CA1052947A - Continuous solution polymerization process - Google Patents
Continuous solution polymerization processInfo
- Publication number
- CA1052947A CA1052947A CA242,532A CA242532A CA1052947A CA 1052947 A CA1052947 A CA 1052947A CA 242532 A CA242532 A CA 242532A CA 1052947 A CA1052947 A CA 1052947A
- Authority
- CA
- Canada
- Prior art keywords
- fact
- process according
- agents
- agent
- reaction
- 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 21
- 238000010528 free radical solution polymerization reaction Methods 0.000 title abstract description 3
- 239000000499 gel Substances 0.000 claims abstract description 27
- -1 vinyl aromatic compounds Chemical class 0.000 claims abstract description 21
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 16
- 239000003999 initiator Substances 0.000 claims abstract description 14
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 13
- 150000001993 dienes Chemical class 0.000 claims abstract description 11
- 230000009849 deactivation Effects 0.000 claims abstract description 9
- 125000001979 organolithium group Chemical group 0.000 claims abstract description 8
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 96
- 239000003795 chemical substances by application Substances 0.000 claims description 72
- 238000006243 chemical reaction Methods 0.000 claims description 58
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical group [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 46
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 38
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 34
- 239000000178 monomer Substances 0.000 claims description 31
- 238000007334 copolymerization reaction Methods 0.000 claims description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 19
- 229920001577 copolymer Polymers 0.000 claims description 18
- 238000012546 transfer Methods 0.000 claims description 18
- 229920002521 macromolecule Polymers 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 16
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 12
- 229910052744 lithium Inorganic materials 0.000 claims description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 150000001340 alkali metals Chemical class 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 229930194542 Keto Natural products 0.000 claims description 3
- 150000004645 aluminates Chemical class 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229920001519 homopolymer Polymers 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 22
- 238000005755 formation reaction Methods 0.000 description 13
- 230000014759 maintenance of location Effects 0.000 description 13
- 238000006276 transfer reaction Methods 0.000 description 5
- 238000010924 continuous production Methods 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-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
- 239000005977 Ethylene Substances 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002900 organolithium compounds Chemical class 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 230000036647 reaction Effects 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical class ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- PDELBHCVXBSVPJ-UHFFFAOYSA-N 2-ethenyl-1,3,5-trimethylbenzene Chemical group CC1=CC(C)=C(C=C)C(C)=C1 PDELBHCVXBSVPJ-UHFFFAOYSA-N 0.000 description 1
- CTHJQRHPNQEPAB-UHFFFAOYSA-N 2-methoxyethenylbenzene Chemical class COC=CC1=CC=CC=C1 CTHJQRHPNQEPAB-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- CGKRFDXHYBJWPO-UHFFFAOYSA-N C(C)[AlH]CC.[Na] Chemical compound C(C)[AlH]CC.[Na] CGKRFDXHYBJWPO-UHFFFAOYSA-N 0.000 description 1
- XTOCNPFOBJKQBK-UHFFFAOYSA-N C1=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12.[Li] Chemical compound C1=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12.[Li] XTOCNPFOBJKQBK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000006621 Wurtz reaction Methods 0.000 description 1
- FNRUENJVQDCBQZ-UHFFFAOYSA-N [Li]CCCCCCCCCCCCCCCCCCCC[Li] Chemical compound [Li]CCCCCCCCCCCCCCCCCCCC[Li] FNRUENJVQDCBQZ-UHFFFAOYSA-N 0.000 description 1
- BZEZSORUWZUMNU-UHFFFAOYSA-N [Li]CCCC[Li] Chemical compound [Li]CCCC[Li] BZEZSORUWZUMNU-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001361 allenes Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- UENPGSSYCLIBMR-UHFFFAOYSA-N anthracene;lithium Chemical compound [Li].C1=CC=CC2=CC3=CC=CC=C3C=C21 UENPGSSYCLIBMR-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000002844 continuous effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical compound [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 1
- ZEFNMRMJJKIGBT-UHFFFAOYSA-N dilithium;pentane Chemical compound [Li+].[Li+].[CH2-]CCC[CH2-] ZEFNMRMJJKIGBT-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- ZMZIEZHJTIVGGP-UHFFFAOYSA-N diphenylmethanone;potassium Chemical compound [K].C=1C=CC=CC=1C(=O)C1=CC=CC=C1 ZMZIEZHJTIVGGP-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- CCZVEWRRAVASGL-UHFFFAOYSA-N lithium;2-methanidylpropane Chemical compound [Li+].CC(C)[CH2-] CCZVEWRRAVASGL-UHFFFAOYSA-N 0.000 description 1
- ZLPHTMMGQHNDDQ-UHFFFAOYSA-N lithium;2-methylbutane Chemical compound [Li+].CC(C)C[CH2-] ZLPHTMMGQHNDDQ-UHFFFAOYSA-N 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- PDZGAEAUKGKKDE-UHFFFAOYSA-N lithium;naphthalene Chemical compound [Li].C1=CC=CC2=CC=CC=C21 PDZGAEAUKGKKDE-UHFFFAOYSA-N 0.000 description 1
- VCPPTNDHEILJHD-UHFFFAOYSA-N lithium;prop-1-ene Chemical compound [Li+].[CH2-]C=C VCPPTNDHEILJHD-UHFFFAOYSA-N 0.000 description 1
- SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 238000006263 metalation reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- URXNVXOMQQCBHS-UHFFFAOYSA-N naphthalene;sodium Chemical compound [Na].C1=CC=CC2=CC=CC=C21 URXNVXOMQQCBHS-UHFFFAOYSA-N 0.000 description 1
- 238000002103 osmometry Methods 0.000 description 1
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 1
- 150000008039 phosphoramides Chemical class 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920005547 polycyclic aromatic hydrocarbon Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 150000005837 radical ions Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- JLZUZNKTTIRERF-UHFFFAOYSA-N tetraphenylethylene Chemical group C1=CC=CC=C1C(C=1C=CC=CC=1)=C(C=1C=CC=CC=1)C1=CC=CC=C1 JLZUZNKTTIRERF-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N trans-Stilbene Natural products C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 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
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)
- Polymerisation Methods In General (AREA)
- Polyesters Or Polycarbonates (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Biological Depolymerization Polymers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7442810A FR2295972A1 (fr) | 1974-12-23 | 1974-12-23 | Polymerisation ou copolymerisation en solution d'un ou plusieurs dienes conjugues avec eventuellement un ou plusieurs composes vinylaromatiques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1052947A true CA1052947A (en) | 1979-04-17 |
Family
ID=9146627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA242,532A Expired CA1052947A (en) | 1974-12-23 | 1975-12-22 | Continuous solution polymerization process |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4136245A (en, 2012) |
| JP (1) | JPS5183685A (en, 2012) |
| AR (1) | AR217800A1 (en, 2012) |
| AT (1) | AT345546B (en, 2012) |
| AU (1) | AU504064B2 (en, 2012) |
| BE (1) | BE836667A (en, 2012) |
| BR (1) | BR7508614A (en, 2012) |
| CA (1) | CA1052947A (en, 2012) |
| CH (1) | CH608508A5 (en, 2012) |
| DE (1) | DE2558139C2 (en, 2012) |
| EG (1) | EG13100A (en, 2012) |
| ES (1) | ES443744A1 (en, 2012) |
| FI (1) | FI59110C (en, 2012) |
| FR (1) | FR2295972A1 (en, 2012) |
| GB (1) | GB1528039A (en, 2012) |
| IE (1) | IE42228B1 (en, 2012) |
| IT (1) | IT1052730B (en, 2012) |
| LU (1) | LU74085A1 (en, 2012) |
| NL (1) | NL165759C (en, 2012) |
| NO (1) | NO147566C (en, 2012) |
| RO (1) | RO66798A (en, 2012) |
| SE (1) | SE414031B (en, 2012) |
| ZA (1) | ZA757961B (en, 2012) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4137391A (en) * | 1976-09-10 | 1979-01-30 | Phillips Petroleum Company | Continuous solution polymerization of a conjugated diene with a monovinylaromatic compound using alkoxysilicon treating agents in the first reactor means of a reactor series |
| US4091198A (en) * | 1976-09-10 | 1978-05-23 | Phillips Petroleum Company | Suppressing gel in the continuous solution polymerization of a conjugated diene with a monovinyl aromatic compound |
| JPS5540734A (en) * | 1978-09-18 | 1980-03-22 | Nippon Zeon Co Ltd | Controlling of mooney viscosity of polybutadiene |
| US4311803A (en) | 1979-05-01 | 1982-01-19 | Phillips Petroleum Company | Continuous solution polymerization process |
| JPS58174125A (ja) * | 1982-04-07 | 1983-10-13 | Nippon Denso Co Ltd | 内燃機関用燃料噴射時期調整装置 |
| US5508366A (en) * | 1994-10-18 | 1996-04-16 | S. C. Johnson & Son, Inc. | Continuous production of reduced gel content hydroxylated addition polymers |
| DE10350998A1 (de) * | 2003-10-30 | 2005-06-02 | Basf Ag | Verfahren zur anionischen Polymerisation von Monomeren in α-Methylstyrol |
| CN101255203B (zh) * | 2007-03-01 | 2010-06-23 | 中国石油化工股份有限公司 | 在共轭二烯和单乙烯芳烃无规共聚物的制备工艺中抑制凝胶的方法 |
| DE102007020451A1 (de) | 2007-04-27 | 2008-10-30 | Lanxess Deutschland Gmbh | Verfahren zur Herstellung von Kautschukmischungen |
| EP2517899A1 (de) | 2011-04-29 | 2012-10-31 | Lanxess Deutschland GmbH | Verfahren zur Herstellung von Kautschukmischungen |
| TW201609825A (zh) * | 2014-03-28 | 2016-03-16 | 辛色姆（英國）有限公司 | 聚合物、製造聚合物之方法及聚合物之用途 |
| EP3029102A1 (en) | 2014-12-05 | 2016-06-08 | Lanxess Elastomers B.V. | Vulcanizable rubber composition |
| KR102154046B1 (ko) * | 2017-10-26 | 2020-09-09 | 주식회사 엘지화학 | 연속식 중합에 의한 공액디엔계 중합체의 제조방법 |
| CN113736042B (zh) * | 2021-11-08 | 2022-03-08 | 天津利安隆新材料股份有限公司 | 高碳醇作为阴离子聚合反应的终止剂的应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE637376A (en, 2012) * | 1958-05-23 | |||
| US3198774A (en) * | 1961-11-14 | 1965-08-03 | Phillips Petroleum Co | Continuous process for the preparation of block copolymers |
| US3207742A (en) * | 1962-03-26 | 1965-09-21 | Exxon Research Engineering Co | Polymerization of 1, 3-dienes in the presence of hexamethylphosphoramide |
| US3331826A (en) * | 1964-03-30 | 1967-07-18 | Firestone Tire & Rubber Co | Polymerization of conjugated diolefins with a lithium based catalyst and a hydrocarbon chain terminator |
| US3366611A (en) * | 1965-01-06 | 1968-01-30 | Phillips Petroleum Co | Preparation of random copolymers |
| US3496154A (en) * | 1965-10-15 | 1970-02-17 | Phillips Petroleum Co | Random copolymerization |
| NL135608C (en, 2012) * | 1966-11-28 | |||
| FR1546396A (fr) * | 1966-12-12 | 1968-11-15 | Firestone Tire & Rubber Co | Procédé de fabrication d'homopolymères de butadiène |
| US3554997A (en) * | 1968-10-02 | 1971-01-12 | Dow Chemical Co | Process for preventing gel formation during polymerization tube reactor |
| JPS5346075B2 (en, 2012) * | 1972-07-11 | 1978-12-11 | ||
| JPS4938105A (en, 2012) * | 1972-08-18 | 1974-04-09 |
-
1974
- 1974-12-23 FR FR7442810A patent/FR2295972A1/fr active Granted
-
1975
- 1975-12-03 NL NL7514084.A patent/NL165759C/xx not_active IP Right Cessation
- 1975-12-10 JP JP50144562A patent/JPS5183685A/ja active Granted
- 1975-12-16 BE BE162762A patent/BE836667A/xx not_active IP Right Cessation
- 1975-12-22 ES ES443744A patent/ES443744A1/es not_active Expired
- 1975-12-22 AU AU87767/75A patent/AU504064B2/en not_active Expired
- 1975-12-22 CA CA242,532A patent/CA1052947A/en not_active Expired
- 1975-12-22 SE SE7514515A patent/SE414031B/xx not_active IP Right Cessation
- 1975-12-22 LU LU74085A patent/LU74085A1/xx unknown
- 1975-12-22 EG EG754/75A patent/EG13100A/xx active
- 1975-12-22 IT IT70168/75A patent/IT1052730B/it active
- 1975-12-22 GB GB52416/75A patent/GB1528039A/en not_active Expired
- 1975-12-23 NO NO754373A patent/NO147566C/no unknown
- 1975-12-23 FI FI753639A patent/FI59110C/fi not_active IP Right Cessation
- 1975-12-23 AT AT982575A patent/AT345546B/de not_active IP Right Cessation
- 1975-12-23 AR AR261738A patent/AR217800A1/es active
- 1975-12-23 CH CH1672075A patent/CH608508A5/xx not_active IP Right Cessation
- 1975-12-23 BR BR7508614*A patent/BR7508614A/pt unknown
- 1975-12-23 ZA ZA00757961A patent/ZA757961B/xx unknown
- 1975-12-23 IE IE2804/75A patent/IE42228B1/en unknown
- 1975-12-23 DE DE2558139A patent/DE2558139C2/de not_active Expired
- 1975-12-23 RO RO7584290A patent/RO66798A/ro unknown
-
1977
- 1977-01-27 US US05/763,114 patent/US4136245A/en not_active Expired - Lifetime
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1052947A (en) | Continuous solution polymerization process | |
| US6492466B2 (en) | Increased throughput in the manufacture of anionic polymers by reduction in polymer cement viscosity through the addition of metal alkyls | |
| Hsieh et al. | Kinetics of alkyllithium initiated polymerizations | |
| EP0648790B1 (en) | In-situ anionic continuous dispersion polymerization process | |
| US4092268A (en) | Catalytic composition | |
| US5753579A (en) | Trans microstructure directing initiator system | |
| Quirk et al. | Dilithium initiators based on 1, 3‐bis (1‐phenylethenyl) benzene. Tetrahydrofuran and lithium sec‐butoxide effects | |
| EP2186837B1 (en) | Aba triblock copolymer and process for producing the same | |
| US6444767B1 (en) | Method for retarded anionic polymerization | |
| US5100965A (en) | Process for synthesizing high trans polymers | |
| US6506862B2 (en) | Process for the preparation of a diene elastomer by anionic polymerization | |
| JPH0215563B2 (en, 2012) | ||
| US3763126A (en) | Random copolymerization of conjugated dienes with monovinyl aromatic monomers | |
| US4189555A (en) | Continuous solution polymerization process | |
| US5063190A (en) | Anionic initiator system for polymerizing monomers | |
| US4136244A (en) | Continuous solution polymerization process | |
| US5216181A (en) | Liquid telechelic polymers having high 1,4-diene structure | |
| Hsieh | Effects of diethylzinc in alkyllithium‐initiated polymerizations | |
| US4202954A (en) | Continuous solution polymerization process | |
| US6300441B1 (en) | Method for the production of an initiator composition for retarded anionic polymerization | |
| US4208498A (en) | Continuous solution polymerization process | |
| EP0096875A1 (en) | Lithium alkoxide diamines as modifiers for polymerization of dienes using lithium-based initiators | |
| CA1145883A (en) | Process for preparing bimodal or multimodal polymers of conjugated dienes | |
| US6384164B2 (en) | Process for the preparation of a branched diene elastomer via an anionic route | |
| EP1177220B1 (en) | A method of anionically polymerizing monomers by contacting the monomers with a monofunctional anionic polymerization initiator |