DE60118005T2 - Verfahren zur herstellung von selektiv hydrierten blockcopolymeren aus vinylaromatischen kohlenwasserstoffen und konjugierten dienen - Google Patents
Verfahren zur herstellung von selektiv hydrierten blockcopolymeren aus vinylaromatischen kohlenwasserstoffen und konjugierten dienen Download PDFInfo
- Publication number
- DE60118005T2 DE60118005T2 DE60118005T DE60118005T DE60118005T2 DE 60118005 T2 DE60118005 T2 DE 60118005T2 DE 60118005 T DE60118005 T DE 60118005T DE 60118005 T DE60118005 T DE 60118005T DE 60118005 T2 DE60118005 T2 DE 60118005T2
- Authority
- DE
- Germany
- Prior art keywords
- alcohol
- cobalt
- polymer
- branched
- chain
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 49
- 229920001400 block copolymer Polymers 0.000 title claims abstract description 37
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 16
- 229930195733 hydrocarbon Natural products 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 229920000642 polymer Polymers 0.000 claims abstract description 81
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 80
- 239000003054 catalyst Substances 0.000 claims abstract description 68
- -1 vinyl aromatic hydrocarbons Chemical class 0.000 claims abstract description 39
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 32
- 239000010941 cobalt Substances 0.000 claims abstract description 32
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000001993 dienes Chemical class 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims abstract description 13
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 8
- 125000003158 alcohol group Chemical group 0.000 claims abstract 5
- 230000008569 process Effects 0.000 claims description 27
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 150000007942 carboxylates Chemical class 0.000 claims description 9
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- KDMCQAXHWIEEDE-UHFFFAOYSA-L cobalt(2+);7,7-dimethyloctanoate Chemical compound [Co+2].CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O KDMCQAXHWIEEDE-UHFFFAOYSA-L 0.000 claims description 5
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 claims description 5
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 claims description 3
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 claims description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000001868 cobalt Chemical class 0.000 claims description 3
- 159000000032 aromatic acids Chemical class 0.000 claims description 2
- AMFIJXSMYBKJQV-UHFFFAOYSA-L cobalt(2+);octadecanoate Chemical compound [Co+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AMFIJXSMYBKJQV-UHFFFAOYSA-L 0.000 claims description 2
- HWVKIRQMNIWOLT-UHFFFAOYSA-L cobalt(2+);octanoate Chemical compound [Co+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O HWVKIRQMNIWOLT-UHFFFAOYSA-L 0.000 claims description 2
- SFLMUHDGSQZDOW-FAOXUISGSA-N coniferin Chemical compound COC1=CC(\C=C\CO)=CC=C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 SFLMUHDGSQZDOW-FAOXUISGSA-N 0.000 claims description 2
- SFLMUHDGSQZDOW-IBEHDNSVSA-N coniferoside Natural products COC1=CC(C=CCO)=CC=C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 SFLMUHDGSQZDOW-IBEHDNSVSA-N 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 2
- IIGAELMXVLEZPM-GRVYQHKQSA-L cobalt(2+);(9z,12z)-octadeca-9,12-dienoate Chemical compound [Co+2].CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O.CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O IIGAELMXVLEZPM-GRVYQHKQSA-L 0.000 claims 1
- LHEFLUZWISWYSQ-CVBJKYQLSA-L cobalt(2+);(z)-octadec-9-enoate Chemical compound [Co+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O LHEFLUZWISWYSQ-CVBJKYQLSA-L 0.000 claims 1
- GEORCJSIKXKERB-UHFFFAOYSA-L cobalt(2+);cyclohexanecarboxylate Chemical compound [Co+2].[O-]C(=O)C1CCCCC1.[O-]C(=O)C1CCCCC1 GEORCJSIKXKERB-UHFFFAOYSA-L 0.000 claims 1
- CTIHZTFULZJBGQ-UHFFFAOYSA-L cobalt(2+);decanoate Chemical compound [Co+2].CCCCCCCCCC([O-])=O.CCCCCCCCCC([O-])=O CTIHZTFULZJBGQ-UHFFFAOYSA-L 0.000 claims 1
- GAYAMOAYBXKUII-UHFFFAOYSA-L cobalt(2+);dibenzoate Chemical compound [Co+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 GAYAMOAYBXKUII-UHFFFAOYSA-L 0.000 claims 1
- ZXTQQLBKWDRTKI-UHFFFAOYSA-L cobalt(2+);dodecanoate Chemical compound [Co+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O ZXTQQLBKWDRTKI-UHFFFAOYSA-L 0.000 claims 1
- FDPHDGUADUFPHZ-UHFFFAOYSA-L cobalt(2+);heptanoate Chemical compound [Co+2].CCCCCCC([O-])=O.CCCCCCC([O-])=O FDPHDGUADUFPHZ-UHFFFAOYSA-L 0.000 claims 1
- SSWSYWBRGQINON-UHFFFAOYSA-L cobalt(2+);hexadecanoate Chemical compound [Co+2].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O SSWSYWBRGQINON-UHFFFAOYSA-L 0.000 claims 1
- NMNZGKIKHBYUNG-UHFFFAOYSA-L cobalt(2+);hexanoate Chemical compound [Co+2].CCCCCC([O-])=O.CCCCCC([O-])=O NMNZGKIKHBYUNG-UHFFFAOYSA-L 0.000 claims 1
- ZEUMJGYFKUTAKD-UHFFFAOYSA-L cobalt(2+);nonanoate Chemical compound [Co+2].CCCCCCCCC([O-])=O.CCCCCCCCC([O-])=O ZEUMJGYFKUTAKD-UHFFFAOYSA-L 0.000 claims 1
- ORPKVCOHQRRGSM-UHFFFAOYSA-L cobalt(2+);tetradecanoate Chemical compound [Co+2].CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O ORPKVCOHQRRGSM-UHFFFAOYSA-L 0.000 claims 1
- BNGNANCNFVQZBM-UHFFFAOYSA-N cobalt;ethyl hexanoate Chemical compound [Co].CCCCCC(=O)OCC BNGNANCNFVQZBM-UHFFFAOYSA-N 0.000 claims 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 claims 1
- 150000003509 tertiary alcohols Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 abstract description 2
- 230000000379 polymerizing effect Effects 0.000 abstract description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 55
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 29
- 239000000243 solution Substances 0.000 description 26
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 22
- 150000001298 alcohols Chemical class 0.000 description 17
- 229910052751 metal Inorganic materials 0.000 description 17
- 239000002184 metal Substances 0.000 description 17
- 229910052759 nickel Inorganic materials 0.000 description 17
- 230000000694 effects Effects 0.000 description 12
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 8
- 230000000737 periodic effect Effects 0.000 description 8
- 229920000428 triblock copolymer Polymers 0.000 description 8
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 230000003197 catalytic effect Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000004568 cement Substances 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000003426 co-catalyst Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 3
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical class C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 2
- WFRBDWRZVBPBDO-UHFFFAOYSA-N 2-methyl-2-pentanol Chemical compound CCCC(C)(C)O WFRBDWRZVBPBDO-UHFFFAOYSA-N 0.000 description 2
- FRDAATYAJDYRNW-UHFFFAOYSA-N 3-methyl-3-pentanol Chemical compound CCC(C)(O)CC FRDAATYAJDYRNW-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
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- 239000005062 Polybutadiene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
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- 238000011161 development Methods 0.000 description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
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- JMWUYEFBFUCSAK-UHFFFAOYSA-L nickel(2+);octadecanoate Chemical compound [Ni+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O JMWUYEFBFUCSAK-UHFFFAOYSA-L 0.000 description 1
- DVTHIMLUHWEZOM-UHFFFAOYSA-L nickel(2+);octanoate Chemical compound [Ni+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O DVTHIMLUHWEZOM-UHFFFAOYSA-L 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- DFOXKPDFWGNLJU-UHFFFAOYSA-N pinacolyl alcohol Chemical compound CC(O)C(C)(C)C DFOXKPDFWGNLJU-UHFFFAOYSA-N 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000011414 polymer cement Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229920006132 styrene block copolymer Polymers 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/02—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type
- C08F297/04—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type polymerising vinyl aromatic monomers and conjugated dienes
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/04—Reduction, e.g. hydrogenation
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Graft Or Block Polymers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22789100P | 2000-08-25 | 2000-08-25 | |
| US227891P | 2000-08-25 | ||
| PCT/US2001/026551 WO2002016449A2 (en) | 2000-08-25 | 2001-08-24 | A method for making selectively hydrogenated block copolymers of vinyl aromatic hydrocarbons and conjugated dienes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60118005D1 DE60118005D1 (de) | 2006-05-11 |
| DE60118005T2 true DE60118005T2 (de) | 2006-08-03 |
Family
ID=22854874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60118005T Expired - Lifetime DE60118005T2 (de) | 2000-08-25 | 2001-08-24 | Verfahren zur herstellung von selektiv hydrierten blockcopolymeren aus vinylaromatischen kohlenwasserstoffen und konjugierten dienen |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7390856B2 (enExample) |
| EP (1) | EP1325042B1 (enExample) |
| JP (1) | JP5007013B2 (enExample) |
| KR (1) | KR100822923B1 (enExample) |
| CN (1) | CN1227270C (enExample) |
| AT (1) | ATE320453T1 (enExample) |
| AU (2) | AU2001286753B2 (enExample) |
| BR (1) | BR0113490A (enExample) |
| CA (1) | CA2420357A1 (enExample) |
| DE (1) | DE60118005T2 (enExample) |
| EA (1) | EA005366B1 (enExample) |
| ES (1) | ES2256289T3 (enExample) |
| MX (1) | MXPA03001649A (enExample) |
| WO (1) | WO2002016449A2 (enExample) |
| ZA (1) | ZA200301460B (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004264346A (ja) * | 2003-02-05 | 2004-09-24 | Sharp Corp | 現像剤及びその製造方法 |
| US7359641B2 (en) * | 2003-07-28 | 2008-04-15 | Emcore Corporation | Modular optical transceiver |
| EP1505080A1 (en) * | 2003-07-28 | 2005-02-09 | KRATON Polymers Research B.V. | Method for partially and selectively hydrogenating polymers made of conjugated dienes |
| US6974260B2 (en) * | 2003-07-30 | 2005-12-13 | Emcore Corporation | Flexible substrate for routing fibers in an optical transceiver |
| CA2775005C (en) | 2009-09-25 | 2015-11-17 | China Petroleum & Chemical Corporation | Isoolefin polymers and process for preparing the same |
| EP2762505B1 (en) * | 2011-09-29 | 2016-09-07 | Mitsubishi Chemical Corporation | Hydrogenated block copolymer, resin composition, film and container |
| KR102020485B1 (ko) | 2013-01-11 | 2019-09-11 | 삼성디스플레이 주식회사 | 블록 공중합체, 그 형성 방법 및 패턴 형성 방법 |
| JP2016538395A (ja) | 2013-11-26 | 2016-12-08 | クレイトン・ポリマーズ・ユー・エス・エル・エル・シー | レーザ焼結粉末、レーザ焼結物品およびレーザ焼結物品を作製する方法 |
| KR102925040B1 (ko) | 2020-11-11 | 2026-02-09 | 주식회사 엘지화학 | 수소화 공액디엔계 중합체 제조방법 |
| KR20240044062A (ko) | 2022-09-28 | 2024-04-04 | 주식회사 엘지화학 | 촉매 조성물 및 이를 이용한 수소화 공액디엔계 중합체의 제조방법 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE307674B (enExample) * | 1963-12-26 | 1969-01-13 | Shell Int Research | |
| US3415759A (en) | 1964-03-11 | 1968-12-10 | Shell Oil Co | Preparation of hydrogenation catalysts |
| GB1268210A (en) * | 1968-04-23 | 1972-03-22 | Bridgestone Tire Co Ltd | Process for hydrogenating polymers |
| US3957914A (en) * | 1973-02-22 | 1976-05-18 | Shell Oil Company | Cyclic polymerization process |
| DE2748884C2 (de) * | 1977-11-02 | 1982-05-19 | Basf Ag, 6700 Ludwigshafen | Verfahren zur katalytischen Hydrierung von Polymerisaten konjugierter Diene |
| JPS61130303A (ja) * | 1984-11-29 | 1986-06-18 | Nippon Zeon Co Ltd | 共役ジエン系重合体の水素化方法 |
| BR8905680A (pt) * | 1988-11-09 | 1990-06-05 | Shell Int Research | Catalisador de hidrogenacao,processo para hidrogenar um composto que contem insaturacao etilencia e/ou aromatica,e composto |
| US5057582A (en) | 1988-12-23 | 1991-10-15 | Shell Oil Company | Hydrogenation catalyst and hydrogenation process wherein said catalyst is used |
| US5151475A (en) | 1991-04-15 | 1992-09-29 | Shell Oil Company | Termination of anionic polymerization |
| CN1031268C (zh) * | 1990-05-14 | 1996-03-13 | 国际壳牌研究有限公司 | 阴离子聚合终止法 |
| US5143990A (en) * | 1990-05-14 | 1992-09-01 | Shell Oil Company | Termination of anionic polymerization using hydrogen |
| US5597872A (en) * | 1990-05-29 | 1997-01-28 | Shell Oil Company | Hydrogenation of polymers having ketone groups |
| US5141997A (en) * | 1990-08-15 | 1992-08-25 | Shell Oil Company | Selective hydrogenation of conjugated diolefin polymers |
| US5132372A (en) * | 1991-09-09 | 1992-07-21 | Shell Oil Company | Process for selective hydrogenation of conjugated diolefin polymers |
| US5206307A (en) * | 1991-09-09 | 1993-04-27 | Shell Oil Company | Process for selective hydrogenation of conjugated diolefin polymers |
| DE4228160A1 (de) * | 1992-08-25 | 1994-03-03 | Basf Ag | Polymerisate auf Basis von konjugierten Dienen |
| US5281696A (en) * | 1992-12-07 | 1994-01-25 | Shell Oil Company | Removal of hydrogenation catalyst from polymer solutions by trialkyl aluminum precipitation |
| IT1279197B1 (it) * | 1994-05-13 | 1997-12-04 | Shell Int Research | Catalizzatori eterogenei di idrogenazione migliorati con ridotta isomerizzazione delle olefine |
| KR0182835B1 (ko) * | 1996-04-26 | 1999-05-15 | 김흥기 | 올레핀성 이중결합을 갖는 리빙중합체의 선택적 수소화 방법 |
| DE19642489A1 (de) * | 1996-10-15 | 1998-04-16 | Basf Ag | Verfahren zur Herstellung von Pfropfcopolymeren |
| KR100267080B1 (ko) * | 1998-08-03 | 2000-10-02 | 박찬구 | 공액디엔 중합체의 수소화 방법 |
| US6222008B1 (en) * | 1999-05-06 | 2001-04-24 | Shell Oil Company | Treatment of polymer solution with acid and ammonia to improve polymer color |
-
2001
- 2001-08-24 WO PCT/US2001/026551 patent/WO2002016449A2/en not_active Ceased
- 2001-08-24 EP EP01966220A patent/EP1325042B1/en not_active Expired - Lifetime
- 2001-08-24 KR KR1020037002678A patent/KR100822923B1/ko not_active Expired - Fee Related
- 2001-08-24 JP JP2002521544A patent/JP5007013B2/ja not_active Expired - Fee Related
- 2001-08-24 AT AT01966220T patent/ATE320453T1/de not_active IP Right Cessation
- 2001-08-24 AU AU2001286753A patent/AU2001286753B2/en not_active Ceased
- 2001-08-24 ES ES01966220T patent/ES2256289T3/es not_active Expired - Lifetime
- 2001-08-24 BR BR0113490-6A patent/BR0113490A/pt not_active IP Right Cessation
- 2001-08-24 AU AU8675301A patent/AU8675301A/xx active Pending
- 2001-08-24 EA EA200300295A patent/EA005366B1/ru not_active IP Right Cessation
- 2001-08-24 DE DE60118005T patent/DE60118005T2/de not_active Expired - Lifetime
- 2001-08-24 MX MXPA03001649A patent/MXPA03001649A/es active IP Right Grant
- 2001-08-24 US US10/362,145 patent/US7390856B2/en not_active Expired - Fee Related
- 2001-08-24 CA CA002420357A patent/CA2420357A1/en not_active Abandoned
- 2001-08-24 CN CNB018163645A patent/CN1227270C/zh not_active Expired - Fee Related
-
2003
- 2003-02-24 ZA ZA200301460A patent/ZA200301460B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1325042B1 (en) | 2006-03-15 |
| ATE320453T1 (de) | 2006-04-15 |
| ES2256289T3 (es) | 2006-07-16 |
| US7390856B2 (en) | 2008-06-24 |
| CA2420357A1 (en) | 2002-02-28 |
| MXPA03001649A (es) | 2004-04-05 |
| KR20030040420A (ko) | 2003-05-22 |
| US20040014902A1 (en) | 2004-01-22 |
| EA200300295A1 (ru) | 2003-08-28 |
| KR100822923B1 (ko) | 2008-04-16 |
| ZA200301460B (en) | 2004-04-19 |
| AU8675301A (en) | 2002-03-04 |
| WO2002016449A3 (en) | 2002-05-16 |
| CN1227270C (zh) | 2005-11-16 |
| AU2001286753B2 (en) | 2005-08-04 |
| EP1325042A2 (en) | 2003-07-09 |
| WO2002016449A2 (en) | 2002-02-28 |
| JP2004506787A (ja) | 2004-03-04 |
| JP5007013B2 (ja) | 2012-08-22 |
| EA005366B1 (ru) | 2005-02-24 |
| DE60118005D1 (de) | 2006-05-11 |
| CN1476451A (zh) | 2004-02-18 |
| BR0113490A (pt) | 2003-07-15 |
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|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8328 | Change in the person/name/address of the agent |
Representative=s name: STOLMAR SCHEELE & PARTNER, 80331 MUENCHEN |