# US 2020/0399405 A1 · Conjugated Diene-Based Polymer and Method for Preparing the Same

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- Number: US 2020/0399405 A1
- Document ID: US20200399405A1
- Status: Published application
- Kind: A1
- Application number: 16/765,028
- Filed: 2018-11-13
- Published: 2020-12-24
- Earliest claimed: 2017-11-22
- Assignees: LG Chem, Ltd.
- Applicants: LG Chem, Ltd.
- Inventors: Su Hwa Kim; Hyo Jin Bae; Sung Ho Park; Soo Young Choi; Jeong Heon Ahn
- Web page: https://patentgrep.com/patent/US20200399405A1

## CPC

- C08F 36/06: Butadiene
- C08F 2/38: Polymerisation using regulators, e.g. chain terminating agents {, e.g. telomerisation}
- C08F 4/52: selected from boron, aluminium, gallium, indium, thallium or rare earths (C08F4/14 takes precedence)
- C08F 8/30: Introducing nitrogen atoms or nitrogen-containing groups
- C08F 36/04: conjugated
- C08F 136/06: Butadiene
- C08L 9/00: Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

A conjugated diene-based polymer catalyzed with a lanthanide rare earth element, and having high linearity and improved compounding properties, and a method for preparing the same are provided. The conjugated diene-based polymer catalyzed with a lanthanide rare earth element has high linearity, and if applied to a rubber composition, may show excellent processability, tensile strength and viscoelasticity.

## Claims

### Claim 1

A conjugated diene-based polymer catalyzed with a lanthanide rare earth element, wherein the conjugated diene-based polymer has a ratio ((−S/R)/MWD) of a stress/relaxation (S/R) value at 100° C. and molecular weight distribution (MWD) of 0.30 or more.

### Claim 2 (depends on 1)

The conjugated diene-based polymer catalyzed with the lanthanide rare earth element according to claim 1, wherein the lanthanide rare earth element comprises a neodymium compound represented by the following Formula 1:
wherein in Formula 1,
Ra to Rc are each independently hydrogen, or an alkyl group of 1 to 12 carbon atoms, where Ra to Rc are not hydrogen at the same time.

### Claim 3 (depends on 2)

The conjugated diene-based polymer catalyzed with the lanthanide rare earth element according to claim 2, wherein the neodymium compound is one or more selected from the group consisting of Nd(2-ethyl hexanoate)3, Nd(neodecanoate)3, Nd(2-ethylhexanoate)3, Nd(2,2-diethyl decanoate)3, Nd(2,2-dipropyl decanoate)3, Nd(2,2-dibutyl decanoate)3, Nd(2,2-dihexyl decanoate)3, Nd(2,2-dioctyl decanoate)3, Nd(2-ethyl-2-propyl decanoate)3, Nd(2-ethyl-2-butyl decanoate)3, Nd(2-ethyl-2-hexyl decanoate)3, Nd(2-propyl-2-butyl decanoate)3, Nd(2-propyl-2-hexyl decanoate)3, Nd(2-propyl-2-isopropyl decanoate)3, Nd(2-butyl-2-hexyl decanoate)3, Nd(2-hexyl-2-octyl decanoate)3, Nd(2-t-butyl decanoate)3, Nd(2,2-diethyl octanoate)3, Nd(2,2-dipropyl octanoate)3, Nd(2,2-dibutyl octanoate)3, Nd(2,2-dihexyl octanoate)3, Nd(2-ethyl-2-propyl octanoate)3, Nd(2-ethyl-2-hexyl octanoate)3, Nd(2,2-diethyl nonanoate)3, Nd(2,2-dipropyl nonanoate)3, Nd(2,2-dibutyl nonanoate)3, Nd(2,2-dihexyl nonanoate)3, Nd(2-ethyl-2-propyl nonanoate)3 and Nd(2-ethyl-2-hexyl nonanoate)3.

### Claim 4

A conjugated diene-based polymer catalyzed with a lanthanide rare earth element, wherein the conjugated diene-based polymer has a ratio ((−S/R)/MWD) of a stress/relaxation (S/R) value at 100° C. and molecular weight distribution (MWD) of 0.30 or more and comprises a functional group derived from a modifier represented by the following Formula 4 or Formula 5:
wherein, in Formula 4 or Formula 5,
Z1 and Z2 are each independently a silane group, N,N-2 substituted aminophenyl group, an imine group or a cyclic amino group,
R1 and R7 are each independently a single bond or a divalent organic group,
R3 and R6 are each independently a single bond or a divalent organic group; or R3 and R6 are trivalent organic groups which are connected with R4 or R5, and R8 or R9, respectively, to form rings, R4 and R8 are each independently a monovalent organic group; or R4 and R8 are divalent organic groups which are connected with R3 or R5, and R6 or R9, respectively, to form rings, and
R5 is a monovalent organic group; or a divalent organic group which is connected with R3 or R4 to form a ring.

### Claim 5 (depends on 1)

A method for preparing the conjugated diene-based polymer catalyzed with the lanthanide rare earth element described in claim 1, comprising:
polymerizing a conjugated diene-based monomer in the presence of a lanthanide rare earth element catalyst composition to prepare an active polymer comprising an organometal part,
wherein the lanthanide rare earth element catalyst composition comprises a lanthanide rare earth element-containing compound, a first alkylating agent, a second alkylating agent, a halide and a conjugated diene-based monomer in a molar ratio of 1:100 to 200:40 to 60:2 to 4:20 to 50.

### Claim 6 (depends on 5)

The method according to claim 5, wherein the catalyst composition is prepared by mixing the lanthanide rare earth element-containing compound, the first alkylating agent, the second alkylating agent, the halide and the conjugated diene-based monomer at a temperature of −30° C. to −20° C., and standing at a temperature of −30° C. to −20° C. for 24 hours to 36 hours.

### Claim 7 (depends on 5)

The method according to claim 5, wherein the lanthanide rare earth element-containing compound comprises a neodymium compound represented by the following Formula 1:
wherein in Formula 1,
Ra to Rc are each independently hydrogen, or an alkyl group of 1 to 12 carbon atoms, where Ra to Rc are not hydrogen at the same time.

### Claim 8 (depends on 5)

The method according to claim 5, wherein the first alkylating agent is one or more aluminoxanes selected from the group consisting of methylaluminoxane, modified methylaluminoxane, ethylaluminoxane, n-propylaluminoxane, isopropylaluminoxane, butylaluminoxane, isobutylaluminoxane, n-pentylaluminoxane, neopentylaluminoxane, n-hexylaluminoxane, n-octylaluminoxane, 2-ethylhexylaluminoxane, cyclohexylaluminoxane, 1-methylcyclopentylaluminoxane, phenylaluminoxane and 2,6-dimethylphenyl aluminoxane.

### Claim 9 (depends on 5)

The method according to claim 5, wherein the second alkylating agent is one or more selected from the group consisting of diethylaluminum hydride, di-n-propylaluminum hydride, diisopropylaluminum hydride, di-n-butylaluminum hydride, diisobutylaluminum hydride, di-n-octylaluminum hydride, diphenylaluminum hydride, di-p-tolylaluminum hydride, dibenzylaluminum hydride, phenylethylaluminum hydride, phenyl-n-propylaluminum hydride, phenylisopropylaluminum hydride, phenyl-n-butylaluminum hydride, phenylisobutylaluminum hydride, phenyl-n-octylaluminum hydride, p-tolylethylaluminum hydride, p-tolyl-n-propylaluminum hydride, p-tolylisopropylaluminum hydride, p-tolyl-n-butylaluminum hydride, p-tolylisobutylaluminum hydride, p-tolyl-n-octylaluminum hydride, benzylethylaluminum hydride, benzyl-n-propylaluminum hydride, benzylisopropylaluminum hydride, benzyl-n-butylaluminum hydride, benzylisobutylaluminum hydride benzyl-n-octylaluminum hydride ethylaluminum dihydride, n-propylaluminum dihydride, isopropylaluminum dihydride, n-butylaluminum dihydride, isobutylaluminum dihydride, and n-octylaluminum dihydride.

### Claim 10 (depends on 5)

The method according to claim 5, further comprising reacting the active polymer with a modifier represented by the following Formula 4 or Formula 5:
wherein in Formula 4 or Formula 5,
Z1 and Z2 are each independently a silane group, N,N-2 substituted aminophenyl group, an imine group or a cyclic amino group,
R1 and R7 are each independently a single bond or a divalent organic group,
R3 and R6 are each independently a single bond or a divalent organic group; or R3 and R6 are trivalent organic groups which are connected with R4 or R5, and R8 or R9, respectively to form rings,
R4 and R8 are each independently a monovalent organic group; or R4 and R8 are divalent organic groups which are connected with R3 or R5, and R6 or R9, respectively, to form rings, and
R5 is a monovalent organic group; or a divalent organic group which is connected with R3 or R4 to form a ring.

### Claim 11 (depends on 4)

A method for preparing the conjugated diene-based polymer catalyzed with a lanthanide rare earth element described in claim 4, comprising:
polymerizing a conjugated diene-based monomer in the presence of a lanthanide rare earth element catalyst composition to prepare an active polymer comprising an organometal part,
wherein the lanthanide rare earth element catalyst composition comprises a lanthanide rare earth element-containing compound, a first alkylating agent, a second alkylating agent, a halide and a conjugated diene-based monomer in a molar ratio of 1:100 to 200:40 to 60:2 to 4:20 to 50.

### Claim 12 (depends on 1)

The conjugated diene-based polymer catalyzed with the lanthanide rare earth element according to claim 1, wherein the ratio ((−S/R)/MWD) of a stress relaxation (S/R) value at 100° C. and molecular weight distribution (MWD) of 0.30 to 0.50.