JP2018513258A5 - - Google Patents
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- Publication number
- JP2018513258A5 JP2018513258A5 JP2017554871A JP2017554871A JP2018513258A5 JP 2018513258 A5 JP2018513258 A5 JP 2018513258A5 JP 2017554871 A JP2017554871 A JP 2017554871A JP 2017554871 A JP2017554871 A JP 2017554871A JP 2018513258 A5 JP2018513258 A5 JP 2018513258A5
- Authority
- JP
- Japan
- Prior art keywords
- tetramethylpiperidine
- oxide
- independently
- polymerization
- compound
- 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 claims 17
- -1 hydroquinone compound Chemical class 0.000 claims 14
- 238000006116 polymerization reaction Methods 0.000 claims 10
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims 8
- 230000002401 inhibitory effect Effects 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 7
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims 6
- FAPCFNWEPHTUQK-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-oxidopiperidin-1-ium-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)[NH+]1[O-] FAPCFNWEPHTUQK-UHFFFAOYSA-N 0.000 claims 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 229930195733 hydrocarbon Natural products 0.000 claims 6
- 150000002430 hydrocarbons Chemical class 0.000 claims 6
- 239000004215 Carbon black (E152) Substances 0.000 claims 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- RVWUHFFPEOKYLB-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-oxidopiperidin-1-ium Chemical compound CC1(C)CCCC(C)(C)[NH+]1[O-] RVWUHFFPEOKYLB-UHFFFAOYSA-N 0.000 claims 2
- HVZQOGWWUPCQPC-UHFFFAOYSA-N 4-butoxy-2,2,6,6-tetramethylpiperidine Chemical compound CCCCOC1CC(C)(C)NC(C)(C)C1 HVZQOGWWUPCQPC-UHFFFAOYSA-N 0.000 claims 2
- AHPXMHKEFQCGBY-UHFFFAOYSA-N 4-ethoxy-1-hydroxy-2,2,6,6-tetramethylpiperidine Chemical compound CCOC1CC(C)(C)N(O)C(C)(C)C1 AHPXMHKEFQCGBY-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 238000000605 extraction Methods 0.000 claims 2
- 238000005194 fractionation Methods 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 238000000746 purification Methods 0.000 claims 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 claims 1
- JSTCPNFNKICNNO-UHFFFAOYSA-N 4-nitrosophenol Chemical compound OC1=CC=C(N=O)C=C1 JSTCPNFNKICNNO-UHFFFAOYSA-N 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 238000005865 alkene metathesis reaction Methods 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 229910021386 carbon form Inorganic materials 0.000 claims 1
- 230000006835 compression Effects 0.000 claims 1
- 238000007906 compression Methods 0.000 claims 1
- 238000006356 dehydrogenation reaction Methods 0.000 claims 1
- 230000003111 delayed effect Effects 0.000 claims 1
- 239000002283 diesel fuel Substances 0.000 claims 1
- 239000000295 fuel oil Substances 0.000 claims 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- 229950000688 phenothiazine Drugs 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 229920005989 resin Polymers 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 230000006641 stabilisation Effects 0.000 claims 1
- 238000011105 stabilization Methods 0.000 claims 1
- 0 *c(cc(c1c2****1)O)c2O Chemical compound *c(cc(c1c2****1)O)c2O 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562150022P | 2015-04-20 | 2015-04-20 | |
| US62/150,022 | 2015-04-20 | ||
| PCT/US2016/028239 WO2016172076A1 (en) | 2015-04-20 | 2016-04-19 | Sterically hindered hydroquinones as antifoulants for unsaturated monomers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018513258A JP2018513258A (ja) | 2018-05-24 |
| JP2018513258A5 true JP2018513258A5 (https=) | 2019-05-30 |
| JP6843067B2 JP6843067B2 (ja) | 2021-03-17 |
Family
ID=57128251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017554871A Active JP6843067B2 (ja) | 2015-04-20 | 2016-04-19 | 不飽和モノマー類の重合を阻害する方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US10155705B2 (https=) |
| EP (2) | EP4628479A3 (https=) |
| JP (1) | JP6843067B2 (https=) |
| KR (1) | KR102616836B1 (https=) |
| CN (1) | CN107532083A (https=) |
| AR (1) | AR104327A1 (https=) |
| BR (1) | BR112017022431B1 (https=) |
| CA (1) | CA2982465C (https=) |
| RU (1) | RU2746125C2 (https=) |
| SA (1) | SA517390157B1 (https=) |
| TW (1) | TWI624480B (https=) |
| WO (1) | WO2016172076A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11180578B2 (en) | 2018-07-13 | 2021-11-23 | Ecolab Usa Inc. | Polymerization inhibitor and retarder compositions with amine stabilizer |
| EP3820836A1 (en) | 2018-07-13 | 2021-05-19 | Ecolab USA, Inc. | Compositions of oxygenated amines and quinone methides as antifoulants for vinylic monomers |
| EP3856792A1 (en) | 2018-09-28 | 2021-08-04 | Ecolab USA, Inc. | Amino-quinone antipolymerants and methods of using |
| US11104626B2 (en) * | 2018-12-20 | 2021-08-31 | Ecolab Usa Inc. | Hydroxylated quinone antipolymerants and methods of using |
| KR102803771B1 (ko) | 2019-07-09 | 2025-05-02 | 에스케이이노베이션 주식회사 | 윤활 조성물 및 이를 이용한 공중합체의 제조 방법 |
| TWI880966B (zh) | 2019-10-11 | 2025-04-21 | 美商藝康美國公司 | 醌甲基化物及銨鹽抗聚合劑組合物及方法 |
| KR102865445B1 (ko) | 2020-02-20 | 2025-09-25 | 에스케이이노베이션 주식회사 | 에틸렌-카르복실산 공중합체의 제조 방법 |
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| SU763313A1 (ru) * | 1978-10-17 | 1980-09-15 | Волгоградский Политехнический Институт | Способ ингибировани термополимеризации стирола |
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| US4487981A (en) | 1983-09-08 | 1984-12-11 | Atlantic Richfield Company | Inhibiting polymerization of vinyl aromatic monomers |
| JPH0689061B2 (ja) | 1988-12-16 | 1994-11-09 | 日本石油株式会社 | ブタジエン低重合体付加物の製造方法 |
| JP2876331B2 (ja) * | 1990-02-28 | 1999-03-31 | 日本石油化学株式会社 | 付加方法 |
| US5290888A (en) | 1990-07-20 | 1994-03-01 | Ciba-Geigy Corporation | Process for stabilizing ethylenically unsaturated compounds and stabilized monomer compositions |
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| US8884038B2 (en) | 2011-06-13 | 2014-11-11 | Nalco Company | Synthesis of 7-acetyleno quinone methide derivatives and their application as vinylic polymerization retarders |
| DE102013204950A1 (de) | 2013-03-20 | 2014-09-25 | Evonik Industries Ag | Verfahren und Zusammensetzung zur Inhibierung der Polymerisation von Cyclopentadienverbindungen |
| CN103342798B (zh) * | 2013-07-16 | 2015-08-19 | 华东理工大学 | 一种低粘度耐高温改性环氧树脂的合成方法 |
| US9399622B2 (en) | 2013-12-03 | 2016-07-26 | Ecolab Usa Inc. | Nitroxide hydroxylamine and phenylenediamine combinations as polymerization inhibitors for ethylenically unsaturated monomer processes |
-
2016
- 2016-04-19 KR KR1020177031676A patent/KR102616836B1/ko active Active
- 2016-04-19 TW TW105112109A patent/TWI624480B/zh active
- 2016-04-19 WO PCT/US2016/028239 patent/WO2016172076A1/en not_active Ceased
- 2016-04-19 JP JP2017554871A patent/JP6843067B2/ja active Active
- 2016-04-19 US US15/132,844 patent/US10155705B2/en active Active
- 2016-04-19 BR BR112017022431-3A patent/BR112017022431B1/pt active IP Right Grant
- 2016-04-19 EP EP25182651.7A patent/EP4628479A3/en active Pending
- 2016-04-19 CN CN201680022901.8A patent/CN107532083A/zh active Pending
- 2016-04-19 RU RU2017139281A patent/RU2746125C2/ru active
- 2016-04-19 EP EP16783672.5A patent/EP3289046A4/en not_active Ceased
- 2016-04-19 CA CA2982465A patent/CA2982465C/en active Active
- 2016-04-20 AR ARP160101084A patent/AR104327A1/es active IP Right Grant
-
2017
- 2017-10-15 SA SA517390157A patent/SA517390157B1/ar unknown
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