US20060014101A1 - Radiation-curable anti-reflective coating system - Google Patents
Radiation-curable anti-reflective coating system Download PDFInfo
- Publication number
- US20060014101A1 US20060014101A1 US11/225,317 US22531705A US2006014101A1 US 20060014101 A1 US20060014101 A1 US 20060014101A1 US 22531705 A US22531705 A US 22531705A US 2006014101 A1 US2006014101 A1 US 2006014101A1
- Authority
- US
- United States
- Prior art keywords
- layer
- refractive index
- coating
- layers
- radiation
- 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.)
- Abandoned
Links
- 239000006117 anti-reflective coating Substances 0.000 title abstract description 30
- 239000000758 substrate Substances 0.000 claims abstract description 39
- 238000009987 spinning Methods 0.000 claims abstract description 13
- 238000007598 dipping method Methods 0.000 claims abstract description 3
- 238000005096 rolling process Methods 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 27
- 239000000178 monomer Substances 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 16
- 230000005855 radiation Effects 0.000 claims description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 9
- 150000003377 silicon compounds Chemical class 0.000 claims description 6
- 238000000151 deposition Methods 0.000 claims description 5
- 238000010894 electron beam technology Methods 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 36
- 239000011248 coating agent Substances 0.000 abstract description 29
- 238000001228 spectrum Methods 0.000 abstract description 8
- 239000000203 mixture Substances 0.000 description 20
- 239000008199 coating composition Substances 0.000 description 18
- 239000000084 colloidal system Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 10
- 150000001282 organosilanes Chemical class 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000002131 composite material Substances 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- 125000003709 fluoroalkyl group Chemical group 0.000 description 8
- -1 polysiloxane Polymers 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- 150000004767 nitrides Chemical class 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-UHFFFAOYSA-N 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- 229920000620 organic polymer Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000000919 ceramic Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 150000001247 metal acetylides Chemical class 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003847 radiation curing Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000012780 transparent material Substances 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VUIMBZIZZFSQEE-UHFFFAOYSA-N 1-(1h-indol-3-yl)ethanone Chemical compound C1=CC=C2C(C(=O)C)=CNC2=C1 VUIMBZIZZFSQEE-UHFFFAOYSA-N 0.000 description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- DZZAHLOABNWIFA-UHFFFAOYSA-N 2-butoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCCC)C(=O)C1=CC=CC=C1 DZZAHLOABNWIFA-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 230000003667 anti-reflective effect Effects 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 239000007769 metal material Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 2
- 238000001029 thermal curing Methods 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- CSUUDNFYSFENAE-UHFFFAOYSA-N (2-methoxyphenyl)-phenylmethanone Chemical compound COC1=CC=CC=C1C(=O)C1=CC=CC=C1 CSUUDNFYSFENAE-UHFFFAOYSA-N 0.000 description 1
- RBKHNGHPZZZJCI-UHFFFAOYSA-N (4-aminophenyl)-phenylmethanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC=C1 RBKHNGHPZZZJCI-UHFFFAOYSA-N 0.000 description 1
- CGCQHMFVCNWSOV-UHFFFAOYSA-N (4-morpholin-4-ylphenyl)-phenylmethanone Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C1=CC=CC=C1 CGCQHMFVCNWSOV-UHFFFAOYSA-N 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- GIVFXLVPKFXTCU-UHFFFAOYSA-N 1,3-diphenylbutan-1-one Chemical compound C=1C=CC=CC=1C(C)CC(=O)C1=CC=CC=C1 GIVFXLVPKFXTCU-UHFFFAOYSA-N 0.000 description 1
- HSOAIPRTHLEQFI-UHFFFAOYSA-N 1-(3,5-diacetylphenyl)ethanone Chemical compound CC(=O)C1=CC(C(C)=O)=CC(C(C)=O)=C1 HSOAIPRTHLEQFI-UHFFFAOYSA-N 0.000 description 1
- SKBBQSLSGRSQAJ-UHFFFAOYSA-N 1-(4-acetylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(C(C)=O)C=C1 SKBBQSLSGRSQAJ-UHFFFAOYSA-N 0.000 description 1
- ZEFQETIGOMAQDT-UHFFFAOYSA-N 1-(4-morpholin-4-ylphenyl)propan-1-one Chemical compound C1=CC(C(=O)CC)=CC=C1N1CCOCC1 ZEFQETIGOMAQDT-UHFFFAOYSA-N 0.000 description 1
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 1
- JKVNPRNAHRHQDD-UHFFFAOYSA-N 1-phenanthren-3-ylethanone Chemical compound C1=CC=C2C3=CC(C(=O)C)=CC=C3C=CC2=C1 JKVNPRNAHRHQDD-UHFFFAOYSA-N 0.000 description 1
- UIFAWZBYTTXSOG-UHFFFAOYSA-N 1-phenanthren-9-ylethanone Chemical compound C1=CC=C2C(C(=O)C)=CC3=CC=CC=C3C2=C1 UIFAWZBYTTXSOG-UHFFFAOYSA-N 0.000 description 1
- MAHPVQDVMLWUAG-UHFFFAOYSA-N 1-phenylhexan-1-one Chemical compound CCCCCC(=O)C1=CC=CC=C1 MAHPVQDVMLWUAG-UHFFFAOYSA-N 0.000 description 1
- LFUMFSBLBVMPTE-UHFFFAOYSA-N 2-acetyl-10h-phenanthren-9-one Chemical compound C1=CC=C2C3=CC=C(C(=O)C)C=C3CC(=O)C2=C1 LFUMFSBLBVMPTE-UHFFFAOYSA-N 0.000 description 1
- YTPSFXZMJKMUJE-UHFFFAOYSA-N 2-tert-butylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(C(C)(C)C)=CC=C3C(=O)C2=C1 YTPSFXZMJKMUJE-UHFFFAOYSA-N 0.000 description 1
- BMVWCPGVLSILMU-UHFFFAOYSA-N 5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-one Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC=CC=C21 BMVWCPGVLSILMU-UHFFFAOYSA-N 0.000 description 1
- HUKPVYBUJRAUAG-UHFFFAOYSA-N 7-benzo[a]phenalenone Chemical compound C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=CC=CC2=C1 HUKPVYBUJRAUAG-UHFFFAOYSA-N 0.000 description 1
- PKICNJBYRWRABI-UHFFFAOYSA-N 9h-thioxanthene 10-oxide Chemical compound C1=CC=C2S(=O)C3=CC=CC=C3CC2=C1 PKICNJBYRWRABI-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- AFPRJLBZLPBTPZ-UHFFFAOYSA-N acenaphthoquinone Chemical compound C1=CC(C(C2=O)=O)=C3C2=CC=CC3=C1 AFPRJLBZLPBTPZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- ZNAAXKXXDQLJIX-UHFFFAOYSA-N bis(2-cyclohexyl-3-hydroxyphenyl)methanone Chemical compound C1CCCCC1C=1C(O)=CC=CC=1C(=O)C1=CC=CC(O)=C1C1CCCCC1 ZNAAXKXXDQLJIX-UHFFFAOYSA-N 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000011817 metal compound particle Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000006120 scratch resistant coating Substances 0.000 description 1
- VSZWPYCFIRKVQL-UHFFFAOYSA-N selanylidenegallium;selenium Chemical compound [Se].[Se]=[Ga].[Se]=[Ga] VSZWPYCFIRKVQL-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052682 stishovite Inorganic materials 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
- 239000010409 thin film Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- AVYKQOAMZCAHRG-UHFFFAOYSA-N triethoxy(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F AVYKQOAMZCAHRG-UHFFFAOYSA-N 0.000 description 1
- MTPVUVINMAGMJL-UHFFFAOYSA-N trimethyl(1,1,2,2,2-pentafluoroethyl)silane Chemical compound C[Si](C)(C)C(F)(F)C(F)(F)F MTPVUVINMAGMJL-UHFFFAOYSA-N 0.000 description 1
- XKGLSKVNOSHTAD-UHFFFAOYSA-N valerophenone Chemical compound CCCCC(=O)C1=CC=CC=C1 XKGLSKVNOSHTAD-UHFFFAOYSA-N 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Images
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/11—Anti-reflection coatings
- G02B1/111—Anti-reflection coatings using layers comprising organic materials
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31507—Of polycarbonate
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31609—Particulate metal or metal compound-containing
- Y10T428/31612—As silicone, silane or siloxane
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31645—Next to addition polymer from unsaturated monomers
Definitions
- the invention relates to coating compositions and more particularly to the radiation curable coating compositions.
- Uncoated, optically transparent plastic and glass substrates such as ophthalmic lenses and cathode ray tube (CRT) screens reflect a portion of incident light.
- the amount of reflection varies with the wavelength, polarization, and angle of incidence of the light as well as the wavelength-dependent refractive index, n, of the material.
- the light loss reflected from the surfaces of uncoated substrates is on the order of about seven percent.
- Significantly more light loss occurs in transparent substrates having a high refractive index (e.g., refractive index on the order of 1.55 or higher).
- One method for reducing light reflection from optically transparent substrates is to coat the surfaces of the substrates with anti-reflective coatings.
- anti-reflective coatings As described in Optical Thin Films User's Handbook by James D. Rancourt, Macmillan Publishing Company, 1987, there are two common anti-reflective coating designs.
- One is the double layer structure of a first or bottom layer having a high refractive index and a second or top layer having a low refractive index with the corresponding thickness of quarter and quarter wavelength.
- the second anti-reflective coating design is the three layer structure of a first or bottom layer having a middle refractive index, a second or middle layer having a high refractive index, and a third or top layer having a low refractive index with the corresponding thickness of quarter, half, and quarter wavelength, respectively.
- the double layer anti-reflective coating has a V-shape pattern of reflectance in the visible wavelength spectrum, while the three layer anti-reflective coating has a broadband pattern of reflectance in the visible wavelength spectrum.
- the materials used for such anti-reflective coatings include oxides, nitrides, and fluorides of silicon (Si), titanium (Ti), aluminum (Al), zirconium (Zr), ashmony (Sb), boyillium (Be), bismuth (Bi), cerium (Ce), magnesium (Mg), hafnium (Hf), lanthanum (La), prascodymium (Pr), tantalum (Ta), etc.
- Numerous anti-reflective coating systems have been disclosed in the U.S. Pat. No. 4,130,672; U.S. Pat. No. 4,172,156; and U.S. Pat. No.5,172,812.
- the anti-reflective coatings in these documents are generally applied on transparent substrates primarily by a vacuum deposition processes, such as evaporation and sputtering. Although vacuum deposition techniques produce high quality anti-reflective coatings, they suffer from high cost limits in small optical laboratories.
- Non-vacuum cost-effective coating processes such as solution coating
- Solution coating processes are disclosed in the U.S. Pat. No. 4,361,598; U.S. Pat. No. 4,966,812; U.S. Pat. No. 5,476,717; U.S. Pat. No. 5,580,819; and U.S. Pat. No. 5,858,526.
- Such anti-reflective coatings made by a coating solution process generally must be cured for a certain amount of time at high temperature (e.g., up to 300° C. or even higher temperatures) to get enough hardness to be suitable.
- UV-curable monomer-containing coating formulations typically contain a photoinitiator which starts the polymerization reaction of the monomers under UV light. Following radiation curing, the coatings become hard and have good chemical resistance. Compared with thermal curing processes, radiation curing processes have more economic advantages such as fast cure of a few seconds, less heat generation, and low energy consumption. Radiation-curable compositions for abrasion and scratch resistant coatings are disclosed in the U.S. Pat. No. 3,989,609; U.S. Pat. No. 6,165,564; U.S. Patent No. 6,228,433; U.S. Pat. No. 6,232,360; and U.S. Pat. No. 6,241,505.
- FIG. 1 is a schematic cross-sectional side view of an anti-reflective coating having a stack of at least two layers on a substrate.
- FIG. 2 is a schematic cross-sectional side view of an anti-reflective coating having a stack of at least three layers on a substrate.
- FIG. 3 is a diagram of the reflectance of the ophthalmic lens without an anti-reflective coating and with an ultraviolet (UV)-cured anti-reflective coating.
- the coating composition comprises a plurality of layers at least one of which is a radiation-curable layer.
- the coating composition is suitable for coating transparent substrates such as glass and plastics, especially ophthalmic lenses.
- Such a coating composition may be selected to have a variety of different reflectance patterns in visible wavelengths.
- One reflectance pattern is a V-shape indicating a relatively narrow reflectance band and another pattern has broader reflectance pattern.
- a V-shaped reflectance pattern describes a reflectance pattern that minimizes reflectance of light (e.g., visible light) at a particular wavelength or around a particular wavelength, for example, at or around 550 nanometers (nm).
- a broader reflectance pattern describes a reflectance pattern that minimizes reflectance of light among a range of wavelengths (e.g., 450 nm to 650 nm). It is appreciate that with the techniques described herein for forming anti-reflective coatings, the V-shape and the broadband shape are optimizable for particular wavelengths or ranges of wavelengths by, for example, modifying the refractive index and thickness of the deposited layers that make-up the coatings.
- the V-shape anti-reflective coating composition described herein may be comprised of two layers: one having, relative to the other, a high refractive index and the other having a low refractive index.
- One arrangement of the layers is the high refractive index layer covered (coated) with the low refractive index layer.
- a broadband anti-reflective coating in one embodiment, may be composed of three layers: one or a first layer, for example, closest to the transparent substrate having, relative to the other layers, a medium refractive index, the one above it, or a second layer having a higher refractive index, and the top or third one having a low refractive index.
- FIG. 1 shows a schematic, cross-sectional view of an apparatus comprising a substrate having a coating composition formed thereon.
- the coating composition in this embodiment, is formed of a plurality of deposited layers at least one of which comprises a radiation-curable (e.g., ultraviolet curable, electron-beam radiation curable, etc.) material.
- FIG. 1 shows apparatus 100 including a substrate with two deposited layers selected to have a V-shape (or single) reflectance pattern in the visible wavelength spectrum.
- substrate 110 is an organic polymer (e.g., plastic), glass, ceramic, or metal material.
- substrate 110 is a transparent material such as an organic polymer or glass.
- hardcoat layer 115 is formed over a surface of substrate 110 (in FIG. 1 , a superior surface) of a material that may be known in the industry.
- One suitable material for hardcoat layer 115 is polysiloxane.
- first deposited layer 120 Overlying a surface of substrate 110 (e.g., a superior surface as shown) and optional hardcoat layer 115 is first deposited layer 120 .
- First deposited layer 120 is selected to have a relatively high index of refraction (e.g., relative to a subsequent layer).
- first deposited layer 120 is a colloid material of a metal compound, including, but not limited to, metal oxides, metal carbides, and metal nitrides combined/modified with a condensation product of an organosilane (e.g., tetramethoxysilane).
- Suitable metal oxides include, but are not limited to, aluminum oxide (Al 2 O 3 ), titanium oxide (e.g., TiO 2 ), zinc oxide, and iron oxide.
- Suitable metal carbides include, but are not limited to, titanium carbide.
- Suitable metal nitrides include, but are not limited to, titanium nitride.
- the metal compounds are preferably crystalline powders made, for example, by vacuum processes or wet processes. Through, for example, a grinding process, the particles are selected to have a particle size suitable for forming a transparent layer or film. One particle size is less than one micron and on the order of one hundred to several hundred nanometers.
- the concentration of the colloids are preferably controlled between 10 and 20 weight percent.
- the colloidal coating solutions that are used to form first deposited layer 120 are made by dispersing the metal compound particles (combined/modified with a condensation product of an organosilane) with a dispersing agent such as an amide-based dispersing agent, e.g., dimethylformamide, and subsequently, diluting the concentrated colloids to 1 to 5 weight percent with solvents.
- Suitable solvents are those that do not destroy the colloidal properties of the colloid, such as alcohols and water.
- the refractive indices of the layers made of the colloids may be adjusted by varying the amount of organosilanes contained therein.
- the organosilanes used for modification of the metal oxides, nitrides, or carbides include, but are not limited to, organosilanes such as tetraalkoxysilane, trialkoxysilane or dialkoxysilane.
- Organosilanes tend to reduce the refractive index of the colloidal particles. In general, the greater the quantity of organosilanes in the surface of the colloidal particles, the lower refractive index of the layer.
- first deposited layer 120 of a V-shape anti-reflective coating has a refractive index that varies, in one example, from 1.45 to 1.75 (e.g., relatively high refractive index).
- first deposited layer 120 of, for example, a colloid is introduced by a spinning process. Spinning continues for about one minute to form a stable layer over a surface of substrate 110 having a thickness on the order of 50 to 150 nm (e.g., 90 nm).
- first deposited layer 120 on substrate 110 is second deposited layer 130 .
- second deposited layer 130 is selected to have a relatively low refractive index, on the order of 1.30 to 1.50.
- Selected material for second deposited layer 130 is a radiation-curable material.
- Acrylate monomers preferably multi-functional (meth)acrylate monomers can be used as binders of the top layer. Any multifunctional (meth)acrylate can be used as long as the selected monomer does not create stability (“gelling”) or viscosity problems of the corresponding coating solution.
- second deposited layer 130 composition include at least one multifunctional (meth)acrylate monomer that has a functionality of at least three.
- Typical (meth)acrylates include, but are not limited to, propoxylated trimethylolpropane triacrylate (CD 501, SARTOMER), ethoxylated trimethyolpropane triacrylate (SR-502, SARTOMET), highly propoxylated (5.5) glyceryl triacrylate (CD9021, SARTOMER), ethoxylated trimethlolprone triacrylate (SR-454HP, SARTOMER), dipentaerythritol pentaacrylate (SR 399, SARTOMER).
- the composition of second deposited layer 130 contains one to ten weight percent of multifunctional (meth)acrylate monomers, preferably, three to six weight percent of the multifinctional (meth)acrylate monomers.
- the monomers polymerize without catalysis under electron beam irradiation.
- a photoinitiator may be included into the top coating solution to initiate or catalyze the polymerization reaction of the monomers when they are placed under ultraviolet (UV) light radiation.
- UV ultraviolet
- the top coating compositions contain on the order of about 10 percent by weight of a photoinitiator. In another embodiment the top coating composition contains preferably 0.5 to 5 percent by weight photoinitiator.
- suitable photoinitiators used include, but are not limited to, 2-butoxy-1,2 diphenylethanone, 2,2-dimethoxy-1,2-diphenylethanone and 2,4,6-trimethylbenzophenone, benzophenone, hydroxycyclohexyl phenylketone, acetophenone, acenaphthenequinone, o-methoxy benzophenone, thioxanthen-9-one, xanthen-9-one, 7H-Benz(de)anthracen-7-one, dibenzosuberone, 1-naphthaldehyde, 4,4′-bis(dimethylamino) benzophenone, fluorine-9-one, 1′-acetonaphthane anthraquinone, 1-indanone, 2-tertbutylanthraquinone, valerophenone, hexanophenone, 3-phenylbutyrophenone, p-morpholinopropiophenone
- fluoroalkyl-containing compounds may be incorporated into the formulation of second deposited layer 130 . It is believed that fluoroalkyl-containing compounds tend to decrease the refractive index of the top layer.
- Suitable fluoroalkyl-containing compounds are the polycondensed products of a mixture of alkoxysilanes. In one embodiment, the mixture may be, but is not limited to, tetraethoxysilane or tetramethoxysilane, and a trialkoxysilane or dialkoxysilane having a perfluoroalkyl group containing from 3 to 20 carbon atoms.
- the chemical structure of a trialkoxysilane is representatively given as follows: C x F 2x+1 Si(OR) 3
- R represents, in one example, a lower C1-C4 alkoxy group selected from the group consisting of methoxy, ethoxy, isopropoxy and n-butoxy, and x varies from 3 to 20.
- the fluoroalkyl-containing silicon compounds are prepared in such a manner that the mixture of the tetraalkoxysilane and the trialkoxysilane or dialkoxysilane having a perfluoroalkyl group is hydrolyzed with water in a single or mixed alcoholic solvent, and then polycondensed.
- An acid such as nitric acid, may be added into the mixture before hydrolysis to act as a catalyst.
- the hydrolysis and polycondensation reaction may run at 30-50° C. for 10-20 hours.
- the polycondensed fluoroalkyl-containing silicon compound is then added into the second deposited layer 130 formulation, wherein the solid content of the fluoroalkyl-containing silicon compound may be at least 0.5 percent by weight. In another embodiment, the solid content of the fluoroalkyl-containing silicon compound may be 2 percent by weight.
- a solvent may further be added into the formulation of second deposited layer 130 .
- the solvent for the top coating composition may be a mixture of an alcohol solvent having a lower boiling point, such as C1-C4 alcohol (methanol and ethanol being preferred), a ketone such as methyl ethyl ketone and methyl propyl ketone, and a viscous solvent having higher boiling point, such as ethylene glycol monomethyl ether and ethylene glycol.
- second deposited layer 130 is introduced by a spinning process. Spinning continues for about one minute to form a stable layer having a thickness on the order of 50 to 150 nm (e.g., 100 nm).
- the composite structure may be cured to harden the deposited layers, particularly second deposited layer 130 .
- the cure is accomplished by exposing apparatus 100 to a radiation source such as an UV or e-beam radiation source (dependent, to an extend on the material selected for second deposited layer 130 ).
- the composite structure (apparatus 100 ) has an anti-reflective property.
- the composite structure is formed of a substrate (e.g., substrate 110 ) of, for example, a transparent material. Overlying substrate 110 (and optional hard coat layer 115 ) is first deposited layer 120 and radiation-curable second deposited layer 130 .
- first deposited layer 120 is selected to have a relatively high refractive index (relative to the individual layers) of, for example, 1.45 to 1.55.
- second deposited layer 130 of, for example, a radiation curable material having a relatively low refractive index on the order of 1.30 to 1.50.
- FIG. 2 shows a schematic, cross-sectional view of an apparatus comprising a coating composition formed thereon.
- the coating composition is selected to have a broadband reflectance pattern in the visible wavelength spectrum.
- apparatus 200 includes substrate 210 of an organic polymer (e.g., plastic), glass, ceramic or metal materials.
- substrate 210 is a transparent material such as an organic polymer or glass.
- first deposited layer 220 is a colloid of a metal compound (e.g., metal oxide, metal nitride, metal carbide, etc.) combined/modified with an organosilane (e.g., tetraoxysilane).
- a metal compound e.g., metal oxide, metal nitride, metal carbide, etc.
- an organosilane e.g., tetraoxysilane
- the material of first deposited layer 220 is similar to the first deposited layer 120 of FIG. 1 .
- the refractive index of first deposited layer 220 is selected to be on the order of 1.45 to 1.55.
- the refractive index may be adjusted by varying the amount of organosilanes contained in the coating solution used to form first deposited layer 220 .
- the concentration of the colloids in the coating solution are preferably controlled between 10 and 20 weight percent and the coating solution may be made by diluting the concentrated colloids with solvents on the order of one to five weight percent.
- the coating solution used to form first deposited layer 220 may be introduced by a spinning process, continuing for about one minute, to form a layer having a thickness on the order of 50to 150nm.
- second deposited layer 230 is Overlying first deposited layer in the structure (apparatus 200 ) of FIG. 2 .
- second deposited layer 230 is also formed from a colloid composition combined/modified with a condensation product of organosilanes.
- second deposited layer 230 is selected to have a refractive index on the order of 1.50 to 1.75.
- second deposited layer 230 may be formed from a coating solution introduced, in one example, by spinning (for about one minute) to a thickness on the order of 90 to 200 nm.
- third deposited layer 240 is selected to be a radiation-curable (e.g., e-beam or UV curable material) similar to second deposited layer 130 described with reference to FIG. 1 and the accompanying text.
- Multi-functional acrylate monomers e.g., (meth)acrylate monomers
- a photoinitiator e.g., in the case of UV curable monomers
- additives such as fluoro-alkyl-containing additives
- Third deposited layer 240 is selected, in an example of forming a composite coating (of three deposited layers), to have a refractive index on the order of 1.30 to 1.50.
- a coating solution may be introduced by spinning onto the surface of substrate 200 (e.g., the superior surface) to a thickness on the order of 50 to 150 nm.
- FIG. 3 shows a representative example of the reflectance of an ophthalmic lens without an anti-reflective coating and with a UV curable anti-reflective coating selected to have a broadband reflectance in the visible spectrum similar to the three layer coating described above with reference to FIG. 2 and the accompanying text.
- the composite structures are described as including a plurality of layers on a substrate. It is appreciated that the individual layers thought possibly distinctly deposited, do not necessarily overlie one another with a distinct interface between each layer. Instead, particularly with spin operations, the plurality of layers may blend together to some extent.
- the method described above to form a composite substrate is a relatively inexpensive, generally simpler method compared to prior techniques as it eliminates the need for expensive evaporators or plasma equipment.
- the formulating of the deposited layer materials do not require complex or expensive equipment.
- Simple film application techniques, including spinning, dipping, rolling, or spraying permit the coating of large complicated shapes, and even simultaneous coating of the inner and outer surfaces of a tube.
- the large scale application of a surface coating is possible without a limit on the size of the part to be coated.
- the method described above and the materials selected eliminate the necessity to heat and/or etch the coating to produce an anti-reflecting film on a substrate.
- the composite coating of the invention is particularly useful for coating various substrates such as glass, ceramics, metals, and organic polymeric materials to increase light transmission, without a need to subject the coating or the substrate to high temperature curing processes.
- Substrates coated with the coating of the invention may be used, for example, in ophthalmic lenses, display filters and solar photovoltaic applications.
- the antireflection coating may be fabricated as follows.
- TEOS tetraethoxysilane
- the mixture was then stirred at 70 degree C. for 5 hours.
- the mixture was dried at 150 degree C. for 6 hours to get SiO 2 -modified TiO 2 powder.
- the powder was crystallized at 700 degree C. for 2 hours.
- the powder was then dispersed into colloid by grinding.
- the solid content of the SiO 2 modified TiO 2 colloid was controlled from 10 to 20 weight percent.
- the colloid was diluted into 1 to 5 weight percent with the solvent mixture of methanol, ethanol, methyl ethyl ketone, and ethylene glycol.
- the preparation of coating composition of the first layer was repeated except that less amount of tetraehoxysilane was added into the TiO 2 colloid. 120 gram of tetraethoxysilane (TEOS) was dropped into 3370 gram of TiO 2 , colloid.
- TEOS tetraethoxysilane
- the polycondensed fluorine-containing silicon compounds are prepared as follows:
- the resulting product was mixed to form a transparent UV-curable composition for the top layer.
- the coating solution for first layer was injected on the front side of the polycarbonate ophthalmic lens during spinning the lens with the speed of 500 to 1500 RPM and then the coated lens was spun more for 1 minute to stabilize the first layer.
- the coating solution for second layer was injected on the surface of the first layer during spinning the lens with the speed of 500 to 1500 RPM and then the coated lens was spun more for 1 minute to stabilize the second layer.
- the coating solution for top layer was injected on the surface of the second layer during spinning the lens with the speed of 500 to 1500 RPM and then the coated lens was spun more for 1 minute to stabilize the top layer.
- the coated lens was cured for 30 seconds with the UV (ultraviolet) light of a medium pressure mercury.
- FIG. 2 shows the reflectance pattern of the ophthalmic lens with the invented UV (ultraviolet)-cured anti-reflective coating.
- the reflectance of the coated lens was broad and less than 2 percent in the visible wavelength.
Abstract
A radiation-curable anti-reflective coating is disclosed. The coating may be deposited on a substrate by spinning, dipping or rolling. The anti-reflective coating may have two layers in which case the anti-reflective coating has a V-shaped reflectance pattern in the visible wavelength spectrum. The anti-reflective coating may have three layers in which case the anti-reflective coating has a broadband reflectance pattern in the visible wavelength spectrum.
Description
- The application is a Divisional of co-pending U.S. Pat. Application Ser. No. 10/001,639, filed Oct. 31, 2001.
- 1. Field of the Invention
- The invention relates to coating compositions and more particularly to the radiation curable coating compositions.
- 2. Description of Related Art
- Uncoated, optically transparent plastic and glass substrates such as ophthalmic lenses and cathode ray tube (CRT) screens reflect a portion of incident light. The amount of reflection varies with the wavelength, polarization, and angle of incidence of the light as well as the wavelength-dependent refractive index, n, of the material. Usually, the light loss reflected from the surfaces of uncoated substrates is on the order of about seven percent. Significantly more light loss occurs in transparent substrates having a high refractive index (e.g., refractive index on the order of 1.55 or higher).
- One method for reducing light reflection from optically transparent substrates is to coat the surfaces of the substrates with anti-reflective coatings. As described in Optical Thin Films User's Handbook by James D. Rancourt, Macmillan Publishing Company, 1987, there are two common anti-reflective coating designs. One is the double layer structure of a first or bottom layer having a high refractive index and a second or top layer having a low refractive index with the corresponding thickness of quarter and quarter wavelength. The second anti-reflective coating design is the three layer structure of a first or bottom layer having a middle refractive index, a second or middle layer having a high refractive index, and a third or top layer having a low refractive index with the corresponding thickness of quarter, half, and quarter wavelength, respectively. The double layer anti-reflective coating has a V-shape pattern of reflectance in the visible wavelength spectrum, while the three layer anti-reflective coating has a broadband pattern of reflectance in the visible wavelength spectrum. The materials used for such anti-reflective coatings include oxides, nitrides, and fluorides of silicon (Si), titanium (Ti), aluminum (Al), zirconium (Zr), ashmony (Sb), boyillium (Be), bismuth (Bi), cerium (Ce), magnesium (Mg), hafnium (Hf), lanthanum (La), prascodymium (Pr), tantalum (Ta), etc. Numerous anti-reflective coating systems have been disclosed in the U.S. Pat. No. 4,130,672; U.S. Pat. No. 4,172,156; and U.S. Pat. No.5,172,812. The anti-reflective coatings in these documents are generally applied on transparent substrates primarily by a vacuum deposition processes, such as evaporation and sputtering. Although vacuum deposition techniques produce high quality anti-reflective coatings, they suffer from high cost limits in small optical laboratories.
- Non-vacuum cost-effective coating processes, such as solution coating, have been developed to replace vacuum deposition processes. Solution coating processes are disclosed in the U.S. Pat. No. 4,361,598; U.S. Pat. No. 4,966,812; U.S. Pat. No. 5,476,717; U.S. Pat. No. 5,580,819; and U.S. Pat. No. 5,858,526. Such anti-reflective coatings made by a coating solution process generally must be cured for a certain amount of time at high temperature (e.g., up to 300° C. or even higher temperatures) to get enough hardness to be suitable. This high curing temperature and long curing process limits the application of the anti-reflective coatings only to glass substrates which are generally not deformed during thermal curing at high temperature. Plastic substrates, such as ophthalmic lenses, are easily deformed or burned at temperatures up to 300° C.
- Radiation curing is used in the coating industry. Under high energy radiation such as ultraviolet (UV) light or electron beam radiation, the monomer-containing solution polymerizes to form a hard layer. UV-curable monomer-containing coating formulations typically contain a photoinitiator which starts the polymerization reaction of the monomers under UV light. Following radiation curing, the coatings become hard and have good chemical resistance. Compared with thermal curing processes, radiation curing processes have more economic advantages such as fast cure of a few seconds, less heat generation, and low energy consumption. Radiation-curable compositions for abrasion and scratch resistant coatings are disclosed in the U.S. Pat. No. 3,989,609; U.S. Pat. No. 6,165,564; U.S. Patent No. 6,228,433; U.S. Pat. No. 6,232,360; and U.S. Pat. No. 6,241,505.
-
FIG. 1 is a schematic cross-sectional side view of an anti-reflective coating having a stack of at least two layers on a substrate. -
FIG. 2 is a schematic cross-sectional side view of an anti-reflective coating having a stack of at least three layers on a substrate. -
FIG. 3 is a diagram of the reflectance of the ophthalmic lens without an anti-reflective coating and with an ultraviolet (UV)-cured anti-reflective coating. - An apparatus comprising a substrate having a coating composition formed thereon is disclosed. In one embodiment, the coating composition comprises a plurality of layers at least one of which is a radiation-curable layer. The coating composition is suitable for coating transparent substrates such as glass and plastics, especially ophthalmic lenses. Such a coating composition may be selected to have a variety of different reflectance patterns in visible wavelengths. One reflectance pattern is a V-shape indicating a relatively narrow reflectance band and another pattern has broader reflectance pattern. Generally speaking, a V-shaped reflectance pattern describes a reflectance pattern that minimizes reflectance of light (e.g., visible light) at a particular wavelength or around a particular wavelength, for example, at or around 550 nanometers (nm). A broader reflectance pattern describes a reflectance pattern that minimizes reflectance of light among a range of wavelengths (e.g., 450 nm to 650 nm). It is appreciate that with the techniques described herein for forming anti-reflective coatings, the V-shape and the broadband shape are optimizable for particular wavelengths or ranges of wavelengths by, for example, modifying the refractive index and thickness of the deposited layers that make-up the coatings.
- The V-shape anti-reflective coating composition described herein may be comprised of two layers: one having, relative to the other, a high refractive index and the other having a low refractive index. One arrangement of the layers is the high refractive index layer covered (coated) with the low refractive index layer. A broadband anti-reflective coating, in one embodiment, may be composed of three layers: one or a first layer, for example, closest to the transparent substrate having, relative to the other layers, a medium refractive index, the one above it, or a second layer having a higher refractive index, and the top or third one having a low refractive index.
-
FIG. 1 shows a schematic, cross-sectional view of an apparatus comprising a substrate having a coating composition formed thereon. The coating composition, in this embodiment, is formed of a plurality of deposited layers at least one of which comprises a radiation-curable (e.g., ultraviolet curable, electron-beam radiation curable, etc.) material.FIG. 1 shows apparatus 100 including a substrate with two deposited layers selected to have a V-shape (or single) reflectance pattern in the visible wavelength spectrum. - Referring to
FIG. 1 , in one embodiment,substrate 110 is an organic polymer (e.g., plastic), glass, ceramic, or metal material. In one embodiment,substrate 110 is a transparent material such as an organic polymer or glass. Optionally formed over a surface of substrate 110 (inFIG. 1 , a superior surface) ishardcoat layer 115 of a material that may be known in the industry. One suitable material forhardcoat layer 115 is polysiloxane. - Overlying a surface of substrate 110 (e.g., a superior surface as shown) and
optional hardcoat layer 115 is first depositedlayer 120. First depositedlayer 120, in one example, is selected to have a relatively high index of refraction (e.g., relative to a subsequent layer). In one embodiment, first depositedlayer 120 is a colloid material of a metal compound, including, but not limited to, metal oxides, metal carbides, and metal nitrides combined/modified with a condensation product of an organosilane (e.g., tetramethoxysilane). Suitable metal oxides include, but are not limited to, aluminum oxide (Al2O3), titanium oxide (e.g., TiO2), zinc oxide, and iron oxide. Suitable metal carbides include, but are not limited to, titanium carbide. Suitable metal nitrides include, but are not limited to, titanium nitride. The metal compounds are preferably crystalline powders made, for example, by vacuum processes or wet processes. Through, for example, a grinding process, the particles are selected to have a particle size suitable for forming a transparent layer or film. One particle size is less than one micron and on the order of one hundred to several hundred nanometers. - The concentration of the colloids are preferably controlled between 10 and 20 weight percent. The colloidal coating solutions that are used to form first deposited
layer 120 are made by dispersing the metal compound particles (combined/modified with a condensation product of an organosilane) with a dispersing agent such as an amide-based dispersing agent, e.g., dimethylformamide, and subsequently, diluting the concentrated colloids to 1 to 5 weight percent with solvents. Suitable solvents are those that do not destroy the colloidal properties of the colloid, such as alcohols and water. - The refractive indices of the layers made of the colloids may be adjusted by varying the amount of organosilanes contained therein. The organosilanes used for modification of the metal oxides, nitrides, or carbides include, but are not limited to, organosilanes such as tetraalkoxysilane, trialkoxysilane or dialkoxysilane. Organosilanes tend to reduce the refractive index of the colloidal particles. In general, the greater the quantity of organosilanes in the surface of the colloidal particles, the lower refractive index of the layer. In one embodiment, first deposited
layer 120 of a V-shape anti-reflective coating has a refractive index that varies, in one example, from 1.45 to 1.75 (e.g., relatively high refractive index). - In one example, first deposited
layer 120 of, for example, a colloid is introduced by a spinning process. Spinning continues for about one minute to form a stable layer over a surface ofsubstrate 110 having a thickness on the order of 50 to 150 nm (e.g., 90 nm). - Referring to
FIG. 1 , overlying first depositedlayer 120 onsubstrate 110 is second depositedlayer 130. In an embodiment whereapparatus 100 ofFIG. 1 is selected to have a. V-shape reflectance band (andfirst layer 120 is selected to have a relatively high index of refraction (e.g., 1.45 to 1.75) over a transparent substrate), second depositedlayer 130 is selected to have a relatively low refractive index, on the order of 1.30 to 1.50. - Selected material for second deposited
layer 130 is a radiation-curable material. Acrylate monomers, preferably multi-functional (meth)acrylate monomers can be used as binders of the top layer. Any multifunctional (meth)acrylate can be used as long as the selected monomer does not create stability (“gelling”) or viscosity problems of the corresponding coating solution. In order to make a hard anti-reflective coating, however, it is desired that second depositedlayer 130 composition include at least one multifunctional (meth)acrylate monomer that has a functionality of at least three. Typical (meth)acrylates include, but are not limited to, propoxylated trimethylolpropane triacrylate (CD 501, SARTOMER), ethoxylated trimethyolpropane triacrylate (SR-502, SARTOMET), highly propoxylated (5.5) glyceryl triacrylate (CD9021, SARTOMER), ethoxylated trimethlolprone triacrylate (SR-454HP, SARTOMER), dipentaerythritol pentaacrylate (SR 399, SARTOMER). Among the acrylates, dipentaerythritol pentaacrylate (SR 399), propoxylated trimethylolpropane triacrylate (CD 501), glyceryl triacrylate (CD9021) are preferred. These monomers may be used alone. However, to adjust the refractive index, hardness and adhesion of the layer, it is preferred to employ two or more monomers. In one embodiment, the composition of second depositedlayer 130 contains one to ten weight percent of multifunctional (meth)acrylate monomers, preferably, three to six weight percent of the multifinctional (meth)acrylate monomers. - In one embodiment, the monomers polymerize without catalysis under electron beam irradiation. In another embodiment, a photoinitiator may be included into the top coating solution to initiate or catalyze the polymerization reaction of the monomers when they are placed under ultraviolet (UV) light radiation. In one embodiment, the top coating compositions contain on the order of about 10 percent by weight of a photoinitiator. In another embodiment the top coating composition contains preferably 0.5 to 5 percent by weight photoinitiator.
- In one embodiment, suitable photoinitiators used include, but are not limited to, 2-butoxy-1,2 diphenylethanone, 2,2-dimethoxy-1,2-diphenylethanone and 2,4,6-trimethylbenzophenone, benzophenone, hydroxycyclohexyl phenylketone, acetophenone, acenaphthenequinone, o-methoxy benzophenone, thioxanthen-9-one, xanthen-9-one, 7H-Benz(de)anthracen-7-one, dibenzosuberone, 1-naphthaldehyde, 4,4′-bis(dimethylamino) benzophenone, fluorine-9-one, 1′-acetonaphthane anthraquinone, 1-indanone, 2-tertbutylanthraquinone, valerophenone, hexanophenone, 3-phenylbutyrophenone, p-morpholinopropiophenone, 4-morpholinobenzophenone, p-diacetyl-benzene, 4-amino-benzophenone, 4′methoxyacetophenone, benzaldehyde, 9-acetylphenanthrene, 2-acetylphenanthrone, 10-thioxanthenone, 3-acetylphenanthrene, 3-acetylindole, 1,3,5-triacetylbenzene and like, including blends thereof. In one embodiment, the photoinitiators, 2-butoxy-1,2 diphenylethanone, 2,2-dimethoxy-1,2-diphenylethanone, 2,4,6-trimethylbenzophenone, and benzophenone are preferable.
- In another embodiment, other additives, such as fluoroalkyl-containing compounds, may be incorporated into the formulation of second deposited
layer 130. It is believed that fluoroalkyl-containing compounds tend to decrease the refractive index of the top layer. Suitable fluoroalkyl-containing compounds are the polycondensed products of a mixture of alkoxysilanes. In one embodiment, the mixture may be, but is not limited to, tetraethoxysilane or tetramethoxysilane, and a trialkoxysilane or dialkoxysilane having a perfluoroalkyl group containing from 3 to 20 carbon atoms. The chemical structure of a trialkoxysilane is representatively given as follows:
CxF2x+1Si(OR)3 - wherein R represents, in one example, a lower C1-C4 alkoxy group selected from the group consisting of methoxy, ethoxy, isopropoxy and n-butoxy, and x varies from 3 to 20.
- In one embodiment, the fluoroalkyl-containing silicon compounds are prepared in such a manner that the mixture of the tetraalkoxysilane and the trialkoxysilane or dialkoxysilane having a perfluoroalkyl group is hydrolyzed with water in a single or mixed alcoholic solvent, and then polycondensed. An acid, such as nitric acid, may be added into the mixture before hydrolysis to act as a catalyst. In one embodiment, the hydrolysis and polycondensation reaction may run at 30-50° C. for 10-20 hours. The polycondensed fluoroalkyl-containing silicon compound is then added into the second deposited
layer 130 formulation, wherein the solid content of the fluoroalkyl-containing silicon compound may be at least 0.5 percent by weight. In another embodiment, the solid content of the fluoroalkyl-containing silicon compound may be 2 percent by weight. - A solvent may further be added into the formulation of second deposited
layer 130. The solvent for the top coating composition may be a mixture of an alcohol solvent having a lower boiling point, such as C1-C4 alcohol (methanol and ethanol being preferred), a ketone such as methyl ethyl ketone and methyl propyl ketone, and a viscous solvent having higher boiling point, such as ethylene glycol monomethyl ether and ethylene glycol. - In one example, second deposited
layer 130 is introduced by a spinning process. Spinning continues for about one minute to form a stable layer having a thickness on the order of 50 to 150 nm (e.g., 100 nm). Following deposition, the composite structure may be cured to harden the deposited layers, particularly second depositedlayer 130. In one embodiment, the cure is accomplished by exposingapparatus 100 to a radiation source such as an UV or e-beam radiation source (dependent, to an extend on the material selected for second deposited layer 130). - In one embodiment, shown in
FIG. 1 , the composite structure (apparatus 100) has an anti-reflective property. The composite structure is formed of a substrate (e.g., substrate 110) of, for example, a transparent material. Overlying substrate 110 (and optional hard coat layer 115) is first depositedlayer 120 and radiation-curable second depositedlayer 130. In an embodiment where the composite structure has a V-shape reflectance pattern in the visible wavelength spectrum, first depositedlayer 120 is selected to have a relatively high refractive index (relative to the individual layers) of, for example, 1.45 to 1.55. Overlying first depositedlayer 120 is second depositedlayer 130 of, for example, a radiation curable material having a relatively low refractive index on the order of 1.30 to 1.50. -
FIG. 2 shows a schematic, cross-sectional view of an apparatus comprising a coating composition formed thereon. In this example, the coating composition is selected to have a broadband reflectance pattern in the visible wavelength spectrum. - Referring to
FIG. 2 ,apparatus 200 includessubstrate 210 of an organic polymer (e.g., plastic), glass, ceramic or metal materials. In one example,substrate 210 is a transparent material such as an organic polymer or glass. - Optionally formed over a surface of substrate 210 (in
FIG. 2 , a superior surface) ishardcoat layer 215 such a polysiloxane. Overlyingoptional hardcoat layer 215 is first depositedlayer 220. In one embodiment, first depositedlayer 220 is a colloid of a metal compound (e.g., metal oxide, metal nitride, metal carbide, etc.) combined/modified with an organosilane (e.g., tetraoxysilane). In this regard, the material of first depositedlayer 220 is similar to the first depositedlayer 120 ofFIG. 1 . In one embodiment, the refractive index of first depositedlayer 220 is selected to be on the order of 1.45 to 1.55. The refractive index may be adjusted by varying the amount of organosilanes contained in the coating solution used to form first depositedlayer 220. The concentration of the colloids in the coating solution are preferably controlled between 10 and 20 weight percent and the coating solution may be made by diluting the concentrated colloids with solvents on the order of one to five weight percent. - The coating solution used to form first deposited
layer 220 may be introduced by a spinning process, continuing for about one minute, to form a layer having a thickness on the order of 50to 150nm. - Overlying first deposited layer in the structure (apparatus 200) of
FIG. 2 is second depositedlayer 230. In one embodiment, second depositedlayer 230 is also formed from a colloid composition combined/modified with a condensation product of organosilanes. In the example of forming a composite coating (of three deposited layers and a broadband spectrum), second depositedlayer 230 is selected to have a refractive index on the order of 1.50 to 1.75. Like first depositedlayer 220, second depositedlayer 230 may be formed from a coating solution introduced, in one example, by spinning (for about one minute) to a thickness on the order of 90 to 200 nm. - Overlying second deposited
layer 230 in the structure (apparatus 200) shown inFIG. 2 is third depositedlayer 240. In one example, third depositedlayer 240 is selected to be a radiation-curable (e.g., e-beam or UV curable material) similar to second depositedlayer 130 described with reference toFIG. 1 and the accompanying text. Multi-functional acrylate monomers (e.g., (meth)acrylate monomers), possibly two or more combined with a photoinitiator (e.g., in the case of UV curable monomers) and possibly containing additives, such as fluoro-alkyl-containing additives, are suitable. Third depositedlayer 240 is selected, in an example of forming a composite coating (of three deposited layers), to have a refractive index on the order of 1.30 to 1.50. A coating solution may be introduced by spinning onto the surface of substrate 200 (e.g., the superior surface) to a thickness on the order of 50 to 150 nm. -
FIG. 3 shows a representative example of the reflectance of an ophthalmic lens without an anti-reflective coating and with a UV curable anti-reflective coating selected to have a broadband reflectance in the visible spectrum similar to the three layer coating described above with reference toFIG. 2 and the accompanying text. - In the above examples, the composite structures are described as including a plurality of layers on a substrate. It is appreciated that the individual layers thought possibly distinctly deposited, do not necessarily overlie one another with a distinct interface between each layer. Instead, particularly with spin operations, the plurality of layers may blend together to some extent.
- The method described above to form a composite substrate is a relatively inexpensive, generally simpler method compared to prior techniques as it eliminates the need for expensive evaporators or plasma equipment. The formulating of the deposited layer materials do not require complex or expensive equipment. Simple film application techniques, including spinning, dipping, rolling, or spraying permit the coating of large complicated shapes, and even simultaneous coating of the inner and outer surfaces of a tube. The large scale application of a surface coating is possible without a limit on the size of the part to be coated. As noted above, there are many prior art anti-reflective surface coatings applied to vitreous substrates. However, the method described above and the materials selected eliminate the necessity to heat and/or etch the coating to produce an anti-reflecting film on a substrate.
- The composite coating of the invention is particularly useful for coating various substrates such as glass, ceramics, metals, and organic polymeric materials to increase light transmission, without a need to subject the coating or the substrate to high temperature curing processes. Substrates coated with the coating of the invention may be used, for example, in ophthalmic lenses, display filters and solar photovoltaic applications.
- Having been generally described, the following example describes a particular embodiment, to illustrate some of the properties and demonstrate the practical advantages thereof, and to allow one skilled in the art to utilize the invention. It is understood that these examples are to be construed as merely illustrative.
- In one embodiment, the antireflection coating may be fabricated as follows.
- 1) The Preparation of Coating Composition of the First Layer with Medium Refractive Index.
- 350 grams of tetraethoxysilane (TEOS) was dropped into water based 20 weight percent TiO2 colloid during stirring. The mixture was then stirred at 70 degree C. for 5 hours. The mixture was dried at 150 degree C. for 6 hours to get SiO2-modified TiO2 powder. The powder was crystallized at 700 degree C. for 2 hours. The powder was then dispersed into colloid by grinding. The solid content of the SiO2 modified TiO2 colloid was controlled from 10 to 20 weight percent. The colloid was diluted into 1 to 5 weight percent with the solvent mixture of methanol, ethanol, methyl ethyl ketone, and ethylene glycol.
- 2) The Preparation of the Coating Composition of the Second Layer with High Refractive Index.
- The preparation of coating composition of the first layer was repeated except that less amount of tetraehoxysilane was added into the TiO2 colloid. 120 gram of tetraethoxysilane (TEOS) was dropped into 3370 gram of TiO2, colloid.
- 3) Preparation of the UV-Curable Coating Composition of the Top Layer with Low Refractive Index.
- The polycondensed fluorine-containing silicon compounds are prepared as follows:
- 25 grams of (tridecafluoro-1,1,2,2-tetrahydrooctyl) triethoxysilane was mixed with 100 grams of tetraethoxysilane (TEOS) and 90 grams of HNO3 aqueous solution (containing 1 gram HNO3). The mixture was left in a closed glass container at 50° C. for 12 hours and then cooled slowly to room temperature. The product was named as FCSC and kept in a refrigerate prior to use. The following ingredients were added in the sequence listed to a plastic container and were mixed gently for 20 minutes.
FCSC 5 grams Methanol 10 grams ethylene glycol monomethyl ether 40 grams Dipentaerythritol pentaacrylate (SR-399, Sartomer) 3.5 grams Highly propoxylatd glyceryl triacrylate 2.5 grams (SR-9021, Sartomer) Finally other two ingredients were added into the mixture: 2,4,6-trimethylbenzophenone 0.5 grams Eethylene glycol monomethyl ether 20 grams - The resulting product was mixed to form a transparent UV-curable composition for the top layer.
- 4) Application and Curing of an Anti-Reflective Coating on an Ophthalmic Lens.
- The coating solution for first layer was injected on the front side of the polycarbonate ophthalmic lens during spinning the lens with the speed of 500 to 1500 RPM and then the coated lens was spun more for 1 minute to stabilize the first layer. Without interruption the coating solution for second layer was injected on the surface of the first layer during spinning the lens with the speed of 500 to 1500 RPM and then the coated lens was spun more for 1 minute to stabilize the second layer. Finally the coating solution for top layer was injected on the surface of the second layer during spinning the lens with the speed of 500 to 1500 RPM and then the coated lens was spun more for 1 minute to stabilize the top layer. The coated lens was cured for 30 seconds with the UV (ultraviolet) light of a medium pressure mercury. The coating process for the front side of the lens was repeated to apply coatings on the backside of the lens.
FIG. 2 shows the reflectance pattern of the ophthalmic lens with the invented UV (ultraviolet)-cured anti-reflective coating. The reflectance of the coated lens was broad and less than 2 percent in the visible wavelength. - In the preceding detailed description, the invention is described with reference to specific embodiments thereof. It will, however, be evident that various modifications and changes may be made thereto without departing from the broader spirit and scope of the invention as set forth in the claims. The specification and drawings are, accordingly, to be regarded in an illustrative rather than a restrictive sense.
Claims (8)
1. A method comprising:
depositing a plurality of layers on a substrate, at least one of which comprises a radiation-curable material; and
curing at least one deposited layer by exposure to a radiation source.
2. The method of claim 1 , wherein the plurality of layers comprises at least two layers, and relative to one another, a first layer has a high refractive index and a second layer has a low refractive index.
3. The method of claim 1 , wherein the plurality of layers comprises at least three layers, and relative to one another, a first layer has a medium refractive index, a second layer has a high refractive index and a third layer has a low refractive index.
4. The method of claim 1 , wherein the radiation source comprises an electron beam.
5. The method of claim 1 , wherein the radiation source comprises ultraviolet light.
6. The method of claim 1 , wherein depositing a plurality of layers on a substrate comprises one of a spinning process, a dipping process, and a rolling process.
7. The method of claim 1 , wherein depositing a plurality of layers comprises depositing a radiation-curable layer of at least one acrylic monomer.
8. The method of claim 7 , wherein the radiation-curable layer comprises at least one (meth)acrylate monomer and a silicon compound.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/225,317 US20060014101A1 (en) | 2001-10-31 | 2005-09-12 | Radiation-curable anti-reflective coating system |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/001,639 US6942924B2 (en) | 2001-10-31 | 2001-10-31 | Radiation-curable anti-reflective coating system |
US11/225,317 US20060014101A1 (en) | 2001-10-31 | 2005-09-12 | Radiation-curable anti-reflective coating system |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/001,639 Division US6942924B2 (en) | 2001-10-31 | 2001-10-31 | Radiation-curable anti-reflective coating system |
Publications (1)
Publication Number | Publication Date |
---|---|
US20060014101A1 true US20060014101A1 (en) | 2006-01-19 |
Family
ID=21697091
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/001,639 Expired - Fee Related US6942924B2 (en) | 2001-10-31 | 2001-10-31 | Radiation-curable anti-reflective coating system |
US11/225,317 Abandoned US20060014101A1 (en) | 2001-10-31 | 2005-09-12 | Radiation-curable anti-reflective coating system |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/001,639 Expired - Fee Related US6942924B2 (en) | 2001-10-31 | 2001-10-31 | Radiation-curable anti-reflective coating system |
Country Status (2)
Country | Link |
---|---|
US (2) | US6942924B2 (en) |
WO (1) | WO2003038480A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2015353551B2 (en) * | 2014-11-25 | 2018-06-28 | Ppg Industries Ohio, Inc. | Curable film-forming sol-gel compositions and anti-glare coated articles formed from them |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003025510A (en) * | 2001-07-16 | 2003-01-29 | Shin Etsu Chem Co Ltd | Multilayered laminate having reflection preventing properties and scratch resistance |
FR2869039B1 (en) * | 2004-04-16 | 2007-11-30 | Essilor Int | PIGMENT COLORED LATEX AND PROCESS FOR TREATING A TRANSPARENT SUBSTRATE USING THE COLOR LATEX. |
US20060065989A1 (en) * | 2004-09-29 | 2006-03-30 | Thad Druffel | Lens forming systems and methods |
US20080041443A1 (en) * | 2006-08-16 | 2008-02-21 | Hnuphotonics | Thinned solar cell |
US7894137B2 (en) * | 2007-04-24 | 2011-02-22 | The Board Of Regents For Oklahoma State University | Omnidirectional antireflection coating |
US8409663B2 (en) * | 2007-04-27 | 2013-04-02 | Guardian Industries Corp. | Method of making a coated glass substrate with heat treatable ultraviolet blocking characteristics |
US20090181532A1 (en) * | 2008-01-10 | 2009-07-16 | International Business Machines Corporation | Integration scheme for extension of via opening depth |
US9376593B2 (en) | 2009-04-30 | 2016-06-28 | Enki Technology, Inc. | Multi-layer coatings |
US9353268B2 (en) | 2009-04-30 | 2016-05-31 | Enki Technology, Inc. | Anti-reflective and anti-soiling coatings for self-cleaning properties |
US8895838B1 (en) * | 2010-01-08 | 2014-11-25 | Magnolia Solar, Inc. | Multijunction solar cell employing extended heterojunction and step graded antireflection structures and methods for constructing the same |
WO2011149694A1 (en) | 2010-05-26 | 2011-12-01 | Corning Incorporated | Ion-exchanging an ar coated glass and process |
US9400343B1 (en) | 2014-04-30 | 2016-07-26 | Magnolia Optical Technologies, Inc. | Highly durable hydrophobic antireflection structures and method of manufacturing the same |
WO2016011071A2 (en) * | 2014-07-14 | 2016-01-21 | Enki Technology, Inc. | High gain durable anti-reflective coating |
US9399720B2 (en) | 2014-07-14 | 2016-07-26 | Enki Technology, Inc. | High gain durable anti-reflective coating |
US9598586B2 (en) | 2014-07-14 | 2017-03-21 | Enki Technology, Inc. | Coating materials and methods for enhanced reliability |
FR3024554B1 (en) * | 2014-07-30 | 2016-09-09 | Essilor Int | OPHTHALMIC LENS COMPRISING A COATING THAT MINIMIZES ULTRAVIOLET REFLECTIONS AND METHOD OF MANUFACTURING SUCH LENS |
US20190033491A1 (en) * | 2017-07-28 | 2019-01-31 | Ppg Industries Ohio, Inc. | Multi-layer antireflective coated articles |
US11583388B2 (en) | 2019-04-05 | 2023-02-21 | Amo Groningen B.V. | Systems and methods for spectacle independence using refractive index writing with an intraocular lens |
US11564839B2 (en) | 2019-04-05 | 2023-01-31 | Amo Groningen B.V. | Systems and methods for vergence matching of an intraocular lens with refractive index writing |
US11678975B2 (en) | 2019-04-05 | 2023-06-20 | Amo Groningen B.V. | Systems and methods for treating ocular disease with an intraocular lens and refractive index writing |
US11529230B2 (en) | 2019-04-05 | 2022-12-20 | Amo Groningen B.V. | Systems and methods for correcting power of an intraocular lens using refractive index writing |
US11583389B2 (en) | 2019-04-05 | 2023-02-21 | Amo Groningen B.V. | Systems and methods for correcting photic phenomenon from an intraocular lens and using refractive index writing |
US11944574B2 (en) | 2019-04-05 | 2024-04-02 | Amo Groningen B.V. | Systems and methods for multiple layer intraocular lens and using refractive index writing |
Citations (46)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US390672A (en) * | 1888-10-09 | Twist-drill | ||
US2553314A (en) * | 1944-07-01 | 1951-05-15 | Gen Electric | Method of rendering materials water repellent |
US3012006A (en) * | 1958-04-24 | 1961-12-05 | Dow Corning | Fluorinated alkyl silanes and their use |
US3244541A (en) * | 1961-02-03 | 1966-04-05 | 29 West Fifteenth Street Corp | Water-repellent compositions and methods of making same |
US3442664A (en) * | 1966-04-26 | 1969-05-06 | Minnesota Mining & Mfg | Treating composition,method of treating and treated surfaces |
US3579540A (en) * | 1968-11-01 | 1971-05-18 | Howard G Ohlhausen | Method for protecting nonporous substrates and for rendering them water repellent |
US3959563A (en) * | 1973-11-02 | 1976-05-25 | General Electric Company | Method for rendering vitreous surfaces water repellant and dirt deposit resistant and articles produced thereby |
US3989609A (en) * | 1973-09-24 | 1976-11-02 | Dennison Manufacturing Company | Radiation curable resistant coatings and their preparation |
UST954010I4 (en) * | 1973-08-24 | 1977-01-04 | International Business Machines Corporation | Method of coating oxidized inorganic substrates with polyimide |
US4130672A (en) * | 1973-10-16 | 1978-12-19 | Hoya Lens Co., Ltd. | Method for coating anti-reflection film on surface of optical material |
US4172156A (en) * | 1976-12-27 | 1979-10-23 | Balzers Aktiengesellschaft Fur Hochvakuumtechnik Und Dunne Schichten | Method of depositing a reflection reducing coating on substrates of organic material |
US4196246A (en) * | 1976-06-23 | 1980-04-01 | Nippon Kogaku K.K. | Anti-reflection film for synthetic resin base |
US4267213A (en) * | 1978-04-11 | 1981-05-12 | Minnesota Mining & Manufacturing Company | Sulfonato-organosilanol compounds and aqueous solutions thereof |
US4273826A (en) * | 1979-12-03 | 1981-06-16 | Owens-Illinois, Inc. | Process of making glass articles having antireflective coatings and product |
US4286024A (en) * | 1980-04-28 | 1981-08-25 | Westinghouse Electric Corp. | Transparent high temperature resistant aluminum silicon oxide monolithic member or coating |
US4361598A (en) * | 1979-08-10 | 1982-11-30 | Westinghouse Electric Corp. | Polymerized solutions for depositing optical oxide coatings |
US4410563A (en) * | 1982-02-22 | 1983-10-18 | The United States Of America As Represented By The Secretary Of The Navy | Repellent coatings for optical surfaces |
US4476156A (en) * | 1983-03-10 | 1984-10-09 | The United States Of America As Represented By The United States Department Of Energy | Low temperature process for obtaining thin glass films |
US4535026A (en) * | 1983-06-29 | 1985-08-13 | The United States Of America As Represented By The United States Department Of Energy | Antireflective graded index silica coating, method for making |
US4599272A (en) * | 1983-09-20 | 1986-07-08 | Olympus Optical Company Limited | Anti-reflection coating for optical component and method for forming the same |
US4609267A (en) * | 1980-12-22 | 1986-09-02 | Seiko Epson Corporation | Synthetic resin lens and antireflection coating |
US4652467A (en) * | 1985-02-25 | 1987-03-24 | The United States Of America As Represented By The United States Department Of Energy | Inorganic-polymer-derived dielectric films |
US4710227A (en) * | 1986-04-28 | 1987-12-01 | The Dow Chemical Company | Dispersion process for ceramic green body |
US4731264A (en) * | 1986-10-03 | 1988-03-15 | Ppg Industries, Inc. | Sol-gel compositions containing silane and alumina |
US4765729A (en) * | 1985-04-30 | 1988-08-23 | Toray Industries, Inc. | Anti-reflection optical article |
US4944962A (en) * | 1987-10-24 | 1990-07-31 | Ito Optical Industrial Co., Ltd. | Method for dirtproofing treatment for plastic lens |
US4966812A (en) * | 1988-01-26 | 1990-10-30 | The United States Of America As Represented By The Department Of Energy | Sol-gel antireflective coating on plastics |
US5061769A (en) * | 1990-12-17 | 1991-10-29 | Allied-Signal Inc. | Fluoropolymers and fluoropolymer coatings |
US5172812A (en) * | 1992-01-23 | 1992-12-22 | Rexham Corporation | Child-resistant paperboard blister package and method of making the same |
US5178955A (en) * | 1990-12-17 | 1993-01-12 | Allied-Signal Inc. | Polymeric anti-reflection coatings and coated articles |
US5198267A (en) * | 1991-09-20 | 1993-03-30 | Allied-Signal Inc. | Fluoropolymer blend anti-reflection coatings and coated articles |
US5225244A (en) * | 1990-12-17 | 1993-07-06 | Allied-Signal Inc. | Polymeric anti-reflection coatings and coated articles |
US5385955A (en) * | 1992-11-05 | 1995-01-31 | Essilor Of America, Inc. | Organosilane coating composition for ophthalmic lens |
US5580819A (en) * | 1995-03-22 | 1996-12-03 | Ppg Industries, Inc. | Coating composition, process for producing antireflective coatings, and coated articles |
US5622784A (en) * | 1986-01-21 | 1997-04-22 | Seiko Epson Corporation | Synthetic resin ophthalmic lens having an inorganic coating |
US5719705A (en) * | 1995-06-07 | 1998-02-17 | Sola International, Inc. | Anti-static anti-reflection coating |
US5746717A (en) * | 1993-03-30 | 1998-05-05 | Aigner; Karl R. | Balloon catheter and device for perfusion with the balloon catheter |
US5770306A (en) * | 1995-03-09 | 1998-06-23 | Dai Nippon Printing Co., Ltd. | Antireflection film containing ultrafine particles, polarizing plate and liquid crystal display device |
US5858526A (en) * | 1993-07-16 | 1999-01-12 | Commissariat A L'energie Atomique | Composite material with a high refractive index, process for producing said composite material and optically active material incorporating said composite material |
US6165564A (en) * | 1999-05-12 | 2000-12-26 | Callaway Golf Company | UV-curable clear coat for golf balls |
US6228433B1 (en) * | 1997-05-02 | 2001-05-08 | Permagrain Products, Inc. | Abrasion resistant urethane coatings |
US6232360B1 (en) * | 1994-02-14 | 2001-05-15 | Bayer Aktiengesellschaft | UV-curable coating compositions and their use for coating polycarbonate molded articles |
US6241505B1 (en) * | 1996-04-19 | 2001-06-05 | Q2100, Inc. | Apparatus for eyeglass lens curing using ultraviolet light |
US6245428B1 (en) * | 1998-06-10 | 2001-06-12 | Cpfilms Inc. | Low reflective films |
US6277485B1 (en) * | 1998-01-27 | 2001-08-21 | 3M Innovative Properties Company | Antisoiling coatings for antireflective surfaces and methods of preparation |
US20020019461A1 (en) * | 1998-11-06 | 2002-02-14 | Takao Yashiro | Radiation-curable metal particles and curable resin compositions comprising these particles |
Family Cites Families (36)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3900672A (en) | 1973-04-04 | 1975-08-19 | Hoya Lens Co Ltd | Process for coating an optical material and the resulting product |
JPS511387A (en) | 1974-05-23 | 1976-01-08 | Canon Kk | |
SE435297B (en) | 1975-08-22 | 1984-09-17 | Bosch Gmbh Robert | OPTICAL REFLECTORS MANUFACTURED BY COATING A REFLECTOR |
JPS5423557A (en) | 1977-07-23 | 1979-02-22 | Ito Kougaku Kougiyou Kk | Optical parts of plastics and method of manufacturing same |
US4338377A (en) | 1979-10-10 | 1982-07-06 | Minnesota Mining And Manufacturing Company | Sulfonato-organosilanol compounds and aqueous solutions thereof |
JPS5747330A (en) | 1980-09-04 | 1982-03-18 | Toray Ind Inc | Production of transparent material with antireflexion properties |
JPS5686980A (en) | 1979-12-18 | 1981-07-15 | Taihoo Kogyo Kk | Antifogging treatment and antifogging agent |
JPS58172245A (en) | 1982-04-02 | 1983-10-11 | Asahi Glass Co Ltd | Surface treating agent for glass |
JPS58211701A (en) | 1982-06-04 | 1983-12-09 | Asahi Glass Co Ltd | Low reflectance glass |
JPS5913201A (en) | 1982-07-15 | 1984-01-24 | Hitachi Ltd | Method for providing antireflection film on synthetic resin lens |
JPS5939714A (en) | 1982-08-31 | 1984-03-05 | Matsumoto Seiyaku Kogyo Kk | Formation of silicon oxide coat |
JPS59231501A (en) | 1983-06-14 | 1984-12-26 | Seiko Epson Corp | Plastic lens |
JPS60258190A (en) | 1984-06-06 | 1985-12-20 | Mitsubishi Gas Chem Co Inc | Novel cyclotrisilazan |
JPS61130902A (en) | 1984-11-30 | 1986-06-18 | Asahi Glass Co Ltd | Plastic lens with antireflective film and capable of easy removal of stain |
JPS6280603A (en) | 1985-10-04 | 1987-04-14 | Toray Ind Inc | Optical article having antireflection characteristic and its preparation |
JPS649222A (en) | 1986-09-18 | 1989-01-12 | Agency Ind Science Techn | Highly conductive poly-2,5-thienylenevinylene composition |
JPS63214791A (en) | 1987-03-04 | 1988-09-07 | 株式会社日立国際電気 | Controller for multiscan crt display device |
JPS63228101A (en) | 1987-03-17 | 1988-09-22 | Nippon Sheet Glass Co Ltd | Antistatic non-reflection plate having stain resistance |
JPS6486101A (en) | 1987-06-18 | 1989-03-30 | Toray Industries | Production of antireflecting article |
JPH02671A (en) | 1987-10-20 | 1990-01-05 | Asahi Optical Co Ltd | Surface-treating agent for anti-reflection coating and surface treatment |
JPH01149808A (en) | 1987-12-04 | 1989-06-12 | Daikin Ind Ltd | Fluorine-containing polymer and use thereof |
JP2678008B2 (en) | 1988-03-22 | 1997-11-17 | 日東電工株式会社 | Manufacturing method of anti-reflection plate |
JPH01309003A (en) | 1988-06-07 | 1989-12-13 | Toray Ind Inc | Antistatic article having water repellency |
JP2671903B2 (en) | 1988-06-17 | 1997-11-05 | 富士通株式会社 | Dynamic random access memory device |
JPH02197801A (en) | 1988-08-18 | 1990-08-06 | Nidek Co Ltd | Optical element with water mark preventive coating film |
JPH0287101A (en) | 1988-09-22 | 1990-03-28 | Nitto Denko Corp | Production of antireflection film |
JPH02130501A (en) | 1988-11-10 | 1990-05-18 | Nitto Denko Corp | Antireflection sheet |
JPH02181701A (en) | 1989-01-07 | 1990-07-16 | Nitto Denko Corp | Production of antireflection film |
JPH0781024B2 (en) | 1989-03-22 | 1995-08-30 | 旭硝子株式会社 | Water repellency. Antifouling transparent base material and structure equipped with the same |
JPH03148603A (en) | 1989-11-04 | 1991-06-25 | Nitto Denko Corp | Polarizing plate |
JPH03195757A (en) | 1989-12-26 | 1991-08-27 | Asahi Glass Co Ltd | Fluorine-containing polymer composition for coating and use thereof |
JPH03266801A (en) | 1990-03-16 | 1991-11-27 | Nitto Denko Corp | Antireflection filter |
JP2858440B2 (en) | 1990-07-09 | 1999-02-17 | 株式会社東京製品開発研究所 | Porous ceramic material impregnated and solidified with an organic film-forming substance that can be vaporized in a vacuum, and a method for forming an organic substance-based deposited film using the same |
FR2680583B1 (en) | 1991-08-22 | 1993-10-08 | Commissariat A Energie Atomique | MATERIAL HAVING ANTI-REFLECTIVE, HYDROPHOBIC AND ABRASION RESISTANCE PROPERTIES AND METHOD FOR DEPOSITING AN ANTI-REFLECTIVE, HYDROPHOBIC AND ABRASION RESISTANT LAYER ON A SUBSTRATE. |
JPH10111401A (en) | 1996-08-14 | 1998-04-28 | Daikin Ind Ltd | Article with antireflection treatment |
US6210858B1 (en) | 1997-04-04 | 2001-04-03 | Fuji Photo Film Co., Ltd. | Anti-reflection film and display device using the same |
-
2001
- 2001-10-31 US US10/001,639 patent/US6942924B2/en not_active Expired - Fee Related
-
2002
- 2002-10-31 WO PCT/US2002/034925 patent/WO2003038480A1/en active Search and Examination
-
2005
- 2005-09-12 US US11/225,317 patent/US20060014101A1/en not_active Abandoned
Patent Citations (47)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US390672A (en) * | 1888-10-09 | Twist-drill | ||
US2553314A (en) * | 1944-07-01 | 1951-05-15 | Gen Electric | Method of rendering materials water repellent |
US3012006A (en) * | 1958-04-24 | 1961-12-05 | Dow Corning | Fluorinated alkyl silanes and their use |
US3244541A (en) * | 1961-02-03 | 1966-04-05 | 29 West Fifteenth Street Corp | Water-repellent compositions and methods of making same |
US3442664A (en) * | 1966-04-26 | 1969-05-06 | Minnesota Mining & Mfg | Treating composition,method of treating and treated surfaces |
US3579540B1 (en) * | 1968-11-01 | 1984-03-20 | ||
US3579540A (en) * | 1968-11-01 | 1971-05-18 | Howard G Ohlhausen | Method for protecting nonporous substrates and for rendering them water repellent |
UST954010I4 (en) * | 1973-08-24 | 1977-01-04 | International Business Machines Corporation | Method of coating oxidized inorganic substrates with polyimide |
US3989609A (en) * | 1973-09-24 | 1976-11-02 | Dennison Manufacturing Company | Radiation curable resistant coatings and their preparation |
US4130672A (en) * | 1973-10-16 | 1978-12-19 | Hoya Lens Co., Ltd. | Method for coating anti-reflection film on surface of optical material |
US3959563A (en) * | 1973-11-02 | 1976-05-25 | General Electric Company | Method for rendering vitreous surfaces water repellant and dirt deposit resistant and articles produced thereby |
US4196246A (en) * | 1976-06-23 | 1980-04-01 | Nippon Kogaku K.K. | Anti-reflection film for synthetic resin base |
US4172156A (en) * | 1976-12-27 | 1979-10-23 | Balzers Aktiengesellschaft Fur Hochvakuumtechnik Und Dunne Schichten | Method of depositing a reflection reducing coating on substrates of organic material |
US4267213A (en) * | 1978-04-11 | 1981-05-12 | Minnesota Mining & Manufacturing Company | Sulfonato-organosilanol compounds and aqueous solutions thereof |
US4361598A (en) * | 1979-08-10 | 1982-11-30 | Westinghouse Electric Corp. | Polymerized solutions for depositing optical oxide coatings |
US4273826A (en) * | 1979-12-03 | 1981-06-16 | Owens-Illinois, Inc. | Process of making glass articles having antireflective coatings and product |
US4286024A (en) * | 1980-04-28 | 1981-08-25 | Westinghouse Electric Corp. | Transparent high temperature resistant aluminum silicon oxide monolithic member or coating |
US4609267A (en) * | 1980-12-22 | 1986-09-02 | Seiko Epson Corporation | Synthetic resin lens and antireflection coating |
US4410563A (en) * | 1982-02-22 | 1983-10-18 | The United States Of America As Represented By The Secretary Of The Navy | Repellent coatings for optical surfaces |
US4476156A (en) * | 1983-03-10 | 1984-10-09 | The United States Of America As Represented By The United States Department Of Energy | Low temperature process for obtaining thin glass films |
US4535026A (en) * | 1983-06-29 | 1985-08-13 | The United States Of America As Represented By The United States Department Of Energy | Antireflective graded index silica coating, method for making |
US4599272A (en) * | 1983-09-20 | 1986-07-08 | Olympus Optical Company Limited | Anti-reflection coating for optical component and method for forming the same |
US4652467A (en) * | 1985-02-25 | 1987-03-24 | The United States Of America As Represented By The United States Department Of Energy | Inorganic-polymer-derived dielectric films |
US4765729A (en) * | 1985-04-30 | 1988-08-23 | Toray Industries, Inc. | Anti-reflection optical article |
US5622784A (en) * | 1986-01-21 | 1997-04-22 | Seiko Epson Corporation | Synthetic resin ophthalmic lens having an inorganic coating |
US4710227A (en) * | 1986-04-28 | 1987-12-01 | The Dow Chemical Company | Dispersion process for ceramic green body |
US4731264A (en) * | 1986-10-03 | 1988-03-15 | Ppg Industries, Inc. | Sol-gel compositions containing silane and alumina |
US4944962A (en) * | 1987-10-24 | 1990-07-31 | Ito Optical Industrial Co., Ltd. | Method for dirtproofing treatment for plastic lens |
US4966812A (en) * | 1988-01-26 | 1990-10-30 | The United States Of America As Represented By The Department Of Energy | Sol-gel antireflective coating on plastics |
US5061769A (en) * | 1990-12-17 | 1991-10-29 | Allied-Signal Inc. | Fluoropolymers and fluoropolymer coatings |
US5178955A (en) * | 1990-12-17 | 1993-01-12 | Allied-Signal Inc. | Polymeric anti-reflection coatings and coated articles |
US5225244A (en) * | 1990-12-17 | 1993-07-06 | Allied-Signal Inc. | Polymeric anti-reflection coatings and coated articles |
US5198267A (en) * | 1991-09-20 | 1993-03-30 | Allied-Signal Inc. | Fluoropolymer blend anti-reflection coatings and coated articles |
US5172812A (en) * | 1992-01-23 | 1992-12-22 | Rexham Corporation | Child-resistant paperboard blister package and method of making the same |
US5385955A (en) * | 1992-11-05 | 1995-01-31 | Essilor Of America, Inc. | Organosilane coating composition for ophthalmic lens |
US5746717A (en) * | 1993-03-30 | 1998-05-05 | Aigner; Karl R. | Balloon catheter and device for perfusion with the balloon catheter |
US5858526A (en) * | 1993-07-16 | 1999-01-12 | Commissariat A L'energie Atomique | Composite material with a high refractive index, process for producing said composite material and optically active material incorporating said composite material |
US6232360B1 (en) * | 1994-02-14 | 2001-05-15 | Bayer Aktiengesellschaft | UV-curable coating compositions and their use for coating polycarbonate molded articles |
US5770306A (en) * | 1995-03-09 | 1998-06-23 | Dai Nippon Printing Co., Ltd. | Antireflection film containing ultrafine particles, polarizing plate and liquid crystal display device |
US5580819A (en) * | 1995-03-22 | 1996-12-03 | Ppg Industries, Inc. | Coating composition, process for producing antireflective coatings, and coated articles |
US5719705A (en) * | 1995-06-07 | 1998-02-17 | Sola International, Inc. | Anti-static anti-reflection coating |
US6241505B1 (en) * | 1996-04-19 | 2001-06-05 | Q2100, Inc. | Apparatus for eyeglass lens curing using ultraviolet light |
US6228433B1 (en) * | 1997-05-02 | 2001-05-08 | Permagrain Products, Inc. | Abrasion resistant urethane coatings |
US6277485B1 (en) * | 1998-01-27 | 2001-08-21 | 3M Innovative Properties Company | Antisoiling coatings for antireflective surfaces and methods of preparation |
US6245428B1 (en) * | 1998-06-10 | 2001-06-12 | Cpfilms Inc. | Low reflective films |
US20020019461A1 (en) * | 1998-11-06 | 2002-02-14 | Takao Yashiro | Radiation-curable metal particles and curable resin compositions comprising these particles |
US6165564A (en) * | 1999-05-12 | 2000-12-26 | Callaway Golf Company | UV-curable clear coat for golf balls |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2015353551B2 (en) * | 2014-11-25 | 2018-06-28 | Ppg Industries Ohio, Inc. | Curable film-forming sol-gel compositions and anti-glare coated articles formed from them |
US10723890B2 (en) | 2014-11-25 | 2020-07-28 | Ppg Industries Ohio, Inc. | Curable film-forming sol-gel compositions and anti-glare coated articles formed from them |
Also Published As
Publication number | Publication date |
---|---|
US6942924B2 (en) | 2005-09-13 |
US20030082399A1 (en) | 2003-05-01 |
WO2003038480A1 (en) | 2003-05-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US20060014101A1 (en) | Radiation-curable anti-reflective coating system | |
US6245428B1 (en) | Low reflective films | |
JP4362509B2 (en) | Antireflection film and method for producing the same | |
EP2718750B1 (en) | Method for obtaining optical articles having superior abrasion resistant properties, and coated articles prepared according to such method | |
TWI314589B (en) | Preparation of a mechanically durable single layer coating with anti-reflective properties | |
US6455103B1 (en) | Method for producing multilayered optical systems | |
TWI518156B (en) | Anti-reflection and anti-glare coating composition, anti-reflection and anti-glare film, and method for preparation of the same | |
US20040156983A1 (en) | Rapid, thermally cured, back side MAR resistant and antireflective coating for ophthalmic lenses | |
KR20090102658A (en) | Method for forming anti-reflection coating and optical element | |
CA2575970A1 (en) | Method of producing a substrate which is coated with a mesoporous layer and use thereof in ophthalmic optics | |
CA2383439A1 (en) | Composition and method for a coating providing anti-reflective and anti-static properties | |
KR20120005413A (en) | Anti-reflection film and method for manufacturing the same | |
WO2011126303A2 (en) | Antireflective coating composition, antireflective film, and preparation method thereof | |
JP2017182065A (en) | Optical element and manufacturing method of the same | |
JP2001296401A (en) | Curable composition for high refractive index film, high refractive index film and antireflection laminated body | |
CN101470218A (en) | Anti-reflection coating, optical member, exchange lens unit and imaging device | |
US7598595B2 (en) | Fabrication of nanoporous antireflection film | |
WO2018180504A1 (en) | Anti-reflection film | |
JPH03145602A (en) | Laminate and production thereof | |
JPS6088901A (en) | Plastic lens | |
JP2002120311A (en) | Structure | |
JPH1184102A (en) | Antifogging coating film and optical part using the same | |
Chang et al. | Preparation of organic–inorganic hybridized dual‐functional antifog/antireflection coatings on plastic substrates | |
JP2001293818A (en) | Reflection preventing hard coat film | |
JPS634201A (en) | Antireflection film |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |