DE69206590T2 - Selektive Hydrierung von Polymeren von konjugierten Diolefinen. - Google Patents
Selektive Hydrierung von Polymeren von konjugierten Diolefinen.Info
- Publication number
- DE69206590T2 DE69206590T2 DE69206590T DE69206590T DE69206590T2 DE 69206590 T2 DE69206590 T2 DE 69206590T2 DE 69206590 T DE69206590 T DE 69206590T DE 69206590 T DE69206590 T DE 69206590T DE 69206590 T2 DE69206590 T2 DE 69206590T2
- Authority
- DE
- Germany
- Prior art keywords
- polymer
- titanium
- hydrogenation
- reagent
- bis
- 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 - Fee Related
Links
- 229920000642 polymer Polymers 0.000 title claims description 68
- 238000005984 hydrogenation reaction Methods 0.000 title claims description 35
- 150000001993 dienes Chemical class 0.000 title claims description 19
- 239000003153 chemical reaction reagent Substances 0.000 claims description 28
- -1 lithium hydrocarbon Chemical class 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 25
- 230000008569 process Effects 0.000 claims description 20
- 150000004678 hydrides Chemical class 0.000 claims description 18
- 239000010936 titanium Substances 0.000 claims description 18
- 239000003513 alkali Substances 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 238000006116 polymerization reaction Methods 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 229910052719 titanium Inorganic materials 0.000 claims description 12
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 239000003505 polymerization initiator Substances 0.000 claims description 7
- 239000005049 silicon tetrachloride Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical class 0.000 claims description 6
- 229910052744 lithium Inorganic materials 0.000 claims description 5
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 claims description 4
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- KSFCHHFBQJDGFF-UHFFFAOYSA-L cyclopenta-1,3-diene;dichlorotitanium Chemical compound Cl[Ti]Cl.C1C=CC=C1.C1C=CC=C1 KSFCHHFBQJDGFF-UHFFFAOYSA-L 0.000 claims description 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical class 0.000 claims description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 125000003545 alkoxy group Chemical class 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 229920001400 block copolymer Polymers 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- 238000007334 copolymerization reaction Methods 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 230000006872 improvement Effects 0.000 claims description 3
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 claims description 3
- 150000002989 phenols Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
- 150000003440 styrenes Chemical class 0.000 claims description 3
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 claims description 2
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 claims description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 2
- BOMPXIHODLVNMC-UHFFFAOYSA-N difluoro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](F)(F)C1=CC=CC=C1 BOMPXIHODLVNMC-UHFFFAOYSA-N 0.000 claims description 2
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000002900 organolithium compounds Chemical class 0.000 claims description 2
- 150000003609 titanium compounds Chemical class 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 23
- 229910000103 lithium hydride Inorganic materials 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 14
- 230000000694 effects Effects 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-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
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical class C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- QTTAWIGVQMSWMV-UHFFFAOYSA-N 3,4-dimethylhexa-1,3-diene Chemical compound CCC(C)=C(C)C=C QTTAWIGVQMSWMV-UHFFFAOYSA-N 0.000 description 1
- OCTVDLUSQOJZEK-UHFFFAOYSA-N 4,5-diethylocta-1,3-diene Chemical compound CCCC(CC)C(CC)=CC=C OCTVDLUSQOJZEK-UHFFFAOYSA-N 0.000 description 1
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical class C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-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
- HIGZGRCLEZNBMJ-UHFFFAOYSA-L O(c1ccccc1)[Ti](Oc1ccccc1)(C1C=CC=C1)C1C=CC=C1 Chemical compound O(c1ccccc1)[Ti](Oc1ccccc1)(C1C=CC=C1)C1C=CC=C1 HIGZGRCLEZNBMJ-UHFFFAOYSA-L 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229910003910 SiCl4 Inorganic materials 0.000 description 1
- MFRXMZYAKSRDMT-UHFFFAOYSA-L [Br-].[Br-].C1(C=CC=C1)[Ti+2]C1C=CC=C1 Chemical compound [Br-].[Br-].C1(C=CC=C1)[Ti+2]C1C=CC=C1 MFRXMZYAKSRDMT-UHFFFAOYSA-L 0.000 description 1
- IPTJKFGGRLMTIC-UHFFFAOYSA-L [I-].[I-].C1(C=CC=C1)[Ti+2]C1C=CC=C1 Chemical compound [I-].[I-].C1(C=CC=C1)[Ti+2]C1C=CC=C1 IPTJKFGGRLMTIC-UHFFFAOYSA-L 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 230000006583 body weight regulation Effects 0.000 description 1
- 238000012662 bulk polymerization Methods 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- WDGICGVEWQIMTQ-UHFFFAOYSA-L cyclopentane;difluorotitanium Chemical compound F[Ti]F.[CH]1[CH][CH][CH][CH]1.[CH]1[CH][CH][CH][CH]1 WDGICGVEWQIMTQ-UHFFFAOYSA-L 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 230000001687 destabilization Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
- 229910000071 diazene Inorganic materials 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/02—Hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C2/00—Treatment of rubber solutions
- C08C2/02—Purification
- C08C2/04—Removal of catalyst residues
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/811,219 US5173537A (en) | 1991-12-20 | 1991-12-20 | Selective hydrogenation of conjugated diolefin poylmers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69206590D1 DE69206590D1 (de) | 1996-01-18 |
| DE69206590T2 true DE69206590T2 (de) | 1996-05-15 |
Family
ID=25205924
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69206590T Expired - Fee Related DE69206590T2 (de) | 1991-12-20 | 1992-12-17 | Selektive Hydrierung von Polymeren von konjugierten Diolefinen. |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5173537A (enExample) |
| EP (1) | EP0549063B1 (enExample) |
| JP (1) | JP3204763B2 (enExample) |
| KR (1) | KR100270296B1 (enExample) |
| CN (1) | CN1045608C (enExample) |
| BR (1) | BR9205044A (enExample) |
| DE (1) | DE69206590T2 (enExample) |
| ES (1) | ES2080435T3 (enExample) |
| MX (1) | MX9207381A (enExample) |
| RU (1) | RU2123012C1 (enExample) |
| TW (1) | TW216426B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5244980A (en) * | 1992-12-07 | 1993-09-14 | Shell Oil Company | Selective hydrogenation of conjugated diolefin polymers with Tebbe's reagent |
| CN1130383C (zh) * | 1996-03-15 | 2003-12-10 | 国际壳牌研究有限公司 | 共轭二烯聚合物的氢化方法及其适用的催化剂组合物 |
| US5814709A (en) * | 1996-04-12 | 1998-09-29 | Shell Oil Company | Process for hydrogenation on conjugataed diene polymers and catalyst composition suitable for use therein |
| US5705571A (en) * | 1996-05-17 | 1998-01-06 | Taiwan Synthetic Rubber Corporation | Process for selective hydrogenation of conjugated diene polymer |
| JPH1053614A (ja) * | 1996-05-29 | 1998-02-24 | Shell Internatl Res Maatschappij Bv | 共役ジエンポリマーの水素化のためのプロセスとこのプロセスで使用するのに適した触媒組成物 |
| JPH10101727A (ja) * | 1996-09-24 | 1998-04-21 | Shell Internatl Res Maatschappij Bv | オレフィン又はポリマーを水素化するための触媒及び方法 |
| TW583027B (en) | 1998-10-30 | 2004-04-11 | Shell Int Research | A method for preparing a hydrogenation catalyst system |
| US6313230B1 (en) * | 1999-09-21 | 2001-11-06 | Industrial Technology Research Institute | Catalyst composition for hydrogenation of conjugated diene based synthetic rubbers |
| KR100348761B1 (ko) * | 1999-11-26 | 2002-08-13 | 금호석유화학 주식회사 | 공액디엔을 포함하는 중합체의 선택적 수소화 방법 |
| KR100332465B1 (ko) * | 2000-02-09 | 2002-04-13 | 박찬구 | 불포화 이중결합을 가진 중합체의 수소화방법 |
| PT2272588E (pt) * | 2009-06-22 | 2013-08-01 | Dynasol Elastomeros Sa | Catalisador para a hidrogenação de compostos insaturados |
| EA029804B1 (ru) * | 2013-01-16 | 2018-05-31 | Асахи Касеи Кемикалз Корпорейшн | Способ получения полимера |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1175640A (en) * | 1967-10-05 | 1969-12-23 | Shell Int Research | Preparation of Improved Conjugated Diene Polymers |
| BE756177A (fr) * | 1969-09-17 | 1971-03-15 | Shell Int Research | Procede de preparation de copolymeres a blocs hydrogenes |
| US4076914A (en) * | 1976-06-08 | 1978-02-28 | Phillips Petroleum Company | Treatment of coupled polymers prior to hydrogenation |
| US4076915A (en) * | 1976-06-08 | 1978-02-28 | Phillips Petroleum Company | Treatment of coupled polymers prior to hydrogenation |
| GB2134909B (en) * | 1983-01-20 | 1986-08-20 | Asahi Chemical Ind | Catalytic hydrogenation of conjugated diene polymer |
| GB2144430B (en) * | 1983-08-04 | 1986-11-19 | Shell Int Research | Hydrogenated modified star-shaped polymers |
| JPS60220147A (ja) * | 1984-04-18 | 1985-11-02 | Asahi Chem Ind Co Ltd | オレフイン水添触媒および該触媒を用いた重合体の水添方法 |
| JPH066639B2 (ja) * | 1984-05-30 | 1994-01-26 | 日本合成ゴム株式会社 | ゴム組成物 |
| JPS6147706A (ja) * | 1984-08-13 | 1986-03-08 | Asahi Chem Ind Co Ltd | リビングポリマ−の水添法 |
| US4656230A (en) * | 1985-07-12 | 1987-04-07 | Phillips Petroleum Company | Hydrogenation process |
| JPS62209102A (ja) * | 1986-03-10 | 1987-09-14 | Asahi Chem Ind Co Ltd | ポリマ−の水添法 |
| JPS62209103A (ja) * | 1986-03-10 | 1987-09-14 | Asahi Chem Ind Co Ltd | ポリマ−の水添方法 |
| JP2577900B2 (ja) * | 1987-02-18 | 1997-02-05 | イハラケミカル工業 株式会社 | ポリ尿素樹脂の製造方法 |
| DE3851586T2 (de) * | 1987-07-16 | 1995-05-24 | Asahi Chemical Ind | Zusammensetzung eines spezifischen Blockmischpolymeres und Verfahren zu deren Herstellung. |
| US5017660A (en) * | 1987-08-04 | 1991-05-21 | Asahi Kasei Kogyo Kabushiki Kaisha | Selectively, partially hydrogenated polymer and rubber composition and impact resistant styrenic resin containing the same |
| JP2718059B2 (ja) * | 1988-04-28 | 1998-02-25 | 日本合成ゴム株式会社 | 重合体の水素添加方法および触媒 |
| EP0398758B1 (en) * | 1989-05-19 | 1999-03-03 | Japan Synthetic Rubber Co., Ltd. | (Modified) Hydrogenated diene block copolymer and composition comprising the same |
| US5039755A (en) * | 1990-05-29 | 1991-08-13 | Shell Oil Company | Selective hydrogenation of conjugated diolefin polymers |
| US5291990A (en) * | 1993-02-16 | 1994-03-08 | Sejzer Daniel A | Product packaging and display system |
-
1991
- 1991-12-20 US US07/811,219 patent/US5173537A/en not_active Expired - Lifetime
-
1992
- 1992-11-26 TW TW081109486A patent/TW216426B/zh active
- 1992-12-16 KR KR1019920024474A patent/KR100270296B1/ko not_active Expired - Fee Related
- 1992-12-17 JP JP33744792A patent/JP3204763B2/ja not_active Expired - Fee Related
- 1992-12-17 CN CN92114489A patent/CN1045608C/zh not_active Expired - Fee Related
- 1992-12-17 EP EP92203993A patent/EP0549063B1/en not_active Expired - Lifetime
- 1992-12-17 ES ES92203993T patent/ES2080435T3/es not_active Expired - Lifetime
- 1992-12-17 BR BR9205044A patent/BR9205044A/pt not_active IP Right Cessation
- 1992-12-17 MX MX9207381A patent/MX9207381A/es not_active IP Right Cessation
- 1992-12-17 RU RU92016286A patent/RU2123012C1/ru active
- 1992-12-17 DE DE69206590T patent/DE69206590T2/de not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH05239126A (ja) | 1993-09-17 |
| DE69206590D1 (de) | 1996-01-18 |
| EP0549063B1 (en) | 1995-12-06 |
| MX9207381A (es) | 1993-07-01 |
| KR100270296B1 (ko) | 2000-10-16 |
| EP0549063A2 (en) | 1993-06-30 |
| CN1073687A (zh) | 1993-06-30 |
| EP0549063A3 (en) | 1993-11-03 |
| TW216426B (enExample) | 1993-11-21 |
| RU2123012C1 (ru) | 1998-12-10 |
| KR930012845A (ko) | 1993-07-21 |
| US5173537A (en) | 1992-12-22 |
| CN1045608C (zh) | 1999-10-13 |
| JP3204763B2 (ja) | 2001-09-04 |
| BR9205044A (pt) | 1993-06-22 |
| ES2080435T3 (es) | 1996-02-01 |
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| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: KRATON POLYMERS RESEARCH B.V., AMSTERDAM, NL |
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| 8328 | Change in the person/name/address of the agent |
Representative=s name: DTS MUENCHEN PATENT- UND RECHTSANWAELTE, 80538 MUENCHEN |
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| 8328 | Change in the person/name/address of the agent |
Representative=s name: DERZEIT KEIN VERTRETER BESTELLT |
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| 8339 | Ceased/non-payment of the annual fee |