CA1244999A - Extrusion process for preparing improved brominated butyl rubber - Google Patents
Extrusion process for preparing improved brominated butyl rubberInfo
- Publication number
- CA1244999A CA1244999A CA000491856A CA491856A CA1244999A CA 1244999 A CA1244999 A CA 1244999A CA 000491856 A CA000491856 A CA 000491856A CA 491856 A CA491856 A CA 491856A CA 1244999 A CA1244999 A CA 1244999A
- Authority
- CA
- Canada
- Prior art keywords
- polymer
- butyl rubber
- bromine
- rubber
- reaction
- 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
Links
- 229920005557 bromobutyl Polymers 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title description 4
- 238000001125 extrusion Methods 0.000 title description 3
- 229920000642 polymer Polymers 0.000 claims abstract description 150
- 238000006243 chemical reaction Methods 0.000 claims abstract description 80
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 78
- 238000000034 method Methods 0.000 claims abstract description 64
- 229920005549 butyl rubber Polymers 0.000 claims abstract description 57
- 230000008569 process Effects 0.000 claims abstract description 51
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 39
- 230000002140 halogenating effect Effects 0.000 claims abstract description 39
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 35
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000002253 acid Substances 0.000 claims abstract description 21
- 239000006227 byproduct Substances 0.000 claims abstract description 17
- 238000005893 bromination reaction Methods 0.000 claims abstract description 16
- 230000031709 bromination Effects 0.000 claims abstract description 13
- 125000000746 allylic group Chemical group 0.000 claims abstract description 12
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 5
- 229920001971 elastomer Polymers 0.000 claims description 45
- 239000005060 rubber Substances 0.000 claims description 44
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 21
- 238000002156 mixing Methods 0.000 claims description 20
- 239000003085 diluting agent Substances 0.000 claims description 14
- 239000011261 inert gas Substances 0.000 claims description 13
- 238000002347 injection Methods 0.000 claims description 13
- 239000007924 injection Substances 0.000 claims description 13
- 239000007789 gas Substances 0.000 claims description 9
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 8
- 230000008707 rearrangement Effects 0.000 claims description 6
- 230000002844 continuous effect Effects 0.000 claims description 4
- 238000005204 segregation Methods 0.000 claims description 4
- VHOQXEIFYTTXJU-UHFFFAOYSA-N Isobutylene-isoprene copolymer Chemical group CC(C)=C.CC(=C)C=C VHOQXEIFYTTXJU-UHFFFAOYSA-N 0.000 claims description 3
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 claims description 3
- 238000012546 transfer Methods 0.000 claims description 3
- JIRDGEGGAWJQHQ-UHFFFAOYSA-N disulfur dibromide Chemical compound BrSSBr JIRDGEGGAWJQHQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 abstract description 2
- 238000005658 halogenation reaction Methods 0.000 description 32
- 230000026030 halogenation Effects 0.000 description 27
- 239000000047 product Substances 0.000 description 19
- 229910052736 halogen Inorganic materials 0.000 description 18
- 238000006386 neutralization reaction Methods 0.000 description 18
- 150000002367 halogens Chemical class 0.000 description 17
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 14
- 239000000463 material Substances 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 150000002500 ions Chemical class 0.000 description 10
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 9
- 150000001993 dienes Chemical group 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- -1 e.g. Substances 0.000 description 8
- 229920005555 halobutyl Polymers 0.000 description 8
- 230000010006 flight Effects 0.000 description 7
- 230000002441 reversible effect Effects 0.000 description 7
- 239000003381 stabilizer Substances 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- 229920002943 EPDM rubber Polymers 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 5
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 5
- 239000008116 calcium stearate Substances 0.000 description 5
- 235000013539 calcium stearate Nutrition 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229920000098 polyolefin Polymers 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000005201 scrubbing Methods 0.000 description 5
- 238000007086 side reaction Methods 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 125000001246 bromo group Chemical group Br* 0.000 description 4
- 238000005660 chlorination reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 239000012433 hydrogen halide Substances 0.000 description 4
- 229910000039 hydrogen halide Inorganic materials 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- 229920003244 diene elastomer Polymers 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 239000002516 radical scavenger Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 2
- 239000005751 Copper oxide Substances 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- DKSMCEUSSQTGBK-UHFFFAOYSA-M bromite Chemical compound [O-]Br=O DKSMCEUSSQTGBK-UHFFFAOYSA-M 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 229910000431 copper oxide Inorganic materials 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000013467 fragmentation Methods 0.000 description 2
- 238000006062 fragmentation reaction Methods 0.000 description 2
- 229910000856 hastalloy Inorganic materials 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 238000013021 overheating Methods 0.000 description 2
- 238000010094 polymer processing Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000002000 scavenging effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 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
- SODQFLRLAOALCF-UHFFFAOYSA-N 1lambda3-bromacyclohexa-1,3,5-triene Chemical compound Br1=CC=CC=C1 SODQFLRLAOALCF-UHFFFAOYSA-N 0.000 description 1
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000331231 Amorphocerini gen. n. 1 DAD-2008 Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 101100065700 Caenorhabditis elegans etc-1 gene Proteins 0.000 description 1
- 101100402341 Caenorhabditis elegans mpk-1 gene Proteins 0.000 description 1
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- 229910000975 Carbon steel Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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- DINOPBPYOCMGGD-VEDJBHDQSA-N Man(a1-2)Man(a1-2)Man(a1-3)[Man(a1-2)Man(a1-3)[Man(a1-2)Man(a1-6)]Man(a1-6)]Man(b1-4)GlcNAc(b1-4)GlcNAc Chemical compound O[C@@H]1[C@@H](NC(=O)C)C(O)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O[C@H]2[C@H]([C@@H](O[C@@H]3[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O[C@@H]3[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O[C@@H]3[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)[C@H](O)[C@@H](CO[C@@H]3[C@H]([C@@H](O[C@@H]4[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)O[C@@H]4[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)O)[C@H](O)[C@@H](CO[C@@H]4[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)O[C@@H]4[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)O)O3)O)O2)O)[C@@H](CO)O1 DINOPBPYOCMGGD-VEDJBHDQSA-N 0.000 description 1
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- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- GZZMEFFUSRGCNW-UHFFFAOYSA-N [Br].[Br] Chemical compound [Br].[Br] GZZMEFFUSRGCNW-UHFFFAOYSA-N 0.000 description 1
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- 239000011651 chromium Substances 0.000 description 1
- AHICWQREWHDHHF-UHFFFAOYSA-N chromium;cobalt;iron;manganese;methane;molybdenum;nickel;silicon;tungsten Chemical compound C.[Si].[Cr].[Mn].[Fe].[Co].[Ni].[Mo].[W] AHICWQREWHDHHF-UHFFFAOYSA-N 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
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- 230000008961 swelling Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
-
- 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
- C08C19/12—Incorporating halogen atoms into the molecule
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/656,664 US4563506A (en) | 1984-09-17 | 1984-10-01 | Extrusion process for preparing improved brominated butyl rubber |
| US656,664 | 1991-02-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1244999A true CA1244999A (en) | 1988-11-15 |
Family
ID=24634033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000491856A Expired CA1244999A (en) | 1984-10-01 | 1985-09-30 | Extrusion process for preparing improved brominated butyl rubber |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4563506A (instruction) |
| EP (1) | EP0197104B1 (instruction) |
| AU (1) | AU591641B2 (instruction) |
| CA (1) | CA1244999A (instruction) |
| DE (1) | DE3584090D1 (instruction) |
| ES (1) | ES8609378A1 (instruction) |
| IN (1) | IN165756B (instruction) |
| NO (1) | NO863101D0 (instruction) |
| WO (1) | WO1986002082A1 (instruction) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4634741A (en) * | 1984-04-05 | 1987-01-06 | Exxon Research & Engineering Co. | Process for preparing improved halogenated butyl rubbers |
| US4649178A (en) * | 1984-10-01 | 1987-03-10 | Exxon Research & Engineering Co. | Process for producing brominated butyl rubber high in primary allylic bromine |
| US5034468A (en) * | 1988-09-15 | 1991-07-23 | Exxon Chemical Patents Inc. | N-halothiosulfonamide modified rubber products |
| US5017662A (en) * | 1988-09-15 | 1991-05-21 | Exxon Chemical Patents, Inc. | Selective catalytic process for preparing N-halothiosulfonamide modified EPDM terpolymers |
| US5034467A (en) * | 1988-09-15 | 1991-07-23 | Exxon Chemical Patents, Inc. | N-halothiosulfonamide-modified non-rubbery thermoplastic polyolefins |
| US5037896A (en) * | 1988-09-15 | 1991-08-06 | Exxon Chemical Patents Inc. | Selective catalytic process for preparing N-halothiosulfonamide modified polyolefins |
| US4956420A (en) * | 1988-09-15 | 1990-09-11 | Exxon Chemical Patents Inc. | Selective catalytic process for controlled modification of ethylene-(alpha-olefin)-diene monomer terpolymer with halothisulfonamide |
| US5102958A (en) * | 1989-12-22 | 1992-04-07 | Exxon Chemical Patents Inc. | Partially crosslinked elastomeric polymers and process for producing the same |
| US5075387A (en) * | 1989-12-22 | 1991-12-24 | Exxon Chemical Patents Inc. | Partially crosslinked elastomeric polymers and process for producing the same |
| FR2681869A1 (fr) * | 1991-09-26 | 1993-04-02 | Atochem | Polypropylene modifie brome a cristallinite controlee, son procede de fabrication et son utilisation comme agent de collage. |
| CA2308442C (en) | 1997-10-28 | 2009-09-01 | Castrol Limited | Processes for preparing grafted copolymers |
| CA2575652A1 (en) * | 2006-02-15 | 2007-08-15 | Lanxess Inc. | Method of halogenating butyl rubber without acid neutralization agents |
| US20120016091A1 (en) * | 2010-07-15 | 2012-01-19 | Parent J Scott | Halogenated Butyl Rubber Having Superior Reactivity |
| DE102013111066A1 (de) * | 2013-10-07 | 2015-04-09 | List Holding Ag | Verfahren zum Herstellen von Halobutyl-Kautschuk |
| CN108472618B (zh) | 2016-01-29 | 2020-04-28 | 埃克森美孚化学专利公司 | 用于生产官能化烯烃基聚合物的系统和方法 |
| WO2024205925A1 (en) * | 2023-03-24 | 2024-10-03 | The University Of North Carolina At Chapel Hill | Depolymerization of aminated all-carbon polymer backbones through aza-cope rearrangements |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE610390A (instruction) * | 1956-12-03 | |||
| BE624565A (instruction) * | 1961-11-09 | |||
| FR2013391A6 (instruction) * | 1968-07-20 | 1970-04-03 | Manifattura Ceramica Poz | |
| BE793236A (fr) * | 1971-12-23 | 1973-06-22 | Stamicarbon | Procede de preparation de copolymeres caoutchouteux halogenes |
| AU7032374A (en) * | 1973-06-28 | 1976-01-08 | Dover Chemical Corp | Chlorbrominated polyisoprene |
| DE2430325A1 (de) * | 1973-06-28 | 1975-01-16 | Dover Chemical Corp | Chlorbromiertes polybutadien und butadien-isopren-copolymere |
| US4185057A (en) * | 1974-05-15 | 1980-01-22 | W Bar E, Inc. | Dewatering of plastic materials with controlled gaseous injection |
| US4288575A (en) * | 1978-12-04 | 1981-09-08 | Exxon Research & Engineering Co. | Conjugated diene butyl elastomer copolymer |
| US4384072A (en) * | 1981-09-30 | 1983-05-17 | Exxon Research & Engineering Co. | Process for the manufacture of halogenated elastomers |
| US4554326A (en) * | 1983-04-01 | 1985-11-19 | Exxon Research & Engineering Co. | Process for the manufacture of halogenated polymers |
| JPS59184204A (ja) * | 1983-04-01 | 1984-10-19 | エクソン・リサ−チ・アンド・エンジニアリング・カンパニ− | ハロゲン化ポリマ−の製造方法 |
-
1984
- 1984-10-01 US US06/656,664 patent/US4563506A/en not_active Expired - Fee Related
-
1985
- 1985-09-26 DE DE8585905024T patent/DE3584090D1/de not_active Expired - Lifetime
- 1985-09-26 WO PCT/US1985/001856 patent/WO1986002082A1/en active IP Right Grant
- 1985-09-26 AU AU49615/85A patent/AU591641B2/en not_active Ceased
- 1985-09-26 EP EP85905024A patent/EP0197104B1/en not_active Expired - Lifetime
- 1985-09-30 ES ES547423A patent/ES8609378A1/es not_active Expired
- 1985-09-30 CA CA000491856A patent/CA1244999A/en not_active Expired
- 1985-10-03 IN IN805/DEL/85A patent/IN165756B/en unknown
-
1986
- 1986-07-31 NO NO1986863101A patent/NO863101D0/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU4961585A (en) | 1986-04-17 |
| NO863101L (no) | 1986-07-31 |
| ES547423A0 (es) | 1986-09-01 |
| US4563506A (en) | 1986-01-07 |
| NO863101D0 (no) | 1986-07-31 |
| IN165756B (instruction) | 1990-01-06 |
| DE3584090D1 (de) | 1991-10-17 |
| WO1986002082A1 (en) | 1986-04-10 |
| EP0197104A4 (en) | 1987-02-03 |
| EP0197104B1 (en) | 1991-09-11 |
| ES8609378A1 (es) | 1986-09-01 |
| EP0197104A1 (en) | 1986-10-15 |
| AU591641B2 (en) | 1989-12-14 |
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| CA1244999A (en) | Extrusion process for preparing improved brominated butyl rubber | |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |