IP Library Granted Patent US 9,663,595
Granted Patent B2
US 9,663,595 · App. 14/451,990 · Granted May 30, 2017

Solid catalyst components for olefin polymerization and methods of making and using the same

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Quick Facts
Patent No.
US 9,663,595
App. No.
14/451,990
Granted
May 30, 2017
Kind
B2
Abstract

Solid catalyst components are disclosed including titanium, magnesium, halogen and an internal electron donor compound having at least one substituted 2-methoxy-1-naphthoate, and catalyst systems containing the catalyst solid components, organoaluminum compounds, and organosilicon compounds. Further, methods of making the catalyst components and the catalyst systems are disclosed as well as methods of polymerizing or copolymerizing alpha-olefins using the catalyst systems.

Claims (41)

1. A solid catalyst component for use in olefinic polymerization, comprising:

a titanium compound,

a magnesium compound, and

an internal electron donor compound,

wherein

the internal electron donor compound comprises a compound represented by formula (II):

wherein:

R 1 is selected from the group consisting of H; a halogen; and a saturated or nonsaturated, linear or branched, cyclic or acyclic C 1 to C 22 hydrocarbyl group, wherein the hydrocarbyl group optionally contains a —O—, —NH—, or —S— group in place of a —CH 2 — group or a —N═ or —S═ group in place of a —C═ group, and wherein the hydrocarbyl group is optionally substituted by one or more halogens; wherein

R 2 is selected from the group consisting of H; a halogen; and a saturated or nonsaturated, linear or branched, cyclic or acyclic C 1 to C 22 hydrocarbyl group, wherein the hydrocarbyl group optionally contains a —O—, —NH—, or —S— group in place of a —CH 2 — group or a —N═ or —S═ group in place of a —C═ group, and wherein the hydrocarbyl group is optionally substituted by one or more halogens; and wherein

R 5 and R 6 are each independently selected from the group consisting of H; a halogen; and a saturated or non-saturated, linear or branched, cyclic or acyclic C 1 to C 22 hydrocarbyl group, wherein the hydrocarbyl group optionally contains a —O—, —NH—, or —S— group in place of a —CH 2 — group or a —N═ or —S═ group in place of a —C═ group, and wherein the hydrocarbyl group is optionally substituted by one or more halogens; and

R 9 , R 10 , R 11 , and R 12 are each independently selected from the group consisting of H; a halogen; and a saturated or non-saturated, linear or branched, cyclic or acyclic C 1 to C 22 hydrocarbyl group, wherein the hydrocarbyl group optionally contains a —O—, —NH—, or —S— group in place of a —CH 2 — group or a —N═ or —S═ group in place of a —C═ group, and wherein the hydrocarbyl group is optionally substituted by one or more halogens.

2. The solid catalyst component of claim 1 , wherein

R 1 is selected from the group consisting of H; a halogen; and a linear or branched C 1 -C 20 alkyl group;

R 2 is selected from the group consisting of H; a halogen; and a linear or branched C 1 -C 20 alkyl group; and

R 5 , R 6 , R 9 , R 10 , R 11 , and R 12 are each H.

3. The solid catalyst component of claim 1 , wherein R 1 and R 2 are independently selected from the group consisting of H and a linear or branched C 1 -C 20 alkyl group.

4. The solid catalyst component of claim 1 , wherein R 2 is methyl.

5. The solid catalyst component of claim 1 , wherein the internal electron donor compound is 2-methoxy-1-naphthoic acid, a branched or linear alkyl 2-methoxy-1-naphthoate, or a branched or linear methyl 2-alkyloxy-1-naphthoate, or a combination of any two or more thereof.

6. The solid catalyst component of claim 1 , wherein the solid catalyst component contains only one internal electron donor compound.

7. The solid catalyst component of claim 1 , further comprising an additional internal electron donor compound.

8. The solid catalyst component of claim 1 , wherein the titanium compound has at least one titanium-halogen bond and the magnesium compound is a magnesium halide, wherein the magnesium halide forms a crystal lattice, and wherein the internal electron donor compound is supported on the magnesium halide crystal lattice.

9. The solid catalyst component of claim 8 , wherein the magnesium halide crystal lattice is a magnesium dichloride crystal lattice.

10. The solid catalyst component of claim 8 , wherein the titanium compound is TiCl 4 or TiCl 3 .

11. A catalyst system for use in olefinic polymerization, the catalyst system comprising:

the solid catalyst component of claim 1 ;

an organoaluminum compound; and

optionally an organosilicon compound.

12. The catalyst system of claim 11 , wherein the organoaluminum compound is an alkyl-aluminum compound.

13. The catalyst system of claim 12 , wherein the alkyl-aluminum compound is a trialkyl aluminum compound.

14. The catalyst system of claim 13 , wherein the trialkyl aluminum compound is selected from the group consisting of triethylaluminum, triisobutylaluminum, and tri-n-octylaluminum, and a combination of any two or more thereof.

15. The catalyst system of claim 11 , wherein the organosilicon compound is present and represented by formula (IV):

R n Si(OR′) 4-n   (IV)

wherein

each R and R′ independently represent a hydrocarbon group, and n is an integer from 0 to 3.

16. The catalyst system of claim 11 , wherein the organosilicon compound is represented by formula (V):

SiRR′ m (OR″) 3-m   (V)

wherein R independently represents a cyclic hydrocarbon or substituted cyclic hydrocarbon group, wherein each R′ and R″ independently represent a hydrocarbon group, and wherein m is an integer from 0 to 2.

17. A process of polymerizing or copolymerizing an olefin monomer, the process comprising:

polymerizing or copolymerizing the olefin monomer in the presence of the catalyst system of claim 11 to form a polymer or a copolymer; and

recovering the polymer or the copolymer.

18. The process of claim 17 , wherein the olefin monomer is selected from the group consisting of ethylene, propylene, 1-butylene, 4-methyl-1-pentene, 1-hexane, 1-octene, and a combination of any two or more thereof.

Assignments (9)
RELEASE OF SECURITY INTEREST Recorded Sep 23, 2021
From: GOLDMAN SACHS BANK USA
To: W. R. GRACE & CO.-CONN.
Reel/Frame 057594/0026 →
TERM LOAN SECURITY AGREEMENT Recorded Sep 23, 2021
From: W. R. GRACE & CO.-CONN.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 057594/0104 →
NOTES SECURITY AGREEMENT Recorded Sep 23, 2021
From: W. R. GRACE & CO.-CONN.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 057594/0156 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 6, 2019
From: W. R. GRACE & CO.-CONN.­
To: BRASKEM AMERICA, INC.; BRASKEM SA; BRASKEM EUROPE GMBH
Reel/Frame 050294/0690 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 6, 2019
From: BRASKEM SA
To: BRASKEM AMERICA, INC.
Reel/Frame 050295/0371 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 6, 2019
From: BRASKEM EUROPE GMBH
To: BRASKEM AMERICA, INC.
Reel/Frame 050295/0922 →
SECURITY INTEREST Recorded Apr 3, 2018
From: W. R. GRACE & CO.-CONN.
To: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
Reel/Frame 045828/0683 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 22, 2016
From: BASF CORPORATION
To: W. R. GRACE & CO. - CONN.
Reel/Frame 040255/0136 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 3, 2014
From: NGUYEN, BINH T.; FERNANDES, JONAS ALVES
To: BASF CORPORATION
Reel/Frame 033882/0674 →