JP2010270053A - Organosilicon compound, and rubber composition, tire, primer composition, coating composition and adhesive, comprising the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a novel compound that greatly decreases a hysteresis loss and greatly enhances abrasion resistance of a rubber composition, a rubber composition comprising the compound and a tire obtained using the rubber composition. <P>SOLUTION: The organosilicon compound includes, in the molecule, a group reactive with silica and a group bearing a sulfur atom and a carbon atom, at the β-position of the sulfur atom, to which a hydrogen atom and an electron-withdrawing group are bonded. The rubber composition comprises a rubber component (A) composed of a natural rubber and/or a diene synthetic rubber and, incorporated therewith, an inorganic filler (B) and the organosilicon compound (C). The tire is obtained using the rubber composition. The organosilicon compound can be used for a primer composition, a coating composition or an adhesive. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

  The present invention relates to an organosilicon compound, a rubber composition containing the organosilicon compound, a tire using the rubber composition, a primer composition containing the organosilicon compound, a coating composition, and an adhesive, and particularly, a rubber. The present invention relates to an organosilicon compound capable of reducing the hysteresis loss of the composition and improving the wear resistance.

  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.

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 inventor, 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. It was found that the level of improvement could not be sufficiently satisfied and there was still 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 containing such a compound, a tire using the rubber composition, a primer composition containing the compound, a coating composition, and an adhesive.

  As a result of intensive studies to achieve the above-mentioned object, the present inventors have found that a group that reacts with silica in the molecule, a sulfur atom, and a hydrogen atom and an electron withdrawing to a carbon atom at the β-position of the sulfur atom. Since the organosilicon compound having a group to which a functional group is bonded has a high reaction rate with an inorganic filler such as silica, the efficiency of the coupling reaction can be improved by adding the organosilicon compound to the rubber component together with the inorganic filler. As a result, it was found that the wear resistance can be greatly improved while greatly reducing the hysteresis loss of the rubber composition, and the present invention has been completed.

  That is, the organosilicon compound of the present invention comprises, in the molecule, a group that reacts with silica, and a group that contains a sulfur atom and a hydrogen atom and an electron withdrawing group bonded to the β-position carbon atom of the sulfur atom. It is characterized by having.

  In a preferred example of the organosilicon compound of the present invention, the group that reacts with silica contains an oxygen atom bonded to a silicon atom.

［式(I)中の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−、−ＮＲ¹⁰−又は−ＣＨ₂−で、Ｒ⁸は−ＯＲ¹⁰、−ＮＲ¹⁰Ｒ¹¹又は−Ｒ¹⁰で、Ｒ⁹は−ＮＲ¹⁰Ｒ¹¹、−ＮＲ¹⁰−ＮＲ¹⁰Ｒ¹¹、−Ｎ＝ＮＲ¹⁰又はＨで、但し、Ｒ¹⁰は−Ｃ_nＨ_2n+1であり、Ｒ¹¹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）又は−(Ｍ−Ｃ_lＨ_2l)_yＣ_sＨ_2s+1（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、Ｒ⁸、ｌ及びｍは上記と同義であり、Ｒ¹²は−ＮＲ¹⁰−、−ＮＲ¹⁰−ＮＲ¹⁰−又は−Ｎ＝Ｎ−で、但し、Ｒ¹⁰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、Ｒ⁶及びＲ⁷はそれぞれ独立して水素原子、炭素数１〜２０の直鎖アルキル基、炭素数３〜２０の分岐アルキル基又は炭素数６〜２０のアリール基であり、
Ａは炭素原子、窒素原子、硫黄原子又はリン原子であり、
Ｂは＝Ｏ又は＝ＮＲ¹³（ここで、Ｒ¹³は、水素原子、炭素数１〜２０の直鎖アルキル基、炭素数３〜２０の分岐アルキル基又は炭素数６〜２０のアリール基である）であり、
Ｄは−Ｏ−、−Ｓ−又は−ＮＲ¹⁴−（ここで、Ｒ¹⁴は、水素原子、炭素数１〜２０の直鎖アルキル基、炭素数３〜２０の分岐アルキル基又は炭素数６〜２０のアリール基である）であり、
ａは０〜２で、ｂは０〜４で、但し、Ａが炭素原子の場合、２ａ＋ｂは３で、Ａが窒素原子の場合、２ａ＋ｂは２で、Ａが硫黄原子の場合、２ａ＋ｂは１、３又は５で、Ａがリン原子の場合、２ａ＋ｂは２又は４である］で表される有機ケイ素化合物が好ましい。 As the organosilicon compound of the present invention, the following general formula (I):

[At least one of R ¹ , R ² and R ³ in the formula (I) 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 ¹⁰ — or —CH ₂ —, and R ⁸ is —OR ¹⁰ , —NR ¹⁰ R; ¹¹ or -R ¹⁰ , R ⁹ is -NR ¹⁰ R ¹¹ , -NR ¹⁰ -NR ¹⁰ R ¹¹ , -N = NR ¹⁰ or H, provided that R ¹⁰ is -C _n H _{2n + 1} , R ¹¹ is _{-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 have the same meanings as mentioned above) or _{- (M-C l H 2l} ) y C s H 2s + 1 (M and l are 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):

(In the formula, M, X, Y, R ⁸ , l and m are as defined above, and R ¹² is —NR ¹⁰ —, —NR ¹⁰ —NR ¹⁰ — or —N═N—, wherein R ¹⁰ Is as defined above) or -M-C ₁ H _2l- (wherein M and l are as defined above),
R ⁵ , R ⁶ and R ⁷ are each independently a hydrogen atom, a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms,
A is a carbon atom, a nitrogen atom, a sulfur atom or a phosphorus atom,
B is ═O or ═NR ¹³ (wherein R ¹³ is a hydrogen atom, a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms. ) And
D is —O—, —S— or —NR ¹⁴ — (where R ¹⁴ is a hydrogen atom, a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, or 6 to 6 carbon atoms). 20 aryl groups),
a is 0-2, b is 0-4, provided that when A is a carbon atom, 2a + b is 3, when A is a nitrogen atom, 2a + b is 2, and when A is a sulfur atom, 2a + b is 1 3 or 5, and when A is a phosphorus atom, 2a + b is 2 or 4].

［式(VI)中のＷは−ＮＲ¹⁰−、−Ｏ−又は−ＣＲ¹⁰Ｒ¹⁸−（ここで、Ｒ¹⁸は−Ｒ¹¹又は−Ｃ_mＨ_2m−Ｒ⁹であり、但し、Ｒ⁹は−ＮＲ¹⁰Ｒ¹¹、−ＮＲ¹⁰−ＮＲ¹⁰Ｒ¹¹、−Ｎ＝ＮＲ¹⁰又はＨであり、Ｒ¹⁰は−Ｃ_nＨ_2n+1で、Ｒ¹¹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）で表され、
Ｒ¹⁵及びＲ¹⁶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）で表され、
Ｒ¹⁷は−Ｍ−Ｃ_lＨ_2l+1又は−Ｍ−Ｃ_lＨ_2l−Ｒ⁹（ここで、Ｍ、ｌ及びＲ⁹は上記と同義である）或いは−(Ｍ−Ｃ_lＨ_2l)_yＣ_sＨ_2s+1（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）で表され、但し、Ｒ¹⁵、Ｒ¹⁶及びＲ¹⁷の一つ以上はＭが−Ｏ−であり、
Ｒ⁴は下記一般式(VII)又は式(VIII)：

（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−、−ＮＲ¹⁰−又は−ＣＨ₂−で、Ｒ⁸は−ＯＲ¹⁰、−ＮＲ¹⁰Ｒ¹¹又は−Ｒ¹⁰で、Ｒ¹²は−ＮＲ¹⁰−、−ＮＲ¹⁰−ＮＲ¹⁰−又は−Ｎ＝Ｎ−であり、但し、Ｒ¹⁰及びＲ¹¹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、Ｒ⁶及びＲ⁷はそれぞれ独立して水素原子、炭素数１〜２０の直鎖アルキル基、炭素数３〜２０の分岐アルキル基又は炭素数６〜２０のアリール基であり、
Ａは炭素原子、窒素原子、硫黄原子又はリン原子であり、
Ｂは＝Ｏ又は＝ＮＲ¹³（ここで、Ｒ¹³は、水素原子、炭素数１〜２０の直鎖アルキル基、炭素数３〜２０の分岐アルキル基又は炭素数６〜２０のアリール基である）であり、
Ｄは−Ｏ−、−Ｓ−又は−ＮＲ¹⁴−（ここで、Ｒ¹⁴は、水素原子、炭素数１〜２０の直鎖アルキル基、炭素数３〜２０の分岐アルキル基又は炭素数６〜２０のアリール基である）であり、
ａは０〜２で、ｂは０〜４で、但し、Ａが炭素原子の場合、２ａ＋ｂは３で、Ａが窒素原子の場合、２ａ＋ｂは２で、Ａが硫黄原子の場合、２ａ＋ｂは１、３又は５で、Ａがリン原子の場合、２ａ＋ｂは２又は４である］で表される有機ケイ素化合物も好ましい。 In addition, as the organosilicon compound of the present invention, the following general formula (VI):

[W in Formula (VI) is —NR ¹⁰ —, —O— or —CR ¹⁰ R ¹⁸ — (wherein R ¹⁸ is —R ¹¹ or —C _m H _2m —R ⁹ , where R ⁹ Is —NR ¹⁰ R ¹¹ , —NR ¹⁰ —NR ¹⁰ R ¹¹ , —N═NR ¹⁰ or H, R ¹⁰ is —C _n H _{2n + 1} , R ¹¹ is —C _q H _{2q + 1} , m, n and q are each independently 0 to 20),
R ¹⁵ and R ¹⁶ 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 ¹⁷ is -M-C ₁ H _{2l + 1} or -M-C ₁ H _2l -R ⁹ (wherein M, l and R ⁹ are as defined above) or-(M-C ₁ H _2l ) _y C _s H _{2s + 1} (M and l are as defined above, y and s are each independently 1 to 20), provided that one or more of R ¹⁵ , R ¹⁶ and R ¹⁷ M is -O-
R ⁴ represents the following general formula (VII) or formula (VIII):

(Wherein M, l and m are as defined above, X and Y are each independently —O—, —NR ¹⁰ — or —CH ₂ —, R ⁸ is —OR ¹⁰ , —NR ¹⁰ R; ¹¹ or -R ¹⁰ , R ¹² is -NR ^10- , -NR ¹⁰ -NR ¹⁰ -or -N = N-, provided that R ¹⁰ and R ¹¹ are as defined above) or -MC _l H _2l- (wherein M and l are as defined above),
R ⁵ , R ⁶ and R ⁷ are each independently a hydrogen atom, a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms,
A is a carbon atom, a nitrogen atom, a sulfur atom or a phosphorus atom,
B is ═O or ═NR ¹³ (wherein R ¹³ is a hydrogen atom, a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms. ) And
D is —O—, —S— or —NR ¹⁴ — (where R ¹⁴ is a hydrogen atom, a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, or 6 to 6 carbon atoms). 20 aryl groups),
a is 0-2, b is 0-4, provided that when A is a carbon atom, 2a + b is 3, when A is a nitrogen atom, 2a + b is 2, and when A is a sulfur atom, 2a + b is 1 3 or 5 and when A is a phosphorus atom, 2a + b is 2 or 4] is also preferable.

  In the preferable organic compound, 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 ⁹ (where R ⁹ and 1 are as defined above). The other is represented by —O—C ₁ H _{2l + 1} (wherein l is as defined above),
R ⁴ is represented by —C ₁ H _2l — (wherein l is as defined above),
R ⁵ is preferably a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

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 ¹⁰ R ¹¹ (where R ¹⁰ , R ¹¹ And l are as defined above),
More preferably, R ⁵ is a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

In the organosilicon compound represented by the above formula (VI), the W is represented by —NR ¹⁰ — (wherein R ¹⁰ is as defined above),
R ¹⁵ and R ¹⁶ are each independently represented by —O—C ₁ H _2l — (wherein l is as defined above),
R ¹⁷ is represented by —O— _Cl H _2l —R ⁹ (wherein R ⁹ and l are as defined above),
R ⁴ is represented by —C ₁ H _2l — (wherein l is as defined above),
R ⁵ is preferably a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

In the organosilicon compound represented by the above formula (VI), the W is represented by —O— or —CR ¹⁰ R ¹¹ — (wherein R ¹⁰ and R ¹¹ are as defined above),
R ¹⁵ and R ¹⁶ are each independently represented by —O—C ₁ H _2l — (wherein l is as defined above),
R ¹⁷ is represented by —O—C ₁ H _{2 1} —NR ¹⁰ R ¹¹ (where R ¹⁰ , R ¹¹ and l are as defined above),
R ⁴ is represented by —C ₁ H _2l — (wherein l is as defined above),
R ⁵ is preferably a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

  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. Here, the silica preferably has a BET surface area of 40 to 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-mentioned organosilicon compound, the coating composition of the present invention is characterized by comprising the above-mentioned organosilicon compound, and the adhesive of the present invention is the above-mentioned It is characterized by including the organosilicon compound of this.

  According to the present invention, the rubber has a group that reacts with silica and a group that contains a sulfur atom and in which a hydrogen atom and an electron withdrawing group are bonded to a carbon atom at the β-position of the sulfur atom. It is possible to provide an organosilicon compound capable of significantly reducing the hysteresis loss of the composition and capable of greatly improving the wear resistance. In addition, a rubber composition containing the organosilicon compound, a tire using the rubber composition, and a primer composition, a coating composition and an adhesive containing the organosilicon compound can be provided.

<Organic silicon compound>
The present invention is described in detail below. In the organosilicon compound of the present invention, a hydrogen atom and an electron-withdrawing group are bonded to a carbon atom (C) in a molecule containing a sulfur atom (S) and a sulfur atom (S). It is characterized by having a group. Here, the group that reacts with silica means a group showing good reactivity capable of sufficiently causing a hydrolysis reaction or a condensation reaction at the interface with silica, and preferably contains an oxygen atom bonded to a silicon atom. It is a group and can contribute to the improvement of the dispersibility of inorganic fillers such as silica. That is, the organosilicon compound preferably has one or more silicon-oxygen bonds (Si-O) in the molecule. Moreover, the organosilicon compound of the present invention has a group containing a sulfur atom in addition to a group that reacts with silica, and the carbon atom located at the β-position of the sulfur atom in the group includes a hydrogen atom and An electron withdrawing group is bound. Thus, the organosilicon compound of the present invention has a carbon-sulfur bond (C—S) in the molecular structure and forms a stable structure. However, since the hydrogen atom and the electron withdrawing group are bonded to the β-position carbon atom of the sulfur atom, the acidity of the hydrogen atom is high. Therefore, by heating the organosilicon compound of the present invention, the hydrogen atom bonded to the β-position carbon atom is eliminated (ie, deprotonation proceeds), the carbon-sulfur bond is cleaved, and the thiol group is removed. It can be generated effectively. Therefore, instead of the conventional silane coupling agent, by adding the organosilicon compound of the present invention to the inorganic filler-containing rubber composition, the reaction between the silane coupling agent and the rubber component is promoted during vulcanization, Coupling efficiency is improved. As a result, it is possible to greatly improve the wear resistance while greatly reducing the hysteresis loss of the rubber composition. In the present invention, the organosilicon compound contains a sulfur atom and has a group in which a hydrogen atom and an electron withdrawing group are bonded to a carbon atom at the β-position of the sulfur atom, thereby improving the coupling efficiency. Therefore, the group that reacts with silica of the organosilicon compound is not particularly limited as long as it is a group that exhibits reactivity with silica, and includes various groups. 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. Furthermore, the organosilicon compound of the present invention forms a stable structure as described above, and can improve workability when not vulcanized. In addition, since the organosilicon compound of the present invention can improve the dispersibility of inorganic fillers such as silica by improving the coupling efficiency, it improves the low rolling resistance of tires, braking performance on wet road surfaces, and steering stability. You can also

  More specifically, the organic silicon compound of the present invention is preferably a compound represented by the above general formula (I) and a compound represented by the above general formula (VI). These organosilicon compounds may be used individually by 1 type, and may be used in combination of 2 or more type.

<< Compound of Formula (I) >>
In the above 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 others are —M—C ₁ H _{2l + 1} (where , M is —O— or —CH ₂ —, l is 0 to 20, preferably in the range of 0 to 10) or — (M—C ₁ H _{2 l} ) _y C _s H _{2s + 1} (M and l is as defined above, and y and s are each independently 1 to 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. 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. 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, a propylene group, etc. are mentioned, This alkylene group may be linear or branched.

In the above formulas (II) and (III), M is —O— or —CH ₂ —, and l is 0 to 20, preferably 0 to 10. Moreover, in said formula (II), m is 0-20, and the range of 0-10 is preferable. Incidentally, -C _m H _{2m + 1,} since m is 0 to 20, hydrogen or an alkyl group having 1 to 20 carbon atoms. The alkyl group having 1 to 20 carbon atoms is as described above.

In the above formula (II), X and Y are each independently —O—, —NR ¹⁰ — or —CH ₂ —. Wherein, R ¹⁰ is -C _n H _{2n + 1, n} is 0 to 20, preferably in the range of 0. 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. R ⁸ is —OR ¹⁰ , —NR ¹⁰ R ¹¹ or —R ¹⁰ . Wherein, R ¹⁰ is _{-C n H 2n + 1, R} 11 is -C _q H _{2q + 1,} n and q are 0 to 20 independently, preferably in the range of 0 . 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. The alkyl group having 1 to 20 carbon atoms is as described above.

In the above formula (III), R ⁹ is —NR ¹⁰ R ¹¹ , —NR ¹⁰ —NR ¹⁰ R ¹¹ , —N═NR ¹⁰ or H. Wherein, R ¹⁰ is _{-C n H 2n + 1, R} 11 is -C _q H _{2q + 1,} n and q are 0 to 20 independently, preferably in the range of 0 . Note that the -C _n H _{2n + 1} and -C _q H _{2q + 1,} is as described above.

In the above formula (I), R ⁴ is represented by the above general formula (IV), formula (V), or —M—C ₁ H _2l —, particularly —C ₁ H _2l —. Wherein M is —O— or —CH ₂ —, and l is 0 to 20, preferably 0 to 10. 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 is as described above.

In the above formulas (IV) and (V), M is —O— or —CH ₂ —, and l and m are 0 to 20, preferably 0 to 10. In the above formula (IV), X and Y are each independently —O—, —NR ¹⁰ — or —CH ₂ —, and R ⁸ is —OR ¹⁰ , —NR ¹⁰ R ¹¹ or —R ¹⁰ . is there. R ¹⁰ and R ¹¹ are as described above. Further, in the above formula (V), R ¹² is —NR ¹⁰ —, —NR ¹⁰ —NR ¹⁰ — or —N═N—, wherein R ¹⁰ is —C _n H _{2n + 1} , the -C _n H _{2n + 1,} as described above.

Further, in the above formula (I), R ⁵ , R ⁶ and R ⁷ are a hydrogen atom, a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms or an aryl having 6 to 20 carbon atoms. It is a group. Here, examples of the linear alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a decyl group, and a dodecyl group. Examples of the branched alkyl group having 3 to 20 carbon atoms include isopropyl group, isobutyl group, isopentyl group, isohexyl group, isooctyl group, and isostearyl group. The aryl group having 6 to 20 carbon atoms includes a phenyl group. Naphthyl group, anthracenyl group, phenanthrenyl group, toluyl group, nonylphenyl group and the like.

In the above formula (I), A is a carbon atom, nitrogen atom, sulfur atom or phosphorus atom, B is ═O or ═NR ¹³ , and D is —O—, —S— or —NR ^14. -. Wherein, R ¹³ and R ¹⁴ are each independently a hydrogen atom, a linear alkyl group having 1 to 20 carbon atoms, branched alkyl group or an aryl group having 6 to 20 carbon atoms having 3 to 20 carbon atoms. In addition, about a C1-C20 linear alkyl group, a C3-C20 branched alkyl group, and a C6-C20 aryl group, it is as above-mentioned.

  Furthermore, in the said formula (I), a is 0-2 and b is 0-4. However, when A is a carbon atom, 2a + b is 3, when A is a nitrogen atom, 2a + b is 2, when A is a sulfur atom, 2a + b is 1, 3 or 5, and when A is a phosphorus atom, 2a + b Is 2 or 4.

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 ⁹ , and the other is —O—C ₁ H _{2l + 1.} R ⁴ is preferably represented by —C ₁ H _2l —, and R ⁵ is a linear alkyl group having 1 to 20 carbon atoms or a branched alkyl group having 3 to 20 carbon atoms. Or it is preferable that it is a C6-C20 aryl group.

Furthermore, in the compound of the above formula (I), at least one of R ¹ , R ² and R ³ is more preferably represented by —O—C ₁ H _{2 1} —NR ¹⁰ R ¹¹ , and R ⁴ is -C _l H _2l - is preferably represented by, that the R ⁵ is a straight-chain alkyl group, branched alkyl group or an aryl group having 6 to 20 carbon atoms having 3 to 20 carbon atoms having 1 to 20 carbon atoms Is preferred.

<< Compound of Formula (VI) >>
In the above formula (VI), W is represented by —NR ¹⁰ —, —O— or —CR ¹⁰ R ¹⁸ —, wherein R ¹⁸ is —R ¹¹ or —C _m H _2m —R ⁹ ; However, R ⁹ is ^{-NR 10 R 11, -NR 10 -NR} 10 R 11, a -N = NR ¹⁰ or H, with R ¹⁰ is _{-C n H 2n + 1, R} 11 is -C _q H _{2q In +1} , m, n, and q are each independently 0-20, and the range of 0-10 is preferable. 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, a propylene group, etc. are mentioned, This 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 formula (VI), R ¹⁵ and R ¹⁶ are each independently represented by —M—C ₁ H _2l —, and R ¹⁷ is —M—C ₁ H _{2l + 1} or —M—C ₁ H _2l —. R ⁹ or — (M—C ₁ H _{2 l} ) _y C _s H _{2s + 1} , where M is —O— or —CH ₂ —, and R ⁹ is —NR ¹⁰ R ¹¹ , —NR ¹⁰ -NR ¹⁰ R ¹¹ , -N = NR ¹⁰ or H, R ¹⁰ is -C _n H _{2n + 1} , R ¹¹ is -C _q H _{2q + 1} , and l, n and q are each independent. 0 to 20 and a range of 0 to 10 is preferable, and y and s are each independently 1 to 20. However, in one or more of R ¹⁵ , R ¹⁶ and R ¹⁷ , 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 is as described above. It is. Moreover, since l is 0 to 20, —C ₁ H _{2l + 1} is hydrogen or an alkyl group having 1 to 20 carbon atoms. Further, -C _s H _{2s + 1,} since s is 1 to 20, an alkyl group having 1 to 20 carbon atoms. Here, the alkyl group having 1 to 20 carbon atoms is as described above. Note that the -C _n H _{2n + 1} and -C _q H _{2q + 1,} is as described above.

In the above formula (VI), R ⁴ is represented by the above general formula (VII) or (VIII), or —M—C ₁ H _2l —, and in particular, —C ₁ H _2l —. Wherein M is —O— or —CH ₂ —, and l is 0 to 20, preferably 0 to 10. In addition, -C _l H _2l- is as described above.

In the above formulas (VII) and (VIII), M is —O— or —CH ₂ —, and l and m are 0 to 20, preferably 0 to 10. In the above formula (VII), X and Y are each independently —O—, —NR ¹⁰ — or —CH ₂ —, and R ⁸ is —OR ¹⁰ , —NR ¹⁰ R ¹¹ or —R ¹⁰ . Yes, where R ¹⁰ is —C _n H _{2n + 1} and R ¹¹ is —C _q H _{2q + 1} . Further, in the above formula (VIII), R ¹² is —NR ¹⁰ —, —NR ¹⁰ —NR ¹⁰ —, or —N═N—, wherein R ¹⁰ is —C _n H _{2n + 1} . Note that the -C _n H _{2n + 1} and -C _q H _{2q + 1,} is as described above.

Further, in the above formula ^{(VI), R 5, R} 6 and R ⁷ are each independently a hydrogen atom, a linear alkyl group having 1 to 20 carbon atoms, the number branched alkyl group or C 3 to 20 carbon atoms 6 ˜20 aryl groups. Here, examples of the linear alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a decyl group, and a dodecyl group. Examples of the branched alkyl group having 3 to 20 carbon atoms include isopropyl group, isobutyl group, isopentyl group, isohexyl group, isooctyl group, and isostearyl group. The aryl group having 6 to 20 carbon atoms includes a phenyl group. Naphthyl group, anthracenyl group, phenanthrenyl group, toluyl group, nonylphenyl group and the like.

Furthermore, in the above formula (VI), A is a carbon atom, nitrogen atom, sulfur atom or phosphorus atom, B is ═O or ═NR ¹³ , and D is —O—, —S— or —NR ^14. -. Wherein, R ¹³ and R ¹⁴ are each independently a hydrogen atom, a linear alkyl group having 1 to 20 carbon atoms, branched alkyl group or an aryl group having 6 to 20 carbon atoms having 3 to 20 carbon atoms. In addition, about a C1-C20 linear alkyl group, a C3-C20 branched alkyl group, and a C6-C20 aryl group, it is as above-mentioned.

  Furthermore, in the said Formula (VI), a is 0-2 and b is 0-4. However, when A is a carbon atom, 2a + b is 3, when A is a nitrogen atom, 2a + b is 2, when A is a sulfur atom, 2a + b is 1, 3 or 5, and when A is a phosphorus atom, 2a + b Is 2 or 4.

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 ¹⁰ —, R ¹⁵ and R ¹⁶ are preferably independently represented by —O—C ₁ H _2l —, and R ¹⁷ is —O—C. Preferably, it is represented by ₁ H _2l -R ⁹ , R ⁴ is preferably represented by -C ₁ H _2l- , and R ⁵ is a linear alkyl group having 1 to 20 carbon atoms, 3 carbon atoms It is preferable that it is a -20 branched alkyl group or a C6-C20 aryl group.

On the other hand, when the W is represented by —O— or —CR ¹⁰ R ¹¹ —, the R ¹⁵ and R ¹⁶ are preferably each independently represented by —O—C ₁ H _2l —. ¹⁷ is preferably represented by —O—C ₁ H _2l —NR ¹⁰ R ¹¹ , R ⁴ is preferably represented by —C ₁ H _2l —, and R ⁵ has 1 to 20 carbon atoms. A linear alkyl group, a branched alkyl group having 3 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms is preferable.

［式(IX)中のＲ¹、Ｒ²、Ｒ³及びＲ⁴は上記と同義であり、Ｑはハロゲンである］で表される化合物に対し、下記一般式(X)：

［式(X)中のＲ⁵、Ｒ⁶、Ｒ⁷、Ａ、Ｂ、Ｄ、ａ及びｂは上記と同義である］で表されるチオール化合物を加え、必要に応じて触媒等を添加し、加熱することで、合成できる。 << Synthesis Method of Organosilicon Compound >>
The organosilicon compound of the present invention includes, for example, the following general formula (IX):

For the compound represented by the formula (IX), R ¹ , R ² , R ³ and R ⁴ are as defined above and Q is a halogen, the following general formula (X):

[R ⁵ , R ⁶ , R ⁷ , A, B, D, a and b in the formula (X) are as defined above], and a catalyst or the like is added if necessary. It can be synthesized by heating.

<< Specific Examples of Organosilicon Compounds >>
Specific examples of the organosilicon compound of the present invention include 2-ethylhexyl-3- (3- (triethoxysilyl) propylthio) propanoate, hexyl-3- (3- (triethoxysilyl) propylthio) propanoate, stearyl-3. -(3- (Triethoxysilyl) propylthio) propanoate, 2-ethylhexyl-3- (3- (diethoxymethylsilyl) propylthio) propanoate, 2-ethylhexyl-3- (3-((ethoxy) 1,3-dioxa -6-methylaza-2-silacyclooctanyl) propylthio) propanoate and the like.

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

  The compounding quantity of the said inorganic filler (B) is the range of 5-140 mass parts with respect to 100 mass parts of said rubber components (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, the braking performance on a wet road surface, and the steering stability are 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>
The primer composition, coating composition, and adhesive of the present invention are characterized by containing the above-mentioned organosilicon compound, and have good primer properties for various workpieces such as glass, various painted surfaces, and porous surfaces. In addition, sufficient coatability and adhesiveness can be exhibited.

  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.

で表される化合物（２-エチルヘキシル-３-(３-(トリエトキシシリル)プロピルチオ)プロパノアート）であることを確認した。
¹Ｈ−ＮＭＲ(CDCl3, 700MHz, δ;ppm) = 4.1(d;2H), 3.8(m;6H), 2.7(t;2H), 2.6(t;2H), 2.3(t;2H), 1.6(m;3H), 1.3(m;17H), 0.9(t;6H), 0.7(t;2H) <Production example of organosilicon compound A>
In an argon atmosphere, charge 12.0 g of 3-chloropropyltriethoxysilane and 10.9 g of 2-ethylhexyl-3-mercaptopropanoate into a reaction vessel (50 ml) and stir from room temperature to 100 ° C for about 1 hour. The temperature rose. Thereafter, the reaction was further carried out at 100 ° C. for 1 hour. At that time, by-product ethanol was removed by using a Dean-Stark apparatus. 35 g of the obtained product was analyzed by various spectrum data, and the following formula (XI):

(2-ethylhexyl-3- (3- (triethoxysilyl) propylthio) propanoate).
¹ H-NMR (CDCl3, 700 MHz, δ; ppm) = 4.1 (d; 2H), 3.8 (m; 6H), 2.7 (t; 2H), 2.6 (t; 2H), 2.3 (t; 2H), 1.6 (m; 3H), 1.3 (m; 17H), 0.9 (t; 6H), 0.7 (t; 2H)

<Production example of organosilicon compound B>
In a 500 mL four-necked eggplant flask under nitrogen atmosphere, 42.2 g of 2-ethylhexyl-3- (3- (triethoxysilyl) propylthio) propanoate, 11.9 g of N-methyldiethanolamine, 0.05 g of titanium tetra-n-butoxide, and 200 mL of xylene Dissolved in. 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) to obtain 2-ethylhexyl-3. 41.7 g of-(3- (ethoxy) 1,3-dioxa-6-methylaza-2-silacyclooctylpropylthio) propanoate were obtained.
¹ H-NMR (CDCl3, 700 MHz, δ; ppm) = 4.1 (d; 2H), 3.8 (m; 6H), 2.7 (t; 2H), 2.6 (t; 2H), 2.5 (m; 4H), 2.3 (m; 5H), 1.6 (m; 3H), 1.3 (m; 11H), 0.9 (t; 6H), 0.7 (t; 2H)

<Preparation and evaluation of rubber composition>
A rubber composition having a formulation according to Table 1 was prepared by kneading with a Banbury mixer. Next, the vulcanization physical property of the obtained rubber composition was measured by the following method. The results are shown in Table 1.

(1) Dynamic viscoelasticity test Using a spectrometer (dynamic viscoelasticity tester) manufactured by Ueshima Seisakusho, tan δ of vulcanized rubber at a frequency of 52 Hz, initial strain of 10%, measurement temperature of 60 ° C, and dynamic strain of 1%. Measured and indicated as an index with the value of tan δ of Comparative Example 1 being 100. 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 the conditions of room temperature and a slip rate of 25%. As an index. 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 Made by Nippon Silica Kogyo Co., Ltd., nip seal AQ, BET surface area = 220m ² / g
* 4 Bis (3-triethoxysilylpropyl) disulfide
* 5 3-Octanoylthio-propyltriethoxysilane
* 6 Nouchi 6C, manufactured by Ouchi Shinsei Chemical Industry
* 7 Nouchi 224, manufactured by Ouchi Shinsei Chemical Industry
* 8 Sunseller D, manufactured by Sanshin Chemical Industry
* 9 Sunseller DM, manufactured by Sanshin Chemical Industry
* 10 Sunseller NS, manufactured by Sanshin Chemical Industry

  From Table 1, by replacing the conventional silane coupling agent (* 4 and * 5) with the organosilicon compound (C) of the present invention, tan δ of the rubber composition is greatly reduced, that is, hysteresis loss. It can be seen that the wear resistance can be greatly improved while significantly reducing the heat resistance and reducing the heat generation.

Claims (17)

  An organosilicon compound having, in its molecule, a group that reacts with silica, and a group containing a sulfur atom and a group having a hydrogen atom and an electron-attracting group bonded to a carbon atom at the β-position of the sulfur atom.   The organosilicon compound according to claim 1, wherein the group that reacts with silica contains an oxygen atom that bonds to a silicon atom. The following general formula (I):

[At least one of R ¹ , R ² and R ³ in the formula (I) 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 ¹⁰ — or —CH ₂ —, and R ⁸ is —OR ¹⁰ , —NR ¹⁰ R; ¹¹ or -R ¹⁰ , R ⁹ is -NR ¹⁰ R ¹¹ , -NR ¹⁰ -NR ¹⁰ R ¹¹ , -N = NR ¹⁰ or H, provided that R ¹⁰ is -C _n H _{2n + 1} , R ¹¹ is _{-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 have the same meanings as mentioned above) or _{- (M-C l H 2l} ) y C s H 2s + 1 (M and l are 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):

(In the formula, M, X, Y, R ⁸ , l and m are as defined above, and R ¹² is —NR ¹⁰ —, —NR ¹⁰ —NR ¹⁰ — or —N═N—, wherein R ¹⁰ Is as defined above) or -M-C ₁ H _2l- (wherein M and l are as defined above),
R ⁵ , R ⁶ and R ⁷ are each independently a hydrogen atom, a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms,
A is a carbon atom, a nitrogen atom, a sulfur atom or a phosphorus atom,
B is ═O or ═NR ¹³ (wherein R ¹³ is a hydrogen atom, a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms. ) And
D is —O—, —S— or —NR ¹⁴ — (where R ¹⁴ is a hydrogen atom, a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, or 6 to 6 carbon atoms). 20 aryl groups),
a is 0 to 2 and b is 0 to 4, provided that when A is a carbon atom, 2a + b is 3, when A is a nitrogen atom, 2a + b is 2, and when A is a sulfur atom, 2a + b is 1 The organic silicon compound according to claim 1, wherein 3 or 5 and A is a phosphorus atom, 2a + b is 2 or 4. The following general formula (VI):

[W in Formula (VI) is —NR ¹⁰ —, —O— or —CR ¹⁰ R ¹⁸ — (wherein R ¹⁸ is —R ¹¹ or —C _m H _2m —R ⁹ , where R ⁹ Is —NR ¹⁰ R ¹¹ , —NR ¹⁰ —NR ¹⁰ R ¹¹ , —N═NR ¹⁰ or H, R ¹⁰ is —C _n H _{2n + 1} , R ¹¹ is —C _q H _{2q + 1} , m, n and q are each independently 0 to 20),
R ¹⁵ and R ¹⁶ 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 ¹⁷ is -M-C ₁ H _{2l + 1} or -M-C ₁ H _2l -R ⁹ (wherein M, l and R ⁹ are as defined above) or-(M-C ₁ H _2l ) _y C _s H _{2s + 1} (M and l are as defined above, y and s are each independently 1 to 20), provided that one or more of R ¹⁵ , R ¹⁶ and R ¹⁷ M is -O-
R ⁴ represents the following general formula (VII) or formula (VIII):

(Wherein M, l and m are as defined above, X and Y are each independently —O—, —NR ¹⁰ — or —CH ₂ —, R ⁸ is —OR ¹⁰ , —NR ¹⁰ R; ¹¹ or -R ¹⁰ , R ¹² is -NR ^10- , -NR ¹⁰ -NR ¹⁰ -or -N = N-, provided that R ¹⁰ and R ¹¹ are as defined above) or -MC _l H _2l- (wherein M and l are as defined above),
R ⁵ , R ⁶ and R ⁷ are each independently a hydrogen atom, a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms,
A is a carbon atom, a nitrogen atom, a sulfur atom or a phosphorus atom,
B is ═O or ═NR ¹³ (wherein R ¹³ is a hydrogen atom, a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms. ) And
D is —O—, —S— or —NR ¹⁴ — (where R ¹⁴ is a hydrogen atom, a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, or 6 to 6 carbon atoms). 20 aryl groups),
a is 0 to 2 and b is 0 to 4, provided that when A is a carbon atom, 2a + b is 3, when A is a nitrogen atom, 2a + b is 2, and when A is a sulfur atom, 2a + b is 1 The organic silicon compound according to claim 1, wherein 3 or 5 and A is a phosphorus atom, 2a + b is 2 or 4.   The organosilicon compound according to claim 3 or 4, 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 ⁹ (where R ⁹ and 1 are as defined above), and the other is —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 organosilicon according to claim 3 or 5, wherein R ⁵ is a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms. Compound. At least one of R ¹ , R ² and R ³ is represented by —O—C ₁ H _{2 1} —NR ¹⁰ R ¹¹ (where R ¹⁰ , R ¹¹ and 1 are as defined above),
The R ⁵ is a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms, according to claim 3, 5 or 6. Organosilicon compounds. W is represented by —NR ¹⁰ — (wherein R ¹⁰ is as defined above),
R ¹⁵ and R ¹⁶ are each independently represented by —O—C ₁ H _2l — (wherein l is as defined above),
R ¹⁷ is represented by —O— _Cl H _2l —R ⁹ (wherein R ⁹ and l are as defined above),
R ⁴ is represented by —C ₁ H _2l — (wherein l is as defined above),
The organosilicon according to claim 4 or 5, wherein R ⁵ is a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms. Compound. W is represented by —O— or —CR ¹⁰ R ¹¹ — (wherein R ¹⁰ and R ¹¹ are as defined above),
R ¹⁵ and R ¹⁶ are each independently represented by —O—C ₁ H _2l — (wherein l is as defined above),
R ¹⁷ is represented by —O—C ₁ H _{2 1} —NR ¹⁰ R ¹¹ (where R ¹⁰ , R ¹¹ and l are as defined above),
R ⁴ is represented by —C ₁ H _2l — (wherein l is as defined above),
The organosilicon according to claim 4 or 5, wherein R ⁵ is a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms. Compound.   An inorganic filler (B) and the organosilicon compound (C) according to any one of claims 1 to 9 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 10 characterized by the above-mentioned.   The rubber composition according to claim 10, wherein the inorganic filler (B) is silica or aluminum hydroxide. The rubber composition according to claim 12, wherein the silica has a BET surface area of 40 to 350 m ² / g.   A tire using the rubber composition according to claim 10.   The primer composition containing the organosilicon compound in any one of Claims 1-9.   The coating composition containing the organosilicon compound in any one of Claims 1-9.   The adhesive agent containing the organosilicon compound in any one of Claims 1-9.