CN101646683B - 迈克尔加合物含氟硅烷 - Google Patents
迈克尔加合物含氟硅烷 Download PDFInfo
- Publication number
- CN101646683B CN101646683B CN2008800107088A CN200880010708A CN101646683B CN 101646683 B CN101646683 B CN 101646683B CN 2008800107088 A CN2008800107088 A CN 2008800107088A CN 200880010708 A CN200880010708 A CN 200880010708A CN 101646683 B CN101646683 B CN 101646683B
- Authority
- CN
- China
- Prior art keywords
- oxygen base
- alkyl
- alkylidene group
- alkylidene
- group
- 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
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- 150000004756 silanes Chemical class 0.000 title abstract description 3
- 239000000203 mixture Substances 0.000 claims abstract description 73
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- 150000001875 compounds Chemical class 0.000 claims abstract description 48
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- 239000008199 coating composition Substances 0.000 claims abstract description 17
- 125000001118 alkylidene group Chemical group 0.000 claims description 79
- 239000001301 oxygen Substances 0.000 claims description 62
- 229910052760 oxygen Inorganic materials 0.000 claims description 62
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- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- BUZRAOJSFRKWPD-UHFFFAOYSA-N isocyanatosilane Chemical class [SiH3]N=C=O BUZRAOJSFRKWPD-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 229910052752 metalloid Inorganic materials 0.000 description 1
- 150000002738 metalloids Chemical class 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 238000006140 methanolysis reaction Methods 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- XWZZZMXGYMXMQX-UHFFFAOYSA-N methyl-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C)C1=CC=C(C)C=C1 XWZZZMXGYMXMQX-UHFFFAOYSA-N 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- CFJYNSNXFXLKNS-UHFFFAOYSA-N p-menthane Chemical compound CC(C)C1CCC(C)CC1 CFJYNSNXFXLKNS-UHFFFAOYSA-N 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 238000001020 plasma etching Methods 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 238000007763 reverse roll coating Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 229920006352 transparent thermoplastic Polymers 0.000 description 1
- 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
- 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
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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 | 2007-03-29 | ||
US11/693,510 US7335786B1 (en) | 2007-03-29 | 2007-03-29 | Michael-adduct fluorochemical silanes |
PCT/US2008/055229 WO2008121469A1 (en) | 2007-03-29 | 2008-02-28 | Michael-adduct fluorochemical silanes |
Publications (2)
Publication Number | Publication Date |
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CN101646683A CN101646683A (zh) | 2010-02-10 |
CN101646683B true CN101646683B (zh) | 2013-12-25 |
Family
ID=39103626
Family Applications (1)
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CN2008800107088A Expired - Fee Related CN101646683B (zh) | 2007-03-29 | 2008-02-28 | 迈克尔加合物含氟硅烷 |
Country Status (5)
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US8015970B2 (en) * | 2007-07-26 | 2011-09-13 | 3M Innovative Properties Company | Respirator, welding helmet, or face shield that has low surface energy hard-coat lens |
US7897678B2 (en) * | 2007-07-26 | 2011-03-01 | 3M Innovative Properties Company | Fluorochemical urethane compounds having pendent silyl groups |
US20110020657A1 (en) * | 2007-12-27 | 2011-01-27 | Cheng-Chung Chang | Protective coating compositions |
CN101959982B (zh) | 2007-12-27 | 2014-08-06 | 3M创新有限公司 | 保护涂层组合物 |
EP2712900A1 (en) * | 2008-03-11 | 2014-04-02 | 3M Innovative Properties Company | Phototools having a protective layer |
CN102307851B (zh) | 2008-12-11 | 2015-05-06 | 3M创新有限公司 | 酰胺连接的全氟聚醚硫醇化合物及其制备方法和用途 |
US8324324B2 (en) * | 2009-06-30 | 2012-12-04 | 3M Innovative Properties Company | Composition and process for preparing curable organofluorine-modified polysilazanes, and polysilazanes prepared thereby |
EP2456823A4 (en) | 2009-07-21 | 2012-12-26 | 3M Innovative Properties Co | CURABLE COMPOSITION, METHOD FOR COATING A PHOTO TOOL, AND COATED PHOTO TOOL |
CN102549042B (zh) | 2009-09-16 | 2015-01-28 | 3M创新有限公司 | 氟化涂料和用其制作的底片 |
US8748060B2 (en) | 2009-09-16 | 2014-06-10 | 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 |
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 |
CN102712758B (zh) | 2009-12-30 | 2014-05-07 | 3M创新有限公司 | 制备聚二有机硅氧烷-聚乙二酰胺共聚物的方法 |
US8907046B2 (en) | 2009-12-30 | 2014-12-09 | 3M Innovative Properties Company | Copolymers with perfluoropolyether segment and multiple aminooxalylamino groups |
US8552124B2 (en) | 2009-12-30 | 2013-10-08 | 3M Innovative Properties Company | Copolymers with perfluoropolyether segment and polydiorganosiloxane segment |
US20110195187A1 (en) * | 2010-02-10 | 2011-08-11 | Apple Inc. | Direct liquid vaporization for oleophobic coatings |
EP2638107A1 (en) | 2010-11-10 | 2013-09-18 | 3M Innovative Properties Company | Hydrophobic fluorinated coatings |
EP2720808B1 (en) | 2011-06-15 | 2016-03-23 | 3M Innovative Properties Company | Hydrophobic hydrocarbon coatings |
US8715779B2 (en) | 2011-06-24 | 2014-05-06 | Apple Inc. | Enhanced glass impact durability through application of thin films |
EP2816046B1 (en) * | 2012-02-17 | 2019-01-23 | AGC Inc. | Fluorinated ether compound, fluorinated ether composition and coating fluid, and substrate having surface-treated layer and method for its production |
JP6127985B2 (ja) * | 2012-02-17 | 2017-05-17 | 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 |
CN104114566B (zh) * | 2012-02-17 | 2017-05-31 | 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 |
JP6625987B2 (ja) | 2013-09-16 | 2019-12-25 | ハネウェル・インターナショナル・インコーポレーテッドHoneywell International Inc. | ポリフッ素含有シロキサン被覆 |
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 |
WO2016094199A1 (en) | 2014-12-08 | 2016-06-16 | 3M Innovative Properties Company | Compounds comprising modified diorganosiloxane polymers |
US10233285B2 (en) | 2014-12-08 | 2019-03-19 | 3M Innovative Properties Company | Fluorinated silane compounds, compositions, and articles |
KR20190072677A (ko) * | 2015-07-31 | 2019-06-25 | 다이킨 고교 가부시키가이샤 | 퍼플루오로(폴리)에테르기 함유 실란 화합물 |
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 |
US20230151149A1 (en) * | 2020-05-14 | 2023-05-18 | 3M Innovative Properties Company | Polymerizable Compositions and Compounds Comprising Perfluorinated Group, Hydrolysable Silane Group, and (Meth)Acryl Group |
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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- 2008-02-28 WO PCT/US2008/055229 patent/WO2008121469A1/en active Application Filing
- 2008-02-28 JP JP2010501039A patent/JP5346006B2/ja not_active Expired - Fee Related
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US6958191B2 (en) * | 2002-08-29 | 2005-10-25 | Shin-Etsu Chemical Co., Ltd. | Lens with stain resistant surface layer |
CN1738686A (zh) * | 2002-12-24 | 2006-02-22 | Ppg工业俄亥俄公司 | 防水表面处理和处理过的制品 |
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WO2008121469A1 (en) | 2008-10-09 |
JP5346006B2 (ja) | 2013-11-20 |
EP2139903A1 (en) | 2010-01-06 |
CN101646683A (zh) | 2010-02-10 |
JP2010522758A (ja) | 2010-07-08 |
US7335786B1 (en) | 2008-02-26 |
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