ES2398053T3 - Inhibición polimérica de monómeros aromáticos vinílicos usando una combinación de metiluro de quinona/alquil hidroxilamina - Google Patents
Inhibición polimérica de monómeros aromáticos vinílicos usando una combinación de metiluro de quinona/alquil hidroxilamina Download PDFInfo
- Publication number
- ES2398053T3 ES2398053T3 ES10704042T ES10704042T ES2398053T3 ES 2398053 T3 ES2398053 T3 ES 2398053T3 ES 10704042 T ES10704042 T ES 10704042T ES 10704042 T ES10704042 T ES 10704042T ES 2398053 T3 ES2398053 T3 ES 2398053T3
- Authority
- ES
- Spain
- Prior art keywords
- inhibitor
- monomers
- retarder
- quinone
- combination
- 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
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 239000000178 monomer Substances 0.000 title claims abstract description 38
- 229920002554 vinyl polymer Polymers 0.000 title claims description 7
- -1 alkyl hydroxylamine Chemical compound 0.000 title description 4
- 230000005764 inhibitory process Effects 0.000 title description 2
- 239000003112 inhibitor Substances 0.000 claims abstract description 54
- 238000000034 method Methods 0.000 claims abstract description 25
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical group [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 13
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 13
- 230000002028 premature Effects 0.000 claims abstract description 5
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 3
- BJEMXPVDXFSROA-UHFFFAOYSA-N 3-butylbenzene-1,2-diol Chemical group CCCCC1=CC=CC(O)=C1O BJEMXPVDXFSROA-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- SZMBYKBVFJKLQB-UHFFFAOYSA-N 3-(hydroxyamino)propan-1-ol Chemical compound OCCCNO SZMBYKBVFJKLQB-UHFFFAOYSA-N 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 229920001174 Diethylhydroxylamine Polymers 0.000 claims description 3
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 238000003860 storage Methods 0.000 claims description 3
- 239000004793 Polystyrene Substances 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 150000004053 quinones Chemical class 0.000 abstract description 2
- 229920000642 polymer Polymers 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 7
- 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 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000006698 induction Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 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
- 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 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
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
Classifications
-
- 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
- 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
- C09K15/08—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen containing a phenol or quinone moiety
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Materials Engineering (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US366154 | 2009-02-05 | ||
| US12/366,154 US7651635B1 (en) | 2009-02-05 | 2009-02-05 | Polymer inhibition of vinyl aromatic monomers using a quinone methide/alkyl hydroxylamine combination |
| PCT/US2010/022977 WO2010091040A1 (en) | 2009-02-05 | 2010-02-03 | Polymer inhibition of vinyl aromatic monomers using a quinone methide/alkyl hydroxomine combination |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2398053T3 true ES2398053T3 (es) | 2013-03-13 |
Family
ID=41559765
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10704042T Active ES2398053T3 (es) | 2009-02-05 | 2010-02-03 | Inhibición polimérica de monómeros aromáticos vinílicos usando una combinación de metiluro de quinona/alquil hidroxilamina |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7651635B1 (enExample) |
| EP (1) | EP2393765B1 (enExample) |
| JP (1) | JP5536106B2 (enExample) |
| KR (1) | KR101613760B1 (enExample) |
| CN (1) | CN102307830B (enExample) |
| BR (1) | BRPI1005420B1 (enExample) |
| CA (1) | CA2750187C (enExample) |
| ES (1) | ES2398053T3 (enExample) |
| SG (1) | SG173564A1 (enExample) |
| TW (1) | TWI461406B (enExample) |
| WO (1) | WO2010091040A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US8884038B2 (en) * | 2011-06-13 | 2014-11-11 | Nalco Company | Synthesis of 7-acetyleno quinone methide derivatives and their application as vinylic polymerization retarders |
| EP2748207B1 (en) | 2011-08-26 | 2016-04-06 | Dorf Ketal Chemicals (India) Private Limited | Additive composition for control and inhibition of polymerization of styrene, and method of preparation and use thereof |
| 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 |
| CN103998404B (zh) * | 2011-12-26 | 2017-12-15 | 多尔夫凯塔尔化学制品（I）私人有限公司 | 用于控制及抑制芳香族乙烯基单体聚合的改良的基于胺的添加剂组合物，及其使用方法 |
| MY182112A (en) * | 2012-08-24 | 2021-01-18 | Dorf Ketal Chemicals India Private Ltd | Composition of quinone methide derivatives and amines for control and inhibition of polymerization of monomers, and method of preparation and use thereof |
| 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 |
| IN2013MU01165A (enExample) * | 2013-03-26 | 2015-04-24 | Dorf Ketal Chemicals India Private Ltd | |
| US9399622B2 (en) | 2013-12-03 | 2016-07-26 | Ecolab Usa Inc. | Nitroxide hydroxylamine and phenylenediamine combinations as polymerization inhibitors for ethylenically unsaturated monomer processes |
| CA3014153C (en) * | 2016-02-13 | 2020-12-15 | Dorf Ketal Chemicals (India) Private Limited | Compositions for control and inhibition of polymerization of vinyl aromatic monomers, and methods of use thereof. |
| KR102763249B1 (ko) | 2018-07-13 | 2025-02-04 | 에코랍 유에스에이 인코퍼레이티드 | 니트록사이드 억제제, 퀴논 메티드 지연제 및 아민 안정화제를 포함하는 단량체 중합 억제용 조성물 |
| CN112513005A (zh) * | 2018-07-13 | 2021-03-16 | 埃科莱布美国股份有限公司 | 氧化胺和甲基化醌的组合物作为乙烯单体的抗污剂 |
| 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 |
| TW202545813A (zh) * | 2024-04-12 | 2025-12-01 | 美商Ｂｌ科技公司 | 增強型苯乙烯聚合阻滯劑及使用方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3390198A (en) * | 1965-12-16 | 1968-06-25 | Koppers Co Inc | Tertiary-butyl-5-methyl catechol as polymerization inhibitor for hot styrene |
| US4003800A (en) | 1976-01-02 | 1977-01-18 | Gulf Research & Development Company | Styrene purification process |
| US4409408A (en) * | 1982-09-24 | 1983-10-11 | Atlantic Richfield Company | Inhibiting polymerization of vinyl aromatic monomers |
| IT1245845B (it) * | 1990-09-17 | 1994-10-25 | Montedipe Srl | Processo per la depurazione di un monomero vinilaromatico. |
| US5446220A (en) | 1994-08-24 | 1995-08-29 | Betz Laboratories, Inc. | Methods 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 |
| US6024894A (en) | 1998-03-25 | 2000-02-15 | Betzdearborn Inc. | Compositions and methods for inhibiting vinyl aromatic monomer polymerization |
| JP4248875B2 (ja) | 2000-10-16 | 2009-04-02 | ケムチュア コーポレイション | 重合抑制剤としての、キノンアルカイドとニトロキシル化合物の混合物 |
| US6685823B2 (en) * | 2000-10-16 | 2004-02-03 | Uniroyal Chemical Company, Inc. | C-nitrosoaniline compounds and their blends as polymerization inhibitors |
| EP1379584B1 (en) * | 2001-03-20 | 2005-08-24 | Ciba Specialty Chemicals Holding Inc. | Flame retardant compositions |
| 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 |
| KR20050107811A (ko) * | 2003-03-17 | 2005-11-15 | 하쿠토 가부시키가이샤 | 방향족 비닐 화합물의 중합 억제제 및 중합 억제 방법 |
-
2009
- 2009-02-05 US US12/366,154 patent/US7651635B1/en active Active
-
2010
- 2010-01-25 TW TW099101907A patent/TWI461406B/zh active
- 2010-02-03 JP JP2011549218A patent/JP5536106B2/ja active Active
- 2010-02-03 CA CA2750187A patent/CA2750187C/en active Active
- 2010-02-03 CN CN201080006847.0A patent/CN102307830B/zh active Active
- 2010-02-03 ES ES10704042T patent/ES2398053T3/es active Active
- 2010-02-03 SG SG2011056546A patent/SG173564A1/en unknown
- 2010-02-03 EP EP10704042A patent/EP2393765B1/en active Active
- 2010-02-03 KR KR1020117018201A patent/KR101613760B1/ko active Active
- 2010-02-03 WO PCT/US2010/022977 patent/WO2010091040A1/en not_active Ceased
- 2010-02-03 BR BRPI1005420-0A patent/BRPI1005420B1/pt active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| JP2012516933A (ja) | 2012-07-26 |
| BRPI1005420B1 (pt) | 2021-05-11 |
| TWI461406B (zh) | 2014-11-21 |
| KR20110122111A (ko) | 2011-11-09 |
| WO2010091040A1 (en) | 2010-08-12 |
| CA2750187C (en) | 2016-05-10 |
| BRPI1005420A2 (pt) | 2020-08-18 |
| CA2750187A1 (en) | 2010-08-12 |
| TW201035046A (en) | 2010-10-01 |
| JP5536106B2 (ja) | 2014-07-02 |
| SG173564A1 (en) | 2011-09-29 |
| EP2393765A1 (en) | 2011-12-14 |
| EP2393765B1 (en) | 2012-12-26 |
| US7651635B1 (en) | 2010-01-26 |
| CN102307830B (zh) | 2014-10-22 |
| CN102307830A (zh) | 2012-01-04 |
| KR101613760B1 (ko) | 2016-04-19 |
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