AU2013307242B2 - Composition of quinone methide derivatives and amines for control and inhibition of polymerization of monomers, and method of preparation and use thereof - Google Patents
Composition of quinone methide derivatives and amines for control and inhibition of polymerization of monomers, and method of preparation and use thereof Download PDFInfo
- Publication number
- AU2013307242B2 AU2013307242B2 AU2013307242A AU2013307242A AU2013307242B2 AU 2013307242 B2 AU2013307242 B2 AU 2013307242B2 AU 2013307242 A AU2013307242 A AU 2013307242A AU 2013307242 A AU2013307242 A AU 2013307242A AU 2013307242 B2 AU2013307242 B2 AU 2013307242B2
- Authority
- AU
- Australia
- Prior art keywords
- quinone methide
- polymerization
- composition
- ppm
- derivatives
- 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.)
- Ceased
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 145
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 title claims abstract description 132
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 106
- -1 quinone methide derivatives Chemical class 0.000 title claims abstract description 84
- 239000000178 monomer Substances 0.000 title claims abstract description 73
- 238000000034 method Methods 0.000 title claims abstract description 59
- 230000005764 inhibitory process Effects 0.000 title claims abstract description 41
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 150000001412 amines Chemical class 0.000 title claims description 49
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 174
- 239000000654 additive Substances 0.000 claims abstract description 81
- 230000000996 additive effect Effects 0.000 claims abstract description 74
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 67
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims abstract description 32
- BYACHAOCSIPLCM-UHFFFAOYSA-N 2-[2-[bis(2-hydroxyethyl)amino]ethyl-(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(CCO)CCN(CCO)CCO BYACHAOCSIPLCM-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000000101 transmission high energy electron diffraction Methods 0.000 claims abstract description 13
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 claims abstract description 9
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 claims description 41
- 229920002554 vinyl polymer Polymers 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 17
- 150000004053 quinones Chemical class 0.000 claims description 11
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 10
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 7
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 2
- CWKVFRNCODQPDB-UHFFFAOYSA-N 1-(2-aminoethylamino)propan-2-ol Chemical compound CC(O)CNCCN CWKVFRNCODQPDB-UHFFFAOYSA-N 0.000 claims 1
- 229940012017 ethylenediamine Drugs 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 abstract description 19
- 150000002148 esters Chemical class 0.000 description 12
- 239000003112 inhibitor Substances 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 230000002195 synergetic effect Effects 0.000 description 6
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229960004418 trolamine Drugs 0.000 description 3
- KKZZSTCINUMTGD-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidin-4-ol Chemical compound CC1C(O)CCN(C)C1(C)C KKZZSTCINUMTGD-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical class O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004151 quinonyl group Chemical group 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- C08F112/00—Homopolymers 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
- C08F112/02—Monomers containing only one unsaturated aliphatic radical
- C08F112/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F112/06—Hydrocarbons
- C08F112/08—Styrene
-
- 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
- C08F2/42—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation using short-stopping 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
-
- 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
-
- 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
- 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
- C09K15/16—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen
- C09K15/18—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen containing an amine or imine moiety
-
- 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
- C09K15/20—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen
- C09K15/24—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen containing a phenol or quinone moiety
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Water Supply & Treatment (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Analytical Chemistry (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN2465/MUM/2012 | 2012-08-24 | ||
| IN2465MU2012 | 2012-08-24 | ||
| PCT/IB2013/056787 WO2014030131A1 (en) | 2012-08-24 | 2013-08-21 | Composition of quinone methide derivatives and amines for control and inhibition of polymerization of monomers, and method of preparation and use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2013307242A1 AU2013307242A1 (en) | 2015-03-12 |
| AU2013307242B2 true AU2013307242B2 (en) | 2016-09-29 |
Family
ID=54187096
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2013307242A Ceased AU2013307242B2 (en) | 2012-08-24 | 2013-08-21 | Composition of quinone methide derivatives and amines for control and inhibition of polymerization of monomers, and method of preparation and use thereof |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US9234057B2 (https=) |
| EP (1) | EP2888212B1 (https=) |
| JP (1) | JP6255405B2 (https=) |
| KR (1) | KR101803750B1 (https=) |
| CN (1) | CN104718181B (https=) |
| AU (1) | AU2013307242B2 (https=) |
| BR (1) | BR112015003564B1 (https=) |
| CA (1) | CA2880244C (https=) |
| ES (1) | ES2686127T3 (https=) |
| MX (1) | MX360426B (https=) |
| MY (1) | MY182112A (https=) |
| PL (1) | PL2888212T3 (https=) |
| RU (1) | RU2632879C2 (https=) |
| SG (1) | SG11201500774WA (https=) |
| TW (1) | TWI610915B (https=) |
| WO (1) | WO2014030131A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2686127T3 (es) | 2012-08-24 | 2018-10-16 | Dorf Ketal Chemicals (India) Private Limited | Composición de derivados de métido de quinona y aminas para el control y la inhibición de la polimerización de monómeros, y procedimiento de preparación y uso de la misma |
| IN2013MU01165A (https=) * | 2013-03-26 | 2015-04-24 | Dorf Ketal Chemicals India Private Ltd | |
| PL3414217T3 (pl) * | 2016-02-13 | 2020-10-19 | Dorf Ketal Chemicals (India) Private Limited | Kompozycje do kontroli i hamowania polimeryzacji monomerów winyloaromatycznych oraz sposoby ich stosowania |
| KR102763208B1 (ko) * | 2018-07-13 | 2025-02-04 | 에코랍 유에스에이 인코퍼레이티드 | 비닐계 단량체에 대한 항파울런트로서의 산소화 아민 및 퀴논 메티드의 조성물 |
| TW202005938A (zh) | 2018-07-13 | 2020-02-01 | 美商藝康美國公司 | 具有胺穩定劑之聚合抑制劑及阻滯劑組合物 |
| 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 |
| 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 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013054353A1 (en) * | 2011-08-26 | 2013-04-18 | Dorf Ketal Chemicals (India) Private Limited | Additive composition for control and inhibition of polymerization of styrene, and method of preparation and use thereof |
| WO2013102930A1 (en) * | 2011-12-26 | 2013-07-11 | Dorf Ketal Chemicals (India) Private Limited | Improved amine based additive composition for control and inhibition of polymerization of aromatic vinyl monomers, and method of use thereof |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2039757C1 (ru) * | 1992-05-15 | 1995-07-20 | Нижнекамское производственное объединение "Нижнекамскнефтехим" | Способ ингибирования полимеризации винилароматических мономеров |
| 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 |
| KR100812038B1 (ko) * | 2000-10-16 | 2008-03-10 | 유니로얄 캐미칼 캄파니, 인크. | 중합 억제제로서 퀴논 알키드와 니트록실 화합물의 블렌드물 |
| US20040034247A1 (en) * | 2002-08-16 | 2004-02-19 | Sherif Eldin | Compositions and methods for inhibiting vinyl aromatic monomer polymerization |
| CN101102984A (zh) * | 2004-12-03 | 2008-01-09 | 科聚亚公司 | 作为聚合抑制剂的与含氮氧自由基的化合物或c-亚硝基苯胺结合的芳族磺酸、胺和硝基酚 |
| US7651635B1 (en) * | 2009-02-05 | 2010-01-26 | Nalco Company | Polymer inhibition of vinyl aromatic monomers using a quinone methide/alkyl hydroxylamine combination |
| US8298440B2 (en) | 2010-06-03 | 2012-10-30 | General Electric Company | Methods and compositions for inhibiting vinyl aromatic monomer polymerization |
| ES2686127T3 (es) * | 2012-08-24 | 2018-10-16 | Dorf Ketal Chemicals (India) Private Limited | Composición de derivados de métido de quinona y aminas para el control y la inhibición de la polimerización de monómeros, y procedimiento de preparación y uso de la misma |
-
2013
- 2013-08-21 ES ES13765802.7T patent/ES2686127T3/es active Active
- 2013-08-21 PL PL13765802T patent/PL2888212T3/pl unknown
- 2013-08-21 US US14/423,218 patent/US9234057B2/en active Active
- 2013-08-21 AU AU2013307242A patent/AU2013307242B2/en not_active Ceased
- 2013-08-21 CA CA2880244A patent/CA2880244C/en active Active
- 2013-08-21 JP JP2015527997A patent/JP6255405B2/ja active Active
- 2013-08-21 KR KR1020157007306A patent/KR101803750B1/ko active Active
- 2013-08-21 SG SG11201500774WA patent/SG11201500774WA/en unknown
- 2013-08-21 EP EP13765802.7A patent/EP2888212B1/en active Active
- 2013-08-21 BR BR112015003564-7A patent/BR112015003564B1/pt active IP Right Grant
- 2013-08-21 RU RU2015109877A patent/RU2632879C2/ru active
- 2013-08-21 MY MYPI2015700524A patent/MY182112A/en unknown
- 2013-08-21 CN CN201380044001.XA patent/CN104718181B/zh active Active
- 2013-08-21 MX MX2015002382A patent/MX360426B/es active IP Right Grant
- 2013-08-21 WO PCT/IB2013/056787 patent/WO2014030131A1/en not_active Ceased
- 2013-08-23 TW TW102130325A patent/TWI610915B/zh active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013054353A1 (en) * | 2011-08-26 | 2013-04-18 | Dorf Ketal Chemicals (India) Private Limited | Additive composition for control and inhibition of polymerization of styrene, and method of preparation and use thereof |
| WO2013102930A1 (en) * | 2011-12-26 | 2013-07-11 | Dorf Ketal Chemicals (India) Private Limited | Improved amine based additive composition for control and inhibition of polymerization of aromatic vinyl monomers, and method of use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| PL2888212T3 (pl) | 2018-11-30 |
| KR20150048797A (ko) | 2015-05-07 |
| MX360426B (es) | 2018-11-01 |
| BR112015003564A2 (pt) | 2017-08-22 |
| TW201412706A (zh) | 2014-04-01 |
| MX2015002382A (es) | 2015-06-03 |
| CA2880244C (en) | 2017-05-16 |
| SG11201500774WA (en) | 2015-02-27 |
| JP6255405B2 (ja) | 2017-12-27 |
| EP2888212A1 (en) | 2015-07-01 |
| MY182112A (en) | 2021-01-18 |
| ES2686127T3 (es) | 2018-10-16 |
| WO2014030131A1 (en) | 2014-02-27 |
| US20150225495A1 (en) | 2015-08-13 |
| RU2015109877A (ru) | 2016-10-20 |
| BR112015003564B1 (pt) | 2021-01-05 |
| JP2015526562A (ja) | 2015-09-10 |
| CA2880244A1 (en) | 2014-02-27 |
| CN104718181A (zh) | 2015-06-17 |
| AU2013307242A1 (en) | 2015-03-12 |
| KR101803750B1 (ko) | 2017-12-01 |
| RU2632879C2 (ru) | 2017-10-11 |
| US9234057B2 (en) | 2016-01-12 |
| TWI610915B (zh) | 2018-01-11 |
| CN104718181B (zh) | 2018-01-30 |
| EP2888212B1 (en) | 2018-06-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |