CA2750187C - Polymer inhibition of vinyl aromatic monomers using a quinone methide/alkyl hydroxomine combination - Google Patents
Polymer inhibition of vinyl aromatic monomers using a quinone methide/alkyl hydroxomine combination Download PDFInfo
- Publication number
- CA2750187C CA2750187C CA2750187A CA2750187A CA2750187C CA 2750187 C CA2750187 C CA 2750187C CA 2750187 A CA2750187 A CA 2750187A CA 2750187 A CA2750187 A CA 2750187A CA 2750187 C CA2750187 C CA 2750187C
- Authority
- CA
- Canada
- Prior art keywords
- inhibitor
- retarder
- monomers
- combination
- quinone methide
- 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
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 239000000178 monomer Substances 0.000 title claims description 37
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 title claims description 34
- 229920002554 vinyl polymer Polymers 0.000 title claims description 7
- 229920000642 polymer Polymers 0.000 title description 14
- 230000005764 inhibitory process Effects 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 title 1
- 239000003112 inhibitor Substances 0.000 claims abstract description 54
- 238000000034 method Methods 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 15
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 14
- 230000002028 premature Effects 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- SZMBYKBVFJKLQB-UHFFFAOYSA-N 3-(hydroxyamino)propan-1-ol Chemical compound OCCCNO SZMBYKBVFJKLQB-UHFFFAOYSA-N 0.000 claims description 3
- 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 2
- 239000004793 Polystyrene Substances 0.000 claims 1
- 229920002223 polystyrene Polymers 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 5
- 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
- -1 nitroxides Chemical class 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
- 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
- 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
- 150000004053 quinones Chemical class 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
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical class C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 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 |
|---|---|---|---|
| US12/366,154 | 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 (2)
| Publication Number | Publication Date |
|---|---|
| CA2750187A1 CA2750187A1 (en) | 2010-08-12 |
| CA2750187C true CA2750187C (en) | 2016-05-10 |
Family
ID=41559765
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2750187A Active CA2750187C (en) | 2009-02-05 | 2010-02-03 | Polymer inhibition of vinyl aromatic monomers using a quinone methide/alkyl hydroxomine combination |
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 |
| MX2014002218A (es) | 2011-08-26 | 2014-05-28 | Dorf Ketal Chemicals India Private Ltd | Composicion aditiva para el control y la inhibicion de la polimerizacion del estireno y metodo de preparacion y uso de la misma. |
| KR102033096B1 (ko) * | 2011-12-09 | 2019-10-16 | 도르프 케탈 케미칼즈 (인디아) 프라이비트 리미티드 | 방향족 비닐 단량체의 중합화의 제어 및 억제를 위한 개선된 첨가제 조성물, 및 그의 사용 방법 |
| 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 |
| WO2014030131A1 (en) * | 2012-08-24 | 2014-02-27 | Dorf Ketal Chemicals (India) Private Limited | 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 |
| BR112018016444B1 (pt) * | 2016-02-13 | 2022-08-16 | Dorf Ketal Chemicals (India) Private Limited | Composição de aditivo à base de amina aprimorada, seu método de uso e método para controle e inibição de monômeros de vinila aromáticos |
| KR102763208B1 (ko) * | 2018-07-13 | 2025-02-04 | 에코랍 유에스에이 인코퍼레이티드 | 비닐계 단량체에 대한 항파울런트로서의 산소화 아민 및 퀴논 메티드의 조성물 |
| WO2020014596A1 (en) | 2018-07-13 | 2020-01-16 | Ecolab Usa Inc. | Composition for inhibiting monomer polymerization comprising a nitroxide inhibitor, a quinone methide retarder and an amine stabilizer |
| 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 |
| WO2025217595A1 (en) * | 2024-04-12 | 2025-10-16 | Bl Technologies, Inc. | Boosted styrene polymerization retarder and method of use |
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 |
| 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 |
| ES2247332T3 (es) * | 2001-03-20 | 2006-03-01 | Ciba Specialty Chemicals Holding Inc. | Composiciones ignifugantes. |
| 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 |
| 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 |
-
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 SG SG2011056546A patent/SG173564A1/en unknown
- 2010-02-03 CN CN201080006847.0A patent/CN102307830B/zh active Active
- 2010-02-03 JP JP2011549218A patent/JP5536106B2/ja active Active
- 2010-02-03 BR BRPI1005420-0A patent/BRPI1005420B1/pt active IP Right Grant
- 2010-02-03 EP EP10704042A patent/EP2393765B1/en active Active
- 2010-02-03 KR KR1020117018201A patent/KR101613760B1/ko active Active
- 2010-02-03 CA CA2750187A patent/CA2750187C/en active Active
- 2010-02-03 ES ES10704042T patent/ES2398053T3/es active Active
- 2010-02-03 WO PCT/US2010/022977 patent/WO2010091040A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| SG173564A1 (en) | 2011-09-29 |
| JP2012516933A (ja) | 2012-07-26 |
| KR101613760B1 (ko) | 2016-04-19 |
| KR20110122111A (ko) | 2011-11-09 |
| JP5536106B2 (ja) | 2014-07-02 |
| US7651635B1 (en) | 2010-01-26 |
| ES2398053T3 (es) | 2013-03-13 |
| CN102307830A (zh) | 2012-01-04 |
| BRPI1005420A2 (pt) | 2020-08-18 |
| CA2750187A1 (en) | 2010-08-12 |
| TW201035046A (en) | 2010-10-01 |
| CN102307830B (zh) | 2014-10-22 |
| BRPI1005420B1 (pt) | 2021-05-11 |
| EP2393765B1 (en) | 2012-12-26 |
| WO2010091040A1 (en) | 2010-08-12 |
| TWI461406B (zh) | 2014-11-21 |
| EP2393765A1 (en) | 2011-12-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2750187C (en) | Polymer inhibition of vinyl aromatic monomers using a quinone methide/alkyl hydroxomine combination | |
| JP4790414B2 (ja) | 芳香族ビニル化合物の重合抑制剤および重合抑制方法 | |
| JP5956568B2 (ja) | ビニルモノマーの重合を阻害するための相乗的組合せ | |
| US9884795B2 (en) | Quinone compounds for inhibiting monomer polymerization | |
| US6960279B2 (en) | Method for stabilizing vinyl aromatic monomers using selected polymerization inhibitors and polymers prepared therewith | |
| CN108164385B (zh) | 在苯乙烯制造期间抑制聚苯乙烯形成的方法和组合物 | |
| KR20210107641A (ko) | 하이드록실화 퀴논 중합방지제 및 이의 사용 방법 | |
| KR101660610B1 (ko) | 퀴논 메타이드의 인-시튜 생성을 통한 스티렌 억제 방법 및 조성물 | |
| EP2000451B1 (en) | Method of inhibiting polymerization of aromatic vinyl compound | |
| JP4871616B2 (ja) | 芳香族ビニル化合物の重合抑制方法 | |
| WO2001023499A1 (en) | Methods and compositions for inhibiting vinyl aromatic monomer polymerization |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20150120 |