JP2004504369A5 - - Google Patents
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- Publication number
- JP2004504369A5 JP2004504369A5 JP2002514071A JP2002514071A JP2004504369A5 JP 2004504369 A5 JP2004504369 A5 JP 2004504369A5 JP 2002514071 A JP2002514071 A JP 2002514071A JP 2002514071 A JP2002514071 A JP 2002514071A JP 2004504369 A5 JP2004504369 A5 JP 2004504369A5
- Authority
- JP
- Japan
- Prior art keywords
- diimide
- vinyl
- phenyl
- benzoquinone
- functional group
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 description 16
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 15
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 10
- 229910000071 diazene Inorganic materials 0.000 description 7
- -1 quinone diimide compound Chemical class 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 6
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WLGPFDXTKQNTTJ-UHFFFAOYSA-N 1-n,4-n-di(butan-2-yl)cyclohexa-2,5-diene-1,4-diimine Chemical compound CCC(C)N=C1C=CC(=NC(C)CC)C=C1 WLGPFDXTKQNTTJ-UHFFFAOYSA-N 0.000 description 1
- SYVOPHRMGQKGRG-UHFFFAOYSA-N 1-n-(2-methylpropyl)-4-n-phenylcyclohexa-2,5-diene-1,4-diimine Chemical compound C1=CC(=NCC(C)C)C=CC1=NC1=CC=CC=C1 SYVOPHRMGQKGRG-UHFFFAOYSA-N 0.000 description 1
- YRZFKLFEZZLQLO-UHFFFAOYSA-N 1-n-butyl-4-n-phenylcyclohexa-2,5-diene-1,4-diimine Chemical compound C1=CC(=NCCCC)C=CC1=NC1=CC=CC=C1 YRZFKLFEZZLQLO-UHFFFAOYSA-N 0.000 description 1
- WMFRXLMQHUUPDX-UHFFFAOYSA-N 1-n-methyl-4-n-phenylcyclohexa-2,5-diene-1,4-diimine Chemical compound C1=CC(=NC)C=CC1=NC1=CC=CC=C1 WMFRXLMQHUUPDX-UHFFFAOYSA-N 0.000 description 1
- ZJOSVJIUNHABQV-UHFFFAOYSA-N 1-n-pentyl-4-n-phenylcyclohexa-2,5-diene-1,4-diimine Chemical compound C1=CC(=NCCCCC)C=CC1=NC1=CC=CC=C1 ZJOSVJIUNHABQV-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- BESOIXIOWFNTDV-UHFFFAOYSA-N 4-n-butan-2-yl-1-n-phenylcyclohexa-2,5-diene-1,4-diimine Chemical compound C1=CC(=NC(C)CC)C=CC1=NC1=CC=CC=C1 BESOIXIOWFNTDV-UHFFFAOYSA-N 0.000 description 1
- UHSJJWAQMJQELM-UHFFFAOYSA-N 4-n-heptan-2-yl-1-n-phenylcyclohexa-2,5-diene-1,4-diimine Chemical compound C1=CC(=NC(C)CCCCC)C=CC1=NC1=CC=CC=C1 UHSJJWAQMJQELM-UHFFFAOYSA-N 0.000 description 1
- JYAVDDDFKCHFDD-UHFFFAOYSA-N 4-n-phenyl-1-n-propylcyclohexa-2,5-diene-1,4-diimine Chemical compound C1=CC(=NCCC)C=CC1=NC1=CC=CC=C1 JYAVDDDFKCHFDD-UHFFFAOYSA-N 0.000 description 1
- JWIODQXDZYESLF-UHFFFAOYSA-N 4-n-tert-butyl-1-n-phenylcyclohexa-2,5-diene-1,4-diimine Chemical compound C1=CC(=NC(C)(C)C)C=CC1=NC1=CC=CC=C1 JWIODQXDZYESLF-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000217 alkyl 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
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- ACFNYGLBKAZUDY-UHFFFAOYSA-N cyclohexa-2,5-diene-1,4-diimine Chemical compound N=C1C=CC(=N)C=C1 ACFNYGLBKAZUDY-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/625,617 US6447649B1 (en) | 2000-07-24 | 2000-07-24 | Polymerization inhibitor for vinyl-containing materials |
| PCT/US2001/018259 WO2002008161A2 (en) | 2000-07-24 | 2001-06-04 | Polymerization inhibitor for vinyl-containing materials |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004504369A JP2004504369A (ja) | 2004-02-12 |
| JP2004504369A5 true JP2004504369A5 (enExample) | 2008-07-31 |
| JP4672963B2 JP4672963B2 (ja) | 2011-04-20 |
Family
ID=24506878
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002514071A Expired - Fee Related JP4672963B2 (ja) | 2000-07-24 | 2001-06-04 | ビニル含有材料の重合防止剤 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US6447649B1 (enExample) |
| EP (1) | EP1305279B1 (enExample) |
| JP (1) | JP4672963B2 (enExample) |
| KR (1) | KR100730847B1 (enExample) |
| AU (1) | AU2001275287A1 (enExample) |
| BR (1) | BR0112727B1 (enExample) |
| DE (1) | DE60109040T2 (enExample) |
| ES (1) | ES2236244T3 (enExample) |
| MX (1) | MXPA03000704A (enExample) |
| TW (1) | TWI247738B (enExample) |
| WO (1) | WO2002008161A2 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR0309629A (pt) * | 2002-05-01 | 2005-03-08 | Ciba Sc Holding Ag | Processo para término de cadeia na polimerização de pvc |
| JP5450300B2 (ja) * | 2009-07-31 | 2014-03-26 | 富士フイルム株式会社 | 放射線硬化性塩化ビニル系樹脂組成物およびその製造方法、塩化ビニル系樹脂、磁気記録媒体、ならびに放射線硬化性塩化ビニル系樹脂用保存安定剤 |
| US8691994B2 (en) * | 2011-02-03 | 2014-04-08 | Nalco Company | Multi-component polymerization inhibitors for ethylenically unsaturated monomers |
| US9090526B2 (en) | 2011-06-13 | 2015-07-28 | Nalco Company | Synergistic combination for inhibiting polymerization of vinyl monomers |
| US9206268B2 (en) | 2011-09-16 | 2015-12-08 | General Electric Company | Methods and compositions for inhibiting polystyrene formation during styrene production |
| JP5752579B2 (ja) * | 2011-12-09 | 2015-07-22 | 伯東株式会社 | 安定化された４−オキソ−２，２，６，６−テトラメチルピペリジン−１−オキシル含有組成物、ビニル化合物の重合禁止剤組成物、及びこれを用いたビニル化合物の重合禁止方法 |
| US9944577B2 (en) | 2012-10-25 | 2018-04-17 | Baker Hughes, A Ge Company, Llc | Hydroquinone compounds for inhibiting monomer polymerization |
| US9611336B2 (en) | 2012-10-25 | 2017-04-04 | Baker Hughes Incorporated | Quinone compounds for inhibiting monomer polymerization |
| US10782541B2 (en) | 2015-11-23 | 2020-09-22 | Carl Zeiss Vision International Gmbh | Method for designing a lens shape and spectacle lens |
| EP3738951B1 (en) * | 2018-11-27 | 2022-09-14 | Boai NKY Medical Holdings Ltd. | Use of a polymerization inhibitor for n-vinyl pyrrolidone monomer |
| ES3002772T3 (en) * | 2018-12-20 | 2025-03-07 | Ecolab Usa Inc | Hydroxylated quinone antipolymerants and methods of using |
| EP4036074A1 (en) * | 2021-01-27 | 2022-08-03 | Evonik Operations GmbH | Method for suppressing the polymerization of unsaturated aromatic monomers |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR7602313A (pt) * | 1975-04-17 | 1976-10-12 | Felt Products Mfg Co | Composicao anaerobica de cola e processo para sua preparacao |
| US4166169A (en) * | 1976-03-05 | 1979-08-28 | Felt Products Mfg. Co. | High-strength anaerobic sealants containing n-nitrosoamine modifier |
| JPS604194A (ja) * | 1983-06-21 | 1985-01-10 | Kanegafuchi Chem Ind Co Ltd | アクリルオキシシラン用安定剤 |
| JP3045175B2 (ja) * | 1990-10-04 | 2000-05-29 | 三井化学株式会社 | 発色性記録材料 |
| 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 |
| US5728872A (en) * | 1994-06-27 | 1998-03-17 | Lutz Riemenschneider | Stabilized acrylic acid compositions |
| DE4437667A1 (de) * | 1994-10-21 | 1996-04-25 | Huels Chemische Werke Ag | Verfahren zur Herstellung von N,N'-disubstituierten p-Chinondiiminen, deren Verwendung und Methacryloxy- oder Acryloxy-Gruppen enthaltende Organosilane, Verfahren zu deren Stabilisierung und deren Herstellung |
| DE4437666A1 (de) * | 1994-10-21 | 1996-04-25 | Huels Chemische Werke Ag | Verfahren zur Herstellung von N,N-disubstituierten p-Chinondiiminen und deren Verwendung |
| US5583247A (en) | 1995-04-14 | 1996-12-10 | Ciba-Geigy Corporation | 7-substituted quinone methides as inhibitors for unsaturated monomers |
| US5648573A (en) | 1995-06-12 | 1997-07-15 | Betzdearborn Inc. | Compositions and methods for inhibiting vinyl aromatic monomer polymerization |
| US5756870A (en) | 1996-05-03 | 1998-05-26 | Betzdearborn Inc. | Methods for inhibiting the polymerization of ethylenically unsaturated monomers |
| US5877344A (en) | 1997-06-13 | 1999-03-02 | Ciba Specialty Chemicals Corporation | Polymerization inhibition of acrylates using blends of nitroxides |
| US5859280A (en) * | 1997-07-01 | 1999-01-12 | Betzdearborn Inc. | Methods for inhibiting the polymerization of vinyl monomers |
| ES2192798T3 (es) * | 1997-10-20 | 2003-10-16 | Flexsys America Lp | Quinonadiimina como aditivo para el caucho. |
-
2000
- 2000-07-24 US US09/625,617 patent/US6447649B1/en not_active Expired - Fee Related
-
2001
- 2001-06-04 DE DE60109040T patent/DE60109040T2/de not_active Expired - Lifetime
- 2001-06-04 EP EP01941980A patent/EP1305279B1/en not_active Expired - Lifetime
- 2001-06-04 BR BRPI0112727-6A patent/BR0112727B1/pt not_active IP Right Cessation
- 2001-06-04 KR KR1020037001027A patent/KR100730847B1/ko not_active Expired - Fee Related
- 2001-06-04 WO PCT/US2001/018259 patent/WO2002008161A2/en not_active Ceased
- 2001-06-04 AU AU2001275287A patent/AU2001275287A1/en not_active Abandoned
- 2001-06-04 ES ES01941980T patent/ES2236244T3/es not_active Expired - Lifetime
- 2001-06-04 MX MXPA03000704A patent/MXPA03000704A/es active IP Right Grant
- 2001-06-04 JP JP2002514071A patent/JP4672963B2/ja not_active Expired - Fee Related
- 2001-07-24 TW TW090118057A patent/TWI247738B/zh not_active IP Right Cessation
-
2002
- 2002-09-04 US US10/235,009 patent/US6592722B2/en not_active Expired - Lifetime
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