Bissilyl compound having silyl group substituted with organoxysilylalkylamino group and method for producing same, and composition and cured product containing same

Abstract

A bissilyl compound having a silyl group substituted with an organoxysilylalkylamino group represented by general formula (1) can rapidly form a film without a catalyst and yields a coating film resistant to cracks and whitening. (R1, R2, R4-R7, R9, and R10 represent an unsubstituted C1-10 monovalent hydrocarbon group, R6 and R7 may bond to each other to form a C2-10 ring structure together with nitrogen atoms, the ring structure may contain at least one element selected from the group consisting of O and N in addition to the nitrogen atoms, R3 and R8 represent a C2-10 divalent hydrocarbon group that may contain at least one element selected from O, N, S, and Si, a represents 0, 1, or 2, l and m each represent 0, 1, or 2, n represents 1, 2, or 3, and p represents 0, 1, or 2.)

Description

Bissilyl compound having a silyl group substituted with an organoxysilylalkylamino group, method for producing the same, and composition and cured product containing the same

[0001] The present invention relates to a bissilyl compound having a silyl group substituted with an organoxysilylalkylamino group, a method for producing the same, and a composition and cured product containing the same.

[0002] Organoxysilane compounds are useful as silane coupling agents, surface treatment agents, resin additives, paint additives, adhesives, coating agents, primers, etc. Known examples of such organoxysilane compounds include tetraorganoxysilane compounds such as tetramethoxysilane and tetraethoxysilane, and triorganoxysilane compounds such as octyltrimethoxysilane, 3-aminopropyltrimethoxysilane, and 3-methacryloxypropyltrimethoxysilane. These organoxysilane compounds, each having one silicon atom in the molecule, have a maximum of four organoxy groups that act as reaction sites when used in the above applications.

[0003] Furthermore, 1,2-bis(trimethoxysilyl)ethane is known as a compound that has many reactive sites and is thought to have a large effect when added. This compound has two silicon atoms in its molecule and therefore six organoxy groups.

[0004] These organoxysilane compounds having many organoxy groups may gel when a hydrolysis condensation reaction occurs during use. To solve this problem, organoxysilane compounds in which dialkylamino groups (secondary amino groups) are partially bonded to silyl groups have been proposed (Patent Document 1).

[0005] JP 2017-141180 A

[0006] When organoxysilane compounds are used, particularly as coating agents or primers, there is a problem that film formation is extremely slow unless a catalyst such as an acid-base compound, a metal compound, etc. In addition, when a compound containing many organoxy groups is used to form a film with a thickness of several tens of micrometers or more using a catalyst, cracks tend to occur as the hydrolysis condensation reaction progresses, and the crosslink density is too high, which causes the film to easily turn white.

[0007] In relation to these points, the organoxysilane compound described in Patent Document 1 generates secondary amines as the hydrolysis condensation reaction proceeds, and these amines act as basic catalysts, resulting in the formation of a coating. Therefore, coating formation is possible without the addition of a catalyst. However, silyl groups partially bonded to dialkylamino groups are not only less susceptible to hydrolysis condensation due to the influence of steric hindrance, but also the resulting dialkylamines are low molecular weight and easily volatile, so there is a need to shorten the coating formation time. In addition, because organoxy groups and amino groups are eliminated by the hydrolysis condensation reaction, cracks are likely to occur as the hydrolysis condensation reaction proceeds, just like compounds containing a large number of organoxy groups, and the problem of the coating being prone to whitening due to excessive crosslink density remains.

[0008] The present invention has been made in view of the above circumstances, and aims to provide a bissilyl compound that can rapidly form a coating without a catalyst and that gives a coating that is less susceptible to cracking and whitening, a method for producing the same, and a composition and cured product containing the same.

[0009]

[0003] As a result of intensive research aimed at solving the above problems, the present inventors have found that by having an organoxysilylalkylamino group on a silicon atom, the influence of steric hindrance is small, the silyl group substituted with the organoxysilylalkylamino group is rapidly hydrolyzed, and the primary aminoalkylorganoxysilane compound produced by the hydrolysis acts as a catalyst and reactant to promote a hydrolysis condensation reaction with a bissilyl compound. As a result, they have found a bissilyl compound having a silyl group substituted with an organoxysilylalkylamino group that can rapidly form a film without a catalyst, and have completed the present invention.

[0010] That is, the present invention provides: 1. a bissilyl compound having a silyl group substituted with an organoxysilylalkylamino group, represented by the following general formula (1): (In the formula, R 1 , R 2 , R 4 ~R 7 , R 9 and R 10 each independently represents an unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, and R 6 and R 7 may be bonded to each other to form a ring structure having 2 to 10 carbon atoms together with the nitrogen atom to which they are bonded, and the ring structure may contain at least one element selected from the group consisting of O and N in addition to the nitrogen atom in a part of the ring; R 3 and R 8 each independently represent a divalent hydrocarbon group having 2 to 10 carbon atoms which may contain at least one element selected from the group consisting of O, N, S, and Si, a represents 0, 1, or 2, l and m each represent 0, 1, or 2, n represents 1, 2, or 3, and p represents 0, 1, or 2. 2. A composition comprising a bissilyl compound having a silyl group substituted with an organoxysilylalkylamino group of formula 1, and an amino group-containing organoxysilane compound represented by the following general formula (2): (In the formula, R 8 ~R 10 and p have the same meanings as above.) 3. A composition comprising a bissilyl compound having a silyl group substituted with an organoxysilylalkylamino group as set forth in 1, and an aprotic solvent; 4. A composition according to 2, further comprising an aprotic solvent; 5. A compound represented by general formula (2): (In the formula, R 8 ~R 10 and p have the same meanings as above), and a primary aminoalkylorganoxysilane compound represented by the following general formula (3): (In the formula, R 1 ~R 75. A method for producing a bissilyl compound having a silyl group substituted with an organoxysilylalkylamino group according to claim 1, which comprises a step of subjecting a bissilyl compound represented by the formula (I) to an amine exchange reaction in the presence of an acidic compound having a pKa of 4 to 12 and an aprotic polar solvent; 6. A method for producing a bissilyl compound having a silyl group substituted with an organoxysilylalkylamino group of 5, which further comprises a step of neutralizing the acidic compound with a solid basic compound; 7. A method for producing a bissilyl compound having a silyl group substituted with an organoxysilylalkylamino group of 5 or 6, wherein the acidic compound having a pKa of 4 to 12 is an amine salt; 8. A method for producing a bissilyl compound having a silyl group substituted with an organoxysilylalkylamino group of 5 or 6, wherein the aprotic polar solvent is a nitrile compound; 9. A cured product obtained by curing the compound of 1 or the composition of 2.

[0011] The bissilyl compound of the present invention, which has a silyl group substituted with an organoxysilylalkylamino group, can rapidly form a coating without the addition of a separate catalyst. In addition, the resulting coating exhibits high hardness without cracking or whitening.

[0012] 1 shows the IR spectrum of Compound 1 obtained in Example 1. 1 1 shows the H-NMR spectrum of Compound 2 obtained in Example 2. 2 shows the IR spectrum of Compound 2 obtained in Example 2. 1 1 shows the H-NMR spectrum of Compound 3 obtained in Example 3. 2 shows the IR spectrum of Compound 3 obtained in Example 3. 1 1 shows the H-NMR spectrum of Compound 4 obtained in Example 4. 2 shows the IR spectrum of Compound 4 obtained in Example 4. 1 1 shows the H-NMR spectrum of Compound 5 obtained in Example 5. 2 shows the IR spectrum of Compound 5 obtained in Example 5. 1 1 shows the H-NMR spectrum of Compound 6 obtained in Example 6. 2 shows the IR spectrum of Compound 6 obtained in Example 6. 11 shows the H-NMR spectrum of Compound 7 obtained in Example 7. 1 shows the IR spectrum of Compound 7 obtained in Example 7. 1 1 shows the H-NMR spectrum of compound 8 obtained in Example 8. 2 shows the IR spectrum of compound 8 obtained in Example 8. 1 FIG. 1 shows a H-NMR spectrum.

[0013] [1] Bissilyl compound having a silyl group substituted with an organoxysilylalkylamino group The bissilyl compound of the present invention having a silyl group substituted with an organoxysilylalkylamino group (hereinafter referred to as "compound (1)") is represented by the following general formula (1):

[0014]

[0015] In general formula (1), R 1 , R 2 , R 4 ~R 7 , R 9 and R 10 are each independently an unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, and more preferably 1 to 3 carbon atoms. 1 , R 2 , R 4 ~R 7 , R 9 and R 10 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, and decyl groups; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, neopentyl, thexyl, and 2-ethylhexyl groups; cyclic alkyl groups such as cyclopentyl and cyclohexyl groups; alkenyl groups such as vinyl, allyl, 1-propenyl, butenyl, and pentenyl groups; aryl groups such as phenyl and tolyl groups; and aralkyl groups such as benzyl and phenethyl groups. 1 , R 2 , R 4 , R 5 , R 9 , R10 is preferably a methyl, ethyl, isopropyl, or phenyl group in view of ease of raw material procurement, and R 6 and R 7 In terms of ease of procurement of raw materials and shortening the drying time to touch, methyl and ethyl groups are preferred.

[0016] Also, R 6 and R 7 may be bonded to each other to form a ring structure having 2 to 10 carbon atoms together with the nitrogen atom to which they are bonded, and this ring structure may contain, in addition to the nitrogen atom, at least one element selected from the group consisting of O and N as part of the ring. Specific examples of such ring structures include pyrrolidine, piperidine, piperazine, N-methylpiperazine, and morpholine rings.

[0017] In general formula (1), R 3 and R 8 R are each independently a divalent hydrocarbon group having 2 to 10 carbon atoms, preferably 2 to 8 carbon atoms, and more preferably 2 to 6 carbon atoms, which may contain at least one element selected from the group consisting of O, N, S, and Si. 3 and R 8 The divalent hydrocarbon group may be linear, branched, or cyclic, and specific examples thereof include linear alkylene groups such as ethylene, trimethylene, tetramethylene, hexamethylene, octamethylene, and decylene groups; branched alkylene groups such as methyltrimethylene and methyltetramethylene groups; cyclic alkylene groups such as cyclohexylene and methylenecyclohexylenemethylene groups; linear alkenylene groups such as butenylene, hexenylene, and octenylene groups; branched alkenylene groups such as isobutenylene groups; arylene groups such as phenylene; and aralkylene groups such as methylenephenylene and methylenephenylenemethylene groups. Among these, R 3 and R 8 In terms of ease of procurement of raw materials and hardness of the resulting coating, a linear alkylene group or aralkylene group having 2 to 8 carbon atoms is preferred.

[0018] Also, R 3 and R 8When the divalent hydrocarbon group contains at least one element selected from the group consisting of O, N, S, and Si, examples of the divalent hydrocarbon group include an alkyleneoxyalkylene group, an alkyleneaminoalkylene group, an alkylenethioalkylene group, and an alkylenedialkylsilylalkylene group.

[0019] Especially R 3 When contains Si, it may have a polydialkylsiloxanyl group represented by the following general formula (4) or a group containing a cyclic siloxane structure represented by the following general formula (5).

[0020]

[0021] In general formula (4), R 11 are each independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, and more preferably 1 to 3 carbon atoms. 11 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, and decyl groups; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, neopentyl, thexyl, and 2-ethylhexyl groups; cyclic alkyl groups such as cyclopentyl and cyclohexyl groups; alkenyl groups such as vinyl, allyl, propenyl, butenyl, and pentenyl groups; aryl groups such as phenyl and tolyl groups; and aralkyl groups such as benzyl and phenethyl groups. 11 From the viewpoint of ease of procurement of raw materials, a linear alkyl group, an alkenyl group, or an aryl group is preferred.

[0022] In addition, R 11 In the monovalent hydrocarbon group, some or all of the hydrogen atoms may be substituted with fluorine atoms. Specific examples of the monovalent hydrocarbon group substituted with fluorine atoms include fluoroalkyl groups such as (3,3,3-trifluoro)propyl, (3,3,4,4,5,5,6,6,6)nonafluorohexyl, and (3,3,4,4,5,5,6,6,7,7,8,8,8)-tridecafluorooctyl.

[0023] In general formula (4), q represents any integer, but is preferably an integer of 0 to 100, more preferably 0 to 80, and even more preferably 0 to 40, from the viewpoint of the hardness of the coating.

[0024] In general formula (5), R 12 are each independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, and more preferably 1 to 3 carbon atoms. 12 The monovalent hydrocarbon group of R 11 The same substituents as those mentioned above can be mentioned.

[0025] In general formula (5), two of A are each independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, and more preferably 1 to 3 carbon atoms, an organoxy group, a trialkoxysilylalkyl group, an alkyldialkoxysilylalkyl group, or a dialkylalkoxysilylalkyl group, and the remaining two of A are substituted or unsubstituted divalent hydrocarbon groups having 1 to 9 carbon atoms, preferably 1 to 6 carbon atoms, and more preferably 1 to 3 carbon atoms (with the total number of carbon atoms being 2 to 10), and these are R 3 The monovalent hydrocarbon group is R 11 The divalent hydrocarbon group includes the same substituents as those shown in R 3 In addition to the groups exemplified by R, a methylene group can also be mentioned. 11 , R 12 and R among A 3 The number of carbon atoms in the two groups that are not bonded to the silicon atoms on both sides of R 3 is not included in the carbon number.

[0026] Specific examples of A as an organoxy group include alkoxy groups having 1 to 3 carbon atoms, such as methoxy, ethoxy, propoxy, and isopropoxy. Specific examples of A as a trialkoxysilylalkyl group include trimethoxysilylethyl, trimethoxysilylpropyl, trimethoxysilylhexyl, trimethoxysilyloctyl, triethoxysilylethyl, triethoxysilylpropyl, triethoxysilylhexyl, and triethoxysilyloctyl. Specific examples of A as an alkyldialkoxysilylalkyl group include methyldimethoxysilylethyl, methyldimethoxysilylpropyl, methyldimethoxysilylhexyl, methyldimethoxysilyloctyl, methyldiethoxysilylethyl, methyldiethoxysilylpropyl, methyldiethoxysilylhexyl, methyldiethoxysilyloctyl, methoxymethyldimethoxysilylethyl, ethoxymethyldiethoxysilylethyl, and phenyldimethoxysilyl. Specific examples of when A is a dialkylalkoxysilylalkyl group include dimethylmethoxysilylethyl, methylphenylmethoxysilylethyl, dimethylethoxysilylethyl, methylphenylethoxysilylethyl, dimethylmethoxysilylhexyl, dimethylmethoxysilyloctyl, dimethylethoxysilylhexyl, and dimethylethoxysilyloctyl groups.

[0027] In general formula (5), r represents any integer, preferably an integer of 0 to 5, more preferably 1 to 5, and even more preferably 1 to 3. If r is too large, there is a possibility that the formed coating will not achieve sufficient hardness.

[0028] In general formula (1), a represents 0, 1, or 2, and is preferably 0 or 1 from the viewpoints of the curing time of the product and the hardness of the resulting coating. 1 and m each represent 0, 1, or 2, and is preferably 0 or 1 from the viewpoints of the curability of the product and the hardness of the resulting coating. n represents 1, 2, or 3, and is preferably 1 or 2 from the viewpoints of the curability of the product and the hardness of the resulting coating. p represents 0, 1, or 2, and is preferably 0 or 1 from the viewpoints of the curability of the product and the hardness of the resulting coating.

[0029] Specific examples of compound (1) include 1-methyldimethoxysilyl-2-(dimethylamino)(trimethoxysilylpropylamino)methylsilylethylene, 1-methyldimethoxysilyl-2-(dimethylamino)(methyldimethoxysilylpropylamino)methylsilylethylene, 1-methyldimethoxysilyl-2-(dimethylamino)(triethoxysilylpropylamino)methylsilylethylene, 1-methyldimethoxysilyl-2-(dimethylamino)(methyldiethoxysilylpropylamino)methylsilylethylene, 1- Methyldimethoxysilyl-6-(dimethylamino)(trimethoxysilylpropylamino)methylsilylhexane, 1-methyldimethoxysilyl-6-(dimethylamino)(methyldimethoxysilylpropylamino)methylsilylhexane, 1-methyldimethoxysilyl-6-(dimethylamino)(triethoxysilylpropylamino)methylsilylhexane, 1-methyldimethoxysilyl-6-(dimethylamino)(methyldiethoxysilylpropylamino)methylsilylhexane, 1-methyldimethoxysilyl-8-(dimethylamino) 1-methyldimethoxysilyl-8-(dimethylamino)(trimethoxysilylpropylamino)methylsilyl octane, 1-methyldimethoxysilyl-8-(dimethylamino)(methyldimethoxysilylpropylamino)methylsilyl octane, 1-methyldimethoxysilyl-8-(dimethylamino)(triethoxysilylpropylamino)methylsilyl octane, 1-methyldimethoxysilyl-8-(dimethylamino)(methyldiethoxysilylpropylamino)methylsilyl octane, 1-methyldimethoxysilyl-2-(diethylamino)(trimethoxysilylpropylamino)methylsilyl octane 1-methyldimethoxysilyl-2-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylethylene, 1-methyldimethoxysilyl-2-(diethylamino)(triethoxysilylpropylamino)methylsilylethylene, 1-methyldimethoxysilyl-2-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethylene, 1-methyldimethoxysilyl-6-(diethylamino)(trimethoxysilylpropylamino)methylsilylhexane,1-methyldimethoxysilyl-6-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylhexane, 1-methyldimethoxysilyl-6-(diethylamino)(triethoxysilylpropylamino)methylsilylhexane, 1-methyldimethoxysilyl-6-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylhexane, 1-methyldimethoxysilyl-8-(diethylamino)(trimethoxysilylpropylamino)methylsilyloctane, 1-methyldimethoxysilyl-8-(di 1-methyldimethoxysilyl-8-(diethylamino)(triethoxysilylpropylamino)methylsilyloctane, 1-methyldimethoxysilyl-8-(diethylamino)(methyldiethoxysilylpropylamino)methylsilyloctane, 1-methyldimethoxysilyl-2-(4-methylpiperazin-1-yl)(trimethoxysilylpropylamino)methylsilylethylene, 1-methyldimethoxysilyl-2-(4-methylpiperazin-1-yl)(trimethoxysilylpropylamino)methylsilylethylene 1-methyldimethoxysilyl-2-(4-methylpiperazin-1-yl)(triethoxysilylpropylamino)methylsilylethylene, 1-methyldimethoxysilyl-2-(4-methylpiperazin-1-yl)(methyldiethoxysilylpropylamino)methylsilylethylene, 1-methyldimethoxysilyl-6-(4-methylpiperazin-1-yl)(trimethoxysilylpropylamino)methylsilylhexane, 1-methyldimethoxysilyl- 6-(4-methylpiperazin-1-yl)(methyldimethoxysilylpropylamino)methylsilylhexane, 1-methyldimethoxysilyl-6-(4-methylpiperazin-1-yl)(triethoxysilylpropylamino)methylsilylhexane, 1-methyldimethoxysilyl-6-(4-methylpiperazin-1-yl)(methyldiethoxysilylpropylamino)methylsilylhexane, 1-methyldimethoxysilyl-8-(4-methylpiperazin-1-yl)(trimethoxysilylpropylamino)methylsilyloctane,1-Methyldimethoxysilyl-8-(4-methylpiperazin-1-yl)(methyldimethoxysilylpropylamino)methylsilyloctane, 1-methyldimethoxysilyl-8-(4-methylpiperazin-1-yl)(triethoxysilylpropylamino)methylsilyloctane, 1-methyldimethoxysilyl-8-(4-methylpiperazin-1-yl)(methyldiethoxysilylpropylamino)methylsilyloctane, 1-trimethoxysilyl-2-(dimethylamino)(trimethoxysilylpropylamino)methylsilylethylene, 1-trimethoxysilyl -2-(dimethylamino)(triethoxysilylpropylamino)methylsilylethylene, 1-trimethoxysilyl-2-(dimethylamino)(methyldiethoxysilylpropylamino)methylsilylethylene, 1-trimethoxysilyl-6-(dimethylamino)(trimethoxysilylpropylamino)methylsilylhexane, 1-trimethoxysilyl-6-(dimethylamino)(methyldimethoxysilylpropylamino)methylsilylhexane, 1-trimethoxysilyl-6-(dimethylamino)(triethoxysilylpropylamino)methylsilylhexane, 1-trimethoxysilyl-6-(dimethylamino)(methyldiethoxysilylpropylamino)methylsilylhexane, 1-trimethoxysilyl-8-(dimethylamino)(trimethoxysilylpropylamino)methylsilyloctane, 1-trimethoxysilyl-8-(dimethylamino)(methyldimethoxysilylpropylamino)methylsilyloctane, 1-trimethoxysilyl-8-(dimethylamino)(triethoxysilylpropylamino)methylsilyloctane, 1-trimethoxysilyl-8-(dimethylamino)(methyldiethoxysilylpropylamino)methylsilyloctane, 1-trimethoxysilyl-2-(diethylamino)(trimethoxysilylpropylamino)methylsilylethylene, 1-trimethoxysilyl-2-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylethylene, 1-trimethoxysilyl-2-(diethylamino)(triethoxysilylpropylamino)methylsilylethylene,1-trimethoxysilyl-2-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethylene, 1-trimethoxysilyl-6-(diethylamino)(trimethoxysilylpropylamino)methylsilylhexane, 1-trimethoxysilyl-6-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylhexane, 1-trimethoxysilyl-6-(diethylamino)(triethoxysilylpropylamino)methylsilylhexane, 1-trimethoxysilyl-6-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylhexane 1-trimethoxysilyl-8-(diethylamino)(trimethoxysilylpropylamino)methylsilylhexane, 1-trimethoxysilyl-8-(diethylamino)(trimethoxysilylpropylamino)methylsilyloctane, 1-trimethoxysilyl-8-(diethylamino)(methyldimethoxysilylpropylamino)methylsilyloctane, 1-trimethoxysilyl-8-(diethylamino)(triethoxysilylpropylamino)methylsilyloctane, 1-trimethoxysilyl-8-(diethylamino)(methyldiethoxysilylpropylamino)methylsilyloctane, 1-trimethoxysilyl-8-(diethylamino)(methyldiethoxysilylpropylamino)methylsilyloctane 1-trimethoxysilyl-2-(4-methylpiperazin-1-yl)(trimethoxysilylpropylamino)methylsilylethylene, 1-trimethoxysilyl-2-(4-methylpiperazin-1-yl)(methyldimethoxysilylpropylamino)methylsilylethylene, 1-trimethoxysilyl-2-(4-methylpiperazin-1-yl)(triethoxysilylpropylamino)methylsilylethylene, 1-trimethoxysilyl-2-(4-methylpiperazin-1-yl)(methyldiethoxysilylpropylamino)methylsilylethylene, 1-trimethoxysilyl-2-(4-methylpiperazin-1-yl)(methyldiethoxysilylpropylamino)methylsilylethylene, trimethoxysilyl-6-(4-methylpiperazin-1-yl)(trimethoxysilylpropylamino)methylsilylhexane, 1-trimethoxysilyl-6-(4-methylpiperazin-1-yl)(methyldimethoxysilylpropylamino)methylsilylhexane, 1-trimethoxysilyl-6-(4-methylpiperazin-1-yl)(triethoxysilylpropylamino)methylsilylhexane, 1-trimethoxysilyl-6-(4-methylpiperazin-1-yl)(methyldiethoxysilylpropylamino)methylsilylhexane,1-trimethoxysilyl-8-(4-methylpiperazin-1-yl)(trimethoxysilylpropylamino)methylsilyl octane, 1-trimethoxysilyl-8-(4-methylpiperazin-1-yl)(methyldimethoxysilylpropylamino)methylsilyl octane, 1-trimethoxysilyl-8-(4-methylpiperazin-1-yl)(triethoxysilylpropylamino)methylsilyl octane, 1-trimethoxysilyl-8-(4-methylpiperazin-1-yl)(methyldiethoxysilylpropylamino)methylsilyl octane, 1- Trimethoxysilyl-2-(diethylamino)(trimethoxysilylpropylamino)methylsilylethylene, 1-trimethoxysilyl-2-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylethylene, 1-trimethoxysilyl-2-(diethylamino)(triethoxysilylpropylamino)methylsilylethylene, 1-trimethoxysilyl-2-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethylene, 1-trimethoxysilyl-6-(diethylamino)(trimethoxysilylpropyl amino)methylsilylhexane, 1-trimethoxysilyl-6-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylhexane, 1-trimethoxysilyl-6-(diethylamino)(triethoxysilylpropylamino)methylsilylhexane, 1-trimethoxysilyl-6-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylhexane, 1-trimethoxysilyl-8-(diethylamino)(trimethoxysilylpropylamino)methylsilyloctane, 1-trimethoxysilyl-8-(diethylamino)(trimethoxysilylpropylamino)methylsilyloctane amino)(methyldimethoxysilylpropylamino)methylsilyl octane, 1-trimethoxysilyl-8-(diethylamino)(triethoxysilylpropylamino)methylsilyl octane, 1-trimethoxysilyl-8-(diethylamino)(methyldiethoxysilylpropylamino)methylsilyl octane, 1-triethoxysilyl-2-(diethylamino)(trimethoxysilylpropylamino)methylsilyl ethylene, 1-triethoxysilyl-2-(diethylamino)(methyldimethoxysilylpropylamino)methylsilyl ethylene,1-triethoxysilyl-2-(diethylamino)(triethoxysilylpropylamino)methylsilylethylene, 1-triethoxysilyl-2-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethylene, 1-triethoxysilyl-6-(diethylamino)(trimethoxysilylpropylamino)methylsilylhexane, 1-triethoxysilyl-6-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylhexane, 1-triethoxysilyl-6-(diethylamino)(triethoxy 1-triethoxysilyl-6-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylhexane, 1-triethoxysilyl-8-(diethylamino)(trimethoxysilylpropylamino)methylsilyloctane, 1-triethoxysilyl-8-(diethylamino)(methyldimethoxysilylpropylamino)methylsilyloctane, 1-triethoxysilyl-8-(diethylamino)(triethoxysilylpropylamino)methylsilyloctane, 1-triethoxysilyl-8-(diethylamino)(triethoxysilylpropylamino)methylsilyloctane, silyl-8-(diethylamino)(methyldiethoxysilylpropylamino)methylsilyloctane, 1-methyldiethoxysilyl-2-(diethylamino)(trimethoxysilylpropylamino)methylsilylethylene, 1-methyldiethoxysilyl-2-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylethylene, 1-methyldiethoxysilyl-2-(diethylamino)(triethoxysilylpropylamino)methylsilylethylene, 1-methyldiethoxysilyl-2-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethylene 1-methyldiethoxysilyl-6-(diethylamino)(trimethoxysilylpropylamino)methylsilylethylene, 1-methyldiethoxysilyl-6-(diethylamino)(trimethoxysilylpropylamino)methylsilylhexane, 1-methyldiethoxysilyl-6-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylhexane, 1-methyldiethoxysilyl-6-(diethylamino)(triethoxysilylpropylamino)methylsilylhexane, 1-methyldiethoxysilyl-6-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylhexane,1-methyldiethoxysilyl-8-(diethylamino)(trimethoxysilylpropylamino)methylsilyloctane, 1-methyldiethoxysilyl-8-(diethylamino)(methyldimethoxysilylpropylamino)methylsilyloctane, 1-methyldiethoxysilyl-8-(diethylamino)(triethoxysilylpropylamino)methylsilyloctane, 1-methyldiethoxysilyl-8-(diethylamino)(methyldiethoxysilylpropylamino)methylsilyloctane, trimethoxysilylmethyl-(diethylamino) (Trimethoxysilylpropylamino)methyl ethyl sulfide, trimethoxysilylmethyl-(diethylamino)(methyldimethoxysilylpropylamino)methyl ethyl sulfide, trimethoxysilylmethyl-(diethylamino)(triethoxysilylpropylamino)methyl ethyl sulfide, trimethoxysilylmethyl-(diethylamino)(methyldiethoxysilylpropylamino)methyl ethyl sulfide, trimethoxysilylpropyl(diethylamino)(trimethoxysilylpropylamino)methyl ethyl sulfide, Trimethoxysilylpropyl(diethylamino)(methyldimethoxysilylpropylamino)methyl ethyl sulfide, trimethoxysilylpropyl(diethylamino)(triethoxysilylpropylamino)methyl ethyl sulfide, trimethoxysilylpropyl(diethylamino)(methyldiethoxysilylpropylamino)methyl ethyl sulfide, methyldimethoxysilylpropyl(diethylamino)(trimethoxysilylpropylamino)methyl ethyl sulfide, methyldimethoxysilylpropyl(diethylamino)(methyldimethoxysilylpropylamino)methyl ethyl sulfide, methyldimethoxysilylpropyl(diethylamino)(methyldiethoxysilylpropylamino)methyl ethyl sulfide, trimethoxysilyl octyl(diethylamino)(trimethoxysilylpropylamino)methyl ethyl sulfide, trimethoxysilyl octyl(diethylamino)(methyldimethoxysilylpropylamino)methyl ethyl sulfide,Trimethoxysilyl octyl(diethylamino)(triethoxysilylpropylamino)methyl ethyl sulfide, trimethoxysilyl octyl(diethylamino)(methyldiethoxysilylpropylamino)methyl ethyl sulfide, 1-trimethoxysilylethyldimethylsilyl-2-(diethylamino)(trimethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-trimethoxysilylethyldimethylsilyl-3-(diethylamino)(trimethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-trimethoxysilylethyldimethylsilyl-4-(diethylamino)(trimethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-trimethoxysilylethyldimethylsilyl-2-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-trimethoxysilylethyldimethylsilyl-3-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-trimethoxysilylethyldimethylsilyl-4-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-trimethoxysilylethyldimethylsilyl-2-(diethylamino)(triethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-trimethoxysilylethyldimethylsilyl-3-(diethylamino)(triethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1 -trimethoxysilylethyldimethylsilyl-4-(diethylamino)(triethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-trimethoxysilylethyldimethylsilyl-2-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-trimethoxysilylethyldimethylsilyl-3-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-trimethoxysilylethyldimethylsilyl-4-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene,1-methyldimethoxysilylethyldimethylsilyl-2-(diethylamino)(trimethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-methyldimethoxysilylethyldimethylsilyl-3-(diethylamino)(trimethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-methyldimethoxysilylethyldimethylsilyl-4-(diethylamino)(trimethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-methyldimethoxysilylethyldimethylsilyl-2-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-methyldimethoxysilylethyldimethylsilyl-3-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-methyldimethoxysilylethyldimethylsilyl-4-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-methyldimethoxysilylethyldimethylsilyl-2-(diethylamino)(trimethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene 1-methyldimethoxysilylethyldimethylsilyl-3-(diethylamino)(triethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-methyldimethoxysilylethyldimethylsilyl-4-(diethylamino)(triethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-methyldimethoxysilylethyldimethylsilyl-2-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene methylsilylethyldimethylsilylbenzene, 1-methyldimethoxysilylethyldimethylsilyl-3-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-methyldimethoxysilylethyldimethylsilyl-4-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-trimethoxysilylethyl-3-(diethylamino)(trimethoxysilylpropylamino)methylsilylethyl-1,1,3,3-tetramethyldisiloxane,1-trimethoxysilylethyl-3-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylethyl-1,1,3,3-tetramethyldisiloxane, 1-trimethoxysilylethyl-3-(diethylamino)(triethoxysilylpropylamino)methylsilylethyl-1,1,3,3-tetramethyldisiloxane, 1-trimethoxysilylethyl-3-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethyl-1,1,3,3-tetramethyldisiloxane, 1-trimethoxy Silylethyl-9-(diethylamino)(trimethoxysilylpropylamino)methylsilylethyl-1,1,3,3,5,5,7,7,9,9-decamethylpentasiloxane, 1-trimethoxysilylethyl-9-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylethyl-1,1,3,3,5,5,7,7,9,9-decamethylpentasiloxane, 1-trimethoxysilylethyl-9-(diethylamino)(triethoxysilylpropylamino)methylsilylethyl-1,1,3,3,5,5,7 ,7,9,9-decamethylpentasiloxane, 1-trimethoxysilylethyl-9-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethyl-1,1,3,3,5,5,7,7,9,9-decamethylpentasiloxane, (α-trimethoxysilylethyl-ω-(diethylamino)(trimethoxysilylpropylamino)methylsilylethyl-polydimethylpolysiloxane, (α-trimethoxysilylethyl-ω-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylethyl- Polydimethylpolysiloxane, (α-trimethoxysilylethyl-ω-(diethylamino)(triethoxysilylpropylamino)methylsilylethyl-polydimethylpolysiloxane, (α-trimethoxysilylethyl-ω-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethyl-polydimethylpolysiloxane, 1-trimethoxysilylethyl-3-(diethylamino)(trimethoxysilylpropylamino)methylsilylethyl-1,3,5,5,7,7-hexamethylcyclotetrasiloxane,1-trimethoxysilylethyl-5-(diethylamino)(trimethoxysilylpropylamino)methylsilylethyl-1,3,3,5,7,7-hexamethylcyclotetrasiloxane, 1-trimethoxysilylethyl-3-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylethyl-1,3,5,5,7,7-hexamethylcyclotetrasiloxane, 1-trimethoxysilylethyl-5-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylethyl-1,3,3,5,7,7-hexamethylcyclotetrasiloxane hexamethylcyclotetrasiloxane, 1-trimethoxysilylethyl-3-(diethylamino)(triethoxysilylpropylamino)methylsilylethyl-1,3,5,5,7,7-hexamethylcyclotetrasiloxane, 1-trimethoxysilylethyl-5-(diethylamino)(triethoxysilylpropylamino)methylsilylethyl-1,3,3,5,7,7-hexamethylcyclotetrasiloxane, 1-trimethoxysilylethyl-3-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethyl- 1,3,5,5,7,7-Hexamethylcyclotetrasiloxane, 1-trimethoxysilylethyl-5-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethyl-1,3,3,5,7,7-hexamethylcyclotetrasiloxane, 1-trimethoxysilylethyl-3-(diethylamino)(trimethoxysilylpropylamino)methylsilylethyl-5,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilylethyl-5-(diethylamino)(trimethoxysilylpropylamino)methylsilylethyl- 1-trimethoxysilylethyl-3-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylethyl-3,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilylethyl-3-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylethyl-5,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilylethyl-5-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylethyl-3,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane,1-trimethoxysilylethyl-3-(diethylamino)(triethoxysilylpropylamino)methylsilylethyl-5,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilylethyl-5-(diethylamino)(triethoxysilylpropylamino)methylsilylethyl-3,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilylethyl-3-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethyl-5,7-di Propyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilylethyl-5-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethyl-3,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilyloctyl-3-(diethylamino)(trimethoxysilylpropylamino)methylsilylethyl-1,3,5,5,7,7-hexamethylcyclotetrasiloxane, 1-trimethoxysilyloctyl-5-(diethylamino)(trimethoxysilylpropylamino)methylsilylethyl-1,3,5,5,7,7-hexamethylcyclotetrasiloxane 1-trimethoxysilyl octyl-3-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylethyl-1,3,5,5,7,7-hexamethylcyclotetrasiloxane, 1-trimethoxysilyl octyl-5-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylethyl-1,3,3,5,7,7-hexamethylcyclotetrasiloxane, 1-trimethoxysilyl octyl -3-(diethylamino)(triethoxysilylpropylamino)methylsilylethyl-1,3,5,5,7,7-hexamethylcyclotetrasiloxane, 1-trimethoxysilyloctyl-5-(diethylamino)(triethoxysilylpropylamino)methylsilylethyl-1,3,3,5,7,7-hexamethylcyclotetrasiloxane, 1-trimethoxysilyloctyl-3-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethyl-1,3,5,5,7,7-hexamethylcyclotetrasiloxane,1-trimethoxysilyl octyl-5-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethyl-1,3,3,5,7,7-hexamethylcyclotetrasiloxane, 1-trimethoxysilyl octyl-3-(diethylamino)(trimethoxysilylpropylamino)methylsilylethyl-5,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilyl octyl-5-(diethylamino)(trimethoxysilylpropylamino)methylsilylethyl-3,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilyl octyl-3-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylethyl-5,7-dipropyl propyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilyl octyl-5-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylethyl-3,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilyl octyl-3-(diethylamino)(triethoxysilylpropylamino)methylsilylethyl-5,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilyl octyl-5-(diethylamino)(triethoxysilylpropylamino)methylsilylethyl-3,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilyl octyl-3-(diethylamino) (methyldiethoxysilylpropylamino)methylsilylethyl-5,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilyloctyl-5-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethyl-3,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-methyldimethoxysilylethyl-3-(diethylamino)(trimethoxysilylpropylamino)methylsilylethyl-1,3,5,5,7,7-hexamethylcyclotetrasiloxane, 1-methyldimethoxysilylethyl-5-(diethylamino)(trimethoxysilylpropylamino)methylsilylethyl-1,3,3,5,7,7-hexamethylcyclotetrasiloxane,1-methyldimethoxysilylethyl-3-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylethyl-1,3,5,5,7,7-hexamethylcyclotetrasiloxane, 1-methyldimethoxysilylethyl-5-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylethyl-1,3,3,5,7,7-hexamethylcyclotetrasiloxane, 1-methyldimethoxysilylethyl-3-(diethylamino)(triethoxysilylpropylamino)methylsilylethyl-1,3,5,5,7,7-hexamethylcyclotetrasiloxane Methylcyclotetrasiloxane, 1-methyldimethoxysilylethyl-5-(diethylamino)(triethoxysilylpropylamino)methylsilylethyl-1,3,3,5,7,7-hexamethylcyclotetrasiloxane, 1-methyldimethoxysilylethyl-3-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethyl-1,3,5,5,7,7-hexamethylcyclotetrasiloxane, 1-methyldimethoxysilylethyl-5-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethyl- 1,3,3,5,7,7-Hexamethylcyclotetrasiloxane, 1-methyldimethoxysilylethyl-3-(diethylamino)(trimethoxysilylpropylamino)methylsilylethyl-5,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-methyldimethoxysilylethyl-5-(diethylamino)(trimethoxysilylpropylamino)methylsilylethyl-3,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-methyldimethoxysilylethyl-3-(diethylamino)(methyldi 1-methyldimethoxysilylethyl-5-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylethyl-3,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-methyldimethoxysilylethyl-3-(diethylamino)(triethoxysilylpropylamino)methylsilylethyl-5,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane,1-methyldimethoxysilylethyl-5-(diethylamino)(triethoxysilylpropylamino)methylsilylethyl-3,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-methyldimethoxysilylethyl-3-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethyl-5,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-methyldimethoxysilylethyl-5-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethyl 1,3,5-tris(trimethoxysilylethyl)-7-(diethylamino)(trimethoxysilylpropylamino)methylsilylethyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1,3,5-tris(methyldimethoxysilylethyl)-7-(diethylamino)(trimethoxysilylpropylamino)methylsilylethyl-1,3,5,7-tetramethylcyclotetrasiloxane San, 1,3,5-tris(trimethoxysilylethyl)-7-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylethyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1,3,5-tris(methyldimethoxysilylethyl)-7-(diethylamino)(methyldimethoxysilylpropylamino)methylsilylethyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1,3,5-tris(trimethoxysilylethyl)-7-(diethylamino)(triethoxy 1,3,5-tris(methyldimethoxysilylethyl)-7-(diethylamino)(triethoxysilylpropylamino)methylsilylethyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1,3,5-tris(trimethoxysilylethyl)-7-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethyl-1,3,5,7-tetramethylcyclotetrasiloxane,1,3,5-tris(methyldimethoxysilylethyl)-7-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-methyldimethoxysilyl-2-bis(trimethoxysilylpropylamino)methylsilylethylene, 1-methyldimethoxysilyl-2-bis(methyldimethoxysilylpropylamino)methylsilylethylene, 1-methyldimethoxysilyl-2-bis(triethoxysilylpropylamino)methylsilylethylene, 1-methyldimethoxysilyl silyl-2-bis(methyldiethoxysilylpropylamino)methylsilylethylene, 1-methyldimethoxysilyl-6-bis(trimethoxysilylpropylamino)methylsilylhexane, 1-methyldimethoxysilyl-6-bis(methyldimethoxysilylpropylamino)methylsilylhexane, 1-methyldimethoxysilyl-6-bis(triethoxysilylpropylamino)methylsilylhexane, 1-methyldimethoxysilyl-6-bis(methyldiethoxysilylpropylamino)methylsilylhexane, 1-methyldimethoxysilyl-8-bis (trimethoxysilylpropylamino)methylsilyl octane, 1-methyldimethoxysilyl-8-bis(methyldimethoxysilylpropylamino)methylsilyl octane, 1-methyldimethoxysilyl-8-bis(triethoxysilylpropylamino)methylsilyl octane, 1-methyldimethoxysilyl-8-bis(methyldiethoxysilylpropylamino)methylsilyl octane, 1-trimethoxysilyl-2-bis(trimethoxysilylpropylamino)methylsilyl ethylene, 1-trimethoxysilyl-2-bis(methyldimethoxysilyl 1-trimethoxysilyl-2-bis(triethoxysilylpropylamino)methylsilylethylene, 1-trimethoxysilyl-2-bis(methyldiethoxysilylpropylamino)methylsilylethylene, 1-trimethoxysilyl-6-bis(trimethoxysilylpropylamino)methylsilylhexane, 1-trimethoxysilyl-6-bis(methyldimethoxysilylpropylamino)methylsilylhexane, 1-trimethoxysilyl-6-bis(triethoxysilylpropylamino)methylsilylhexane,1-trimethoxysilyl-6-bis(methyldiethoxysilylpropylamino)methylsilylhexane, 1-trimethoxysilyl-8-bis(trimethoxysilylpropylamino)methylsilyloctane, 1-trimethoxysilyl-8-bis(methyldimethoxysilylpropylamino)methylsilyloctane, 1-trimethoxysilyl-8-bis(triethoxysilylpropylamino)methylsilyloctane, 1-trimethoxysilyl-8-bis(methyldiethoxysilylpropylamino)methylsilyloctane, 1-trimethoxysilyl 1-trimethoxysilyl-2-bis(trimethoxysilylpropylamino)methylsilylethylene, 1-trimethoxysilyl-2-bis(methyldimethoxysilylpropylamino)methylsilylethylene, 1-trimethoxysilyl-2-bis(triethoxysilylpropylamino)methylsilylethylene, 1-trimethoxysilyl-2-bis(methyldiethoxysilylpropylamino)methylsilylethylene, 1-trimethoxysilyl-6-bis(trimethoxysilylpropylamino)methylsilylhexane, 1-trimethoxysilyl-6-bis(methyldimethoxysilylpropylamino)methylsilylhexane 1-trimethoxysilyl-6-bis(triethoxysilylpropylamino)methylsilylhexane, 1-trimethoxysilyl-6-bis(methyldiethoxysilylpropylamino)methylsilylhexane, 1-trimethoxysilyl-8-bis(trimethoxysilylpropylamino)methylsilyloctane, 1-trimethoxysilyl-8-bis(methyldimethoxysilylpropylamino)methylsilyloctane, 1-trimethoxysilyl-8-bis(triethoxysilylpropylamino)methylsilylhexane Methylsilyl octane, 1-trimethoxysilyl-8-bis(methyldiethoxysilylpropylamino)methylsilyl octane, 1-triethoxysilyl-2-bis(trimethoxysilylpropylamino)methylsilylethylene, 1-triethoxysilyl-2-bis(methyldimethoxysilylpropylamino)methylsilylethylene, 1-triethoxysilyl-2-bis(triethoxysilylpropylamino)methylsilylethylene, 1-triethoxysilyl-2-bis(methyldiethoxysilylpropylamino)methylsilylethylene,1-triethoxysilyl-6-bis(trimethoxysilylpropylamino)methylsilylhexane, 1-triethoxysilyl-6-bis(methyldimethoxysilylpropylamino)methylsilylhexane, 1-triethoxysilyl-6-bis(triethoxysilylpropylamino)methylsilylhexane, 1-triethoxysilyl-6-bis(methyldiethoxysilylpropylamino)methylsilylhexane, 1-triethoxysilyl-8-bis(trimethoxysilylpropylamino)methylsilyloctane, 1-triethoxysilyl-8-bis(methyldimethoxysilylpropylamino)methylsilyl octane, 1-triethoxysilyl-8-bis(triethoxysilylpropylamino)methylsilyl octane, 1-triethoxysilyl-8-bis(methyldiethoxysilylpropylamino)methylsilyl octane, 1-methyldiethoxysilyl-2-bis(trimethoxysilylpropylamino)methylsilylethylene, 1-methyldiethoxysilyl-2-bis(methyldimethoxysilylpropylamino)methylsilylethylene, 1-methyldiethoxysilyl-2-bis(triethoxysilylpropylamino)methylsilylethylene, 1-methyldiethoxysilyl-2-bis(methyldiethoxysilylpropylamino)methylsilylethylene, 1-methyldiethoxysilyl-6-bis(trimethoxysilylpropylamino)methylsilylhexane, 1- Methyldiethoxysilyl-6-bis(methyldimethoxysilylpropylamino)methylsilylhexane, 1-methyldiethoxysilyl-6-bis(triethoxysilylpropylamino)methylsilylhexane, 1-methyldiethoxysilyl-6-bis(methyldiethoxysilylpropylamino)methylsilylhexane, 1-methyldiethoxysilyl-8-bis(trimethoxysilylpropylamino)methylsilyloctane, 1-methyldiethoxysilyl-8-bis(methyldimethoxysilylpropylamino)methylsilyloctane, 1-methyldiethoxysilyl-8-bis(triethoxysilylpropylamino)methylsilyloctane, 1-methyldiethoxysilyl-8-bis(methyldiethoxysilylpropylamino)methylsilyloctane, trimethoxysilylmethyl-bis(trimethoxysilylpropylamino)methylethyl sulfide,Trimethoxysilylmethyl-bis(methyldimethoxysilylpropylamino)methyl ethyl sulfide, trimethoxysilylmethyl-bis(triethoxysilylpropylamino)methyl ethyl sulfide, trimethoxysilylmethyl-bis(methyldiethoxysilylpropylamino)methyl ethyl sulfide, trimethoxysilylpropyl bis(trimethoxysilylpropylamino)methyl ethyl sulfide, trimethoxysilylpropyl bis(methyldimethoxysilylpropylamino)methyl ethyl sulfide, trimethoxysilylpropyl bis(triethoxysilylpropylamino)methyl ethyl sulfide, trimethoxysilylpropyl bis(methyldiethoxysilylpropylamino)methyl ethyl sulfide, methyldimethoxysilylpropyl bis(trimethoxysilylpropylamino)methyl ethyl sulfide, methyldimethoxysilylpropyl bis(methyldimethoxysilylpropylamino)methyl ethyl sulfide, methyldimethoxysilylpropyl bis(triethoxysilylpropylamino)methyl ethyl sulfide, methyldimethoxysilylpropyl trimethoxysilyl octyl bis(trimethoxysilyl propylamino)methyl ethyl sulfide, trimethoxysilyl octyl bis(trimethoxysilyl propylamino)methyl ethyl sulfide, trimethoxysilyl octyl bis(methyldimethoxysilyl propylamino)methyl ethyl sulfide, trimethoxysilyl octyl bis(triethoxysilyl propylamino)methyl ethyl sulfide, trimethoxysilyl octyl bis(methyldiethoxysilyl propylamino)methyl ethyl sulfide, 1-trimethoxysilylethyldimethylsilyl-2-bis(trimethoxysilyl propylamino)methylsilylethyldimethylsilylbenzene, 1-trimethoxysilylethyldimethylsilyl-3-bis(trimethoxysilyl propylamino)methylsilylethyldimethylsilylbenzene, 1-trimethoxysilylethyldimethylsilyl-4-bis(trimethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-trimethoxysilylethyldimethylsilyl-2-bis(methyldimethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene,1-Trimethoxysilylethyldimethylsilyl-3-bis(methyldimethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-trimethoxysilylethyldimethylsilyl-4-bis(methyldimethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-trimethoxysilylethyldimethylsilyl-2-bis(triethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-trimethoxysilylethyldimethylsilyl-3-bis(triethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-trimethoxysilylethyldimethylsilyl-4-bis(triethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-trimethoxysilylethyldimethylsilyl-2-bis(methyldiethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-trimethoxysilylethyldimethylsilyl-3-bis(methyldiethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-trimethoxysilylethyldimethylsilyl

[0034] dimethylsilyl-4-bis(methyldiethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-methyldimethoxysilylethyldimethylsilyl-2-bis(trimethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-methyldimethoxysilylethyldimethylsilyl-3-bis(trimethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-methyldimethoxysilylethyldimethylsilyl-4-bis(trimethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-methyldimethoxysilylethyldimethylsilyl-2-bis(methyldimethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-methyldimethoxysilylethyldimethylsilyl-3-bis(methyldimethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-methyldimethoxysilylethyldimethylsilyl-4-bis(methyldimethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene,1-methyldimethoxysilylethyldimethylsilyl-2-bis(triethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-methyldimethoxysilylethyldimethylsilyl-3-bis(triethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-methyldimethoxysilylethyldimethylsilyl-4-bis(triethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-methyldimethoxysilylethyldimethylsilyl-2-bis(methyldiethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-methyldimethoxysilylethyldimethylsilyl-3-bis(methyldiethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-methyldimethoxysilylethyldimethylsilyl-4-bis(methyldiethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene, 1-trimethoxysilylethyl-3-bis(trimethoxysilylpropylamino)methylsilylethyl-1,1,3,3-tetramethylsilyl tetramethyldisiloxane, 1-trimethoxysilylethyl-3-bis(methyldimethoxysilylpropylamino)methylsilylethyl-1,1,3,3-tetramethyldisiloxane, 1-trimethoxysilylethyl-3-bis(triethoxysilylpropylamino)methylsilylethyl-1,1,3,3-tetramethyldisiloxane, 1-trimethoxysilylethyl-3-bis(methyldiethoxysilylpropylamino)methylsilylethyl-1,1,3,3-tetramethyldisiloxane, 1-trimethoxysilylethyl 1-trimethoxysilylethyl-9-bis(trimethoxysilylpropylamino)methylsilylethyl-1,1,3,3,5,5,7,7,9,9-decamethylpentasiloxane, 1-trimethoxysilylethyl-9-bis(methyldimethoxysilylpropylamino)methylsilylethyl-1,1,3,3,5,5,7,7,9,9-decamethylpentasiloxane, 1-trimethoxysilylethyl-9-bis(triethoxysilylpropylamino)methylsilylethyl-1,1,3,3,5,5,7,7,9,9-decamethylpentasiloxane,1-trimethoxysilylethyl-9-bis(methyldiethoxysilylpropylamino)methylsilylethyl-1,1,3,3,5,5,7,7,9,9-decamethylpentasiloxane, α-trimethoxysilylethyl-ω-bis(trimethoxysilylpropylamino)methylsilylethyl-polymethylpolysiloxane, α-trimethoxysilylethyl-ω-bis(methyldimethoxysilylpropylamino)methylsilylethyl-polymethylpolysiloxane, α-trimethoxysilylethyl-ω-bis(triethoxysilylpropylamino)methylsilylethyl-polymethylpolysiloxane, α-trimethoxysilylethyl -ω-bis(methyldiethoxysilylpropylamino)methylsilylethyl-polymethylpolysiloxane, 1-trimethoxysilylethyl-3-bis(trimethoxysilylpropylamino)methylsilylethyl-1,3,5,5,7,7-hexamethylcyclotetrasiloxane, 1-trimethoxysilylethyl-5-bis(trimethoxysilylpropylamino)methylsilylethyl-1,3,3,5,7,7-hexamethylcyclotetrasiloxane, 1-trimethoxysilylethyl-3-bis(methyldimethoxysilylpropylamino)methylsilylethyl-1,3,5,5,7,7-hexamethylcyclotetrasiloxane , 1-trimethoxysilylethyl-5-bis(methyldimethoxysilylpropylamino)methylsilylethyl-1,3,3,5,7,7-hexamethylcyclotetrasiloxane, 1-trimethoxysilylethyl-3-bis(triethoxysilylpropylamino)methylsilylethyl-1,3,5,5,7,7-hexamethylcyclotetrasiloxane, 1-trimethoxysilylethyl-5-bis(triethoxysilylpropylamino)methylsilylethyl-1,3,5,5,7,7-hexamethylcyclotetrasiloxane methylsilylethyl-1,3,3,5,7,7-hexamethylcyclotetrasiloxane, 1-trimethoxysilylethyl-3-bis(methyldiethoxysilylpropylamino)methylsilylethyl-1,3,5,5,7,7-hexamethylcyclotetrasiloxane, 1-trimethoxysilylethyl-5-bis(methyldiethoxysilylpropylamino)methylsilylethyl-1,3,3,5,7,7-hexamethylcyclotetrasiloxane,1-trimethoxysilylethyl-3-bis(trimethoxysilylpropylamino)methylsilylethyl-5,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilylethyl-5-bis(trimethoxysilylpropylamino)methylsilylethyl-3,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilylethyl-3-bis(methyldimethoxysilylpropylamino)methylsilylethyl-5,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane siloxane, 1-trimethoxysilylethyl-5-bis(methyldimethoxysilylpropylamino)methylsilylethyl-3,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilylethyl-3-bis(triethoxysilylpropylamino)methylsilylethyl-5,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilylethyl-5-bis(triethoxysilylpropylamino)methylsilylethyl-3,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane tetrasiloxane, 1-trimethoxysilylethyl-3-bis(methyldiethoxysilylpropylamino)methylsilylethyl-5,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilylethyl-5-bis(methyldiethoxysilylpropylamino)methylsilylethyl-3,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilyloctyl-3-bis(trimethoxysilylpropylamino)methylsilylethyl-1,3,5,5,7,7-hexamethylcyclo tetrasiloxane, 1-trimethoxysilyl octyl-5-bis(trimethoxysilylpropylamino)methylsilylethyl-1,3,3,5,7,7-hexamethylcyclotetrasiloxane, 1-trimethoxysilyl octyl-3-bis(methyldimethoxysilylpropylamino)methylsilylethyl-1,3,5,5,7,7-hexamethylcyclotetrasiloxane, 1-trimethoxysilyl octyl-5-bis(methyldimethoxysilylpropylamino)methylsilylethyl-1,3,3,5,7,7-hexamethylcyclotetrasiloxane,1-trimethoxysilyl octyl-3-bis(triethoxysilylpropylamino)methylsilylethyl-1,3,5,5,7,7-hexamethylcyclotetrasiloxane, 1-trimethoxysilyl octyl-5-bis(triethoxysilylpropylamino)methylsilylethyl-1,3,3,5,7,7-hexamethylcyclotetrasiloxane, 1-trimethoxysilyl octyl-3-bis(methyldiethoxysilylpropylamino)methylsilylethyl-1,3,5,5,7,7-hexamethylcyclotetrasiloxane, 1-trimethoxysilyl octyl 1-trimethoxysilyl octyl-5-bis(methyldiethoxysilylpropylamino)methylsilylethyl-1,3,3,5,7,7-hexamethylcyclotetrasiloxane, 1-trimethoxysilyl octyl-3-bis(trimethoxysilylpropylamino)methylsilylethyl-5,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilyl octyl-5-bis(trimethoxysilylpropylamino)methylsilylethyl-3,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilyl octyl 1-trimethoxysilyl octyl-3-bis(methyldimethoxysilylpropylamino)methylsilylethyl-5,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilyl octyl-5-bis(methyldimethoxysilylpropylamino)methylsilylethyl-3,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilyl octyl-3-bis(triethoxysilylpropylamino)methylsilylethyl-5,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilyl octyl-3-bis(triethoxysilylpropylamino)methylsilylethyl-5,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane silyloctyl-5-bis(triethoxysilylpropylamino)methylsilylethyl-3,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilyloctyl-3-bis(methyldiethoxysilylpropylamino)methylsilylethyl-5,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilyloctyl-5-bis(methyldiethoxysilylpropylamino)methylsilylethyl-3,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane,1-methyldimethoxysilylethyl-3-bis(trimethoxysilylpropylamino)methylsilylethyl-1,3,5,5,7,7-hexamethylcyclotetrasiloxane, 1-methyldimethoxysilylethyl-5-bis(trimethoxysilylpropylamino)methylsilylethyl-1,3,3,5,7,7-hexamethylcyclotetrasiloxane, 1-methyldimethoxysilylethyl-3-bis(methyldimethoxysilylpropylamino)methylsilylethyl-1,3,5,5,7,7-hexamethylcyclotetrasiloxane, 1-methyldimethoxysilylethyl 1-methyldimethoxysilylethyl-5-bis(methyldimethoxysilylpropylamino)methylsilylethyl-1,3,3,5,7,7-hexamethylcyclotetrasiloxane, 1-methyldimethoxysilylethyl-3-bis(triethoxysilylpropylamino)methylsilylethyl-1,3,5,5,7,7-hexamethylcyclotetrasiloxane, 1-methyldimethoxysilylethyl-5-bis(triethoxysilylpropylamino)methylsilylethyl-1,3,3,5,7,7-hexamethylcyclotetrasiloxane, 1-methyldimethoxysilylethyl methylsilylethyl-3-bis(methyldiethoxysilylpropylamino)methylsilylethyl-1,3,5,5,7,7-hexamethylcyclotetrasiloxane, 1-methyldimethoxysilylethyl-5-bis(methyldiethoxysilylpropylamino)methylsilylethyl-1,3,3,5,7,7-hexamethylcyclotetrasiloxane, 1-methyldimethoxysilylethyl-3-bis(trimethoxysilylpropylamino)methylsilylethyl-5,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-methyldimethoxysilyl ethyl-5-bis(trimethoxysilylpropylamino)methylsilylethyl-3,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-methyldimethoxysilylethyl-3-bis(methyldimethoxysilylpropylamino)methylsilylethyl-5,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-methyldimethoxysilylethyl-5-bis(methyldimethoxysilylpropylamino)methylsilylethyl-3,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane,1-methyldimethoxysilylethyl-3-bis(triethoxysilylpropylamino)methylsilylethyl-5,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-methyldimethoxysilylethyl-5-bis(triethoxysilylpropylamino)methylsilylethyl-3,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-methyldimethoxysilylethyl-3-bis(methyldiethoxysilylpropylamino)methylsilylethyl-5,7-dipropyl-1 ,3,5,7-tetramethylcyclotetrasiloxane, 1-methyldimethoxysilylethyl-5-bis(methyldiethoxysilylpropylamino)methylsilylethyl-3,7-dipropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1,3,5-tris(trimethoxysilylethyl)-7-bis(trimethoxysilylpropylamino)methylsilylethyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1,3,5-tris(methyldimethoxysilylethyl)-7-bis(trimethoxysilylpropylamino)methylsilylethyl-1,3,5,7-tetramethylcyclotetrasiloxane 1,3,5-tris(trimethoxysilylethyl)-7-bis(methyldimethoxysilylpropylamino)methylsilylethyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1,3,5-tris(methyldimethoxysilylethyl)-7-bis(methyldimethoxysilylpropylamino)methylsilylethyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1,3,5-tris(methyldimethoxysilylethyl)-7-bis(methyldimethoxysilylpropylamino)methylsilylethyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1,3,5-tris(trimethoxysilylethyl)-7-bis(methyldimethoxysilylpropylamino)methylsilylethyl-1,3,5,7-tetramethylcyclotetrasiloxane 1,3,5-tris(methyldimethoxysilylethyl)-7-bis(triethoxysilylpropylamino)methylsilylethyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1,3,5-tris(methyldimethoxysilylethyl)-7-bis(triethoxysilylpropylamino)methylsilylethyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1,3,5-tris(trimethoxysilylethyl)-7-bis(methyldiethoxysilylpropylamino)methylsilylethyl-1,3,5,7-tetramethylcyclotetrasiloxane,1,3,5-tris(methyldimethoxysilylethyl)-7-bis(methyldiethoxysilylpropylamino)methylsilylethyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-trimethoxysilylethyl-2-dimethyl(trimethoxysilylpropylamino)ethylene, 1-trimethoxysilylethyl-2-dimethyl(methyldimethoxysilylpropylamino)ethylene, 1-trimethoxysilylethyl-2-dimethyl(triethoxysilylpropylamino)ethylene, 1-trimethoxysilylethyl-2-dimethyl(methyldiethoxysilylpropylamino)ethylene, 1-methyldimethoxysilylethyl-2-dimethyl(trimethoxysilylpropylamino)ethylene, 1-methyldimethoxysilylethyl-2-dimethyl(methyldimethoxysilylpropylamino)ethylene, 1-methyldimethoxysilylethyl-2-dimethyl(triethoxysilylpropylamino)ethylene, 1-methyldimethoxysilylethyl Examples of such silylethyl include 1-triethoxysilylethyl-2-dimethyl(methyldiethoxysilylpropylamino)ethylene, 1-triethoxysilylethyl-2-dimethyl(trimethoxysilylpropylamino)ethylene, 1-triethoxysilylethyl-2-dimethyl(methyldimethoxysilylpropylamino)ethylene, 1-triethoxysilylethyl-2-dimethyl(triethoxysilylpropylamino)ethylene, 1-triethoxysilylethyl-2-dimethyl(methyldiethoxysilylpropylamino)ethylene, 1-methyldiethoxysilylethyl-2-dimethyl(trimethoxysilylpropylamino)ethylene, 1-methyldiethoxysilylethyl-2-dimethyl(methyldimethoxysilylpropylamino)ethylene, 1-methyldiethoxysilylethyl-2-dimethyl(triethoxysilylpropylamino)ethylene, and 1-methyldiethoxysilylethyl-2-dimethyl(methyldiethoxysilylpropylamino)ethylene.

[0030] [2] Compositions Containing Bissilyl Compounds Having Silyl Groups Substituted with Organoxysilylalkylamino Groups Compound (1) of the present invention can be used alone or as a composition. For example, it may be used as a composition containing an aprotic solvent (hereinafter referred to as "Composition 1") as long as it does not affect Compound (1). Specific examples of aprotic solvents include aliphatic hydrocarbon compounds having 5 to 20 carbon atoms such as pentane, hexane, cyclohexane, octane, isooctane, nonane, decane, dodecane, and isododecane; aromatic hydrocarbon compounds having 6 to 10 carbon atoms such as benzene, toluene, and xylene; ether compounds such as diethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 4-methyltetrahydropyran, cyclopentyl methyl ether, and dioxane; ester compounds such as ethyl acetate, isopropyl acetate, and butyl acetate; and nitrile compounds such as acetonitrile, propionitrile, butyronitrile, and isobutyronitrile. and organosilicon compounds having 1 to 10 silicon atoms, such as tetraethylsilane, hexamethyldisiloxane, octamethyltrisiloxane, tris(trimethylsiloxy)methylsilane, 3,5-diethyl-1,1,1,3,5,7,7,7-octamethyltetrasiloxane, octamethylcyclotetrasiloxane, decamethyltetrasiloxane, decamethylcyclopentasiloxane, and dodecamethylpentasiloxane. These aprotic solvents may be used alone or in combination of two or more. Among these, aliphatic hydrocarbon compounds having 8 to 12 carbon atoms and organosilicon compounds having 1 to 8 silicon atoms are more preferred from the standpoint of safety.

[0031] In composition 1, the amount of the aprotic solvent used is not particularly limited, but is an amount such that the concentration of compound (1) becomes preferably 0.1 to 90% by mass, more preferably 1 to 90% by mass, and even more preferably 2 to 80% by mass.

[0032] Furthermore, compound (1) of the present invention can also be used as a composition (hereinafter referred to as “composition 2”) containing compound (1) and an amino group-containing organoxysilane compound represented by the following general formula (2) (hereinafter also referred to as “compound (2)”):

[0033] (In the formula, R 8 ~R 10 and p have the same meaning as above.

[0034] Specific examples of compound (2) include aminoalkyltriorganoxysilane compounds such as aminomethyltrimethoxysilane, aminomethyltriethoxysilane, aminopropyltrimethoxysilane, aminopropyltriethoxysilane, aminooctyltrimethoxysilane, aminooctyltriethoxysilane, aminoethylaminopropyltrimethoxysilane, aminoethylaminopropyltriethoxysilane, aminopropylaminopropyltrimethoxysilane, aminopropylaminopropyltriethoxysilane, aminoethylaminoethylaminopropyltrimethoxysilane, aminoethylaminoethylaminopropyltriethoxysilane, aminoethyltrimethoxysilylmethylsulfide, and aminoethyltriethoxysilylmethylsulfide; aminopropylmethyldimethoxysilane, aminopropylmethyldiethoxysilane, and aminoethylaminopropylmethyldimethoxysilane. aminoalkyl alkyl diorganoxysilane compounds such as aminoethyl aminopropyl methyl diethoxysilane, aminopropyl aminopropyl methyl dimethoxysilane, aminopropyl aminopropyl methyl diethoxysilane, aminoethyl aminoethyl aminopropyl methyl dimethoxysilane, and aminoethyl aminoethyl aminopropyl methyl diethoxysilane; and aminoalkyl dialkyl organoxysilane compounds such as aminopropyl dimethyl methoxysilane, aminopropyl dimethyl ethoxysilane, aminoethyl aminopropyl dimethyl methoxysilane, aminoethyl aminopropyl dimethyl ethoxysilane, aminopropyl aminopropyl dimethyl methoxysilane, aminopropyl aminopropyl dimethyl ethoxysilane, aminoethyl aminoethyl aminopropyl dimethyl methoxysilane, and aminoethyl aminoethyl aminopropyl dimethyl ethoxysilane.

[0035] In composition 2, the blending ratio of compound (1) to compound (2) is not particularly limited. From the viewpoint of the hardness of the coating film, the amount of compound (2) is preferably 1 to 20 mass %, more preferably 2 to 15 mass %, and even more preferably 3 to 10 mass %, relative to the total mass of compound (1) and compound (2).

[0036] Composition 2 can be used without a solvent, but a solvent may be used as long as it does not affect Compound (1) or Compound (2). Specific examples of the solvent include the same solvents as those exemplified for Composition 1 containing the solvent, and in this case, an aprotic solvent is also preferred.

[0037] Although the compound (1) and compositions 1 and 2 of the present invention can be cured without a catalyst, a catalyst may be added to the extent that cracking and whitening do not occur. Examples of catalysts include at least one metal compound selected from titanium compounds, aluminum compounds, zinc compounds, and tin compounds, acidic compounds, basic compounds, etc. Specific examples of titanium compounds include tetraalkyl orthotitanates such as tetrabutyl orthotitanate, tetramethyl orthotitanate, tetraethyl orthotitanate, tetrapropyl orthotitanate, and tetraisopropyl orthotitanate, as well as their partial hydrolysis condensates and titanium acylate. Specific examples of aluminum compounds include aluminum trihydroxide, aluminum alcoholates, aluminum acylates, aluminum acylate salts, aluminosiloxy compounds, and aluminum metal chelate compounds. Specific examples of zinc compounds include zinc octoate and zinc 2-ethylhexanoate. Specific examples of tin compounds include dioctyltin dioctate and dioctyltin dilaurate. Specific examples of acidic compounds include hydrogen chloride, hydrogen bromide, hydrogen iodide, nitric acid, sulfuric acid, acetic acid, and methanesulfonic acid. Specific examples of basic compounds include ammonia, sodium hydroxide, and potassium hydroxide. These catalysts may be used alone or in combination of two or more.

[0038] The amount of the catalyst used is not particularly limited, but from the viewpoint of exerting the effect of the catalyst, it is preferably 0.01 to 10 mass % and more preferably 0.1 to 5 mass % relative to the mass of compound (1) or the total mass of compound (1) and compound (2).

[0039] Compositions 1 and 2 of the present invention can be obtained by mixing compound (1) with a solvent, compound (2), a catalyst, and other additives, if necessary, while taking care to avoid moisture contamination, to obtain a homogeneous solution. Specifically, the components can be handled under an inert gas atmosphere such as nitrogen or argon to avoid moisture contamination.

[0040] [3] Method for Producing a Bissilyl Compound Having a Silyl Group Substituted with an Organoxysilylalkylamino Group Next, a method for producing compound (1) will be described. The production method of the present invention comprises a step of subjecting compound (2) described above and a bissilyl compound represented by the following general formula (3) (hereinafter also referred to as compound (3)) to an amine exchange reaction in the presence of an acidic compound having a pKa of 4 to 12 and an aprotic polar solvent.

[0041] (In the formula, R 1 ~R 7 , a, l and m have the same meanings as above.)

[0042] Specific examples of compound (3) include 1-trimethoxysilyl-2-bis(dimethylamino)methylsilylethylene, 1-trimethoxysilyl-6-bis(dimethylamino)methylsilylhexane, 1-trimethoxysilyl-8-bis(dimethylamino)methylsilyloctane, 1-triethoxysilyl-2-bis(dimethylamino)methylsilylethylene, 1-triethoxysilyl-6-bis(dimethylamino)methylsilylhexane, 1-triethoxysilyl-8-bis(dimethylamino)methylsilyloctane, and 1-trimethoxysilyl 1-triethoxysilyl-2-bis(diethylamino)methylsilylethylene, 1-trimethoxysilyl-6-bis(diethylamino)methylsilylhexane, 1-trimethoxysilyl-8-bis(diethylamino)methylsilyloctane, 1-triethoxysilyl-2-bis(diethylamino)methylsilylethylene, 1-triethoxysilyl-6-bis(diethylamino)methylsilylhexane, 1-triethoxysilyl-8-bis(diethylamino)methylsilyloctane, 1-trimethoxysilyl-2-bis(4-methylpiperazin-1-yl)methylsilyl ethylene, 1-trimethoxysilyl-6-bis(4-methylpiperazin-1-yl)methylsilylhexane, 1-trimethoxysilyl-8-bis(4-methylpiperazin-1-yl)methylsilyloctane, 1-triethoxysilyl-2-bis(4-methylpiperazin-1-yl)methylsilylethylene, 1-triethoxysilyl-6-bis(4-methylpiperazin-1-yl)methylsilylhexane, 1-triethoxysilyl-8-bis(4-methylpiperazin-1-yl)methylsilyloctane, 1-trimethoxy ... (dimethylamino)phenylsilylethylene, 1-trimethoxysilyl-6-bis(dimethylamino)phenylsilylhexane, 1-trimethoxysilyl-8-bis(dimethylamino)phenylsilyloctane, 1-triethoxysilyl-2-bis(dimethylamino)phenylsilylethylene, 1-triethoxysilyl-6-bis(dimethylamino)phenylsilylhexane, 1-triethoxysilyl-8-bis(dimethylamino)phenylsilyloctane, 1-trimethoxysilyl-2-bis(diethylamino)phenylsilylethylene,1-trimethoxysilyl-6-bis(diethylamino)phenylsilylhexane, 1-trimethoxysilyl-8-bis(diethylamino)phenylsilyloctane, 1-triethoxysilyl-2-bis(diethylamino)phenylsilylethylene, 1-triethoxysilyl-6-bis(diethylamino)phenylsilylhexane, 1-triethoxysilyl-8-bis(diethylamino)phenylsilyloctane, 1-trimethoxysilyl-2-bis(4-methylpiperazin-1-yl)phenylsilylethylene, 1-trimethoxysilyl-6-bis (4-methylpiperazin-1-yl)phenylsilylhexane, 1-trimethoxysilyl-8-bis(4-methylpiperazin-1-yl)phenylsilyloctane, 1-triethoxysilyl-2-bis(4-methylpiperazin-1-yl)phenylsilylethylene, 1-triethoxysilyl-6-bis(4-methylpiperazin-1-yl)phenylsilylhexane, 1-triethoxysilyl-8-bis(4-methylpiperazin-1-yl)phenylsilyloctane, 1-trimethoxysilylethyl-3-bis(diethylamino)methylsilylethyl -1,1,3,3-tetramethyldisiloxane, 1-trimethoxysilylethyl-9-bis(diethylamino)methylsilylethyl-1,1,3,3,5,5,7,7,9,9-decamethylpentasiloxane, α-trimethoxysilylethyl-ω-bis(diethylamino)methylsilylethyl-polymethylpolysiloxane, 1-triethoxysilylethyl-3-bis(diethylamino)methylsilylethyl-1,1,3,3-tetramethyldisiloxane, 1-triethoxysilylethyl-9-bis(diethylamino)methylsilylethyl-1,1, 3,3,5,5,7,7,9,9-decamethylpentasiloxane, α-triethoxysilylethyl-ω-bis(diethylamino)methylsilylethyl-polymethylpolysiloxane, trimethoxysilylmethyl-bis(diethylamino)methylethyl sulfide, trimethoxysilylpropyl-bis(diethylamino)methylethyl sulfide, trimethoxysilyloctyl-bis(diethylamino)methylethyl sulfide, 1-trimethoxysilylethyldimethylsilyl-4-bis(diethylamino)methylsilylethyldimethylsilylbenzene,Trialkoxysilyl-bis(dialkylamino)alkylalkanes such as triethoxysilylmethyl-bis(diethylamino)methylethyl sulfide, triethoxysilylpropyl-bis(diethylamino)methylethyl sulfide, triethoxysilyloctyl-bis(diethylamino)methylethyl sulfide, and 1-triethoxysilylethyldimethylsilyl-4-bis(diethylamino)methylsilylethyldimethylsilylbenzene; 1-methyldimethoxysilyl-2-bis(dimethylamino)methylsilylethylene, 1-methyl Dimethoxysilyl-6-bis(dimethylamino)methylsilylhexane, 1-methyldimethoxysilyl-8-bis(dimethylamino)methylsilyloctane, 1-methyldiethoxysilyl-2-bis(dimethylamino)methylsilylethylene, 1-methyldiethoxysilyl-6-bis(dimethylamino)methylsilylhexane, 1-methyldiethoxysilyl-8-bis(dimethylamino)methylsilyloctane, 1-methyldimethoxysilyl-2-bis(diethylamino)methylsilylethylene, 1-methyldimethoxysilyl-6-bis(di 1-methyldiethoxysilyl-6-bis(diethylamino)methylsilylhexane, 1-methyldimethoxysilyl-8-bis(diethylamino)methylsilyloctane, 1-methyldiethoxysilyl-2-bis(diethylamino)methylsilylethylene, 1-methyldiethoxysilyl-6-bis(diethylamino)methylsilylhexane, 1-methyldiethoxysilyl-8-bis(diethylamino)methylsilyloctane, 1-methyldimethoxysilyl-2-bis(4-methylpiperazin-1-yl)methylsilylethylene, 1-methyldimethoxysilyl-6-bis(4-methylpiperazin-1-yl)methylsilyl 1-methyldiethoxysilyl-6-bis(4-methylpiperazin-1-yl)methylsilylhexane, 1-methyldimethoxysilyl-8-bis(4-methylpiperazin-1-yl)methylsilyl octane, 1-methyldiethoxysilyl-2-bis(4-methylpiperazin-1-yl)methylsilylethylene, 1-methyldiethoxysilyl-6-bis(4-methylpiperazin-1-yl)methylsilylhexane, 1-methyldiethoxysilyl-8-bis(4-methylpiperazin-1-yl)methylsilyl octane, 1-methyldimethoxysilyl-2-bis(dimethylamino)phenylsilylethylene,1-methyldimethoxysilyl-6-bis(dimethylamino)phenylsilylhexane, 1-methyldimethoxysilyl-8-bis(dimethylamino)phenylsilyloctane, 1-methyldiethoxysilyl-2-bis(dimethylamino)phenylsilylethylene, 1-methyldiethoxysilyl-6-bis(dimethylamino)phenylsilylhexane, 1-methyldiethoxysilyl-8-bis(dimethylamino)phenylsilyloctane, 1-methyldimethoxysilyl-2-bis(diethylamino)phenylsilylethylene, 1-methyldi Methoxysilyl-6-bis(diethylamino)phenylsilylhexane, 1-methyldimethoxysilyl-8-bis(diethylamino)phenylsilyloctane, 1-methyldiethoxysilyl-2-bis(diethylamino)phenylsilylethylene, 1-methyldiethoxysilyl-6-bis(diethylamino)phenylsilylhexane, 1-methyldiethoxysilyl-8-bis(diethylamino)phenylsilyloctane, 1-methyldimethoxysilyl-2-bis(4-methylpiperazin-1-yl)phenylsilylethylene, 1-methyl dimethoxysilyl-6-bis(4-methylpiperazin-1-yl)phenylsilylhexane, 1-methyldimethoxysilyl-8-bis(4-methylpiperazin-1-yl)phenylsilyloctane, 1-methyldiethoxysilyl-2-bis(4-methylpiperazin-1-yl)phenylsilylethylene, 1-methyldiethoxysilyl-6-bis(4-methylpiperazin-1-yl)phenylsilylhexane, 1-methyldiethoxy ... silylethyl-3-bis(diethylamino)methylsilylethyl-1,1,3,3-tetramethyldisiloxane, 1-methyldimethoxysilylethyl-9-bis(diethylamino)methylsilylethyl-1,1,3,3,5,5,7,7,9,9-decamethylpentasiloxane, α-methyldimethoxysilylethyl-ω-bis(diethylamino)methylsilylethyl-polymethylpolysiloxane, 1-methyldiethoxysilylethyl-3-bis(diethylamino)methylsilylethyl-1,1,3,3-tetramethyldisiloxane,1-methyldiethoxysilylethyl-9-bis(diethylamino)methylsilylethyl-1,1,3,3,5,5,7,7,9,9-decamethylpentasiloxane, α-methyldiethoxysilylethyl-ω-bis(diethylamino)methylsilylethyl-polymethylpolysiloxane, methyldimethoxysilylmethyl-bis(diethylamino)methylethyl sulfide, methyldimethoxysilylpropyl-bis(diethylamino)methylethyl sulfide, methyldimethoxysilyloctyl-bis(diethylamino)methylethyl sulfide, 1-methyldimethoxysilylethyldimethylsilyl-4-bis(diethylamino)methylsilylethyldimethylsilylbenzene, methyldiethoxysilylmethyl-bis(diethylamino)methylethyl sulfide, methyldiethoxysilylpropyl-bis(diethylamino)methyl alkylalkoxysilyl-bis(dialkylamino)alkylalkanes such as ethyl sulfide, methyldiethoxysilyl octyl-bis(diethylamino)methyl ethyl sulfide, and 1-methyldiethoxysilylethyldimethylsilyl-4-bis(diethylamino)methylsilylethyldimethylsilylbenzene; 1-dimethylmethoxysilyl-2-bis(dimethylamino)methylsilylethylene, 1-dimethylmethoxysilyl-6-bis(dimethylamino)methylsilylhexane, 1-dimethylmethoxysilyl-8-bis(dimethylamino)methylsilyloctane, 1-dimethylethoxysilyl-2-bis(dimethylamino)methylsilylethylene, 1-dimethylethoxysilyl-6-bis(dimethylamino)methylsilylhexane, and 1-dimethylethoxysilyl-8-bis(dimethylamino)methylsilyloctane; 1-dimethylmethoxysilyl-2-bis(diethylamino)methylsilylethylene, 1-dimethylmethoxysilyl-6-bis(diethylamino)methylsilylhexane, 1-dimethylmethoxysilyl-8-bis(diethylamino)methylsilyloctane, 1-dimethylethoxysilyl-2-bis(diethylamino)methylsilylethylene, 1-dimethylethoxysilyl-6-bis(diethylamino)methylsilylhexane, 1-dimethylethoxysilyl-8-bis(diethylamino)methylsilyloctane,1-dimethylmethoxysilyl-2-bis(4-methylpiperazin-1-yl)methylsilylethylene, 1-dimethylmethoxysilyl-6-bis(4-methylpiperazin-1-yl)methylsilylhexane, 1-dimethylmethoxysilyl-8-bis(4-methylpiperazin-1-yl)methylsilyloctane, 1-dimethylethoxysilyl-2-bis(4-methylpiperazin-1-yl)methylsilylethylene, 1-dimethylethoxysilyl-6-bis(4-methylpiperazin-1-yl)methylsilylhexane, 1-dimethylethoxysilyl- 8-bis(4-methylpiperazin-1-yl)methylsilyl octane, 1-dimethylmethoxysilyl-2-bis(dimethylamino)phenylsilylethylene, 1-dimethylmethoxysilyl-6-bis(dimethylamino)phenylsilylhexane, 1-dimethylmethoxysilyl-8-bis(dimethylamino)phenylsilyl octane, 1-dimethylethoxysilyl-2-bis(dimethylamino)phenylsilylethylene, 1-dimethylethoxysilyl-6-bis(dimethylamino)phenylsilylhexane, 1-dimethylethoxysilyl-8-bis (Dimethylamino)phenylsilyl octane, 1-dimethylmethoxysilyl-2-bis(diethylamino)phenylsilyl ethylene, 1-dimethylmethoxysilyl-6-bis(diethylamino)phenylsilylhexane, 1-dimethylmethoxysilyl-8-bis(diethylamino)phenylsilyl octane, 1-dimethylethoxysilyl-2-bis(diethylamino)phenylsilyl ethylene, 1-dimethylethoxysilyl-6-bis(diethylamino)phenylsilylhexane, 1-dimethylethoxysilyl-8-bis(diethylamino)phenyl silyl octane, 1-dimethylmethoxysilyl-2-bis(4-methylpiperazin-1-yl)phenylsilylethylene, 1-dimethylmethoxysilyl-6-bis(4-methylpiperazin-1-yl)phenylsilylhexane, 1-dimethylmethoxysilyl-8-bis(4-methylpiperazin-1-yl)phenylsilyl octane, 1-dimethylethoxysilyl-2-bis(4-methylpiperazin-1-yl)phenylsilylethylene, 1-dimethylethoxysilyl-6-bis(4-methylpiperazin-1-yl)phenylsilylhexane,1-dimethylethoxysilyl-8-bis(4-methylpiperazin-1-yl)phenylsilyloctane, 1-dimethylmethoxysilylethyl-3-bis(diethylamino)methylsilylethyl-1,1,3,3-tetramethyldisiloxane, 1-dimethylmethoxysilylethyl-9-bis(diethylamino)methylsilylethyl-1,1,3,3,5,5,7,7,9,9-decamethylpentasiloxane, α-dimethylmethoxysilylethyl-ω-bis(diethylamino)methylsilylethyl-polymethylpolysiloxane, 1-dimethylethoxysilylethyl-3-bis(diethylamino)methylsilylethyl-1,1,3,3,5,5,7,7,9,9-tetramethyldisiloxane dimethylethoxysilylethyl-3-bis(diethylamino)methylsilylethyl-1,1,3,3-tetramethyldisiloxane, 1-dimethylethoxysilylethyl-9-bis(diethylamino)methylsilylethyl-1,1,3,3,5,5,7,7,9,9-decamethylpentasiloxane, α-dimethylethoxysilylethyl-ω-bis(diethylamino)methylsilylethyl-polymethylpolysiloxane, dimethylmethoxysilylmethyl-bis(diethylamino)methylethyl sulfide, dimethylmethoxysilylpropyl-bis(diethylamino) ) methyl ethyl sulfide, dimethylmethoxysilyl octyl-bis(diethylamino) methyl ethyl sulfide, 1-dimethylmethoxysilylethyl dimethylsilyl-4-bis(diethylamino) methylsilylethyl dimethylsilylbenzene, dimethylethoxysilylmethyl-bis(diethylamino) methyl ethyl sulfide, dimethylethoxysilylpropyl-bis(diethylamino) methyl ethyl sulfide, dimethylethoxysilyl octyl-bis(diethylamino) methyl ethyl sulfide, 1-dimethylethoxysilylethyl dimethyl dialkylalkoxysilyl-bis(dialkylamino)alkylalkanes such as methylsilyl-4-bis(diethylamino)methylsilylethyldimethylsilylbenzene; 1-trimethoxysilyl-2-tris(dimethylamino)silylethylene, 1-triethoxysilyl-2-tris(dimethylamino)silylethylene, 1-trimethoxysilyl-2-tris(diethylamino)silylethylene, 1-triethoxysilyl-2-tris(diethylamino)silylethylene, 1-trimethoxysilyl-2-tris(morpholino)silylethylene,Examples of such alkyldialkoxysilyl-tris(dialkylamino)alkanes include 1-triethoxysilyl-2-tris(dialkylamino)alkanes such as 1-triethoxysilyl-2-tris(dimethylamino)silylethylene, 1-methyldiethoxysilyl-2-tris(dimethylamino)silylethylene, 1-methyldimethoxysilyl-2-tris(diethylamino)silylethylene, 1-methyldiethoxysilyl-2-tris(diethylamino)silylethylene, 1-methyldimethoxysilyl-2-tris(morpholino)silylethylene, and 1-methyldiethoxysilyl-2-tris(morpholino)silylethylene.

[0043] The acidic compound used in the transamination reaction is an acidic compound having a pKa of 4 to 12, preferably a pKa of 7 to 10. Use of such an acidic compound can reduce side reactions and increase the amount of compound (1) produced. Specific examples of acidic compounds having a pKa of 4 to 12 include carboxylic acids such as acetic acid, propionic acid, hexanoic acid, and octanoic acid; ammonium halides such as ammonium chloride and ammonium bromide; amine hydrogen halides such as diethylamine hydrochloride and diethylamine hydrobromide; ammonium sulfates such as ammonium sulfate and ammonium amidosulfate; ammonium sulfonates such as ammonium methanesulfonate and ammonium dodecylbenzenesulfonate; and sulfonamides such as p-toluenesulfonamide and o-toluenesulfonamide. Among these, ammonium halides, amine hydrogen halides, and ammonium sulfonates are preferred, with amine hydrogen halides being more preferred, in terms of their reaction-accelerating effect and the generation of fewer by-products.

[0044] The amount of the acidic compound having a pKa of 4 to 12 used is not particularly limited, but is preferably 0.000001 to 0.02 mol, more preferably 0.000005 to 0.01 mol, and even more preferably 0.00001 to 0.005 mol relative to the number of moles of compound (3). The transamination reaction temperature is preferably 30 to 150°C, more preferably 50 to 110°C. The transamination reaction time is preferably 30 to 600 minutes, more preferably 60 to 600 minutes, and even more preferably 60 to 300 minutes.

[0045] In the production method of the present invention, compound (1) can be efficiently produced by using an aprotic polar solvent. Examples of the solvent that can be used include nitrile compounds such as acetonitrile, propionitrile, butyronitrile, and isobutyronitrile; ether compounds such as tetrahydrofuran, 2-methyltetrahydrofuran, tetrahydropyran, 4-methyltetrahydropyran, and cyclopentyl methyl ether; and amide compounds such as N,N-dimethylformamide, dimethylacetamide, and N-methylpyrrolidone. Among these, nitrile compounds that have a high reaction-accelerating effect and are less likely to cause side reactions are preferred, and acetonitrile is most preferred.

[0046] The acidic compound having a pKa of 4 to 12 can be neutralized after the reaction to enhance the stability of compound (1) and compositions 1 and 2. In this case, the basic compound used for neutralization is not particularly limited, but a solid basic compound is preferred. Specific examples of solid basic compounds include aluminum hydroxide, hydrosaltite, magnesium silicate, aluminum silicate, aluminum oxide, and magnesium oxide, which may be used alone or in combination of two or more. Commercially available solid basic compounds can be used, such as the Kyoward series (Kyoward 100, 200, 300, 500, 600, 700, and 2000) manufactured by Kyowa Chemical Industry Co., Ltd.

[0047] The amount of the solid basic compound used is not particularly limited, but is preferably 1.0 to 2.0 moles, more preferably 1.0 to 1.8 moles, and even more preferably 1.2 to 1.8 moles relative to the number of moles of the acidic compound having a pKa of 4 to 12 used.

[0048] It is preferable to separate the salt generated by the neutralization reaction and the excess solid basic compound. The separation method is not particularly limited, but separation by filtration is convenient.

[0049] To isolate the target compound (1) or compound (1) and compound (2) from the reaction solution obtained by the above series of reactions, an appropriate purification method can be selected from purification methods commonly used in organic synthesis, such as filtration, distillation, vacuum stripping, various types of chromatography, treatment with an adsorbent, etc. Among these, purification by vacuum stripping or distillation is preferred from the viewpoints of production efficiency and the ability to achieve a high purity of the target product.

[0050] [4] Cured product The cured product of the present invention is a product obtained by curing compound (1) itself or compound (1) and compound (2), specifically a cured product obtained by curing alkoxysilyl groups contained in compound (1) or compound (2) through hydrolysis and condensation reaction. When a solvent is contained, the solvent may or may not be volatilized before curing, or the curing may be carried out while volatilizing the solvent.

[0051] The curing temperature can be from room temperature to heated. There are no particular restrictions on the temperature as long as it does not adversely affect the substrate, but to maintain reactivity, it is preferably 0 to 250°C, more preferably 20 to 180°C, and even more preferably 20 to 150°C. In addition, since the composition reacts with moisture in the air, the relative humidity is preferably 15 to 100%, more preferably 25 to 80%.

[0052] The surface of a substrate made of an inorganic material or an organic material or the like is coated with compound (1), composition 1 or composition 2 of the present invention, and then the coated substrate can be cured by reacting the coated substrate with moisture in the air.

[0053] Specific examples of inorganic materials include metal, glass, silica, alumina, talc, calcium carbonate, and carbon. The shape of these materials is not particularly limited, and they may be in the form of a plate, sheet, fiber, or powder. Commonly used types of glass such as E-glass, C-glass, and quartz glass can be used as the glass, and glass fibers may also be used. The glass fibers may be aggregates thereof, and may be, for example, fiber bundles, twisted yarns, woven fabrics, etc. of glass-based (filament) fibers having a fiber diameter of 3 to 30 μm.

[0054] Specific examples of organic materials include resin materials such as polyethylene, polypropylene, polystyrene, poly(meth)acrylic, polyvinyl chloride, polycarbonate, nylon, polyurethane, polybutylene terephthalate, polyethylene terephthalate, ABS (a polymer of acrylonitrile, butadiene, and styrene), melamine, phenol, epoxy, and polyimide, as well as elastomers and rubber materials such as polybutadiene rubber, polyisopropylene rubber, nitrile rubber, neoprene rubber, polysulfide, and urethane rubber. The shape of the substrate is not particularly limited, and may be any of a plate, sheet, fiber, and powder.

[0055] As a method for applying to a substrate, a known application method can be employed, such as brush coating, sponge coating, cloth coating, spray coating, wire bar coating, blade coating, roll coating, dipping, spin coating, etc. In addition, for powdery materials such as silica, alumina, talc, calcium carbonate, etc., a mixing method can be employed in which compound (1), composition 1, or composition 2 is directly mixed with the substrate in a mixer or mill.

[0056] EXAMPLES The present invention will be explained in more detail below with reference to examples, comparative examples and synthesis examples, but the present invention is not limited to the following examples.

[0057] [Example 1-1] (In the formula, Me represents a methyl group, and Et represents an ethyl group. The same applies hereinafter.)

[0058] The interior of a four-necked glass flask equipped with a stirrer, thermometer, and reflux condenser was purged with nitrogen, and 32.1 g (0.100 mol) of 1-methyldimethoxysilyl-2-bis(diethylamino)methylsilylethylene, 26.9 g (0.150 mol) of 3-aminopropyltrimethoxysilane, 0.054 g (0.0010 mol) of ammonium chloride, and 20 g of acetonitrile were added and refluxed for 3 hours. Analysis of the reaction solution by gas chromatography revealed the formation of diethylamine, confirming the progress of the amine exchange reaction. 2.2 g of Kyoward 500SH (manufactured by Kyowa Chemical Industry Co., Ltd., the same applies hereinafter) was added to the resulting reaction solution and stirred at room temperature for 1 hour. The resulting mixture was stripped of diethylamine and acetonitrile, and filtered to obtain 43 g of compound 1 (a mixture of 1-methyldimethoxysilyl-2-(diethylamino)(trimethoxysilylpropylamino)methylsilylethylene and 1-methyldimethoxysilyl-2-bis(trimethoxysilylpropylamino)methylsilylethylene). The IR chart of the resulting compound 1 is shown in FIG. 1 The H-NMR chart is shown in FIG. 1 H-NMR analysis showed that the peak due to diethylamine was reduced, and IR analysis showed that the peak at 3393 cm -1 The peak (NH) was confirmed, confirming that the target compound was produced by the progress of the transamination reaction. Furthermore, the results of GC analysis indicated that the blending ratio of 3-aminopropyltrimethoxysilane was 0.7% by mass.

[0059] [Example 1-2]

[0060] The interior of a four-necked glass flask equipped with a stirrer, thermometer, and reflux condenser was purged with nitrogen, and 32.1 g (0.100 mol) of 1-methyldimethoxysilyl-2-bis(diethylamino)methylsilylethylene, 22.2 g (0.100 mol) of 3-(aminoethylamino)propyltrimethoxysilane, 0.054 g (0.0010 mol) of ammonium chloride, and 20 g of acetonitrile were added and refluxed for 3 hours. Analysis of the reaction solution by gas chromatography revealed the production of diethylamine, confirming the progress of the amine exchange reaction. 2.2 g of Kyoward 500SH (Kyowa Chemical Industry Co., Ltd.) was added to the resulting reaction solution, and the mixture was stirred at room temperature for 1 hour. Diethylamine and acetonitrile were stripped from the resulting mixture, and the mixture was filtered to obtain 36 g of compound 2 (1-methyldimethoxysilyl-2-(diethylamino)(trimethoxysilylpropylaminoethylamino)methylsilylethylene). The IR chart of the resulting compound 2 is shown in Figure 3. 1 The H-NMR chart is shown in FIG. 1 H-NMR analysis showed that the peak due to diethylamine was reduced, and IR analysis showed that the peak at 3380 cm -1 The peak (NH) was confirmed, confirming that the target compound was produced by the progress of the transamination reaction. Furthermore, the results of GC analysis showed that the blending ratio of 3-(aminoethylamino)propyltrimethoxysilane was 0 mass%.

[0061] [Examples 1-3]

[0062] The interior of a four-necked glass flask equipped with a stirrer, thermometer, and reflux condenser was purged with nitrogen, and 32.1 g (0.100 mol) of 1-methyldimethoxysilyl-2-bis(diethylamino)methylsilylethylene, 28.7 g (0.150 mol) of 3-aminopropylmethyldiethoxysilane, 0.027 g (0.00050 mol) of ammonium chloride, and 20 g of acetonitrile were added and refluxed for 3 hours. Analysis of the reaction solution by gas chromatography revealed the formation of diethylamine, confirming the progress of the amine exchange reaction. 1.2 g of Kyoward 500SH (Kyowa Chemical Industry Co., Ltd.) was added to the resulting reaction solution and stirred at room temperature for 1 hour. The resulting mixture was stripped of diethylamine and acetonitrile, and filtered to obtain 43 g of compound 3 (a mixture of 1-methyldimethoxysilyl-2-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethylene and 1-methyldimethoxysilyl-2-bis(methyldiethoxysilylpropylamino)methylsilylethylene). The IR chart of the resulting compound 3 is shown in FIG. 1 The H-NMR chart is shown in FIG. 1 H-NMR analysis showed that the peak due to diethylamine was reduced, and IR analysis showed that the peak at 3388 cm -1 The peak (NH) was confirmed, confirming that the target compound was produced by the progress of the transamination reaction. Furthermore, the results of GC analysis indicated that the blending ratio of 3-aminopropylmethyldiethoxysilane was 0.8 mass%.

[0063] [Examples 1-4]

[0064] The interior of a four-necked glass flask equipped with a stirrer, thermometer, and reflux condenser was purged with nitrogen, and 32.1 g (0.100 mol) of 1-methyldimethoxysilyl-2-bis(diethylamino)methylsilylethylene, 28.7 g (0.150 mol) of 3-aminopropyltriethoxysilane, 0.055 g (0.00050 mol) of diethylamine hydrochloride, and 20 g of acetonitrile were added and refluxed for 3 hours. Analysis of the reaction solution by gas chromatography revealed the formation of diethylamine, confirming the progress of the amine exchange reaction. 1.2 g of Kyoward 500SH (Kyowa Chemical Industry Co., Ltd.) was added to the resulting reaction solution, and the mixture was stirred at room temperature for 1 hour. The resulting mixture was stripped of diethylamine and acetonitrile, and filtered to obtain 47 g of compound 4 (a mixture of 1-methyldimethoxysilyl-2-(diethylamino)(triethoxysilylpropylamino)methylsilylethylene and 1-methyldimethoxysilyl-2-bis(triethoxysilylpropylamino)methylsilylethylene). The IR chart of the resulting compound 4 is shown in FIG. 1 The H-NMR chart is shown in FIG. 1 H-NMR analysis showed that the peak due to diethylamine was reduced, and IR analysis showed that the peak at 3388 cm -1 The peak (NH) was confirmed, confirming that the target compound was produced by the progress of the transamination reaction. Furthermore, the results of GC analysis indicated that the blending ratio of 3-aminopropyltriethoxysilane was 0.6 mass%.

[0065] [Examples 1-5]

[0066] The interior of a four-necked glass flask equipped with a stirrer, thermometer, and reflux condenser was purged with nitrogen, and 33.7 g (0.100 mol) of 1-trimethoxysilyl-2-bis(diethylamino)methylsilylethylene, 28.7 g (0.150 mol) of 3-aminopropylmethyldiethoxysilane, 0.027 g (0.00050 mol) of ammonium chloride, and 20 g of acetonitrile were added and refluxed for 3 hours. Analysis of the reaction solution by gas chromatography revealed the formation of diethylamine, confirming the progress of the amine exchange reaction. 1.2 g of Kyoward 500SH (Kyowa Chemical Industry Co., Ltd.) was added to the resulting reaction solution and stirred at room temperature for 1 hour. The resulting mixture was stripped of diethylamine and acetonitrile, and filtered to obtain 44 g of compound 5 (a mixture of 1-trimethoxysilyl-2-(diethylamino)(methyldiethoxysilylpropylamino)methylsilylethylene and 1-trimethoxysilyl-2-bis(methyldiethoxysilylpropylamino)methylsilylethylene). The IR chart of the resulting compound 6 is shown in FIG. 1 The H-NMR chart is shown in FIG. 1 H-NMR analysis showed that the peak due to diethylamine was reduced, and IR analysis showed that the peak at 3389 cm -1 The peak (NH) was confirmed, confirming that the target compound was produced by the progress of the transamination reaction. Furthermore, the results of GC analysis indicated that the blending ratio of 3-aminopropylmethyldiethoxysilane was 0.7 mass%.

[0067] [Examples 1-6]

[0068] The interior of a four-necked glass flask equipped with a stirrer, thermometer, and reflux condenser was purged with nitrogen, and 49.7 g (0.100 mol) of 1-trimethoxysilylethyl-3-bis(diethylamino)methylsilylethyl-1,1,3,3-tetramethyldisiloxane, 26.9 g (0.150 mol) of 3-aminopropyltrimethoxysilane, 0.027 g (0.00050 mol) of ammonium chloride, and 20 g of acetonitrile were added and refluxed for 3 hours. Analysis of the reaction solution by gas chromatography revealed the formation of diethylamine, confirming the progress of the amine exchange reaction. 1.2 g of Kyoward 500SH (Kyowa Chemical Industry Co., Ltd.) was added to the resulting reaction solution, and the mixture was stirred at room temperature for 1 hour. The resulting mixture was stripped of diethylamine and acetonitrile and filtered to obtain 59 g of compound 6 (a mixture of 1-trimethoxysilylethyl-3-(diethylamino)(trimethoxysilylpropylamino)methylsilylethyl-1,1,3,3-tetramethyldisiloxane and 1-trimethoxysilylethyl-3-bis(trimethoxysilylpropylamino)methylsilylethyl-1,1,3,3-tetramethyldisiloxane). The IR chart of the resulting compound 7 is shown in FIG. 1 The H-NMR chart is shown in FIG. 1 H-NMR analysis showed that the peak due to diethylamine was reduced, and IR analysis showed that the peak at 3394 cm -1 The peak (NH) was confirmed, confirming that the target compound was produced by the progress of the transamination reaction. Furthermore, the results of GC analysis indicated that the blending ratio of 3-aminopropyltrimethoxysilane was 0.7% by mass.

[0069] [Examples 1-7]

[0070] The interior of a four-necked glass flask equipped with a stirrer, thermometer, and reflux condenser was purged with nitrogen, and 41.1 g (0.100 mol) of trimethoxysilylpropyl-bis(diethylamino)methyl ethyl sulfide, 26.9 g (0.150 mol) of 3-aminopropyltrimethoxysilane, 0.0027 g (0.00050 mol) of ammonium chloride, and 20 g of acetonitrile were added and refluxed for 3 hours. Analysis of the reaction solution by gas chromatography revealed the formation of diethylamine, confirming the progress of the amine exchange reaction. 1.2 g of Kyoward 500SH (Kyowa Chemical Industry Co., Ltd.) was added to the resulting reaction solution and stirred at room temperature for 1 hour. The diethylamine and acetonitrile were stripped from the resulting mixture, which was then filtered to obtain 50 g of compound 7 (a mixture of trimethoxysilylpropyl-(diethylamino)(trimethoxysilylpropylamino)methyl ethyl sulfide and trimethoxysilylpropyl-bis(trimethoxysilylpropylamino)methyl ethyl sulfide). The IR chart of the obtained compound 8 is shown in FIG. 1 The H-NMR chart is shown in FIG. 1 H-NMR analysis showed that the peak due to diethylamine was reduced, and IR analysis showed that the peak at 3389 cm -1 The peak (NH) was confirmed, confirming that the target compound was produced by the progress of the transamination reaction. Furthermore, the results of GC analysis indicated that the blending ratio of 3-aminopropyltrimethoxysilane was 0.8% by mass.

[0071] [Examples 1-8]

[0072] The interior of a four-necked glass flask equipped with a stirrer, thermometer, and reflux condenser was purged with nitrogen, and 55.7 g (0.100 mol) of 1-trimethoxysilylethyldimethylsilyl-4-bis(diethylamino)methylsilylethyldimethylsilylbenzene, 26.9 g (0.150 mol) of 3-aminopropyltrimethoxysilane, 0.027 g (0.00050 mol) of ammonium chloride, and 20 g of acetonitrile were added and refluxed for 3 hours. Analysis of the reaction solution by gas chromatography revealed the formation of diethylamine, confirming the progress of the amine exchange reaction. 1.2 g of Kyoward 500SH (Kyowa Chemical Industry Co., Ltd.) was added to the resulting reaction solution, and the mixture was stirred at room temperature for 1 hour. The resulting mixture was stripped of diethylamine and acetonitrile, and filtered to obtain 62 g of compound 8 (a mixture of 1-trimethoxysilylethyldimethylsilyl-4-(diethylamino)(trimethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene and 1-trimethoxysilylethyldimethylsilyl-4-bis(trimethoxysilylpropylamino)methylsilylethyldimethylsilylbenzene). The IR chart of the resulting compound 10 is shown in FIG. 1 The H-NMR chart is shown in FIG. 1 H-NMR analysis showed that the peak due to diethylamine was reduced, and IR analysis showed that the peak at 3393 cm -1 The peak (NH) was confirmed, confirming that the target compound was produced by the progress of the transamination reaction. Furthermore, the results of GC analysis indicated that the blending ratio of 3-aminopropyltrimethoxysilane was 0.7% by mass.

[0073] [Examples 1-9]

[0074] The same procedure as in Example 1-3 was carried out except that ammonium chloride was replaced with 0.055 g (0.00050 mol) of diethylamine hydrochloride, and 47 g of product was obtained. 1 H-NMR analysis confirmed that the same compound 3 as in Example 1-3 was produced. Furthermore, the results of GC analysis showed that the blending ratio of 3-aminopropylmethyldiethoxysilane was 0.7% by mass.

[0075] [Examples 1-10]

[0076] The same procedure as in Example 1-4 was repeated except that diethylamine hydrobromide was used in place of diethylamine hydrochloride (0.0077 g, 0.00050 mol), and 46 g of the product was obtained. 1 H-NMR analysis confirmed that the same compound 4 as in Example 1-4 was produced.

[0077] [Examples 1-11]

[0078] The same procedure as in Example 1-4 was carried out except that diethylamine hydrochloride was replaced with 0.0066 g (0.00050 mol) of ammonium sulfate, and 48 g of product was obtained. 1 H-NMR analysis confirmed that the same compound 4 as in Example 1-4 was produced.

[0079] [Examples 1-12]

[0080] The same procedure as in Example 1-4 was carried out except that diethylamine hydrochloride was replaced with 0.086 g (0.0050 mol) of p-toluenesulfonamide, and 47 g of product was obtained. 1 H-NMR analysis confirmed that the same compound 4 as in Example 1-4 was produced.

[0081] Example 1-13 The same procedure as in Example 1-4 was repeated, except that the amount of 3-aminopropyltriethoxysilane used was 37.6 g (0.170 mol). Analysis of the reaction solution by gas chromatography revealed that diethylamine was produced, confirming the progress of the amine exchange reaction, but that 3-aminopropyltriethoxysilane remained. 57 g of product was obtained. 1 H-NMR analysis showed that the peaks derived from diethylamine were reduced. 1 H-NMR analysis confirmed that the same compound 4 as in Examples 1-4 was produced. GC analysis revealed that the blending ratio of 3-aminopropyltriethoxysilane was 7% by mass. It was confirmed that the composition was composed of compound 4 and 3-aminopropyltriethoxysilane.

[0082] [Synthesis Example] Synthesis of 1-methyldimethoxysilyl-2-bis(diethylamino)methylsilylethylene

[0083] According to the procedure of Example 2 of Patent Document 1, a comparative compound (1-methyldimethoxysilyl-2-bis(diethylamino)methylsilylethylene) represented by the above structural formula was obtained.

[0084] Example 2-1 Compound 1 obtained in Example 1-1 was applied to a cleaned polished steel plate (10 cm x 15 cm) and a soda glass (7 cm x 15 cm) using a bar coater to a wet thickness of 30 μm, to obtain test specimens. The obtained polished steel plate test specimens were left to stand in an environment of 25°C and 50% relative humidity, and the time until the test specimens were dry to the touch (tack-free time), that is, the time until Compound 1 no longer adheres to the fingertips when touching the surface of the test specimen, was measured using the method specified in JIS K5600-1-1. The results are shown in Table 1. Furthermore, after the test specimens had reached dry to the touch, they were left to stand for one day at room temperature (15 to 20°C), and the appearance of the coating was visually evaluated according to the following criteria. ◯: No change in transparent coating ×: Occurrence of cracks and peeling Whitening: Whitening of coating The coated soda glass test pieces were left to stand at room temperature (around 23°C) for one week, and the hardness of the coating was measured by the method specified in JIS K5600-5-4. The results are shown in Table 1.

[0085] [Examples 2-2 to 2-8 and Comparative Examples] Evaluations were carried out in the same manner as in Example 2-1, except that Compound 1 was replaced with Compounds 2 to 8 obtained in Examples 1-2 to 1-8 and the comparative compounds obtained in Synthesis Examples. The results are shown in Table 1.

[0086]

[0087] As shown in Table 1, the results of Examples 2-1 to 2-8 indicate that the bissilyl compound of the present invention having a silyl group substituted with an organoxysilylalkylamino group can form a film in a short time without the addition of a catalyst, and the resulting film not only has sufficient hardness with a pencil hardness of 3H or more, but also does not suffer from cracking or whitening. On the other hand, the results of the comparative example indicate that the comparative compound was able to form a film without the addition of a catalyst, but required a long time for film formation. Furthermore, the resulting film also suffered from whitening and cracking.

Claims

1. A bissilyl compound having a silyl group substituted with an organoxysilylalkylamino group, represented by the following general formula (1): (In the formula, R 1 , R 2 , R 4 ~R 7 , R 9 and R 10 each independently represents an unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, 6 and R 7 may be bonded to each other to form a ring structure having 2 to 10 carbon atoms together with the nitrogen atom to which they are bonded, and the ring structure may contain at least one element selected from the group consisting of O and N in addition to the nitrogen atom in a part of the ring; R 3 and R 8 each independently represents a divalent hydrocarbon group having 2 to 10 carbon atoms which may contain at least one element selected from the group consisting of O, N, S, and Si; a represents 0, 1, or 2; l and m each represent 0, 1, or 2; n represents 1, 2, or 3; and p represents 0, 1, or 2.

2. A composition comprising the bissilyl compound having a silyl group substituted with an organoxysilylalkylamino group as described in claim 1, and an amino group-containing organoxysilane compound represented by the following general formula (2): (In the formula, R 8 ~R 10 and p have the same meaning as above.

3. A composition comprising the bissilyl compound having a silyl group substituted with an organoxysilylalkylamino group as defined in claim 1 and an aprotic solvent.

4. The composition of claim 2 further comprising an aprotic solvent.

5. General formula (2) (In the formula, R 8 ~R 10 and p are as defined above), and a primary aminoalkylorganoxysilane compound represented by the following general formula (3): (In the formula, R 1 ~R 7and m are as defined above.) in the presence of an acidic compound having a pKa of 4 to 12 and an aprotic polar solvent, the method for producing a bissilyl compound having a silyl group substituted with an organoxysilylalkylamino group according to claim 1, comprising the step of subjecting a bissilyl compound represented by the following formula (I):

6. A method for producing a bissilyl compound having a silyl group substituted with an organoxysilylalkylamino group as claimed in claim 5, further comprising a step of neutralizing said acidic compound with a solid basic compound.

7. The method for producing a bissilyl compound having a silyl group substituted with an organoxysilylalkylamino group according to claim 5 or 6, wherein the acidic compound having a pKa of 4 to 12 is an amine salt.

8. The method for producing a bissilyl compound having a silyl group substituted with an organoxysilylalkylamino group according to claim 5 or 6, wherein the aprotic polar solvent is a nitrile compound.

9. A cured product obtained by curing the compound according to claim 1 or the composition according to claim 2.

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