WO2014099465A1 - Reactive polyoxazolines having a perfluorinated group - Google Patents
Reactive polyoxazolines having a perfluorinated group Download PDFInfo
- Publication number
- WO2014099465A1 WO2014099465A1 PCT/US2013/074016 US2013074016W WO2014099465A1 WO 2014099465 A1 WO2014099465 A1 WO 2014099465A1 US 2013074016 W US2013074016 W US 2013074016W WO 2014099465 A1 WO2014099465 A1 WO 2014099465A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- compound
- integer
- carbon atoms
- reactive
- 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
- 0 C*C(C)(CC*(C(C)(C)*(C)C)[N+](N)[O-])*(C)C Chemical compound C*C(C)(CC*(C(C)(C)*(C)C)[N+](N)[O-])*(C)C 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0233—Polyamines derived from (poly)oxazolines, (poly)oxazines or having pendant acyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/48—Polymers modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
- C09D179/02—Polyamines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
Definitions
- alkylene refers to a divalent group that is a radical of an alkane and includes groups that are linear, branched, cyclic, bicyclic, or a combination thereof. Unless otherwise indicated, the alkylene group typically has 1 to 30 carbon atoms. In some embodiments, the alkylene group has 1 to 20 carbon atoms, 1 to 10 carbon atoms, 1 to 6 carbon atoms, or 1 to 4 carbon atoms. Examples of alkylene groups include, but are not limited to, methylene, ethylene, 1,3 -propylene, 1 ,2-propylene, 1 ,4-butylene, 1 ,4-cyclohexylene, and 1 ,4-cyclohexyldimethylene.
- aryloxy refers to a monovalent group having an oxy group bonded directly to an aryl group.
- reactive group refers to a functionality that will react with itself and/or another molecule (e.g., through polymerizing or crosslinking) to form a polymeric network. Such group can also be referred to as a "polymerizable group.”
- the polymerizable group often includes a group that can undergo a free radical reaction such as an ethylenically unsaturated group. Alternatively, the polymerizable group can undergo a hydrolysis and/or condensation reaction.
- Such polymerizable groups include hydro lyzable silyl groups.
- reactive group refers to a first group that can react with a second group on a substrate surface to attach the first group to substrate though the formation of a covalent bond. Such group can also be referred to as a "substrate-reactive group.”
- the substrate-reactive group typically includes a hydrolyzable silyl group.
- R 1 is selected from H, an alkyl group, an aryl group, and combinations thereof. In certain embodiments, R 1 is H, a (Cl-C20)alkyl group, a (C6-C12)aryl group, a (C6- C12)ar(Cl-C20)alkyl group, or a (Cl-C20)alk(C6-C12)aryl group. In certain embodiments, R 1 is selected from H, methyl, and ethyl.
- R 3 is a polymerizable group, in particular an ethylenically unsaturated group selected from a vinyl group, a vinylether group, a (meth)acryloyloxy group, and a
- R f is a perfluonnated alkyl group. In certain embodiments, R f is a perfluorinated (Cl-C5)alkyl group. In certain embodiments, R f is a perfluonnated C4 alkyl group.
- x is an integer from 2 to 20. In certain embodiments, x is 2 to 10. In certain embodiments, x is 2 to 6.
- -0-C(0)-CH CH-C(0)-0-; n is greater than 10; x is 2 to 20; and y is at least 1.
- R 1 is selected from H, an alkyl group, an aryl group, and combinations thereof;
- R 2 is
- R 1 is selected from H, an alkyl group, an aryl group, and combinations thereof;
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Paints Or Removers (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14/648,733 US9718920B2 (en) | 2012-12-19 | 2013-12-10 | Reactive polyoxazolines having a perfluorinated group |
| EP13815880.3A EP2935403B1 (en) | 2012-12-19 | 2013-12-10 | Reactive polyoxazolines having a perfluorinated group |
| CN201380066738.1A CN104870520B (zh) | 2012-12-19 | 2013-12-10 | 具有全氟化基团的反应性聚噁唑啉 |
| JP2015549455A JP6445454B2 (ja) | 2012-12-19 | 2013-12-10 | パーフルオロ基を有する反応性ポリオキサゾリン |
| US15/633,980 US10087287B2 (en) | 2012-12-19 | 2017-06-27 | Reactive polyoxazolines having a perfluorinated group |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261739150P | 2012-12-19 | 2012-12-19 | |
| US61/739,150 | 2012-12-19 |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US14/648,733 A-371-Of-International US9718920B2 (en) | 2012-12-19 | 2013-12-10 | Reactive polyoxazolines having a perfluorinated group |
| US15/633,980 Continuation US10087287B2 (en) | 2012-12-19 | 2017-06-27 | Reactive polyoxazolines having a perfluorinated group |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2014099465A1 true WO2014099465A1 (en) | 2014-06-26 |
Family
ID=49917243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2013/074016 Ceased WO2014099465A1 (en) | 2012-12-19 | 2013-12-10 | Reactive polyoxazolines having a perfluorinated group |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US9718920B2 (enExample) |
| EP (1) | EP2935403B1 (enExample) |
| JP (1) | JP6445454B2 (enExample) |
| CN (1) | CN104870520B (enExample) |
| WO (1) | WO2014099465A1 (enExample) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9556340B2 (en) | 2012-12-19 | 2017-01-31 | 3M Innovative Properties Company | Polyoxazoline copolymers |
| WO2017205244A1 (en) | 2016-05-23 | 2017-11-30 | Microban Products Company | Touch screen cleaning and protectant composition |
| US10834922B2 (en) | 2014-11-26 | 2020-11-17 | Microban Products Company | Surface disinfectant with residual biocidal property |
| US10842147B2 (en) | 2014-11-26 | 2020-11-24 | Microban Products Company | Surface disinfectant with residual biocidal property |
| US10925281B2 (en) | 2014-11-26 | 2021-02-23 | Microban Products Company | Surface disinfectant with residual biocidal property |
| US11033023B2 (en) | 2014-11-26 | 2021-06-15 | Microban Products Company | Surface disinfectant with residual biocidal property |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4656669A1 (en) * | 2024-05-28 | 2025-12-03 | Arkema France | Fluorinated copolymers based on an oligo(2-oxazoline) macromonomer |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0244828A2 (en) * | 1986-05-07 | 1987-11-11 | Daikin Industries, Limited | Fluorine-containing polymer and process for preparing the same |
| EP0616256A1 (de) * | 1993-03-16 | 1994-09-21 | Agfa-Gevaert AG | Farbfotografisches Aufzeichnungsmaterial |
| EP1219661A1 (en) * | 1999-08-04 | 2002-07-03 | NanoCarrier Co., Ltd. | Block copolymer having polymer segment derived from oxazoline |
| WO2010089484A1 (fr) * | 2009-02-09 | 2010-08-12 | Creat | Procédé de fonctionnalisation d'un substrat textile en vue de lui conférer des propriétés hydrophobes et oléophobes |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3198754A (en) * | 1962-01-02 | 1965-08-03 | Minnesota Mining & Mfg | Aziridine derivatives and polymers thereof |
| US3483141A (en) * | 1964-07-13 | 1969-12-09 | Allied Chem | Carbon-nitrogen backbone chain polymers |
| US3640909A (en) * | 1969-02-17 | 1972-02-08 | Dow Chemical Co | Substituted acylated polyimine resins |
| US3575890A (en) * | 1969-02-26 | 1971-04-20 | Allied Chem | Oxazine and oxazoline derived c-n backbone polymers |
| US4011376A (en) * | 1975-03-03 | 1977-03-08 | The Dow Chemical Company | Novel reaction products of allyl halides or vinylbenzyl halides with oxazolines (or oxazines) |
| GB8323241D0 (en) | 1983-08-30 | 1983-09-28 | Ici Plc | Coating compositions |
| US4659777A (en) * | 1985-11-27 | 1987-04-21 | Thoratec Laboratories Corp. | Polysiloxane/poly(oxazoline) copolymers |
| US4910268A (en) | 1987-04-22 | 1990-03-20 | Shiro Kobayashi | Acryl type macromonomer having a polyethyleneimine derivative chain and process for producing the same, as well as graft polymer having a polyethyleneimine derivative chain as the graft chain and process for producing the same |
| JP2680434B2 (ja) * | 1989-07-25 | 1997-11-19 | 武夫 三枝 | オキサゾリンポリマー/シリカ複合成形体の製造方法 |
| JP2841611B2 (ja) * | 1990-01-11 | 1998-12-24 | ダイキン工業株式会社 | フッ素系界面活性剤 |
| US5219662A (en) | 1991-05-23 | 1993-06-15 | E. I. Du Pont De Nemours And Company | Biocompatible polyurethanes by treatment with polyoxazoline block copolymers |
| JP2732989B2 (ja) * | 1992-07-30 | 1998-03-30 | 信越化学工業株式会社 | ポリオキサゾリン変性シランおよびその製造方法 |
| US5472838A (en) * | 1993-03-16 | 1995-12-05 | Agfa-Gevaert Ag | Process for the production of a silver halide emulsion |
| US5338428A (en) * | 1993-05-28 | 1994-08-16 | California Institute Of Technology | Poly(N-Acylalkylenimine) electrophoresis support media |
| US5418277A (en) * | 1994-04-26 | 1995-05-23 | E. I. Du Pont De Nemours And Company | Aqueous ink jet inks containing fluorinated polymers |
| US6162877A (en) | 1998-12-04 | 2000-12-19 | Hercules Incorporated | Hydrophobically modified comb copolymers |
| AR024237A1 (es) | 1998-12-21 | 2002-09-25 | Novartis Ag | Copolimeros en bloque anfifilicos, procedimiento y precursores para su preparacion, y articulo moldeado obtenible a partir de los mismos |
| US7858108B2 (en) | 2003-10-21 | 2010-12-28 | Richard Nagler | Elutable surface coating |
| US20070100128A1 (en) * | 2005-10-28 | 2007-05-03 | Eastman Kodak Company | Segmented poly(ethyleneimine) compositions |
| EP1849450B1 (de) | 2006-04-28 | 2009-11-25 | Ivoclar Vivadent AG | Dentalwerkstoffe auf der Basis radikalisch polymerisierbarer Makromere mit antimikrobieller Wirkung |
| EP1897626A1 (en) | 2006-09-05 | 2008-03-12 | SurfaceSolutions GmbH | Dirt-resistant and non adhesive flat material |
| US7585919B2 (en) | 2006-09-26 | 2009-09-08 | 3M Innovative Properties Company | Polymer derived from monomers with long-chain aliphatic, poly(oxyalkylene) and substrate-reactive groups |
| WO2008097786A2 (en) | 2007-02-05 | 2008-08-14 | Dow Global Technologies Inc. | Modified polyamide membrane |
| US8263104B2 (en) | 2007-06-08 | 2012-09-11 | Northwestern University | Polymer nanofilm coatings |
| KR101150285B1 (ko) | 2008-06-05 | 2012-05-25 | 허준혁 | 내오염성이 우수한 수처리용 분리막 및 이의 제조방법 |
| US8816004B2 (en) | 2010-12-14 | 2014-08-26 | 3M Innovative Properties Company | Oxazolinyl-containing polymers and grafted compounds prepared from the oxazolinyl-containing polymers |
| SG10201605381PA (en) | 2011-06-30 | 2016-08-30 | Hempel As | Fouling control coating compositions |
| WO2013123507A1 (en) | 2012-02-17 | 2013-08-22 | Bacterin International, Inc. | Composition of and method for forming reduced viscosity polymeric coatings |
| CN104884541B (zh) | 2012-12-19 | 2017-05-03 | 3M创新有限公司 | 聚噁唑啉共聚物 |
-
2013
- 2013-12-10 EP EP13815880.3A patent/EP2935403B1/en not_active Not-in-force
- 2013-12-10 WO PCT/US2013/074016 patent/WO2014099465A1/en not_active Ceased
- 2013-12-10 CN CN201380066738.1A patent/CN104870520B/zh not_active Expired - Fee Related
- 2013-12-10 US US14/648,733 patent/US9718920B2/en not_active Expired - Fee Related
- 2013-12-10 JP JP2015549455A patent/JP6445454B2/ja not_active Expired - Fee Related
-
2017
- 2017-06-27 US US15/633,980 patent/US10087287B2/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0244828A2 (en) * | 1986-05-07 | 1987-11-11 | Daikin Industries, Limited | Fluorine-containing polymer and process for preparing the same |
| EP0616256A1 (de) * | 1993-03-16 | 1994-09-21 | Agfa-Gevaert AG | Farbfotografisches Aufzeichnungsmaterial |
| EP1219661A1 (en) * | 1999-08-04 | 2002-07-03 | NanoCarrier Co., Ltd. | Block copolymer having polymer segment derived from oxazoline |
| WO2010089484A1 (fr) * | 2009-02-09 | 2010-08-12 | Creat | Procédé de fonctionnalisation d'un substrat textile en vue de lui conférer des propriétés hydrophobes et oléophobes |
Non-Patent Citations (3)
| Title |
|---|
| KOBAYASHI SHIRO ET AL: "Synthesis of acryl- and methacryl-type macromonomers and telechelics by utilizing living polymerization of 2-oxazolines", MACROMOLECULES, vol. 22, no. 7, July 1989 (1989-07-01), pages 2878 - 2884, XP002722096 * |
| KOBAYASHI, S ET AL: "Synthesis of a Nonionic Polymer Surfactant from Cyclic Imino Ethers by the Initiator Method", MACROMOLECULES, vol. 20, no. 8, 1987, pages 1729 - 1734, XP002722095 * |
| R. WEBERSKIRCH ET AL: "Design and synthesis of a two compartment micellar system based on the self-association behavior of poly(N-acylethyleneimine) end-capped with a fluorocarbon and a hydrocarbon chain", MACROMOLECULAR CHEMISTRY AND PHYSICS, vol. 201, no. 10, 1 June 2000 (2000-06-01), pages 995 - 1007, XP055109078, ISSN: 1022-1352, DOI: 10.1002/1521-3935(20000601)201:10<995::AID-MACP995>3.0.CO;2-T * |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9556340B2 (en) | 2012-12-19 | 2017-01-31 | 3M Innovative Properties Company | Polyoxazoline copolymers |
| US10834922B2 (en) | 2014-11-26 | 2020-11-17 | Microban Products Company | Surface disinfectant with residual biocidal property |
| US10842147B2 (en) | 2014-11-26 | 2020-11-24 | Microban Products Company | Surface disinfectant with residual biocidal property |
| US10925281B2 (en) | 2014-11-26 | 2021-02-23 | Microban Products Company | Surface disinfectant with residual biocidal property |
| US11026418B2 (en) | 2014-11-26 | 2021-06-08 | Microban Products Company | Surface disinfectant with residual biocidal property |
| US11033023B2 (en) | 2014-11-26 | 2021-06-15 | Microban Products Company | Surface disinfectant with residual biocidal property |
| US11134674B2 (en) | 2014-11-26 | 2021-10-05 | Microban Products Company | Surface disinfectant with residual biocidal property |
| US11134678B2 (en) | 2014-11-26 | 2021-10-05 | Microban Products Company | Surface disinfectant with residual biocidal property |
| WO2017205244A1 (en) | 2016-05-23 | 2017-11-30 | Microban Products Company | Touch screen cleaning and protectant composition |
| EP3463368A4 (en) * | 2016-05-23 | 2019-12-25 | Microban Products Company | CLEANING AND PROTECTIVE COMPOSITION FOR TOUCH SCREENS |
| US11503824B2 (en) | 2016-05-23 | 2022-11-22 | Microban Products Company | Touch screen cleaning and protectant composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JP6445454B2 (ja) | 2018-12-26 |
| EP2935403A1 (en) | 2015-10-28 |
| US20170291992A1 (en) | 2017-10-12 |
| CN104870520A (zh) | 2015-08-26 |
| US9718920B2 (en) | 2017-08-01 |
| JP2016503093A (ja) | 2016-02-01 |
| CN104870520B (zh) | 2018-04-06 |
| US10087287B2 (en) | 2018-10-02 |
| EP2935403B1 (en) | 2018-05-16 |
| US20150329673A1 (en) | 2015-11-19 |
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