# US 2018/0022852 A1 · Organic zinc compound comprising polyolefin-polystyrene block copolymer, and method for preparing the same

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- Number: US 2018/0022852 A1
- Document ID: US20180022852A1
- Status: Published application
- Kind: A1
- Application number: 15/549,343
- Filed: 2016-01-21
- Published: 2018-01-25
- Earliest claimed: 2015-02-10
- Assignees: LG Chem, Ltd.
- Applicants: LG Chem, Ltd.
- Inventors: Bun Yeoul Lee; Jong Yeob Jeon; Geun Ho Park
- Web page: https://patentgrep.com/patent/US20180022852A1

## CPC

- C08F 297/083: {the monomers being ethylene or propylene}
- C07F 3/06: Zinc compounds
- C07F 17/00: Metallocenes
- C07F 19/00: Metal compounds according to more than one of main groups C07F1/00 - C07F17/00
- C08F 112/08: Styrene
- C08F 295/00: Macromolecular compounds obtained by polymerisation using successively different catalyst types without deactivating the intermediate polymer
- C08F 297/02: using a catalyst of the anionic type
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

The present invention relates to an organic zinc compound comprising a styrene-based polymer or a polyolefin-polystyrene block copolymer at both ends. Also, the present invention relates to a method for preparing the organic zinc compound, the method preparing an intermediate by coordination-polymerizing an olefin monomer using a transition metal catalyst, and then performing anionic polymerization by inserting an alkyllithium compound, an amine ligand, and a styrene-based monomer into the intermediate. Accordingly, the present invention can provide a method for preparing a commercially useful styrene-based polymer or polyolefin-polystyrene block copolymer directly from an olefin monomer and a styrene monomer in a one-pot manner.

## Claims

### Claim 1

An organic zinc compound represented by Formula 1:
where R1 and R2 are each independently hydrogen or an alkyl group having 1 to 20 carbon atoms; Ar is an aryl group having 6 to 20 carbon atoms; A is a hydrocarbon group having 1 to 20 carbon atoms; an average value of a1 and a2 is approximately 0 to 10,000; and an average value of b1 and b2 is approximately 10 to 1,000.

### Claim 2 (depends on 1)

The organic zinc compound of claim 1, wherein R1 and R2 of Formula 1 are each independently any one of hydrogen, a methyl group, an ethyl group, a butyl group, a hexyl group and an octyl group; Ar is a phenyl group; A is any one of a methyl group, an ethyl group, a hexyl group, a phenyl group and a benzyl group.

### Claim 3 (depends on 1)

The organic zinc compound of claim 1, wherein the organic zinc compound is represented by Formula 1A below:
where R3, R4, R5 and R6 are each independently any one of hydrogen, a methyl group, an ethyl group, a butyl group, a hexyl group and an octyl group, R3 and R4 are not the same, R5 and R6 are not the same; Ar is a phenyl group; A is a methyl group, an ethyl group, a hexyl group, a phenyl group or a benzyl group; p and 1-p are mole fractions of respective repeating blocks constituting a repeating unit a1, p ranges from approximately more than 0 less than 1; q and 1-q are mole fractions of respective repeating blocks constituting a repeating unit a2, q ranges from approximately more than 0 less than 1; an average value of a1 and a2 is approximately more than 0 to 10,000; and an average value of b1 and b2 is approximately 10 to 1,000.

### Claim 4 (depends on 3)

The organic zinc compound of claim 3, wherein any one of R3 and R4 of Formula 1A is hydrogen, and the other one is a methyl group, an ethyl group, a butyl group or a hexyl group; any one of R5 and R6 is hydrogen, and the other one is a methyl group, an ethyl group, a butyl group or a hexyl group.

### Claim 5

A method for preparing an organic zinc compound represented by Formula 1 below, the method comprising:
a first step of preparing a compound represented by Formula 3 through coordination polymerization of an olefin monomer using a transition metal catalyst in the presence of organic zinc represented by Formula 2; and
a second step of sequentially adding an alkyl lithium compound represented by Formula 4, an amine ligand represented by Formula 5 and a styrene-based monomer to the compound represented by Formula 3 to perform anionic polymerization:
where R1 and R2 are each independently hydrogen or an alkyl group having 1 to 20 carbon atoms; Ar is an aryl group having 6 to 20 carbon atoms; A is a hydrocarbon group having 1 to 20 carbon atoms; an average value of a1 and a2 is approximately 0 to 10,000; and
an average value of b1 and b2 is approximately 10 to 1,000; and
(A)2Zn [Formula 2]
where A is a hydrocarbon group having 1 to 20 carbon atoms; and
where R1 and R2 are each independently hydrogen or an alkyl group having 1 to 20 carbon atoms; A is a hydrocarbon group having 1 to 20 carbon atoms; and an average value of a1 and a2 ranges from approximately 0 to 10,000;
B—Li [Formula 4]
where B is an alkyl group having 1 to 20 carbon atoms;
where R51 and R52 are each independently a hydrocarbon group having 1 to 20 carbon atoms, and z is an integer of approximately 2 or 3.

### Claim 6 (depends on 5)

The method of claim 5, wherein the olefin monomer (CH2═CH—R) is ethylene, propylene, 1-butene, 1-hexene, 1-octene, 1-decene or a mixture thereof, and the styrene-based monomer (ArCH═CH2) is styrene.

### Claim 7 (depends on 5)

The method of claim 5, wherein the olefin monomer (CH2═CH—R) is a mixture of any one of propylene, 1-butene, 1-hexene and 1-octene; and ethylene, and the styrene-based monomer (ArCH═CH2) is styrene.

### Claim 8 (depends on 5)

The method of claim 5, wherein A of Formula 2 is one of a methyl group, an ethyl group, a hexyl group, a phenyl group and a benzyl group.

### Claim 9 (depends on 5)

The method of claim 5, wherein the transition metal catalyst is a transition metal compound represented by Formula 6A or 6B below:
In Formula 6A, R61 is hydrogen or methyl, and R62 is hydrogen or phenyl;

### Claim 10 (depends on 5)

The method of claim 5, wherein the polymerization in the first step is performed by solution polymerization using a solvent containing one or more of isobutane, hexane, cyclohexane and methylcyclohexane.

### Claim 11 (depends on 5)

The method of claim 5, wherein the alkyl lithium compound is n-BuLi.

### Claim 12 (depends on 5)

The method of claim 5, wherein the amine ligand is a compound represented by Formula 5 is a compound in which R51 is methyl, R52 is hydrogen, and z is approximately 2.

### Claim 13 (depends on 5)

The method of claim 5, wherein a molar ratio of the alkyl lithium compound and the amine ligand is approximately 1:0.5 to 1:1.5.