JP2003510380A - イソブチレン、ジオレフィンモノマーおよびスチレン系モノマーのハロゲン化ターポリマー - Google Patents
イソブチレン、ジオレフィンモノマーおよびスチレン系モノマーのハロゲン化ターポリマーInfo
- Publication number
- JP2003510380A JP2003510380A JP2001525244A JP2001525244A JP2003510380A JP 2003510380 A JP2003510380 A JP 2003510380A JP 2001525244 A JP2001525244 A JP 2001525244A JP 2001525244 A JP2001525244 A JP 2001525244A JP 2003510380 A JP2003510380 A JP 2003510380A
- Authority
- JP
- Japan
- Prior art keywords
- monomer
- halogenated butyl
- methyl
- polymer
- butyl polymer
- 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.)
- Revoked
Links
- 239000000178 monomer Substances 0.000 title claims abstract description 96
- 229920001897 terpolymer Polymers 0.000 title claims description 44
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 title claims description 22
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 title claims description 13
- 150000001993 dienes Chemical class 0.000 title 1
- 229920000642 polymer Polymers 0.000 claims abstract description 76
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 43
- 239000000203 mixture Substances 0.000 claims abstract description 39
- 150000005673 monoalkenes Chemical class 0.000 claims abstract description 23
- 230000032683 aging Effects 0.000 claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 24
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical group CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 230000002140 halogenating effect Effects 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical group CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 8
- RCJMVGJKROQDCB-UHFFFAOYSA-N 1,3-dimethyl-1,3-butadiene Natural products CC=CC(C)=C RCJMVGJKROQDCB-UHFFFAOYSA-N 0.000 claims description 6
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 claims description 6
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 claims description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 6
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 6
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 claims description 4
- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 claims description 3
- RCJMVGJKROQDCB-SNAWJCMRSA-N (3e)-2-methylpenta-1,3-diene Chemical compound C\C=C\C(C)=C RCJMVGJKROQDCB-SNAWJCMRSA-N 0.000 claims description 3
- BOGRNZQRTNVZCZ-AATRIKPKSA-N (3e)-3-methylpenta-1,3-diene Chemical compound C\C=C(/C)C=C BOGRNZQRTNVZCZ-AATRIKPKSA-N 0.000 claims description 3
- BOGRNZQRTNVZCZ-UHFFFAOYSA-N 1,2-dimethyl-butadiene Natural products CC=C(C)C=C BOGRNZQRTNVZCZ-UHFFFAOYSA-N 0.000 claims description 3
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 claims description 3
- JLSUFZZPRVNDIW-UHFFFAOYSA-N 1-ethenylcyclohexa-1,3-diene Chemical compound C=CC1=CC=CCC1 JLSUFZZPRVNDIW-UHFFFAOYSA-N 0.000 claims description 3
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 3
- DZPCYXCBXGQBRN-UHFFFAOYSA-N 2,5-Dimethyl-2,4-hexadiene Chemical compound CC(C)=CC=C(C)C DZPCYXCBXGQBRN-UHFFFAOYSA-N 0.000 claims description 3
- XNUNYHQZMMREQD-UHFFFAOYSA-N 2-methylhepta-1,6-diene Chemical compound CC(=C)CCCC=C XNUNYHQZMMREQD-UHFFFAOYSA-N 0.000 claims description 3
- SLQMKNPIYMOEGB-UHFFFAOYSA-N 2-methylhexa-1,5-diene Chemical compound CC(=C)CCC=C SLQMKNPIYMOEGB-UHFFFAOYSA-N 0.000 claims description 3
- DRWYRROCDFQZQF-UHFFFAOYSA-N 2-methylpenta-1,4-diene Chemical compound CC(=C)CC=C DRWYRROCDFQZQF-UHFFFAOYSA-N 0.000 claims description 3
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 claims description 3
- SUWJESCICIOQHO-UHFFFAOYSA-N 4-methylhex-1-ene Chemical compound CCC(C)CC=C SUWJESCICIOQHO-UHFFFAOYSA-N 0.000 claims description 3
- AQYKIROTAGYYQK-UHFFFAOYSA-N 5,5-dimethyl-3-methylidenehex-1-ene Chemical compound CC(C)(C)CC(=C)C=C AQYKIROTAGYYQK-UHFFFAOYSA-N 0.000 claims description 3
- NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 claims 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims 2
- MXXWOMGUGJBKIW-YPCIICBESA-N piperine Chemical compound C=1C=C2OCOC2=CC=1/C=C/C=C/C(=O)N1CCCCC1 MXXWOMGUGJBKIW-YPCIICBESA-N 0.000 claims 2
- 229940075559 piperine Drugs 0.000 claims 2
- WVWHRXVVAYXKDE-UHFFFAOYSA-N piperine Natural products O=C(C=CC=Cc1ccc2OCOc2c1)C3CCCCN3 WVWHRXVVAYXKDE-UHFFFAOYSA-N 0.000 claims 2
- 235000019100 piperine Nutrition 0.000 claims 2
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 claims 1
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 claims 1
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 claims 1
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 claims 1
- 229930006722 beta-pinene Natural products 0.000 claims 1
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 claims 1
- 229920005555 halobutyl Polymers 0.000 abstract description 9
- 238000005452 bending Methods 0.000 abstract description 3
- 230000003993 interaction Effects 0.000 abstract description 2
- 239000003431 cross linking reagent Substances 0.000 abstract 1
- 229920001971 elastomer Polymers 0.000 description 15
- 239000005060 rubber Substances 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 230000031709 bromination Effects 0.000 description 6
- 238000005893 bromination reaction Methods 0.000 description 6
- 229920005549 butyl rubber Polymers 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 238000010586 diagram Methods 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 238000001069 Raman spectroscopy Methods 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 3
- 239000008116 calcium stearate Substances 0.000 description 3
- 235000013539 calcium stearate Nutrition 0.000 description 3
- 239000004568 cement Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000004636 vulcanized rubber Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 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
- 238000002156 mixing Methods 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-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
- 230000009257 reactivity Effects 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 241001441571 Hiodontidae Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229920005557 bromobutyl Polymers 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
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- GQIJYUMTOUBHSH-IJIVKGSJSA-N piperyline Chemical compound C=1C=C2OCOC2=CC=1/C=C/C=C/C(=O)N1CCCC1 GQIJYUMTOUBHSH-IJIVKGSJSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000000518 rheometry Methods 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
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 239000003643 water by type 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
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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2,282,900 | 1999-09-20 | ||
| CA2282900A CA2282900C (en) | 1999-09-20 | 1999-09-20 | Halogenated terpolymers of isobutylene, diolefin monomer and styrenic monomer |
| PCT/CA2000/001044 WO2001021672A1 (en) | 1999-09-20 | 2000-09-19 | Halogenated terpolymers of isobutylene, diolefin monomer and styrenic monomer |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012000222A Division JP5450671B2 (ja) | 1999-09-20 | 2012-01-04 | イソブチレン、ジオレフィンモノマーおよびスチレン系モノマーのハロゲン化ターポリマー |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003510380A true JP2003510380A (ja) | 2003-03-18 |
| JP2003510380A5 JP2003510380A5 (enExample) | 2009-06-04 |
Family
ID=4164170
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001525244A Revoked JP2003510380A (ja) | 1999-09-20 | 2000-09-19 | イソブチレン、ジオレフィンモノマーおよびスチレン系モノマーのハロゲン化ターポリマー |
| JP2012000222A Expired - Lifetime JP5450671B2 (ja) | 1999-09-20 | 2012-01-04 | イソブチレン、ジオレフィンモノマーおよびスチレン系モノマーのハロゲン化ターポリマー |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012000222A Expired - Lifetime JP5450671B2 (ja) | 1999-09-20 | 2012-01-04 | イソブチレン、ジオレフィンモノマーおよびスチレン系モノマーのハロゲン化ターポリマー |
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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005060704A (ja) * | 2003-08-14 | 2005-03-10 | Bayer Inc | 過酸化物加硫性ブチル配合物 |
Families Citing this family (38)
| 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 |
| 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 |
| KR101467650B1 (ko) | 2010-03-24 | 2014-12-01 | 란세스 인터내쇼날 에스에이 | 고무 이오노머 및 중합체 나노복합체의 제조 방법 |
| CA2807732A1 (en) | 2010-08-13 | 2012-02-16 | Lanxess Inc. | Butyl ionomer latex |
| TW201235359A (en) | 2010-11-24 | 2012-09-01 | Lanxess Inc | Ionomers comprising pendant vinyl groups and processes for preparing same |
| JP2015502439A (ja) | 2011-12-22 | 2015-01-22 | ランクセス・インターナショナル・エス・アー | アジド化共重合体及びその製造方法 |
| JP2015500915A (ja) | 2011-12-22 | 2015-01-08 | ランクセス・インターナショナル・エス・アー | 硬化重合体の製造方法 |
| TW201518370A (zh) * | 2013-06-27 | 2015-05-16 | Lanxess Butyl Pte Ltd | 固化的彈性體及其製備方法 |
| CN104592466B (zh) * | 2013-10-30 | 2018-02-02 | 中国石油化工股份有限公司 | 一种卤化聚合物及其制备方法 |
| CN104592465B (zh) * | 2013-10-30 | 2017-03-08 | 中国石油化工股份有限公司 | 一种多嵌段卤化聚合物及其制备方法 |
| US12415915B2 (en) | 2018-02-20 | 2025-09-16 | Exxonmobil Chemical Patents Inc. | Isobutylene-containing compositions and articles made thereof |
| WO2019221919A1 (en) * | 2018-05-17 | 2019-11-21 | Exxonmobil Chemical Patents Inc. | Isobutylene-containing compositions and articles made thereof |
| WO2021126625A1 (en) | 2019-12-17 | 2021-06-24 | Exxonmobil Chemical Patents Inc. | Functionalized polymers tread additive for improved winter tire performance |
| EP4077528B1 (en) | 2019-12-17 | 2024-09-18 | ExxonMobil Chemical Patents Inc. | Functionalized polymers tread additive to improve all-season tire performance |
| WO2021126623A1 (en) | 2019-12-17 | 2021-06-24 | Exxonmobil Chemical Patents Inc. | Functionalized polymers as tread additive for improved wet braking and rolling resistance in high silica summer tire |
| US12459295B2 (en) | 2019-12-17 | 2025-11-04 | Exxonmobil Chemical Patents Inc. | Functionalized polymers tread additive to improve tire performance for immiscible all-season tread |
| CN114867783B (zh) | 2019-12-17 | 2024-10-22 | 埃克森美孚化学专利公司 | 用于改进含有高聚丁二烯水平的四季胎面的轮胎性能的官能化聚合物胎面添加剂 |
| CN114846069B (zh) | 2019-12-17 | 2024-08-27 | 埃克森美孚化学专利公司 | 用于改进低二氧化硅夏季轮胎的湿滑制动和滚动阻力的官能化聚合物胎面添加剂 |
| US20230039642A1 (en) | 2019-12-17 | 2023-02-09 | Exxonmobil Chemical Patents Inc. | Functionalized Polymers Tread Additive To Improve Truck And Bus Radial Tire Performance |
| US20250135684A1 (en) | 2021-10-29 | 2025-05-01 | ExxonMobil Technology and Engineering Company | Extrusion Processes |
| CN113968926B (zh) * | 2021-10-29 | 2023-01-13 | 大连理工大学 | 一类乙烯/α-烯烃/功能化苯乙烯衍生物三元共聚物及其制备方法 |
| EP4422839A1 (en) | 2021-10-29 | 2024-09-04 | ExxonMobil Chemical Patents Inc. | Method of forming a composition comprising a functionalized polymer |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51109989A (enExample) * | 1975-02-24 | 1976-09-29 | Goodyear Tire & Rubber | |
| JPS53130737A (en) * | 1977-04-09 | 1978-11-15 | Tokai Rubber Ind Ltd | Adhesive composition |
| JPS5714636A (en) * | 1980-06-13 | 1982-01-25 | Exxon Research Engineering Co | Chlorinated butyl rubber/brominated butyl rubber blend compound with improved adhesive properties |
| JPH02150408A (ja) * | 1988-05-27 | 1990-06-08 | Exxon Chem Patents Inc | パラ―アルキルスチレン／イソオレフィン共重合体 |
| JPH04224812A (ja) * | 1990-03-26 | 1992-08-14 | Goodyear Tire & Rubber Co:The | ハロブチルゴムの主鎖を有するコームポリマー |
| JPH05330307A (ja) * | 1992-06-02 | 1993-12-14 | Polytec Design:Kk | タイヤのインナーライナー |
| JPH08113006A (ja) * | 1995-08-31 | 1996-05-07 | Sumitomo Rubber Ind Ltd | 空気入りタイヤ |
| JPH1077376A (ja) * | 1996-08-06 | 1998-03-24 | Bayer Ag | 低ハロゲン含量のハロゲン化ブチルゴム |
| JP2001506286A (ja) * | 1996-08-01 | 2001-05-15 | エクソン・ケミカル・パテンツ・インク | 過酷さに耐えるエラストマーの用途用の低臭素イソブチレン―４―ブロモメチルスチレンコポリマー組成物 |
Family Cites Families (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2513183A (en) | 1945-02-09 | 1950-06-27 | Sun Oil Co | Copolymer products |
| US2497458A (en) | 1945-05-26 | 1950-02-14 | Sun Oil Co | Butadiene-styrene copolymer tackified with isoolefin-diolefin-styrene copolymer |
| US2539523A (en) | 1947-02-14 | 1951-01-30 | Atlantic Refining Co | Polymerization of olefin mixtures |
| US2631953A (en) | 1949-03-12 | 1953-03-17 | Standard Oil Dev Co | Bonding isoolefin-diolefin rubber to metal by an isoolefin-styrenediolefin resin and a modified natural rubber tie ply |
| FR65758E (enExample) * | 1950-04-18 | 1956-03-12 | ||
| NL170646B (nl) * | 1951-06-30 | Western Electric Co | Werkwijze voor het in een vlak oppervlak van een voorwerp vormen van verdiepte delen. | |
| US2676950A (en) | 1951-11-29 | 1954-04-27 | Standard Oil Dev Co | Low unsaturation curable tripolymer resins from a diolefin, an alkene and styrene orhomologue thereof |
| US2804448A (en) * | 1954-06-01 | 1957-08-27 | Goodrich Co B F | Novel method for preparing rubbery chlorinated isoolefin-polyolefin interpolymer derivatives |
| GB842557A (en) | 1956-07-16 | 1960-07-27 | Exxon Research Engineering Co | Chemical modification of isoolefin-multiolefin copolymers |
| US2891595A (en) | 1956-07-31 | 1959-06-23 | Exxon Research Engineering Co | Chlorinated rubbery copolymers |
| US2994578A (en) | 1957-04-04 | 1961-08-01 | Equipment Des Ind Chimiques S | Method of selectively separating hydrogen sulphide from gases containing hydrogen sulphide and carbon dioxide |
| US2968041A (en) | 1958-09-25 | 1961-01-17 | John F Skold | Applicator for surgical clamps |
| US2965621A (en) | 1959-01-02 | 1960-12-20 | Exxon Research Engineering Co | Process for halogenating rubbery copolymers |
| US3042662A (en) * | 1959-05-26 | 1962-07-03 | Exxon Research Engineering Co | Process for halogenating copolymers |
| US3560458A (en) | 1964-05-01 | 1971-02-02 | Exxon Research Engineering Co | Process for polymerization of cationically polymerizable monomers |
| US3948868A (en) | 1969-04-03 | 1976-04-06 | Exxon Research And Engineering Company | Homogeneous styrene/isoolefin copolymers |
| US3808177A (en) | 1971-06-08 | 1974-04-30 | Exxon Research Engineering Co | High molecular weight,high unsaturation c4-c10 isoolefin conjugated diene copolymers |
| US4026966A (en) | 1974-12-09 | 1977-05-31 | Exxon Research And Engineering Company | Preparation of modified elastomers |
| US4145490A (en) | 1975-09-25 | 1979-03-20 | E. I. Du Pont De Nemours And Company | Carboxylated copolymers of isobutylene and a vinylbenzene |
| US5162445A (en) | 1988-05-27 | 1992-11-10 | Exxon Chemical Patents Inc. | Para-alkylstyrene/isoolefin copolymers and functionalized copolymers thereof |
| US4779657A (en) | 1987-12-28 | 1988-10-25 | Polysar Limited | Rubber compositions |
| US6013727A (en) | 1988-05-27 | 2000-01-11 | Exxon Chemical Patents, Inc. | Thermoplastic blend containing engineering resin |
| EP0494857B1 (en) | 1989-10-03 | 1995-07-19 | Exxon Chemical Patents Inc. | Thermoplastic graft copolymers and their use as compatibilizers |
| WO1992011322A2 (en) | 1990-12-20 | 1992-07-09 | Exxon Chemical Patents Inc. | Uv/eb curable butyl copolymers for lithographic and corrosion-resistant coating applications |
| DE4401934A1 (de) | 1994-01-24 | 1995-07-27 | Sp Reifenwerke Gmbh | Kautschukmischung, daraus hergestellte Reifenlauffläche und Reifen mit dieser Reifenlauffläche |
| US5907234A (en) | 1995-08-04 | 1999-05-25 | Siemens Aktiengesellschaft | Thyristor-switched capacitor bank |
| DE19528766C1 (de) | 1995-08-04 | 1997-01-16 | Siemens Ag | Thyristorgeschaltete Kondensatorbank |
| CA2174794C (en) | 1996-04-23 | 2009-09-22 | Gabor Kaszas | Improved polymer bromination process in solution |
| US5681901A (en) * | 1996-07-24 | 1997-10-28 | Exxon Chemical Patents Inc. | Process for halogenating isomonoolefin copolymers |
| CA2282900C (en) | 1999-09-20 | 2011-02-01 | Bayer Inc. | Halogenated terpolymers of isobutylene, diolefin monomer and styrenic monomer |
| JP3529313B2 (ja) | 1999-12-27 | 2004-05-24 | 住友ゴム工業株式会社 | トレッド用ゴム組成物 |
| JP2002065898A (ja) | 2000-08-28 | 2002-03-05 | Sumitomo Rubber Ind Ltd | 糸巻きゴルフボール |
| WO2002098927A1 (en) | 2001-06-04 | 2002-12-12 | Exxonmobil Chemical Patents Inc. | Cured robber components for use with pharmaceutical devices |
| ITMI20012168A1 (it) | 2001-10-18 | 2003-04-18 | Enichem Spa | Polimeri vinilaromatici espandibili e procedimento per la loro preparazione |
| ATE428734T1 (de) | 2001-12-10 | 2009-05-15 | Exxonmobil Chem Patents Inc | Elastomere zusammensetzungen |
| US7329697B2 (en) | 2001-12-10 | 2008-02-12 | Exxonmobil Chemical Patents Inc. | Elastomeric compositions |
| CA2383474A1 (en) | 2002-04-26 | 2003-10-26 | Bayer Inc. | Rubber composition for tire treads |
| WO2004044051A1 (en) | 2002-11-07 | 2004-05-27 | Exxonmobil Chemical Patents Inc. | Elastomeric blend for air barriers comprising low glass transition temperature petroleum hydrocarbon resins |
| DE10360592A1 (de) | 2003-12-19 | 2005-07-28 | Beiersdorf Ag | Pflastersystem zur Verabreichung von Antihistaminika |
-
1999
- 1999-09-20 CA CA2282900A patent/CA2282900C/en not_active Expired - Lifetime
-
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
-
2003
- 2003-03-17 US US10/390,113 patent/US6960632B2/en not_active Expired - Lifetime
-
2005
- 2005-08-19 US US11/208,320 patent/US7402633B2/en not_active Expired - Lifetime
-
2008
- 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
-
2012
- 2012-01-04 JP JP2012000222A patent/JP5450671B2/ja not_active Expired - Lifetime
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51109989A (enExample) * | 1975-02-24 | 1976-09-29 | Goodyear Tire & Rubber | |
| JPS53130737A (en) * | 1977-04-09 | 1978-11-15 | Tokai Rubber Ind Ltd | Adhesive composition |
| JPS5714636A (en) * | 1980-06-13 | 1982-01-25 | Exxon Research Engineering Co | Chlorinated butyl rubber/brominated butyl rubber blend compound with improved adhesive properties |
| JPH02150408A (ja) * | 1988-05-27 | 1990-06-08 | Exxon Chem Patents Inc | パラ―アルキルスチレン／イソオレフィン共重合体 |
| JPH04224812A (ja) * | 1990-03-26 | 1992-08-14 | Goodyear Tire & Rubber Co:The | ハロブチルゴムの主鎖を有するコームポリマー |
| JPH05330307A (ja) * | 1992-06-02 | 1993-12-14 | Polytec Design:Kk | タイヤのインナーライナー |
| JPH08113006A (ja) * | 1995-08-31 | 1996-05-07 | Sumitomo Rubber Ind Ltd | 空気入りタイヤ |
| JP2001506286A (ja) * | 1996-08-01 | 2001-05-15 | エクソン・ケミカル・パテンツ・インク | 過酷さに耐えるエラストマーの用途用の低臭素イソブチレン―４―ブロモメチルスチレンコポリマー組成物 |
| JPH1077376A (ja) * | 1996-08-06 | 1998-03-24 | Bayer Ag | 低ハロゲン含量のハロゲン化ブチルゴム |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005060704A (ja) * | 2003-08-14 | 2005-03-10 | Bayer Inc | 過酸化物加硫性ブチル配合物 |
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 |
| TW591042B (en) | 2004-06-11 |
| RU2002110664A (ru) | 2003-11-20 |
| CN1159351C (zh) | 2004-07-28 |
| EP1228106A1 (en) | 2002-08-07 |
| 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 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2003510380A (ja) | イソブチレン、ジオレフィンモノマーおよびスチレン系モノマーのハロゲン化ターポリマー | |
| KR100195663B1 (ko) | 타이어 트레드용 조성물 | |
| JP2764765B2 (ja) | タイヤカーカス用組成物 | |
| US5182333A (en) | Production of rubbery isoolefin polymers | |
| US20070203306A1 (en) | Method of halogenating butyl rubber without acid neutralization agents | |
| EP0678529A2 (en) | Improved processing isoolefin polymers | |
| JP2715185B2 (ja) | タイヤインナーライナー用組成物 | |
| CA2106311C (en) | Composition for mold curing elements | |
| WO1992016587A2 (en) | Composition for mold curing elements | |
| JP2557304B2 (ja) | タイヤのサイドウォール用組成物 | |
| DE60302177T2 (de) | Gummimischung für Reifenlaufflächen | |
| WO1991019761A1 (en) | Composition for dynamic means | |
| HK1050539B (en) | Halogenated terpolymers of isobutylene, diolefin monomer and styrenic monomer | |
| USH1922H (en) | Coating composition |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20070919 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20070919 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20081202 |
|
| A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A711 Effective date: 20090309 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20100607 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20100615 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20100914 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20100922 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20101013 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20101020 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20101215 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20110125 |
|
| AA91 | Notification that invitation to amend document was cancelled |
Free format text: JAPANESE INTERMEDIATE CODE: A971091 Effective date: 20110208 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110322 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20110622 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20110629 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110720 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20110830 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120104 |
|
| A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20120123 |
|
| A912 | Re-examination (zenchi) completed and case transferred to appeal board |
Free format text: JAPANESE INTERMEDIATE CODE: A912 Effective date: 20120217 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20121120 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20121126 |