# US 2017/0283522 A1 · Metallocene compound, metallocene-supported catalyst, and method of preparing polyolefin using the same

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- Number: US 2017/0283522 A1
- Document ID: US20170283522A1
- Status: Published application
- Kind: A1
- Application number: 15/507,968
- Filed: 2015-12-15
- Published: 2017-10-05
- Earliest claimed: 2014-12-15
- Assignees: LG Chem, Ltd.
- Applicants: LG Chem, Ltd.
- Inventors: Sung Min LEE; Bog Ki HONG; Kyung Kin CHO; Se Young KIM; Chang Woan HAN; Ki Soo LEE; Eun Kyoung SONG
- Web page: https://patentgrep.com/patent/US20170283522A1

## CPC

- C08F 4/65922: {containing at least two cyclopentadienyl rings, fused or not}
- C07C 13/465: Indenes; Completely or partially hydrogenated indenes
- C07D 221/18: Ring systems of four or more rings
- C08F 4/652: Pretreating with metals or metal-containing compounds
- C08F 4/6592: containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
- C08F 10/00: Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F 12/00: Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Provided are a novel metallocene compound, a metallocene-supported catalyst, and a method of preparing a polyolefin using the same. The metallocene-supported catalyst according to the present disclosure exhibits a high polymerization activity even when the metallocene compound is supported on a support, thereby showing an excellent activity and preparing a polyolefin having a high molecular weight.

## Claims

### Claim 1

A metallocene compound represented by the following Chemical Formula 1:
wherein M is a Group 4 transition metal;
B is carbon, silicon, or germanium;
Q1 and Q2 are the same as or different from each other, and each independently hydrogen, halogen, a C1 to C20 alkyl group, a C2 to C20 alkenyl group, a C6 to C20 aryl group, a C7 to C20 alkylaryl group, a C7 to C20 arylalkyl group, a C1 to C20 alkoxy group, a C2 to C20 alkoxyalkyl group, a C3 to C20 heterocycloalkyl group, or a C5 to C20 heteroaryl group;
X1 and X2 are the same as or different from each other, and each independently halogen, a C1 to C20 alkyl group, a C2 to C20 alkenyl group, a C6 to C20 aryl group, a nitro group, an amido group, a C1 to C20 alkylsilyl group, a C1 to C20 alkoxy group, or a C1 to C20 sulfonate group;
one of C1 and C2 is represented by the following Chemical Formula 2a, and the other is represented by the following Chemical Formula 2b:
in Chemical Formula 2a, R1 to R9 are the same as or different from each other, and each independently hydrogen, a C1 to C20 alkyl group, a C2 to C20 alkenyl group, a C1 to C20 alkoxy group, a C1 to C20 alkylsilyl group, a C1 to C20 silylalkyl group, a C6 to C20 aryl group, a C7 to C20 alkylaryl group, or a C7 to C20 arylalkyl group;
in Chemical Formula 2b, R10 and R12 to R15 are hydrogen,
R11 is a C1 to C20 alkyl group, a C2 to C20 alkenyl group, a C1 to C20 alkylsilyl group, a C1 to C20 silylalkyl group, a C1 to C20 alkoxysilyl group, a C1 to C20 ether group, a C1 to C20 silylether group, a C1 to C20 silyloxy group, a C1 to C20 alkoxy group, a C2 to C20 alkoxyalkyl group, a C6 to C20 aryl group, a C7 to C20 alkylaryl group, or a C7 to C20 arylalkyl group.

### Claim 2 (depends on 1)

The metallocene compound of claim 1, wherein R1 to R9 of Chemical isopropyl group, an n-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, an ethylene group, a propylene group, a butenyl group, a phenyl group, a benzyl group, a naphthyl group, a methoxy group, an ethoxy group, or a tert-butoxyhexyl group, and R11 of Chemical Formula 2b is a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, an ethylene group, a propylene group, a butenyl group, a phenyl group, a benzyl group, a naphthyl group, a trimethylsilyl group, a triethylsilyl group, a tripropylsilyl group, a tributylsilyl group, a triisopropylsilyl group, a trimethylsilylmethyl group, a tert-butyldimethylsilylether group, a methoxy group, an ethoxy group, or a tert-butoxyhexyl group.

### Claim 3 (depends on 1)

The metallocene compound of claim 1, wherein Q1 and Q2 of Chemical Formula 1 are a methyl group or a tert-butoxyhexyl group.

### Claim 4 (depends on 1)

The metallocene compound of claim 1, wherein the compound represented by Chemical Formula 2a is one of the following structural formulae:

### Claim 5 (depends on 1)

The metallocene compound of claim 1, wherein the compound represented by Chemical Formula 2b is one of the following structural formulae:

### Claim 6 (depends on 1)

The metallocene compound of claim 1, wherein the compound represented by Chemical Formula 1 is one of the following structural formulae:

### Claim 7 (depends on 1)

A metallocene-supported catalyst, comprising the metallocene compound of claim 1;
a cocatalyst compound; and
a support.

### Claim 8 (depends on 7)

The metallocene-supported catalyst of claim 7, wherein the cocatalyst compound comprises one or more of compounds represented by the following Chemical Formula 3, Chemical Formula 4, and Chemical Formula 5:
—[AL(R16)—O]n— [Chemical Formula 3]
wherein R16s are the same as or different from each other, and each independently halogen; C1 to C20 hydrocarbon; or halogen-substituted C1 to C20 hydrocarbon; and
n is an integer of 2 or more;
J(R17)3 [Chemical Formula 4]
wherein R17s are the same as defined in Chemical Formula 3; and
J is aluminum or boron;
[E-H]+[ZA4]− or [E]+[ZA4]− [Chemical Formula 5]
wherein E is a neutral or cationic Lewis acid;
H is a hydrogen atom;
Z is a Group 13 element; and
As are the same as or different from each other, and each independently a C6 to C20 aryl group or a C1 to C20 alkyl group, of which one or more hydrogen atoms are unsubstituted or substituted with halogen, C1 to C20 hydrocarbon, alkoxy, or phenoxy.

### Claim 9 (depends on 7)

The metallocene-supported catalyst of claim 7, wherein the support is one or more selected from the group consisting of silica, silica-alumina, and silica-magnesia

### Claim 10 (depends on 7)

The metallocene-supported catalyst of claim 7, wherein a weight ratio of the transition metal of the metallocene compound to the support is 1:10 to 1:1,000.

### Claim 11 (depends on 7)

The metallocene-supported catalyst of claim 7, wherein a weight ratio of the cocatalyst compound to the support is 1:1 to 1:100.

### Claim 12 (depends on 7)

A method of preparing a polyolefin, the method comprising polymerizing olefinic monomers in the presence of the metallocene-supported catalyst of claim 7.

### Claim 13 (depends on 12)

The method of claim 12, wherein the polymerization is performed by a solution polymerization process, a slurry process, or a gas phase process.

### Claim 14 (depends on 12)

The method of claim 12, wherein the olefinic monomer comprises one or more monomers selected from the group consisting of ethylene, propylene, 1-butene, 1-hexene, 1-octene, 1-pentene, 4-methyl-1-pentene, 1-heptene, 1-decene, 1-undecene, 1-dodecene, norbornene, ethylidenenorbornene, styrene, alpha-methylstyrene, and 3-chloromethylstyrene.

### Claim 15 (depends on 12)

A polyolefin prepared by the preparation method of claim 12.

### Claim 16 (depends on 15)

The polyolefin of claim 15, wherein a weight average molecular weight is 200,000 g/mol to 900,000 g/mol.