IP Library Granted Patent US 9,434,799
Granted Patent B2
US 9,434,799 · App. 14/724,300 · Granted Sep 6, 2016

Procatalyst composition with substituted 1,2-phenylene aromatic diester internal donor and method

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Quick Facts
Patent No.
US 9,434,799
App. No.
14/724,300
Granted
Sep 6, 2016
Kind
B2
Abstract

Disclosed are procatalyst compositions having an internal electron donor which include a substituted phenylene aromatic diester and optionally an electron donor component. Ziegler-Natta catalyst compositions containing the present procatalyst compositions exhibit high activity and produce propylene-based olefins with broad molecular weight distribution.

Claims (29)

1. A procatalyst composition comprising:

a combination of a magnesium moiety, a titanium moiety and an internal electron donor comprising a substituted phenylene aromatic diester having the structure (I):

wherein:

(A) R 1 -R 14 are the same or different, each of R 1 -R 14 is selected from the group consisting of hydrogen, a substituted hydrocarbyl group having 1 to 20 carbon atoms, an unsubstituted hydrocarbyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a heteroatom, and combinations thereof, and at least one of R 1 -R 14 is not hydrogen; and

(B) at least one or two, or three, or four R groups of R 1 -R 4 is selected from a substituted hydrocarbyl group having 1 to 20 carbon atoms, an unsubstituted hydrocarbyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a heteroatom, and combinations thereof.

2. The procatalyst composition of claim 1

wherein at least one of R 5 -R 14 is selected from the group consisting of a substituted hydrocarbyl group having 1 to 20 carbon atoms, an unsubstituted hydrocarbyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a heteroatom, and combinations thereof.

3. The procatalyst composition of claim 1 wherein at least one of R 5 -R 14 is selected from the group consisting of a substituted hydrocarbyl group having 1 to 20 carbon atoms, an unsubstituted hydrocarbyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a heteroatom and combinations thereof.

4. The procatalyst composition of claim 1 wherein at least one of R 5 -R 9 and at least one of R 10 -R 14 is selected from the group consisting of a substituted hydrocarbyl group having 1 to 20 carbon atoms, an unsubstituted hydrocarbyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a heteroatom, and combinations thereof.

5. The procatalyst composition of claim 1 wherein R 1 and R 3 are the same or different and each is selected from the group consisting of a C 1 -C 8 alkyl group, a C 3 -C 6 group, a cycloalkyl group, and a substituted C 3 -C 6 cycloalkyl group.

6. The procatalyst composition of claim 1 wherein R 1 and R 3 are the same or different and each is selected from the group consisting of a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a t-butyl group, an isobutyl group, a sec-butyl group, a 2,4,4-trimethylpentan-2-yl group, a cyclopentyl group, a cyclohexyl group, and combinations thereof.

7. The procatalyst composition of claim 1 wherein R 2 and R 4 are hydrogen.

8. The procatalyst composition of claim 1 wherein R 1 is a methyl group and R 3 is a t-butyl group.

9. The procatalyst composition of claim 1 wherein each of R 1 and R 3 is an isopropyl group.

10. The procatalyst composition of claim 1 wherein R 1 , R 3 and R 4 are hydrogen and R 2 is selected from the group consisting of a substituted hydrocarbyl group having 1 to 20 carbon atoms, an unsubstituted hydrocarbyl group having 1 to 20 carbon atoms, and combinations thereof.

11. The procatalyst composition of claim 10 wherein R 2 is selected from the group consisting of C 1 -C 8 alkyl group, a C 3 -C 6 cycloalkyl group, and a substituted C 3 -C 6 cycloalkyl group.

12. The procatalyst composition of claim 10 wherein R 2 is selected from the group consisting of a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a t-butyl group, an isobutyl group, a sec-butyl group, a 2,4,4-trimethylpentan-2-yl group, a cyclopentyl group, and a cyclohexyl group.

13. The procatalyst composition of claim 11 wherein R 2 is selected from the group consisting of a methyl group and a t-butyl group.

14. The procatalyst composition of claim 1 wherein R 2 and R 3 are hydrogen and R 1 and R 4 are the same or different, each of R 1 and R 4 is selected from the group consisting of a substituted hydrocarbyl group having 1 to 20 carbon atoms, an unsubstituted hydrocarbyl group having 1 to 20 carbon atoms, and combinations thereof.

15. The procatalyst composition of claim 14 wherein R 1 and R 4 are the same or different and each is selected from the group consisting of a C 1 -C 8 alkyl group, a C 3 -C 6 cycloalkyl group, and a substituted C 3 -C 6 cycloalkyl group.

16. The procatalyst composition of claim 14 wherein R 1 and R 4 are the same or different and each is selected from the group consisting of a methyl group, an ethyl, an n-propyl group, an isopropyl group, a sec-butyl group, an isobutyl group, a cyclopentyl group, and a cyclohexyl group, and combinations thereof.

17. The procatalyst composition of claim 1 comprising an electron donor component selected from the group consisting of a phthalate, a benzoate, a diether, and combinations thereof.

18. A catalyst composition comprising:

the procatalyst composition of claim 1 ; and

a cocatalyst.

19. The catalyst composition of claim 18 comprising a member selected from the group consisting of an external electron donor, an activity limiting agent, and combinations thereof.

20. A process for producing an olefin-based polymer comprising:

contacting, under polymerization conditions, an olefin with the catalyst composition of claim 18 ; and

forming an olefin-based polymer.

Assignments (15)
RELEASE OF SECURITY INTEREST SUPPLEMENT NO. 2, RECORDED AT REEL/FRAME 072519/0265 Recorded Feb 2, 2026
From: WILMINGTON TRUST, NATIONAL ASSOCIATION
To: W. R. GRACE & CO.-CONN.
Reel/Frame 074612/0591 →
NOTES SECURITY INTEREST Recorded Jan 29, 2026
From: W. R. GRACE & CO.-CONN.; ADVANCED REFINING TECHNOLOGIES LLC
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
Reel/Frame 074532/0229 →
SECURITY INTEREST Recorded Aug 19, 2025
From: W. R. GRACE & CO.-CONN.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 072519/0240 →
SECURITY AGREEMENT (NOTES) Recorded Aug 19, 2025
From: W. R. GRACE & CO.-CONN.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
Reel/Frame 072520/0653 →
SECURITY INTEREST Recorded Aug 19, 2025
From: W. R. GRACE & CO.-CONN.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 072519/0265 →
SECURITY INTEREST Recorded Apr 2, 2023
From: W. R. GRACE & CO.-CONN.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 063199/0472 →
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 →
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 Aug 1, 2016
From: UNION CARBIDE CHEMICALS & PLASTICS TECHNOLOGY LLC; DOW GLOBAL TECHNOLOGIES LLC
To: W. R. GRACE & CO.-CONN.
Reel/Frame 039304/0424 →
CHANGE OF NAME Recorded Jul 29, 2016
From: DOW GLOBAL TECHNOLOGIES INC.
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 039515/0138 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 28, 2016
From: UNION CARBIDE CHEMICALS & PLASTICS TECHNOLOGY LLC
To: DOW GLOBAL TECHNOLOGIES INC.
Reel/Frame 039282/0151 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 26, 2016
From: CHEN, LINFENG; TAO, TAO
To: UNION CARBIDE CHEMICALS & PLASTICS TECHNOLOGY LLC
Reel/Frame 039259/0681 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 26, 2016
From: LEUNG, TAK W.
To: DOW GLOBAL TECHNOLOGIES INC.
Reel/Frame 039259/0781 →