-tetramethoxydisiloxane, 1,3-bis(octylaminomethyl)-1,1,3,3-tetramethoxydisiloxane, 1,3-bis(phenylaminomethyl)-1,1,3,3-tetramethoxydisiloxane, 1,3-bis(morpholinomethyl)-1,1,3,3-tetramethoxydisiloxane, 1,3-bis(piperazinomethyl)-1,1,3,3-tetramethoxydisiloxane, 1,3-bis(methylpiperazinomethyl)-1,1,3,3-tetramethoxydisiloxane, 1,3-bis(diethylaminomethyl)-1,1,3,3-tetraethoxydisiloxane, 1,3-bis(dimethylaminomethyl)-1,1,3,3-tetraethoxydisiloxane, 1,3-bis(dibutylaminomethyl)-1,1,3, 3-Tetraethoxydisiloxane, 1,3-bis(butylaminomethyl)-1,1,3,3-tetraethoxydisiloxane, 1,3-bis(octylaminomethyl)-1,1,3,3-tetraethoxydisiloxane, 1,3-bis(phenylaminomethyl)-1,1,3,3-tetraethoxydisiloxane, 1,3-bis(morpholinomethyl)-1,1,3,3-tetraethoxydisiloxane, 1,3-bis(piperazinomethyl)-1,1,3,3-tetraethoxydisiloxane, 1,3-bis(methylpiperazinomethyl)-1,1,3,3-tetra Ethoxydisiloxane, 1,3-bis(diethylaminooctyl)-1,1,3,3-tetramethoxydisiloxane, 1,3-bis(dimethylaminooctyl)-1,1,3,3-tetramethoxydisiloxane, 1,3-bis(dibutylaminooctyl)-1,1,3,3-tetramethoxydisiloxane, 1,3-bis(butylaminooctyl)-1,1,3,3-tetramethoxydisiloxane, 1,3-bis(octylaminooctyl)-1,1,3,3-tetramethoxydisiloxane, 1,3-bis(phenylaminooctyl)-1,1,3,3 -tetramethoxydisiloxane, 1,3-bis(morpholinooctyl)-1,1,3,3-tetramethoxydisiloxane, 1,3-bis(piperazinooctyl)-1,1,3,3-tetramethoxydisiloxane, 1,3-bis(methylpiperazinooctyl)-1,1,3,3-tetramethoxydisiloxane, 1,3-bis(diethylaminooctyl)-1,1,3,3-tetraethoxydisiloxane, 1,3-bis(dimethylaminooctyl)-1,1,3,3-tetraethoxydisiloxane, 1,3-bis(dibutylaminooctyl)-1,1,3,3-Tetraethoxydisiloxane, 1,3-bis(butylaminooctyl)-1,1,3,3-tetraethoxydisiloxane, 1,3-bis(octylaminooctyl)-1,1,3,3-tetraethoxydisiloxane, 1,3-bis(phenylaminooctyl)-1,1,3,3-tetraethoxydisiloxane, 1,3-bis(morpholinooctyl)-1,1,3,3-tetraethoxydisiloxane, 1,3-bis(piperazine) 1,3-bis(aminoalkyl)1,1,3,3-tetraalkoxydisiloxane compounds such as 1,3-bis(diethylaminopropyl)-1,3-dimethoxy-1,3-dimethyldisiloxane and 1,3-bis(dimethylaminopropyl)-1,3-dimethoxy-1,3-dimethyldisiloxane; -1,3-dimethyldisiloxane, 1,3-bis(dibutylaminopropyl)-1,3-dimethoxy-1,3-dimethyldisiloxane, 1,3-bis(butylaminopropyl)-1,3-dimethoxy-1,3-dimethyldisiloxane, 1,3-bis(octylaminopropyl)-1,3-dimethoxy-1,3-dimethyldisiloxane, 1,3-bis(phenylaminopropyl)-1,3-dimethoxy-1,3-dimethyldisiloxane Examples of suitable 1,3-bis(aminoalkyl)-1,3-dialkoxy-1,3-dialkyldisiloxane compounds include 1,3-bis(aminoalkyl)-1,3-dialkoxy-1,3-dialkyldisiloxane compounds such as 1,3-bis(morpholinopropyl)-1,3-dimethoxy-1,3-dimethyldisiloxane, 1,3-bis(piperazinopropyl)-1,3-dimethoxy-1,3-dimethyldisiloxane, and 1,3-bis(methylpiperazinopropyl)-1,3-dimethoxy-1,3-dimethyldisiloxane. [Example]

[0039] The present invention will be explained in more detail below with reference to Synthesis Examples, Examples and Comparative Examples, but the present invention is not limited to the following Examples. In the examples and comparative examples, purity is determined by gas chromatography analysis (hereinafter also referred to as "GC analysis").

[0040] [Synthesis Example 1] Synthesis of an oligosiloxane compound from diethylaminopropyltrimethoxysilane A flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer was charged with 706.2 g (3.000 mol) of diethylaminopropyltrimethoxysilane. 16.2 g (0.900 mol) of water was added dropwise, and the mixture was stirred at 70°C for 3 hours. The reaction mixture was distilled until the kettle temperature reached 220°C / 0.2 kPa. 129 g of 1,3-bis(diethylaminopropyl)-1,1,3,3-tetramethoxydisiloxane was obtained, and 389 g of diethylaminopropyltrimethoxysilane was recovered, yielding 120 g of an oligosiloxane compound, a hydrolysis condensate of diethylaminopropyltrimethoxysilane. GC analysis of this oligosiloxane compound confirmed that it did not contain diethylaminopropyltrimethoxysilane or 1,3-bis(diethylaminopropyl)-1,1,3,3-tetramethoxydisiloxane, but rather contained 1,3,5-tris(diethylaminopropyl)1,1,3,5,5-pentamethoxytrisiloxane or an oligosiloxane compound that had undergone a more advanced hydrolysis and condensation reaction.

[0041] [Example 1] Preparation of 1,3-bis(diethylaminopropyl)-1,1,3,3-tetramethoxydisiloxane A flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer was charged with 43.8 g of the oligosiloxane compound obtained in Synthesis Example 1 and 298.8 g of diethylaminopropyltrimethoxysilane. 0.2 g of a 28% by weight solution of sodium methoxide in methanol was added and stirred at room temperature for 1 hour. GC analysis of the resulting reaction solution revealed the formation of 1,3-bis(diethylaminopropyl)-1,1,3,3-tetramethoxydisiloxane. 0.5 g of oleic acid was added to the reaction solution, which was then stirred at room temperature to neutralize it, and distilled, yielding 55 g of 1,3-bis(diethylaminopropyl)-1,1,3,3-tetramethoxydisiloxane and 269 g of diethylaminopropyltrimethoxysilane. After distillation, 12 g of the component remained in the reactor. The reaction liquid using 43.8 g of oligosiloxane compound was distilled, and since 12 g of components remained after the reaction, (43.8 - 12) / 43.8 x 100 = 73% of the oligosiloxane compound was recovered as 1,3-bis(diethylaminopropyl)-1,1,3,3-tetramethoxydisiloxane and diethylaminopropyltrimethoxysilane.

[0042] [Synthesis Example 2] Synthesis of oligosiloxane compound from morpholinopropylmethyldimethoxysilane A flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer was charged with 233 g (1.00 mol) of morpholinopropylmethyldimethoxysilane and 1 g of 28% by weight sodium methoxide methanol solution. 14.4 g (0.800 mol) of water was added dropwise and the mixture was stirred at 70°C for 1 hour. 0.5 g of acetic acid was added to the reaction mixture and stirred at room temperature for 30 minutes. The resulting reaction mixture was distilled to 260°C / 0.3 kPa. 43 g of 1,3-bis(morpholinopropyl)-1,3-dimethoxy-1,3-dimethyldisiloxane was obtained, and 43 g of morpholinopropylmethyldimethoxysilane was recovered, yielding 136 g of an oligosiloxane compound, a hydrolysis condensation product of morpholinopropylmethyldimethoxysilane. GC analysis of this oligosiloxane compound confirmed that it did not contain morpholinopropylmethyldimethoxysilane or 1,3-bis(morpholinopropyl)-1,3-dimethoxy-1,3-dimethyldisiloxane, but rather contained 1,3,5-tris(morpholinopropyl)-1,5-dimethoxy-1,3,5-trimethyltrisiloxane or a siloxane compound that had undergone a more advanced hydrolysis and condensation reaction.

[0043] [Example 2] Preparation of 1,3-bis(morpholinopropyl)-1,3-dimethoxy-1,3-dimethyldisiloxane A flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer was charged with 50 g of the oligosiloxane compound obtained in Synthesis Example 2 and 118 g of morpholinopropylmethyldimethoxysilane. 0.2 g of a 28% by weight solution of sodium methoxide in methanol was added and stirred at room temperature for 1 hour. GC analysis of the resulting reaction solution revealed the formation of 1,3-bis(morpholinopropyl)-1,3-dimethoxy-1,3-dimethyldisiloxane. 0.5 g of oleic acid was added to the reaction solution, which was then stirred at room temperature to neutralize it, and distilled, yielding 50 g of 1,3-bis(morpholinopropyl)-1,3-dimethoxy-1,3-dimethyldisiloxane and 88 g of morpholinopropylmethyldimethoxysilane. After distillation, 26 g of the component remained in the reactor. A reaction liquid using 50 g of oligosiloxane compound was distilled, and since 26 g of components remained after the reaction, (50 - 26) / 50 x 100 = 48% of the oligosiloxane compound was recovered as 1,3-bis(morpholinopropyl)-1,3-dimethoxy-1,3-dimethyldisiloxane and morpholinopropylmethyldimethoxysilane.

[0044] [Comparative Example 1] Synthesis of 1,3-bis(diethylaminopropyl)-1,1,3,3-tetramethoxydisiloxane 1,3-bis(diethylaminopropyl)-1,1,3,3-tetramethoxydisiloxane was produced in the same manner as in Example 1. When the reaction solution obtained without neutralizing the sodium methoxide was distilled, only the monomer diethylaminopropyltrimethoxysilane was recovered, and no 1,3-bis(diethylaminopropyl)-1,1,3,3-tetramethoxydisiloxane was distilled out.

[0045] [Comparative Example 2] Synthesis of 1,3-bis(diethylaminopropyl)-1,1,3,3-tetramethoxydisiloxane 1,3-bis(diethylaminopropyl)-1,1,3,3-tetramethoxydisiloxane was produced in the same manner as in Example 1, except that 0.2 g of trifluoromethanesulfonic acid was used instead of 0.2 g of a 28 mass % methanol solution of sodium methoxide. When the reaction solution obtained without neutralizing trifluoromethanesulfonic acid was distilled, only the monomer diethylaminopropyltrimethoxysilane was recovered, and no 1,3-bis(diethylaminopropyl)-1,1,3,3-tetramethoxydisiloxane was distilled out.

[0046] The results of Synthesis Examples 1 and 2 and Examples 1 and 2 demonstrate that a disiloxane compound can be produced from an aminoalkylalkoxyoligosiloxane compound, which is a mixture of trisiloxane or higher, and an aminoalkylalkoxysilane compound, which is a monomer compound. In this case, the amount of components that were not recovered by distillation and remained in the reactor was less than the amount of the oligosiloxane compound, which was the raw material used in the reaction. This demonstrates that disiloxane compounds can be produced efficiently from components that would previously have been discarded, leading to a reduction in waste. Furthermore, the results of the comparative examples show that when distillation is carried out without neutralizing the catalyst, only the monomer compound is distilled off, and the desired aminoalkylalkoxydisiloxane compound is not obtained at all.

Claims

[Claim 1] The following general formula (1) 【Chemistry 1】 [In the formula, R 1 each independently represents an unsubstituted divalent hydrocarbon group having 1 to 8 carbon atoms; R 2 and R 3 each independently represents an unsubstituted monovalent hydrocarbon group having 1 to 6 carbon atoms, and X represents R 2 or OR 3 Each A independently represents the following general formula (2): 【Chemistry 2】 (In the formula, R 4 and R 5 each independently represents a hydrogen atom or an unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms which may contain an oxygen atom or a nitrogen atom, and may be bonded to each other to form a ring structure, but R 4 and R 5 Except when both are hydrogen atoms.) is a group represented by n is 0 or 1, and m is an integer from 1 to 6. and an aminoalkylalkoxyoligosiloxane compound represented by the following general formula (3): 【Transformation 3】 (In the formula, R 1 ~R 3 , A and n have the same meanings as above. and a neutralization step of adding a metal hydroxide or a metal alkoxide to a mixture of an aminoalkylalkoxysilane compound represented by the following general formula (4), which includes a distillation step after the neutralization step, and 【Chemistry 4】 (In the formula, R 1 ~R 3 , A and n have the same meanings as above. A method for producing an aminoalkylalkoxydisiloxane compound represented by the formula:

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