Method for producing nitrogen-containing polyfunctional organoxysilane compound

Abstract

To provide a method for reacting a primary amine with a haloalkylalkoxysilane under mild reaction conditions of normal pressure and 130°C or lower without generating water due to neutralization and without using a large excess amount of base.SOLUTION: A secondary amine is used in the production of a compound represented by formula (3) or (3') by reacting an amine represented by formula (1) or (1') with a haloalkoxysilane. In formula (1) or (1'), R1, R2 and R3 are each a hydrocarbon group, R4 and R5 are each H or the like, X is a single bond or the like, and n is 1-3. In formula (3) or (3'), R10 is a group represented by formula (4), R4' and R5' are each a monovalent hydrocarbon group, and X' is a single bond or the like.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a method for producing nitrogen-containing polyfunctional organoxysilane compounds that are useful as silane coupling agents, surface treatment agents, resin additives, paint additives, adhesives, etc. [Background technology]

[0002] Nitrogen-containing organoxysilane compounds are useful, for example, as silane coupling agents, surface treatment agents, resin additives, paint additives, and adhesives. Known examples of such nitrogen-containing organoxysilane compounds include organoxysilane compounds having a primary amino group such as aminopropyltrimethoxysilane, organoxysilane compounds having a secondary amino group such as N-phenylaminopropyltrimethoxysilane, and organoxysilane compounds having a tertiary amino group such as dimethylaminopropyltrimethoxysilane.

[0003] When used in the above applications, these silane compounds having amino groups have at most three organoxy groups such as alkoxy groups that act as reaction sites and only one silicon atom to which the organoxy group such as alkoxy group is bonded, and therefore the effect of adding them may be limited. Furthermore, examples of compounds that have many reactive sites and are thought to have a significant effect when added include tris(trimethoxysilylpropyl)amine, which has nine organoxy groups such as alkoxy groups and three silicon atoms, and Patent Document 1 uses this compound as an effective adhesive for metal surfaces.

[0004] A known method for producing such nitrogen-containing organoxysilane compounds having a large number of organoxy groups is to subject one mole of a primary amine compound to a substitution reaction with two equivalents of a haloalkylalkoxysilane compound. For example, in Patent Document 2, an ethylenediamine derivative containing two corresponding trimethoxysilyl groups is produced by reacting N,N-dialkylethylenediamine with 3-chloropropyltrimethoxysilane. In Patent Document 3, 3-aminophenylbenzoate is reacted with 3-chloropropyltriethoxysilane using potassium carbonate as a base to produce an aniline derivative having two corresponding triethoxysilyl groups introduced therein. In Patent Document 4, a tertiary amine compound having three trialkoxysilyl groups is produced by reacting 3-aminopropyltrimethoxysilane with 3-chloropropyltriethoxysilane using triethylamine as a base. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Publication No. 7-228702 [Patent Document 2] Japanese Patent Application Laid-Open No. 2011-121906 [Patent Document 3] International Publication No. 2011 / 045389 [Patent Document 4] German Patent Publication No. 102015225879 Summary of the Invention [Problem to be solved by the invention]

[0006] However, in the substitution reaction between a primary amine compound and multiple haloalkylalkoxysilane compounds, the intermediate secondary amine compound captures the by-product hydrogen halide and forms a hydrohalide salt with poor reactivity, significantly slowing the reaction rate before the desired tertiary amine compound is obtained. In fact, in Patent Document 2, a base is not used to neutralize the hydrogen halide, so the yield of the desired tertiary amine compound is significantly low. Therefore, in order to obtain the desired tertiary amine compound efficiently and in high yield, it is necessary to add a compound with a basicity equal to or stronger than that of the intermediate secondary amine compound to neutralize the hydrogen halide. In this regard, Patent Document 3 uses potassium carbonate as a base, but when an inorganic base is used, the water produced by neutralization hydrolyzes the organoxysilyl group, making it essentially unsuitable for producing organoxysilane compounds. Furthermore, in Patent Document 4, triethylamine, a tertiary amine compound, is used as the base, and a large excess of triethylamine is reacted under pressure of 3 to 4 atmospheres and a high temperature of 175° C. As described above, a method requiring a large excess of base under pressure and high temperature is problematic in terms of productivity, since it requires a large energy cost and generates waste.

[0007] The present invention has been made in view of the above circumstances, and an object of the present invention is to provide a method for producing a nitrogen-containing polyfunctional organoxysilane compound, which can be carried out in a substitution reaction between a primary amine compound and a haloalkylalkoxysilane compound under mild reaction conditions of atmospheric pressure and 130°C or less, without generating water due to neutralization or using a large excess amount of base. [Means for solving the problem]

[0008] As a result of extensive research to solve the above-mentioned problems, the present inventors have found that by using a secondary amine having at least one bulky substituent such as a secondary or tertiary alkyl group as a base in an amount equimolar to the hydrogen halide produced in a substitution reaction between a primary amine compound and a haloalkylalkoxysilane compound, the corresponding nitrogen-containing polyfunctional organoxysilane compound can be produced in high yield and high purity under mild reaction conditions of atmospheric pressure (0.09 to 0.11 MPa) and a temperature of 130°C or lower, thereby completing the present invention.

[0009] That is, the present invention 1. The following general formula (1) or (1') [ka] (In the formula, R 1 represents a monovalent hydrocarbon group having 1 to 18 carbon atoms that is unsubstituted or substituted with a group other than an amino group, and R 2 and R3 represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 3 carbon atoms, and R 4 and R 5 represents a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 18 carbon atoms, and X represents a single bond or NR 6 represents R 6 represents a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 18 carbon atoms, and R 5 and R 6 may be bonded to each other to form a ring together with the nitrogen atom to which they are bonded, and n represents an integer of 1 to 3. and an amine compound represented by the following general formula (2): [ka] (In the formula, R 7 represents an unsubstituted divalent hydrocarbon group having 1 to 10 carbon atoms, which may contain a heteroatom; R 8 and R 9 each independently represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, Y represents a chlorine atom, bromine atom, or iodine atom, and m represents an integer of 0 to 2. and a haloalkylalkoxysilane compound represented by the following general formula (3) or (3'): [ka] [(wherein, R 1 ~R 3 and n have the same meaning as above, R 10 is represented by the following general formula (4): [ka] (In the formula, R 7 ~R 9 and m have the same meaning as above. R represents an alkoxysilylalkyl group represented by 4’ and R 5’ is R 10 or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 18 carbon atoms, and X ’ is a single bond or NR6’ represents R 6’ is R 10 or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 18 carbon atoms.)] In a method for producing a nitrogen-containing polyfunctional organoxysilane compound represented by the following general formula (5), [ka] (In the formula, R 11 represents a branched or cyclic saturated monovalent hydrocarbon group having 3 to 10 carbon atoms, in which the carbon atom bonded to the nitrogen atom is branched, and which may have a heteroatom interposed therebetween; R 12 represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, which may have a heteroatom interposed therebetween (however, branched or cyclic saturated monovalent hydrocarbon groups having 3 to 10 carbon atoms, in which the carbon atom bonded to the nitrogen atom is branched, are excluded), or a branched or cyclic saturated monovalent hydrocarbon group having 3 to 10 carbon atoms, in which the carbon atom bonded to the nitrogen atom is branched, which may have a heteroatom interposed therebetween. 11 and R 12 may be bonded to each other to form a ring together with the nitrogen atom to which they are attached. A method for producing a nitrogen-containing polyfunctional organoxysilane compound using a secondary amine compound represented by the following formula (I): 2. R in the general formula (5) 11 and R 12 the combination is any one of a combination of secondary alkyl groups having 3 to 10 carbon atoms, a combination of cycloalkyl groups having 3 to 10 carbon atoms, a combination of a secondary alkyl group having 3 to 10 carbon atoms and a primary alkyl group having 1 to 10 carbon atoms, a combination of a cycloalkyl group having 3 to 10 carbon atoms and a primary alkyl group having 1 to 10 carbon atoms, a combination of a tertiary alkyl group having 4 to 10 carbon atoms and a primary alkyl group having 1 to 10 carbon atoms, and a combination of tertiary alkyl groups having 4 to 10 carbon atoms. 3. A method for producing a nitrogen-containing polyfunctional organoxysilane compound according to 1 or 2, wherein the secondary amine compound represented by the general formula (5) is any one of the following: [ka] to provide. [Effects of the Invention]

[0010] According to the present invention, by using a bulky secondary amine as a base in the substitution reaction between a primary amine compound and a haloalkylalkoxysilane compound, the corresponding nitrogen-containing polyfunctional organoxysilane compound can be produced in high yield and high purity under mild reaction conditions. DETAILED DESCRIPTION OF THE INVENTION

[0011] The present invention will be specifically described below. The method for producing a nitrogen-containing polyfunctional organoxysilane compound of the present invention is a method for producing a nitrogen-containing polyfunctional organoxysilane compound represented by the following general formula (3) or (3') (hereinafter referred to as compound (3) or compound (3')) by subjecting an amine compound represented by the following general formula (1) or (1') (hereinafter referred to as compound (1) or compound (1')) to a substitution reaction with a haloalkylalkoxysilane compound represented by the following general formula (2) (hereinafter referred to as compound (2)), in which a secondary amine compound represented by the following general formula (5) (hereinafter referred to as compound (5)) is used as a base.

[0012] [ka]

[0013] In the above general formulas (1) and (3), R 1 represents a monovalent hydrocarbon group having 1 to 18 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 3 to 10 carbon atoms, and even more preferably 3 to 8 carbon atoms, which is unsubstituted or substituted with a group other than an amino group. R 1The 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, n-nonyl, n-decyl, n-dodecyl, n-hexadecyl, and n-octadecyl; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, isohexyl, isoheptyl, isooctyl, and tert-octyl; cyclic alkyl groups such as cyclopentyl and cyclohexyl; alkenyl groups such as allyl, butenyl, and methallyl (2-methyl-2-propenyl); aryl groups such as phenyl, tolyl, and xylyl; and aralkyl groups such as benzyl and phenethyl.

[0014] Among these, R 1 As the alkyl group, a linear alkyl group having 3 to 10 carbon atoms, which is unsubstituted or substituted with a group other than an amino group, an alkenyl group, an aryl group, or an aralkyl group is preferred, and from the viewpoints of easy availability of raw materials and high reactivity in particular, a linear alkyl group having 3 to 8 carbon atoms is more preferred, and an n-propyl group, an n-butyl group, an n-hexyl group, or an n-octyl group is even more preferred. Some or all of the hydrogen atoms of these monovalent hydrocarbon groups may be substituted with other substituents, excluding amino groups. Examples of such substituents include alkoxy groups having 1 to 3 carbon atoms, such as methoxy, ethoxy, and propoxy; halogen atoms such as fluorine, chlorine, and bromine; aryl groups having 6 to 10 carbon atoms, such as phenyl and tolyl; aralkyl groups having 7 to 10 carbon atoms, such as benzyl and phenethyl; and alkoxysilyl groups, such as cyano, ester, ether, carbonyl, acyl, sulfide, and trialkoxysilyl groups. One or more of these groups may be used in combination. The substitution positions of these substituents are not particularly limited, and the number of substituents is also not limited. As described below, alkoxysilyl groups are preferred as the substituents.

[0015] Specific examples of compound (1) include linear alkylamines such as methylamine, ethylamine, n-propylamine, n-butylamine, n-pentylamine, n-hexylamine, n-heptylamine, n-octylamine, n-nonylamine, n-decylamine, n-undecylamine, n-dodecylamine, n-hexadecylamine, and n-octadecylamine; and branched alkylamines such as isopropylamine, isobutylamine, sec-butylamine, tert-butylamine, isopentylamine, neopentylamine, isohexylamine, isoheptylamine, isooctylamine, 2-ethylhexylamine, and tert-octylamine. cyclic alkylamines such as cyclopentylamine and cyclohexylamine; alkenylamines such as allylamine, butenylamine, methallylamine, hexenylamine and octenylamine; arylamines such as aniline and toluidine; aralkylamines such as benzylamine and phenethylamine; and alkoxysilyl group-containing alkylamines such as 3-(trimethoxysilyl)propylamine, 3-(dimethoxymethylsilyl)propylamine, 3-(methoxydimethylsilyl)propylamine, 3-(triethoxysilyl)propylamine, 3-(diethoxymethylsilyl)propylamine and 3-(ethoxydimethylsilyl)propylamine.

[0016] Among these, from the viewpoints of easy availability of raw materials and high reactivity, linear alkylamines and alkoxysilyl group-containing alkylamines are preferred, and n-propylamine, n-butylamine, n-hexylamine, n-octylamine, 3-(trimethoxysilyl)propylamine, and 3-(triethoxysilyl)propylamine are even more preferred. The amine compound represented by general formula (1) may be commercially available or may be produced by a conventional method, such as a method of dehydrating an alcohol with ammonia.

[0017] In the above general formulas (1') and (3'), R 2 and R 3represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 3 carbon atoms, preferably 1 to 2 carbon atoms, and more preferably 1 carbon atom. R 2 and R 3 The divalent hydrocarbon group may be either linear or branched, and specific examples thereof include methylene, ethylene, trimethylene, and propylene groups. Among these, R 2 and R 3 As the alkyl group, an unsubstituted linear alkylene group having 1 to 2 carbon atoms is preferred, and from the viewpoint of easy availability of raw materials in particular, a methylene group or an ethylene group is more preferred, with a methylene group being even more preferred.

[0018] In the above general formula (1′), R 4 and R 5 represents a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 18 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 5 carbon atoms. R 4 and R 5 When R is a substituted or unsubstituted monovalent hydrocarbon group having 1 to 18 carbon atoms, the monovalent hydrocarbon group may be linear, branched, or cyclic. Specific examples thereof include those mentioned above in R 1 Examples of the substituents include the same monovalent hydrocarbon groups as those exemplified above.

[0019] Among these, R 4 and R 5 As the alkyl group, a substituted or unsubstituted linear alkyl group, alkenyl group, aryl group, or aralkyl group having 1 to 10 carbon atoms is preferable, and from the viewpoint of easy availability of raw materials in particular, an alkyl group having 1 to 4 carbon atoms is more preferable, and a methyl group, an ethyl group, an n-propyl group, or an n-butyl group is even more preferable. Some or all of the hydrogen atoms of these monovalent hydrocarbon groups may be substituted with other substituents, and examples of such substituents include those mentioned above in R 1 The substituents include the same as those of the substituted monovalent hydrocarbon groups exemplified in 1., and one or more of these may be used in combination. There are no particular limitations on the substitution positions of these substituents, and there are no particular limitations on the number of substituents.

[0020] In the above general formula (1′), X is a single bond or NR 6 represents R 6 represents a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 18 carbon atoms, and R 6 is R 5 may be bonded to each other to form a ring together with the nitrogen atom to which they are attached. R 6 When R is a substituted or unsubstituted monovalent hydrocarbon group having 1 to 18 carbon atoms, the monovalent hydrocarbon group may be linear, branched, or cyclic. Specific examples thereof include those mentioned above in R 1 Examples of the substituents include the same monovalent hydrocarbon groups as those exemplified above.

[0021] Among these, R 6 As the alkyl group, a substituted or unsubstituted linear alkyl group, alkenyl group, aryl group, or aralkyl group having 1 to 10 carbon atoms is preferable, and from the viewpoint of easy availability of raw materials in particular, an alkyl group having 1 to 4 carbon atoms is more preferable, and a methyl group, an ethyl group, an n-propyl group, or an n-butyl group is even more preferable. Some or all of the hydrogen atoms of these monovalent hydrocarbon groups may be substituted with other substituents, and examples of such substituents include those mentioned above in R 1 Examples of the substituents include the same substituents as those of the substituted monovalent hydrocarbon groups exemplified above.

[0022] Also, R 5 and R 6 Examples of the ring structure formed by bonding together with the nitrogen atom to which they are bonded include a piperazine ring.

[0023] In the above general formula (1′), n represents an integer of 1 to 3, and preferably an integer of 1 to 2.

[0024] Specific examples of compound (1') include ethylenediamine compounds such as ethylenediamine, N-methylethylenediamine, N,N-dimethylethylenediamine, N-ethylethylenediamine, N,N-diethylethylenediamine, N-propylethylenediamine, N,N-dipropylethylenediamine, N-butylethylenediamine, and N,N-dibutylethylenediamine; propylenediamine compounds such as propylenediamine, N-methylpropylenediamine, N,N-dimethylpropylenediamine, N-ethylpropylenediamine, N,N-diethylpropylenediamine, N-propylpropylenediamine, N,N-dipropylpropylenediamine, N-butylpropylenediamine, and N,N-dibutylpropylenediamine; butylenediamine, N-methyl butylenediamine compounds such as butylenediamine, N,N-dimethylbutylenediamine, N-ethylbutylenediamine, N,N-diethylbutylenediamine, N-propylbutylenediamine, N,N-dipropylbutylenediamine, N-butylbutylenediamine, and N,N-dibutylbutylenediamine; diethylenetriamine compounds such as diethylenetriamine, 2,2'-diamino-N-methyldiethylamine, 2,2'-diamino-N-ethyldiethylamine, 2,2'-diamino-N-propyldiethylamine, and 2,2'-diamino-N-butyldiethylamine; piperazine compounds such as N-(2-aminoethyl)piperazine and 1,4-bis(3-aminopropyl)piperazine; triethylenetetramine; and 1,6-diaminohexane.

[0025] Among these, from the viewpoint of easy availability of raw materials, ethylenediamine compounds, propylenediamine compounds, butylenediamine compounds, and piperazine compounds are preferred, and ethylenediamine, N-methylethylenediamine, N-ethylethylenediamine, propylenediamine, butylenediamine, and N-(2-aminoethyl)piperazine are more preferred. Compound (1') may be commercially available or may be produced according to a conventionally known method, for example, by subjecting an amine compound to an addition reaction with an aziridine compound.

[0026] In the above general formula (2), R 7 represents an unsubstituted divalent hydrocarbon group having 1 to 10 carbon atoms, preferably 1 to 8 carbon atoms, more preferably 1 to 5 carbon atoms, and even more preferably 1 to 3 carbon atoms, which may contain a heteroatom. R 7 The divalent hydrocarbon group may be linear, branched, or cyclic, and specific examples thereof include alkylene groups such as methylene, ethylene, trimethylene, tetramethylene, isobutylene, hexamethylene, octamethylene, decamethylene, cyclohexylene, and methylenecyclohexylene; alkenylene groups such as butynylene, propenylene, butenylene, hexenylene, and octenylene; arylene groups such as phenylene; and aralkylene groups such as methylenephenylene and methylenephenylenemethylene. Among these, R 7 As the alkyl group, an unsubstituted linear alkylene group having 1 to 8 carbon atoms is preferred, and from the viewpoint of easy availability of raw materials, a methylene group, a trimethylene group, or an octamethylene group is more preferred. These divalent hydrocarbon groups may have one or more heteroatoms in the molecular chain, such as ether groups, carbonyl groups, amino groups, and sulfide groups.

[0027] In the above general formula (2), R 8 and R 9 each independently represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, preferably 1 to 5 carbon atoms, and more preferably 1 to 3 carbon atoms. R 8 and R 9The 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, n-nonyl, and n-decyl; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, isohexyl, isoheptyl, isooctyl, and tert-octyl; cyclic alkyl groups such as cyclopentyl and cyclohexyl; alkenyl groups such as vinyl, allyl, 1-propenyl, butenyl, and methallyl (2-methyl-2-propenyl); aryl groups such as phenyl, tolyl, and xylyl; and aralkyl groups such as benzyl and phenethyl.

[0028] Among these, R 8 and R 9 As the group, a substituted or unsubstituted linear, branched or cyclic alkyl group, alkenyl group, aryl group or aralkyl group having 1 to 5 carbon atoms is preferred, and from the viewpoint of easy availability of raw materials in particular, an unsubstituted linear alkyl group having 1 to 3 carbon atoms is more preferred, and a methyl group or an ethyl group is even more preferred. Some or all of the hydrogen atoms of these monovalent hydrocarbon groups may be substituted with other substituents, such as alkoxy groups having 1 to 3 carbon atoms, such as methoxy, ethoxy, and propoxy; halogen atoms, such as fluorine, chlorine, and bromine; aryl groups having 6 to 10 carbon atoms, such as phenyl and tolyl; aralkyl groups having 7 to 10 carbon atoms, such as benzyl and phenethyl; cyano, amino, ester, ether, carbonyl, acyl, and sulfide groups, and one or more of these may be used in combination. There are no particular limitations on the substitution positions of these substituents, and there are no limitations on the number of substituents.

[0029] In the above general formula (2), Y represents a halogen atom such as fluorine, chlorine, bromine, or iodine, and from the viewpoint of high reactivity, chlorine, bromine, and iodine are preferred, and from the viewpoint of easy availability of raw materials, chlorine is particularly preferred.

[0030] Specific examples of compound (2) include (chloroalkyl)trialkoxysilanes such as (chloromethyl)trimethoxysilane, (3-chloropropyl)trimethoxysilane, (8-chlorooctyl)trimethoxysilane, (chloromethyl)triethoxysilane, (3-chloropropyl)triethoxysilane, and (8-chlorooctyl)triethoxysilane; (chloromethyl)dimethoxymethylsilane, (3-chloropropyl)dimethoxymethylsilane, (8-chlorooctyl)dimethoxymethylsilane, and (chloromethyl)diethoxymethylsilane. (chloroalkyl)dialkoxyalkylsilanes such as (chloromethyl)methoxydimethylsilane, (3-chloropropyl)methoxydimethylsilane, (8-chlorooctyl)methoxydimethylsilane, (chloromethyl)ethoxydimethylsilane, (3-chloropropyl)ethoxydimethylsilane, and (8-chlorooctyl)ethoxydimethylsilane; and (chloroalkyl)alkoxydialkylsilanes such as (chloromethyl)methoxydimethylsilane, (3-chloropropyl)methoxydimethylsilane, (8-chlorooctyl)ethoxydimethylsilane.

[0031] Among these, from the viewpoints of availability and a large number of functions, (chloroalkyl)trialkoxysilanes such as (chloromethyl)trialkoxysilane and (3-chloropropyl)trialkoxysilane are preferred, and (chloromethyl)trimethoxysilane, (chloromethyl)triethoxysilane, (3-chloropropyl)trimethoxysilane, and (3-chloropropyl)triethoxysilane are more preferred. Compound (2) may be commercially available or may be produced according to a conventionally known method, such as a method of subjecting a halogenated alkenyl compound and a hydrosilane compound to a hydrosilylation reaction.

[0032] In the above substitution reaction, the amount of compound (2) used is not particularly limited, but is preferably in the range of 0.9 to 2.0 moles, more preferably 1.0 to 1.1 moles, per mole of N-H of compound (1) or (1').

[0033] In the above general formula (5), R 11 represents a branched or cyclic saturated monovalent hydrocarbon group having 3 to 10 carbon atoms, preferably 3 to 8 carbon atoms, and more preferably 3 to 6 carbon atoms, in which the carbon atom bonded to the nitrogen atom is branched, and which may have a heteroatom interposed therebetween. Also, R 12 represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, preferably 1 to 8 carbon atoms, and more preferably 1 to 6 carbon atoms, which may have a heteroatom interposed therebetween (however, branched or cyclic saturated monovalent hydrocarbon groups having 3 to 10 carbon atoms in which the carbon atom bonded to the nitrogen atom is branched are excluded), or a branched or cyclic saturated monovalent hydrocarbon group having 3 to 10 carbon atoms, preferably 3 to 8 carbon atoms, and more preferably 3 to 6 carbon atoms, which may have a heteroatom interposed therebetween, in which the carbon atom bonded to the nitrogen atom is branched.

[0034] R 11 and R 12 The branched or cyclic saturated monovalent hydrocarbon group may be either branched or cyclic, and specific examples thereof include branched alkyl groups such as isopropyl, sec-butyl, tert-butyl, and tert-amyl groups; and cyclic alkyl groups such as cyclopropyl, cyclopentyl, cyclohexyl, and adamantyl groups.

[0035] R 12 The 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, n-nonyl, and n-decyl; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, isohexyl, isoheptyl, isooctyl, and tert-octyl; cyclic alkyl groups such as cyclopentyl and cyclohexyl; alkenyl groups such as allyl, butenyl, and methallyl (2-methyl-2-propenyl); and aralkyl groups such as benzyl and phenethyl.

[0036] Among these, R 11As the alkyl group, a substituted or unsubstituted saturated alkyl group having 3 to 8 carbon atoms is preferred, and from the viewpoint of easy availability of raw materials, a saturated alkyl group having 3 to 6 carbon atoms is particularly preferred, with an isopropyl group, a tert-butyl group, or a cyclohexyl group being even more preferred. Some or all of the hydrogen atoms of these monovalent hydrocarbon groups may be substituted with other substituents, such as alkoxy groups having 1 to 3 carbon atoms, such as methoxy, ethoxy, and propoxy; halogen atoms, such as fluorine, chlorine, and bromine; aryl groups having 6 to 10 carbon atoms, such as phenyl and tolyl; aralkyl groups having 7 to 10 carbon atoms, such as benzyl and phenethyl; cyano groups, ester groups, ether groups, carbonyl groups, acyl groups, and sulfide groups, and these may be used alone or in combination of two or more. There are no particular limitations on the substitution positions of these substituents, and there are no limitations on the number of substituents.

[0037] Among these, R 12 As the alkyl group, a substituted or unsubstituted alkyl group, alkenyl group, or aralkyl group having 1 to 8 carbon atoms is preferable, and from the viewpoints of easy availability of raw materials and high basicity, a linear or cyclic alkyl group having 1 to 6 carbon atoms is particularly preferable, and a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-hexyl group, an isopropyl group, or a cyclohexyl group is even more preferable. Some or all of the hydrogen atoms of these monovalent hydrocarbon groups may be substituted with other substituents, such as alkoxy groups having 1 to 3 carbon atoms, such as methoxy, ethoxy, and propoxy; halogen atoms, such as fluorine, chlorine, and bromine; aryl groups having 6 to 10 carbon atoms, such as phenyl and tolyl; aralkyl groups having 7 to 10 carbon atoms, such as benzyl and phenethyl; cyano groups, ester groups, ether groups, carbonyl groups, acyl groups, and sulfide groups, and these may be used alone or in combination of two or more. There are no particular limitations on the substitution positions of these substituents, and there are no limitations on the number of substituents.

[0038] Also, R 11 and R 12may be bonded to each other to form a ring together with the nitrogen atom to which they are attached, forming, for example, a piperidine ring.

[0039] R 11 and R 12 As the combinations thereof, any of the following are preferred: a combination of secondary alkyl groups having 3 to 10 carbon atoms; a combination of cycloalkyl groups having 3 to 10 carbon atoms; a combination of a secondary alkyl group having 3 to 10 carbon atoms and a primary alkyl group having 1 to 10 carbon atoms; a combination of a cycloalkyl group having 3 to 10 carbon atoms and a primary alkyl group having 1 to 10 carbon atoms; a combination of a tertiary alkyl group having 4 to 10 carbon atoms and a primary alkyl group having 1 to 10 carbon atoms; and a combination of tertiary alkyl groups having 4 to 10 carbon atoms; and any of the following are more preferred: a combination of secondary alkyl groups having 3 to 8 carbon atoms; a combination of cycloalkyl groups having 5 to 8 carbon atoms; a combination of secondary alkyl groups having 3 to 8 carbon atoms and a primary alkyl group having 1 to 8 carbon atoms; a combination of cycloalkyl groups having 3 to 10 carbon atoms and a primary alkyl group having 1 to 8 carbon atoms; a combination of tertiary alkyl groups having 4 to 8 carbon atoms and a primary alkyl group having 1 to 8 carbon atoms; and a combination of tertiary alkyl groups having 4 to 8 carbon atoms.

[0040] Specific examples of compound (5) include N-alkyl or cycloalkylisopropylamines such as N-methylisopropylamine, N-ethylisopropylamine, N-propylisopropylamine, diisopropylamine, N-isopropylbutylamine, N-isopropylhexylamine, and N-isopropylcyclohexylamine; N-alkyl or cycloalkylcyclohexylamines such as N-methylcyclohexylamine, N-ethylcyclohexylamine, N-propylcyclohexylamine, N-isopropylcyclohexylamine, N-butylcyclohexylamine, N-hexylcyclohexylamine, and dicyclohexylamine; alkyl-tert-butylamines such as N-methyl-tert-butylamine, N-ethyl-tert-butylamine, N-propyl-tert-butylamine, and N-tert-butylhexylamine; di-sec-butylamine, 2,2,6,6-tetramethylpiperidine, and N-methyladamantylamine.

[0041] Among these, from the viewpoint of easy availability, N-alkyl or cycloalkyl isopropylamine, N-alkyl or cycloalkyl cyclohexylamine, alkyl-tert-butylamine, di-sec-butylamine, and 2,2,6,6-tetramethylpiperidine are preferred, and from the viewpoint of fewer side reactions, N-alkyl or cycloalkyl isopropylamine, and N-alkyl or cycloalkyl cyclohexylamine are more preferred, with diisopropylamine and dicyclohexylamine being even more preferred. Compound (5) may be commercially available or may be produced according to a conventionally known method, for example, by subjecting an amine to a reductive amination reaction with a carbonyl compound.

[0042] In the above substitution reaction, the amount of compound (5) used is not particularly limited, but is preferably in the range of 0.9 to 2.0 moles, more preferably 1.0 to 1.1 moles, per mole of N-H of compound (1) or (1').

[0043] The substitution reaction can be carried out in the presence or absence of an organic solvent. Specific examples of usable organic solvents include hydrocarbon solvents such as benzene, toluene, and xylene; ether solvents such as diethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 4-methyltetrahydropyran, and dioxane; ester solvents such as ethyl acetate and butyl acetate; aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, and N-methylpyrrolidone; and alcohol solvents such as methanol and ethanol. These solvents may be used alone or in combination of two or more. When a solvent is used, the amount thereof is not particularly limited, but is preferably in the range of 0.05 to 10.0 liters, more preferably 0.08 to 0.2 liters, per 1 mol of N-H of compound (1) or (1').

[0044] There is no limitation on the pressure during the reaction, but it is preferable to carry out the reaction at normal pressure. The reaction temperature is not particularly limited, but is preferably 20 to 200° C., more preferably 50 to 130° C. The reaction time is also not particularly limited, but is preferably 1 to 40 hours, more preferably 1 to 24 hours. The reaction is preferably carried out in an atmosphere of an inert gas such as nitrogen or argon.

[0045] In the substitution reaction, a catalyst may be used to shorten the reaction time. The catalyst is preferably a quaternary onium salt, and specific examples include tetrabutylammonium bromide, tetrabutylammonium iodide, tetrabutylphosphonium bromide, and tributylmethylphosphonium iodide.

[0046] The hydrohalide salt of compound (5) produced in the above substitution reaction can be removed by filtration after the reaction is complete, or can be regenerated by adding a more strongly basic amine compound such as 1,8-diazabicyclo[5.4.0]-7-undecene after the reaction is complete.

[0047] In the above general formulas (3) and (3′), R 10 represents an alkoxysilylalkyl group represented by the following general formula (4), and specific examples thereof include an alkoxysilylalkyl group corresponding to the raw material compound (2).

[0048] [ka] (In the formula, R 7 ~R 9 and m have the same meaning as above.)

[0049] In the above general formula (3'), R 4’ and R 5’ is R in compound (1'). 4 and R 5 are hydrogen atoms, the above R 10 R in compound (1') represents 4 and R 5 When represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 18 carbon atoms, each represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 18 carbon atoms.

[0050] In the above general formula (3'), X ’ is a single bond or NR 6’ R in compound (1') represents 6 is a hydrogen atom, the above R 10 R in compound (1') represents 6 When R is a substituted or unsubstituted monovalent hydrocarbon group having 1 to 18 carbon atoms, it represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 18 carbon atoms.

[0051] The nitrogen-containing polyfunctional organoxysilane compounds represented by the general formulas (3) and (3') obtained by the production method of the present invention can be further purified before use by various purification methods such as distillation, filtration, washing, column separation, etc., depending on the desired quality. Purification by distillation is particularly preferred to achieve high purity. [Example]

[0052] EXAMPLES The present invention will be specifically explained below with reference to examples and comparative examples, but the present invention is not limited to the following examples. The reaction rate was calculated from the area ratio % of the raw material amine compound, the intermediate secondary amine compound, and the target nitrogen-containing polyfunctional organoxysilane compound, as analyzed by gas chromatography. The purity of the polyfunctional organoxysilane compound is a value measured under the following gas chromatography measurement conditions. [Gas chromatography measurement conditions] Gas chromatograph: GC-2014 (Shimadzu Corporation) Packed column: Silicone SE-30 (GL Sciences, Inc.) Detector:TCD Detector temperature: 300℃ Inlet temperature: 300℃ Temperature program: 70°C (0 min) → 10°C / min → 300°C (10 min) Carrier gas: Helium (50 ml / min) Injection volume: 1μl

[0053] [Example 1] The inside of a four-neck flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer was replaced with nitrogen, and nitrogen gas was passed through the open end of the top of the reflux condenser to prevent outside air from mixing in. 50.6 g (500 mmol) of hexylamine, 181.0 g (1000 mmol) of dicyclohexylamine, 1.7 g (5 mmol) of tributylmethylphosphonium iodide, and 15.0 g of acetonitrile were charged and stirred. Next, 198.7 g (1000 mmol) of (3-chloropropyl)trimethoxysilane was added dropwise over 1 hour while adjusting the internal temperature to 120°C, and the mixture was stirred at 120-130°C for 9 hours under atmospheric pressure. A small amount of the reaction mixture was sampled and the conversion calculated by gas chromatography, revealing that the conversion of hexylamine to N,N-bis[3-(trimethoxysilyl)propyl]-1-hexanamine was 95.1%. The reaction mixture was cooled to 80°C, and 80.0 g of acetonitrile and 147.4 g (970 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene were added dropwise, followed by stirring at 80°C for 30 minutes. The reaction mixture was separated into two layers, and the lower layer was removed by separation to obtain 414.0 g of a crude product. 1.0 g of a 28% by mass sodium methoxide methanol solution was added to the crude product, and the mixture was distilled at 80 Pa to obtain N,N-bis[3-(trimethoxysilyl)propyl]-1-hexaneamine in a yield of 85.5% and a purity of 99.2%.

[0054] [Example 2] The inside of a four-neck flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer was replaced with nitrogen, and nitrogen gas was passed through the open end of the top of the reflux condenser to prevent outside air from mixing in. 50.6 g (500 mmol) of hexylamine, 101.2 g (1000 mmol) of diisopropylamine, 1.7 g (5 mmol) of tributylmethylphosphonium iodide, and 15.0 g of acetonitrile were charged and stirred. Next, 198.7 g (1000 mmol) of (3-chloropropyl)trimethoxysilane was added dropwise over 1 hour while adjusting the internal temperature to 120°C, and the mixture was stirred at 120-130°C for 9 hours under atmospheric pressure. A small amount of the reaction mixture was sampled and the conversion calculated by gas chromatography, revealing that the conversion of hexylamine to N,N-bis[3-(trimethoxysilyl)propyl]-1-hexaneamine was 86.5%. The reaction mixture was cooled to 80°C, and 80.0 g of acetonitrile and 147.4 g (970 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene were added dropwise, followed by stirring at 80°C for 30 minutes. The reaction mixture was separated into two layers, and the lower layer was removed by separation to obtain 345.5 g of crude product. 1.1 g of 28% by mass sodium methoxide methanol solution was added to the crude product, and the mixture was distilled at 80 Pa to obtain N,N-bis[3-(trimethoxysilyl)propyl]-1-hexaneamine in a yield of 76.3% and a purity of 98.5%.

[0055] [Example 3] The inside of a four-neck flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer was replaced with nitrogen, and nitrogen gas was passed through the open end of the reflux condenser to prevent outside air from mixing in. 5.1 g (50 mmol) of hexylamine, 14.1 g (100 mmol) of 2,2,6,6-tetramethylpiperidine, 0.2 g (0.5 mmol) of tributylmethylphosphonium iodide, and 1.5 g of acetonitrile were charged and stirred. Next, 19.9 g (1000 mmol) of (3-chloropropyl)trimethoxysilane was added dropwise over 1 hour while adjusting the internal temperature to 120°C, and the mixture was stirred at 120-130°C for 9 hours under atmospheric pressure. A small amount of the reaction mixture was sampled and the conversion calculated by gas chromatography, revealing that the conversion of hexylamine to N,N-bis[3-(trimethoxysilyl)propyl]-1-hexanamine was 87.1%. The reaction mixture was cooled to 80°C, and 8.0 g of acetonitrile and 14.7 g (97 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene were added dropwise, followed by stirring at 80°C for 30 minutes. The reaction mixture was separated into two layers, and the lower layer was removed by separation to obtain 38.5 g of crude product. 0.1 g of 28% by mass sodium methoxide methanol solution was added to the crude product, and the mixture was distilled at 80 Pa to obtain N,N-bis[3-(trimethoxysilyl)propyl]-1-hexaneamine in a yield of 75.1% and a purity of 98.1%.

[0056] [Example 4] The inside of a four-neck flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer was replaced with nitrogen, and 89.5 g (500 mmol) of (3-aminopropyl)trimethoxysilane, 181.0 g (1000 mmol) of dicyclohexylamine, 3.4 g (10 mmol) of tetrabutylphosphonium bromide, and 15.0 g of acetonitrile were charged and stirred while nitrogen gas was passed through the open end of the top of the reflux condenser to prevent outside air from mixing in. Next, 182.1 g (1000 mmol) of (3-chloropropyl)methyldimethoxysilane was added dropwise over 1 hour while adjusting the internal temperature to 120°C, and the mixture was stirred at 120-130°C for 24 hours under atmospheric pressure. A small amount of the reaction mixture was sampled and the reaction rate was calculated by gas chromatography, revealing that the conversion rate from (3-aminopropyl)trimethoxysilane to 3-(trimethoxysilyl)-N,N-bis[3-(methyldimethoxysilyl)propyl]-1-propanamine was 94.1%. The reaction mixture was cooled to 80°C, and 80.0 g of acetonitrile and 147.4 g (970 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene were added dropwise, followed by stirring at 80°C for 30 minutes. The reaction mixture was separated into two layers, and the lower layer was removed by separation to obtain 434.5 g of a crude product. 0.9 g of a 28% by mass sodium methoxide methanol solution was added to the crude product, and the mixture was distilled at 80 Pa to obtain 3-(trimethoxysilyl)-N,N-bis[3-(methyldimethoxysilyl)propyl]-1-propanamine in a yield of 78.4% and a purity of 99.4%.

[0057] [Example 5] A four-neck flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer was purged with nitrogen, and 22.0 g (250 mmol) of N-ethylethylenediamine, 136.0 g (750 mmol) of dicyclohexylamine, 2.6 g (7.5 mmol) of tributylmethylphosphonium iodide, and 25.0 g of acetonitrile were charged and stirred while nitrogen gas was passed through the open end of the top of the reflux condenser to prevent outside air from mixing in. Next, 149.1 g (750 mmol) of (3-chloropropyl)trimethoxysilane was added dropwise over 30 minutes while adjusting the internal temperature to 115°C, and the mixture was stirred at 115-130°C for 9 hours under atmospheric pressure. A small amount of the reaction mixture was sampled and the reaction rate was calculated by gas chromatography, which showed that the conversion rate from N-ethylethylenediamine to N-ethyl-N,N',N'-tris[3-(trimethoxysilyl)propyl]ethylenediamine was 95.0%. The reaction mixture was cooled to 80°C, and 10.0 g of acetonitrile and 114.3 g (750 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene were added dropwise, followed by stirring at 80°C for 30 minutes. The reaction mixture was separated into two layers, and the lower layer was removed by separation to obtain 288.4 g of crude product. 0.9 g of 28% by mass sodium methoxide methanol solution was added to the crude product, and the mixture was distilled at 200 Pa to obtain N-ethyl-N,N',N'-tris[3-(trimethoxysilyl)propyl]ethylenediamine in 81.1% yield and 98.1% purity.

[0058] [Example 6] A four-neck flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer was purged with nitrogen, and 32.3 g (250 mmol) of N-(2-aminoethyl)piperazine, 136.0 g (750 mmol) of dicyclohexylamine, 2.6 g (7.5 mmol) of tributylmethylphosphonium iodide, and 25.0 g of acetonitrile were charged and stirred while nitrogen gas was passed through the open end of the top of the reflux condenser to prevent outside air from mixing in. Next, 164.0 g (825 mmol) of (3-chloropropyl)trimethoxysilane was added dropwise over 30 minutes while adjusting the internal temperature to 115°C, and the mixture was stirred at 115-130°C for 16 hours under atmospheric pressure. A small amount of the reaction mixture was sampled and the conversion was calculated by gas chromatography, revealing that the conversion from N-(2-aminoethyl)piperazine to N,N,4-tris[3-(trimethoxysilyl)propyl]-1-piperazineethanamine was 96.9%. The reaction mixture was cooled to 80°C, and 45.0 g of acetonitrile and 114.3 g (750 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene were added dropwise, followed by stirring at 80°C for 30 minutes. The lower layer of the reaction mixture was removed by separation to obtain 306.5 g of crude product. 2.4 g of 28% by mass sodium methoxide methanol solution was added to the crude product, and low-boiling components were distilled off at 200 Pa to obtain N,N,4-tris[3-(trimethoxysilyl)propyl]-1-piperazineethanamine in 90.7% yield and 94.2% purity. This was further purified by distillation at 30 Pa to obtain N,N,4-tris[3-(trimethoxysilyl)propyl]-1-piperazineethanamine in 66.9% yield and 99.2% purity.

[0059] [Comparative Example 1] The inside of a four-neck flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer was replaced with nitrogen, and nitrogen gas was passed through the open end of the top of the reflux condenser to prevent outside air from mixing in. 50.6 g (500 mmol) of hexylamine, 129.3 g (1000 mmol) of N,N-diisopropylethylamine, 1.7 g (5 mmol) of tributylmethylphosphonium iodide, and 15.0 g of acetonitrile were charged and stirred. Next, 198.7 g (1000 mmol) of (3-chloropropyl)trimethoxysilane was added dropwise over 1 hour while adjusting the internal temperature to 120°C, and the mixture was stirred at 120-130°C for 9 hours under atmospheric pressure. The reaction mixture was cooled to 80°C, and 80.0 g of acetonitrile and 147.4 g (970 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene were added dropwise, followed by stirring at 80°C for 30 minutes. A small amount of the reaction mixture was sampled and analyzed by gas chromatography. The conversion rate of hexylamine to the target compound, N,N-bis[3-(trimethoxysilyl)propyl]-1-hexaneamine, was 11.3%. The conversion rate of hexylamine to the intermediate secondary amine compound, N-[3-(trimethoxysilyl)propyl]-1-hexaneamine, was 77.2%. It was also confirmed that a large amount of unreacted (3-chloropropyl)trimethoxysilane remained. Since the amount of the target N,N-bis[3-(trimethoxysilyl)propyl]-1-hexanamine produced was small, distillation purification was not carried out.

[0060] Comparative Example 2 A four-neck flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer was purged with nitrogen. Nitrogen gas was passed through the open end of the reflux condenser to prevent outside air from mixing in. 50.6 g (500 mmol) of hexylamine, 152.2 g (1000 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene, 1.7 g (5 mmol) of tributylmethylphosphonium iodide, and 15.0 g of acetonitrile were then charged and stirred. Next, 198.7 g (1000 mmol) of (3-chloropropyl)trimethoxysilane was added dropwise over 1 hour while adjusting the internal temperature to 120°C, followed by stirring at 120-130°C for 9 hours under atmospheric pressure. A small amount of the reaction mixture was sampled and analyzed by gas chromatography. The conversion rate of hexylamine to the target compound, N,N-bis[3-(trimethoxysilyl)propyl]-1-hexaneamine, was 28.0%. The conversion rate of hexylamine to the intermediate secondary amine compound, N-[3-(trimethoxysilyl)propyl]-1-hexaneamine, was 72.0%. (3-Chloropropyl)trimethoxysilane had been completely consumed. The reaction mixture was cooled to 80°C, and 80.0 g of acetonitrile was added dropwise. The mixture was then stirred at 80°C for 30 minutes. The lower layer of the reaction mixture was separated into two layers, and the resulting mixture was separated to obtain 125.5 g of crude product. 0.3 g of a 28% by mass sodium methoxide methanol solution was added to the crude product, and the mixture was distilled at 80 Pa to obtain N,N-bis[3-(trimethoxysilyl)propyl]-1-hexanamine in a yield of 13.2% and a purity of 98.9%.

[0061] As described above, in Examples 1 to 6, by using a secondary amine compound having a specific structure according to the present invention as a base, the reaction was carried out under mild conditions of atmospheric pressure and 130°C or lower, and in all cases the corresponding nitrogen-containing polyfunctional organoxysilane compound was produced at a high reaction rate, in high yield, and with high purity.

[0062] On the other hand, in Comparative Example 1, hexylamine and (3-chloropropyl)trimethoxysilane were reacted under the same conditions as in Examples 1 to 3, using the tertiary amine compound diisopropylethylamine as the base. However, the target product, N,N-bis[3-(trimethoxysilyl)propyl]-1-hexaneamine, was only produced at a low reaction rate. Instead, the intermediate secondary amine compound, N-[3-(trimethoxysilyl)propyl]-1-hexaneamine, was obtained as the main component, and a large amount of (3-chloropropyl)trimethoxysilane was confirmed to remain. From this, it is believed that the intermediate secondary amine compound, which has stronger basicity than diisopropylamine, captured the by-product hydrogen chloride and formed a hydrohalide salt with poor reactivity, which significantly reduced the reaction rate.

[0063] In Comparative Example 2, hexylamine and (3-chloropropyl)trimethoxysilane were reacted using the strongly basic amidine compound 1,8-diazabicyclo[5.4.0]-7-undecene as the base under the same conditions as in Examples 1 to 3. However, the target product, N,N-bis[3-(trimethoxysilyl)propyl]-1-hexanamine, was produced only at a low reaction rate, resulting in a significantly low isolation yield. Since (3-chloropropyl)trimethoxysilane was completely consumed, it is believed that the 1,8-diazabicyclo[5.4.0]-7-undecene reacted with (3-chloropropyl)trimethoxysilane preferentially over the intermediate secondary amine compound, N-[3-(trimethoxysilyl)propyl]-1-hexanamine, resulting in a low yield of the target product, N,N-bis[3-(trimethoxysilyl)propyl]-1-hexanamine.

Claims

1. The following general formula (1) or (1′): 【Chemistry 1】 (In the formula, R 1 represents a monovalent hydrocarbon group having 1 to 18 carbon atoms which is unsubstituted or substituted with a group other than an amino group, and R 2 and R 3 represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 3 carbon atoms, R 4 and R 5 represents a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 18 carbon atoms, and X represents a single bond or NR 6 represents R 6 represents a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 18 carbon atoms; R 5 and R 6 may be bonded to each other to form a ring together with the nitrogen atom to which they are bonded, and n represents an integer of 1 to 3. and an amine compound represented by the following general formula (2): 【Chemistry 2】 (In the formula, R 7 represents an unsubstituted divalent hydrocarbon group having 1 to 10 carbon atoms, which may contain a heteroatom; R 8 and R 9 each independently represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, Y represents a chlorine atom, bromine atom, or iodine atom, and m represents an integer of 0 to 2. and a haloalkylalkoxysilane compound represented by the following general formula (3) or (3′): 【Transformation 3】 [(wherein, R 1 ~R 3 and n have the same meaning as above, R 10 is represented by the following general formula (4): 【Chemistry 4】 (In the formula, R 7 ~R 9 and m have the same meanings as above. R represents an alkoxysilylalkyl group represented by 4’ and R 5’ is R 10 or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 18 carbon atoms; X ’ is a single bond or NR 6’ represents R 6’ is R 10 or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 18 carbon atoms. In the method for producing a nitrogen-containing polyfunctional organoxysilane compound represented by the following general formula (5), 【Transformation 5】 (In the formula, R 11 represents a branched or cyclic saturated monovalent hydrocarbon group having 3 to 10 carbon atoms, in which the carbon atom bonded to the nitrogen atom is branched, and which may have a heteroatom interposed therebetween; R 12 represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, which may have a heteroatom interposed therebetween (however, branched or cyclic saturated monovalent hydrocarbon groups having 3 to 10 carbon atoms in which the carbon atom bonded to the nitrogen atom is branched are excluded), or a branched or cyclic saturated monovalent hydrocarbon group having 3 to 10 carbon atoms, which may have a heteroatom interposed therebetween, in which the carbon atom bonded to the nitrogen atom is branched. 11 and R 12 may be bonded to each other to form a ring together with the nitrogen atom to which they are attached. A method for producing a nitrogen-containing polyfunctional organoxysilane compound using a secondary amine compound represented by the following formula (I):

2. R in the general formula (5) 11 and R 12 the combination of the above is any one of a combination of secondary alkyl groups having 3 to 10 carbon atoms, a combination of cycloalkyl groups having 3 to 10 carbon atoms, a combination of a secondary alkyl group having 3 to 10 carbon atoms and a primary alkyl group having 1 to 10 carbon atoms, a combination of a cycloalkyl group having 3 to 10 carbon atoms and a primary alkyl group having 1 to 10 carbon atoms, a combination of a tertiary alkyl group having 4 to 10 carbon atoms and a primary alkyl group having 1 to 10 carbon atoms, and a combination of tertiary alkyl groups having 4 to 10 carbon atoms.

3. 3. The method for producing a nitrogen-containing polyfunctional organoxysilane compound according to claim 1, wherein the secondary amine compound represented by the general formula (5) is any one of the following: 【Transformation 6】

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