JP2010270049A - Organosilicon compound, and rubber composition, tire, primer composition, coating composition and adhesive, each using the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a new compound which can largely reduce the hysteresis loss of a rubber composition and can greatly improve the abrasion resistance, to provide a rubber composition containing the compound, and to provide a tire using the rubber composition. <P>SOLUTION: There are provided: the organosilicon compound represented by a specific structural formula; a rubber composition prepared by compounding a rubber component (A) comprising natural rubber and/or a diene-based synthetic rubber with an inorganic filler (B) and the organosilicon compound (C); and a tire using the rubber composition. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

  The present invention relates to an organosilicon compound, a rubber composition containing the organosilicon compound, a primer composition, a coating composition and an adhesive, and a tire using the rubber composition, and in particular, hysteresis loss of the rubber composition. It is related with the organosilicon compound which can improve abrasion resistance while lowering.

  Recently, from the viewpoint of vehicle safety, it is required to improve the safety of tires on wet road surfaces. In addition, from the viewpoint of reducing carbon dioxide emissions due to increased interest in environmental issues, it is also required to further reduce fuel consumption of vehicles.

  In response to these demands, conventionally, as a technique for achieving both improvement in performance on a wet road surface of a tire and reduction in rolling resistance, a technique of using an inorganic filler such as silica as a filler of a rubber composition used for a tire tread is known. It is known to be effective. However, the rubber composition containing an inorganic filler such as silica reduces the rolling resistance of the tire, improves the braking performance on the wet road surface, and improves the handling stability, but has a high unvulcanized viscosity and multistage kneading. Therefore, there is a problem in workability. Therefore, in a rubber composition containing an inorganic filler such as silica, the breaking strength and wear resistance are greatly reduced, and problems such as vulcanization delay and poor filler dispersion occur.

  Therefore, when an inorganic filler such as silica is blended with the rubber composition for tread, the unvulcanized viscosity of the rubber composition is reduced, the modulus and wear resistance are ensured, and the hysteresis loss is further reduced. It is essential to add a silane coupling agent. The silane coupling agent is also widely used for applications other than rubber compositions such as primer compositions, coating compositions and adhesives.

US Pat. No. 3,842,111 US Pat. No. 3,873,489

  However, since the silane coupling agent is expensive, the blending cost increases due to the blending of the silane coupling agent. Also, the addition of a dispersion improver decreases the unvulcanized viscosity of the rubber composition and improves workability, but also decreases the wear resistance. Furthermore, when the dispersion improver is a highly ionic compound, a decrease in workability such as roll adhesion is also observed. Furthermore, as a result of investigation by the present inventors, even when an inorganic filler such as silica is blended as a filler, even when a conventional silane coupling agent is added, the hysteresis loss of the rubber composition is reduced and the wear resistance is reduced. However, it was found that there was still room for improvement. Silane coupling agents are also used in primer compositions, coating compositions, adhesives, etc. as described above. However, when the adherend is a hybrid material composed of an organic material and an inorganic material, a conventional silane cup is used. It has been found that primer compositions, coating compositions, adhesives, and the like using a ring agent do not have sufficient adhesion and affinity at the interface between the organic material and the inorganic material, and still have room for improvement.

  Accordingly, an object of the present invention is to solve the above-mentioned problems of the prior art, and to provide a novel compound capable of greatly reducing the hysteresis loss of the rubber composition and greatly improving the wear resistance. . Another object of the present invention is to provide a rubber composition, a primer composition, a coating composition and an adhesive containing such a compound, and a tire using the rubber composition.

  As a result of intensive studies to achieve the above-mentioned object, the present inventors have found that the organosilicon compound represented by a specific structural formula has a high reaction rate with an inorganic filler such as silica. By blending with the rubber component together with the filler, the efficiency of the coupling reaction is improved, the hysteresis loss of the rubber composition is greatly reduced, and the wear resistance is greatly improved. The present inventors have found that it is effective in improving the adhesion and affinity at the interface between the hybrid material composed of an organic material and an inorganic material, and completed the present invention.

［式中、Ｒ¹、Ｒ²及びＲ³は、少なくとも一つが下記一般式(II)又は式(III)：

（式中、Ｍは−Ｏ−又は−ＣＨ₂−で、Ｘ及びＹはそれぞれ独立して−Ｏ−、−ＮＲ⁸−又は−ＣＨ₂−で、Ｒ⁶は−ＯＲ⁸、−ＮＲ⁸Ｒ⁹又は−Ｒ⁸で、Ｒ⁷は−ＮＲ⁸Ｒ⁹、−ＮＲ⁸−ＮＲ⁸Ｒ⁹又は−Ｎ＝ＮＲ⁸で、但し、Ｒ⁸は−Ｃ_nＨ_2n+1であり、Ｒ⁹は−Ｃ_qＨ_2q+1であり、ｌ、ｍ、ｎ及びｑはそれぞれ独立して０〜２０である）で表わされ、その他が−Ｍ−Ｃ_lＨ_2l+1（ここで、Ｍ及びｌは上記と同義である）或いは−（Ｍ−Ｃ_lＨ_2l）_yＣ_sＨ_2s+1（ここで、Ｍは上記と同義であり、ｙ及びｓはそれぞれ独立して１〜２０である）で表わされ、但し、Ｒ¹、Ｒ²及びＲ³の一つ以上はＭが−Ｏ−であり、
Ｒ⁴は下記一般式(IV)又は式(V)：

（式中、Ｍ、Ｘ、Ｙ、Ｒ⁶、ｌ及びｍは上記と同義であり、Ｒ¹⁰は−ＮＲ⁸−、−ＮＲ⁸−ＮＲ⁸−又は−Ｎ＝Ｎ−で、但し、Ｒ⁸は上記と同義である）或いは−Ｍ−Ｃ_lＨ_2l−（ここで、Ｍ及びｌは上記と同義である）で表され、
Ｒ⁵は上記一般式(II)又は式(III)或いは−Ｃ_lＨ_2l−Ｒ¹¹（ここで、Ｒ¹¹は−ＮＲ⁸Ｒ⁹、−ＮＲ⁸−ＮＲ⁸Ｒ⁹、−Ｎ＝ＮＲ⁸、Ｈ、又は−Ｍ−Ｃ_mＨ_2m+1或いは炭素数６〜２０の芳香族炭化水素基であり、但し、Ｒ⁸、Ｒ⁹、Ｍ、ｌ及びｍは上記と同義である）で表わされる］で表わされることを特徴とする。 That is, the first organosilicon compound of the present invention has the following general formula (I):

[In the formula, at least one of R ¹ , R ² and R ³ is represented by the following general formula (II) or formula (III):

(In the formula, M is —O— or —CH ₂ —, X and Y are each independently —O—, —NR ⁸ — or —CH ₂ —, and R ⁶ is —OR ⁸ , —NR ⁸ R. ⁹ or -R ⁸ , R ⁷ is -NR ⁸ R ⁹ , -NR ⁸ -NR ⁸ R ⁹ or -N = NR ⁸ , provided that R ⁸ is -C _n H _{2n + 1} and R ⁹ is a _{-C q H 2q + 1, l} , m, n and q are represented by independently 0 to 20), others _{-M-C l H 2l + 1} ( wherein, M and l is as defined above) or _{- (M-C l H 2l} ) y C s H 2s + 1 ( wherein, M is as defined above, y and s are 1 to 20 independently Wherein at ^{least one} of R ¹ , R ² and R ³ is M is —O—,
R ⁴ represents the following general formula (IV) or formula (V):

(Wherein, M, X, Y, R 6, l and m are as defined above, R ¹⁰ is ^{-NR 8 -, - NR 8 -NR} 8 - or -N = N-a, provided that, R ⁸ Is as defined above) or -M-C ₁ H _2l- (wherein M and l are as defined above),
R ⁵ represents the above general formula (II), formula (III), or —C ₁ H _2l —R ¹¹ (where R ¹¹ represents —NR ⁸ R ⁹ , —NR ⁸ —NR ⁸ R ⁹ , —N═NR ^8). , H, or —M—C _m H _{2m + 1} or an aromatic hydrocarbon group having 6 to 20 carbon atoms, provided that R ⁸ , R ⁹ , M, l and m are as defined above. It is characterized by being expressed.

［式中、Ｗは−ＮＲ⁸−、−Ｏ−又は−ＣＲ⁸Ｒ¹⁵−（ここで、Ｒ¹⁵は−Ｒ⁹又は−Ｃ_mＨ_2m−Ｒ⁷であり、但し、Ｒ⁷は−ＮＲ⁸Ｒ⁹、−ＮＲ⁸−ＮＲ⁸Ｒ⁹又は−Ｎ＝ＮＲ⁸であり、Ｒ⁸は−Ｃ_nＨ_2n+1で、Ｒ⁹は−Ｃ_qＨ_2q+1で、ｍ、ｎ及びｑはそれぞれ独立して０〜２０である）で表わされ、
Ｒ¹²及びＲ¹³はそれぞれ独立して−Ｍ−Ｃ_lＨ_2l−（ここで、Ｍは−Ｏ−又は−ＣＨ₂−で、ｌは０〜２０である）で表わされ、
Ｒ¹⁴は−Ｍ−Ｃ_lＨ_2l+1又は−Ｍ−Ｃ_lＨ_2l−Ｒ⁷（ここで、Ｍ、Ｒ⁷及びｌは上記と同義である）或いは−（Ｍ−Ｃ_lＨ_2l）_yＣ_sＨ_2s+1（ここで、Ｍ及びｌは上記と同義であり、ｙ及びｓはそれぞれ独立して１〜２０である）で表わされ、但し、Ｒ¹²、Ｒ¹³及びＲ¹⁴の一つ以上はＭが−Ｏ−であり、
Ｒ⁴は下記一般式(IV)又は式(V)：

（式中、Ｍ、ｌ及びｍは上記と同義であり、Ｘ及びＹはそれぞれ独立して−Ｏ−、−ＮＲ⁸−又は−ＣＨ₂−で、Ｒ⁶は−ＯＲ⁸、−ＮＲ⁸Ｒ⁹又は−Ｒ⁸で、Ｒ¹⁰は−ＮＲ⁸−、−ＮＲ⁸−ＮＲ⁸−又は−Ｎ＝Ｎ−であり、但し、Ｒ⁸及びＲ⁹は上記と同義である）或いは−Ｍ−Ｃ_lＨ_2l−（ここで、Ｍ及びｌは上記と同義である）で表され、
Ｒ⁵は下記一般式(II)又は式(III)：

（式中、Ｍ、Ｘ、Ｙ、Ｒ⁶、Ｒ⁷、ｌ及びｍは上記と同義である）或いは−Ｃ_lＨ_2l−Ｒ¹¹（ここで、Ｒ¹¹は−ＮＲ⁸Ｒ⁹、−ＮＲ⁸−ＮＲ⁸Ｒ⁹、−Ｎ＝ＮＲ⁸、Ｈ、又は−Ｍ−Ｃ_mＨ_2m+1或いは炭素数６〜２０の芳香族炭化水素基であり、但し、Ｒ⁸、Ｒ⁹、Ｍ、ｌ及びｍは上記と同義である）で表わされる］で表わされることを特徴とする。 The second organosilicon compound of the present invention has the following general formula (VI):

Wherein W is —NR ⁸ —, —O— or —CR ⁸ R ¹⁵ — (wherein R ¹⁵ is —R ⁹ or —C _m H _2m —R ⁷ , where R ⁷ is —NR ⁸ R ⁹ , —NR ⁸ —NR ⁸ R ⁹ or —N═NR ⁸ , R ⁸ is —C _n H _{2n + 1} , R ⁹ is —C _q H _{2q + 1} , m, n and q Are each independently 0 to 20),
R ¹² and R ¹³ are each independently represented by —M—C ₁ H _{2 1} — (wherein M is —O— or —CH ₂ —, and 1 is 0 to 20),
R ¹⁴ is -M-C _l H _{2l + 1} or ^{_{-M-C l H 2l -R 7}} ( wherein, M, R ⁷ and l have the same meanings as mentioned above), or _{- (M-C l H 2l} ) _y C _s H _{2s + 1} (wherein M and l are as defined above, y and s are each independently 1 to 20), provided that R ¹² , R ¹³ and R ¹⁴ One or more of M is -O-
R ⁴ represents the following general formula (IV) or formula (V):

Wherein M, l and m are as defined above, X and Y are each independently —O—, —NR ⁸ — or —CH ₂ —, and R ⁶ is —OR ⁸ , —NR ⁸ R ⁹ or -R ^8, R ¹⁰ is ^{-NR 8 -, - NR 8 -NR} 8 - or -N = a N-, provided that, R ⁸ and R ⁹ are as defined above) or -M-C _l H _2l- (wherein M and l are as defined above),
R ⁵ represents the following general formula (II) or formula (III):

(Wherein, M, X, Y, R ⁶ , R ⁷ , l and m are as defined above) or —C ₁ H _2l —R ¹¹ (where R ¹¹ is —NR ⁸ R ⁹ , —NR ⁸ —NR ⁸ R ⁹ , —N═NR ⁸ , H, or —M—C _m H _{2m + 1} or an aromatic hydrocarbon group having 6 to 20 carbon atoms, provided that R ⁸ , R ⁹ , M, l and m are the same as defined above)].

  In the organosilicon compound of the present invention, the M is preferably —O—.

In the organosilicon compound represented by the above formula (I), at least one of R ¹ , R ² and R ³ is —O—C ₁ H _{2 1} —R ⁷ (where R ⁷ and 1 are as defined above). And the others are represented by —O—C ₁ H _{2l + 1} (where l is as defined above),
R ⁴ is represented by —C ₁ H _2l — (wherein l is as defined above),
The R ⁵ is preferably represented by —C ₁ H _2l —R ¹¹ (where R ¹¹ and l are as defined above).

In the organosilicon compound represented by the above formula (I), at least one of R ¹ , R ² and R ³ is —O—C ₁ H _{2 1} —NR ⁸ R ⁹ (where R ⁸ , R ⁹ and l is as defined above),
A linear or branched alkyl group represented by R ⁵ —C _l H _{2l + 1} (wherein l is as defined above), or an aromatic hydrocarbon group having 6 to 20 carbon atoms; More preferably it is.

In the organosilicon compound represented by the above formula (VI), the W is represented by —NR ⁸ — (wherein R ⁸ is as defined above),
R ¹² and R ¹³ are each independently represented by —O—C ₁ H _2l — (wherein l is as defined above),
R ¹⁴ is represented by —O—C _l H _2l —R ⁷ (wherein R ⁷ and l are as defined above),
R ⁴ is represented by —C ₁ H _2l — (wherein l is as defined above),
A linear or branched alkyl group, or an aromatic hydrocarbon group having 6 to 20 carbon atoms, in which R ⁵ is represented by —C ₁ H _{2l + 1} (wherein l is as defined above). Is preferred.

In the organosilicon compound represented by the above formula (VI), the W is represented by —O— or —CR ⁸ R ⁹ — (wherein R ⁸ and R ⁹ are as defined above),
R ¹² and R ¹³ are each independently represented by —O—C ₁ H _2l — (wherein l is as defined above),
R ¹⁴ is represented by —O—C ₁ H _{2 1} —NR ⁸ R ⁹ (wherein R ⁸ , R ⁹ and l are as defined above),
R ⁴ is represented by —C ₁ H _2l — (wherein l is as defined above),
It is also preferable that R ⁵ is represented by —C _l H _{2l + 1} (where l is as defined above).

  Moreover, the rubber composition of the present invention comprises an inorganic filler (B) and the above organosilicon compound (C) in a rubber component (A) made of natural rubber and / or a diene synthetic rubber. It is characterized by becoming.

The rubber composition of the present invention is obtained by blending 5 to 140 parts by mass of the inorganic filler (B) with respect to 100 parts by mass of the rubber component (A) composed of the natural rubber and / or the diene synthetic rubber.
Furthermore, it is preferable that 1-20 mass% of the compounding quantity of the said inorganic filler (B) is included for the said organosilicon compound (C).

In a preferred example of the rubber composition of the present invention, the inorganic filler (B) is silica or aluminum hydroxide. Wherein the silica is preferably BET surface area of 40~350 m ² / g.

  The tire of the present invention is characterized by using the above rubber composition.

  Furthermore, the primer composition of the present invention is characterized by containing the above organosilicon compound, the coating composition of the present invention is characterized by comprising the above organosilicon compound, and the adhesive of the present invention comprises the above organosilicon compound. It is characterized by including a compound.

  According to the present invention, it has a specific molecular structure containing a nitrogen atom (N) and a sulfur atom (S) and having a silicon-oxygen bond (Si-O), and greatly reduces the hysteresis loss of the rubber composition. In addition, it is possible to provide an organosilicon compound capable of greatly improving wear resistance. Moreover, the rubber composition containing this organosilicon compound, the tire using this rubber composition, and the primer composition, coating composition, and adhesive agent containing this organosilicon compound can be provided.

<Organic silicon compound>
The present invention is described in detail below. The first organosilicon compound of the present invention is represented by the above general formula (I), and the second organosilicon compound of the present invention is represented by the above general formula (VI). These organosilicon compounds of the present invention may be used singly or in combination of two or more. The organosilicon compound of the present invention contains a nitrogen-containing functional group such as an amino group, an imino group, a substituted amino group, or a substituted imino group that has a high affinity with the surface of an inorganic filler such as silica, so that the nitrogen atom is not shared. The electron pair can participate in the reaction between the organosilicon compound and the inorganic filler, and the coupling reaction rate is high. Therefore, by adding the organosilicon compound of the present invention to the inorganic filler-containing rubber composition instead of the conventional silane coupling agent, the coupling efficiency is improved, and as a result, the hysteresis loss of the rubber composition is reduced. It is possible to greatly improve the wear resistance while greatly reducing. In addition, since the organosilicon compound of the present invention has high addition efficiency, a high effect can be obtained even in a small amount, and it contributes to reduction of the blending cost.

  The organosilicon compound of the present invention preferably has 1 to 6 silicon-oxygen bonds (Si-O). When the organosilicon compound has 1 to 6 silicon-oxygen bonds (Si-O), the reactivity with an inorganic filler such as silica is high, and the coupling efficiency is further improved.

<< Compound of Formula (I) >>
In the general formula (I), at least one of R ¹ , R ² and R ³ is represented by the above general formula (II) or formula (III), and the other is -M-C ₁ H _{2l + 1} (here M is —O— or —CH ₂ —, and l is 0 to 20) or — (M—C ₁ H _2l ) _y C _s H _{2s + 1} (where M is —O— or —CH ₂ —, 1 is 0-20, and y and s are each independently 1-20. Provided that M is —O— in one or more of R ¹ , R ² and R ³ . In addition, since l is 0 to 20, -C _l H _{2l + 1} is hydrogen or an alkyl group having 1 to 20 carbon atoms. Here, as the alkyl group having 1 to 20 carbon atoms, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, dodecyl group, tridecyl group, tetradecyl group, Examples include a pentadecyl group, a hexadecyl group, a heptadecyl group, a stearyl group, and the like. The alkyl group may be linear or branched. In addition, since l is 0 to 20, —C ₁ H _2l — is a single bond or an alkylene group having 1 to 20 carbon atoms. Here, as a C1-C20 alkylene group, a methylene group, ethylene group, trimethylene group, propylene group, tetramethylene group, hexamethylene group, octamethylene group, decamethylene group, dodecamethylene group, tetradecamethylene group, A hexadecamethylene group, an octadecamethylene group and the like can be mentioned, and the alkylene group may be linear or branched. Further, -C _s H _{2s + 1,} since s is 1 to 20, an alkyl group having 1 to 20 carbon atoms. Here, as the alkyl group having 1 to 20 carbon atoms, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, dodecyl group, tridecyl group, tetradecyl group, Examples include a pentadecyl group, a hexadecyl group, a heptadecyl group, a stearyl group, and the like. The alkyl group may be linear or branched. Further, y is a number of repetitions of the (M-C _l H _2l) units is 1-20. In addition, it is preferable that M in the (M-C ₁ H _2l ) unit is —O— (oxygen).

In the above formulas (II) and (III), M is —O— or —CH ₂ —, and 1 is 0-20. In the above formula (II), m is 0-20.

In the above formula (II), X and Y are each independently —O—, —NR ⁸ — or —CH ₂ —. Wherein, R ⁸ is -C _n H _{2n + 1, n} is 0 to 20. Note that -C _n H _{2n + 1} is hydrogen or an alkyl group having 1 to 20 carbon atoms because n is 0 to 20. Here, as the alkyl group having 1 to 20 carbon atoms, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, dodecyl group, tridecyl group, tetradecyl group, Examples include a pentadecyl group, a hexadecyl group, a heptadecyl group, a stearyl group, and the like. The alkyl group may be linear or branched.

In the above formula (II), R ⁶ is —OR ⁸ , —NR ⁸ R ⁹ or —R ⁸ . Wherein, R ⁸ is _{-C n H 2n + 1, R} 9 is -C _q H _{2q + 1,} n and q are 0 to 20 independently. Note that the -C _n H _{2n + 1,} are as described above, -C _q H _{2q + 1,} since q is 0 to 20, hydrogen or an alkyl group having 1 to 20 carbon atoms. Here, as the alkyl group having 1 to 20 carbon atoms, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, dodecyl group, tridecyl group, tetradecyl group, Examples include a pentadecyl group, a hexadecyl group, a heptadecyl group, a stearyl group, and the like. The alkyl group may be linear or branched.

In the above formula (III), R ⁷ is —NR ⁸ R ⁹ , —NR ⁸ —NR ⁸ R ⁹ or —N═NR ⁸ . Wherein, R ⁸ is _{-C n H 2n + 1, R} 9 is -C _q H _{2q + 1,} n and q are 0 to 20 independently. Note that the -C _n H _{2n + 1} and -C _q H _{2q + 1,} is as described above.

In the above general formula (I), R ⁴ is represented by the above general formula (IV) or (V), or -M-C ₁ H _2l- , particularly -C ₁ H _2l-. Wherein M is —O— or —CH ₂ — and l is 0-20. In addition, since l is 0 to 20, —C ₁ H _2l — is a single bond or an alkylene group having 1 to 20 carbon atoms. Here, as a C1-C20 alkylene group, a methylene group, ethylene group, trimethylene group, propylene group, tetramethylene group, hexamethylene group, octamethylene group, decamethylene group, dodecamethylene group, tetradecamethylene group, A hexadecamethylene group, an octadecamethylene group and the like can be mentioned, and the alkylene group may be linear or branched.

In the above formulas (IV) and (V), M is —O— or —CH ₂ —, and l and m are 0-20. -C _l H _2l- in the formulas (IV) and (V) is as described above. Further, -C _m H _2m in formula (IV) and (V) - Since m is 0 to 20, a single bond or an alkylene group with 1 to 20 carbon atoms. Here, as a C1-C20 alkylene group, a methylene group, ethylene group, trimethylene group, propylene group, tetramethylene group, hexamethylene group, octamethylene group, decamethylene group, dodecamethylene group, tetradecamethylene group, A hexadecamethylene group, an octadecamethylene group and the like can be mentioned, and the alkylene group may be linear or branched. In the above formula (IV), X and Y are each independently —O—, —NR ⁸ — or —CH ₂ —, and R ⁶ is —OR ⁸ , —NR ⁸ R ⁹ or —R ⁸ . is there. R ⁸ and R ⁹ are as described above. Further, in the above formula (V), R ¹⁰ is —NR ⁸ —, —NR ⁸ —NR ⁸ — or —N═N—, wherein R ⁸ is —C _n H _{2n + 1} , the -C _n H _{2n + 1,} as described above.

R ⁵ in the above general formula (I) is represented by the above general formula (II) or (III), or —C ₁ H _2l —R ¹¹ , particularly —C ₁ H _{2l + 1} . Preferably, R ¹¹ is —NR ⁸ R ⁹ , —NR ⁸ —NR ⁸ R ⁹ , —N═NR ⁸ , H, or —M—C _m H _{2m + 1} or 6 carbon atoms. -20 aromatic hydrocarbon groups, provided that R ⁸ , R ⁹ , M, l and m are as defined above. Incidentally, -C _l H _2l - for and -C _l H _{2l + 1} is are as described above. Further, -C _m H _{2m + 1,} since m is 0-20, a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, wherein the alkyl group having 1 to 20 carbon atoms, a methyl group, Ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, stearyl group, etc. The alkyl group may be linear or branched. Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms include aryl groups such as phenyl group, tolyl group, xylyl group, cumenyl group, naphthylene group and tolylene group, and aralkyl groups such as benzyl group and phenethyl group. .

In the compound of the above formula (I), M is preferably —O— (oxygen). In this case, M is -CH ₂ - are highly reactive with an inorganic filler such as silica as compared to compounds wherein.

In the compound of the above formula (I), at least one of R ¹ , R ² and R ³ is represented by —O—C ₁ H _2l —R ⁷ , and the other is —O—C ₁ H _{2l +.} is preferably represented by _1, the R ⁴ is -C _l H _2l - is preferably represented by the above R ⁵ is preferably represented by -C _l H _2l -R ^11.

Further, in the compound of the above formula (I), it is more preferable that at least one of R ¹ , R ² and R ³ is represented by —O—C ₁ H _{2 1} —NR ⁸ R ⁹ , and R ⁴ represents — Preferably, it is represented by C ₁ H _2l —, and the above R ⁵ is a linear or branched alkyl group represented by —C ₁ H _{2l + 1} , or an aromatic hydrocarbon group having 6 to 20 carbon atoms. Is more preferable.

<< Compound of Formula (VI) >>
In the above general formula (VI), W is represented by —NR ⁸ —, —O— or —CR ⁸ R ¹⁵ —, wherein R ¹⁵ is —R ⁹ or —C _m H _2m —R ⁷ . Provided that R ⁷ is —NR ⁸ R ⁹ , —NR ⁸ —NR ⁸ R ⁹ or —N═NR ⁸ , R ⁸ is —C _n H _{2n + 1} , and R ⁹ is —C _q H _{2q. +1} , m, n, and q are each independently 0-20. Incidentally, -C _m H _2m -, since m is 0-20, a single bond or an alkylene group with 1 to 20 carbon atoms. Here, as a C1-C20 alkylene group, a methylene group, ethylene group, trimethylene group, propylene group, tetramethylene group, hexamethylene group, octamethylene group, decamethylene group, dodecamethylene group, tetradecamethylene group, A hexadecamethylene group, an octadecamethylene group and the like can be mentioned, and the alkylene group may be linear or branched. Moreover, -C _n H _{2n + 1} and -C _q H _{2q + 1,} since n and q are 0 to 20, hydrogen or an alkyl group having 1 to 20 carbon atoms. Here, as the alkyl group having 1 to 20 carbon atoms, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, dodecyl group, tridecyl group, tetradecyl group, Examples include a pentadecyl group, a hexadecyl group, a heptadecyl group, a stearyl group, and the like. The alkyl group may be linear or branched.

In the general formula (VI), R ¹² and R ¹³ are each independently -M-C _l H _2l - is represented by, R ¹⁴ is -M-C _l H _{2l + 1} or -M-C _l H _2l -R ^7, or - is represented by _{(M-C l H 2l)} y C s H 2s + 1, wherein, M is -O- or -CH ₂ -, R ⁷ is -NR ⁸ R ⁹ a -NR ⁸ -NR ⁸ R ⁹ or -N = NR ^8, R ⁸ is -C _n H _{2n + 1,} with R ⁹ is _{-C q H 2q + 1, l} , n and q are each independently And y and s are each independently 1-20. However, in one or more of R ¹² , R ¹³ and R ¹⁴ , M is —O—. In addition, since l is 0 to 20, —C ₁ H _2l — is a single bond or an alkylene group having 1 to 20 carbon atoms. Here, the alkylene group having 1 to 20 carbon atoms includes a methylene group, And ethylene group, trimethylene group, propylene group, tetramethylene group, hexamethylene group, octamethylene group, decamethylene group, dodecamethylene group, tetradecamethylene group, hexadecamethylene group, octadecamethylene group, etc. May be linear or branched. -C _l H _{2l + 1} is hydrogen or an alkyl group having 1 to 20 carbon atoms because l is 0 to 20, wherein the alkyl group having 1 to 20 carbon atoms is a methyl group, Ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, stearyl group, etc. The alkyl group may be linear or branched. Note that the -C _n H _{2n + 1} and -C _q H _{2q + 1,} is as described above. Further, -C _s H _{2s + 1,} since s is 1 to 20, an alkyl group having 1 to 20 carbon atoms, wherein the alkyl group having 1 to 20 carbon atoms, a methyl group, an ethyl group Propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, stearyl group, etc., the alkyl group May be linear or branched. Further, y is a number of repetitions of the (M-C _l H _2l) units is 1-20. In addition, it is preferable that M in the (M-C ₁ H _2l ) unit is —O— (oxygen).

In the general formula (VI), R ⁴ is represented by the above general formula (IV) or (V), or -M-C ₁ H _2l- , particularly -C ₁ H _2l-. Where M is —O— or —CH ₂ — and l is 0-20. In addition, -C _l H _2l- is as described above.

In the above formulas (IV) and (V), M is —O— or —CH ₂ —, and l and m are 0-20. In the above formula (IV), X and Y are each independently —O—, —NR ⁸ — or —CH ₂ —, and R ⁶ is —OR ⁸ , —NR ⁸ R ⁹ or —R ⁸ . Yes, where R ⁸ is —C _n H _{2n + 1} and R ⁹ is —C _q H _{2q + 1} . Further, in the above formula (V), R ¹⁰ is —NR ⁸ —, —NR ⁸ —NR ⁸ —, or —N═N—, wherein R ⁸ is —C _n H _{2n + 1} . Note that the -C _n H _{2n + 1} and -C _q H _{2q + 1,} is as described above.

In the general formula (VI), R ⁵ is represented by the general formula (II) or (III), or —C ₁ H _2l —R ¹¹ , and in particular, —C ₁ H _{2l + 1} . Preferably, R ¹¹ is —NR ⁸ R ⁹ , —NR ⁸ —NR ⁸ R ⁹ , —N═NR ⁸ , H, or —M—C _m H _{2m + 1} or 6 carbon atoms. -20 aromatic hydrocarbon groups, provided that R ⁸ , R ⁹ , M, l and m are as defined above. In addition, -C _l H _2l -and -C _l H _{2l + 1} are as described above, and -C _m H _{2m + 1} is hydrogen or carbon number 1 because m is 0-20. In which the alkyl group having 1 to 20 carbon atoms is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, decyl, dodecyl. Group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, stearyl group and the like, and the alkyl group may be linear or branched. Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms include aryl groups such as phenyl group, tolyl group, xylyl group, cumenyl group, naphthylene group and tolylene group, and aralkyl groups such as benzyl group and phenethyl group. .

In the compound of the above formula (VI), M is preferably —O— (oxygen). In this case, M is -CH ₂ - are highly reactive with an inorganic filler such as silica as compared to compounds wherein.

When W is represented by —NR ⁸ —, R ¹² and R ¹³ are preferably each independently represented by —O—C ₁ H _2l —, and R ¹⁴ is represented by —O—C ₁ H. is preferably represented by _2l -R ^7, it said R ⁴ is -C _l H _2l - is preferably represented by the above R ⁵ is -C _l H _{2l + 1} with linear or branched represented It is preferably an alkyl group or an aromatic hydrocarbon group having 6 to 20 carbon atoms.

On the other hand, when the W is represented by —O— or —CR ⁸ R ⁹ —, the R ¹² and R ¹³ are preferably each independently represented by —O—C ₁ H _2l —, and the R ¹⁴ is It is preferably represented by —O—C ₁ H _2l —NR ⁸ R ⁹ , R ⁴ is preferably represented by —C ₁ H _2l —, and R ⁵ is represented by —C ₁ H _{2l + 1.} It is preferable.

<< Synthesis Method of Organosilicon Compound >>
The organosilicon compound of the present invention is represented, for example, by the above general formula (I), R ¹ , R ² and R ³ are represented by -M-C ₁ H _{2 1 + 1} , R ¹ , R ² For compounds in which one or more of M in R ³ is —O—, 2- (dimethylamino) ethanol, 2- (diethylamino) ethanol, 2- (dimethylamino) propanol, 2- (diethylamino) propanol, N - an amine compound such as methyl diethanol amine was added, further p- toluenesulfonic acid as a catalyst, and an acid such as hydrochloric acid, was added titanium tetra n- butoxide and titanium alkoxide, by heating, of R ^1, R ² and R ³ One or more is substituted with a monovalent nitrogen-containing group represented by formula (II) or formula (III), or R ¹ and R ² are divalent nitrogen-containing groups represented by —R ¹² —W—R ¹³ —. Can be synthesized by substituting Further, optionally, an alcohol compound such as 2- (2-butoxyethoxy) ethanol is added and heated to _convert one or more of R ¹ , R ² and R ³ _to- (M-C ₁ H _{2 l} ) _y C _s H _{2s +} may be substituted with a monovalent group represented by _1.

<< Specific Examples of Organosilicon Compounds >>
Specifically, as the organosilicon compound of the present invention, 3-methylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-propylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-butylxanthogenate- Propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-pentylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-hexyl Xanthogenate-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-octylxanthogenate-propyl (ethoxy) 1,3-dioxa-6- Tyraza-2-silacyclooctane, 3-nonylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-decylxanthogenate-propyl (ethoxy) 1,3- Dioxa-6-methylaza-2-silacyclooctane, 3-undecylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-dodecylxanthogenate-propyl (ethoxy) ) 1,3-Dioxa-6-methylaza-2-silacyclooctane, 3-stearylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-benzylxanthogenate -Propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-phenylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-methyl Aza-2-silacyclooctane, 3-methylxanthogenate-propyl (methyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methylxanthogenate-propyl (ethyl) 1,3- Dioxa-6-methylaza-2-silacyclooctane, 3-methylxanthogenate-propyl (propyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methylxanthogenate-propyl (butyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methylxanthogenate-propyl (hexyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methylxanthogenate- Propyl (decyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methylxanthogenate-propyl (stearyl) 1,3-dioxa-6-methylaza-2-silacycloocta 3-methylxanthogenate-propyl (butoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methylxanthogenate-propyl (methoxy) 1,3-dioxa-6-methylaza- 2-Silacyclooctane, 3-methylxanthogenate-propyl (hexanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methylxanthogenate-propyl (decanoxy) 1,3-dioxa- 6-Methylaza-2-silacyclooctane, 3-methylxanthogenate-propyl (dodecanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methylxanthogenate-propyl (2- (butoxy Ethoxy) ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methylxanthogenate-propyl (methyl) 1,3-dioxa-6-methylaza-2-silacy Black octane,
3-ethylxanthogenate-propyl (methyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (ethyl) 1,3-dioxa-6-methylaza-2- Silacyclooctane, 3-ethylxanthogenate-propyl (butyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (decyl) 1,3-dioxa-6- Methylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (stearyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (methoxy) 1,3- Dioxa-6-methylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (butoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-ethylxanthogene -Propyl (octanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (decanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3- Ethyl xanthogenate-propyl (dodecanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-ethyl xanthogenate-propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa-6- Methylaza-2-silacyclooctane, 3-pentylxanthogenate-propyl (methyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-pentylxanthogenate-propyl (ethyl) 1,3- Dioxa-6-methylaza-2-silacyclooctane, 3-pentylxanthogenate-propyl (butyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-pentyl Santogenate-propyl (decyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-pentylxanthogenate-propyl (dodecyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3 -Pentylxanthogenate-propyl (stearyl) 1,3-dioxa-6-methylaza-2-silacyclooctane,
3-pentylxanthogenate-propyl (methoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-pentylxanthogenate-propyl (butoxy) 1,3-dioxa-6-methylaza-2- Silacyclooctane, 3-pentylxanthogenate-propyl (octanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-pentylxanthogenate-propyl (decanoxy) 1,3-dioxa-6- Methylaza-2-silacyclooctane,
3-pentylxanthogenate-propyl (dodecanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-pentylxanthogenate-propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa- 6-methylaza-2-silacyclooctane, 3-octylxanthogenate-propyl (methyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-octylxanthogenate-propyl (ethyl) 1, 3-Dioxa-6-methylaza-2-silacyclooctane, 3-octylxanthogenate-propyl (butyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-octylxanthogenate-propyl ( Decyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-octylxanthogenate-propyl (dodecyl) 1,3-dioxa-6-methylaza-2-silaci Looctane, 3-octylxanthogenate-propyl (methoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-octylxanthogenate-propyl (butoxy) 1,3-dioxa-6-methylaza- 2-silacyclooctane, 3-octylxanthogenate-propyl (hexanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-octylxanthogenate-propyl (octanoxy) 1,3-dioxa- 6-methylaza-2-silacyclooctane, 3-octylxanthogenate-propyl (decanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-octylxanthogenate-propyl (dodecanoxy) 1, 3-Dioxa-6-methylaza-2-silacyclooctane, 3-octylxanthogenate-propyl (2- (butoxyethoxy) ethoxy) 1,3-di Kisa -6 Mechiruaza 2-silacyclooctane,
3-decylxanthogenate-propyl (methyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-decylxanthogenate-propyl (ethyl) 1,3-dioxa-6-methylaza-2- Silacyclooctane, 3-decylxanthogenate-propyl (butyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-decylxanthogenate-propyl (hexyl) 1,3-dioxa-6- Methylaza-2-silacyclooctane, 3-decylxanthogenate-propyl (octyl) 1,3-dioxa-6-methylaza-2-silacyclooctane,
3-decylxanthogenate-propyl (decyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-decylxanthogenate-propyl (dodecyl) 1,3-dioxa-6-methylaza-2- Silacyclooctane, 3-decylxanthogenate-propyl (stearyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-decylxanthogenate-propyl (methoxy) 1,3-dioxa-6- Methylaza-2-silacyclooctane, 3-decylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-decylxanthogenate-propyl (butoxy) 1,3- Dioxa-6-methylaza-2-silacyclooctane, 3-decylxanthogenate-propyl (decanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-decylxan Genate-propyl (dodecanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-decylxanthogenate-propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa-6-methylaza-2 -Silacyclooctane, 3-methylxanthogenate-propyl (ethoxy) 1,3-dioxa-5-methylaza-2-silacycloheptane, 3-methylxanthogenate-propyl (ethoxy) 1,3-dioxa-5 -Methylaza-2-silacyclooctane, 3-methylxanthogenate-propyl (ethoxy) 1,3-dioxa-5-methylaza-2-silacyclononane, 3-methylxanthogenate-propyl (ethoxy) 1,3 -Dioxa-6-methylaza-2-silacyclononane, 3-methylxanthogenate-propyl (ethoxy) 1,3-dioxa-5-methylaza-2-silacyclodecane, 3-methylxan Genate-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclodecane, 3-methylxanthogenate-propyl (ethoxy) 1,3-dioxa-7-methylaza-2-silacyclodecane, 3 -Methylxanthogenate-propyl (ethoxy) 1,3-dioxa-5-methylaza-2-silacyclododecane, 3-methylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-sila Cyclododecane, 3-methylxanthogenate-propyl (ethoxy) 1,3-dioxa-7-methylaza-2-silacyclododecane, 3-methylxanthogenate-propyl (ethoxy) 1,3-dioxa-8-methylaza -2-Silacyclododecane, 3-methylxanthogenate-ethyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methylxanthogenate-hexyl (ethoxy) Ii) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methylxanthogenate-octyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methylxanthogen Nate-decyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-methylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-ethylaza-2-silacyclooctane, 3 -Methylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-methylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-hexylaza-2-sila Cyclooctane,
3-methylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-octylaza-2-silacyclooctane, 3-methylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-decylaza-2- Silacyclooctane, 3-methylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (ethoxy) 1,3-dioxa-6- Dodecylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (methyl) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (ethoxy) 1,3- Dioxa-6-decylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (methyl) 1,3-dioxa-6-decylaza-2-silacyclooctane, 3-ethylxa Togenate-propyl (ethoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (methyl) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3 -Pentylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-pentylxanthogenate-propyl (methyl) 1,3-dioxa-6-dodecylaza-2-sila Cyclooctane, 3-pentylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-decylaza-2-silacyclooctane, 3-pentylxanthogenate-propyl (methyl) 1,3-dioxa-6-decylaza -2-Silacyclooctane, 3-pentylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-pentylxanthogene To-propyl (methyl) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-decylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3 -Decylxanthogenate-propyl (methyl) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-decylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-decylaza-2-sila Cyclooctane,
3-decylxanthogenate-propyl (methyl) 1,3-dioxa-6-decylaza-2-silacyclooctane, 3-decylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-butylaza-2- Silacyclooctane, 3-decylxanthogenate-propyl (methyl) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-methylxanthogenate-propyl (ethyl) 1,3-dioxa-6- Ethylaza-2-silacyclooctane, 3-methylxanthogenate-propyl (ethyl) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-methylxanthogenate-propyl (ethyl) 1,3- Dioxa-6-dodecylaza-2-silacyclooctane, 3-methylxanthogenate-propyl (decyl) 1,3-dioxa-6-ethylaza-2-silacyclooctane, 3-methylxanthogenate Pyr (decyl) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-methylxanthogenate-propyl (decyl) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-methyl Xanthogenate-propyl (decanoxy) 1,3-dioxa-6-ethylaza-2-silacyclooctane, 3-methylxanthogenate-propyl (decanoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane 3-methylxanthogenate-propyl (decanoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-methylxanthogenate-propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa -6-Butylaza-2-silacyclooctane, 3-methylxanthogenate-propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane 3-ethylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-ethylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-butylaza-2 -Silacyclooctane, 3-ethylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (methyl) 1,3-dioxa-6 -Ethylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (methyl) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (methyl) 1,3 -Dioxa-6-dodecylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (ethyl) 1,3-dioxa-6-ethylaza-2-silacyclooctane, 3-ethylxanthogen Tert-propyl (ethyl) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (ethyl) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (ethyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (decyl) 1,3-dioxa-6-methylaza-2- Silacyclooctane, 3-ethylxanthogenate-propyl (decyl) 1,3-dioxa-6-ethylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (decyl) 1,3-dioxa-6- Butylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (decyl) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (decanoxy) 1, -Dioxa-6-methylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (decanoxy) 1,3-dioxa-6-ethylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (decanoxy) ) 1,3-dioxa-6-butylaza-2-silacyclooctane,
3-ethylxanthogenate-propyl (decanoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa- 6-Methylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa-6-ethylaza-2-silacyclooctane, 3-ethylxanthogenate- Propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-ethylxanthogenate-propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa-6 -Dodecylaza-2-silacyclooctane, 3-pentylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-ethylaza-2-silacyclooctane, 3-pentylxanthogene Tert-propyl (ethoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-pentylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-pentylxanthogenate-propyl (methyl) 1,3-dioxa-6-ethylaza-2-silacyclooctane, 3-pentylxanthogenate-propyl (methyl) 1,3-dioxa-6-butylaza-2- Silacyclooctane, 3-pentylxanthogenate-propyl (methyl) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-pentylxanthogenate-propyl (ethyl) 1,3-dioxa-6- Ethylaza-2-silacyclooctane, 3-pentylxanthogenate-propyl (ethyl) 1,3-dioxa-6-butylaza-2-silacyclooctane,
3-pentylxanthogenate-propyl (ethyl) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-pentylxanthogenate-propyl (ethyl) 1,3-dioxa-6-methylaza-2- Silacyclooctane, 3-pentylxanthogenate-propyl (decyl) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-pentylxanthogenate-propyl (decyl) 1,3-dioxa-6- Ethylaza-2-silacyclooctane, 3-pentylxanthogenate-propyl (decyl) 1,3-dioxa-6-butylaza-2-silacyclooctane, 3-pentylxanthogenate-propyl (decyl) 1,3- Dioxa-6-dodecylaza-2-silacyclooctane, 3-pentylxanthogenate-propyl (decanoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane, 3-penty Xanthogenate-propyl (decanoxy) 1,3-dioxa-6-ethylaza-2-silacyclooctane, 3-pentylxanthogenate-propyl (decanoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane 3-pentylxanthogenate-propyl (decanoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-pentylxanthogenate-propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa -6-Methylaza-2-silacyclooctane, 3-pentylxanthogenate-propyl (2- (butoxyethoxy) ethoxy 1,3-dioxa-6-ethylaza-2-silacyclooctane, 3-pentylxanthogenate- Propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa-6-butylaza-2-silacyclooctane,
3-Pentylxanthogenate-propyl (2- (butoxyethoxy) ethoxy) 1,3-dioxa-6-dodecylaza-2-silacyclooctane, 3-methylxanthogenate-propyl (didimethylaminoethoxy) monoethoxysilane 3-methylxanthogenate-propyl (dimethylaminoethoxy) diethoxysilane, 3-ethylxanthogenate-propyl (didimethylaminoethoxy) monoethoxysilane, 3-propylxanthogenate-propyl (didimethylaminoethoxy) Monoethoxysilane, 3-butylxanthogenate-propyl (didimethylaminoethoxy) monoethoxysilane, 3-pentylxanthogenate-propyl (didimethylaminoethoxy) monoethoxysilane, 3-hexylxanthogenate-propyl Dimethylaminoethoxy) monoethoxysila 3-octylxanthogenate-propyl (didimethylaminoethoxy) monoethoxysilane, 3-decylxanthogenate-propyl (didimethylaminoethoxy) monoethoxysilane, 3-dodecylxanthogenate-propyl (didimethylaminoethoxy) ) Monoethoxysilane, 3-stearylxanthogenate-propyl (didimethylaminoethoxy) monoethoxysilane, 3-benzylxanthogenate-propyl (didimethylaminoethoxy) monoethoxysilane, 3-phenylxanthogenate-propyl ( Didimethylaminoethoxy) monoethoxysilane, 3-ethylxanthogenate-propyl (dimethylaminoethoxy) diethoxysilane, 3-propylxanthogenate-propyl (dimethylaminoethoxy) diethoxysilane, 3-butylxanthogenate- The Pyr (dimethylaminoethoxy) diethoxysilane, 3-pentylxanthogenate-propyl (dimethylaminoethoxy) diethoxysilane, 3-hexylxanthogenate-propyl (dimethylaminoethoxy) diethoxysilane, 3-octylxanthogenate -Propyl (dimethylaminoethoxy) diethoxysilane, 3-decylxanthogenate-propyl (dimethylaminoethoxy) diethoxysilane, 3-dodecylxanthogenate-propyl (dimethylaminoethoxy) diethoxysilane, 3-stearylxanthogen Nate-propyl (dimethylaminoethoxy) diethoxysilane, 3-benzylxanthogenate-propyl (dimethylaminoethoxy) diethoxysilane, 3-phenylxanthogenate-propyl (dimethylaminoethoxy) diethoxysilane, 3-methyl Xanthogenate-propyl (didimethylaminoethoxy) monomethylsilane, 3-methylxanthogenate-propyl (didimethylaminoethoxy) monoethylsilane, 3-methylxanthogenate-propyl (didimethylaminoethoxy) monobutylsilane, 3-methylxanthogenate-propyl (didimethylaminoethoxy) monooctylsilane, 3-methylxanthogenate-propyl (didimethylaminoethoxy) monodecylsilane, 3-methylxanthogenate-propyl (didimethylaminoethoxy) Monododecylsilane, 3-methylxanthogenate-propyl (didimethylaminoethoxy) monostearylsilane, 3-methylxanthogenate-propyl (dimethylaminoethoxy) dimethylsilane, 3-methylxanthogenate-propyl (dimethylaminoethoxy) ) Diethylsilane, 3-methylxanthogenate-propyl (dimethylaminoethoxy) dibutylsilane, 3-methylxanthogenate-propyl (dimethylaminoethoxy) dioctylsilane, 3-methylxanthogenate-propyl (dimethylaminoethoxy) didecylsilane, 3-methylxanthogenate-propyl (dimethylaminoethoxy) didodecylsilane, 3-methylxanthogenate-propyl (dimethylaminoethoxy) distearylsilane, 3-methylxanthogenate-propyl (didimethylaminoethoxy) monomethoxy Silane, 3-methylxanthogenate-propyl (didimethylaminoethoxy) monobutoxysilane, 3-methylxanthogenate-propyl (didimethylaminoethoxy) monooctanoxysilane, 3-methylxanthogenate-propyl (didioxy) Tilaminoethoxy) monodecanoxysilane, 3-methylxanthogenate-propyl (didimethylaminoethoxy) monododecanoxysilane, 3-methylxanthogenate-propyl (dimethylaminoethoxy) dimethoxysilane, 3-methylxan Togenate-propyl (dimethylaminoethoxy) dibutoxysilane, 3-methylxanthogate-propyl (dimethylaminoethoxy) dioctanoxysilane, 3-methylxanthogenate-propyl (dimethylaminoethoxy) didecanoxysilane, 3-methylxanthogenate-propyl (dimethylaminoethoxy) didodecanoxysilane, 3-methylxanthogenate-propyl (dimethylaminoethoxy) di (2- (butoxyethoxy) ethoxysilane, 3-methylxanthogenate- Ethyl (didimethylaminoethoxy) monoeth Xylsilane, 3-methylxanthogenate-butyl (didimethylaminoethoxy) monoethoxysilane, 3-methylxanthogenate-pentyl (didimethylaminoethoxy) monoethoxysilane, 3-methylxanthogenate-hexyl (didimethylamino) Ethoxy) monoethoxysilane, 3-methylxanthogenate-heptyl (didimethylaminoethoxy) monoethoxysilane, 3-methylxanthogenate-octyl (didimethylaminoethoxy) monoethoxysilane, 3-methylxanthogenate-decyl (Didimethylaminoethoxy) monoethoxysilane, 3-methylxanthogenate-dodecyl (didimethylaminoethoxy) monoethoxysilane, 3-methylxanthogenate-ethyl (dimethylaminoethoxy) diethoxysilane, 3-methylxanthogen Nate-butyl (di Tilaminoethoxy) diethoxysilane, 3-methylxanthogenate-pentyl (dimethylaminoethoxy) diethoxysilane, 3-methylxanthogenate-hexyl (dimethylaminoethoxy) diethoxysilane, 3-methylxanthogenate-heptyl (Dimethylaminoethoxy) diethoxysilane, 3-methylxanthogenate-octyl (dimethylaminoethoxy) diethoxysilane, 3-methylxanthogenate-decyl (dimethylaminoethoxy) diethoxysilane, 3-methylxanthogenate- Dodecyl (dimethylaminoethoxy) diethoxysilane,
3-methylxanthogenate-propyl (didiethylaminoethoxy) monoethoxysilane, 3-methylxanthogenate-propyl (didipropylaminoethoxy) monoethoxysilane, 3-methylxanthogenate-propyl (didibutylaminoethoxy) mono Ethoxysilane, 3-methylxanthogenate-propyl (didipentylaminoethoxy) monoethoxysilane, 3-methylxanthogenate-propyl (didihexylaminoethoxy) monoethoxysilane, 3-methylxanthogenate-propyl (didioctyl) Aminoethoxy) monoethoxysilane, 3-methylxanthogenate-propyl (didi-2-ethylhexylaminoethoxy) monoethoxysilane, 3-methylxanthogenate-propyl (dididecylaminoethoxy) monoethoxysilane, 3-methylxanthogen -Propyl (dididodecylaminoethoxy) monoethoxysilane, 3-methylxanthogenate-propyl (diethylaminoethoxy) diethoxysilane, 3-methylxanthogenate-propyl (dipropylaminoethoxy) diethoxysilane, 3- Methylxanthogenate-propyl (dibutylaminoethoxy) diethoxysilane, 3-methylxanthogenate-propyl (dipentylaminoethoxy) diethoxysilane, 3-methylxanthogenate-propyl (dihexylaminoethoxy) diethoxysilane, 3 -Methylxanthogenate-propyl (dioctylaminoethoxy) diethoxysilane, 3-methylxanthogenate-propyl (di-2-ethylhexylaminoethoxy) diethoxysilane, 3-methylxanthogenate-propyl (didecylaminoethoxy) Dietoki Silane, 3-methylxanthogenate-propyl (didodecylaminoethoxy) diethoxysilane, 3-methylxanthogenate-propyl (didimethylaminomethoxy) monoethoxysilane, 3-methylxanthogenate-propyl (didimethylamino) (Propoxy) monoethoxysilane, 3-methylxanthogenate-propyl (didimethylaminobutoxy) monoethoxysilane, 3-methylxanthogenate-propyl (didimethylaminopentoxy) monoethoxysilane, 3-methylxanthogenate- Propyl (didimethylamino octanoxy) monoethoxysilane, 3-methylxanthogenate-propyl (didimethylaminodecanoxy) monoethoxysilane, 3-methylxanthogenate-propyl (dimethylaminomethoxy) diethoxysilane, 3-methylxanthogenate -Propyl (dimethylaminopropoxy) diethoxysilane, 3-methylxanthogenate-propyl (dimethylaminobutoxy) diethoxysilane, 3-methylxanthogenate-propyl (dimethylaminopentoxy) diethoxysilane, 3-methylxan Togenate-propyl (dimethylaminooctanoxy) diethoxysilane, 3-methylxanthogenate-propyl (dimethylaminodecanoxy) diethoxysilane, 3-ethylxanthogenate-propyl (didimethylaminomethoxy) monoethoxy Silane, 3-ethylxanthogenate-propyl (dimethylaminomethoxy) diethoxysilane, 3-pentylxanthogenate-propyl (didimethylaminomethoxy) monoethoxysilane, 3-pentylxanthogenate-propyl (dimethylaminomethoxy) Diethoxysila 3-ethylxanthogenate-propyl (didimethylaminomethoxy) monomethylsilane, 3-ethylxanthogenate-propyl (dimethylaminomethoxy) dimethylsilane, 3-pentylxanthogenate-propyl (didimethylaminomethoxy) monomethylsilane 3-pentylxanthogenate-propyl (dimethylaminomethoxy) dimethylsilane,
3-methylxanthogenate-propyl (didimethylaminomethoxy) monoethylsilane, 3-methylxanthogenate-propyl (dimethylaminomethoxy) diethylsilane, 3-ethylxanthogenate-propyl (didimethylaminomethoxy) monoethyl Silane, 3-ethylxanthogenate-propyl (dimethylaminomethoxy) diethylsilane, 3-pentylxanthogenate-propyl (didimethylaminomethoxy) monoethylsilane, 3-pentylxanthogenate-propyl (dimethylaminomethoxy) diethyl Silane, 3-methylxanthogenate-propyl (didimethylaminomethoxy) monodecylsilane, 3-methylxanthogenate-propyl (dimethylaminomethoxy) didecylsilane, 3-ethylxanthogenate-propyl (didimethylaminomethoxy) monodecyl Silane, 3-ethylxanthogenate-propyl (dimethylaminomethoxy) didecylsilane, 3-pentylxanthogenate-propyl (didimethylaminomethoxy) monodecylsilane, 3-pentylxanthogenate-propyl (dimethylaminomethoxy) didecylsilane, 3-methylxanthogenate-propyl (didimethylaminomethoxy) monodecanoxysilane, 3-methylxanthogenate-propyl (dimethylaminomethoxy) didecanoxysilane, 3-ethylxanthogenate-propyl (didimethylamino) Methoxy) monodecanoxysilane, 3-ethylxanthogenate-propyl (dimethylaminomethoxy) didecanoxysilane, 3-pentylxanthogenate-propyl (didimethylaminomethoxy) monodecanoxysilane, 3-pentylxan Togenate-Pro Ru (dimethylaminomethoxy) didecanoxysilane, 3-methylxanthogenate-propyl (didimethylaminomethoxy) mono (2- (butoxyethoxy) ethoxy) silane, 3-methylxanthogenate-propyl (dimethylaminomethoxy) Di (2- (butoxyethoxy) ethoxy) silane, 3-ethylxanthogenate-propyl (didimethylaminomethoxy) mono (2- (butoxyethoxy) ethoxy) silane, 3-ethylxanthogenate-propyl (dimethylaminomethoxy) ) Di (2- (butoxyethoxy) ethoxy) silane, 3-pentylxanthogenate-propyl (didimethylaminomethoxy) mono (2- (butoxyethoxy) ethoxy) silane, 3-pentylxanthogenate-propyl (dimethylamino) Methoxy) di (2- (butoxyethoxy) ethoxy) silane, 3-ethylxanthogenate Pyr (didimethylaminoethoxy) monomethylsilane, 3-ethylxanthogenate-propyl (dimethylaminoethoxy) dimethylsilane, 3-pentylxanthogenate-propyl (didimethylaminoethoxy) monomethylsilane, 3-ethylxanthogenate- Propyl (didimethylaminoethoxy) monomethylsilane, 3-ethylxanthogenate-propyl (dimethylaminoethoxy) dimethylsilane, 3-pentylxanthogenate-propyl (didimethylaminoethoxy) monomethylsilane, 3-pentylxanthogenate- Propyl (dimethylaminoethoxy) dimethylsilane, 3-ethylxanthogenate-propyl (didimethylaminoethoxy) monodecylsilane, 3-ethylxanthogenate-propyl (dimethylaminoethoxy) didecylsilane, 3-pentylxa Togenate-propyl (didimethylaminoethoxy) monodecylsilane, 3-pentylxanthogenate-propyl (dimethylaminoethoxy) didecylsilane,
3-ethylxanthogenate-propyl (didimethylaminoethoxy) monodecanoxysilane, 3-ethylxanthogenate-propyl (dimethylaminoethoxy) didecanoxysilane, 3-pentylxanthogenate-propyl (didimethylamino) Ethoxy) monodecanoxysilane, 3-pentylxanthogenate-propyl (dimethylaminoethoxy) didecanoxysilane, 3-ethylxanthogenate-propyl (didimethylaminoethoxy) mono (2- (butoxyethoxy) ethoxy) Silane, 3-ethylxanthogenate-propyl (dimethylaminoethoxy) di (2- (butoxyethoxy) ethoxy) silane, 3-pentylxanthogenate-propyl (didimethylaminoethoxy) mono (2- (butoxyethoxy) ethoxy Silane,
3-pentylxanthogenate-propyl (dimethylaminoethoxy) di (2- (butoxyethoxy) ethoxy) silane, 3-ethylxanthogenate-propyl (didimethylaminobutoxy) monoethoxysilane, 3-ethylxanthogenate- Propyl (dimethylaminobutoxy) diethoxysilane, 3-pentylxanthogenate-propyl (didimethylaminobutoxy) monoethoxysilane, 3-pentylxanthogenate-propyl (dimethylaminobutoxy) diethoxysilane, 3-ethylxanthogen Nate-propyl (didimethylaminobutoxy) monomethylsilane, 3-ethylxanthogenate-propyl (dimethylaminobutoxy) dimethylsilane, 3-pentylxanthogenate-propyl (didimethylaminobutoxy) monomethylsilane, 3-pentylxanthogen Neop Pyr (dimethylaminobutoxy) dimethylsilane, 3-methylxanthogenate-propyl (didimethylaminobutoxy) monoethylsilane, 3-methylxanthogenate-propyl (dimethylaminobutoxy) diethylsilane, 3-ethylxanthogenate- Propyl (didimethylaminobutoxy) monoethylsilane, 3-ethylxanthogenate-propyl (dimethylaminobutoxy) diethylsilane,
3-pentylxanthogenate-propyl (didimethylaminobutoxy) monoethylsilane, 3-pentylxanthogenate-propyl (dimethylaminobutoxy) diethylsilane, 3-methylxanthogenate-propyl (didimethylaminobutoxy) monodecyl Silane, 3-methylxanthogenate-propyl (dimethylaminobutoxy) didecylsilane, 3-ethylxanthogenate-propyl (didimethylaminobutoxy) monodecylsilane, 3-ethylxanthogenate-propyl (dimethylaminobutoxy) didecylsilane, 3-pentylxanthogenate-propyl (didimethylaminobutoxy) monodecylsilane, 3-pentylxanthogenate-propyl (dimethylaminobutoxy) didecylsilane, 3-methylxanthogenate-propyl (didimethylaminobutoxy) Decanoxysilane, 3-methylxanthogenate-propyl (dimethylaminobutoxy) didecanoxysilane, 3-ethylxanthogenate-propyl (didimethylaminobutoxy) monodecanoxysilane, 3-ethylxanthogenate-propyl (dimethyl) Aminobutoxy) didecanoxysilane, 3-pentylxanthogenate-propyl (didimethylaminobutoxy) monodecanoxysilane, 3-pentylxanthogenate-propyl (dimethylaminobutoxy) didecanoxysilane, 3-methylxan Togenate-propyl (didimethylaminobutoxy) mono (2- (butoxyethoxy) ethoxy) silane, 3-methylxanthogenate-propyl (dimethylaminobutoxy) di (2- (butoxyethoxy) ethoxy) silane, 3-ethyl Xanthogenate-propyl (didimethylaminobutoxy B) Mono (2- (butoxyethoxy) ethoxy) silane, 3-ethylxanthogenate-propyl (dimethylaminobutoxy) di (2- (butoxyethoxy) ethoxy) silane, 3-pentylxanthogenate-propyl (didimethyl) Aminobutoxy) mono (2- (butoxyethoxy) ethoxy) silane, 3-pentylxanthogenate-propyl (dimethylaminobutoxy) di (2- (butoxyethoxy) ethoxy) silane, 3-ethylxanthogenate-propyl (di) Diethylaminomethoxy) monoethoxysilane, 3-ethylxanthogenate-propyl (diethylaminomethoxy) diethoxysilane, 3-pentylxanthogenate-propyl (didiethylaminomethoxy) monoethoxysilane, 3-pentylxanthogenate-propyl (diethylamino) Methoxy) diethoxysilane, 3-ethylxan Genate-propyl (didiethylaminomethoxy) monomethylsilane, 3-ethylxanthogenate-propyl (diethylaminomethoxy) dimethylsilane, 3-pentylxanthogenate-propyl (didiethylaminomethoxy) monomethylsilane, 3-pentylxanthogenate-propyl (Diethylaminomethoxy) dimethylsilane, 3-methylxanthogenate-propyl (didiethylaminomethoxy) monoethylsilane, 3-methylxanthogenate-propyl (diethylaminomethoxy) diethylsilane, 3-ethylxanthogenate-propyl (didiethylamino) Methoxy) monoethylsilane, 3-ethylxanthogenate-propyl (diethylaminomethoxy) diethylsilane, 3-pentylxanthogenate-propyl (didiethylaminomethoxy) monoethylsilane, 3- Pentylxanthogenate-propyl (diethylaminomethoxy) diethylsilane, 3-methylxanthogenate-propyl (didiethylaminomethoxy) monodecylsilane, 3-methylxanthogenate-propyl (diethylaminomethoxy) didecylsilane,
3-ethylxanthogenate-propyl (didiethylaminomethoxy) monodecylsilane, 3-ethylxanthogenate-propyl (diethylaminomethoxy) didecylsilane, 3-pentylxanthogenate-propyl (didiethylaminomethoxy) monodecylsilane, 3- Pentylxanthogenate-propyl (diethylaminomethoxy) didecylsilane, 3-methylxanthogenate-propyl (didiethylaminomethoxy) monodecanoxysilane, 3-methylxanthogenate-propyl (diethylaminomethoxy) didecanoxysilane, 3- Ethyl xanthogenate-propyl (didiethylaminomethoxy) monodecanoxysilane, 3-ethylxanthogenate-propyl (diethylaminomethoxy) didecanoxysilane, 3-pentylxanthogenate-propyl (didiethylacetate) Nomethoxy) monodecanoxysilane, 3-pentylxanthogenate-propyl (diethylaminomethoxy) didecanoxysilane, 3-methylxanthogenate-propyl (didiethylaminomethoxy) mono (2- (butoxyethoxy) ethoxy) silane, 3-methylxanthogenate-propyl (diethylaminomethoxy) di (2- (butoxyethoxy) ethoxy) silane, 3-ethylxanthogenate-propyl (didiethylaminomethoxy) mono (2- (butoxyethoxy) ethoxy) silane, 3 -Ethylxanthogenate-propyl (diethylaminomethoxy) di (2- (butoxyethoxy) ethoxy) silane, 3-pentylxanthogenate-propyl (didiethylaminomethoxy) mono (2- (butoxyethoxy) ethoxy) silane, 3- Pentylxanthogenate-propyl (diethylaminomethoxy) di (2- (Butoxyethoxy) ethoxy) silane, 3-ethylxanthogenate-propyl (didiethylaminoethoxy) monomethylsilane, 3-ethylxanthogenate-propyl (diethylaminoethoxy) dimethylsilane, 3-pentylxanthogenate-propyl (Didiethylaminoethoxy) monomethylsilane, 3-ethylxanthogenate-propyl (didiethylaminoethoxy) monomethylsilane, 3-ethylxanthogenate-propyl (diethylaminoethoxy) dimethylsilane, 3-pentylxanthogenate-propyl (didiethylamino) Ethoxy) monomethylsilane, 3-pentylxanthogenate-propyl (diethylaminoethoxy) dimethylsilane, 3-ethylxanthogenate-propyl (didiethylaminoethoxy) monodecylsilane, 3-ethylxanthogene 3-propyl (diethylaminoethoxy) didecylsilane, 3-pentylxanthogenate-propyl (didiethylaminoethoxy) monodecylsilane, 3-pentylxanthogenate-propyl (diethylaminoethoxy) didecylsilane, 3-ethylxanthogenate-propyl Diethylaminoethoxy) monodecanoxysilane, 3-ethylxanthogenate-propyl (diethylaminoethoxy) didecanoxysilane, 3-pentylxanthogenate-propyl (didiethylaminoethoxy) monodecanoxysilane, 3-pentylxanthogen Nate-propyl (diethylaminoethoxy) didecanoxysilane, 3-ethylxanthogenate-propyl (didiethylaminoethoxy) mono (2- (butoxyethoxy) ethoxy) silane, 3-ethylxanthogenate-propyl (diethylacetate) Minoethoxy) di (2- (butoxyethoxy) ethoxy) silane, 3-pentylxanthogenate-propyl (didiethylaminoethoxy) mono (2- (butoxyethoxy) ethoxy) silane, 3-pentylxanthogenate-propyl (diethylaminoethoxy) ) Di (2- (butoxyethoxy) ethoxy) silane, 3-ethylxanthogenate-propyl (didiethylaminobutoxy) monoethoxysilane, 3-ethylxanthogenate-propyl (diethylaminobutoxy) diethoxysilane, 3-pentylxan Togenate-propyl (didiethylaminobutoxy) monoethoxysilane, 3-pentylxanthogenate-propyl (diethylaminobutoxy) diethoxysilane, 3-ethylxanthogenate-propyl (didiethylaminobutoxy) monomethylsilane, 3-ethylxanthogen Neop Lopyl (diethylaminobutoxy) dimethylsilane, 3-pentylxanthogenate-propyl (didiethylaminobutoxy) monomethylsilane, 3-pentylxanthogenate-propyl (diethylaminobutoxy) dimethylsilane, 3-methylxanthogenate-propyl (didiethylamino) Butoxy) monoethylsilane, 3-methylxanthogenate-propyl (diethylaminobutoxy) diethylsilane, 3-ethylxanthogenate-propyl (didiethylaminobutoxy) monoethylsilane, 3-ethylxanthogenate-propyl (diethylaminobutoxy) Diethylsilane, 3-pentylxanthogenate-propyl (didiethylaminobutoxy) monoethylsilane, 3-pentylxanthogenate-propyl (diethylaminobutoxy) diethylsilane, 3-methylxan Geneto - propyl (di diethylamino-butoxy) mono decyl silane, 3-methyl xanthogenate - propyl (diethylamino butoxy) Jideshirushiran,
3-ethylxanthogenate-propyl (didiethylaminobutoxy) monodecylsilane, 3-ethylxanthogenate-propyl (diethylaminobutoxy) didecylsilane, 3-pentylxanthogenate-propyl (didiethylaminobutoxy) monodecylsilane, 3- Pentylxanthogenate-propyl (diethylaminobutoxy) didecylsilane, 3-methylxanthogenate-propyl (didiethylaminobutoxy) monodecanoxysilane, 3-methylxanthogenate-propyl (diethylaminobutoxy) didecanoxysilane, 3- Ethyl xanthogenate-propyl (didiethylaminobutoxy) monodecanoxysilane, 3-ethylxanthogenate-propyl (diethylaminobutoxy) didecanoxysilane, 3-pentylxanthogenate-propyl (didiethylacetate) Nobutoxy) monodecanoxysilane, 3-pentylxanthogenate-propyl (diethylaminobutoxy) didecanoxysilane, 3-methylxanthogenate-propyl (didiethylaminobutoxy) mono (2- (butoxyethoxy) ethoxy) silane, 3-methylxanthogenate-propyl (diethylaminobutoxy) di (2- (butoxyethoxy) ethoxy) silane, 3-ethylxanthogenate-propyl (didiethylaminobutoxy) mono (2- (butoxyethoxy) ethoxy) silane, 3 3-ethylxanthogenate-propyl (diethylaminobutoxy) di (2- (butoxyethoxy) ethoxy) silane, 3-pentylxanthogenate-propyl (didiethylaminobutoxy) mono (2- (butoxyethoxy) ethoxy) silane, 3- Pentylxanthogenate-propyl (diethylaminobutoxy) di And (2- (butoxyethoxy) ethoxy) silane.

<Rubber composition>
The rubber composition of the present invention is obtained by blending an inorganic filler (B) and the above-mentioned organosilicon compound (C) with a rubber component (A) made of natural rubber and / or a diene synthetic rubber. Preferably, the rubber component (A) composed of natural rubber and / or diene synthetic rubber is blended with 5 to 140 parts by weight of the inorganic filler (B), and the above organic The silicon compound (C) is blended in an amount of 1 to 20% by mass based on the blending amount of the inorganic filler (B).

  Here, when the content of the organosilicon compound (C) is less than 1% by mass of the blending amount of the inorganic filler (B), the effect of reducing the hysteresis loss of the rubber composition and the effect of improving the wear resistance are ineffective. On the other hand, if it exceeds 20% by mass, the effect is saturated.

  The rubber component (A) of the rubber composition of the present invention comprises natural rubber and / or a diene synthetic rubber. Here, examples of the diene synthetic rubber include styrene-butadiene copolymer rubber (SBR), polybutadiene rubber (BR), polyisoprene rubber (IR), butyl rubber (IIR), and ethylene-propylene copolymer. These rubber components (A) may be used alone or in a blend of two or more.

  Examples of the inorganic filler (B) used in the rubber composition of the present invention include silica, aluminum hydroxide, alumina, clay, calcium carbonate, etc. Among these, silica and aluminum hydroxide are preferable from the viewpoint of reinforcement. Silica is preferred and particularly preferred. When the inorganic filler (B) is silica, the organosilicon compound (C) has a functional group having a high affinity for the silanol group on the silica surface and / or a functional group having a high affinity for the silicon atom (Si). For this reason, the coupling efficiency is greatly improved, the hysteresis loss of the rubber composition is reduced, and the effect of improving the wear resistance becomes more remarkable. In addition, there is no restriction | limiting in particular as silica, Wet silica (hydrous silicic acid), dry-type silica (anhydrous silicic acid), etc. can be used, On the other hand, as aluminum hydroxide, Heidilite (registered trademark, Showa Denko) Are preferably used.

The silica is preferably BET surface area of 40~350 m ² / g. When the BET surface area of silica is 40 m ² / g or less, the particle size of the silica is too large and wear resistance is greatly reduced. When the BET surface area of silica is 350 m ² / g or more, Since the particle diameter of the silica is too small, hysteresis loss is greatly increased.

  The blending amount of the inorganic filler (B) is preferably in the range of 5 to 140 parts by mass with respect to 100 parts by mass of the rubber component (A). If the blending amount of the inorganic filler (B) is less than 5 parts by mass with respect to 100 parts by mass of the rubber component (A), the effect of reducing the hysteresis is insufficient, while if it exceeds 140 parts by mass, the workability is increased. This is because of the remarkable deterioration.

  In addition to the rubber component (A), inorganic filler (B), and organosilicon compound (C), the rubber composition of the present invention contains compounding agents commonly used in the rubber industry, such as carbon black, softeners. Vulcanizing agents, vulcanization accelerators, anti-aging agents, zinc white, stearic acid and the like can be appropriately blended depending on the purpose. As these compounding agents, commercially available products can be suitably used. In addition, the rubber composition of the present invention is blended with the rubber component (A), together with the inorganic filler (B) and the organosilicon compound (C), and various compounding agents appropriately selected as necessary. It can be produced by hot-pressing, extruding or the like.

<Tire>
The tire of the present invention is characterized by using the above rubber composition, and the above rubber composition is preferably used for the tread. In the tire of the present invention, the rolling resistance is greatly reduced, and the wear resistance is also greatly improved. The tire of the present invention has a conventionally known structure and is not particularly limited, and can be produced by a normal method. In addition, when the tire of the present invention is a pneumatic tire, the gas filled in the tire may be normal or air with adjusted oxygen partial pressure, or an inert gas such as nitrogen, argon, or helium. .

<Primer composition, coating composition and adhesive>
Furthermore, the primer composition of the present invention is characterized by containing the above organosilicon compound, the coating composition of the present invention is characterized by comprising the above organosilicon compound, and the adhesive of the present invention comprises the above organosilicon compound. It is characterized by including a compound. The above-described organosilicon compound of the present invention has a high affinity even if it is a hydroxy group other than a silanol group, so that it can also promote reactions with various inorganic compounds having a hydroxy group, and is a hybrid material of an organic material and an inorganic material. It is effective in improving the adhesion and affinity at the interface. Therefore, the primer composition, coating composition, and adhesive containing the organosilicon compound can improve the adhesion and affinity at the interface between the organic material and the inorganic material.

  Here, the primer composition of the present invention may contain a catalyst composed of a metal or a metal compound such as tin or titanium as a curing accelerating component in addition to the organosilicon compound, and the viscosity of the primer composition. In order to adjust this, an organic solvent may be included. Moreover, the coating composition of this invention can contain a pigment, a metal particle, resin, and also an organic solvent and water other than the said organosilicon compound. Furthermore, the adhesive of the present invention can contain a resin, and further an organic solvent for adjusting the viscosity of the adhesive, in addition to the organosilicon compound. The primer composition, the coating composition, and the adhesive of the present invention can be prepared by a known method by mixing a compounding agent and a solvent appropriately selected according to the purpose, together with the organosilicon compound.

  Hereinafter, the present invention will be described in more detail with reference to examples. However, the present invention is not limited to the following examples.

で表わされる３-エチルキサントゲネート-プロピルトリエトキシシラン［有機ケイ素化合物（Ｃ−１）］27.6 gを得た。生成物の¹Ｈ−ＮＭＲでの分析結果を以下に示す。
¹Ｈ−ＮＭＲ（CDCl₃, 700MHz, δ;ppm）= 4.6(q;2H), 3.8(m;6H), 3.1(t;2H), 1.8(m;2H), 1.4(m;3H), 1.2(t;9H), 0.7(t;2H) <Production Example 1 of Organosilicon Compound>
In a 500 mL four-necked eggplant flask, 16.0 g of potassium ethyl xanthate was dissolved in 200 mL of acetone in a nitrogen atmosphere, and the temperature was raised to 40 ° C. To this solution, 24.1 g of 3-chloropropyltriethoxysilane was added dropwise and stirred for 3 days. Thereafter, the precipitated potassium chloride is filtered off and the solvent is removed by a rotary evaporator at 20 hPa / 40 ° C., and then at 10 Pa / 150 ° C. using a rotary pump and a cold trap (dry ice + ethanol). The remaining low boiling impurities are removed and the following chemical formula:

27.6 g of 3-ethylxanthogenate-propyltriethoxysilane [organosilicon compound (C-1)] represented by the formula: The results of ¹ H-NMR analysis of the product are shown below.
¹ H-NMR (CDCl ₃ , 700 MHz, δ; ppm) = 4.6 (q; 2H), 3.8 (m; 6H), 3.1 (t; 2H), 1.8 (m; 2H), 1.4 (m; 3H), 1.2 (t; 9H), 0.7 (t; 2H)

で表わされる３-ペンチルキサントゲネート-プロピルトリエトキシシラン［有機ケイ素化合物（Ｃ−２）］30.0 gを得た。生成物の¹Ｈ−ＮＭＲでの分析結果を以下に示す。
¹Ｈ−ＮＭＲ（CDCl₃, 700MHz, δ;ppm）= 4.6(q;2H), 3.8(m;6H), 3.1(t;2H), 1.8(m;2H), 1.4(m;3H), 1.2(t;9H), 0.7(t;2H) <Production Example 2 of organosilicon compound>
In a 500 mL four-necked eggplant flask, 20.2 g of potassium amyl xanthate was dissolved in 200 mL of acetone in a nitrogen atmosphere, and the temperature was raised to 40 ° C. To this solution, 24.1 g of 3-chloropropyltriethoxysilane was added dropwise and stirred for 3 days. Thereafter, the precipitated potassium chloride is filtered off and the solvent is removed by a rotary evaporator at 20 hPa / 40 ° C., and then at 10 Pa / 150 ° C. using a rotary pump and a cold trap (dry ice + ethanol). The remaining low boiling impurities are removed and the following chemical formula:

30.0 g of 3-pentylxanthogenate-propyltriethoxysilane [organosilicon compound (C-2)] represented by the formula: The results of ¹ H-NMR analysis of the product are shown below.
¹ H-NMR (CDCl ₃ , 700 MHz, δ; ppm) = 4.6 (q; 2H), 3.8 (m; 6H), 3.1 (t; 2H), 1.8 (m; 2H), 1.4 (m; 3H), 1.2 (t; 9H), 0.7 (t; 2H)

で表わされる３-エチルキサントゲネート-プロピル(エトキシ)１,３-ジオキサ-６-メチルアザ-２-シラシクロオクタン［有機ケイ素化合物（Ｃ−３）］27.0 gを得た。生成物の¹Ｈ−ＮＭＲでの分析結果を以下に示す。
¹Ｈ−ＮＭＲ（CDCl₃, 700MHz, δ;ppm）= 4.6(q;2H), 3.8(m;6H), 3.1(t;2H), 2.5(m;4H), 2.4(s;3H), 1.8(m;2H), 1.4(m;3H), 1.2(t;3H), 0.7(t;2H) <Production Example 3 of organosilicon compound>
In a 500 mL four-necked eggplant flask, 27.6 g of 3-ethylxanthogenate-propyltriethoxysilane, 10.0 g of N-methyldiethanolamine and 0.05 g of titanium tetra-n-butoxide obtained in a nitrogen atmosphere were dissolved in 200 mL of xylene. The temperature was raised to 150 ° C. and stirred for 6 hours. Thereafter, the solvent was removed by a rotary evaporator at 20 hPa / 40 ° C., and then the remaining volatile components were removed by a rotary pump (10 Pa) and a cold trap (dry ice + ethanol).

27.0 g of 3-ethylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane [organosilicon compound (C-3)] represented by the formula: The results of ¹ H-NMR analysis of the product are shown below.
¹ H-NMR (CDCl ₃ , 700 MHz, δ; ppm) = 4.6 (q; 2H), 3.8 (m; 6H), 3.1 (t; 2H), 2.5 (m; 4H), 2.4 (s; 3H), 1.8 (m; 2H), 1.4 (m; 3H), 1.2 (t; 3H), 0.7 (t; 2H)

<Production Example 4 of organosilicon compound>
In a 500 mL four-necked eggplant flask, 16.0 g of potassium ethyl xanthate was dissolved in 200 mL of acetone in a nitrogen atmosphere, and the temperature was raised to 40 ° C. To this solution, 18.3 g of 3-chloropropyldimethoxymethylsilane was added dropwise and stirred for 3 days. Thereafter, the precipitated potassium chloride is filtered off and the solvent is removed by a rotary evaporator at 20 hPa / 40 ° C., and then at 10 Pa / 150 ° C. using a rotary pump and a cold trap (dry ice + ethanol). The remaining low boiling impurities were removed to obtain 22.1 g of 3-ethylxanthogenate-propyldimethoxymethylsilane.

で表わされる３-エチルキサントゲネート-プロピル(メチル)１,３-ジオキサ-６-メチルアザ-２-シラシクロオクタン［有機ケイ素化合物（Ｃ−４）］25.0 gを得た。生成物の¹Ｈ−ＮＭＲでの分析結果を以下に示す。
¹Ｈ−ＮＭＲ（CDCl₃, 700MHz, δ;ppm）= 4.6(q;2H), 3.8(m;4H), 3.1(t;2H), 2.5(m;4H), 2.4(s;3H), 1.8(m;2H), 1.4(m;3H), 0.7(t;2H), 0.1(s;3H) Next, in a 500 mL four-necked eggplant flask, 22.1 g of 3-ethylxanthogenate-propyldimethoxymethylsilane, 9.8 g of N-methyldiethanolamine, and 0.05 g of titanium tetra-n-butoxide obtained in a nitrogen atmosphere were added to 200 mL of xylene. After dissolution, the temperature was raised to 150 ° C. and stirred for 6 hours. Thereafter, the solvent was removed by a rotary evaporator at 20 hPa / 40 ° C., and then the remaining volatile components were removed by a rotary pump (10 Pa) and a cold trap (dry ice + ethanol).

25.0 g of 3-ethylxanthogenate-propyl (methyl) 1,3-dioxa-6-methylaza-2-silacyclooctane [organosilicon compound (C-4)] represented by the formula: The results of ¹ H-NMR analysis of the product are shown below.
¹ H-NMR (CDCl ₃ , 700 MHz, δ; ppm) = 4.6 (q; 2H), 3.8 (m; 4H), 3.1 (t; 2H), 2.5 (m; 4H), 2.4 (s; 3H), 1.8 (m; 2H), 1.4 (m; 3H), 0.7 (t; 2H), 0.1 (s; 3H)

で表わされる３-ペンチルキサントゲネート-プロピル(エトキシ)１,３-ジオキサ-６-メチルアザ-２-シラシクロオクタン［有機ケイ素化合物（Ｃ−５）］27.0 gを得た。生成物の¹Ｈ−ＮＭＲでの分析結果を以下に示す。
¹Ｈ−ＮＭＲ（CDCl₃, 700MHz, δ;ppm）= 4.6(q;2H), 3.8(m;6H), 3.1(t;2H), 2.5(m;4H), 2.4(s;3H), 1.8(m;2H), 1.4(m;2H), 1.2(t;7H), 1.0(t;3H), 0.7(t;2H) <Production Example 5 of organosilicon compound>
In a 500 mL four-necked eggplant flask, 30.0 g of 3-pentylxanthogenate-propyltriethoxysilane, 10.0 g of N-methyldiethanolamine and 0.05 g of titanium tetra-n-butoxide obtained in a nitrogen atmosphere were dissolved in 200 mL of xylene. The temperature was raised to 150 ° C. and stirred for 6 hours. Thereafter, the solvent was removed by a rotary evaporator at 20 hPa / 40 ° C., and then the remaining volatile components were removed by a rotary pump (10 Pa) and a cold trap (dry ice + ethanol).

27.0 g of 3-pentylxanthogenate-propyl (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane [organosilicon compound (C-5)] represented by the formula: The results of ¹ H-NMR analysis of the product are shown below.
¹ H-NMR (CDCl ₃ , 700 MHz, δ; ppm) = 4.6 (q; 2H), 3.8 (m; 6H), 3.1 (t; 2H), 2.5 (m; 4H), 2.4 (s; 3H), 1.8 (m; 2H), 1.4 (m; 2H), 1.2 (t; 7H), 1.0 (t; 3H), 0.7 (t; 2H)

で表わされる３-ペンチルキサントゲネート-プロピル(ジジメチルアミノエトキシ)メチルシラン［有機ケイ素化合物（Ｃ−６）］32.5 gを得た。生成物の¹Ｈ−ＮＭＲでの分析結果を以下に示す。
¹Ｈ−ＮＭＲ（CDCl₃, 700MHz, δ;ppm）= 4.6(q;2H), 3.8(m;4H), 3.1(t;2H), 2.5(m;4H), 2.2(s;12H), 1.8(m;2H), 1.4(m;3H), 0.7(t;2H), 0.1(s;3H) <Production Example 6 of organosilicon compound>
After dissolving 22.1 g of 3-pentylxanthogenate-propyldimethoxymethylsilane, 14.6 g of N-dimethylaminoethanol and 0.05 g of titanium tetra-n-butoxide in 200 mL of xylene in a 500 mL four-necked eggplant flask The temperature was raised to 150 ° C. and stirred for 6 hours. Thereafter, the solvent was removed by a rotary evaporator at 20 hPa / 40 ° C., and then the remaining volatile components were removed by a rotary pump (10 Pa) and a cold trap (dry ice + ethanol).

32.5 g of 3-pentylxanthogenate-propyl (didimethylaminoethoxy) methylsilane [organosilicon compound (C-6)] represented by the formula: The results of ¹ H-NMR analysis of the product are shown below.
¹ H-NMR (CDCl ₃ , 700 MHz, δ; ppm) = 4.6 (q; 2H), 3.8 (m; 4H), 3.1 (t; 2H), 2.5 (m; 4H), 2.2 (s; 12H), 1.8 (m; 2H), 1.4 (m; 3H), 0.7 (t; 2H), 0.1 (s; 3H)

で表わされる３-エチルキサントゲネート-プロピル(２-(２-ブトキシエトキシ)エトキシ)１,３-ジオキサ-６-メチルアザ-２-シラシクロオクタン［有機ケイ素化合物（Ｃ−７）］47.7gを得た。生成物の¹Ｈ−ＮＭＲでの分析結果を以下に示す。
¹Ｈ−ＮＭＲ（CDCl₃, 700MHz, δ;ppm）= 4.6(q;2H), 3.8(m;6H), 3.5(m;8H), 3.1(t;2H), 2.5(m;4H), 2.4(s;3H), 1.8(m;2H), 1.4(m;7H), 0.9(t;3H), 0.7(t;2H) <Production Example 7 of Organosilicon Compound>
In a 500 mL four-necked eggplant flask, 32.6 g of 3-ethylxanthogenate-propyltriethoxysilane, 11.9 g of N-methyldiethanolamine, and 0.05 g of titanium tetra-n-butoxide were dissolved in 200 mL of xylene in a nitrogen atmosphere. The temperature was raised to 150 ° C. and stirred for 6 hours. Subsequently, 16.2 g of 2- (2-butoxyethoxy) ethanol was added dropwise and stirred for 2 hours. Thereafter, the solvent was removed by a rotary evaporator at 20 hPa / 40 ° C., and then the remaining volatile components were removed by a rotary pump (10 Pa) and a cold trap (dry ice + ethanol).

47.7 g of 3-ethylxanthogenate-propyl (2- (2-butoxyethoxy) ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctane [organosilicon compound (C-7)] represented by the formula Obtained. The results of ¹ H-NMR analysis of the product are shown below.
¹ H-NMR (CDCl ₃ , 700 MHz, δ; ppm) = 4.6 (q; 2H), 3.8 (m; 6H), 3.5 (m; 8H), 3.1 (t; 2H), 2.5 (m; 4H), 2.4 (s; 3H), 1.8 (m; 2H), 1.4 (m; 7H), 0.9 (t; 3H), 0.7 (t; 2H)

<Preparation and evaluation of rubber composition>
The rubber composition of the mixing | blending prescription according to Tables 1-6 was knead | mixed and prepared with the Banbury mixer. Next, the vulcanization physical property of the obtained rubber composition was measured by the following method. The results are shown in Tables 1-6.

(1) Dynamic viscoelasticity Using a spectrometer (dynamic viscoelasticity measuring test machine) manufactured by Ueshima Seisakusho, the tan δ of vulcanized rubber was measured at a frequency of 52 Hz, initial strain of 10%, measurement temperature of 60 ° C, and dynamic strain of 1%. In Tables 1 to 3, the value of tan δ of Comparative Example 1 is shown as an index as 100. In Table 4, the value of tan δ of Comparative Example 12 is shown as an index as 100. In Table 5, the value of tan δ of Comparative Example 16 is shown. In Table 6, the value of tan δ of Comparative Example 20 was set as 100 and displayed as an index. The smaller the index value, the lower the tan δ, indicating that the rubber composition is less exothermic.

(2) Abrasion resistance test In accordance with JIS K 6264-2: 2005, a test was performed using a Lambone-type abrasion tester under conditions of room temperature and a slip rate of 25%. The reciprocal of the wear amount is displayed as an index as 100, and in Table 4, the reciprocal of the wear amount of Comparative Example 12 is displayed as an index as 100, and in Table 5, the reciprocal of the wear amount of Comparative Example 16 is displayed as an index as 100. 6, the index was displayed with the reciprocal of the wear amount of Comparative Example 20 as 100. The larger the index value, the smaller the wear amount and the better the wear resistance.

* 1 JSR, emulsion polymerization SBR, # 1500
* 2 Asahi Carbon, # 80
* 3 Tosoh Silica Industry Co., Ltd., nip seal AQ, BET surface area = 220 m ² / g
* 4 Bis (3-triethoxysilylpropyl) disulfide
* 5 3-Octanoylthio-propyltriethoxysilane
* 6 Nouchi 6C, manufactured by Ouchi Shinsei Chemical Industry
* 7 Ouchi Shinsei Chemical Industry, Nocrack 224
* 8 Sanshin Chemical Industry, Sunseller D
* 9 Sanshin Chemical Industry, Sunseller DM
* 10 Sanshin Chemical Industry, Sunseller NS
* 11 Made by JSR, emulsion polymerization SBR, # 1712, with 37.5 parts by weight of aromatic oil for 100 parts by weight of rubber component
* 12 RSS # 3
* 13 Asahi Carbon, # 78
* 14 N-cyclohexylbenzothiazole-2-sulfenamide
* 15 Ouchi Shinsei Chemical Industries, Noxeller TOT-N

  From Tables 1-6, it replaces with the conventional silane coupling agent (* 4 and * 5), and mix | blends the organosilicon compound (C) of this invention, The tan-delta of a rubber composition is reduced significantly, ie, It can be seen that the wear resistance can be greatly improved while the hysteresis loss is greatly reduced to reduce heat generation.

  Further, from the comparison between the rubber composition of the comparative example containing the organosilicon compound (C-1 to C-2) and the rubber composition of the example containing the organosilicon compound (C-3 to C-7), a nitrogen-containing functional group was obtained. When an organosilicon compound that does not contain a group is added to the rubber composition, the low heat build-up cannot be sufficiently improved, or the wear resistance cannot be sufficiently improved. It can be seen that it is impossible to achieve both.

Claims (15)

The following general formula (I):

[In the formula, at least one of R ¹ , R ² and R ³ is represented by the following general formula (II) or formula (III):

(In the formula, M is —O— or —CH ₂ —, X and Y are each independently —O—, —NR ⁸ — or —CH ₂ —, and R ⁶ is —OR ⁸ , —NR ⁸ R. ⁹ or -R ⁸ , R ⁷ is -NR ⁸ R ⁹ , -NR ⁸ -NR ⁸ R ⁹ or -N = NR ⁸ , provided that R ⁸ is -C _n H _{2n + 1} and R ⁹ is a _{-C q H 2q + 1, l} , m, n and q are represented by independently 0 to 20), others _{-M-C l H 2l + 1} ( wherein, M and l is as defined above) or _{- (M-C l H 2l} ) y C s H 2s + 1 ( wherein, M is as defined above, y and s are 1 to 20 independently Wherein at ^{least one} of R ¹ , R ² and R ³ is M is —O—,
R ⁴ represents the following general formula (IV) or formula (V):

(Wherein, M, X, Y, R 6, l and m are as defined above, R ¹⁰ is ^{-NR 8 -, - NR 8 -NR} 8 - or -N = N-a, provided that, R ⁸ Is as defined above) or -M-C ₁ H _2l- (wherein M and l are as defined above),
R ⁵ represents the above general formula (II), formula (III), or —C ₁ H _2l —R ¹¹ (where R ¹¹ represents —NR ⁸ R ⁹ , —NR ⁸ —NR ⁸ R ⁹ , —N═NR ^8). , H, or —M—C _m H _{2m + 1} or an aromatic hydrocarbon group having 6 to 20 carbon atoms, provided that R ⁸ , R ⁹ , M, l and m are as defined above. An organosilicon compound characterized by the above. The following general formula (VI):

Wherein W is —NR ⁸ —, —O— or —CR ⁸ R ¹⁵ — (wherein R ¹⁵ is —R ⁹ or —C _m H _2m —R ⁷ , where R ⁷ is —NR ⁸ R ⁹ , —NR ⁸ —NR ⁸ R ⁹ or —N═NR ⁸ , R ⁸ is —C _n H _{2n + 1} , R ⁹ is —C _q H _{2q + 1} , m, n and q Are each independently 0 to 20),
R ¹² and R ¹³ are each independently represented by —M—C ₁ H _{2 1} — (wherein M is —O— or —CH ₂ —, and 1 is 0 to 20),
R ¹⁴ is -M-C _l H _{2l + 1} or ^{_{-M-C l H 2l -R 7}} ( wherein, M, R ⁷ and l have the same meanings as mentioned above), or _{- (M-C l H 2l} ) _y C _s H _{2s + 1} (wherein M and l are as defined above, y and s are each independently 1 to 20), provided that R ¹² , R ¹³ and R ¹⁴ One or more of M is -O-
R ⁴ represents the following general formula (IV) or formula (V):

Wherein M, l and m are as defined above, X and Y are each independently —O—, —NR ⁸ — or —CH ₂ —, and R ⁶ is —OR ⁸ , —NR ⁸ R ⁹ or -R ^8, R ¹⁰ is ^{-NR 8 -, - NR 8 -NR} 8 - or -N = a N-, provided that, R ⁸ and R ⁹ are as defined above) or -M-C _l H _2l- (wherein M and l are as defined above),
R ⁵ represents the following general formula (II) or formula (III):

(Wherein, M, X, Y, R ⁶ , R ⁷ , l and m are as defined above) or —C ₁ H _2l —R ¹¹ (where R ¹¹ is —NR ⁸ R ⁹ , —NR ⁸ —NR ⁸ R ⁹ , —N═NR ⁸ , H, or —M—C _m H _{2m + 1} or an aromatic hydrocarbon group having 6 to 20 carbon atoms, provided that R ⁸ , R ⁹ , M, l and m are the same as defined above)].   The organosilicon compound according to claim 1, wherein M is —O—. At least one of R ¹ , R ² and R ³ is represented by —O—C ₁ H _{2 1} —R ⁷ (where R ⁷ and 1 are as defined above), and the others are —O—C. _l H _{2l + 1} (where l is as defined above),
R ⁴ is represented by —C ₁ H _2l — (wherein l is as defined above),
The organosilicon compound according to claim 1 or 3, wherein R ⁵ is represented by -C _l H _2l -R ¹¹ (wherein R ¹¹ and l are as defined above). At least one of R ¹ , R ² and R ³ is represented by —O—C ₁ H _{2 1} —NR ⁸ R ⁹ (where R ⁸ , R ⁹ and 1 are as defined above),
A linear or branched alkyl group represented by R ⁵ —C _l H _{2l + 1} (wherein l is as defined above), or an aromatic hydrocarbon group having 6 to 20 carbon atoms; The organosilicon compound according to claim 1, 3 or 4. W is represented by —NR ⁸ — (wherein R ⁸ is as defined above),
R ¹² and R ¹³ are each independently represented by —O—C ₁ H _2l — (wherein l is as defined above),
R ¹⁴ is represented by —O—C _l H _2l —R ⁷ (wherein R ⁷ and l are as defined above),
R ⁴ is represented by —C ₁ H _2l — (wherein l is as defined above),
A linear or branched alkyl group, or an aromatic hydrocarbon group having 6 to 20 carbon atoms, wherein R ⁵ is represented by —C _l H _{2l + 1} (wherein l is as defined above). The organosilicon compound according to claim 2, wherein the organosilicon compound is present. W is represented by —O— or —CR ⁸ R ⁹ — (wherein R ⁸ and R ⁹ are as defined above),
R ¹² and R ¹³ are each independently represented by —O—C ₁ H _2l — (wherein l is as defined above),
R ¹⁴ is represented by —O—C ₁ H _{2 1} —NR ⁸ R ⁹ (wherein R ⁸ , R ⁹ and l are as defined above),
R ⁴ is represented by —C ₁ H _2l — (wherein l is as defined above),
4. The organosilicon compound according to claim 2, wherein R ⁵ is represented by —C ₁ H _{2l + 1} (wherein l is as defined above).   An inorganic filler (B) and the organosilicon compound (C) according to any one of claims 1 to 7 are blended with a rubber component (A) made of natural rubber and / or a diene synthetic rubber. Rubber composition. To 100 parts by mass of the rubber component (A) composed of the natural rubber and / or diene synthetic rubber, 5 to 140 parts by mass of the inorganic filler (B)
Furthermore, 1-20 mass% of the compounding quantity of the said inorganic filler (B) is included for the said organosilicon compound (C), The rubber composition of Claim 8 characterized by the above-mentioned.   The rubber composition according to claim 8, wherein the inorganic filler (B) is silica or aluminum hydroxide. The rubber composition according to claim 10, wherein the silica has a BET surface area of 40 to 350 m ² / g.   A tire using the rubber composition according to any one of claims 8 to 11.   The primer composition containing the organosilicon compound in any one of Claims 1-7.   The coating composition containing the organosilicon compound in any one of Claims 1-7.   An adhesive comprising the organosilicon compound according to claim 1.