Cyclic aminoorganoxysilane compound and method for producing the same

Abstract

To provide a silane compound that is obtained as a liquid without gelation, that has a greater effect of addition when used as a silane coupling agent, a surface treatment agent, a resin additive, a paint additive, an adhesive agent, or the like, and that generates a smaller amount of low-boiling alcohols when applied to the above applications.SOLUTION: There is provided a cyclic aminoorganoxysilane compound represented by general formula (1) (wherein R1 and R2 are each an unsubstituted divalent hydrocarbon group having 1 to 10 carbon atoms, R3 to R6 are each an unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, R7, R9, R10, and R11 are each a hydrogen atom or an unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, R8 is an unsubstituted divalent hydrocarbon group having 1 to 10 carbon atoms and optionally interposed by an oxygen atom, and a, b, and n are each independently 0, 1, or 2).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a cyclic aminoorganoxysilane compound useful as a silane coupling agent, a surface treatment agent, a resin additive, a paint additive, an adhesive, etc., and a method for producing the same. [Background technology]

[0002] Silane compounds having an amino group are useful as silane coupling agents, surface treatment agents, resin additives, paint additives, adhesives, etc. Known examples of such silane compounds having an amino group 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] However, these silane compounds only have one amino group and one organoxysilyl group per molecule, and when used as silane coupling agents, surface treatment agents, resin additives, paint additives, adhesives, etc., the effects of introducing functional groups may be limited.

[0004] To solve the above problems, Patent Documents 1 to 3 propose tertiary aminosilane compounds having an intramolecular organoxysilyl group. These compounds generate hydroxyl groups in addition to the amino groups they originally contain when reacting with moisture. These hydroxyl groups have a strong interaction with epoxy, urethane, polycarbonate resins, and the like, making the introduction of the functional group more effective. Furthermore, the intramolecular organoxy group does not generate low-boiling alcohols such as methanol or ethanol when reacting with moisture, making them useful as compounds with low environmental impact. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Laid-Open No. 2010-120925 [Patent Document 2] Japanese Patent Application Laid-Open No. 2014-001152 [Patent Document 3] Japanese Patent Application Publication No. 2019-218299 Summary of the Invention [Problem to be solved by the invention]

[0006] The compounds of Patent Documents 1 and 2 each have one amino group, one hydroxyl group that is generated by reaction with water, and one organoxysilyl group as functional groups per molecule. However, in recent years, with the diversification of uses in silane coupling agents, surface treatment agents, resin additives, paint additives, adhesives, etc., there has been a demand for silane compounds with greater additive effects. Therefore, based on Patent Document 1, it has been considered to use a diamine compound such as ethylenediamine as the amine compound, but this would result in gelation of the target product, making it difficult to use in the above-mentioned applications. Furthermore, based on Patent Document 2, it has been considered to use a polyepoxy compound as the epoxy compound, but because the product of the reaction between the epoxy compound and aminosilane contains NH groups, these NH groups further react with the epoxy groups, resulting in gelation, making this also difficult to use in the above-mentioned applications.

[0007] On the other hand, the compound of Patent Document 3 has one amino group, one hydroxyl group generated by reaction with water, and two organoxysilyl groups as functional groups per molecule. However, even in this case, if an attempt is made to increase the number of functional groups by converting the amine compound into a diamine compound or the epoxy compound into a polyepoxy compound in order to obtain more functional groups, gelation may occur, making it difficult to use the compound for the above-mentioned purposes.

[0008] The present invention has been made in view of the above circumstances, and an object of the present invention is to provide a silane compound which can be obtained as a liquid without gelling, which has a greater additive effect when used as a silane coupling agent, surface treatment agent, resin additive, paint additive, adhesive, etc., and which generates less low-boiling alcohol when used in the above applications, and a method for producing the same. [Means for solving the problem]

[0009] As a result of extensive research into achieving the above-mentioned object, the present inventors have discovered that a specific cyclic aminoorganoxysilane compound can be obtained as a liquid without gelation, that the additive effect is greater when used as a silane coupling agent, surface treatment agent, resin additive, paint additive, adhesive, etc., and that the generation of low-boiling alcohols is reduced when used in the above-mentioned applications, and have thus completed the present invention.

[0010] That is, the present invention provides: 1. A cyclic aminoorganoxysilane compound represented by the following general formula (1): [ka] (In the formula, R 1 and R 2 is an unsubstituted divalent hydrocarbon group of 1 to 10 carbon atoms, and R 3 ~R 6 is an unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, and R 7 , R 9 , R 10 and R 11 is a hydrogen atom or an unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, and R 8 represents an unsubstituted divalent hydrocarbon group having 1 to 10 carbon atoms which may contain an oxygen atom, and a, b, and n are 0, 1, or 2. 2. The following general formula (2) [ka] (In the formula, R 1 ~R 6 , a and b have the same meanings as above.) and an aminoorganoxysilane compound represented by the following general formula (3): [ka] (In the formula, R 7 ~R 11 and n have the same meaning as above.) A method for producing a cyclic aminoorganoxysilane compound of 1 by reacting an epoxy compound represented by the formula: to provide. [Effects of the Invention]

[0011] The cyclic aminoorganoxysilane compound of the present invention is obtained as a liquid without gelation and exhibits a greater effect when added than conventionally known compounds, making it useful as a silane coupling agent, surface treatment agent, resin additive, paint additive, adhesive, etc. Another advantage is that when used in the above applications, it generates less low-boiling alcohols. [Brief explanation of the drawings]

[0012] [Figure 1] 1H-NMR spectrum of 1,4-bis[2,2-dimethoxy-6-(3-trimethoxysilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethoxy]butane obtained in Example 1. [Figure 2] 1 is an IR spectrum of 1,4-bis[2,2-dimethoxy-6-(3-trimethoxysilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethoxy]butane obtained in Example 1. [Figure 3] 1H-NMR spectrum of trimethylolpropane tris[2,2-dimethoxy-6-(3-trimethoxysilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethyl]ether obtained in Example 2. [Figure 4]1 is an IR spectrum of trimethylolpropane tris[2,2-dimethoxy-6-(3-trimethoxysilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethyl]ether obtained in Example 2. DETAILED DESCRIPTION OF THE INVENTION

[0013] The cyclic aminoorganoxysilane compound of the present invention is a compound represented by the following general formula (1) (hereinafter referred to as "compound (1)").

[0014] [ka]

[0015] In the above general formula (1), R 1 and R 2 is an unsubstituted divalent hydrocarbon group having 1 to 10 carbon atoms, preferably 1 to 5 carbon atoms, and more preferably 1 to 3 carbon atoms. R 1 The divalent hydrocarbon group may be either linear or branched, and specific examples thereof include alkylene groups such as methylene, ethylene, trimethylene, propylene, 1-methyltrimethylene, isobutylene, tetramethylene, hexamethylene, octamethylene, and decamethylene; arylene groups such as phenylene and methylphenylene; and aralkylene groups such as ethylenephenylene and ethylenephenylenemethylene. Among these, R 1 and R 2 As the alkyl group, an unsubstituted linear alkylene group having 1 to 3 carbon atoms is preferred, and from the viewpoint of easy availability of raw materials, a methylene group, an ethylene group, or a trimethylene group is even more preferred.

[0016] In the above general formula (1), R 3 ~R 6 is 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 3 ~R 6The 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.

[0017] Among these, unsubstituted linear, branched, or cyclic alkyl groups and alkenyl groups having 1 to 10 carbon atoms, and aryl and aralkyl groups having 6 to 10 carbon atoms are preferred, and from the viewpoint of easy availability of raw materials, methyl groups and phenyl groups are even more preferred.

[0018] In the above general formula (1), R 7 , R 9 , R 10 and R 11 is a hydrogen atom or an unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, and specific examples of the unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms include R 3 ~R 6 The same groups as those shown below can be mentioned.

[0019] In the above general formula (1), R 8 is an unsubstituted divalent hydrocarbon group having 1 to 10 carbon atoms which may contain an oxygen atom therebetween, and specific examples of the unsubstituted divalent hydrocarbon group having 1 to 10 carbon atoms which does not contain an oxygen atom therebetween include R 1 and R 2 The same groups as those shown below can be mentioned. When an oxygen atom is present, specific examples include an oxamethylene group, an oxaethylene group, a methyleneoxamethylene group, and an oxaphenylene group.

[0020] Specific examples of compound (1) include 1,7-bis[2,2-dimethoxy-4-(trimethoxysilylmethyl)-1-oxa-4-aza-2-silacyclohexane-6-yl]octane, 1,7-bis[2-methoxy-2-methyl-4-(dimethoxymethylsilylmethyl)-1-oxa-4-aza-2-silacyclohexane-6-yl]octane, 1,7-bis[2,2-dimethyl-4-(methoxydimethylsilylmethyl)-1-oxa-4-aza-2-silacyclohexane-6-yl]octane, 1,7 -Bis[2,2-diethoxy-4-(triethoxysilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-yl]octane, 1,7-bis[2-ethoxy-2-methyl-4-(diethoxymethylsilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-yl]octane, 1,7-bis[2,2-dimethyl-4-(ethoxydimethylsilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-yl]octane, 1,7-bis[2,2-dimethoxy-6-(3 -trimethoxysilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-yl]octane, 1,7-bis[2-methoxy-2-methyl-6-(3-dimethoxymethylsilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-yl]octane, 1,7-bis[2,2-dimethyl-6-(3-methoxydimethylsilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-yl]octane, 1,7-bis[2,2-diethoxy-6-(3-triethoxysilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-yl]octane reaction products of 1,7-dioctadiene epoxide with aminoorganoxysilane compounds, such as 1,7-bis[2-ethoxy-2-methyl-6-(3-diethoxymethylsilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-yl]octane, 1,7-bis[2,2-dimethyl-6-(3-ethoxydimethylsilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-yl]octane, and 1,7-bis[2,2-dimethyl-6-(3-ethoxydimethylsilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-yl]octane;1,2-bis[2,2-dimethoxy-4-(trimethoxysilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-ylmethoxy]ethane, 1,2-bis[2-methoxy-2-methyl-4-(dimethoxymethylsilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-ylmethoxy]ethane, 1,2-bis[2,2-dimethyl-4-(methoxydimethylsilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-ylmethoxy]ethane, 1,2-bis[2,2-diethoxy 4-(triethoxysilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-ylmethoxy]ethane, 1,2-bis[2-ethoxy-2-methyl-4-(diethoxymethylsilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-ylmethoxy]ethane, 1,2-bis[2,2-dimethyl-4-(ethoxydimethylsilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-ylmethoxy]ethane, 1,2-bis[2,2-dimethoxy-6-(3-trimethoxysilyl) 1,2-bis[2-methoxy-2-methyl-6-(3-dimethoxymethylsilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethoxy]ethane, 1,2-bis[2,2-dimethyl-6-(3-methoxydimethylsilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethoxy]ethane, 1,2-bis[2,2-diethoxy-6-(3-triethoxysilylpropyl) -1-oxa-6-aza-2-silacyclooctan-8-ylmethoxy]ethane, 1,2-bis[2-ethoxy-2-methyl-6-(3-diethoxymethylsilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethoxy]ethane, 1,2-bis[2,2-dimethyl-6-(3-ethoxydimethylsilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethoxy]ethane, and other reaction products of ethylene glycol diglycidyl ethers with aminoorganoxysilane compounds;1,4-bis[2,2-dimethoxy-4-(trimethoxysilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-ylmethoxy]butane, 1,4-bis[2-methoxy-2-methyl-4-(dimethoxymethylsilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-ylmethoxy]butane, 1,4-bis[2,2-dimethyl-4-(methoxydimethylsilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-ylmethoxy]butane, 1,4-bis[2,2-diethoxy 4-(triethoxysilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-ylmethoxy]butane, 1,4-bis[2-ethoxy-2-methyl-4-(diethoxymethylsilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-ylmethoxy]butane, 1,4-bis[2,2-dimethyl-4-(ethoxydimethylsilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-ylmethoxy]butane, 1,4-bis[2,2-dimethoxy-6-(3-trimethoxysilyl propyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethoxy]butane, 1,4-bis[2-methoxy-2-methyl-6-(3-dimethoxymethylsilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethoxy]butane, 1,4-bis[2,2-dimethyl-6-(3-methoxydimethylsilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethoxy]butane, 1,4-bis[2,2-diethoxy-6-(3-triethoxysilylpropyl)-1 reaction products of 1,4-butanediol diglycidyl ether with aminoorganoxysilane compounds, such as 1,4-oxa-6-aza-2-silacyclooctan-8-ylmethoxy]butane, 1,4-bis[2-ethoxy-2-methyl-6-(3-diethoxymethylsilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethoxy]butane, and 1,4-bis[2,2-dimethyl-6-(3-ethoxydimethylsilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethoxy]butane;Glycerol tris[2,2-dimethoxy-4-(trimethoxysilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-ylmethyl] ether, glycerol tris[2-methoxy-2-methyl-4-(dimethoxymethylsilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-ylmethyl] ether, glycerol tris[2,2-dimethyl-4-(methoxydimethylsilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-ylmethyl] ether, glycerol tris[2,2-diethoxy-4-(triethoxysilylmethyl)-1 -oxa-4-aza-2-silacyclohexan-6-ylmethyl] ether, glycerol tris[2-ethoxy-2-methyl-4-(diethoxymethylsilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-ylmethyl] ether, glycerol tris[2,2-dimethyl-4-(ethoxydimethylsilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-ylmethyl] ether, glycerol tris[2,2-dimethoxy-6-(3-trimethoxysilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethyl] ether; Glycerol tris[2-methoxy-2-methyl-6-(3-dimethoxymethylsilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethyl] ether, glycerol tris[2,2-dimethyl-6-(3-methoxydimethylsilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethyl] ether, glycerol tris[2,2-diethoxy-6-(3-triethoxysilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethyl] ether glycerol triglycidyl ethers such as glycerol tris[2-ethoxy-2-methyl-6-(3-diethoxymethylsilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethyl] ether and glycerol tris[2,2-dimethyl-6-(3-ethoxydimethylsilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethyl] ether, and reaction products of glycerol triglycidyl ethers with aminoorganoxysilane compounds; trimethylolpropane tris[2,2-dimethoxy-4-(trimethyl Trimethylolpropane tris[2-methoxy-2-methyl-4-(dimethoxymethylsilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-ylmethyl] ether, trimethylolpropane tris[2,2-dimethyl-4-(methoxydimethylsilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-ylmethyl] ether, trimethylolpropane tris[2,2-diethoxy -4-(triethoxysilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-ylmethyl] ether, trimethylolpropane tris[2-ethoxy-2-methyl-4-(diethoxymethylsilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-ylmethyl] ether, trimethylolpropane tris[2,2-dimethyl-4-(ethoxydimethylsilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-ylmethyl] ether, trimethylolpropane tris[2,2-Dimethoxy-6-(3-trimethoxysilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethyl] ether, trimethylolpropane tris[2-methoxy-2-methyl-6-(3-dimethoxymethylsilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethyl] ether, trimethylolpropane tris[2,2-dimethyl-6-(3-methoxydimethylsilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethyl] ether, trimethylol Trimethylolpropane tris[2,2-diethoxy-6-(3-triethoxysilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethyl] ether, Trimethylolpropane tris[2-ethoxy-2-methyl-6-(3-diethoxymethylsilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethyl] ether, Trimethylolpropane tris[2,2-dimethyl-6-(3-ethoxydimethylsilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethyl] ] ether, and reaction products of aminoorganoxysilane compounds; pentaerythritol tetrakis[2,2-dimethoxy-4-(trimethoxysilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-ylmethyl] ether, pentaerythritol tetrakis[2-methoxy-2-methyl-4-(dimethoxymethylsilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-ylmethyl] ether, pentaerythritol tetrakis[2,2-dimethy pentaerythritol tetrakis[2,2-diethoxy-4-(triethoxysilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-ylmethyl]ether, pentaerythritol tetrakis[2-ethoxy-2-methyl-4-(diethoxymethylsilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-ylmethyl]ether, pentaerythritol tetrakis[2,2-Dimethyl-4-(ethoxydimethylsilylmethyl)-1-oxa-4-aza-2-silacyclohexan-6-ylmethyl] ether, pentaerythritol tetrakis[2,2-dimethoxy-6-(3-trimethoxysilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethyl] ether, pentaerythritol tetrakis[2-methoxy-2-methyl-6-(3-dimethoxymethylsilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethyl] ether, pentaerythritol tetrakis[2,2-dimethyl-6-(3-methoxydimethylsilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethyl] Examples of such glycidyl ethers include reaction products of pentaerythritol tetraglycidyl ethers with aminoorganoxysilane compounds, such as pentaerythritol tetrakis[2,2-diethoxy-6-(3-triethoxysilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethyl]ether, pentaerythritol tetrakis[2-ethoxy-2-methyl-6-(3-diethoxymethylsilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethyl]ether, and pentaerythritol tetrakis[2,2-dimethyl-6-(3-ethoxydimethylsilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethyl]ether.

[0021] Next, a method for producing the compound (1) of the present invention will be described. Compound (1) can be produced, for example, by reacting an aminoorganoxysilane compound represented by the following general formula (2) (hereinafter referred to as "compound (2)") with an epoxy compound represented by the following general formula (3) (hereinafter referred to as "compound (3)").

[0022] [ka] (In the formula, R 1 ~R 6 , a and b have the same meanings as above.)

[0023] [ka] (In the formula, R 7 ~R 11 and n have the same meaning as above.)

[0024] Specific examples of compound (2) include bis(alkoxysilylmethyl)amines such as bis(trimethoxysilylmethyl)amine, bis(dimethoxymethylsilylmethyl)amine, bis(methoxydimethylsilylmethyl)amine, bis(triethoxysilylmethyl)amine, bis(diethoxymethylsilylmethyl)amine, and bis(ethoxydimethylsilylmethyl)amine; and bis(alkoxysilylpropyl)amines such as bis(3-trimethoxysilylpropyl)amine, bis(3-dimethoxymethylsilylpropyl)amine, bis(3-methoxydimethylsilylpropyl)amine, bis(3-triethoxysilylpropyl)amine, bis(3-diethoxymethylsilylpropyl)amine, and bis(3-ethoxydimethylsilylpropyl)amine.

[0025] Compound (2) may be commercially available or may be produced by a conventional method, such as reacting an aminoalkylorganoxysilane compound with a haloalkylorganoxysilane compound.

[0026] Specific examples of compound (3) include 1,7-dioctadiene epoxide, ethylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, glycerol triglycidyl ether, trimethylolpropane triglycidyl ether, and pentaerythritol tetraglycidyl ether.

[0027] The compounding ratio of compound (2) to compound (3) is not particularly limited, but from the viewpoints of reactivity and productivity, the compound (2) is preferably 0.2 to 3.0 moles, more preferably 0.5 to 2 moles, per mole of epoxy group in compound (3).

[0028] The reaction temperature for 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.

[0029] Although the above reaction proceeds without a catalyst, a basic catalyst or an acid catalyst can be used to increase the reaction rate. Specific examples of the basic catalyst include sodium hydroxide, potassium hydroxide, sodium methoxide, sodium ethoxide, a methanol solution of sodium methoxide, and an ethanol solution of sodium ethoxide. On the other hand, specific examples of the acid catalyst include inorganic acids such as sulfuric acid, hydrochloric acid, and nitric acid; sulfonic acid compounds such as methanesulfonic acid, benzenesulfonic acid, toluenesulfonic acid, dodecylbenzenesulfonic acid, and trifluoromethanesulfonic acid; and salts thereof. The amount of catalyst used is not particularly limited, but from the viewpoints of reactivity and productivity, it is preferably 0.0001 to 0.2 mol, more preferably 0.001 to 0.1 mol, per 1 mol of epoxy groups in compound (3).

[0030] The above reaction proceeds without a solvent, but a solvent can also be used. Specific 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; chlorinated hydrocarbon solvents such as dichloromethane and chloroform; and alcohol solvents such as methanol, ethanol, 1-propanol, and 2-propanol. These solvents may be used alone or in combination of two or more.

[0031] The target product can be recovered from the reaction mixture obtained as described above by a conventional method such as distillation or distillation off of low boiling point compounds. The obtained target product may be stored or used after diluting with the above-mentioned solvent to prevent gelation. [Example]

[0032] The present invention will be specifically explained below by showing examples, but the present invention is not limited to the following examples.

[0033] [Example 1] A flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer was charged with 136.6 g (0.4 mol) of bis(3-trimethoxysilylpropyl)amine and 28 g of methanol, to which 42.5 g (0.21 mol) of 1,4-butanediol diglycidyl ether was added dropwise over 1 hour at 70-80°C, and the mixture was stirred at that temperature for 10 hours. The reaction solution was concentrated and then subjected to thin-film distillation, yielding 98.5 g of distillate at a wall temperature of 290°C and a pressure of 25 kPa.

[0034] Mass spectrum of the obtained distillate, 1 H-NMR and IR spectra were measured, and the resulting compound was identified as 1,4-bis[2,2-dimethoxy-6-(3-trimethoxysilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethoxy]butane. [Mass Spectrum] m / z 789,639,366,290,121,84 [ 1 H-NMR spectrum (chloroform-d solvent) This is shown in chart form in Figure 1. [IR spectrum] This is shown in chart form in Figure 2.

[0035] [Example 2] A flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer was charged with 204.9 g (0.6 mol) of bis(3-trimethoxysilylpropyl)amine and 42 g of methanol, and 90.7 g (0.21 mol) of trimethylolpropane triglycidyl ether was added dropwise at 70-80°C over 1 hour, followed by stirring at that temperature for 8 hours. The reaction solution was concentrated to obtain 276.9 g of a concentrate. 180 g of toluene was added to the resulting concentrate to obtain a toluene solution.

[0036] The resulting toluene solution 1 H-NMR and IR spectra were measured, and the results confirmed that the compound obtained was trimethylolpropane tris[2,2-dimethoxy-6-(3-trimethoxysilylpropyl)-1-oxa-6-aza-2-silacyclooctan-8-ylmethyl] ether. [ 1 H-NMR spectrum (chloroform-d solvent) This is shown in chart form in Figure 3. [IR spectrum] This is shown in chart form in Figure 4.

Claims

1. A cyclic aminoorganoxysilane compound represented by the following general formula (1): 【Chemical 1】 (In the formula, R 1 and R 2 is an unsubstituted divalent hydrocarbon group having 1 to 10 carbon atoms, and R 3 ~R 6 is an unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, and R 7 , R 9 , R 10 and R 11 is a hydrogen atom or an unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, and R 8 represents an unsubstituted divalent hydrocarbon group having 1 to 10 carbon atoms which may contain an oxygen atom, and a, b, and n each independently represent 0, 1, or 2.

2. The following general formula (2) 【Chemistry 2】 (In the formula, R 1 ~R 6 , a and b have the same meanings as above.) and an aminoorganoxysilane compound represented by the following general formula (3): 【Chemistry 3】 (In the formula, R 7 ~R 11 and n have the same meaning as above.) 2. The method for producing a cyclic aminoorganoxysilane compound according to claim 1, wherein an epoxy compound represented by the formula:

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