IP Library Granted Patent US 8,088,872
Granted Patent B2
US 8,088,872 · App. 12/622,889 · Granted Jan 3, 2012

Procatalyst composition including silyl ester internal donor and method

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Quick Facts
Patent No.
US 8,088,872
App. No.
12/622,889
Granted
Jan 3, 2012
Kind
B2
Abstract

The present disclosure provides silyl esters and silyl diol esters suitable as internal electron donors in procatalysts for polymer production. Disclosed are procatalyst compositions formed from a procatalyst precursor and an internal electron donor that is a silyl ester or a silyl diol ester. The procatalyst compositions can be used with a cocatalyst and optionally an external electron donor and/or an activity limiting agent to form a Ziegler-Nana catalyst composition. The present catalyst compositions exhibit high catalyst activity and form olefin-based polymers with broad molecular weight distribution, favorable flexural modulus, and high isotacticity.

Claims (24)

1. A procatalyst composition comprising:

a combination of a magnesium moiety, a titanium moiety, and an internal electron donor, the internal electron donor comprising a silyl ester of the structure

wherein m is 1 denoting a hydrocarbyl with the same number of carbon atoms, n is 1 denoting a hydrocarbyl with same number of carbon atoms,

R 1 -R 7 are the same or different and each 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, and combinations thereof; and

X is an electron donating group.

2. The procatalyst composition of claim 1 wherein X is selected from the group consisting of —C(═O)OR, —O(O═)CR, —(O═)CNHR, —(O═)CNRR′, —NH(O═)CR, —NR′(O═)CR, —C(═O)R, —OR, —NHR, —NR′R, —SR, —OP(OR′)(OR), —OP(═O)(OR′)(OR), —S(═O)R, —S(═O) 2 R, —OS(═O) 2 (OR), and combinations thereof; and

R and R′ are the same or different and each of R and R′ 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.

3. The procatalyst composition of claim 1 comprising an internal electron donor of the structure

wherein R 1 -R 8 are the same or different and each 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, and combinations thereof.

4. The procatalyst composition of claim 1 comprising an internal electron donor of the structure

5. The procatalyst composition of claim 1 wherein R 3 -R 6 are hydrogen, R 1 and R 2 are the same or different and each is selected from the group consisting of hydrogen, a C 1 -C 6 alkyl group, and combinations thereof.

6. The procatalyst composition claim 1 wherein each of R 1 and R 2 is selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, and combinations thereof.

7. The procatalyst composition of claim 1 wherein R 1 and R 2 are both methyl.

8. The procatalyst composition of claim 1 wherein R 1 is methyl and R 2 is ethyl.

9. The procatalyst composition of claim 1 wherein R 1 and R 2 are both ethyl.

10. The procatalyst composition of claim 1 wherein R 1 is methyl and R 2 is isobutyl.

11. The procatalyst composition of claim 1 wherein the silyl ester comprises bis(benzoyloxy)dimethylsilane.

12. The procatalyst composition of claim 1 wherein the silyl ester comprises bis(benzoyloxy)diethylsilane.

13. The procatalyst composition of claim 1 wherein the silyl ester comprises bis(benzoyloxy)ethylmethylsilane.

14. The procatalyst composition of claim 1 wherein the silyl ester comprises bis(benzoyloxy)isobutylmethylsilane.

15. A catalyst composition comprising:

a procatalyst composition of claim 1 ; and

a cocatalyst.

16. The catalyst composition of claim 15 comprising a member selected from the group consisting of an external electron donor, an activity limiting agent, and combinations thereof.

Assignments (15)
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 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 Feb 17, 2023
From: W.R. GRACE & CO.-CONN.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 062792/0510 →
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 →
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 →
SECURITY INTEREST Recorded Apr 3, 2018
From: W. R. GRACE & CO.-CONN.
To: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
Reel/Frame 045828/0683 →
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 →
CHANGE OF NAME Recorded Mar 21, 2011
From: DOW GLOBAL TECHNOLOGIES INC.
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 025990/0488 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 21, 2010
From: LEUNG, TAK W.
To: DOW GLOBAL TECHNOLOGIES INC.
Reel/Frame 023823/0974 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 21, 2010
From: CHEN, LINFENG; TAO, TAO
To: UNION CARBIDE CHEMICALS & PLASTICS TECHNOLOGY LLC
Reel/Frame 023823/0981 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 21, 2010
From: UNION CARBIDE CHEMICALS & PLASTICS TECHNOLOGY LLC
To: DOW GLOBAL TECHNOLOGIES INC.
Reel/Frame 023824/0033 →