JPH036265A - Coating composition - Google Patents
Coating compositionInfo
- Publication number
- JPH036265A JPH036265A JP1138714A JP13871489A JPH036265A JP H036265 A JPH036265 A JP H036265A JP 1138714 A JP1138714 A JP 1138714A JP 13871489 A JP13871489 A JP 13871489A JP H036265 A JPH036265 A JP H036265A
- Authority
- JP
- Japan
- Prior art keywords
- coating composition
- film
- coating
- refractive index
- organic compound
- 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.)
- Granted
Links
- 239000008199 coating composition Substances 0.000 title claims abstract description 14
- 239000011248 coating agent Substances 0.000 claims abstract description 39
- 238000000576 coating method Methods 0.000 claims abstract description 39
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 claims abstract description 15
- 229910001635 magnesium fluoride Inorganic materials 0.000 claims abstract description 14
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 claims abstract description 13
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 13
- 229910001634 calcium fluoride Inorganic materials 0.000 claims abstract description 12
- 239000010419 fine particle Substances 0.000 claims abstract description 12
- 239000002245 particle Substances 0.000 claims abstract description 11
- 239000003999 initiator Substances 0.000 claims abstract description 9
- 239000000178 monomer Substances 0.000 claims abstract description 9
- 239000007787 solid Substances 0.000 claims abstract description 5
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims abstract description 4
- 239000011347 resin Substances 0.000 abstract description 13
- 229920005989 resin Polymers 0.000 abstract description 13
- 238000002156 mixing Methods 0.000 abstract description 3
- 239000000986 disperse dye Substances 0.000 abstract description 2
- 238000000465 moulding Methods 0.000 abstract 1
- 230000005855 radiation Effects 0.000 abstract 1
- 239000010408 film Substances 0.000 description 40
- 239000000463 material Substances 0.000 description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 10
- -1 fluoroalkyl silane compound Chemical class 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 229920003023 plastic Polymers 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000004033 plastic Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 229920001296 polysiloxane Polymers 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical group C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- DAUQEQSACMZHDS-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(F)(C(F)(F)F)C(F)(F)F DAUQEQSACMZHDS-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- 238000007605 air drying Methods 0.000 description 2
- 238000000137 annealing Methods 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- 239000012965 benzophenone Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000008119 colloidal silica Substances 0.000 description 2
- 239000006059 cover glass Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- XHAFIUUYXQFJEW-UHFFFAOYSA-N 1-chloroethenylbenzene Chemical compound ClC(=C)C1=CC=CC=C1 XHAFIUUYXQFJEW-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- BUJVPKZRXOTBGA-UHFFFAOYSA-N 2-trimethoxysilylethyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCOC(=O)C=C BUJVPKZRXOTBGA-UHFFFAOYSA-N 0.000 description 1
- BVEYJWQCMOVMAR-UHFFFAOYSA-N 5-Hydroxy-4-octanone Chemical compound CCCC(O)C(=O)CCC BVEYJWQCMOVMAR-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 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 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- MBHRHUJRKGNOKX-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methanol Chemical compound NC1=NC(N)=NC(NCO)=N1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- HTKFORQRBXIQHD-UHFFFAOYSA-N allylthiourea Chemical compound NC(=S)NCC=C HTKFORQRBXIQHD-UHFFFAOYSA-N 0.000 description 1
- 229960001748 allylthiourea Drugs 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000003945 anionic surfactant Substances 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
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 description 1
- 229920000402 bisphenol A polycarbonate polymer Polymers 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229920001109 fluorescent polymer Polymers 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000010954 inorganic particle Substances 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000002032 methanolic fraction Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- QCTJRYGLPAFRMS-UHFFFAOYSA-N prop-2-enoic acid;1,3,5-triazine-2,4,6-triamine Chemical compound OC(=O)C=C.NC1=NC(N)=NC(N)=N1 QCTJRYGLPAFRMS-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Landscapes
- Eyeglasses (AREA)
- Surface Treatment Of Optical Elements (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Paints Or Removers (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、プラスチックレンズなど光学用途に適した透
明樹脂成型品のコーティング用の組成物に関する。更に
は、透明樹脂成型品の表面反射を低く抑え、且つ分散染
料による染色が可能であり、表面硬度を高く保つことが
出来るコーティング材料を提供するものである。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a composition for coating transparent resin molded products suitable for optical applications such as plastic lenses. Furthermore, it is an object of the present invention to provide a coating material that can suppress the surface reflection of a transparent resin molded product, can be dyed with a disperse dye, and can maintain high surface hardness.
本発明は、低い屈折率のコーテイング膜を与えるための
コーティング組成物で、フッ化マグネシウム、またはフ
ッ化カルシウム、またはフッ化マグネシウム及びフッ化
カルシウムの混合物よりなる微粒子と、光で重合硬化す
る有機バインダーとして重合性有機化合物及び光重合開
始剤微粒子からなる組成物である。The present invention is a coating composition for providing a coating film with a low refractive index, comprising fine particles of magnesium fluoride, calcium fluoride, or a mixture of magnesium fluoride and calcium fluoride, and an organic binder that is polymerized and cured by light. It is a composition consisting of a polymerizable organic compound and photopolymerization initiator fine particles.
従来、反射防止の方法としては真空蒸着の方法が一般的
で、無機ガラスのみならず、酸化ケイ素や酸化ジルコニ
ウム等の酸化物材料をよ、プラスチック材料へも応用さ
れている。Vacuum deposition has conventionally been a common method for antireflection, and has been applied not only to inorganic glasses but also to oxide materials such as silicon oxide and zirconium oxide, and to plastic materials.
また、特開昭61−18901号には、フルオロアルキ
ル基を有するビ久シラン化合物を成分とするコーティン
グ組成物が開示されている。これは、プラスチックレン
ズなどへの応用が出来ることが記載されている。Further, JP-A-61-18901 discloses a coating composition containing a bikusilane compound having a fluoroalkyl group as a component. It is stated that this can be applied to plastic lenses, etc.
また、表面はパーフルオロポリマー化する方法が公知で
ある(機能性歯ふっ崇高分子、P79、日刊工業新聞社
、昭和55年出版)。Furthermore, a method of perfluoropolymerizing the surface is known (Functional Dental Fluorescent Polymer, P79, Nikkan Kogyo Shimbun, published in 1980).
一方、表面硬度の高い膜を形成する方法としてハードコ
ートが一般的である0例として、例えば、特開昭57−
20968、同57−128755号等に、光重合性ハ
ードコート塗料が開示されており、耐薬品性の向上、耐
擦傷性の向上がはかられている。On the other hand, as an example of a common method of forming a film with high surface hardness by hard coating, for example, JP-A-57-
No. 20968, No. 57-128755, etc., disclose photopolymerizable hard coat paints, which are intended to improve chemical resistance and scratch resistance.
しかし、透明材料の反射防止に適したコーティング材料
は、以下にのべる課題を有する。However, coating materials suitable for antireflection of transparent materials have the following problems.
すなわち従来の技術の内、最も実用化の進んでいる真空
蒸着による薄膜形成の方法でtよ、■ 高真空が必要で
あること、
If 大面積を均一にコーティングすることが困難で
ある。That is, among the conventional techniques, the method of forming a thin film by vacuum evaporation, which is the most widely used method, has the following drawbacks: (1) High vacuum is required; and (1) It is difficult to uniformly coat a large area.
Ill 設備に多大なコストがかかることなど、産業
上の問題点のゆえにパネルや低価格の光学用途の部品な
ど実用化困難である。Due to industrial problems such as the high cost of equipment, it is difficult to put it into practical use in panels and low-cost optical parts.
更にまた、得られるコーテイング膜は、緻密な構造の無
機質の薄膜が得られるが、そのため可どう性が劣り、プ
ラスチック基材等への密着性が不充分である。そして、
染色など後加工も不可能であるという欠点を有する。Furthermore, although the resulting coating film is an inorganic thin film with a dense structure, it has poor flexibility and insufficient adhesion to plastic substrates and the like. and,
It has the disadvantage that post-processing such as dyeing is not possible.
更にまた、得られた成型物品は耐衝撃性が劣り、プラス
チックの長所を生かせないという課題もある。Furthermore, the resulting molded article has poor impact resistance, and there is also the problem that the advantages of plastic cannot be utilized.
更にまたフッ化マグネシウムやフッ化カルシウムは、光
学的に屈折率が低いことから興味深いものの、蒸着では
、非常に高温での条件でコーティングを行なう必要が有
りプラスチック材料に可能な条件で蒸着すると膜は脆く
密着性の不充分な物しか出来ない状況であった。Furthermore, although magnesium fluoride and calcium fluoride are interesting because they have a low optical refractive index, they must be coated under extremely high temperature conditions during vapor deposition, and if they are vapor deposited under conditions that are possible on plastic materials, the film will not form. The situation was such that only products that were brittle and had insufficient adhesion could be produced.
またイオンブレーティングやCVD法等が研究されてい
るが、まだ実用的ではない。Further, although ion brating and CVD methods are being studied, they are not yet practical.
次に、特開昭61−18901号に開示されたフルオロ
アルキル系シラン化合物を成分とするコーティング組成
物は、比較的低い屈折率を得ることは出来るが、硬さ、
染色性等の点で実用上不充分である。Next, although the coating composition containing a fluoroalkyl silane compound disclosed in JP-A No. 61-18901 can obtain a relatively low refractive index, it has a high hardness and
Practically unsatisfactory in terms of dyeability, etc.
また、表面をフッ素化する方法においても、硬さ、染色
性の特性が得られない。Further, even in the method of fluorinating the surface, properties such as hardness and dyeability cannot be obtained.
一方、表面硬度の高い膜として開示されている特開昭5
7−20968、同57−128755号の光重合性ハ
ードコートの例では、耐薬品性の向上、耐擦傷性の向上
は可能であるが、この素材は屈折率がほとんどの物が1
.5であり、反射防止の効果はえられない。On the other hand, JP-A No. 5, which is disclosed as a film with high surface hardness,
7-20968 and 57-128755, it is possible to improve chemical resistance and scratch resistance, but most of these materials have a refractive index of 1.
.. 5, and no anti-reflection effect can be obtained.
本発明は、これらの課題を解決するために鋭意検討を行
なった結果えられたもので屈折率1.30から1.45
の低い屈折率の塗膜を与える組成物に関するものである
。The present invention was achieved as a result of intensive studies to solve these problems, and has a refractive index of 1.30 to 1.45.
The invention relates to a composition that provides a coating film with a low refractive index.
即ち、本発明は、活性エネルギー線硬化型コーティング
組成物において、全固形分中、Aを10〜70重1パー
セント、Bを90〜30重量パーセントとからなること
を特徴とするコーティング組成物である。That is, the present invention is an active energy ray-curable coating composition characterized in that A is 10 to 70% by weight and B is 90 to 30% by weight based on the total solid content. .
ここで、Aは、粒径1〜50ミリミクロンのフッ化マグ
ネシウム、または/及びフッ化カルシウムの微粒子で、
Bは、重合性有機化合物及び光重合開始剤である。Here, A is fine particles of magnesium fluoride or/and calcium fluoride with a particle size of 1 to 50 millimicrons,
B is a polymerizable organic compound and a photopolymerization initiator.
以下、本発明を更に詳細に説明する。The present invention will be explained in more detail below.
A成分のフッ化マグネシウムおよびフッ化カルシウムは
、バルク状態での屈折率が、フッ化マグネシウム(Mg
Fa)が、1.38で、フッ化カルシウム(CaF2)
が1.25と低く、塗膜として、屈折率1.20から1
,45を得るために適した素材である。Component A, magnesium fluoride and calcium fluoride, has a refractive index in the bulk state of magnesium fluoride (Mg
Fa) is 1.38, calcium fluoride (CaF2)
The refractive index is as low as 1.25, and as a coating film, the refractive index is 1.20 to 1.
, 45.
ここで、Aは、粒径1〜50ミリミクロンのフッ化マグ
ネシウム、または/及びフッ化カルシウムの微粒子で、
Bは、重合性有機化合物及び光重合開始剤である。Here, A is fine particles of magnesium fluoride or/and calcium fluoride with a particle size of 1 to 50 millimicrons,
B is a polymerizable organic compound and a photopolymerization initiator.
以下、本発明を更に詳細に説明する。The present invention will be explained in more detail below.
A成分のフッ化マグネシウム(MgF2)及びフッ化カ
ルシウム(CaFp)は、バルク状態での屈折率が、M
g F tが1□ 38で、CaF2が1.25と低
く、塗膜として、屈折率1.20から1゜45のものを
得るために適した素材である。Component A, magnesium fluoride (MgF2) and calcium fluoride (CaFp), has a refractive index in the bulk state of M
It has a low g F t of 1□38 and a low CaF2 of 1.25, making it a material suitable for obtaining a coating film with a refractive index of 1.20 to 1°45.
しかし、従来は微粒子化が困難で十分な分散体がなかっ
たが、近年、気相法及び液相法での高度に微小化した分
散物が得られるようになった(例えば、日本経済産業新
聞、昭和62年3月31日版)、これらをきっかけとし
て、金属化合物微粒子の開発が幾つかなされており、両
フッ化物とも使用可能な材料が選択出来る。However, in the past, it was difficult to make fine particles and there was no sufficient dispersion, but in recent years it has become possible to obtain highly fine dispersions using gas phase and liquid phase methods (for example, Nihon Keizai Shimbun , March 31, 1986 edition), these developments have led to the development of several metal compound fine particles, and materials that can be used with both fluorides can be selected.
この粒子の大きさとしては、成膜した時に、光学的に透
明になることが必須であるため限定される。即ち、光の
散乱を引き起こさない為に、また、バインダーと良く混
合出来るように、粒径1〜50ミリミクロンの微粒子が
好ましい。The size of these particles is limited because it is essential that the film becomes optically transparent when formed. That is, in order not to cause light scattering and to be able to mix well with the binder, fine particles having a particle size of 1 to 50 millimicrons are preferable.
粒径が50ミリミクロン以上では、塗膜が白濁し、1ミ
リミクロン以下では、粒子性が減少しポリ酸の性質が強
くなるため、得られた膜の強度が不充分となり適当では
ない。If the particle size is 50 millimicrons or more, the coating film becomes cloudy, and if it is less than 1 millimicron, the particle size decreases and the polyacid properties become strong, resulting in insufficient strength of the obtained film, which is not suitable.
このAの微粒子は好ましくは溶媒に分散したゾルを用い
るか、微粒子をコーテイング液に分散させる方法により
調整する。The fine particles of A are preferably prepared by using a sol dispersed in a solvent or by dispersing the fine particles in a coating liquid.
次に、B成分である重合性有機化合物及び光重合開始剤
について説明する。Next, the polymerizable organic compound and photopolymerization initiator, which are component B, will be explained.
重合性有機化合物とは、一分子中に2個以上の(メタ)
アクリロイル基を有する多官能モノマーあるいはプレポ
リマーが用いられる。これらの化合物の例としては、
(ポリ)エチレングリコール、
(ポリ)プロピレングリコール、
ヘキサンジオール、
グリセリン、
トリメヂロールプロパン、
などのジ或いはトリ(メタ)アクリレートや、ペンタエ
リスリトール、
ジペンタエリスリトール、
ソルビトール、
などのトリ、テトラまたはへキサ(メタ)アクリレート
等が挙げられる。また、ジアリリデンペンタエリスリッ
ト等の不飽和シクロアセクール化合物に、2−ヒドロエ
チル(メタ)アクリレート等の重合性不飽和基を尋人し
たスピラン(メタ)アクリレートも、基材への接着性を
向上させる為に有効である。硬化膜の硬さを増す為に、
前記の反応性官能基の数の多い物を増したり、更にビス
フェノールAやヒドロキノン骨格にエチレンオキシドを
付加した多価アルコールのジ(メタ)アクリレートを用
いることが効果的である。その他、粘着性を向上させる
為に、ポリブタジェン等の樹脂中の反応性基をアクリル
化した多価アクリレートを用い、また、シリコンオリゴ
マー末端にアクリル基を有するシリコンアクリレートや
、メチロールメラミンと2−ヒドロキシエチル(メタ)
アクリレートから誘導されるメラミンアクリレート等を
用い、塗膜の耐熱性や耐薬品性を改善することができる
。この他にエチレングリコール等の多価アルコールとフ
タル酸等の多塩基酸から誘導されるポリエステルのジ(
メタ)アクリレートやポリウレタンアクリレートなども
使用できる。Polymerizable organic compounds are two or more (meta) molecules in one molecule.
A polyfunctional monomer or prepolymer having an acryloyl group is used. Examples of these compounds include di- or tri(meth)acrylates such as (poly)ethylene glycol, (poly)propylene glycol, hexanediol, glycerin, trimedylolpropane, pentaerythritol, dipentaerythritol, sorbitol, Examples include tri, tetra, or hexa(meth)acrylates such as. In addition, spiran (meth)acrylate, which is obtained by adding a polymerizable unsaturated group such as 2-hydroethyl (meth)acrylate to an unsaturated cycloacecool compound such as diarylidenepentaerythritol, also has good adhesion to the substrate. It is effective for improving To increase the hardness of the cured film,
It is effective to increase the number of the above-mentioned reactive functional groups, or to use di(meth)acrylate of a polyhydric alcohol with ethylene oxide added to bisphenol A or hydroquinone skeleton. In addition, in order to improve adhesiveness, polyvalent acrylates such as polybutadiene, which are made by acrylating reactive groups in resins, are used, silicone acrylates with acrylic groups at the terminals of silicone oligomers, methylolmelamine and 2-hydroxyethyl (meta)
Melamine acrylate derived from acrylate can be used to improve the heat resistance and chemical resistance of the coating film. In addition, polyester di(
Meta)acrylates and polyurethane acrylates can also be used.
これらの多価(メタ)アクリレートは、一種以上組み合
わせて使うと良く、その使用mは全組成物の30〜90
重皿パーセントであることが必要である。すなわち30
重皿パーセント未満では光重合後も硬さが充分でなく、
90重皿パーセント以上では、屈折率が低くならず反射
防止特性が不充分である。また、これら多価アクリレー
トはオリゴマーとしても使用できる。It is best to use one or more of these polyvalent (meth)acrylates in combination, and the amount of m used is 30 to 90% of the total composition.
It is necessary to have a heavy plate percentage. i.e. 30
If it is less than the heavy plate percentage, the hardness will not be sufficient even after photopolymerization,
If the ratio is more than 90%, the refractive index will not be lowered and the antireflection properties will be insufficient. Moreover, these polyvalent acrylates can also be used as oligomers.
但し、これらの希釈用の反応性モノマーに対し、一分子
中に二個以上の(メタ)アクリロイル基を有する多官能
モノマーあるいはプレポリマーの1は、全重合性有機化
合物中、少なくとも40重回パーセントが必要である。However, with respect to these reactive monomers for dilution, one of the polyfunctional monomers or prepolymers having two or more (meth)acryloyl groups in one molecule accounts for at least 40 percent of the total polymerizable organic compounds. is necessary.
40fifiパーセント以下では耐薬品性、硬さが劣り
好ましくない、またこれら以外の反応性モノマーとして
次のものを加えることが有用である。If it is less than 40 fifi percent, the chemical resistance and hardness will be poor and it is not preferable, and it is useful to add the following reactive monomers other than these.
希釈用反応性モノマーの例として
メチル(メタ)アクリレート、
エチル(メタ)アクリレート、
2−エチルへキシルアクリレート、
ブチル(メタ)アクリレート、
グリシジル(メタ)アクリレート、
(メタ)アクリロニトリル、
ヒドロキシエチル(メタ)アクリレート、ヒドロキシプ
ロピル(メタ)アクリレート、酢酸ビニル、
スチレン、
α−メチルスチレン、
α−クロロスチレン、
(メタ)アクリルアミド、
N、 N−ジメチル(メタ)アクリルアミドビニルナ
フタリン、
ビニルカルバゾール、
γ−メタクリロイルオキシプロピルトリメトキシシラン
、
β−アクリロイルオキシエチルトリメトキシシラン、
等が用いられる。この使用目的は、B成分のうちの多官
能モノマー成分の粘度を下げ塗布作業性を向上させると
ともに、重合したとき、塗膜に適度な弾力性、密着性を
与える為に必要である。即ち、多官能七ツマー成分のみ
で適度な弾力性と剛直さを産みだす組成物を組み合わせ
た場合は、この反応希釈成分は無くてもよいが、一般に
二重1部以上用いた方が均質な硬化膜が得られる。また
、この反応希釈成分を全重合性有機化合物中60重皿パ
ーセント以上用いると、硬化膜の耐薬品性や硬度が不充
分である。Examples of reactive monomers for dilution include methyl (meth)acrylate, ethyl (meth)acrylate, 2-ethylhexyl acrylate, butyl (meth)acrylate, glycidyl (meth)acrylate, (meth)acrylonitrile, and hydroxyethyl (meth)acrylate. , hydroxypropyl (meth)acrylate, vinyl acetate, styrene, α-methylstyrene, α-chlorostyrene, (meth)acrylamide, N, N-dimethyl (meth)acrylamide vinylnaphthalene, vinylcarbazole, γ-methacryloyloxypropyltrimethoxy Silane, β-acryloyloxyethyltrimethoxysilane, etc. are used. This purpose is necessary to lower the viscosity of the polyfunctional monomer component of component B and improve coating workability, and to impart appropriate elasticity and adhesion to the coating film when polymerized. In other words, when combining a composition that produces appropriate elasticity and stiffness with only the polyfunctional 7-mer component, this reaction diluent component may be omitted, but generally it is better to use 1 part or more of the 7-mer component to achieve a homogeneous result. A cured film is obtained. Furthermore, if this reaction diluent component is used in an amount of 60% or more based on the total polymerizable organic compounds, the chemical resistance and hardness of the cured film will be insufficient.
続いて、B成分中の光重合開始剤は、ベンゾインや、ベ
ンゾインメチルエーテル、ベンゾインエチルエーテル等
、ベンゾインエーテル類やベンゾフェノンをはじめとす
る、ベンゾフェノン類、アセトフェノン類、ブチロイン
、アントラキノン、ジフェニルジスルフィド、ベンジル
ジメチルアセタール類、アゾイソブチロニトリル等を単
独あるいは、二種以上混合して使用する。使用量は、硬
化成分の0.01〜5重量部が適当であり、0゜O1重
皿部以下では、重合が充分進まず、5重量部以上加えて
も効果は向上しない、この他、光1合開始剤と併せて、
光増感剤を併用することも効果がある。かかる化合物の
例としては、n−ブチルアミン、
ジ−n−ブチルアミン、
トリーn−ブチルホスフィンアリルチオ尿素、ジエチル
アミノエチルメタクリレート
トリエチレンテトラミン、
等がある。Subsequently, the photopolymerization initiator in component B is benzoin, benzoin ethers and benzophenone, such as benzoin methyl ether, benzoin ethyl ether, benzophenones, acetophenones, butyroin, anthraquinone, diphenyl disulfide, and benzyl dimethyl. Acetals, azoisobutyronitrile, etc. may be used alone or in combination of two or more. The appropriate amount to use is 0.01 to 5 parts by weight of the curing component; if the amount is less than 0°O, polymerization will not proceed sufficiently, and if more than 5 parts by weight is added, the effect will not improve. In conjunction with the 1st initiator,
It is also effective to use a photosensitizer together. Examples of such compounds include n-butylamine, di-n-butylamine, tri-n-butylphosphine allylthiourea, diethylaminoethyl methacrylate triethylenetetramine, and the like.
主要成分は以上であるが、これら以外に一般的な添加成
分を加えることも有用である。その中でも、シラン材料
は、数々の利点をもつ、即ちシリカ微粒子として、粒径
1〜100μmのコロイダルシリカはアルコール等の溶
剤分散型シリカゾル、水分酸シリカゾル等が市販されて
おり、好適である0本成分は、硬化樹脂層に、幾分かの
剛直さと耐薬品性を付与するのに効果がある。このシリ
カ成分の効果は、硬化被膜中に1fflJ!パーセント
から10重1パーセントの範囲で添加可能である。The main ingredients are listed above, but it is also useful to add general additive ingredients in addition to these. Among them, silane materials have a number of advantages, namely, as fine silica particles, colloidal silica with a particle size of 1 to 100 μm is commercially available as solvent-dispersed silica sol such as alcohol, hydrous acid silica sol, etc., and is suitable. The components are effective in imparting some stiffness and chemical resistance to the cured resin layer. The effect of this silica component is 1fflJ! in the cured film! It can be added in a range of 1% to 10% by weight.
10重1パーセントを越えると硬化膜の硬さと弾力性が
不充分となり、クラックを発生する為、有用ではない。If it exceeds 10% by weight, the hardness and elasticity of the cured film will be insufficient and cracks will occur, so it is not useful.
このようにして得られる被膜用組成物は、必要に応じ、
溶剤に希釈して用いることができる。溶剤としては、ア
ルコール類、エステル類、ケトン類、エーテル類の溶剤
が用いられる。また、塗布面の欠陥を改良する為に、シ
リコーン系界面活性剤、フッ素系界面活性剤、カチオン
、アニオン等のイオン系界面活性剤やノニオン系界面活
性剤、また、チキントロピー剤や、スリップ剤としてシ
リコンオイルなどを加えることも有用である。この他、
熱重合を抑え塗液を安定化させる為に、ベンジルトリメ
チルアンモニウムクロライドやベンゾチアゾール、ハイ
ドロキノン等の貯蔵安定剤を加えることができる。The film composition obtained in this way may be
It can be used after being diluted with a solvent. As the solvent, alcohols, esters, ketones, and ethers are used. In addition, in order to improve defects on the coated surface, silicone surfactants, fluorine surfactants, ionic surfactants such as cationic and anionic surfactants, nonionic surfactants, chicken tropic agents, slip agents, etc. It is also useful to add silicone oil or the like. In addition,
In order to suppress thermal polymerization and stabilize the coating solution, a storage stabilizer such as benzyltrimethylammonium chloride, benzothiazole, or hydroquinone can be added.
本発明を応用実施する方tムについて、いくらか述べる
。使用する光源は、200〜400nmの光線を一秒か
ら数分照射すればよい、また、ランプは、キセノンラン
プ、低圧水銀ランプ、中圧水銀ランプ、高圧水銀ランプ
、超高圧水銀ランプを用いる。このときの雲囲気は空気
中あるいは不活性ガス中で行なう。Some details will be given on how to apply and implement the present invention. The light source to be used may irradiate a light beam of 200 to 400 nm for one second to several minutes, and the lamp used may be a xenon lamp, a low-pressure mercury lamp, a medium-pressure mercury lamp, a high-pressure mercury lamp, or an ultra-high-pressure mercury lamp. The cloud enclosure at this time is performed in air or in an inert gas.
また、塗布は、浸漬法、スプレー法、ロールコート法、
スピンコード法、フローコート法などにより、所定の厚
さの硬化被覆膜を生成させることが出来る。Application methods include dipping, spraying, roll coating,
A cured coating film of a predetermined thickness can be produced by a spin code method, a flow coat method, or the like.
また、膜厚は、最も反射が低くなる膜厚をとることが望
ましいがその場合は、光の設計波長を約500nmとす
ると、0.1μ以下となる。塗膜によるハードコートを
めざす場合、1〜30μの厚さに塗布することも勿論可
能である。この反射防止機能を1呼るための理想的な膜
の屈折率は、空気、本発明による塗膜基剤(または、硬
化皮膜層)の屈折率をそれぞれ、nil n+、
”tとするとnl二f「r]iである時が最も反射の少
ないものとなる。Further, it is desirable that the film thickness has the lowest reflection, but in that case, if the design wavelength of light is about 500 nm, it will be 0.1 μm or less. When aiming at a hard coat using a coating film, it is of course possible to apply the coating to a thickness of 1 to 30 μm. The ideal refractive index of the film for this anti-reflection function is nil n+, nil n+,
When ``t'' is nl2f'r]i, there is the least reflection.
また、基材の処理は、アルカリや酸によるエツチング洗
浄や酸素、アルゴン等のガスプラズマで表面処理を行な
うことにより密着性を向上させることができる場合もあ
り、適宜選択することが好ましい、基材としては、透明
なプラスチック材料が適している0例としては、ポリカ
ーボネート、ポリスチレン、ポリアリルカーボネート、
ポリアクリル、ポリエステル、ポリエーテル、シリコン
樹脂、フッ素系光学樹脂等の他、無機ガラス類への加工
も有効である。In addition, adhesion can sometimes be improved by etching cleaning with alkali or acid or surface treatment with gas plasma such as oxygen or argon, and it is preferable to select the appropriate treatment for the base material. Examples of suitable transparent plastic materials include polycarbonate, polystyrene, polyallyl carbonate,
In addition to polyacrylic, polyester, polyether, silicone resin, fluorine-based optical resin, etc., processing into inorganic glasses is also effective.
以下、実施例により更に詳細に説明する。なお、実施例
中の部は、重量部を示す。Hereinafter, it will be explained in more detail with reference to Examples. In addition, parts in Examples indicate parts by weight.
実施例1
ペンタエリスリトールテトラアクリレート3゜0部、ト
リメチロールプロパントリアクリレート2.0部、パー
フルオロイソプロピルメタアクリレート3.0部、エタ
ノール水分散フッ化マグネシウムゾル(粒径10〜20
ミリミクロン、固形分20%)40部を混合したのち、
酢酸エチル50部を加えた溶液に、ベンゾインメチルエ
ーテル0゜1部および、シリコン系界面活性剤(日本ユ
ニカー−製、商品名rY7002J)300ppmを添
加し塗液を調整した。この塗液をCR−39レンズ(商
品名°°セイコーブラックス”セイコーエプソン@¥g
1)に塗布を行ない、毎分3000回転でレンズを回転
させて、奈分な液を振りきった。これを406Cで20
分間風乾した後、4KW高圧水銀灯を用い、両面を各々
光源直下15cmに配置し、3.0秒間、照射した。こ
のようにして得られた硬化被膜の厚みは、約0. 1μ
であり、硬さ、光沢ともにすぐれたものであった。Example 1 3.0 parts of pentaerythritol tetraacrylate, 2.0 parts of trimethylolpropane triacrylate, 3.0 parts of perfluoroisopropyl methacrylate, ethanol water-dispersed magnesium fluoride sol (particle size 10-20
After mixing 40 parts of millimicrons (solid content 20%),
A coating solution was prepared by adding 0.1 part of benzoin methyl ether and 300 ppm of a silicone surfactant (manufactured by Nippon Unicar, trade name: rY7002J) to a solution containing 50 parts of ethyl acetate. Apply this coating liquid to the CR-39 lens (product name °° Seiko Blacks” Seiko Epson @¥g
1) was applied, and the lens was rotated at 3000 revolutions per minute to shake off the remaining liquid. This is 406C for 20
After air-drying for a minute, both surfaces were placed 15 cm directly below the light source and irradiated for 3.0 seconds using a 4KW high-pressure mercury lamp. The thickness of the cured film thus obtained was approximately 0. 1μ
It had excellent hardness and gloss.
く試験と結果〉
得られたレンズは、次に述べる方法で試験を行ない、そ
の結果を第−表に示した。Tests and Results The obtained lenses were tested in the following manner, and the results are shown in Table 1.
a)屈折率:塗膜の屈折率は、シリコンウェハーに同一
条件で形成した塗膜を、エリプリメーターにより測定し
た。a) Refractive index: The refractive index of the coating film was measured using an elliplymeter on a coating film formed on a silicon wafer under the same conditions.
b)反射防止特性:片面の表面反射率をパーセントでし
めした。b) Antireflection properties: The surface reflectance of one side is expressed as a percentage.
C)耐摩耗性: #0000スチールウールで1kg
の荷重をかけ、10往復、表面を摩擦し、傷のついた程
度を目視で次の段階に分けて評価した。C) Abrasion resistance: 1kg with #0000 steel wool
The surface was rubbed 10 times with a load of
A: 1cmx3cmの範囲に全く傷がつかない。A: There was no damage at all within a 1cm x 3cm area.
B: 上記範囲内に1〜10本の傷がつく。B: 1 to 10 scratches within the above range.
C:上記範囲内に10〜100本の傷がつく。C: 10 to 100 scratches are made within the above range.
D=無数の傷がついているが、平滑な表面が残っている
。D = Countless scratches, but a smooth surface remains.
E:表面についた傷のため平滑な表面は残っていない。E: No smooth surface remains due to scratches on the surface.
d)耐水・耐薬品性:水、アルコール、灯油中に48時
間浸漬し、表面状態を調べた。d) Water resistance/chemical resistance: The surface condition was examined by immersing it in water, alcohol, and kerosene for 48 hours.
e)耐酸・耐洗剤性:0.IN塩酸および1%ママレモ
ンくライオン油脂畑製)水溶液に12時間浸漬し、表面
状態を調べた。e) Acid/detergent resistance: 0. It was immersed in an aqueous solution of IN hydrochloric acid and 1% Mama Lemon (manufactured by Lion Oil and Fat Field) for 12 hours, and the surface condition was examined.
f)耐候性: キャノンランプによるサンシャインウェ
ザ−メーターに100時間暴露した後の表面状態を調べ
た。f) Weather resistance: The surface condition was examined after being exposed to a sunshine weather meter using a Cannon lamp for 100 hours.
g)密着性:硬化被膜あるいは、反射防止コート薄膜と
レンズの密着性は、JI3D−0202に準じてクロカ
ットテープ試験によって行なった。g) Adhesion: The adhesion between the cured film or the antireflection coat thin film and the lens was determined by a crocut tape test according to JI3D-0202.
即ち、ナイフを用い、レンズ表面に1mm”のマス目を
100個形成させる1次に、そのうえへセロファン接着
テープ(日東科学0菊製“セロテープ′)を強くおしつ
けた後、表面から90°方向へ急に引っばり剥離したの
ち、コート膜の残っているマス目をもって密着性指標と
した。That is, first, use a knife to form 100 squares of 1 mm on the lens surface, then firmly press cellophane adhesive tape (Cellotape' manufactured by Nitto Kagaku Kiku) on the lens surface, and then apply it in a 90° direction from the surface. After the film was suddenly pulled off and peeled off, the remaining squares of the coat film were used as an index of adhesion.
h)染色性:得られたサンプルを、プラスチックレンズ
染色用溶液(セイコーエプソン■製ブラックス染色剤ア
ンバー)に90@05分間浸漬し染色濃度が30%以上
のものを良とした。h) Dyeability: The obtained sample was immersed in a plastic lens dyeing solution (Blacks dyeing agent Amber manufactured by Seiko Epson ■) for 90@05 minutes, and those with a dyeing concentration of 30% or more were judged as good.
実施例2
ジペンタエリスリトールへキサアクリレート25部、ペ
ンタエリスリトールトリアクリレート25部、テトラヒ
ドロフルフリルアクリレート5部に、ジアリリデンペン
タエリスリットのアクリレートエステル(昭和高分子■
製部品名“スビラツクT−500″)30部、パーフル
オロヘキシルエチルジメタクリレート10部、酢酸ブチ
ル50部を加え、混合攪拌しつつ、実施例1のフッ化マ
グネシウム400部、及びフッ素系界面活性剤0゜3部
を加え塗液とした。この塗液に、ポリメタクリル酸メチ
ルを、1400kg/cm”の圧力で射出成形後、アニ
ーリングによって歪みを補正した75mmφのサングラ
スレンズを浸漬し、実施例1と同様に塗布および硬化さ
せた。この硬化膜は、0.5μでひっかき強度の強いも
のであった。Example 2 Acrylate ester of diarylidene pentaerythritol (Showa Kobunshi ■
Add 30 parts of product part name "Subirak T-500"), 10 parts of perfluorohexylethyl dimethacrylate, and 50 parts of butyl acetate, and while stirring, add 400 parts of magnesium fluoride of Example 1 and the fluorine-based surfactant. 3 parts of 0° was added to prepare a coating liquid. Polymethyl methacrylate was injection molded at a pressure of 1400 kg/cm'' and a 75 mm diameter sunglass lens whose distortion was corrected by annealing was immersed in this coating solution, and the coating and curing were performed in the same manner as in Example 1. The film had a high scratch strength of 0.5μ.
評価結果を実施例1と同様に第−表に示した。The evaluation results are shown in Table 1 in the same manner as in Example 1.
実施例3
ジベタエリスリトールへキサアクリレート30部、ジペ
ンタエリスリトールペンタアクリレート20部、ジペン
タエリスリトールテトラアクリレート5部、パーフルオ
ロイソプロピルメタクリレート15部、2.2−ビス−
(4−アクリロイルオキシジェトキシヘキシル)プロパ
ン20部、γ−メタクリロキシプロピルトリメトキシシ
ラン15部、イソプロピルアルコール10部、酢酸メチ
ル30部を混°合攪拌しつつ、水分散フッ化カルシウム
ゾル(粒径5〜10ミリミクロン、固形分30%)30
0部をゆっくり加え、均一な溶液とした。これに前述の
シリコン系界面活性剤0.3部を加え塗液とした。この
塗液に、高屈折率レンズ(商品名“セイコーハイロード
°°ノンコートレンズ、セイコーエプソン畑製)を浸漬
し、引き上げ速度30cm/minで引き上げることに
より塗布した。これを40” Cで20分間風乾した後
、窒素雰囲気下、20W低圧水銀灯を用い、両面を各々
光源直下2cmに配置し60秒間照射を行ない硬化皮膜
をえた。このときの膜厚は、2.5μであり透明性にす
ぐれたものであった。Example 3 30 parts of dibetaerythritol hexaacrylate, 20 parts of dipentaerythritol pentaacrylate, 5 parts of dipentaerythritol tetraacrylate, 15 parts of perfluoroisopropyl methacrylate, 2.2-bis-
While stirring 20 parts of (4-acryloyloxyjetoxyhexyl)propane, 15 parts of γ-methacryloxypropyltrimethoxysilane, 10 parts of isopropyl alcohol, and 30 parts of methyl acetate, water-dispersed calcium fluoride sol (particle size 5-10 millimicrons, solid content 30%) 30
0 part was slowly added to form a homogeneous solution. 0.3 parts of the silicone surfactant described above was added to this to prepare a coating liquid. A high refractive index lens (trade name: "Seiko High Road °° Non-Coated Lens, manufactured by Seiko Epson Field") was immersed in this coating solution and applied by pulling it up at a pulling speed of 30 cm/min. This was applied at 40"C for 20 minutes. After air drying, both surfaces were placed 2 cm directly below the light source and irradiated for 60 seconds using a 20 W low pressure mercury lamp in a nitrogen atmosphere to obtain a cured film. The film thickness at this time was 2.5 μm and had excellent transparency.
評価結果を実施例1と同様に第−表に示した。The evaluation results are shown in Table 1 in the same manner as in Example 1.
実施例4
塗液の調整、塗布および硬化は、実施例2と同様に行な
い、ポリメタクリル酸メチルのかわりに、ビスフェノー
ルA型ポリカーボネート樹脂(三菱化成■製、商品名“
”N0VAREX”)を射出成形後、アニーリングによ
って歪みを補正した75mmφのプラルンズを用いるこ
とにより、高屈折率で耐衝撃性に富むレンズをえた。こ
のようにして得られたレンズの評価試験結果を第−表に
示す。Example 4 The preparation, application, and curing of the coating liquid were carried out in the same manner as in Example 2, and instead of polymethyl methacrylate, bisphenol A polycarbonate resin (manufactured by Mitsubishi Kasei ■, trade name "
By injection molding "N0VAREX" and then using a 75 mm diameter prairens whose distortion was corrected by annealing, a lens with a high refractive index and high impact resistance was obtained. Table 1 shows the evaluation test results for the lenses thus obtained.
比較例1
実施例1の塗膜の調整時、メタノール水分散フッ化マグ
ネシウムゾルを除いた組成物を用いること以外は、実施
例1と同様にして得られたレンズの評価試験結果を第−
表に示す。Comparative Example 1 The results of the evaluation test of a lens obtained in the same manner as in Example 1 except that the composition excluding the methanol-water-dispersed magnesium fluoride sol was used when preparing the coating film in Example 1 were evaluated.
Shown in the table.
比較例2
実施例2において、塗液として、γ−グリシドキシプロ
ビルトリメトキシシラン12部、メタノール分数コロイ
ダルシリカ19部、メチルトリメトキシシラン29部、
酢酸0.1部、及び0,05規定塩酸水20部を混合し
80°Cで2時間反応させたのち、エチルセロソルブ1
6部、化塩素アンモニウム0. 3部を加えコーテイン
グ液を調整した。この塗液を用い、塗布後、 100°
Cで1時間硬化させること以外は、実施例2と同様に行
ない、この評価試験結果を第−表に示す。Comparative Example 2 In Example 2, the coating liquid contained 12 parts of γ-glycidoxypropyltrimethoxysilane, 19 parts of methanol fraction colloidal silica, 29 parts of methyltrimethoxysilane,
After mixing 0.1 part of acetic acid and 20 parts of 0.05N hydrochloric acid and reacting at 80°C for 2 hours, ethyl cellosolve 1
6 parts, ammonium chloride 0. A coating solution was prepared by adding 3 parts. Using this coating liquid, after coating, 100°
The evaluation test results are shown in Table 1. The evaluation test results are shown in Table 1. The evaluation test results are shown in Table 1.
比較例3
実施例1において、コーティングによる硬化膜形成のか
わりに、SiO2からなる無機ハードコート層を1μm
もうけ、レンズを作製した。評価結果を第−表に示す。Comparative Example 3 In Example 1, instead of forming a cured film by coating, a 1 μm inorganic hard coat layer made of SiO2 was applied.
He made some money and made lenses. The evaluation results are shown in Table 1.
本コーティング組成物は、それ自体として屈折率が低い
フッ化マグネシウム(屈折率1.25)を用い、バイン
ダ成分として、これら無機粒子と反応・作用し強固な硬
い膜形成可能な重合性有機化合物を用いたため、塗布・
硬化して得られた膜は、均質で強固な、屈折率の低い膜
を形成する。This coating composition uses magnesium fluoride (refractive index 1.25), which itself has a low refractive index, and contains a polymerizable organic compound that reacts and acts with these inorganic particles to form a strong, hard film as a binder component. Because it was used, it was applied and
The cured film forms a homogeneous, strong film with a low refractive index.
このため、表面反射(r)は、フレネルの式(1)%式
%)
・・・・・式(1)
(ここでnlは空気の屈折率、nlは基剤の屈折率、n
3は本塗膜の屈折率である。)膜厚が4分の1の奇数倍
で上記最小値をとることができる。理想的には、例えば
屈折率1.6の基材なら、屈折率1゜26の薄膜につい
て、4分の1の奇数倍の膜厚をとる波長の光反射は零と
なる。このような作用により、本コーチ、イング組成物
は、反射を低減させるための効果を生かせるものである
。すなわち本発明では、塗膜の屈折率は1.30〜1.
45の間で選択でき、反射は0.2〜3パーセントにお
さえられる。Therefore, the surface reflection (r) is expressed by Fresnel's formula (1) (% formula %) ... Formula (1) (where nl is the refractive index of air, nl is the refractive index of the base material, n
3 is the refractive index of the actual coating film. ) The above minimum value can be achieved when the film thickness is an odd multiple of 1/4. Ideally, for example, in the case of a base material with a refractive index of 1.6, the light reflection of a wavelength that is an odd multiple of a quarter of the thickness of a thin film with a refractive index of 1°26 will be zero. Due to this action, the present coaching composition can effectively reduce reflection. That is, in the present invention, the refractive index of the coating film is 1.30 to 1.30.
45, and reflections are kept between 0.2 and 3 percent.
本発明の効果は、プラスチックレンズ材料として、 (
メタ)アクリル樹脂をはじめとしてスチレン樹脂、カー
ボネート樹脂、アリル樹脂、アリルカーボネート樹脂、
ビ4ル樹脂、ポリエステル樹脂、ポリエーテル樹脂、更
に新たなモノマーやコモノマーの重合体など各種機能を
もった樹脂に応用し得られる。すなわち、染色可能で、
安価に大面積に製造でき、かつ優れた耐擦傷性と良好な
密着性を有する反射防止機能薄膜を得ることができる。The effect of the present invention is that as a plastic lens material, (
Including meth)acrylic resin, styrene resin, carbonate resin, allyl resin, allyl carbonate resin,
It can be applied to resins with various functions such as vinyl resin, polyester resin, polyether resin, and polymers of new monomers and comonomers. i.e. dyeable,
It is possible to obtain an antireflection functional thin film that can be produced in a large area at low cost and has excellent scratch resistance and good adhesion.
従って、眼鏡レンズをはじめとして、それ以外にも、カ
メラレンズ、光ビーム、集光レンズや光拡散用レンズ等
、光学用レンズとして、民生用或いは産業用に広く応用
することができる。更に本発明による効果は、ウォッチ
ガラスやデイスプレィ用カバーガラス等の透過ガラス、
またカバーガラス等、光学用途の透明プラスチック全般
に応用利用が可能であり、えられる効果は多大である。Therefore, it can be widely applied not only to eyeglass lenses but also as optical lenses such as camera lenses, light beam lenses, condensing lenses, and light diffusion lenses for consumer and industrial purposes. Furthermore, the effects of the present invention can be applied to transparent glasses such as watch glasses and display cover glasses;
Furthermore, it can be applied to all transparent plastics for optical applications, such as cover glasses, and the effects that can be obtained are great.
Claims (3)
いて、全固形分中、Aを10〜70重量パーセント、B
を90〜30重量パーセントとからなることを特徴とす
るコーティング組成物。 A、粒径1〜50ミリミクロンのフッ化マグネシウム、
または/及びフッ化カルシウムの微粒子。 B、重合性有機化合物及び光重合開始剤。(1) In the active energy ray-curable coating composition, A is 10 to 70% by weight and B is 10 to 70% by weight based on the total solid content.
90 to 30 percent by weight of a coating composition. A, magnesium fluoride with a particle size of 1 to 50 millimicrons;
or/and fine particles of calcium fluoride. B, polymerizable organic compound and photopolymerization initiator.
重量パーセントは、一分子中に2個以上の(メタ)アク
リロイル基を有する多官能モノマーあるいはプレポリマ
ーからなることを特徴とする請求項1記載のコーティン
グ組成物。(2) at least 40 of the components of the polymerizable organic compound;
2. The coating composition according to claim 1, wherein the weight percent consists of a polyfunctional monomer or prepolymer having two or more (meth)acryloyl groups in one molecule.
折率が1.30から1.45であることを特徴とする請
求項1記載のコーティング組成物。(3) The coating composition according to claim 1, wherein the coating film obtained by the coating composition has a refractive index of 1.30 to 1.45.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1138714A JP2730185B2 (en) | 1989-05-31 | 1989-05-31 | Coating composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1138714A JP2730185B2 (en) | 1989-05-31 | 1989-05-31 | Coating composition |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH036265A true JPH036265A (en) | 1991-01-11 |
JP2730185B2 JP2730185B2 (en) | 1998-03-25 |
Family
ID=15228414
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP1138714A Expired - Lifetime JP2730185B2 (en) | 1989-05-31 | 1989-05-31 | Coating composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP2730185B2 (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000034396A1 (en) * | 1998-12-09 | 2000-06-15 | Nippon Kayaku Kabushiki Kaisha | Hard coating material and film obtained with the same |
US6110987A (en) * | 1996-07-16 | 2000-08-29 | Showa Denko K.K. | Photocurable composition and curing process therefor |
US6383620B1 (en) | 1996-08-14 | 2002-05-07 | Daikin Industries, Ltd. | Antireflection article |
JP4061656B2 (en) * | 1993-12-28 | 2008-03-19 | ダイキン工業株式会社 | Coating composition and painted product |
JP2008158470A (en) * | 2006-11-30 | 2008-07-10 | Seiko Epson Corp | Product having organic layer of low-refractive index |
WO2012053427A1 (en) * | 2010-10-18 | 2012-04-26 | 株式会社ニコン | Optical thin film, multilayer optical thin film, optical element, method for producing optical element, and coating liquid for forming optical thin film |
JP2014199328A (en) * | 2013-03-29 | 2014-10-23 | Hoya株式会社 | Dyed lens and method of producing the same |
-
1989
- 1989-05-31 JP JP1138714A patent/JP2730185B2/en not_active Expired - Lifetime
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4061656B2 (en) * | 1993-12-28 | 2008-03-19 | ダイキン工業株式会社 | Coating composition and painted product |
US6110987A (en) * | 1996-07-16 | 2000-08-29 | Showa Denko K.K. | Photocurable composition and curing process therefor |
US6383620B1 (en) | 1996-08-14 | 2002-05-07 | Daikin Industries, Ltd. | Antireflection article |
WO2000034396A1 (en) * | 1998-12-09 | 2000-06-15 | Nippon Kayaku Kabushiki Kaisha | Hard coating material and film obtained with the same |
US6713170B1 (en) | 1998-12-09 | 2004-03-30 | Nippon Kayaku Kabushiki Kaisha | Hard coating material and film comprising the same |
JP2008158470A (en) * | 2006-11-30 | 2008-07-10 | Seiko Epson Corp | Product having organic layer of low-refractive index |
WO2012053427A1 (en) * | 2010-10-18 | 2012-04-26 | 株式会社ニコン | Optical thin film, multilayer optical thin film, optical element, method for producing optical element, and coating liquid for forming optical thin film |
JP2014199328A (en) * | 2013-03-29 | 2014-10-23 | Hoya株式会社 | Dyed lens and method of producing the same |
Also Published As
Publication number | Publication date |
---|---|
JP2730185B2 (en) | 1998-03-25 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5130503B2 (en) | Antireflection film | |
CN101796146B (en) | Self-assembling antireflective coating comprising surface modified high refractive index nanoparticles | |
CN110031919B (en) | Low refractive layer and anti-reflection film including the same | |
US20100238397A1 (en) | Coating composition and optical mar-resistant tintable coating | |
JPH0314879A (en) | Coating composition | |
US4308119A (en) | Abrasion-resistant optical coating composition containing pentaerythritol based polyacrylates and cellulose esters | |
CN107438778B (en) | Low-index layer and antireflective coating comprising the low-index layer | |
US4399192A (en) | Radiation cured abrasion resistant coatings of pentaerythritol acrylates and cellulose esters on polymeric substrates | |
JPH01197570A (en) | Low-refractive index hard coating agent | |
TW202007735A (en) | Hard coating layered optical film , polarizer comprising the same, and image display comprising the hard coating layered optical film and/or the polarizer comprising the same | |
JP2010195901A (en) | Resin composition for hard coat, process of producing resin composition for hard coat, and substrate for anti-reflection coating | |
JPH0314880A (en) | Coating composition | |
JP2000080169A (en) | Active energy ray curable coating composition | |
US4407855A (en) | Method for forming an abrasion resistant coating from cellulose ester and pentaerythritol acrylates | |
JP2730185B2 (en) | Coating composition | |
JPH1192750A (en) | Antistatic composition and antistatic antireflection film | |
JP3436492B2 (en) | Thin article having a wear-resistant thin film and optical disc | |
JP2012242833A (en) | Composition for forming low refractive index layer, and antireflection film, polarizing plate and display device using the same | |
JPH03145602A (en) | Laminate and production thereof | |
JPH01210433A (en) | Coating composition | |
JPH0228267A (en) | Coating composition | |
JPH10268111A (en) | Nonglare sheet | |
JP3220906B2 (en) | Composition for coating | |
KR100904037B1 (en) | Anti-reflection coating composition and anti-reflection film using the same | |
JPH03281613A (en) | Composition |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20081219 Year of fee payment: 11 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20081219 Year of fee payment: 11 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20091219 Year of fee payment: 12 |
|
EXPY | Cancellation because of completion of term | ||
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20091219 Year of fee payment: 12 |