Catalysts containing per-ortho aryl substituted aryl or heteroaryl substituted nitrogen donors

• US 6,579,823 B2
• Filed: 08/31/2001
• Issued: 06/17/2003
• Est. Priority Date: 02/18/2000
• Status: Expired due to Fees

• Current Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Original Assignee: Eastman Chemical Company
• Inventors: Smith, Thomas William, Lavoie, Gino Georges, Pearson, Jason Clay, Moody, Leslie Shane, Ponasik, James Allen Jr., Killian, Christopher Moore, Barrett, Anthony Gerard Martin, Mackenzie, Peter Borden
• Primary Examiner(s): Bell, Mark L.
• Assistant Examiner(s): PASTERCZYK, JAMES W
• Application Number:
  US09/942,877
• Publication Number:
  US 20020049135A1
• Time in Patent Office: 655 Days
• Field of Search: 502/155, 502/167, 502/168, 502/102, 502/103, 502/117, 526/135, 526/171, 526/131, 526/134, 526/172
• US Class Current: 502/167
• CPC Class Codes: C07C 2/32 as complexes, e.g. acetyl-acetonates complexes of salts of acids of halogen C07C2/20
• CPC Class Codes: C07C 205/06 having nitro groups bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C07C 211/52 the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
• CPC Class Codes: C07C 233/56 having carbon atoms of carboxamide groups bound to carbon atoms of carboxyl groups, e.g. oxamides
• CPC Class Codes: C07C 251/08 being acyclic
• CPC Class Codes: C07C 251/20 having carbon atoms of imino groups being part of rings other than six-membered aromatic rings
• CPC Class Codes: C07C 2531/22 Organic complexes
• CPC Class Codes: C07C 257/02 with replacement of the other oxygen atom of the carboxyl group by halogen atoms, e.g. imino-halides
• CPC Class Codes: C07C 257/14 having carbon atoms of amidino groups bound to acyclic carbon atoms
• CPC Class Codes: C07C 2603/20 Acenaphthenes; Hydrogenated acenaphthenes
• CPC Class Codes: C07D 207/32 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 207/34 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 207/50 Nitrogen atoms
• CPC Class Codes: C07D 209/48 with oxygen atoms in positions 1 and 3, e.g. phthalimide
• CPC Class Codes: C07D 265/30 not condensed with other rings
• CPC Class Codes: C07D 295/30 non-acylated
• CPC Class Codes: C07D 309/34 having three or more double bonds between ring members or between ring members and non-ring members
• CPC Class Codes: C07D 319/12 not condensed with other rings
• CPC Class Codes: C07D 339/08 Six-membered rings
• CPC Class Codes: C07D 401/14 containing three or more hetero rings
• CPC Class Codes: C07D 409/14 : containing three or more hetero rings
• CPC Class Codes: C07F 15/045 : without a metal-carbon linkage
• CPC Class Codes: C07F 17/00 : Metallocenes
• CPC Class Codes: C07F 7/003 : without C-Metal linkages
• CPC Class Codes: C07F 7/0812 : comprising a heterocyclic ring
• CPC Class Codes: C08F 10/00 : Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
• CPC Class Codes: C08F 110/02 : Ethene
• CPC Class Codes: C08F 110/14 : Monomers containing five or more carbon atoms
• CPC Class Codes: C08F 210/14 : Monomers containing five or more carbon atoms
• CPC Class Codes: C08F 210/16 : Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
• CPC Class Codes: C08F 2500/02 : Low molecular weight, e.g. <100,000 Da.
• CPC Class Codes: C08F 2500/03 : Narrow molecular weight distribution, i.e. Mw/Mn < 3
• CPC Class Codes: C08F 2500/04 : Broad molecular weight distribution, i.e. Mw/Mn > 6
• CPC Class Codes: C08F 2500/09 : Long chain branches
• CPC Class Codes: C08F 2500/10 : Short chain branches
• CPC Class Codes: C08F 4/7006 : NN
• CPC Class Codes: C08F 4/7027 : OO
• CPC Class Codes: C08F 4/80 : selected from iron group metals or platinum group metals

Abstract

Catalyst compositions useful for the polymerization of olefins are disclosed. These compositions comprise a Group 8-10 metal complex comprising a bidentate or variable denticity ligand comprising one or two nitrogen donor atom or atoms independently substituted by an aromatic or heteroaromatic ring(s), wherein the ortho positions of said ring(s) are substituted by aryl or heteroaryl groups. Also disclosed are processes for the polymerization of olefins using the catalyst compositions.

Claims

1. A catalyst composition useful for the polymerization of olefins, which comprises a Group 8-10 metal complex comprising a bidentate or variable denticity ligand comprising two nitrogen donor atoms independently substituted by aromatic or heteroaromatic rings, wherein the ortho positions of said rings are substituted by aryl or heteroaryl groups.

2. A catalyst composition useful for the polymerization of ethylene, which comprises either (i) a compound of formula ee1, (ii) the reaction product of a metal complex of formula ff1 and a second compound Y¹, or (iii) the reaction product of Ni(1,5-cyclooctadiene)₂, B(C₆F₅)₃, a ligand selected from the group consisting of Set 18, and optionally an olefin;

wherein;

L² is a ligand selected from the group consisting of Set 18;

T is H, hydrocarbyl, substituted hydrocarbyl, or other group capable of inserting an olefin;

L is an olefin or a neutral donor group capable of being displaced by an olefin;

in addition, T and L may be bonded together to form a π

-allyl or π

-benzyl group;

X⁻

is BF₄⁻

, B(C₆F₅)₄⁻

, BPh₄⁻

, or another weakly coordinating anion;

Q and W¹ are each independently fluoro, chloro, bromo or iodo, hydrocarbyl, substituted hydrocarbyl, heteroatom attached hydrocarbyl, heteroatom attached substituted hydrocarbyl, or collectively sulfate, or may be bonded together to form a π

-allyl, π

-benzyl, or acac group;

Y¹ is either (i) a metal hydrocarbyl capable of abstracting acac from ff1 in exchange for either alkyl or another group capable of inserting an olefin, (ii) a neutral Lewis acid capable of abstracting Q⁻

or W¹⁻

from ff1 to form a weakly coordinating anion, a cationic Lewis acid whose counterion is a weakly coordinating anion, or a Bronsted acid whose conjugate base is a weakly coordinating anion, or (iii) a Lewis acid capable of reacting with a π

-allyl or π

-benzyl group, or a substituent thereon, in ff1 to initiate olefin polymerization;

R^3a,b are each independently H, alkyl, hydrocarbyl, substituted hydrocarbyl, 2,4,6-triphenylphenyl, heteroatom connected hydrocarbyl, heteroatom connected substituted hydrocarbyl, or fluoroalkyl; and

Ar^1a-d are each independently phenyl, 4-alkylphenyl, 4-tert-butylphenyl, 4-trifluoromethylphenyl, 4-hydroxyphenyl, 4-(heteroatom attached hydrocarbyl)-phenyl, 4-(heteroatom attached substituted hydrocarbyl)-phenyl, or 1-naphthyl.

3. The composition according to claim 2, wherein the metal complex of formula ff1 is selected from the group consisting of Set 19;

wherein;

R^3a,b are each independently H, methyl, phenyl, 4-methoxyphenyl, or 4-tert-butylphenyl;

Ar^1a-d are each independently phenyl, 4-methylphenyl, 4-tert-butylphenyl, 4-trifluoromethylphenyl, or 1-naphthyl; and

X⁻

is BF₄⁻

, B(C₆F₅)₄⁻

, BPh₄⁻

, or another weakly coordinating anion.

4. The composition according to claim 2, further comprising a solid support.

5. The composition according to claim 3, wherein Ar^1a-d are 4-tert-butylphenyl or 1-naphthyl.

6. A process for the polymerization of olefins, comprising contacting one or more olefins with the catalyst composition of claim 2.

7. The process according to claim 6, wherein the second compound Y¹ is trimethylaluminum, and said metal complex is contacted with the trimethylaluminum in a gas phase olefin polymerization reactor.

8. A catalyst composition comprising a Group 8-10 transition metal complex which comprises a ligand selected from group consisting of the formula kk1 and kk2;

wherein;

Ar^2a,b are each independently aromatic or heteroaromatic groups wherein the ortho positions are substituted by aryl or heteroaryl groups;

M¹ is a metal selected from the group consisting of Groups 3, 4, 5, 6, 13, and 14, or is Cu, P or As when the ligand is of formula kk1 and M¹ is a metal selected from the group consisting of Groups 3, 4, 5, 6, 13, and 14 when the ligand is of formula kk2; and

L_n are ancillary ligands or groups which satisfy the valency of M¹, such that M¹ is either a neutral, monoanionic or cationic metal center, with suitable counterions such that said catalyst composition has no net charge.

9. A process for the polymerization of olefins, comprising contacting one or more olefins with the catalyst composition of claim 8.