DE2257480C3 - Verfahren zur Herstellung von Copolymeren des Isobutylens - Google Patents
Verfahren zur Herstellung von Copolymeren des IsobutylensInfo
- Publication number
- DE2257480C3 DE2257480C3 DE2257480A DE2257480A DE2257480C3 DE 2257480 C3 DE2257480 C3 DE 2257480C3 DE 2257480 A DE2257480 A DE 2257480A DE 2257480 A DE2257480 A DE 2257480A DE 2257480 C3 DE2257480 C3 DE 2257480C3
- Authority
- DE
- Germany
- Prior art keywords
- cocatalyst
- isoprene
- polymer
- mmol
- weight
- 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
- 238000000034 method Methods 0.000 title claims description 18
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 title claims description 12
- 229920001577 copolymer Polymers 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 44
- 239000003054 catalyst Substances 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 150000002902 organometallic compounds Chemical class 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- SLLGVCUQYRMELA-UHFFFAOYSA-N chlorosilicon Chemical compound Cl[Si] SLLGVCUQYRMELA-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 description 37
- 239000000460 chlorine Substances 0.000 description 31
- 229920005549 butyl rubber Polymers 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000010936 titanium Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000000630 rising effect Effects 0.000 description 7
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- 238000007334 copolymerization reaction Methods 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- -1 carbonium ions Chemical class 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 238000004073 vulcanization Methods 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229960003750 ethyl chloride Drugs 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 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
- 125000001931 aliphatic group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 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
- 239000003085 diluting agent Substances 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-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
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000004071 soot 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
- 239000000725 suspension Substances 0.000 description 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 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
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
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
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)
- Polymerization Catalysts (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT31725/71A IT946101B (it) | 1971-11-26 | 1971-11-26 | Procedimento per la produzione di polimeri e copolimeri dell isobu tilene |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2257480A1 DE2257480A1 (de) | 1973-05-30 |
| DE2257480B2 DE2257480B2 (de) | 1978-07-20 |
| DE2257480C3 true DE2257480C3 (de) | 1979-03-15 |
Family
ID=11234273
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2257480A Expired DE2257480C3 (de) | 1971-11-26 | 1972-11-23 | Verfahren zur Herstellung von Copolymeren des Isobutylens |
Country Status (20)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5223465A (en) * | 1990-03-16 | 1993-06-29 | Tonen Corporation | Olefin polymerization catalyst |
| NL1004004C2 (nl) * | 1996-09-11 | 1998-03-12 | Dsm Nv | Werkwijze voor de polymerisatie van 2-gesubstitueerde 1-alkenen. |
| PL3224267T3 (pl) * | 2014-11-25 | 2021-07-12 | Versalis S.P.A. | Kompleks fosfinowy wanadu, układ katalityczny zawierający wspomniany kompleks fosfinowy wanadu i sposób (ko)polimeryzacji sprzężonych dienów |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL95675C (enrdf_load_stackoverflow) * | 1955-07-11 |
-
0
- BE BE791406D patent/BE791406A/xx unknown
-
1971
- 1971-11-26 IT IT31725/71A patent/IT946101B/it active
-
1972
- 1972-10-27 CS CS7200007256A patent/CS181228B2/cs unknown
- 1972-11-01 ZA ZA727775A patent/ZA727775B/xx unknown
- 1972-11-14 FR FR7240269A patent/FR2160850B1/fr not_active Expired
- 1972-11-20 ES ES409025A patent/ES409025A1/es not_active Expired
- 1972-11-20 CH CH1684472A patent/CH562268A5/xx not_active IP Right Cessation
- 1972-11-20 RO RO7200072863A patent/RO63619A/ro unknown
- 1972-11-21 TR TR17238A patent/TR17238A/xx unknown
- 1972-11-22 SU SU1847810A patent/SU505370A3/ru active
- 1972-11-23 DE DE2257480A patent/DE2257480C3/de not_active Expired
- 1972-11-24 LU LU66534A patent/LU66534A1/xx unknown
- 1972-11-24 AT AT1005672A patent/AT318234B/de not_active IP Right Cessation
- 1972-11-24 GB GB5452772A patent/GB1407418A/en not_active Expired
- 1972-11-24 DD DD167135A patent/DD103008A5/xx unknown
- 1972-11-24 PL PL1972159065A patent/PL91689B1/pl unknown
- 1972-11-24 HU HUSA2428A patent/HU167046B/hu unknown
- 1972-11-24 NL NL727215941A patent/NL153889B/xx unknown
- 1972-11-27 JP JP11813172A patent/JPS5336511B2/ja not_active Expired
- 1972-11-27 CA CA157,683A patent/CA994949A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES409025A1 (es) | 1975-10-16 |
| DE2257480B2 (de) | 1978-07-20 |
| AT318234B (de) | 1974-10-10 |
| AU4788272A (en) | 1974-04-26 |
| NL7215941A (enrdf_load_stackoverflow) | 1973-05-29 |
| LU66534A1 (enrdf_load_stackoverflow) | 1973-02-01 |
| DE2257480A1 (de) | 1973-05-30 |
| FR2160850B1 (enrdf_load_stackoverflow) | 1976-04-23 |
| ZA727775B (en) | 1973-07-25 |
| FR2160850A1 (enrdf_load_stackoverflow) | 1973-07-06 |
| TR17238A (tr) | 1976-08-03 |
| HU167046B (enrdf_load_stackoverflow) | 1975-07-28 |
| SU505370A3 (ru) | 1976-02-28 |
| CS181228B2 (en) | 1978-03-31 |
| BE791406A (fr) | 1973-03-01 |
| NL153889B (nl) | 1977-07-15 |
| DD103008A5 (enrdf_load_stackoverflow) | 1974-01-05 |
| CH562268A5 (enrdf_load_stackoverflow) | 1975-05-30 |
| PL91689B1 (enrdf_load_stackoverflow) | 1977-03-31 |
| CA994949A (en) | 1976-08-10 |
| RO63619A (fr) | 1978-08-15 |
| GB1407418A (en) | 1975-09-24 |
| IT946101B (it) | 1973-05-21 |
| JPS4864174A (enrdf_load_stackoverflow) | 1973-09-05 |
| JPS5336511B2 (enrdf_load_stackoverflow) | 1978-10-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| EHJ | Ceased/non-payment of the annual fee |