WO1995025757A1 - Thermoplastic elastomeric stereoblock olefin polymers methods and metallocene catalysts - Google Patents
Thermoplastic elastomeric stereoblock olefin polymers methods and metallocene catalysts Download PDFInfo
- Publication number
- WO1995025757A1 WO1995025757A1 PCT/US1995/003597 US9503597W WO9525757A1 WO 1995025757 A1 WO1995025757 A1 WO 1995025757A1 US 9503597 W US9503597 W US 9503597W WO 9525757 A1 WO9525757 A1 WO 9525757A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- bis
- catalyst
- indenyl
- phenyl
- polymerization
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 52
- 229920000098 polyolefin Polymers 0.000 title claims abstract description 26
- 229920001169 thermoplastic Polymers 0.000 title claims abstract description 17
- 239000004416 thermosoftening plastic Substances 0.000 title claims abstract description 17
- 239000012968 metallocene catalyst Substances 0.000 title claims description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 179
- -1 polypropylene Polymers 0.000 claims abstract description 158
- 229920000642 polymer Polymers 0.000 claims abstract description 149
- 239000004743 Polypropylene Substances 0.000 claims abstract description 128
- 229920001155 polypropylene Polymers 0.000 claims abstract description 123
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 99
- 239000003446 ligand Substances 0.000 claims abstract description 59
- 239000004711 α-olefin Substances 0.000 claims abstract description 28
- 230000008569 process Effects 0.000 claims abstract description 20
- 150000001336 alkenes Chemical class 0.000 claims abstract description 14
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000003780 insertion Methods 0.000 claims abstract description 6
- 230000037431 insertion Effects 0.000 claims abstract description 6
- 229920013639 polyalphaolefin Polymers 0.000 claims abstract description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 86
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 76
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 63
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 61
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 33
- 238000002844 melting Methods 0.000 claims description 31
- 230000008018 melting Effects 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 238000009826 distribution Methods 0.000 claims description 24
- 229910052735 hafnium Inorganic materials 0.000 claims description 23
- 239000000178 monomer Substances 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 20
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 17
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 claims description 16
- JEKOISATHYKFFC-UHFFFAOYSA-L [Cl-].[Cl-].C=1C=CC=CC=1C1=CC2=CC=CC=C2C1[Zr+2]C(C1=CC=CC=C1C=1)C=1C1=CC=CC=C1 Chemical compound [Cl-].[Cl-].C=1C=CC=CC=1C1=CC2=CC=CC=C2C1[Zr+2]C(C1=CC=CC=C1C=1)C=1C1=CC=CC=C1 JEKOISATHYKFFC-UHFFFAOYSA-L 0.000 claims description 15
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 14
- 150000004703 alkoxides Chemical class 0.000 claims description 14
- 229910052726 zirconium Inorganic materials 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- 150000003624 transition metals Chemical class 0.000 claims description 13
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims description 12
- 229910052719 titanium Inorganic materials 0.000 claims description 12
- 229910052723 transition metal Inorganic materials 0.000 claims description 12
- BSBXLZYWGGAVHD-UHFFFAOYSA-N 2-phenyl-1h-indene Chemical compound C=1C2=CC=CC=C2CC=1C1=CC=CC=C1 BSBXLZYWGGAVHD-UHFFFAOYSA-N 0.000 claims description 10
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 claims description 10
- 239000005977 Ethylene Substances 0.000 claims description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 229920002725 thermoplastic elastomer Polymers 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 150000004678 hydrides Chemical class 0.000 claims description 7
- 229910052768 actinide Inorganic materials 0.000 claims description 6
- 150000001255 actinides Chemical class 0.000 claims description 6
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 6
- 150000002602 lanthanoids Chemical class 0.000 claims description 6
- VRDNNNLJFDLINN-UHFFFAOYSA-N 2-(3,5-dimethylphenyl)-1h-indene Chemical compound CC1=CC(C)=CC(C=2CC3=CC=CC=C3C=2)=C1 VRDNNNLJFDLINN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052732 germanium Inorganic materials 0.000 claims description 5
- 229910052738 indium Inorganic materials 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- OOMWCTNFDPFYPJ-UHFFFAOYSA-N 2-(2,3,4,5-tetrafluorophenyl)-1h-indene Chemical compound FC1=C(F)C(F)=CC(C=2CC3=CC=CC=C3C=2)=C1F OOMWCTNFDPFYPJ-UHFFFAOYSA-N 0.000 claims description 3
- FOJNNWYEBRTDGR-UHFFFAOYSA-N 2-(3-phenylphenyl)-1h-indene Chemical compound C=1C2=CC=CC=C2CC=1C(C=1)=CC=CC=1C1=CC=CC=C1 FOJNNWYEBRTDGR-UHFFFAOYSA-N 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 3
- DWDOUGVYTPUAHL-UHFFFAOYSA-L [Cl-].[Cl-].C=1C=CC=CC=1C1=CC2=CC=CC=C2C1[Hf+2]C(C1=CC=CC=C1C=1)C=1C1=CC=CC=C1 Chemical compound [Cl-].[Cl-].C=1C=CC=CC=1C1=CC2=CC=CC=C2C1[Hf+2]C(C1=CC=CC=C1C=1)C=1C1=CC=CC=C1 DWDOUGVYTPUAHL-UHFFFAOYSA-L 0.000 claims description 3
- QRFNTKKJZQSYOJ-UHFFFAOYSA-L [Cl-].[Cl-].CC1=CC(C)=CC(C=2C(C3=CC=CC=C3C=2)[Hf+2]C2C3=CC=CC=C3C=C2C=2C=C(C)C=C(C)C=2)=C1 Chemical compound [Cl-].[Cl-].CC1=CC(C)=CC(C=2C(C3=CC=CC=C3C=2)[Hf+2]C2C3=CC=CC=C3C=C2C=2C=C(C)C=C(C)C=2)=C1 QRFNTKKJZQSYOJ-UHFFFAOYSA-L 0.000 claims description 3
- FFKMNVDOXYDERH-UHFFFAOYSA-L [Cl-].[Cl-].CC1=CC(C)=CC(C=2C(C3=CC=CC=C3C=2)[Zr+2]C2C3=CC=CC=C3C=C2C=2C=C(C)C=C(C)C=2)=C1 Chemical compound [Cl-].[Cl-].CC1=CC(C)=CC(C=2C(C3=CC=CC=C3C=2)[Zr+2]C2C3=CC=CC=C3C=C2C=2C=C(C)C=C(C)C=2)=C1 FFKMNVDOXYDERH-UHFFFAOYSA-L 0.000 claims description 3
- NNOWGHVLRPULHV-UHFFFAOYSA-L [Cl-].[Cl-].FC(F)(F)C1=CC(C(F)(F)F)=CC(C=2C(C3=CC=CC=C3C=2)[Zr+2]C2C3=CC=CC=C3C=C2C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C1 Chemical compound [Cl-].[Cl-].FC(F)(F)C1=CC(C(F)(F)F)=CC(C=2C(C3=CC=CC=C3C=2)[Zr+2]C2C3=CC=CC=C3C=C2C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C1 NNOWGHVLRPULHV-UHFFFAOYSA-L 0.000 claims description 3
- RDZGPTZXRRTEQM-UHFFFAOYSA-L [Cl-].[Cl-].[Hf++](C1C(=Cc2ccccc12)c1cccc(c1)-c1ccccc1)C1C(=Cc2ccccc12)c1cccc(c1)-c1ccccc1 Chemical compound [Cl-].[Cl-].[Hf++](C1C(=Cc2ccccc12)c1cccc(c1)-c1ccccc1)C1C(=Cc2ccccc12)c1cccc(c1)-c1ccccc1 RDZGPTZXRRTEQM-UHFFFAOYSA-L 0.000 claims description 3
- KUNZSLJMPCDOGI-UHFFFAOYSA-L [Cl-].[Cl-].[Hf+2] Chemical compound [Cl-].[Cl-].[Hf+2] KUNZSLJMPCDOGI-UHFFFAOYSA-L 0.000 claims description 3
- YMMSDIGEFSDGJB-UHFFFAOYSA-L [Cl-].[Cl-].[Zr++](C1C(=Cc2ccccc12)c1cccc(c1)-c1ccccc1)C1C(=Cc2ccccc12)c1cccc(c1)-c1ccccc1 Chemical compound [Cl-].[Cl-].[Zr++](C1C(=Cc2ccccc12)c1cccc(c1)-c1ccccc1)C1C(=Cc2ccccc12)c1cccc(c1)-c1ccccc1 YMMSDIGEFSDGJB-UHFFFAOYSA-L 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000007517 lewis acids Chemical class 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 claims description 3
- ITXJNKGMQMKZEN-UHFFFAOYSA-N 2-(4-phenylphenyl)-1h-indene Chemical compound C=1C2=CC=CC=C2CC=1C(C=C1)=CC=C1C1=CC=CC=C1 ITXJNKGMQMKZEN-UHFFFAOYSA-N 0.000 claims description 2
- JRYGTHNAWRDDQH-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-1h-indene Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C=2CC3=CC=CC=C3C=2)=C1 JRYGTHNAWRDDQH-UHFFFAOYSA-N 0.000 claims description 2
- 239000004698 Polyethylene Substances 0.000 claims description 2
- PFBSXYAEHOKVNU-UHFFFAOYSA-L [Cl-].[Cl-].C=1C=C(C=2C=CC=CC=2)C=CC=1C1=CC2=CC=CC=C2C1[Zr+2]C(C1=CC=CC=C1C=1)C=1C(C=C1)=CC=C1C1=CC=CC=C1 Chemical compound [Cl-].[Cl-].C=1C=C(C=2C=CC=CC=2)C=CC=1C1=CC2=CC=CC=C2C1[Zr+2]C(C1=CC=CC=C1C=1)C=1C(C=C1)=CC=C1C1=CC=CC=C1 PFBSXYAEHOKVNU-UHFFFAOYSA-L 0.000 claims description 2
- HCKVFBMVBHAZSL-UHFFFAOYSA-L [Cl-].[Cl-].FC(F)(F)C1=CC(C(F)(F)F)=CC(C=2C(C3=CC=CC=C3C=2)[Hf+2]C2C3=CC=CC=C3C=C2C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C1 Chemical compound [Cl-].[Cl-].FC(F)(F)C1=CC(C(F)(F)F)=CC(C=2C(C3=CC=CC=C3C=2)[Hf+2]C2C3=CC=CC=C3C=C2C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C1 HCKVFBMVBHAZSL-UHFFFAOYSA-L 0.000 claims description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 2
- 229920000573 polyethylene Polymers 0.000 claims description 2
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 2
- 239000002685 polymerization catalyst Substances 0.000 claims 15
- 239000007809 chemical reaction catalyst Substances 0.000 claims 4
- 239000010703 silicon Substances 0.000 claims 4
- WOVWBSZAHWTRFK-UHFFFAOYSA-L [Cl-].[Cl-].Fc1cc(C2=Cc3ccccc3C2[Zr++]C2C(=Cc3ccccc23)c2cc(F)c(F)c(F)c2F)c(F)c(F)c1F Chemical compound [Cl-].[Cl-].Fc1cc(C2=Cc3ccccc3C2[Zr++]C2C(=Cc3ccccc23)c2cc(F)c(F)c(F)c2F)c(F)c(F)c1F WOVWBSZAHWTRFK-UHFFFAOYSA-L 0.000 claims 2
- 229960004132 diethyl ether Drugs 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- BHAFZZGVLHFLRZ-UHFFFAOYSA-N 2-(2-phenylphenyl)-1h-indene Chemical compound C=1C2=CC=CC=C2CC=1C1=CC=CC=C1C1=CC=CC=C1 BHAFZZGVLHFLRZ-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical group COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims 1
- LMQHEQRZIZSUQY-UHFFFAOYSA-L [Cl-].[Cl-].[Hf++](C1C(=Cc2ccccc12)c1ccc(cc1)-c1ccccc1)C1C(=Cc2ccccc12)c1ccc(cc1)-c1ccccc1 Chemical compound [Cl-].[Cl-].[Hf++](C1C(=Cc2ccccc12)c1ccc(cc1)-c1ccccc1)C1C(=Cc2ccccc12)c1ccc(cc1)-c1ccccc1 LMQHEQRZIZSUQY-UHFFFAOYSA-L 0.000 claims 1
- 229920000058 polyacrylate Polymers 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 13
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 238000006317 isomerization reaction Methods 0.000 abstract description 6
- 230000000704 physical effect Effects 0.000 abstract description 5
- 229920000089 Cyclic olefin copolymer Polymers 0.000 abstract description 2
- 230000004075 alteration Effects 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 198
- 239000000243 solution Substances 0.000 description 110
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
- 239000007787 solid Substances 0.000 description 44
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 42
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 38
- 238000005481 NMR spectroscopy Methods 0.000 description 37
- 239000002904 solvent Substances 0.000 description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
- 239000000203 mixture Substances 0.000 description 27
- 238000002360 preparation method Methods 0.000 description 24
- 238000001914 filtration Methods 0.000 description 23
- 238000003756 stirring Methods 0.000 description 23
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 22
- 238000010992 reflux Methods 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 20
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 18
- 229910001220 stainless steel Inorganic materials 0.000 description 18
- 239000010935 stainless steel Substances 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 15
- 239000000523 sample Substances 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
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- 229910052786 argon Inorganic materials 0.000 description 13
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- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 10
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 230000035882 stress Effects 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- MDFLZWDNYLIUMV-UHFFFAOYSA-N 1-phenyl-2,3-dihydroinden-1-ol Chemical compound C1CC2=CC=CC=C2C1(O)C1=CC=CC=C1 MDFLZWDNYLIUMV-UHFFFAOYSA-N 0.000 description 3
- FGDKINIWCWEWLN-UHFFFAOYSA-N 2-[4-(trifluoromethyl)phenyl]-1h-indene Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC2=CC=CC=C2C1 FGDKINIWCWEWLN-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F10/04—Monomers containing three or four carbon atoms
- C08F10/06—Propene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/02—Ethene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/04—Monomers containing three or four carbon atoms
- C08F110/06—Propene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/14—Monomers containing five or more carbon atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/619—Component covered by group C08F4/60 containing a transition metal-carbon bond
- C08F4/61908—Component covered by group C08F4/60 containing a transition metal-carbon bond in combination with an ionising compound other than alumoxane, e.g. (C6F5)4B-X+
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/619—Component covered by group C08F4/60 containing a transition metal-carbon bond
- C08F4/61912—Component covered by group C08F4/60 containing a transition metal-carbon bond in combination with an organoaluminium compound
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/6592—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
- C08F4/65922—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not
- C08F4/65925—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not two cyclopentadienyl rings being mutually non-bridged
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/943—Polymerization with metallocene catalysts
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S977/00—Nanotechnology
- Y10S977/70—Nanostructure
- Y10S977/788—Of specified organic or carbon-based composition
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU21911/95A AU697375B2 (en) | 1994-03-24 | 1995-03-24 | Thermoplastic elastomeric stereoblock olefin polymers methods and metallocene catalysts |
MX9604245A MX9604245A (en) | 1994-03-24 | 1995-03-24 | Thermoplastic elastomeric stereoblock olefin polymers methods and metallocene catalysts. |
SK1202-96A SK120296A3 (en) | 1994-03-24 | 1995-03-24 | Thermoplastic elastomeric stereoblock olefin polymers methods and metallocene catalysts |
US08/702,440 US5969070A (en) | 1994-03-24 | 1995-03-24 | Thermoplastic elastomeric olefin polymers |
BR9507184A BR9507184A (en) | 1994-03-24 | 1995-03-24 | Stereoblastic olefin polymers thermoplastic processes and metallocene catalysts |
JP52480395A JP3754071B2 (en) | 1994-03-24 | 1995-03-24 | Thermoplastic elastic stereoblock olefin polymer, process and metallocene catalyst |
EP95914812A EP0802935A4 (en) | 1994-03-24 | 1995-03-24 | Thermoplastic elastomeric stereoblock olefin polymers methods and metallocene catalysts |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/218,210 | 1994-03-24 | ||
US08/218,210 US5594080A (en) | 1994-03-24 | 1994-03-24 | Thermoplastic elastomeric olefin polymers, method of production and catalysts therefor |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US08/218,210 Continuation-In-Part US5594080A (en) | 1994-03-24 | 1994-03-24 | Thermoplastic elastomeric olefin polymers, method of production and catalysts therefor |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US09/110,691 Division US6566544B1 (en) | 1994-03-24 | 1998-07-07 | Catalysts for thermoplastic elastomeric olefin polymers |
Publications (1)
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WO1995025757A1 true WO1995025757A1 (en) | 1995-09-28 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/US1995/003597 WO1995025757A1 (en) | 1994-03-24 | 1995-03-24 | Thermoplastic elastomeric stereoblock olefin polymers methods and metallocene catalysts |
Country Status (13)
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US (3) | US5594080A (en) |
EP (1) | EP0802935A4 (en) |
JP (2) | JP3754071B2 (en) |
KR (2) | KR100372667B1 (en) |
CN (1) | CN1120182C (en) |
AU (1) | AU697375B2 (en) |
BR (1) | BR9507184A (en) |
CA (1) | CA2186105A1 (en) |
CZ (1) | CZ277396A3 (en) |
MX (1) | MX9604245A (en) |
PL (1) | PL316415A1 (en) |
SK (1) | SK120296A3 (en) |
WO (1) | WO1995025757A1 (en) |
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Also Published As
Publication number | Publication date |
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BR9507184A (en) | 1997-10-07 |
US5594080A (en) | 1997-01-14 |
AU697375B2 (en) | 1998-10-01 |
KR100390258B1 (en) | 2003-10-10 |
CN1172488A (en) | 1998-02-04 |
PL316415A1 (en) | 1997-01-06 |
US5969070A (en) | 1999-10-19 |
AU2191195A (en) | 1995-10-09 |
JP2005226078A (en) | 2005-08-25 |
CZ277396A3 (en) | 1997-03-12 |
JP3754071B2 (en) | 2006-03-08 |
US6566544B1 (en) | 2003-05-20 |
MX9604245A (en) | 1997-12-31 |
CA2186105A1 (en) | 1995-09-28 |
EP0802935A1 (en) | 1997-10-29 |
SK120296A3 (en) | 2001-02-12 |
KR100372667B1 (en) | 2003-02-17 |
EP0802935A4 (en) | 1998-09-30 |
CN1120182C (en) | 2003-09-03 |
JPH09510745A (en) | 1997-10-28 |
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