JP2006525411A5 - - Google Patents
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- Publication number
- JP2006525411A5 JP2006525411A5 JP2006509268A JP2006509268A JP2006525411A5 JP 2006525411 A5 JP2006525411 A5 JP 2006525411A5 JP 2006509268 A JP2006509268 A JP 2006509268A JP 2006509268 A JP2006509268 A JP 2006509268A JP 2006525411 A5 JP2006525411 A5 JP 2006525411A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- allenyl
- groups
- aryl
- alkyl
- 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.)
- Pending
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- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000005282 allenyl group Chemical group 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000012986 chain transfer agent Substances 0.000 claims description 5
- 125000005022 dithioester group Chemical group 0.000 claims description 5
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical group CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- 125000002560 nitrile group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 238000010526 radical polymerization reaction Methods 0.000 claims description 2
- 238000007142 ring opening reaction Methods 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims 7
- 239000003999 initiator Substances 0.000 claims 4
- IEJPPSMHUUQABK-UHFFFAOYSA-N 2,4-diphenyl-4h-1,3-oxazol-5-one Chemical group O=C1OC(C=2C=CC=CC=2)=NC1C1=CC=CC=C1 IEJPPSMHUUQABK-UHFFFAOYSA-N 0.000 claims 3
- 229920001577 copolymer Polymers 0.000 claims 3
- 238000012644 addition polymerization Methods 0.000 claims 1
- 125000005647 linker group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000006413 ring segment Chemical group 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- -1 4,4- dimethyl-5-oxo-4,5-dihydro - oxazol-2-yl Chemical group 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 2
- BGPJLYIFDLICMR-UHFFFAOYSA-N 1,4,2,3-dioxadithiolan-5-one Chemical compound O=C1OSSO1 BGPJLYIFDLICMR-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002825 nitriles Chemical group 0.000 description 1
- PQZOEWCOBPDXBH-UHFFFAOYSA-N o-ethyl 1-(4,4-dimethyl-5-oxo-1,3-oxazol-2-yl)ethylsulfanylmethanethioate Chemical compound CCOC(=S)SC(C)C1=NC(C)(C)C(=O)O1 PQZOEWCOBPDXBH-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/429,438 US6753391B1 (en) | 2003-05-05 | 2003-05-05 | Ring-opened azlactone chain transfer agents for radical polymerization |
| PCT/US2004/009092 WO2004099276A1 (en) | 2003-05-05 | 2004-03-25 | Ring-opened azlactone chain transfer agents for radical polymerization |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006525411A JP2006525411A (ja) | 2006-11-09 |
| JP2006525411A5 true JP2006525411A5 (enExample) | 2007-05-24 |
Family
ID=32469319
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006509268A Pending JP2006525411A (ja) | 2003-05-05 | 2004-03-25 | ラジカル重合のための開環アズラクトン連鎖移動剤 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US6753391B1 (enExample) |
| EP (1) | EP1620482B1 (enExample) |
| JP (1) | JP2006525411A (enExample) |
| CN (1) | CN100526357C (enExample) |
| AT (1) | ATE378362T1 (enExample) |
| DE (1) | DE602004010092T2 (enExample) |
| WO (1) | WO2004099276A1 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6992217B2 (en) * | 2002-12-11 | 2006-01-31 | 3M Innovative Properties Company | Ring-opened azlactone initiators for atom transfer radical polymerization |
| US6894133B2 (en) * | 2002-12-11 | 2005-05-17 | 3M Innovative Properties Company | Azlactone initiators for atom transfer radical polymerization |
| US6908952B2 (en) * | 2003-03-21 | 2005-06-21 | 3M Innovative Properties Company | Ring-opened azlactone photoiniferters for radical polymerization |
| US6969744B2 (en) * | 2003-06-19 | 2005-11-29 | University Of Southern Mississippi | Living and quasiliving cationic telechelic polymers quenched by N-substituted pyrrole and methods for their preparation |
| JP2007515538A (ja) * | 2003-12-23 | 2007-06-14 | ザ ユニバーシティ オブ リーズ | 連鎖移動剤を使用した重合 |
| EP1786843A4 (en) * | 2004-08-20 | 2011-08-31 | Chevron Oronite Co | PROCESS FOR PREPARING POLYOLEFINES WITH EXO-OLEFIN CHAIN ENDS |
| US7705090B2 (en) * | 2004-08-20 | 2010-04-27 | Chevron Oronite Company Llc | Method for preparing polyolefins containing a high percentage of exo-olefin chain ends |
| CN100336834C (zh) * | 2005-05-11 | 2007-09-12 | 浙江大学 | 油溶性引发剂引发活性细乳液聚合法制备微胶囊的方法 |
| EP1969397B1 (en) * | 2005-12-14 | 2017-11-08 | Novartis AG | Method for preparing silicone hydrogels |
| US7816459B2 (en) * | 2005-12-30 | 2010-10-19 | Chevron Oronite Company Llc | Method for preparing polyolefins containing vinylidine end groups using polymeric nitrogen compounds |
| US8013073B2 (en) * | 2005-12-30 | 2011-09-06 | Chevron Oronite Company Llc | Method for preparing polyolefins containing vinylidine end groups using nonaromatic heterocyclic compounds |
| US8394897B2 (en) * | 2008-03-25 | 2013-03-12 | Chevron Oronite Company Llc | Production of vinylidene-terminated polyolefins via quenching with monosulfides |
| US8063154B2 (en) * | 2008-06-24 | 2011-11-22 | The University Of Southern Mississippi | Preparation of exo-olefin terminated polyolefins via quenching with alkoxysilanes or ethers |
| US8133954B2 (en) | 2008-10-22 | 2012-03-13 | Chevron Oronite Company Llc | Production of vinylidene-terminated and sulfide-terminated telechelic polyolefins via quenching with disulfides |
| US8344073B2 (en) | 2009-01-16 | 2013-01-01 | The University Of Southern Mississippi | Functionalization of polyolefins with phenoxy derivatives |
| US8552122B2 (en) | 2009-03-31 | 2013-10-08 | The University Of Southern Mississippi | Amine-terminated telechelic polymers and precursors thereto and methods for their preparation |
| US8133960B2 (en) * | 2009-06-16 | 2012-03-13 | Bausch & Lomb Incorporated | Biomedical devices |
| US8083348B2 (en) * | 2009-06-16 | 2011-12-27 | Bausch & Lomb Incorporated | Biomedical devices |
| US8394898B2 (en) | 2009-07-31 | 2013-03-12 | The University Of Southern Mississippi | In situ formation of hydroxy chain end functional polyolefins |
| US8492491B2 (en) | 2010-06-10 | 2013-07-23 | Chevron Oronite Company Llc | Methods for producing telechelic polyolefins from terpene initiators |
| US8592527B2 (en) | 2010-06-14 | 2013-11-26 | University Of Southern Mississippi | Vinyl ether end-functionalized polyolefins |
| CN102336877B (zh) * | 2011-05-20 | 2013-01-09 | 上海大学 | 在水分散相中聚合制备高分子及高分子纳米颗粒的方法 |
| US8969484B2 (en) | 2011-07-08 | 2015-03-03 | Chevron Oronite Company Llc | Methods of producing mono- and multi-functional polymers from terpene-based initiators |
| FR2987837B1 (fr) * | 2012-03-09 | 2014-03-14 | Rhodia Operations | Polymerisation radicalaire controlee en dispersion eau-dans-l'eau |
| CN103524651B (zh) * | 2013-10-12 | 2016-03-16 | 三明学院 | 一种流平剂和防缩孔剂 |
| EP3481872B1 (en) | 2016-07-11 | 2020-04-08 | 3M Innovative Properties Company | Polymeric material and methods of making using controlled radical initiators |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5763548A (en) | 1995-03-31 | 1998-06-09 | Carnegie-Mellon University | (Co)polymers and a novel polymerization process based on atom (or group) transfer radical polymerization |
| US5807937A (en) | 1995-11-15 | 1998-09-15 | Carnegie Mellon University | Processes based on atom (or group) transfer radical polymerization and novel (co) polymers having useful structures and properties |
| ATE210684T1 (de) * | 1996-07-10 | 2001-12-15 | Du Pont | POLYMERISATION MIT ßLIVINGß KENNZEICHEN |
| FR2764892B1 (fr) | 1997-06-23 | 2000-03-03 | Rhodia Chimie Sa | Procede de synthese de polymeres a blocs |
| JP2001506423A (ja) | 1997-07-11 | 2001-05-15 | ベーセー コンポネンツ ホールディングス ベー ヴェー | 高電圧抵抗及びこのような高電圧抵抗を有する高電圧電源 |
| US6143848A (en) | 1997-10-23 | 2000-11-07 | The B.F.Goodrich Company | End-functionalized polymers by controlled free-radical polymerization process and polymers made therefrom |
| BR9815179A (pt) | 1997-12-18 | 2000-10-10 | Du Pont | Processo para produzir um polìmero, polìmero, composição de revestimento e agente de transferência de cadeia. |
| TW574236B (en) | 2000-09-25 | 2004-02-01 | Ciba Sc Holding Ag | Process for controlled radical polymerization in aqueous dispersion |
| US6569969B2 (en) | 2000-09-28 | 2003-05-27 | Symyx Technologies, Inc. | Control agents for living-type free radical polymerization, methods of polymerizing and polymers with same |
| US6894133B2 (en) * | 2002-12-11 | 2005-05-17 | 3M Innovative Properties Company | Azlactone initiators for atom transfer radical polymerization |
| US6992217B2 (en) * | 2002-12-11 | 2006-01-31 | 3M Innovative Properties Company | Ring-opened azlactone initiators for atom transfer radical polymerization |
| US6680362B1 (en) * | 2003-02-05 | 2004-01-20 | 3M Innovative Properties Company | Ring-opened azlactone initiators for nitroxide-mediated polymerization |
| US6677413B1 (en) * | 2003-02-05 | 2004-01-13 | 3M Innovative Properties Company | Azlactone initiators for nitroxide-mediated polymerization |
| US6747104B1 (en) * | 2003-03-21 | 2004-06-08 | 3M Innovative Properties Company | Azlactone photoiniferters for radical polymerization |
-
2003
- 2003-05-05 US US10/429,438 patent/US6753391B1/en not_active Expired - Lifetime
-
2004
- 2004-03-23 US US10/807,007 patent/US6841637B2/en not_active Expired - Lifetime
- 2004-03-25 WO PCT/US2004/009092 patent/WO2004099276A1/en not_active Ceased
- 2004-03-25 JP JP2006509268A patent/JP2006525411A/ja active Pending
- 2004-03-25 AT AT04760501T patent/ATE378362T1/de not_active IP Right Cessation
- 2004-03-25 DE DE602004010092T patent/DE602004010092T2/de not_active Expired - Lifetime
- 2004-03-25 CN CNB2004800120830A patent/CN100526357C/zh not_active Expired - Fee Related
- 2004-03-25 EP EP04760501A patent/EP1620482B1/en not_active Expired - Lifetime
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