KR20180075383A - Novel lithium compounds and method for preparing the same - Google Patents

Abstract

The present invention relates to a novel lithium compound, and more specifically, provides a novel lithium compound represented by chemical formula 1, and a manufacturing method thereof. In the chemical formula 1, the definitions of each substituent are the same as defined in the description of the present invention. The novel lithium compound of the present invention is excellent in solubility in a hydrocarbon solvent, is capable of acting as a functional group contained as a functional group at one end of a polymer and has excellent affinity with a filler in the polymer after polymerization is initiated.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel lithium compound and a process for producing the same. BACKGROUND OF THE INVENTION [0002]

The present invention relates to a novel lithium compound, and more particularly, to a lithium compound having a novel structure as an initiator for initiating polymerization of a conjugated diene-based polymer and a method for producing the same.

Recently, as a rubber material for a tire, there has been demanded a conjugated diene polymer having low rolling resistance, excellent abrasion resistance, tensile properties, and adjustment stability represented by wet road surface resistance, in accordance with recent demand for low fuel consumption in automobiles.

In order to reduce the rolling resistance of the tire, there is a method of reducing the hysteresis loss of the vulcanized rubber. As the evaluation index of such vulcanized rubber, repulsive elasticity of 50 DEG C to 80 DEG C, tan delta, Goodrich heat, and the like are used. That is, a rubber material having a large rebound resilience at that temperature or a small tan δ and Goodrich heating is preferable.

Natural rubbers, polyisoprene rubbers, polybutadiene rubbers, and the like are known as rubber materials having a small hysteresis loss, but these have a problem that wet road surface resistance is small. Recently, a conjugated diene polymer or copolymer such as styrene-butadiene rubber (hereinafter referred to as SBR) or butadiene rubber (hereinafter referred to as BR) has been produced by emulsion polymerization or solution polymerization and is used as a rubber for a tire . Of these, the greatest advantage of solution polymerization over emulsion polymerization is that vinyl structure content and styrene content, which define rubber properties, can be arbitrarily controlled and molecular weight and physical properties, etc., can be controlled by coupling, It can be adjusted. Therefore, it is easy to change the structure of the finally prepared SBR or BR, and it is possible to reduce the movement of the chain terminal due to bonding or modification of the chain terminal and increase the bonding force with the filler such as silica or carbon black, It is widely used as a rubber material.

When such a solution-polymerized SBR is used as a rubber material for a tire, by increasing the vinyl content in the SBR, it is possible to increase the glass transition temperature of the rubber to control tire properties such as running resistance and braking force, Proper control can reduce fuel consumption. The solution-polymerized SBR is prepared by using an anionic polymerization initiator, and chain ends of the formed polymer are bonded or denatured by using various modifiers. For example, U.S. Patent No. 4,397,994 discloses a technique in which an active anion at the chain terminal of a polymer obtained by polymerizing styrene-butadiene in a nonpolar solvent using alkyllithium, a monofunctional initiator, is bonded using a binder such as a tin compound Respectively.

As described above, an organic lithium initiator is mainly used as an anionic polymerization initiator. Such an organ lithium initiator is usually used as it is, or a modifier initiator capable of providing a functional group to the polymer is used. However, the organolithium initiator or the denaturation initiator conventionally used has poor solubility in a hydrocarbon solvent, which results in a slow polymerization initiation rate and low cost efficiency.

US 4397994 A US 8362164 B2

Disclosure of the Invention The present invention has been conceived to solve the problems of the prior art described above. It is an object of the present invention to provide a polymer having excellent solubility in a hydrocarbon solvent and being contained as a functional group at one end of a polymer after polymerization initiation, And a method for producing the same.

According to one embodiment of the present invention for solving the above problems, the present invention provides a compound represented by the following Formula 1:

[Chemical Formula 1]

In Formula 1, M may be an alkali metal, R ¹ is a group 1 group having 1 to 30 hydrocarbon group, or - [R ⁷ O] _n R number ⁸ days and, R ^2, R ³ and R ⁸ are each R ⁴ and R ⁷ may each independently be a divalent hydrocarbon group having 1 to 30 carbon atoms, and R ⁵ and R ⁶ each independently represent a divalent hydrocarbon group having 1 to 10 carbon atoms May be a hydrocarbon group, and n may be an integer of 1 to 10.

The present invention also relates to a process for preparing a compound represented by the following formula (S1) by reacting a compound represented by the following formula (2) with a compound represented by the following formula (3); Reacting a compound represented by the following formula (4) with a compound represented by the following formula (5) to prepare a compound represented by the following formula (6); And a step (S3) of reacting a compound represented by the following formula (6) with a compound represented by the following formula (3): < EMI ID =

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In the above formulas 2 to 6, M may be an alkali metal, R ¹ may be a monovalent hydrocarbon group having 1 to 30 carbon atoms, or - [R ⁷ O] _n R ⁸ , and R ² , R ³ , R ⁸ And R ⁹ may each independently be a monovalent hydrocarbon group having 1 to 30 carbon atoms, R ⁴ and R ⁷ each independently may be a divalent hydrocarbon group having 1 to 30 carbon atoms, and R ⁵ and R ⁶ are each independently a carbon number Lt; / RTI > may be a divalent hydrocarbon group of 1 to 10, and n may be an integer of 1 to 10.

The novel lithium compound according to the present invention is excellent in solubility in a hydrocarbon solvent and is easy to initiate polymerization and has a good starting speed when used as a polymerization initiator and is included as a functional group at one end of the polymer , And functions as a functional group having excellent affinity with a filler in the polymer, thereby ultimately improving the physical properties of the polymer and the rubber composition containing the same.

Hereinafter, the present invention will be described in detail in order to facilitate understanding of the present invention.

The terms and words used in the description of the present invention and in the claims should not be construed to be limited to ordinary or dictionary terms and the inventor should appropriately interpret the concept of the term appropriately The present invention should be construed in accordance with the meaning and concept consistent with the technical idea of the present invention.

The novel lithium compound according to the present invention may be a compound represented by the following Formula 1:

[Chemical Formula 1]

In Formula 1, M may be an alkali metal, R ¹ is a group 1 group having 1 to 30 hydrocarbon group, or - [R ⁷ O] _n R number ⁸ days and, R ^2, R ³ and R ⁸ are each R ⁴ and R ⁷ may each independently be a divalent hydrocarbon group having 1 to 30 carbon atoms, and R ⁵ and R ⁶ each independently represent a divalent hydrocarbon group having 1 to 10 carbon atoms May be a hydrocarbon group, and n may be an integer of 1 to 10.

As specific examples, M may be Li, Na, or K, and R ¹ is an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkyl group having 5 to 20 carbon atoms R ⁷ O] _n R ⁸ , R ² , R ³ and R ⁸ each independently represent an alkyl group having 1 to 20 carbon atoms, an alkyl group having 2 to 20 carbon atoms An alkenyl group, an alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms, R ⁴ and R ⁷ each independently represent an alkylene group having 1 to 20 carbon atoms, R ⁵ and R ⁶ may each independently be an alkylene group having 1 to 5 carbon atoms, and n may be an integer of 1 to 8.

More specifically, in the above formula (1), M may be Li, and R ¹ represents an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or - [R ⁷ O] _n R can be ⁸ days, R ^2, R ³ and R ⁸ are each independently can be an aryl date having 1 to 10 carbon alkyl group, having 5 to 10, a cycloalkyl group, or 6 to 10 carbon atoms of, R ⁴ is C 3 -C R ⁵ and R ⁶ may each independently be an alkylene group having 1 to 5 carbon atoms, R ⁷ may be an alkylene group having 1 to 10 carbon atoms, and n may be an integer of 1 to 5 have.

In the present invention, the term "monovalent hydrocarbon group" means a monovalent atomic group in which a monovalent alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkyl group containing at least one unsaturated bond, And the minimum number of carbon atoms of the substituent represented by the monovalent hydrocarbon may be determined depending on the kind of each substituent.

In the present invention, the term "divalent hydrocarbon group" means a divalent hydrocarbon group having 2 or more carbon-hydrogen bonds, such as a divalent alkylene group, an alkenylene group, an alkynylene group, a cycloalkylene group, a cycloalkylene group containing at least one unsaturated bond, And the minimum number of carbon atoms of the substituent represented by the divalent hydrocarbon may be determined depending on the kind of each substituent.

In the present invention, the term "alkyl group" may mean a monovalent aliphatic saturated hydrocarbon, and includes linear alkyl groups such as methyl, ethyl, propyl and butyl, and isopropyl, sec-butyl, May be meant to include both branched alkyl groups such as tert-butyl and neo-pentyl.

In the present invention, the term 'alkylene group' may mean a bivalent aliphatic saturated hydrocarbon such as methylene, ethylene, propylene, and butylene.

The term " alkenyl group " in the present invention may mean an alkyl group containing one or more double bonds.

The term " alkynyl group " in the present invention may mean an alkyl group containing one or two or more triple bonds.

In the present invention, the term "cycloalkyl group" may mean a cyclic saturated hydrocarbon or a cyclic unsaturated hydrocarbon containing one or more unsaturated bonds.

In the present invention, the term "aryl group" may mean a cyclic aromatic hydrocarbon, or may be a monocyclic aromatic hydrocarbon having one ring formed, or a polycyclic aromatic hydrocarbon having two or more rings bonded thereto hydrocarbon < / RTI >

According to one embodiment of the present invention, the compound represented by Formula 1 may be one selected from the group consisting of compounds represented by Formulas 1-1 to 1-3.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

On the other hand, the compound represented by the formula (1) may be a polymerization initiator for polymerization of a conjugated diene-based polymer. That is, the compound represented by the formula (1) serves to initiate polymerization in the polymerization of the conjugated diene-based polymer, and may be a modifying initiator which is included as a functional group at one end of the polymer after polymerization is initiated.

In the present invention, the term "denaturation initiator" may mean a polymerization initiator for initiating a polymerization reaction, and the polymerization initiator may include a modifying functional group of the polymer.

When the compound represented by the formula (1) contains N atom, Si atom and O atom simultaneously in the molecule, when the functional group derived from the compound represented by the formula (1) is included at one end of the polymer, The polymer is excellent in affinity, and interaction between the polymer and the filler is possible, whereby the polymer and the filler are easily compounded, and the physical properties of the rubber composition including the polymer and the filler are improved. Further, the compound represented by the above formula (1) as R ⁴ in the molecule a divalent hydrocarbon group, and specific examples of a carbon number of 1 to 30, R ⁴ represents an alkylene group having 1 to 20 carbon atoms, more specific examples, R ⁴ is C 3 -C An alkylene group having 1 to 20 carbon atoms, the solubility in hydrocarbon solvent is excellent at the start of polymerization. The hydrocarbon solvent is not particularly limited, but may be one or more selected from the group consisting of n-pentane, n-hexane, n-heptane, isooctane, cyclohexane, toluene, benzene and xylene. For example, the compound represented by Formula 1 has a solubility in a hydrocarbon solvent, particularly, a hexane solvent of 0.30 g / ml to 0.80 g / ml, 0.30 g / ml to 0.60 g / ml, or 0.30 g / ml to 0.40 g / ml. When the polymerization is started within this range, the activity is excellent and the initiation rate is excellent.

The term "conjugated diene polymer" in the present invention means a modified conjugated diene polymer containing a conjugated diene monomer-derived repeating unit and having at one end thereof a functional group derived from the compound represented by the formula (1) The conjugated diene polymer may contain a repeating unit derived from an aromatic vinyl monomer together with the repeating unit derived from the conjugated diene monomer.

The conjugated diene monomer-derived repeating unit may mean a repeating unit formed by polymerization of the conjugated diene monomer, and examples of the conjugated diene monomer include 1,3-butadiene, 2,3-dimethyl-1,3-butadiene 1,3-butadiene, and 2-halo-1,3-butadiene (wherein halo means a halogen atom), from the group consisting of methyl, ethyl, It may be at least one selected.

The repeating unit derived from an aromatic vinyl monomer may mean a repeating unit formed by polymerization of an aromatic vinyl monomer, and examples of the aromatic vinyl monomer include styrene,? -Methylstyrene, 3-methylstyrene, 4-methylstyrene, 4- Styrene, 1-vinylnaphthalene, 4-cyclohexylstyrene, 4- (p-methylphenyl) styrene and 1-vinyl-5-hexylnaphthalene.

When the modified conjugated diene polymer is a copolymer containing an aromatic vinyl monomer-derived repeating unit, the modified conjugated diene polymer preferably contains 50 to 95% by weight, 55 to 90% by weight, or 60 to 90% by weight, And 10 to 45% by weight, or 10 to 40% by weight, based on the total amount of the aromatic vinyl monomer and the aromatic vinyl monomer, and has excellent rolling resistance, wet road surface resistance and abrasion resistance within this range It is effective.

On the other hand, the conjugated diene polymer in which the polymerization is initiated and polymerized from the compound represented by the formula (1) has an anionic active site remaining at the other end other than one end where the functional group derived from the compound represented by the formula (1) Additional denaturation reaction may be possible, and accordingly, it may be possible to prepare a modified conjugated diene polymer in which both ends are modified. The modifier may mean a compound for modifying the conjugated diene polymer. Specific examples of the modifier include an alkoxysilane-based modifier that may include a solvent affinity, a filler-affinity functional group, and the like. When the conjugated diene polymer is a copolymer, the copolymer may be a random copolymer, and in this case, there is an excellent balance between physical properties. In the random copolymer, the repeating units constituting the copolymer are randomly arranged It can mean that

According to the present invention, there is provided a process for preparing a compound represented by the formula (1), which comprises reacting a compound represented by the following formula (2) with a compound represented by the following formula (3) ); Reacting a compound represented by the following formula (4) with a compound represented by the following formula (5) to prepare a compound represented by the following formula (6); And a step (S3) of reacting a compound represented by the following formula (6) with a compound represented by the following formula (3): < EMI ID =

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In the above Chemical Formulas 2 to 6, M and R ¹ to R ⁸ are defined as in Chemical Formula 1, R ⁹ is a monovalent hydrocarbon group having 1 to 30 carbon atoms, and specific examples thereof include an alkyl group having 1 to 20 carbon atoms , An alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms. More specific examples thereof include an alkyl group having 1 to 10 carbon atoms, Or a cycloalkyl group having 6 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms.

According to one embodiment of the present invention, in the step (S1), the molar ratio of the compound represented by the formula (2) and the compound represented by the formula (3) (the compound represented by the formula (2) : 1 to 2, 1: 1 to 1.5, or 1: 1 to 1.1, and the side reaction is minimized within this range.

As another example, the step (S1) may be carried out at a temperature of from -30 DEG C to 0 DEG C, from -25 DEG C to -5 DEG C, or from -20 DEG C to -5 DEG C, the side reaction is minimized within this range, The compound represented by the following formula (2) and the compound represented by the following formula (3) are selectively reacted and bound at a ratio of 1: 1.

According to an embodiment of the present invention, in the step (S2), the molar ratio of the compound represented by the formula (4) and the compound represented by the formula (5) (the compound represented by the formula (4) : 1 to 2, 1: 1 to 1.5, or 1: 1, and the side reaction is minimized within this range.

As another example, the step (S2) may be carried out at a temperature of -30 캜 to 30 캜, -25 캜 to 25 캜, or -20 캜 to 20 캜, and the side reaction is minimized within this range .

According to an embodiment of the present invention, in step (S3), the molar ratio of the compound represented by Formula 6 to the compound represented by Formula 3 (compound represented by Formula 6: the compound represented by Formula 3) : 1 to 2, 1: 1 to 1.5, or 1: 1 to 1.1, and the side reaction is minimized within this range.

As another example, the step (S3) may be carried out at a temperature of -30 ° C to 0 ° C, -25 ° C to -5 ° C, or -20 ° C to -5 ° C, and within this range, .

The steps (S1), (S2) and (S3) are carried out independently of each other under a nitrogen or inert gas atmosphere at a pressure of 0.1 bar to 0.5 bar, 0.1 bar to 0.3 bar, or 0.1 bar to 0.2 bar And the introduction of outside air within this range is blocked, so that the reaction proceeds in a closed system, minimizing side reactions and having an excellent yield. The inert gas may be, for example, helium, neon, or argon.

As another example, the steps (S1), (S2), and (S3) above may be performed independently of one another by using an aliphatic hydrocarbon having 1 to 20 carbon atoms, an alicyclic hydrocarbon having 5 to 20 carbon atoms, an aromatic hydrocarbon solvent having 6 to 20 carbon atoms, Linear hydrocarbon solvents such as benzene, toluene and the like; aromatic hydrocarbon solvents having 5 to 8 carbon atoms such as benzene, toluene and the like; nonpolar organic solvents such as benzene, toluene and the like; Or in a polar organic solvent such as diethyl ether, methyl t-butyl ether, tetrahydrofuran (THF) and the like.

As a specific example, in the above step (S1), the compound represented by the general formula (2) may be put on a solution in which the compound represented by the general formula (2) is dissolved in the polar organic solvent in the state of being dissolved in the nonpolar organic solvent, In step (S2), the compound represented by formula (4) may be added onto a solution in which the compound represented by formula (5) is dissolved in the polar organic solvent in the state that the compound represented by formula (5) is dissolved in the nonpolar organic solvent. The compound represented by the general formula (6) may be added onto a solution in which the compound represented by the general formula (3) is dissolved in the polar organic solvent, with the compound represented by the general formula (3) dissolved in the nonpolar organic solvent.

In the preparation of the compound according to the compound of the present invention, each of the above steps can be carried out continuously, and at least one step selected from the group consisting of a solvent removal step and a washing step is carried out for each step, And can be performed individually. The solvent removal process and the cleaning process may be performed according to a conventional method.

Hereinafter, the present invention will be described in more detail with reference to Examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the invention.

Example

Example 1

Preparation of the compound represented by the formula 4-1

29.4 ml (4.5 wt%, 11.4 mmol) of a piperazine solution in which piperazine represented by the following formula (2-1) was dissolved in methyl t-butyl ether (MTBE) was added dropwise at -20 ° C under an argon atmosphere of 0.1 bar butyllithium 5.1 ml (23 wt%, 12.5 mmol) of a n-butyllithium solution dissolved in a hexane solvent was added and stirred while raising the temperature to room temperature to obtain 1.0 g of a compound represented by the following formula 4-1.

[Formula 2-1]

[Formula 4-1]

Preparation of the compound represented by the formula (6-1)

30 ml (4.5 wt%, 10.6 mmol) of a solution prepared by dissolving 1.0 g of the compound of the formula 4-1 prepared above in methyl t-butyl ether (MTBE) was added dropwise at -20 ° C under an argon atmosphere of 0.1 bar. 6.9 ml (50 wt%, 10.6 mmol) of a solution obtained by dissolving 4.7 g of the compound represented by the general formula (5-1) in hexane was added and the reaction was carried out with stirring while raising the temperature to room temperature, 2.8 g of a compound represented by the formula 6-1 was obtained and a ¹ H nuclear magnetic resonance spectroscopic spectrum was observed.

[Formula 5-1]

[Formula 6-1]

^{1 H NMR (500 MHz, DMSO} ) δ 3.46-3.35 (m, 4H), 2.67 (s, 8H), 1.50-1.23 (m, 1H), 1.07-1.05 (m, 4H), 0.61 (m, 2H) , 0.08 (s, 6H).

Preparation of Compound Represented by Formula 1-1

30 ml (4.5 wt%, 3.6 mmol) of a solution of 1.0 g of the compound represented by the formula (6-1) prepared above in methyl t-butyl ether (MTBE) -butyl lithium is added to an n- butyllithium solution 1.6 ml (23 wt%, 3.9 mmol) dissolved in a hexane solvent, and to the mixture was stirred while warming up to room temperature to give compound 0.9 g of the formula 1-1, and ¹ H nuclear magnetic resonance spectroscopy was observed.

[Formula 1-1]

^{1 H NMR (500 MHz, DMSO} ) δ 3.46-3.35 (m, 4H), 2.71 (s, 4H), 2.68 (s, 4H), 1.50-1.23 (m, 1H), 1.07-1.05 (m, 4H) , 0.61 (m, 2H), 0.08 (s, 6H).

Example 2

Preparation of the compound represented by the formula (6-2)

(4.5 wt%, 10.6 mmol) obtained by dissolving 1.0 g of the compound represented by the formula (4-1) in methyl t-butyl ether (MTBE) was added dropwise at -20 & , 5.4 g (50 wt%, 10.6 mmol) of a solution of 2.7 g of the compound represented by the following formula (6) in hexane was added, and the reaction was allowed to proceed while raising the temperature to room temperature. 3.0 g of the indicated compound was obtained, and ¹ H nuclear magnetic resonance spectroscopy was observed. At this time, the compound represented by Formula 4-1 was prepared in the same manner as in Example 1.

[Formula 5-2]

[Formula 6-2]

¹ H NMR (500 MHz, DMSO)? 3.52 (s, 4H), 3.46-3.35 (m, 4H), 2.67 , 0.61 (m, 2H), 0.08 (s, 6H).

Preparation of the compound represented by the general formula (1-2)

30 ml (4.5 wt%, 3.3 mmol) of a solution prepared by dissolving 1.0 g of the compound represented by the above formula 6-2 in methyl t-butyl ether (MTBE) was added dropwise at -20 ° C under an argon atmosphere -butyl lithium is added to an n- butyllithium solution 1.6 ml (23 wt%, 3.4 mmol) dissolved in a hexane solvent, and to the mixture was stirred while warming up to room temperature to give compound 0.9 g of the formula 1-2, and ¹ H nuclear magnetic resonance spectroscopy was observed.

[Formula 1-2]

¹ H NMR (500 MHz, DMSO)? 3.52 (s, 4H), 3.46-3.35 (m, 4H), 2.67 , 0.61 (m, 2H), 0.08 (s, 6H).

Example 3

Preparation of the compound represented by the formula (6-3)

(4.5 wt%, 10.6 mmol) obtained by dissolving 1.0 g of the compound represented by the formula (4-1) in methyl t-butyl ether (MTBE) was added dropwise at -20 ° C under an argon atmosphere of 0.1 bar 7.2 g (50 wt%, 10.6 mmol) of a solution of 3.6 g of a compound represented by the following formula (6) in hexane was added and the mixture was stirred at the room temperature while stirring to remove LiCl. 3.8 g of the indicated compound was obtained, and a ¹ H nuclear magnetic resonance spectroscopic spectrum was observed. At this time, the compound represented by Formula 4-1 was prepared in the same manner as in Example 1.

[Formula 5-3]

[Formula 6-3]

¹ H NMR (500 MHz, DMSO)? 3.52 (s, 12H), 3.46-3.35 (m, 4H), 2.67 , 0.61 (m, 2H), 0.08 (s, 6H).

Preparation of the compound represented by the general formula 1-3

30 ml (4.5 wt%, 3.3 mmol) of the compound obtained by dissolving 1.29 g of the compound represented by the above formula 6-3 in methyl t-butyl ether (MTBE) was added dropwise at -20 ° C under an argon atmosphere -butyl lithium is added to an n- butyllithium solution 1.6 ml (23 wt%, 3.4 mmol) dissolved in a hexane solvent, and to the mixture was stirred while warming up to room temperature to give the 1.2 g compound represented by the formula 1-3, and ¹ H nuclear magnetic resonance spectroscopy was observed.

[Formula 1-3]

^{1 H NMR (500 MHz, DMSO} ) δ 3.52 (s, 12H), 3.46-3.35 (m, 4H), 2.67 (s, 8H), 1.46-1.42 (m, 6H), 1.07-0.96 (m, 3H) , 0.61 (m, 2H), 0.08 (s, 6H).

Claims (12)

A compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
M is an alkali metal,
R ¹ is a monovalent hydrocarbon group having 1 to 30 carbon atoms, or - [R ⁷ O] _n R ⁸ ,
R ² , R ³ and R ⁸ are each independently a monovalent hydrocarbon group of 1 to 30 carbon atoms,
R ⁴ and R ⁷ are each independently a divalent hydrocarbon group of 1 to 30 carbon atoms,
R ⁵ and R ⁶ are each independently a divalent hydrocarbon group of 1 to 10 carbon atoms,
n is an integer of 1 to 10; The method according to claim 1,
In Formula 1,
M is Li, Na, or K,
R ¹ is an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or - [R ⁷ O] _n R < ⁸ &
R ² , R ³ and R ⁸ each independently represents an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, Lt; / RTI &
R ⁴ and R ⁷ are each independently an alkylene group having 1 to 20 carbon atoms,
R ⁵ and R ⁶ are each independently an alkylene group having 1 to 5 carbon atoms,
and n is an integer of 1 to 8. The method according to claim 1,
In Formula 1,
M is Li,
R ¹ is an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or - [R ⁷ O] _n R ⁸ ,
R ² , R ³ and R ⁸ are each independently an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms,
R ⁴ is an alkylene group having 3 to 20 carbon atoms,
R ⁵ and R ⁶ are each independently an alkylene group having 1 to 5 carbon atoms,
R ⁷ is an alkylene group having 1 to 10 carbon atoms,
and n is an integer of 1 to 5. The method according to claim 1,
Wherein the compound represented by the formula (1) is one selected from the group consisting of compounds represented by the following formulas (1-1) to (1-3).
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

The method according to claim 1,
Wherein the compound represented by the formula (1) is a polymerization initiator for polymerization of a conjugated diene-based polymer. Reacting a compound represented by the following formula (2) with a compound represented by the following formula (3) to prepare a compound represented by the following formula (S1);
Reacting a compound represented by the following formula (4) with a compound represented by the following formula (5) to prepare a compound represented by the following formula (6); And
Reacting a compound represented by the following formula (6) with a compound represented by the following formula (3): < EMI ID =
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In the above formulas 2 to 6,
M is an alkali metal,
R ¹ is a monovalent hydrocarbon group having 1 to 30 carbon atoms, or - [R ⁷ O] _n R ⁸ ,
R ² , R ³ , R ⁸ and R ⁹ are each independently a monovalent hydrocarbon group of 1 to 30 carbon atoms,
R ⁴ and R ⁷ are each independently a divalent hydrocarbon group of 1 to 30 carbon atoms,
R ⁵ and R ⁶ are each independently a divalent hydrocarbon group of 1 to 10 carbon atoms,
n is an integer of 1 to 10; The method according to claim 6,
Wherein the molar ratio of the compound represented by the formula (2) to the compound represented by the formula (3) (compound represented by the formula (2): the compound represented by the formula (3)) in the step (S1) is 1: 1 to 2. The method according to claim 6,
Wherein the step (S1) is carried out at a temperature of from -30 占 폚 to 0 占 폚. The method according to claim 6,
Wherein the molar ratio of the compound represented by the formula (4) to the compound represented by the formula (5) (compound represented by the formula (4): the compound represented by the formula (5)) is 1: 1 to 2 in the step (S2). The method according to claim 6,
Wherein the step (S2) is carried out at a temperature of from -30 占 폚 to 30 占 폚. The method according to claim 6,
Wherein the molar ratio of the compound represented by the formula (6) to the compound represented by the formula (3) (compound represented by the formula (6): the compound represented by the formula (3)) is 1: 1 to 2 in the step (S3). The method according to claim 6,
Wherein the step (S3) is carried out at a temperature of -30 ° C to 0 ° C.