DE1165862B - Verfahren zur Herstellung von linearen kristallinen Polypentadienen - Google Patents
Verfahren zur Herstellung von linearen kristallinen PolypentadienenInfo
- Publication number
- DE1165862B DE1165862B DEM52818A DEM0052818A DE1165862B DE 1165862 B DE1165862 B DE 1165862B DE M52818 A DEM52818 A DE M52818A DE M0052818 A DEM0052818 A DE M0052818A DE 1165862 B DE1165862 B DE 1165862B
- Authority
- DE
- Germany
- Prior art keywords
- cis
- cobalt
- pentadiene
- polypentadiene
- process according
- 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
- 238000000034 method Methods 0.000 title claims description 18
- 229920000642 polymer Polymers 0.000 claims description 23
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims description 18
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 8
- 150000001869 cobalt compounds Chemical class 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 8
- 229930192474 thiophene Natural products 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims description 7
- 125000005234 alkyl aluminium group Chemical group 0.000 claims description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Chemical class 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 239000002879 Lewis base Substances 0.000 claims description 4
- 150000007527 lewis bases Chemical class 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- -1 Cobalt halide Chemical class 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- 150000004700 cobalt complex Chemical class 0.000 claims description 3
- 229920002521 macromolecule Polymers 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 150000001868 cobalt Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 229940125904 compound 1 Drugs 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 238000006116 polymerization reaction Methods 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- 238000002441 X-ray diffraction Methods 0.000 description 5
- 239000008139 complexing agent Substances 0.000 description 5
- BKFAZDGHFACXKY-UHFFFAOYSA-N cobalt(II) bis(acetylacetonate) Chemical compound [Co+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O BKFAZDGHFACXKY-UHFFFAOYSA-N 0.000 description 4
- AMFIJXSMYBKJQV-UHFFFAOYSA-L cobalt(2+);octadecanoate Chemical compound [Co+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AMFIJXSMYBKJQV-UHFFFAOYSA-L 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000001226 reprecipitation Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- HRLHOWWCFUKTIY-UHFFFAOYSA-L dichloroalumanylium Chemical compound Cl[Al+]Cl HRLHOWWCFUKTIY-UHFFFAOYSA-L 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- NMVXHZSPDTXJSJ-UHFFFAOYSA-L 2-methylpropylaluminum(2+);dichloride Chemical compound CC(C)C[Al](Cl)Cl NMVXHZSPDTXJSJ-UHFFFAOYSA-L 0.000 description 1
- HLBZWYXLQJQBKU-UHFFFAOYSA-N 4-(morpholin-4-yldisulfanyl)morpholine Chemical compound C1COCCN1SSN1CCOCC1 HLBZWYXLQJQBKU-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229920003193 cis-1,4-polybutadiene polymer Polymers 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- QAEKNCDIHIGLFI-UHFFFAOYSA-L cobalt(2+);2-ethylhexanoate Chemical compound [Co+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O QAEKNCDIHIGLFI-UHFFFAOYSA-L 0.000 description 1
- FJDJVBXSSLDNJB-LNTINUHCSA-N cobalt;(z)-4-hydroxypent-3-en-2-one Chemical compound [Co].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FJDJVBXSSLDNJB-LNTINUHCSA-N 0.000 description 1
- PLTOVEJYEUZSKT-UHFFFAOYSA-N cobalt;pyridine Chemical compound [Co].C1=CC=NC=C1 PLTOVEJYEUZSKT-UHFFFAOYSA-N 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 229920001580 isotactic polymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229920001576 syndiotactic polymer Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and 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
- C08F36/04—Homopolymers and 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
-
- 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
- C08F136/045—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 conjugated hydrocarbons other than butadiene or 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)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT886961 | 1961-05-13 | ||
| IT1869361 | 1961-10-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1165862B true DE1165862B (de) | 1964-03-19 |
Family
ID=26326117
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEM52818A Pending DE1165862B (de) | 1961-05-13 | 1962-05-11 | Verfahren zur Herstellung von linearen kristallinen Polypentadienen |
| DEM54498A Pending DE1184087B (de) | 1961-05-13 | 1962-10-15 | Verfahren zur Herstellung von linearen kristallinen Polypentadienen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEM54498A Pending DE1184087B (de) | 1961-05-13 | 1962-10-15 | Verfahren zur Herstellung von linearen kristallinen Polypentadienen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3301839A (en, 2012) |
| BE (1) | BE617545A (en, 2012) |
| DE (2) | DE1165862B (en, 2012) |
| GB (1) | GB931900A (en, 2012) |
| NL (1) | NL278166A (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5446117A (en) * | 1993-08-19 | 1995-08-29 | Queen's University At Kingston | Process for producing amorphous syndiotactic polystyrene |
| DE19512116A1 (de) * | 1995-04-04 | 1996-10-10 | Bayer Ag | Gasphasenpolymerisation von konjugierten Dienen in Gegenwart von Allylverbindungen der seltenen Erden |
| CN110256618A (zh) * | 2019-05-31 | 2019-09-20 | 宁波金海晨光化学股份有限公司 | 一种顺式-1,4结构的聚间戊二烯及其制备方法和应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL111783C (en, 2012) * | 1955-10-17 | |||
| US3020269A (en) * | 1957-01-10 | 1962-02-06 | Union Carbide Corp | Butadiene polymerization |
| AT213051B (de) * | 1958-04-24 | 1961-01-25 | Montedison Spa | Verfahren zum Polymerisieren von Diolefinen mit wenigstens einer Vinyldoppelbindung |
| BE588028A (en, 2012) * | 1959-02-27 | |||
| US3040016A (en) * | 1960-03-28 | 1962-06-19 | Shell Oil Co | Polymerization process |
-
0
- NL NL278166D patent/NL278166A/xx unknown
- BE BE617545D patent/BE617545A/xx unknown
-
1962
- 1962-03-30 GB GB12326/62A patent/GB931900A/en not_active Expired
- 1962-05-09 US US193528A patent/US3301839A/en not_active Expired - Lifetime
- 1962-05-11 DE DEM52818A patent/DE1165862B/de active Pending
- 1962-10-15 DE DEM54498A patent/DE1184087B/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL278166A (en, 2012) | |
| BE617545A (en, 2012) | |
| GB931900A (en) | 1963-07-24 |
| US3301839A (en) | 1967-01-31 |
| DE1184087B (de) | 1964-12-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1794361B1 (de) | Polymere des propylens oder butens | |
| DE2059378A1 (de) | Verfahren zur Herstellung von 1,2-Polybutadien | |
| DE1174074B (de) | Verfahren zur Herstellung eines kautschuk-artigen Polymerisats von 1,3-Butadien | |
| DE1770444C3 (de) | Kristalline Polypentename | |
| DE1143333B (de) | Verfahren zur Herstellung von Polybutadien | |
| DE2904598C2 (en, 2012) | ||
| DE1294007B (de) | Verfahren zur Herstellung von Butadienpolymeren | |
| DE1133548B (de) | Verfahren zum Polymerisieren von konjugierten Diolefinen mit wenigstens einer endstaendigen Vinyldoppelbindung | |
| DE2823303A1 (de) | Verfahren zur herstellung von 1.2-polybutadienen mit eingestelltem molekulargewicht | |
| DE2246442A1 (de) | Verfahren zur polymerisierung von cycloolefinen | |
| DE1156239B (de) | Verfahren zur Herstellung von kristallinen 1,3-Butadienpolymeren | |
| DE1104703B (de) | Verfahren zur Herstellung von 1, 3-Butadienpolymeren | |
| DE1165862B (de) | Verfahren zur Herstellung von linearen kristallinen Polypentadienen | |
| DE1093093B (de) | Polymerisationskatalysator | |
| DE1816089B2 (de) | Verfahren zum herstellen von regellosen coplymeren aus conjugierten dienen mit 4 12 kohlenstoffatomen und vinylsubstitu ierten aromatischen kohlenwasserstoffen | |
| DE1258095B (de) | Verfahren zur Polymerisation von konjugierten Diolefinen | |
| CH455293A (de) | Verfahren zur Herstellung von neuen olefinisch ungesättigten Carboxylgruppen aufweisenden Verbindungen mit hohem Molekulargewicht | |
| DE2237573A1 (de) | Stabilisierte olefin-terpolymerisate und verfahren zu ihrer herstellung | |
| DE1091754B (de) | Verfahren zur Polymerisation von Vinylaethern | |
| AT212565B (de) | Verfahren zur Polymerisation von wenigstens eine Vinyldoppelbindung enthaltenden Diolefinen | |
| DE1620931A1 (de) | Verfahren zur Polymerisation und Mischpolymerisation konjugierter Diene | |
| DE1292845B (de) | Verfahren zur Herstellung von Polybutadien mit ueberwiegender 1, 2-Struktur | |
| DE1178601B (de) | Verfahren zur Herstellung von Mischpolymerisaten des Isobutylens | |
| DE1251033B (de) | I Verfahren zur katalytischen Polymerisation oder Mischpolymerisation von Diolefmen | |
| DE1252418B (de) | Verfahren zur Herstellung von Butadienpol-ymensaten |