JP5602800B2 - 芳香族ビニル化合物の重合抑制方法 - Google Patents
芳香族ビニル化合物の重合抑制方法 Download PDFInfo
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- JP5602800B2 JP5602800B2 JP2012170992A JP2012170992A JP5602800B2 JP 5602800 B2 JP5602800 B2 JP 5602800B2 JP 2012170992 A JP2012170992 A JP 2012170992A JP 2012170992 A JP2012170992 A JP 2012170992A JP 5602800 B2 JP5602800 B2 JP 5602800B2
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- Prior art keywords
- group
- carbon atoms
- acid
- aromatic vinyl
- compound
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Classifications
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/42—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic
- C07C15/44—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic the hydrocarbon substituent containing a carbon-to-carbon double bond
- C07C15/46—Styrene; Ring-alkylated styrenes
-
- 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
-
- 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
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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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
この発明の態様(1)においては、前記(A)成分の一般式(I)表示の含窒素芳香族化合物が、メチレンバイオレット、レソルフィン及びフェノチアジン−3−オキサイドから選ばれた少なくとも1種であることができる。
(A)成分(含窒素芳香族化合物)
A−1 :メチレンバイオレット(東京化成工業社製)
A−2 :レソルフィン(東京化成工業社製)
A−3 :クレシルバイオレット(Aldrichi Chemical社製)
A−4 :チオニン(Aldrichi Chemical社製)
A−5 :メチレンブルー(東京化成工業社製)
A−6 :インジゴ
A−7 :インジゴカーミン
A−8 :キノキサリン
A−9 :1−メチルキノキサリン
A−10:フェナジン
A−11:3−アミノ−7−ヒドロキシ−2−メチルフェナジン
A−12:テトラベンゾ[a、c、h、j]フェナジン
B−1:ドデシルベンゼンスルホン酸
B−2:ペンタデシルベンゼンスルホン酸
B−3:キシレンスルホン酸
B−4:クメンスルホン酸
B−5:p−トルエンスルホン酸
B−6:メタンスルホン酸
B−7:硫酸(98%)
DNBP:2,4−ジニトロ−6−sec−ブチルフェノール
H−TEMPO:4−ヒドロキシ−2,2,6,6−テトラメチルピペリジン−1−オキシル
還流冷却器を備えた4つ口セパラブルフラスコにスチレンモノマー100gを入れ、表1の重合抑制剤を所定量加え(各薬剤の配合割合は下に示した)、高純度窒素ガスを30分間吹き込んで溶存酸素を除いた。次いでこれを120℃に保持し、一定時間毎に内容物の一部を取り出してサンプリングし、液中のポリマー生成量(ppm)を測定した。サンプリング液の9倍容量のメタノールを加えてポリマーを液中に懸濁状態で析出させ、濾過してポリマー重量を秤量し、モノマー中のポリマー生成量%として求めた。なお、本実験を始める前に、スチレンモノマーをアルカリ洗浄してモノマー中に含まれる重合禁止剤(t−ブチルカテコール)を除き、水洗、乾燥した。得られた結果を表1に示す。
Claims (4)
- 芳香族ビニル化合物の製造、精製、貯蔵あるいは輸送工程において、(A)下記一般式(III)で示される含窒素芳香族化合物と、(B)下記一般式(V)で示されるスルホン酸化合物を添加することを特徴とする芳香族ビニル化合物の重合抑制方法。
- 前記(A)成分の一般式(III)表示の含窒素芳香族化合物が、インジゴ及び/又はインジゴカーミンである請求項1記載の芳香族ビニル化合物の重合抑制方法。
- 前記(B)成分の一般式(V)表示のスルホン酸化合物が、トルエンスルホン酸、キシレンスルホン酸、クメンスルホン酸、ドデシルベンゼンスルホン酸、ペンタデシルベンゼンスルホン酸及びジノニルナフタレンスルホン酸から選ばれた少なくとも1種である請求項1または2のうちいずれかに記載の芳香族ビニル化合物の重合抑制方法。
- 前記(A)成分の含窒素芳香族化合物と前記(B)成分のスルホン酸化合物を重量比で5:95〜95:5の範囲で組み合わせて添加する請求項1ないし3のうちいずれかに記載の芳香族ビニル化合物の重合抑制方法。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2012170992A JP5602800B2 (ja) | 2006-03-24 | 2012-08-01 | 芳香族ビニル化合物の重合抑制方法 |
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2006082572 | 2006-03-24 | ||
JP2006082572 | 2006-03-24 | ||
JP2006082571 | 2006-03-24 | ||
JP2006082571 | 2006-03-24 | ||
JP2012170992A JP5602800B2 (ja) | 2006-03-24 | 2012-08-01 | 芳香族ビニル化合物の重合抑制方法 |
Related Parent Applications (1)
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JP2008507462A Division JP5142983B2 (ja) | 2006-03-24 | 2007-03-23 | 芳香族ビニル化合物の重合抑制方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2012214497A JP2012214497A (ja) | 2012-11-08 |
JP5602800B2 true JP5602800B2 (ja) | 2014-10-08 |
Family
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Family Applications (2)
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JP2008507462A Expired - Fee Related JP5142983B2 (ja) | 2006-03-24 | 2007-03-23 | 芳香族ビニル化合物の重合抑制方法 |
JP2012170992A Expired - Fee Related JP5602800B2 (ja) | 2006-03-24 | 2012-08-01 | 芳香族ビニル化合物の重合抑制方法 |
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JP2008507462A Expired - Fee Related JP5142983B2 (ja) | 2006-03-24 | 2007-03-23 | 芳香族ビニル化合物の重合抑制方法 |
Country Status (7)
Country | Link |
---|---|
US (2) | US8246858B2 (ja) |
EP (2) | EP2000451B1 (ja) |
JP (2) | JP5142983B2 (ja) |
KR (1) | KR101103158B1 (ja) |
CN (1) | CN101410355B (ja) |
CA (1) | CA2646342C (ja) |
WO (1) | WO2007111237A1 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9228126B2 (en) * | 2011-12-09 | 2016-01-05 | Dorf Ketal Chemicals (India) Private Limited | Additive composition for control and inhibition of polymerization of aromatic vinyl monomers, and method of use thereof |
BR112014015767B1 (pt) * | 2011-12-26 | 2021-05-18 | Dorf Ketal Chemicals (I) Private Limited | composição aditiva melhorada baseada em amina para o controle e inibição da polimerização de monômeros vinil aromáticos incluindo estireno, uso da dita composição e método para controlar e inibir a polimerização de monômeros vinil aromáticos incluindo estireno |
Family Cites Families (22)
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US2812329A (en) * | 1955-08-10 | 1957-11-05 | Phillips Petroleum Co | Heterocyclic nitrogen compound polymer inhibitors |
DE1074030B (de) * | 1957-01-19 | 1960-01-28 | Chemische Werke Hüls Aktiengesellschaft, Marl (Kr. Recklinghausen) | Stabilisierungsmittel für vinylgruppenhaltige, aliphatische, aromatische und heterocyclische Verbindungen gegen Polymerisation |
NL266444A (ja) * | 1960-06-29 | |||
US3379728A (en) * | 1966-09-12 | 1968-04-23 | Eastman Kodak Co | Phenazine-1, 4-dicarboxylic acids and esters thereof |
DE1643205A1 (de) * | 1967-03-23 | 1972-05-10 | Wacker Chemie Gmbh | Stabilisierung von monomeren,aethylenisch ungesaettigten Verbindungen |
US4425223A (en) | 1983-03-28 | 1984-01-10 | Atlantic Richfield Company | Method for minimizing fouling of heat exchangers |
US4654450A (en) | 1986-02-24 | 1987-03-31 | Atlantic Richfield Company | Inhibiting polymerization of vinyl aromatic monomers |
JPS63316745A (ja) | 1987-06-19 | 1988-12-26 | Mitsubishi Petrochem Co Ltd | 芳香族ビニル化合物の重合防止方法 |
JPH01165534A (ja) | 1987-12-22 | 1989-06-29 | Mitsubishi Petrochem Co Ltd | スチレン類の重合防止剤 |
US5157175A (en) * | 1991-09-09 | 1992-10-20 | Nalco Chemical Company | Composition and method for inhibition of styrene polymerization |
US5254760A (en) | 1992-07-29 | 1993-10-19 | Ciba-Geigy Corporation | Inhibiting polymerization of vinyl aromatic monomers |
JP3545440B2 (ja) | 1993-12-16 | 2004-07-21 | 伯東株式会社 | 芳香族不飽和化合物の粘度上昇抑制剤およびその方法 |
US5824829A (en) | 1993-12-16 | 1998-10-20 | Baker Hughes Incorporated | Hydrocarbon viscosity inhibitor and inhibiting method |
GB2285983B (en) * | 1994-01-25 | 1997-10-29 | Sumitomo Chemical Co | A method of inhibiting polymerization of vinyl compound and polymerization inhibitor used therein |
JP3673292B2 (ja) | 1994-07-27 | 2005-07-20 | 伯東株式会社 | ビニル化合物を扱う工程でのファウリング防止方法 |
JP3788950B2 (ja) * | 2001-04-25 | 2006-06-21 | 伯東株式会社 | 芳香族ビニル化合物の重合抑制方法 |
JP4834250B2 (ja) * | 2001-07-31 | 2011-12-14 | 伯東株式会社 | 芳香族ビニル化合物の重合抑制方法 |
JP4223222B2 (ja) * | 2002-03-19 | 2009-02-12 | 伯東株式会社 | 芳香族ビニル化合物の重合抑制方法 |
JP3990585B2 (ja) * | 2002-03-26 | 2007-10-17 | 伯東株式会社 | 芳香族ビニル化合物の重合抑制方法 |
CN100522902C (zh) * | 2003-03-17 | 2009-08-05 | 伯东株式会社 | 芳香族乙烯基化合物的聚合抑制剂以及聚合抑制方法 |
US7696290B2 (en) * | 2004-12-03 | 2010-04-13 | Crompton Corporation | Aromatic sulfonic acids, amines, and nitrophenols in combination with nitroxyl radical-containing compounds or C-nitrosanilines as polymerization inhibitors |
JP4871616B2 (ja) * | 2006-03-08 | 2012-02-08 | 伯東株式会社 | 芳香族ビニル化合物の重合抑制方法 |
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2007
- 2007-03-23 JP JP2008507462A patent/JP5142983B2/ja not_active Expired - Fee Related
- 2007-03-23 WO PCT/JP2007/055968 patent/WO2007111237A1/ja active Application Filing
- 2007-03-23 KR KR1020087024618A patent/KR101103158B1/ko active IP Right Grant
- 2007-03-23 EP EP07739409.6A patent/EP2000451B1/en not_active Expired - Fee Related
- 2007-03-23 CN CN2007800106112A patent/CN101410355B/zh not_active Expired - Fee Related
- 2007-03-23 EP EP15188577.9A patent/EP2995601B1/en not_active Expired - Fee Related
- 2007-03-23 US US12/224,748 patent/US8246858B2/en not_active Expired - Fee Related
- 2007-03-23 CA CA2646342A patent/CA2646342C/en not_active Expired - Fee Related
-
2012
- 2012-06-20 US US13/528,290 patent/US8551364B2/en not_active Expired - Fee Related
- 2012-08-01 JP JP2012170992A patent/JP5602800B2/ja not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
EP2995601B1 (en) | 2017-02-01 |
KR20080112279A (ko) | 2008-12-24 |
CA2646342C (en) | 2015-02-10 |
JPWO2007111237A1 (ja) | 2009-08-13 |
CA2646342A1 (en) | 2007-10-04 |
EP2000451A2 (en) | 2008-12-10 |
US20120264985A1 (en) | 2012-10-18 |
CN101410355A (zh) | 2009-04-15 |
JP5142983B2 (ja) | 2013-02-13 |
US8551364B2 (en) | 2013-10-08 |
EP2995601A1 (en) | 2016-03-16 |
US8246858B2 (en) | 2012-08-21 |
WO2007111237A1 (ja) | 2007-10-04 |
EP2000451B1 (en) | 2016-03-23 |
CN101410355B (zh) | 2013-09-18 |
JP2012214497A (ja) | 2012-11-08 |
EP2000451A9 (en) | 2009-03-25 |
KR101103158B1 (ko) | 2012-01-04 |
EP2000451A4 (en) | 2014-07-09 |
US20090149682A1 (en) | 2009-06-11 |
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