IP Library Granted Patent US 9,045,570
Granted Patent B2
US 9,045,570 · App. 14/022,425 · Granted Jun 2, 2015

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

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Quick Facts
Patent No.
US 9,045,570
App. No.
14/022,425
Filed
Sep 10, 2013
Granted
Jun 2, 2015
Kind
B2
Art Unit
1671
USPC
562/124
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 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

two consecutive R groups in R 1 -R 4 are linked to form a cyclic structure.

2. The procatalyst composition of claim 1 wherein R 1 -R 2 form a C 6 membered ring and each of R 3 -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.

3. The procatalyst composition of claim 1 wherein each of R 3 -R 14 is hydrogen.

4. The procatalyst composition of claim 1 wherein the substituted phenylene aromatic diester has the structure (IV)

and each of R 3 -R 14 is hydrogen.

5. The procatalyst composition of claim 1 wherein R 2 -R 3 form a C 6 membered ring and each of R 1 , R 4 and R 5 -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.

6. The procatalyst composition of claim 5 wherein each of R 1 , R 4 and R 5 -R 14 is hydrogen.

7. The procatalyst composition of claim 1 wherein the substituted phenylene aromatic diester has the structure (V)

and each of R 1 , R 4 and R 5 -R 14 is hydrogen.

8. A catalyst composition comprising the procatalyst of claim 1 ;

a cocatalyst; and

an activity limiting agent comprising an aliphatic mono-carboxylic acid ester.

9. The catalyst composition of claim 8 comprising an external electron donor comprising an alkoxysilane.

10. 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 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;

two consecutive R groups in R 5 -R 9 are linked to form a cyclic structure; and

two consecutive R groups in R 10 -R 14 are linked to form a cyclic structure.

11. The procatalyst composition of claim 10 wherein the substituted phenylene aromatic diester has the structure (II)

and each of R 2 , R 4 , R 5 -R 7 and R 10 -R 12 is hydrogen.

12. The procatalyst composition of claim 10 wherein the substituted phenylene aromatic diester has the structure (III)

and each of R 2 , R 4 , R 5 , R 6 , R 9 , R 10 , R 11 , and R 14 is hydrogen.

13. A catalyst composition comprising the procatalyst of claim 10 ;

a cocatalyst; and

an activity limiting agent comprising an aliphatic mono-carboxylic acid ester.

14. The catalyst composition of claim 13 comprising an external electron donor comprising an alkoxysilane.

Assignments (13)
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 072519/0265 →
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 Apr 2, 2023
From: W. R. GRACE & CO.-CONN.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 063199/0472 →
NOTES SECURITY AGREEMENT Recorded Sep 23, 2021
From: W. R. GRACE & CO.-CONN.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 057594/0156 →
TERM LOAN SECURITY AGREEMENT Recorded Sep 23, 2021
From: W. R. GRACE & CO.-CONN.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 057594/0104 →
RELEASE OF SECURITY INTEREST Recorded Sep 23, 2021
From: GOLDMAN SACHS BANK USA
To: W. R. GRACE & CO.-CONN.
Reel/Frame 057594/0026 →
SECURITY INTEREST Recorded Apr 3, 2018
From: W. R. GRACE & CO.-CONN.
To: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
Reel/Frame 045828/0683 →
RELEASE OF SECURITY AGREEMENT RECORDED AT REEL/FRAME NO.: 032159/0384 Recorded Apr 3, 2018
From: GOLDMAN SACHS BANK USA, AS THE COLLATERAL AGENT
To: W.R. GRACE & CO.-CONN.
Reel/Frame 045832/0887 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE NAME TO "W. R. GRACE & CO. - CONN." PREVIOUSLY RECORDED ON REEL 032554 FRAME 0730. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNEE NAME WAS PREVIOUSLY INCORRECTLY LISTED IN THE RECORDATION COVER SHEET DATED 3/28/2014 AS "W. R. GRACE & CO. CONN.". Recorded Apr 2, 2014
From: DOW GLOBAL TECHNOLOGIES LLC; UNION CARBIDE CHEMICALS & PLASTICS TECHNOLOGY LLC
To: W. R. GRACE & CO. - CONN.
Reel/Frame 032589/0554 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 28, 2014
From: DOW GLOBAL TECHNOLOGIES LLC; UNION CARBIDE CHEMICALS & PLASTICS TECHNOLOGY LLC
To: W. R. GRACE & CO. CONN.
Reel/Frame 032554/0730 →
SECURITY AGREEMENT Recorded Feb 4, 2014
From: W.R. GRACE & CO.-CONN.
To: GOLDMAN SACHS BANK USA, AS THE COLLATERAL AGENT
Reel/Frame 032159/0384 →