SG182558A1 - Common solvent process for producing high molecular weight halogenated rubber - Google Patents
Common solvent process for producing high molecular weight halogenated rubber Download PDFInfo
- Publication number
- SG182558A1 SG182558A1 SG2012052510A SG2012052510A SG182558A1 SG 182558 A1 SG182558 A1 SG 182558A1 SG 2012052510 A SG2012052510 A SG 2012052510A SG 2012052510 A SG2012052510 A SG 2012052510A SG 182558 A1 SG182558 A1 SG 182558A1
- Authority
- SG
- Singapore
- Prior art keywords
- rubber
- medium
- process according
- monomer
- solution
- Prior art date
Links
- 229920001971 elastomer Polymers 0.000 title claims abstract description 79
- 239000005060 rubber Substances 0.000 title claims abstract description 79
- 238000000034 method Methods 0.000 title claims abstract description 77
- 230000008569 process Effects 0.000 title claims abstract description 72
- 239000002904 solvent Substances 0.000 title description 29
- 239000000178 monomer Substances 0.000 claims abstract description 108
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 61
- 239000000203 mixture Substances 0.000 claims abstract description 26
- -1 bromobutyl Chemical group 0.000 claims abstract description 13
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 35
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical group CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 34
- 238000009835 boiling Methods 0.000 claims description 29
- 239000003795 chemical substances by application Substances 0.000 claims description 22
- 229920000642 polymer Polymers 0.000 claims description 22
- 229920005549 butyl rubber Polymers 0.000 claims description 20
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 19
- 239000007787 solid Substances 0.000 claims description 17
- 239000007800 oxidant agent Substances 0.000 claims description 14
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 230000002140 halogenating effect Effects 0.000 claims description 11
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 7
- 239000012429 reaction media Substances 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 238000005658 halogenation reaction Methods 0.000 abstract description 34
- 230000026030 halogenation Effects 0.000 abstract description 33
- 238000010528 free radical solution polymerization reaction Methods 0.000 abstract description 10
- 229920005557 bromobutyl Polymers 0.000 abstract description 4
- 230000002349 favourable effect Effects 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 53
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 14
- 238000005893 bromination reaction Methods 0.000 description 13
- 238000004821 distillation Methods 0.000 description 13
- 230000031709 bromination Effects 0.000 description 11
- 238000000746 purification Methods 0.000 description 11
- 238000000926 separation method Methods 0.000 description 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 10
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229920005555 halobutyl Polymers 0.000 description 7
- 229940050176 methyl chloride Drugs 0.000 description 7
- 239000002002 slurry Substances 0.000 description 7
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 6
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical compound CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 6
- PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
- 125000004968 halobutyl group Chemical group 0.000 description 6
- 150000005826 halohydrocarbons Chemical class 0.000 description 6
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- CXOWYJMDMMMMJO-UHFFFAOYSA-N 2,2-dimethylpentane Chemical compound CCCC(C)(C)C CXOWYJMDMMMMJO-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000004568 cement Substances 0.000 description 3
- 239000012320 chlorinating reagent Substances 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 230000000153 supplemental effect Effects 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- DKSMCEUSSQTGBK-UHFFFAOYSA-M bromite Chemical compound [O-]Br=O DKSMCEUSSQTGBK-UHFFFAOYSA-M 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 235000013844 butane Nutrition 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000011020 pilot scale process Methods 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- AMGNHZVUZWILSB-UHFFFAOYSA-N 1,2-bis(2-chloroethylsulfanyl)ethane Chemical compound ClCCSCCSCCCl AMGNHZVUZWILSB-UHFFFAOYSA-N 0.000 description 1
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 description 1
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 1
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical class CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 229920005556 chlorobutyl Polymers 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- VRLDVERQJMEPIF-UHFFFAOYSA-N dbdmh Chemical compound CC1(C)N(Br)C(=O)N(Br)C1=O VRLDVERQJMEPIF-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical class OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 235000013849 propane Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- XUXNAKZDHHEHPC-UHFFFAOYSA-M sodium bromate Chemical compound [Na+].[O-]Br(=O)=O XUXNAKZDHHEHPC-UHFFFAOYSA-M 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005406 washing Methods 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/18—Introducing halogen atoms or halogen-containing groups
- C08F8/20—Halogenation
- C08F8/22—Halogenation by reaction with free halogens
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10000524 | 2010-01-20 | ||
| PCT/EP2011/050530 WO2011089092A1 (en) | 2010-01-20 | 2011-01-17 | Common solvent process for producing high molecular weight halogenated rubber |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SG182558A1 true SG182558A1 (en) | 2012-08-30 |
Family
ID=42199522
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SG10201500432QA SG10201500432QA (en) | 2010-01-20 | 2011-01-17 | Common solvent process for producing high molecular weight halogenated rubber |
| SG2012052510A SG182558A1 (en) | 2010-01-20 | 2011-01-17 | Common solvent process for producing high molecular weight halogenated rubber |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SG10201500432QA SG10201500432QA (en) | 2010-01-20 | 2011-01-17 | Common solvent process for producing high molecular weight halogenated rubber |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US9273161B2 (OSRAM) |
| EP (1) | EP2525987B1 (OSRAM) |
| JP (1) | JP5781092B2 (OSRAM) |
| KR (2) | KR101709022B1 (OSRAM) |
| CN (1) | CN102753359B (OSRAM) |
| CA (1) | CA2787228C (OSRAM) |
| IN (1) | IN2012DN06387A (OSRAM) |
| MY (1) | MY162735A (OSRAM) |
| PL (1) | PL2525987T3 (OSRAM) |
| RU (1) | RU2586976C2 (OSRAM) |
| SG (2) | SG10201500432QA (OSRAM) |
| TW (1) | TWI519546B (OSRAM) |
| WO (1) | WO2011089092A1 (OSRAM) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9486088B2 (en) | 2005-09-12 | 2016-11-08 | Rtc Industries, Inc. | Product management display system |
| MY160881A (en) * | 2010-03-24 | 2017-03-31 | Arlanxeo Deutschland Gmbh | Process for the production of water and solvent-free polymers |
| EP2850131B1 (en) * | 2012-05-15 | 2017-07-26 | Bridgestone Corporation | Halogenated diene rubber for tires |
| RU2695670C2 (ru) * | 2014-04-30 | 2019-07-25 | Арланксео Сингапур Пте. Лтд. | Бутиловый каучук с новым распределением последовательностей мономерных звеньев |
| CN105218719B (zh) * | 2014-06-16 | 2017-06-06 | 中国石油化工股份有限公司 | 制备卤化丁基橡胶的方法及由此得到的卤化丁基橡胶 |
| US20170174795A1 (en) * | 2014-07-24 | 2017-06-22 | Arlanxeo Singapore Pte. Ltd. | Ultrapure copolymers |
| SG10202111129XA (en) * | 2017-04-12 | 2021-11-29 | Reliance Industries Ltd | Process for preparing halogenated isobutylene isoprene rubber |
| RU2020106316A (ru) | 2017-07-12 | 2021-08-12 | Арланксео Дойчланд Гмбх | Способ производства изоолефиновых полимеров с улучшенным получением инициирующей системы |
| RU2764774C2 (ru) | 2017-07-13 | 2022-01-21 | Арланксео Дойчланд Гмбх | Способ производства полимеров изобутена с улучшенным регулированием температуры |
| CN119735718A (zh) | 2018-12-17 | 2025-04-01 | 阿朗新科新加坡私人有限公司 | 使用叔醚生产异烯烃聚合物的方法 |
| EP3898716A4 (en) * | 2018-12-21 | 2023-01-11 | Arlanxeo Singapore Pte. Ltd. | Halogen recovery in a wet process for halogenating unsaturated isoolefin copolymer |
| JP7254183B2 (ja) | 2018-12-27 | 2023-04-07 | アランセオ・シンガポール・プライヴェート・リミテッド | 塩素化ブチルゴムを生成するための方法 |
| US12344699B2 (en) | 2020-09-18 | 2025-07-01 | Lg Chem, Ltd. | Method for halogenating isobutene-isoprene copolymer |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2964489A (en) * | 1956-07-16 | 1960-12-13 | Exxon Research Engineering Co | Process of chlorinating butyl rubber and vulcanizing the chlorinated product |
| US2969331A (en) | 1958-06-04 | 1961-01-24 | Ncr Co | Process of making dual-walled oil containing capsules |
| US3018275A (en) * | 1958-12-30 | 1962-01-23 | Exxon Research Engineering Co | Halogenation of low unsaturation rubbery polymers in the presence of oxidizing agen |
| US3257349A (en) * | 1963-09-17 | 1966-06-21 | Exxon Research Engineering Co | Purifying recycle streams in integrated process for preparing halogenated butyl rubber and butyl rubber latex |
| US3361725A (en) * | 1965-06-02 | 1968-01-02 | Exxon Research Engineering Co | Process for preparation of solution butyl rubbers using a major amount of air2x and a minor amount of airx2 as catalyst |
| US3932371A (en) | 1966-05-17 | 1976-01-13 | Exxon Research And Engineering Company | Process for preparing low bulk viscosity polymers |
| CA1019095A (en) | 1973-06-25 | 1977-10-11 | Lev N. Vladykin | Method for preparing butyl rubber |
| US4057681A (en) * | 1975-06-06 | 1977-11-08 | Exxon Research & Engineering Co. | Process for homogeneously polymerized high unsaturation C4-C10 isoolefin conjugated diene copolymers |
| IT1134567B (it) | 1980-12-03 | 1986-08-13 | Ente Giprokautchuk L | Reattore per la polimerizzazione di idrocarburi in soluzione od in sospensione |
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-
2011
- 2011-01-17 EP EP11700280.8A patent/EP2525987B1/en not_active Not-in-force
- 2011-01-17 KR KR1020157004011A patent/KR101709022B1/ko not_active Expired - Fee Related
- 2011-01-17 PL PL11700280T patent/PL2525987T3/pl unknown
- 2011-01-17 CN CN201180008617.2A patent/CN102753359B/zh active Active
- 2011-01-17 JP JP2012549323A patent/JP5781092B2/ja active Active
- 2011-01-17 SG SG10201500432QA patent/SG10201500432QA/en unknown
- 2011-01-17 US US13/522,762 patent/US9273161B2/en active Active
- 2011-01-17 IN IN6387DEN2012 patent/IN2012DN06387A/en unknown
- 2011-01-17 WO PCT/EP2011/050530 patent/WO2011089092A1/en active Application Filing
- 2011-01-17 KR KR1020127021554A patent/KR20120120311A/ko not_active Ceased
- 2011-01-17 MY MYPI2012003260A patent/MY162735A/en unknown
- 2011-01-17 CA CA2787228A patent/CA2787228C/en active Active
- 2011-01-17 RU RU2012135376/04A patent/RU2586976C2/ru active
- 2011-01-17 SG SG2012052510A patent/SG182558A1/en unknown
- 2011-01-19 TW TW100101876A patent/TWI519546B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2013517362A (ja) | 2013-05-16 |
| CA2787228A1 (en) | 2011-07-28 |
| CN102753359B (zh) | 2015-12-16 |
| KR101709022B1 (ko) | 2017-02-21 |
| JP5781092B2 (ja) | 2015-09-16 |
| PL2525987T3 (pl) | 2017-07-31 |
| EP2525987A1 (en) | 2012-11-28 |
| MY162735A (en) | 2017-07-14 |
| RU2012135376A (ru) | 2014-02-27 |
| TW201144331A (en) | 2011-12-16 |
| WO2011089092A1 (en) | 2011-07-28 |
| US9273161B2 (en) | 2016-03-01 |
| CA2787228C (en) | 2018-07-31 |
| EP2525987B1 (en) | 2016-08-24 |
| US20130137832A1 (en) | 2013-05-30 |
| KR20150027844A (ko) | 2015-03-12 |
| SG10201500432QA (en) | 2015-03-30 |
| IN2012DN06387A (OSRAM) | 2015-10-02 |
| CN102753359A (zh) | 2012-10-24 |
| RU2586976C2 (ru) | 2016-06-10 |
| KR20120120311A (ko) | 2012-11-01 |
| TWI519546B (zh) | 2016-02-01 |
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