TW591042B - A halogenated butyl polymer and the process for preparing the same - Google Patents
A halogenated butyl polymer and the process for preparing the same Download PDFInfo
- Publication number
- TW591042B TW591042B TW089119287A TW89119287A TW591042B TW 591042 B TW591042 B TW 591042B TW 089119287 A TW089119287 A TW 089119287A TW 89119287 A TW89119287 A TW 89119287A TW 591042 B TW591042 B TW 591042B
- Authority
- TW
- Taiwan
- Prior art keywords
- polymer
- monomer
- weight
- weight percent
- halogenated butyl
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 64
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 title claims abstract description 32
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000000178 monomer Substances 0.000 claims abstract description 55
- 239000000203 mixture Substances 0.000 claims abstract description 32
- 150000005673 monoalkenes Chemical class 0.000 claims abstract description 12
- 230000003679 aging effect Effects 0.000 claims abstract description 6
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical group CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 7
- 229920001897 terpolymer Polymers 0.000 claims description 7
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005977 Ethylene Substances 0.000 claims description 6
- 230000002079 cooperative effect Effects 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 230000002140 halogenating effect Effects 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 4
- 239000000539 dimer Substances 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 230000005070 ripening Effects 0.000 claims description 4
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims 8
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 claims 4
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims 4
- -1 3-Pentylpenta-1,3-diene Chemical compound 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- JLSUFZZPRVNDIW-UHFFFAOYSA-N 1-ethenylcyclohexa-1,3-diene Chemical compound C=CC1=CC=CCC1 JLSUFZZPRVNDIW-UHFFFAOYSA-N 0.000 claims 2
- RCJMVGJKROQDCB-UHFFFAOYSA-N 2-methylpenta-1,3-diene Chemical compound CC=CC(C)=C RCJMVGJKROQDCB-UHFFFAOYSA-N 0.000 claims 2
- 150000001993 dienes Chemical class 0.000 claims 2
- NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 claims 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims 1
- PIMKIZUVIMAVSF-UHFFFAOYSA-N 1-(2-phenylethyl)-9h-fluorene Chemical compound C=1C=CC=2C3=CC=CC=C3CC=2C=1CCC1=CC=CC=C1 PIMKIZUVIMAVSF-UHFFFAOYSA-N 0.000 claims 1
- LLVWLCAZSOLOTF-UHFFFAOYSA-N 1-methyl-4-[1,4,4-tris(4-methylphenyl)buta-1,3-dienyl]benzene Chemical compound C1=CC(C)=CC=C1C(C=1C=CC(C)=CC=1)=CC=C(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 LLVWLCAZSOLOTF-UHFFFAOYSA-N 0.000 claims 1
- PZDCDQOCUSGCQZ-UHFFFAOYSA-N 1-prop-1-en-2-yl-9H-fluorene Chemical compound C1C2=CC=CC=C2C2=C1C(C(=C)C)=CC=C2 PZDCDQOCUSGCQZ-UHFFFAOYSA-N 0.000 claims 1
- DZPCYXCBXGQBRN-UHFFFAOYSA-N 2,5-Dimethyl-2,4-hexadiene Chemical compound CC(C)=CC=C(C)C DZPCYXCBXGQBRN-UHFFFAOYSA-N 0.000 claims 1
- CNPVJWYWYZMPDS-UHFFFAOYSA-N 2-methyldecane Chemical compound CCCCCCCCC(C)C CNPVJWYWYZMPDS-UHFFFAOYSA-N 0.000 claims 1
- XNUNYHQZMMREQD-UHFFFAOYSA-N 2-methylhepta-1,6-diene Chemical compound CC(=C)CCCC=C XNUNYHQZMMREQD-UHFFFAOYSA-N 0.000 claims 1
- SLQMKNPIYMOEGB-UHFFFAOYSA-N 2-methylhexa-1,5-diene Chemical compound CC(=C)CCC=C SLQMKNPIYMOEGB-UHFFFAOYSA-N 0.000 claims 1
- DRWYRROCDFQZQF-UHFFFAOYSA-N 2-methylpenta-1,4-diene Chemical compound CC(=C)CC=C DRWYRROCDFQZQF-UHFFFAOYSA-N 0.000 claims 1
- IWTYTFSSTWXZFU-UHFFFAOYSA-N 3-chloroprop-1-enylbenzene Chemical compound ClCC=CC1=CC=CC=C1 IWTYTFSSTWXZFU-UHFFFAOYSA-N 0.000 claims 1
- SUWJESCICIOQHO-UHFFFAOYSA-N 4-methylhex-1-ene Chemical compound CCC(C)CC=C SUWJESCICIOQHO-UHFFFAOYSA-N 0.000 claims 1
- VDVYFCGXZAUSBJ-UHFFFAOYSA-N C1(=CC=CC=2C3=CC=CC=C3CC12)C(CC=C)C Chemical compound C1(=CC=CC=2C3=CC=CC=C3CC12)C(CC=C)C VDVYFCGXZAUSBJ-UHFFFAOYSA-N 0.000 claims 1
- HOKMCLIFBCNTSO-UHFFFAOYSA-N CC(=CC=C(C)C1=CC=CC2=C1CC3=CC=CC=C32)C4=CC=CC5=C4CC6=CC=CC=C65 Chemical compound CC(=CC=C(C)C1=CC=CC2=C1CC3=CC=CC=C32)C4=CC=CC5=C4CC6=CC=CC=C65 HOKMCLIFBCNTSO-UHFFFAOYSA-N 0.000 claims 1
- JYNNGBORKIYNMX-UHFFFAOYSA-N CC(CCC(C)C1=CC=CC2=C1CC3=CC=CC=C32)C4=CC=CC5=C4CC6=CC=CC=C65 Chemical compound CC(CCC(C)C1=CC=CC2=C1CC3=CC=CC=C32)C4=CC=CC5=C4CC6=CC=CC=C65 JYNNGBORKIYNMX-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229940127089 cytotoxic agent Drugs 0.000 claims 1
- APPOKADJQUIAHP-UHFFFAOYSA-N hexa-2,4-diene Chemical compound CC=CC=CC APPOKADJQUIAHP-UHFFFAOYSA-N 0.000 claims 1
- 230000035800 maturation Effects 0.000 claims 1
- 239000013589 supplement Substances 0.000 claims 1
- 229920005555 halobutyl Polymers 0.000 abstract description 2
- 239000003431 cross linking reagent Substances 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- 239000013638 trimer Substances 0.000 description 18
- 230000032683 aging Effects 0.000 description 15
- 229920001971 elastomer Polymers 0.000 description 14
- 239000005060 rubber Substances 0.000 description 14
- 229920005549 butyl rubber Polymers 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 230000007423 decrease Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000004636 vulcanized rubber Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 235000021355 Stearic acid Nutrition 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
- 239000008117 stearic acid Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000031709 bromination Effects 0.000 description 3
- 238000005893 bromination reaction Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000779 smoke Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 230000003712 anti-aging effect Effects 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000011414 polymer cement Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 238000005829 trimerization reaction Methods 0.000 description 2
- BJEMXPVDXFSROA-UHFFFAOYSA-N 3-butylbenzene-1,2-diol Chemical compound CCCCC1=CC=CC(O)=C1O BJEMXPVDXFSROA-UHFFFAOYSA-N 0.000 description 1
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241001441571 Hiodontidae Species 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- 238000001069 Raman spectroscopy Methods 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229920005557 bromobutyl Polymers 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 239000013521 mastic Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- BJEYNNFDAPPGST-UHFFFAOYSA-N oxirene Chemical compound O1C=C1 BJEYNNFDAPPGST-UHFFFAOYSA-N 0.000 description 1
- 238000009840 oxygen flask method Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000007613 slurry method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 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
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)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2282900A CA2282900C (en) | 1999-09-20 | 1999-09-20 | Halogenated terpolymers of isobutylene, diolefin monomer and styrenic monomer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW591042B true TW591042B (en) | 2004-06-11 |
Family
ID=4164170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW089119287A TW591042B (en) | 1999-09-20 | 2000-09-20 | A halogenated butyl polymer and the process for preparing the same |
Country Status (10)
| Country | Link |
|---|---|
| US (4) | US6960632B2 (enExample) |
| EP (1) | EP1228106B1 (enExample) |
| JP (2) | JP2003510380A (enExample) |
| CN (1) | CN1159351C (enExample) |
| AU (1) | AU7262900A (enExample) |
| BR (2) | BR0017502B1 (enExample) |
| CA (1) | CA2282900C (enExample) |
| RU (1) | RU2002110664A (enExample) |
| TW (1) | TW591042B (enExample) |
| WO (1) | WO2001021672A1 (enExample) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2282900C (en) * | 1999-09-20 | 2011-02-01 | Bayer Inc. | Halogenated terpolymers of isobutylene, diolefin monomer and styrenic monomer |
| RU2303044C2 (ru) * | 2001-12-10 | 2007-07-20 | Эксонмобил Кемикэл Пейтентс Инк. | Галогенированные тройные сополимеры на изоолефиновой основе и их использование в композициях для применения в пневматической диафрагме, такой как внутренняя оболочка шины или камера для пневматической шины |
| US7329697B2 (en) | 2001-12-10 | 2008-02-12 | Exxonmobil Chemical Patents Inc. | Elastomeric compositions |
| ATE428734T1 (de) * | 2001-12-10 | 2009-05-15 | Exxonmobil Chem Patents Inc | Elastomere zusammensetzungen |
| CA2383474A1 (en) * | 2002-04-26 | 2003-10-26 | Bayer Inc. | Rubber composition for tire treads |
| CA2438024C (en) * | 2003-08-14 | 2013-05-28 | Bayer Inc. | Peroxide curable butyl formulations |
| CA2465407C (en) * | 2004-04-28 | 2012-11-13 | Rui Resendes | Peroxide curable butyl formulations |
| CA2551997C (en) * | 2005-08-26 | 2014-05-27 | Lanxess Inc. | Novel methods for the preparation of butyl graft copolymers |
| US7294768B1 (en) | 2005-09-27 | 2007-11-13 | Monsanto Technology Llc | Soybean variety 0384279 |
| EP2502742B1 (en) | 2005-10-27 | 2017-06-21 | ExxonMobil Chemical Patents Inc. | Construction comprising tie layer for pneumatic tire |
| US7585914B2 (en) * | 2005-11-09 | 2009-09-08 | Exxonmobil Chemical Patents Inc. | Thermoplastic elastomer compositions and methods for making the same |
| CA2575652A1 (en) * | 2006-02-15 | 2007-08-15 | Lanxess Inc. | Method of halogenating butyl rubber without acid neutralization agents |
| US7767743B2 (en) * | 2006-03-10 | 2010-08-03 | Exxonmobil Chemical Patents Inc. | Processable branched isoolefin-alkylstyrene elastomers |
| BRPI0818579A2 (pt) * | 2007-10-19 | 2011-09-13 | Lanxess Inc | compostos de borracha de butila compreendendo um sistema modificador de três componentes mistos |
| JP5632858B2 (ja) | 2009-02-13 | 2014-11-26 | ランクセス・インク． | 再生ブチルアイオノマー及び再生方法 |
| BRPI1008436A2 (pt) | 2009-02-13 | 2020-02-27 | Lanxess Inc. | Ionomeros de butila para uso na reducao de uma populacao de e/ou prevencao do acumulo de organismos e revestimentos feitos a partir deles |
| GB2474356A (en) * | 2009-10-07 | 2011-04-13 | Bromine Compounds Ltd | Preparation of bromine-containing copolymers |
| MY160881A (en) | 2010-03-24 | 2017-03-31 | Arlanxeo Deutschland Gmbh | Process for the production of water and solvent-free polymers |
| WO2011117297A1 (en) | 2010-03-24 | 2011-09-29 | Lanxess International Sa | Process for the production of water and solvent-free halobutyl rubbers |
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1999
- 1999-09-20 CA CA2282900A patent/CA2282900C/en not_active Expired - Lifetime
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2000
- 2000-09-19 BR BRPI0017502-1A patent/BR0017502B1/pt not_active IP Right Cessation
- 2000-09-19 JP JP2001525244A patent/JP2003510380A/ja not_active Revoked
- 2000-09-19 BR BR0014125-9A patent/BR0014125A/pt not_active Application Discontinuation
- 2000-09-19 RU RU2002110664/04A patent/RU2002110664A/ru not_active Application Discontinuation
- 2000-09-19 WO PCT/CA2000/001044 patent/WO2001021672A1/en not_active Ceased
- 2000-09-19 EP EP00960245.9A patent/EP1228106B1/en not_active Expired - Lifetime
- 2000-09-19 CN CNB00813135XA patent/CN1159351C/zh not_active Expired - Lifetime
- 2000-09-19 AU AU72629/00A patent/AU7262900A/en not_active Abandoned
- 2000-09-20 TW TW089119287A patent/TW591042B/zh not_active IP Right Cessation
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- 2003-03-17 US US10/390,113 patent/US6960632B2/en not_active Expired - Lifetime
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- 2005-08-19 US US11/208,320 patent/US7402633B2/en not_active Expired - Lifetime
-
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- 2008-06-03 US US12/156,501 patent/US20090018297A1/en not_active Abandoned
- 2008-06-25 US US12/146,078 patent/US7868100B2/en not_active Expired - Fee Related
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- 2012-01-04 JP JP2012000222A patent/JP5450671B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP5450671B2 (ja) | 2014-03-26 |
| BR0017502B1 (pt) | 2013-03-05 |
| CA2282900C (en) | 2011-02-01 |
| CN1374972A (zh) | 2002-10-16 |
| WO2001021672A1 (en) | 2001-03-29 |
| RU2002110664A (ru) | 2003-11-20 |
| CN1159351C (zh) | 2004-07-28 |
| EP1228106A1 (en) | 2002-08-07 |
| JP2003510380A (ja) | 2003-03-18 |
| US6960632B2 (en) | 2005-11-01 |
| JP2012062492A (ja) | 2012-03-29 |
| US20090018297A1 (en) | 2009-01-15 |
| US7402633B2 (en) | 2008-07-22 |
| US20080275190A1 (en) | 2008-11-06 |
| EP1228106B1 (en) | 2016-03-16 |
| HK1050539A1 (en) | 2003-06-27 |
| US20030220454A1 (en) | 2003-11-27 |
| US20060116484A1 (en) | 2006-06-01 |
| BR0014125A (pt) | 2002-05-14 |
| US7868100B2 (en) | 2011-01-11 |
| AU7262900A (en) | 2001-04-24 |
| CA2282900A1 (en) | 2001-03-20 |
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