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US 6,174,975 B1Granted
Polymerization of olefins
AssigneeE.I. du Pont de Nemours and Company
InventorsLynda Kaye Johnson, Alison Margaret Anne Bennett, Lin Wang, Anju Parthasarathy, Elisabeth Hauptman, Robert D. Simpson, Jerald Feldman, Edward Bryan Coughlin, Steven Dale Ittel
Life of this patent
Estimating the term…
Abstract
Selected olefins such as ethylene and α-olefins are polymerized by nickel [II] complexes of certain monoanionic ligands. The polyolefins are useful in many applications such as molding resins, film, fibers and others. Also described are many novel nickel compounds and their precursors, as well a novel ligands.
Claims35
A process for the polymerization of an olefin selected from one or more of R67CH═CH2, cyclopentene, a styrene, a norbornene or H2C═CH(CH2),CO2R77, comprising, contacting, at a temperature of about −100° C. to about +200° C., R67CH═CH2, cyclopentene, a styrene, a norbornene, or H2C═CH(CH2)sCO2R77 , optionally a Lewis acid, and a compound of the formula:
- wherein:
- Ar1, Ar2, Ar4, Ar5, Ar10, Ar11, Ar12 and Ar13 are each independently aryl or substituted aryl;
- R1 and R2 are each independently hydrogen, hydrocarbyl, substituted hydrocarbyl, or R1 and R2 taken together form a ring, and R3 is hydrogen, hydrocarbyl or substituted hydrocarbyl or R1, R2 and R3 taken together form a ring;
- A is a π-allyl or π-benzyl group;
- R10 and R15 are each independently hydrogen, hydrocarbyl or substituted hydrocarbyl;
- R11, R12, R13, R14, R16, R17, R18, R19, R20, R21, R30, R31, R32, R33, R34, R35 R50, R51, R52, R53 and R54 are each independently hydrogen, hydrocarbyl, substituted hydrocarbyl, an inert functional group, and provided that any two of these groups vicinal to one another taken together may form a ring;
- K is N or CR27;
- R22 is hydrocarbyl, substituted hydrocarbyl, —SR117, —OR117, or —NR1182, R24 is hydrogen, a functional group, hydrocarbyl or substituted hydrocarbyl, and R27 is hydrocarbyl or substituted hydrocarbyl, and provided that R22 and R24 or R24 and R27 taken together may form a ring;
- R117 is hydrocarbyl or substituted hydrocarbyl;
- each R118 is independently hydrogen, hydrocarbyl or substituted hydrocarbyl;
- G and L are both N or G is CR57 and L is CR55;
- R55, R56 and R57 are each independently hydrogen, hydrocarbyl or substituted hydrocarbyl, or any two of R55, R56 and R57 taken together form a ring;
- R67 is hydrogen, alkyl or substituted alkyl;
- R77 is hydrocarbyl or substituted hydrocarbyl;
- R78 is hydrocarbyl or substituted hydrocarbyl;
- R79, R80, R81, R82, R83, R84, R85, R86, R87, R88 and R89 are each independently hydrogen, hydrocarbyl, substituted hydrocarbyl, or a functional group;
- R90, R91, R92 and R93 are each independently hydrocarbyl or substituted hydrocarbyl;
- R94 and R95 are each independently hydrocarbyl or substituted hydrocarbyl;
- R96, R97, R98, and R99 are each independently hydrogen, hydrocarbyl, substituted hydrocarbyl or a functional group;
- R100, R101, R102, R103, R104, R105, R106, and R107 are each independently hydrogen, hydrocarbyl, substituted hydrocarbyl, or a functional group;
- R109, R110, R111, R112, R113, R114, R115 and R116 are each independently hydrogen, hydrocarbyl, substituted hydrocarbyl or a functional group;
- s is an integer of 1 or more;
- and
- R28 and R29 are each independently hydrogen, hydrocarbyl or substituted hydrocarbyl;
- and provided that when H2C═CH(CH2)sCO2R77 is present, R67CH═CH2 is also present.
22 more elements
A process for the polymerization of an olefin selected from one or more of R67CH═CH2, a styrene, a norbornene or H2C═CH(CH2)sCO2R77, comprising, contacting, at a temperature of about −100° C. to about +200° C., R67CH═CH2, cyclopentene, a styrene, a norbornene, or H2C═CH(CH2)sCO2R77, optionally a Lewis acid, and a compound of the formula:
- wherein:
- L1 is a neutral monodentate ligand which may be displaced by said olefin, and L2 is a monoanionic monodentate ligand, or L1 and L2 taken together are a monoanionic bidentate ligand, provided that said monoanionic monodentate ligand or said monoanionic bidentate ligand may add to said olefin;
- Ar1, Ar2, Ar4, Ar5, Ar10, Ar11, Ar12 and Ar13 are each independently aryl or substituted aryl;
- R1 and R2 are each independently hydrogen, hydrocarbyl, substituted hydrocarbyl, or R1 and R2 taken together form a ring, and R3 is hydrogen, hydrocarbyl or substituted hydrocarbyl or R1, R2 and R3 taken together form a ring;
- A is a π-allyl or π-benzyl group;
- R10 and R15 are each independently hydrogen, hydrocarbyl or substituted hydrocarbyl;
- R11, R12, R13, R14, R16, R17, R18, R19, R20, R21, R30, R31, R32, R33, R34, R35 R50, R51, R52, R53 and R54 are each independently hydrogen, hydrocarbyl, substituted hydrocarbyl, an inert functional group, and provided that any two of these groups vicinal to one another taken together may form a ring;
- K is N or CR27;
- R22 is hydrocarbyl, substituted hydrocarbyl, —SR117, —OR117, or —NR1182, R24 is hydrogen, a functional group, hydrocarbyl or substituted hydrocarbyl, and R27 is hydrocarbyl or substituted hydrocarbyl, and provided that R22 and R24 or R24 and R27 taken together may form a ring;
- R117 is hydrocarbyl or substituted hydrocarbyl;
- each R118 is independently hydrogen, hydrocarbyl or substituted hydrocarbyl;
- G and L are both N or G is CR57 and L is CR55;
- R55, R56 and R57 are each independently hydrogen, hydrocarbyl or substituted hydrocarbyl, or any two of R55, R56 and R57 taken together form a ring;
- R67 is hydrogen, alkyl or substituted alkyl;
- R77 is hydrocarbyl or substituted hydrocarbyl;
- R78 is hydrocarbyl or substituted hydrocarbyl;
- R79, R80, R81, R82, R83, R84, R85, R86, R87, R88 and R89 are each independently hydrogen, hydrocarbyl, substituted hydrocarbyl, or a functional group;
- R90, R91, R92 and R93 are each independently hydrocarbyl or substituted hydrocarbyl;
- R94 and R95 are each independently hydrocarbyl or substituted hydrocarbyl;
- R96, R97, R98, and R99 are each independently hydrogen, hydrocarbyl, substituted hydrocarbyl or a functional group;
- both of T are S (sulfur) or NH (amino);
- each E is N (nitrogen) or CR108 wherein R108 is hydrogen, hydrocarbyl, substituted hydrocarbyl or a functional group;
- R100, R101, R102, R103, R104, R105, R106, and R107 are each independently hydrogen, hydrocarbyl, substituted hydrocarbyl, or a functional group;
- R109, R110, R111, R112, R113, R114, R115 and R116 are each independently hydrogen, hydrocarbyl, substituted hydrocarbyl or a functional group;
- s is an integer of 1 or more;
- and
- R28 and R 29 are each independently hydrogen, hydrocarbyl or substituted hydrocarbyl;
- and provided that when H2C═CH(CH2)sCO2R77 is present, R67CH═CH2 is also present.
25 more elements
Dependencies are inferred from the claim text.