DE2218160C2 - Copolymeres von Äthylen und einem Dien - Google Patents
Copolymeres von Äthylen und einem DienInfo
- Publication number
- DE2218160C2 DE2218160C2 DE2218160A DE2218160A DE2218160C2 DE 2218160 C2 DE2218160 C2 DE 2218160C2 DE 2218160 A DE2218160 A DE 2218160A DE 2218160 A DE2218160 A DE 2218160A DE 2218160 C2 DE2218160 C2 DE 2218160C2
- Authority
- DE
- Germany
- Prior art keywords
- diene
- ethylene
- polymer
- carbon
- activation energy
- 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
- 150000001993 dienes Chemical class 0.000 title claims description 43
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims description 28
- 239000005977 Ethylene Substances 0.000 title claims description 28
- 229920001577 copolymer Polymers 0.000 title claims description 26
- 229920000642 polymer Polymers 0.000 claims description 83
- 230000004913 activation Effects 0.000 claims description 23
- 150000005673 monoalkenes Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 7
- 239000012967 coordination catalyst Substances 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- -1 vanadium oxychloride compound Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims 1
- 125000005234 alkyl aluminium group Chemical group 0.000 claims 1
- 238000010924 continuous production Methods 0.000 claims 1
- 238000000034 method Methods 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000003054 catalyst Substances 0.000 description 19
- 238000002474 experimental method Methods 0.000 description 15
- 239000000203 mixture Substances 0.000 description 11
- 239000000155 melt Substances 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 230000009257 reactivity Effects 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical compound C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920001897 terpolymer Polymers 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 229920001038 ethylene copolymer Polymers 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- RMDKEBZUCHXUER-UHFFFAOYSA-N 4-methylbicyclo[2.2.1]hept-2-ene Chemical compound C1CC2C=CC1(C)C2 RMDKEBZUCHXUER-UHFFFAOYSA-N 0.000 description 1
- GAMYSBRQIMQFIO-UHFFFAOYSA-N CC1C2C=CC(C1)C2.CC2C1C=CC(C2)C1 Chemical compound CC1C2C=CC(C1)C2.CC2C1C=CC(C2)C1 GAMYSBRQIMQFIO-UHFFFAOYSA-N 0.000 description 1
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 229920001198 elastomeric copolymer Polymers 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 238000012994 industrial processing Methods 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000010128 melt processing Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000005514 radiochemical analysis Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-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
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
- C08F210/18—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers with non-conjugated dienes, e.g. EPT 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
- C08F210/02—Ethene
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)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Laminated Bodies (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA110,608A CA980498A (en) | 1971-04-16 | 1971-04-16 | Ethylene polymers with long chain branching |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2218160A1 DE2218160A1 (de) | 1972-10-26 |
| DE2218160C2 true DE2218160C2 (de) | 1986-03-06 |
Family
ID=4089395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2218160A Expired DE2218160C2 (de) | 1971-04-16 | 1972-04-14 | Copolymeres von Äthylen und einem Dien |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3984610A (OSRAM) |
| JP (1) | JPS5722327B1 (OSRAM) |
| CA (1) | CA980498A (OSRAM) |
| DE (1) | DE2218160C2 (OSRAM) |
| FR (1) | FR2136468A5 (OSRAM) |
| GB (1) | GB1382336A (OSRAM) |
| IT (1) | IT951431B (OSRAM) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4102761A (en) * | 1974-01-03 | 1978-07-25 | The Firestone Tire & Rubber Company | Radiation cure of synthetic rubbers |
| US4851489A (en) * | 1983-04-25 | 1989-07-25 | Exxon Research & Engineering Company | Long chain branching in polyolefins from Ziegler-Natta catalysts |
| GB8509452D0 (en) * | 1985-04-12 | 1985-05-15 | Du Pont Canada | Colour of polymers |
| NL8502747A (nl) * | 1985-10-09 | 1987-05-04 | Stamicarbon | Gemodificeerd polyetheen, werkwijze voor het bereiden van gemodificeerd polyetheen, en produkten vervaardigd uit gemodificeerd polyetheen. |
| DE3621763A1 (de) * | 1986-06-28 | 1988-01-21 | Bayer Ag | Verfahren zur herstellung von verzweigtem niederdruckpolyethen, neue niederdruckpolyethene und praeformierte bifunktionelle katalysatoren |
| JP2538625B2 (ja) * | 1987-11-13 | 1996-09-25 | 三井石油化学工業株式会社 | 分枝α−オレフイン系ランダム共重合体およびその製法 |
| JP2714564B2 (ja) * | 1989-03-28 | 1998-02-16 | 東燃株式会社 | ヘプタジエン重合体及びその製造方法 |
| WO1991017194A1 (en) * | 1990-05-07 | 1991-11-14 | Exxon Chemical Patents Inc. | UNSATURATED α-OLEFIN COPOLYMERS AND METHOD FOR PREPARATION THEREOF |
| US5525695A (en) * | 1991-10-15 | 1996-06-11 | The Dow Chemical Company | Elastic linear interpolymers |
| US6300451B1 (en) | 1994-10-24 | 2001-10-09 | Exxon Chemical Patents Inc. | Long-chain branched polymers and their production |
| US5670595A (en) * | 1995-08-28 | 1997-09-23 | Exxon Chemical Patents Inc. | Diene modified polymers |
| US5814714A (en) * | 1995-11-30 | 1998-09-29 | The Dow Chemical Company | Mono-olefin/polyene interpolymers, method of preparation, compositions containing the same, and articles made thereof |
| DE19622272A1 (de) * | 1996-06-03 | 1997-12-04 | Basf Ag | Copolymere von Alk-1-enen und a,beta-Dienen mit erhöhtem Viskositätsindex |
| US20030211280A1 (en) | 1997-02-28 | 2003-11-13 | Shaw Industries, Inc. | Carpet, carpet backings and methods |
| US7338698B1 (en) | 1997-02-28 | 2008-03-04 | Columbia Insurance Company | Homogeneously branched ethylene polymer carpet, carpet backing and method for making same |
| WO1998038376A1 (en) | 1997-02-28 | 1998-09-03 | Shaw Industries, Inc. | Carpet, carpet backings and methods |
| US6294631B1 (en) | 1998-12-15 | 2001-09-25 | Exxonmobil Chemical Patents Inc. | Hyperbranched polymers by coordination polymerization |
| US6699955B1 (en) * | 1999-11-19 | 2004-03-02 | E. I. Du Pont De Nemours And Company | Copolymerization of ethylene and dienes |
| US6509431B1 (en) * | 2000-01-18 | 2003-01-21 | Exxonmobil Oil Corporation | Terpolymers |
| MY131000A (en) * | 2001-03-16 | 2007-07-31 | Dow Global Technologies Inc | High melt strength polymers and method of making same |
| AR040146A1 (es) * | 2002-06-04 | 2005-03-16 | Union Carbide Chem Plastic | Composiciones de polimeros y metodo para fabricar canos |
| US9982081B2 (en) | 2016-02-12 | 2018-05-29 | Exxonmobil Chemical Patents Inc. | Cyclic olefin copolymers and methods of making them |
| US10550252B2 (en) | 2017-04-20 | 2020-02-04 | Chevron Phillips Chemical Company Lp | Bimodal PE resins with improved melt strength |
| US10920029B2 (en) | 2018-02-28 | 2021-02-16 | Exxonmobil Chemical Patents Inc. | Polyethylene and cyclic olefin copolymer blend compositions with oxygen barrier properties and articles made therefrom |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB863373A (en) | 1956-11-05 | 1961-03-22 | Du Pont | Polymers of cyclic dienes and process of preparing them |
| BE614644A (OSRAM) * | 1957-07-17 | |||
| US2933480A (en) * | 1959-06-17 | 1960-04-19 | Du Pont | Sulfur vulcanizable unsaturated elastomeric interpolymers of monoolefins and diolefins |
| US3146221A (en) * | 1960-11-25 | 1964-08-25 | Nat Distillers Chem Corp | Copolymeric compositions |
| NL122499C (OSRAM) * | 1962-08-17 | |||
| DE1300251B (de) * | 1963-09-21 | 1969-07-31 | Huels Chemische Werke Ag | Verfahren zur Herstellung von Olefin-Mischpolymerisaten |
| US3351621A (en) * | 1964-02-06 | 1967-11-07 | Chevron Res | Copolymerization with alpha, omega-dienes |
| GB1081626A (en) | 1964-05-06 | 1967-08-31 | Bayer Ag | Copolymers of ethylene and norborna-2.5-diene |
| US3379515A (en) * | 1965-04-09 | 1968-04-23 | Eddie G. Lindstrom | High molecular weight imide substituted polymers as fuel detergents |
| FR1481696A (fr) * | 1965-06-01 | 1967-05-19 | Pittsburgh Plate Glass Co | Polyéthylène de bas poids moléculaire et son procédé de fabrication |
| US3467637A (en) * | 1965-06-01 | 1969-09-16 | Ppg Industries Inc | Low molecular weight olefin interpolymers prepared in the presence of bicyclo(2.2.1)hepta-2,5-diene |
| FR1492157A (fr) * | 1965-06-01 | 1967-08-18 | Pittsburgh Plate Glass Co | Interpolymères d'hydrocarbures éthyléniques et leur procédé de fabrication |
| CA849081A (en) | 1967-03-02 | 1970-08-11 | Du Pont Of Canada Limited | PRODUCTION OF ETHYLENE/.alpha.-OLEFIN COPOLYMERS OF IMPROVED PHYSICAL PROPERTIES |
| NL153224C (nl) | 1967-03-24 | 1982-09-16 | Du Pont | Werkwijze voor het bereiden van een onverzadigd copolymeer. |
-
1971
- 1971-04-16 CA CA110,608A patent/CA980498A/en not_active Expired
-
1972
- 1972-04-11 GB GB1661772A patent/GB1382336A/en not_active Expired
- 1972-04-13 US US05/243,867 patent/US3984610A/en not_active Expired - Lifetime
- 1972-04-14 DE DE2218160A patent/DE2218160C2/de not_active Expired
- 1972-04-15 JP JP3739772A patent/JPS5722327B1/ja active Pending
- 1972-04-15 IT IT23163/72A patent/IT951431B/it active
- 1972-04-17 FR FR7213395A patent/FR2136468A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1382336A (en) | 1975-01-29 |
| US3984610A (en) | 1976-10-05 |
| DE2218160A1 (de) | 1972-10-26 |
| FR2136468A5 (OSRAM) | 1972-12-22 |
| CA980498A (en) | 1975-12-23 |
| IT951431B (it) | 1973-06-30 |
| JPS5722327B1 (OSRAM) | 1982-05-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OGA | New person/name/address of the applicant | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |