DE2636930A1 - Verfahren zur herstellung von copolymeren mit elastomereigenschaften durch copolymerisation von olefinmonomeren - Google Patents
Verfahren zur herstellung von copolymeren mit elastomereigenschaften durch copolymerisation von olefinmonomerenInfo
- Publication number
- DE2636930A1 DE2636930A1 DE19762636930 DE2636930A DE2636930A1 DE 2636930 A1 DE2636930 A1 DE 2636930A1 DE 19762636930 DE19762636930 DE 19762636930 DE 2636930 A DE2636930 A DE 2636930A DE 2636930 A1 DE2636930 A1 DE 2636930A1
- Authority
- DE
- Germany
- Prior art keywords
- olefin monomers
- butadiene
- weight
- copolymers
- phosgene
- 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.)
- Withdrawn
Links
- 239000000178 monomer Substances 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 15
- 150000001336 alkenes Chemical class 0.000 title claims description 13
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 13
- 229920001971 elastomer Polymers 0.000 title claims description 10
- 239000000806 elastomer Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 5
- 238000007334 copolymerization reaction Methods 0.000 title description 2
- 229920001577 copolymer Polymers 0.000 claims description 26
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 19
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 9
- 238000000197 pyrolysis Methods 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims description 2
- 230000032683 aging Effects 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 18
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical class CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 4
- 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 4
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 4
- 230000003712 anti-aging effect Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 3
- 150000005673 monoalkenes Chemical class 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012452 mother liquor Substances 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
- 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
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- 229910002018 Aerosil® 300 Inorganic materials 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 244000043261 Hevea brasiliensis Species 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
- 229920002367 Polyisobutene Polymers 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920005606 polypropylene copolymer Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010063 rubber manufacturing process Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 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
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—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
- C08F236/04—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
- C08F236/06—Butadiene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/04—Monomers containing three or four carbon atoms
- C08F210/08—Butenes
- C08F210/10—Isobutene
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)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU75MU00000542A HU172849B (hu) | 1975-08-19 | 1975-08-19 | Sposob poluchenija ehlastomernogo kopolimera iz izobutilena i butadiena |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2636930A1 true DE2636930A1 (de) | 1977-03-03 |
Family
ID=10999717
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762636930 Withdrawn DE2636930A1 (de) | 1975-08-19 | 1976-08-17 | Verfahren zur herstellung von copolymeren mit elastomereigenschaften durch copolymerisation von olefinmonomeren |
Country Status (12)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4572496A (en) * | 1983-09-08 | 1986-02-25 | Moore Business Forms, Inc. | Trim rewinder with automatic stop |
| DE19718201A1 (de) * | 1997-04-30 | 1998-11-05 | Bayer Ag | Neue Terpolymere aus Isoolefinen, konjugierten Diolefinen und ein- oder mehrfach ungesättigten organischen Verbindungen |
| CA2383474A1 (en) * | 2002-04-26 | 2003-10-26 | Bayer Inc. | Rubber composition for tire treads |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1327664A (en) | 1970-05-14 | 1973-08-22 | Bridgestone Tire Co Ltd | Method for manufacturing butadiene-propylene copolymers |
| US3808177A (en) * | 1971-06-08 | 1974-04-30 | Exxon Research Engineering Co | High molecular weight,high unsaturation c4-c10 isoolefin conjugated diene copolymers |
| US3850897A (en) * | 1971-11-26 | 1974-11-26 | Snam Progetti | Procedure for the production of polymers and copolymers of isobutylene |
-
1975
- 1975-08-19 HU HU75MU00000542A patent/HU172849B/hu not_active IP Right Cessation
-
1976
- 1976-08-16 US US05/714,655 patent/US4097658A/en not_active Expired - Lifetime
- 1976-08-16 FR FR7624854A patent/FR2321510A1/fr active Granted
- 1976-08-16 CS CS765319A patent/CS190731B1/cs unknown
- 1976-08-17 DE DE19762636930 patent/DE2636930A1/de not_active Withdrawn
- 1976-08-17 SU SU762387309A patent/SU828973A3/ru active
- 1976-08-17 NL NL7609116A patent/NL7609116A/xx not_active Application Discontinuation
- 1976-08-18 IT IT26323/76A patent/IT1076933B/it active
- 1976-08-18 GB GB34459/76A patent/GB1504236A/en not_active Expired
- 1976-08-18 BE BE169903A patent/BE845297A/xx not_active IP Right Cessation
- 1976-08-18 DD DD194373A patent/DD125412A1/xx unknown
- 1976-08-18 JP JP51097818A patent/JPS5235287A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CS190731B1 (en) | 1979-06-29 |
| IT1076933B (it) | 1985-04-27 |
| SU828973A3 (ru) | 1981-05-07 |
| US4097658A (en) | 1978-06-27 |
| GB1504236A (en) | 1978-03-15 |
| BE845297A (fr) | 1976-12-16 |
| FR2321510B3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-05-11 |
| JPS5235287A (en) | 1977-03-17 |
| DD125412A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-04-20 |
| HU172849B (hu) | 1978-12-28 |
| NL7609116A (nl) | 1977-02-22 |
| FR2321510A1 (fr) | 1977-03-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |