JP5346006B2 - マイケル付加化合物フルオロケミカルシラン - Google Patents
マイケル付加化合物フルオロケミカルシラン Download PDFInfo
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- JP5346006B2 JP5346006B2 JP2010501039A JP2010501039A JP5346006B2 JP 5346006 B2 JP5346006 B2 JP 5346006B2 JP 2010501039 A JP2010501039 A JP 2010501039A JP 2010501039 A JP2010501039 A JP 2010501039A JP 5346006 B2 JP5346006 B2 JP 5346006B2
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 94
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- 229910000077 silane Inorganic materials 0.000 title description 26
- 238000006845 Michael addition reaction Methods 0.000 title description 8
- 239000000758 substrate Substances 0.000 claims abstract description 67
- 239000008199 coating composition Substances 0.000 claims abstract description 20
- 238000000576 coating method Methods 0.000 claims description 46
- 125000002947 alkylene group Chemical group 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 239000011248 coating agent Substances 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
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- 125000003118 aryl group Chemical group 0.000 claims description 22
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- 229910044991 metal oxide Inorganic materials 0.000 claims description 17
- 150000004706 metal oxides Chemical class 0.000 claims description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 14
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- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 4
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- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
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- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- 239000004642 Polyimide Substances 0.000 description 3
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
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- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
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- UNPYQHQUDMGKJW-UHFFFAOYSA-N 6-trimethoxysilylhex-1-en-3-one Chemical compound CO[Si](OC)(OC)CCCC(=O)C=C UNPYQHQUDMGKJW-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 2
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- JAHMEIUBFPYPIM-UHFFFAOYSA-N methyl-tris(propan-2-ylperoxy)silane Chemical compound CC(C)OO[Si](C)(OOC(C)C)OOC(C)C JAHMEIUBFPYPIM-UHFFFAOYSA-N 0.000 description 1
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- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical group 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
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- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
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- GNQQPTRATSISPA-UHFFFAOYSA-N triethoxy(2-ethylbutyl)silane Chemical compound CCO[Si](OCC)(OCC)CC(CC)CC GNQQPTRATSISPA-UHFFFAOYSA-N 0.000 description 1
- ALVYUZIFSCKIFP-UHFFFAOYSA-N triethoxy(2-methylpropyl)silane Chemical compound CCO[Si](CC(C)C)(OCC)OCC ALVYUZIFSCKIFP-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- RFXMNCFJFSYLMT-UHFFFAOYSA-N triethyl 2-ethylbutyl silicate Chemical compound CCO[Si](OCC)(OCC)OCC(CC)CC RFXMNCFJFSYLMT-UHFFFAOYSA-N 0.000 description 1
- XYJRNCYWTVGEEG-UHFFFAOYSA-N trimethoxy(2-methylpropyl)silane Chemical compound CO[Si](OC)(OC)CC(C)C XYJRNCYWTVGEEG-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Surface Treatment Of Glass (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/693,510 US7335786B1 (en) | 2007-03-29 | 2007-03-29 | Michael-adduct fluorochemical silanes |
| US11/693,510 | 2007-03-29 | ||
| PCT/US2008/055229 WO2008121469A1 (en) | 2007-03-29 | 2008-02-28 | Michael-adduct fluorochemical silanes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010522758A JP2010522758A (ja) | 2010-07-08 |
| JP2010522758A5 JP2010522758A5 (OSRAM) | 2011-02-10 |
| JP5346006B2 true JP5346006B2 (ja) | 2013-11-20 |
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| JP2010501039A Expired - Fee Related JP5346006B2 (ja) | 2007-03-29 | 2008-02-28 | マイケル付加化合物フルオロケミカルシラン |
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| US (1) | US7335786B1 (OSRAM) |
| EP (1) | EP2139903B1 (OSRAM) |
| JP (1) | JP5346006B2 (OSRAM) |
| CN (1) | CN101646683B (OSRAM) |
| WO (1) | WO2008121469A1 (OSRAM) |
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| EP2235124B1 (en) | 2007-12-27 | 2015-07-29 | 3M Innovative Properties Company | Protective coating compositions |
| US20110020657A1 (en) * | 2007-12-27 | 2011-01-27 | Cheng-Chung Chang | Protective coating compositions |
| US8663874B2 (en) * | 2008-03-11 | 2014-03-04 | 3M Innovative Properties Company | Hardcoat composition |
| WO2010068531A1 (en) * | 2008-12-11 | 2010-06-17 | 3M Innovative Properties Company | Amide-linked perfluoropolyether thiol compounds and processes for their preparation and use |
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| US9096712B2 (en) | 2009-07-21 | 2015-08-04 | 3M Innovative Properties Company | Curable compositions, method of coating a phototool, and coated phototool |
| EP2478034A1 (en) | 2009-09-16 | 2012-07-25 | 3M Innovative Properties Company | Fluorinated coating and phototools made therewith |
| US8420281B2 (en) | 2009-09-16 | 2013-04-16 | 3M Innovative Properties Company | Epoxy-functionalized perfluoropolyether polyurethanes |
| US8748060B2 (en) | 2009-09-16 | 2014-06-10 | 3M Innovative Properties Company | Fluorinated coating and phototools made therewith |
| JP5669257B2 (ja) * | 2009-10-27 | 2015-02-12 | 信越化学工業株式会社 | フルオロオキシアルキレン基含有ポリマー組成物および該組成物を含む表面処理剤並びに該表面処理剤で表面処理された物品 |
| CN102666666A (zh) | 2009-12-22 | 2012-09-12 | 3M创新有限公司 | 制备架藏稳定的可固化聚硅氮烷的方法及由此制得的聚硅氮烷 |
| US8907120B2 (en) | 2009-12-30 | 2014-12-09 | 3M Innovative Properties Company | Perfluoropolyether-containing compounds with oxalylamino groups |
| US8552124B2 (en) | 2009-12-30 | 2013-10-08 | 3M Innovative Properties Company | Copolymers with perfluoropolyether segment and polydiorganosiloxane segment |
| JP5777635B2 (ja) | 2009-12-30 | 2015-09-09 | スリーエム イノベイティブ プロパティズ カンパニー | ペルフルオロポリエーテルセグメント及び複数のアミノオキサリルアミノ基を有するコポリマー |
| WO2011082069A1 (en) | 2009-12-30 | 2011-07-07 | 3M Innovative Properties Company | Methods of making polydiorganosiloxane polyoxamide copolymers |
| US20110195187A1 (en) * | 2010-02-10 | 2011-08-11 | Apple Inc. | Direct liquid vaporization for oleophobic coatings |
| CN103201331B (zh) | 2010-11-10 | 2014-12-17 | 3M创新有限公司 | 疏水性氟化涂层 |
| CN103596701B (zh) | 2011-06-15 | 2016-08-24 | 3M创新有限公司 | 疏水性烃涂层 |
| US8715779B2 (en) | 2011-06-24 | 2014-05-06 | Apple Inc. | Enhanced glass impact durability through application of thin films |
| EP2816045B1 (en) | 2012-02-17 | 2019-04-03 | AGC Inc. | Fluorinated ether compound, fluorinated ether composition and coating fluid, and substrate having surface-treated layer and method for its production |
| CN104114564B (zh) | 2012-02-17 | 2017-06-30 | 旭硝子株式会社 | 含氟醚化合物、含氟醚组合物及涂覆液以及具有表面处理层的基材及其制造方法 |
| WO2013121986A1 (ja) * | 2012-02-17 | 2013-08-22 | 旭硝子株式会社 | 含フッ素エーテル化合物、含フッ素エーテル組成物およびコーティング液、ならびに表面処理層を有する基材およびその製造方法 |
| WO2015038454A1 (en) | 2013-09-16 | 2015-03-19 | Honeywell International Inc. | Poly fluorine-containing siloxane coatings |
| CN104007491B (zh) * | 2014-05-16 | 2015-10-28 | 中科院广州化学有限公司 | 一种基于笼型倍半硅氧烷构建的抗反射涂层及其制备方法与应用 |
| CN107108880A (zh) | 2014-12-08 | 2017-08-29 | 3M创新有限公司 | 氟化硅烷化合物、组合物及制品 |
| WO2016094199A1 (en) | 2014-12-08 | 2016-06-16 | 3M Innovative Properties Company | Compounds comprising modified diorganosiloxane polymers |
| CN107428786B (zh) * | 2015-07-31 | 2019-04-30 | 大金工业株式会社 | 含有全氟(聚)醚基的硅烷化合物 |
| CN109415392A (zh) * | 2016-06-27 | 2019-03-01 | 3M创新有限公司 | 含氟化合物哌嗪甲酰胺 |
| CN109535362A (zh) * | 2018-11-16 | 2019-03-29 | 上海东大化学有限公司 | 一种氟硅改性聚醚聚合物及其制备方法 |
| CN109851775A (zh) * | 2019-02-21 | 2019-06-07 | 浙江诺诚技术发展有限公司 | 一种高全氟聚醚含量的抗指纹剂及其制备方法 |
| CN115515993B (zh) * | 2020-05-14 | 2024-11-08 | 3M创新有限公司 | 包含全氟化基团、可水解硅烷基团和(甲基)丙烯酰基基团的可聚合组合物和化合物 |
| US12517285B2 (en) | 2020-05-14 | 2026-01-06 | 3M Innovative Properties Company | Multilayer optical films comprising at least one fluorinated (co)polymer layer made using a fluorinated photoinitiator, and methods of making and using the same |
| EP4150404A4 (en) | 2020-05-14 | 2024-05-29 | 3M Innovative Properties Company | FLUORINATED PHOTOINITIATORS AND LAYERS OF FLUORINATED (CO)POLYMERS MANUFACTURED USING THEM |
| US12305063B2 (en) | 2020-05-14 | 2025-05-20 | 3M Innovative Properties Company | Fluorinated coupling agents and fluorinated (co)polymer layers made using the same |
| KR102484993B1 (ko) * | 2022-05-11 | 2023-01-09 | 에스케이이노베이션 주식회사 | 광학 다층 구조체, 이의 제조방법 및 이를 포함하는 윈도우 커버 필름 |
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| TWI265304B (en) * | 2002-08-29 | 2006-11-01 | Shinetsu Chemical Co | Lens with stain resistant surface layer |
| US6811884B2 (en) * | 2002-12-24 | 2004-11-02 | Ppg Industries Ohio, Inc. | Water repellant surface treatment and treated articles |
| US6923921B2 (en) | 2002-12-30 | 2005-08-02 | 3M Innovative Properties Company | Fluorinated polyether compositions |
| JP4309694B2 (ja) * | 2003-05-09 | 2009-08-05 | 株式会社日立製作所 | 撥水膜を有する物品及びその製法 |
| US7217440B2 (en) | 2003-06-13 | 2007-05-15 | Essilor International Compagnie Generale D'optique | Process for replacing an initial outermost coating layer of a coated optical lens with a different coating layer or by depositing thereon a different coating layer |
| JP4370846B2 (ja) * | 2003-07-30 | 2009-11-25 | ソニー株式会社 | 防汚性ハードコートおよびその製造方法、ならびに防汚性基材 |
| US7652115B2 (en) | 2003-09-08 | 2010-01-26 | 3M Innovative Properties Company | Fluorinated polyether isocyanate derived silane compositions |
| US6991826B2 (en) | 2004-04-20 | 2006-01-31 | 3M Innovative Properties Company | Antisoiling coatings for antireflective substrates |
| EP1738001A2 (en) | 2004-04-23 | 2007-01-03 | ASM America, Inc. | In situ doped epitaxial films |
| US7101618B2 (en) | 2004-05-07 | 2006-09-05 | 3M Innovative Properties Company | Article comprising fluorochemical surface layer |
| US20050249940A1 (en) | 2004-05-07 | 2005-11-10 | 3M Innovative Properties Company | Fluoropolyether poly(meth)acryl compounds |
| US7342080B2 (en) | 2004-05-07 | 2008-03-11 | 3M Innovative Properties Company | Polymerizable compositions, methods of making the same, and composite articles therefrom |
| US20060216524A1 (en) | 2005-03-23 | 2006-09-28 | 3M Innovative Properties Company | Perfluoropolyether urethane additives having (meth)acryl groups and hard coats |
-
2007
- 2007-03-29 US US11/693,510 patent/US7335786B1/en not_active Expired - Fee Related
-
2008
- 2008-02-28 JP JP2010501039A patent/JP5346006B2/ja not_active Expired - Fee Related
- 2008-02-28 EP EP08730917A patent/EP2139903B1/en not_active Not-in-force
- 2008-02-28 CN CN2008800107088A patent/CN101646683B/zh not_active Expired - Fee Related
- 2008-02-28 WO PCT/US2008/055229 patent/WO2008121469A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP2139903A1 (en) | 2010-01-06 |
| CN101646683B (zh) | 2013-12-25 |
| WO2008121469A1 (en) | 2008-10-09 |
| JP2010522758A (ja) | 2010-07-08 |
| US7335786B1 (en) | 2008-02-26 |
| CN101646683A (zh) | 2010-02-10 |
| EP2139903B1 (en) | 2012-07-11 |
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