IP Library Granted Patent US 8,633,126
Granted Patent B2
US 8,633,126 · App. 12/956,091 · Granted Jan 21, 2014

Three and four atom bridged dicarbonate compounds as internal donors in catalysts for polypropylene manufacture

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Quick Facts
Patent No.
US 8,633,126
App. No.
12/956,091
Granted
Jan 21, 2014
Kind
B2
Abstract

A solid, hydrocarbon-insoluble, catalyst component useful in polymerizing olefins, said catalyst component containing magnesium, titanium, and halogen, and further containing an internal electron donor having a structure: [R 1 —O—C(O)—O—] x R 2 wherein R 1 is independently at each occurrence, an aliphatic or aromatic hydrocarbon, or substituted hydrocarbon group containing from 1 to 20 carbon atoms; x is 2-4; and R 2 is an aliphatic or aromatic hydrocarbon, or substituted hydrocarbon group containing from 1 to 20 carbon atoms, provided that there are from 3 to 4 atoms in the shortest chain connecting a first R 1 —O—C(O)—O— group and a second R 1 —O—C(O)—O— group.

Claims (23)

1. A solid, hydrocarbon-insoluble catalyst component useful in polymerizing olefins, said catalyst component containing magnesium, titanium, and halogen, and further containing an internal electron donor having a structure:

[R 1 —O—C(O)—O—] x R 2

wherein R 1 is independently at each occurrence, an aliphatic or aromatic hydrocarbon, or substituted hydrocarbon group containing from 1 to 20 carbon atoms; x is 2-4; and R 2 is an aliphatic or aromatic hydrocarbon, or substituted hydrocarbon group containing from 1 to 20 carbon atoms, provided that there are from 3 to 4 atoms in the shortest chain connecting a first R 1 —O—C(O)—O— group and a second R 1 —O—C(O)—O— group.

2. The catalyst component of claim 1 where x=2.

3. The catalyst component of claim 1 where each R 1 is an aliphatic hydrocarbon.

4. The catalyst component of claim 1 where each R 1 is an aromatic hydrocarbon.

5. The catalyst component of claim 1 where R 2 is a 1,8-disubstituted naphthylene moiety.

6. The catalyst component of claim 1 where R 2 is a 2,2′-disubstituted biphenyl moiety.

7. The catalyst component of claim 1 where R 2 is a straight or branched alkyl moiety, provided that there are from 3 to 4 atoms in the shortest chain connecting a first R 1 —O—C(O)—O— group and a second R 1 —O—C(O)—O— group.

8. The catalyst component of claims 5 where each R 1 is an aliphatic hydrocarbon.

9. The catalyst component of claims 5 where each R 1 is methyl, ethyl, propyl, butyl, or isobutyl.

10. The catalyst component of claim 1 where the internal electron donor comprises one of the following compounds: dimethyl naphthalene-1,8-diyl dicarbonate; diethyl naphthalene-1,8-diyl dicarbonate; dipropyl naphthalene-1,8-diyl dicarbonate; dibutyl naphthalene-1,8-diyl dicarbonate; diisobutyl naphthalene-1,8-diyl dicarbonate; or biphenyl-2,2′-diyl diethyl dicarbonate.

11. The catalyst component of claim 1 where the internal electron donor comprises one of the following compounds: diethyl naphthalene-1,8-diyl dicarbonate; dipropyl naphthalene-1,8-diyl dicarbonate; or dibutyl naphthalene-1,8-diyl dicarbonate.

12. The catalyst component of claim 1 which is optionally combined with a single component SCA, a mixed component SCA, or an activity limiting agent.

13. The catalyst component of claim 12 where the mixed component SCA contains an activity limiting agent or an organic ester as a component.

14. The catalyst component of claim 13 which is optionally combined with an organoaluminum compound.

15. A method of polymerizing an olefin comprising contacting the olefin with a catalyst component containing magnesium, titanium, and halogen, and further containing an internal electron donor having a structure:

[R 1 —O—C(O)—O—] x R 2

wherein R 1 is independently at each occurrence, an aliphatic or aromatic hydrocarbon, or substituted hydrocarbon group containing from 1 to 20 carbon atoms; x is 2-4; and R 2 is an aliphatic or aromatic hydrocarbon, or substituted hydrocarbon group containing from 1 to 20 carbon atoms, provided that there are from 3 to 4 atoms in the shortest chain connecting a first R 1 —O—C(O)—O— group and a second R 1 —O—C(O)—O— group.

16. A method of polymerizing an olefin comprising contacting the olefin with a catalyst component of claim 2 .

17. A compound for use as an internal electron donor having a structure selected from the group consisting of:

wherein R 1 is independently at each occurrence, an aliphatic or aromatic hydrocarbon, or substituted hydrocarbon group containing from 3 to 20 carbon atoms; R 2 is H or a C 1 -C 20 hydrocarbon; and R 3 is a C 1 -C 20 aliphatic hydrocarbon group.

18. The compounds of claim 17 wherein at least one R 1 group is an unbranched carbon chain.

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 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 →
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 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 →
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 →
CORRECTIVE ASSIGNMENT TO CORRECT THE PAPER WORK WAS NOT COMPLETE WHEN ORGINALY UPLOADED. PREVIOUSLY RECORDED ON REEL 026407 FRAME 0036. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENTS. Recorded Jun 13, 2011
From: COALTER, JOSEPH N., III; LEUNG, TAK W.; TAO, TAO; GAO, KUANQIANG
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 026436/0209 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 8, 2011
From: COALTER, JOSEPH N., III; LEUNG, TAK W.; TAO, TAO; GAO, KUANQIANG
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 026407/0036 →