SG184023A1 - Process for the production of water and solvent-free hydrogenated nitrile rubbers - Google Patents
Process for the production of water and solvent-free hydrogenated nitrile rubbers Download PDFInfo
- Publication number
- SG184023A1 SG184023A1 SG2012067526A SG2012067526A SG184023A1 SG 184023 A1 SG184023 A1 SG 184023A1 SG 2012067526 A SG2012067526 A SG 2012067526A SG 2012067526 A SG2012067526 A SG 2012067526A SG 184023 A1 SG184023 A1 SG 184023A1
- Authority
- SG
- Singapore
- Prior art keywords
- extruder
- fluid
- nitrile rubber
- hydrogenated nitrile
- process pursuant
- Prior art date
Links
- 229920000459 Nitrile rubber Polymers 0.000 title claims abstract description 122
- 238000000034 method Methods 0.000 title claims abstract description 104
- 230000008569 process Effects 0.000 title claims abstract description 82
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 238000004519 manufacturing process Methods 0.000 title abstract description 6
- 229920000642 polymer Polymers 0.000 claims abstract description 33
- 150000002825 nitriles Chemical class 0.000 claims abstract description 24
- 150000001993 dienes Chemical class 0.000 claims abstract description 23
- 239000000178 monomer Substances 0.000 claims abstract description 21
- 239000012530 fluid Substances 0.000 claims description 122
- 238000007872 degassing Methods 0.000 claims description 73
- 150000001875 compounds Chemical class 0.000 claims description 52
- 238000005984 hydrogenation reaction Methods 0.000 claims description 37
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 25
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 21
- -1 ethlylene Chemical compound 0.000 claims description 21
- 238000003303 reheating Methods 0.000 claims description 21
- 229920001971 elastomer Polymers 0.000 claims description 20
- 239000005060 rubber Substances 0.000 claims description 19
- 238000001816 cooling Methods 0.000 claims description 18
- 239000003960 organic solvent Substances 0.000 claims description 18
- 238000005649 metathesis reaction Methods 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 238000004898 kneading Methods 0.000 claims description 13
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 238000004891 communication Methods 0.000 claims description 11
- 238000011144 upstream manufacturing Methods 0.000 claims description 10
- 239000003039 volatile agent Substances 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 9
- 230000033228 biological regulation Effects 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 6
- 238000012545 processing Methods 0.000 claims description 6
- 238000005507 spraying Methods 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 238000005453 pelletization Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 238000009825 accumulation Methods 0.000 claims description 3
- 239000002826 coolant Substances 0.000 claims description 3
- 238000006073 displacement reaction Methods 0.000 claims description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 2
- 239000001273 butane Substances 0.000 claims description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 2
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- 229960004132 diethyl ether Drugs 0.000 claims description 2
- 239000001282 iso-butane Substances 0.000 claims description 2
- 239000012528 membrane Substances 0.000 claims description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 2
- 239000003345 natural gas Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052756 noble gas Inorganic materials 0.000 claims description 2
- 150000002835 noble gases Chemical class 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 30
- OFHCOWSQAMBJIW-AVJTYSNKSA-N alfacalcidol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C OFHCOWSQAMBJIW-AVJTYSNKSA-N 0.000 abstract 1
- 229920006168 hydrated nitrile rubber Polymers 0.000 description 37
- 239000000047 product Substances 0.000 description 37
- 239000003054 catalyst Substances 0.000 description 29
- 150000002148 esters Chemical class 0.000 description 21
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 18
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 239000012855 volatile organic compound Substances 0.000 description 14
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 13
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 12
- 229940018560 citraconate Drugs 0.000 description 11
- 238000001035 drying Methods 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- 241001441571 Hiodontidae Species 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 150000005690 diesters Chemical class 0.000 description 9
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 9
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 8
- 229910052703 rhodium Inorganic materials 0.000 description 8
- 239000010948 rhodium Substances 0.000 description 8
- 238000006731 degradation reaction Methods 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 6
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 125000005907 alkyl ester group Chemical group 0.000 description 6
- 230000015556 catabolic process Effects 0.000 description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 5
- 150000007860 aryl ester derivatives Chemical class 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 description 5
- 229940117389 dichlorobenzene Drugs 0.000 description 5
- 239000001530 fumaric acid Substances 0.000 description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 5
- 239000011976 maleic acid Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 150000002763 monocarboxylic acids Chemical class 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
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- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 4
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
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- 239000007983 Tris buffer Substances 0.000 description 4
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- 238000009835 boiling Methods 0.000 description 4
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- 125000004966 cyanoalkyl group Chemical group 0.000 description 4
- 238000005265 energy consumption Methods 0.000 description 4
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- 238000002360 preparation method Methods 0.000 description 4
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
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- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
- C08L9/02—Copolymers with acrylonitrile
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C1/00—Treatment of rubber latex
- C08C1/02—Chemical or physical treatment of rubber latex before or during concentration
- C08C1/075—Concentrating
- C08C1/12—Concentrating by evaporation
-
- 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
-
- 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
-
- 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
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F236/12—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated with nitriles
-
- 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
- C08F6/00—Post-polymerisation treatments
- C08F6/001—Removal of residual monomers by physical means
- C08F6/003—Removal of residual monomers by physical means from polymer solutions, suspensions, dispersions or emulsions without recovery of the polymer therefrom
-
- 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
- C08F6/00—Post-polymerisation treatments
- C08F6/06—Treatment of polymer solutions
- C08F6/10—Removal of volatile materials, e.g. solvents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L15/00—Compositions of rubber derivatives
- C08L15/005—Hydrogenated nitrile rubber
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)
- Dispersion Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10157846A EP2368917B1 (en) | 2010-03-25 | 2010-03-25 | Process for the production of water and solvent-free hydrogenated nitrile rubbers |
| PCT/EP2011/054285 WO2011117214A1 (en) | 2010-03-25 | 2011-03-22 | Process for the production of water and solvent-free hydrogenated nitrile rubbers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SG184023A1 true SG184023A1 (en) | 2012-10-30 |
Family
ID=42244425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SG2012067526A SG184023A1 (en) | 2010-03-25 | 2011-03-22 | Process for the production of water and solvent-free hydrogenated nitrile rubbers |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US9249236B2 (enExample) |
| EP (2) | EP2368917B1 (enExample) |
| JP (1) | JP5712411B2 (enExample) |
| KR (1) | KR101442376B1 (enExample) |
| CN (1) | CN102812052B (enExample) |
| BR (1) | BR112012024357A2 (enExample) |
| CA (1) | CA2792843A1 (enExample) |
| SG (1) | SG184023A1 (enExample) |
| TW (1) | TWI494324B (enExample) |
| WO (1) | WO2011117214A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101412845B1 (ko) * | 2010-03-24 | 2014-06-27 | 란세스 인터내쇼날 에스에이 | 무수 무용매 중합체의 제조 방법 |
| EP2368917B1 (en) * | 2010-03-25 | 2013-01-09 | LANXESS International SA | Process for the production of water and solvent-free hydrogenated nitrile rubbers |
| CN103450397B (zh) * | 2012-05-28 | 2015-05-13 | 中国石油天然气股份有限公司 | 一种丁腈橡胶的制备方法 |
| EP2676969B1 (en) * | 2012-06-22 | 2016-06-01 | University Of Waterloo | Tandem metathesis and hydrogenation of diene-based polymers in latex |
| KR20140144076A (ko) | 2013-06-10 | 2014-12-18 | 주식회사 엘지화학 | 3원계 탄성 공중합체의 제조 방법 |
| TWI653245B (zh) * | 2013-12-30 | 2019-03-11 | Arlanxeo Deutschland Gmbh | 含有苯酚之氫化腈橡膠 |
| TWI649335B (zh) | 2013-12-30 | 2019-02-01 | 德商艾朗希歐德意志有限公司 | 含酚之氫化腈橡膠 |
| WO2016030467A2 (de) * | 2014-08-27 | 2016-03-03 | List Holding Ag | Verfahren zur verbesserung der isolation von polymerlösungen |
| WO2016152890A1 (ja) * | 2015-03-26 | 2016-09-29 | 日本ゼオン株式会社 | 重合体溶液と水との分離方法 |
| EP3283538B1 (de) | 2015-04-13 | 2019-06-19 | ARLANXEO Deutschland GmbH | Emissionsarme, nitrilkautschuke enthaltende pulverförmige mischungen |
| CN118698146A (zh) * | 2024-06-24 | 2024-09-27 | 广东众和工程设计有限公司 | 一种氢化丁腈橡胶的间歇生产设备和间歇生产方法 |
| WO2026146054A1 (en) | 2024-12-30 | 2026-07-09 | ARLANXEO High Performance Elastomers (Changzhou) Co., Ltd. | Packaging arrangement for an optionally hydrogenated nitrile rubber |
Family Cites Families (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2995829A (en) * | 1957-06-18 | 1961-08-15 | Firestone Tire & Rubber Co | Method and apparatus for drying and cooling sub-divided material |
| BE587252A (enExample) | 1959-02-07 | |||
| US3700637A (en) | 1970-05-08 | 1972-10-24 | Shell Oil Co | Diene-nitrile rubbers |
| DE2539132C2 (de) | 1975-09-03 | 1987-04-09 | Bayer Ag, 5090 Leverkusen | Verwendung hydrierter Dien-Copolymere als temperaturbeständige Materialien auf dem Dichtungssektor |
| DE2612827C3 (de) * | 1976-03-26 | 1982-11-18 | Werner & Pfleiderer, 7000 Stuttgart | Schneckenstrangpresse zur kontinuierlichen Aufbereitung und Entgasung von Elastomeren und Polymeren mit einer Viskosität über 1000 d Pa s |
| US4508592A (en) * | 1976-08-04 | 1985-04-02 | Exxon Research & Engineering Co. | Elastomer extrusion drying with gas injection |
| US4198265A (en) * | 1977-11-30 | 1980-04-15 | The Firestone Tire & Rubber Company | Method of removing volatiles from an elastomer |
| JPS5653104A (en) * | 1979-10-09 | 1981-05-12 | Mitsui Petrochem Ind Ltd | Separation of polymer from polymer solution |
| NL8203281A (nl) | 1982-08-21 | 1984-03-16 | Stamicarbon | Inrichting en werkwijze voor het winnen van polymeer uit een oplossing. |
| CA1220300A (en) | 1982-12-08 | 1987-04-07 | Polysar Limited | Polymer hydrogenation process |
| CA1203047A (en) | 1982-12-08 | 1986-04-08 | Hormoz Azizian | Polymer hydrogenation process |
| DE3329974A1 (de) | 1983-08-19 | 1985-02-28 | Bayer Ag, 5090 Leverkusen | Herstellung von hydrierten nitrilkautschuken |
| DE3433392A1 (de) | 1984-09-12 | 1986-03-20 | Bayer Ag, 5090 Leverkusen | Hydrierung nitrilgruppenhaltiger ungesaettigter polymerer |
| DE3529252A1 (de) | 1985-08-16 | 1987-02-19 | Bayer Ag | Verfahren zur selektiven hydrierung ungesaettigter verbindungen |
| DE3540918A1 (de) | 1985-11-19 | 1987-05-21 | Bayer Ag | Verfahren zur selektiven hydrierung ungesaettigter verbindungen |
| DE3541689A1 (de) | 1985-11-26 | 1987-05-27 | Bayer Ag | Verfahren zur selektiven hydrierung nitrilgruppenhaltiger ungesaettigter polymerer |
| US4909898A (en) | 1986-10-01 | 1990-03-20 | Polysar Limited | Polymer recovery from solution |
| US4816525A (en) | 1987-07-06 | 1989-03-28 | University Of Waterloo | Polymer hydrogenation process |
| DE3932019C1 (enExample) | 1989-09-26 | 1991-05-08 | Bayer Ag, 5090 Leverkusen, De | |
| DE4025781A1 (de) | 1990-08-15 | 1992-02-20 | Bayer Ag | Hydrierte butadien/isopren/(meth-)acrylnitril- copolymerisate |
| US5241013A (en) * | 1992-09-02 | 1993-08-31 | Polysar Rubber Corporation | Catalytic hydrogenation of nitrile rubber |
| US5283021A (en) | 1993-06-14 | 1994-02-01 | Chi Mei Corporation | Process for removing the solvent from an elastomeric polymer solution |
| DE19537113C1 (de) * | 1995-10-05 | 1997-03-13 | Bayer Ag | Verfahren zur Herstellung von thermoplastischem Polymergranulat aus Polymerlösungen |
| JP3717213B2 (ja) * | 1995-10-31 | 2005-11-16 | 旭化成ケミカルズ株式会社 | ブロック共重合体の回収方法 |
| DE19914143A1 (de) | 1999-03-27 | 2000-09-28 | Bayer Ag | Vorrichtung und Verfahren zum Entgasen von Kunststoffen, insbesondere von hochmolekularen Polycarbonatlösungen |
| JP4459340B2 (ja) * | 1999-11-19 | 2010-04-28 | 電気化学工業株式会社 | ポリマー溶液からポリマーを回収する方法及び装置 |
| DE10008531A1 (de) | 2000-02-24 | 2001-09-13 | List Ag Arisdorf | Verfahren zum Behandeln eines Produktes in zumindest einem Mischkneter |
| US6403761B2 (en) | 2000-06-22 | 2002-06-11 | Jsr Corporation | Method for recovering a polymer |
| CA2329844A1 (en) | 2000-12-28 | 2002-06-28 | Bayer Inc. | Esbo enhanced hydrogenation |
| CA2350280A1 (en) * | 2001-06-12 | 2002-12-12 | Bayer Inc. | Low molecular weight hydrogenated nitrile rubber |
| TW593386B (en) | 2001-06-12 | 2004-06-21 | Bayer Inc | Process for the preparation of low molecular weight hydrogenated nitrile rubber |
| US6841623B2 (en) | 2001-06-29 | 2005-01-11 | Bayer Inc. | Low molecular weight nitrile rubber |
| DE10224886A1 (de) | 2002-06-05 | 2003-12-18 | Bayer Ag | Verfahren zur Herstellung von Emulsionspolymeren mit hoher Reinheit |
| CA2462011A1 (en) * | 2004-02-23 | 2005-08-23 | Bayer Inc. | Process for the preparation of low molecular weight nitrile rubber |
| EP1757623A1 (en) * | 2005-07-14 | 2007-02-28 | Lanxess Inc. | Process for the preparation of low mooney nitrile terpolymers |
| ATE538139T1 (de) | 2005-08-30 | 2012-01-15 | Lanxess Deutschland Gmbh | Verwendung von katalysatoren für den metatheseabbau von nitrilkautschuk |
| DE102005061628A1 (de) | 2005-12-21 | 2007-06-28 | Lanxess Deutschland Gmbh | Hydrierter Nitrilkautschuk mit enger Molekulargewichtsverteilung, ein Verfahren zu seiner Herstellung und seine Verwendung |
| US7666950B2 (en) * | 2006-06-01 | 2010-02-23 | Lanxess Deutschland Gmbh | Process for preparing hydrogenated nitrile rubbers |
| WO2008011477A2 (en) * | 2006-07-20 | 2008-01-24 | Albemarle Corporation | Process technology for recovering brominated styrenic polymers from reaction mixtures in which they are formed and/or converting such mixtures into pellets or into granules or pastilles |
| EP2130868B1 (en) * | 2007-03-29 | 2011-11-30 | Zeon Corporation | Nitrile copolymer rubber composition and nitrile copolymer latex composition |
| DE102007024010A1 (de) | 2007-05-22 | 2008-11-27 | Lanxess Deutschland Gmbh | Nitrilkautschuke |
| DE102007024011A1 (de) | 2007-05-22 | 2008-11-27 | Lanxess Deutschland Gmbh | Nitrilkautschuke |
| DE102007024008A1 (de) | 2007-05-22 | 2008-11-27 | Lanxess Deutschland Gmbh | Nitrilkautschuke |
| EP2027920B1 (de) | 2007-08-21 | 2014-10-08 | LANXESS Deutschland GmbH | Katalysatoren für Metathese-Reaktionen |
| CN101616982B (zh) | 2008-01-16 | 2012-11-14 | 横滨橡胶株式会社 | 氯化橡胶组合物及软管 |
| MX2011002606A (es) * | 2008-09-12 | 2011-06-24 | Lanxess Corp | Composiciones de hnbr con niveles de carga muy altos que tienen excelente capacidad de procesado y resistencia a fluidos agresivos. |
| EP2368917B1 (en) * | 2010-03-25 | 2013-01-09 | LANXESS International SA | Process for the production of water and solvent-free hydrogenated nitrile rubbers |
-
2010
- 2010-03-25 EP EP10157846A patent/EP2368917B1/en active Active
-
2011
- 2011-03-22 WO PCT/EP2011/054285 patent/WO2011117214A1/en not_active Ceased
- 2011-03-22 EP EP11709411A patent/EP2550300A1/en not_active Withdrawn
- 2011-03-22 CA CA2792843A patent/CA2792843A1/en not_active Abandoned
- 2011-03-22 SG SG2012067526A patent/SG184023A1/en unknown
- 2011-03-22 CN CN201180015931.3A patent/CN102812052B/zh active Active
- 2011-03-22 BR BR112012024357A patent/BR112012024357A2/pt not_active IP Right Cessation
- 2011-03-22 JP JP2013500462A patent/JP5712411B2/ja active Active
- 2011-03-22 KR KR1020127027739A patent/KR101442376B1/ko active Active
- 2011-03-24 TW TW100110019A patent/TWI494324B/zh active
-
2013
- 2013-05-01 US US13/874,930 patent/US9249236B2/en active Active
-
2015
- 2015-12-21 US US14/976,278 patent/US10882980B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| BR112012024357A2 (pt) | 2016-05-24 |
| CN102812052B (zh) | 2014-07-09 |
| KR20130027487A (ko) | 2013-03-15 |
| CA2792843A1 (en) | 2011-09-29 |
| WO2011117214A1 (en) | 2011-09-29 |
| TWI494324B (zh) | 2015-08-01 |
| US20160145425A1 (en) | 2016-05-26 |
| EP2368917B1 (en) | 2013-01-09 |
| CN102812052A (zh) | 2012-12-05 |
| TW201200527A (en) | 2012-01-01 |
| JP2013523902A (ja) | 2013-06-17 |
| US20140024784A1 (en) | 2014-01-23 |
| US9249236B2 (en) | 2016-02-02 |
| JP5712411B2 (ja) | 2015-05-07 |
| KR101442376B1 (ko) | 2014-09-17 |
| EP2368917A1 (en) | 2011-09-28 |
| EP2550300A1 (en) | 2013-01-30 |
| US10882980B2 (en) | 2021-01-05 |
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