TWI412779B - 具有〈甲基〉丙烯酸基團之全氟聚醚胺甲酸乙酯添加劑與堅硬塗層 - Google Patents
具有〈甲基〉丙烯酸基團之全氟聚醚胺甲酸乙酯添加劑與堅硬塗層 Download PDFInfo
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- TWI412779B TWI412779B TW95109966A TW95109966A TWI412779B TW I412779 B TWI412779 B TW I412779B TW 95109966 A TW95109966 A TW 95109966A TW 95109966 A TW95109966 A TW 95109966A TW I412779 B TWI412779 B TW I412779B
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- meth
- urethane
- acrylate
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- 239000010702 perfluoropolyether Substances 0.000 title claims description 84
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims description 51
- 239000000654 additive Substances 0.000 title abstract description 35
- 230000003287 optical effect Effects 0.000 claims abstract description 56
- 239000002344 surface layer Substances 0.000 claims abstract description 24
- 239000000203 mixture Substances 0.000 claims description 122
- 238000000576 coating method Methods 0.000 claims description 101
- 239000011248 coating agent Substances 0.000 claims description 89
- 239000000463 material Substances 0.000 claims description 55
- 150000001875 compounds Chemical class 0.000 claims description 51
- 239000002245 particle Substances 0.000 claims description 45
- 239000000758 substrate Substances 0.000 claims description 43
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 41
- -1 acrylate compound Chemical class 0.000 claims description 41
- 239000010410 layer Substances 0.000 claims description 39
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 37
- 229910052757 nitrogen Inorganic materials 0.000 claims description 35
- 229910052731 fluorine Inorganic materials 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 239000008199 coating composition Substances 0.000 claims description 27
- 239000011737 fluorine Substances 0.000 claims description 25
- 125000005842 heteroatom Chemical group 0.000 claims description 25
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 239000000047 product Substances 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 239000004215 Carbon black (E152) Substances 0.000 claims description 18
- 229930195733 hydrocarbon Natural products 0.000 claims description 18
- 229910052809 inorganic oxide Inorganic materials 0.000 claims description 18
- 150000003254 radicals Chemical class 0.000 claims description 18
- 150000002430 hydrocarbons Chemical class 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 16
- 125000000524 functional group Chemical group 0.000 claims description 16
- 125000005647 linker group Chemical group 0.000 claims description 16
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 claims description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 239000006224 matting agent Substances 0.000 claims description 10
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 10
- 229910000420 cerium oxide Inorganic materials 0.000 claims description 9
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical group [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 claims description 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 8
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
- 239000003431 cross linking reagent Substances 0.000 claims description 7
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 230000001681 protective effect Effects 0.000 claims description 7
- 150000007970 thio esters Chemical class 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
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- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical group NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 5
- 229910044991 metal oxide Inorganic materials 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 3
- 229920006295 polythiol Chemical class 0.000 claims description 3
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- 239000001301 oxygen Substances 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 2
- GHXRTKWGBSEVQW-UHFFFAOYSA-J [C+4].C(C=C)(=O)[O-].NC(=O)OCC.C(C=C)(=O)[O-].C(C=C)(=O)[O-].C(C=C)(=O)[O-] Chemical compound [C+4].C(C=C)(=O)[O-].NC(=O)OCC.C(C=C)(=O)[O-].C(C=C)(=O)[O-].C(C=C)(=O)[O-] GHXRTKWGBSEVQW-UHFFFAOYSA-J 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- 125000006292 cyclic linker group Chemical group 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 description 78
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 16
- 239000003054 catalyst Substances 0.000 description 16
- 239000012975 dibutyltin dilaurate Substances 0.000 description 16
- 238000007789 sealing Methods 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
- 229920000058 polyacrylate Polymers 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000012948 isocyanate Substances 0.000 description 13
- 229940070721 polyacrylate Drugs 0.000 description 13
- 150000002513 isocyanates Chemical class 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- GTELLNMUWNJXMQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO GTELLNMUWNJXMQ-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
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- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 5
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- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
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- C07C235/08—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
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Applications Claiming Priority (1)
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| US7759447B2 (en) * | 2005-11-17 | 2010-07-20 | Bayer Materialscience Llc | Low surface energy, ethylenically unsaturated polyisocyanate addition compounds and their use in coating compositions |
| US8012567B2 (en) | 2006-01-12 | 2011-09-06 | 3M Innovative Properties Company | Light-collimating film |
| US7413807B2 (en) * | 2006-04-14 | 2008-08-19 | 3M Innovative Properties Company | Fluoroalkyl silicone composition |
| US7407710B2 (en) * | 2006-04-14 | 2008-08-05 | 3M Innovative Properties Company | Composition containing fluoroalkyl silicone and hydrosilicone |
| US7410704B2 (en) * | 2006-04-14 | 2008-08-12 | 3M Innovative Properties Company | Composition containing fluoroalkyl hydrosilicone |
| US20070285779A1 (en) * | 2006-06-13 | 2007-12-13 | Walker Christopher B | Optical films comprising high refractive index and antireflective coatings |
| US7575847B2 (en) * | 2006-06-13 | 2009-08-18 | 3M Innovative Properties Company | Low refractive index composition comprising fluoropolyether urethane compound |
| US20070285778A1 (en) * | 2006-06-13 | 2007-12-13 | Walker Christopher B | Optical films comprising high refractive index and antireflective coatings |
| US7537828B2 (en) * | 2006-06-13 | 2009-05-26 | 3M Innovative Properties Company | Low refractive index composition comprising fluoropolyether urethane compound |
| US20070292679A1 (en) * | 2006-06-14 | 2007-12-20 | 3M Innovative Properties Company | Optical article having an antistatic fluorochemical surface layer |
| JP5220286B2 (ja) * | 2006-06-15 | 2013-06-26 | 日東電工株式会社 | 防眩性ハードコートフィルム、それを用いた偏光板および画像表示装置 |
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| US7745653B2 (en) * | 2007-03-08 | 2010-06-29 | 3M Innovative Properties Company | Fluorochemical compounds having pendent silyl groups |
| US8568888B2 (en) | 2007-03-15 | 2013-10-29 | Nanovere Technologies, Inc. | Dendritic polyurethane coating |
| US8206827B2 (en) * | 2007-03-15 | 2012-06-26 | Nanovere Technologies, Llc | Dendritic polyurethane coating |
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- 2012-02-15 US US13/396,669 patent/US8476398B2/en not_active Expired - Lifetime
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2013
- 2013-06-03 US US13/908,102 patent/US8729211B2/en not_active Expired - Fee Related
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2014
- 2014-04-08 US US14/247,379 patent/US8981151B2/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0870778A1 (en) * | 1997-04-08 | 1998-10-14 | Ausimont S.p.A. | Modified hydrogenated polymers |
| TW200508270A (en) * | 2001-06-27 | 2005-03-01 | Daikin Ind Ltd | Surface-treating agent composition and use of the same |
| WO2004044062A1 (ja) * | 2002-11-13 | 2004-05-27 | Asahi Glass Company, Limited | 活性エネルギー線硬化型被覆用組成物および該組成物の硬化物からなる被膜を有する成形品 |
| TW200428020A (en) * | 2003-03-31 | 2004-12-16 | Lintec Corp | Film for optical applications |
Also Published As
| Publication number | Publication date |
|---|---|
| US8147966B2 (en) | 2012-04-03 |
| KR20130063551A (ko) | 2013-06-14 |
| TW200639422A (en) | 2006-11-16 |
| EP1866355B1 (en) | 2017-08-23 |
| US20060216500A1 (en) | 2006-09-28 |
| EP1866355A1 (en) | 2007-12-19 |
| WO2006102383A1 (en) | 2006-09-28 |
| US20100160595A1 (en) | 2010-06-24 |
| US8476398B2 (en) | 2013-07-02 |
| US20130261280A1 (en) | 2013-10-03 |
| KR20070114190A (ko) | 2007-11-29 |
| US7718264B2 (en) | 2010-05-18 |
| JP5118017B2 (ja) | 2013-01-16 |
| US20120142883A1 (en) | 2012-06-07 |
| JP2008538195A (ja) | 2008-10-16 |
| US20060216524A1 (en) | 2006-09-28 |
| US8729211B2 (en) | 2014-05-20 |
| US20140221689A1 (en) | 2014-08-07 |
| CN101146840B (zh) | 2011-06-15 |
| KR101397831B1 (ko) | 2014-05-20 |
| CN101146840A (zh) | 2008-03-19 |
| US8981151B2 (en) | 2015-03-17 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |