RU2586976C2 - Способ получения высокомолекулярного галогенированного каучука с использованием общего растворителя - Google Patents
Способ получения высокомолекулярного галогенированного каучука с использованием общего растворителя Download PDFInfo
- Publication number
- RU2586976C2 RU2586976C2 RU2012135376/04A RU2012135376A RU2586976C2 RU 2586976 C2 RU2586976 C2 RU 2586976C2 RU 2012135376/04 A RU2012135376/04 A RU 2012135376/04A RU 2012135376 A RU2012135376 A RU 2012135376A RU 2586976 C2 RU2586976 C2 RU 2586976C2
- Authority
- RU
- Russia
- Prior art keywords
- rubber
- monomers
- medium
- mixture
- monomer
- Prior art date
Links
- 229920001971 elastomer Polymers 0.000 title claims abstract description 76
- 239000005060 rubber Substances 0.000 title claims abstract description 76
- 238000000034 method Methods 0.000 title claims abstract description 68
- 239000002904 solvent Substances 0.000 title description 28
- 239000000178 monomer Substances 0.000 claims abstract description 116
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 64
- 238000009835 boiling Methods 0.000 claims abstract description 31
- 239000000203 mixture Substances 0.000 claims abstract description 30
- 229920000642 polymer Polymers 0.000 claims abstract description 22
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 21
- -1 cyclic aliphatic hydrocarbons Chemical class 0.000 claims abstract description 20
- 230000002140 halogenating effect Effects 0.000 claims abstract description 13
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims abstract description 12
- 239000012429 reaction media Substances 0.000 claims abstract description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 37
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical group CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 34
- 229920005549 butyl rubber Polymers 0.000 claims description 21
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 18
- 239000007787 solid Substances 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000007800 oxidant agent Substances 0.000 claims description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 7
- 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 27
- 230000026030 halogenation Effects 0.000 abstract description 26
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 239000000126 substance Substances 0.000 abstract description 7
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 239000006227 byproduct Substances 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 3
- 238000005516 engineering process Methods 0.000 abstract description 3
- 230000009467 reduction Effects 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 54
- 230000008569 process Effects 0.000 description 34
- 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 16
- 238000004821 distillation Methods 0.000 description 13
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
- 230000031709 bromination Effects 0.000 description 10
- 238000005893 bromination reaction Methods 0.000 description 10
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 10
- 229920005555 halobutyl Polymers 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 238000000926 separation method Methods 0.000 description 9
- 125000004968 halobutyl group Chemical group 0.000 description 8
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 8
- 229940050176 methyl chloride Drugs 0.000 description 8
- 238000000746 purification Methods 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 6
- CXOWYJMDMMMMJO-UHFFFAOYSA-N 2,2-dimethylpentane Chemical compound CCCC(C)(C)C CXOWYJMDMMMMJO-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
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 6
- 150000008282 halocarbons 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
- 238000004140 cleaning Methods 0.000 description 5
- 238000004064 recycling Methods 0.000 description 5
- 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
- 229920005557 bromobutyl Polymers 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000047 product 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
- 238000005265 energy consumption Methods 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 238000012545 processing Methods 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
- 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
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
- 230000008901 benefit Effects 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
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000012320 chlorinating reagent Substances 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 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
- 230000001706 oxygenating effect Effects 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 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
- 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 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
- 239000003463 adsorbent Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 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
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 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
- 239000003518 caustics Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 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
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000012045 crude solution Substances 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
- 230000007613 environmental effect Effects 0.000 description 1
- MGDOJPNDRJNJBK-UHFFFAOYSA-N ethylaluminum Chemical compound [Al].C[CH2] MGDOJPNDRJNJBK-UHFFFAOYSA-N 0.000 description 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 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
- 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
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase 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
- 150000002739 metals Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000000962 organic group Chemical group 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 compound 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
- 238000011020 pilot scale process Methods 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
- 238000002360 preparation method Methods 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
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000010063 rubber manufacturing process Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002002 slurry Substances 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
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- NYCVSSWORUBFET-UHFFFAOYSA-M sodium;bromite Chemical compound [Na+].[O-]Br=O NYCVSSWORUBFET-UHFFFAOYSA-M 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10000524.8 | 2010-01-20 | ||
| 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 (2)
| Publication Number | Publication Date |
|---|---|
| RU2012135376A RU2012135376A (ru) | 2014-02-27 |
| RU2586976C2 true RU2586976C2 (ru) | 2016-06-10 |
Family
ID=42199522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2012135376/04A RU2586976C2 (ru) | 2010-01-20 | 2011-01-17 | Способ получения высокомолекулярного галогенированного каучука с использованием общего растворителя |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US9273161B2 (enEXAMPLES) |
| EP (1) | EP2525987B1 (enEXAMPLES) |
| JP (1) | JP5781092B2 (enEXAMPLES) |
| KR (2) | KR20120120311A (enEXAMPLES) |
| CN (1) | CN102753359B (enEXAMPLES) |
| CA (1) | CA2787228C (enEXAMPLES) |
| IN (1) | IN2012DN06387A (enEXAMPLES) |
| MY (1) | MY162735A (enEXAMPLES) |
| PL (1) | PL2525987T3 (enEXAMPLES) |
| RU (1) | RU2586976C2 (enEXAMPLES) |
| SG (2) | SG182558A1 (enEXAMPLES) |
| TW (1) | TWI519546B (enEXAMPLES) |
| WO (1) | WO2011089092A1 (enEXAMPLES) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2763541C2 (ru) * | 2017-04-12 | 2021-12-30 | Релианс Индастрис Лимитид | Способ получения галогенированного изобутилен-изопренового каучука |
| RU2783209C1 (ru) * | 2018-12-21 | 2022-11-10 | Арланксео Сингапур Пте. Лтд. | Извлечение галогена в способе галогенирования ненасыщенного изоолефинового сополимера |
Families Citing this family (12)
| 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 |
| US10626201B2 (en) | 2014-04-30 | 2020-04-21 | Arlanxeo Singapore Pte. Ltd. | Butyl rubber with new sequence distribution |
| 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 |
| CA2955907A1 (en) * | 2014-07-24 | 2016-01-28 | Arlanxeo Singapore Pte. Ltd. | Ultrapure copolymers |
| EP3652223A1 (en) | 2017-07-12 | 2020-05-20 | ARLANXEO Deutschland GmbH | Process for the production of isoolefin polymers with improved initiator system preparation |
| WO2019011814A1 (en) | 2017-07-13 | 2019-01-17 | Arlanxeo Deutschland Gmbh | PROCESS FOR THE PRODUCTION OF ISOBUTENE POLYMERS WITH ENHANCED TEMPERATURE CONTROL |
| US12129319B2 (en) | 2018-12-17 | 2024-10-29 | Arlanxeo Singapore Pte. Ltd. | Process for the production of isoolefin polymers using a tertiary ether |
| CA3122590A1 (en) * | 2018-12-21 | 2020-06-25 | Arlanxeo Singapore Pte. Ltd. | Continuous process for producing halogenated isoolefin copolymer |
| WO2020132742A1 (en) | 2018-12-27 | 2020-07-02 | ARLANXEO Canada Inc. | Process for producing chlorinated butyl rubber |
| EP4105244B1 (en) | 2020-09-18 | 2024-09-04 | Lg Chem, Ltd. | Method for halogenating isobutene-isoprene copolymer |
Citations (7)
| 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 |
| 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 |
| US5681901A (en) * | 1996-07-24 | 1997-10-28 | Exxon Chemical Patents Inc. | Process for halogenating isomonoolefin copolymers |
| RU2148589C1 (ru) * | 1993-02-10 | 2000-05-10 | Прессиндустрия АГ | Непрерывный способ и устройство для галогенирования эластомеров |
| RU2177952C2 (ru) * | 1999-03-23 | 2002-01-10 | Щербань Георгий Трофимович | Способ получения галоидированного бутилкаучука |
| RU2263682C2 (ru) * | 2001-04-02 | 2005-11-10 | Открытое акционерное общество "Нижнекамскнефтехим" | Способ непрерывного получения галогенированных эластомеров и устройство для его осуществления |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| US5071913A (en) * | 1987-12-11 | 1991-12-10 | Exxon Chemical Patents Inc. | Rubbery isoolefin polymers exhibiting improved processability |
| US5182333A (en) * | 1987-12-11 | 1993-01-26 | Exxon Chemical Patents Inc. | Production of rubbery isoolefin polymers |
| US5021509A (en) | 1989-09-01 | 1991-06-04 | Exxon Chemical Patents Inc. | Butyl rubber compositions having improved adhesion to polyester |
| CA2252295C (en) * | 1998-10-30 | 2007-07-17 | Bayer Inc. | Improved process for preparation of butyl rubber utilizing activated alkylaluminum halides |
| JP5025843B2 (ja) * | 2000-03-03 | 2012-09-12 | 住友ゴム工業株式会社 | 外皮用ゴム組成物 |
| CA2308257A1 (en) * | 2000-05-05 | 2001-11-05 | Adam A. Gronowski | Process for preparation of butyl rubber having broad molecular weight distribution |
| TWI283257B (en) * | 2000-12-12 | 2007-07-01 | Lanxess Deutschland Gmbh | A process for the preparation of an isobutene/isoprene-copolymer |
| CA2329552C (en) * | 2000-12-22 | 2010-04-13 | Bayer Inc. | An improved process for the preparation of butyl rubber utilizing alkylaluminum dihalides and aluminoxanes |
| JP2005511829A (ja) * | 2001-12-10 | 2005-04-28 | エクソンモービル・ケミカル・パテンツ・インク | ハロゲン化イソオレフィン系ターポリマー |
| CA2390046A1 (en) * | 2002-06-28 | 2003-12-28 | Bayer Inc. | Method for improving the processability of butyl polymers |
| RU2373226C2 (ru) * | 2004-12-29 | 2009-11-20 | Эксонмобил Кемикэл Пейтентс Инк. | Подобранные эластомерные смеси и их применение в изделиях |
| DE602005018973D1 (de) * | 2005-10-27 | 2010-03-04 | Yokohama Rubber Co Ltd | Thermoplastische elastomerzusammensetzung mit geringer permeabilität |
| ATE511522T1 (de) * | 2005-12-28 | 2011-06-15 | Exxonmobil Chem Patents Inc | Halogenierungsverfahren |
| US7629397B2 (en) * | 2006-06-23 | 2009-12-08 | Exxonmobil Chemical Patents Inc. | Phase separation process utilizing a hydrofluorocarbon |
| CN100558762C (zh) * | 2006-08-03 | 2009-11-11 | 江苏圣杰实业有限公司 | 制造卤化橡胶状聚合物的方法 |
| CA2604409C (en) * | 2006-12-22 | 2015-04-07 | Lanxess Inc. | Butyl rubber ionomer nanocomposites |
| CN102083868B (zh) * | 2008-07-15 | 2013-06-19 | 朗盛国际股份公司 | 用于生产高分子量卤代丁基橡胶的常规溶剂方法 |
| KR101473542B1 (ko) * | 2010-01-20 | 2014-12-16 | 란세스 인터내쇼날 에스에이 | 고분자량 브로민화 고무를 제조하기 위한 공통 용매 방법 |
-
2011
- 2011-01-17 KR KR1020127021554A patent/KR20120120311A/ko not_active Ceased
- 2011-01-17 SG SG2012052510A patent/SG182558A1/en unknown
- 2011-01-17 JP JP2012549323A patent/JP5781092B2/ja active Active
- 2011-01-17 SG SG10201500432QA patent/SG10201500432QA/en unknown
- 2011-01-17 WO PCT/EP2011/050530 patent/WO2011089092A1/en active Application Filing
- 2011-01-17 RU RU2012135376/04A patent/RU2586976C2/ru active
- 2011-01-17 PL PL11700280T patent/PL2525987T3/pl unknown
- 2011-01-17 KR KR1020157004011A patent/KR101709022B1/ko not_active Expired - Fee Related
- 2011-01-17 CA CA2787228A patent/CA2787228C/en active Active
- 2011-01-17 CN CN201180008617.2A patent/CN102753359B/zh active Active
- 2011-01-17 IN IN6387DEN2012 patent/IN2012DN06387A/en unknown
- 2011-01-17 US US13/522,762 patent/US9273161B2/en active Active
- 2011-01-17 EP EP11700280.8A patent/EP2525987B1/en not_active Not-in-force
- 2011-01-17 MY MYPI2012003260A patent/MY162735A/en unknown
- 2011-01-19 TW TW100101876A patent/TWI519546B/zh not_active IP Right Cessation
Patent Citations (7)
| 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 |
| 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 |
| RU2148589C1 (ru) * | 1993-02-10 | 2000-05-10 | Прессиндустрия АГ | Непрерывный способ и устройство для галогенирования эластомеров |
| US5681901A (en) * | 1996-07-24 | 1997-10-28 | Exxon Chemical Patents Inc. | Process for halogenating isomonoolefin copolymers |
| RU2177952C2 (ru) * | 1999-03-23 | 2002-01-10 | Щербань Георгий Трофимович | Способ получения галоидированного бутилкаучука |
| RU2263682C2 (ru) * | 2001-04-02 | 2005-11-10 | Открытое акционерное общество "Нижнекамскнефтехим" | Способ непрерывного получения галогенированных эластомеров и устройство для его осуществления |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2763541C2 (ru) * | 2017-04-12 | 2021-12-30 | Релианс Индастрис Лимитид | Способ получения галогенированного изобутилен-изопренового каучука |
| RU2783209C1 (ru) * | 2018-12-21 | 2022-11-10 | Арланксео Сингапур Пте. Лтд. | Извлечение галогена в способе галогенирования ненасыщенного изоолефинового сополимера |
| RU2787159C1 (ru) * | 2018-12-21 | 2022-12-29 | Арланксео Сингапур Пте. Лтд. | Непрерывный способ получения галогенированного изоолефинового сополимера |
Also Published As
| Publication number | Publication date |
|---|---|
| US9273161B2 (en) | 2016-03-01 |
| EP2525987A1 (en) | 2012-11-28 |
| CA2787228A1 (en) | 2011-07-28 |
| EP2525987B1 (en) | 2016-08-24 |
| US20130137832A1 (en) | 2013-05-30 |
| TW201144331A (en) | 2011-12-16 |
| KR20150027844A (ko) | 2015-03-12 |
| SG10201500432QA (en) | 2015-03-30 |
| CN102753359A (zh) | 2012-10-24 |
| MY162735A (en) | 2017-07-14 |
| TWI519546B (zh) | 2016-02-01 |
| IN2012DN06387A (enEXAMPLES) | 2015-10-02 |
| JP5781092B2 (ja) | 2015-09-16 |
| KR20120120311A (ko) | 2012-11-01 |
| CN102753359B (zh) | 2015-12-16 |
| KR101709022B1 (ko) | 2017-02-21 |
| JP2013517362A (ja) | 2013-05-16 |
| PL2525987T3 (pl) | 2017-07-31 |
| RU2012135376A (ru) | 2014-02-27 |
| SG182558A1 (en) | 2012-08-30 |
| WO2011089092A1 (en) | 2011-07-28 |
| CA2787228C (en) | 2018-07-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2586976C2 (ru) | Способ получения высокомолекулярного галогенированного каучука с использованием общего растворителя | |
| RU2584424C2 (ru) | Способ получения высокомолекулярного бромированного каучука с использованием общего растворителя | |
| RU2510402C2 (ru) | Способ с общим растворителем для получения высокомолекулярного галогенированного бутилкаучука | |
| US9657158B2 (en) | Process for producing brominated butyl rubber | |
| RU2584255C2 (ru) | Способ производства галобутильных иономеров | |
| RU2559326C9 (ru) | Способ производства полимерных нанокомпозитов |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC41 | Official registration of the transfer of exclusive right |
Effective date: 20170417 |