JP5536106B2 - キノンメチド/アルキルヒドロキシルアミンの組み合わせを用いる、ビニル芳香族モノマーの重合阻害法 - Google Patents
キノンメチド/アルキルヒドロキシルアミンの組み合わせを用いる、ビニル芳香族モノマーの重合阻害法 Download PDFInfo
- Publication number
- JP5536106B2 JP5536106B2 JP2011549218A JP2011549218A JP5536106B2 JP 5536106 B2 JP5536106 B2 JP 5536106B2 JP 2011549218 A JP2011549218 A JP 2011549218A JP 2011549218 A JP2011549218 A JP 2011549218A JP 5536106 B2 JP5536106 B2 JP 5536106B2
- Authority
- JP
- Japan
- Prior art keywords
- inhibitor
- retarder
- combination
- vinyl aromatic
- alkylhydroxylamine
- 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 description 24
- 238000006116 polymerization reaction Methods 0.000 title claims description 15
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 title claims description 14
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 7
- 229920002554 vinyl polymer Polymers 0.000 title claims description 7
- 230000002401 inhibitory effect Effects 0.000 title claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 16
- 150000004053 quinones Chemical class 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000006243 chemical reaction Methods 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
- 230000006698 induction Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- SZMBYKBVFJKLQB-UHFFFAOYSA-N 3-(hydroxyamino)propan-1-ol Chemical compound OCCCNO SZMBYKBVFJKLQB-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229920001174 Diethylhydroxylamine Polymers 0.000 description 2
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000005525 methide group Chemical group 0.000 description 2
- -1 nitroxides Chemical class 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 230000002028 premature Effects 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
- 238000011161 development Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003860 storage Methods 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)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Analytical Chemistry (AREA)
- Materials Engineering (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
第一の実施例では、従来技術の遅延剤−阻害剤の組み合わせであるHPHA阻害剤及びDNBP遅延剤のサンプルと、7−置換−キノンメチド遅延剤及びHPHA阻害剤を含む、本発明の遅延剤−阻害剤の組み合わせとの比較を行った。前記遅延剤は、各サンプルに対して、モノマー重量に比較して、350ppmの用量で加え、及び前記阻害剤は、連続的に撹拌されたタンク反応器に、モノマー重量に比較して、150ppmの用量で加えた。2つのサンプルは120℃まで加熱され、及び1時間その温度に保たれた。従来技術のサンプルは、539ppmの望まれないポリマーをもたらした一方、本発明の遅延剤−阻害剤の組み合わせは、単に38.5ppmの望まれないポリマーをもたらしただけであった。このことは、本発明の遅延剤−阻害剤の組み合わせが、単に従来技術の組み合わせによる結果を毒性なしで実現するのみでなく、実際に予期しないほどの、非常に優れた成績をもたらすことを実証した。
第二の実施例では、従来技術の遅延剤−阻害剤の組み合わせである、HPHA阻害剤及びDNBP遅延剤を含むサンプルと、本発明の遅延剤−阻害剤の組み合わせである、7−置換−キノンメチド遅延剤及びHPHA阻害剤を含むサンプルの比較が行われた。前記遅延剤は、各サンプルに対して、モノマー重量に比較して、350ppmの用量で加え、及び前記阻害剤は、連続的に撹拌されたタンク反応器に、モノマー重量に比較して、22.5ppmの用量で加えた。2つのサンプルは120℃まで加熱され、及び1時間その温度に保たれた。従来技術のサンプルは、573ppmの望まれないポリマーをもたらした一方、本発明の遅延剤−阻害剤の組み合わせは、単に62ppmの望まれないポリマーをもたらしただけであった。このことは、本発明の遅延剤−阻害剤の組み合わせが、追加の阻害剤を加えることのできない、緊急的な状況において、更に望まれないポリマーの生成を徹底的に防止する能力があることを実証した。
Claims (1)
- ビニル芳香族モノマーに、少なくとも1つの阻害剤、及び少なくとも1つの遅延剤組成物を含む組成物の有効量を加えることによる、前記モノマーの未成熟重合を阻害する方法であって、前記阻害剤がアルキルヒドロキシルアミンであり、並びに前記遅延剤が、2,6−ジ−t−ブチル−7−シアノキノンメチドを含む7−置換−キノンメチドである方法。
Applications Claiming Priority (3)
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 |
US12/366,154 | 2009-02-05 | ||
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 (3)
Publication Number | Publication Date |
---|---|
JP2012516933A JP2012516933A (ja) | 2012-07-26 |
JP2012516933A5 JP2012516933A5 (ja) | 2013-03-21 |
JP5536106B2 true JP5536106B2 (ja) | 2014-07-02 |
Family
ID=41559765
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011549218A Active JP5536106B2 (ja) | 2009-02-05 | 2010-02-03 | キノンメチド/アルキルヒドロキシルアミンの組み合わせを用いる、ビニル芳香族モノマーの重合阻害法 |
Country Status (11)
Country | Link |
---|---|
US (1) | US7651635B1 (ja) |
EP (1) | EP2393765B1 (ja) |
JP (1) | JP5536106B2 (ja) |
KR (1) | KR101613760B1 (ja) |
CN (1) | CN102307830B (ja) |
BR (1) | BRPI1005420B1 (ja) |
CA (1) | CA2750187C (ja) |
ES (1) | ES2398053T3 (ja) |
SG (1) | SG173564A1 (ja) |
TW (1) | TWI461406B (ja) |
WO (1) | WO2010091040A1 (ja) |
Families Citing this family (15)
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 |
US8884038B2 (en) * | 2011-06-13 | 2014-11-11 | Nalco Company | Synthesis of 7-acetyleno quinone methide derivatives and their application as vinylic polymerization retarders |
US9090526B2 (en) | 2011-06-13 | 2015-07-28 | Nalco Company | Synergistic combination for inhibiting polymerization of vinyl monomers |
MY167399A (en) | 2011-08-26 | 2018-08-16 | Dorf Ketal Chemicals India Private Ltd | Additive composition for control and inhibition of polymerization of styrene, and method of preparation and use thereof |
PL2788303T3 (pl) * | 2011-12-09 | 2015-12-31 | Dorf Ketal Chemicals India Private Ltd | Ulepszona kompozycja dodatków do kontroli i hamowania polimeryzacji aromatycznych monomerów winylowych oraz sposób jej stosowania |
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 |
AU2013307242B2 (en) * | 2012-08-24 | 2016-09-29 | 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 (ja) * | 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 |
JP6530868B2 (ja) * | 2016-02-13 | 2019-06-12 | ドルフ ケタール ケミカルズ (インディア)プライヴェート リミテッド | ビニル芳香族モノマーの重合を制御及び阻害するための組成物及びその使用方法 |
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 |
TWI826485B (zh) | 2018-07-13 | 2023-12-21 | 美商藝康美國公司 | 作為乙烯系單體之防垢劑之含氧胺及醌甲基化物之組合物 |
TW202114976A (zh) * | 2019-10-11 | 2021-04-16 | 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 |
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 |
KR100812038B1 (ko) | 2000-10-16 | 2008-03-10 | 유니로얄 캐미칼 캄파니, 인크. | 중합 억제제로서 퀴논 알키드와 니트록실 화합물의 블렌드물 |
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 |
WO2004083156A1 (ja) * | 2003-03-17 | 2004-09-30 | Hakuto Co., Ltd. | 芳香族ビニル化合物の重合抑制剤および重合抑制方法 |
-
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 WO PCT/US2010/022977 patent/WO2010091040A1/en active Application Filing
- 2010-02-03 JP JP2011549218A patent/JP5536106B2/ja active Active
- 2010-02-03 EP EP10704042A patent/EP2393765B1/en active Active
- 2010-02-03 ES ES10704042T patent/ES2398053T3/es active Active
- 2010-02-03 SG SG2011056546A patent/SG173564A1/en unknown
- 2010-02-03 CN CN201080006847.0A patent/CN102307830B/zh active Active
- 2010-02-03 BR BRPI1005420-0A patent/BRPI1005420B1/pt active IP Right Grant
- 2010-02-03 KR KR1020117018201A patent/KR101613760B1/ko active IP Right Grant
- 2010-02-03 CA CA2750187A patent/CA2750187C/en active Active
Also Published As
Publication number | Publication date |
---|---|
EP2393765A1 (en) | 2011-12-14 |
TW201035046A (en) | 2010-10-01 |
CN102307830A (zh) | 2012-01-04 |
KR101613760B1 (ko) | 2016-04-19 |
WO2010091040A1 (en) | 2010-08-12 |
US7651635B1 (en) | 2010-01-26 |
JP2012516933A (ja) | 2012-07-26 |
CN102307830B (zh) | 2014-10-22 |
ES2398053T3 (es) | 2013-03-13 |
BRPI1005420B1 (pt) | 2021-05-11 |
BRPI1005420A2 (pt) | 2020-08-18 |
CA2750187A1 (en) | 2010-08-12 |
KR20110122111A (ko) | 2011-11-09 |
SG173564A1 (en) | 2011-09-29 |
EP2393765B1 (en) | 2012-12-26 |
TWI461406B (zh) | 2014-11-21 |
CA2750187C (en) | 2016-05-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5536106B2 (ja) | キノンメチド/アルキルヒドロキシルアミンの組み合わせを用いる、ビニル芳香族モノマーの重合阻害法 | |
RU2600169C2 (ru) | Композиция присадки для контроля и ингибирования полимеризации стирола и способ ее получения и использования | |
JP5336844B2 (ja) | 重合阻害剤としてのオルト−ニトロソフェノール | |
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 | |
US20060020089A1 (en) | Method for stabilizing vinyl aromatic monomers using selected polymerization inhibitors and polymers prepared | |
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 | |
TW201307277A (zh) | 合成7-乙炔基亞甲基醌之衍生物及其作為乙烯聚合阻滯劑之應用 | |
JP2016520674A (ja) | 脂肪族モノマーの重合の制御及び禁止のための添加剤組成物、並びにその製造方法及び使用方法 | |
EP2912109B1 (en) | Quinone compounds for inhibiting monomer polymerization | |
TWI255292B (en) | Methods and compositions for inhibiting vinyl aromatic monomer polymerization | |
EP0553210A1 (en) | BENZOQUINONEIMINES USED AS POLYMERIZATION INHIBITORS FOR AN AROMATIC VINYL SERIES. | |
JP2005281218A (ja) | 芳香族ビニル化合物の重合抑制方法 | |
JP2006176417A (ja) | 芳香族ビニル化合物の重合抑制方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130131 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20130131 |
|
RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20130207 |
|
RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20130515 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20131216 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140107 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140324 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20140415 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20140423 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5536106 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |