DE2123802C3 - Verfahren zur Herstellung eines Mischpolymerisates aus Propylen und einem polymerisierbaren Dien - Google Patents
Verfahren zur Herstellung eines Mischpolymerisates aus Propylen und einem polymerisierbaren DienInfo
- Publication number
- DE2123802C3 DE2123802C3 DE19712123802 DE2123802A DE2123802C3 DE 2123802 C3 DE2123802 C3 DE 2123802C3 DE 19712123802 DE19712123802 DE 19712123802 DE 2123802 A DE2123802 A DE 2123802A DE 2123802 C3 DE2123802 C3 DE 2123802C3
- Authority
- DE
- Germany
- Prior art keywords
- component
- propylene
- catalyst
- copolymer
- amount
- 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
Links
- 229920001577 copolymer Polymers 0.000 title claims description 30
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 title claims description 25
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 7
- 150000001993 dienes Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 239000003054 catalyst Substances 0.000 claims description 33
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 26
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 16
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- NLLZTRMHNHVXJJ-UHFFFAOYSA-J titanium tetraiodide Chemical compound I[Ti](I)(I)I NLLZTRMHNHVXJJ-UHFFFAOYSA-J 0.000 claims description 3
- 125000005287 vanadyl group Chemical group 0.000 claims description 3
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000007334 copolymerization reaction Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 6
- 229950011008 tetrachloroethylene Drugs 0.000 description 6
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- -1 polypropylene Polymers 0.000 description 5
- 230000032683 aging Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229920003193 cis-1,4-polybutadiene polymer Polymers 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000010355 oscillation Effects 0.000 description 2
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920005606 polypropylene copolymer Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- YLKNSDRJZIWQEH-UHFFFAOYSA-N ClC1=CC=C(C=C1)Cl.C(C)(C)(C)OO Chemical compound ClC1=CC=C(C=C1)Cl.C(C)(C)(C)OO YLKNSDRJZIWQEH-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000003679 aging effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- IHMJGECIBWVWIV-UHFFFAOYSA-N azet-2-yl(phenyl)methanone Chemical compound C=1C=CC=CC=1C(=O)C1=NC=C1 IHMJGECIBWVWIV-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- OEERIBPGRSLGEK-UHFFFAOYSA-N carbon dioxide;methanol Chemical compound OC.O=C=O OEERIBPGRSLGEK-UHFFFAOYSA-N 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- GYMBTLRVABDEHT-UHFFFAOYSA-N chlorobenzene;dichloromethane Chemical compound ClCCl.ClC1=CC=CC=C1 GYMBTLRVABDEHT-UHFFFAOYSA-N 0.000 description 1
- AILPTUURQRJHHF-UHFFFAOYSA-N diethyl(2-methylpropyl)alumane Chemical compound CC[Al](CC)CC(C)C AILPTUURQRJHHF-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000004941 influx Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 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
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000006864 oxidative decomposition reaction Methods 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000005401 pressed glass Substances 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- JQPMDTQDAXRDGS-UHFFFAOYSA-N triphenylalumane Chemical compound C1=CC=CC=C1[Al](C=1C=CC=CC=1)C1=CC=CC=C1 JQPMDTQDAXRDGS-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/04—Monomers containing three or four carbon atoms
- C08F210/06—Propene
-
- 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
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers 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
- C08F236/04—Copolymers 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
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4054670 | 1970-05-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2123802A1 DE2123802A1 (de) | 1971-11-18 |
| DE2123802B2 DE2123802B2 (de) | 1974-10-17 |
| DE2123802C3 true DE2123802C3 (de) | 1975-06-12 |
Family
ID=12583431
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712123802 Expired DE2123802C3 (de) | 1970-05-14 | 1971-05-13 | Verfahren zur Herstellung eines Mischpolymerisates aus Propylen und einem polymerisierbaren Dien |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE2123802C3 (enExample) |
| FR (1) | FR2091549A5 (enExample) |
| GB (1) | GB1327664A (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU172849B (hu) | 1975-08-19 | 1978-12-28 | Muenyagipari Kutato Intezet | Sposob poluchenija ehlastomernogo kopolimera iz izobutilena i butadiena |
| DE2706118C2 (de) * | 1977-02-14 | 1982-12-09 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von alternierenden aus Butadien- und Propyleneinheiten aufgebauten Copolymerisaten |
| WO2017040005A1 (en) | 2015-08-31 | 2017-03-09 | Bridgestone Corporation | Copolymerization of polyenes and alkenes |
| EP3428200B1 (en) * | 2016-03-11 | 2022-05-04 | JSR Corporation | Polymerization catalyst, copolymer, polymer composition, and crosslinked polymer |
-
1971
- 1971-05-13 DE DE19712123802 patent/DE2123802C3/de not_active Expired
- 1971-05-13 FR FR7117297A patent/FR2091549A5/fr not_active Expired
- 1971-05-13 GB GB1482871A patent/GB1327664A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2091549A5 (enExample) | 1972-01-14 |
| DE2123802A1 (de) | 1971-11-18 |
| DE2123802B2 (de) | 1974-10-17 |
| GB1327664A (en) | 1973-08-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1570275A1 (de) | Verfahren zur Herstellung von hohe cis-1,4-Anteile enthaltenden Mischpolymeren von Butadien mit Styrol oder alpha-Alkylstyrolen | |
| DE1420503A1 (de) | Verfahren zur Polymerisation von aethylenisch ungesaettigten Kohlenwasserstoffen | |
| DE2549168A1 (de) | Verfahren zur polymerisation von konjugierten diolefinmonomeren und katalysator zur durchfuehrung dieses verfahrens | |
| DE1795738B2 (de) | Polypentenamere, deren doppelbindungen im wesentlichen cis-konfiguration aufweisen | |
| DE2123802C3 (de) | Verfahren zur Herstellung eines Mischpolymerisates aus Propylen und einem polymerisierbaren Dien | |
| DE2437104A1 (de) | Verfahren zur herstellung von cyclopenten-copolymeren | |
| DE1089972B (de) | Herstellung von Misch-Polymerisaten aus olefinisch-ungesaettigten Monomeren | |
| DE1595184B1 (de) | Verfahren zur Polymerisation eines konjugierten Diens | |
| DE2315489C2 (de) | Elastomeres Copolymerisat aus Äthylen, mindestens einem alpha-Monoolefin von niedrigem Molekulargewicht und mindestens einem Trien sowie Verfahren zur Herstellung desselben | |
| DE1595293A1 (de) | Verfahren zum Herstellen von Mischpolymerisaten | |
| DE2441015A1 (de) | Katalysatorsysteme fuer die polymerisation von konjugierten diolefinen | |
| DE1816089B2 (de) | Verfahren zum herstellen von regellosen coplymeren aus conjugierten dienen mit 4 12 kohlenstoffatomen und vinylsubstitu ierten aromatischen kohlenwasserstoffen | |
| DE1595665C3 (de) | Verfahren zur Herstellung von Äthylenpolymerisaten | |
| DE1178601B (de) | Verfahren zur Herstellung von Mischpolymerisaten des Isobutylens | |
| DE1745267A1 (de) | Verfahren zur Herstellung von cis-1,4-Polymeren des Butadien | |
| DE1151941B (de) | Verfahren zur Herstellung von Mischpolymerisaten aus Dienpolymerisaten und ª‡-Olefinen | |
| DE1128145B (de) | Verfahren zur Herstellung eines Polymerisats mit trans-1,4-Struktur aus einem konjugierten diolefinischen Kohlenwasserstoff | |
| DE1258095B (de) | Verfahren zur Polymerisation von konjugierten Diolefinen | |
| DE2933609A1 (de) | Verfahren zur herstellung von 1.2-polybutadienen | |
| DE1745197A1 (de) | Polymerisationsverfahren | |
| DE2440951A1 (de) | Polymere des butadiens mit endstaendigen hydroxygruppen | |
| DE2359586A1 (de) | Verfahren zur polymerisation von ungesaettigten verbindungen | |
| DE1570275C (de) | Verfahren zur Herstellung von hohen eis 1,4 Anteile enthaltenden Mischpolyme ren von Butadien mit Styrol oder alpha Alkylstyrolen | |
| DE1901900A1 (de) | Verfahren zur Erhoehung des Molekulargewichtes von Polymerisaten und zur Einfuehrungvon Endgruppen | |
| DE2000119A1 (de) | Katalysatorsystem und Verfahren zur stereospezifischen Polymerisation von Butadien |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |