DE1173656C2 - Verfahren zur polymerisation von butadien oder isopren - Google Patents
Verfahren zur polymerisation von butadien oder isoprenInfo
- Publication number
- DE1173656C2 DE1173656C2 DE1956P0030040 DEP0030040A DE1173656C2 DE 1173656 C2 DE1173656 C2 DE 1173656C2 DE 1956P0030040 DE1956P0030040 DE 1956P0030040 DE P0030040 A DEP0030040 A DE P0030040A DE 1173656 C2 DE1173656 C2 DE 1173656C2
- Authority
- DE
- Germany
- Prior art keywords
- addition
- catalyst
- butadiene
- polymer
- isoprene
- 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
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 title claims description 52
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title claims description 42
- 238000000034 method Methods 0.000 title claims description 36
- 238000006116 polymerization reaction Methods 0.000 title claims description 20
- 229920000642 polymer Polymers 0.000 claims description 51
- 239000003054 catalyst Substances 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 28
- 239000003085 diluting agent Substances 0.000 claims description 20
- 229920002857 polybutadiene Polymers 0.000 claims description 19
- 239000005062 Polybutadiene Substances 0.000 claims description 16
- NLLZTRMHNHVXJJ-UHFFFAOYSA-J titanium tetraiodide Chemical group I[Ti](I)(I)I NLLZTRMHNHVXJJ-UHFFFAOYSA-J 0.000 claims description 14
- -1 titanium halide Chemical class 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000000178 monomer Substances 0.000 claims description 9
- 238000011925 1,2-addition Methods 0.000 claims description 8
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 8
- 229920001195 polyisoprene Polymers 0.000 claims description 8
- 229920001971 elastomer Polymers 0.000 claims description 7
- 238000012360 testing method Methods 0.000 claims description 7
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 6
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 5
- 239000005060 rubber Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 3
- 229910052708 sodium Inorganic materials 0.000 claims 3
- 239000011734 sodium Substances 0.000 claims 3
- 229910052719 titanium Inorganic materials 0.000 claims 3
- 239000010936 titanium Substances 0.000 claims 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 2
- 150000001340 alkali metals Chemical group 0.000 claims 2
- 229910052792 caesium Chemical group 0.000 claims 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical group [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims 2
- 229910052700 potassium Inorganic materials 0.000 claims 2
- 239000011591 potassium Substances 0.000 claims 2
- 229910052701 rubidium Inorganic materials 0.000 claims 2
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical group [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 229910000809 Alumel Inorganic materials 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- 238000009825 accumulation Methods 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 230000008602 contraction Effects 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 230000006855 networking Effects 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 230000002441 reversible effect Effects 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 29
- 238000013459 approach Methods 0.000 description 22
- 229910010082 LiAlH Inorganic materials 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 240000002636 Manilkara bidentata Species 0.000 description 7
- 235000016302 balata Nutrition 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000008033 biological extinction Effects 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- 238000004073 vulcanization Methods 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000004071 soot Substances 0.000 description 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 210000004072 lung Anatomy 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-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
- 238000002835 absorbance Methods 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- YAGKRVSRTSUGEY-UHFFFAOYSA-N ferricyanide Chemical compound [Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] YAGKRVSRTSUGEY-UHFFFAOYSA-N 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000006069 physical mixture Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 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
- 239000004636 vulcanized rubber Substances 0.000 description 1
- 239000008096 xylene 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B28—WORKING CEMENT, CLAY, OR STONE
- B28B—SHAPING CLAY OR OTHER CERAMIC COMPOSITIONS; SHAPING SLAG; SHAPING MIXTURES CONTAINING CEMENTITIOUS MATERIAL, e.g. PLASTER
- B28B1/00—Producing shaped prefabricated articles from the material
- B28B1/29—Producing shaped prefabricated articles from the material by profiling or strickling the material in open moulds or on moulding surfaces
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B28—WORKING CEMENT, CLAY, OR STONE
- B28B—SHAPING CLAY OR OTHER CERAMIC COMPOSITIONS; SHAPING SLAG; SHAPING MIXTURES CONTAINING CEMENTITIOUS MATERIAL, e.g. PLASTER
- B28B7/00—Moulds; Cores; Mandrels
- B28B7/0064—Moulds characterised by special surfaces for producing a desired surface of a moulded article, e.g. profiled or polished moulding surfaces
-
- 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)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- Ceramic Engineering (AREA)
- Mechanical Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54103655A | 1955-10-17 | 1955-10-17 | |
| US54103355A | 1955-10-17 | 1955-10-17 | |
| US579429A US3050513A (en) | 1955-10-17 | 1956-04-20 | Process and catalyst for production of rubbery polymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1173656B DE1173656B (de) | 1975-05-22 |
| DE1173656C2 true DE1173656C2 (de) | 1975-05-22 |
Family
ID=27415342
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1956P0030040 Expired DE1173656C2 (de) | 1955-10-17 | 1956-10-15 | Verfahren zur polymerisation von butadien oder isopren |
| DE19561420647 Pending DE1420647A1 (de) | 1955-10-17 | 1956-10-15 | Verfahren und Katalysator zum Polymerisieren von Dienen mit konjugierten Doppelbindungen |
| DEP30038A Pending DE1174074B (de) | 1955-10-17 | 1956-10-15 | Verfahren zur Herstellung eines kautschuk-artigen Polymerisats von 1,3-Butadien |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19561420647 Pending DE1420647A1 (de) | 1955-10-17 | 1956-10-15 | Verfahren und Katalysator zum Polymerisieren von Dienen mit konjugierten Doppelbindungen |
| DEP30038A Pending DE1174074B (de) | 1955-10-17 | 1956-10-15 | Verfahren zur Herstellung eines kautschuk-artigen Polymerisats von 1,3-Butadien |
Country Status (8)
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL236107A (US07915450-20110329-C00059.png) * | 1954-12-02 | |||
| DE1174072B (de) * | 1957-07-26 | 1964-07-16 | Dunlop Rubber Co | Verfahren zur Polymerisation von konjugierten Diolefinen |
| US3105828A (en) * | 1957-12-30 | 1963-10-01 | Shell Oil Co | Polymerizing diolefins with alkyl lithium catalyst in tetrahydrofuran solvent |
| US3232920A (en) * | 1958-03-06 | 1966-02-01 | Phillips Petroleum Co | Preparation of rubbery polymers of butadiene |
| NL258909A (US07915450-20110329-C00059.png) * | 1958-09-17 | |||
| NL244821A (US07915450-20110329-C00059.png) * | 1958-10-30 | |||
| DE1139646B (de) * | 1958-12-19 | 1962-11-15 | Goodrich Gulf Chem Inc | Verfahren zur Polymerisation von Butadien-(1, 3)-Kohlenwasserstoffen |
| NL120307C (US07915450-20110329-C00059.png) * | 1959-04-07 | |||
| US3067189A (en) * | 1959-12-24 | 1962-12-04 | Shell Oil Co | Diene polymerization catalyst |
| NL259400A (US07915450-20110329-C00059.png) * | 1959-12-26 | |||
| NL112343C (US07915450-20110329-C00059.png) * | 1960-02-20 | |||
| US3057840A (en) * | 1960-02-23 | 1962-10-09 | Phillips Petroleum Co | Method for controlling the temperature in a butadiene polymerization process |
| US3139468A (en) * | 1960-06-20 | 1964-06-30 | Phillips Petroleum Co | Altering dimension of vulcanized transpolybutadiene and heating to cause same to appoach original shape |
| US3066129A (en) * | 1960-07-15 | 1962-11-27 | Phillips Petroleum Co | Production of rubbery polymers with a lithium aluminum hydride-titanium chloride-iodine catalyst |
| NL267714A (US07915450-20110329-C00059.png) * | 1960-08-08 | |||
| GB933418A (en) * | 1960-09-30 | 1963-08-08 | Firestone Tire & Rubber Co | Polymerization of butadiene |
| DE1173655B (de) * | 1960-10-03 | 1964-07-09 | Phillips Petroleum Co | Verfahren zur Herstellung von kautschukartigen Polymerisaten aus 1, 3-Butadien |
| NL271399A (US07915450-20110329-C00059.png) * | 1960-11-19 | |||
| US3166609A (en) * | 1960-11-21 | 1965-01-19 | Phillips Petroleum Co | Blends of trans-polybutadiene with rubber |
| NL273421A (US07915450-20110329-C00059.png) * | 1961-01-12 | |||
| BE612732A (US07915450-20110329-C00059.png) * | 1961-01-18 | |||
| ES273651A1 (es) * | 1961-01-31 | 1962-04-01 | Lymer Corp Ltd | Un procedimiento de producir un polimero de butadieno |
| US3254069A (en) * | 1961-02-27 | 1966-05-31 | Firestone Tire & Rubber Co | Preparation of high cis-1, 4 polybutadiene |
| BE616725A (US07915450-20110329-C00059.png) * | 1961-04-20 | |||
| BE617545A (US07915450-20110329-C00059.png) * | 1961-05-13 | |||
| US3205214A (en) * | 1961-05-15 | 1965-09-07 | Firestone Tire & Rubber Co | Piperylene polymerization |
| DE1157399B (de) * | 1961-06-21 | 1963-11-14 | Polymer Corp | Verfahren zur Herstellung eines Polymerisats mit trans-1, 4-Struktur aus einem konjugierten diolefinischen Kohlenwasserstoff |
| NL130130C (US07915450-20110329-C00059.png) * | 1961-07-17 | |||
| DE1302747B (US07915450-20110329-C00059.png) * | 1961-08-30 | 1971-09-23 | Philips Petroleum Co | |
| US3202646A (en) * | 1961-09-25 | 1965-08-24 | Phillips Petroleum Co | Production of cis-polybutadiene in an aromatic-aliphatic mixed diluent |
| US3182052A (en) * | 1961-11-20 | 1965-05-04 | Phillips Petroleum Co | Process for producing cis-1, 4-polybutadiene of reduced cold-flow |
| US3243481A (en) * | 1962-01-08 | 1966-03-29 | Dow Chemical Co | Process for making graft copolymers of vinyl aromatic compounds and stereospecific rubbers |
| US3223694A (en) * | 1962-03-20 | 1965-12-14 | Phillips Petroleum Co | Process and catalyst for production of rubbery polymers |
| US3213160A (en) * | 1962-09-17 | 1965-10-19 | Phillips Petroleum Co | Blends of synthetic trans-polyisoprene and trans-polybutadiene |
| US3244773A (en) * | 1962-09-28 | 1966-04-05 | Phillips Petroleum Co | Addition of trans-polybutadiene to prevent cold flow in cis-polybutadiene |
| US3248288A (en) * | 1963-04-30 | 1966-04-26 | Phillips Petroleum Co | Low weathering rate solid pest control composition and method |
| US3258440A (en) * | 1963-05-29 | 1966-06-28 | Phillips Petroleum Co | Preparation of cis-polybutadiene latex with sorbitans, sorbides or monoolefin-maleic anhydride copolymer |
| US3506527A (en) * | 1965-04-30 | 1970-04-14 | Phillips Petroleum Co | Laminates containing trans-polybutadiene |
| US4020008A (en) * | 1974-03-01 | 1977-04-26 | Phillips Petroleum Company | Catalysts for producing high trans-polybutadiene |
| US3926933A (en) * | 1974-03-01 | 1975-12-16 | Phillips Petroleum Co | Catalysts for producing high trans-polybutadiene |
| US4020007A (en) * | 1974-04-25 | 1977-04-26 | Phillips Petroleum Company | Catalyst for preparation of polybutadiene |
| US3896102A (en) * | 1974-04-25 | 1975-07-22 | Phillips Petroleum Co | Preparation of polybutadiene |
| US4035570A (en) * | 1975-01-23 | 1977-07-12 | Phillips Petroleum Company | Method and catalyst for the production of high trans-polyalkadiene |
| US4310582A (en) * | 1977-06-20 | 1982-01-12 | Phillips Petroleum Company | Blends of trans-polybutadiene and medium vinyl polybutadiene |
| US4579701A (en) * | 1984-09-24 | 1986-04-01 | The Dow Chemical Company | Method for obtaining low densities with particulate expandable polystyrene |
| US6677013B1 (en) | 1998-04-17 | 2004-01-13 | Pechiney Emballage Flexible Europe | Transparent multilayer polypropylene container with barrier protection |
| JP3627586B2 (ja) | 1999-09-03 | 2005-03-09 | 日本ゼオン株式会社 | リチウムイオン二次電池電極用バインダー、およびその利用 |
| KR100344230B1 (ko) | 1999-10-13 | 2002-07-24 | 금호석유화학 주식회사 | 산소분자를 이용한 하이드록시 고 1,4-시스 폴리부타디엔의 제조방법 |
| MXPA04003914A (es) | 2001-10-24 | 2004-06-21 | Pechiney Emballage Flexible Eu | Envase de polipropileno y proceso para fabricarlo. |
| ITMI20111652A1 (it) | 2011-09-14 | 2013-03-15 | Polimeri Europa Spa | Complesso oss-azotato di lantanidi, sistema catalitico comprendente detto complesso osso-azotato e procedimento per la (co)polimerizzazione di dieni coniugati |
| ITMI20111650A1 (it) | 2011-09-14 | 2013-03-15 | Polimeri Europa Spa | Complesso bis-imminico di lantanidi, sistema catalitico comprendente detto complesso bis-imminico e procedimento per la (co)polimerizzazione di dieni coniugati |
| ITMI20111651A1 (it) | 2011-09-14 | 2013-03-15 | Polimeri Europa Spa | Complesso bis-immino piridinico di lantanidi, sistema catalitico comprendente detto complesso bis-immino piridinico e procedimento per la (co)polimerizzazione di dieni coniugati |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1058056A (en) * | 1911-11-04 | 1913-04-08 | Farbenfab Vorm Bayer F & Co | Caoutchouc substances and process of making same. |
| US2699457A (en) * | 1950-06-21 | 1955-01-11 | Ziegler Karl | Polymerization of ethylene |
| NL88143C (US07915450-20110329-C00059.png) * | 1952-12-06 | |||
| CH363436A (de) * | 1954-06-08 | 1962-07-31 | Montedison Spa | Als Folie, Faser oder Faden geformtes Erzeugnis und Verfahren zu dessen Herstellung |
| US2721189A (en) * | 1954-08-30 | 1955-10-18 | Du Pont | Polymeric bicyclo-(2, 2, 1)-2-heptene |
| BE638937A (US07915450-20110329-C00059.png) * | 1955-12-16 |
-
0
- NL NL121436D patent/NL121436C/xx active
- NL NL111783D patent/NL111783C/xx active
- NL NL211454D patent/NL211454A/xx unknown
- BE BE551851D patent/BE551851A/xx unknown
- NL NL299756D patent/NL299756A/xx unknown
-
1955
- 1955-10-17 GB GB31589/56A patent/GB845200A/en not_active Expired
-
1956
- 1956-04-20 US US579429A patent/US3050513A/en not_active Expired - Lifetime
- 1956-10-15 DE DE1956P0030040 patent/DE1173656C2/de not_active Expired
- 1956-10-15 DE DE19561420647 patent/DE1420647A1/de active Pending
- 1956-10-15 DE DEP30038A patent/DE1174074B/de active Pending
- 1956-10-16 FR FR723827A patent/FR1247307A/fr not_active Expired
- 1956-10-17 GB GB7717/60A patent/GB852277A/en not_active Expired
- 1956-10-17 GB GB20787/59A patent/GB848067A/en not_active Expired
- 1956-10-17 CH CH1213261A patent/CH366399A/fr unknown
- 1956-10-17 CH CH360499D patent/CH360499A/fr unknown
- 1956-10-17 GB GB20786/59A patent/GB848064A/en not_active Expired
- 1956-10-17 GB GB20785/59A patent/GB848065A/en not_active Expired
-
1963
- 1963-06-28 DK DK309863AA patent/DK114443B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL299756A (US07915450-20110329-C00059.png) | |
| GB848067A (en) | 1960-09-14 |
| DE1173656B (de) | 1975-05-22 |
| DE1420647A1 (de) | 1968-10-24 |
| FR1247307A (fr) | 1960-10-24 |
| DE1174074B (de) | 1964-07-16 |
| GB845200A (en) | 1960-08-17 |
| US3050513A (en) | 1962-08-21 |
| GB848065A (en) | 1960-09-14 |
| NL211454A (US07915450-20110329-C00059.png) | |
| DK114443B (da) | 1969-06-30 |
| CH360499A (fr) | 1962-02-28 |
| NL121436C (US07915450-20110329-C00059.png) | |
| CH366399A (fr) | 1962-12-31 |
| GB852277A (en) | 1960-10-26 |
| GB848064A (en) | 1960-09-14 |
| BE551851A (US07915450-20110329-C00059.png) | |
| NL111783C (US07915450-20110329-C00059.png) |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 |