CA2277164C - Method of controlling polymer molecular weight and structure - Google Patents

Method of controlling polymer molecular weight and structure Download PDF

Info

Publication number
CA2277164C
CA2277164C CA002277164A CA2277164A CA2277164C CA 2277164 C CA2277164 C CA 2277164C CA 002277164 A CA002277164 A CA 002277164A CA 2277164 A CA2277164 A CA 2277164A CA 2277164 C CA2277164 C CA 2277164C
Authority
CA
Canada
Prior art keywords
substituted
alkyl
iii
group
aryl
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.)
Expired - Fee Related
Application number
CA002277164A
Other languages
English (en)
French (fr)
Other versions
CA2277164A1 (en
Inventor
Albert G. Anderson
Alexei Gridnev
Graeme Moad
Ezio Rizzardo
San Hoa Thang
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.)
Commonwealth Scientific and Industrial Research Organisation
EIDP Inc
Original Assignee
Commonwealth Scientific and Industrial Research Organisation
EI Du Pont de Nemours and Co
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 Commonwealth Scientific and Industrial Research Organisation, EI Du Pont de Nemours and Co filed Critical Commonwealth Scientific and Industrial Research Organisation
Priority to CA002486907A priority Critical patent/CA2486907A1/en
Publication of CA2277164A1 publication Critical patent/CA2277164A1/en
Application granted granted Critical
Publication of CA2277164C publication Critical patent/CA2277164C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/32—One oxygen atom
    • C07D233/38—One oxygen atom with acyl radicals or hetero atoms directly attached to ring nitrogen atoms
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
    • 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
    • C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
    • C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
    • 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
    • C08F4/00—Polymerisation catalysts
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
    • 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
    • C08F2438/00—Living radical polymerisation
    • C08F2438/02—Stable Free Radical Polymerisation [SFRP]; Nitroxide Mediated Polymerisation [NMP] for, e.g. using 2,2,6,6-tetramethylpiperidine-1-oxyl [TEMPO]

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polymerization Catalysts (AREA)
  • Graft Or Block Polymers (AREA)
  • Polymerisation Methods In General (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA002277164A 1997-01-10 1998-01-07 Method of controlling polymer molecular weight and structure Expired - Fee Related CA2277164C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA002486907A CA2486907A1 (en) 1997-01-10 1998-01-07 Method of controlling polymer molecular weight and structure

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US3472797P 1997-01-10 1997-01-10
US60/034,727 1997-01-10
PCT/US1998/000601 WO1998030601A2 (en) 1997-01-10 1998-01-07 Method of controlling polymer molecular weight and structure

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA002486907A Division CA2486907A1 (en) 1997-01-10 1998-01-07 Method of controlling polymer molecular weight and structure

Publications (2)

Publication Number Publication Date
CA2277164A1 CA2277164A1 (en) 1998-07-16
CA2277164C true CA2277164C (en) 2005-11-08

Family

ID=21878221

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002277164A Expired - Fee Related CA2277164C (en) 1997-01-10 1998-01-07 Method of controlling polymer molecular weight and structure

Country Status (10)

Country Link
US (3) US6271340B1 (enExample)
EP (1) EP0951485B1 (enExample)
JP (1) JP2001508485A (enExample)
KR (1) KR100504055B1 (enExample)
CN (2) CN1280314C (enExample)
AU (1) AU750626B2 (enExample)
BR (1) BR9807104A (enExample)
CA (1) CA2277164C (enExample)
DE (2) DE69829588T2 (enExample)
WO (1) WO1998030601A2 (enExample)

Families Citing this family (54)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH693416A5 (de) 1998-03-09 2003-07-31 Ciba Sc Holding Ag 1-Alkoxypolyalkylpiperidinderivate und ihre Verwendung als Polymerisationsregler.
CA2337482A1 (en) * 1998-07-31 2000-02-17 Ciba Specialty Chemicals Holding Inc. Open chain alkoxyamine compounds and their use as polymerization regulators
ATE279447T1 (de) * 1998-09-29 2004-10-15 Ciba Sc Holding Ag Verfahren zur herstellung von polymeren enthaltend endständige n-0 gruppen
FR2784111B1 (fr) 1998-10-06 2003-08-01 Atochem Elf Sa Polymerisatin radicalaire en presence de plusieurs radicaux libres stables
TWI225483B (en) * 1998-10-16 2004-12-21 Ciba Sc Holding Ag Heterocyclic alkoxyamines as regulators in controlled radical polymerization process
WO2000053640A1 (en) * 1999-03-09 2000-09-14 Symyx Technologies, Inc. Controlled free radical emulsion and water-based polymerizations and seeded methodologies
US6472486B2 (en) 1999-03-09 2002-10-29 Symyx Technologies, Inc. Controlled stable free radical emulsion polymerization processes
US6875831B1 (en) * 1999-07-02 2005-04-05 Ciba Specialty Chemicals Corp. Mono and multifunctional alkoxyamines for the preparation of functionalized macromers
DE60027309T2 (de) 1999-07-02 2006-08-31 Symyx Technologies, Inc., Santa Clara Polymerverzweigungen zur immobilisierung von molekülen auf oberflächen oder substraten, wobei die polymere wasserlösliche oder wasserdispergierbare segmente und sonden aufweisen
US6716948B1 (en) 1999-07-31 2004-04-06 Symyx Technologies, Inc. Controlled-architecture polymers and use thereof as separation media
DE60015553T2 (de) * 1999-08-12 2005-10-27 Ciba Speciality Chemicals Holding Inc. Polymermischungen mit verbesserter schlagfestigkeit
JP4883515B2 (ja) * 1999-09-08 2012-02-22 ポリセリックス リミテッド 均一分子量ポリマー
WO2001023435A1 (en) * 1999-09-30 2001-04-05 Noveon Ip Holdings Corp. Polymerization compositions and methods
TW541303B (en) 2000-03-22 2003-07-11 Ciba Sc Holding Ag 2,2,6,6 diethyl-dimethyl-1-alkoxy-piperidine compounds and their corresponding 1-oxides
DE10036801A1 (de) 2000-07-28 2002-02-07 Tesa Ag Acrylathaftklebemassen mit enger Molekulargewichtsverteilung
TWI225492B (en) 2000-09-25 2004-12-21 Ciba Sc Holding Ag Composition and process for enhancing controlled free radical polymerization
US7205161B2 (en) 2001-01-10 2007-04-17 Symyx Technologies, Inc. Polymer brushes for immobilizing molecules to a surface or substrate having improved stability
US6547840B2 (en) 2001-04-02 2003-04-15 Ciba Specialty Chemicals Corporation Candle wax stabilized with imidazolidines
US6849679B2 (en) 2001-05-21 2005-02-01 Ciba Specialty Chemicals Corporation Pigment compositions with modified block copolymer dispersants
EP1283240A1 (en) * 2001-07-31 2003-02-12 Ciba SC Holding AG Imidazolidinone derivatives
US20030073835A1 (en) 2001-07-31 2003-04-17 Dario Lazzari Imidazolidinone derivatives
DE10149083A1 (de) 2001-10-05 2003-04-17 Tesa Ag Acrylathaftklebemassen mit enger Molekulargewichtsverteilung
DE10149084A1 (de) 2001-10-05 2003-06-18 Tesa Ag UV-vernetzbare Acrylathaftschmelzhaftkleber mit enger Molekulargewichtsverteilung
US6762263B2 (en) * 2002-02-01 2004-07-13 Atofina Chemicals, Inc. High-solids coatings resins via controlled radical polymerization
US7375175B2 (en) * 2002-08-19 2008-05-20 National Starch And Chemical Investment Holding Corporation Dispersions containing living radicals
US6841636B2 (en) 2002-08-19 2005-01-11 National Starch And Chemical Investment Holding Corporation Dispersions containing living radicals
FR2852961B1 (fr) * 2003-03-26 2006-07-07 Atofina Nouveau procede de synthese/fabrication de films acryliques
FR2852963A1 (fr) * 2003-03-26 2004-10-01 Atofina Nouveau procede de synthese/fabrication de films acryliques
DE10322830A1 (de) * 2003-05-19 2004-12-09 Tesa Ag Verfahren zur kontinuierlichen Herstellung von Polymeren aus vinylischen Verbindungen durch Substanz-beziehungsweise Lösungsmittelpolymerisation
JP4046678B2 (ja) * 2003-10-15 2008-02-13 横浜ゴム株式会社 タイヤトレッド用ゴム組成物及びそれを用いた空気入りタイヤ
US7632882B2 (en) * 2005-01-13 2009-12-15 E.I. Du Pont De Nemours And Company Rheology control agents for coating compositions
US7652121B2 (en) * 2005-01-13 2010-01-26 E.I. Du Pont De Nemours And Company Rheology control agents for coating compositions
US20060155021A1 (en) * 2005-01-13 2006-07-13 Lenges Christian P Coating compositions containing rheology control agents
US7741510B2 (en) * 2005-01-13 2010-06-22 E. I. Du Pont De Nemours And Company Rheology control agents
JP4046734B2 (ja) 2005-01-18 2008-02-13 横浜ゴム株式会社 ポリマーの変性方法
US20060173142A1 (en) * 2005-02-01 2006-08-03 Hildeberto Nava Functionalized thermosetting resin systems
US7009011B1 (en) * 2005-05-31 2006-03-07 Xerox Corporation Copolymers of maleic anhydride by stable free redical polymerization
US20070028806A1 (en) * 2005-08-03 2007-02-08 Piro Bonnie D Coating compositions having improved appearance containing coated titanium dioxide pigments
JP5068765B2 (ja) * 2005-12-14 2012-11-07 ノバルティス アーゲー シリコーンヒドロゲルの製造方法
US9051473B2 (en) * 2006-06-14 2015-06-09 Axalta Coating Systems Ip Co., Llc Clear coating compositions comprising dispersed silica nono-particles and processes for using
CA2649178A1 (en) * 2006-06-14 2007-12-21 Jun Lin Coated substrate having enhanced scratch and mar resistance
US20080021147A1 (en) * 2006-06-14 2008-01-24 Jun Lin Process for forming a dispersion of silica nano-particles
US20090274947A1 (en) * 2006-09-12 2009-11-05 Peter Nesvadba Imidazolidinone nitroxides as electrode materials for energy storage devices
WO2009077396A1 (en) * 2007-12-18 2009-06-25 Basf Se Biodiesel cold flow improver
RU2013103600A (ru) 2010-06-29 2014-08-10 Басф Се Способ улучшения свойств текучести расплавов полимеров
TWI413648B (zh) * 2010-12-31 2013-11-01 Chi Mei Corp 共軛二烯－乙烯基芳香烴共聚物及其製備方法
US20140298591A1 (en) 2011-10-25 2014-10-09 Basf Se Use of comb or block copolymers as soil antiredeposition agents and soil release agents in laundry processes
WO2014154508A1 (en) 2013-03-27 2014-10-02 Basf Se Block copolymers as soil release agents in laundry processes
FR3030525B1 (fr) * 2014-12-18 2018-05-11 Arkema France Polymerisation radicalaire d'alcoxyamines a basse temperature
CN104788594B (zh) * 2015-04-16 2018-07-24 厦门大学 一种端氨基聚合物的制备方法
JP7356875B2 (ja) 2019-11-20 2023-10-05 キリンホールディングス株式会社 カチオン性重合開始剤
EP3875566B1 (de) 2020-03-06 2023-01-11 Henkel AG & Co. KGaA Nitroxidverbindungen in wasch- oder reinigungsmitteln
HUE070248T2 (hu) 2020-11-04 2025-05-28 Alcon Inc Eljárás fotokróm kontaktlencsék elõállítására
WO2023209570A1 (en) 2022-04-26 2023-11-02 Alcon Inc. Method for making embedded hydrogel contact lenses

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1528233A (fr) * 1966-06-15 1968-06-07 Sankyo Co Nouveaux composés 4-oxoimidazolidine-1-oxydes tétrasubstitués en position-2, 2, 5, 5 et procédé pour leur préparation
CH579117A5 (enExample) * 1973-06-22 1976-08-31 Ciba Geigy Ag
DE2621947A1 (de) * 1975-05-23 1976-12-09 Ciba Geigy Ag Neue hydroxide von 3-alkyl-4-oxo- imidazolidinen
DE3486145T2 (de) 1983-07-11 1993-09-23 Commw Scient Ind Res Org Verfahren zur polymerisation und nach diesem verfahren hergestellte polymere.

Also Published As

Publication number Publication date
WO1998030601A3 (en) 1998-12-03
AU750626B2 (en) 2002-07-25
WO1998030601A2 (en) 1998-07-16
CN1249759A (zh) 2000-04-05
US20020061989A1 (en) 2002-05-23
EP0951485B1 (en) 2003-04-02
DE69829588T2 (de) 2006-01-19
CN1280314C (zh) 2006-10-18
DE69829588D1 (de) 2005-05-04
JP2001508485A (ja) 2001-06-26
US6271340B1 (en) 2001-08-07
KR20000070015A (ko) 2000-11-25
CN1824655A (zh) 2006-08-30
US20030149208A1 (en) 2003-08-07
DE69812885T2 (de) 2004-01-29
DE69812885D1 (de) 2003-05-08
CA2277164A1 (en) 1998-07-16
KR100504055B1 (ko) 2005-07-27
EP0951485A2 (en) 1999-10-27
AU6022998A (en) 1998-08-03
BR9807104A (pt) 2000-04-25

Similar Documents

Publication Publication Date Title
EP0951485B1 (en) Method of controlling polymer molecular weight and structure
Moad et al. Advances in RAFT polymerization: the synthesis of polymers with defined end-groups
JP4886109B2 (ja) リビング性を有する重合方法およびその方法で製造されるポリマー
US6855840B2 (en) Chain transfer agents for raft polymerization in aqueous media
US8569441B2 (en) Process for transforming the end groups of polymers
JP2000515181A (ja) リビング特性を持つ重合
EP1399488A1 (en) Improved heterocycle containing control agents for living-type free radical polymerization
JP4138024B2 (ja) マクロモノマーの合成方法
Miura et al. ‘Living’radical polymerization of styrene mediated by spiro ring-substituted piperidinyl-N-oxyl radicals. The effect of the spiro rings on the control of polymerization
US6388004B1 (en) Method of controlling polymer molecular weight and structure
US20030191262A1 (en) Chain transfer agents for raft polymerization in aqueous media
EP1178010A1 (en) Colorless aqueous ammonium sulfide solution
CA2486907A1 (en) Method of controlling polymer molecular weight and structure
MXPA99006330A (en) Method of controlling polymer molecular weight and structure
AU2002300378B2 (en) Ammonium Sulfide Solution
Bshena Selected aspects of RAFT agents: the use of thiophene as an activating group in the RAFT mediated polymerization of styrene and the stereo-controlled polymerization of MMA via RAFT
EP3049416A1 (en) Triazine mediated living radical controlled polymerization

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed