JP6118347B2 - 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 - Google Patents
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 Download PDFInfo
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- JP6118347B2 JP6118347B2 JP2014555737A JP2014555737A JP6118347B2 JP 6118347 B2 JP6118347 B2 JP 6118347B2 JP 2014555737 A JP2014555737 A JP 2014555737A JP 2014555737 A JP2014555737 A JP 2014555737A JP 6118347 B2 JP6118347 B2 JP 6118347B2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/20—Use of additives, e.g. for stabilisation
-
- 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
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
- C08F2/40—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation using retarding agents
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
式中、R3及びR4は、同一でも異なってもよく、水素、アルキル、アリール、アルカリール又はヒドロキシアルキル基から選択され、炭素数約3〜約20を有することが好ましい。一実施形態では、ヒドロキシルアミンは、1,1’−(ヒドロキシイミノ)ビス(2−プロパノール)である。ヒドロキシルアミンに関する詳細は、Arhancetの米国特許第6024894号(本特許の先行技術として援用する)に示される。
Claims (20)
- ビニル芳香族モノマーの重合を抑制する組成物であって、
(1)ヒドロキシベンジルアルコールと、
(2)脱水触媒と
を含む組成物。 - 成分(1)と(2)が1〜99重量%の(1):99〜1重量%の(2)の量比で存在する、請求項1記載の組成物。
- 成分(1):(2)の重量比が2:1〜20:1である、請求項2記載の組成物。
- 前記ビニル芳香族モノマーがスチレン、ブロモスチレン、ジビニルベンゼン及びα−メチルスチレンからなる群から選択されるものである、請求項1乃至請求項3のいずれか1項記載の組成物。
- 脱水触媒(2)がi)アルキル−、アリール−及びアルキルアリール−スルホン酸並びにii)C2〜C36飽和又は不飽和カルボン酸から選択される酸である、請求項1乃至請求項4のいずれか1項記載の組成物。
- 脱水触媒がアルキル−、アリール−又はアルキルアリール−スルホン酸である、請求項5記載の組成物。
- ヒドロキシベンジルアルコールがジ−tert−ブチルヒドロキシベンジルアルコールである、請求項1乃至請求項6のいずれか1項記載の組成物。
- 脱水触媒がドデシルベンゼンスルホン酸又はp−トルエンスルホン酸である、請求項1乃至請求項7のいずれか1項記載の組成物。
- さらに、(3)ヒドロキシルアミン化合物を含んでいて、ヒドロキシルアミンが成分(1)と(2)の合計量を基準にして1〜99重量%の量で存在する、請求項1乃至請求項8のいずれか1項記載の組成物。
- さらに、(4)ニトロキシル化合物を含んでいて、成分(4)が成分(1)と(2)の合計量を基準にして1〜99重量%の量で存在する、請求項1乃至請求項9のいずれか1項記載の組成物。
- ビニルモノマーの重合を抑制する方法であって、(1)ヒドロキシベンジルアルコールと(2)脱水触媒をモノマーに添加することを含む方法。
- 成分(1)と(2)が1〜99重量%の(1):99〜1重量%の(2)の量比で存在する、請求項11記載の方法。
- 成分(1):(2)の重量比が2:1〜20:1であり、成分(1)と(2)をビニルモノマー百万部を基準にして10〜10000ppmの合計量でビニルモノマーに添加する、請求項11又は請求項12記載の方法。
- 脱水触媒が、i)アルキル−、アリール−及びアルキルアリール−スルホン酸並びにii)C6〜C22飽和又は不飽和カルボン酸から選択される酸である、請求項11乃至請求項13のいずれか1項記載の方法。
- ヒドロキシベンジルアルコールがジ−tert−ブチルヒドロキシベンジルアルコールである、請求項11乃至請求項14のいずれか1項記載の方法。
- 酸がドデシルベンゼンスルホン酸又はp−トルエンスルホン酸である、請求項14記載の方法。
- さらに、(3)ヒドロキシルアミン化合物をビニルモノマーに添加することを含んでいて、ヒドロキシルアミンが、ビニルモノマー百万部を基準にして1〜10000ppmのヒドロキシルアミン換算量で添加される、請求項11乃至請求項16のいずれか1項記載の方法。
- さらに、(4)ニトロキシル化合物をビニルモノマーに添加することを含んでいて、ニトロキシル化合物が、ビニルモノマー百万部を基準にして1〜10000ppmの量で添加される、請求項11乃至請求項17のいずれか1項記載の方法。
- ビニルモノマーの重合を抑制する方法であって、請求項1の組成物の有効量をビニルモノマーに添加することを含む方法。
- 前記組成物が、ジ−tert−ブチルヒドロキシベンジルアルコールとドデシルベンゼンスルホン酸又はp−トルエンスルホン酸とを含む、請求項19記載の方法。
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 JP2015505579A5 (ja) | 2016-03-17 |
JP6118347B2 true 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 (ja) |
EP (1) | EP2809634B1 (ja) |
JP (1) | JP6118347B2 (ja) |
KR (1) | KR101660610B1 (ja) |
CN (1) | CN104105680A (ja) |
BR (1) | BR112014018620A8 (ja) |
CA (1) | CA2862034A1 (ja) |
SG (1) | SG11201404399SA (ja) |
TW (1) | TWI558750B (ja) |
WO (1) | WO2013116611A1 (ja) |
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 |
CN108884004B (zh) * | 2016-02-13 | 2020-02-25 | 多尔夫凯塔尔化学制品(I)私人有限公司 | 用于控制和抑制乙烯基芳族单体聚合的组合物,及其使用方法 |
CN112533902A (zh) | 2018-07-13 | 2021-03-19 | 埃科莱布美国股份有限公司 | 抑制单体聚合的包含氮氧化物抑制剂、醌甲基化物阻滞剂和胺稳定剂的组合物 |
EP3820836A1 (en) | 2018-07-13 | 2021-05-19 | Ecolab USA, Inc. | Compositions of oxygenated amines and quinone methides as antifoulants for vinylic monomers |
Family Cites Families (23)
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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 (ja) * | 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 |
WO2002033026A1 (en) * | 2000-10-16 | 2002-04-25 | Uniroyal Chemical Company, Inc. | Blends of quinone alkide and nitroxyl compounds as polymerization inhibitors |
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 |
JP4790414B2 (ja) | 2003-03-17 | 2011-10-12 | 伯東株式会社 | 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 BR BR112014018620A patent/BR112014018620A8/pt not_active Application Discontinuation
- 2013-02-01 KR KR1020147021068A patent/KR101660610B1/ko active IP Right Grant
- 2013-02-01 CA CA2862034A patent/CA2862034A1/en not_active Abandoned
- 2013-02-01 JP JP2014555737A patent/JP6118347B2/ja active Active
- 2013-02-01 SG SG11201404399SA patent/SG11201404399SA/en unknown
- 2013-02-01 WO PCT/US2013/024297 patent/WO2013116611A1/en active Application Filing
- 2013-02-01 CN CN201380007842.3A patent/CN104105680A/zh active Pending
- 2013-02-01 EP EP13705321.1A patent/EP2809634B1/en not_active Not-in-force
Also Published As
Publication number | Publication date |
---|---|
SG11201404399SA (en) | 2014-08-28 |
JP2015505579A (ja) | 2015-02-23 |
WO2013116611A1 (en) | 2013-08-08 |
TWI558750B (zh) | 2016-11-21 |
BR112014018620A2 (ja) | 2017-06-20 |
KR20140119054A (ko) | 2014-10-08 |
CA2862034A1 (en) | 2013-08-08 |
US8901362B2 (en) | 2014-12-02 |
KR101660610B1 (ko) | 2016-09-27 |
EP2809634B1 (en) | 2018-01-31 |
CN104105680A (zh) | 2014-10-15 |
EP2809634A1 (en) | 2014-12-10 |
US20130204053A1 (en) | 2013-08-08 |
TW201336907A (zh) | 2013-09-16 |
BR112014018620A8 (pt) | 2017-07-11 |
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