CA2420357A1 - A method for making selectively hydrogenated block copolymers of vinyl aromatic hydrocarbons and conjugated dienes - Google Patents
A method for making selectively hydrogenated block copolymers of vinyl aromatic hydrocarbons and conjugated dienes Download PDFInfo
- Publication number
- CA2420357A1 CA2420357A1 CA002420357A CA2420357A CA2420357A1 CA 2420357 A1 CA2420357 A1 CA 2420357A1 CA 002420357 A CA002420357 A CA 002420357A CA 2420357 A CA2420357 A CA 2420357A CA 2420357 A1 CA2420357 A1 CA 2420357A1
- Authority
- CA
- Canada
- Prior art keywords
- alcohol
- cobalt
- living chain
- terminated
- polymer
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 52
- -1 vinyl aromatic hydrocarbons Chemical class 0.000 title claims abstract description 51
- 229920001400 block copolymer Polymers 0.000 title claims abstract description 40
- 229920002554 vinyl polymer Polymers 0.000 title claims abstract description 18
- 150000001993 dienes Chemical class 0.000 title claims abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 84
- 229920000642 polymer Polymers 0.000 claims abstract description 80
- 239000003054 catalyst Substances 0.000 claims abstract description 71
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 35
- 239000010941 cobalt Substances 0.000 claims abstract description 35
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 13
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 5
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 111
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 27
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 15
- 150000007942 carboxylates Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000003158 alcohol group Chemical group 0.000 claims description 7
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 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
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 claims description 4
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-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
- 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
- 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
- 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
- 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
- 150000003509 tertiary alcohols Chemical class 0.000 claims 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 51
- 238000005984 hydrogenation reaction Methods 0.000 description 43
- 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
- 229910052759 nickel Inorganic materials 0.000 description 18
- 150000001298 alcohols Chemical class 0.000 description 17
- 229910052751 metal Inorganic materials 0.000 description 17
- 239000002184 metal Substances 0.000 description 17
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 239000004594 Masterbatch (MB) Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
- 229930195733 hydrocarbon Natural products 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
- 150000002430 hydrocarbons Chemical class 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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 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
- 229920001577 copolymer Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 3
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- 229960004132 diethyl ether Drugs 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000004519 manufacturing process Methods 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
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical class C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 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
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000004793 Polystyrene 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
- 239000012298 atmosphere Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000010960 commercial process Methods 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 150000003440 styrenes Chemical group 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- FGQLGYBGTRHODR-UHFFFAOYSA-N 2,2-diethoxypropane Chemical compound CCOC(C)(C)OCC FGQLGYBGTRHODR-UHFFFAOYSA-N 0.000 description 1
- XRMVWAKMXZNZIL-UHFFFAOYSA-N 2,2-dimethyl-1-butanol Chemical compound CCC(C)(C)CO XRMVWAKMXZNZIL-UHFFFAOYSA-N 0.000 description 1
- HMSVXZJWPVIVIV-UHFFFAOYSA-N 2,2-dimethylpentan-3-ol Chemical compound CCC(O)C(C)(C)C HMSVXZJWPVIVIV-UHFFFAOYSA-N 0.000 description 1
- IKECULIHBUCAKR-UHFFFAOYSA-N 2,3-dimethylbutan-2-ol Chemical compound CC(C)C(C)(C)O IKECULIHBUCAKR-UHFFFAOYSA-N 0.000 description 1
- HGDVHRITTGWMJK-UHFFFAOYSA-N 2,6-dimethylheptan-2-ol Chemical compound CC(C)CCCC(C)(C)O HGDVHRITTGWMJK-UHFFFAOYSA-N 0.000 description 1
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 description 1
- KRIMXCDMVRMCTC-UHFFFAOYSA-N 2-methylhexan-2-ol Chemical compound CCCCC(C)(C)O KRIMXCDMVRMCTC-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- ALRXDIKPRCRYAU-UHFFFAOYSA-N 2-methylpropan-2-ol Chemical compound CC(C)(C)O.CC(C)(C)O ALRXDIKPRCRYAU-UHFFFAOYSA-N 0.000 description 1
- LASHFHLFDRTERB-UHFFFAOYSA-N 2-propylpentan-1-ol Chemical compound CCCC(CO)CCC LASHFHLFDRTERB-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- DLHQZZUEERVIGQ-UHFFFAOYSA-N 3,7-dimethyl-3-octanol Chemical compound CCC(C)(O)CCCC(C)C DLHQZZUEERVIGQ-UHFFFAOYSA-N 0.000 description 1
- CFWIFHZJKFFDFU-UHFFFAOYSA-N 3-ethyl-2,2-dimethylpentan-3-ol Chemical compound CCC(O)(CC)C(C)(C)C CFWIFHZJKFFDFU-UHFFFAOYSA-N 0.000 description 1
- XKIRHOWVQWCYBT-UHFFFAOYSA-N 3-ethylpentan-3-ol Chemical compound CCC(O)(CC)CC XKIRHOWVQWCYBT-UHFFFAOYSA-N 0.000 description 1
- KMTDMTZBNYGUNX-UHFFFAOYSA-N 4-methylbenzyl alcohol Chemical compound CC1=CC=C(CO)C=C1 KMTDMTZBNYGUNX-UHFFFAOYSA-N 0.000 description 1
- CJSBUWDGPXGFGA-UHFFFAOYSA-N 4-methylpenta-1,3-diene Chemical compound CC(C)=CC=C CJSBUWDGPXGFGA-UHFFFAOYSA-N 0.000 description 1
- ZVEWFTICTSQBDM-UHFFFAOYSA-N 4-methylphenol Chemical compound [CH2]C1=CC=C(O)C=C1 ZVEWFTICTSQBDM-UHFFFAOYSA-N 0.000 description 1
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 description 1
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 description 1
- OAOABCKPVCUNKO-UHFFFAOYSA-N 8-methyl Nonanoic acid Chemical compound CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 150000003938 benzyl alcohols Chemical class 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- XZKRXPZXQLARHH-UHFFFAOYSA-N buta-1,3-dienylbenzene Chemical compound C=CC=CC1=CC=CC=C1 XZKRXPZXQLARHH-UHFFFAOYSA-N 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 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
- 230000001419 dependent effect Effects 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 238000007429 general method Methods 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
- 229910052741 iridium Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 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
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 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
- 125000005474 octanoate group Chemical group 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
- IWDCLRJOBJJRNH-UHFFFAOYSA-N para-hydroxytoluene Natural products CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 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
- 238000002360 preparation method Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000007670 refining Methods 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
- 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22789100P | 2000-08-25 | 2000-08-25 | |
| US60/227,891 | 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 (1)
| Publication Number | Publication Date |
|---|---|
| CA2420357A1 true CA2420357A1 (en) | 2002-02-28 |
Family
ID=22854874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002420357A Abandoned CA2420357A1 (en) | 2000-08-25 | 2001-08-24 | A method for making selectively hydrogenated block copolymers of vinyl aromatic hydrocarbons and conjugated dienes |
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 |
| 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 |
| DE60118005T2 (de) | 2006-08-03 |
| BR0113490A (pt) | 2003-07-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE10052183B4 (de) | Katalysatorzusammensetzung zur Hydrierung von Synthesekautschuken auf der Grundlage konjugierter Diene | |
| JP4248872B2 (ja) | 重合体の水素添加方法 | |
| US7390856B2 (en) | Method for making selectively hydrogenated block copolymers of vinyl aromatic hydrocarbons and conjugated dienes | |
| CN111085271B (zh) | 制备氢化苯乙烯-共轭二烯共聚物的加氢催化剂及制备方法、加氢方法和氢化共聚物 | |
| AU2001286753A1 (en) | A method for making selectively hydrogenated block copolymers of vinyl aromatic hydrocarbons and conjugated dienes | |
| JP2955528B2 (ja) | オレフィン性二重結合を有するリビング重合体の選択的水素化方法 | |
| JP5166658B2 (ja) | 水素化触媒系の製造方法 | |
| KR100267080B1 (ko) | 공액디엔 중합체의 수소화 방법 | |
| US4113930A (en) | Hydrogenated 1,3-cyclohexadiene/1,3-butadiene copolymers | |
| KR19980056208A (ko) | 리빙중합체내의 올레핀성 이중결합의 선택적 수소화 방법 | |
| CA3021383A1 (en) | Process and catalyst for hydrogen mediated saline hydride initiated anionic chain transfer polymerization | |
| EP0438288A2 (en) | Method of synthesising a selective olefin hydrogenation catalyst | |
| US9211532B2 (en) | Catalyst for the hydrogenation of unsaturated compounds | |
| TWI415681B (zh) | 觸媒系統及選擇性氫化製程 | |
| US5814710A (en) | Process for selective hydrogenation of unsaturated polymers | |
| US5061668A (en) | Hydrogenation catalyst and hydrogenation process wherein said catalyst is used | |
| KR100722015B1 (ko) | 공액 디엔으로 구성된 중합체의 부분 선택적 수소화 방법 | |
| US5013798A (en) | Hydrogenation catalyst and hydrogenation process wherein said catalyst is used | |
| EP0460737A1 (en) | Hydrogenation of polymers | |
| KR100356533B1 (ko) | 공액디엔 중합체의 선택적 수소화 방법 | |
| KR20000051055A (ko) | 공액디엔 중합체의 수소화 방법 | |
| KR19990015840A (ko) | 올레핀성 리빙중합체의 이중결합의 선택적 수소화를 위한 신촉매제조 및 이를 이용한 수첨 방법 | |
| MXPA97004619A (en) | Procedure for the production of cauchoshidrogena |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |