CN1159351C - 异丁烯、二烯烃单体和苯乙烯系单体的卤化三元共聚物 - Google Patents
异丁烯、二烯烃单体和苯乙烯系单体的卤化三元共聚物 Download PDFInfo
- Publication number
- CN1159351C CN1159351C CNB00813135XA CN00813135A CN1159351C CN 1159351 C CN1159351 C CN 1159351C CN B00813135X A CNB00813135X A CN B00813135XA CN 00813135 A CN00813135 A CN 00813135A CN 1159351 C CN1159351 C CN 1159351C
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- China
- Prior art keywords
- monomer
- polymer
- butyl polymer
- halogenated butyl
- methyl
- 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 - Lifetime
Links
- 239000000178 monomer Substances 0.000 title claims abstract description 66
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 title claims description 7
- 229920001897 terpolymer Polymers 0.000 title description 36
- 150000001993 dienes Chemical class 0.000 title 1
- 229920000642 polymer Polymers 0.000 claims abstract description 48
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 30
- 239000000203 mixture Substances 0.000 claims abstract description 26
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- 230000003679 aging effect Effects 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 7
- 230000026030 halogenation Effects 0.000 claims description 6
- 238000005658 halogenation reaction Methods 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 4
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 4
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 4
- 238000003878 thermal aging Methods 0.000 claims description 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims description 2
- JLSUFZZPRVNDIW-UHFFFAOYSA-N 1-ethenylcyclohexa-1,3-diene Chemical compound C=CC1=CC=CCC1 JLSUFZZPRVNDIW-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
- -1 bromobutyl Chemical group 0.000 claims description 2
- 229920005557 bromobutyl Polymers 0.000 claims description 2
- NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 claims description 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N ethyl ethylene Natural products CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 1
- 229920005555 halobutyl Polymers 0.000 abstract description 9
- 230000003993 interaction Effects 0.000 abstract description 2
- 239000003431 cross linking reagent Substances 0.000 abstract 1
- 150000005673 monoalkenes Chemical class 0.000 abstract 1
- 229920001971 elastomer Polymers 0.000 description 22
- 230000032683 aging Effects 0.000 description 14
- 230000031709 bromination Effects 0.000 description 14
- 238000005893 bromination reaction Methods 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 11
- 229910052794 bromium Inorganic materials 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 238000003483 aging Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VHOQXEIFYTTXJU-UHFFFAOYSA-N Isobutylene-isoprene copolymer Chemical group CC(C)=C.CC(=C)C=C VHOQXEIFYTTXJU-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-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
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000004568 cement Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 239000004636 vulcanized rubber Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 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 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 238000001069 Raman spectroscopy Methods 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 229920005549 butyl rubber Polymers 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 125000003454 indenyl group Chemical class C1(C=CC2=CC=CC=C12)* 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
- 239000011414 polymer cement Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 230000003245 working effect Effects 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 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
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 230000000996 additive 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
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000428 dust Substances 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
- 230000002140 halogenating effect Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 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
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000011218 segmentation Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 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
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005486 sulfidation Methods 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 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
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- 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)
Abstract
Description
实施例 | [p-MeSt]1(mol/L) | [St]1(mol/L) | Mw,×103 | Mw/Mn | [IP](mol%) | [p-MeSt]2(mol%) | [St]2(mol%) |
1 | - | - | 474 | 4.3 | 1.37 | - | - |
2 | 0.055 | - | 440 | 2.9 | 1.26 | 2.63 | - |
3 | 0.11 | - | 375 | 2.9 | 1.12 | 5.3 | - |
4 | 0.22 | - | 400 | 2.2 | 0.86 | 10.6 | - |
5 | - | 0.055 | 580 | 4.2 | 1.24 | - | 0.83 |
6 | - | 0.11 | 540 | 4.6 | 1.15 | - | 1.71 |
7 | - | 0.22 | 475 | 4.4 | 1.00 | - | 3.58 |
实施例 | 1 | 2 | 3 | 4 | 5 | 6 | 7 |
溴化前 | |||||||
1,4-IP(mol%) | 1.46 | 1.26 | 1.12 | 0.86 | 1.24 | 1.15 | 1 |
p-MeSt(mol%) | - | 2.63 | 5.3 | 10.6 | - | - | - |
St(mol%) | - | - | - | - | 0.83 | 1.71 | 3.6 |
溴化后 | |||||||
p-MeSt(mol%) | - | 2.69 | 5.29 | 11.3 | - | - | - |
St(mol%) | - | - | - | - | 0.97 | 1.81 | 4.05 |
1,4-IP(mol%) | 0.39 | 0.21 | 0.16 | 0 | 0.44 | 0.3 | 0.3 |
外取代(mol%) | 0.97 | 0.87 | 0.79 | 0.63 | 0.71 | 0.85 | 0.7 |
内取代(mol%) | 0.05 | 0.04 | 0.04 | 0.03 | 0.04 | 0.05 | 0.03 |
内取代CDB(mol%) | 0.03 | 0.02 | 0.02 | 0.02 | 0.02 | 0.03 | 0.03 |
总的一级溴化结构(mol%) | 1.05 | 0.93 | 0.85 | 0.68 | 0.77 | 0.93 | 0.76 |
实施例 | pMeSt(mol%) | St(mol%) | 由HNMR测得的Br含量(mol%) | 由氧瓶燃烧测得的Br含量(mol%) |
1 | - | - | 1.02 | 1.16 |
2 | 2.69 | - | 1.02 | 1.04 |
3 | 5.29 | - | 0.95 | 1.13 |
4 | 11.26 | - | 0.84 | 1.33 |
5 | - | 0.97 | 0.78 | 1.3 |
6 | - | 1.81 | 0.9 | 1.49 |
7 | - | 4.05 | 0.73 | 1.54 |
实施例 | 1 | 2 | 3 | 4 | 5 | 6 | 7 |
外取代(mol%) | 0.97 | 0.87 | 0.79 | 0.63 | 0.71 | 0.85 | 0.7 |
pMeSt(mol%) | - | 2.69 | 5.29 | 11.26 | - | - | - |
St(mol%) | - | - | - | - | 0.97 | 1.81 | 4.05 |
焦烧时间01(min.) | 10.26 | 2.71 | 2.89 | 4.24 | 4.84 | 3.63 | 4.18 |
Tc50(min.) | 13.36 | 4.03 | 4.12 | 5.78 | 6.59 | 5.02 | 5.77 |
Tc90(min.) | 21.31 | 6.74 | 10.25 | 20.91 | 9.69 | 10.75 | 9.71 |
Mh(dNm) | 18.57 | 22.48 | 18.79 | 17.98 | 18.35 | 18.81 | 20.69 |
Ml(dNm) | 7.77 | 8.51 | 6.35 | 7 | 8.97 | 6.47 | 8.4 |
δ扭矩(dNm) | 10.81 | 13.96 | 12.43 | 10.98 | 9.37 | 12.35 | 12.29 |
实施例 | 1 | 2 | 3 | 5 | 6 | 7 |
未老化的 | ||||||
模量@100%(MPa) | 0.33 | 0.38 | 0.37 | 0.39 | 0.42 | 0.4 |
模量@300%(MPa) | 0.45 | 0.56 | 0.52 | 0.56 | 0.6 | 0.63 |
最终拉伸强度(MPa) | 3.5 | 2.1 | 2.7 | 4.1 | 4 | 3.4 |
最终伸长率(%) | 1055 | 910 | 1020 | 965 | 880 | 850 |
硬度Shore A2(pts.) | 23 | 26 | 28 | 25 | 24 | 25 |
120℃下在空气中老化168小时 | ||||||
模量@100%(MPa) | 0.36 | 0.41 | 0.4 | - | - | - |
模量@300%(MPa) | 0.67 | 0.75 | 0.72 | - | - | - |
最终拉伸强度(MPa) | 2.6 | 1.9 | 1.9 | - | - | - |
最终伸长率(%) | 670 | 570 | 595 | - | - | - |
硬度Shore A2(pts.) | 26 | 28 | 28 | - | - | - |
实施例 | 1 | 2 | 3 | 5 | 6 | 7 |
140℃下在空气中老化168小时 | ||||||
模量@100%(MPa) | 0.17 | 0.3 | 0.29 | 0.27 | - | - |
模量@300%(MPa) | 0.29 | 0.53 | 0.51 | 0.47 | - | - |
最终拉伸强度(MPa) | 1.8 | 2.1 | 2.2 | 2.8 | - | - |
最终伸长率(%) | 805 | 670 | 725 | 850 | - | - |
硬度Shore A2(pts) | 23 | 27 | 26 | 21 | - | - |
Claims (6)
Applications Claiming Priority (2)
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 |
CA2282900 | 1999-09-20 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1374972A CN1374972A (zh) | 2002-10-16 |
CN1159351C true CN1159351C (zh) | 2004-07-28 |
Family
ID=4164170
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB00813135XA Expired - Lifetime CN1159351C (zh) | 1999-09-20 | 2000-09-19 | 异丁烯、二烯烃单体和苯乙烯系单体的卤化三元共聚物 |
Country Status (11)
Country | Link |
---|---|
US (4) | US6960632B2 (zh) |
EP (1) | EP1228106B1 (zh) |
JP (2) | JP2003510380A (zh) |
CN (1) | CN1159351C (zh) |
AU (1) | AU7262900A (zh) |
BR (2) | BR0014125A (zh) |
CA (1) | CA2282900C (zh) |
HK (1) | HK1050539A1 (zh) |
RU (1) | RU2002110664A (zh) |
TW (1) | TW591042B (zh) |
WO (1) | WO2001021672A1 (zh) |
Families Citing this family (39)
Publication number | Priority date | Publication date | Assignee | Title |
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CA2282900C (en) * | 1999-09-20 | 2011-02-01 | Bayer Inc. | Halogenated terpolymers of isobutylene, diolefin monomer and styrenic monomer |
CN1602320B (zh) * | 2001-12-10 | 2011-06-15 | 埃克森美孚化学专利公司 | 弹性体组合物 |
CA2469348A1 (en) * | 2001-12-10 | 2003-06-19 | Exxonmobil Chemical Patents Inc. | Halogenated isoolefin based terpolymers |
EP1465948A4 (en) * | 2001-12-10 | 2004-12-29 | Exxonmobil Chem Patents Inc | ELASTOMERIC COMPOSITIONS |
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 |
RU2485148C9 (ru) * | 2007-10-19 | 2013-11-10 | Лэнксесс Инк. | Смеси на основе бутилового каучука, содержащие трехкомпонентную смешанную систему модификаторов |
EP2396374B1 (en) | 2009-02-13 | 2020-08-05 | ARLANXEO Deutschland GmbH | Butyl ionomers for use in reducing a population of and/or preventing accumulation of organisms and coatings made therefrom |
CA2752504A1 (en) | 2009-02-13 | 2010-08-19 | Lanxess Inc. | Recycled butyl ionomers and recycling processes |
GB2474356A (en) * | 2009-10-07 | 2011-04-13 | Bromine Compounds Ltd | Preparation of bromine-containing copolymers |
WO2011117277A1 (en) | 2010-03-24 | 2011-09-29 | Lanxess International Sa | Process for the production of rubber ionomers and polymer nanocomposites |
SG183822A1 (en) | 2010-03-24 | 2012-10-30 | Lanxess Int Sa | Process for the production of water and solvent-free polymers |
KR101562430B1 (ko) | 2010-03-24 | 2015-10-21 | 란세스 인터내쇼날 에스에이 | 무수 무용매 할로부틸 고무의 제조 방법 |
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TW201235359A (en) | 2010-11-24 | 2012-09-01 | Lanxess Inc | Ionomers comprising pendant vinyl groups and processes for preparing same |
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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 JP JP2001525244A patent/JP2003510380A/ja not_active Revoked
- 2000-09-19 BR BR0014125-9A patent/BR0014125A/pt not_active Application Discontinuation
- 2000-09-19 EP EP00960245.9A patent/EP1228106B1/en not_active Expired - Lifetime
- 2000-09-19 WO PCT/CA2000/001044 patent/WO2001021672A1/en active Application Filing
- 2000-09-19 BR BRPI0017502-1A patent/BR0017502B1/pt not_active IP Right Cessation
- 2000-09-19 CN CNB00813135XA patent/CN1159351C/zh not_active Expired - Lifetime
- 2000-09-19 AU AU72629/00A patent/AU7262900A/en not_active Abandoned
- 2000-09-19 RU RU2002110664/04A patent/RU2002110664A/ru not_active Application Discontinuation
- 2000-09-20 TW TW089119287A patent/TW591042B/zh not_active IP Right Cessation
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2003
- 2003-03-17 US US10/390,113 patent/US6960632B2/en not_active Expired - Lifetime
- 2003-04-10 HK HK03102633A patent/HK1050539A1/xx not_active IP Right Cessation
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2005
- 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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US7868100B2 (en) | 2011-01-11 |
CN1374972A (zh) | 2002-10-16 |
US7402633B2 (en) | 2008-07-22 |
US20080275190A1 (en) | 2008-11-06 |
EP1228106A1 (en) | 2002-08-07 |
BR0017502B1 (pt) | 2013-03-05 |
HK1050539A1 (en) | 2003-06-27 |
BR0014125A (pt) | 2002-05-14 |
RU2002110664A (ru) | 2003-11-20 |
WO2001021672A1 (en) | 2001-03-29 |
CA2282900A1 (en) | 2001-03-20 |
US20030220454A1 (en) | 2003-11-27 |
CA2282900C (en) | 2011-02-01 |
TW591042B (en) | 2004-06-11 |
JP2012062492A (ja) | 2012-03-29 |
EP1228106B1 (en) | 2016-03-16 |
US20060116484A1 (en) | 2006-06-01 |
JP5450671B2 (ja) | 2014-03-26 |
JP2003510380A (ja) | 2003-03-18 |
US6960632B2 (en) | 2005-11-01 |
US20090018297A1 (en) | 2009-01-15 |
AU7262900A (en) | 2001-04-24 |
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