DE2534493C2 - Verfahren zur Herstellung von Äthylen-Butadien-Copolymerisaten - Google Patents
Verfahren zur Herstellung von Äthylen-Butadien-CopolymerisatenInfo
- Publication number
- DE2534493C2 DE2534493C2 DE2534493A DE2534493A DE2534493C2 DE 2534493 C2 DE2534493 C2 DE 2534493C2 DE 2534493 A DE2534493 A DE 2534493A DE 2534493 A DE2534493 A DE 2534493A DE 2534493 C2 DE2534493 C2 DE 2534493C2
- Authority
- DE
- Germany
- Prior art keywords
- ethylene
- butadiene
- vanadium
- copolymers
- polymerization
- 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 66
- 238000000034 method Methods 0.000 title claims description 16
- 230000008569 process Effects 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title description 13
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 40
- 239000003054 catalyst Substances 0.000 claims description 30
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 24
- 239000005977 Ethylene Substances 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 7
- 238000007334 copolymerization reaction Methods 0.000 claims description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
- 238000006116 polymerization reaction Methods 0.000 description 27
- 239000000243 solution Substances 0.000 description 25
- 229910052720 vanadium Inorganic materials 0.000 description 24
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 23
- 239000000203 mixture Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- -1 vanadium (III) halide Chemical class 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 239000000499 gel Substances 0.000 description 11
- 238000009826 distribution Methods 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 230000035945 sensitivity Effects 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 150000003682 vanadium compounds Chemical class 0.000 description 6
- 125000005287 vanadyl group Chemical group 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 229920001897 terpolymer Polymers 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 229920001903 high density polyethylene Polymers 0.000 description 3
- 239000004700 high-density polyethylene Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VHFUHRXYRYWELT-UHFFFAOYSA-N methyl 2,2,2-trichloroacetate Chemical compound COC(=O)C(Cl)(Cl)Cl VHFUHRXYRYWELT-UHFFFAOYSA-N 0.000 description 3
- 150000002902 organometallic compounds Chemical class 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 3
- 238000004073 vulcanization Methods 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910021551 Vanadium(III) chloride Inorganic materials 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HQYCOEXWFMFWLR-UHFFFAOYSA-K vanadium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[V+3] HQYCOEXWFMFWLR-UHFFFAOYSA-K 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- RWUHMISXOUGVKX-OWOJBTEDSA-N (e)-2,3,4,4,4-pentachlorobut-2-enoic acid Chemical class OC(=O)C(\Cl)=C(/Cl)C(Cl)(Cl)Cl RWUHMISXOUGVKX-OWOJBTEDSA-N 0.000 description 1
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 1
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- LVZPKYYPPLUECL-UHFFFAOYSA-N 1-chloro-4-(trichloromethyl)benzene Chemical compound ClC1=CC=C(C(Cl)(Cl)Cl)C=C1 LVZPKYYPPLUECL-UHFFFAOYSA-N 0.000 description 1
- NMVXHZSPDTXJSJ-UHFFFAOYSA-L 2-methylpropylaluminum(2+);dichloride Chemical compound CC(C)C[Al](Cl)Cl NMVXHZSPDTXJSJ-UHFFFAOYSA-L 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- HLHNOIAOWQFNGW-UHFFFAOYSA-N 3-bromo-4-hydroxybenzonitrile Chemical compound OC1=CC=C(C#N)C=C1Br HLHNOIAOWQFNGW-UHFFFAOYSA-N 0.000 description 1
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229920008712 Copo Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910021552 Vanadium(IV) chloride Inorganic materials 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- HQMRIBYCTLBDAK-UHFFFAOYSA-M bis(2-methylpropyl)alumanylium;chloride Chemical compound CC(C)C[Al](Cl)CC(C)C HQMRIBYCTLBDAK-UHFFFAOYSA-M 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- IZMHKHHRLNWLMK-UHFFFAOYSA-M chloridoaluminium Chemical compound Cl[Al] IZMHKHHRLNWLMK-UHFFFAOYSA-M 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- SJMLNDPIJZBEKY-UHFFFAOYSA-N ethyl 2,2,2-trichloroacetate Chemical compound CCOC(=O)C(Cl)(Cl)Cl SJMLNDPIJZBEKY-UHFFFAOYSA-N 0.000 description 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000011953 free-radical catalyst Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000004059 quinone derivatives Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- ZJGSQAUGHPGIQF-UHFFFAOYSA-N triethynylalumane Chemical compound C#C[Al](C#C)C#C ZJGSQAUGHPGIQF-UHFFFAOYSA-N 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical group C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 150000003681 vanadium Chemical class 0.000 description 1
- JTJFQBNJBPPZRI-UHFFFAOYSA-J vanadium tetrachloride Chemical compound Cl[V](Cl)(Cl)Cl JTJFQBNJBPPZRI-UHFFFAOYSA-J 0.000 description 1
- PSDQQCXQSWHCRN-UHFFFAOYSA-N vanadium(4+) Chemical compound [V+4] PSDQQCXQSWHCRN-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- ZUBNXRHITOZMOO-UHFFFAOYSA-N zinc;octadecanoic acid;oxygen(2-) Chemical compound [O-2].[Zn+2].CCCCCCCCCCCCCCCCCC(O)=O ZUBNXRHITOZMOO-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin 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
- C08F210/02—Ethene
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT25933/74A IT1017868B (it) | 1974-08-02 | 1974-08-02 | Procedimento per la preparazione in alta resa di copolimeri dello etilene con 1.3 butadiene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2534493A1 DE2534493A1 (de) | 1976-02-12 |
| DE2534493C2 true DE2534493C2 (de) | 1982-02-25 |
Family
ID=11218175
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2534493A Expired DE2534493C2 (de) | 1974-08-02 | 1975-08-01 | Verfahren zur Herstellung von Äthylen-Butadien-Copolymerisaten |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS5137983A (en, 2012) |
| AT (1) | AT342859B (en, 2012) |
| AU (1) | AU8286475A (en, 2012) |
| BE (1) | BE832053A (en, 2012) |
| BR (1) | BR7504978A (en, 2012) |
| CA (1) | CA1043943A (en, 2012) |
| DD (1) | DD119253A5 (en, 2012) |
| DE (1) | DE2534493C2 (en, 2012) |
| DK (1) | DK351575A (en, 2012) |
| ES (1) | ES440486A1 (en, 2012) |
| FR (1) | FR2280654A1 (en, 2012) |
| GB (1) | GB1519473A (en, 2012) |
| HU (1) | HU170894B (en, 2012) |
| IL (1) | IL47730A0 (en, 2012) |
| IT (1) | IT1017868B (en, 2012) |
| LU (1) | LU73122A1 (en, 2012) |
| MW (1) | MW4275A1 (en, 2012) |
| NL (1) | NL7509283A (en, 2012) |
| NO (1) | NO752703L (en, 2012) |
| RO (1) | RO68285A (en, 2012) |
| SE (1) | SE7508740L (en, 2012) |
| SU (1) | SU707523A3 (en, 2012) |
| TR (1) | TR18961A (en, 2012) |
| ZA (2) | ZA754374B (en, 2012) |
| ZM (1) | ZM10075A1 (en, 2012) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52156195A (en) * | 1976-06-22 | 1977-12-26 | Mitsubishi Chem Ind Ltd | Production of solid catalyst and olefin polymers |
| JPS52156795A (en) * | 1976-06-23 | 1977-12-27 | Mitsubishi Chem Ind Ltd | Production of solid catalyst and olefin polymers |
| US4322450A (en) | 1979-09-24 | 1982-03-30 | Scott Paper Company | Surface replication on a coated substrate |
| US4427732A (en) | 1980-10-02 | 1984-01-24 | Scott Paper Company | Surface replication on a coated substrate |
| US4607019A (en) * | 1984-12-12 | 1986-08-19 | Exxon Research & Engineering Co. | Polymerization catalyst, production and use |
| US4579835A (en) * | 1984-12-12 | 1986-04-01 | Exxon Research & Engineering Co. | Polymerization catalyst, production and use |
| IT1263862B (it) * | 1993-03-31 | 1996-09-04 | Enichem Polimeri | Procedimento per la (co)polimerizzazione dell'etilene |
| US5342907A (en) * | 1993-06-28 | 1994-08-30 | Union Carbide Chemicals & Plastics Technology Corporation | Ethylene/propylene copolymer rubbers |
| US5480850A (en) * | 1993-06-28 | 1996-01-02 | Union Carbide Chemical & Plastics Technology Corporation | Ethylene/propylene copolymer rubbers |
| US5416053A (en) * | 1993-06-28 | 1995-05-16 | Union Carbide Chemicals & Plastics Technology Corporation | Homogenous polyethylenes and ethylene/propylene copolymers rubbers |
| US5332793A (en) * | 1993-06-28 | 1994-07-26 | Union Carbide Chemicals & Plastics Technology Corporation | Ethylene/propylene copolymer rubbers |
| US5502127A (en) * | 1994-03-31 | 1996-03-26 | Union Carbide Chemicals & Plastics Technology Corporation | Process for production of homogeneous polyethylene |
| US5492986A (en) * | 1994-03-31 | 1996-02-20 | Union Carbide Chemicals & Plastics Technology Corporation | Process for producing homogeneous polyethylenes |
| US5410003A (en) * | 1994-03-31 | 1995-04-25 | Union Carbide Chemicals & Plastics Technology Corporation | Process for production of homogeneous polyethylenes |
| IT1269805B (it) * | 1994-05-20 | 1997-04-15 | Enichem Spa | Catalizzatore per la (co)polimerizzazione dell'etilene e procedimento per il suo ottenimento |
| WO2017040005A1 (en) | 2015-08-31 | 2017-03-09 | Bridgestone Corporation | Copolymerization of polyenes and alkenes |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3055875A (en) * | 1960-07-05 | 1962-09-25 | Union Carbide Corp | Modified ethylene polymers |
| US3301834A (en) * | 1963-09-11 | 1967-01-31 | Hercules Inc | Polymerization of olefins |
| FR1477275A (fr) * | 1965-05-08 | 1967-04-14 | Huels Chemische Werke Ag | Procédé pour préparer des copolymères amorphes de poids moléculaire élevé, à partir de l-oléfines seules ou en métlange avec des poly-oléfines |
| DE1720643A1 (de) * | 1967-04-05 | 1971-06-16 | Bunawerke Huels Gmbh | Verfahren zur Herstellung von amorphen Copolymeren aus AEthylen und hoeheren alpha-Olefinen in Suspensionen mit modifizierten metallorganischen Mischkatalysatoren |
-
1974
- 1974-08-02 IT IT25933/74A patent/IT1017868B/it active
-
1975
- 1975-07-08 ZA ZA00754374A patent/ZA754374B/xx unknown
- 1975-07-08 ZA ZA00754377A patent/ZA754377B/xx unknown
- 1975-07-09 AU AU82864/75A patent/AU8286475A/en not_active Expired
- 1975-07-12 MW MW42/75A patent/MW4275A1/xx unknown
- 1975-07-17 GB GB30117/75A patent/GB1519473A/en not_active Expired
- 1975-07-18 IL IL47730A patent/IL47730A0/xx unknown
- 1975-07-21 CA CA231,871A patent/CA1043943A/en not_active Expired
- 1975-07-22 ZM ZM100/75A patent/ZM10075A1/xx unknown
- 1975-07-29 FR FR7523696A patent/FR2280654A1/fr active Granted
- 1975-07-29 ES ES440486A patent/ES440486A1/es not_active Expired
- 1975-07-29 TR TR18961A patent/TR18961A/xx unknown
- 1975-07-30 DD DD187569A patent/DD119253A5/xx unknown
- 1975-07-30 SU SU752156911A patent/SU707523A3/ru active
- 1975-07-31 LU LU73122A patent/LU73122A1/xx unknown
- 1975-08-01 AT AT599875A patent/AT342859B/de not_active IP Right Cessation
- 1975-08-01 BE BE158880A patent/BE832053A/xx unknown
- 1975-08-01 DK DK351575A patent/DK351575A/da unknown
- 1975-08-01 HU HU75SA00002829A patent/HU170894B/hu unknown
- 1975-08-01 JP JP50093238A patent/JPS5137983A/ja active Pending
- 1975-08-01 SE SE7508740A patent/SE7508740L/xx unknown
- 1975-08-01 NO NO752703A patent/NO752703L/no unknown
- 1975-08-01 DE DE2534493A patent/DE2534493C2/de not_active Expired
- 1975-08-02 RO RO7583049A patent/RO68285A/ro unknown
- 1975-08-04 BR BR7504978*A patent/BR7504978A/pt unknown
- 1975-08-04 NL NL7509283A patent/NL7509283A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ATA599875A (de) | 1977-08-15 |
| ZA754374B (en) | 1976-07-28 |
| TR18961A (tr) | 1978-01-19 |
| NL7509283A (nl) | 1976-02-04 |
| FR2280654A1 (fr) | 1976-02-27 |
| MW4275A1 (en) | 1976-10-13 |
| GB1519473A (en) | 1978-07-26 |
| DK351575A (da) | 1976-02-03 |
| NO752703L (en, 2012) | 1976-02-03 |
| ZM10075A1 (en) | 1976-04-21 |
| SU707523A3 (ru) | 1979-12-30 |
| DD119253A5 (en, 2012) | 1976-04-12 |
| HU170894B (hu) | 1977-09-28 |
| IT1017868B (it) | 1977-08-10 |
| JPS5137983A (en, 2012) | 1976-03-30 |
| DE2534493A1 (de) | 1976-02-12 |
| CA1043943A (en) | 1978-12-05 |
| LU73122A1 (en, 2012) | 1976-03-02 |
| BR7504978A (pt) | 1976-07-27 |
| AU8286475A (en) | 1977-01-13 |
| FR2280654B1 (en, 2012) | 1979-08-24 |
| ZA754377B (en) | 1976-07-28 |
| SE7508740L (sv) | 1976-02-03 |
| ES440486A1 (es) | 1977-02-16 |
| BE832053A (fr) | 1976-02-02 |
| AT342859B (de) | 1978-04-25 |
| RO68285A (ro) | 1980-08-15 |
| IL47730A0 (en) | 1975-10-15 |
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| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |