TWI461406B - 使用亞甲基醌／烷基羥胺組合之乙烯基芳族單體的聚合物抑制 - Google Patents
使用亞甲基醌／烷基羥胺組合之乙烯基芳族單體的聚合物抑制 Download PDFInfo
- Publication number
- TWI461406B TWI461406B TW099101907A TW99101907A TWI461406B TW I461406 B TWI461406 B TW I461406B TW 099101907 A TW099101907 A TW 099101907A TW 99101907 A TW99101907 A TW 99101907A TW I461406 B TWI461406 B TW I461406B
- Authority
- TW
- Taiwan
- Prior art keywords
- inhibitor
- monomer
- retarder
- combination
- butyl
- Prior art date
Links
- 239000000178 monomer Substances 0.000 title claims description 29
- 229920002554 vinyl polymer Polymers 0.000 title claims description 7
- 229920000642 polymer Polymers 0.000 title description 16
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 title 2
- 125000000217 alkyl group Chemical group 0.000 title 1
- 230000005764 inhibitory process Effects 0.000 title 1
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 title 1
- 239000003112 inhibitor Substances 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 13
- 238000006116 polymerization reaction Methods 0.000 claims description 13
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- -1 7-substituted-methylene fluorenes Chemical class 0.000 claims description 7
- BJEMXPVDXFSROA-UHFFFAOYSA-N 3-butylbenzene-1,2-diol Chemical compound CCCCC1=CC=CC(O)=C1O BJEMXPVDXFSROA-UHFFFAOYSA-N 0.000 claims description 5
- 230000002028 premature Effects 0.000 claims description 5
- SZMBYKBVFJKLQB-UHFFFAOYSA-N 3-(hydroxyamino)propan-1-ol Chemical compound OCCCNO SZMBYKBVFJKLQB-UHFFFAOYSA-N 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- IRXXTOXNJURUHK-UHFFFAOYSA-N C(C)(C)(C)C1=CC2=CC3=CC(C(=CC3=C2C=C1)C(C)(C)C)=CC(=O)O Chemical compound C(C)(C)(C)C1=CC2=CC3=CC(C(=CC3=C2C=C1)C(C)(C)C)=CC(=O)O IRXXTOXNJURUHK-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
- 239000004793 Polystyrene Substances 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 238000012545 processing Methods 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 description 8
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 6
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 5
- 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
- 150000002923 oximes Chemical class 0.000 description 4
- 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 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- IDBOAVAEGRJRIZ-UHFFFAOYSA-N methylidenehydrazine Chemical compound NN=C IDBOAVAEGRJRIZ-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-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
- 238000011161 development Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 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
- 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/366,154 US7651635B1 (en) | 2009-02-05 | 2009-02-05 | Polymer inhibition of vinyl aromatic monomers using a quinone methide/alkyl hydroxylamine combination |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201035046A TW201035046A (en) | 2010-10-01 |
| TWI461406B true TWI461406B (zh) | 2014-11-21 |
Family
ID=41559765
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW099101907A TWI461406B (zh) | 2009-02-05 | 2010-01-25 | 使用亞甲基醌／烷基羥胺組合之乙烯基芳族單體的聚合物抑制 |
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 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09176215A (ja) * | 1995-04-14 | 1997-07-08 | Ciba Geigy Ag | 不飽和モノマーのための阻害剤としての７−置換キノンメチド |
| US20040097619A1 (en) * | 2001-03-20 | 2004-05-20 | Troutman Malisa V. | Flame retardant compositions |
| CN1761638A (zh) * | 2003-03-17 | 2006-04-19 | 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 |
| US20060155140A1 (en) * | 2000-10-16 | 2006-07-13 | Uniroyal Chemical Company, Inc A Corporation Of The State Of Delaware | Blends of quinone alkide and nitroxyl compounds as polymerization inhibitors |
Family Cites Families (8)
| 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 |
| US6024894A (en) * | 1998-03-25 | 2000-02-15 | Betzdearborn Inc. | Compositions and methods for inhibiting vinyl aromatic monomer polymerization |
| 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 |
-
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
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09176215A (ja) * | 1995-04-14 | 1997-07-08 | Ciba Geigy Ag | 不飽和モノマーのための阻害剤としての７−置換キノンメチド |
| US20060155140A1 (en) * | 2000-10-16 | 2006-07-13 | Uniroyal Chemical Company, Inc A Corporation Of The State Of Delaware | Blends of quinone alkide and nitroxyl compounds as polymerization inhibitors |
| US20040097619A1 (en) * | 2001-03-20 | 2004-05-20 | Troutman Malisa V. | Flame retardant compositions |
| CN1761638A (zh) * | 2003-03-17 | 2006-04-19 | 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 |
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 |
| CA2750187C (en) | 2016-05-10 |
| EP2393765A1 (en) | 2011-12-14 |
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