JP2015505579A5 - - Google Patents
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- JP2015505579A5 JP2015505579A5 JP2014555737A JP2014555737A JP2015505579A5 JP 2015505579 A5 JP2015505579 A5 JP 2015505579A5 JP 2014555737 A JP2014555737 A JP 2014555737A JP 2014555737 A JP2014555737 A JP 2014555737A JP 2015505579 A5 JP2015505579 A5 JP 2015505579A5
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- Prior art keywords
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- 238000000034 method Methods 0.000 claims 13
- 239000000178 monomer Substances 0.000 claims 12
- 229920002554 vinyl polymer Polymers 0.000 claims 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 9
- -1 di-tert-butylhydroxybenzyl alcohol Chemical compound 0.000 claims 8
- 239000003054 catalyst Substances 0.000 claims 6
- 230000018044 dehydration Effects 0.000 claims 6
- 238000006297 dehydration reaction Methods 0.000 claims 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims 4
- CQRYARSYNCAZFO-UHFFFAOYSA-N o-hydroxybenzyl alcohol Natural products OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 claims 4
- BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical compound OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 claims 4
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical group CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 claims 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 claims 3
- 238000006116 polymerization reaction Methods 0.000 claims 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims 2
- 125000005418 aryl aryl group Chemical group 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 1
- YMOONIIMQBGTDU-VOTSOKGWSA-N [(e)-2-bromoethenyl]benzene Chemical compound Br\C=C\C1=CC=CC=C1 YMOONIIMQBGTDU-VOTSOKGWSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/364,554 | 2012-02-02 | ||
| US13/364,554 US8901362B2 (en) | 2012-02-02 | 2012-02-02 | Methods and compositions for styrene inhibition via in situ generation of quinone methides |
| PCT/US2013/024297 WO2013116611A1 (en) | 2012-02-02 | 2013-02-01 | Methods and compositions for styrene inhibition via in situ generation of quinone methides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015505579A JP2015505579A (ja) | 2015-02-23 |
| JP2015505579A5 true JP2015505579A5 (enExample) | 2016-03-17 |
| JP6118347B2 JP6118347B2 (ja) | 2017-04-19 |
Family
ID=47741287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014555737A Active JP6118347B2 (ja) | 2012-02-02 | 2013-02-01 | 現場生成キノンメチドによるスチレン抑制方法及び組成物 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8901362B2 (enExample) |
| EP (1) | EP2809634B1 (enExample) |
| JP (1) | JP6118347B2 (enExample) |
| KR (1) | KR101660610B1 (enExample) |
| CN (1) | CN104105680A (enExample) |
| BR (1) | BR112014018620A8 (enExample) |
| CA (1) | CA2862034A1 (enExample) |
| SG (1) | SG11201404399SA (enExample) |
| TW (1) | TWI558750B (enExample) |
| WO (1) | WO2013116611A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9206268B2 (en) * | 2011-09-16 | 2015-12-08 | General Electric Company | Methods and compositions for inhibiting polystyrene formation during styrene production |
| JP6530868B2 (ja) * | 2016-02-13 | 2019-06-12 | ドルフ ケタール ケミカルズ （インディア）プライヴェート リミテッド | ビニル芳香族モノマーの重合を制御及び阻害するための組成物及びその使用方法 |
| US10869444B2 (en) | 2018-07-13 | 2020-12-22 | Ecolab Usa Inc. | Compositions of oxygenated amines and quinone methides as antifoulants for vinylic monomers |
| EP3820846B1 (en) | 2018-07-13 | 2024-01-03 | Ecolab USA, Inc. | Composition for inhibiting monomer polymerization comprising a nitroxide inhibitor, a quinone methide retarder and an amine stabilizer |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3925488A (en) | 1971-05-24 | 1975-12-09 | Ethyl Corp | Process for the production of 1,3,5-trimethy-2,4,6-tris(3,5-di-tert-alkyl-4-hydroxybenzyl)benzene |
| US4032547A (en) | 1976-02-23 | 1977-06-28 | Gulf Research & Development Company | Quinone alkide synthesis system |
| TW225522B (enExample) * | 1992-02-24 | 1994-06-21 | Ciba Geigy Ag | |
| US5254760A (en) | 1992-07-29 | 1993-10-19 | Ciba-Geigy Corporation | Inhibiting polymerization of vinyl aromatic monomers |
| US5470440A (en) | 1994-04-19 | 1995-11-28 | Betz Laboratories, Inc. | Method for inhibiting vinyl aromatic monomer polymerization |
| US5616774A (en) * | 1995-04-14 | 1997-04-01 | Ciba-Geigy Corporation | Inhibition of unsaturated monomers with 7-aryl quinone methides |
| US6409887B1 (en) | 1996-07-15 | 2002-06-25 | Aah Marks And Company Limited | Polymerization inhibitor |
| US6024894A (en) | 1998-03-25 | 2000-02-15 | Betzdearborn Inc. | Compositions and methods for inhibiting vinyl aromatic monomer polymerization |
| US6376728B1 (en) * | 2000-06-20 | 2002-04-23 | Hercules Incorporated | Method, composition and mixture for inhibiting monomer polymerization |
| US6388155B1 (en) | 2000-08-01 | 2002-05-14 | Abb Lummus Global Inc. | Styrene dehydrogenation reactor effluent treatment |
| KR100812038B1 (ko) * | 2000-10-16 | 2008-03-10 | 유니로얄 캐미칼 캄파니, 인크. | 중합 억제제로서 퀴논 알키드와 니트록실 화합물의 블렌드물 |
| US6960279B2 (en) * | 2002-05-06 | 2005-11-01 | Fina Technology, Inc. | Method for stabilizing vinyl aromatic monomers using selected polymerization inhibitors and polymers prepared therewith |
| US6926820B2 (en) | 2002-09-20 | 2005-08-09 | G.E. Betz, Inc. | Inhibition of viscosity increase and fouling in hydrocarbon streams including unsaturation |
| WO2004083156A1 (ja) * | 2003-03-17 | 2004-09-30 | Hakuto Co., Ltd. | 芳香族ビニル化合物の重合抑制剤および重合抑制方法 |
| US7128826B2 (en) | 2003-07-31 | 2006-10-31 | General Electric Company | Polymerization inhibitor for styrene dehydrogenation units |
| GB0521319D0 (en) * | 2005-10-20 | 2005-11-30 | A H Marks And Company Ltd | Method |
| DE102007052891A1 (de) * | 2007-11-02 | 2009-05-07 | Evonik Degussa Gmbh | Verfahren zur Stabilisierung von olefinisch ungesättigten Monomeren |
| US8298440B2 (en) * | 2010-06-03 | 2012-10-30 | General Electric Company | Methods and compositions for inhibiting vinyl aromatic monomer polymerization |
| GB201011594D0 (en) * | 2010-07-09 | 2010-08-25 | Nufarm Uk Ltd | Retarder composition |
| US20120217444A1 (en) * | 2011-02-28 | 2012-08-30 | Shengxia Liu | Composition and method for inhibiting premature polymerization |
| US9090526B2 (en) * | 2011-06-13 | 2015-07-28 | Nalco Company | Synergistic combination for inhibiting polymerization of vinyl monomers |
| US8884038B2 (en) * | 2011-06-13 | 2014-11-11 | Nalco Company | Synthesis of 7-acetyleno quinone methide derivatives and their application as vinylic polymerization retarders |
| US9206268B2 (en) * | 2011-09-16 | 2015-12-08 | General Electric Company | Methods and compositions for inhibiting polystyrene formation during styrene production |
-
2012
- 2012-02-02 US US13/364,554 patent/US8901362B2/en not_active Expired - Fee Related
-
2013
- 2013-01-24 TW TW102102707A patent/TWI558750B/zh not_active IP Right Cessation
- 2013-02-01 KR KR1020147021068A patent/KR101660610B1/ko not_active Expired - Fee Related
- 2013-02-01 WO PCT/US2013/024297 patent/WO2013116611A1/en not_active Ceased
- 2013-02-01 CA CA2862034A patent/CA2862034A1/en not_active Abandoned
- 2013-02-01 JP JP2014555737A patent/JP6118347B2/ja active Active
- 2013-02-01 EP EP13705321.1A patent/EP2809634B1/en not_active Not-in-force
- 2013-02-01 CN CN201380007842.3A patent/CN104105680A/zh active Pending
- 2013-02-01 SG SG11201404399SA patent/SG11201404399SA/en unknown
- 2013-02-01 BR BR112014018620A patent/BR112014018620A8/pt not_active Application Discontinuation
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