# US 11,028,189 B2 · Preparation method of anionic polymerization initiator, device for manufacturing anionic polymerization initiator and anionic polymerization initiator prepared therefrom

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- Number: US 11,028,189 B2
- Document ID: US11028189B2
- Status: Granted
- Kind: B2
- Application number: 15/744,565
- Filed: 2016-07-27
- Published: 2018-07-26
- Granted: 2021-06-08
- Earliest claimed: 2015-09-17
- Assignees: LG Chem, Ltd.
- Applicants: LG Chem, Ltd.
- Inventors: Jae Hoon Choe; Jong Young Choi; Jung Yong Lee; Dong Cheol Choe; Hyun Ju Kim; Hyeon Hui Kim; Jong Min Shin; Woong Chan Jeong; Kwang Ho Song
- Web page: https://patentgrep.com/patent/US11028189B2

## CPC

- C08F 2/01: characterised by special features of the polymerisation apparatus used
- B01F 25/422: between stacked plates, e.g. grooved or perforated plates
- C07F 1/02: Lithium compounds
- C08F 2/04: Polymerisation in solution (C08F2/32 takes precedence)
- C08F 2/44: Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
- C08F 2/60: Polymerisation by the diene synthesis
- C08F 4/08: of alkali metals
- C08F 4/10: of alkaline earth metals, zinc, cadmium, mercury, copper or silver
- C08F 236/10: with vinyl-aromatic monomers
- C08F 236/14: containing elements other than carbon and hydrogen
- C08K 5/19: Quaternary ammonium compounds
- C08K 5/3432: Six-membered rings
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- B01F: MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING (mixing paints B44D3/06)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## Abstract

An method for preparing an anion polymerization initiator, a device for preparing the same and an anion polymerization initiator prepared therefrom are provided. And the method for preparing an anion polymerization initiator according to present invention is characterized in that an amine compound of Formula 1 and/or Formula 2; an organometallic compound; and/or a conjugated diene compound are introduced in the form of a solution and reacted.

## Claims

### Claim 1

A method for preparing an anionic polymerization initiator comprising:
introducing an amine compound of Formula 2 below and an organometallic compound into a continuous reactor to react them:
wherein,
R23, R24 and R25 independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 1 to 6 carbon atoms or an alkynyl group having 1 to 6 carbon atoms,
Y represents nitrogen, oxygen or sulfur,
R26 is absent when Y is oxygen or sulfur, and represents an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 1 to 6 carbon atoms, an alkynyl group having 1 to 6 carbon atoms or a hetero atom when Y is nitrogen, and
b is an integer of 1 to 20.

### Claim 2 (depends on 1)

The method for preparing an anionic polymerization initiator according to claim 1, wherein
the compound of Formula 2 is a compound of Formula 4 below:
wherein,
Rc and Rd independently represent hydrogen or an alkyl group having 1 to 6 carbon atoms,
Y represents nitrogen, oxygen or sulfur,
R26 is absent when Y is oxygen or sulfur, and represents an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 1 to 6 carbon atoms, an alkynyl group having 1 to 6 carbon atoms or a hetero atom when Y is nitrogen, and
c is an integer of 1 to 10.

### Claim 3 (depends on 1)

The method for preparing an anionic polymerization initiator according to claim 1, wherein
the organometallic compound comprises at least one selected from the group consisting of an organic alkali metal compound and an organic alkaline earth metal compound.

### Claim 4 (depends on 1)

The method for preparing an anionic polymerization initiator according to claim 1, further comprising
supplying a conjugated diene compound to the continuous reactor after the reacting of the amine compound of Formula 2 and the organometallic compound.

### Claim 5 (depends on 1)

The method for preparing an anionic polymerization initiator according to claim 1, wherein
a molar ratio of the amine compound of Formula 2 and the organometallic compound is 5:1 to 1:5.

### Claim 6 (depends on 4)

The method for preparing an anionic polymerization initiator according to claim 4, wherein
a molar ratio of the amine compound of Formula 2 and the conjugated diene compound is 1:1 to 1:100.

### Claim 7 (depends on 1)

The method for preparing an anionic polymerization initiator according to claim 1, wherein the continuous reactor comprises
a mixer; and
a first inflow line and a second inflow line, connected to said mixer,
wherein the first inflow line supplies the amine compound of Formula 2, and the second inflow line supplies the organometallic compound.

### Claim 8 (depends on 7)

The method for preparing an anionic polymerization initiator according to claim 7, wherein
the mixer comprises a first mixer and a second mixer, connected in series, and
comprises a first and second inflow lines connected to the first mixer; and a third inflow line connected to the second mixer, and
the third inflow line supplies a conjugated diene compound.

### Claim 9 (depends on 8)

The method for preparing an anionic polymerization initiator according to claim 8, wherein
one or more of the first and second mixers are a static mixer.

### Claim 10 (depends on 9)

The method for preparing an anionic polymerization initiator according to claim 9, wherein
the static mixers are each independently at least one selected from the group consisting of a plate mixer, a Kenics mixer and a Sulzer mixer.

### Claim 11 (depends on 8)

The method for preparing an anionic polymerization initiator according to claim 8, wherein
one or more of the first and second mixers are a microreactor,
said microreactor comprises a plurality of microchannels repeating branching and joining.

### Claim 12 (depends on 8)

The method for preparing an anionic polymerization initiator according to claim 8, wherein
one or more of the first and second mixers have a structure in which a static mixer and a microreactor are connected.

### Claim 13 (depends on 8)

The method for preparing an anionic polymerization initiator according to claim 8, wherein
a reaction temperature of the first mixer is −80° C. to 100° C. and a reaction time in the first mixer is 0.001 to 90 minutes, and
a reaction temperature of the second mixer is 10° C. to 100° C. and a reaction time in the second mixer is 1 to 60 minutes.

### Claim 14 (depends on 1)

The method for preparing an anionic polymerization initiator according to claim 1, wherein
the anionic polymerization initiator is selected from compounds of Formula 11 or 12 below:
wherein,
R21 and R22 independently represent an alkyl group having 1 to 6 carbon atoms,
Y represents nitrogen, oxygen or sulfur,
R26 is absent when Y is oxygen or sulfur, and represents an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 1 to 6 carbon atoms, an alkynyl group having 1 to 6 carbon atoms or a hetero atom when Y is nitrogen, and
R27 represents alkenyl lithium having 1 to 20 carbon atoms, alkenyl sodium having 1 to 20 carbon atoms, alkenyl potassium having 1 to 20 carbon atoms, alkenyl magnesium bromide having 1 to 6 carbon atoms or alkenyl magnesium chloride having 1 to 6 carbon atoms.