DE1253917B - Verfahren zur Loesungspolymerisation von Isopren - Google Patents
Verfahren zur Loesungspolymerisation von IsoprenInfo
- Publication number
- DE1253917B DE1253917B DEF46132A DEF0046132A DE1253917B DE 1253917 B DE1253917 B DE 1253917B DE F46132 A DEF46132 A DE F46132A DE F0046132 A DEF0046132 A DE F0046132A DE 1253917 B DE1253917 B DE 1253917B
- Authority
- DE
- Germany
- Prior art keywords
- weight
- parts
- polymerization
- isoprene
- catalyst
- 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.)
- Ceased
Links
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 title claims description 40
- 238000000034 method Methods 0.000 title claims description 14
- 238000010528 free radical solution polymerization reaction Methods 0.000 title claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 35
- 239000003054 catalyst Substances 0.000 claims description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 15
- 229910052782 aluminium Inorganic materials 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000001350 alkyl halides Chemical class 0.000 claims description 7
- 150000003609 titanium compounds Chemical class 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- 239000000460 chlorine Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 7
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 229920001195 polyisoprene Polymers 0.000 description 6
- -1 titanium (IV) chloride Isoprene Chemical compound 0.000 description 6
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 125000001246 bromo group Chemical group Br* 0.000 description 4
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229920003211 cis-1,4-polyisoprene Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QXSZNDIIPUOQMB-UHFFFAOYSA-N 1,1,2,2-tetrabromoethane Chemical compound BrC(Br)C(Br)Br QXSZNDIIPUOQMB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- QUMDOMSJJIFTCA-UHFFFAOYSA-N 1,1,2-tribromoethane Chemical compound BrCC(Br)Br QUMDOMSJJIFTCA-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RJMDFMUPJANPGX-UHFFFAOYSA-N 1,2-dibromo-1,2-dichloroethane Chemical compound ClC(Br)C(Cl)Br RJMDFMUPJANPGX-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- AQZGPSLYZOOYQP-UHFFFAOYSA-N Diisoamyl ether Chemical compound CC(C)CCOCCC(C)C AQZGPSLYZOOYQP-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 241001441571 Hiodontidae Species 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure 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
- C08F136/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F136/02—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F136/04—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F136/08—Isoprene
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF46132A DE1253917B (de) | 1965-05-24 | 1965-05-24 | Verfahren zur Loesungspolymerisation von Isopren |
| US532587A US3502636A (en) | 1965-05-24 | 1966-03-08 | Solution polymerization of isoprene with aluminium trialkyl titanium tetrachloride catalyst activated by ethers and halogenated alkanes |
| NL666606139A NL149187B (nl) | 1965-05-24 | 1966-05-05 | Werkwijze voor de bereiding van polyisopreen met overwegend 1,4-cis-bindingen. |
| GB22928/66A GB1073329A (en) | 1965-05-24 | 1966-05-23 | Solution polymerization of isoprene with aluminium trialkyl titanium tetrachloride catalysts |
| FR62595A FR1480824A (fr) | 1965-05-24 | 1966-05-23 | Polymérisation en solution de l'isoprène en présence de catalyseurs de trialkylaluminium/tétrachlorure de titane, activés par des éthers et des alcanes halogénés |
| BE681438D BE681438A (enExample) | 1965-05-24 | 1966-05-23 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF46132A DE1253917B (de) | 1965-05-24 | 1965-05-24 | Verfahren zur Loesungspolymerisation von Isopren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1253917B true DE1253917B (de) | 1967-11-09 |
Family
ID=7100856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF46132A Ceased DE1253917B (de) | 1965-05-24 | 1965-05-24 | Verfahren zur Loesungspolymerisation von Isopren |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3502636A (enExample) |
| BE (1) | BE681438A (enExample) |
| DE (1) | DE1253917B (enExample) |
| FR (1) | FR1480824A (enExample) |
| GB (1) | GB1073329A (enExample) |
| NL (1) | NL149187B (enExample) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB817308A (en) * | 1956-07-02 | 1959-07-29 | Kellogg M W Co | Novel catalyst composition, preparation and use thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL103545C (enExample) * | 1956-01-18 | |||
| BE559727A (enExample) * | 1956-08-02 | |||
| US3180858A (en) * | 1961-03-09 | 1965-04-27 | Phillips Petroleum Co | Molecular weight control of cis-polyisoprene |
-
1965
- 1965-05-24 DE DEF46132A patent/DE1253917B/de not_active Ceased
-
1966
- 1966-03-08 US US532587A patent/US3502636A/en not_active Expired - Lifetime
- 1966-05-05 NL NL666606139A patent/NL149187B/xx unknown
- 1966-05-23 BE BE681438D patent/BE681438A/xx unknown
- 1966-05-23 GB GB22928/66A patent/GB1073329A/en not_active Expired
- 1966-05-23 FR FR62595A patent/FR1480824A/fr not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB817308A (en) * | 1956-07-02 | 1959-07-29 | Kellogg M W Co | Novel catalyst composition, preparation and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6606139A (enExample) | 1966-11-25 |
| NL149187B (nl) | 1976-04-15 |
| BE681438A (enExample) | 1966-10-31 |
| US3502636A (en) | 1970-03-24 |
| FR1480824A (fr) | 1967-05-12 |
| GB1073329A (en) | 1967-06-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0011184B2 (de) | Katalysator, dessen Herstellung und Verwendung zur Lösungspolymerisation von konjugierten Dienen | |
| DE69004712T2 (de) | Verfahren zur Herstellung von Polybutadien mit verbesserter Verarbeitkeit. | |
| DE2027905B2 (de) | Verfahren zur herstellung von polyalkenameren | |
| DE1223559B (de) | Verfahren zur Herstellung von cis-1, 4-Polyisopren | |
| DE2028935C3 (de) | Polyalkenamere und Verfahren zu deren Herstellung | |
| DE1213120B (de) | Verfahren zur Polymerisation von Butadien | |
| DE2830080A1 (de) | Katalysator, dessen herstellung und verwendung zur loesungspolymerisation von butadien | |
| DE1445365B2 (de) | Verfahren zum Polymerisieren von Isopren | |
| EP0217004B1 (de) | Verfahren zur Einstellung der cis-trans-Doppelbindungskonfiguration bei Polyalkenameren | |
| DE2046722A1 (de) | Verfahren zur Herstellung cyclischer oelfimsch ungesättigter Kohlenwasser stoff polymere | |
| DE1795738A1 (de) | Polypentenamere, deren doppelbindungen im wesentlichen cis-konfiguration aufweisen | |
| DE1945358C3 (de) | Niedermolekulare Polyalkenamere und Verfahren zu deren Herstellung | |
| DE2105161B2 (de) | Verfahren zur herstellung von fluessigen polybutenameren | |
| DE2028716C3 (de) | Verfahren zur Herstellung von Polyalkenameren | |
| DE1253917B (de) | Verfahren zur Loesungspolymerisation von Isopren | |
| DE2838303A1 (de) | Verfahren zur herstellung von cyclopentenpolymeren und -copolymeren | |
| DE1251029B (de) | Verfah ren zur Polymerisation \on Isopren | |
| DE1909226C3 (de) | Verfahren zur Herstellung von Cycloolefinpolymeri säten | |
| DE1151941B (de) | Verfahren zur Herstellung von Mischpolymerisaten aus Dienpolymerisaten und ª‡-Olefinen | |
| DE1943360A1 (de) | Verfahren zur Polymerisation ungesaettigter alicyclischer Verbindungen | |
| DE2006776C3 (enExample) | ||
| DE2046063C3 (de) | Verfahren zur Herstellung von Polyisopren | |
| DE1251033B (de) | I Verfahren zur katalytischen Polymerisation oder Mischpolymerisation von Diolefmen | |
| DE1520479B2 (de) | Verfahren zur Herstellung von cis-1,4-Polybutadien | |
| AT275852B (de) | Verfahren zur Herstellung von Mischpolymerisaten kontrollierten Molekulargewichtes |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHV | Ceased/renunciation |