ES2627022T3 - Combinación sinérgica para inhibir la polimerización de monómeros de vinilo - Google Patents
Combinación sinérgica para inhibir la polimerización de monómeros de vinilo Download PDFInfo
- Publication number
- ES2627022T3 ES2627022T3 ES12800052.8T ES12800052T ES2627022T3 ES 2627022 T3 ES2627022 T3 ES 2627022T3 ES 12800052 T ES12800052 T ES 12800052T ES 2627022 T3 ES2627022 T3 ES 2627022T3
- Authority
- ES
- Spain
- Prior art keywords
- compound
- tert
- quinone
- butyl
- methylide
- 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.)
- Active
Links
- 239000000178 monomer Substances 0.000 title claims abstract description 43
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 42
- 229920002554 vinyl polymer Polymers 0.000 title claims abstract description 23
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title claims abstract description 14
- 239000011885 synergistic combination Substances 0.000 title description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims abstract description 141
- -1 quinone methylide compound Chemical class 0.000 claims abstract description 85
- 229910000071 diazene Inorganic materials 0.000 claims abstract description 53
- 239000000203 mixture Substances 0.000 claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 27
- 229940126062 Compound A Drugs 0.000 claims abstract description 25
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims abstract description 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 11
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 10
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims abstract description 9
- 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 abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 6
- 150000002825 nitriles Chemical class 0.000 claims abstract description 6
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims abstract description 4
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 claims description 38
- 239000003112 inhibitor Substances 0.000 claims description 35
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 14
- HRLDHROCDBYHAU-UHFFFAOYSA-N 2,6-ditert-butyl-4-[(3,5-ditert-butyl-4-hydroxyphenyl)methylidene]cyclohexa-2,5-dien-1-one Chemical compound C1=C(C(C)(C)C)C(=O)C(C(C)(C)C)=CC1=CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 HRLDHROCDBYHAU-UHFFFAOYSA-N 0.000 claims description 5
- VWJMHEHVAHYPDI-UHFFFAOYSA-N 2-(3,5-ditert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)acetonitrile Chemical compound CC(C)(C)C1=CC(=CC#N)C=C(C(C)(C)C)C1=O VWJMHEHVAHYPDI-UHFFFAOYSA-N 0.000 claims description 5
- HCUWXYBKPSKTAB-UHFFFAOYSA-N 4-benzylidene-2,6-ditert-butylcyclohexa-2,5-dien-1-one Chemical compound C1=C(C(C)(C)C)C(=O)C(C(C)(C)C)=CC1=CC1=CC=CC=C1 HCUWXYBKPSKTAB-UHFFFAOYSA-N 0.000 claims description 5
- 230000005764 inhibitory process Effects 0.000 claims description 5
- UKYDGPJEHLNYFS-UHFFFAOYSA-N 2,6-ditert-butyl-4-(methoxymethylidene)cyclohexa-2,5-dien-1-one Chemical compound COC=C1C=C(C(C)(C)C)C(=O)C(C(C)(C)C)=C1 UKYDGPJEHLNYFS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000004151 quinonyl group Chemical group 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 15
- 229920000642 polymer Polymers 0.000 description 13
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- 230000006698 induction Effects 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- IKKZTMLWHZAQKF-UHFFFAOYSA-N 1-n,4-n-bis(5-methylhexan-2-yl)cyclohexa-2,5-diene-1,4-diimine Chemical compound CC(C)CCC(C)N=C1C=CC(=NC(C)CCC(C)C)C=C1 IKKZTMLWHZAQKF-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
- MHKBMNACOMRIAW-UHFFFAOYSA-N 2,3-dinitrophenol Chemical class OC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O MHKBMNACOMRIAW-UHFFFAOYSA-N 0.000 description 1
- JCRIDWXIBSEOEG-UHFFFAOYSA-N 2,6-dinitrophenol Chemical compound OC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O JCRIDWXIBSEOEG-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
- SZMBYKBVFJKLQB-UHFFFAOYSA-N 3-(hydroxyamino)propan-1-ol Chemical compound OCCCNO SZMBYKBVFJKLQB-UHFFFAOYSA-N 0.000 description 1
- VKDQWXQGUDNQLB-UHFFFAOYSA-N 4-n-(5-methylhexan-2-yl)-1-n-phenylcyclohexa-2,5-diene-1,4-diimine Chemical compound C1=CC(=NC(C)CCC(C)C)C=CC1=NC1=CC=CC=C1 VKDQWXQGUDNQLB-UHFFFAOYSA-N 0.000 description 1
- YQCPRPMNFQIXEQ-UHFFFAOYSA-N 4-n-hexan-2-yl-1-n-phenylcyclohexa-2,5-diene-1,4-diimine Chemical compound C1=CC(=NC(C)CCCC)C=CC1=NC1=CC=CC=C1 YQCPRPMNFQIXEQ-UHFFFAOYSA-N 0.000 description 1
- QHJIRTVISXHLRI-UHFFFAOYSA-N 6-methyl-4,6-dinitrocyclohexa-1,3-dien-1-ol Chemical compound [O-][N+](=O)C1(C)CC([N+]([O-])=O)=CC=C1O QHJIRTVISXHLRI-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 230000002613 anti-polymerizing effect Effects 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 150000001785 cerium compounds Chemical class 0.000 description 1
- ACFNYGLBKAZUDY-UHFFFAOYSA-N cyclohexa-2,5-diene-1,4-diimine Chemical class N=C1C=CC(=N)C=C1 ACFNYGLBKAZUDY-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/603—Unsaturated compounds containing a keto groups being part of a ring of a six-membered ring, e.g. quinone methides
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201113158979 | 2011-06-13 | ||
| US13/158,979 US9090526B2 (en) | 2011-06-13 | 2011-06-13 | Synergistic combination for inhibiting polymerization of vinyl monomers |
| PCT/US2012/041883 WO2012173925A2 (en) | 2011-06-13 | 2012-06-11 | Synergistic combination for inhiibiting polymerization of vinyl monomers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2627022T3 true ES2627022T3 (es) | 2017-07-26 |
Family
ID=47293705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES12800052.8T Active ES2627022T3 (es) | 2011-06-13 | 2012-06-11 | Combinación sinérgica para inhibir la polimerización de monómeros de vinilo |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9090526B2 (https=) |
| EP (1) | EP2726451B1 (https=) |
| JP (1) | JP5956568B2 (https=) |
| KR (1) | KR101949324B1 (https=) |
| CN (1) | CN103502194B (https=) |
| BR (1) | BR112013030733B1 (https=) |
| CA (1) | CA2835880C (https=) |
| ES (1) | ES2627022T3 (https=) |
| MX (1) | MX337993B (https=) |
| SG (1) | SG194958A1 (https=) |
| TW (1) | TWI580671B (https=) |
| WO (1) | WO2012173925A2 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8901362B2 (en) * | 2012-02-02 | 2014-12-02 | General Electric Company | Methods and compositions for styrene inhibition via in situ generation of quinone methides |
| IN2013MU01165A (https=) * | 2013-03-26 | 2015-04-24 | Dorf Ketal Chemicals India Private Ltd | |
| 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 |
| US20210040125A1 (en) * | 2018-11-27 | 2021-02-11 | Boai Nky Medical Holdings Ltd | Polymerization inhibitor for n-vinyl pyrrolidone monomer and use thereof |
| 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 |
| CN115490711B (zh) * | 2021-06-18 | 2024-08-20 | 唐山师范学院 | 4-（3-苯硼酸）亚甲基-2,6-二叔丁基-2,5-环己二烯-1-酮化合物的合成和应用 |
| CN116553996A (zh) * | 2023-07-07 | 2023-08-08 | 吉林金海化工新材料有限公司 | 一种阻聚剂及其应用 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4003800A (en) * | 1976-01-02 | 1977-01-18 | Gulf Research & Development Company | Styrene purification process |
| US4774374A (en) | 1987-06-12 | 1988-09-27 | Uniroyal Chemical Company, Inc. | Stabilized vinyl aromatic composition |
| US4912247A (en) * | 1989-01-19 | 1990-03-27 | Betz Laboratories, Ltd. | Enhancement of aromatic amine inhibition of acrylate monomer polymerization by addition of mannich products |
| US5221764A (en) | 1992-02-18 | 1993-06-22 | Betz Laboratories, Inc. | Methods and compositions for inhibiting acrylic acid polymerization |
| US5470440A (en) * | 1994-04-19 | 1995-11-28 | Betz Laboratories, Inc. | Method for inhibiting vinyl aromatic monomer polymerization |
| US5583247A (en) | 1995-04-14 | 1996-12-10 | Ciba-Geigy Corporation | 7-substituted quinone methides as inhibitors for unsaturated monomers |
| US5616774A (en) * | 1995-04-14 | 1997-04-01 | Ciba-Geigy Corporation | Inhibition of unsaturated monomers with 7-aryl quinone methides |
| US5648573A (en) | 1995-06-12 | 1997-07-15 | Betzdearborn Inc. | Compositions and methods for inhibiting vinyl aromatic monomer polymerization |
| US5955643A (en) | 1997-10-17 | 1999-09-21 | Nalco/Exxon Energy Chemicals, L.P. | Composition and method for inhibiting polymerization during the anaerobic of styrene |
| JP4249897B2 (ja) | 1997-10-20 | 2009-04-08 | フレクシス アメリカ エル． ピー． | ゴム添加剤としてのキノンジイミン |
| 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 |
| US6447649B1 (en) * | 2000-07-24 | 2002-09-10 | Ge Betz, Inc. | Polymerization inhibitor for vinyl-containing materials |
| US7045647B2 (en) | 2000-10-16 | 2006-05-16 | Uniroyal Chemical Company, Inc. | Blends of quinone alkide and nitroxyl compounds and polymerization inhibitors |
| US6685823B2 (en) * | 2000-10-16 | 2004-02-03 | Uniroyal Chemical Company, Inc. | C-nitrosoaniline compounds and their blends 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 |
| DE102007052891A1 (de) * | 2007-11-02 | 2009-05-07 | Evonik Degussa Gmbh | Verfahren zur Stabilisierung von olefinisch ungesättigten Monomeren |
| US8247593B2 (en) | 2008-05-13 | 2012-08-21 | Nalco Company | Process for preparing substituted 7-cyano quinone methides |
| US7651635B1 (en) | 2009-02-05 | 2010-01-26 | Nalco Company | Polymer inhibition of vinyl aromatic monomers using a quinone methide/alkyl hydroxylamine combination |
-
2011
- 2011-06-13 US US13/158,979 patent/US9090526B2/en active Active
-
2012
- 2012-06-08 TW TW101120624A patent/TWI580671B/zh active
- 2012-06-11 SG SG2013084397A patent/SG194958A1/en unknown
- 2012-06-11 EP EP12800052.8A patent/EP2726451B1/en active Active
- 2012-06-11 BR BR112013030733A patent/BR112013030733B1/pt active IP Right Grant
- 2012-06-11 CA CA2835880A patent/CA2835880C/en active Active
- 2012-06-11 ES ES12800052.8T patent/ES2627022T3/es active Active
- 2012-06-11 CN CN201280021222.0A patent/CN103502194B/zh active Active
- 2012-06-11 JP JP2014515900A patent/JP5956568B2/ja active Active
- 2012-06-11 MX MX2013013686A patent/MX337993B/es active IP Right Grant
- 2012-06-11 WO PCT/US2012/041883 patent/WO2012173925A2/en not_active Ceased
- 2012-06-11 KR KR1020147000906A patent/KR101949324B1/ko active Active
Also Published As
| Publication number | Publication date |
|---|---|
| MX337993B (es) | 2016-03-30 |
| EP2726451B1 (en) | 2017-03-22 |
| US9090526B2 (en) | 2015-07-28 |
| KR20140041730A (ko) | 2014-04-04 |
| MX2013013686A (es) | 2014-01-08 |
| TWI580671B (zh) | 2017-05-01 |
| CA2835880A1 (en) | 2012-12-20 |
| EP2726451A4 (en) | 2015-03-18 |
| CN103502194A (zh) | 2014-01-08 |
| JP5956568B2 (ja) | 2016-07-27 |
| EP2726451A2 (en) | 2014-05-07 |
| KR101949324B1 (ko) | 2019-02-18 |
| WO2012173925A2 (en) | 2012-12-20 |
| US20120316369A1 (en) | 2012-12-13 |
| JP2014527509A (ja) | 2014-10-16 |
| CN103502194B (zh) | 2016-08-17 |
| BR112013030733A2 (pt) | 2016-12-06 |
| CA2835880C (en) | 2018-03-13 |
| WO2012173925A3 (en) | 2013-04-25 |
| TW201302699A (zh) | 2013-01-16 |
| BR112013030733B1 (pt) | 2019-12-24 |
| SG194958A1 (en) | 2013-12-30 |
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