IP Library Granted Patent US 9,637,575
Granted Patent B2
US 9,637,575 · App. 14/588,379 · Granted May 2, 2017

Catalyst system, olefin polymerization catalyst components comprising at least an internal electron donor compound, and methods of making and using the same

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Quick Facts
Patent No.
US 9,637,575
App. No.
14/588,379
Granted
May 2, 2017
Kind
B2
Abstract

An olefin polymerization catalyst component comprising an internal electron donor compound shown in formula (I) below is provided in this disclosure: wherein X is O, S, NR a , PR b , or POOR c , R a is independently hydrogen, halogen, carbonyl hydrocarbon, linear or branched unsaturated or saturated alkyl hydrocarbon, cyclic, aromatic, or aliphatic hydrocarbon, R b is independently hydrogen, halogen, carbonyl hydrocarbon, linear or branched unsaturated or saturated alkyl hydrocarbon, linear or branched unsaturated or saturated alkoxy hydrocarbon, cyclic, aromatic, or aliphatic hydrocarbon, R c is independently hydrogen, carbonyl hydrocarbon, linear or branched unsaturated or saturated alkyl hydrocarbon, cyclic, aromatic, or aliphatic hydrocarbon, R1-R8 are identical or different hydrogen, halogen, linear or branched unsaturated or saturated C 1 -C 30 alkyl, alone or in combination with C 5 -C 30 substituted or unsubstituted 5-or 6-membered aliphatic or aromatic hydrocarbon rings, each of R a , R b , R c , and/or R1-R8 are optionally substituted with halogen.

Claims (52)

1. An olefin polymerization catalyst component comprising an internal electron donor compound represented by formula (I):

wherein:

X is O, S, NR a , PR b , or POOR c ,

R a is hydrogen, halogen, a carbonyl hydrocarbon, a linear or branched unsaturated or saturated alkyl hydrocarbon, or an unsubstituted or halogen-substituted moiety selected from the group consisting of a cyclic, an aromatic, and an aliphatic hydrocarbon,

R b is hydrogen, halogen, a carbonyl hydrocarbon, a linear or branched unsaturated or saturated alkyl hydrocarbon, a linear or branched unsaturated or saturated alkoxy hydrocarbon, or an unsubstituted or halogen-substituted moiety selected from the group consisting of a cyclic, an aromatic, and an aliphatic hydrocarbon,

R c is hydrogen, a carbonyl hydrocarbon, a linear or branched unsaturated or saturated alkyl hydrocarbon, or an unsubstituted or halogen-substituted moiety selected from the group consisting of a cyclic, an aromatic, and an aliphatic hydrocarbon, and

R1-R8 are identical or different and are hydrogen, halogen, a linear or branched unsaturated or saturated C1-C30 alkyl, or an unsubstituted or halogen-substituted moiety selected from the group consisting of C5-C30 substituted or unsubstituted 5-or 6-membered aliphatic and aromatic hydrocarbon rings.

2. The olefin polymerization catalyst component of claim 1 , wherein R1 and R2 and/or R7 and R8 form a 5-or 6-membered aliphatic or aromatic hydrocarbon ring optionally substituted with halogen; and R3 is linear or branched unsaturated or saturated C 1 -C 12 alkyl or R3 is linear or branched C 1 -C 12 alkoxy.

3. The olefin polymerization catalyst component of claim 1 , wherein X is O.

4. The olefin polymerization catalyst component of claim 1 , wherein the internal electron donor compound is (D-1) shown below

5. A catalyst system for polymerization of an olefin comprising:

a) the olefin polymerization catalyst component of claim 1 further comprising a titanium halide and/or a magnesium halide;

b) an organoaluminum compound; and

c) optionally an external electron donor.

6. The catalyst system of claim 5 , wherein the magnesium halide is magnesium chloride and the titanium halide is TiCl 4 or TiCl 3 .

7. The catalyst system of claim 5 , wherein the organoaluminum compound is an alkyl-aluminum compound.

8. The catalyst system of claim 7 , wherein the alkyl-aluminum compound is a trialkyl aluminum compound.

9. The catalyst system of claim 8 , wherein the trialkyl aluminum compound is selected from the group consisting of triethylaluminum, triisobutylaluminum, and tri-n-octylaluminum, and combinations thereof.

10. The catalyst system of claim 5 further comprising esters, phthalate compounds, ketones, and/or ethers.

11. A process for polymerizing or copolymerizing an olefin, the process comprising

(a) providing a catalyst system of claim 5 ;

(b) polymerizing or copolymerizing the olefin in a presence of the catalyst system to form a polymer or a copolymer; and

(c) recovering the polymer or the copolymer.

12. The process of claim 11 , wherein the olefin is selected from the group consisting of ethylene, propylene, 1-butylene, 4-methyl-1-pentente, 1-hexene, 1-octene, and mixtures thereof.

13. A catalyst system for polymerization of an olefin, the catalyst system comprising a catalyst component comprising an internal electron donor compound represented by formula (I):

wherein:

X is O, S, NR a , PR b , or POOR c ,

R a is hydrogen, halogen, a carbonyl hydrocarbon, a linear or branched unsaturated or saturated alkyl hydrocarbon, or an unsubstituted or halogen-substituted moiety selected from the group consisting of a cyclic, an aromatic, and an aliphatic hydrocarbon,

R b is hydrogen, halogen, a carbonyl hydrocarbon, a linear or branched unsaturated or saturated alkyl hydrocarbon, a linear or branched unsaturated or saturated alkoxy hydrocarbon, or an unsubstituted or halogen-substituted moiety selected from the group consisting of a cyclic, an aromatic, and an aliphatic hydrocarbon,

R c is hydrogen, a carbonyl hydrocarbon, a linear or branched unsaturated or saturated alkyl hydrocarbon, or an unsubstituted or halogen-substituted moiety selected from the group consisting of a cyclic, an aromatic, and an aliphatic hydrocarbon, and

R1-R8 are identical or different and are hydrogen, halogen, a linear or branched unsaturated or saturated C1-C30 alkyl, or an unsubstituted or halogen-substituted moiety selected from the group consisting of C5-C30 substituted or unsubstituted 5-or 6-membered aliphatic and aromatic hydrocarbon rings.

14. The catalyst system of claim 13 , wherein X is O;

R1 and R2 and/or R7 and R8 form a 5-or 6-membered hydrocarbon ring optionally substituted with halogen; and

R3 is linear or branched unsaturated or saturated C 1 -C 12 alkyl or R3 is linear or branched C 1 -C 12 alkoxy.

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

the olefin polymerization catalyst component of claim 1 ;

an organoaluminum compound; and

an organosilicon compound.

16. The catalyst system of claim 15 , wherein the organoaluminum compound is an alkyl-aluminum compound.

17. The catalyst system of claim 16 , wherein the alkyl-aluminum compound is a trialkyl aluminum compound.

18. The catalyst system of claim 17 , wherein the trialkyl aluminum compound is selected from the group consisting of triethylaluminum, triisobutylaluminum, and tri-n-octylaluminum, and combinations thereof.

19. The catalyst system of claim 15 , wherein the organosilicon compound is represented by chemical formula (II):

R n Si(OR′) 4-n   (II)

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

20. The catalyst system of claim 15 , wherein the organosilicon compound is represented by chemical formula (III):

SiRR′ m (OR″) 3-m   (III)

wherein R 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.

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

(i) providing the catalyst system of claim 15 ;

(ii) polymerizing or copolymerizing the olefin monomer in the presence of the catalyst system to form a polymer or a copolymer; and

(iii) recovering the polymer or the copolymer.

22. The process of claim 21 , wherein the olefin monomer is selected from the group consisting of ethylene, propylene, 1-butylene, 4-methyl-1-pentene, 1-hexane, 1-octene, and combinations 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 May 23, 2016
From: NGUYEN, BINH THANH; FERNANDES, JONAS ALVES
To: BASF CORPORATION
Reel/Frame 038678/0988 →