DE2635790A1 - Neue vulkanisierbare olefin-copolymere - Google Patents
Neue vulkanisierbare olefin-copolymereInfo
- Publication number
- DE2635790A1 DE2635790A1 DE19762635790 DE2635790A DE2635790A1 DE 2635790 A1 DE2635790 A1 DE 2635790A1 DE 19762635790 DE19762635790 DE 19762635790 DE 2635790 A DE2635790 A DE 2635790A DE 2635790 A1 DE2635790 A1 DE 2635790A1
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- copolymers according
- reaction
- copolymers
- isobutene
- 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.)
- Pending
Links
- 229920000089 Cyclic olefin copolymer Polymers 0.000 title description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 47
- 229920000642 polymer Polymers 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 229920001577 copolymer Polymers 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 16
- 150000001993 dienes Chemical class 0.000 claims description 14
- 229920005549 butyl rubber Polymers 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 150000001336 alkenes Chemical class 0.000 claims description 8
- -1 polyene hydrocarbon Chemical class 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- CGMDPTNRMYIZTM-NKYSMPERSA-N (2e,4e,6e)-octa-2,4,6-triene Chemical compound C\C=C\C=C\C=C\C CGMDPTNRMYIZTM-NKYSMPERSA-N 0.000 description 8
- CGMDPTNRMYIZTM-UHFFFAOYSA-N Sarohornene Natural products CC=CC=CC=CC CGMDPTNRMYIZTM-UHFFFAOYSA-N 0.000 description 8
- 238000004073 vulcanization Methods 0.000 description 8
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 238000007334 copolymerization reaction Methods 0.000 description 5
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 238000013329 compounding Methods 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 4
- USKZHEQYENVSMH-YDFGWWAZSA-N 1,3,5-Heptatriene Chemical compound C\C=C\C=C\C=C USKZHEQYENVSMH-YDFGWWAZSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 150000004291 polyenes Chemical class 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- GQVMHMFBVWSSPF-SOYUKNQTSA-N (4E,6E)-2,6-dimethylocta-2,4,6-triene Chemical compound C\C=C(/C)\C=C\C=C(C)C GQVMHMFBVWSSPF-SOYUKNQTSA-N 0.000 description 2
- UBFBTMRIJJRZOA-AATRIKPKSA-N (4e)-2,7-dimethylocta-2,4,6-triene Chemical compound CC(C)=C\C=C\C=C(C)C UBFBTMRIJJRZOA-AATRIKPKSA-N 0.000 description 2
- AFVDZBIIBXWASR-AATRIKPKSA-N (E)-1,3,5-hexatriene Chemical compound C=C\C=C\C=C AFVDZBIIBXWASR-AATRIKPKSA-N 0.000 description 2
- LWHDQPLUIFIFFT-UHFFFAOYSA-N 2,3,5,6-tetrabromocyclohexa-2,5-diene-1,4-dione Chemical compound BrC1=C(Br)C(=O)C(Br)=C(Br)C1=O LWHDQPLUIFIFFT-UHFFFAOYSA-N 0.000 description 2
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 2
- GQVMHMFBVWSSPF-UHFFFAOYSA-N cis-alloocimene Natural products CC=C(C)C=CC=C(C)C GQVMHMFBVWSSPF-UHFFFAOYSA-N 0.000 description 2
- 229960003750 ethyl chloride Drugs 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 238000006011 modification reaction Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 150000005671 trienes Chemical class 0.000 description 2
- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 description 1
- BOBLSBAZCVBABY-WPWUJOAOSA-N 1,6-diphenylhexatriene Chemical compound C=1C=CC=CC=1\C=C\C=C\C=C\C1=CC=CC=C1 BOBLSBAZCVBABY-WPWUJOAOSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- DFWCPLGXFMSUCW-UHFFFAOYSA-N 3-(dimethylamino)propyl carbamimidothioate;hydron;dichloride Chemical compound Cl.Cl.CN(C)CCCSC(N)=N DFWCPLGXFMSUCW-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 229940082150 encore Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000006101 laboratory sample Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229940073584 methylene chloride Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005377 tertiary alkyl halides Chemical class 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 238000000196 viscometry Methods 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/04—Monomers containing three or four carbon atoms
- C08F210/08—Butenes
- C08F210/10—Isobutene
- C08F210/12—Isobutene with conjugated diolefins, e.g. butyl rubber
Landscapes
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT26222/75A IT1040387B (it) | 1975-08-08 | 1975-08-08 | Procedimento per la preparazione di copolimeri contenenti insatu razioni dieniche coniugate e copolimeri cosi ottenuti |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2635790A1 true DE2635790A1 (de) | 1977-02-10 |
Family
ID=11218978
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762635790 Pending DE2635790A1 (de) | 1975-08-08 | 1976-08-09 | Neue vulkanisierbare olefin-copolymere |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS5222083A (enExample) |
| AT (1) | AT345550B (enExample) |
| AU (1) | AU1641376A (enExample) |
| BE (1) | BE844976A (enExample) |
| CA (1) | CA1098648A (enExample) |
| DD (1) | DD125911A5 (enExample) |
| DE (1) | DE2635790A1 (enExample) |
| DK (1) | DK355376A (enExample) |
| ES (1) | ES450919A1 (enExample) |
| FI (1) | FI762253A7 (enExample) |
| FR (1) | FR2320315A1 (enExample) |
| GB (1) | GB1549645A (enExample) |
| IL (1) | IL50153A0 (enExample) |
| IT (1) | IT1040387B (enExample) |
| LU (1) | LU75554A1 (enExample) |
| NL (1) | NL7608849A (enExample) |
| NO (1) | NO762719L (enExample) |
| PT (1) | PT65449B (enExample) |
| SE (1) | SE7608869L (enExample) |
| ZA (1) | ZA764468B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113185639A (zh) * | 2021-04-29 | 2021-07-30 | 四川大学 | 一种高强度低松弛聚异戊二烯橡胶及其制备方法 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5454233A (en) * | 1977-10-07 | 1979-04-28 | Yahata Electric Works | High voltage generator |
| GB2110706B (en) * | 1981-12-11 | 1985-08-07 | Anic Spa | Isobutylene-triene copolymers |
| BRPI1107079A2 (pt) * | 2010-08-31 | 2013-01-22 | Goodyear Tire & Rubber | copolÍmeros de monâmeros de trieno conjugados para interaÇço melhorada com enchimento |
| CN116284528B (zh) * | 2023-02-20 | 2024-12-13 | 北京化工大学 | 一种异丁烯与别罗勒烯及其衍生物共聚物及其制备方法 |
-
1975
- 1975-08-08 IT IT26222/75A patent/IT1040387B/it active
-
1976
- 1976-07-26 ZA ZA764468A patent/ZA764468B/xx unknown
- 1976-07-28 IL IL50153A patent/IL50153A0/xx unknown
- 1976-07-30 AU AU16413/76A patent/AU1641376A/en not_active Expired
- 1976-08-05 FI FI762253A patent/FI762253A7/fi not_active Application Discontinuation
- 1976-08-05 NO NO762719A patent/NO762719L/no unknown
- 1976-08-06 SE SE7608869A patent/SE7608869L/xx unknown
- 1976-08-06 JP JP51093266A patent/JPS5222083A/ja active Pending
- 1976-08-06 DD DD194237A patent/DD125911A5/xx unknown
- 1976-08-06 ES ES450919A patent/ES450919A1/es not_active Expired
- 1976-08-06 PT PT65449A patent/PT65449B/pt unknown
- 1976-08-06 DK DK355376A patent/DK355376A/da unknown
- 1976-08-06 LU LU75554A patent/LU75554A1/xx unknown
- 1976-08-06 BE BE169634A patent/BE844976A/xx unknown
- 1976-08-09 NL NL7608849A patent/NL7608849A/xx not_active Application Discontinuation
- 1976-08-09 DE DE19762635790 patent/DE2635790A1/de active Pending
- 1976-08-09 AT AT590476A patent/AT345550B/de not_active IP Right Cessation
- 1976-08-09 FR FR7624351A patent/FR2320315A1/fr active Granted
- 1976-08-09 CA CA258,675A patent/CA1098648A/en not_active Expired
- 1976-08-09 GB GB32946/76A patent/GB1549645A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113185639A (zh) * | 2021-04-29 | 2021-07-30 | 四川大学 | 一种高强度低松弛聚异戊二烯橡胶及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5222083A (en) | 1977-02-19 |
| NO762719L (enExample) | 1977-02-09 |
| IT1040387B (it) | 1979-12-20 |
| FI762253A7 (enExample) | 1977-02-09 |
| LU75554A1 (enExample) | 1977-03-25 |
| NL7608849A (nl) | 1977-02-10 |
| ES450919A1 (es) | 1977-08-16 |
| AT345550B (de) | 1978-09-25 |
| PT65449A (en) | 1976-09-01 |
| BE844976A (fr) | 1977-02-07 |
| FR2320315A1 (fr) | 1977-03-04 |
| SE7608869L (sv) | 1977-02-09 |
| IL50153A0 (en) | 1976-09-30 |
| DD125911A5 (enExample) | 1977-06-01 |
| FR2320315B1 (enExample) | 1980-05-16 |
| PT65449B (en) | 1978-02-10 |
| ZA764468B (en) | 1977-09-28 |
| GB1549645A (en) | 1979-08-08 |
| ATA590476A (de) | 1978-01-15 |
| DK355376A (da) | 1977-02-09 |
| AU1641376A (en) | 1978-02-02 |
| CA1098648A (en) | 1981-03-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |