CA2088012C - Procede de fabrication en continu de copolymeres a bloc vinylaromatique - Google Patents
Procede de fabrication en continu de copolymeres a bloc vinylaromatiqueInfo
- Publication number
- CA2088012C CA2088012C CA002088012A CA2088012A CA2088012C CA 2088012 C CA2088012 C CA 2088012C CA 002088012 A CA002088012 A CA 002088012A CA 2088012 A CA2088012 A CA 2088012A CA 2088012 C CA2088012 C CA 2088012C
- Authority
- CA
- Canada
- Prior art keywords
- reactor
- monomer
- copolymer
- vinyl aromatic
- living
- 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 - Fee Related
Links
- 238000000034 method Methods 0.000 title claims description 19
- 238000010924 continuous production Methods 0.000 title claims description 5
- 229920001400 block copolymer Polymers 0.000 title abstract description 8
- 229920001577 copolymer Polymers 0.000 claims abstract description 42
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 39
- 239000000178 monomer Substances 0.000 claims abstract description 38
- 150000001993 dienes Chemical class 0.000 claims abstract description 20
- 229920000642 polymer Polymers 0.000 claims abstract description 20
- 229920005989 resin Polymers 0.000 claims abstract description 5
- 239000011347 resin Substances 0.000 claims abstract description 5
- 229920001971 elastomer Polymers 0.000 claims abstract description 4
- 239000000806 elastomer Substances 0.000 claims abstract description 4
- 239000000243 solution Substances 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 239000003505 polymerization initiator Substances 0.000 claims description 17
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims description 15
- 238000002347 injection Methods 0.000 claims description 15
- 239000007924 injection Substances 0.000 claims description 15
- 125000000129 anionic group Chemical group 0.000 claims description 11
- 238000007334 copolymerization reaction Methods 0.000 claims description 11
- 239000007822 coupling agent Substances 0.000 claims description 11
- 239000003999 initiator Substances 0.000 claims description 11
- -1 vinyl aromatic hydrocarbon Chemical class 0.000 claims description 10
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 8
- 239000012429 reaction media Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 9
- 238000005859 coupling reaction Methods 0.000 abstract description 7
- 230000008878 coupling Effects 0.000 abstract description 6
- 238000010168 coupling process Methods 0.000 abstract description 6
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- 239000004793 Polystyrene Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000008187 granular material Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- 238000009826 distribution Methods 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 235000012424 soybean oil Nutrition 0.000 description 4
- 239000003549 soybean oil Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000003849 aromatic solvent Substances 0.000 description 3
- 238000005086 pumping Methods 0.000 description 3
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VDNSZPNSUQRUMS-UHFFFAOYSA-N 1-cyclohexyl-4-ethenylbenzene Chemical compound C1=CC(C=C)=CC=C1C1CCCCC1 VDNSZPNSUQRUMS-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
- VVTGQMLRTKFKAM-UHFFFAOYSA-N 1-ethenyl-4-propylbenzene Chemical compound CCCC1=CC=C(C=C)C=C1 VVTGQMLRTKFKAM-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 101000835998 Homo sapiens SRA stem-loop-interacting RNA-binding protein, mitochondrial Proteins 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 229920001744 Polyaldehyde Polymers 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 102100025491 SRA stem-loop-interacting RNA-binding protein, mitochondrial Human genes 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000002902 bimodal effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229920005605 branched copolymer Polymers 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- JMNDBSWHIXOJLR-UHFFFAOYSA-N ethylbenzene;styrene Chemical compound CCC1=CC=CC=C1.C=CC1=CC=CC=C1 JMNDBSWHIXOJLR-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
- C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C08G81/021—Block or graft polymers containing only sequences of polymers of C08C or C08F
- C08G81/022—Block or graft polymers containing only sequences of polymers of C08C or C08F containing sequences of polymers of conjugated dienes and of polymers of alkenyl aromatic compounds
-
- 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
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/02—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type
- C08F297/04—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type polymerising vinyl aromatic monomers and conjugated dienes
- C08F297/044—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type polymerising vinyl aromatic monomers and conjugated dienes using a coupling agent
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Graft Or Block Polymers (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Containers Having Bodies Formed In One Piece (AREA)
- Control And Safety Of Cranes (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9201075 | 1992-01-31 | ||
| FR9201075A FR2686886A1 (fr) | 1992-01-31 | 1992-01-31 | Procede de fabrication en continu de copolymeres a bloc vinylaromatique. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2088012A1 CA2088012A1 (fr) | 1993-08-01 |
| CA2088012C true CA2088012C (fr) | 1999-12-07 |
Family
ID=9426199
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002088012A Expired - Fee Related CA2088012C (fr) | 1992-01-31 | 1993-01-25 | Procede de fabrication en continu de copolymeres a bloc vinylaromatique |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0554142B1 (enExample) |
| JP (1) | JPH07681B2 (enExample) |
| AT (1) | ATE153682T1 (enExample) |
| CA (1) | CA2088012C (enExample) |
| DE (1) | DE69310943T2 (enExample) |
| ES (1) | ES2102614T3 (enExample) |
| FI (1) | FI108458B (enExample) |
| FR (1) | FR2686886A1 (enExample) |
| NO (1) | NO300596B1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19804912A1 (de) | 1998-02-07 | 1999-08-12 | Basf Ag | Kontinuierliches Verfahren zur Herstellung thermoplastischer Formmassen |
| WO2000075193A1 (en) | 1999-06-08 | 2000-12-14 | Kaneka Corporation | Method of continuous cationic living polymerization |
| US6448353B1 (en) | 2000-02-08 | 2002-09-10 | 3M Innovative Properties Company | Continuous process for the production of controlled architecture materials |
| US7632916B2 (en) | 2002-08-02 | 2009-12-15 | 3M Innovative Properties Company | Process to modify polymeric materials and resulting compositions |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2111966B2 (de) * | 1971-03-12 | 1979-03-08 | Basf Ag, 6700 Ludwigshafen | Kontinuierliches Verfahren zur Herstellung von Blockcopolymerisaten |
| US4390663A (en) * | 1981-02-17 | 1983-06-28 | Atlantic Richfield Company | Semi-continuous process for making star-block copolymers |
| US4346193A (en) * | 1981-05-04 | 1982-08-24 | Atlantic Richfield Company | Continuous process for making star-block copolymers |
| US4485210A (en) * | 1983-04-06 | 1984-11-27 | Atlantic Richfield Company | Process for the continuous production of star-block copolymers of a monovinyl aromatic monomer and a conjugated diene |
| FR2662167B1 (fr) * | 1990-05-16 | 1994-04-01 | Atochem | Procede de fabrication de resine styrenique transparente et resistante au choc. |
-
1992
- 1992-01-31 FR FR9201075A patent/FR2686886A1/fr active Granted
-
1993
- 1993-01-19 AT AT93400121T patent/ATE153682T1/de active
- 1993-01-19 ES ES93400121T patent/ES2102614T3/es not_active Expired - Lifetime
- 1993-01-19 EP EP93400121A patent/EP0554142B1/fr not_active Expired - Lifetime
- 1993-01-19 DE DE69310943T patent/DE69310943T2/de not_active Expired - Fee Related
- 1993-01-25 CA CA002088012A patent/CA2088012C/fr not_active Expired - Fee Related
- 1993-01-28 NO NO930295A patent/NO300596B1/no unknown
- 1993-01-29 FI FI930384A patent/FI108458B/fi active
- 1993-02-01 JP JP5036122A patent/JPH07681B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2088012A1 (fr) | 1993-08-01 |
| ES2102614T3 (es) | 1997-08-01 |
| FR2686886A1 (fr) | 1993-08-06 |
| DE69310943D1 (de) | 1997-07-03 |
| FI930384A0 (fi) | 1993-01-29 |
| FI108458B (fi) | 2002-01-31 |
| FI930384L (fi) | 1993-08-01 |
| JPH05339326A (ja) | 1993-12-21 |
| JPH07681B2 (ja) | 1995-01-11 |
| NO930295L (no) | 1993-08-02 |
| DE69310943T2 (de) | 1997-11-20 |
| NO300596B1 (no) | 1997-06-23 |
| ATE153682T1 (de) | 1997-06-15 |
| EP0554142A1 (fr) | 1993-08-04 |
| EP0554142B1 (fr) | 1997-05-28 |
| FR2686886B1 (enExample) | 1995-02-24 |
| NO930295D0 (no) | 1993-01-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP3612572A1 (fr) | Synthese en continu de copolymere d'ethylene et de butadiene | |
| EP3612573A1 (fr) | Synthese en continu de copolymere d'ethylene et de butadiene | |
| EP3390465B1 (fr) | Copolymere d'ethylene et de butadiene de microstructure homogene | |
| CA2742774C (fr) | Procede d'ammonolyse de l'acide 11-bromoundecanoique | |
| EP3390466B1 (fr) | Copolymere d'ethylene et de butadiene de microstructure homogene | |
| WO2022112699A1 (fr) | Polymère tribloc diénique riche en éthylène ayant un bloc statistique et deux blocs terminaux polyéthylène | |
| WO2017109325A1 (fr) | Procédé de synthèse d'un élastomère thermoplastique comprenant au moins un bloc poly(alpha-méthylstyrène) | |
| FR3086661A1 (fr) | Procede de synthese d'un elastomere thermoplastique comprenant au moins un bloc poly(alpha-methylstyrene) | |
| FR2839724A1 (fr) | Procedes de polymerisation radicalaire pour preparer des polymeres halogenes et polymeres halogenes | |
| EP0554142B1 (fr) | Procédé de fabrication en continu de copolymères à bloc vinylaromatique | |
| FR2503716A1 (fr) | Procede pour la preparation d'elastomeres acryliques reticules | |
| FR2921372A1 (fr) | Procede de recuperation d'un polymere a partir d'une solution | |
| CA2088023C (fr) | Nouveaux materiaux plastiques formes de copolymeres heterogenes de fluorure de vinylidene et de chlortrifluorethylene, utilisation et procede de fabrication | |
| CA2040454C (fr) | Procede de fabrication de resine styrenique transparente et resistante au choc | |
| CA2248534C (fr) | Procede de fabrication de polyamides | |
| CN107955100A (zh) | 一种定点功能化聚烯烃材料的方法及其连续生产方法 | |
| EP0411990A1 (fr) | Copolymère de fluorure de vinylidène et d'éthylène, son procédé d'obtention, son application comme agent d'adhésion | |
| JP2010235790A (ja) | 分子量分画された導電性高分子化合物の製造方法 | |
| FR2651236A1 (fr) | Procede de polymerisation du methacrylate de methyle. | |
| FR2543311A1 (fr) | Procede et dispositif de fabrication d'une fibre optique en matiere plastique | |
| BE681517A (enExample) | ||
| EP0034086B1 (fr) | Procédé de synthèse de polymères et de copolymères à base de chloroformiate de vinyle | |
| RU2225871C2 (ru) | Способ переработки форполимера метилметакрилата и удаления из него свободного мономера | |
| FR2554111A1 (fr) | Procede d'obtention en continu de copolymeres | |
| BE824226A (fr) | Procede de fabrication d'une resine copolymere a blocs transparente et produit obtenu |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |