IP Library Granted Patent US 8,318,626
Granted Patent B2
US 8,318,626 · App. 12/714,686 · Granted Nov 27, 2012

Internal and external donor compounds for olefin polymerization catalysts III

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Quick Facts
Patent No.
US 8,318,626
App. No.
12/714,686
Granted
Nov 27, 2012
Kind
B2
Abstract

The present invention relates to solid catalyst components comprising titanium, magnesium, halogen and an internal electron donor compound containing at least one 1,8-naphthyl diester compound. The 1,8-naphthyl diester compounds include naphthalene-1,8-diyl dicycloalkanecarboxylate derivatives, dicycloalkenecarboxylate derivatives, 8-(cycloalkanecarbonyloxy)naphthalene-1-yl benzoate derivatives, and 8-(cycloalkenecarbonyloxy)naphthalene-1-yl benzoate derivatives. The present invention further relates to catalyst systems containing the catalyst solid components, organoaluminum compounds, and organosilicon compounds. The present invention also relates to methods of making the solid catalyst components and the catalyst systems, and methods of polymerizing or copolymerizing alpha-olefins using the catalyst systems.

Claims (15)

1. A solid catalyst component for use in olefinic polymerization, comprising titanium, magnesium, halogen and an internal electron donor compound, wherein said internal electron donor compound comprises at least one 1,8-naphthyl diester compound represented by chemical formula (I):

wherein R 1 -R 6 are independently hydrogen, halogen, C 1 -C 6 linear or branched alkyl, C 6 -C 10 cycloalkyl, phenyl, C 7 -C 10 alkylaryl, or C 7 -C 18 arylalkyl radicals;

R 7 and R 8 , which are identical or different, are C 1 -C 20 linear or branched alkyl, C 5 -C 20 cycloalkyl, C 5 -C 20 cycloalkenyl, C 5 -C 20 cyclodialkenyl, phenyl, C 7 -C 18 alkylaryl, or C 7 -C 18 arylalkyl radicals.

2. The solid catalyst component according to claim 1 comprising a titanium compound having at least one titanium-halogen bond and the internal electron donor compound supported on a magnesium halide crystal lattice.

3. The solid catalyst component according to claim 1 comprising a titanium compound having at least one titanium-halogen bond and the internal electron donor compound supported on a magnesium dichloride crystal lattice.

4. The solid catalyst component according to claim 2 or 3 , wherein the titanium compound is TiCl 4 or TiCl 3 .

5. A solid catalyst component for use in olefinic polymerization, comprising a reaction product of a titanium compound, a magnesium compound, and an internal electron donor compound, wherein said internal electron donor compound comprises at least one 1,8-naphtyl diester compound represented by chemical formula (I)

wherein R 1 -R 6 are independently hydrogen, halogen, C 1 -C 6 linear or branched alkyl, C 6 -C 10 cycloalkyl, phenyl, C 7 -C 10 alkylaryl, or C 7 -C 18 arylalkyl radicals;

R 7 and R 8 , which are identical or different, are C 1 -C 20 linear or branched alkyl, C 5 -C 20 cycloalkyl, C 5 -C 20 cycloalkenyl, C 5 -C 20 cyclodialkenyl, phenyl, C 7 -C 18 alkylaryl, or C 7 -C 18 arylalkyl radicals.

6. The solid catalyst component according to claim 1 or 5 , wherein said 1,8-naphthyl diester compound of the formula (I) is selected from the group consisting of naphthalene-1,8-diyl dicycloalkanecarboxylate derivative, naphthalene-1,8-diyl dicycloalkenecarboxylate derivative, 8-(cycloakanecarbonyloxy)naphthalene-1-yl benzoate derivative, and 8-(cycloakenecarbonyloxy)naphthalene-1-yl benzoate derivative.

7. The solid catalyst component according to claim 6 , wherein said naphthalene-1,8-diyl dicycloalkanecarboxylate derivative is selected from the group consisting of naphthalene-1,8-diyl dicyclohexanecarboxylate, naphthalene-1,8-diyl di-2-methylcyclohexanecarboxylate, naphthalene-1,8-diyl di-3-methylcyclohexanecarboxylate, and naphthalene-1,8-diyl di-4-methylcyclohexanecarboxylate.

8. The solid catalyst component according to claim 6 , wherein said naphthalene-1,8-diyl dicycloalkenecarboxylate derivative is selected from the group consisting of naphthalene-1,8-diyl dicyclohex-1-enecarboxylate, naphthalene-1,8-diyl dicyclohex-2-enecarboxylate, and naphthalene-1,8-diyl dicyclohex-3-enecarboxylate.

9. The solid catalyst component according to claim 6 , wherein said 8-(cycloakanecarbonyloxy)naphthalene-1-yl benzoate derivative is selected from the group consisting of 8-(cyclohexanecarbonyloxy)naphthalene-1-yl benzoate, 8-(2-methylcyclohexanecarbonyloxy)naphthalene-1-yl benzoate, 8-(3-methylcyclohexanecarbonyloxy)naphthalene-1-yl benzoate, 8-(4-methylcyclohexanecarbonyloxy)naphthalene-1-yl benzoate, 8-(2-methylcyclohexanecarbonyloxy)naphthalene-1-yl 2-methylbenzoate, 8-(3-methylcyclohexanecarbonyloxy)naphthalene-1-yl 2-methylbenzoate, 8-(4-methylcyclohexanecarbonyloxy)naphthalene-1-yl 2-methylbenzoate, 8-(2-methylcyclohexanecarbonyloxy)naphthalene-1-yl 3-methylbenzoate, 8-(3-methylcyclohexanecarbonyloxy)naphthalene-1-yl 3-methylbenzoate, 8-(4-methylcyclohexanecarbonyloxy)naphthalene-1-yl 3-methylbenzoate, 8-(2-methylcyclohexanecarbonyloxy)naphthalene-1-yl 4-methylbenzoate, 8-(3-methylcyclohexanecarbonyloxy)naphthalene-1-yl 4-methylbenzoate, and 8-(4-methylcyclohexanecarbonyloxy)naphthalene-1-yl 4-methylbenzoate.

10. The solid catalyst component according to claim 6 , wherein said 8-(cycloakenecarbonyloxy)naphthalene-1-yl benzoate derivative is selected from the group consisting of 8-(cyclohex-1-enecarbonyloxy)naphthalene-1-yl benzoate, 8-(cyclohex-2-enecarbonyloxy)naphthalene-1-yl benzoate, 8-(cyclohex-3-enecarbonyloxy)naphthalene-1-yl benzoate, 8-(cyclohex-1-enecarbonyloxy)naphthalene-1-yl 2-methylbenzoate, 8-(cyclohex-2-enecarbonyloxy)naphthalene-1-yl 2-methylbenzoate, 8-(cyclohex-3-enecarbonyloxy)naphthalene-1-yl 2-methylbenzoate, 8-(cyclohex-1-enecarbonyloxy)naphthalene-1-yl 3-methylbenzoate, 8-(cyclohex-2-enecarbonyloxy)naphthalene-1-yl 3-methylbenzoate, 8-(cyclohex-3-enecarbonyloxy)naphthalene-1-yl 3-methylbenzoate, 8-(cyclohex-1-enecarbonyloxy)naphthalene-1-yl 4-methylbenzoate, 8-(cyclohex-2-enecarbonyloxy)naphthalene-1-yl 4-methylbenzoate, 8-(cyclohex-3-enecarbonyloxy)naphthalene-1-yl 4-methylbenzoate, 8-(2-methylcyclohex-1-enecarbonyloxy)naphthalene-1-yl benzoate, 8-(2-methylcyclohex-2-enecarbonyloxy)naphthalene-1-yl benzoate, 8-(2-methylcyclohex-3-enecarbonyloxy)naphthalene-1-yl benzoate, 8-(2-methylcyclohex-1-enecarbonyloxy)naphthalene-1-yl 2-methylbenzoate, 8-(2-methylcyclohex-2-enecarbonyloxy)naphthalene-1-yl 2-methylbenzoate, 8-(2-methylcyclohex-3-enecarbonyloxy)naphthalene-1-yl 2-methylbenzoate, 8-(2-methylcyclohex-1-enecarbonyloxy)naphthalene-1-yl 3-methylbenzoate, 8-(2-methylcyclohex-2-enecarbonyloxy)naphthalene-1-yl 3-methylbenzoate, 8-(2-methylcyclohex-3-enecarbonyloxy)naphthalene-1-yl 3-methylbenzoate, 8-(2-methylcyclohex-1-enecarbonyloxy)naphthalene-1-yl 4-methylbenzoate, 8-(2-methylcyclohex-2-enecarbonyloxy)naphthalene-1-yl 4-methylbenzoate, 8-(2-methylcyclohex-3-enecarbonyloxy)naphthalene-1-yl 4-methylbenzoate, 8-(3-methylcyclohex-1-enecarbonyloxy)naphthalene-1-yl benzoate, 8-(3-methylcyclohex-2-enecarbonyloxy)naphthalene-1-yl benzoate, 8-(3-methylcyclohex-3-enecarbonyloxy)naphthalene-1-yl benzoate, 8-(3-methylcyclohex-1-enecarbonyloxy)naphthalen-1-yl 2-methylbenzoate, 8-(3-methylcyclohex-2-enecarbonyloxy)naphthalene-1-yl 2-methylbenzoate, 8-(3-methylcyclohex-3-enecarbonyloxy)naphthalene-1-yl 2-methylbenzoate, 8-(3-methylcyclohex-1-enecarbonyloxy)naphthalene-1-yl 3-methylbenzoate, 8-(3-methylcyclohex-2-enecarbonyloxy)naphthalene-1-yl 3-methylbenzoate, 8-(3-methylcyclohex-3-enecarbonyloxy)naphthalene-1-yl 3-methylbenzoate, 8-(3-methylcyclohex-1-enecarbonyloxy)naphthalene-1-yl 4-methylbenzoate, 8-(3-methylcyclohex-2-enecarbonyloxy)naphthalene-1-yl 4-methylbenzoate, 8-(3-methylcyclohex-3-enecarbonyloxy)naphthalene-1-yl 4-methylbenzoate, 8-(4-methylcyclohex-1-enecarbonyloxy)naphthalene-1-yl benzoate, 8-(4-methylcyclohex-2-enecarbonyloxy)naphthalene-1-yl benzoate, 8-(4-methylcyclohex-3-enecarbonyloxy)naphthalene-1-yl benzoate, 8-(4-methylcyclohex-1-enecarbonyloxy)naphthalene-1-yl 2-methylbenzoate, 8-(4-methylcyclohex-2-enecarbonyloxy)naphthalene-1-yl 2-methylbenzoate, 8-(4-methylcyclohex-3-enecarbonyloxy)naphthalene-1-yl 2-methylbenzoate, 8-(4-methylcyclohex-1-enecarbonyloxy)naphthalene-1-yl 3-methylbenzoate, 8-(4-methylcyclohex-2-enecarbonyloxy)naphthalene-1-yl 3-methylbenzoate, 8-(4-methylcyclohex-3-enecarbonyloxy)naphthalene-1-yl 3-methylbenzoate, 8-(4-methylcyclohex-1-enecarbonyloxy)naphthalene-1-yl 4-methylbenzoate, 8-(4-methylcyclohex-2-enecarbonyloxy)naphthalene-1-yl 4-methylbenzoate, and 8-(4-methylcyclohex-3-enecarbonyloxy)naphthalene-1-yl 4-methylbenzoate.

11. The solid catalyst component according to claim 1 or 5 having a surface area (by B.E.T. method) between about 10 and about 1,000 m 2 /g.

Assignments (7)
RELEASE OF SECURITY INTEREST Recorded Sep 23, 2021
From: GOLDMAN SACHS BANK USA
To: W. R. GRACE & CO.-CONN.
Reel/Frame 057594/0026 →
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 050295/0009 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 6, 2019
From: BRASKEM EUROPE GMBH
To: BRASKEM AMERICA, INC.
Reel/Frame 050295/0665 →
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 Mar 1, 2010
From: CHANG, MAIN
To: BASF CATALYSTS LLC
Reel/Frame 024005/0405 →