CA2979828C - The use of stable lipophilic hydroxylamine compounds for inhibiting polymerization of vinyl monomers - Google Patents

The use of stable lipophilic hydroxylamine compounds for inhibiting polymerization of vinyl monomers Download PDF

Info

Publication number
CA2979828C
CA2979828C CA2979828A CA2979828A CA2979828C CA 2979828 C CA2979828 C CA 2979828C CA 2979828 A CA2979828 A CA 2979828A CA 2979828 A CA2979828 A CA 2979828A CA 2979828 C CA2979828 C CA 2979828C
Authority
CA
Canada
Prior art keywords
polymerization
butyl
unsaturated compound
vinyl
styrene
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
Application number
CA2979828A
Other languages
English (en)
French (fr)
Other versions
CA2979828A1 (en
Inventor
Jonathan MASERE
Andrew Neilson
Russell Watson
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ecolab USA Inc
Original Assignee
Ecolab USA Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Ecolab USA Inc filed Critical Ecolab USA Inc
Publication of CA2979828A1 publication Critical patent/CA2979828A1/en
Application granted granted Critical
Publication of CA2979828C publication Critical patent/CA2979828C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
    • C07D211/94—Oxygen atom, e.g. piperidine N-oxide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/62—Use of additives, e.g. for stabilisation
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Water Supply & Treatment (AREA)
  • Engineering & Computer Science (AREA)
  • Analytical Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Hydrogenated Pyridines (AREA)
  • Polymerisation Methods In General (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
CA2979828A 2015-03-18 2016-03-17 The use of stable lipophilic hydroxylamine compounds for inhibiting polymerization of vinyl monomers Active CA2979828C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201562134811P 2015-03-18 2015-03-18
US62/134,811 2015-03-18
PCT/US2016/022731 WO2016149433A1 (en) 2015-03-18 2016-03-17 The use of stable lipophilic hydroxylamine compounds for inhibiting polymerization of vinyl monomers

Publications (2)

Publication Number Publication Date
CA2979828A1 CA2979828A1 (en) 2016-09-22
CA2979828C true CA2979828C (en) 2023-08-29

Family

ID=56919278

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2979828A Active CA2979828C (en) 2015-03-18 2016-03-17 The use of stable lipophilic hydroxylamine compounds for inhibiting polymerization of vinyl monomers

Country Status (12)

Country Link
US (1) US9914701B2 (https=)
EP (1) EP3271331B1 (https=)
JP (1) JP6730303B2 (https=)
KR (1) KR102583199B1 (https=)
CN (1) CN107406388B (https=)
AR (1) AR103961A1 (https=)
BR (1) BR112017018283B1 (https=)
CA (1) CA2979828C (https=)
ES (1) ES2912329T3 (https=)
RU (1) RU2715559C2 (https=)
TW (1) TWI680964B (https=)
WO (1) WO2016149433A1 (https=)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2870125T3 (es) * 2017-03-09 2021-10-26 Ecolab Usa Inc Composiciones de inhibidores de polimerización
EP3947271A1 (en) 2019-04-02 2022-02-09 Ecolab Usa Inc. Pure chlorine dioxide generation system with reduced acid usage
TW202348787A (zh) 2022-04-01 2023-12-16 美商藝康美國公司 用於乙烯系單體流之高苛刻度加工的防汙劑組成物
TW202404930A (zh) 2022-04-01 2024-02-01 美商藝康美國公司 在共軛二烯單體之萃取蒸餾期間減少非所要之乳化聚合
TW202348786A (zh) 2022-04-01 2023-12-16 美商藝康美國公司 用於蒸氣空間應用之防汙劑組成物

Family Cites Families (62)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2455745A (en) 1943-11-19 1948-12-07 Olin Mathieson Stabilization of styrene and polymerizable ring chlorinated styrenes
US2783271A (en) 1954-06-29 1957-02-26 Allied Chem & Dye Corp Continuous production of methacrylic acid esters
US2810651A (en) 1954-12-28 1957-10-22 Universal Oil Prod Co Stabilization of organic compounds
US2965685A (en) 1958-06-24 1960-12-20 Monsanto Chemicals Polymerization inhibitor
NL131752C (https=) 1960-09-08
US3320305A (en) 1964-01-28 1967-05-16 Exxon Research Engineering Co Process for converting nitriles
US3696050A (en) 1970-08-03 1972-10-03 Eastman Kodak Co Polymerization inhibitors for vinyl monomers and unsaturated polyesters
US3704235A (en) 1971-01-11 1972-11-28 Commissariat Energie Atomique Stable free radicals of the nitroxide type derived from tropane ring compounds
US4202742A (en) 1979-04-30 1980-05-13 Westinghouse Electric Corp. Photopolymerization of ethylenically unsaturated monomers
US4293347A (en) 1980-01-21 1981-10-06 The Dow Chemical Company Process for depolymerization of acrylic acid polymers
US4487981A (en) 1983-09-08 1984-12-11 Atlantic Richfield Company Inhibiting polymerization of vinyl aromatic monomers
US4590231A (en) * 1983-10-11 1986-05-20 Ciba-Geigy Corporation Polyolefin compositions stabilized against degradation using hydroxylamine derivatives
JPH0689061B2 (ja) 1988-12-16 1994-11-09 日本石油株式会社 ブタジエン低重合体付加物の製造方法
US5290888A (en) * 1990-07-20 1994-03-01 Ciba-Geigy Corporation Process for stabilizing ethylenically unsaturated compounds and stabilized monomer compositions
KR100193146B1 (ko) * 1990-07-20 1999-06-15 월터 클리웨인, 한스-피터 위트린 안정화된 단량체 조성물
US5221498A (en) 1991-07-22 1993-06-22 Betz Laboratories, Inc. Methods and compositions for inhibitoring polymerization of vinyl monomers
US5235056A (en) 1992-04-22 1993-08-10 Ciba-Geigy Corporation Substituted 1-hydroxy-2,6-diaryl-4-piperidone ketals and polymer compositions stabilized therewith
RU2039757C1 (ru) * 1992-05-15 1995-07-20 Нижнекамское производственное объединение "Нижнекамскнефтехим" Способ ингибирования полимеризации винилароматических мономеров
US5648574A (en) 1992-10-21 1997-07-15 Betzdearborn Inc. Compositions and methods for inhibiting vinyl aromatic monomer polymerization
US5728872A (en) 1994-06-27 1998-03-17 Lutz Riemenschneider Stabilized acrylic acid compositions
US5489720A (en) 1994-06-30 1996-02-06 Betz Laboratories, Inc. Methods for inhibiting vinyl aromatic monomer polymerization
US5426257A (en) 1994-06-30 1995-06-20 Betz Laboratories, Inc. Compositions and methods for inhibiting vinyl aromatic monomer polymerization
US5626745A (en) 1994-10-27 1997-05-06 Water Recycling Systems, Inc. Waste water purification system
US5583247A (en) 1995-04-14 1996-12-10 Ciba-Geigy Corporation 7-substituted quinone methides as inhibitors for unsaturated monomers
US5648573A (en) 1995-06-12 1997-07-15 Betzdearborn Inc. Compositions and methods for inhibiting vinyl aromatic monomer polymerization
CN1194256A (zh) * 1997-03-20 1998-09-30 希巴特殊化学控股公司 聚合抑制方法
DE19811602A1 (de) * 1997-03-20 1998-11-12 Ciba Geigy Ag Polymerisationsinhibitor-Verfahren
US5932735A (en) 1997-06-13 1999-08-03 Ciba Specialty Chemicals Corporation Derivatives of 1-oxyl-4-hydroxy-2,2,6,6-tetramethylpiperidine as polymerization inhibitors for (meth)acrylate monomers
RU2223985C2 (ru) * 1997-07-23 2004-02-20 Циба Спешиалти Кемикалз Холдинг Инк. Ингибирование пожелтения целлюлозы и бумаги с использованием нитроксидов и других совместно вводимых добавок
US6020435A (en) 1997-11-05 2000-02-01 Rohm And Haas Company Process for preparing polymer core shell type emulsions and polymers formed therefrom
ID26028A (id) 1998-03-03 2000-11-16 Nippon Zeon Co Komposisi penghambat polimerisasi, penghambat polimerisasi dan metode penghambatan polimerisasi
TWI224995B (en) * 1998-03-19 2004-12-11 Ciba Sc Holding Ag Stabilization of wood substrates
JP2002524471A (ja) 1998-09-09 2002-08-06 ベイカー ヒューズ インコーポレイテッド ヒンダードヒドロキシルアミンを使用したビニルモノマーの重合禁止剤
DE69904848T2 (de) 1998-09-09 2003-11-06 Baker-Hughes Inc., Houston Inhibierung der polymerisation von styrolmonomeren mit substituierten dihydroxyarenen und stickoxiden
US6599326B1 (en) 1999-01-20 2003-07-29 Ciba Specialty Chemicals Corporation Inhibition of pulp and paper yellowing using hydroxylamines and other coadditives
CA2260310A1 (en) 1999-01-25 2000-07-25 Rene Dijkstra Sulfuric acid recovery process and apparatus
US6180231B1 (en) 1999-03-31 2001-01-30 Union Carbide Chemicals & Plastics Technology Corporation Crosslinkable polyethylene composition
DE60000708T2 (de) 1999-06-28 2003-07-24 Rohm And Haas Co., Philadelphia Verfahren zur Herstellung von (Meth)acrylsäure
BR0013364A (pt) 1999-08-18 2002-10-29 Nalco Exxon Energy Chem Lp Métodos para inibir a polimerização e conseq ente incrustação da fase vapor de um sistema monomérico, e para inibir incrustação de polimerização em um sistema monomérico, e, composição antipolimerizante
MXPA02001952A (es) * 1999-09-15 2002-08-20 Ciba Sc Holding Ag Compuestos de clorhidirna y cationicos que tienen un alta afinidad hacia la pulpa o papel.
ES2292487T3 (es) 1999-12-03 2008-03-16 Chemtura Corporation Composicion y metodo para inhibir la polimerizacion y el crecimiento polimerico.
US6525146B1 (en) 2000-04-03 2003-02-25 Baker Hughes Incorporated Inhibition of popcorn polymer growth
US6340729B1 (en) * 2000-07-26 2002-01-22 Atofina Chemicals, Inc. Process of polymerizing vinyl chloride with hydroxylamines
US20030009031A1 (en) * 2001-04-30 2003-01-09 Mikolaj Jawosiuk Novel hindered spiro-ketal nitroxides
JP4563820B2 (ja) 2003-01-29 2010-10-13 チバ ホールディング インコーポレーテッド インクジェットインクおよび記録材料
WO2005041905A2 (en) 2003-10-30 2005-05-12 Ciba Specialty Chemicals Holding Inc. Stabilized body care products, household products, textiles and fabrics
US7282136B2 (en) 2004-05-26 2007-10-16 Nalco Company Method of dispersing hydrocarbon foulants in hydrocarbon processing fluids
KR100676996B1 (ko) 2005-01-18 2007-02-01 여천엔씨씨 주식회사 1,3-부타디엔의 중합방지제 및 이것을 투입하는1,3-부타디엔의 중합방지방법
WO2007003508A1 (en) 2005-06-30 2007-01-11 Ciba Specialty Chemicals Holding Inc. Stabilized electrochromic media
CA2624900A1 (en) 2005-10-04 2007-04-19 The Research Foundation Of State University Of New York Fibronectin polypeptides and methods of use
GB0521319D0 (en) 2005-10-20 2005-11-30 A H Marks And Company Ltd Method
US7985826B2 (en) 2006-12-22 2011-07-26 Reichhold, Inc. Molding resins using renewable resource component
CA2678363A1 (en) * 2007-02-16 2008-08-21 Othera Holding, Inc. Drug resistance reversal in neoplastic disease
BRPI0807571A2 (pt) 2007-02-22 2014-07-01 Othera Holding Inc Compostos de hidroxilamina e métodos de seu uso
JP2010537991A (ja) 2007-08-31 2010-12-09 アーケマ・インコーポレイテッド アクリル酸及びアクリレートプロセスにおける重合及び汚れの抑制方法
DE102008061611A1 (de) 2007-12-19 2009-06-25 Basf Se Verhinderung der Polymerisation in Wasser-Aromaten-Mischungen
US8247593B2 (en) 2008-05-13 2012-08-21 Nalco Company Process for preparing substituted 7-cyano quinone methides
EP2233505A1 (en) 2009-03-23 2010-09-29 Total Petrochemicals Research Feluy Stabilised compositions comprising olefins
CN102795966B (zh) 2011-05-24 2014-09-03 江苏恒祥化工有限责任公司 控制1,4-环己烷二甲醇精馏过程中聚合的方法
US8884038B2 (en) 2011-06-13 2014-11-11 Nalco Company Synthesis of 7-acetyleno quinone methide derivatives and their application as vinylic polymerization retarders
DE102013204950A1 (de) 2013-03-20 2014-09-25 Evonik Industries Ag Verfahren und Zusammensetzung zur Inhibierung der Polymerisation von Cyclopentadienverbindungen
US9399622B2 (en) 2013-12-03 2016-07-26 Ecolab Usa Inc. Nitroxide hydroxylamine and phenylenediamine combinations as polymerization inhibitors for ethylenically unsaturated monomer processes

Also Published As

Publication number Publication date
JP2018511592A (ja) 2018-04-26
JP6730303B2 (ja) 2020-07-29
EP3271331B1 (en) 2022-03-02
CN107406388B (zh) 2021-06-18
TW201704212A (zh) 2017-02-01
CN107406388A (zh) 2017-11-28
RU2715559C2 (ru) 2020-03-02
CA2979828A1 (en) 2016-09-22
EP3271331A1 (en) 2018-01-24
BR112017018283A2 (pt) 2018-04-10
KR20170129242A (ko) 2017-11-24
RU2017132514A (ru) 2019-04-18
EP3271331A4 (en) 2018-08-15
AR103961A1 (es) 2017-06-14
RU2017132514A3 (https=) 2019-08-28
US20160272586A1 (en) 2016-09-22
TWI680964B (zh) 2020-01-01
WO2016149433A1 (en) 2016-09-22
ES2912329T3 (es) 2022-05-25
US9914701B2 (en) 2018-03-13
BR112017018283B1 (pt) 2022-07-12
KR102583199B1 (ko) 2023-09-25

Similar Documents

Publication Publication Date Title
JP2855399B2 (ja) ビニル芳香族モノマーの重合禁止
CA2979828C (en) The use of stable lipophilic hydroxylamine compounds for inhibiting polymerization of vinyl monomers
US9957209B2 (en) Use of quinone methides as antipolymerants for vinylic monomers
CN1082499C (zh) 含单体和稳定剂的混合物
CN100522902C (zh) 芳香族乙烯基化合物的聚合抑制剂以及聚合抑制方法
CA2982465C (en) Sterically hindered hydroquinones as antifoulants for unsaturated monomers
EP0845448B1 (en) Inhibiting polymerization of vinyl aromatic monomers
EP1937726A1 (en) Inhibition of polymerisation
JP2003520259A (ja) 不飽和単量体の重合抑制
KR100450603B1 (ko) 중합 반응 억제제
MX2007015247A (es) Orto-nitrosofenoles como inhibidores de polimerizacion.
KR20010079776A (ko) 장애 히드록실아민을 이용한 비닐 모노머 중합반응 억제방법
JP3534701B2 (ja) 不飽和有機化合物を重合から安定化する方法
JP2008222702A (ja) ビニル基含有化合物の重合防止剤および重合防止方法
JP4165812B2 (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
KR101151478B1 (ko) 중합 억제제로서 술폰화된 니트로페놀
JP2006176417A (ja) 芳香族ビニル化合物の重合抑制方法

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20210310

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 9TH ANNIV.) - STANDARD

Year of fee payment: 9

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20241106

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT DETERMINED COMPLIANT

Effective date: 20241106

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20241106

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 10TH ANNIV.) - STANDARD

Year of fee payment: 10

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20251104

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20251104