DE2142684A1 - Verfahren zum Herstellen farbloser, vinylreicher Dienpolymerer - Google Patents
Verfahren zum Herstellen farbloser, vinylreicher DienpolymererInfo
- Publication number
- DE2142684A1 DE2142684A1 DE19712142684 DE2142684A DE2142684A1 DE 2142684 A1 DE2142684 A1 DE 2142684A1 DE 19712142684 DE19712142684 DE 19712142684 DE 2142684 A DE2142684 A DE 2142684A DE 2142684 A1 DE2142684 A1 DE 2142684A1
- Authority
- DE
- Germany
- Prior art keywords
- temperature
- dimethyl ether
- polymerization
- weight
- parts
- 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
- 150000001993 dienes Chemical class 0.000 title claims description 15
- 229920000642 polymer Polymers 0.000 title description 21
- 238000000034 method Methods 0.000 title description 17
- 229920002554 vinyl polymer Polymers 0.000 title description 14
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title description 13
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 64
- 238000006116 polymerization reaction Methods 0.000 claims description 33
- 239000003054 catalyst Substances 0.000 claims description 14
- 239000000178 monomer Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 239000003607 modifier Substances 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- -1 alkali metal hydrocarbon Chemical class 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 238000013021 overheating Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000002826 coolant Substances 0.000 description 3
- 230000017525 heat dissipation Effects 0.000 description 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-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
- IRDQNLLVRXMERV-UHFFFAOYSA-N CCCC[Na] Chemical compound CCCC[Na] IRDQNLLVRXMERV-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- URXNVXOMQQCBHS-UHFFFAOYSA-N naphthalene;sodium Chemical compound [Na].C1=CC=CC2=CC=CC=C21 URXNVXOMQQCBHS-UHFFFAOYSA-N 0.000 description 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- IJZBERUKRLKPEL-UHFFFAOYSA-N (2-methyl-1-phenylprop-2-enyl)benzene Chemical compound C=1C=CC=CC=1C(C(=C)C)C1=CC=CC=C1 IJZBERUKRLKPEL-UHFFFAOYSA-N 0.000 description 1
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
- NYUXIFDLNGQOLF-UHFFFAOYSA-N 1-chloro-4-ethenylnaphthalene Chemical compound C1=CC=C2C(Cl)=CC=C(C=C)C2=C1 NYUXIFDLNGQOLF-UHFFFAOYSA-N 0.000 description 1
- RSMGGUQMXYWDEX-UHFFFAOYSA-N 1-cyclohexyl-2-ethenylnaphthalene Chemical compound C=CC1=CC=C2C=CC=CC2=C1C1CCCCC1 RSMGGUQMXYWDEX-UHFFFAOYSA-N 0.000 description 1
- VDNSZPNSUQRUMS-UHFFFAOYSA-N 1-cyclohexyl-4-ethenylbenzene Chemical compound C1=CC(C=C)=CC=C1C1CCCCC1 VDNSZPNSUQRUMS-UHFFFAOYSA-N 0.000 description 1
- DHOXBCSHDGACEZ-UHFFFAOYSA-N 1-hex-5-enylnaphthalene Chemical compound C1=CC=C2C(CCCCC=C)=CC=CC2=C1 DHOXBCSHDGACEZ-UHFFFAOYSA-N 0.000 description 1
- OGMSGZZPTQNTIK-UHFFFAOYSA-N 1-methyl-2-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1C OGMSGZZPTQNTIK-UHFFFAOYSA-N 0.000 description 1
- SYEOAIBCORNGJS-UHFFFAOYSA-N 1-n,4-n-bis(1-ethyl-5-methylcyclohexa-2,4-dien-1-yl)benzene-1,4-diamine Chemical compound C=1C=C(NC2(CC)C=CC=C(C)C2)C=CC=1NC1(CC)CC(C)=CC=C1 SYEOAIBCORNGJS-UHFFFAOYSA-N 0.000 description 1
- MUFTXXUPGWDJLU-UHFFFAOYSA-N 1-phenylprop-2-enylbenzene Chemical compound C=1C=CC=CC=1C(C=C)C1=CC=CC=C1 MUFTXXUPGWDJLU-UHFFFAOYSA-N 0.000 description 1
- LCJNYCWJKAWZKZ-UHFFFAOYSA-N 1-prop-1-en-2-ylnaphthalene Chemical compound C1=CC=C2C(C(=C)C)=CC=CC2=C1 LCJNYCWJKAWZKZ-UHFFFAOYSA-N 0.000 description 1
- RJFCFNWLPJRCLR-UHFFFAOYSA-N 1-prop-2-enylnaphthalene Chemical compound C1=CC=C2C(CC=C)=CC=CC2=C1 RJFCFNWLPJRCLR-UHFFFAOYSA-N 0.000 description 1
- GCUMYNSADGZQBV-UHFFFAOYSA-N 1-propan-2-yl-2-prop-1-en-2-ylnaphthalene Chemical compound C1=CC=C2C(C(C)C)=C(C(C)=C)C=CC2=C1 GCUMYNSADGZQBV-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- XBTCBCUOVVISEQ-UHFFFAOYSA-N 2-phenylbut-3-en-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C=C)(C)C1=CC=CC=C1 XBTCBCUOVVISEQ-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- UKZZSQRNPVODAJ-UHFFFAOYSA-N CCCCCCCCCC[Na] Chemical compound CCCCCCCCCC[Na] UKZZSQRNPVODAJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- XSKGTWYZHRFPLU-UHFFFAOYSA-N benzylbenzene;lithium Chemical compound [Li].C=1C=CC=CC=1CC1=CC=CC=C1 XSKGTWYZHRFPLU-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000000460 chlorine Chemical group 0.000 description 1
- 229910052801 chlorine Chemical group 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- XBEREOHJDYAKDA-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].CC[CH2-] XBEREOHJDYAKDA-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- IJJSYKQZFFGIEE-UHFFFAOYSA-N naphthalene;potassium Chemical compound [K].C1=CC=CC2=CC=CC=C21 IJJSYKQZFFGIEE-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 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
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7141370A | 1970-09-11 | 1970-09-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2142684A1 true DE2142684A1 (de) | 1972-03-23 |
Family
ID=22101158
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712142684 Pending DE2142684A1 (de) | 1970-09-11 | 1971-08-26 | Verfahren zum Herstellen farbloser, vinylreicher Dienpolymerer |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3686158A (https=) |
| AT (1) | AT323404B (https=) |
| AU (1) | AU464901B2 (https=) |
| BE (1) | BE772414A (https=) |
| BR (1) | BR7105936D0 (https=) |
| CA (1) | CA995395A (https=) |
| CH (1) | CH552637A (https=) |
| DE (1) | DE2142684A1 (https=) |
| ES (1) | ES394991A1 (https=) |
| FR (1) | FR2106276A5 (https=) |
| GB (1) | GB1343940A (https=) |
| NL (1) | NL7112517A (https=) |
| SE (1) | SE366999B (https=) |
| ZA (1) | ZA715009B (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2255313B1 (https=) * | 1973-12-20 | 1976-10-08 | Gole Jean | |
| US3899406A (en) * | 1974-04-26 | 1975-08-12 | Firestone Tire & Rubber Co | Antioxidants for ultraviolet curable high vinyl polybutadienes |
| US5061765A (en) * | 1990-10-22 | 1991-10-29 | The Goodyear Tire & Rubber Company | Process for the synthesis of a high vinyl isoprene-butadiene copolymer |
| TWI486367B (zh) * | 2012-05-30 | 2015-06-01 | Nippon Soda Co | 聚胺甲酸酯 |
-
1970
- 1970-09-11 US US71413A patent/US3686158A/en not_active Expired - Lifetime
-
1971
- 1971-07-27 ZA ZA715009A patent/ZA715009B/xx unknown
- 1971-08-02 SE SE09875/71A patent/SE366999B/xx unknown
- 1971-08-03 CA CA119,711A patent/CA995395A/en not_active Expired
- 1971-08-24 GB GB3975271A patent/GB1343940A/en not_active Expired
- 1971-08-26 CH CH1253371A patent/CH552637A/xx not_active IP Right Cessation
- 1971-08-26 DE DE19712142684 patent/DE2142684A1/de active Pending
- 1971-09-01 AT AT759971A patent/AT323404B/de not_active IP Right Cessation
- 1971-09-09 BR BR5936/71A patent/BR7105936D0/pt unknown
- 1971-09-09 BE BE772414A patent/BE772414A/xx unknown
- 1971-09-10 NL NL7112517A patent/NL7112517A/xx unknown
- 1971-09-10 FR FR7132730A patent/FR2106276A5/fr not_active Expired
- 1971-09-10 AU AU33353/71A patent/AU464901B2/en not_active Expired
- 1971-09-11 ES ES394991A patent/ES394991A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7112517A (https=) | 1972-03-14 |
| AU3335371A (en) | 1973-03-15 |
| AT323404B (de) | 1975-07-10 |
| BR7105936D0 (pt) | 1973-04-17 |
| CA995395A (en) | 1976-08-17 |
| SE366999B (https=) | 1974-05-13 |
| ZA715009B (en) | 1972-04-26 |
| CH552637A (de) | 1974-08-15 |
| ES394991A1 (es) | 1974-12-01 |
| FR2106276A5 (https=) | 1972-04-28 |
| GB1343940A (en) | 1974-01-16 |
| AU464901B2 (en) | 1975-09-11 |
| BE772414A (fr) | 1972-03-09 |
| US3686158A (en) | 1972-08-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |