DE2352980C3 - Verfahren zur Herstellung von kristallinen Propen-Äthen-Buten-1-Terpolymeren - Google Patents
Verfahren zur Herstellung von kristallinen Propen-Äthen-Buten-1-TerpolymerenInfo
- Publication number
- DE2352980C3 DE2352980C3 DE2352980A DE2352980A DE2352980C3 DE 2352980 C3 DE2352980 C3 DE 2352980C3 DE 2352980 A DE2352980 A DE 2352980A DE 2352980 A DE2352980 A DE 2352980A DE 2352980 C3 DE2352980 C3 DE 2352980C3
- Authority
- DE
- Germany
- Prior art keywords
- butene
- weight
- propene
- parts
- athens
- 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
- 238000000034 method Methods 0.000 title claims description 21
- 229920001897 terpolymer Polymers 0.000 title claims description 16
- 230000008569 process Effects 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- IYYGCUZHHGZXGJ-UHFFFAOYSA-N but-1-ene;ethene;prop-1-ene Chemical compound C=C.CC=C.CCC=C IYYGCUZHHGZXGJ-UHFFFAOYSA-N 0.000 title description 10
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 62
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 61
- 238000006116 polymerization reaction Methods 0.000 claims description 42
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 31
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 claims description 23
- 229920000642 polymer Polymers 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 238000010626 work up procedure Methods 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 32
- 238000007792 addition Methods 0.000 description 17
- 238000000691 measurement method Methods 0.000 description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 8
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 7
- 229920001155 polypropylene Polymers 0.000 description 7
- -1 polypropylene Polymers 0.000 description 7
- 239000004743 Polypropylene Substances 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 239000001273 butane Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 6
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 229920001400 block copolymer Polymers 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 125000005234 alkyl aluminium group Chemical group 0.000 description 4
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 4
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VVUILVMDMIIETB-UHFFFAOYSA-K [Ti].Cl[Al](Cl)Cl Chemical class [Ti].Cl[Al](Cl)Cl VVUILVMDMIIETB-UHFFFAOYSA-K 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 3
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- PZASAAIJIFDWSB-CKPDSHCKSA-N 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-CKPDSHCKSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 230000007306 turnover Effects 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
- C08F210/16—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
-
- 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
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/06—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the coordination type
- C08F297/08—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the coordination type polymerising mono-olefins
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2352980A DE2352980C3 (de) | 1973-10-23 | 1973-10-23 | Verfahren zur Herstellung von kristallinen Propen-Äthen-Buten-1-Terpolymeren |
| US05/515,334 US3959409A (en) | 1973-10-23 | 1974-10-16 | Process for the production of crystalline propene-ethene-butene-1 terpolymers |
| FR7434902A FR2248291B1 (enExample) | 1973-10-23 | 1974-10-17 | |
| IT53647/74A IT1023083B (it) | 1973-10-23 | 1974-10-21 | Procedimento per produrre terpolimeri cristallini di propene etene eutene i |
| GB45662/74A GB1479198A (en) | 1973-10-23 | 1974-10-22 | Process for the manufacture of crystalline propylene-ethylene-butene-1 terpolymers |
| BE149761A BE821337A (fr) | 1973-10-23 | 1974-10-22 | Procede de production de terpolymeres cristallins du propylene avec l'ethylene et le butene-1 |
| JP49121056A JPS5933601B2 (ja) | 1973-10-23 | 1974-10-22 | 結晶性プロピレン−エテン−ブテン−１三元共重合体の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2352980A DE2352980C3 (de) | 1973-10-23 | 1973-10-23 | Verfahren zur Herstellung von kristallinen Propen-Äthen-Buten-1-Terpolymeren |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2352980A1 DE2352980A1 (de) | 1975-04-24 |
| DE2352980B2 DE2352980B2 (de) | 1979-07-12 |
| DE2352980C3 true DE2352980C3 (de) | 1980-03-13 |
Family
ID=5896143
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2352980A Expired DE2352980C3 (de) | 1973-10-23 | 1973-10-23 | Verfahren zur Herstellung von kristallinen Propen-Äthen-Buten-1-Terpolymeren |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3959409A (enExample) |
| JP (1) | JPS5933601B2 (enExample) |
| BE (1) | BE821337A (enExample) |
| DE (1) | DE2352980C3 (enExample) |
| FR (1) | FR2248291B1 (enExample) |
| GB (1) | GB1479198A (enExample) |
| IT (1) | IT1023083B (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS607645B2 (ja) * | 1976-04-19 | 1985-02-26 | チッソ株式会社 | 共重合体ポリプロピレン用触媒の重合前活性化による該共重合体の製造法 |
| DE2637991A1 (de) * | 1976-08-24 | 1978-03-02 | Hoechst Ag | Kunststoffolie aus copolymeren und verfahren zur herstellung derselben |
| DE2637990A1 (de) * | 1976-08-24 | 1978-03-02 | Hoechst Ag | Propylen-terpolymer |
| DE2637978B2 (de) * | 1976-08-24 | 1979-10-25 | Hoechst Ag, 6000 Frankfurt | HeiBsiegelfähige Kunststoffolie und Verfahren zu ihrer Herstellung |
| DE2715349C3 (de) * | 1977-04-06 | 1980-05-22 | Chemische Werke Huels Ag, 4370 Marl | Verwendung von teilkristallinem statistisch copolymerisiertem Polypropylen zur Herstellung von Isolierungen elektrischer Kabel |
| JPS6042805B2 (ja) * | 1979-02-27 | 1985-09-25 | 日石三菱株式会社 | 共重合体の製法 |
| JPS55115416A (en) * | 1979-02-27 | 1980-09-05 | Nippon Oil Co Ltd | Manufacture of copolymer |
| DE2930108C2 (de) * | 1979-07-25 | 1982-11-25 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur Herstellung von weitgehend amorphen Buten-1 Propen-Ethen-Terpolymeren mit hohem Erweichungspunkt |
| JPS6024805B2 (ja) * | 1979-09-05 | 1985-06-14 | 日石三菱株式会社 | 共重合体の製法 |
| JPS6042807B2 (ja) * | 1980-04-11 | 1985-09-25 | チッソ株式会社 | エチレンプロピレンα−オレフイン三元共重合体の製造方法 |
| US4351930A (en) * | 1981-02-05 | 1982-09-28 | El Paso Polyolefins Company | Propylene copolymerization process and product |
| JPS6035364B2 (ja) * | 1981-07-10 | 1985-08-14 | 三井東圧化学株式会社 | プロピレンのブロック共重合体の製造法 |
| JPS58162620A (ja) * | 1982-03-23 | 1983-09-27 | Mitsubishi Petrochem Co Ltd | オレフイン系ブロツク共重合体 |
| US4978720A (en) * | 1983-06-15 | 1990-12-18 | Exxon Research And Engineering Company | Olefinic chlorosilane and olefinic halide functional group containing polymers and method of forming the same |
| US4634745A (en) * | 1985-04-01 | 1987-01-06 | United States Steel Corporation | Terpolymer production |
| JPS62502405A (ja) * | 1985-04-01 | 1987-09-17 | アリステツク ケミカル コ−ポレイシヨン | タ−ポリマ−の製造 |
| JPH02106601U (enExample) * | 1989-02-10 | 1990-08-24 | ||
| US11649301B2 (en) * | 2018-06-12 | 2023-05-16 | Dow Global Technologies Llc | Activator-nucleator formulations |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE551997A (enExample) * | 1955-10-21 | |||
| US3197452A (en) * | 1955-11-30 | 1965-07-27 | Montedison Spa | Method for preparing prevailingly to substantially isotactic crude polymerizates of butene-1 |
| US2918457A (en) * | 1957-09-26 | 1959-12-22 | Sun Oil Co | Copolymer of propylene and butene-1 |
| US3162620A (en) * | 1961-05-04 | 1964-12-22 | Du Pont | Ethylene polymers prepared in the form of a coherent film at a quiescent liquid catalyst surface |
| NL296509A (enExample) * | 1962-09-10 | |||
| US3332921A (en) * | 1963-11-01 | 1967-07-25 | Phillips Petroleum Co | 1-butene-propylene copolymers |
| US3461110A (en) * | 1965-06-02 | 1969-08-12 | Petro Tex Chem Corp | Process for producing polyolefin polymers |
| US3520859A (en) * | 1965-12-09 | 1970-07-21 | Dart Ind Inc | Suspension polymerization method for preparing elastomeric hydrocarbon interpolymers |
| DE1931421C3 (de) * | 1969-06-20 | 1973-12-06 | Chemische Werke Huels Ag, 4370 Marl | Zähflüssige Massen und Verfahren zu deren Herstellung |
-
1973
- 1973-10-23 DE DE2352980A patent/DE2352980C3/de not_active Expired
-
1974
- 1974-10-16 US US05/515,334 patent/US3959409A/en not_active Expired - Lifetime
- 1974-10-17 FR FR7434902A patent/FR2248291B1/fr not_active Expired
- 1974-10-21 IT IT53647/74A patent/IT1023083B/it active
- 1974-10-22 BE BE149761A patent/BE821337A/xx not_active IP Right Cessation
- 1974-10-22 GB GB45662/74A patent/GB1479198A/en not_active Expired
- 1974-10-22 JP JP49121056A patent/JPS5933601B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2352980A1 (de) | 1975-04-24 |
| US3959409A (en) | 1976-05-25 |
| BE821337A (fr) | 1975-02-17 |
| FR2248291A1 (enExample) | 1975-05-16 |
| JPS5933601B2 (ja) | 1984-08-16 |
| IT1023083B (it) | 1978-05-10 |
| GB1479198A (en) | 1977-07-06 |
| JPS5073991A (enExample) | 1975-06-18 |
| DE2352980B2 (de) | 1979-07-12 |
| FR2248291B1 (enExample) | 1980-03-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: HUELS AG, 4370 MARL, DE |
|
| 8339 | Ceased/non-payment of the annual fee |