EA005366B1 - Способ получения селективно гидрированных блок-сополимеров винилароматических углеводородов и сопряженных диенов - Google Patents
Способ получения селективно гидрированных блок-сополимеров винилароматических углеводородов и сопряженных диенов Download PDFInfo
- Publication number
- EA005366B1 EA005366B1 EA200300295A EA200300295A EA005366B1 EA 005366 B1 EA005366 B1 EA 005366B1 EA 200300295 A EA200300295 A EA 200300295A EA 200300295 A EA200300295 A EA 200300295A EA 005366 B1 EA005366 B1 EA 005366B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- alcohol
- cobalt
- living
- branched
- terminal
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims abstract description 85
- 238000000034 method Methods 0.000 title claims abstract description 48
- -1 vinyl aromatic hydrocarbons Chemical class 0.000 title claims abstract description 46
- 150000001993 dienes Chemical class 0.000 title claims abstract description 18
- 229920002554 vinyl polymer Polymers 0.000 title claims abstract description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 103
- 239000003054 catalyst Substances 0.000 claims abstract description 80
- 229920001400 block copolymer Polymers 0.000 claims abstract description 45
- 239000010941 cobalt Substances 0.000 claims abstract description 31
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 31
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 23
- 150000007942 carboxylates Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims description 7
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 6
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 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 4
- 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
- 150000001868 cobalt Chemical class 0.000 claims description 3
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 claims description 2
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 claims description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 2
- 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
- 239000011347 resin Substances 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- DKMDKUXBJJWYDU-UHFFFAOYSA-J C(CCCCCCCCCCC)(=O)[O-].[Co+2].[Co+2].C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-] Chemical compound C(CCCCCCCCCCC)(=O)[O-].[Co+2].[Co+2].C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-] DKMDKUXBJJWYDU-UHFFFAOYSA-J 0.000 claims 2
- 150000002148 esters Chemical class 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
- 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
- BNGNANCNFVQZBM-UHFFFAOYSA-N cobalt;ethyl hexanoate Chemical compound [Co].CCCCCC(=O)OCC BNGNANCNFVQZBM-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 48
- 238000006243 chemical reaction Methods 0.000 description 34
- 239000000243 solution Substances 0.000 description 26
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 24
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 20
- 229910052751 metal Inorganic materials 0.000 description 18
- 239000002184 metal Substances 0.000 description 18
- 150000001298 alcohols Chemical class 0.000 description 17
- 230000000694 effects Effects 0.000 description 14
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 11
- 239000004594 Masterbatch (MB) Substances 0.000 description 10
- 229910052759 nickel Inorganic materials 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 238000002474 experimental method 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
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 8
- 150000002739 metals Chemical class 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 6
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- 229910052744 lithium Inorganic materials 0.000 description 6
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- 238000004132 cross linking Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- FJIABHSGECXHBM-UHFFFAOYSA-L decanoate;nickel(2+) Chemical compound [Ni+2].CCCCCCCCCC([O-])=O.CCCCCCCCCC([O-])=O FJIABHSGECXHBM-UHFFFAOYSA-L 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- POCNHGFJLGYFIK-UHFFFAOYSA-N methylcyclooctane Chemical compound CC1CCCCCCC1 POCNHGFJLGYFIK-UHFFFAOYSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 1
- 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
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 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
- 125000000962 organic group Chemical group 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 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
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 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
- 230000001629 suppression Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22789100P | 2000-08-25 | 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 |
|---|---|
| EA200300295A1 EA200300295A1 (ru) | 2003-08-28 |
| EA005366B1 true EA005366B1 (ru) | 2005-02-24 |
Family
ID=22854874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200300295A EA005366B1 (ru) | 2000-08-25 | 2001-08-24 | Способ получения селективно гидрированных блок-сополимеров винилароматических углеводородов и сопряженных диенов |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7390856B2 (OSRAM) |
| EP (1) | EP1325042B1 (OSRAM) |
| JP (1) | JP5007013B2 (OSRAM) |
| KR (1) | KR100822923B1 (OSRAM) |
| CN (1) | CN1227270C (OSRAM) |
| AT (1) | ATE320453T1 (OSRAM) |
| AU (2) | AU8675301A (OSRAM) |
| BR (1) | BR0113490A (OSRAM) |
| CA (1) | CA2420357A1 (OSRAM) |
| DE (1) | DE60118005T2 (OSRAM) |
| EA (1) | EA005366B1 (OSRAM) |
| ES (1) | ES2256289T3 (OSRAM) |
| MX (1) | MXPA03001649A (OSRAM) |
| WO (1) | WO2002016449A2 (OSRAM) |
| ZA (1) | ZA200301460B (OSRAM) |
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 |
| EP1505080A1 (en) | 2003-07-28 | 2005-02-09 | KRATON Polymers Research B.V. | Method for partially and selectively hydrogenating polymers made of conjugated dienes |
| US7359641B2 (en) * | 2003-07-28 | 2008-04-15 | Emcore Corporation | Modular optical transceiver |
| 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 |
| CN103827157B (zh) * | 2011-09-29 | 2017-05-31 | 三菱化学株式会社 | 氢化嵌段共聚物、树脂组合物、膜及容器 |
| KR102020485B1 (ko) | 2013-01-11 | 2019-09-11 | 삼성디스플레이 주식회사 | 블록 공중합체, 그 형성 방법 및 패턴 형성 방법 |
| EP3074465B1 (en) | 2013-11-26 | 2019-08-28 | Kraton Polymers U.S. LLC | Laser sintering powder, laser sintering article, and a method of making a laser sintering article |
| KR20220064208A (ko) | 2020-11-11 | 2022-05-18 | 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 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1020720A (en) * | 1963-12-26 | 1966-02-23 | Shell Int Research | Process for the catalytic hydrogenation of block copolymers |
| DE1920403A1 (de) * | 1968-04-23 | 1969-10-30 | Bridgestone Tire Co Ltd | Katalysator zum Hydrieren von Polymeren und seine Verwendung zur selektiven Hydrierung von olefinischen Doppelbindungen in Kohlenwasserstoffpolymeren |
| US3957914A (en) * | 1973-02-22 | 1976-05-18 | Shell Oil Company | Cyclic polymerization process |
| DE2748884A1 (de) * | 1977-11-02 | 1979-05-03 | Basf Ag | Verfahren zur katalytischen hydrierung von diolefinpolymerisaten |
| WO1991018025A2 (en) * | 1990-05-14 | 1991-11-28 | Shell Internationale Research Maatschappij B.V. | Termination of anionic polymerization |
| US5281696A (en) * | 1992-12-07 | 1994-01-25 | Shell Oil Company | Removal of hydrogenation catalyst from polymer solutions by trialkyl aluminum precipitation |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3415759A (en) * | 1964-03-11 | 1968-12-10 | Shell Oil Co | Preparation of hydrogenation catalysts |
| 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 |
| 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 |
| US5206307A (en) * | 1991-09-09 | 1993-04-27 | Shell Oil Company | Process for 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 |
| DE4228160A1 (de) * | 1992-08-25 | 1994-03-03 | Basf Ag | Polymerisate auf Basis von konjugierten Dienen |
| 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 MX MXPA03001649A patent/MXPA03001649A/es active IP Right Grant
- 2001-08-24 KR KR1020037002678A patent/KR100822923B1/ko not_active Expired - Fee Related
- 2001-08-24 DE DE60118005T patent/DE60118005T2/de not_active Expired - Lifetime
- 2001-08-24 CA CA002420357A patent/CA2420357A1/en not_active Abandoned
- 2001-08-24 US US10/362,145 patent/US7390856B2/en not_active Expired - Fee Related
- 2001-08-24 EA EA200300295A patent/EA005366B1/ru not_active IP Right Cessation
- 2001-08-24 AT AT01966220T patent/ATE320453T1/de not_active IP Right Cessation
- 2001-08-24 JP JP2002521544A patent/JP5007013B2/ja not_active Expired - Fee Related
- 2001-08-24 BR BR0113490-6A patent/BR0113490A/pt not_active IP Right Cessation
- 2001-08-24 EP EP01966220A patent/EP1325042B1/en not_active Expired - Lifetime
- 2001-08-24 WO PCT/US2001/026551 patent/WO2002016449A2/en not_active Ceased
- 2001-08-24 AU AU8675301A patent/AU8675301A/xx active Pending
- 2001-08-24 ES ES01966220T patent/ES2256289T3/es not_active Expired - Lifetime
- 2001-08-24 CN CNB018163645A patent/CN1227270C/zh not_active Expired - Fee Related
- 2001-08-24 AU AU2001286753A patent/AU2001286753B2/en not_active Ceased
-
2003
- 2003-02-24 ZA ZA200301460A patent/ZA200301460B/en unknown
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1020720A (en) * | 1963-12-26 | 1966-02-23 | Shell Int Research | Process for the catalytic hydrogenation of block copolymers |
| DE1920403A1 (de) * | 1968-04-23 | 1969-10-30 | Bridgestone Tire Co Ltd | Katalysator zum Hydrieren von Polymeren und seine Verwendung zur selektiven Hydrierung von olefinischen Doppelbindungen in Kohlenwasserstoffpolymeren |
| US3957914A (en) * | 1973-02-22 | 1976-05-18 | Shell Oil Company | Cyclic polymerization process |
| DE2748884A1 (de) * | 1977-11-02 | 1979-05-03 | Basf Ag | Verfahren zur katalytischen hydrierung von diolefinpolymerisaten |
| WO1991018025A2 (en) * | 1990-05-14 | 1991-11-28 | Shell Internationale Research Maatschappij B.V. | Termination of anionic polymerization |
| US5281696A (en) * | 1992-12-07 | 1994-01-25 | Shell Oil Company | Removal of hydrogenation catalyst from polymer solutions by trialkyl aluminum precipitation |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2004506787A (ja) | 2004-03-04 |
| ATE320453T1 (de) | 2006-04-15 |
| CA2420357A1 (en) | 2002-02-28 |
| BR0113490A (pt) | 2003-07-15 |
| CN1476451A (zh) | 2004-02-18 |
| KR100822923B1 (ko) | 2008-04-16 |
| ES2256289T3 (es) | 2006-07-16 |
| DE60118005D1 (de) | 2006-05-11 |
| AU8675301A (en) | 2002-03-04 |
| US7390856B2 (en) | 2008-06-24 |
| EP1325042A2 (en) | 2003-07-09 |
| US20040014902A1 (en) | 2004-01-22 |
| EP1325042B1 (en) | 2006-03-15 |
| DE60118005T2 (de) | 2006-08-03 |
| EA200300295A1 (ru) | 2003-08-28 |
| AU2001286753B2 (en) | 2005-08-04 |
| WO2002016449A2 (en) | 2002-02-28 |
| MXPA03001649A (es) | 2004-04-05 |
| ZA200301460B (en) | 2004-04-19 |
| KR20030040420A (ko) | 2003-05-22 |
| WO2002016449A3 (en) | 2002-05-16 |
| CN1227270C (zh) | 2005-11-16 |
| JP5007013B2 (ja) | 2012-08-22 |
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| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): AM AZ BY KZ KG MD TJ TM RU |