Substituted pyridyl amine catalysts, complexes and compositions
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C07F-007/00
B01J-031/00
C08F-004/44
출원번호
US-0992789
(2001-11-06)
발명자
/ 주소
Boussie, Thomas R.
Diamond, Gary M.
Goh, Christopher
Hall, Keith A.
LaPointe, Anne M.
Leclerc, Margarete K.
Lund, Cheryl
Murphy, Vince
출원인 / 주소
Symyx Technologies, Inc.
대리인 / 주소
Venable LLP
인용정보
피인용 횟수 :
36인용 특허 :
21
초록▼
New ligands, compositions, metal-ligand complexes and arrays with pyridyl-amine ligands are disclosed that catalyze the polymerization of monomers into polymers. Certain of these catalysts with hafnium metal centers have high performance characteristics, including higher comonomer incorporation into
New ligands, compositions, metal-ligand complexes and arrays with pyridyl-amine ligands are disclosed that catalyze the polymerization of monomers into polymers. Certain of these catalysts with hafnium metal centers have high performance characteristics, including higher comonomer incorporation into ethylene/olefin copolymers, where such olefins are for example, 1-octene, isobutylene or styrene. Certain of the catalysts are particularly effective at polymerizing propylene to high molecular weight isotactic polypropylene in a solution process at a variety of polymerization conditions.
대표청구항▼
1. A composition comprising: (1) a ligand characterized by the following general formula: wherein R 1is characterized by the general formula: wherein E is either carbon or nitrogen, Q 1and Q5are substituents on the R1ring at a position ortho to E, with Q1and Q5are independentl
1. A composition comprising: (1) a ligand characterized by the following general formula: wherein R 1is characterized by the general formula: wherein E is either carbon or nitrogen, Q 1and Q5are substituents on the R1ring at a position ortho to E, with Q1and Q5are independently selected from the group consisting of alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl and silyl, but provided that Q1and Q5are not both methyl; Q″ qrepresents additional possible substituents on the ring, with q being 1, 2, 3, 4 or 5 and Q″ being selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, substituted heteroalkyl, heterocycloalkyl, substituted hetercycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxyl, aryloxyl, silyl, boryl, phosphino, amino, thio, seleno, halide, nitro, and combinations thereof, T is a bridging group selected group consisting of —CR 2R3— and —SiR2R3— with R2selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, substituted heteroalkyl, heterocycloalkyl, substituted hetercycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxyl, aryloxyl, silyl, boryl, phosphino, amino, thio, seleno, halide, nitro, and combinations thereof; R3selected from the group consisting of aryl, substituted aryl, heteroaryl, and substituted heteroaryl; and provided that R2is different from R3; J″ is selected from the group consisting of heteroaryl and substituted heteroaryl; (2) a metal precursor compound characterized by the general formula M(L) nwherein M is either hafnium or zirconium and each L is independently selected from the group consisting of halide, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, substituted heteroalkyl heterocycloalkyl, substituted heterocycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxy, aryloxy, hydroxy, boryl, silyl, amino, amine, hydrido, allyl, diene, seleno, phosphino, phosphine, carboxylates, thio, 1,3-dionates, oxalates, carbonates, nitrates, sulphates, ethers, thioethers and combinations thereof or optionally two or more L groups are joined into a ring structure; n is 1, 2, 3, 4, 5, or 6; and (3) optionally, at least one activator. 2. The composition of claim 1, wherein said ligand is characterized by the formula:wherein each of R 4, R5, R6and R7is independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, substituted heteroalkyl, heterocycloalkyl, substituted hetercycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxyl, aryloxyl, silyl, boryl, phosphino, amino, thio, seleno, halide, nitro, and combinations thereof; and optionally, any combination of R1, R,2, R3, R4, R5, R6or R7may be joined together in a ring structure.3. The composition of claim 2, wherein said ligand is characterized by the general formula:such that E is carbon and wherein Q 2, Q3and Q4are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, substituted heteroalkyl, heterocycloalkyl, substituted hetercycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxyl, aryloxyl, silyl, boryl, phosphino, amino, thio, seleno, nitro, and combinations thereof; optionally two or more of Q2, Q3and Q4are joined together in a ring structure.4. The composition of claim 2, wherein said ligand is characterized by the general formula:such that T is —CR 2R3— and wherein R10, R11, R12and R13are each independently selected from the group consisting of hydrogen, halide, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, substituted heteroalkyl, heterocycloalkyl, substituted hetercycloal kyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxy, aryloxy, silyl, boryl, phosphino, amino, thio, seleno, nitro, and combinations thereof; optionally, two or more R10, R11, R12and R13groups may be joined to form a fused ring system having from 3-50 non-hydrogen atoms; and R 14is selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, substituted heteroalkyl, heterocycloalkyl, substituted hetercycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxy, aryloxy, silyl, boryl, phosphino, amino, thio, seleno, halide, nitro, and combinations thereof.5. The composition of claim 4, wherein said ligand is characterized by the formula:such that E is carbon and wherein Q 2, Q3and Q4are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, substituted heteroalkyl, heterocycloalkyl, substituted hetercycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxyl, aryloxyl, silyl, boryl, phosphino, amino, thio, seleno, nitro, and combinations thereof; optionally two or more of Q2, Q3and Q4are joined together in a ring structure.6. The composition of either of claims 1,2,3,4 or5 wherein M is hafnium.7. A metal-ligand complex characterized by the following formula: wherein R 1is characterized by the general formula: wherein E is either carbon or nitrogen, Q 1and Q5are substituents on the R1ring at a position ortho to E, with Q1and Q5being independently selected from the group consisting of alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl and silyl, but provided that Q1and Q5are not both methyl; Q″ qrepresents additional possible substituents on the ring, with q being 1, 2, 3, 4 or 5 and Q″ being selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, substituted heteroalkyl, heterocycloalkyl, substituted hetercycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxyl, aryloxyl, silyl, boryl, phosphino, amino, thio, seleno, halide, nitro, and combinations thereof; T is a bridging group selected group consisting of —CR 2R3— and —SiR2R3— with R2selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, substituted heteroalkyl, heterocycloalkyl, substituted hetercycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxyl, aryloxyl, silyl, boryl, phosphino, amino, thio, seleno, halide, nitro, and combinations thereof; R3selected from the group consisting of aryl, substituted aryl, heteroaryl, and substituted heteroaryl; and provided that R2is different from R3; J″ is selected from the group consisting of heteroaryl and substituted heteroaryl; each L is independently selected from the group consisting of halide, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, substituted heteroalkyl heterocycloalkyl, substituted heterocycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxy, aryloxy, hydroxy, boryl, silyl, amino, amine, hydrido, allyl, diene, seleno, phosphino, phosphine, carboxylates, thio, 1,3-dionates, oxalates, carbonates, nitrates, sulphates, ethers, thioethers and combinations thereof or optionally two or more L groups are joined into a ring structure; n is 1, 2, 3, 4, 5, or 6; and x is 1. 8. The metal complex of claim 7 having the formula:wherein each of R 4, R5, R6and R7is independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, substituted heteroalkyl, heterocycloalkyl, substituted hetercycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxyl, aryloxyl, silyl, boryl, phosphino, amino, thio, seleno, halide, nit ro, and combinations thereof; and optionally, any combination of R1, R2, R3, R4, R5, R6or R7may be joined together in a ring structure.9. The metal complex of claim 8 having the formula:such that E is carbon and wherein Q 2, Q3and Q4are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, substituted heteroalkyl, heterocycloalkyl, substituted hetercycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxyl, aryloxyl, silyl, boryl, phosphino, amino, thio, seleno, nitro, and combinations thereof; optionally two or more of Q2, Q3and Q4are joined together in a ring structure.10. The metal complex of claim 8, wherein said complex is characterized by the formula:such that T is —CR 2R3— and wherein R10, R11, R12and R13are each independently selected from the group consisting of hydrogen, halide, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, substituted heteroalkyl, heterocycloalkyl, substituted hetercycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxy, aryloxy, silyl, boryl, phosphino, amino, thio, seleno, nitro, and combinations thereof; optionally, two or more R10, R11, R12and R13groups may be joined to form a fused ring system having from 3-50 non-hydrogen atoms; and R 14is selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, substituted heteroalkyl, heterocycloalkyl, substituted hetercycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxy, aryloxy, silyl, boryl, phosphino, amino, thio, seleno, halide, nitro, and combinations thereof.11. The metal complex of claim 10, wherein said complex is characterized by the general formula:such that E is carbon and wherein Q 2, Q3and Q4are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, substituted heteroalkyl, heterocycloalkyl, substituted hetercycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxyl, aryloxyl, silyl, boryl, phosphino, amino, thio, seleno, nitro, and combinations thereof; optionally two or more of Q2, Q3and Q4are joined together in a ring structure.12. A metal complex characterized by the formula: where M is zirconium or hafnium; wherein R 1is characterized by the general formula: wherein E is either carbon or nitrogen, Q 1and Q5are substituents on the R1ring at a position ortho to E, with Q1and Q5are independently selected from the group consisting of alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl and silyl, but provided that Q1and Q5are not both methyl; Q″ qrepresents additional possible substituents on the ring, with q being 1, 2, 3, 4 or 5 and Q″ being selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, substituted heteroalkyl, heterocycloalkyl, substituted hetercycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxyl, aryloxyl, silyl, boryl, phosphino, amino, thio, seleno, halide, nitro, and combinations thereof; T is a bridging group selected group consisting of —CR 2R3— and —SiR2R3— with R2selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, substituted heteroalkyl, heterocycloalkyl, substituted hetercycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxyl, aryloxyl, silyl, boryl, phosphino, amino, thio, seleno, halide, nitro, and combinations thereof; R3selected from the group consisting of aryl, substituted aryl, heteroaryl, and substituted heteroaryl; and provided that R2is different from R3; J′″ being selected from the group of substituted heteroaryls with 2 atoms bonded to the metal M, at least one of those 2 atoms being a heteroatom, and with one atom of J′″ is bonded to M via a dative bond, the other through a covalent bond; and L 1and L2are independently selected from the group consisting of halide, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, substituted heteroalkyl, heterocycloalkyl, substituted heterocycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxy, aryloxy, hydroxy, boryl, silyl, amino, amine, hydrido, allyl, diene, seleno, phosphino, phosphine, carboxylates, thio, 1,3-dionates, oxalates, carbonates, nitrates, sulphates, ethers, thioethers and combinations thereof or optionally the two L groups are joined into a ring structure.13. The complex of claim 12, wherein said complex is characterized by the formula: wherein each of R 4, R5and R6is independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, substituted heteroalkyl, heterocycloalkyl, substituted hetercycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxyl, aryloxyl, silyl, boryl, phosphino, amino, thio, seleno, halide, nitro, and combinations thereof; and optionally, any combination of R1, R2, R3, R4, R5, or R6may be joined together in a ring structure; and E″ is either carbon or nitrogen and is part of a cyclic aryl, substituted aryl, heteroaryl, or substituted heteroaryl group. 14. The metal complex of claim 13, wherein said complex is characterized by the formula:wherein R 10, R11, R12and R13are each independently selected from the group consisting of hydrogen, halide, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, substituted heteroalkyl, heterocycloalkyl, substituted hetercycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxy, aryloxy, silyl, boryl, phosphino, amino, thio, seleno, nitro, and combinations thereof, optionally, two or more R10, R11, R12and R13groups may be joined to form a fused ring system having from 3-50 non-hydrogen atoms.15. The metal complex of claim 14, wherein said complex is characterized by the formula:wherein Q 2, Q3and Q4are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, substituted heteroalkyl, heterocycloalkyl, substituted hetercycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxyl, aryloxyl, silyl, boryl, phosphino, amino, thio, seleno, nitro, and combinations thereof; or optionally, two of Q2, Q3and Q4are joined together in a ring structure.16. The composition or complex of either of claims 1,2,3,4,5,7,8,9,10,11,12,13,14 or15 wherein R2is hydrogen.17. The composition or complex of claim 16, wherein each of R4, R5and R6is hydrogen.18. The composition or complex of claim 17, wherein R3is selected from the group consisting of benzyl, phenyl, naphthyl, 2-biphenyl, 2-dimethylaminophenyl, 2-methoxyphenyl, anthracenyl, mesityl, 2-pyridyl, 3,5-dimethylphenyl, o-tolyl, and phenanthrenyl.19. The composition or complex of claim 18, wherein Q1and Q5are both isopropyl; or both ethyl; or both sec-butyl; or Q1is methyl and Q5is isopropyl; or Q1is ethyl and Q5is sec-butyl.20. The composition or complex of claim 19, wherein R10, R11, R12, R13, are each hydrogen; or one or more of R10, R11, R12, R13are methyl, fluoro, trifluoromethyl, methoxy, or dimethylamino; or R10and R11are joined to form a benzene ring and R12and R13are each hydrogen.21. The composition or complex of either of claims 2,3,8,9,13 or14, wherein each of R4and R5is hydrogen and R6is either hydrogen or is joined to R7to form a fused ring system.22. The composition or complex of either of claims 1,2,3,4,5,7,8,9,10,11,12,13,14 or15, wherein R3is selected from the group consisting of benzyl, phenyl, naphthyl, 2-biphenyl, 2-dimethylaminophenyl, 2-methoxyphenyl, anthracenyl, mesityl, 2-pyridyl, 3,5-dimethylphenyl, o-tolyl, and phenanthrenyl.23. T he composition or complex of either of claims 1,2,3,4,5,7,8,9,10,11,12,13,14 or15 wherein Q1and Q5are, independently, selected from the group consisting of —CH2R15, —CHR16R17and methyl, provided that not both Q1and Q5are methyl, wherein R15is selected from the group consisting of alkyl, substituted alkyl, aryl and substituted aryl; R16and R17are independently selected from the group consisting of alkyl, substituted alkyl, aryl and substituted aryl; and optionally R16and R17are joined together in a ring structure having from 3-50 non-hydrogen atoms.24. The composition or complex of claim 23, wherein Q2, Q3, and Q4are each hydrogen and Q1and Q5are both isopropyl; or both ethyl; or both sec-butyl; or Q1is methyl and Q5is isopropyl; or Q1is ethyl and Q5is sec-butyl.25. The composition or complex of either of claims 1,2,3,4,5,7,8,9,10,11,12,13,14 or15, wherein R1or the variables Q1, Q2, Q3, Q4and Q5are chosen so that the R1moiety is selected from the group consisting of 2,6—(Pri)2—C6H3—; 2-Pri-6-Me—C6H3—; 2,6-Et2—C6H3—; and 2-sec-butyl-6-Et—C6H3—.26. The composition or complex of either of claims 2,3,8 or9, wherein R7is aryl, substituted aryl, heteroaryl or substituted heteroaryl.27. The composition or complex of claim 26, wherein R7is selected from the group consisting of phenyl, napthyl, mesityl, anthracenyl and phenanthrenyl.28. The composition or complex of either of claims 4,5,10 or11, wherein R10, R11, R12, R13, are each hydrogen; or one or more of R10, R11, R12, R13are methyl, fluoro, trifluoromethyl, methoxy, or dimethylamino; or R10and R11are joined to form a benzene ring and R12and R13are each hydrogen.29. The composition or complex of either of claims 2,3,4,5,8,9,10,11,13,14 or15, wherein two or more of R4, R5, R6and R7is joined to form a fused ring system having from 3-50 non-hydrogen atoms in addition to the pyridine ring and/or R4, R5and R6are each independently selected from the group consisting of alkyl, aryl, halide, alkoxy, aryloxy, amino, and thio.30. The composition or complex of either of claims 4,5,10,11 or15, wherein R6and R10are joined to form a ring system having from 5-50 non-hydrogen atoms.
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