KR102065652B1 - Modifying agent, preparation method of modified conjugated diene polymer using the modifying agent and modified conjugated diene polymer - Google Patents

Abstract

The present invention provides a rubber modifier compound, a method for producing a modified conjugated diene-based polymer using the same, a modified conjugated diene-based polymer prepared from the production method, a rubber composition comprising the modified conjugated diene-based polymer and a tire prepared from the rubber composition It is about. Accordingly, the rubber modifier compound may be used as a modifier for rubber, in particular, a conjugated diene-based polymer, to be bonded to the conjugated diene-based polymer chain to easily introduce a filler affinity functional group. Therefore, the modified conjugated diene-based polymer prepared using the rubber modifier compound may have excellent affinity with the filler, and as a result, the processed article (eg, tire) manufactured from the rubber composition including the polymer may have a tensile strength, Abrasion resistance and wet road resistance properties may be excellent.

Description

Modifying agent, preparation method of modified conjugated diene polymer using the modifying agent and modified conjugated diene polymer

The present invention provides a rubber modifier compound, a method for producing a modified conjugated diene-based polymer using the same, a modified conjugated diene-based polymer prepared from the production method, a rubber composition comprising the modified conjugated diene-based polymer and a tire prepared from the rubber composition It is about.

In recent years, with the demand for low fuel consumption for automobiles, there has been a demand for conjugated diene-based polymers having low rolling resistance, excellent wear resistance and tensile properties, and adjusting stability represented by wet skid resistance.

In order to reduce the rolling resistance of the tire, there is a method of reducing the hysteresis loss of the vulcanized rubber. As an evaluation index of the vulcanized rubber, a repulsive elasticity of 50 ° C. to 80 ° C., tan δ, Goodrich heating and the like are used. That is, a rubber material having a high rebound elasticity at the above temperature or a small tan δ or good rich heat generation is preferable.

As a rubber material having a low hysteresis loss, natural rubber, polyisoprene rubber, polybutadiene rubber and the like are known, but these have a problem of low wet skid resistance. Recently, conjugated diene-based (co) polymers such as styrene-butadiene rubber (hereinafter referred to as SBR) or butadiene rubber (hereinafter referred to as BR) have been produced by emulsion polymerization or solution polymerization and used as rubber for tires. . Among them, the greatest advantage of solution polymerization over emulsion polymerization is that the vinyl structure content and styrene content that define rubber properties can be arbitrarily controlled, and molecular weight and physical properties can be adjusted by coupling or modification. It can be adjusted. Therefore, it is easy to change the structure of the final manufactured SBR or BR rubber, and the movement of the chain ends can be reduced by the binding or modification of the chain ends, and the bonding strength with fillers such as silica or carbon black can be increased. It is widely used as a rubber material for tires.

When the solution-polymerized SBR is used as a rubber material for tires, the vinyl content in the SBR is increased to increase the glass transition temperature of the rubber, thereby controlling tire required properties such as running resistance and braking force, and properly adjusting the glass transition temperature. By adjusting the fuel consumption can be reduced.

The solution polymerization SBR is prepared using an anionic polymerization initiator, and is used by binding or modifying the chain ends of the formed polymer using various modifiers.

For example, US Pat. No. 4,397,994 discloses a technique in which the active anion at the chain end of a polymer obtained by polymerizing styrene-butadiene in a nonpolar solvent using alkyllithium, a monofunctional initiator, using a binder such as a tin compound. It was.

Meanwhile, carbon black and silica are used as reinforcing fillers for tire treads. When silica is used as reinforcing fillers, low hysteresis loss and wet skid resistance are improved. However, the hydrophilic surface silica has a disadvantage of poor dispersibility due to low affinity with rubber compared to the hydrophobic surface carbon black, so that a separate silane coupler may be used to improve dispersibility or to impart a bond between silica and rubber. It is necessary to use a ring agent.

Thus, a method of introducing a functional group having affinity or reactivity with silica to the rubber molecule terminal portion, but the effect is not sufficient.

Therefore, there is a need for development of a rubber having high affinity with fillers including silica.

US 4,397,994 A

The present invention has been made to solve the problems of the prior art, an object of the present invention is to provide a compound for a rubber modifier that can provide a filler, in particular a silica-based filler affinity functional group.

Another object of the present invention is to provide a method for producing a modified conjugated diene-based polymer using the compound for the rubber modifier.

Another object of the present invention is to provide a modified conjugated diene-based polymer prepared from the above production method.

In addition, another object of the present invention to provide a rubber composition comprising the modified conjugated diene-based polymer.

Furthermore, another object of the present invention is to provide a tire made from the rubber composition.

In order to solve the above problems, a compound represented by the following formula (1) is provided.

[Formula 1]

In Chemical Formula 1,

R ₁ is an alkylene group having 1 to 10 carbon atoms,

R ₂ to R ₆ are each independently an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms,

n and m are each independently an integer from 1 to 10.

In addition, the present invention is to prepare an active polymer in which the alkali metal is bonded to at least one end by polymerizing a conjugated diene monomer or an aromatic vinyl monomer and a conjugated diene monomer in the presence of an organic alkali metal compound in a hydrocarbon solvent (step 1 ); And it provides a method for producing a modified conjugated diene-based polymer comprising the step (step 2) of reacting the active polymer with the compound represented by the formula (1).

In addition, there is provided a modified conjugated diene-based polymer prepared by the above production method.

In addition, it provides a rubber composition comprising the modified conjugated diene-based polymer.

Furthermore, there is provided a tire made from the rubber composition.

Compound represented by the formula (1) according to the present invention can be used as a modifier for rubber, in particular conjugated diene-based polymer, it is coupled to the conjugated diene-based polymer chain can be easily introduced filler affinity functional group.

In the production method according to the present invention, a modified conjugated diene-based polymer having excellent modification rate can be easily prepared by using the compound represented by Formula 1.

In addition, the modified conjugated diene-based polymer according to the present invention may be excellent in affinity with the filler, in particular, silica-based filler by the combination of a compound-derived group represented by the formula (1), such as a siloxane group and an amine group in the polymer chain.

In addition, the rubber composition according to the present invention may be excellent in workability by including a modified conjugated diene-based polymer having excellent affinity with the filler, and as a result, the processed product (for example, a tire) manufactured using the rubber composition may be tensile. Strength, wear resistance and wet road resistance properties may be excellent.

Hereinafter, the present invention will be described in more detail to aid in understanding the present invention.

The terms or words used in this specification and claims are not to be construed as limiting in their usual or dictionary meanings, and the inventors may appropriately define the concept of terms in order to best describe their invention. It should be interpreted as meaning and concept corresponding to the technical idea of the present invention based on the principle that the present invention.

The present invention provides a compound for rubber modifiers that can provide an affinity functional group with reinforcing fillers, especially silica based fillers.

The compound according to an embodiment of the present invention is characterized by represented by the following formula (1).

[Formula 1]

In Chemical Formula 1,

R ₁ is an alkylene group having 1 to 10 carbon atoms,

R ₂ to R ₆ are each independently an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms,

n and m are each independently an integer from 1 to 10.

Specifically, in Formula 1, R ₁ is an alkylene group having 1 to 6 carbon atoms, R ₂ to R ₄ are independently an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, R ₅ and R ₆ May be independently an alkyl group having 1 to 6 carbon atoms.

In addition, in Chemical Formula 1, R ₁ is an alkylene group having 1 to 3 carbon atoms, R ₂ to R ₄ are each independently an alkoxy group having 1 to 3 carbon atoms, and R ₅ and R ₆ are each independently 1 to 3 carbon atoms. It may be an alkyl group.

More specifically, Formula 1 may be a compound represented by the following Formula 2.

[Formula 2]

In Formula 2, n and m may be each independently an integer of 1 to 10.

In addition, the compound represented by Formula 1 may be a rubber modifier as described above.

Specifically, the compound represented by Formula 1 may be a modifier for conjugated diene polymer. Herein, the conjugated diene polymer may be a conjugated diene monomer homopolymer or a copolymer of a conjugated diene monomer and an aromatic vinyl monomer.

The present invention also provides a method for producing a modified conjugated diene polymer using the compound represented by the formula (1).

The production method according to an embodiment of the present invention is an active polymer in which an alkali metal is bonded to at least one terminal by polymerizing a conjugated diene monomer or an aromatic vinyl monomer and a conjugated diene monomer in the presence of an organic alkali metal compound in a hydrocarbon solvent. Preparing (step 1); And reacting the active polymer with the compound represented by Chemical Formula 1 (step 2).

Step 1 is a step for preparing an active polymer having an alkali metal bonded to at least one end thereof, and is performed by polymerizing a conjugated diene monomer or a conjugated diene monomer and an aromatic vinyl monomer in the presence of an organic alkali metal compound in a hydrocarbon solvent. Can be.

The polymerization of step 1 may be to use a conjugated diene monomer alone or a conjugated diene monomer and an aromatic vinyl monomer together as a monomer. That is, the polymer prepared by the above production method according to an embodiment of the present invention may be a homopolymer derived from a conjugated diene monomer or a copolymer derived from a conjugated diene monomer and an aromatic vinyl monomer.

When the modified conjugated diene polymer is a copolymer of a conjugated diene monomer and an aromatic vinyl monomer, the copolymer may be a random copolymer.

Here, the "random copolymer" may indicate that the structural units constituting the copolymer are randomly arranged.

The conjugated diene monomer is not particularly limited, but for example, 1,3-butadiene, 2,3-dimethyl-1,3-butadiene, piperylene, 3-butyl-1,3-octadiene, isoprene and 2-phenyl It may be one or more selected from the group consisting of -1,3-butadiene.

When the conjugated diene-based monomer and the aromatic vinyl monomer are used together as the monomer, the conjugated diene-based monomer is 60% by weight or more, specifically, in the finally prepared modified conjugated diene-based polymer. 60 wt% to 90 wt%, more specifically, 60 wt% to 85 wt%.

The aromatic vinyl monomer is not particularly limited, but for example, styrene, α-methylstyrene, 3-methylstyrene, 4-methylstyrene, 4-propylstyrene, 1-vinylnaphthalene, 4-cyclohexylstyrene, 4- (p It may be one or more selected from the group consisting of -methylphenyl) styrene and 1-vinyl-5-hexylnaphthalene.

When the conjugated diene monomer and the aromatic vinyl monomer are used together as the monomer, the aromatic vinyl monomer may be 40% by weight or less of the aromatic vinyl monomer-derived unit in the finally prepared modified conjugated diene polymer. It may be used in an amount comprised from 10% by weight to 40% by weight, more specifically 15% by weight to 40% by weight.

Herein, the "derived unit" may refer to a component, a structure, or the substance itself resulting from a substance.

The hydrocarbon solvent is not particularly limited but may be, for example, one or more selected from the group consisting of n-pentane, n-hexane, n-heptane, isooctane, cyclohexane, toluene, benzene and xylene.

The organoalkali metal compound may be used in an amount of 0.01 mmol to 10 mmol based on 100 g of the total monomer.

 The organoalkali metal compound is not particularly limited, but for example, methyllithium, ethyllithium, propyllithium, n-butyllithium, s-butyllithium, t-butyllithium, hexyllithium, n-decyllithium, t-octylithium, Phenyllithium, 1-naphthyllithium, n-eicosilium, 4-butylphenyllithium, 4-tolyllithium, cyclohexyllithium, 3,5-di-n-heptylcyclohexyllithium, 4-cyclopentyllithium, naph At least one member selected from the group consisting of sodium sodium, naphthyl potassium, lithium alkoxide, sodium alkoxide, potassium alkoxide, lithium sulfonate, sodium sulfonate, potassium sulfonate, lithium amide, sodium amide, potassium amide, lithium isopropylamide Can be.

The polymerization of step 1 may be performed by further adding a polar additive as needed, the polar additive may be added to 0.001 parts by weight to 10 parts by weight based on 100 parts by weight of the total monomer. Specifically, the content may be added in an amount of 0.001 part by weight to 1 part by weight, more specifically 0.005 part by weight to 0.1 part by weight, based on 100 parts by weight of the total monomers.

The polar additives include tetrahydrofuran, ditetrahydrofurylpropane, diethyl ether, cycloamal ether, dipropyl ether, ethylene dimethyl ether, ethylene dimethyl ether, diethyl glycol, dimethyl ether, tertiary butoxyethoxyethane, bis It may be one or more selected from the group consisting of (3-dimethylaminoethyl) ether, (dimethylaminoethyl) ethyl ether, trimethylamine, triethylamine, tripropylamine and tetramethylethylenediamine.

In the manufacturing method according to an embodiment of the present invention, when the conjugated diene-based monomer and the aromatic vinyl-based monomer are copolymerized by using the polar additive, the reaction rate can be easily compensated for by forming a random copolymer. Can be induced.

The polymerization of step 1 may be carried out through adiabatic polymerization, or isothermal polymerization.

Here, adiabatic polymerization refers to a polymerization method including a step of polymerizing with self-heating reaction without adding heat after the addition of the organoalkali metal compound, and the isothermal polymerization is an arbitrary heat after adding the organoalkali metal compound. It represents a polymerization method for maintaining a constant temperature of the polymer by adding or taking away heat.

The polymerization may be performed at a temperature range of -20 ° C to 200 ° C, specifically 0 ° C to 150 ° C, and more specifically 10 ° C to 120 ° C.

Step 2 is a step of reacting the active polymer with a compound represented by Formula 1 to prepare a modified conjugated diene-based polymer.

In this case, the compound represented by Chemical Formula 1 may be as described above.

The compound represented by Chemical Formula 1 may be used in a ratio of 0.1 mol to 10 mol with respect to the total number of moles of the organic alkali metal compound.

The reaction of step 2 according to an embodiment of the present invention is a modification reaction for introducing a functional group into the polymer, each reaction may be performed for 10 minutes to 5 hours in a temperature range of 10 ℃ to 120 ℃.

The preparation method according to an embodiment of the present invention may further include one or more steps of recovering and drying the solvent and the unreacted monomer, if necessary after step 2 above.

In addition, the present invention provides a modified conjugated diene-based polymer prepared from the above production method.

The modified conjugated diene-based polymer according to an embodiment of the present invention may include a compound derived group represented by the formula (1). That is, the modified conjugated diene-based polymer may be modified by a compound represented by the formula (1).

The modified conjugated diene-based polymer has a siloxane group and an amine group bonded to the polymer chain may be excellent in affinity with the filler, in particular silica filler. Accordingly, the physical properties of the rubber composition including the modified conjugated diene-based polymer may be excellent, and consequently, the tensile strength of a molded article, such as a tire, manufactured using the rubber composition may be excellent. Abrasion resistance and wet road resistance can be improved.

In addition, the modified conjugated diene-based polymer may have a number average molecular weight of 10,000 g / mol to 2,000,000 g / mol, specifically may be 10,000 g / mol to 1,000,000 g / mol.

The modified conjugated diene-based polymer may have a weight average molecular weight of 10,000 g / mol to 3,000,000 g / mol, specifically may be 100,000 g / mol to 200,000 g / mol.

The modified conjugated diene-based polymer may be a polydispersity index of 0.5 to 10, specifically 1 to 4.

In addition, the modified conjugated diene-based polymer may have a vinyl content of 5% by weight or more, specifically 10% by weight or more, more specifically 10% by weight to 50% by weight, and the glass transition temperature when the vinyl content is in the above range. Can be adjusted to an appropriate range, and when applied to a tire, not only the properties required for the tire such as driving resistance and braking force are excellent, but also it has an effect of reducing fuel consumption.

In this case, the vinyl content represents the content of the 1,2-added conjugated diene monomer instead of 1,4-addition based on 100% by weight of the conjugated diene polymer composed of a monomer having a vinyl group or a conjugated diene monomer.

In addition, the present invention provides a rubber composition comprising the modified conjugated diene-based polymer.

The rubber composition may include 0.1 to 200 parts by weight of a filler based on 100 parts by weight of the modified conjugated diene-based polymer, and the filler may be a silica-based filler, a carbon black-based filler, or a combination thereof.

In addition, the rubber composition may further include other diene polymers as needed in addition to the modified conjugated diene polymer, and the diene polymer may be, for example, styrene-butadiene polymer, butadiene polymer, natural rubber, or a combination thereof. .

In addition, the present invention provides a tire manufactured using the rubber composition.

The tire may include a tire or a tire tread.

Hereinafter, the present invention will be described in more detail with reference to Examples and Experimental Examples. However, the following Examples and Experimental Examples are provided to illustrate the present invention, and the scope of the present invention is not limited only to these examples.

Example 1

0.5 g of 1-vinylimidazole and 0.4 g of propyllithium were added to a 20 L autoclave reactor, and the temperature inside the reactor was raised to 40 ° C. Here, 270 g of styrene, 710 g of 1,3 butadiene, 5000 g of normal hexane, 0.86 g of DTP (2,2-di (2-tetrahydrofuryl) propane) as a polar additive was added thereto, and the reactor was kept at 40 ° C. And adiabatic heating reaction was carried out. After 20 minutes, 20 g of 1,3-butadiene was added to cap the SSBR ends with butadiene. After 5 minutes, 5 mmol of the compound of the formula (i) was added thereto, followed by a modification for 15 minutes. Thereafter, the polymerization reaction was stopped using ethanol, and 5 ml of a solution in which 0.3 wt% of BHT (butylated hydroxytoluene), an antioxidant, was dissolved in hexane was added. The resulting polymer was placed in hot water heated with steam, stirred to remove the solvent, and then dried in rolls to remove residual solvent and water to prepare a modified styrene-butadiene copolymer.

(i)

(i)

Example 2

A modified styrene-butadiene copolymer was prepared in the same manner as in Example 1 except that 0.6 g of 1-vinylimidazole and 0.5 g of propyllithium were used.

Comparative example

A commercially available commercial styrene-butadiene copolymer (5025-2HM grade, LANXESS) was used for the experiment.

Experimental Example 1

The weight average molecular weight (Mw), the number average molecular weight (Mn), the polydispersity index (PDI), the component analysis, and the pattern viscosity (MV) were measured for each copolymer of Examples 1 and 2 and Comparative Examples, respectively. . The results are shown in Table 1 below.

1) Component Analysis

Styrene derived units (SM) and vinyl content in each copolymer were measured using NMR.

2) Molecular Weight Analysis

The weight average molecular weight (Mw) and the number average molecular weight (Mn) of each copolymer were measured by gel permeation chromatograph (GPC) analysis under 40 ° C. At this time, the column (column) was used by combining two PLgel Olexis bag of Polymer Laboratories Co., Ltd. and one PLgel mixed-C column, all of the newly replaced column was a mixed bed column. In addition, PS (polystyrene) was used as the GPC standard material in the molecular weight calculation. The polydispersity index (PDI) was calculated as the ratio (Mw / Mn) of the weight average molecular weight and the number average molecular weight measured by the above method.

3) Mooney viscosity analysis

The Mooney viscosity of each copolymer was measured by MV-2000 (Alpha Technologies Co., Ltd.) for 15 minutes or more of each sample weight 15g or more for 1 minute and then at 100 ℃ for 4 minutes.

division Component Analysis (NMR) GPC Mooney viscosity (MV) Styrene vinyl Mw (g / mol, × 10 ⁴ ) Mn (g / mol, × 10 ⁴ ) PDI Example 1 27.3 43.1 553 384 1.4 80 Example 2 27.5 43.3 630 420 1.6 78 Comparative example 27 43 690 390 1.8 61

Experimental Example 2

Tensile and viscoelastic properties were measured in order to compare and analyze the physical properties of the rubber compositions including the copolymers of Examples 1 and 2 and Comparative Examples and molded articles prepared therefrom. The results are shown in Table 2 below.

1) Preparation of Rubber Composition

Each rubber composition was prepared in two proportions. First, the rubber composition comprising the copolymer of Example 1 and Comparative Example was prepared in the component ratio shown in S-1 of Table 2, and the copolymer of Example 2 in the component ratio shown in S-2 of Table 2 below Prepared. Each rubber composition was prepared through a first stage kneading, a second stage kneading and a third stage kneading. At this time, the amount of the substance except the modified conjugated diene copolymer is shown based on 100 parts by weight of the modified conjugated diene copolymer. In the first stage kneading, bis (3-triethoxysilylpropyl) tetrasulfide as a copolymer, silica and a silane coupling agent at 80 rpm using a half-barrier attached with a temperature control device and a process oil oil, TDAE), antioxidant (TMDQ), antioxidant, zinc oxide (ZnO), stearic acid (stearic acid) and wax were mixed and kneaded. At this time, the temperature of the kneader was controlled and the primary blend was obtained at a discharge temperature of 140 ° C to 150 ° C. In the second stage kneading, after cooling the primary blend to room temperature, a rubber accelerator (CZ) and a sulfur powder were added to the kneader and mixed at a temperature of 60 ° C. or lower to obtain a secondary blend. Thereafter, the second blend was molded in a third stage kneading, and vulcanized in a vulcanization press at 180 to 90 minutes for each vulcanized rubber.

division S-1 (part by weight) S-2 (parts by weight) Copolymer 100 137.5 Silica 70 70 Coupling agent 11.02 11.2 Process oil 33.75 - Anti-aging 2.0 2.0 Antioxidant 2.0 2.0 Zinc oxide 3.0 3.0 Stearic acid 2.0 2.0 Wax 1.0 - Rubber accelerator 1.75 1.75 Yellow powder 1.5 1.5

2) tensile properties

Tensile properties were prepared in accordance with the tensile test method of ASTM 412 (thickness 25 mm, length 80 mm) and measured the tensile strength at the time of cutting the specimen and the tensile stress (300% modulus) at 300% elongation. Specifically, tensile properties were measured at a rate of 50 cm / min at room temperature using a Universal Test Machin 4204 (Instron Co., Ltd.) tensile tester to obtain tensile strength and tensile stress at 300% elongation.

3) viscoelastic properties

Viscoelastic properties were measured by using a dynamic mechanical analyzer (TA, Inc.) in a torsion mode at a frequency of 10 Hz and the deformation at each measurement temperature (-60 ° C. to 60 ° C.) to measure Tan δ. The Payne effect (ΔG ′) is expressed as the difference between the minimum and maximum values at 0.28% to 40% of the strain. The smaller the Payne effect, the better the dispersibility of the filler. In addition, the higher the low temperature 0 [deg.] C Tan δ, the better the wet road surface resistance. The lower the high temperature 60 [deg.] C. Tan δ, the lower the hysteresis loss, and the lower the cloud resistance (fuel efficiency).

division Example 1 Example 2 Comparative Example 1 Tensile Properties Tensile strength (kgf / cm ² ) 213 193 161 300% tensile stress (kgf / cm ² ) 132 130 98 Viscoelastic Tan δ at 0 ° C (Index) 0.967 0.978 0.647 Tan δ at 60 ℃ (Index) 0.101 0.108 0.133 △ G 'at 60 ℃ 0.25 0.29 0.56

As shown in Table 3, the tensile properties and viscoelastic properties of the rubber composition comprising the modified styrene-butadiene copolymers of Examples 1 and 2 prepared using a modifier according to an embodiment of the present invention It was confirmed that it is superior to the rubber composition including the coalescence.

Specifically, the rubber composition comprising the modified styrene-butadiene copolymers of Examples 1 and 2 prepared using the modifying agent according to an embodiment of the present invention includes the styrene-butadiene copolymer of the comparative example which is not modified. It was confirmed that the Tan δ value at 0 ° C. and the Tan δ value at 60 ° C. decreased compared with the rubber composition. This is a result showing that the modified styrene-butadiene copolymer prepared by using the modifier according to an embodiment of the present invention has excellent resistance and rolling resistance characteristics on wet road surface, and high fuel efficiency.

In addition, the rubber composition comprising the modified styrene-butadiene copolymer of Examples 1 and 2 prepared by using the modifier according to an embodiment of the present invention is a rubber comprising a styrene-butadiene copolymer of the comparative example is not modified It was confirmed that the value of ΔG ′ relative to the composition was almost half the level. This is a result indicating that the rubber composition including the modified styrene-butadiene copolymer according to an embodiment of the present invention may have excellent silica dispersibility.

Claims (24)

Compound represented by the following formula (1):
[Formula 1]

In Chemical Formula 1,
R ₁ is an alkylene group having 1 to 10 carbon atoms,
R ₂ to R ₆ are each independently an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms,
n and m are each independently an integer from 1 to 10.
The method according to claim 1,
In Chemical Formula 1,
R ₁ is an alkylene group having 1 to 6 carbon atoms,
R ₂ to R ₄ are each independently an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms,
R ₅ and R ₆ are each independently an alkyl group having 1 to 6 carbon atoms.
The method according to claim 1,
In Chemical Formula 1,
R ₁ is an alkylene group having 1 to 3 carbon atoms,
R ₂ to R ₄ are each independently alkoxy group having 1 to 3 carbon atoms,
R ₅ and R ₆ are each independently an alkyl group having 1 to 3 carbon atoms.
The method according to claim 1,
Formula 1 is a compound represented by the following formula (2):
[Formula 2]

In Chemical Formula 2,
n and m are each independently an integer from 1 to 10.
The method according to claim 1,
The compound is a rubber modifier.
The method according to claim 1,
The compound is a modifier for conjugated diene polymer.
The method according to claim 6,
The conjugated diene-based polymer is a conjugated diene monomer homopolymer or a copolymer of a conjugated diene monomer and an aromatic vinyl monomer.
1) polymerizing a conjugated diene monomer or an aromatic vinyl monomer and a conjugated diene monomer in the presence of an organic alkali metal compound to prepare an active polymer having an alkali metal bonded to at least one end thereof in a hydrocarbon solvent; And
2) A method of producing a modified conjugated diene-based polymer comprising the step of reacting the active polymer with a compound represented by the formula (1)
[Formula 1]

In Chemical Formula 1,
R ₁ is an alkylene group having 1 to 10 carbon atoms,
R ₂ to R ₆ are each independently an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms,
n and m are each independently an integer from 1 to 10.
The method according to claim 8,
The organoalkali metal compound is a method for producing a modified conjugated diene-based polymer that is used in 0.01 mmol to 10 mmol based on a total of 100 g of the monomer.
The method according to claim 8,
The organoalkali metal compound is methyllithium, ethyllithium, propyllithium, n-butyllithium, s-butyllithium, t-butyllithium, hexyllithium, n-decyllithium, t-octylithium, phenyllithium, 1-naphthyl Lithium, n-eicosilium, 4-butylphenyllithium, 4-tolyllithium, cyclohexyllithium, 3,5-di-n-heptylcyclohexyllithium, 4-cyclopentyllithium, naphthyl sodium, naphthyl potassium, Of the modified conjugated diene-based polymer is one or more selected from the group consisting of lithium alkoxide, sodium alkoxide, potassium alkoxide, lithium sulfonate, sodium sulfonate, potassium sulfonate, lithium amide, sodium amide, potassium amide, lithium isopropylamide Manufacturing method.
The method according to claim 8,
The polymerization of step 1) is a method for producing a modified conjugated diene-based polymer further by adding a polar additive.
The method according to claim 11,
The polar additive is a method for producing a modified conjugated diene-based polymer is added in an amount of 0.001 to 10 parts by weight relative to 100 parts by weight of the total monomer.
The method according to claim 8,
Formula 1 is a method for producing a modified conjugated diene-based polymer that is a compound represented by the formula (2):
[Formula 2]

In Chemical Formula 2,
n and m are each independently an integer from 1 to 10.

The method according to claim 8,
The compound represented by Formula 1 is a method for producing a modified conjugated diene-based polymer that is used in a ratio of 0.1 mol to 10 mol relative to the total number of moles of the organic alkali metal compound.
Modified conjugated diene-based polymer comprising a compound derived group represented by the formula (1) according to claim 1
[Formula 1]

In Chemical Formula 1,
R ₁ is an alkylene group having 1 to 10 carbon atoms,
R ₂ to R ₆ are each independently an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms,
n and m are each independently an integer from 1 to 10.
The method according to claim 15,
Wherein said polymer is a conjugated diene monomer homopolymer or a copolymer of a conjugated diene monomer and an aromatic vinyl monomer.
The method according to claim 15,
The polymer is a modified conjugated diene-based polymer having a number average molecular weight of 1,000 g / mol to 2,000,000 g / mol.
The method according to claim 15,
The polymer is a modified conjugated diene-based polymer having a polydispersity index of 0.5 to 10.
The method according to claim 15,
The polymer is modified conjugated diene-based polymer having a vinyl content of 5% by weight to 50% by weight.
A rubber composition comprising the modified conjugated diene-based polymer of claim 15.
The method of claim 20,
The rubber composition is a rubber composition comprising 20 to 90% by weight of the modified conjugated diene-based polymer.
The method of claim 20,
The rubber composition comprises 0.1 to 200 parts by weight of a filler based on 100 parts by weight of the polymer.
The method according to claim 22,
The filler is a silica-based filler, a carbon black filler or a combination thereof.
A tire made from the rubber composition of claim 20.