Nitrogen-containing silane compound and method for producing the same

Abstract

To provide a compound useful as a polymer modifier, which makes it possible to more effectively improve characteristics of a polymer compound by introduction of a functional group.SOLUTION: The invention provides a nitrogen-containing silane compound represented by the general formula (1) in the figure. In the formula: R1 represents a hydrogen atom or an unsubstituted monovalent hydrocarbon group; R2 and R3 each independently represent an unsubstituted monovalent hydrocarbon group or -OR5, where R5 represents an unsubstituted monovalent hydrocarbon group; R4 represents an unsubstituted divalent hydrocarbon group; A represents a group represented by the general formula (3) in the figure or the like; and R6 and R7 represent a monovalent hydrocarbon group in which a heteroatom may be interposed or a triorganosilyl group, and may be bonded to each other to form a ring together with the nitrogen atom to which they are bonded.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a novel nitrogen-containing silane compound and a method for producing the same. [Background technology]

[0002] Various attempts have been made to improve the properties of polymer compounds, and one known example is a method of introducing a functional group into a polymer compound.

[0003] As one of the above-mentioned functional group introduction methods, a method is known in which a compound having both a double bond and a functional group is reacted with a monomer to introduce a functional group into a polymer compound. For example, Patent Document 1 proposes a method using 1-[{N,N-bis(trimethylsilylamine)}dimethylsilyl}-2-{(4-vinylphenyl)dimethylsilyl}ethane, and Patent Document 2 proposes a method using 6-(N,N-bistrimethylsilylamino)myrcene. It is known that when a polymer compound having such introduced functional groups is used in a rubber composition for tires, the interaction with silica, which is the main filler in the rubber composition, is improved. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Special Publication No. 2018-513897 [Patent Document 2] Special Publication No. 2022-519481 Summary of the Invention [Problem to be solved by the invention]

[0005] In the method of Patent Document 1, a highly reactive Si-N bond is introduced into a polymer compound, and then the polymer compound is bonded to a silanol group on the silica surface via a siloxane bond, thereby improving the affinity between the polymer and silica. However, there is room for further improvement in the dispersibility of silica. On the other hand, in the method of Patent Document 2, the functional group introduced is an amino group, and therefore the hydrogen bonds possessed by the amino group enable the silica to be dispersed, and at the same time, the high polarity of the amino group increases the interaction with the silica itself, so that the effect of introducing the functional group is high. However, since a conjugated diene structure in which the double bond portion is substituted is formed, the reactivity during the introduction of the functional group is low, and there is a possibility that the functional group cannot be sufficiently introduced into the polymer compound.

[0006] The present invention has been made in view of the above circumstances, and an object of the present invention is to provide a novel nitrogen-containing silane compound that is useful as a polymer modifier and that enables more effective improvement of the properties of a polymer compound by introducing a functional group, and a method for producing the same. [Means for solving the problem]

[0007] As a result of extensive investigations aimed at achieving the above object, the present inventors have found that a specific nitrogen-containing silane compound is useful as a modifier that can more effectively improve the interaction between silica and a polymer compound and the dispersibility of silica, and have thus completed the present invention.

[0008] That is, the present invention provides 1. A nitrogen-containing silane compound represented by the following general formula (1): [ka] [In the formula, R 1 represents a hydrogen atom or an unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, R 2 and R 3 each independently represents an unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms or a group represented by the following general formula (2): -OR 5 (2) (In the formula, R 5 represents an unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms. R 4 represents an unsubstituted divalent hydrocarbon group having 1 to 20 carbon atoms, A represents a group represented by the following general formula (3) or a group represented by the following general formula (4). [ka] (In the formula, R 6 and R 7 represents a monovalent hydrocarbon group having 1 to 20 carbon atoms which may be interrupted by a heteroatom or a triorganosilyl group, which may be bonded to each other to form a ring having 2 to 20 carbon atoms together with the nitrogen atom to which they are bonded. [ka] (In the formula, R 8 represents an unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms or a triorganosilyl group; R 9 and R 10 each independently represents a divalent hydrocarbon group having 1 to 20 carbon atoms; R 11 represents CH or a nitrogen atom.)] 2. The following general formula (5) [ka] (In the formula, R 2 ~R 4 and A have the same meaning as above, R 12 represents an unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms. and a nitrogen-containing silane compound represented by the following general formula (6): [ka] (In the formula, R 1 has the same meaning as above, and X represents a chlorine atom, a bromine atom, or an iodine atom. The method for producing the nitrogen-containing silane compound according to claim 1, comprising reacting a Grignard reagent represented by the formula: to provide. Effect of the Invention

[0009] INDUSTRIAL APPLICABILITY The nitrogen-containing silane compound of the present invention is useful as a polymer modifier, etc., since it can more effectively improve the interaction between silica and a polymer and the dispersibility of silica. [Brief description of the drawings]

[0010] [Figure 1] 1 is a 1H-NMR spectrum of 4-[(3-diethylaminopropyl)dimethoxysilyl]styrene obtained in Example 1. [Diagram 2] 1 is an IR spectrum of 4-[(3-diethylaminopropyl)dimethoxysilyl]styrene obtained in Example 1. [Diagram 3] 1H-NMR spectrum of 4-[3-(4-methylpiperazin-1-yl)propyl]dimethoxysilyl]styrene obtained in Example 2. [Figure 4] 1 is an IR spectrum of 4-[3-(4-methylpiperazin-1-yl)propyl]dimethoxysilyl]styrene obtained in Example 2. [Diagram 5] 1H-NMR spectrum of 1-[4-[(3-diethylaminopropyl)dimethoxysilyl]]phenyl-1-phenylethylene obtained in Example 3. [Figure 6] 1 is an IR spectrum of 1-[4-[(3-diethylaminopropyl)dimethoxysilyl]]phenyl-1-phenylethylene obtained in Example 3. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0011] The nitrogen-containing silane compound of the present invention is a compound represented by the following general formula (1) (hereinafter referred to as "compound (1)").

[0012] [ka]

[0013] In the above general formula (1), R 1is a hydrogen atom or an unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms. R 1 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, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, and n-icosyl; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, thexyl, and 2-ethylhexyl; cyclic alkyl groups such as cyclopentyl and cyclohexyl; alkenyl groups such as vinyl, allyl, 1-propenyl, 1-butenyl, and 1-pentenyl; aryl groups such as phenyl, tolyl, and xylyl; and aralkyl groups such as benzyl and phenethyl.

[0014] Among these, R 1 is preferably a hydrogen atom, an unsubstituted linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, an unsubstituted linear, branched or cyclic alkenyl group having 2 to 10 carbon atoms, an unsubstituted aryl group having 6 to 10 carbon atoms, or an unsubstituted aralkyl group having 7 to 10 carbon atoms, and is more preferably a hydrogen atom, a methyl group, or a phenyl group, particularly from the viewpoint of easy availability of raw materials.

[0015] In the above general formula (1), R 2 and R 3 are each independently an unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms or an organoxy group represented by the following general formula (2), and each is preferably an organoxy group represented by the following general formula (2). -OR 5 (2) In formula (2), R 5 R is an unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms. 2 , R 3 and R 5 As the monovalent hydrocarbon group, R 1 The same groups as those shown below can be mentioned.

[0016] In the above general formula (1), R 4 represents an unsubstituted divalent hydrocarbon group having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 5 carbon atoms. Specific examples include alkylene groups such as methylene, ethylene, methylethylene, trimethylene, methylpropylene, tetramethylene, hexamethylene, octamethylene, decamethylene, and isobutylene groups; arylene groups such as phenylene and methylphenylene groups; and aralkylene groups such as ethylenephenylene and ethylenephenylenemethylene groups.

[0017] R 4 In the case where is a single bond and A is a group represented by general formula (3), when compound (1) is used as a polymer modifier, the N-Si bond is cleaved by hydrolysis or the like, the amino group contained in A is removed from the polymer, and the interaction between the polymer compound and silica is lost. In contrast, due to the presence of an unsubstituted divalent hydrocarbon group having 1 to 20 carbon atoms as in the present invention, even after use as a polymer modifier, the amino group is not removed by cleavage, and it is possible to allow the amino group, which has a large interaction with silica, to remain in the polymer, thereby making it possible to increase the interaction between the polymer compound and silica.

[0018] In the above general formula (1), A is a group represented by the following general formula (3) or (4).

[0019] [ka]

[0020] In the above general formula (3), R 6 and R 7 is a monovalent hydrocarbon group having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms, which may have a heteroatom such as an oxygen atom or a sulfur atom interposed therebetween, or a triorganosilyl group. R 6 and R 7The 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-tetradecyl, n-hexadecyl, n-octadecyl, and n-icosyl; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, thexyl, and 2-ethylhexyl; cyclic alkyl groups such as cyclopentyl and cyclohexyl; alkenyl groups such as vinyl, allyl, propenyl, 1-butenyl, and 1-pentenyl; aryl groups such as phenyl, tolyl, and xylyl; and aralkyl groups such as benzyl and phenethyl.

[0021] Among these, R 6 and R 7 is preferably a hydrogen atom, an unsubstituted linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, an unsubstituted linear, branched or cyclic alkenyl group having 2 to 10 carbon atoms, an unsubstituted aryl group having 6 to 10 carbon atoms, or an unsubstituted aralkyl group having 7 to 10 carbon atoms, and is more preferably a hydrogen atom, a methyl group, or a phenyl group, particularly from the viewpoint of easy availability of raw materials.

[0022] Also, R 6 and R 7 may be bonded to each other to form a ring having 2 to 20 carbon atoms together with the nitrogen atom to which they are bonded. Examples of such a ring include a piperidine ring, a piperazine ring, a pyrrolidine ring, and a morpholine ring.

[0023] Specific examples of the triorganosilyl group include trialkylsilyl groups having an alkyl group having 1 to 6 carbon atoms, such as trimethylsilyl, ethyldimethylsilyl, diethylmethylsilyl, triethylsilyl, tri-n-propylsilyl, triisopropylsilyl, tri-n-butylsilyl, triisobutylsilyl, trisec-butylsilyl, tert-butyldimethylsilyl, tricyclopentylsilyl, and tricyclohexylsilyl groups; triarylsilyl groups having an aryl group having 6 to 10 carbon atoms, such as a triphenylsilyl group; and alkyldiarylsilyl groups having an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 10 carbon atoms, such as a tert-butyldiphenylsilyl group.

[0024] In the above general formula (4), R 8 is an unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 5 carbon atoms, or a triorganosilyl group, specific examples of which include R 6 and R 7 The same groups as those shown below can be mentioned.

[0025] R 9 and R 10 are each independently an unsubstituted divalent hydrocarbon group having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 5 carbon atoms. Specific examples thereof include alkylene groups such as methylene, ethylene, methylethylene, trimethylene, methylpropylene, tetramethylene, hexamethylene, octamethylene, decamethylene, and isobutylene groups; arylene groups such as phenylene and methylphenylene groups; and aralkylene groups such as ethylenephenylene and ethylenephenylenemethylene groups. R 11 represents CH or a nitrogen atom.

[0026] Specific examples of compound (1) include 4-(dimethylaminomethyldimethylsilyl)styrene, 4-(diethylaminomethyldimethylsilyl)styrene, 4-(dibutylaminomethyldimethylsilyl)styrene, 4-[(N,N-bistrimethylsilyl)aminomethyldimethylsilyl]styrene, 4-(morpholinomethyldimethylsilyl)styrene, 4-[(4-methylpiperazin-1-yl)methyldimethylsilyl]styrene, 4-[(3-dimethylaminopropyl)dimethylsilyl]styrene, 4-[ (3-diethylaminopropyl)dimethylsilyl]styrene, 4-[(3-dibutylaminopropyl)dimethylsilyl]styrene, 4-[3-[(N,N-bistrimethylsilyl)aminopropyl]dimethylsilyl]styrene, 4-[(3-morpholinopropyl)dimethylsilyl]styrene, 4-[3-(4-methylpiperazin-1-yl)propyl]dimethylsilyl]styrene, 4-(dimethylaminomethylmethoxymethylsilyl)styrene, 4-(diethylaminomethylmethoxymethylsilyl)styrene Styrene, 4-(dibutylaminomethylmethoxymethylsilyl)styrene, 4-[(N,N-bistrimethylsilyl)aminomethylmethoxymethylsilyl]styrene, 4-(morpholinomethylmethoxymethylsilyl)styrene, 4-[(4-methylpiperazin-1-yl)methylmethoxymethylsilyl]styrene, 4-[(3-dimethylaminopropyl)methoxymethylsilyl]styrene, 4-[(3-diethylaminopropyl)methoxymethylsilyl]styrene, 4-[(3-dibutylaminopropyl )methoxymethylsilyl]styrene, 4-[3-[(N,N-bistrimethylsilyl)aminopropyl]methoxymethylsilyl]styrene, 4-[(3-morpholinopropyl)methoxymethylsilyl]styrene, 4-[3-(4-methylpiperazin-1-yl)propyl]methoxymethylsilyl]styrene, 4-(dimethylaminomethyldimethoxysilyl)styrene, 4-(diethylaminomethyldimethoxysilyl)styrene, 4-(dibutylaminomethyldimethoxysilyl)styrene, 4-[(N,N-bistrimethylsilyl)aminomethyldimethoxysilyl]styrene, 4-(morpholinomethyldimethoxysilyl)styrene, 4-[(4-methylpiperazin-1-yl)methyldimethoxysilyl]styrene, 4-[(3-dimethylaminopropyl)dimethoxysilyl]styrene, 4-[(3-diethylaminopropyl)dimethoxysilyl]styrene, 4-[(3-dibutylaminopropyl)dimethoxysilyl]styrene, 4-[3-[(N,N-bistrimethylsilyl)aminopropyl]dimethoxysilyl]styrene, 4-[(3-morpholinopropyl)dimethoxysilyl]styrene, 4-[3-(4-methylpiperazin-1-yl)propyl]dimethoxysilyl]styrene, 4-(dimethylaminomethylethoxymethylsilyl)styrene, 4-(diethylaminomethylethoxymethylsilyl)styrene, 4-(dibutylaminomethylethoxymethylsilyl)styrene, 4-[(N,N-bistrimethylsilyl)aminopropyl]dimethoxysilyl]styrene, 4-(morpholinomethylethoxymethylsilyl)styrene, 4-[(4-methylpiperazin-1-yl)methylethoxymethylsilyl]styrene, 4-[(3-dimethylaminopropyl)ethoxymethylsilyl]styrene, 4-[(3-diethylaminopropyl)ethoxymethylsilyl]styrene, 4-[(3-dibutylaminopropyl)ethoxymethylsilyl]styrene, 4-[3- [(N,N-bistrimethylsilyl)aminopropyl]ethoxymethylsilyl]styrene, 4-[(3-morpholinopropyl)ethoxymethylsilyl]styrene, 4-[3-(4-methylpiperazin-1-yl)propyl]ethoxymethylsilyl]styrene, 4-(dimethylaminomethyldiethoxysilyl)styrene, 4-(diethylaminomethyldiethoxysilyl)styrene, 4-(dibutylaminomethyldiethoxysilyl)styrene, 4-[(N,N-bistrimethylsilyl)aminomethyldiethoxysilyl]styrene, 4-(morpholinomethyldiethoxysilyl)styrene, 4-[(4-methylpiperazin-1-yl)methyldiethoxysilyl]styrene, 4-[(3-dimethylaminopropyl)diethoxysilyl]styrene, 4-[(3-diethylaminopropyl)diethoxysilyl]styrene, 4-[(3-dibutylaminopropyl)diethoxysilyl]styrene, 4-[3-[(N,N-bistrimethylsilyl)aminopropyl]diethoxysilyl]styrene, 4-[(3-morpholinopropyl) 4-[3-(4-methylpiperazin-1-yl)propyl]diethoxysilyl]styrene, 3-(dimethylaminomethyldimethylsilyl)styrene, 3-(diethylaminomethyldimethylsilyl)styrene, 3-(dibutylaminomethyldimethylsilyl)styrene, 3-[(N,N-bistrimethylsilyl)aminomethyldimethylsilyl]styrene, 3-(morpholinomethyldimethylsilyl)styrene, 3-[(4-methylpiperazin-1-yl)methyldimethylsilyl]styrene, 3-[(3-dimethylaminopropyl) 3-[(3-propyl)dimethylsilyl]styrene, 3-[(3-diethylaminopropyl)dimethylsilyl]styrene, 3-[(3-dibutylaminopropyl)dimethylsilyl]styrene, 3-[3-[(N,N-bistrimethylsilyl)aminopropyl]dimethylsilyl]styrene, 3-[(3-morpholinopropyl)dimethylsilyl]styrene, 3-[3-(4-methylpiperazin-1-yl)propyl]dimethylsilyl]styrene, 3-(dimethylaminomethylmethoxymethylsilyl)styrene, 3-(diethylaminomethylmethoxymethylsilyl)styrene , 3-(dibutylaminomethylmethoxymethylsilyl)styrene, 3-[(N,N-bistrimethylsilyl)aminomethylmethoxymethylsilyl]styrene, 3-(morpholinomethylmethoxymethylsilyl)styrene, 3-[(4-methylpiperazin-1-yl)methylmethoxymethylsilyl]styrene, 3-[(3-dimethylaminopropyl)methoxymethylsilyl]styrene, 3-[(3-diethylaminopropyl)methoxymethylsilyl]styrene, 3-[(3-dibutylaminopropyl)methoxymethylsilyl]styrene, 3-[3-[(N,N-bistrimethylsilyl)aminopropyl]methoxymethylsilyl]styrene, 3-[(3-morpholinopropyl)methoxymethylsilyl]styrene, 3-[3-(4-methylpiperazin-1-yl)propyl]methoxymethylsilyl]styrene, 3-(dimethylaminomethyldimethoxysilyl)styrene, 3-(diethylaminomethyldimethoxysilyl)styrene, 3-(dibutylaminomethyldimethoxysilyl)styrene, 3-[(N,N-bistrimethylsilyl)aminomethyldimethoxysilyl]styrene, 3-(morpholinomethyldimethoxysilyl)styrene, 3-[(4-methylpiperazin-1-yl)methyldimethoxysilyl]styrene, 3-[(3-dimethylaminopropyl)dimethoxysilyl]styrene, 3-[(3-diethylaminopropyl)dimethoxysilyl]styrene, 3-[(3-dibutylaminopropyl)dimethoxysilyl]styrene, 3-[3-[(N,N-bistrimethylsilyl)aminomethyldimethoxysilyl]styrene, methylsilyl)aminopropyl]dimethoxysilyl]styrene, 3-[(3-morpholinopropyl)dimethoxysilyl]styrene, 3-[3-(4-methylpiperazin-1-yl)propyl]dimethoxysilyl]styrene, 3-(dimethylaminomethylethoxymethylsilyl)styrene, 3-(diethylaminomethylethoxymethylsilyl)styrene, 3-(dibutylaminomethylethoxymethylsilyl)styrene, 3-[(N,N-bistrimethylsilyl)aminomethylethoxymethylsilyl]styrene, 3-(morpholinomethylethoxymethylsilyl)styrene, 3-[(4-methylpiperazin-1-yl)methylethoxymethylsilyl]styrene, 3-[(3-dimethylaminopropyl)ethoxymethylsilyl]styrene, 3-[(3-diethylaminopropyl)ethoxymethylsilyl]styrene, 3-[(3-dibutylaminopropyl)ethoxymethylsilyl]styrene, 3-[3-[(N,N-bistrimethylsilyl)aminopropyl]ethoxymethylsilyl]styrene, 3-[(3-morpholinopropyl)ethoxymethylsilyl]styrene, 3-[3-(4-methylpiperazin-1-yl)propyl]ethoxymethylsilyl]styrene, 3-(dimethylaminomethyldiethoxysilyl)styrene, 3-(diethylaminomethyldiethoxysilyl)styrene, 3-(dibutylaminomethyldiethoxysilyl)styrene, 3-[(N,N-bistrimethylsilyl)aminomethyldiethoxysilyl]styrene, 3-(morpholinomethyldi ethoxysilyl)styrene, 3-[(4-methylpiperazin-1-yl)methyldiethoxysilyl]styrene, 3-[(3-dimethylaminopropyl)diethoxysilyl]styrene, 3-[(3-diethylaminopropyl)diethoxysilyl]styrene, 3-[(3-dibutylaminopropyl)diethoxysilyl]styrene, 3-[3-[(N,N-bistrimethylsilyl)aminopropyl]diethoxysilyl]styrene, 3-[(3-morpholinopropyl)diethoxysilyl]styrene, 3-[3-(4-methylpiperazin-1-yl)propyl n-Diethoxysilyl]styrene, 2-(dimethylaminomethyldimethylsilyl)styrene, 2-(diethylaminomethyldimethylsilyl)styrene, 2-(dibutylaminomethyldimethylsilyl)styrene, 2-[(N,N-bistrimethylsilyl)aminomethyldimethylsilyl]styrene, 2-(morpholinomethyldimethylsilyl)styrene, 2-[(4-methylpiperazin-1-yl)methyldimethylsilyl]styrene, 2-[(3-dimethylaminopropyl)dimethylsilyl]styrene, 2-[(3-diethylaminopropyl)dimethyl silyl]styrene, 2-[(3-dibutylaminopropyl)dimethylsilyl]styrene, 2-[3-[(N,N-bistrimethylsilyl)aminopropyl]dimethylsilyl]styrene, 2-[(3-morpholinopropyl)dimethylsilyl]styrene, 2-[3-(4-methylpiperazin-1-yl)propyl]dimethylsilyl]styrene, 2-(dimethylaminomethylmethoxymethylsilyl)styrene, 2-(diethylaminomethylmethoxymethylsilyl)styrene, 2-(dibutylaminomethylmethoxymethylsilyl)styrene, 2-[(N,N-bistrimethylsilyl)aminomethylmethoxymethylsilyl]styrene, 2-(morpholinomethylmethoxymethylsilyl)styrene, 2-[(4-methylpiperazin-1-yl)methylmethoxymethylsilyl]styrene, 2-[(3-dimethylaminopropyl)methoxymethylsilyl]styrene, 2-[(3-diethylaminopropyl)methoxymethylsilyl]styrene, 2-[(3-dibutylaminopropyl)methoxymethylsilyl]styrene, 2-[3-[(N,N-bistrimethylsilyl)aminopropyl]methoxymethylsilyl]styrene, 2-[(3-morpholinopropyl)methoxymethylsilyl]styrene, 2-[3-(4-methylpiperazin-1-yl)propyl]methoxymethyl silyl]styrene, 2-(dimethylaminomethyldimethoxysilyl)styrene, 2-(diethylaminomethyldimethoxysilyl)styrene, 2-(dibutylaminomethyldimethoxysilyl)styrene, 2-[(N,N-bistrimethylsilyl)aminomethyldimethoxysilyl]styrene, 2-(morpholinomethyldimethoxysilyl)styrene, 2-[(4-methylpiperazin-1-yl)methyldimethoxysilyl]styrene, 2-[(3-dimethylaminopropyl)dimethoxysilyl]styrene, 2-[(3-diethylaminopropyl)dimethoxysilyl]styrene, 2-[(3-dibutylaminopropyl)dimethoxysilyl]styrene, 2-[3-[(N,N-bistrimethylsilyl)aminopro, pyl]dimethoxysilyl]styrene, 2-[(3-morpholinopropyl)dimethoxysilyl]styrene, 2-[3-(4-methylpiperazin-1-yl)propyl]dimethoxysilyl]styrene, 2-(dimethylaminomethylethoxymethylsilyl)styrene, 2-(diethylaminomethylethoxymethylsilyl)styrene, 2-(dibutylaminomethylethoxymethylsilyl)styrene, 2-[(N,N-bistrimethylsilyl)aminomethylethoxymethylsilyl]styrene, 2-(morpholinomethylethoxymethylsilyl)styrene, 2-[(4-methylpiperazin-1-yl)methylethoxymethylsilyl]styrene, 2-[(3-dimethylaminopropyl)ethoxymethylsilyl]styrene, 2-[(3-diethylaminopropyl)ethoxymethylsilyl]styrene, 2-[(3-dibutylaminopropyl)ethoxymethylsilyl]styrene, 2-[3-[(N,N-bis 2-[(3-morpholinopropyl)ethoxymethylsilyl]styrene, 2-[3-(4-methylpiperazin-1-yl)propyl]ethoxymethylsilyl]styrene, 2-(dimethylaminomethyldiethoxysilyl)styrene, 2-(diethylaminomethyldiethoxysilyl)styrene, 2-(dibutylaminomethyldiethoxysilyl)styrene, 2-[(N,N- bis(trimethylsilyl)aminomethyldiethoxysilyl]styrene, 2-(morpholinomethyldiethoxysilyl)styrene, 2-[(4-methylpiperazin-1-yl)methyldiethoxysilyl]styrene, 2-[(3-dimethylaminopropyl)diethoxysilyl]styrene, 2-[(3-diethylaminopropyl)diethoxysilyl]styrene, 2-[(3-dibutylaminopropyl)diethoxysilyl]styrene, 2-[3-[(N,N-bistrimethylsilyl)aminopropyl]diethoxysilyl]styrene, 2-[(3-morpholinopropyl)diethoxysilyl]styrene, 2-[3-(4-methylpiperazin-1-yl)propyl]diethoxysilyl]styrene, 1-[4-(dimethylaminomethyldimethylsilyl)]phenyl-1-phenylethylene, 1-[4-(diethylaminomethyldimethylsilyl)]phenyl-1-phenylethylene, 1-[4-(dibutylaminomethyldimethylsilyl)]phenyl-1-phenylethylene, 1-[4-[(N,N-bistrimethylsilyl)aminomethyldimethylsilyl]]phenyl-1-phenylethylene, 1-[4-(morpholinomethyldimethylsilyl)]phenyl-1-phenylethylene, 1-[4-[(4-methylpiperazin-1-yl)methyldimethylsilyl]]phenyl-1-phenylethylene, 1-[4-[(3-dimethylaminopropyl)dimethylsilyl] ]phenyl-1-phenylethylene, 1-[4-[(3-diethylaminopropyl)dimethylsilyl]phenyl-1-phenylethylene, 1-[4-[(3-dibutylaminopropyl)dimethylsilyl]phenyl-1-phenylethylene, 1-[4-[3-[(N,N-bistrimethylsilyl)aminopropyl]dimethylsilyl]phenyl-1-phenylethylene, 1-[4-[(3-morpholinopropyl)dimethylsilyl]phenyl-1-phenylethylene, 1-[4-[3-(4-methylpiperazin-1-yl)propyl]dimethylsilyl]phenyl-1-phenylethylene, 1-[4-(dimethylaminomethylmethoxymethylsilyl)]phenyl-1-phenylethylene, 1-[4-(diethylaminomethylmethoxymethylsilyl)]phenyl-1-phenylethylene, 1-[4-(dibutylaminomethylmethoxymethylsilyl)]phenyl-1-phenylethylene, 1-[4-[(N,N-bis(trimethylsilyl)aminomethylmethoxymethylsilyl]]phenyl-1-phenylethylene, 1-[4-(morpholinomethylmethoxymethylsilyl)]phenyl-1-phenylethylene, 1-[4-[(4-methylpiperazin-1-yl)methylmethoxymethylsilyl]]phenyl-1-phenylethylene, 1-[4-[(3-dimethylaminopropyl)methoxymethylsilyl]]phenyl-1-phenylethylene, 1-[4-[(3-diethylaminopropyl)methoxymethyl 1-[4-[(3-dibutylaminopropyl)methoxymethylsilyl]]phenyl-1-phenylethylene, 1-[4-[3-[(N,N-bistrimethylsilyl)aminopropyl]methoxymethylsilyl]]phenyl-1-phenylethylene, 1-[4-[(3-morpholinopropyl)methoxymethylsilyl]]phenyl-1-phenylethylene, 1-[4-[3-(4-methylpiperazin-1-yl)propyl]methoxymethylsilyl]] Phenyl-1-phenylethylene, 1-[4-(dimethylaminomethyldimethoxysilyl)]phenyl-1-phenylethylene, 1-[4-(diethylaminomethyldimethoxysilyl)]phenyl-1-phenylethylene, 1-[4-(dibutylaminomethyldimethoxysilyl)]phenyl-1-phenylethylene, 1-[4-[(N,N-bistrimethylsilyl)aminomethyldimethoxysilyl]]phenyl-1-phenylethylene, 1-[4-(morpholinomethyldimethoxysilyl)] Phenyl-1-phenylethylene, 1-[4-[(4-methylpiperazin-1-yl)methyldimethoxysilyl]]phenyl-1-phenylethylene, 1-[4-[(3-dimethylaminopropyl)dimethoxysilyl]]phenyl-1-phenylethylene, 1-[4-[(3-diethylaminopropyl)dimethoxysilyl]]phenyl-1-phenylethylene, 1-[4-[(3-dibutylaminopropyl)dimethoxysilyl]]phenyl-1-phenylethylene, 1-[4-[3-[(N,N-bis(trimethylsilyl)aminopropyl]dimethoxysilyl]]phenyl-1-phenylethylene, 1-[4-[(3-morpholinopropyl)dimethoxysilyl]]phenyl-1-phenylethylene, 1-[4-[3-(4-methylpiperazin-1-yl)propyl]dimethoxysilyl]]phenyl-1-phenylethylene, 1-[4-(dimethylaminomethylethoxymethylsilyl)]phenyl-1-phenylethylene, 1-[4-(diethylaminomethylethoxymethylsilyl)] Phenyl-1-phenylethylene, 1-[4-(dibutylaminomethylethoxymethylsilyl)]phenyl-1-phenylethylene, 1-[4-[(N,N-bistrimethylsilyl)aminomethylethoxymethylsilyl]]phenyl-1-phenylethylene, 1-[4-(morpholinomethylethoxymethylsilyl)]phenyl-1-phenylethylene, 1-[4-[(4-methylpiperazin-1-yl)methylethoxymethylsilyl]]phenyl-1-phenylethylene, 1-[4-[(3 -dimethylaminopropyl)ethoxymethylsilyl]]phenyl-1-phenylethylene, 1-[4-[(3-diethylaminopropyl)ethoxymethylsilyl]]phenyl-1-phenylethylene, 1-[4-[(3-dibutylaminopropyl)ethoxymethylsilyl]]phenyl-1-phenylethylene, 1-[4-[3-[(N,N-bistrimethylsilyl)aminopropyl]ethoxymethylsilyl]]phenyl-1-phenylethylene, 1-[4-[(3-morpholinopropyl)ethoxymethylsilyl]]phenyl-1-phenylethylene, 1-[4-[3-(4-methylpiperazin-1-yl)propyl]ethoxymethylsilyl]]phenyl-1-phenylethylene, 1-[4-(dimethylaminomethyldiethoxysilyl)]phenyl-1-phenylethylene, 1-[4-(diethylaminomethyldiethoxysilyl)]phenyl-1-phenylethylene, 1-[4-(dibutylaminomethyldiethoxysilyl)]phenyl-1-phenylethylene, 1-[4-[(N,N-bis(trimethylsilyl)aminomethyldiethoxysilyl]]phenyl-1-phenylethylene, 1-[4-(morpholinomethyldiethoxysilyl)]phenyl-1-phenylethylene, 1-[4-[(4-methylpiperazin-1-yl)methyldiethoxysilyl]]phenyl-1-phenylethylene, 1-[4-[(3-dimethylaminopropyl)diethoxysilyl]]phenyl-1-phenylethylene, 1-[4-[(3-diethylaminopropyl)diethoxysilyl]]phenyl-1- Phenylethylene, 1-[4-[(3-dibutylaminopropyl)diethoxysilyl]]phenyl-1-phenylethylene, 1-[4-[3-[(N,N-bistrimethylsilyl)aminopropyl]diethoxysilyl]]phenyl-1-phenylethylene, 1-[4-[(3-morpholinopropyl)diethoxysilyl]]phenyl-1-phenylethylene, 1-[4-[3-(4-methylpiperazin-1-yl)propyl]diethoxysilyl]]phenyl-1-phenylethylene, and the like.

[0027] Next, the method for producing the compound (1) of the present invention will be described. Compound (1) can be produced, for example, by reacting a nitrogen-containing silane compound represented by the following general formula (5) (hereinafter referred to as "compound (5)") with a Grignard reagent represented by the following general formula (6) (hereinafter referred to as "compound (6)").

[0028] [ka] (In the formula, R 2 ~R 4 and A have the same meaning as above, and R 12 represents an unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms.

[0029] [ka] (In the formula, R 1 has the same meaning as above, and X represents a chlorine atom, a bromine atom, or an iodine atom.

[0030] Specific examples of compound (5) include dimethylaminomethylmethoxydimethylsilane, diethylaminomethylmethoxydimethylsilane, dibutylaminomethylmethoxydimethylsilane, (N,N-bistrimethylsilyl)aminomethylmethoxydimethylsilane, morpholinomethylmethoxydimethylsilane, (4-methylpiperazin-1-yl)methylmethoxydimethylsilane, (3-dimethylaminopropyl)methoxydimethylsilane, (3-diethylaminopropyl)methoxydimethylsilane, (3-dibutylaminopropyl)methylmethoxydimethylsilane, 3-[(N,N-bistrimethylsilyl)aminopropyl]methoxydimethylsilane, (3-morpholinopropyl)methoxydimethylsilane, 3-[(4-methylpiperazin-1-yl)propyl]methoxydimethylsilane, dimethylaminomethyldimethoxymethylsilane, diethylaminomethyldimethoxymethylsilane, dibutylaminomethyldimethoxymethylsilane, (N,N-bistrimethylsilyl)aminomethyldimethoxymethylsilane, morpholinomethyl ... morpholinomethylmethoxydimethylsilane, dimethylaminomethyldimethoxymethylsilane, diethylaminomethyldimethoxymethylsilane, dibutylaminomethyldimethoxymethylsilane, morpholinomethylmethoxydimethylsilane, dimethylaminomethyldimethoxymethylsilane, diethylaminomethyldimethoxymethylsilane, dibutylaminomethyldimethoxymethylsilane, dimethylaminomethyldimethoxymethylsilane, dimethylaminomethyldimethoxymethylsilane, diethylaminomethyldimethoxymethylsilane, diethylaminomethyldimethoxymethylsilane, dibutylaminomethyldimethoxymethylsilane, morpholinomethylmethoxydimethylsilane, dimethylaminomethyldimethoxymethylsilane, diethylaminomethyldimethoxymethylsilane, diethylaminomethyldimethoxymethylsilane, dibutylaminomethyldimethoxymethylsilane, N,N-bistrimethylsilyl)aminopropyl]dimethoxymethylsilane, (4-methylpiperazin-1-yl)methyldimethoxymethylsilane, (3-dimethylaminopropyl)dimethoxymethylsilane, (3-diethylaminopropyl)dimethoxymethylsilane, (3-dibutylaminopropyl)methyldimethoxymethylsilane, 3-[(N,N-bistrimethylsilyl)aminopropyl]dimethoxymethylsilane, (3-morpholinopropyl)dimethoxymethylsilane, 3-[(4-methylpiperazin-1-yl)propyl]dimethoxymethylsilane silane, dimethylaminomethyltrimethoxysilane, diethylaminomethyltrimethoxysilane, dibutylaminomethyltrimethoxysilane, (N,N-bistrimethylsilyl)aminomethyltrimethoxysilane, morpholinomethyltrimethoxysilane, (4-methylpiperazin-1-yl)methyltrimethoxysilane, (3-dimethylaminopropyl)trimethoxysilane, (3-diethylaminopropyl)trimethoxysilane, (3-dibutylaminopropyl)methyltrimethoxysilane, 3-[(N,N-bis(trimethylsilyl)aminopropyl]trimethoxysilane, (3-morpholinopropyl)trimethoxysilane, 3-[(4-methylpiperazin-1-yl)propyl]trimethoxysilane, dimethylaminomethylethoxydimethylsilane, diethylaminomethylethoxydimethylsilane, dibutylaminomethylethoxydimethylsilane, (N,N-bis(trimethylsilyl)aminomethylethoxydimethylsilane, morpholinomethylethoxydimethylsilane, (4-methylpiperazin-1-yl)methylethoxydimethylsilane, (3-dimethylaminomethylethoxydimethylsilane, (3-ethylaminopropyl)ethoxydimethylsilane, (3-diethylaminopropyl)ethoxydimethylsilane, (3-dibutylaminopropyl)methylethoxydimethylsilane, 3-[(N,N-bistrimethylsilyl)aminopropyl]ethoxydimethylsilane, (3-morpholinopropyl)ethoxydimethylsilane, 3-[(4-methylpiperazin-1-yl)propyl]ethoxydimethylsilane, dimethylaminomethyldiethoxymethylsilane, diethylaminomethyldiethoxymethylsilane, dibutylaminomethyldiethoxymethylsilane, ( N,N-bistrimethylsilyl)aminomethyldiethoxymethylsilane, morpholinomethyldiethoxymethylsilane, (4-methylpiperazin-1-yl)methyldiethoxymethylsilane, (3-dimethylaminopropyl)diethoxymethylsilane, (3-diethylaminopropyl)diethoxymethylsilane, (3-dibutylaminopropyl)methyldiethoxymethylsilane, 3-[(N,N-bistrimethylsilyl)aminopropyl]diethoxymethylsilane, (3-morpholinopropyl)diethoxymethylsilane, 3-[(4-methylpiperazin -1-yl)propyl]diethoxymethylsilane, dimethylaminomethyltriethoxysilane, diethylaminomethyltriethoxysilane, dibutylaminomethyltriethoxysilane, (N,N-bistrimethylsilyl)aminomethyltriethoxysilane, morpholinomethyltriethoxysilane, (4-methylpiperazin-1-yl)methyltriethoxysilane, (3-dimethylaminopropyl)triethoxysilane, (3-diethylaminopropyl)triethoxysilane, (3-dibutylaminopropyl)methyltriethoxysilane, 3-[(N,N-bis(trimethylsilyl)aminopropyl]triethoxysilane, (3-morpholinopropyl)triethoxysilane, 3-[(4-methylpiperazin-1-yl)propyl]triethoxysilane, etc.

[0031] Specific examples of compound (6) include 4-styrylmagnesium chloride, 4-styrylmagnesium bromide, 4-styrylmagnesium iodide, 3-styrylmagnesium chloride, 3-styrylmagnesium bromide, 3-styrylmagnesium iodide, 2-styrylmagnesium chloride, 2-styrylmagnesium bromide, 2-styrylmagnesium iodide, 4-(1-phenylvinyl)phenylmagnesium chloride, 4-(1-phenylvinyl)phenylmagnesium bromide, and 4-(1-phenylvinyl)phenylmagnesium iodide.

[0032] The compounding ratio of compound (5) and compound (6) is not particularly limited, but from the viewpoints of reactivity and productivity, the compound (6) is preferably 0.1 to 3.0 mol, more preferably 0.5 to 2 mol, per 1 mol of compound (5).

[0033] The reaction temperature of the above reaction is not particularly limited, but is preferably −40 to 200° C., more preferably 0 to 150° C. The reaction time is also not particularly limited, but is preferably 1 to 40 hours, more preferably 1 to 20 hours. The reaction atmosphere is preferably an inert gas atmosphere such as nitrogen or argon.

[0034] The above reaction proceeds without a solvent, but a solvent can also be used. Examples of the solvent include hydrocarbon solvents such as pentane, hexane, cyclohexane, heptane, isooctane, benzene, toluene, and xylene, ether solvents such as diethyl ether, tetrahydrofuran, and dioxane, ester solvents such as ethyl acetate and butyl acetate, aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, and N-methylpyrrolidone, and chlorinated hydrocarbon solvents such as dichloromethane and chloroform. These solvents may be used alone or in combination of two or more.

[0035] From the reaction mixture thus obtained, the target product can be recovered by a conventional method such as distillation or removal of low boiling point compounds. EXAMPLES

[0036] The present invention will be described in detail below with reference to examples, but the present invention is not limited to the following examples.

[0037] [Example 1] A flask equipped with a stirrer, reflux condenser, dropping funnel and thermometer was charged with 23.5g (0.1 mol) of (3-diethylaminopropyl)trimethoxysilane and 30ml of toluene, to which 43g of a tetrahydrofuran solution of 4-styrylmagnesium chloride (0.1 mol) was added dropwise over 1 hour at 20-30°C, and the mixture was stirred at that temperature for 1 hour. After filtering the reaction solution, the filtrate was distilled to obtain 14.1g of a fraction with a boiling point of 151-153°C / 0.3kPa.

[0038] Mass spectrum of the obtained fraction. 1 H-NMR and IR spectra were measured, and the results confirmed that the compound obtained was 4-[(3-diethylaminopropyl)dimethoxysilyl]styrene. [Mass Spectrum] m / z 307,193,163,133,117,86 [ 1 H-NMR spectrum (chloroform-d solvent) This is shown in chart in Figure 1. [IR spectrum] This is shown in chart in Figure 2.

[0039] [Example 2] A flask equipped with a stirrer, a reflux condenser, a dropping funnel, and a thermometer was charged with 26.2 g (0.1 mol) of (3-[(4-methylpiperazin-1-yl)propyl]trimethoxysilane and 30 ml of toluene, and 43 g of a tetrahydrofuran solution of 4-styrylmagnesium chloride (0.1 mol) was added dropwise at 20-30°C over 1 hour, followed by stirring at that temperature for 1 hour. The reaction liquid was filtered, and the filtrate was distilled to obtain 5.0 g of a fraction having a boiling point of 168-169°C / 0.2 kPa.

[0040] Mass spectrum of the obtained fraction. 1 The H-NMR spectrum and IR spectrum were measured, and the results confirmed that the compound obtained was 4-[3-(4-methylpiperazin-1-yl)propyl]dimethoxysilyl]styrene. [Mass Spectrum] m / z 334,193,163,133,113,70 [ 1 H-NMR spectrum (chloroform-d solvent) This is shown in chart in Figure 3. [IR spectrum] This is shown in chart in Figure 4.

[0041] [Example 3] A flask equipped with a stirrer, reflux condenser, dropping funnel and thermometer was charged with 23.5g (0.1 mol) of (3-diethylaminopropyl)trimethoxysilane and 30ml of toluene, to which 50g of a tetrahydrofuran solution of 4-(1-phenylvinyl)phenylmagnesium chloride (0.1 mol) was added dropwise over 1 hour at 20-30°C, and the mixture was stirred at that temperature for 1 hour. After filtering the reaction solution, the filtrate was distilled to obtain 15.3g of a fraction with a boiling point of 174-177°C / 0.03kPa.

[0042] Mass spectrum of the obtained fraction. 1 H-NMR spectrum and IR spectrum were measured, and the results confirmed that the compound obtained was 1-[4-[(3-diethylaminopropyl)dimethoxysilyl]]phenyl-1-phenylethylene. [Mass Spectrum] m / z 383,269,239,193,174,86 [ 1 H-NMR spectrum (chloroform-d solvent) This is shown in chart in Figure 5. [IR spectrum] This is shown in chart in Figure 6.

Claims

1. A nitrogen-containing silane compound represented by the following general formula (1): 【Chemistry 1】 [In the formula, R 1 represents a hydrogen atom or an unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, R 2 and R 3 each independently represents an unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms or a group represented by the following general formula (2): -OR 5 (2) (In the formula, R 5 represents an unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms. R 4 represents an unsubstituted divalent hydrocarbon group having 1 to 20 carbon atoms, A represents a group represented by the following general formula (3) or a group represented by the following general formula (4). 【Chemistry 2】 (In the formula, R 6 and R 7 represents a monovalent hydrocarbon group having 1 to 20 carbon atoms, which may be interrupted by a heteroatom, or a triorganosilyl group, which may be bonded to each other to form a ring having 2 to 20 carbon atoms together with the nitrogen atom to which they are bonded. 【Chemistry 3】 (In the formula, R 8 represents an unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms or a triorganosilyl group; R 9 and R 10 each independently represents a divalent hydrocarbon group having 1 to 20 carbon atoms; R 11 represents C—H or a nitrogen atom.)

2. The following general formula (5) 【Chemistry 4】 (In the formula, R 2 ~R 4 and A are as defined above, R 12 represents an unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms. and a nitrogen-containing silane compound represented by the following general formula (6): 【Chemistry 5】 (In the formula, R 1 has the same meaning as above, and X represents a chlorine atom, a bromine atom, or an iodine atom.

2. The method for producing the nitrogen-containing silane compound according to claim 1, wherein a Grignard reagent represented by the following formula (I) is reacted with the nitrogen-containing silane compound.

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