DE1157788B - Verfahren zur Herstellung von Polymerisaten des Butadiens - Google Patents
Verfahren zur Herstellung von Polymerisaten des ButadiensInfo
- Publication number
- DE1157788B DE1157788B DEF34636A DEF0034636A DE1157788B DE 1157788 B DE1157788 B DE 1157788B DE F34636 A DEF34636 A DE F34636A DE F0034636 A DEF0034636 A DE F0034636A DE 1157788 B DE1157788 B DE 1157788B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- butadiene
- catalysts
- lithium aluminum
- titanium
- 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
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title claims description 46
- 229920000642 polymer Polymers 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000003054 catalyst Substances 0.000 claims description 25
- -1 titanium halides Chemical class 0.000 claims description 14
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 12
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000005527 organic iodine compounds Chemical class 0.000 claims description 4
- 150000001351 alkyl iodides Chemical class 0.000 claims description 3
- 150000002497 iodine compounds Chemical class 0.000 claims description 3
- 238000012545 processing Methods 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- 150000002902 organometallic compounds Chemical class 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 229920002857 polybutadiene Polymers 0.000 description 23
- 239000005062 Polybutadiene Substances 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- 238000006116 polymerization reaction Methods 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 229910010082 LiAlH Inorganic materials 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 229920001971 elastomer Polymers 0.000 description 5
- 239000000806 elastomer Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 229910010199 LiAl Inorganic materials 0.000 description 4
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000007717 exclusion Effects 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- OKJPEAGHQZHRQV-UHFFFAOYSA-N iodoform Chemical compound IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 4
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 244000043261 Hevea brasiliensis Species 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920003052 natural elastomer Polymers 0.000 description 3
- 229920001194 natural rubber Polymers 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229910001868 water Inorganic materials 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- ANGGPYSFTXVERY-UHFFFAOYSA-N 2-iodo-2-methylpropane Chemical compound CC(C)(C)I ANGGPYSFTXVERY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- ANOOTOPTCJRUPK-UHFFFAOYSA-N 1-iodohexane Chemical compound CCCCCCI ANOOTOPTCJRUPK-UHFFFAOYSA-N 0.000 description 1
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- ZRYCRPNCXLQHPN-UHFFFAOYSA-N 3-hydroxy-2-methylbenzaldehyde Chemical compound CC1=C(O)C=CC=C1C=O ZRYCRPNCXLQHPN-UHFFFAOYSA-N 0.000 description 1
- IBGRFDRULKDMDS-UHFFFAOYSA-N 4-hexyl-3h-1,3-benzothiazole-2-thione Chemical compound CCCCCCC1=CC=CC2=C1N=C(S)S2 IBGRFDRULKDMDS-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-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
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- ZIQPQYFSSSHQBP-UHFFFAOYSA-N acetyl 2,3-dihydroxypropanoate Chemical compound CC(=O)OC(=O)C(O)CO ZIQPQYFSSSHQBP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001361 allenes Chemical class 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 230000002929 anti-fatigue Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000010692 aromatic oil Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- UBAZGMLMVVQSCD-UHFFFAOYSA-N carbon dioxide;molecular oxygen Chemical compound O=O.O=C=O UBAZGMLMVVQSCD-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229920003211 cis-1,4-polyisoprene Polymers 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000006232 furnace black Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- FUCOMWZKWIEKRK-UHFFFAOYSA-N iodocyclohexane Chemical compound IC1CCCCC1 FUCOMWZKWIEKRK-UHFFFAOYSA-N 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-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
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 1
- NLLZTRMHNHVXJJ-UHFFFAOYSA-J titanium tetraiodide Chemical compound I[Ti](I)(I)I NLLZTRMHNHVXJJ-UHFFFAOYSA-J 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000008096 xylene Substances 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
- 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
- C08F136/06—Butadiene
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)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE635919D BE635919A (en, 2012) | 1961-08-08 | ||
| NL296313D NL296313A (en, 2012) | 1961-08-08 | ||
| BE621195D BE621195A (en, 2012) | 1961-08-08 | ||
| DEF34636A DE1157788B (de) | 1961-08-08 | 1961-08-08 | Verfahren zur Herstellung von Polymerisaten des Butadiens |
| US212471A US3275614A (en) | 1961-08-08 | 1962-07-25 | Process of producing cis-1, 4-polybutadiene with a catalyst containing an organic iodine compound |
| GB30408/62A GB965029A (en) | 1961-08-08 | 1962-08-08 | Process for the manufacture of polybutadiene |
| DEF37562A DE1241120B (de) | 1961-08-08 | 1962-08-10 | Verfahren zur Herstellung von Polymerisaten des Butadiens mit vorwiegend 1, 4-cis-Struktur |
| DEF37802A DE1181426B (de) | 1961-08-08 | 1962-09-13 | Verfahren zur Herstellung von Polymerisaten des Butadiens |
| FR943977A FR1365742A (fr) | 1961-08-08 | 1963-08-07 | Procédé de polymérisation du 1, 3-butadiène |
| GB31383/63A GB972106A (en) | 1961-08-08 | 1963-08-08 | A process for polymerising buta-1,3-diene |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF34636A DE1157788B (de) | 1961-08-08 | 1961-08-08 | Verfahren zur Herstellung von Polymerisaten des Butadiens |
| DEF37562A DE1241120B (de) | 1961-08-08 | 1962-08-10 | Verfahren zur Herstellung von Polymerisaten des Butadiens mit vorwiegend 1, 4-cis-Struktur |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1157788B true DE1157788B (de) | 1963-11-21 |
Family
ID=25975073
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF34636A Pending DE1157788B (de) | 1961-08-08 | 1961-08-08 | Verfahren zur Herstellung von Polymerisaten des Butadiens |
| DEF37562A Pending DE1241120B (de) | 1961-08-08 | 1962-08-10 | Verfahren zur Herstellung von Polymerisaten des Butadiens mit vorwiegend 1, 4-cis-Struktur |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF37562A Pending DE1241120B (de) | 1961-08-08 | 1962-08-10 | Verfahren zur Herstellung von Polymerisaten des Butadiens mit vorwiegend 1, 4-cis-Struktur |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3275614A (en, 2012) |
| BE (2) | BE621195A (en, 2012) |
| DE (2) | DE1157788B (en, 2012) |
| GB (2) | GB965029A (en, 2012) |
| NL (1) | NL296313A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4176219A (en) * | 1977-05-30 | 1979-11-27 | Japan Synthetic Rubber Co., Ltd. | Process for the production of 1,2-polybutadiene with regulated molecular weight |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL126426C (en, 2012) * | 1963-04-15 | |||
| GB1090667A (en) * | 1964-07-23 | 1967-11-15 | Polymer Corp | Elastomeric butadiene polymer |
| US3451537A (en) * | 1966-02-28 | 1969-06-24 | Minnesota Mining & Mfg | Pressure-sensitive adhesive tape |
| US4020007A (en) * | 1974-04-25 | 1977-04-26 | Phillips Petroleum Company | Catalyst for preparation of polybutadiene |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3118864A (en) * | 1954-08-16 | 1964-01-21 | Du Pont | Process of polymerizing conjugated alkadienes |
| IT544926A (en, 2012) * | 1954-08-16 | Du Pont | ||
| US3072630A (en) * | 1955-03-08 | 1963-01-08 | Du Pont | Polymerization of ethylene using coordination catalyst system with a halide promotor |
| US3101328A (en) * | 1955-03-23 | 1963-08-20 | Phillips Petroleum Co | Polymerization of olefins and catalysts therefor |
| US2944048A (en) * | 1955-12-30 | 1960-07-05 | Phillips Petroleum Co | Process and catalyst for production of olefin polymers |
| GB827464A (en) * | 1956-05-01 | 1960-02-03 | Distillers Co Yeast Ltd | Polymerisation process |
| FR1256231A (fr) * | 1959-04-13 | 1961-03-17 | Firestone Tire & Rubber Co | Polymérisation du butadiène |
| BE605475A (en, 2012) * | 1959-06-19 | |||
| NL283426A (en, 2012) * | 1961-09-28 |
-
0
- BE BE635919D patent/BE635919A/xx unknown
- BE BE621195D patent/BE621195A/xx unknown
- NL NL296313D patent/NL296313A/xx unknown
-
1961
- 1961-08-08 DE DEF34636A patent/DE1157788B/de active Pending
-
1962
- 1962-07-25 US US212471A patent/US3275614A/en not_active Expired - Lifetime
- 1962-08-08 GB GB30408/62A patent/GB965029A/en not_active Expired
- 1962-08-10 DE DEF37562A patent/DE1241120B/de active Pending
-
1963
- 1963-08-08 GB GB31383/63A patent/GB972106A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4176219A (en) * | 1977-05-30 | 1979-11-27 | Japan Synthetic Rubber Co., Ltd. | Process for the production of 1,2-polybutadiene with regulated molecular weight |
Also Published As
| Publication number | Publication date |
|---|---|
| NL296313A (en, 2012) | |
| US3275614A (en) | 1966-09-27 |
| GB972106A (en) | 1964-10-07 |
| BE635919A (en, 2012) | |
| GB965029A (en) | 1964-07-29 |
| BE621195A (en, 2012) | |
| DE1241120B (de) | 1967-05-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69004712T2 (de) | Verfahren zur Herstellung von Polybutadien mit verbesserter Verarbeitkeit. | |
| DE1217617B (de) | Verfahren zur Herstellung von mit Schwefel vulkanisierbaren Mischpolymerisaten | |
| DE1128143B (de) | Verfahren zur Polymerisation von aliphatischen konjugierten Diolefinen | |
| DE1300242B (en, 2012) | ||
| DE1620927A1 (de) | Verfahren zur Herstellung von hohem cis-1,4-Polybutadien | |
| DE1158714B (de) | Verfahren zur Herstellung von Mischpolymerisaten des AEthylens mit 1-Olefinen | |
| DE1157788B (de) | Verfahren zur Herstellung von Polymerisaten des Butadiens | |
| DE1226307B (de) | Verfahren zur Herstellung von 1,4-cis-Polydienen | |
| DE1122708B (de) | Verfahren zur Polymerisation oder Mischpolymerisation von konjugierten Diolefinen | |
| EP0132636B1 (de) | Katalysatorsystem und seine Verwendung zur Herstellung von EPDM-Kautschuk | |
| DE1745750B1 (de) | Verfahren zur Herstellung eines Polymerisates mit niedrigem Vinylgehalt | |
| DE1520302A1 (de) | Verfahren zur Herstellung von Polymeren von ungesaettigten Kohlenwasserstoffen | |
| DE1157787B (de) | Verfahren zur Herstellung von Polybutadien | |
| DE1160186B (de) | Verfahren zur Herstellung von kautschukartigen Polymerisaten des Butadiens | |
| DE2338627C2 (de) | Verfahren zur Herstellung von modifizierten Dienpolymeren | |
| DE1154636B (de) | Verfahren zur Herstellung von Polymerisaten aus Butadien-(1, 3) | |
| DE1164096B (de) | Verfahren zur Herstellung von Polybutadien | |
| DE1144923B (de) | Verfahren zur Herstellung von Polybutadien | |
| DE1165863B (de) | Verfahren zur Herstellung von Polybutadien | |
| DE1181425B (de) | Verfahren zur Herstellung von Polymerisaten aus Butadien-(1, 3) | |
| DE1720064C3 (de) | Verfahren zum Vulkanisieren von Polymerisaten aus Polydiolefinen und Copolymerisaten aus mindestens zwei alpha-Olefinen und einem oder mehreren Multienen | |
| DE2325313C3 (de) | Verfahren zur Herstellung thermostabiler Block-Copolymerisate | |
| AT226432B (de) | Verfahren zur Herstellung linearer, amorpher, hochmolekularer, elastomerer Copolymeren | |
| DE1964653A1 (de) | Neue AEthylen-Propylen-1,3-Butadien-Copolymere,ihre Herstellung und Verwendung | |
| DE1251029B (de) | Verfah ren zur Polymerisation \on Isopren |