FI59110C - Foerfarande foer kontinuerlig loesningspolymerisation av minst en konjugerad dien eller minst en konjugerad dien och minst en vinylaromatisk foerening - Google Patents
Foerfarande foer kontinuerlig loesningspolymerisation av minst en konjugerad dien eller minst en konjugerad dien och minst en vinylaromatisk foerening Download PDFInfo
- Publication number
- FI59110C FI59110C FI753639A FI753639A FI59110C FI 59110 C FI59110 C FI 59110C FI 753639 A FI753639 A FI 753639A FI 753639 A FI753639 A FI 753639A FI 59110 C FI59110 C FI 59110C
- Authority
- FI
- Finland
- Prior art keywords
- reaction
- toluene
- process according
- days
- conjugation
- Prior art date
Links
- 238000006116 polymerization reaction Methods 0.000 title claims description 14
- 230000021615 conjugation Effects 0.000 title 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 85
- 238000006243 chemical reaction Methods 0.000 claims description 54
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical group [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 43
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 38
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 37
- 239000000178 monomer Substances 0.000 claims description 32
- 239000003795 chemical substances by application Substances 0.000 claims description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 23
- 238000007334 copolymerization reaction Methods 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 229920001577 copolymer Polymers 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- 229920002521 macromolecule Polymers 0.000 claims description 14
- 229920000642 polymer Polymers 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 11
- 230000009849 deactivation Effects 0.000 claims description 10
- 239000012986 chain transfer agent Substances 0.000 claims description 9
- 239000003999 initiator Substances 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 150000001340 alkali metals Chemical class 0.000 claims description 8
- 229910021645 metal ion Inorganic materials 0.000 claims description 8
- 229910052744 lithium Inorganic materials 0.000 claims description 7
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 5
- 150000002894 organic compounds Chemical class 0.000 claims description 5
- 125000001979 organolithium group Chemical group 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 150000002900 organolithium compounds Chemical class 0.000 claims description 4
- 229920001519 homopolymer Polymers 0.000 claims description 3
- 239000007810 chemical reaction solvent Substances 0.000 claims description 2
- 150000003440 styrenes Chemical class 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 239000000499 gel Substances 0.000 description 22
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 20
- 238000002474 experimental method Methods 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 11
- -1 vinyl aromatic compound Chemical class 0.000 description 11
- 150000001993 dienes Chemical class 0.000 description 8
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 6
- 238000006276 transfer reaction Methods 0.000 description 6
- 239000011734 sodium Substances 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 4
- 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 description 3
- 230000004913 activation Effects 0.000 description 3
- 229940073608 benzyl chloride Drugs 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 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
- 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
- 230000003213 activating effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 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
- 230000000052 comparative effect Effects 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- ZMZIEZHJTIVGGP-UHFFFAOYSA-N diphenylmethanone;potassium Chemical compound [K].C=1C=CC=CC=1C(=O)C1=CC=CC=C1 ZMZIEZHJTIVGGP-UHFFFAOYSA-N 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 2
- CCZVEWRRAVASGL-UHFFFAOYSA-N lithium;2-methanidylpropane Chemical compound [Li+].CC(C)[CH2-] CCZVEWRRAVASGL-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000012360 testing method Methods 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
- 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 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- RCJMVGJKROQDCB-UHFFFAOYSA-N 1,3-dimethyl-1,3-butadiene Natural products CC=CC(C)=C RCJMVGJKROQDCB-UHFFFAOYSA-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
- ZMYIIHDQURVDRB-UHFFFAOYSA-N 1-phenylethenylbenzene Chemical group C=1C=CC=CC=1C(=C)C1=CC=CC=C1 ZMYIIHDQURVDRB-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
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-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
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 1
- ZTWAGSREJICJIX-UHFFFAOYSA-N C(=C)C=C=CC1=C(C=CC=C1)C=C Chemical compound C(=C)C=C=CC1=C(C=CC=C1)C=C ZTWAGSREJICJIX-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
- SGNBEQXWGWKCBH-UHFFFAOYSA-N COC(CO[AlH2])OC.[Na] Chemical compound COC(CO[AlH2])OC.[Na] SGNBEQXWGWKCBH-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-UHFFFAOYSA-N Dicyclopentadiene Chemical compound C1C2C3CC=CC3C1C=C2 HECLRDQVFMWTQS-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001361 allenes Chemical class 0.000 description 1
- 150000004645 aluminates Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 1
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical class 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
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical compound [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000000816 ethylene group Chemical class [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 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
- SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 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
- 238000005192 partition Methods 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 229920000570 polyether Polymers 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 class CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction 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
- 150000003512 tertiary amines 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
- 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)
Claims (7)
1. Förfarande för kontinuerlig lösningshomo- eller lösningskopolymerination av minst en konjugerad C^-Cg-dien eller minst en konjugerad C^-Cg-dien och minst en C^-C^-alkylsubstituerad eller osubstituerad styren i ett kolväte-lösningsmedel under användning av en litiumorganisk initiator och minst on reaktor, tili vilken de i ett kolvätelösningsmedel lösta monoraererna kontinuer-ligt leds och frän vilken även lösningen av homopolymererna eller kopolymerernn , oon bildats, och lösningen av monomererna, som ej reagerat, kontinuerligt av_ leds kännetecknat därav, att polymerisationsreaktionen utförs i en reaktor av öppen typ vid en temperatur av 20-110°C i närvaro av ett deakti-veringssystem, som förhindrar bildandet av geler, vilket deaktiveringssystem ornf attar a) minst ett ämne, som deaktiverar de levande makromolekylerna, vilket ämne är ett kedjeöverföringsämne med ett läge, som kan lvi n da. en metall.jon, vilket läge omfattar ett rörligt väte eller en substituerbar halogen, eller ett termineringsämne, som med relativ lag reaktionshastighet spjälkar kollit iunbindr. in ^en i produkten, som bildats, utan att väsentligen päverka reaktionens fortskridande, och b) eventuellt ett eller flera ämnen, som ökar reaktionshastigheten hos den levande polymeren, som bildats pä deaktiveringsämnet eller -ämnen, varvid ämnet är en polarisk organisk förening och/eller ett metalljoner avgivande ämne, som är ett alkoholat av en aikaLimetall, varvid aikalimetallen är en annan än litium, eller en komplexblandning av en alkalimetall och en aluminium- organisk förening, varvid deaktiveringsämne eller ämnen och initiator är när- varande i sädana proportioner, att förhallandet mellan deaktiveringshastig- heten för de levande makromolekylerna och hastigheten för polymerisations- -5 -3 reaktionens fortskridande är MO - 5· 10
2. Förfarande enligt patentkravet 1, kännetecknat därav, att deaktiveringssystemet och reaktionslösningsmedlet utgörs av toluen.
3. Förfarande enligt patentkravet 1, kännetecknat därav, att deaktiveringssystemet utgörs av toluen och tetrahydrofuran, varvid koncentrationen av tetrahydrofuranen i toluenet är mellan 50 och 5 000 ppm. 1*. Förfarande enligt patentkravet 1, kännetecknat därav, att deaktiveringssystemet utgörs av hexametylfosfortriamid och ett alifatickt, cykloalifatiskt eller aromatiskt kolvätelösningsmedel.
5. Förfarande enligt patentkravet U, kännetecknat därav, att molförhällandet mellan hexametylfosfortriamiden och den litiumorganiska föreningen är mellan 0,2 och 2.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7442810 | 1974-12-23 | ||
| 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 (3)
| Publication Number | Publication Date |
|---|---|
| FI753639A7 FI753639A7 (sv) | 1976-06-24 |
| FI59110B FI59110B (fi) | 1981-02-27 |
| FI59110C true FI59110C (fi) | 1981-06-10 |
Family
ID=9146627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI753639A FI59110C (fi) | 1974-12-23 | 1975-12-23 | Foerfarande foer kontinuerlig loesningspolymerisation av minst en konjugerad dien eller minst en konjugerad dien och minst en vinylaromatisk foerening |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4136245A (sv) |
| JP (1) | JPS5183685A (sv) |
| AR (1) | AR217800A1 (sv) |
| AT (1) | AT345546B (sv) |
| AU (1) | AU504064B2 (sv) |
| BE (1) | BE836667A (sv) |
| BR (1) | BR7508614A (sv) |
| CA (1) | CA1052947A (sv) |
| CH (1) | CH608508A5 (sv) |
| DE (1) | DE2558139C2 (sv) |
| EG (1) | EG13100A (sv) |
| ES (1) | ES443744A1 (sv) |
| FI (1) | FI59110C (sv) |
| FR (1) | FR2295972A1 (sv) |
| GB (1) | GB1528039A (sv) |
| IE (1) | IE42228B1 (sv) |
| IT (1) | IT1052730B (sv) |
| LU (1) | LU74085A1 (sv) |
| NL (1) | NL165759C (sv) |
| NO (1) | NO147566C (sv) |
| RO (1) | RO66798A (sv) |
| SE (1) | SE414031B (sv) |
| ZA (1) | ZA757961B (sv) |
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 |
| WO2015145175A1 (en) * | 2014-03-28 | 2015-10-01 | Synthomer (Uk) Limited | Polymer, method of making a polymer and uses of said polymer |
| 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 (sv) * | 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 (sv) * | 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 (sv) * | 1972-07-11 | 1978-12-11 | ||
| JPS4938105A (sv) * | 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 LU LU74085A patent/LU74085A1/xx unknown
- 1975-12-22 SE SE7514515A patent/SE414031B/sv not_active IP Right Cessation
- 1975-12-22 GB GB52416/75A patent/GB1528039A/en not_active Expired
- 1975-12-22 EG EG754/75A patent/EG13100A/xx active
- 1975-12-22 IT IT70168/75A patent/IT1052730B/it active
- 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 ES ES443744A patent/ES443744A1/es not_active Expired
- 1975-12-23 FI FI753639A patent/FI59110C/fi not_active IP Right Cessation
- 1975-12-23 ZA ZA00757961A patent/ZA757961B/xx unknown
- 1975-12-23 DE DE2558139A patent/DE2558139C2/de not_active Expired
- 1975-12-23 BR BR7508614*A patent/BR7508614A/pt unknown
- 1975-12-23 CH CH1672075A patent/CH608508A5/xx not_active IP Right Cessation
- 1975-12-23 AR AR261738A patent/AR217800A1/es active
- 1975-12-23 IE IE2804/75A patent/IE42228B1/en unknown
- 1975-12-23 RO RO7584290A patent/RO66798A/ro unknown
- 1975-12-23 NO NO754373A patent/NO147566C/no unknown
- 1975-12-23 AT AT982575A patent/AT345546B/de not_active IP Right Cessation
-
1977
- 1977-01-27 US US05/763,114 patent/US4136245A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| IT1052730B (it) | 1981-07-20 |
| GB1528039A (en) | 1978-10-11 |
| LU74085A1 (sv) | 1976-11-11 |
| AR217800A1 (es) | 1980-04-30 |
| IE42228B1 (en) | 1980-07-02 |
| ES443744A1 (es) | 1977-04-16 |
| US4136245A (en) | 1979-01-23 |
| NL165759C (nl) | 1981-05-15 |
| NO754373L (sv) | 1976-06-24 |
| FR2295972B1 (sv) | 1978-06-23 |
| NO147566C (no) | 1983-05-04 |
| SE414031B (sv) | 1980-07-07 |
| AU504064B2 (en) | 1979-10-04 |
| FI753639A7 (sv) | 1976-06-24 |
| FI59110B (fi) | 1981-02-27 |
| DE2558139A1 (de) | 1976-07-01 |
| ATA982575A (de) | 1978-01-15 |
| CH608508A5 (sv) | 1979-01-15 |
| SE7514515L (sv) | 1976-06-24 |
| AU8776775A (en) | 1977-06-30 |
| EG13100A (en) | 1980-07-31 |
| JPS5183685A (en) | 1976-07-22 |
| FR2295972A1 (fr) | 1976-07-23 |
| JPS5514085B2 (sv) | 1980-04-14 |
| IE42228L (en) | 1976-06-23 |
| BR7508614A (pt) | 1976-08-24 |
| NL7514084A (nl) | 1976-06-25 |
| NL165759B (nl) | 1980-12-15 |
| CA1052947A (en) | 1979-04-17 |
| BE836667A (fr) | 1976-06-16 |
| AT345546B (de) | 1978-09-25 |
| ZA757961B (en) | 1976-12-29 |
| DE2558139C2 (de) | 1982-12-09 |
| RO66798A (ro) | 1980-01-15 |
| NO147566B (no) | 1983-01-24 |
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Legal Events
| Date | Code | Title | Description |
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| MA | Patent expired | ||
| MA | Patent expired |
Owner name: MICHELIN & CIE (COMPAGNIE GENERALE DES |