IP Library › Granted Patent US 11,912,811
Granted Patent B2
US 11,912,811 · App. 17/431,608 · Granted Feb 27, 2024

Catalyst composition, cleaning liquid composition containing the same, and method of cleaning polymerization apparatus using the cleaning liquid composition

Inventors: Eun Gyeong Lee (Daejeon, KR); Hong Soo Lee (Daejeon, KR)
Assignee: LG Chem, Ltd.
C08F4/60C08F2/008C08F236/10
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Quick Facts
Patent No.
US 11,912,811
App. No.
17/431,608
Granted
Feb 27, 2024
Kind
B2
Abstract

The present invention relates to a catalyst composition containing: one or more selected from the group consisting of a transition metal compound represented by Formula 1 and a transition metal compound represented by Formula 3, and dialkyl L-tartrate; a cleaning liquid composition containing the catalyst composition; and a method of cleaning a polymerization apparatus using the cleaning liquid composition, wherein all the variables are described herein.

Claims (41)

1. A catalyst composition comprising: dialkyl L-tartrate; and one or more selected from the group consisting of a transition metal compound represented by the following Formula 1 and a transition metal compound represented by the following Formula 3:

wherein

M is ruthenium or osmium,

A is oxygen (O), nitrogen (N), or sulfur (S), and if A is oxygen (O) or sulfur (S), R 11 does not exist,

X 1 and X 2 are each independently halogen,

R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms,

R 7 and R 8 are each independently hydrogen or an electron withdrawing group,

R 9 is a direct bond or an alkylene group having 1 to 10 carbon atoms, and

R 10 and R 11 are each independently an alkyl group having 1 to 10 carbon atoms or a substituent represented by the following Formula 2,

wherein

Y is oxygen (O), nitrogen (N), or sulfur (S), and if Y is oxygen (O) or sulfur (S), R 14 does not exist,

R 12 is an alkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 3 to 10 carbon atoms, or an arylene group having 6 to 10 carbon atoms,

R 13 and R 14 are each independently hydrogen, an alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms, and

* represents a bonding position with A,

wherein

M is ruthenium or osmium,

R 1 and R 2 are each independently hydrogen or a substituent represented by the following Formula 4, and at least one of R 1 or R 2 is a substituent represented by the following Formula 4,

X 1 and X 2 are each independently halogen, and

Ph is a phenyl group, and

wherein

R 3 and R 4 are each independently an alkyl group having 1 to 10 carbon atoms; or

R 3 and R 4 are linked together, and with N to which they are attached to form a saturated or unsaturated 5-membered ring.

2. The catalyst composition of claim 1 , wherein the transition metal compound represented by Formula 1 is a transition metal compound represented by the following Formula 5:

wherein

M and R 7 are each as defined in claim 1 .

3. The catalyst composition of claim 1 , wherein the transition metal compound represented by Formula 1 is a transition metal compound represented by the following Formula 5-1:

4. The catalyst composition of claim 1 , wherein the transition metal compound represented by Formula 3 is a transition metal compound represented by the following Formula 6:

wherein

M, R 1 , and R 2 are each as defined in claim 1 .

5. The catalyst composition of claim 1 , wherein the transition metal compound represented by Formula 3 is a transition metal compound represented by the following Formula 6-1:

wherein

M is ruthenium.

6. The catalyst composition of claim 1 , wherein the dialkyl L-tartrate is one or more selected from the group consisting of diethyl L-tartrate and dibutyl L-tartrate.

7. The catalyst composition of claim 1 , wherein the dialkyl L-tartrate is included in an amount of 1 to 25 equivalents relative to 1 equivalent of one or more selected from the group consisting of the transition metal compound represented by Formula 1 and the transition metal compound represented by Formula 3.

8. A method of cleaning a polymerization apparatus, the method comprising: a step of injecting the catalyst composition of claim 1 into a polymerization apparatus containing a diene-based polymer, and a step of performing an olefin cross metathesis.

9. The method of claim 8 , further comprising, before the olefin cross metathesis step, a step of swelling the diene-based polymer in the polymerization apparatus with a hydrocarbon-based solvent.

10. The method of claim 9 , further comprising, before the swelling step or the olefin cross metathesis step, a step of preparing the diene-based polymer in the presence of a catalyst system by polymerization in the polymerization apparatus, wherein the catalyst system contains a rare earth metal compound and an organoaluminum compound.

11. The method of claim 8 , wherein one or more monomers selected from the group consisting of an olefin-based monomer, a conjugated diene-based monomer, and an aromatic vinyl-based monomer are further injected to perform the olefin cross metathesis of the diene-based polymer.

12. The method of claim 8 , wherein the olefin cross metathesis of the diene-based polymer is performed at a temperature of 60° C. or more.

13. The method of claim 8 , wherein the diene-based polymer is one selected from the group consisting of butadiene rubber, isoprene rubber, styrene-butadiene rubber, and styrene-butadiene-styrene block copolymer.

14. The method of claim 8 , where the one or more selected from the group consisting of a transition metal compound represented by Formula 1 and a transition metal compound represented by Formula 3 is included in an amount of 0.001 to 1 part by weight per 100 parts by weight of the diene-based polymer.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 24, 2021
From: LEE, EUN GYEONG; LEE, HONG SOO
To: LG CHEM, LTD.
Reel/Frame 057269/0253 →
Priority Claims (1)
KR 10-2020-0041908 · Apr 7, 2020 · national
Continuity (1)
Related Publication 20220162351A1 · May 26, 2022