JP2009545654A - スチレン重合体中におけるリチウムの低減 - Google Patents
スチレン重合体中におけるリチウムの低減 Download PDFInfo
- Publication number
- JP2009545654A JP2009545654A JP2009522946A JP2009522946A JP2009545654A JP 2009545654 A JP2009545654 A JP 2009545654A JP 2009522946 A JP2009522946 A JP 2009522946A JP 2009522946 A JP2009522946 A JP 2009522946A JP 2009545654 A JP2009545654 A JP 2009545654A
- Authority
- JP
- Japan
- Prior art keywords
- weight
- styrene polymer
- range
- amount
- water
- 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.)
- Withdrawn
Links
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 title claims abstract description 161
- 229920000642 polymer Polymers 0.000 title claims abstract description 81
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 229910052744 lithium Inorganic materials 0.000 title claims abstract description 34
- 239000000203 mixture Substances 0.000 claims abstract description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 48
- 238000000034 method Methods 0.000 claims abstract description 43
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims abstract description 28
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000010438 heat treatment Methods 0.000 claims abstract description 19
- 229910001416 lithium ion Inorganic materials 0.000 claims abstract description 19
- 239000007788 liquid Substances 0.000 claims abstract description 18
- 229930195734 saturated hydrocarbon Natural products 0.000 claims abstract description 14
- 239000007791 liquid phase Substances 0.000 claims abstract description 7
- 239000003505 polymerization initiator Substances 0.000 claims description 13
- 125000001979 organolithium group Chemical group 0.000 claims description 12
- 238000006116 polymerization reaction Methods 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 5
- 239000000047 product Substances 0.000 description 18
- 239000012074 organic phase Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 14
- 239000004793 Polystyrene Substances 0.000 description 11
- 229920002223 polystyrene Polymers 0.000 description 11
- 239000008346 aqueous phase Substances 0.000 description 10
- 125000000129 anionic group Chemical group 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 5
- -1 polybutylene terephthalate Polymers 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 230000031709 bromination Effects 0.000 description 3
- 238000005893 bromination reaction Methods 0.000 description 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- SGVUHPSBDNVHKL-UHFFFAOYSA-N 1,3-dimethylcyclohexane Chemical compound CC1CCCC(C)C1 SGVUHPSBDNVHKL-UHFFFAOYSA-N 0.000 description 2
- QRMPKOFEUHIBNM-UHFFFAOYSA-N 1,4-dimethylcyclohexane Chemical compound CC1CCC(C)CC1 QRMPKOFEUHIBNM-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 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
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- BTOVVHWKPVSLBI-UHFFFAOYSA-N 2-methylprop-1-enylbenzene Chemical compound CC(C)=CC1=CC=CC=C1 BTOVVHWKPVSLBI-UHFFFAOYSA-N 0.000 description 1
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-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
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003999 initiator Substances 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
- 238000010550 living polymerization reaction Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012815 thermoplastic material 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
- C08F6/00—Post-polymerisation treatments
- C08F6/02—Neutralisation of the polymerisation mass, e.g. killing the catalyst also removal of catalyst residues
-
- 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
- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/06—Hydrocarbons
- C08F12/08—Styrene
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83462906P | 2006-08-01 | 2006-08-01 | |
| PCT/US2007/074278 WO2008016810A1 (en) | 2006-08-01 | 2007-07-25 | Lithium reduction in styrenic polymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009545654A true JP2009545654A (ja) | 2009-12-24 |
| JP2009545654A5 JP2009545654A5 (https=) | 2010-08-12 |
Family
ID=38291011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009522946A Withdrawn JP2009545654A (ja) | 2006-08-01 | 2007-07-25 | スチレン重合体中におけるリチウムの低減 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20100016530A1 (https=) |
| EP (1) | EP2046844B1 (https=) |
| JP (1) | JP2009545654A (https=) |
| KR (1) | KR20090034929A (https=) |
| CN (1) | CN101495521B (https=) |
| AT (1) | ATE491731T1 (https=) |
| BR (1) | BRPI0714918A2 (https=) |
| CA (1) | CA2659058A1 (https=) |
| DE (1) | DE602007011276D1 (https=) |
| ES (1) | ES2357264T3 (https=) |
| IL (1) | IL196791A0 (https=) |
| MX (1) | MX2009001038A (https=) |
| PL (1) | PL2046844T3 (https=) |
| TW (1) | TW200813097A (https=) |
| WO (1) | WO2008016810A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019043033A1 (en) * | 2017-08-31 | 2019-03-07 | Ineos Styrolution Group Gmbh | PROCESS FOR THE PREPARATION OF STYRENE POLYMERS WITH LOW STABILITY AND STABLE COLOR |
| EP3676301B1 (en) | 2017-08-31 | 2023-05-10 | INEOS Styrolution Group GmbH | Process for the preparation of styrenic polymers having an improved color stability |
| WO2025176772A1 (en) * | 2024-02-22 | 2025-08-28 | Ineos Styrolution Group Gmbh | Recovery of metal compounds from polymers obtained by anionic polymerization |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2366546A (en) * | 1942-05-14 | 1945-01-02 | Westvaco Chlorine Products Cor | Method of decolorizing aqueous solution of alkali metal hydroxides |
| US2979509A (en) * | 1957-05-06 | 1961-04-11 | Phillips Petroleum Co | Treatment of polymers produced by alkali metal catalyzed polymerization |
| US3621077A (en) * | 1968-11-01 | 1971-11-16 | Goodrich Co B F | Solvent resistant thermoplastic polymers |
| DE2332796A1 (de) * | 1973-06-28 | 1975-01-16 | Huels Chemische Werke Ag | Verfahren zur herstellung rieselfaehiger, pulverfoermiger kautschuk-fuellstoffmischungen |
| US4033829A (en) * | 1974-12-26 | 1977-07-05 | Monsanto Company | Process for inhibiting polymerization of styrene during distillation |
| US4587330A (en) * | 1985-02-22 | 1986-05-06 | Atlantic Richfield Company | Purification of polymer solutions |
| BE1000914A4 (fr) * | 1987-09-21 | 1989-05-16 | Labofina Sa | Procede de decoloration de polymeres resineux du type vinylaromatique-diene conjugue. |
| US4992529A (en) * | 1987-10-29 | 1991-02-12 | Shell Oil Company | Method for separating metal contaminants from organic polymers |
| JP3063908B2 (ja) * | 1989-03-13 | 2000-07-12 | ザ ダウ ケミカル カンパニー | アニオン重合によるポリマーの製造方法 |
| US5358981A (en) * | 1992-12-07 | 1994-10-25 | Shell Oil Company | Solvent-free water-based emulsions of anionically polymerized polymers |
| DE69509448T2 (de) * | 1994-07-18 | 1999-09-02 | Bridgestone Corp. | Elastomere und Produkte mit niedriger Hysteresis und Verfahren zu deren Herstellung |
| TW370534B (en) * | 1995-01-24 | 1999-09-21 | Shell Internattonale Res Mij B V | Process for manufacturing isoprene containing block copolymers |
| US6232408B1 (en) * | 1996-09-26 | 2001-05-15 | Albemarle Corporation | Brominated polstyrenic resins |
| US6136914A (en) * | 1998-03-13 | 2000-10-24 | Bridgestone Corporation | Anionic polymerization initiators for preparing macro-branched diene rubbers |
| US6448353B1 (en) * | 2000-02-08 | 2002-09-10 | 3M Innovative Properties Company | Continuous process for the production of controlled architecture materials |
| US6759498B2 (en) * | 2000-05-08 | 2004-07-06 | Asahi Kadei Kabushiki Kaisha | Process for producing styrene resin reduced in content of low-molecular ingredient |
| DE10053324A1 (de) * | 2000-10-27 | 2002-05-08 | Basf Ag | Verfahren zum Kettenabbruch bei der anionischen Polymerisation |
| US6657028B1 (en) * | 2002-08-01 | 2003-12-02 | Albemarle Corporation | Anionic polymerization process |
-
2007
- 2007-07-25 CN CN2007800283920A patent/CN101495521B/zh not_active Expired - Fee Related
- 2007-07-25 US US12/374,138 patent/US20100016530A1/en not_active Abandoned
- 2007-07-25 EP EP07813318A patent/EP2046844B1/en not_active Not-in-force
- 2007-07-25 KR KR1020097001842A patent/KR20090034929A/ko not_active Withdrawn
- 2007-07-25 ES ES07813318T patent/ES2357264T3/es active Active
- 2007-07-25 PL PL07813318T patent/PL2046844T3/pl unknown
- 2007-07-25 DE DE602007011276T patent/DE602007011276D1/de active Active
- 2007-07-25 WO PCT/US2007/074278 patent/WO2008016810A1/en not_active Ceased
- 2007-07-25 CA CA002659058A patent/CA2659058A1/en not_active Abandoned
- 2007-07-25 MX MX2009001038A patent/MX2009001038A/es unknown
- 2007-07-25 BR BRPI0714918-2A patent/BRPI0714918A2/pt not_active IP Right Cessation
- 2007-07-25 AT AT07813318T patent/ATE491731T1/de not_active IP Right Cessation
- 2007-07-25 JP JP2009522946A patent/JP2009545654A/ja not_active Withdrawn
- 2007-07-26 TW TW096127189A patent/TW200813097A/zh unknown
-
2009
- 2009-01-29 IL IL196791A patent/IL196791A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX2009001038A (es) | 2009-02-06 |
| CN101495521A (zh) | 2009-07-29 |
| BRPI0714918A2 (pt) | 2013-05-28 |
| KR20090034929A (ko) | 2009-04-08 |
| CA2659058A1 (en) | 2008-02-07 |
| ES2357264T3 (es) | 2011-04-20 |
| TW200813097A (en) | 2008-03-16 |
| CN101495521B (zh) | 2011-04-27 |
| US20100016530A1 (en) | 2010-01-21 |
| PL2046844T3 (pl) | 2011-05-31 |
| ATE491731T1 (de) | 2011-01-15 |
| EP2046844B1 (en) | 2010-12-15 |
| IL196791A0 (en) | 2009-11-18 |
| DE602007011276D1 (de) | 2011-01-27 |
| EP2046844A1 (en) | 2009-04-15 |
| WO2008016810A1 (en) | 2008-02-07 |
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